First Time

My Brother Saves Halloween – Part 1

First Time, Illustrated, Incest, Masturbation, Oral, Siblings, Straight, Tommy Linarcos, Tweens |

This story was written as part of a proposed “contest” between myself and three other writers.  Five prompt terms were randomly chosen from categories and would have to be part of each story in some fashion.  The contest wound up not happening, but I liked the idea I’d gotten and wrote it, anyway.

The prompt terms were:  incest / brother-sister / Halloween / rainy day / must include the line: “You and I in a little toy shop, buy a bag of balloons with the money we’ve got.” (Whether you’ve recognized this or not, all of Jason Crow’s stories begin with a song lyric – go ahead, go back and look if you don’t believe me! – so I pulled a lyric randomly from a select group when the terms were chosen.)  I don’t know if I’d have won the contest, but I hope you enjoy the story. 

The first half is a lot of character-building, very story-heavy.  These things were very important to your narrator, Katie, who needed to tell you about them for you to understand the rest of her story.  Please don’t skip it the first time reading – the “action” is always better, always means more, when you are invested in the characters.  (The next time you read it, you can skip to where you want to!)

Cheers,

Tommy L.

My Brother Saves Halloween – Part 1
By
Tommy Linarcos

“You and I in a little toy shop, buy a bag of balloons with the money we’ve got,” my brother sang near my ear.  I giggled, but was more interested in his hands on my waist — not tight, just… right there… on my hips, as if he were supporting himself while he leaned down that little bit.  That made me smile, and shiver a little.  A good shiver.  I liked when we were friends, when we were close.

My brother paid for the balloons and all the other stuff we’d picked to make Halloween costumes out of, and we left the store.  He took my hand and we headed back to our hotel to get creative.

Here’s the deal.  My aunt was finally getting married to her beau on the Saturday after Halloween.  They really liked Halloween — it was when they’d met!  I don’t want to say that my mom forced me and my brother to go to the wedding, because she didn’t.  We like our aunt, and wanted to go.  My mom’s like, “Katie, I’m afraid you and Henry have to take a few days off of school because we’re going to Chicago for Aunt Marcy’s wedding!” and I pretended to be mad — all “awwww, dang!” and stuff, but laughing.  Mom knew!  The only thing against it was that we’d miss Halloween with our friends, but we’d have our cousins.  Or so we thought.

My aunt lives somewhere in Chicago, and it’s always fun to visit her a couple times a year.  We go for a week every summer, and either spring break or winter break, and do different things, or sometimes just hang out when our cousins come meet us there or we head out to their houses. 

Back in spring, right around Easter, we stayed at this Wolf Lodge place in the Chicago suburbs.  There were a ton of water slides there and it was fun playing with Henry on those.  I’ll tell you right now: my brother is hot!  At least to me and my friends.  My cousins got to stay there, too, so it was fun all-around, but I secretly liked hanging all over my nearly-naked big brother as we’d slide down a big slide together — my “needing” him for safety!  He was always careful of my boobs when he’d hold onto me, or toss me in the water, but not of my butt, and I never minded that!

We live in Nebraska, so it’s fun to go to the Big City a couple times a year, and I don’t mean Omaha!  At home, there’s a lot of land and not a lot to do.  If me and Henry didn’t have our bikes, I don’t know what we’d do.  We’re not farmers, though my dad is — he runs Mr. Tyrell’s operation.  We live in the Omaha suburbs, kind of in-between Omaha and Lincoln, near the Platte River, but that really just means there’s some distance between our house and fun stuff.  Not like you can swim in the Platte, anyway.  And yeah, I hate it when my cousins ask about what it’s like when the cows are flying around from all the tornados…  (I’ve seen one tornado.)

Life out there revolves around the corn.  For the last two summers, Henry did some detasseling and roguing work for a few weeks for good money, and this is the first year I got to go and work with him, too.  I hated it and didn’t last the season.  I should have known when the boss was like, “A twelve-year-old girl?  You won’t last.”  He was right, I didn’t last a week, honestly.  There was only one other young girl there that first day, but a few teenage girls stuck it out, I’m told.  It was odd watching my brother dress in long sleeves and such for work on hot days.  Back home in the summer, all he wears is a pair of shorts and his Cornhuskers hat, so he got himself a nice tan, anyhow, and he’s building up some muscles, so I really like it when he rides shirtless and I get to see them.  In the summer, anyway.

So, when I’m talking about a trip to the city, I mean Chicago.  A real city where the buildings just don’t stop and Lake Michigan is so big it might as well be the ocean!

Anyway…

We’d been forgotten about on Halloween.  I’ll admit, it kind of hurt.  No, it really hurt. 

We got here Thursday, taking Amtrak in with Mom (Dad would come later), and were staying at this big hotel downtown.  Aunt Marcy and her fiancée Ronald came to have dinner with us, and so did my mom’s brother Uncle Ted and his wife Aunt Frannie, and my Uncle Bill and Aunt Trisha, but none of their kids came — too fancy a restaurant for all the kids.  They all said we could come to their places for Halloween tricks-n-treats and they’d come get us.

The next day, Halloween, the adults were doing the wedding rehearsal in one of the dining room/conference room places down on the third floor, and then they were going to have a dinner and hang out and get drunk the rest of the night, so all of our cousins were at home going Trick-or-Treating or going to a friend’s Halloween party. 

And Henry and me were left here, in the hotel.  We were supposed to have gone to one of their houses and they’d help us with costumes and we’d go Trick-or-Treating with the cousins.  Hell, we’d have gone even if it was just with the littler kids, if someone had come out to pick us up.  Or if we knew the bus routes.

Just the wedding party people showed up.  Nobody showed to get us.  We waited.  We didn’t have their numbers, so we couldn’t call.  We could have gone down to hang out with the rehearsal crowd, but we would have just been in the way, waiting for it to end, looking pathetic.

So we sat in the lobby for an hour after we expected to get picked up.  There’s only so many times you can read the comics in the newspaper.  Then my brother stood up and made a decision.

“C’mon, Katie,” Henry said as he took my hand, “we’re goin’ costume shoppin’.”  There was something stuck in our brains from when we were little that Henry had to hold my hand when we went places.  I was just-turned twelve this summer, and Henry would be fourteen come January, but he still did it, and there was no way I was going to stop him.  We left the hotel lobby and walked out onto Michigan Avenue.

There’s just something about the city!  It just feels different!  There’s electricity in the air!  People moving fast, some talkin’ to themselves on the phone, men in suits, ladies with shopping bags, teenagers or college kids dressed however they want to, and some dressed like people in the movies.  All the cars… I bet there were as many cars passing us by right there than in the whole of Lincoln!  And when I looked down the street, the street just kept going, it didn’t end at a field.

“Hey!” Henry was pointing to a hole in the middle of the street that cars were driving down into.  “That’s from Batman!  When, in Batman Dark Knight, they go down into the street underneath Gotham City?  That’s it!”  He was so excited, but he never let go of my hand.  We’d seen some movies with Chicago in it before when we’d come out so we could see if we recognized anything, like Ferris Bueller and The Fugitive, but seeing Batman stuff always made Henry happy.

Down the street, there was this one giant slanty building with big giant Xs on it all the way up, and no matter how much walking we did, we never got closer to it!

“Henry, why ain’t we getting any closer to that building?  It’s just always… down there… and we keep walking, and it’s still down there!” I asked my brother.  I’m not dumb, but what the heck?

“That’s the John Hancock building,” Henry told me, as if that explained it all.

I had to giggle.  “Hand cock!”

“Yeah, I’ll give you hand cock!” Henry laughed right back.  He put his free hand in his pocket and thumped it out a few times, guaranteeing I kept laughing.  I had to look around quickly to see who saw us.  No one, really.  Just my brother, smiling at me with a big grin, his blonde hair falling over his eye.  He had it long in front on one side, and when he popped up out of the water in the pool, he could swing his head and shoot water at you with that hair, and he was pretty darn accurate!

“So, where’s the Serious Tower?” I asked him when I stopped giggling.

“In-land a bit, away from the lake so it don’t fall in the water if the beach erodes.”  He pointed to our left.  Used to be the tallest building in the world, but I still couldn’t see it because of all the other tall buildings.

It was actually kind of cold, so I was glad we were dressed for travel.  My mom says when she was young here, it actually snowed one Halloween, and she had to wear her winter coat over her Little Mermaid dress!  I hoped it wasn’t going to snow, though it did feel a little like rain, but Henry said that it might just be because we were right next to the lake.

Not that I didn’t like walking and looking at the people and the buildings, but…  “Henry, where are we going?”  We had to pull over out of the flow of people, standing next to a street lamp that people would walk around us naturally.  It was cool that some of the people were dressed for Halloween — the girls, mostly, in black and with color-sprayed hair, though we did see some boys who looked kinda like zombies.

Henry turned around in a circle, nice and slow, looking at the names of the stores.  “I thought there might be a good store around here, like a Target or something we could get costumes in.”

“What do we need costumes for?  Ain’t nobody come to get us for tricks-n-treats,” I reminded him.

“Katie, we may be stuck here in Chicago, but this is where they make candy!  And there’s all these people in black and orange, and everybody knows it’s Halloween, and all we need is some good costume and we can go Trick-or-Treating in these places right here.  And there’s got to be some homes and apartments somewhere off this main street, you know?”  My brother looked determined.  I admired that about him.  No forgettin’ uncle was going to ruin our Halloween!

Then me and Henry spotted it at the same time.  A Walgreens!  That was something we knew!

So we were at the Walgreens buying supplies to make Halloween costumes out of.  There was a big Chicago souvenirs section, but there wasn’t much in the Halloween section except candy because this was a “downtown” store, so no Spider-Man or Pikachu costumes, and no Batman costume, which disappointed Henry.  So we had to be creative.

“What if…” Henry began as we wandered down the aisles.  He picked up a little stuffed dog next to the birthday cards.  “I wear my wedding suit and tape this dog to me and some makeup for bruises and a beard?  I could be John Wick!”

I caught on to what he was talking about being creative.  I picked up three stuffed little kittens.  “I can pin these to one of the hotel robes, wear the complimentary slippers, and be a crazy cat lady!”  I could curl my hair weird with mom’s curling iron.

Next, I found a bag of purple balloons.  “Could blow these up, pin ‘em on me, I’m a bunch of grapes!”  That was a good ‘maybe.’  We took the balloons, too.

We saw some toys from Jurassic World.  “If you wore your shorts, and my button-down shirt,” Henry was thinking, “you could be that woman from Jurassic Park 1.  We just need to make a badge or something, maybe with a stuffed dinosaur?”

We picked up a box of markers.  There was stationery in the hotel room to draw on.

We passed into the clothing aisle.  There were some red leggings.  “I wear these, and your red Cornhuskers shirt inside-out, and a green wool hat, and I’m a bottle of sriracha!”  We both went, “M’eh…” but I put ‘em in the basket.  A red wool hat could make us into a horrid, horrid lawn gnome, if we could find something for a beard?  No.  There was a leotard, and if I paired it up with something, I could be Barbie, maybe tape paper wheels to my shoes and she could be rollerblading…  Complicated, but I could do anything as a Barbie if I stick out my chest and smile a lot.  I got some boobs, now — not big, but they’re there.  I told that to Henry, and that we could make him into a Ken, so we went to the beauty aisle and found Aqua Net hairspray, as an option.

“Blue hairspray?” Henry found a colored spray can nearby.  “Hey, you could be that sad blue girl from Inside Out?”

“I don’t know if that would work,” I said.  “I think I saw that girl outside, like in real life.  So, not a costume.”

On our way back to clothing, we passed the automotive section and I picked up a chamois.  I held it at Henry’s waist.  “Tarzan?” I kidded.  Yeah, I was kidding, but part of me imagined Henry nearly-naked wearing it.  I mean, I’ve seen him swimming and how he runs around, but having him wear it on purpose would be fun!

Henry picked up a second chamois.  “Only if you be Jane!”  He held the chamois across my boobs. 

Now my imagination went nuts, but I held it together.  “Sorry, that’ll never hold these puppies…” I said, holding my right boob with my free hand.  Henry laughed, but looked at me a little longer, then put the two chamois away.

Back in clothing: “Some big mittens, and be that Bernie guy from Congress?”  M’eh…  “An umbrella and be some kind of Mary Poppins?”  M’eh…  “This wife-beater t-shirt, my jeans, paint on a mustache, and be Freddy Mercury?” 

“That’s a maybe,” I said, picturing my brother’s bare arms.

“A blue t-shirt…  Look around, maybe there’s at least a Superman shirt, or I can get this plain one and color an S on paper.  There’s glasses over by the pharmacist.  With my suit coat, I could be Clark Kent?”  Henry seemed to like that, so we took the blue tee.

