My first time

[stopsandwaits]

Although I identify as straight, my first sexual experiences were with another guy. We fooled around several times in the woods near my house, taking turns blowing each other, and fucking each other, but never to orgasm. One night, he spent the night at my house and after everyone had gone to bed, we decided to play truth or dare. After some oral and manual foreplay, I dared him to fuck me until he came. He agreed and got the Vaseline for lube. His cock was thick and about 6 1/2 inches and curved up. I lay n my stomach, naked, as he rubbed the Vaseline on his cock and my asshole. Although I was nervous, I was also excited as I felt the warm head of his cock press against my asshole. I grunted a little as he entered me and had a sensation of feeling full, once he was entirely inside. As he picked up the pace, I moaned louder and louder as he fucked me. Before too long, he stiffened and came in my ass. As he pulled out, I had a feeling of wanting more, but he was done. By the time I got some tissues, the come was leaking from my ass. I’ve never had another man come inside me, but it is one of my go to fantasies.

[jemstone]

My "first time" playing with another penis did not include oral or anal sex, but we did frot and more. My story, "Scout Grope," here on ST tells the story.

[mash2014]

My first conscious sexual interaction was with another guy. I went over to his house and in his bedroom, we were chatting. It was a warm summer night and he suddenly took off his shirt and pulled down his pants. I got semi aroused and opened my pants. In no time he was rubbing me and so I did the same. We had been drinking heavily and we got naked and oraled each other. After a while I puked my guts out. And From there things went south. To this day I know I would go all the way if not for being intoxicated. And ever since I've had a desire to be with a man. With the caveat that no drugs or alcohol will be involved. I want to feel and be felt by a man.

[ruthborn]

I was 15 and I had told my room mate at school (boarding school) how I had gotten sucked off by a guy in the park toilets one night and the conversation turned into him wondering what other guys looked like naked. I offered to show him mine if he showed me his and we both ended up getting undressed and showing each other our bodies. Looking turned into touching and I remember touching his chest, holding the back of his head in my hands and groping his butt. Of course we also ended up exploring each other’s now-hard dicks and he asked me if he could touch mine, to which I said “sure” and opened my legs for him to see everything. I remember him being very involved in inspecting my boyhood. There was a lot of gripping and squeezing and pulling and peeling. He would grip my entire genitalia at the point where it connected into my pelvis and pull. He pulled and squeezed my balls and I remember enjoying him stretching my sac out and gripping each ball in his hands and telling me he could feel the tubes connecting to them. He also seemed to love playing with my foreskin (he didn’t have one). We did all the things two naked, hard and horny boys do to each other, we rubbed our dicks together and made them kiss. We poked each other’s sacs with them. I remember that he had peeled my foreskin back and was looking at the full pink meat of my penis’ head when he wondered what our penises tasted like. Now I was more than eager to have another mouth take my penis and I was pretty curious about what one would feel and taste like in my mouth so I suggested that we could suck on each other if he didn’t tell anyone.
So that’s what we did; we got on the floor and lay on our sides next to each other in a kind of 69 position and put each other’s hard teen wieners in our mouths. I have to admit, it was a pretty meh experience. Particularly compared to my experience with the older guy. It was probably the position we were in that made it kinda sub par. Anyway, after a while it was getting kinda tiring but I admit I was enjoying just having his dick in my mouth, plus I wanted to make him cum. A few minutes more of tolerating the bad position I decided to take control and pushed him onto his back with me on top of him on my hands and knees and from there I had a much easier time of swallowing him. He had stopped sucking me when I moved us and so I ended up rotating around while still sucking him until I was on my knees between his legs, my hands holding his hips and his hands on my head as I just devoured his penis. I remember feeling like I was a wolf or a wild cat just ferociously eating his dick off and his hands and bouncing hips were eagerly encouraging me to do it.
Obviously by the end of it all he came and I got to experience a penis erupting in my mouth for the first time and I got to taste and eat boy seed. After a bit of lying on the ground naked catching our breath we went to have our showers and then went to bed.
The next night we were already in bed when he asked what his sperm tasted like (I remember saying it was fine) and if he could suck on me and taste mine. I said sure and he came over to my bed, pulled my bed sheets up, pulled my boxer shorts off and did all the things I did to him the night before. He kept going on me until I came for him and I remember him saying that he liked the way my dick tasted.
We kept sucking on each other periodically over the next two years until I moved schools.

