Category: First Time (Page 3 of 58)

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Date Night Discovery
by
Jason Crow

Date Night Discovery

“What are you looking at?” I asked, a bit snarky, as I noticed a guy staring at me from the bar. The man seemed like a typical hillbilly, so full of himself that he resembled a cartoon version of him. Despite his attempt to undress me with his eyes, I was here just to get hammered with my roommate and best friend, Gemma, and had no interest in him. However, when I checked on Gemma, I found her in a corner, kissing a guy whose hands roamed over her body. Great!

Gemma and I often went out together, and it wasn’t unusual for us to end the night separately, each going home with someone. Since I was twenty-five and she was a year older, we felt free to do as we pleased and had no problems doing so. We even ended up in bed together after a wild night, but we both agreed that we enjoyed the company of hot guys a lot more.

Finding attractive guys on a Saturday night like this wasn’t a challenge for us. We basically looked the same. Firm C-cup boobs that we loved to accentuate with loads of cleavage, smooth muscular bellies, and tight asses showcased in either tight jeans or short skirts. The only difference was Gemma’s blonde hair compared to my dark-brown locks. Currently, my hair cascaded in loose curls around my shoulders, though during the day, I usually wore it in a ponytail.

The hillbilly, who had been eyeing me, walked over. I sighed deeply, not in the mood to reject another guy, when I noticed someone else checking me out. He appeared a bit younger, and I even doubted if he was allowed to drink yet.

However, he looked amazing standing there. He was tall, blonde, had piercing blue eyes, and a tight white T-shirt showcasing his muscular chest and bronzed skin. I winked at him and put my hair behind my ear, signaling my interest. He responded with a warm smile, and I knew I had him hooked.

“Hi. I have to ask you… Are you a parking ticket? Because you’ve got FINE written all over you,” the guy who was eyeing me earlier said as he got close to me.

I looked at him as he checked me out from top to bottom. He looked at me as if I was a piece of meat, his face smug about his opening line. I opened my mouth to tell him to go fuck himself when the guy in the white T-shirt appeared.

“Really, dude? You think that kind of cheesy line will work on such a beautiful lady?”

“I… uhm…” the hillbilly stammered.

“Wanna dance?” the guy in the white T-shirt asked, extending his hand.

“Love to!”

We hit the dance floor, dancing for a few minutes before finding ourselves talking at one end of the room.

“I’m Steve,” he said, smiling broadly, and asked, “You want some pickup lines?”

I shook my head, but he didn’t wait for an answer. With a massive grin on his face, he began. “If I could rearrange the alphabet, I’d put ‘U’ and ‘I’ together.”

“Oh boy…” I said, laughing loudly.

“Don’t worry. There’s more where that came from,” he chuckled, “Like… Well, here I am. What are your other two wishes?”

“Jesus…”

“Are you a magician? Because when I’m looking at you, you make everyone else disappear!”

“Stop it!” I laughed.

“I think your father is a thief! He stole two stars from heaven and put them in your beautiful eyes.”

He continued with pickup lines as if I wasn’t even there, a straight face intact. By now, I was laughing loudly and playfully slapped his chest.

“I’m not usually religious, but when I saw you, I knew you were the answer to my prayers.”

“I mean it! Stop it!” I said and kept my hand on his chest, enjoying the feeling of his muscular pecs under my fingers.

“I didn’t think anyone would actually use these lines anymore. That guy apparently didn’t get the memo.”

I wiped a tear from my eye and said, “Guess not. Thanks for saving me. I’m Carol.”

This was the start of a fantastic evening. We drank some drinks. Well… we drank a lot, actually. I learned that, according to his fake ID, Steve was twenty-one. But he actually was only nineteen. This put me off at first because I never went to bed with a guy this young.

But the more we talked and drank, the more attractive he became. He was sophisticated, funny, well-dressed, and simply looked like a young Adonis. I lay my hand on his jeans as we started kissing and slowly moved it toward his crotch. He didn’t object, and when I cupped the bulge in his pants, I was surprised by how well-endowed he felt.

“Wanna go to my place?” I asked, feeling the urge to get him inside me and ride his cock like a cowgirl.

“Sorry! I can’t,” he said, noticing my disappointment. “But we can go to my place if you want.”

“You’ve got your own place?”

“Well… not exactly. I still live with my parents. And my little brother is home alone now. I promised my dad that I’d watch him.”

“Oh…” I said, looking disappointed again.

“Don’t worry. He’s twelve and won’t bother us. I promise! And I think we can have a lot of fun together.”

He leaned in, nibbling on the sensitive spot under my ear, his hand moving up over my leg and under my skirt. The moment his fingers brushed over the laced front of my tiny string and his teeth gently scraped my neck, I was a goner.

“Let’s go,” I hoarsely said.

Steve ordered an Uber, and we headed out. As we stood outside waiting, I checked my phone and saw Gemma had sent me a text saying she was at our apartment with the guy she had met earlier. During the ride, Steve couldn’t keep his hands off me. I wasn’t a prude, but seeing the driver’s eyes constantly checking us out in the rear-view mirror was a bit of a turn-off. Despite that, I didn’t mind him squeezing my boobs every now and then.