Food was down the next aisle forward.  We put a bag of Doritos and some Ruffles in our handbasket, and some little donuts, then chose two Cokes apiece — I got Vanilla, Henry got Cherry.  You need stuff like that for TV watching in the room, you know?  There was those little boxes of cereal…  “Could tape these to you and be a cereal killer?  Find or make a knife?  Tape them to your shirt, do crazy eyes?”  That was a maybe, but it reminded us to get some tape, too, since we kept thinking we could tape things to ourselves.

I put a plant on my head.  “Get a yellow tablecloth for a poncho and I’m a pineapple?”  M’eh…

“Here’s some silk roses.  Wear your dress and you could be The Bachelorette!” Henry suggested.

That was a maybe.  “I’d have to be pretty for anyone to get it…”

“You are pretty,” Henry told me.

I had to stop.  That floored me!  “You… you think I’m pretty, Henry?”

My brother blushed a bit.  Here we were in the middle of Walgreens and I kind of put him on the spot.  But what else could I say?  It was a thrill and a mystery at the same time!

“Hey, don’t take this the wrong way, like weird, or anything,” he started, kind of shifting.  “You’re my sister, and everything, but even I can see you’re a hot little number and I’m gonna have to keep my friends away from you, one day soon.”

I didn’t know what to say.  This was… I couldn’t believe it!  The words were spinning in my head and I had to…  I threw my arms around Henry, bashing his ribs with the handbasket, my ear pressed to his chest.  “Do you really mean that, Henry?”

I heard his “Of course, I do” through his body, the air in his lungs just reverberating into my ear.  His hands were around me, his one hand stroking my long gold hair, but then I felt him pulling away.

Oh… yeah… we were still in the middle of Walgreens.

“C’mon, let’s go buy this stuff and get back to figure out what we’re gonna do,” he told me.  And that’s when he sang in my ear, at the counter when I was taking the stuff out of the basket, and he saw the balloons, again.

I love my brother.

On the way back to the hotel, we stopped at this guy’s stand in the big Millennium Park with the mirror bean thing in it and bought some overpriced hotdogs.  They were good hotdogs, but apparently, ketchup is not allowed on hotdogs in Chicago.

Up in our room, we ate the dogs and fries and felt less angry with food in our stomach.  I guess we got a pretty good room for this special occasion, a suite.  There was this fancy sitting room with a couch and chairs and a table and windows and everything; our mom’s bedroom had one big bed in it she’d be sharing with Dad when he made it into town; and Henry and I had our own bedroom with two single beds in it.  They probably thought they were doing us a favor.  Most times when we travelled, we all got one room with two big beds, and I had to share with Henry — which I didn’t mind, at all.  But with actual bedrooms, we knew Mom and Dad wanted to snuggle this weekend.  With two single beds, though, I couldn’t slide over in my sleep and spoon with Henry.  But at least we had privacy.  And our own washroom, which was nice.

We dumped out our supplies on the desk by the TV.  We got the puppy, three kitties, balloons, a blue shirt, an eight-pack of little cereals, six fake roses, a pair of cheap kiddie sunglasses, a sleeveless undershirt, a leotard, red leggings, green wool hat, Aqua Net hairspray, some tape, scissors, Doritos, Ruffles, little gem donuts, and two Cokes.  (The Cokes went into the fridge because we bought two root beers from the hotdog guy.)  The whole thing cost a lot more than Henry wanted to spend, but he had his money from our summer job, and we wanted to give ourselves the options.

We had to get going on these costumes if we wanted to get out there and find tricks-n-treats.  Henry took off his Nike shirt and then his jeans, figuring he’d try ‘Clark Kent,’ first.  Stripping down to our underwear was no big deal — we saw each other like that every day.  But when Henry stood there in just his blue briefs and his socks…  “Hey, if we went back and got you blue leggings, you could be Superman!” I said.

There he was, almost naked.  It was different looking at him in his underwear.  When he was in his shorts, his butt was the same shape, sure, but it looked different in his briefs, like he showed the actual curve.  His front was very different, too — in his shorts, his dick was just a bulge, but here it had shape, you could tell where each of the parts were and what they were doing!

But he stood there, his getting-muscular chest, his arms with summer-work biceps, his strong legs, and that underwear, socks for boots, and he looked like a superhero.  He seemed to consider it.

“I know what you mean,” he said to the floor, looking at his legs and undies, “but we’re not going back.  We should’ve thought of that before.  I’ll bet you there was a Dracula cape there, somewhere.  If we got all black stuff, I could be Bruce Wayne, like after fighting the Joker, like when he got home and he took off his mask.”  Then he looked at our stuff on the table.  He picked up my red leggings.  “But, with these, and my Cornhuskers shirt inside-out, maybe I could be The Flash…”

He tried to step into them, realizing he needed his socks off, then got the leggings up to his thighs, finally realizing his briefs needed to be on the outside of the leggings.

My brother took off his underwear.  I saw his butt.  His real butt.  He was turned away from me, but I couldn’t look away.  My brother was naked.  He put on the leggings, then his briefs, and then his red shirt, and turned to me.  “Yes?  No?”

I was still a little dazed.  “The leggings actually make your legs look skinnier,” I was able to say when I came to my senses.  The combination really didn’t look good, even for a cheap costume.

“Yeah, that’s what I figured…” Henry said, then sat down and took everything off, again.  I couldn’t, like, stand up and run in front of him to look, but just knowing he was briefly naked in my presence, again, was unbelievable.  I didn’t say a thing.  Just enjoyed it.

He found and dressed in his khakis, the new blue tee, and with his button-down shirt open.  Then he got about coloring a Superman S shield on hotel stationery.  I, meanwhile, taped the three kittens to the hotel robe and tried that on.  “Crazy Cat Lady?” I modeled for Henry.

“What are you going to wear under it?  Your jeans, like that?” he asked.  He popped the lenses out of the cheap sunglasses and had his Clark Kent glasses.

I wasn’t sure.  It wasn’t a sexy costume, just funny.  I’d have to mess up my hair.  “Maybe my pajama pants?”

“How about the grapes or the sriracha?”

I ditched the robe and then I had to face the same choice Henry had.  Do I change into the red leggings in the bedroom, or just do it out here, like he had?  I went for broke and decided to tease him back, just to see his reaction.  I stripped down to my bra and panties in front of my brother.  Nothing he hasn’t seen before, but we were here.  “Hand me your red shirt,” I asked as I put the leggings on.

My brother watched me.  He didn’t give me the shirt until the leggings were on.

“With them over your underwear, they’re all bunched up,” he said, clearly looking at my ass. 

I went to the mirror and turned around.  “Yeah, but with the shirt, you can’t see them.”  Henry shrugged, and then helped me out by coloring a “Sriracha” label.

I put on the green wool cap; I thought I looked funny, in a good way.  Henry topped himself off with his suit coat, we took a couple pictures of ourselves (I wish I’d had my camera out when Henry flashed me his butt!), we made sure we had a room key and a couple Walgreens loot bags, and went out into the halls as Clark Kent and Sriracha!

We tried knocking on a room door down our hall.  No answer.  We tried another.  No answer.  The third door said, “What do you want?” 

We sang “Trick or treat!” 

The door said, “Go away.”

We had to figure that would happen.  We had better luck at the next door.  We knocked and it opened.  A man with no shirt stood there.  He had pants and shoes, but no shirt.  He was very hairy, like chest, shoulders, and his back!  I didn’t know men could grow hair on their backs!  He also had some shave cream on his neck, so I guess I knew what we’d caught him at.

“Trick or treat!” we sang.

“Hey-ey… Look at youse!  Yeah, it’s Halloween, I get it.  I didn’t even think kids could…”  He looked down the hall both ways, maybe to see if there were more kids, or any adults nearby.  “Hey, I ain’t got no candy, but youse kids got some nerve, I’ll tell you.  Here.”

He reached into his back pocket and pulled out his wallet.  He flicked a couple one dollar bills at our Walgreens bags.

“What are you, a CPA?” he asked Henry.  Henry’s shirt had fallen closed and he opened it to show the S.  “Well, that’s a pretty cheap Superman, guy.  Where’s the effort?  And you, doll-face, I tell you… You wear something sexier, show a little skin instead of dressing up as a Keebler Elf, and I’d give you a few more bucks, you know what I mean?”

I didn’t know what to say to that.  Henry picked up the dollars.

“Hey, Merry Christmas!” the guy said and closed the door.

We went right back to our room.

Once I was in, I pulled off the stupid hat and threw it against the wall, then I ripped off the red shirt and collapsed on my bed.  “This is stupid!  We’re stupid for even trying!”  I felt like crying, and maybe I was, a little.  My eyes were wet.

Henry came over behind me and put his arms around me.  I raised up a bit to let him.  “Don’t pay attention to that gorilla-guy, he’s just an asshole.”

“Gorilla-guy!” I sniff-laughed.  From then on, Henry and I would refer to the ‘gorilla-guy’ in many private jokes.

“But you are a doll-face.  I told you…” he whispered in my ear, “…you are really pretty.”

That did make me smile.  “You know my friends and me all think you’re hot…”

“Your friends… and you?” he repeated.  Oops, I did say that, didn’t I?

I sat up.  “Mm-hm.  I’m your sister, I can judge you.  You look good after all that work this summer.”  And I left it at that.

We went back out by our costume supplies.  What else could I be instead of stupid sriracha?  With my back to Henry, I took off my bra, then stepped into the yellow leotard.  “Maybe gorilla-guy was right, though.  What if I showed more skin and did the Barbie costume?”

“You don’t have to do that…” Henry said, looking right at my chest.  I knew my nipples were pointy right then, but I was feeling a little daring.  Henry did call me pretty, after all.

“Yeah, my underwear is all bunchy, still.  I could take that off,” I teased, “and do a pony tail.  Do you think that would be Barbie enough?”

“You… you could try…” Henry coughed.

I really didn’t like the Barbie combination.  I had no idea what to do with it.  “Yeah, no…  I’m gonna go with the Cat Lady, but I’ll wear my shorts underneath, show some leg.”

And that’s what I went with.  Henry decided to try one a little more Halloweeny, too, like he’d made some effort, and taped four cereal boxes to the sleeveless undershirt, punctured the boxes with the four plastic knives we got from the hotdog guy (why, I don’t know — what do you need knives for with hotdogs?), put his jeans back on, and gave himself some stubble with my mom’s mascara.  We snapped some photos and we were back out the door.

We decided not to go door-to-door to the guest rooms, this time, but went downstairs and hit the front desk and the Concierge.  Both of them, I am happy to report, had a big bag of candy at their desks!  We got full-size Three Musketeers and Kit Kats from the front desk lady, and full-size Reese’s Cups and MilkyWays from the Concierge.  We were going to try the bell captain, but the Concierge quietly shook his head at us.  The front desk lady waved us back over.

“You kids should hit the stores while they’re still open,” she told us.  “Usually, whoever is at the closest-in counter has something, even if it’s just Smarties or Tootsie Pops.  The college kids like to trick-or-treat, thinking it’s funny, but the stores like the good will and surprise them.”

That was exactly what we were hoping to find out!  We started out for the street when the Concierge stopped us.  “Kids, I hate to tell you, but it’s gotten colder out there, now.”  We should have remembered.  It was cold before, too.  “Bring a coat or… change your costume a little?  Like padding or… pants?”

This was going to be the third costume change!  But with four candy bars and two dollars in our bags, this was what we wanted, dang it!

In the elevator, Henry knew he couldn’t put his coat over the cereal boxes — the whole look would be ruined.  Would he go back to Clark Kent?  He decided to try the John Wick look.  I could pad my robe and wear pants, I knew, but I suddenly wondered if people would think I was a homeless person?  When Henry decided on John Wick, I had the idea of matching him, like we might’ve done with Barbie and Ken.

In our room, Henry changed pretty quickly into his good suit he brought for the wedding, taping the little stuffed dog to his shoulder.  He was painting John Wick’s beard on his face with Mom’s mascara brush when I came back from Mom’s room.

I was in my nice dress for the wedding, a red, street-length gown with open shoulders, but I wore the leggings underneath, and borrowed my mom’s black jacket to keep out the chill.  I’d put on a little makeup — not much — and used the curling iron on my long, golden hair, making it flip just below my shoulders, and applied lots of Aqua Net for the wind.  And I carried the six fake roses.

“What do you think?”

Henry was stunned, making me very happy.  “Doll-face, you are not pretty.  You are beautiful!”

I couldn’t hide my smile, and I gave Henry one of my roses.  “Will you accept this rose?”

When he took the flower from me, he leaned in and kissed me.  He kissed me!  A real kiss!  On the lips!  And not a quick birthday peck, a real kiss!  I felt that one right down to my toes.  At first, he just kissed my lips, but when he didn’t pull away, I kissed him back.  When we broke the kiss, I had to shake the stars out of my eyes, but a smile, I’m afraid, was glued to my face, now.

