Experimented with friend during sleepovers

[14471]

Wow. Your situation is so similar to mine.
We had an unspoken agreement that we would do to eachother what the other one did.

My friend was more of the instigator. He was about eight months older than me. I dont know if someone showed him stuff before me. But, he was more knowledgeable.

We would give eachother back rubs too. Usually, in the dark. So everything was intensified. Because you could only feel what was happening.
We took turns tickling eachothers backs. As lightly as possible, tracing our fingers up and down. Our "boundry" was the waistband of our underwear.
It started out as a sort of dare. When we switched positions and it was my turn to be tickled, I inched my underwear down a little. When he discovered this by exploring in the dark, he just chuckled. Then, continued down as far as my underwear.

Ofcourse, when it was my turn to tickle him, his underwear was also pulled down further. Daring me to tickle him lower as well. Which I did.

Eventually, our underwear was down to our knees, or even off.
That was always scary to be totally naked. Just incase someone came down the stairs, like his parents. But we became bolder as time went on. His parents would rarely come down to the basement when we were down there. But we would still freeze if the door at the top of the stairs opened if one of them hollered down for some reason.
It wouldn't take us too long to get our erections back.

Like you, when my friends hands couldn't get further between my legs, I would lift my hips off the bed so he could reach me.
He would stroke me like that for a while. His arm between my legs. His fingers wrapped around my boner.

Then, we would switch and I would do the same to him.
After a while, I would have my head on the pillow with my butt up. On my knees. My friend reaching between my legs, stroking me or reaching around my waist to stroke me. Our erections hung stiffly away from our bodies. Leaking on the towel that we would place under our bodies. He would rub my precum ooze over the tip of my penis and along the length of it as he played with me.
As he knelt behind me, I could feel his stiffie poking at me and bouncing against my butt and legs. He would rub himself between my butt cheeks. Smearing his juice on me.

Then we would switch. I would do everything that he did to me. That's just how it worked. Each time we switched one of us would go a little further. Daring the other to do the same when it was their turn. Hoping that the other one would do it. So we didn't have to ask to have it done.

We would do this for hours. Getting as hard and leaky as possible without coming. Until, we just couldn't hold it back any longer. Then, we would agree to finish the other off.

We usually waited til we were both about to cum. We knew that, once we came, we usually didn't want to play any more. We would lose our interest in continuing. So we tried to cum at the same time. That way we both got what we wanted.

[effinjeff1965]

Dude, if it weren't for a few small details, I would be pretty sure you were the buddy I played with. I'm still not sure you're not. LOL.

Kidding aside, yeah, your experience is a lot like mine. It would be fun to hear what my friend's thoughts about our past would be. I would hope he would say exactly what you've said. I wonder what your friend thinks about it now. You and I remember our experiences fondly. I hope my buddy does too. (And all of the buddies I played with.) Do you think your bud does?

[14471]

I hope that my friend remembers it as fondly as I do.
I always thought it would be interesting if we found ourselves in a situation alone, on a camping trip or something. We get into our sleeping bags and lay in the dark. Then, out of the blue, he asks, "Do you want to tickle"? Just like he used to do when we were young.
"Sure. Why not?" "Its not like we haven't done it before". I tell him.

[effinjeff1965]

I hope that my friend remembers it as fondly as I do.
I always thought it would be interesting if we found ourselves in a situation alone, on a camping trip or something. We get into our sleeping bags and lay in the dark. Then, out of the blue, he asks, "Do you want to tickle"? Just like he used to do when we were young.
"Sure. Why not?" "Its not like we haven't done it before". I tell him.

I get that. I mentioned in an earlier post about the one buddy I ran into at a wedding recently. I toyed with the idea of bringing up the past, but back then I was not much of an instigator, and apparently that hasn't changed and i thought it better just to leave it alone.

In another post I mentioned one of the buddies reconnecting with me on Facebook, and though we messaged back and forth to catch up, we didn't talk about that. I went to a class reunion a few years ago and he was there. I was interested to see if maybe there was something there, but he brought along his wife and young son, so that didn't go anywhere. I spent more time talking to his wife than I did to him.