We stopped at a huge mansion in a part of town I rarely visited since it was reserved for the wealthy. After my recent unemployment, I had even fewer reasons to be there.

As we walked toward the front door, I was amazed by the fantastic house Steve lived in. Okay, it was his father’s house, but still. It was modern, white with black accents, and the way the lights made it stand out in the night gave it a ‘fuck you, we’re loaded!’ vibe.

In the living room, the table in front of the TV was littered with a half-full pizza box, empty soda bottles, ice cream packages, and other stuff I couldn’t make out. But before I could take a good look at it, Steve was all over me.

As we went up to his room, I was stunned by how big this place was. But Steve was very good at keeping me occupied, so before I knew it, we were inside his room. I didn’t waste any time and dropped to my knees. After I unbuckled his pants and pulled them down, I sucked in a breath.

Inside his white Calvin Klein boxers, a monster tented out the fabric. I couldn’t wait to see it, so I pulled the black waistband forward and freed his hard cock. It stood at a forty-five-degree angle from his hairless groin, and the seven, probably eight inches of throbbing meat was something I’d only seen in porn so far.

It was the first time I had sex with a guy who’d shaved himself. Somehow, this turned me on even more. I’d always thought it would feel like having sex with a little boy, but now that I looked at this massive cock on a hairless groin, I felt a tremble inside my cunt. I didn’t waste any more time, licked my lips, and eagerly went down on his massive pole.

It turned out that he knew how to use his tool! After I sucked him off for a while, cramping my jaws in the process, he entered me. Thankfully, he did it with care because I haven’t felt this stretched before. But once he started going, he was like the energizer rabbit. He came quickly, which he later blamed on my more than excellent blowjob. But after he came, he stayed hard and just kept on going.

We fucked for almost an hour, but after he came for the third time, it was over. I only managed one orgasm during this fucking frenzy, and that was when he went down on me. He was just too big for me to really push me over the edge. But maybe the alcohol had something to do with that, too.

“You’re staying the night?” Steve asked as he lay down next to me.

“If you don’t mind…”

“Of course not.”

We pulled up the thin bedsheets, each on our own side of the bed. Steve yawned loudly, and before I knew it, I was out like a light.

* * *

“Steve?”

I opened my eyes, and it took me a moment to realize where I was. Steve was lying to my right with his back toward me and didn’t move.

“Steve?”

I lifted my head and looked at the door. There, in the dim hallway light, was a smaller copy of the guy who was lying next to me. He was standing there in just his bright-green boxer briefs, looking helplessly into the room.

“Get lost, Bri,” Steve grumbled next to me.

“But…”

The boy sniffed and looked so vulnerable as he stood there. But at the same time, I couldn’t help myself and let my eyes roam over his boyish body. I liked how his hairless body almost radiated in the hallway lights. This only lasted for the lesser half of a second, but I couldn’t deny it happened.

“I had a bad dream, and… my tummy hurts,” he softly said and sniffed again, “can I sleep with you?”

Steve didn’t respond, and I heard his breathing deepen, and he was asleep again.

“Well, that’s a dick move,” I thought to myself.

The boy shifted his weight from one foot to the other and was about to turn around. I was completely naked under the sheets, so I hesitated for a moment. But looking at his smooth, tight body and the thought of feeling it next to me triggered something inside. I didn’t want to admit it, but I found this young boy extremely interesting. And I blamed my motherly instincts for wanting to comfort him.

So, right before he turned around, I whispered, “Hey, kid! You can come over here if you want.”

His face lit up, and he strained his neck to see who I was. After a couple of seconds, he stepped into the room, tiptoed around the bed, and stood next to me. My eyes landed briefly on his crotch, and I was impressed by the bulge in his underwear. What was wrong with me? This was a freaking kid!

“Who are you?” he asked softly.

“I’m Carol. A friend of your brother. Who are you?”

“I’m Brian,” he said, and a sly smile spread across his face, which was an odd contrast with his puffy eyes.

“Lemme scoot over so you can get in.”

I turned to my left side so my back was toward Steve’s. I moved back a little and lifted the sheet a bit as an invitation for Brian to get in. I was careful to not lift it too high. He caught on and crawled into the bed with his back toward me. I draped my arm over his midsection and kissed his hair. He smelled like a mix of popcorn and axe body spray, which brought a smile to my face.

He scooted backward so his back was pressed against my front and chuckled. I felt my hard nipples press against his shoulder blades, but surprisingly, it didn’t bother me one bit.

“You’re naked,” he whispered secretively as if he told me something he wasn’t allowed to know.

“Yeah… didn’t bring my PJ’s with me.”

“Did you do… sexy stuff together?”

“That’s kind of a personal question,” I said and stroked the soft skin on his chest, “but, yeah. We did.”

“I thought so. I heard you guys earlier. Wha- OW!”

He cramped up and pushed his body firmer against mine. I felt sorry for the kid and tried soothing him by kissing him on his cheek.

“It’s my tummy…” he whined.