We took a couple photos, grabbed our Walgreens bags, and took the elevator down.  We got a very approving smile from the Concierge as we went outside.  Henry took my hand, like he always did.

When we walked down Michigan Avenue, now we looked like we belonged.  Well, we were certainly dressed right, although Henry’s fake beard — and the doggie — kind of gave us away as kids out for tricks-n-treats.

Not every store had candy for us.  We got a few “Oh, I’m sorry, but aren’t you cute!” responses, but Carrie the desk lady was right and we did get candy at other places.  No more full-size ones, but we did get a lot of M&Ms, Snickers, MilkyWays, and suckers I don’t know the brand of.  One department store had candy, but since the closest desk was cosmetics, the girl there let me try on a nice lipstick to go with my dress and gave me some perfume samples — which was really cool!

Our favorite place was this soul food restaurant.  The lady not only gave us some M&Ms, but felt so bad we hadn’t had dinner, yet, sat us down and gave us plates with samples of short rib street tacos, fried green tomatoes with lump crab, collard green dip and chips, and some parmesan truffle fries.  This was, hands-down, the best stuff we’d ever tasted!  And it was just appetizers, she told us, because the entrée stuff was portioned.  Henry tried to pay, but the lady wouldn’t hear of it, and her husband, who had been cooking in back, came out and recognized Henry’s costume right away.

“Money’s no good — Not if you can’t spend it,” he told Henry, which Henry loved, because it was a line from John Wick, I guess.  The lady wanted to know who John Wick was, and then the man and Henry both said, “John wasn’t exactly the boogeyman.  He was the one you sent to kill the fuckin’ boogeyman!”

Henry said he should have a fake gun, but both the man and lady reacted immediately and said a fake gun is the worst thing you can have in Chicago!  I’m like, Okayyyy…

We asked about any homes in the area to go to, and she said there were some west of the Loop, but things get kind of ‘empty’ in the south Loop at night, and now that it was dark out already, we should either stick to well-lit places or head back.

We took a couple selfies with the couple, and I gave them each a flower, and we were on our way.  (Before the wedding on Saturday, we brought our dad back here for lunch!)

We went as far north as the Chicago River — which isn’t as big as the Missouri, but it was definitely deeper than the Platte, and this lady told us the Chicago River runs backwards for some weird reason — and we still hadn’t reached that John Hand Cock building!  We decided to head back to the hotel.

On the way there, it started raining.  Yep, it started light, and we hoped that would be it, but it got heavy real fast.  There was no avoiding it.  We tried running, but I was in my strappy flats and skidding, luckily still holding Henry’s hand so I didn’t fall.  We tried waiting it out in a doorway, but we were soaked and kept having to move for people.  We just got on with it and made it back to the hotel lobby as soon as we could.

When we got inside, we realized not only was my dress ruined, but Mom’s jacket, and Henry’s whole suit was, too.  I was starting to cry when our friends, Mr. Thomas the Concierge and Carrie, the front desk lady, came to our rescue.  Carrie assured me the things weren’t ruined — just incredibly wet!

We were to undress in our room and call down.  They would have a valet pick up our clothes and have them cleaned and pressed.  They wouldn’t be ready until tomorrow, but we didn’t need them until before the wedding, and our mother didn’t need to know — until the bill came at check-out!

I gave them each one of my wet roses, keeping the last one for myself.

When we were changing, Henry came sliding in front of the windows only in his white button-down shirt and socks, singing into the root beer cup.  “Just take those old-time rock and roll songs and put ‘em on the shelf…”  He was trying to do the Tom Cruise thing from that old movie where he sings in his underwear.  Definitely cheered me up!

But Henry’s shirt and underwear were wet like mine, and they had to go, too.  Our undies and socks were drying over the shower rod, but the nice clothes all went downstairs, somewhere, with the valet.  We were cold, but didn’t bother taking hot showers, just dried off with towels, combed out our hair, and wrapped up.

So that’s how we wound up naked under our plush hotel robes, alone in our room, staring out at the rain on Halloween night.

“You want some tea?” Henry asked me.  “I could use something hot to warm up with, you know?”  There was both a coffee maker and a hot water thingy in the little kitchen area.

I checked out the selection and chose chamomile because I remembered that’s the kind that Peter Rabbit drank in the story.  Henry put a little honey in it and made it very nice for me.

We turned the TV on, but wound up leaving it on the TV guide channel because it was playing a radio station as its soundtrack and the music was kind of Halloweeny — not “Monster Mash” but, like, “The Killing Moon” and Lana Del Rey singing “Season of the Witch.”  We didn’t want to watch anything, we just wanted to relax.  The channel also had the weather forecast — rain this evening.  Who’d a-thunk it?  If only we’d put that on when we were building costumes.

Now that we were settled, we dumped out our bags of loot.  There was a little water, but at least the non-recyclable wrappers kept our chocolate dry!  “Dang!” Henry exclaimed, “we actually got us a pretty good haul.  It’s probably not what we’d have got if we went with Little Ronnie and the others in their neighborhood, but we did pretty good for a couple of left-behind kids.”  We traded a look that showed we still felt a little betrayed.  “Trade you a Kit Kat for your Payday?”  He knew I liked Kit Kats.

We couldn’t help but dig into our haul.  We’d had a good supper at the soul food place, so this was dessert!  So, three candy bars in our bellies, we sat back on the little couch with our bare feet up on the table, looking out at the rain, mugs of hot tea in our hands.

Henry shut off the lamp so we could see the storm over the lake, better.  It was night out, and the city had lot of lights so the clouds were well-lit from below.  And with the big park between our hotel and the lake, we had a pretty good view.  Lots of lightning flashes!  We were just sittin’ there, us all lit up by the blue light of the TV, and I let my head roll over onto Henry’s shoulder.

Henry put his arm around me.  “Well, doll-face, we had us an adventure.”

End of Part one

Copyright 2025 – Tommy Linarcos
All rights reserved

8

My Brother Saves Halloween – Part 1 Read More »

Day Job Shenanigans – Part three

Adult/Youth, Boy/Woman Sex, First Time, Illustrated, Oral, Pics, Straight |

Day Job Shenanigans – Part three
By
Jason Crow

It was the first week of fall break in the local school district, and it turned out to be two busy weeks for StyleFocus. I even had to disappoint two potential customers, but I could eventually squeeze them in next weekend after two cancelations.

I steered my car through the busy morning traffic. My current mission: Trevor Henderson, son of some hotshot financial CEO who was barely home, and his trophy wife.

Mrs. Henderson’s main task was to be pretty and keep their social life together. She was also known for the fundraisers she organized, but raising her son wasn’t one of her strengths. So, when she heard about me from one of her friends, she was on the phone immediately to find out how I could help her.

But she wasn’t a fool. Turned out she had me do a test run first on her neighbor’s young son. When that went well, I got the call to take on Trevor. Trevor was twelve years old, but Mrs. Henderson’s body didn’t show any signs of giving birth. This was probably primarily thanks to her skilled plastic surgeon and her personal trainer. Or her tennis pro. They all had tennis instructors like Brian’s mom did.

I arrived to pick up Trevor at their stately manor. I parked the car, made sure my dark-brown hair looked perfect, and touched up a bit of lipstick before closing the mirror and sun visor. I got out, adjusted my plaid skirt, and made sure the cleavage of my firm, C-cup boobs was modest enough for a mother who was about to send her son with me.

“Of course, Mrs. Henderson. I’ll make sure we’ll be back by three with some outfits both Trevor and you will love,” I said politely at the door. I noticed a very pretty girl up on the stairs, giving me a look-over, likely Mrs. Henderson’s daughter. I briefly wondered if I could open my Personal Shopper service to young girls. And then Trevor arrived.

Trevor was by far the cutest boy I took shopping. Even cuter than Damian and right up my alley when it came to looks and age. He was thin. A bit on the skinny side even. He recently had a growth spurt, and the top of his head now ended just below my nose. He’d inherited his mother’s genes because he had a handsome face, and his short blonde hair fitted him perfectly. His blonde hair, combined with his blue eyes, reminded me of Brian, which unleashed a familiar torrent of feelings.

I knew I had to be careful here. If any of the boys I flirted with would talk to their parents about it, I would be finished. The way I recklessly tumbled into my thing with Brian was way too risky. Looking back, I could’ve easily ended up in jail if Brian hadn’t been the discrete boy he turned out to be. It probably had everything to do with the way his parents handled their relationship, but still…

During my time with Brian, I did learn a lot of valuable lessons. First, I would end the relationship sooner. Second, the boy needed to be able to keep his mouth shut, just like Brian. And third, I needed pictures of him. With Brian, I only had the ones after we broke up, and I wish I had more.

But Trevor was a potential candidate for me. He was a quiet boy, didn’t have many friends, and always answered the questions I asked reservedly. I was optimistic that I could convince him to keep his mouth shut without too much trouble.

On the drive over to The Style Haven, Trevor was personable and open to chit-chat now that he was away from the glare of his mother, just like the rest of my young clients. This boded well.

“Hi, Carol,” one of the friendly store employees greeted.

“Hi, Mimi!” I greeted her enthusiastically, even though I knew there was no way her name was Mimi.

It was probably something like Brittany, Daisy, or Harriet, considering where she came from. But because Dad ran stores with high-end brands, he insisted his employees had ‘fun names’ as he called it. Apparently, he thought that Mimi was fun…

The Style Haven was a store for the young and young at heart. Its focus was selling all the high-end brands for both boys and girls. The age range was from preteen or young adult at about nine or ten years old all the way toward the leaving for college section. The stores had a very modern look and breathed a very sleek and stylish aura. The employees were almost only women, all dressed in short skirts and high heels, but still looked chic and classy.

Mimi walked with us on her too-high heels, unlocked the room for us, held the door open, and nodded at Trevor. I might have been mistaken, but I could swear she checked out the boy’s ass as he entered the room. I couldn’t blame her. He had a fine-looking ass.

“Thanks, Mimi!” I said and closed the door behind me. I made sure Trevor could see and hear me lock it.

“Why’s that?” he asked.

“It’s a private shopping experience. This way, we won’t be disturbed,” I said, as if it was the most logical thing to lock yourself in a room with a nearly teenage boy who was about to strip.

I walked over to the fancy-looking oak table and dropped my purse on it. The room was only nine-by-twelve, but by the way I arranged it, it looked bigger. In both of my father’s shops, he’d remodeled a separate room for me to work from, made from three smaller fitting rooms and the hallway. It would be private, and I helped decorate and furnish them to make sure it would look impressive. On one side of the room, there was a couch with fluffy pillows on it and a comfortable chair next to it. The lighting in the room was warm and dim, except for the bright spotlight where the mirror was. And in the corner, a thick black curtain hung from the ceiling, ending about twenty inches above the ground.

In the middle of the other wall, there was a rack with about a dozen sets of pants and tops I had chosen. On the table was a small ice bucket, a selection of soda and water, and four clean glasses. Next to that was the stack of underwear, socks, and t-shirts I had selected for Trevor.

One of the unique things I did with my shopping service was that I held short interviews with both the mother or father and the kid that I would take with me. I asked them all sorts of questions. Some were complete bullshit, but I managed to keep a straight face when they were struggling to find an answer.

But I had always been good at reading people. After a couple of minutes, I usually had a pretty good picture of what the kid wanted and, more importantly, what the parent didn’t like. In the end, the parents had to pay for everything, so I needed to keep them happy.

But I also learned that when their son was happy with what we bought, the parents would quickly be happy, too. I had one boy early on who insisted on a skater look, but the mother wanted him in slacks and a shirt. A huge difference! But I managed to find a bit of a mix by not going all-in on the skater look and some cool shirts and decent-looking pants. When his mother saw him and realized how happy he was, she told me we needed to do another run.

“So, Trevor…” I said to him as he checked out the room.

He turned to look at me, and I saw some nervousness in his eyes. This wasn’t the first boy who was nervous when we started, and I knew from my experiences so far that I had to start slowly. I opened my Spotify app and started the playlist I had created. The speakers in the ceiling came to life, and Taylor Swift began to sing. The songs would gradually change from poppy to sexy without laying it on too thick.

“Do you want to have a drink first,” I said as I pointed to the table, “or do you just want to start and get it over with?”

“I, uhm… I just…”

I looked at his frame, started browsing the rack, and handed him a pair of slim, straight jeans, a blue shirt, and a hoodie. I smiled warmly at him and said, “Let’s just get going then. And don’t worry so much. You can change behind that curtain. When you’re done, come to the mirror, and we’ll see how things look. Okay?”

He nodded, and I could see him blushing. This was a shy boy! Cool. I like a challenge.

