Can you remember the first time cumming inside someone or being cummed inside?

[DaveMack]

When I was 16, there was this guy named John. He was about 30 and lived by himself. The parents of my friend Ken, knew him quite well and my Ken and I had been mowing his lawn and doing yard work and general clean up for him for three summers and he would pay us a few bucks. He seemed like a really cool guy and lots of us kids liked him.
In the winter when it was cold and we had no place to go several of us guys would often go over to his place and hang out if we had nothing else to do. We would watch TV or play board games. He always had board games and snacks and stuff we thought he was pretty cool. Most of the guys in the group had known each other since grade school and when we hit puberty we explored masturbation together. Some of us had done circle jerks but no touching of each other. We would sit around and jerk off and comment on each others cock size and how much you came. Back when you were 11 and 12 you didn't cum much so it was a big deal.
Anyway, one Saturday night in January Ken and I went over to his place. It was cold as hell and there was only one movie theatre in town and it was showing an adult movie that weekend and we couldn't get in. We had gone to the skating rink and nobody there. Went to a couple of other hangouts and nobody there. Just too damn cold. We didn't feel like going home so we went to John's.
That particular night with just Ken and I there John started asking us questions about how we felt about girls and questions like that. We talked for a while and then he asked us if we had ever done a circle jerk. Ken and I were both a bit embarassed but answered yes.
John then asked if we would like to see some Playboy magazines. Of course we would. So John gets a handful of magazines and we are all looking at them and John asks if we want to jerk off. We thought about it for a minute. I guess we were a bit shy about showing our cocks to a real adult man but after a few minutes and a little teasing from John, we agreed.
Ken and I had seen each others dicks before so no big deal but we were both watching when John pulled his out because neither of us had seen an adult man hard before. We were both impressed. He was a lot bigger than we were. We both commented on the size and John said not to worry we would grow a lot more as we got older.
Each of us picked a magazine and found a woman we liked and started jerking. I was concentrating on a cute brunette in my mag and Ken was focussed on a blonde. John had a magazine and was jerking too. After a while I happened to look up and John was looking at me as he jerked not at his mag. I didn't think anything of it and went back to the business at hand and soon shot. Ken was shortly after. John didn't cum.
After we put our cocks away, Ken seemed to get a bit embarassed and wanted to leave so he said he would see me tomorrow and he took off. It was about 8 o'clock. That left John and me. John said Ken seemed a bit embarassed and I agreed. He asked me if I was embarassed and I said well, a little. John told me I had a nice cock and what we did was normal and I shouldn't be embarassed. He said he thought I had a really nice cock.
That compliment made me feel something. It wasn't excitement just kind of a nice warm feeling inside. John offered me a beer which I took cause we didn't get to drink very often. While we were drinking John just casually talked about guys circle jerking and how it was relaxing for guys to do that. When I finished my beer.
John asked if I had ever jerked other guys when we cirlcled jerked. I said no I had never done that. He asked if I had ever thought about it and the truth was I hadn't. Then he asked me if I would like to and said I hadn't thought about it but I might. So John suggested we go back into the living room and try jerking each other on the couch. I said ok and we went.
When we got in there he said since there was no one else around, why don't we just take off our pants and shorts altogether it would make it easier. I agreed and there we were sitting naked from the waist down on his couch.
I was nervous as hell but excited too and I was hard. John was hard too and his cock was way bigger than mine. He started. He said I'll jerk you a bit first then you do me. I agreed. The touch of his hand on my cock was electric. It was very exciting. While I had been fucking the girl I mentioned in the story above, she never touched us. She just laid back and we banged her. She never touched us and didn't want to be fingered or anything so I had never had anyone touch my cock before.
John got me feeling quite good and then he stopped and asked me to stroke his. I was very tentative at first but I found I liked the feel of it, the heat and the softness. Having jerked myself about a zillion times by that age the feeling was not unfamiliar but at the same time different and exciting.