My hand moved down from his chest to rub him over his belly. Feeling his soft, velvety skin under my fingertips was something I’ve never felt before. Usually, there’d be hairs down there one way or the other, but this boy’s skin was as smooth as a baby’s ass. Feeling his developing muscles was a weird contrast, but I absolutely loved how it felt.

“Better?” I asked as I gently rubbed over his belly.

“I guess…”

“What’s wrong with your tummy?” I asked after gently rubbing it for a while.

“Dunno.”

“Did you eat too much ice cream, maybe?”

“Maybe…”

“Probably…” I chuckled.

“Steve lets me eat what I want as long as I don’t tell Mom or Dad.”

“I see. And where are your parents?”

“Mom is at a tennis tournament somewhere in Florida with her teacher. And Dad is on another business trip with his secretary.”

Oh wow! It can’t be more cliché than this. Filthy-rich parents pretending to be married but screwing around as much as they want. And their kids need to figure it out on their own. I felt sorry for the boy lying in front of me.

“Steve was supposed to watch me, but I don’t need a babysitter anymore. Had my birthday last month, and now I’m already twelve, you know?”

“I see. You’re a big boy”. I can tell.”

“Yeah… He does this all the time. Every Saturday evening, he buys me pizza and stuff so he can go out and find a girlfriend. He usually does…” Brian said and giggled as I put a finger in his belly button, ”Usually not as nice as you, by the way.”

It didn’t bother me one bit that Steve slept around like this. I did precisely the same, and we both knew what was happening here.

We were quiet for a few moments. As I rubbed his soft belly, an evil little voice whispered inside my head. It was wondering if this sweet boy was this soft and smooth everywhere… I dismissed this thought at first, but it just kept coming back, no matter how hard I pushed it away.

As if my hand had a mind of its own, it moved down and brushed the skin right along the elastic waistband of his boxers. I didn’t know what it was, but I just had to know. My fingers moved to the side of his little body, and right below his hipbone, his boxers had a tiny bit of space between his skin.

“How’s your tummy?” I whispered.

“A little better.”

I slid my fingers under the elastic waistband and moved them toward his front. They were still just under the waistband, but I wanted to see how he reacted to this.

I loved how his silky-smooth skin felt under my fingertips, and I whispered a soft “Good” into his ears.

“Yeah. Your fingers feel really good.”

As he said this, I slowly moved them down and rubbed my fingers in the same circular motion over his skin, just as I did on his tummy. I hoped this would keep up the pretense of helping him as I was aiming for my goal.

Further and further down I went. By now, I must be low enough to feel something, but he was still completely bare. The circles I was making with my fingers were smaller now, and a tingle shot through my pussy as I realized I was rubbing the pubic area of a twelve-year-old boy. I never knew I wanted this, but as I went down this path, I was amazed at how excited I was.

My heart was beating in my throat, and my pussy was slippery as hell by now. I was still a bit sore from being pounded by Steve’s big cock, but this quickly got to the background as my excitement grew.

When I accidentally brushed against the base of his boydick, he softly sucked in a breath. I didn’t want to overstay my welcome here or scare him off, so I moved a bit upwards again and whispered a soft, “Sorry.”

“It’s okay. This feels nice.”

I needed to divert the attention away, so I asked, “What was your dream about? I heard it helps to talk about your dreams.”

“Two big spiders were chasing me down an old house. Then I ran outside, and the garden was one big graveyard,” he whispered and took a deep breath.

“Sounds scary,” I said and kept making small circles with my fingers over his bare pubes.

“As I was running towards the gate, zombies came crawling out of the graves. I kept on running, but I tripped. And that’s when the zombies got to me. One of them bit me in my neck, and that’s when I woke up.”

“Poor boy… Think you can sleep now?” I asked and kept on moving my fingers around.

“I guess so…”

“Let’s try and get some sleep then, okay?” I said, kissing him on his ear and keeping my fingers inside his underwear.

“I was afraid you’d send me away…”

“Of course not. You can stay with me for the rest of the night.”

“You’re cool…”

“You too,” I chuckled.

I got comfortable, but I kept my hand where it was. I could relax my arm since my fingers were held in place by the elastic waistband. I felt the warmth of his young body against me, his soft, hairless skin under my fingers, and I knew, deep down, that I had tapped into some deep, hidden desires I never consciously realized I had.

His body relaxed in my arms, and his breathing deepened. I squeezed my legs together to release some of the building pressure and felt the long night and alcohol pushing me down to the land of the sleeping.

“Maybe it’s just the alcohol,” was the final, comforting thought thatshot through me right before I drifted off.

* * *

I felt a hand on my shoulder and movement behind me. I was still lying there with the twelve-year-old boy pressed against my naked body with my hand inside his underwear. But when a muscular chest pressed against my back, I felt a bit of panic.

“Hey,” Steve whispered, “I see you met Brian. Would you mind looking after him for a couple of hours?”

I turned my head to look at him and must’ve looked confused.

“He’s a good kid, but I’ve… I’ve got somewhere I need to be,” he said and showed his phone to somehow make his point.

“Uhm…” I mumbled, still half-sleeping but already excited to be alone with him.

