#Teen #Threesome #Tween #Virgin
I’ve had a lot of crazy experiences over the years and decided to write about them to share.
My name is Jake and this was in the early 2000s. My summer had been a rollercoaster. Just when I thought things were going okay, my mom split with her boyfriend and we had to move into a trailer park. The trailer was a decent size, but it was definitely a downgrade from the house we’d been living in. Being the new kid in the neighborhood, I didn’t exactly make friends quickly. Most of the time, I was stuck alone, especially with mom working long hours at the hospital. She felt sorry for me, so for my 14th birthday just before school started, she got me a computer. That little box of circuits and lights became my ticket out of boredom and into the world of online gaming and, before I knew it, internet porn. It filled the empty hours after school, becoming my secret sanctuary from the mundane.
Shortly after the school year kicked off, my mom started carpooling with a neighbor, a single mom named Kristen, who had a daughter, Stephanie. She was 11, a few years behind me in the 6th grade and at the same middle school as me. She apparently had it even rougher than me, living in a place that was falling apart. So, Kristen started leaving Steph with me after school. I wasn’t thrilled at first, thinking it would mess up my “me time,” but she mostly kept to herself, heading to the bathroom to change into her after-school gear and then either watching TV or playing with friends outside. I’d lock myself in my room, indulge in a little porn and pleasure, and then get to my games.
But one day, our routines collided. I had to make a mad dash to the bathroom and accidentally barged in on Steph while she was in the middle of changing into her swimsuit. She was naked, and the sight of her took me by surprise. We both froze, and I stumbled out, feeling like the world’s biggest creep. I went to the other bathroom to do my business, and when I came out, she was already gone outside with friends.
She was really the first girl I had seen naked in real life that I could remember and the image of her nude body was burned into my mind. I went to my bedroom layed on the bed, closed my eyes and started stroking my cock. I had the radio going and didn’t bother locking the door since nobody was home anyway. I was really getting into it when I though I heard a noise. I opened my eyes and saw Stephanie in her swimsuit standing in the doorway staring at me. I screamed at her to get out and she ran down to the hall half crying.
I felt bad so I went to the living room and she was sitting there in tears just staring at the TV. I sat down next to her and apologized. I told her she can’t tell anyone what she saw and she agreed. A few minutes later she asked what I was doing. I told her I was making myself feel good. She said she thought I was sleeping until she saw me playing with myself. I told her I was thinking about girls when I do that. She wanted to know what kind of girls and I told her I was thinking about seeing her naked. She had a look of shock on her face and just kind of ignored me. After a few minutes she asked if I was mad that she interrupted what I was doing. I just said I didn’t get to finish. She told me I could go finish if I wanted and she wouldn’t bother me. I decided to try my luck and said I forgot what you look like naked already. She said, “Oh okay,” and went back to looking at the TV.
A few more minutes went by and she said, “I can show you again if it makes you feel better.” I knew this was my chance. I said okay, but let’s go to my room. We got to my room and I laid on the bed. She just stood there looking at me obviously nervous. I told her she could take off her swimsuit and sit in my chair. She hesitantly took it off and sat down. I took off my shirt and pulled out my cock and started at her body while stroking it. Her eyes got wide and she just started at my cock. I told her she can make herself feel good if she rubs herself too. She awkwardly started touching and rubbing herself obviously not knowing exactly what to do but you could see her jerk every once in a while when she’d hit a spot. I think she was too nervous to enjoy herself. After a couple minutes, I shot a huge load all over my stomach. I grabbed a sock and cleaned it up. She asked me if I was done, I said yes. She quickly grabbed her swimsuit put it on quick and ran back out to the living room. By the time I got back out there, she was outside with friends. I didn’t know what to think at that point.
The next day we were back to our usual routine, she went to the bathroom to change and I locked myself in the bedroom. After a couple minutes I heard a soft knock on my door. I opened it and Stephanie was standing there. She asked me what I was doing. I said working on my computer. She said, “Oh okay.” I went to close the door and she says, “Wanna do what we did yesterday?” I couldn’t say yes fast enough. She came in my room and I laid on the bed, she stripped down and sat in my chair. As soon as I came, she grabbed her clothes, put them on and left.