The friend I've mentioned the most here isn't on Facebook, but his wife is. She's from the same small town, so I knew who she was, but I wasn't friends with her so it would be awkward to send her a friend request. I did look at her photos though, and he looks the same, maybe a little burlier than he was way back when.

That friend lived on my block as did a third buddy, who was a year older. Though the one friend was the youngest, he was the ringleader in all things, sexual and non-sexual. The older guy and I played a few times on sleepovers, but I remember it being tamer, maybe since we were both followers. I learned from the other friend, and it looked like the third guy did as well. I was on a sleepover at that third guy's house and we were in his bed and had pulled down our pajama bottoms and were goofing around and hard. His mom came in and caught us. She told us to pull up our pants and go to sleep. It was embarrassing, but no one ever said another word about it. I couldn't help but notice that we didn't have any more sleepovers after that even though we remained friends and his mom was still nice to me. Sadly, his mom died of cancer a year or so later, but almost immediately after that he started inviting me on sleepovers again. I never asked but I assumed he didn't want to ask me because his mom would worry we were going to mess around, but after she died, no one knew. His dad was still alive, of course, so either he didn't care or he didn't know.

Sex play started up with that guy again, though one day he showed me a book on teen sexuality on his dad's dresser. He said his dad left it there for him to read. We pored through it. They were Catholic and the book was written by a priest, so the info was a little skewed, but we didn't know. We looked at the chapter on homosexuality and it said that gay sex was a sin. Though we knew that our sex play wasn't something to advertise, we hadn't thought it was sinful or anything. I remember saying that if that were the case, we probably shouldn't play anymore, and he agreed. I was a little disappointed to stop, but I didn't sweat it.

Things cooled off for years. I started hanging out with different friends and there was no playing around going on with that group. I didn't care since I had been more interested in girls, though I wasn't getting any real experience with them. By then I was more into solo sex and jacking off.

I started hanging around with the neighborhood crowd again and figured out that my alpha friend was still playing. He had recruited a few other guys from the neighborhood and we would go in the fort he had built in their alley and we'd play Truth or Dare. The games would start mostly with "Truth," though eventually one of us would dare another and it would go from there. I remember I was dared to do a strip tease and when I got naked one of the other guys was so overcome by lust that he tackled me and rubbed his face in my crotch and played with my dick. I was a little surprised he would get so bold in front of the rest of the guys, but I think he was so aroused that he couldn't help it. Other dares were around stroking each other's cocks or lying on top of each other for 30 seconds and things like that. Now that I think of it, I don't remember alpha boy participating so much as orchestrating, but the rest of us jumped in with both feet. He did get involved too, but I think he liked directing the rest of us. I remember meeting up with some of the guys in the fort for one-on-one play, but I liked the group stuff too.

During that time i spent the night at the third guy's place, and he told me that alpha boy had told him about our games in his fort, which was kind of embarrassing, but it wasn't a big deal. That's just how things were then. This buddy hadn't taken part in those games. He didn't mind that we played, but he didn't do that anymore. I didn't know if was more that he didn't think he should do that stuff anymore (even if he still wanted to) or if he just didn't want to. He did, however, ask me if I jacked off. He said he did it once a week or so. I jacked off pretty much every day--sometimes multiple times a day--but I coolly said, "yeah, me too. Maybe once a week or so." He asked if I wanted to jack off with him now. I said sure. We were sleeping in his backyard in their camper. We were each in or own sleeping bag but next to each other. We both jacked off, but in the dark I couldn't see him too well and we didn't touch each other. We talked as we stroked. I had been jacking off for years, but I'd only started shooting jism recently and it didn't yet come out every time I beat off. When I came in his camper nothing came out. I quietly had my orgasm, but didn't say anything. He told me he was going to come. He came and wiped up with his handkerchief. He asked if I had cum. I said that i had. He asked what I did with my cum. I didn't want to admit that nothing had come out, so I told him I wiped it on my sleeping bag.

