Steve the Crossdressing Cat Lover
- 2 years ago
- 9
- 0
Steve Sleeps Over free porn video
This story takes place about 4 years ago. Steve was 15 years old back then. He has brown hair and glasses, and in general looked like your stereotypical nerd. He was thin though, and his ass looked like it could have been on a girl. That was possibly an exaggeration, but you get my point. At this point he have been friends since 4th grade (by this time we were sophomores in high school), and throughout middle school I thought I had something of a man crush on him. Then I got a girlfriend in high school, and thus convinced myself that the “man crush” thing was just a phase, but even then I would have strange fantasies involving him. Well, apparently there was more to this “man crush” thing than I originally thought, and I learned this when I invited him to a sleep over.
This was my first sleepover with anyone, and 16 years old (my age) does seem like a late time for that to happen, but we were friends so when I invited him he obliged willingly. The night started off pretty normal; some pizza, videogames, and late night TV. It’s around night time when ideas started popping into my head…. I offered Steve some hot chocolate (this was in January, which I should have mentioned earlier), and he obliged to that as well. I made us both a cup while he stayed downstairs. I made his cup extra large though, and poured a shitload of Nyquil into it. No, it’s not ketemine or rufies, and I’m starting to wish I had some of that. He drank his very quickly, but mentioned how bitter it seemed to taste to him. Oops.
Around 1am most of the shows on TV started to suck and we both decided that it was time for bed. I don’t know how long it actually took him to fall asleep, but I waited at least a half hour laying on the floor counting to myself until I was reasonably sure he was fast asleep. Oh yeah, he was sleeping on the couch while I was on the floor, a pretty important detail. When I lifted my head up and looked at him, he was lying on his stomach, wearing a white tee shirt and light blue pajama pants. He had only one blanket covering him, and it was a pretty small one too. I poked him in the shoulder gently, whispering “toooom, toooom, you awake”? No response, and I poked him a little harder. The only movement out of him was his rhythmic breathing. Perfect. I quietly walked upstairs to the kitchen and pulled out a pair of scissors and a flashlight. Back downstairs, I kneeled at the couch and slowly lifted up his blanket. Even in the dim moon light I could clearly see the plaid blue pattern in his pajama shorts and the wrinkles and folds of the fabric.
I pinched a piece of fabric right between his beautiful asscheeks, lifted it up, and snipped off a piece about two centimeters long and maybe half a cm wide. By now my hands were trembling almost uncontrollably. I lifted up the flashlight and peered into the hole I just made. To my absolute delight, I learned that Steve doesn’t wear anything under his pajamas. Still holding the flashlight in one hand, my other hand rested firmly on his left asscheek and spread it away from his other one. Now I could see just how accurate my cut was, and very accurate it was. I could just barely see the top part of his rosebud through the hole, though it was slightly obscured by dark hairs. Against my better judgment, I dropped the flashlight and, since I already knew where everything was, used my free hand to slide an index finger into the pajama hole, between his asscheeks, and rubbed it against his asshole. It felt very warm, and a little moist (as to be expected). I could feel his sphincter muscle contract from my touch, but even then his breathing remained constant.
I was almost in a state of euphoria. I stuck my tongue into the hole of the fabric and poked around. I heard a very short, quiet moan from him, but otherwise nothing happened. I pulled the blanket back over him, walked upstairs, and got a bottle of dish soap. I squired a little onto my finger and rubbed it against my own asshole, just to make sure it wasn’t some citrus shit that would burn him. Back downstairs again, I slid my now well lubed finger back against his asshole and, very carefully, started wriggling it back and forth, with each repetition sliding a tiny bit further into his butthole. He was constantly tightening up, loosening up, then tightening again. But, as usual, his breathing didn’t change. I got as far as my second knuckle until he began to stir. He clumsily turned onto his back, but I was too terrified to move. When he settled back down after a few seconds, he was laying on my wrist and hand, with my finger still up his ass. Carefully I slid my finger out and my hand from beneath him.
By now the blanket had also pretty well fallen off of him, and I could see a general outline of his crotch. The waistband of his pajama pants was very tight, but the fabric itself was quite loose. He was also flaccid, so there was no huge bulge in the fabric for me to marvel at. With the flashlight back in my hand, I peered at his general pelvic region to find anything like a button or a fly opening. I shielded part of the light with my free hand so it wouldn’t shine in his face and wake him up. I found a button opening in the front of his pajamas, but it seemed very high up. I dropped the flashlight and picked up the scissors and cut off the button (why I didn’t simply unbutton it I still do not know). Now, with my free hand I slid my finger into his fly and down, poking through pubic hair and the top of his circumcised dick. Apparently he sleeps with his cock in the “up” position, much like myself. It was a marvelous feeling, but I wanted more. I put the fabric around his fly into the scissors and cut downward, making the fly about twice as long as it used to be. And yes, I was very careful so I wouldn’t slice is cock in half. That would have pretty well ended our friendship right then and there.