[mash2014]

I was 15 and I had told my room mate at school (boarding school) how I had gotten sucked off by a guy in the park toilets one night and the conversation turned into him wondering what other guys looked like naked. I offered to show him mine if he showed me his and we both ended up getting undressed and showing each other our bodies. Looking turned into touching and I remember touching his chest, holding the back of his head in my hands and groping his butt. Of course we also ended up exploring each other’s now-hard dicks and he asked me if he could touch mine, to which I said “sure” and opened my legs for him to see everything. I remember him being very involved in inspecting my boyhood. There was a lot of gripping and squeezing and pulling and peeling. He would grip my entire genitalia at the point where it connected into my pelvis and pull. He pulled and squeezed my balls and I remember enjoying him stretching my sac out and gripping each ball in his hands and telling me he could feel the tubes connecting to them. He also seemed to love playing with my foreskin (he didn’t have one). We did all the things two naked, hard and horny boys do to each other, we rubbed our dicks together and made them kiss. We poked each other’s sacs with them. I remember that he had peeled my foreskin back and was looking at the full pink meat of my penis’ head when he wondered what our penises tasted like. Now I was more than eager to have another mouth take my penis and I was pretty curious about what one would feel and taste like in my mouth so I suggested that we could suck on each other if he didn’t tell anyone.
So that’s what we did; we got on the floor and lay on our sides next to each other in a kind of 69 position and put each other’s hard teen wieners in our mouths. I have to admit, it was a pretty meh experience. Particularly compared to my experience with the older guy. It was probably the position we were in that made it kinda sub par. Anyway, after a while it was getting kinda tiring but I admit I was enjoying just having his dick in my mouth, plus I wanted to make him cum. A few minutes more of tolerating the bad position I decided to take control and pushed him onto his back with me on top of him on my hands and knees and from there I had a much easier time of swallowing him. He had stopped sucking me when I moved us and so I ended up rotating around while still sucking him until I was on my knees between his legs, my hands holding his hips and his hands on my head as I just devoured his penis. I remember feeling like I was a wolf or a wild cat just ferociously eating his dick off and his hands and bouncing hips were eagerly encouraging me to do it.
Obviously by the end of it all he came and I got to experience a penis erupting in my mouth for the first time and I got to taste and eat boy seed. After a bit of lying on the ground naked catching our breath we went to have our showers and then went to bed.
The next night we were already in bed when he asked what his sperm tasted like (I remember saying it was fine) and if he could suck on me and taste mine. I said sure and he came over to my bed, pulled my bed sheets up, pulled my boxer shorts off and did all the things I did to him the night before. He kept going on me until I came for him and I remember him saying that he liked the way my dick tasted.
We kept sucking on each other periodically over the next two years until I moved schools.

Wow! I enjoyed reading about your experience. Very descriptive. I wish mine would had been like that but drugs and alcohol gave me a different point of view. For some years I questioned many things but I concluded that I regret the fact that I experimented under the influence but not the act itself. As I grew older I started to fantasize about doing it again but sober and recently I started to open myself up to express, at least here, what I would want to do. Maybe these last six months I have desired more intensely than ever to be with a man.