Bear in mind that despite the fact I had been fucking a girl (very badly) for a couple of years, I was very inexperienced about most things to do with sex. I didn't know what we were doing was bi or gay or any of that. I didn't even know what bi or gay was. To me it was just an aspect of sex I didn't know existed so while nervous, I was not frightened. Quite the opposite I found it very exciting and arousing.
Stroking John's cock felt very comfortable and the more I did it the more exciting it became. My cock got even harder. At that point, John said you know, there are things men can do to each other that are a lot more fun than just jerking. I asked what that was. He explained that men can have sex with each other just like men have sex with women just that we use our asses cause we don't have cunts.
Now I may have been inexperienced and didn't know what this action was called but when he said that, my ass actual clamped and tingled and my cock actually jumped cause I was so excited.
John just looked at me. I remember my mouth got dry and I looked at him. The excitement was so powerful I could barely speak but I asked if we could try it. John said are you sure you want to do it. I said yes.
He said ok we can try it but lets go into my bedroom. In the bedroom he took off my shirt and undershirt then removed his own. We were at the foot of the bed and he came and wrapped his arms around me and kissed me. I still remembe how much I enjoyed that feeling. He was still kissing me when he reached down and touched my cock and stroked it. My knees buckled and he lowered me gently to the bed.
We lay there for a minute My pulse was pounding and my breathing was ragged. I didn't know exactly what was coming but I wanted it whatever it might be.
John rolled me onto my stomach and spread my legs. He very gently and softly kissed my ass cheeks and licked the backs of my legs. Eventuallly his tongue found its way to my ass where he slowly licked then probed with his hot tongue.
He did this for what seemed like a year but must have only been a few minutes. Then he said ok I'm going to put something on your ass that will make this easier and he put some kind of lube on my ass opening. Then he very gently worked it in with his fingers. As he finger slowly entered me I was crazy excited. He got it in all the way and just moved it around I bit. I know I moaned at that time.
Then he got me to raise my stomach up and he put a pillow under me. He pushed me back down and pulled my legs apart and laid on me. I could feel the heat of his cock against my ass and he began gently kissing my neck and sucking my ears. I knew he was excited too. I could hear the ragged catch in his breath as he said ok now, I'm going to put my cock in very very slowly. All you have to do is relax. If it hurts tell me and I'll stop ok. I said yes.
My ass was on fire. I felt his cock move against my opening and then slowly start to enter. He was very slow and very gentle. There was no pain just a slight discomfort for a moment as the thick part of his knob passed through my opening. He held very very still at that moment, still kissing my neck. My cock was so hard at that moment it hurt.
John worked his cock in an inch at a time. I knew when he was all the way in because I could feel his belly against my ass cheeks and his advance stopped. Again, he laid there for some time allowing me to adjust to the sensation. And, I LOVED the sensation. After a while he snaked his hand under my belly and grabbed my cock in his hand and then he slowly started to stroke. I was going crazy. There is this wonderful feeling in my ass and now my cock is being stroked. I was in heaven.
As John became more aroused he increased his tempo and also increased the speed at which he was jerking me. At some point I remember pushing my ass back to meet his thrusts. It just felt so damn good. Then he was pounding like crazy. He grabbed my hips and pulled me back on to his cock. He had let go of my cock and was just fucking the hell out of me and I was fucking back.
In a moment he stiffened and then blew his load in me. I was so excited that a second after I blew my own load all over the pillow.
We must have lain there for 10 minutes or more catching our breath. After that we got up and had a shower. John washed me and I washed him and we were kissing and necking in the shower like a man and woman. Somehow, it just felt normal. We talked for a while after we got dressed and it was getting to be time for me to go. He asked me if I'd like to do it again and I said I would.
So, there I was 16 years old and I'd learned to fuck girls and men. John and I continued to see each other until I was 21. Over the years he taught me to suck cock, introduced me to other men and several women and I learned a great deal about sex and myself.
When I was 21 John transferred to another city. We visited a couple of times but then lost touch. I never will forget him though.
I think that in part, it is what he taught me that allows me to be a good cuck/slave/sissy for my hotwife.

