Date: Sun, 7 Jun 2020 19:04:35 +0000 From: Valerius Catullus Subject: A Different Sort of Sleepover (Bisexual, Transgender, Young Friends, High School) A different sort of sleepover Billy and I had been eagerly awaiting this sleepover for a while now. It was always a welcome break from the usual routine and we always found fun things to do at each other's houses. My house was alright but I preferred his because of the way it was set up. It was on a wooded hill, set back from the road, with lots of places to hide behind boulders and trees. Not to mention the house with its odd configuration of side hallways, small cluttered rooms and closets with dozens of secret nooks in them. We had been the closest of friends since the second grade and had spent all those summers and breaks playing games, exploring both houses and swimming in the lake at the park down the road from his house. His parents always took me along on family outings and we had even taken a boy scout trip to Washington together once. We played soccer and baseball and the occasional video game, and expounded on any subject our young minds came up with, letting our thoughts flow and wander where they would. But in the past year or so, our carefree outings and wanderings had taken on a different tone. The summer afternoons spent at the lake in the park now focused our gazes on the shapes and exposed skin of our fellow swimmers and our long discussions were now done in voices that had dropped in register. The need and pressure in our bodies had increased to the point of taking up most of our attention and I noticed he just as often as I hid a hardon beneath the murky waters of the lake. What I had not told him was that even as I hungrily watched the round asses and small perky breasts of our female classmates bounce beneath the tight, wet fabric of their bikinis, I also wondered what it would be like to touch Billy for more than just an instant as I rarely had dared. His swimming trunks were slightly small on him and allowed me to get a good view of the shape of his ass and a good idea of the bulge he had in the front of it. His supple body was smaller and more graceful than mine even though he had started school late and was actually a year older than me. This time his parents had been involved in some community cleanup project and were exhausted by the time we got back to the house. Billy's douchebag older brother Carl had borrowed one of their cars to go party with his friends overnight somewhere. His older sister Debbie was cloistered in her room with her friend Jen. Both girls were the objects of my wet dreams and fantasies but having them out of the way meant we had the run of the entire downstairs once his parents went to sleep. There was a back room that functioned as a sort of game room/TV room but it was rarely used and had piles of old furniture and boxes of books and pictures in storage. That made it an ideal place to hide. We sometimes had sleepovers there but Carl was enough of an annoyance to make that rare. Now that he was out we dragged every spare blanket, pillow and cushion down there and hung out for a while watching TV. We were talking about rumours we had heard of which girls would do more than kiss on dates. We agreed that most of our fellow Middle School students who claimed to have gone past second base were probably full of shit. That led us to speculate on what would happen when we got to high school. "I heard some girls have sleepovers where they get naked" I said. "It's true!" Billy answered, his blue eyes lighting up, "I've seen it" "Bullshit. Where the hell would you have gotten close enough to any high school girls to know?" I retorted, sure he was lying. "Well...my sister for one. She has sleepovers all the time. They usually wear pajamas but I've seen it twice now where she and Jen were completely naked running from the shower to the bedroom. Jen grabbed Debbie's ass. I wonder if they fuck?" He was blushing all the way to the roots of his blonde hair and I noticed his shorts, the only thing he was wearing, was tented by what looked like a sizable erection. My cock was rock hard too, thinking about his sister with her light brown curly hair and grey eyes smiling as she ran nude down the hall, smiling over her shoulder as a hand reached out to grab her, her more full figured blonde friend, chasing her with mischief in her eyes. But what would happen after that? "I don't think so." I said. "How would they ever satisfy each other? They don't have the right equipment." "Well I've seen them kiss before. And Debbie grabbed Jen's tit once. Maybe they rub each other's pussies with their hands." The thought of that was somehow disappointing. What a waste it would be. I wished it could be me with one of them and my dick was painfully hard, hidden beneath the sheets. I slipped my shorts and boxers off in the dark, quietly to get some relief. "No man, girls need dick. I bet I could help with that. And maybe they were just kissing to practice. Ellen and Leslie do that. They told me." Billy scoffed at that "Well they have nice asses but almost no boobs. High school girls can get any guy they want. And I've caught them giggling about rubbing each other with this". He showed me a little yellow jar with a blue label that read Vaseline with some sort of jelly inside. I took a boy and then tried to wipe it off on my leg, finding the gliding, lubricant feel of it strangely exciting. I turned over on my stomach, pressing my hard-on into the sleeping bag and sheets, quietly grinding my hips as I told him that rubbing each other like that seemed a bit gross when they could get fucked by anyone they liked. Billy complained of the summer heat making his clothes stick to his skin. Something inspired me to tell him in a nervous voice "You know it's more comfortable without any clothes. I sometimes take mine off. Like now. It's just too hot and humid tonight." "Really? Are you telling the truth?" He asked hesitantly. "See for yourself" I said, and grabbed his hand, which I then guided under my sheet. I slid his hand from just under my arm slowly down my side to my thigh, then back up, lingering on my naked hip. It sent a thrill through my body and an electric tingle through my cock. "Wow. You really are nude" he said in wonder. Maybe it is worth a try. I heard him fumbling in the dark with his