I could fit my entire hand into his fly. I adjusted his crotch so that his member would be plainly visible in the moonlight and, a few seconds later, in my flashlight . I slowly stroked and squeezed him until he became extremely hard. His cock was about 7inches long when hard, bigger than mine (don’t laugh at me). Temptation overtook me, I kissed the head of his member gently, then licked it, then I embraced all 7 inches into my mouth with lust. It was a tad salty, and I could feel his pulse against my tongue. Still he seemed to be fast asleep. For what seemed like an eternity later, he burst and much to my sudden horror, seemed to wake up. I got one full squirt of his cum into my mouth. As I pulled back in panic his second squirt got me in my face. His awakening seemed to have been a dud though, he grumbled to himself in his sleep, jostled around a bit back onto his stomach, and was quiet once more.
Once my heartbeat slowed back down to normal I decided that the night was a success and fell to sleep. The next morning I woke up earlier than he did, finding him still lying on his stomach. Entertaining the idea of a second round, I poked him in his shoulder again. To my disappointment, he woke up this time. “Good morning Steve”. “Good morning (you don’t need to know my name)”. After a very brief and meaningless morning conversation, he got up and walked to the bathroom to change. As I watched him leave I could still see the work I did to the back of his pajamas, which made me start to worry again. What if he noticed that something had clearly changed to his attire? It was a very real and worrying possibility, but thankfully he didn’t appear to notice (or didn’t think anything of it). He walked back out of the bathroom fully dressed. The rest of the morning was spent playing more games until his parents picked up a little after noon.
Ever since that night I have become a hardcore somnophiliac, performing similar “activities” with my younger cousin and some of my sister’s friends when she had sleepovers. My cousin sleeps like a rock, you could do pretty well anything to him (and I have) and he won’t move a muscle. Most of my sisters friends are disappointingly light sleepers, although there was one who I managed to stick my whole index finger into her asshole as well, albeit very, very slowly and carefully. My trusty flashlight and scissors have yet to let me down… and I damn well hope they never do.
*****As you could have probably guessed, “Steve” isn’t the character’s real name. This is based on a true story. Have a problem with that? Fuck you, there’s crap on this site that’s shitloads worse than this. -->
This was my first sleepover with anyone, and 16 years old (my age) does seem like a late time for that to happen, but we were friends so when I invited him he obliged willingly. The night started off pretty normal; some pizza, videogames, and late night TV. It’s around night time when ideas started popping into my head…. I offered Steve some hot chocolate (this was in January, which I should have mentioned earlier), and he obliged to that as well. I made us both a cup while he stayed downstairs. I made his cup extra large though, and poured a shitload of Nyquil into it. No, it’s not ketemine or rufies, and I’m starting to wish I had some of that. He drank his very quickly, but mentioned how bitter it seemed to taste to him. Oops.
Around 1am most of the shows on TV started to suck and we both decided that it was time for bed. I don’t know how long it actually took him to fall asleep, but I waited at least a half hour laying on the floor counting to myself until I was reasonably sure he was fast asleep. Oh yeah, he was sleeping on the couch while I was on the floor, a pretty important detail. When I lifted my head up and looked at him, he was lying on his stomach, wearing a white tee shirt and light blue pajama pants. He had only one blanket covering him, and it was a pretty small one too. I poked him in the shoulder gently, whispering “toooom, toooom, you awake”? No response, and I poked him a little harder. The only movement out of him was his rhythmic breathing. Perfect. I quietly walked upstairs to the kitchen and pulled out a pair of scissors and a flashlight. Back downstairs, I kneeled at the couch and slowly lifted up his blanket. Even in the dim moon light I could clearly see the plaid blue pattern in his pajama shorts and the wrinkles and folds of the fabric.