“I’ll pay you!” he blurted, pressing his lower body against mine, “One way or the other…”

His seductive smile did nothing to me now. Last night, it had gotten me instantly wet, but seeing it now and feeling his soft, massive dick against my back, did absolutely nothing. I was feeling tired and wanted him to leave as quickly as possible, so I whispered, “Sure. No problem.”

“Thanks! You’re a lifesaver, uhm…”

“It’s Carol.”

“Thanks, Carol! Later.”

He gave me a kiss on my cheek and got out of bed. He was moving fast, and I figured it must be something important. In my arms, Brian slept like a baby and didn’t even flinch as the bed shook.

But I was instantly awake when I felt something brush against my fingers. It was a very brief contact, but a touch that made my pussy quiver. This was his little stiffie! And it was incredibly close to my fingers!

Now, I was fighting a mental battle about what to do. The sensible part of me told me I should pull my hand out of his undies. But the naughty part of me had to know what he felt like in the dick department. And that’s when I felt it touch my finger again.

I didn’t know what it was that pushed me over the edge. I was well aware that it was a million kinds of wrong to touch the dickie of a barely twelve-year-old boy. But somehow, it was different with this boy. At least, that’s what I told myself.

Ever so carefully, I moved my fingers upward. Almost immediately, I touched the skin of his shaft. The radiant heat coming from it wasn’t at all different from a grown man’s dick. I softly traced my fingers around the shaft so I could touch the underside and size him up properly. As I did this, I had goosebumps all over my body, and my pussy was instantly sopping wet again. But I didn’t care. I had a goal.

Once I had my fingers on the underside of his stiffie, I moved them down towards his balls. When I felt his dick move inside his body and his sack started, I stopped moving down. It was difficult to move further down without moving my body and wake him. And I wasn’t here for his little balls. I wanted to feel what he was packing.

I took a breath to steady my nerves and moved my fingers. My thumb and index finger were at each side of his shaft, and my middle finger was in the middle. I didn’t know what to expect when I started sliding upward. Two, maybe three inches of throbbing boy meat?

I slowly moved my fingers, savoring every piece of him and careful not to wake him. My pussy contracted sharply when it really dawned on me what I was doing. The moment I reached his cut glans, I realized he was big. It was probably four, four-and-a-half inches without his cock head. He was made from the same gene pool as his massively hung brother, so it shouldn’t be a surprise. But this only added to the youthful sexiness this boy oozed. 

I was careful around his glans because this was his most sensitive spot, and I definitely didn’t want to wake him and explain what I was doing. But there was just one more thing I had to know. So, I wrapped my fingers around his shaft and gripped it. I was only touching it and careful not to squeeze or stimulate it in any way. I was surprised by its slenderness. Because of his brother’s monster between his legs, I had expected the same here. But he clearly had some growing to do in the girth department. I didn’t care. I fucking loved his long, slender cock in my fist. And at that moment, I didn’t care that it belonged to a young boy.

This soft, sexy body in my arms had unlocked a part of me that I knew had always been there but hidden deeply away in the crypts of my core. I had just pushed it away every time it roared its ugly head. But the smooth, shaven body of his brother and this young adolescent sexiness in my arms were just too much. It had blown off the lid from this part of my soul, and it would never get back on. There was no more denying. I loved boys!

This epiphany didn’t upset me as much as I expected. I had always known. I was just too chicken to accept this fact. But now that I did, I didn’t know what to do with it. Should I jack him? Should I wake him and let him fuck my brain out? Should I do nothing and hope my feelings will go down eventually?

After giving it some thought, I figured it was probably best to do nothing. My female body was a weapon here. This boy was probably curious about girls and women, and I would use that to my advantage. It was best to let him set the pace here. But this didn’t mean I had to let go of his hard boydick! If he’d wake up and have a problem with it, I could always say it happened in my sleep and get away with it.

I figured I might try and get some sleep. Not that I’d be able to sleep like this, but there was no harm in trying. I gave it a gentle squeeze, and it tried twitching in my fist. He didn’t move a muscle, and I smiled broadly. I couldn’t control myself and did it again with the same result.

I resisted the temptation to do more and settled in again despite knowing it was probably useless.

* * *

I was startled by the movement next to me. My arm was still draped over Brian’s body, and my hand was on his hip now. My underarm was on his pubic bone, but I couldn’t feel his dick. I panicked for a moment. Did he wake up with my fist around his stiffie? But since he was still living here and not squirming away from me, I was probably okay.

He softly chuckled. I could hardly hear it, but I felt his body shake a little as he did. I fluttered my eyes and opened them. Seeing his angelic, Adonis-like face in the golden morning light made my heart melt instantly. His eyes were locked on my chest, and he didn’t even realize I was awake.

Inside his underwear, there was movement. As he was checking out my boobs, he grew hard. Before long, I felt him press against my underarm. I didn’t move and made sure to feel as much of his boner as possible.

When he chuckled again, I asked, “What’s up?”

“Your boobs are showing.”

“So?” I asked and moved my body a bit so my arms weren’t in the way anymore, and he could see them better. As I did this, my hand rested right on his boner. But he was so focused on my tits that he didn’t even notice.

