Yeah, I had a mate like this*.
We grew up in the same neighbourhood, and when we were younger we went to the same school, but only ever hung out on weekends, after school, or if there was a house party with somebody we both knew. I guess looking back, we were friends by circumstance because our parents knew each other (both single mums, probably had a lot in common).
Whenever his mum worked nights, he would stay over at mine, sleeping on a roll-out trundle next to my single bed. We would stay up late talking shit, and it was during one of these late night chats that I told him I might be bi. He dated heaps of girls all through school, including some of my friends, and by all accounts, was 100% straight. I don't know what his mums roster was, but he'd stay over a couple of nights a month, most months.
Years go by, and he continued to sleep at mine when his mum worked nights, even when he was definitely old enough to stay home alone. We had our own traditions by this point, down to the games we'd play, movies we'd watch and pizza we'd eat.
I can't remember exactly when it started, but at some point he began jerking off when he woke up. At first, he tried to be subtle. He would take long, slow strokes to be as quiet as possible. Because I was higher up on a proper bed frame, I could see everything without him knowing I was awake. Although, it didn't really matter because most of the time his eyes were squeezed shut (and his lips pressed tightly together, which really turned me on for some reason - it's weird the things that just hit different).
As he got closer to finishing, he would inevitably speed up - but as soon as the sheet rustled, he would slow down again. Eventually he'd just slip the sheet off and go balls to the wall until he came, usually all over his abs and chest. He would rub the cum into his skin, so that by the time I "woke up" there was no evidence left.
In those early days, he really seemed to be trying not to wake me, so I didn't have the heart to tell him that I probably caught him nearly every single time.
As time went on, he became more brazen, sleeping in later and openly wanking in the bright morning sunlight without any qualms over how loud he was being. He didn't give a shit if his breathing got hella heavy/raspy, and sometimes he would moan a little.
When he used to try and be quiet, I found it really hot and kinda sweet. But by the time he didn't care anymore, it was becoming sort of annoying and awkward. Sometimes he would take ages to cum, and I'd just lay there trying to maintain slow breathing to seem like I was still asleep, wishing he would hurry up.
I distinctly remember the morning when everything changed. I really needed to piss. By this time his morning wank routine had been going on for nearly two years, and I'd never interrupted him before he finished. But this time, I had to "catch" him in the act, so I could get to the bathroom.
As soon as I sat up in in bed, he came. He was literally still shooting ropes as we both started laughing, which broke the tension I guess. The first couple of ropes shot him in the face and hair, which we both thought was fucking hilarious, and afterwards he told me (in a really matter-of-fact way) that he'd never cum that much or hard before.
After this incident, the gloves were off. If I woke up while he was jackin it, I would just step over him and get ready for the day. We slipped into this routine where I'd make some flippant comment, throw a pillow at him, or just try to distract him by doing something stupid or by being a dickhead, like coming back in with a wet handtowel and throwing it at his dick.
While I would do this, he always stared me dead in the eyes, with this stupid grin on his face, like we were playing a game of eye contact chicken - but I never gave him the satisfaction of responding in any way to that. Sometimes I'd initiate conversation or whatever, and this always made him cum super quick and super hard. Even though it sounds really lewd, at the time it just felt like we were doing it for shits and giggles. The more I gave him shit for it, the less he cared about it.
As I reached a certain age, I decided that I really should upgrade to a double bed. I'd had a few people in my room by this point, but we'd only ever made out and done over-the-pants stuff, and I was convinced it was because I still had a kids bed.
Once my mum agreed to get me a double bed, I told him that we won't be able to have sleep-overs anymore because there wouldn't be room for the trundle bed. Can't remember exactly how the convo went, but he was basically like, "nah we can just top and tail, it'll be fine". The way he said it so casually made me feel like, duh, why did I make it such a big deal?
Of course, the first night in bed together was super weird. A double bed wasn't nearly as wide as I thought it would be, so we ended up being a lot closer than I expected. The first time our limbs brushed it literally felt like little jolts of electricity. I have no idea why we never actually slept top and tail... we probably forgot or thought it was a dumb idea in practice.
Like every other time, we stayed up late chatting, and I remember having this thought as I drifted off: there's no way he'll jack off now that we're physically so close.
Ha I was wrong.
The next morning I open my eyes and he's like 5 inches away, jackin off and grinning like an idiot, veins popping in his neck. His non-dominant hand was gripping my forearm, which felt weirdly intimate.