Inside these private rooms, I quickly learned that as long as their mother was out of the way, the boys didn’t care too much about being seen barely dressed. It was almost always the same. When we’d start, they would change behind the curtain, but after just a couple of back-and-forth movements, they didn’t bother with the curtain anymore. That was also the reason why I positioned the clothes on the other side of the room.

The good thing about boys this age was that I didn’t have to think about elaborate schemes to get what I wanted. The simplest tricks would work, like dressing in a schoolgirl outfit. I’d be surprised if it was any different with this cutie.

“Is a Coke okay?” I asked over my shoulder toward the curtain.

“Yeah, that’s fine,” he said, and I could hear him fumbling with his clothes.

I turned up the heat a little, sat down in the chair, and looked at the curtain. As his pants dropped and his hairless legs came into view, I hesitated for a moment. I could go behind the curtain to check him out, but that would probably scare him off. No, I needed the gentle approach for this one.

I poured him a glass of Coke and a Mountain Dew for myself. I was constantly eyeing what he was doing, feeling the tension inside me building. After all, he was the cutest boy I had taken out shopping so far, and I was anxious to see how far I could take this. Preferably all the way.

After a couple of moments, his bare legs were covered with denim, and he stepped into the room, straightening his hoodie and looking at me with an approving smile.

“You like it?” I asked.

He stood in front of the mirror, checked his reflection, and said, “Yeah. I look… cool.”

“Yeah… you do,” I said, standing behind him, “Do you mind if I take a picture of you so we can review it later?”

The whole reviewing argument was a bullshit reason, of course. But if there was one important lesson I’ve learned from my time with Brian, it was that I only had a couple of pics from him. With my new boys, this needed to change.

“Sure!” Trevor said, oblivious to my ulterior motives.

“Great,” I said, opened my camera app, stepped back, and made sure his entire body was in the picture.

“Perfect. Turn to the side, please,” I said, which he obediently did, “Thanks. Now, show me your back.”

He turned his back toward me, and I made sure to snap as many pictures as I could. Despite him being too overdressed for my liking, Trevor still looked mighty fine.

“Alright. That’s done,” I said and sighed a bit, “It’s just that…

I made sure to look thoughtfully at his reflection. I openly checked him out and made sure he saw me looking at his ass.

“But, what?” he asked.

“Well… I…” I cleared my throat and made sure I looked uncomfortable, “I… uhm… you’ve got a cute butt. And in these pants…”

“Pfft!” he scoffed, “cute butt…”

“What!? I mean it! You’ve got a cute butt and nice, broad shoulders. You should own up to that! We need to accentuate your strong points.” I said, looking at him with a determined expression.

He checked me out to see if I was serious and asked, “Really? And…. my shoulders!? I don’t even have any real muscles yet…”

“They look nice on you. And they make you look more mature,” I said, feeding into something every boy wanted to hear.

“You really think so?”

“Of course! Here, take off your hoodie,” I said and was pleased to see that he didn’t question me.

As he pulled his sweater over his head, his T-shirt rode up a little, showcasing a small strip of skin above his jeans. The waistband of his classic cotton boxers was also visible. When I first met him, I already figured he was a classic underwear kind of guy. Well… technically, his mother was. I just wasn’t sure if it would be tighty-whiteys or classic boxers. Now I had my answer.

His innie belly button looked cute on him, and his skin was tight and flawless. A bit on the pale side, but I liked it! He handed me the sweater, and I placed it on the table. We turned to look in the mirror, and I stood behind him, my hands on his bony shoulders.

“See?” I asked.

“See what?”

“Your upper body is diamond-shaped. This is something not many boys your age have.”

“Diamond-shaped?” he asked, clearly a bit confused.

“Yeah,” I said excitedly, “you uhm… the triangular muscles from your neck to your broad shoulders and then toward your narrow waist.”

His shoulders felt great under my squeezing hands, and I was looking forward to seeing him shirtless. But he looked suspiciously at me in the mirror as if he thought I was mocking him.

“Diamond? Don’t you mean more like a kite shape?” he laughed at himself. “I’m so skinny I could fly away.”

I stood behind him but looked him in the eyes through the mirror. “Clothes make the man. You may have heard that before, but it’s true. When you dress well for your body type, it gives you confidence, and that attitude shows on you. And believe me, girls notice that.”

I could see him considering that.

“Wait,” I said and selected another shirt from the rack with my right hand. I made sure to keep my left on his shoulder so he would stay put.

“Here, try this on, and you’ll see what I mean,” I said.

By keeping my hand on his shoulder, I more or less told him to change in front of me. If he made a move to go toward the curtain, I knew it would get difficult with him. Not impossible, but difficult.

He hesitated a moment. But when he started taking off his shirt, a tiny tingle shot through me, and I knew this was going somewhere. He quickly changed his shirt, but the fast glance I got at his exposed chest was very encouraging. A tight belly, signs of developing pecs, but nowhere near muscular, and prominent collarbones with broad and bony shoulders.

After he pulled down the tight white shirt, which was barely long enough to reach the top of his pants, I stood behind him with my hands on his shoulders. I looked at him in the mirror and said, “See? Your triangular muscles accentuate your shoulders beautifully.”

As I said this, I squeezed his shoulders and let my fingers trace the outline of his muscles. “And, uhm… if you don’t mind, take off your shirt again so I can show you what I mean by that diamond-shaped upper body,” I softly said while locking eyes with him through the mirror.

He didn’t wait this time. His hands moved down, and he started lifting his shirt. I took it from him and placed it on his other shirt. Now that I could stare unobstructed at his upper body, I felt my pussy moisten considerably.

“Look,” I said and traced a line with my fingers from his neck, over his triangular muscles, toward the bony endpoints of his shoulders.

After I reached the end of his shoulders, I stepped closer. I made sure he could feel my hard nipples on his back, and since they were only covered by the thin fabric of my blouse and bustier, I was sure he noticed.

“From here…” I whispered in his ear. Goosebumps spread all over his upper body as I slowly traced my fingers down over his chest. After touching his hard nipples, I slowly kept moving down over his chest toward his belly. My fingers were on both sides of his cute belly button, moving toward each other to outline the downward triangle, and I slowly kept moving down.

“To here…,” I whispered even softer, my lips against his ear.

My fingers were now touching the waistband of his boxers, and I pushed it down a little. There wasn’t much room to move, but my intentions couldn’t be missed. Trevor swallowed audibly and nodded ever so slightly.

“That’s the diamond-shaped upper body I was talking about,” I whispered as my lips brushed his earlobe and my hands lay on his tight belly, my fingers as close to his pubic area as possible with these clothes.

“I…” he cleared his throat, “I guess you’re right…”

I pressed my tits even harder against his back and smiled inwardly as he swallowed again. In the mirror, his obvious boner couldn’t be missed. This meant it was time for my next move.

“These jeans look nice. But would you mind trying on another pair for me?” I asked as I stepped back a little, and my hands moved to his sides.

“It’s… uhm… sure…” Trevor croaked.

“Great! Here…,” I said and reluctantly let go of his sides and stepped back to hand him the tight, skinny jeans.

This was another make-or-break moment. I was pretty confident that he’d change in here, but there was still a decent chance that, because of his boner, he’d go behind the curtain. But when he started undoing the buttons on the jeans he had on, I knew he’d leave his virginity behind him today.

Right before the front of his boxers came into view, he turned around. He probably didn’t want to offend me or anything like that, something cute and innocent that I liked so much in these young boys. But I didn’t mind. I got a quick glance at the tent his hard-on created in his cotton boxers, and he was endowed enough to make a difference. He wasn’t hung like Brian, but he didn’t need to be hung at all. He just needed to be hard and willing. That was enough for me.

As he was pulling up his jeans, I checked out his boxer-clad ass. It was yet another confirmation that these old-school boxershorts should be legally banned. They’re asexual and do absolutely nothing good for his body. I could barely make out where his hips ended and his ass started. “Hmm… maybe boxer briefs would work better for you…” I said quietly but audibly, assessing the clothing like the professional I was.

But when he pulled up his jeans and started stuffing his junk into the front, the contours of his fine little ass appeared. After a few moments of him trying to close the zipper, I could see him look down at his crotch, and I noticed him blushing. He’d managed to close the zipper and button, but it was obvious he was embarrassed about his visible boner. Time for me to spring into action.

“I was right,” I said excitedly, “you’ve got the cutest butt!”

He shrugged, didn’t say anything, and kept his back toward me. When I asked him to turn around, he shook his head and stayed put.

“Don’t worry, Trevor, I know you’ve, uhm… got an erection,” I said softly.

He turned his head and looked at me with panic in his eyes. I took him by his shoulders and gently made him turn to face me. I forced myself to keep looking him in his eyes and refrained from looking down, but it took some willpower to do so.

“Look, Trevor… having boners is natural. There’s nothing wrong with it or to be ashamed about. Heck! It would be weird if you didn’t have one right now. And if you’re worried about me talking to someone about it, don’t be. What happens in this room stays in this room. I signed a contract with your parents. So even if I wanted, which I don’t, I’m legally bound to that contract.”

That last bit was a lie, but the panic in Trevor’s eyes faded, and he was checking me out to see if I was serious. After he decided I was, his lips curled up ever so slightly into a barely noticeable smile.

“You know what?” I said and openly checked out the front of his pants, “You’ve got nothing to be ashamed of, and you should own it!”

“Yeah, right… tell that to the girls in school…” he scoffed.

“I’ll let you in on a little secret here… girls do like to see it. They’re just terrible at how they react to it. Believe me, girls are as curious about boys as boys are about girls, and I’m sure they’ll think you’re very interesting after seeing your boner. Especially in these pants.”

“You really think so?”

“I know so. I was a girl once, too, you know?” I said, moving my hands from his shoulders to caress his sides and put him at ease.

“Now… let me take a look at you,” I said and stepped back, eyeing him from top to bottom.

I didn’t want to emphasize the situation in his pants, so I cheerfully said, “Turn around so I can have a complete look at you in these pants.”

He did as I told him, and after he turned around and faced me again, I could feel the tension between us was almost gone. “You look good, Trevor. Don’t let anyone tell you otherwise!”

“Thanks, Carol,” he said, and I could tell he meant it.

“Hey! Do you mind if I take a couple more pics? That way, we can clearly see the difference in styles.”

Trevor shrugged, and I took another few shots of him. This time, he was shirtless, and he had a visible boner, so most of these pics would end up in my special folder on my laptop. After the picture, a silence fell between us, and I noticed his boner twitch a few times in his pants as he glanced at my chest when he thought I wasn’t looking. It was time for the simplest but most effective move there was with boys.

“You know what?” I said with a bit of annoyance in my voice.

“What?”

“It’s freaking hot in here!” I said, and I looked around as if I was looking for the source of the heat.

“Yeah… you’re right,” Trevor answered.  

It wasn’t that hot, actually. After we came in, I set the temperature a little higher than usual, but it was nowhere near hot in here. The only hot thing in here was the shirtless teenage boy in front of me. But Trevor played along, which was enough.

“Do you mind if I take off my blouse?” I asked sweetly.

“Uhm…” Trevor softly said, but once he realized he’d see more of me, he shrugged and said, “Sure!”

This one was always an easy one. Under my white blouse, I’d wear a red, almost see-through, lacy, bustier cami top that ended just above my belly button. Between my boobs, there was a zipper from top to bottom, which made it easy to take it off or put it on. I deliberately chose this one because it gave me plenty of opportunities to work the boys on this. It was still slightly modest, but only because I wasn’t completely topless. The lace did hide parts of my breasts and nipples, but at the same time, it left nothing to the imagination.

“You’re cool,” I said and started unbuttoning my blouse.

I quickly unbuttoned the rest and pulled it off. As I placed my blouse on top of the other clothes, I felt Trevor’s eyes all over my upper body. I stood up straight and looked at this wide-eyed boy staring at my chest, and I smiled inwardly.

Trevor’s eyes were locked on my chest. My tits were somewhat covered by the lacy fabric of the bustier, and the fact that I was showing yet another underaged boy my boobs, made my pussy quiver in delight. I kept trying to make eye contact with Trevor, but he made absolutely no attempt to hide the fact that he was staring at my chest.

I’ll never grow tired of looking at the face of a boy who’s looking at his first real-life pair of boobs. Even though I wasn’t topless, there was still enough to be seen. And without exception, the look of awe and wonder on a boy’s face is priceless. The same was true with Trevor, although the second and third time I showed those kids my boobs, they were still staring as if it was their first. Guess they never grow tired of boobs. I noticed another twitch in Trevor’s pants as my nipples were now so hard I was positive I could cut glass with them.

“Aahhh, that’s better,” I said, exaggerating things a little.