[masai76a]

Hi my name is joshua from KENYA MOMBASA BEACH AFRICA and i remember my first cumming inside a whire pussy at the beach here in mombasa ,it was my really first white woman sex and she wanted me cum inside her,she was very smooth and hot also her pussy was creampied and i had to grind every inch to penetrate her tight pussy disregarding her groining as i drive deep in her

[USMC_BAREBACKER]

An 18 year old Filipina bar girl in Olongapo City, RP

[easy2]

I was in high school. Had a girl friend that would at first just jerk me off, then she started too blow me too, after a while she let me fuck her, her first cock, but i always had to pull out too cum. after a while her older sister took her to the doctor and got her on the pill.I remember cumming in her felt sooo good , it was the first time for both of us. To this day I think she gave the best blow jobs I ever had. She loved to suck cock.

[burllleee]

Originally Posted by easy2

I was in high school. Had a girl friend that would at first just jerk me off, then she started too blow me too, after a while she let me fuck her, her first cock, but i always had to pull out too cum. after a while her older sister took her to the doctor and got her on the pill.I remember cumming in her felt sooo good , it was the first time for both of us. To this day I think she gave the best blow jobs I ever had. She loved to suck cock.

Oh wow Easy. Sounds to me like you should try and get in touch with her again. She probably has the same memories and would love to suck you off and let you fuck her again for old times sake
Please keep posting, thanks

[monel58]

1st time cumming inside a pussy was also 1st pussy and 1st creampie I had. I was at a party, all the kids were in a back bedroom being babysat by the oldest girl there, while the adults were in the front of the house partiing. So we were playing the usual games when the sitter says lets play in the dark hide and seek and switched off the light. I searched around and found her in the bed under the covers with my older brother (who's hung like a horse even at that age) humping away like crazy. Being a curious younger brother I pestered them with questions until she whispered leave us along for a while and you can go next. After my brother grunted a few times and rolled off she whispered OK get on top of me, she pulled my little cock out rubbed it up and down her dripping slit until it wormed it's little way up there. She got me pumping in her and boy did it feel great!!! It didn't take long until I was pumping what must have been just clear fluid into her hot, tight, slippery pussy. She pushed me off and we out of the bed covers and zipped up, light back on just in time for one of the Moms to check on us.

[burllleee]

Originally Posted by monel58

1st time cumming inside a pussy was also 1st pussy and 1st creampie I had. I was at a party, all the kids were in a back bedroom being babysat by the oldest girl there, while the adults were in the front of the house partiing. So we were playing the usual games when the sitter says lets play in the dark hide and seek and switched off the light. I searched around and found her in the bed under the covers with my older brother (who's hung like a horse even at that age) humping away like crazy. Being a curious younger brother I pestered them with questions until she whispered leave us along for a while and you can go next. After my brother grunted a few times and rolled off she whispered OK get on top of me, she pulled my little cock out rubbed it up and down her dripping slit until it wormed it's little way up there. She got me pumping in her and boy did it feel great!!! It didn't take long until I was pumping what must have been just clear fluid into her hot, tight, slippery pussy. She pushed me off and we out of the bed covers and zipped up, light back on just in time for one of the Moms to check on us.

That's hot Monel
I like the way she told you that you can go next. Did you ever get to do her again after that night? Sounds like she might have been a good little slut and liked getting fucked. I loved those young girls that were still learning and loved it.
Please keep posting, thanks

[boomer1959]

Damn That was a hot story!

[monel58]

She "babysat" several times but I didn't get to have sloppy seconds but a few more times, she was sitting just us two and my brother didn't want to share. She was horny as all hell sometimes because the couple of other times I fucked her she tired my brother out so she came out and had me try and finish her off. One time she must have been super horny and not been able to find a "big" cock to satisfy her so she took a bunch of "young" guys from the block to an old shack behind the apartment building. It was dark in the shack with just a single candle burning, an old mattress on a rickity bed. She lined us up and had us pull out our weiners, than she pulled off her shorts and panties laid down with her legs spread wide and had us jump on and hump her one at a time, i was lucky and got a second turn before we heard some noise and scrambled out of there. Well a few weeks later the shack burned down and someone must have talked because her family moved out of the building not long after, a pity because her's was the hottest, tightess pussy i have ever had, even after getting banged by my brother and a train a boys.

[burllleee]

Originally Posted by monel58

She "babysat" several times but I didn't get to have sloppy seconds but a few more times, she was sitting just us two and my brother didn't want to share. She was horny as all hell sometimes because the couple of other times I fucked her she tired my brother out so she came out and had me try and finish her off. One time she must have been super horny and not been able to find a "big" cock to satisfy her so she took a bunch of "young" guys from the block to an old shack behind the apartment building. It was dark in the shack with just a single candle burning, an old mattress on a rickity bed. She lined us up and had us pull out our weiners, than she pulled off her shorts and panties laid down with her legs spread wide and had us jump on and hump her one at a time, i was lucky and got a second turn before we heard some noise and scrambled out of there. Well a few weeks later the shack burned down and someone must have talked because her family moved out of the building not long after, a pity because her's was the hottest, tightess pussy i have ever had, even after getting banged by my brother and a train a boys.

Damn, I hate they moved. She sounds like a really nice little whore. I just loved fucking those young girls that enjoyed getting screwed. They were so much fun .
I knew several in school and some of them got pregnant but still loved to fuck every chance they got before, during and after they were pregnant. I remember this one that got pregnant when she was only 14 and right after she had the baby her Mom put her on birth control pills. She really went wild then and pretty much every guy I knew fucked her.
One night at a dance at school we got her to go out to my friend's car and he and I fucked her. i went first and then watched him fuck her. That made me get another hard on after I saw him shoot his load in her so I crawled on her and did her again. While I was doing her he went in and told some other guys what we were doing and about 4 of them came out and took a turn with her too. I watched most of the time and everytime one of them got off her you could see the cum run out of her pussy. My buddy's car had a big wet spot on the backseat after everybody finished with her and she got out
She told me she remembered the first time a guy shot off in her. It was her older sister's boyfriend and she was only 12 at the time. She said she loved the way it felt and she never wanted a boy to wear a rubber after that.