“I’ve never seen boobs before.”

“You can look. I don’t mind.”

“They’re cool.”

“Thanks!” I said, hesitated for a moment, and said, “You can touch them if you want.”

“Really?” he asked, and his face lit up.

His boner twitched violently under my fingers, but he didn’t seem to notice. Because my hand was touching him in its entirety, I could size him up even more accurately. One thing was clear. He was big for his tiny frame!

Reluctantly, I lifted my hand from his underwear-clad boner and turned to my back to give him all the access he needed. I smiled warmly at him as he looked nervously at me. He extended his hand, and I saw it was shaking a bit, which was adorably cute. But the moment his hand touched my right boob and he squeezed it softly, all the cuteness was gone. The electricity that shot through me went from the back of my spine straight into my sopping wet cunt.

This pubescent boy feeling me up was incredibly sexy, naughty, and forbidden at the same time. I absolutely loved it and wanted nothing more than to keep this up.

But Brian didn’t need encouragement. He was bold enough to fondle my boob and switch to the other one without me urging him on. He started toying with my rock-hard nipple, squeezing it gently. I let out a soft moan as he did this, and he looked worriedly at me.

“Did I hurt you?”

“No. Not at all!” I said, smiling warmly at him, “This feels really good.”

“You’re so soft…” he whispered to no one in particular and continued feeling me up.

I loved what he was doing to me. But I was so horned up by now that I wanted to take this a step further. So, with my foot, I started sliding down the bedsheet. Brian didn’t notice and just kept squeezing my boobs. I glanced down, seeing I was lying there completely naked now without the sheet covering me. He was lying there in his bright green boxers, with an unmistakable tent inside.

As if he snapped out of a trance, he looked down at my body and whispered, “WOW!”

“If you want to, you can also touch me there. I don’t mind,” I said as casually as possible.

He swallowed audibly, nodded, and moved his hands over my belly toward my pussy. He didn’t take it slowly. He had a goal, and he wanted it now. But his fingers felt electric on my skin, nevertheless.

“You’ve got hairs down there,” he said as he brushed his fingers over the top of my neatly trimmed Brazilian.

“Yeah,” my trembling voice managed to croak.

I was having a hard time keeping it together as this small Adonis explored my most intimate parts.

“Steve doesn’t have hairs,” he said, his hands going lower and lower, exploring every inch between my legs, “he shaves it.”

“I grpg-“ I groaned as he brushed over my lips. I cleared my throat and calmed my nerves. “I know. I noticed last night.”

“Right…”

After a couple of moments, he perked up, lifted his head to look at me, and excitedly asked, “Hey! I’ve got a couple of hairs now. Wanna see?”

Did I want to see? Really?! This adorable innocence was new to me, but it reminded me he was still just a boy.

“I’d love to!” I answered, equally excited, without sounding creepy.

A strange emptiness washed over me when he let go of my body and turned to his back. But I knew I was in for a treat, so the emptiness quickly made way for excitement. He pulled down the front of his boxers and exposed his bare pubes. I felt my mouth water as I looked at his groin.

“See?” he said proudly.

Beside his sexy, slightly muscular belly with bare pubes and the hint of his dick’s base, I didn’t see anything. Not a single hair was there. He must’ve seen me looking because he softly said, “You’ll have to look closer…”

He didn’t have to tell me twice! I moved in closer, and as my face was inches away from his groin, I smelled a sweet, musky scent I came to love so much after I smelled it for the first time on this young stud.

“Here!” he said and pointed at a barely noticeable blonde hair right above the base of his dick.

I had to stifle a giggle but nodded enthusiastically to put him at ease. I started feeling bold, extended my fingers, and touched it. I noticed a tiny other one and rubbed it, too.

“Here’s another one.”

“Cool!

An idea popped up as I felt myself grow slipperier by the minute. So, I looked him in the eye and asked, “Want me to check your balls?”

This made him visibly uncomfortable, and I knew I had to act quickly. I smiled my warmest smile and said, “You’re getting bigger now, so there might be some hairs down there now.”

“But… I…”

“Don’t worry,” I said soothingly.

I didn’t give him time to think and started pulling at the legs of his boxers. He didn’t protest or stop me, but he wasn’t actively helping me either. But I didn’t care. I had to see him. All of him. I made up my mind then and there that I’d do everything I could to teach him how to have sex with a woman. And I was going to be that woman!

The moment his boxers got caught under his ass, he lifted his hips, and they slid down halfway past his upper legs. My eyes immediately went to his hard boy cock between his legs. And I was genuinely impressed. I’ve been fucked by grown guys smaller than this barely twelve-year-old boy. Up until now, I only had a mental picture of it by using my fingers. But now I saw him in all his glory, and I could see he was five inches from his cut tip to his base. His shaft was as thick as my thumb, which only accentuated his length. The small, marble-sized balls inside his hairless sack completed this sexy stud next to me.

I pulled his boxers off completely before he could stop me and drank in the sight. He looked insecure and vulnerable but also sexy as fuck lying there for me to play with. I kept up the pretense of checking his sac and let my fingers roam all over it and the base of his dick.