This pattern continued through the winter for most of the school year. After school, I’d wait for the knock on the door, my heart racing. We never talked about it outside of the room, but when we were there, it was like we had our own little secret world. She’d ask if she could change in my room, and I’d eagerly say yes, watching her peel off her school clothes and sit in my chair. Each time, she touched herself a little more confidently, and I could see the pleasure growing on her face. It was weird, but also kind of amazing, like we were discovering something together that no one else knew about.
But one day, about a month before school was about to let out for the summer, everything changed. Steph got off the bus with her friend Maddy. Maddy was a redhead a year older than her, and she had a body that had already blossomed into something that drew the eyes of the boys in the trailer park. She was from the rougher side of the trailer park, where kids grew up fast and didn’t always follow the same rules as everyone else.
When we got inside, Steph looked at me with a mischievous spark in her eyes, something I hadn’t seen before. “Jake,” she said, “I told Maddy about us. She’s really curious, and I think she’d like to try it too.”
My heart skipped a beat. I pretended like I didn’t know what she was talking about, playing dumb. “What do you mean?” I asked, trying to sound as casual as possible.
“You know,” she giggled, her cheeks flushing a shade of pink that was almost as red as Maddy’s hair. “What we do after school.”
Maddy looked at me with a mix of curiosity and challenge. I couldn’t believe it. My mind was racing with a million thoughts, but mostly, I was trying to figure out how to get out of this without it turning into a disaster. “I don’t know what you’re talking about,” I said, trying to sound as nonchalant as possible.
“Come on, Jake,” Maddy said, her voice dripping with a knowing smirk. “Steph told me all about it. She said you guys watch each other…you know…do stuff.”
My mind was racing. I didn’t know if I should be freaked out or flattered. But the look on Steph’s face, the way she was biting her lip, it was clear she wasn’t joking. I took a deep breath and sat down on the edge of my bed, trying to play it cool. To my astonishment, both girls started to peel off their clothes without another word. Maddy’s eyes never left mine, daring me to look away. I couldn’t. I watched as they both revealed their young, unblemished bodies to me.
They looked so different. Steph was petite, her skin a soft canvas of freckles and curves that were just beginning to form. Maddy, on the other hand, was more developed, with breasts that were already pushing against the fabric of her bra. They stood there, naked and unabashed, waiting for my next move. I felt a strange mix of excitement and fear, like I was standing on the edge of a cliff, not knowing if the rush of wind was going to push me over.
I got on my bed and started stroking myself, trying to act like it was just another day. The girls sat across from me, side by side in the chair, their legs slightly apart. They began to touch themselves too, their eyes on me as if they were watching a movie. I’d never felt so exposed, so…studied. My hand moved faster and faster, my eyes jumping from one to the other, trying to take it all in. Maddy’s hand moved in circles over her budding breasts, her nipples hardening under her touch. Steph was more tentative, her fingers gliding over her flat stomach and down to the little patch of hair between her legs.
Maddy leaned in, her voice low and sultry. “Is that all you guys do?” she asked, her eyes never leaving my cock. “Just watch?” My heart was racing so fast, I couldn’t even answer. But Steph, she was different. She looked up at me, a hint of something in her eyes I hadn’t seen before—curiosity, maybe even a bit of desire. “I’ve never actually touched him,” she admitted, her voice barely above a whisper.
Maddy didn’t wait for my response. She strutted over to the bed, her hips swaying with a confidence that seemed to have bloomed overnight. She took my hand and guided it to her own chest, her skin hot and smooth under my fingertips. Then she knelt down and took my cock in her hand, stroking it gently. The feeling was electric, and I couldn’t help but moan. She smirked up at me before leaning down and putting her mouth on it. The sensation was overwhelming, like nothing I’d ever felt before. It was like she was taking control, showing us both that she was ready to play this game.
Steph watched us, wide-eyed and still a little nervous. But as Maddy’s movements grew more deliberate, something in her expression changed. She slid off the chair and onto the floor, closer to us. I could see her hand sneak between her legs, her fingers starting to move faster as she watched. Maddy glanced over, catching her friend’s gaze, and then looked back up at me with a question in her eyes. I nodded, and she let go of my cock, moving aside so Steph could take over.
Steph’s touch was lighter, more tentative than Maddy’s. She looked at me for guidance, and I whispered, “It’s okay,” trying to reassure her. She started to stroke me, her hand shaking a little. I reached out and took her hand in mine, showing her the rhythm that felt good. She looked up at me, her eyes searching for approval, and I gave her a nod. With each stroke, she grew more confident, her hand moving more smoothly.