That was the last time I did anything with him. I still played with the others in the fort, but shortly after that my family moved to a different town and by then I wasn't going to try anything with the kids at my new school so that sort of play mostly stopped except for summers when the farm buddy I mentioned earlier would come to stay with his married sister who happened to live across the street from us in the new town. His sister's husband was the brother-in-law who gave him the porn mags. We were in their basement one night while his sister and brother-in-law were out. My friend was babysitting his nieces and nephew, but they were in bed, so we helped ourselves to the bar in their basement and he pulled out a hardcore mag that belonged to his bro-in-law. We looked at it together, and I was aroused like you wouldn't believe because that was the first time I'd seen pics of guys with boners and saw them penetrating the women.

We started talking about which guy in the magazine our cocks looked the most like. My buddy suddenly pulled his shorts down to show me, and there was his cock standing straight up. He told me he was bi. I said that I thought I was too. He asked me if I wanted a blowjob. I played it all cool, like I didn't care, but of course I wanted him to. He came over to my chair and pulled my shorts down with my boner popping straight up. He started sucking on me. All I could think about was the fact that I had jerked off earlier that day so I didn't know how much cum would come out when I shot and I would be embarrassed if it wasn't much. He kept sucking and I came in his mouth. He kept sucking for a bit and then stopped and milked my cock, looking for cum. He asked if I had cum and I said I had. I figured enough had come out for him to taste, so it wasn't too embarrassing though he did had to ask me to be sure.

Unfortunately, at that point, when I came, I kind of freaked out and said, "That wouldn't have happened if I wasn't drunk." He said that he would have still done it even if he was sober. He was more highly evolved than I was. I went home. He came over the next day, and I was so freaked out I could barely look him in the eye. He sensed what was up and left. We didn't hang out the rest of that visit, but the next time he stayed at his sister's, we hung out like nothing had happened, though we didn't fool around again.

[varvara]

and why only in the night? I usually slept at night. Still sleeping.

[14471]

I guess, in my case anyway, night time was when we were more excited. We played around outside all day. We did a few naughty things. But, at night, when it was dark and everyone else was asleep, that's when we got excited. There was also something about it being dark that made it more comfortable.
It was awkward for two straight boys to be experimenting in broad daylight. But at night, it seemed safer. More private.

[effinjeff1965]

I guess, in my case anyway, night time was when we were more excited. We played around outside all day. We did a few naughty things. But, at night, when it was dark and everyone else was asleep, that's when we got excited. There was also something about it being dark that made it more comfortable.
It was awkward for two straight boys to be experimenting in broad daylight. But at night, it seemed safer. More private.

I agree with this completely. I remember my buddy and I would watch TV and do regular things on sleepovers---until we went to bed. Then things started happening. It WAS just more private.

[stopsandwaits]

I would have sleepovers with a friend of mine. It started off as truth or dare that would eventually become sexual. Eventually, it ended up I would be the bottom and would suck him off before he fucked me. Still my go to fantasy

[misslb]

Yes, I have great memories of experimenting with friends at sleepovers growing up. Typical girls talk about boys and sex sometimes got us talking about masturbating, and sometimes we masturbated with each other

[bossathenova7]

I only had one experience experimenting with a friend. We were around 13 I think. We had rented a movie that showed some boobs. When my parents were out we watched those parts again. We started daring each other to do things - dance around, strip tease, stuff like that. At one point we asked each other if we’d ever done anything with another guy and we both said yes. We agreed to suck each other. So we took turns. Neither of us could really cum yet, so it just went to dry orgasms.

It was the only time it happened. Looking back I wish we had kept going, we could have had a lot of fun.

[latinababii]

It was the first of 2 times where I ever did stuff with another girl. She was a friend from high school that was staying with me and my family while her parents were away. I never really had a crush on her but she was hot. She played for the school soccer team had brown hair with highlights, about 5’5, didnt have big boobs but her ass and legs were incredible. I found myself constantly checking her out whenever she wore shorts.

Anyway, one night we were in the basement watching a movie and there was a scene of this girl masturbating while dreaming of her crush fingering her. I remember us talking about it and whether we’d ever kiss a girl or let that happen followed by other sexual questions. Towards the end she admitted to me that she usually masturbates every night before bed but hasn’t been able to since she’s been staying at my house.