“You’re really a big boy!” I said hoarsely and wrapped my hand around his shaft.

“Aaahh!” he grunted.

I smiled at his reaction. I was probably the first person besides himself ever who ever touched his boner. I moved my hand upward, and he whimpered softly as I did this.

“You like this, huh?”

He nodded vigorously as I slowly moved my fist up and down over his slender erection. He fitted perfectly in my fist, and I was amazed at how sensitive he was, especially around his blunt dickhead. He was rock-hard, and as it slid through my fist, I knew then and there that I needed him to fuck me. But if I’d let him enter me now, he’d probably last only a few seconds. I needed him to cum first, so we could both enjoy his devirgination to the max.

All my inhibitions were gone by now. I was going to fuck this boy’s virginity away, and I’d make it count! Before I knew it, my lips wrapped around his dickhead, and I tasted his sweet but still boyish musky taste of his dick. There was a hint of saltiness mixed with the sweet bitterness of a day without a shower. I abso-fucking-lutely loved it!

“Wha- what are you… ooohhh…” Brian moaned as he realized what was happening.

His long, slender cock fitted perfectly in my mouth. It was long enough to hit the back of my throat and thin enough so I could work my tongue the way I wanted. Every time I lapped over the underside of his cock head, he squirmed and moaned louder. This kid was experiencing all sorts of new feelings he couldn’t place, but he clearly loved every second of it.

I moved my hand from the base of his young cock and started toying with his lovely little balls. The squirming and moaning got even more intense as I did this, and I heard his breathing getting shallower. Good!

His balls pulled up in his sack, a clear indication he was about to cum. In the corner of my eye, I saw his hands gripping the sheet and his knuckles white from clenching his fists.

His ass lifted off the bed, and he started fucking my mouth. He was rapidly approaching the point of no return, and I wondered if this was his first-ever orgasm or not. And was he able to shoot cum or not? If he could, what would it taste like?

All these thoughts shot through my head as I gave this cute little blonde his first-ever blowjob. And when he whimpered, “Stop! I’m… gonna… pee…” I knew it was his first. And I was the one to give it to him! He’d remember me forever, and an incredible sense of pride and power washed over me.

He tried squirming away from under me, but I didn’t let him. I doubled my efforts, and a moment later, his thin boy cock thickened in my mouth. A high-pitched groan filled the room, and when his dick started kicking in my mouth, my pussy contracted sharply, and I almost came without touching myself.

His dick kicked violently at least seven or eight times as it tried shooting his non-existent sperm into my mouth. He was firing blanks, and I was ever so slightly disappointed by that because I was extremely curious about its taste. But at the same time, it was exciting as fuck to get a boy this young off.

After the twitching of his cock died down, he collapsed on the bed and was completely limp. With an obscene pop, I let his dick get out of my mouth and looked at him to see if he was alright. He was looking wide-eyed at me, and his face was a mix of excitement and wonder. Now that I could look at him properly in all his naked glory, I let my eyes roam over his young, sexy body and made as many mental pictures as possible. I knew I’d get off on this for months!

“What was…” he panted.

“That was a blowjob,” I smiled and laid down next to him and draped my arm over his chest to caress his chest and belly.

“And when I… I thought I needed to pee, but…”

“That was an orgasm. Or cum, which is a word I like better. You’re really a big boy now!”

“Wow!” he exclaimed. Next, he propped himself up on his elbows and excitedly asked, “That was… can we do that again?”

I chuckled at the expression on his face and his shameless eagerness. I let my hand wander down, and as I wrapped my fingers around his boner, I wasn’t surprised he hadn’t lost any of his stiffness.

“Sure! What do you wanna do?”

“Dunno…” but as a wicked grin spread across his face, I knew what he wanted.

“What?” I asked innocently, feeling my dripping cunt contract again.

“Can we do, you know… real sex stuff?”

A tremble shot through me, and I asked, “Real sex stuff?” as if I didn’t know what he meant.

“Yeah… when I stick my, you know… in your…” his boner twitched in my fist as he said this, and his face and upper chest turned crimson red.

“I think we can do that,” I said, smiling wickedly myself. His blush faded away, and his face lit up, “But only if you use the grown-up words for it…”

“Wh- what… oh!” he whispered, but as my words landed, his blush was back with a vengeance.

 I squeezed his dick but didn’t make any move. I wanted this sexy young stud to say it himself. I didn’t know why I wanted it, but the idea alone was an immense turn-on.

“I… I wanna… fuck… you!”

“Hmmmm…” I purred, “I want you to fuck me too!”

He quickly got up from the mattress and sat on his knees between my spread legs. I looked down, and between my tits was this bronzed young, slightly muscular blonde boy with his hard cock sticking up from his groin. If this was the last thing I ever saw, I’d die a happy woman.

“Where… where do I put my thingy?”

“Grown-up words, remember?”

“Where does my… dick… go?”

Good enough.

I spread my lips and pointed at my opening. I couldn’t resist the urge and slid my index finger inside. A shiver shot through me, and I almost came as I looked at his amazed face. As I pulled my finger out, he nodded ever so slightly and scooted forward.

