Hey readers, here's a little note about me and my story :) I'm 18 right now, writing this story as a freshman in college about something that happened last year. This first chapter is 100% true, but I plan on writing some more about what I wish had happened during the sleepover. Chapters 2 and onwards have been written and are much spicier >:)
Feel free to email me with any thoughts, comments, or whatever else!
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Chapter 1: Steamy Night
Sleepovers have always been fun for me. I never really had them growing up, my first one was in middle school where I had barely any friends, and my second was in my sophomore year of high school. But more recently, once things started opening up from COVID after a long long wait, I have been going to more than ever.
I should give some backstory about myself. My name is Henry. Writing this, I recently graduated high school and am going to community college as a freshman. Most of what happens in this story, however, was during my senior year of high school when I was 17.
I'm tall, about 6'1". I'm also super skinny only weighing 130-140 pounds. I'd say I'm fairly cute, my eyes are hazel with very long lashes. I'm over half Italian which made me much hairier than I wish I was, but I trim all my body hair to be very short. My cock is 6.1", completely straight, uncut with a normal thickness.
I'm pretty much only into twink-looking guys, finding people 2ish years younger than me is generally the most attractive. At 17, I would find hot someone at 15, maybe 14 if they were more mature, all the way up to 18. This is the age group that most of my friends are, the youngest being a sophomore, and a few juniors, but most are seniors like myself.
I haven't had much experience with relationships. I was obsessed with one guy for multiple teen drama-filled years, and eventually, a few months after this story, I got into a sweet relationship with him until he moved away. The furthest I've gone sexually is him touching my dick during a friend hangout in our friend's bed- we just laid there under the covers, horny, playing with each other's dicks. But that was it, we didn't even get to finishing. I was definitely (and still am) a virgin (not kissless anymore, fortunately), and around this time I was horny, like, all the time.
Sleepovers, and by extension, sleep play, were a different level of horny. I don't notice myself getting especially hard while sleeping at home alone, but whenever there is anyone remotely cute in my room or bed, I am hard for hours and hours- pretty much all night long. The first time I noticed this was when I shared my bed with my friend Jacob when he was 15 and I had just turned 17. My platonic best friend was also in the bed putting me in the middle and getting us closer together, and something about being so close to Jacob made me harder than normal.
Through the night I was tranced in a half-sleep, half-horny version of myself. I imagined a great idea would be to increase my pleasure somehow. While he was deeply asleep, I would inch closer and closer with my hands and my body until I was pressed against him, both lying on our backs. I turned to face him with my boner through my shorts mere inches from my body. I rested my hand against his arm, continuing and placing it on his chest. I essentially cuddled him, my cock throbbing in my pants but making no contact. I got too nervous to do anything else and just fell asleep with my arm cradling his chest and feeling his body inches away from my own.
During another group sleepover, I shared my bed with Jacob again. But instead this time it was just us two in my bed, my friends finding other spots to sleep more comfortably than 3 people sharing my queen bed. That night, being turned on so hard from our last sleepover, my brain told me to do so many things, however, my body wouldn't let me. I didn't feel like I could get that close to him even if he was asleep. If somehow Jacob woke up, there wouldn't be the excuse of a cramped bed to ease the awkwardness.
There was one upside to the increased space, and that was my ability to move around. More specifically, I was able to touch and play with my bulge without the fear of someone waking up from the movements. I really enjoy edging myself, so my goal with these sleepovers isn't to cum fast but to spread and build up the pleasure so that in the morning when they leave, I can rip off my clothes and spray my pent-up cum on myself.
This being my second sleepover though, I was experimenting. With my pleasurable bulge in my shorts, I very slowly scooted close to him, my hand inches away from his warm torso under the covers. Irrationally terrified of waking Jacob up, I didn't want to move if I could help it, but my cock was throbbing with the cute body next to me. My other hand inched closer to my bulge under the covers, finally wrapping my hand around my shaft through the fabric.
Holding my cloth-covered cock with my right hand, I got my thumb and started very slowly and gently rubbing the tip in circles, my right hand still barely brushing against Jacob who was sound asleep. My body was probably 8 inches away from him but here I was, my finger going up and down and around the very tip of my diamond-hard cock through my shorts. I noticed it getting stickier as I went on, precum filling the fabric. While my body wanted me to moan, I had to quietly control my breathing to avoid waking my friend beside me. In my dark, silent, and warm room, I quickened the circles of my thumb, going around and around feeling the pleasure build and build. I couldn't stop breathing faster and heavier, my body mildly squirming from more pleasure than I had felt in months. I barely started rubbing up and down my shaft through my shorts continuing the circular motion with my finger.
The slight movement of my foreskin up and down combined with the friction of the fabric on my head was too much for my highly horny head. With a quiet grunt and a few heavy breaths, I came loads in my underwear inches from Jacob sleeping. I could feel a few drops seep through the two layers of tight fabric onto my hand, most of my many shots of cum ending up in my underwear spreading around my cock area. I looked over at Jacob, still fast asleep, his cute warm body still radiating towards mine.
How I wish I could cuddle him and grind against him, maybe stick it in him- I just knew it wouldn't happen but it didn't matter. I was in bliss from my edged orgasm inches from such a cute guy, having barely touched my dick through layers of fabric but still causing myself to explode. My cock began to deflate, the movement spreading the warm thick cum throughout my underwear as I drifted to sleep. Jacob, completely unaware of what had happened, continued lying there with his short, soft snores.
The next morning, my underwear was still moist. There was a strong smell of cum emanating from under my and Jacob's bedsheets. I was worried Jacob would smell it when he woke up and I momentarily freaked out, but regardless I noticed I was getting hard. I got up and cleaned the few non-soaked drops of my goo from my undies with some toilet paper, trying to air out my comforter of the moist smell before Jacob awoke. Minutes later when he finally did wake up I could still smell my pleasure from the night before but it was significantly better and he didn't say a word. He was completely clueless about what had happened and I intended on it staying that way. I let him and my other friends go within about an hour, awaiting the time when I could jerk off again from the total hotness of that entire night. I just couldn't wait until the next sleepover where I could continue bringing myself into bliss.