Because I'd gotten into bed first, I was against the wall, so I had to somehow manoeuvre my clumsy, lankyass body over him. I knew he could see me mentally calculating how he would do this, and he seemed to really enjoy the prospect. As I clambered over him, like we were playing a depraved game of twister, I KNEW he was speeding up so he could try and cum at the most awkward moment. For a second, as I had one leg on the ground, and one knee on the bed, I felt his furiously jacking knuckles brush against my dick or balls, which were obviously just flopping about in my boxers. I managed to spring off the bed just before he could cum, altogether avoiding that sticky situation (pun intended).
As we became more comfortable, we relaxed into what are probably just normal sleeping patterns - big spoon/little spoon, tangled limbs, etc.
Sometimes, I would feel his boner pressing into my ass or thigh during the night, and I'd apply some pressure back but never went any further than that. Oh, just unlocked a memory! I would sometimes position my open palm close to his dick, in case he rolled over onto it. He never did though. I think at this point, I was really working out my sexuality, and I was just curious to just see what another dick felt like.
Things went on like this, probably for a little while, but inevitably it began to change. I think people would say I was a late bloomer, but around this time my hormones really started to activate.
I have no idea where I got the confidence or the audacity, but one morning while he was jacking off, I placed my hand on his thigh. I thought I was being real slick, pretending I was still asleep, but looking back it would've been super obvious that I was awake because I was just kind of stroking his skin with my fingers lol.
Even though my eyes were closed, I could sense that he was definitely into it. When I opened my eyes, he was already looking at me, but for the first time he wasn't gooning or being an idiot. He looked like he was in pain, but in a nice way. His cheeks were flushed and he looked so innocent, not like the dickhead I was used to.
My mouth was dry, and my hands were sweaty, but I didn't care. My fingers danced across his skin, playing between the smooth and hairy parts. Even though I didn't take my eyes off his dick, I could tell he was watching me as I skipped along his balls and taint, responding to his reactions with different pressure, strokes and squeezes until he came (which didn't take long). As soon as he came, he was laughing and being a larrikan again.
We never fully fucked or anything, and even though we took things further I worked out that he much preferred to be a performer over a participant.
I can't even remember why we stopped, probably a range of factors. We both started dating pretty seriously, and reached an age where we were literally too old to be having sleepovers.
* for the sake of lpsg, anything sexual totally happened after we were 18, so get your mind out of the gutter.
We grew up in the same neighbourhood, and when we were younger we went to the same school, but only ever hung out on weekends, after school, or if there was a house party with somebody we both knew. I guess looking back, we were friends by circumstance because our parents knew each other (both single mums, probably had a lot in common).
Whenever his mum worked nights, he would stay over at mine, sleeping on a roll-out trundle next to my single bed. We would stay up late talking shit, and it was during one of these late night chats that I told him I might be bi. He dated heaps of girls all through school, including some of my friends, and by all accounts, was 100% straight. I don't know what his mums roster was, but he'd stay over a couple of nights a month, most months.
Years go by, and he continued to sleep at mine when his mum worked nights, even when he was definitely old enough to stay home alone. We had our own traditions by this point, down to the games we'd play, movies we'd watch and pizza we'd eat.
I can't remember exactly when it started, but at some point he began jerking off when he woke up. At first, he tried to be subtle. He would take long, slow strokes to be as quiet as possible. Because I was higher up on a proper bed frame, I could see everything without him knowing I was awake. Although, it didn't really matter because most of the time his eyes were squeezed shut (and his lips pressed tightly together, which really turned me on for some reason - it's weird the things that just hit different).
As he got closer to finishing, he would inevitably speed up - but as soon as the sheet rustled, he would slow down again. Eventually he'd just slip the sheet off and go balls to the wall until he came, usually all over his abs and chest. He would rub the cum into his skin, so that by the time I "woke up" there was no evidence left.
In those early days, he really seemed to be trying not to wake me, so I didn't have the heart to tell him that I probably caught him nearly every single time.
As time went on, he became more brazen, sleeping in later and openly wanking in the bright morning sunlight without any qualms over how loud he was being. He didn't give a shit if his breathing got hella heavy/raspy, and sometimes he would moan a little.
When he used to try and be quiet, I found it really hot and kinda sweet. But by the time he didn't care anymore, it was becoming sort of annoying and awkward. Sometimes he would take ages to cum, and I'd just lay there trying to maintain slow breathing to seem like I was still asleep, wishing he would hurry up.
I distinctly remember the morning when everything changed. I really needed to piss. By this time his morning wank routine had been going on for nearly two years, and I'd never interrupted him before he finished. But this time, I had to "catch" him in the act, so I could get to the bathroom.