I remember telling her “I totally understand it really wouldn’t bother me one bit you could do it here right now and I wouldn’t mind” She just looked at me for a second before asking “Really?” To which I confirmed.

I didn’t expect it but she just said “if you say so” and proceeded to pull her shorts and panties down to her knees and just started masturbating right next to me. I watched her for a few seconds all the while I’m getting soaking wet. I couldn’t believe she was doing this in front of me. Not to mention how incredibly hot it was or how amazing her bare pussy looks between her sexy legs. I wanted to touch her so badly..

She then turned to me and said “I’m sorry I just really need to cum right now” “if your sorry then I am to” I replied before pulling down my pants and underwear to join her. So there we were both intently watching each other pleasure ourselves. I couldn’t resist the temptation and began rubbing her leg from ankle to thigh. She smiled at me and did the same. So I then just slid my hand up grabbed hers to move it and rubbed her pussy. We then faced each other and rubbed my pussy to each matching the others pace. We went faster and faster until I couldn’t hold it anymore and told her “omg your gonna make me cu... I’m cumming I’m cumming!” I came so hard I was convulsing. I couldn’t focus at that point and she ended up making herself cum but when she did she threw her legs over my shoulders while I kissed and gently licked them.

TBC..

[timcrav]

When I was about 8 or 9 my best friend and I would spend a lot of time during sleep-overs talking about beautiful-naked-girls (all one word) while we lay in bed in the dark, getting hard. We never touched each other, although he once said he'd rub my cock if I wanted, but I said no. Once we sat in a dark closet with a girl our age, our pants down, shining a flashlight between each others' legs. My clearest memory of a sleep-over at his house is about how one night after we'd gone to bed and the lights were off and we were supposed to be asleep his father came into the bedroom and quietly lifted the covers off me and shone a light on me. Years later I decided that he'd probably been hoping to see me naked or at least with my pajamas down. In a way I hoped he had - I liked thinking about him leaving the room with a hard-on!

[kitten]

I think that at some point I had experimented with or attempted to experiment with all my close girlfriends as a kid. I remember hiding in closets with one girl from church, I don't remember details but I know we were up to no good in a touchy feely way.
A girl down the block whom I had many sleepovers with used to make-out with me and we would watch porn on her parents TV when we were left alone. Eventually leading to us getting completely naked on several occasions and rubbing our almost hairless kitties together. I remember we would suck eachothers tiny nipples and touch one another down there. I remember the feelings i got when we did this as if it was yesterday. She eventually stopped wanting to play which sucked, but soon after I started actually dating boys and the sleepover shenanigans became less and less.

[ragoguy]

Yes, I still think about all the times My J/O buddy Ron and I had... We would Jack each other Off , and all so We would Suck each others Cock, I would swallow his Cum, but he spit mine out, but I didn't care it still felt Fantastic... We started about 12 I think and continued all thru school till graduation... We both got married but we would still do each other when we could , right up to about maybe 50 or 55 when him and his wife moved way out to N.M. , have not seen him since, but have had some fone sex with him a couple of times... Just remember, Nobody can EVER take away Your Memories, they last a life time ...

[toesucker17]

I'd taught myself how to masturbate at age 13 by getting naked and humping my bed on my stomach until I came. I continued to masturbate that way just about every night until this one night that following summer, I was staying over at my friend's house (he was a year younger than me). I don't even remember how it started but we ended up getting naked in his bed, I think because he said it would feel better. After getting each other horny by talking about hot girls we knew, he started jacking off. I then flipped over on my stomach & started humping the bed and he looks over at me & is like "Dude, what the fuck are you doing? I told him I was masturbating, & so he showed me how to do it properly. So we jacked off together, cumming at about the same time. We didn't touch each other, but for some reason I kept feeling compelled to rub my bare feet on his bare feet. He didn't seem to care. That happened every time we got the chance, then about a year later, it was summer 2002 and he was spending the night again, we were naked and masturbating in bed when he suddenly rolled over on top of me and started grinding on me. This was new and a little scary but it felt so good! He was kissing my nipples and grinding his cock on my cock. Eventually he came on my chest, and then grabbed my cock and jerked me off until I came.

