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