As soon as I sat up in in bed, he came. He was literally still shooting ropes as we both started laughing, which broke the tension I guess. The first couple of ropes shot him in the face and hair, which we both thought was fucking hilarious, and afterwards he told me (in a really matter-of-fact way) that he'd never cum that much or hard before.
After this incident, the gloves were off. If I woke up while he was jackin it, I would just step over him and get ready for the day. We slipped into this routine where I'd make some flippant comment, throw a pillow at him, or just try to distract him by doing something stupid or by being a dickhead, like coming back in with a wet handtowel and throwing it at his dick.
While I would do this, he always stared me dead in the eyes, with this stupid grin on his face, like we were playing a game of eye contact chicken - but I never gave him the satisfaction of responding in any way to that. Sometimes I'd initiate conversation or whatever, and this always made him cum super quick and super hard. Even though it sounds really lewd, at the time it just felt like we were doing it for shits and giggles. The more I gave him shit for it, the less he cared about it.
As I reached a certain age, I decided that I really should upgrade to a double bed. I'd had a few people in my room by this point, but we'd only ever made out and done over-the-pants stuff, and I was convinced it was because I still had a kids bed.
Once my mum agreed to get me a double bed, I told him that we won't be able to have sleep-overs anymore because there wouldn't be room for the trundle bed. Can't remember exactly how the convo went, but he was basically like, "nah we can just top and tail, it'll be fine". The way he said it so casually made me feel like, duh, why did I make it such a big deal?
Of course, the first night in bed together was super weird. A double bed wasn't nearly as wide as I thought it would be, so we ended up being a lot closer than I expected. The first time our limbs brushed it literally felt like little jolts of electricity. I have no idea why we never actually slept top and tail... we probably forgot or thought it was a dumb idea in practice.
Like every other time, we stayed up late chatting, and I remember having this thought as I drifted off: there's no way he'll jack off now that we're physically so close.
Ha I was wrong.
The next morning I open my eyes and he's like 5 inches away, jackin off and grinning like an idiot, veins popping in his neck. His non-dominant hand was gripping my forearm, which felt weirdly intimate.
Because I'd gotten into bed first, I was against the wall, so I had to somehow manoeuvre my clumsy, lankyass body over him. I knew he could see me mentally calculating how he would do this, and he seemed to really enjoy the prospect. As I clambered over him, like we were playing a depraved game of twister, I KNEW he was speeding up so he could try and cum at the most awkward moment. For a second, as I had one leg on the ground, and one knee on the bed, I felt his furiously jacking knuckles brush against my dick or balls, which were obviously just flopping about in my boxers. I managed to spring off the bed just before he could cum, altogether avoiding that sticky situation (pun intended).
As we became more comfortable, we relaxed into what are probably just normal sleeping patterns - big spoon/little spoon, tangled limbs, etc.
Sometimes, I would feel his boner pressing into my ass or thigh during the night, and I'd apply some pressure back but never went any further than that. Oh, just unlocked a memory! I would sometimes position my open palm close to his dick, in case he rolled over onto it. He never did though. I think at this point, I was really working out my sexuality, and I was just curious to just see what another dick felt like.
Things went on like this, probably for a little while, but inevitably it began to change. I think people would say I was a late bloomer, but around this time my hormones really started to activate.
I have no idea where I got the confidence or the audacity, but one morning while he was jacking off, I placed my hand on his thigh. I thought I was being real slick, pretending I was still asleep, but looking back it would've been super obvious that I was awake because I was just kind of stroking his skin with my fingers lol.
Even though my eyes were closed, I could sense that he was definitely into it. When I opened my eyes, he was already looking at me, but for the first time he wasn't gooning or being an idiot. He looked like he was in pain, but in a nice way. His cheeks were flushed and he looked so innocent, not like the dickhead I was used to.
My mouth was dry, and my hands were sweaty, but I didn't care. My fingers danced across his skin, playing between the smooth and hairy parts. Even though I didn't take my eyes off his dick, I could tell he was watching me as I skipped along his balls and taint, responding to his reactions with different pressure, strokes and squeezes until he came (which didn't take long). As soon as he came, he was laughing and being a larrikan again.
We never fully fucked or anything, and even though we took things further I worked out that he much preferred to be a performer over a participant.
I can't even remember why we stopped, probably a range of factors. We both started dating pretty seriously, and reached an age where we were literally too old to be having sleepovers.
* for the sake of lpsg, anything sexual totally happened after we were 18, so get your mind out of the gutter.