For the next 2 years we messed around every chance we got. In bed, in the pool changing room, in his dad's garage, the woods (I'll never forget the time he humped me against a tree. Each time we would get naked and grind our cocks together while sucking each other's nipples, and whoever would cum first would then stroke the other off. It was especially fun when he'd be home alone. I'd come over and we'd spend the day totally naked humping each other's cocks, our bare feet interlocked, cumming over and over again and being as vocal as we wanted. We eventually started exchanging blowjobs, he first blew me after cumming on me after another grinding session, and the next time we fooled around I blew him in his dad's garage, I remember the taste and the warmth. I remember not liking it at first but as I got more into it the more I liked it. He didn't cum in my mouth that first time, he pulled out and came on my bare chest (yay for being shirtless) and I absolutely loved that feeling. Also a few times we even gave each other footjobs in his backyard jacuzzi while his mom was right inside the kitchen. By now we both knew what being gay was and how it was looked down on, (especially considering we went to Catholic school) so we told ourselves we weren't gay (by now I was also becoming very attracted to girls as well) we told ourselves we were just two horny virgins looking for an orgasm. And for a long time I believed it...

Sadly, the messing around with my friend ended after 2 years. He got a girlfriend and lost his virginity and didn't need me anymore. He and I never messed around again and eventually drifted apart. In a frustrating twist he's actually become a rabid anti-gay bible thumper while I am a semi-closeted bisexual man.

[don111]

at my friends house when we were about 13, we had to shower together to save water. He would show me how he would take the shower rose off and let a direct stream of water hit his knob. I was intrigued, as at that time my foreskin was too tight to retract(oh for some adult advice) and his did retract. I just thought from reading education books that he was circumcised and I wasn't. I now think he was showing me how he used to masturbate, using the shower...oh if I hadn't been so naive. Wish I had dropped to my knees for him now!

[russ195]

at my friends house when we were about 13, we had to shower together to save water. He would show me how he would take the shower rose off and let a direct stream of water hit his knob. I was intrigued, as at that time my foreskin was too tight to retract(oh for some adult advice) and his did retract. I just thought from reading education books that he was circumcised and I wasn't. I now think he was showing me how he used to masturbate, using the shower...oh if I hadn't been so naive. Wish I had dropped to my knees for him now!

Don't suppose you used to live in Arkansas?

[don111]

at my friends house when we were about 13, we had to shower together to save water. He would show me how he would take the shower rose off and let a direct stream of water hit his knob. I was intrigued, as at that time my foreskin was too tight to retract(oh for some adult advice) and his did retract. I just thought from reading education books that he was circumcised and I wasn't. I now think he was showing me how he used to masturbate, using the shower...oh if I hadn't been so naive. Wish I had dropped to my knees for him now!

Don't suppose you used to live in Arkansas?

hehe sorry no it wasn't me that showered with you!

[anon1122]

Experimented with my friends younger brother at sleepovers.. was my only experience with another male. We were both young and a couple years apart. It really started with the younger brother he would constantly run around pulling his pants down or showing his penis. That progressed to him pulling it out whenever he had a boner and he would try to poke me with it thinking it was funny. This went on for awhile until one day he tried to push his hard little dick on to me and I just grabbed it squeezing hard. He started humping my hand and when I let go he ran off giggling.

One night we happened to be laying on the same bed and he pulled it out again and rubbed it on my hand under the covers. I began to play with it a little bit and decided to jerk him off. So I stroked his little shaft with my thumb and index finger until he came. I actually really enjoyed doing it to him. The next time we were playing hide and seek and we both hid in a closet facing each other in the dark. We both had shorts on and I slid my hand up his leg to grab his penis. I was jerking him off again when I felt his hand run up my leg and into my shorts. He grabbed my dick and we were jerking each other off. I came first this time closely followed by him and it became a routine thing whenever we were together..

[sunnygirl]

I think this is a very common thing growing up, it certainly was for me. Largely it was just being dared just to kiss other girls, but with some friends, especially if there was just two of us, it went on to become more.
With one friend it began with sleeping naked together in the same bed to begin with, but inevitably, as hands wandered, it turned into masturbating each other.