He grabbed the base of his cock, moved his body, and aimed at my opening. The moment his blunt dickhead touched the entrance of my pussy, I had to resist the urge to push him inside with my legs. But I had to keep my cool and not scare the little kid away. So, I steadied my nerves, took a deep breath, and hoarsely whispered, “Good! Now push it in…”

He swallowed audibly, and the tip of his tongue peeked out of the corner of his mouth as he concentrated on his task. It was incredibly adorable and blazing hot at the same time.

But as he entered me, I started to lose my cool. My dripping cunt was on fire, and the preteen cock that was entering me only added to the fire. He was about halfway inside when I couldn’t take it any longer. He was moving so slowly that it almost hurt. It was cute he was being careful, but I needed him to fuck my brains out!

So, I grabbed him by his arms and pulled him on top of me. It was a little rougher than I intended, but he didn’t seem to mind too much. Once his whole body lay on top of me, I placed my hands on his cute little butt and whispered, “Fuck me, big boy… fuck me!!”

With one final push of his hips, he was completely inside. His hairless groin pressed firmly against my clit, and his eyes locked onto mine. His mouth was open, and the look of amazement on his face matched my feeling of victory for having this boy inside and on top of me.

“Ohh… you…” he groaned and held himself perfectly still.

I was so close to cumming at that moment that even the slightest movement would set me off. But he kept lying still on top of me, and his slender cock didn’t move an inch. The combination of his small body and thin cock was unbelievably hot. I had expected to be a little disappointed by it, especially after being fucked by the thick monster his brother was packing. But the opposite was true! Because he was thinner than anyone I had ever fucked before, my pussy had more room to move but was still stimulated over its entire length.

And because of his small frame, his head was on my tits and not breathing down my face, which wasn’t that pleasant most of the time either. These two things combined were my definitive confirmation that I only wanted to fuck young boys from that moment on. But my young lover still hadn’t moved an inch, so I squeezed one of his ass cheeks and said, “Start moving. It’s even better.”

“I just move my thi-… dick in and out now?”

Another tremble shot through me as he said this, and I could only nod. Under my fingers, I felt the skin of his ass move. It was delicate and firm at the same time, and I could feel every muscle move under his soft, hairless skin. The moment his cock started sliding back, I let out a groan. I couldn’t help myself anymore. But my inexperienced lover stopped moving immediately and looked worriedly at me.

“Did I hurt you?”

“Oh no! You’re doing great! It feels so good. I can’t hold back my moans!”

A light clicked on inside his head, and he asked, “Are you gonna make a cum too?”

Hearing him talk with this enthusiasm and naivety was so amazing that I just had to talk dirty to him. So, I looked him deep into his eyes and said, “Your stiff cock is so perfect! If you start fucking me good and strong, I’ll cum so hard, you’re never gonna believe it. My hot cunt will suck your cock dry, I promise!”

His insecure look made way for a shit-eating grin. And he started pulling back again. But way too soon, he pushed back in. It was frustrating knowing his five-incher had more room to move and more chances to please me. But he needed to figure this out for himself.

When his bald pubes smashed against my clit again, I felt I was already at the peak of my arousal, and another moan escaped my lips. But this time, he didn’t stop. He pulled back, and as the rim of his dickhead slowly slid out, I felt my insides ripple over his shaft. I’ve never felt this before. But then again, I was usually fucked by thicker cocks.

He pulled back further than last time, and I wondered when he’d stop. It was obvious he was completely inexperienced because last time, he had pulled back less than halfway, and now he kept on going. I tried pushing on his ass to warn him, but a heartbeat later, he slipped out, and his wet dickhead rubbed over that sensitive spot between my asshole and pussy.

“I’m… I’m sorry,” he stammered but didn’t make a move.

My right hand sneaked between our bodies, and I quickly lined him up again. I smiled at his worried face, but when his dickhead slid in, he grinned and pushed inside. He didn’t go slow this time, though. He pushed in hard, and his groin slapped against mine.

All this clumsiness, combined with another push of his soft, bald pubes against my clit, pushed me over the edge unexpectedly. Usually, my build-up was way longer and almost agonizingly slow. But this time, this smooth little boy with his long, slender, but rock-hard cock pushed me over instantly. The combination of being fucked by a cuter-than-cute boy this young, the dirty talk, the clumsy inexperience, and the look of wonder on his face was just too much.

I firmly grabbed his ass as the waves of pleasure rolled over me. My pussy had enough room to contract but was filled up enough to still be stimulated by this thin, throbbing piece of flesh. I had to shut my eyes, arced my back, and grunted deeply. But this green-as-grass young lover between my thighs didn’t give a shit about it. He just kept sliding in and out of me. And I didn’t care one bit.

With the thicker cocks, I needed time and space to let my orgasm hit me. But with this young lad pounding away, it didn’t matter. Heck, it was way better than I’d ever had in my whole life! I couldn’t stop moaning as my orgasm kept rumbling, and this boy kept stimulating me. It was like a perfect storm. My cum urged him on, and his prepubescent cock kept enhancing my orgasm.