own clothes, and then he kicked off the sheet. "I'm still hot and sticky. Maybe we should lose the sheets". He then kicked off his and pulled mine down. He ran his hand back up from my thigh to my waist, then softly slid it over to my ass and squeezed. "You seem cool and dry after being naked longer. Maybe the girls are onto something after all." As he said this, he rubbed my ass cheeks and slowly explored the crack of my ass with his fingers. I spread my legs and raised my hips slightly to make it easier for him. Having his fingers probing at my entrance was exhilarating but I found myself wanting to turn and take pressure off my cock. I turned to face Billy, and said "We should have started having girl sleepovers earlier. It looks like we have a lot to learn from them.", I then moved in and touched my lips to his. He seemed slightly surprised, but a moment later he kissed back. He murmured something about practice and then parted my lips with his tongue. I eagerly kissed back and entwined my tongue with his as I ran my hand up his thigh to his hip, then felt for his package. His stiff cock was thicker and longer than mine and felt silky smooth and warm in my hand. I wondered if it was bigger because at 14 he was a year older than me? He moaned into my mouth as I stroked it and started grinding into me. I moved my hand to his heavy ball sac and caressed it as our cocks touched deliciously. It was almost too much, but then he suddenly pulled back and started kissing down my neck to my chest. I writhed and submitted to his caresses as I gave myself to the pleasure. Somehow I ended up turned with my back to him as he kissed my neck. I felt him pull me close and grind into me as I pushed back into him and opened my legs. I felt his thick cock pushing against my ass and I relaxed to open to him. I squeezed and he moaned in pleasure. He pushed and I could feel the head of his dick pushing against my sphincter. Part of me feared his large tool and part of me ached for it. I wondered if this was how a girl felt just before a boy took her. He pushed but could not quite enter me. I eagerly squeezed and relaxed on him and he kept grinding on me until I felt him spasm and heard him groan. Then I felt his hot seed shooting between my asscheeks and run down my leg. I turned to kiss him and then noticed the jar of Vaseline. I mentioned to him that we had not tried that yet, and we rubbed it on each other's cocks. His was very sensitive and at half mast but started to come back to life as I rubbed it. Mine was painfully hard as I lay him on his back and started to push on his cheeks as he wrapped his legs around me. Just then, we heard laughter and both jumped in shock and fear at being caught. "Don't stop on our account. I always know my brother was a little bitch." Debbie was there with a bemused look on her face, her grey eyes dancing, her curly brown hair wild around her face. She was naked to the waist, with her small pert breasts exposed and large puffy nipples standing at attention. She had one hand in her panties and was wearing nothing else. Jen was next to her, wavy blonde hair glinting in the not quite light. Her much fuller breasts swaying free and her own hand under her short skirt. A hungry smile was on her full lips. "Debbie! What the hell! How long have you been there?" Billy said as he nearly jumped. "We saw and heard everything. " Said Jen. "And we're really enjoying the show so keep going". "Yes, Don't stop or I'll tell mom and dad everything". Both girls were gorgeous and obviously comfortable with sex and I was already so horny I just pushed into Billy, expecting an ass job like I gave him. Instead, Jen got behind me and started kissing me while she grabbed my dick and pushed me deeper into him. "His pussy needs to be penetrated. Don't stop now" She said, and I felt his sphincter resist for a moment, then open to me as I slammed in. He had gone soft and to my surprise his sister took him in her mouth ad sucked him back to hardness. Jen was still kissing my neck and I could feel her breasts on my back. She wriggled out of her skirt and panties and then pressed herself to me again. To my shock, I felt a hardness pressing against my ass, warm and smooth. Debbie smiled at my surprise. "You were right. I would never touch another woman's pussy. Vagina is gross unless it's mine. And I wouldn't let any girl touch me because they can't satisfy me. But Jen is not just any girl. She's better equipped. As she said this, Jen was lubing my ass and her cock and now she pushed against me as I slid back into Billy. I felt her push through, aided by the Vaseline and into me with a sudden thrust. I gasped at the sudden feeling of fullness and stopped moving while all the way inside Billy, adjusting to it all. Billy was hard again and Debbie carefully straddled him. She put some lube on his cock, pulled her thong aside and sat on his dick, taking him in her ass and then started rocking back and forth. She left her pussy covered but reached under them and started working it furiously with her hand. As Jen fucked me, I felt a new sort of pleasure deep inside. I hungrily rocked into her, adjusting to her rhythm as I fucked Billy as hard as I could. He screamed in pleasure as his older sister bounced on his cock and made out with me. I squeezed Jen's dick with my ass and Debbie's tits with my hands while I made love to Billy. I remember wishing it would last longer but then I heard a little whimpering sound from behind me and Jen's penis spasmed as she came and filled my ass with her cum. She leaned on me, spent but with her cock still inside me as I fucked harder and felt Billy's ass squeezing me over and over again in rhythm. I was kissing Debbie and felt her orgasm go through her as Billy came inside her and she rubbed herself. She moved off him and I could see cum dripping from her ass as I lost all control and shot jet after jet of hot jizz into my friend's ass. As we lay spent on the floor, three of us naked with our cocks spent and softening, and the other still wearing her soaked panties, all glistening with sweat, Debbie swore us to secrecy about the whole thing but promised we would have a lot more sleepovers from now on. She was true to her word and that day was just the beginning of our adventure. From that day on my three lovers were a major part of my life.