I placed my hand under Trevor’s chin so he looked me in the eyes instead of at my nipples. A look of apology appeared in his eyes, but I would have nothing of that. Instead, I smiled at him and softly asked, “Do you think you can find the diamond shape on my body?”

Trevor swallowed audibly as I took both his hands, extended his fingers, and placed them on my throat. I gently moved his hands in the right way, and after his hormones took over, he started moving his hands by himself. I kept looking him in his eyes, but he only had eyes for where his fingers were touching me. He hesitated only a moment when he reached the swell of my breasts. His hands were shaking as they moved down over my boobs toward my belly button.

Once he reached my skirt, he stammered a soft, “I… I, uhm… I think it’s like this…”

“I think you’re right…” I whispered.

I looked him in his eyes as I slowly unzipped my bustier. The soft sound of the zipper filled the room, and Trevor couldn’t keep his eyes away from the skin that was slowly being exposed on my chest.

Once the zipper was undone and the bustier hung open but still didn’t reveal any forbidden flesh, Trevor quickly looked at me. I pulled away one side of the bustier a little to give Trevor a hint of what was to come, and his eyes were immediately on my chest again.

I took one of his hands, placed it on the exposed skin, and whispered, “You can touch me if you want…”

He didn’t need to think this one over. This offer landed right in the middle of his pool of hormones with a big splash. Before I knew it, he cupped my right boob. A heartbeat later, his other hand moved up from my belly button and went straight toward my left tit, cupping it firmly. As he gently felt around my boobs, I noticed how his mouth was open a little bit, which was adorable. But his probing fingers on my tits blew the lid off my rapidly expanding horniness. I ditched my bustier and stood there topless in front of this adolescent boy who was eagerly fondling my tits.

“You like ‘em?” I asked and heard the trembling of all the anticipation in my voice.

“Yeah… they’re amazing and the… oh wow! They’re so soft…”

“Well… you aren’t,” I stated matter-of-factly.

After a few more moments of probing around, he looked up at me with an expression that I couldn’t place. It was somewhere between horny as fuck, and embarrassed as hell. I guess it was a mixture of both.

“Wh- what do you mean? You just sai…” he asked but kept gently kneading my boobs.

“It looks… uncomfortable,” I interrupted him and eyed the rigid tube of flesh that was pointing toward his left hip.

“It, uhm… it is…”

“I think the first pair of jeans work better on you, but it might also have something to do with the underwear you’re wearing. It’ll probably stay in place a bit better and will feel more comfortable with boxer briefs.”

I stepped back, and an almost overwhelming sense of emptiness washed over me as his hands left my boobs. But I knew it was for the greater good. I never left my lock with his eyes, though, so I just took hold of the top box of underwear from the table. I had his size in the four most popular brands, as I’d learned from my clients. They didn’t want to be the one kid in their locker room with store-brand underwear bought by their moms.

I opened the Tommy Hilfiger box and fished out a pair of mint-blue boxer briefs with white seams and a white waistband. The Hilfiger logo was unmistakably there in the middle at the top, and the word ‘Tommy’ was written in dark blue letters all over the waistband.

I handed it to him, and I could see the struggle in his eyes. I smiled warmly at him as he was fighting his internal battle. His eyes went briefly to my chest, and I thought I saw something change in him – the raising of an eyebrow, maybe, but something.

“Just turn around. I won’t look,” I said, and I actually felt sorry for the kid.

“Okay,” he softly answered.

“Well… maybe at your butt…” I chuckled as he started working on the button of his jeans.

I could see a sparkle in his eyes as a smile appeared on his face, and he said, “Go ahead. I heard through the grapevine that I’ve got a cute ass.”

“Really?” I said, amused at how he opened up, “Have to see it for myself, then…”

And with that, he turned around and shimmied out of his tight jeans. His dark blue boxers came down a bit, too, and I got a first glance at a bit of his bum crack. The moment he realized what had happened, he pulled them up and chuckled an amused, “Whoops!”

This made me smile. He was getting more and more comfortable around me, which made everything so much easier. After he stepped out of his pants, he stood up straight and hooked his thumbs in the waistband of his ugly-as-fuck boxers. He hesitated a moment but then slid them down without further ado. But when he stood back straight to grab his Tommy boxers… oh boy! I’m a sucker for boy’s asses, especially the round, firm ones. And Trevor easily qualified in the top three of cute asses!

“Nice…” I purred.

He opened his mouth to say something. He even took a breath for that. But nothing came out. This inexperienced boy wasn’t ready for snappy comments back and forth, yet. They were so cute when they wanted to act all grown up but lacked some life experience. Instead of trying to continue, he just stepped into his boxer briefs and quickly pulled them up. I didn’t mind too much because they hugged his ass perfectly, and I was about to finally see the outline of his dick. He was fumbling a bit at his front, adjusting his junk, and I couldn’t wait to check out his front.

“Hmm… this is nice,” he said softly.

“Told you so. Turn around,” I said.

I expected him to hesitate, but instead, he turned around and smiled broadly at me, exposing his boxer-clad boner. It pointed straight upwards, and the mint-blue fabric accentuated it perfectly. The white seams at the front made it almost look obscene. Almost.

“You look… sexy,” I whispered and tried looking uncomfortable as I said this.

“Oh…” he answered, and I could see a tiny but proud smile appear in the corner of his mouth. He craned his neck a bit to look at his backside in the tri-fold mirrors. “You’re right!”

“Yeah…” I said, trying my best to not rip off his boxers and impale myself on his hard cock.

“These are way more comfortable than my old boxers. Especially when I… you know…” he said and gestured toward his boner.

“Lemme see,” I said, feeling horny as hell, and I squatted in front of him.

Now I was at eye level with his crotch, and as I looked at his upward-pointing boner, my pussy contracted sharply. He was about four inches hard, and since the rim of his dickhead was clearly visible, I assumed he was cut.

“It looks like it fits you perfectly,” I said as I pretended to only look at how these boxers fitted him. “Is Hilfiger okay with you?” I ran my hands from the waistband, down over his hips, and slowly toward his front.

“Tommy’s are fine,” he whispered. As my fingers moved closer toward his straining dick, it twitched hard again.

It was as if my fingers had a mind of their own as they moved back up toward the waistband. “Then let’s get these wrapped up for you,” I breathed.

I grabbed the waistband and pulled it forward and down before Trevor had a chance to react. And there it was. Right in front of my eyes. Four inches long, almost perfectly straight, with just a tiny bend to his left. A thick vein ran over his shaft, and a reddish, pointy dickhead topped off his circumcised cock. And the small, light brownish-colored patch of sparse pubes was so incredibly sexy…

“Wha- what…” he stammered, probably stunned by my sudden move.

I didn’t listen. I moved my head forward while letting out a soothing “Sshh…” My lips touched his glans, and I let him slip inside my mouth easily. I made sure to apply a little pressure with my lips, and according to the low moan I heard above me, he liked what I was doing.

The moment his cockhead was inside, and my tongue licked his piss slit, I was surprised to taste the sweet and salty taste of his precum. It wasn’t much and barely noticeable, but it was definitely there.

My hands were still holding onto his boxers, and I started pulling them down further. All the while, I was licking all around his dickhead. When his boxers were around his ankles, he caught on and stepped out of them. That’s when my fingers came into play, and I started toying with his grape-sized balls. They hung loose in his sack and were a little bigger than I was used to with other boys.  

I looked up at Trevor, and the look on his face was priceless!! All the new feelings he was experiencing, along with shock and wonder, were poured into an expression I’d never forget. I locked my eyes on his and slowly but steadily moved my lips down over his shaft.

His hands went to my head, but unlike Damian, who always wound up fucking my face that way, Trevor just ran his fingers through my dark-brown hair, slowly, softly, like he really cared how much work I put into managing my hair.

I could easily take him in all the way without gagging, and I actually enjoyed feeling his pointy dickhead at the back of my throat. But the tickling of his soft pubes against my nose made this a winning combination.

I pulled back, grabbed the base of his cock, and let him slip out of my mouth. I kept looking at him intensely, exaggeratedly licked his dickhead, and asked, “You taste good… do you like it?”

“I… oh… yess… I’m…” he stammered incoherently.

“Good,” I said and took him in all the way, again.

Boys like Trevor had a hair trigger on their first blowjob. They’d cum without warning, but judging by the hint of precum I tasted before, I’d be treated to at least a small drop of his boy juice. And what was even better was that after he came, he’d be able to fuck me longer and probably give me a couple of orgasms.

“Oh, Carol…” he moaned.

I moved my hand from the base of his cock to one of his soft but firm ass cheeks, and I wanted to feel his ass muscles move. But in my mouth, his thin shaft thickened, and I heard him sharply suck in a breath.

“Here it comes…” I thought.

And sure enough, Trevor grunted deeply and pushed his hips forward as his caveman brain told him to shove his seed deep into the warm place his cock was in at the moment. A heartbeat later, a small drop of watery cum splashed against the back of my throat. I assumed this was it, but four more spurts followed, all with the same force and the same small amount of cum. This boy sure shot a lot for his young age!

I swirled his cum through my mouth, savoring the sweet and salty taste. I sucked him for a little while more, and after I was sure nothing more would come out, I pulled off, and a loud ‘pop’ filled the room.

“Wha- w- was that a b- blowjob?” he asked, still panting heavily and looking at his rock-hard boner to see if it wasn’t broken.

“It sure was,” I chuckled, “Did you like it?”

I know I was asking the obvious here, but I loved the reaction I’d get to this question. And sure enough, while nodding vigorously, he exclaimed, “YEAH! It was… WOW!!!”

“Good!”

“But… why?” Trevor asked.

I got to my feet, unceremoniously unzipped my skirt, and let it drop to the floor. His eyes widened again as he looked at my now naked body. I kept my Brazilian neatly trimmed for these moments, and it always paid off. I looked seriously at him and said, “Because I think you’re hot, and I want you to fuck me. And I don’t want you to cum too quickly, so that’s why.”

He looked flabbergasted at me, but I didn’t wait for an answer. I grabbed his hand and walked backward toward the couch, guiding him with me. His rock-hard cock hardly bounced as he walked, and he only had eyes for my pussy now. If I’d taken him out into the store like this, I’m sure he wouldn’t even notice.

I lay down on the couch on my back and spread my legs. I pulled my lips a bit apart to show him my insides. His eyes were locked on my pussy, which made me want to get him worked up even more. So, with my free hand, I slid two fingers inside, which caused Trevor to let out a soft, “Oh wow…”

“Get over here, Trevor,” I hoarsely said.

He simply nodded, got on the couch, and sat on his knees between my legs. I could see he was nervous. But, unlike all the other boys, he scooted forward, grabbed his cock by its base, and aimed his pointy dickhead right at my entrance.

“Ohh… Yeah… that’s it…” I whispered as his tip touched my entrance.

He looked down between our bodies, where his virginity would soon be gone. I could see a bit of his face, and the look of concentration on it was adorable. I let go of my pussy, and as my outer lips hugged his cockhead, he let out a short gasp. I placed both my hands on his tight ass and gave it a soft push.

“Just push it in… you’ll love it!” I whispered.

That was all the encouragement he needed. I felt his ass muscles tense under my fingers, and his hips moved forward, causing his little dickhead to enter me for the very first time. I heard myself moan as the realization of taking the virginity of yet another young boy landed.

Usually, they either pushed in firmly and hard, or they’d be overly slow and careful. But with Trevor, he kept a slow pace but still kept sliding in. This was a new one for me. The little cutie was a natural!

When his almost hairless crotch mashed against my clit, I came. It was so sudden and unexpected that I grunted deeply, and I firmly squeezed his ass. Trevor stopped moving and looked at me with wonder in his eyes. “What was that?” he asked.

“You just gave me an orgasm,” I grinned.

“Oh,” he said with disappointment in his voice.

It took me a second to realize what was going on. But I quickly figured out that he’d probably think things were done after one of us had an orgasm. Oh, how I loved those sweet, inexperienced boys…

“Don’t stop!” I said and patted him on his ass, “Fuck me. Let’s have some more fun!”

“I thought that since you, you know… I had to stop.”

“Girls can come multiple times. And this was just a small one. If you keep going, my orgasms will be better. Don’t mind me, just fuck me with that wonderful cock of yours!”

I loved talking dirty to these young boys, especially when I was getting excited. It turned me on so much to see the mixed feelings on their faces. They probably never heard a woman talk to them like that before and were confused about it. But at the same time, it turned them on to hear those words come out of my mouth.

And Trevor was no exception. He nodded ever so slightly and started sliding out. Usually, they always pulled out too far, but Trevor managed to stop right on time and slide back in. This would be a good fuck, for sure!

“Yeahhhh…. that’s it, baby! Fuck me!”

Trevor looked straight into my eyes as he pushed back inside. He whispered a barely audible, “fuck… you’re… wet… aahhh… and your wet puss… ohh…” and he kept on looking at me as he pulled out. And back in. His look got more and more focused and more confident each time he pistoned in and out of me.