Then, she leaned in, her warm breath ghosting over my skin, and she took me into her mouth. It was clumsy at first, her teeth scraping against me, but she quickly figured out how to use her tongue. I moaned, unable to help it, my eyes rolling back in my head. She took me deeper, and I felt a thrill of excitement and fear mingling together. Maddy watched us, her hand moving between her own legs, her eyes glazed with arousal.
I could feel the pressure building, my balls tightening, and I knew I was going to cum. “I’m gonna…,” I warned her, but she didn’t stop. I came hard, spurts of cum filling her mouth. She gagged a little, and some of it spilled out, trickling down her chin. Maddy was there in an instant, her tongue darting out to lick it up, a grin spreading across her face like a devil who’d just been offered a soul.
Maddy pulled back, wiping her mouth with the back of her hand, and looked up at me with a glint in her eyes. “That was fun,” she said, her voice thick with the promise of more to come. Steph looked up at me, her hand still on my cock, and nodded in agreement, her cheeks still a rosy pink.
They both giggled, the tension in the room shattering like glass. It was weird, but it felt…good. Like we’d just shared some secret that no one else in the trailer park would ever understand. They started to get dressed, their clothes seemingly appearing out of thin air as they slipped into them like it was the most natural thing in the world. I watched, my heart still hammering in my chest, as they pulled their shirts over their heads and slid their shorts up over their hips. It was like watching a magic trick, except the trick was that two girls had just given me the best few minutes of my life.
The next day, it was just Steph again. She didn’t knock this time. She just walked into my room, a little more confident than before, and came straight over to the bed. She climbed up and straddled me before I even had a chance to get undressed. Her hand reached down and unzipped my pants, pulling out my cock. Then she leaned in and took me into her mouth, her eyes never leaving mine. I felt her warm, wet tongue on me and my hands instinctively went to her hips, holding her there as she started to move.
It was like she’d been practicing. Her movements were smoother, more deliberate. She sucked harder and took more of me in each time, her cheeks hollowing out as she bobbed her head up and down. I could feel my orgasm building, the muscles in my stomach tightening. I didn’t say anything, just enjoyed the sensation of her lips around me. It was like she was hungry for it, eager to make me feel good. And when I came, it was with a gasp, my whole body tensing up. She didn’t stop until I was completely drained.
Then she smiled at me, got dressed and left, just like that. This became our new routine. She’d come into my room, we’d both get naked, and she’d suck me off before getting dressed and going about her day. We didn’t talk about it, didn’t even look at each other differently outside of those moments. It was like it was our little secret, something that existed only in that space and time. This went on for a couple weeks until about a week before school was to get out for the summer.
Maddy got off the bus with Steph again, and she had that same look in her eyes as she had the first day she joined us. I could feel the heat radiating off of her, and it was clear she was eager to take things further. We went straight to my bedroom and closed the door. I was a little nervous about what she had in mind, but also incredibly turned on.
We all sat on the bed, looking at each other for a moment before we started to get undressed. The tension in the room was thick, and I could see that both girls were feeling it too. We began to touch ourselves, our eyes locked onto each other’s bodies. I couldn’t believe that this was happening again, but with Maddy here, it felt like the stakes were so much higher.
Steph started off by taking my cock into her mouth, just like she had been doing for the past few weeks. Her technique had improved, and it was clear she enjoyed the power she had over me. But as she was sucking me off, Maddy slid under her and began licking her pussy. I could feel Steph moaning with my cock in her mouth.
Then, just as I was about to cum, Steph pulled away, leaving me on the edge. Maddy looked up at me with a wicked smile. “My turn,” she purred, and before I knew it, she was straddling me, her wet pussy hovering over my erect cock. I didn’t have time to process what was happening before she lowered herself down onto me, taking me inside her.
The feeling was like nothing I’d ever experienced before. She was so warm, so tight, and she started to move, her hips rocking back and forth as she took charge. Steph looked up at me, her eyes wide with excitement, watching as Maddy began to ride me. It was like watching a porn scene unfold right in front of me, but it was real. Too real. I could feel the heat of her, the wetness of her, and the friction was driving me wild.