Our bodies merged into one as I lost my connection with reality. I squeezed his ass, moaned incoherent sentences, and only saw his blonde little concentrated face in front of mine. Everything else was gone. It was just this fantastic fuck, and the one long orgasm that came with it.

But this couldn’t last forever. In front of me, his concentrated face morphed into one of pure lust and excitement. He was slamming his groin against mine with such force now that a grown man would hurt me. But his tiny frame and small hips weren’t capable of this yet.

When his eyes crossed and he slammed into me even firmer and stayed there, I knew it was happening. The mere thought of his young cock trying to shoot his jizz into me was enough to push me even harder down the rabbit hole my current orgasm had become.

I felt him thicken, and his eyes crossed. My pussy was gripping him firmly, and as he let out a loud, “Aaaahhh!!!” his five inches of boy meat started kicking inside me furiously. This caused all the muscles in my lower abdomen to spasm, and I was sure I’d have a muscle ache for days because of its strength. Even though nothing came out, his cock tried all it could to shoot deep inside of me. With grown men, their dicks would kick four or five, maybe six times. But this young stud’s cock just kept on kicking, sending me off again!

I lost count by then, but looking back, it was like one big organic orgasm, and the separate ones had morphed into one. After he came, he dropped down and lay his body on top of mine. I kissed him on his neck and rubbed him gently over his back, letting him enjoy his devirginizing first fuck. Damn! I took this boy’s virginity! He’d remember me for the rest of his life. And if he even knew how good it was for me!

This was the moment it really dawned on me that I only wanted to fuck young, virgin boys from that moment on. I knew it was a gazillion kinds of wrong, but I didn’t care! I never had the urge to be married with children, and I was perfectly fine on my own. I just wanted to get fucked regularly, and I knew I could pull this off. I just had to work for it, but the reward was well worth it!

Brian was regaining his breath, but his little cock was still rock-hard. “Another perk of fucking young boys!” I thought to myself. I squeezed my pussy, causing his dick to twitch, and the cutest giggle came from his mouth. He lifted his head and smiled wickedly at me, a smile that melted my insides.

“Now you’ve made your cum, didn’t you?”

I’d have to explain to him how to talk about sex, but now I opted for a simple reply. “Oh yeah! You did great!”

“Did I give you your cum?”

“You sure did! More than once, actually!”

“Oh wow… cool!”

Seeing his proud face was just too cute. I leaned in and kissed him on his girlish lips. My little loverboy immediately caught on and kissed me back hungrily. I squeezed my pussy again and was pleased he responded with another twitch of his boner. Good! He hadn’t lost any of his stiffness.

He broke the kiss, slid his hips back and forth, and eagerly asked, “Can we do it again?”

“Sure! But… when will your brother be back?”

“Dunno. He’s usually back at two. He’s at Aunt Julie’s. He always goes there on a Sunday when Mom and Dad are gone. I think they do sexy stuff because he always smells… different when he gets home.”

I couldn’t blame his aunt. Steve was a good fuck. A very good fuck, actually. But as I checked the alarm clock on the nightstand, I was thrilled to see we still had over four hours of fun ahead of us.

We fucked three more times that morning. This stud just kept on going! We headed over to the bathroom, and he finally went limp as we walked. But I would have none of that. So, during the shower we took together, I sucked him off the best I could, and we had our final fuck in there.

After Steve got home, he thanked me extensively and offered to give me my payment upstairs. Brian was right, and he did smell like sex. Good for them! But I smiled warmly at Steve, politely turned down his offer, and winked at Brian, who chuckled softly.  

We said our goodbyes, and when my Uber arrived, Brian and Steve waved goodbye. As I walked up to the door of my apartment, Gemma just waved a good-looking jock goodbye, and as we passed each other in the hallway, we nodded politely to each other, the grin on the guy’s face saying it all.

“And?” Gemma asked, “Was your fuck as good as mine?”

“Better!” I smiled.

I thought about little Brian all week. I just couldn’t get him out of my head. Every night, I fingered myself silly with images of his magnificent body filling my head. When Gemma asked me to go dancing with her next Saturday, I came up with a lame excuse. The moment she was gone, I stepped into my car and drove over to Brian. I parked a little out of sight, but I could still see the front door of the mansion. Sure enough, only ten minutes after I arrived, Steve came out of the front door, all dressed up, and I heard him say, “Don’t wait up, Bri! I’ll probably be back tomorrow at two!”

He shut the front door and stepped into a car that pulled up. I couldn’t see her properly, but I guessed her to be in her mid-forties and, judging by her Mercedes, a wealthy woman. It wouldn’t surprise me if this was his aunt making a booty call.

I waited another five minutes, slipped off my underwear, straightened my skirt, and walked over to the front door. When Brian opened the door, he excitedly slammed his body into mine in a firm hug and said, “You’re back!”

I sure was, and I was in for another night of countless sex with a hot, preteen boy.

The end

Copyright 2024 – Jason Crow
All rights reserved

Hoc videre posset altera pars

P.S. Are you interested in the process of how I created images?? Here’s a link to a couple of the images that didn’t make it.