“Fuck your… with my hard cock…” he whispered again, sending shivers down my spine.

“Yeah!! You are fucking me with your hard cock!” I said, looking him deep into his eyes.

He must’ve realized what he was mumbling because he looked at me as if he just said something wrong. But I quickly pushed that thought out of his head by saying, “You fuck my wet pussy! Fuck me! Fuck me, and keep talking like that!”

His small, bony hips slammed against my thighs as loud slaps of flesh on flesh filled the room. His mouth was slightly open now, and I heard myself moan as the pressure inside kept building. Since he showed no signs of being close to cumming, I knew for sure this was going to be a good one.

“I’m fucking… you’re so… your hot cunt…” Trevor stammered incoherently.

“Oh, fuck! Oh, yes! Oh, baby! Ohnngg! Fuck, fuck!” I heard myself grunt.

Trevor just kept slamming into me in a steady rhythm. He was panting heavily by now but kept looking at me. It was strange and hot as fuck at the same time. The pressure inside reached a boiling point as my young lover picked up the pace. Now, each time he slammed into me, his pubic bone smashed my clit. It was almost painful, but the pleasure it gave me was so overwhelming that it pushed back the pain. And when his eyes crossed and his cock started kicking, I came. And oh boy, did I cum!!

“Ahh! Shooting… oohhh… my cum inside… aaaghhh!”

My vision blurred, and my pussy contracted sharper than ever before. Or that’s how it felt, at least. I felt the drops of cum my almost teenage lover produced hit the walls of my pussy, and another surge shot through me. A couple of moments after that, his body collapsed on top of mine.

I rubbed his ass with one hand and caressed his hair with the other. I could feel the sweat between our bodies, but this didn’t matter. All that mattered was his still rock-hard dick kicking every now and then inside my sopping pussy.

“How was it?” I whispered.

“Freaking amazing!” he whispered back.

“Good! I liked it a lot, too. And you know what?”

He lifted his head and looked at me, “What?”

I smiled and said, “Now you’re no longer a virgin.”

Usually, when I said this, their faces would light up, but all he said was, “Oh…”

And then it suddenly dawned on me…

“You’ve done this before?” I asked and couldn’t hold back my surprise.

His eyes showed that his secret was out but that he didn’t want to be busted. He looked nervously at me and said, “You have to promise to keep it a secret!”

I grinned broadly and said, “Look, honey… if what we did,” I felt his cock twitch inside, “heck… what we’re still doing, ever comes out, I’ll go to jail for the rest of my life. So I think we’ve got that part covered, don’t you? I guess you don’t have to worry about that…”

“Oh, right…” he said, and his cute smile returned.

“So tell me! Who’s the lucky one?”

“It’s… uhm…” he cleared his throat, took a deep breath, and said, “it’s my sister, Olivia…”

I didn’t see that one coming. Not by a long shot!! I knew he had a sister who was a little over a year older than he was. I believe I saw her when I picked Trevor up that day. She was a pretty girl with all the assets in all the right places. So, I tried to act cool and said, “Olivia, huh? She’s pretty…”

His cock twitched again the moment I said this. He simply nodded and said, “I went into her room a couple of months ago to ask for help with my homework. While she was shouting that I should knock and stuff, I stood there, frozen. I couldn’t move. She was lying naked on her bed, trying to grab the sheets, but they were all tangled up, so that didn’t work.”

“Was she…” I asked, feeling myself grow horny again.

“Yeah. She was completely naked, and a small thing was sticking out of her, uhm, you know… pussy,” he said, and a slight blush appeared around his nose.

“I love to hear you say the dirty words…”” I whispered and squeezed his hard cock with my pussy.

“The vibrator was still in her cunt…” he said, grinning, “I was stuck there… like I couldn’t move. I was wearing sweatpants and the old boxers, you know? So, my… dick was… you know, sticking out like it was before… and Olivia saw it, and she couldn’t stop looking, either.”

“Well… that was awkward…” I chuckled.

“Yeah… I felt so embarrassed! I turned around and ran back to my room.”

“And then what?” I asked and squeezed his ass, savoring its firmness and softness at the same time.

“She came to my room after a few minutes and said she wanted to talk about it. So, we talked about how embarrassing it was for both of us, and I apologized for not knocking. After talking a bit more, she asked if she could see my pen- uhm, dick. At first, I didn’t want to, but after she promised to show me her boobs, I said yes.”

By now, Trevor was slowly moving in and out of me again. It wasn’t really fucking yet, but the start was there.

“Then what happened?” I whispered, realizing how wet I was again from this story.

“She opened her robe and showed me her tits. I was hard as a rock when I pulled down my pants, and she just dropped her robe and was naked. She got on my bed, and before I knew it, I was… fucking my sister’s hot cunt…”

“You’re fucking me now,” I said, smiling broadly at him as his ass moved up and down under my kneading hands.

“You’re so hot!”

“Your sister is, oohhh, also hot…”

“Yeah…” he panted.

“Did you ever do it again?”

He nodded excitedly and started picking up the pace.

“We do it almost every day now… ahhh…” he groaned as my finger sneaked toward his hole. “She never gave me a blowjob, though. We just fuck.”

“You should, aaahhh… eat her out sometime. She’ll lov… ah… fuck, you’re good! She’ll love it and will probably re… ooohhh… return the favor.”

“You mean… lick her pussy?”

“Yeah. It’s basically the girl’s version of a blowjob.”

He looked questioningly at me, and after a moment, it seemed to click inside, and he nodded with a sexy grin on his face.

Then he got serious and picked up the pace, excitedly slamming into my cunt. I thought he was close again, but after his previous two cums, he lasted longer than I expected. I absolutely loved how he kept slamming into me. I had two small cums as he just kept on going.

“Oohhh… I’m close…” he groaned. “Fucking your hot cunt is so… Ohhh…”

“Don’t cum yet! I’m also… hhhmmm… Fuck me with that hard cock of yours!” I grunted.

“I’m fucking you so… ahhh… we’re fucking so… Fuck! Fuck!”

Hearing him talk dirty without me urging him on made my pussy tingle all over. Those tingles traveled up my spine straight into my brain. And I heard myself groan, “YES! Fill me up with your hot cum! You make my cunt so fucking wet! Fuck me, my hot fuckboy! Fuck me…”

He managed to postpone his cum just long enough for me. I came hard again with the image of little Trevor fucking his big sister’s brains out. And the moment I came, Trevor shot another load of his watery cum inside of me.

After that, we lay for a while, Trevor continuously massaging my breasts. He was still fascinated; my C cups must be bigger than whatever Olivia’s got.

When we pulled ourselves upright, we had some drinks and looked at some of the clothes he liked. It felt great walking around naked with this sexy young stud. He chose some items, nixed some others, and we created a couple of outstanding looks together. I threw in a few pairs of socks and all the boxer briefs that were on the table. He said he was done with his uncomfortable cotton boxers. Good! We’d take three sets of clothes back home, and I’d keep two behind for future use. I explained to Trevor that this meant more time to fuck the next time, which was an excellent idea, according to him.

I asked him if he was okay with another set of pics, but this time, for my personal collection, he agreed on one condition. He had to have a selfie where he was fucking me. I allowed it after he promised to keep my face out of the frame. I made it perfectly clear that I would go to jail if anyone found out it was me. Since Trevor was a smart kid, he clearly got the message, and I trusted him enough to go through with it. Especially since I’d get to have loads of nudes from this cutie.

After that, I taught him the basics of eating pussy. It turned out that he was a quick learner, and he almost made me cum. But since it was time to get going, and I wanted to fuck him one last time, I pushed him onto his back and sank down over his hard little cock. The girl on top was also a first for him, but he enjoyed playing with my tits during this fuck tremendously.

After we cleaned up and were about to head out into the store and back to the car, Trevor gave me a tight hug.

“Thank you,” he said into my shoulder.

“It’s been my pleasure,” I told him and brushed his hair.

It took him a second, but he got the double-entendre. He snickered but then clarified, “No, I mean… besides the sex stuff, which was incredible…”  He looked up at me. “It’s been nice having someone actually listen to me and like who I am. Help me look good, and likes how I look and… you know, cares what I think. Thank you.”

This was so sweet that I almost teared up. It was probably due to all the hormones shooting through me, but it was a nice moment between us. I just hugged him back.

Unlike with other boys, I didn’t have to explain myself any further here or go into the rules of our new relationship. Trevor knew he had to keep his mouth shut. And not a single fiber in my body doubted him. That’s also the reason why he turned out to be the only kid I worked with who had my picture.

Asking his sister to come with us next time did cross my mind briefly, but I’d have to explain myself too much, and it would raise too many questions. I took boys out shopping, after all. Not girls. And besides, I wanted this little horndog all for myself! But business was business. Maybe I could go out and hire my first employee to take girls shopping. I wondered if Mimi was up for a promotion… I noticed lately that she always checked out the boy’s asses when she thought nobody was watching her, and this also might open up some new opportunities.

Trevor’s mother thanked me and even gave me a substantial tip for finally getting him to wear proper clothes. However, she was disappointed we didn’t come home with new shoes. I told her we’d have to take care of that soon. Right before I left, Trevor’s sister walked by in the background, wearing a spaghetti top and extremely short and tight shorts, something a bit too revealing for the autumn weather, I would think. She threw a quick glance at her brother and headed upstairs.

I wondered if Trevor could pull it off again after such an intense morning with me. But at twelve-going-on-thirteen, he probably had more stamina than what was good for him. And it wasn’t my problem since I was already planning another appointment with his mother.

He gave me another hug, and his mother smiled at me, thanking me once more. As I drove home, I was picturing Trevor eating out his sister’s pussy and was glad I had another session planned with a different cute twelve-year-old this evening. This would be our second get-together, so I was in for a full hour of uninterrupted sex with a kid that didn’t know how to stop fucking me.

During the drive, my mind drifted off, and I thought about the last couple of months. StyleFocus had given me so much more than just fantastic sex with preteen boys. I finally found something useful to do with my life, and this was a job I thoroughly enjoyed doing. It helped me so much with getting my act together, and it boosted my relationships with Gemma and my father even more. I was no longer a hot mess that couldn’t hold a job for six months in a row. I was now a business owner and damn good at what I did.

So, yeah… StyleFocus was probably the best thing that happened to me, and the best way to satisfy my newly found desires!

The end

Copyright 2024 – Jason Crow
All rights reserved

Ibi habetis. Prima mihi valde subnectam fabulam. Spero te placuisse.

21

Day Job Shenanigans – Part three Read More »

Day Job Shenanigans – Part two

Adult/Youth, Boy/Woman Sex, First Time, Illustrated, Oral, Pics, Straight, Teens |

Day Job Shenanigans – Part two
By
Jason Crow

Everything changed for me some time ago. My fascination with young boys began when, one night at a club, I met a young man who took me back to his house. We spent the night together, but in the morning, I met his brother Brian, a twelve-year-old boy who had awakened my inner boy lover. His young, soft, and tight body blew off the lid that had been firmly attached for so many years. I took the boy’s virginity, and we made love the rest of the day. In the first few months, we had met in secret. We had many opportunities to do this since his parents were gone a lot, and his big brother, Steve, couldn’t care less about what his little brother was up to.

But after about a year, Brian started growing. His voice broke, his muscles expanded, and his long, slender cock wasn’t that slender anymore. And his watery cum, which was like nectar from the gods themselves, thickened and got muskier with each time he came. And he came a lot when we were together. He was still plenty of fun in the sack, but he just didn’t give me that energetic spark I felt when this had all started. When we’d met, he was quite the innocent boy; that year later, he’d become a very worldly young man.

Thankfully, he knew how to keep his mouth shut. It would have been easy for him to brag about me to his friends, but he just wasn’t like that. We came close to being busted once, but that was when he stayed over at my place. Later, it turned out to be the last time I’d had sex with him, and I was in the kitchen making us early breakfast. I heard the door open, and my heart stopped. It was my roommate Gemma, who was home way too early.

“What an asshole!” Gemma sighed as she threw her keys on the counter and sat at the table. Her blonde hair hung in her face, so she quickly pulled it into a ponytail. Her stylish clothes looked like she’d dressed in a hurry. She was supposed to be spending the night at this one guy’s house, an asshole’s house, apparently.

My mind was racing. Brian was in my room and didn’t know Gemma was home. I didn’t stage the couch with blankets this time because Gemma never came home this early, and I wasn’t going to drive Brian home until ten.

I tried acting cool and asked, “I thought you said he was such a great guy and gentleman?”

“Well… he was. Until his wife came home unexpectedly. He said he’d divorced her, but- oh?”