Maddy’s breasts bounced with each movement, and her red hair cascaded down her back as she leaned forward, her mouth finding mine in a hungry kiss. It was like she was claiming me, marking me as hers for the moment. And then she started to bounce faster, her breath hitching as she got closer to her own climax. I could feel it building inside her, and it was all I could do to hang on.
Steph watched us, her eyes wide with a mix of curiosity and arousal. She had never seen anything like this before, and it was clear she wanted more. But she knew better than to interrupt. This was Maddy’s show now. And what a show it was. Maddy’s movements grew more erratic as she approached her peak, her nails digging into my shoulders. And then she was there, her body convulsing around me, her pussy clenching tight as she came.
I couldn’t hold back anymore. I felt the pressure build, my balls tightening, and with a grunt, I came deep inside her. She threw her head back, her mouth open in a silent scream, as she felt me fill her with my cum. It was like a dam had broken, and all my pent-up tension and desire flooded into her. For a moment, we were one, our bodies joined in the most primal of ways. She collapsed on top of me, her chest heaving with the effort of her orgasm.
Maddy gave me a playful kiss, her eyes gleaming with mischief, and climbed off. She didn’t bother to clean up, just hopped off the bed and started to get dressed like nothing had happened. I watched as she pulled her shorts over her hips and tugged her shirt down, covering up the body that had just been displayed so brazenly. Steph was sitting there, her eyes wide, looking at us like she’d just seen a unicorn. She hadn’t said a word, but her hand was still between her legs, moving slowly.
I looked at her, my heart racing. I didn’t know what to say or do. This was all so new to me, and now it had gotten so much more complicated. But she just gave me a small, knowing smile. “Wow,” she said, her voice barely above a whisper. “That was…different.”
They both got dressed quickly, as if they’d done it a hundred times before. Steph’s eyes never left mine, and I could see the question in them. She was looking for some kind of reassurance, but I didn’t know what to give her. Maddy, on the other hand, was all business. She zipped up her shorts, tugged her shirt down, and flashed me a grin that was pure devilry.
“See you tomorrow, Jake,” she said, her voice dripping with innuendo. Then she turned and walked out of the room, her hips swaying like she was leaving behind a trail of fire. Steph followed, a little slower, her cheeks still flushed from the exertion. She paused in the doorway and gave me a shy smile before disappearing behind her friend.
The last week of school, Steph came over alone like usual. We didn’t really talk much about Maddy. Steph would come over, strip down, give me a blowjob, I would finish in her mouth and she’d change clothes then leave.
When summer vacation came, our mothers decided Steph would come over when they left for work and spend the day here. She wouldn’t have to stay inside all day, but at least let me know where she’d be. The first few days we continued our after school routine in the morning. She’d come over and wake me up after a long night of gaming, give me a blowjob and leave to go play with friends.
After about a week, on morning I asked Steph when she was going to invite Maddy over again. Steph told me that Maddy went away to stay at her dad’s for the summer.
Steph could tell that I was bummed out, and she looked at me with a mix of concern and curiosity. “What’s wrong?” she asked, her voice small. “You miss her?”
“It’s not just that,” I mumbled, trying to find the right words. “It’s just…it felt good, you know?”
Steph looked at me with a newfound curiosity, her eyes searching my face for answers. “What felt good?” she asked, her voice softer now.
I took a deep breath, trying to gather my thoughts. “You know,” I said, “when her and I…you know.”
Steph nodded, understanding dawning in her eyes. “We could do it if you want.”
My heart raced at her words. “Yeah,” I said, my voice hoarse with desire. “Let’s do it.”
We both stripped down, our eyes locked as we revealed ourselves to each other once again. The room was filled with the scent of our arousal, the heat of the early summer day making our bodies stick to the bed sheets. She climbed on top of me, straddling my waist, and I could see the hunger in her eyes as she took my cock in her hand. She was so much more confident now, so much more in control. She lowered herself onto me, and the feeling was incredible—like coming home to something that was always meant to be.
Her movements were slow and deliberate, her hips rocking as she took me all the way in. She bit her lip, her eyes never leaving mine, as she started to bounce. I could feel every inch of her, and it was like she was worshipping me with her body. I reached up to cup her breasts, feeling the weight of them in my hands, and she leaned down to kiss me, her tongue dancing with mine as we found a rhythm. It was like we were lost in a dance that only we knew the steps to.