I pinched a piece of fabric right between his beautiful asscheeks, lifted it up, and snipped off a piece about two centimeters long and maybe half a cm wide. By now my hands were trembling almost uncontrollably. I lifted up the flashlight and peered into the hole I just made. To my absolute delight, I learned that Steve doesn’t wear anything under his pajamas. Still holding the flashlight in one hand, my other hand rested firmly on his left asscheek and spread it away from his other one. Now I could see just how accurate my cut was, and very accurate it was. I could just barely see the top part of his rosebud through the hole, though it was slightly obscured by dark hairs. Against my better judgment, I dropped the flashlight and, since I already knew where everything was, used my free hand to slide an index finger into the pajama hole, between his asscheeks, and rubbed it against his asshole. It felt very warm, and a little moist (as to be expected). I could feel his sphincter muscle contract from my touch, but even then his breathing remained constant.
I was almost in a state of euphoria. I stuck my tongue into the hole of the fabric and poked around. I heard a very short, quiet moan from him, but otherwise nothing happened. I pulled the blanket back over him, walked upstairs, and got a bottle of dish soap. I squired a little onto my finger and rubbed it against my own asshole, just to make sure it wasn’t some citrus shit that would burn him. Back downstairs again, I slid my now well lubed finger back against his asshole and, very carefully, started wriggling it back and forth, with each repetition sliding a tiny bit further into his butthole. He was constantly tightening up, loosening up, then tightening again. But, as usual, his breathing didn’t change. I got as far as my second knuckle until he began to stir. He clumsily turned onto his back, but I was too terrified to move. When he settled back down after a few seconds, he was laying on my wrist and hand, with my finger still up his ass. Carefully I slid my finger out and my hand from beneath him.
By now the blanket had also pretty well fallen off of him, and I could see a general outline of his crotch. The waistband of his pajama pants was very tight, but the fabric itself was quite loose. He was also flaccid, so there was no huge bulge in the fabric for me to marvel at. With the flashlight back in my hand, I peered at his general pelvic region to find anything like a button or a fly opening. I shielded part of the light with my free hand so it wouldn’t shine in his face and wake him up. I found a button opening in the front of his pajamas, but it seemed very high up. I dropped the flashlight and picked up the scissors and cut off the button (why I didn’t simply unbutton it I still do not know). Now, with my free hand I slid my finger into his fly and down, poking through pubic hair and the top of his circumcised dick. Apparently he sleeps with his cock in the “up” position, much like myself. It was a marvelous feeling, but I wanted more. I put the fabric around his fly into the scissors and cut downward, making the fly about twice as long as it used to be. And yes, I was very careful so I wouldn’t slice is cock in half. That would have pretty well ended our friendship right then and there.
I could fit my entire hand into his fly. I adjusted his crotch so that his member would be plainly visible in the moonlight and, a few seconds later, in my flashlight . I slowly stroked and squeezed him until he became extremely hard. His cock was about 7inches long when hard, bigger than mine (don’t laugh at me). Temptation overtook me, I kissed the head of his member gently, then licked it, then I embraced all 7 inches into my mouth with lust. It was a tad salty, and I could feel his pulse against my tongue. Still he seemed to be fast asleep. For what seemed like an eternity later, he burst and much to my sudden horror, seemed to wake up. I got one full squirt of his cum into my mouth. As I pulled back in panic his second squirt got me in my face. His awakening seemed to have been a dud though, he grumbled to himself in his sleep, jostled around a bit back onto his stomach, and was quiet once more.
Once my heartbeat slowed back down to normal I decided that the night was a success and fell to sleep. The next morning I woke up earlier than he did, finding him still lying on his stomach. Entertaining the idea of a second round, I poked him in his shoulder again. To my disappointment, he woke up this time. “Good morning Steve”. “Good morning (you don’t need to know my name)”. After a very brief and meaningless morning conversation, he got up and walked to the bathroom to change. As I watched him leave I could still see the work I did to the back of his pajamas, which made me start to worry again. What if he noticed that something had clearly changed to his attire? It was a very real and worrying possibility, but thankfully he didn’t appear to notice (or didn’t think anything of it). He walked back out of the bathroom fully dressed. The rest of the morning was spent playing more games until his parents picked up a little after noon.
Ever since that night I have become a hardcore somnophiliac, performing similar “activities” with my younger cousin and some of my sister’s friends when she had sleepovers. My cousin sleeps like a rock, you could do pretty well anything to him (and I have) and he won’t move a muscle. Most of my sisters friends are disappointingly light sleepers, although there was one who I managed to stick my whole index finger into her asshole as well, albeit very, very slowly and carefully. My trusty flashlight and scissors have yet to let me down… and I damn well hope they never do.
*****As you could have probably guessed, “Steve” isn’t the character’s real name. This is based on a true story. Have a problem with that? Fuck you, there’s crap on this site that’s shitloads worse than this. -->
Lynne
- 28.03.2022
- 10
- 0