I looked at what Gemma was looking at since she stopped talking and was staring wide-eyed at my bedroom door. Brian was standing there in all his naked glory, looking freaked out.

“I… I can’t find fresh towels,” he said, quickly getting his act together.

He didn’t act shy or try to cover up, which, as I later learned, saved me. I saw a glimmer in Gemma’s eyes, but she didn’t say anything. Gemma and I walked around the apartment without clothes whenever it suited us, but it was just us. This was different.

“They’re in the bathroom. Come on, I’ll show you,” I said, surprised at how calm I sounded.

“I’ve already put my sheets in your bedroom,” he said as we headed to the bathroom.

“Thanks!” I answered and flashed him a thumbs-up for his quick thinking.

As we entered the bathroom, I breathed a sigh of relief, and Brian pretended to wipe his forehead with a relieved expression.

When I returned to the kitchen, Gemma looked at me. There wasn’t any judgment on her face, just curiosity. I weighed my options. I couldn’t possibly tell her the truth. She wouldn’t understand.

“It’s almost impossible to get some clothes on that kid,” I said casually, “He’d walk around naked all day if I’d let him.”

She grew a smile and said, “I figured that much. Why don’t you let him?” she grinned, cleared her throat, and continued, “Since, uhm… he’s hung like a pony…”

“Gem!” I said, acting offended but glad she didn’t judge.

“Don’t tell me you didn’t notice!”

“Yeah… well…” I pretended to stammer, “he is…”

“He’s looking mighty fine! In a year or two, I’d take his cherry in a heartbeat,” Gemma chuckled.

I shook my head and pretended to be busy with breakfast.

“What!?” Gemma pressed, “Didn’t you see the ass on that boy?”

“I did,” I said evasively.

“Fuck! And that snake between his legs…”

“You’re still horny… he’s barely thirteen, Gem…”

“I know. But still…”

After Brian had taken his shower, he was smart enough to stay naked to keep up the pretense of walking around naked all the time. He later told me he’d heard Gemma and me talking while he was in the bathroom and figured this was the smart thing to do. And after I pressed on a little, he admitted that he liked the attention.

But to me, this whole thing was too close for comfort. I thought about it extensively but decided I needed to end this. We had another Saturday evening planned where I’d stay the night at his house and leave Sunday afternoon. I decided that this would be the last time I’d fuck my little lover boy. The fact that I felt nervous like a schoolgirl for breaking up with this almost fourteen-year-old boy was all the confirmation I needed.

When Brian answered the door that night, he was fully dressed, which was uncommon for him. Usually, on such a night, he’d be in just his tight boxers, showcasing his prominent bulge. The look on his face wasn’t too promising, either.

“What’s up, Bri?” I asked as he stepped outside and closed the door.

“I… I… I think we need to…” he stammered, and I could see a tear form in the corner of his eye.

“Did someone find out about us!?” I asked, panic clearly seeping through.

Thankfully, he shook his head. It turned out that his parents had another huge fight and were finally getting a divorce. Right now, his mother was gone for about another hour to arrange everything for their departure, and his father was off to his mistress. Their aunt was there to look after the kids, but she was in the dining room with Steve. 

Brian and his mother would move in with his other aunt in Hawaii for at least half a year, and Steve would stay here with his father. It was all really sudden, but based on the stories Brian had told me, it was not that unexpected, at all. Brian assured me that Steve and his aunt would stay in the dining room that night so we could still do sexy stuff in his room. But that would be way too risky, so we just talked for a while.

Brian insisted we’d stay in touch by texting each other. I told him about the risks of being exposed, and he agreed. We’d keep things to a bare minimum and decided on no pics.

It turned out, not surprisingly, that the breakup with the young Adonis was easier for me than for him. He did send me a couple of nudes, which I carefully stored in a hidden, encrypted folder in my computer and were masturbation material for months. But after a while, Brian got himself a girlfriend, and our contact faded, which was fine. Sad, but fine. Being the one who took his virginity at a young age, and therefore being in his memories forever, was such a great consolation.

I think the breakup was easier for me because it coincided with the start of my new career. I had a degree in Art that I wasn’t using, and despite all my efforts to land a decent job, I was once again unemployed. The excuse to let me go this time? The company’s dire economic situation required cutbacks. It wasn’t me. No! If it was up to my manager, she’d never let me go.

It didn’t matter. This was another dead-end job, anyway. My fourth job in four years. I needed to find that one thing I liked and was good at. The only problem was that this was easier said than done. I was thinking about my options as I entered the apartment.

“Huh!? Back already?” Gemma asked, buck naked and drying her hair as the steam from her shower exited the bathroom.

My eyes quickly roamed over her firm tits and tight ass, but she immediately noticed something was up.

She sat down at the table and looked worriedly at me. “What’s up, Carol?”

I sighed, sat down opposite her, and said, “I’m laid off. Again!” 

“No!” Gemma exclaimed with her face full of disbelief, “Fuck that! Why!?”

“Something about the economic downturn or some shit like that. Don’t know, don’t care,” I said as I slumped down in my chair, trying to act blasé about it.

Gemma held her head in her hands and said, “Fuck, Carol! Why?”

“I wish I knew. I guess it’s finally time to call my dad.”

My father was a pretty successful businessman. He had a couple clothing stores in the area, and business was booming. Dad and Mom divorced, then it was just me and Dad for a time. After a while, Dad met a wonderful woman whom he married. We got along well, and after the wedding, we were a typical family again.

I had a carefree life, and when I went to college, Dad paid for everything. He wasn’t overly excited when I chose a more artistic major, but when I explained that this would help him in his business since I combined it with an economics minor, he was okay with it and never gave me a hard time about it.

But I didn’t want to go and work for him after I graduated. I wanted to spread my wings and find out for myself what was out there. After we talked about this, my father accepted my choice and actually encouraged me to live my own life. So, I found myself a lovely apartment in the city, and together with my best friend from college, Gemma, we moved in there.

“I can cough up the rent on my own for a while, and you know that!” Gemma told me.

“But I don’t wanna live out of your pocket, and you know that, too,” I said and tried to smile at my naked best friend.

“It will only be temporary. It’s more important that you’ll get a job you like.”

“You’re the best, Gem!” I sighed, feeling relieved and glad I had such a good friend.

“Alright. Let’s make a list of things you’re good at and things you like,” Gemma said and looked for a pen and a piece of paper.

She got to her feet and walked over to the living room. As my eyes were fixed on her naked ass, I started thinking about what I liked. I knew exactly what I liked, but I couldn’t say that to her.

When Gemma came back, she’d put on her silk kimono and was carrying two glasses, a bottle of white wine, and her laptop. I joined her on the couch. As she filled the glasses, I smiled at her cleavage. Her kimono hung open and was closed below her belly button. Her nipples were hidden by the silky fabric, but just barely. Our first and only attempt at having sex together hadn’t been a great success. Otherwise, I’d probably be all over her by now.

“Alright. You have your Theater and Arts degree that you’re not really using, but that’s a start. Now… a list. What are your strengths?” Gemma asked as she held out her glass and touched mine.

Yeah, what were they? When I went to college, it was mostly to party. I didn’t fail any classes, though. I got an Art degree and studied various forms like directing theatre, fashion design, and I did makeup for the theater and student films. Still, I actually did better in my business classes. 

“I… uhm…” I stammered, feeling a bit uneasy about opening myself up this much, “I’m creative?”

“Creative…” Gemma said as she started typing, “we can work with that. What else?”

I chuckled and said, “I give killer head…”

Gemma laughed at that and said, “There are some jobs where this is a huge plus…”

“I don’t think I’m looking for such a job…”

She looked thoughtfully in the distance and said, “We’d make a great couple as exclusive and expensive prostitutes, you know?” and she smiled broadly.

I smiled back at her and realized once again how much Gemma and I looked alike. Tight, fit bodies that we liked to show off in the gym three nights a week, where we’d turn lots of heads as we walked around. We’d squeeze ourselves into tight-fitting yoga pants and equally tight crop tops to show off our asses and C-cup breasts perfectly, and the cleavage was admired by all the men around us each time we bent over. Gemma’s blonde hair, as opposed to my dark-brown locks, was the main difference between us, really.

“If this doesn’t work out, I can always make a career move,” I said seriously.

She shook her head, “I don’t think it’ll help my career, though,” Gemma sighed.

Gemma was a fantastic marketing strategist. She interned at one of the best firms in the area, and they snapped her up when it was done. She’s rising fast and has her eye on becoming the youngest VP in the history of the company. She could easily afford an apartment of her own, but she said she liked my company and the down-to-earth vibe the neighborhood oozed. I wasn’t jealous or anything, but I sure wished my life was as much on-track as Gemma’s.

“So… you’re creative with blowing a guy… what else?”

“I like shopping… and I keep up with the latest trends…” I said weakly and shrugged. God! I sounded like Paris Hilton but without her money. What did I really want to do?

“Good. Go on…”

“I’d like to do something with clothes or costumes. I loved the backstage work in the theater I did when I was in college. But there’s hardly any work in that. It’s just that… I wish I could do more in that area than just picking up the phone and processing orders, you know?”

“Yeah. I get that. We need to find something more related to that. Anything else we can add to the list?” Gemma asked.

“I… I like kids?”

Gemma looked at me with a surprised look on her face. We’d talked about this before, and we both agreed we didn’t want to have kids. This was too much of a hassle and would limit us in how we wanted to live our lives. So, I could understand the surprised face.

I shrugged and said, “During one of the company’s fundraisers, I had to watch several groups of boys, and I had a great time. They listened to me and behaved themselves without any problems.”

“Did you promise to show them your tits if they behaved?” Gemma laughed.

I had to admit that this had been a tempting idea and had crossed my mind at the time. But the groups of ten- to thirteen-year-old boys I’d supervised had already been ogling my cleavage and ass constantly, so there really had been no need for promises. I’d even seen a couple of tented pants and became instantly wet at the realization that I was the cause of that.

“Maybe…” I said, making Gemma roll her eyes.

“You’re evil, you know that?”  Then she considered. “Well, you did have fun babysitting that Brian kid.”

So, Gemma and I talked some more about what I liked and didn’t like. By the time we emptied our second bottle of wine, I was feeling a pretty strong alcohol buzz. Thinking about Brian got me a little horny. Seeing Gemma’s kimono slip open got me even hornier. I put my arms around her. “I don’t want to think about this anymore tonight,” I whined.

“What do you want to do, then?” Gemma asked, as tipsy as I was.

That was a loaded question. I decided to give it a shot. “I want to lick your pussy.”

I could see Gemma think it over. “All right.”

With delight, I pulled open her kimono and pushed her back on the couch.

* * *

The following day, after having moved together to her bedroom and making a better-than-before effort at fun sex, I woke up with a slight hangover. Not too bad because we’d taken time out to eat some leftovers in the fridge, and I had a bottle of water.   But Gemma was awake early, so I missed out on waking up with her. She came back naked from the washroom, sat on the bed, and looked me in the eyes.

“I’ve got it!” Gemma softly said but didn’t say anything else.

“What?!” I asked, sitting up and waiting for her answer.

“Don’t judge me here. And hear me out before you say anything. Promise?”

“Of course!” I answered, curious as hell by now.

“What do boys hate doing?” Gemma asked.

“Uhm… showering. Going to church. Eating vegetables… lots of things.”

“Shopping for clothes!” Gemma exclaimed as if she’d just solved world hunger.

“Right…” I said, not sure where this was going.

“And their mothers maybe hate taking their kids shopping even more. So… you take them shopping for new outfits. For a small commission, of course…”

I had to let this sink in for a moment. Take boys out shopping? I was good at shopping. And by focusing on boys, I might even see a couple of them in their underwear. Just like with Brian before he stepped into bed with me and his soft, firm body pressed….

“Carol!? Hello??” Gemma said, snapping me half out of my daydream.

“I… I’m sorry. I think that’s…” I forced myself not to react too excitedly, “You know what!? I like it!”

“I know you’re actually good at shopping. I’ve seen you do it enough to know that much. And the little brother from that Steve guy you babysat a couple of times… he adores you! You just need a good marketing campaign and ridiculously overvalue yourself so the society ladies who are too busy screwing their tennis instructors think you’re the best – because you’re not gonna get the soccer moms. I’ll do the marketing for free, of course,” Gemma said, being the torrent of words she could be when she was excited about something.

“A Personal Shopper. I think this could actually work, you know?” I said, feeling hyped after the idea sunk in a little.

“Of course, it will! But you’ll need a logo… and a name… and…”

“StyleFocus,” I said, interrupting my best friend.

She thought about it for a moment and nodded approvingly. “That’ll work.”  The rest of the day was filled with the design of the overall look and feel for the public image of my business: logos, a website, and a mission statement. We contacted my father and showed him what we’d come up with. He said he liked the concept of my company, and we set up a business relationship with his stores. He was delighted to be a part of it, and Gemma got to add his business to her company’s clients.