I could feel myself quickly getting closer and closer to the edge, the sensation building until it was all I could think about. It might have only lasted a couple minutes but I came hard deep inside her.
As I lay there, trying to catch my breath, Steph gave me a knowing smile and climbed off me. She didn’t say anything, just got dressed with a casualness that made me feel like we’d been doing this forever. It was weird, but also incredibly hot. She pulled her shirt over her head and tugged her shorts up over her hips, her pussy still glistening with our combined juices. I watched her, unable to tear my eyes away, as she moved around the room, picking up her discarded clothes.
“I’m going to go play with my friends,” she said, her voice still a little shaky from our encounter then left.
After thinking about it, I was suprised at how easily I slid into her. (She later confided to me that her and Maddy had experimented before and played with different brushes and other things.)
The days stretched out before me, long and empty without the distraction of school. But at least I had Steph. We fell into a new routine, one that started with her slipping into my bed in the mornings and ended with her leaving to spend the day playing outside. We tried different positions—missionary, doggy style, even her on top—but it was always over quickly. It was like she had become a silent participant in my fantasies, letting me do what I wanted without much protest.
It was only a couple weeks into summer vacation when she suggested a change. She climbed onto the bed, looking at me with a hint of boredom in her eyes. “Do you want me to just suck you off today?” she asked, her voice devoid of its usual enthusiasm. I could tell she was just going through the motions.
I took a deep breath, feeling a twinge of disappointment but also a spark of something new. “No,” I said firmly, “I want to try something different.” She looked at me curiously as I pushed her back onto the bed and spread her legs apart. I’d been watching a lot of porn, and there was one thing I hadn’t tried yet—going down on a girl.
I leaned in, my tongue tentatively touching her clit. She gasped, her body arching off the bed. I licked and kissed her, exploring the folds of her young pussy with my mouth. She was so wet, so warm, and she tasted…sweet, like a secret garden that had just been discovered. I could feel her hips start to rock against me, her hands tangling in the bed sheets. Her breath grew ragged, and she started to moan, her body tensing.
It was like I had unlocked some kind of secret code, and suddenly she was alive with pleasure. She had never felt this way before, and it was all because of me. I licked and sucked, my tongue delving into her, feeling her walls tighten around me. And then, just as I was about to pull away, she started to cum. Her body trembled, her legs clamping around my head as she let out a high-pitched whine that was music to my ears. It was the most beautiful sound I had ever heard, and it made me want to do it again and again.
When she was done, she looked up at me with a mix of amazement and gratitude. “That was…wow,” she said, her cheeks flushed with color. I couldn’t help but feel a sense of pride, like I had just discovered the meaning of life. I climbed on top of her and slid my cock into her tight and incredibly wet pussy pumping her until I came.
This newfound skill of mine became our go-to move. Every morning, she’d come over, we’d make out for a bit, and then I’d go down on her until she screamed with pleasure. Only after she came would I allow myself to fuck her, filling her up with my cum. It was like a switch had been flipped in her head, and she was suddenly insatiable for more. She’d ride me, her legs wrapped around my waist, her nails digging into my back as she urged me deeper, her breath coming in short, sharp gasps. And every time she came, it was like watching a star explode, bright and beautiful.
But then, about a month before school started, everything changed again. Steph turned 12, and with it came her first period. She was scared, and so was I. We talked about it, but she didn’t want to risk getting pregnant. So we agreed to stick to oral, mostly. We would sometimes start out with sex and me finishing in her mouth. It was a weird adjustment, going from fucking like rabbits to just blowjobs and eating her out. But I could tell she enjoyed it, and that was all that mattered.
Her mother also decided that since she was 12 now, she could stay home alone, so she didn’t come over as often as she used to. It was like she was slowly pulling away from our secret little world. But she had her own life and her own friends.
Just before the school year was set to begin, my mother broke the news that she had managed to save enough for us to leave the trailer park and move into a proper house. The reality of our impending move weighed heavily on me, knowing that our secret rituals would have to come to an end.
We sold the trailer, and I watched as the place where I’d experienced some of the most intense moments of pleasure in my life was packed up and carted away. The day we moved, I saw Steph outside her trailer, watching us leave. I felt a pang of regret that we wouldn’t be able to continue our little game.
I started high school in a different district and never really saw Steph or Maddy after that.
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#Teen #Threesome #Tween #Virgin