That day, StyleFocus was born. And I’m still grateful to this day that my best friend Gemma assisted with its birth.

My new career turned out to be even better than expected. Most of my charges were nine and ten-year-old boys, dozens of them in this first year. They were cool, but only there to pay the bills. My main interest was in the eleven to thirteen-year range. Those were the most fun on multiple levels. I’ve taken out over fifty of these. Seventeen of them were very cute twelve-year-olds. Yes, I keep detailed records of them on my laptop. I noticed that in the thirteen-year range, the boys were becoming more independent, so this group, unfortunately, was the smallest. But this wouldn’t stop me from trying to get into their pants…

End of part two

Copyright 2024 – Jason Crow
All rights reserved

Adhuc inops? An nimis perspicuum est et scivistis post paucas paragraphos?

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Day Job Shenanigans – Part two Read More »

Day Job Shenanigans – Part one

Adult/Youth, Boy/Woman Sex, First Time, Oral, Straight |

Day Job Shenanigans – Part one
By
Jason Crow

Where it began, I can’t begin to know when. All I knew was that right now, I was doing the thing I liked best, and it was currently lighting up my entire insides. My tits were tingling all over, and my pussy was already soaking wet. The reason for this was simple. My thumbs were inside this thirteen-year-old boy’s boxer briefs, slowly pulling them down here in the clothing store fitting room.

“Ohh, yeah…” Damian whispered hoarsely above me.

“Mhhh…” I purred.

His small bush of reddish-colored pubes came into view. There were a couple more hairs there than the last time I looked at his pubes. Gazing at him, I felt my pussy tremble. Two seconds later, his hard, almost four-inch cock sprang free. It was so stiff it hardly bounced as it was freed from its confinement. Without waiting a second longer, I wrapped my mouth around his slender cockhead.

“Ohhh!!” Damian moaned above me, and he placed his hands on my head.

This was what my little lover liked best! I kept my mouth around his cock and let my tongue explore his spongy cut dickhead while my hands kept pulling down his purple and white striped boxers. My eyes moved up over his scrawny chest, seeking his eyes. When our eyes met, I made a show of licking his small dick like a popsicle and smiled inwardly at his hornier-than-horny face.

My hands moved up to cup his small and hairless but extremely tight ass, and I went for it for real. I knew that no matter what I did, this boy would cum quickly, anyway, since he’d anticipated this moment for weeks. But I wanted him to have fun. And there was almost nothing better than having a young cock in my mouth, so I wanted to enjoy the feeling of this slim tube of flesh the best I could.

I kept bobbing up and down, feeling his ass muscles move under my fingers. I considered aiming for his hole for a brief moment, but as the pitch of his moans grew higher, I focused all my attention on his cock. He was getting close.

I cupped his grape-sized balls and gave them a gentle squeeze. This would delay his orgasm for about another thirty seconds, and I let my tongue explore the entire length of his rock-hard dick. I loved the texture of his shaft and made sure to lick it everywhere I could. But when he approached the inevitable point of no return, I focused on the underside of his glans.

Up until now, at barely thirteen years old, just half my age, Damian had shot blanks. But in the car ride over here, he boasted that he could shoot, now. I sure hoped this was true and that it was not just a tiny drop on his piss slit. The good thing was that I was about to find out any second now. I released his balls, and I moved my hand under my skirt, where my pantyless pussy was aching for some relief.

“I’m… Ohh… I think I… oohhh!” Damian groaned above me and started moving his hips.

My right hand was still on his firm ass, and I made sure he couldn’t move his hips too much. I had to hold on as if my life depended on it as he tried fucking my face frantically. The moment his fingers dug into my skull and his thin cock fattened a little, I let the fingers of my left hand rub through my slit briefly. I didn’t want to cum yet, but the tension and anticipation was simply too much for me to handle. I shoved his boxers down to his ankles, ready for him to step out of them. He kicked them toward the fitting room mirror. 

Damian groaned loudly and suddenly kept perfectly still as his penis started kicking in my mouth. This was it. Would I be treated with… Oh yes! After two violent kicks of his cock, a small but powerful blast hit me at the back of my throat. And a second one landed on my tongue immediately after the first. I would never, ever grow tired of the taste of young boy spunk. It was a bazillion times better than the thick, musky stuff older guys shot. Granted, that was also pretty enjoyable, but the sweet, watery stuff that didn’t contain actual sperm yet – that was the best. By far! And I was treated with two small globs and a little dribble from the tip that I eagerly lapped up.

“Ohhh…” Damian exhaled, coming down from his orgasm.

I let go of his ass, and he immediately dropped into the chair behind him. I smiled at the goofy expression he always had after an orgasm and was pleased to see his cock was still sticking up and hadn’t lost any of its stiffness.

“That was… it was… I did, didn’t I?” he asked, still panting a bit. He reached forward to touch my hair, wrapping one of my loose, dark-brown curls in his fingers. 

“You sure did. You actually shot some cum!” I said as I let his sperm swirl through my mouth, savoring the taste as long as possible. I licked my lips for him. “So good…”

“It… I… oh, wow!” he exclaimed and slumped back in the chair.

I was so horned up by now that I just had to do something. My hand was under my skirt, lightly caressing my pussy. Damian looked at me and said, “I wanna see your tits…”

I still don’t know if he was aware of the effect this had on me. Seducing young boys was one thing, but being bossed around by them was even hotter. So, even if I wanted to resist, there was no way I could. I was like wax in his hands, and my hands almost involuntarily started lifting my shirt. The moment my breasts were revealed and the cool air made my nipples grow even harder, I heard Damian whisper a soft, “Oh, wow…” as if he was looking at my tits for the very first time.

I pushed my chest forward a bit, and as his eyes drank in the sight of my exposed boobs, I bit my lower lip. In his lap, his dick gave a violent twitch, and I knew he was more than ready for more. Yet another perk of fucking young boys. Even after cumming seconds ago, seeing my tits and the idea of fucking me kept him going.

“Can I… I mean… is it okay if we, you know…”

“We’ve talked about this, Hotshot…” I said, my eyes still on his rock-hard cock.

“Oh, right… I, uhm…” he cleared his throat, sat up straight and said, “I wanna fuck you, Carol. Get naked.”

“Ohh! That’s more like it, Hotshot!” I hissed, got up, and unzipped my skirt.

As it fell to the floor, Damian’s eyes roamed up and down over my body unabashedly. His hand gripped his cock and gave it an absentminded squeeze. I needed that cock inside me as soon as possible, so I lay down on the carpeted floor and spread my legs. Getting fucked on the floor wasn’t my first choice, but it was the quickest way to get him inside. Damian complained last time about how he couldn’t get a decent grip with his knees or feet on the room’s couch. So, by doing it on the floor, he could get rough if he wanted to. I knew I wanted that…

His eyes were glued to my cunt, and with my left hand, I spread my lips for him while my right pinched my nipple. He swallowed audibly and got off the chair. As he dropped to his knees between my legs, his boner hardly moved. Of all the boys I’ve seen naked and erect, Damian undoubtedly had the stiffest cock of them all. Unfortunately, he had lost his act about being in control and became a little boy again. I didn’t mind too much, though, as I watched his cockhead inch closer and closer to my sopping-wet entrance.

“There you go…” I whispered as the tip of his dick touched my pussy lips.

“Ohhh, Carol… You’re so freakin’ hot!” he said while looking in my eyes.

He talked about tits and fucking before, but when it finally came to actually fucking me, he always got this focused look on his face. This little red-headed cutie was adorable! But when he pushed himself inside with one strong push and his pubes mashed against mine, all this cuteness was gone, and he was my little fuck-boy again. He entered me for the third time since I met him, and it was just as hot as when he had before. There wasn’t the thrill of taking a boy’s virginity, but Damian compensated for this by tirelessly pistoning in and out of me. This kid had a stamina that a grown man would envy.

Feeling my clit being squashed under his small frame almost pushed me over the edge right away. His stiff little cock had such an upward angle that his dickhead rubbed over my G-spot with every thrust of his bony hips. Damian didn’t wait for me to get accustomed to being fucked. He just went for it, and I loved that about him.

He breathed a little laugh, and I noticed he was looking beyond me. He was watching himself fucking me in the room’s tri-fold mirror, the little scamp! “Who’s that boy over there?” I playfully asked.

“That’s me,” he replied between slams. “Me fucking you…”

“What are you doing?” I encouraged him.

“Fucking you… fucking your pussy!”

“Yeah, fuck my pussy…”

My hands cupped his firm little ass as the good feeling started washing over me. Feeling the bones of his hips slam against my thighs was another turn-on. I knew I’d be sore for the rest of the day down there, but damn! This boy was good! After three or four slams of his pubic bone against my clit, and the overstimulation of my G-spot, I came. It was sudden and unexpected, but a fantastic orgasm nevertheless!

But Damian didn’t seem to care. He just kept on pounding away, his mouth a little open, and his eyes unfocused. He was in the zone! The best thing was that I knew this wasn’t the end of it. I would come a couple of times more before he’d freeze, and his hard little cock would kick violently inside my pussy, triggering my final orgasm.

Thankfully, I was right! After four somewhat smaller orgasms, my little lover froze in my arms, and he threw his head back. The muscles in his neck tensed, his shoulders were shaking to hold himself upright, and he grunted deeply. And sure enough, a heartbeat later, his little cock started kicking, which sent me over the edge for the final time. This final push of his pelvis was the one that really did it! My little stud managed to do his magic once again. I came hard, and my belly muscles contracted so sharply that I had to bend my body a little. Damian didn’t care. He was in a world of his own as he came back down from his second orgasm in under ten minutes.

He dropped his body on top of mine and was panting heavily. I loved feeling the weight of his thin body on top of mine. His head was lying on my chest, and I smelled his freshly washed red hair. My hands caressed his back as he regained his breath. His skin felt velvety under my fingers, smooth with a light sheen of perspiration.

After a couple of moments, Damian asked, “Did you pee?” 

“No. Your cock made me cum so hard that I spurted a bit, too.”

“Cool! Now we both can shoot,” he chuckled.

I gave him a tight hug and patted him on his ass. It was time to go now. Good thing he was okay with the clothes I showed him after we entered the changing room here at The Style Haven. But then again, he’d also be okay if I’d picked out a summer dress for him instead of the jeans and tops. And I couldn’t blame him, considering what we did instead of trying on clothes.

“Can we do this again next week?” he asked as he stepped into his boxer briefs.

“I’m sorry, Hotshot. That would make your mom suspicious, don’t you think?”

He sighed deeply, looked at the floor, and disappointedly said, “Guess you’re right.”

“But don’t worry! This means it’ll be even more fun next time,” I said, and I could see his frown turn into a smile. “Don’t forget, holidays will be here soon, and you need a new outfit for church!”

We finished dressing, and I gathered the clothing items that Damian would be taking home today. I made the purchase on my special account, and we headed out to my car. During the drive home, we made small talk as if nothing out of the ordinary had happened. With Damian, I had no concerns whatsoever about him accidentally talking to his mom or his friends about us. He wasn’t a bragger or a talker, and he didn’t have lots of friends.

His mother was pleased with the result and thanked me for helping her out. But when Damian walked off for a moment to put the bags into his room, his mother whispered, “I think he has a crush on you!”

My heart froze.

“It’s so cute!” she chuckled, “He takes a shower before you get here, and he acts all nervous when he’s waiting for you.”

“I… uhm…” I tried to smile like I was embarrassed.

“Don’t worry, dear! You know how boys are. I think it’s adorable. He shou…”

Damian was back and smiled warmly at me. His mother laid her hands on his shoulders and said, “Thanks again, Carol. Are we square?”

“Yes. The transaction should appear on your account tomorrow. Let me know if there’s anything you’d like to return,” I said so professionally.

“I’d like to add a little something for you…” she hinted.

“No need,” I assured Damian’s mother. “I get plenty of satisfaction just seeing him smile!”  When he cums inside of me…. I added mentally. “Damian is a great kid.”

“What do you say to Carol?” his mother asked, clearly not yet accustomed to the idea her son wasn’t nine years old anymore.

“Thanks, Carol!” he said timidly, but couldn’t hide the sparkle in his eye.

“No problem, Hotshot,” I said and winked at him. “Thanks for choosing StyleFocus as your Personal Shopper,” I said to his mother.

I turned around and waved goodbye over my shoulder. After I started the car and drove off, my heartbeat finally started to calm. A couple of moments later, my phone rang, and it was my dad.

“Hey, Dad!”

“Hey, Pumpkin. You’re coming over later?”

“Of course! Today is the first anniversary of StyleFocus. We need to celebrate!”

End of part one

Copyright 2024 – Jason Crow
All rights reserved

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