[mash2014]

I was 15 and I had told my room mate at school (boarding school) how I had gotten sucked off by a guy in the park toilets one night and the conversation turned into him wondering what other guys looked like naked. I offered to show him mine if he showed me his and we both ended up getting undressed and showing each other our bodies. Looking turned into touching and I remember touching his chest, holding the back of his head in my hands and groping his butt. Of course we also ended up exploring each other’s now-hard dicks and he asked me if he could touch mine, to which I said “sure” and opened my legs for him to see everything. I remember him being very involved in inspecting my boyhood. There was a lot of gripping and squeezing and pulling and peeling. He would grip my entire genitalia at the point where it connected into my pelvis and pull. He pulled and squeezed my balls and I remember enjoying him stretching my sac out and gripping each ball in his hands and telling me he could feel the tubes connecting to them. He also seemed to love playing with my foreskin (he didn’t have one). We did all the things two naked, hard and horny boys do to each other, we rubbed our dicks together and made them kiss. We poked each other’s sacs with them. I remember that he had peeled my foreskin back and was looking at the full pink meat of my penis’ head when he wondered what our penises tasted like. Now I was more than eager to have another mouth take my penis and I was pretty curious about what one would feel and taste like in my mouth so I suggested that we could suck on each other if he didn’t tell anyone.
So that’s what we did; we got on the floor and lay on our sides next to each other in a kind of 69 position and put each other’s hard teen wieners in our mouths. I have to admit, it was a pretty meh experience. Particularly compared to my experience with the older guy. It was probably the position we were in that made it kinda sub par. Anyway, after a while it was getting kinda tiring but I admit I was enjoying just having his dick in my mouth, plus I wanted to make him cum. A few minutes more of tolerating the bad position I decided to take control and pushed him onto his back with me on top of him on my hands and knees and from there I had a much easier time of swallowing him. He had stopped sucking me when I moved us and so I ended up rotating around while still sucking him until I was on my knees between his legs, my hands holding his hips and his hands on my head as I just devoured his penis. I remember feeling like I was a wolf or a wild cat just ferociously eating his dick off and his hands and bouncing hips were eagerly encouraging me to do it.
Obviously by the end of it all he came and I got to experience a penis erupting in my mouth for the first time and I got to taste and eat boy seed. After a bit of lying on the ground naked catching our breath we went to have our showers and then went to bed.
The next night we were already in bed when he asked what his sperm tasted like (I remember saying it was fine) and if he could suck on me and taste mine. I said sure and he came over to my bed, pulled my bed sheets up, pulled my boxer shorts off and did all the things I did to him the night before. He kept going on me until I came for him and I remember him saying that he liked the way my dick tasted.
We kept sucking on each other periodically over the next two years until I moved schools.

Wow! I enjoyed reading about your experience. Very descriptive. I wish mine would had been like that but drugs and alcohol gave me a different point of view. For some years I questioned many things but I concluded that I regret the fact that I experimented under the influence but not the act itself. As I grew older I started to fantasize about doing it again but sober and recently I started to open myself up to express, at least here, what I would want to do. Maybe these last six months I have desired more intensely than ever to be with a man.

[goodniteswearer89]

My first time playing with another penis was when I was in the middle of going thru puberty it was my younger bro who is a few years younger than me and was just getting ready to start puberty. He came into my room one night and said he heard some friends of his talking about jerking off and asked if I knew what it was and how to do it. I told him I would show him next time we were home alone. A few days later we were home alone and he came into my room and asked me to show him so I told him to strip naked and I did the same. I then pulled up this website and showed him some stories about other brothers doing it along with brother and sisters doing it after reading a few stories I noticed he was getting hard and so was I. I then showed him on me by rubbing my penis he then copied what I was doing but said he didn’t feel anything so I then showed him by taking his penis in my hand and rubbing it up and down until he said he felt like he had to pee I told him that he was about to feel really good and kept going until he had a dry orgasm. It wasn’t until we did it again a few weeks later that he actually produced cum he asked me what that was and I then told him it was cum and it is what gets a girl pregnant when you have sex. Later on I explained to him some more things and showed him how to give a blow job. We only did that once though

[14471]

Although I identify as straight, my first sexual experiences were with another guy. We fooled around several times in the woods near my house, taking turns blowing each other, and fucking each other, but never to orgasm. One night, he spent the night at my house and after everyone had gone to bed, we decided to play truth or dare. After some oral and manual foreplay, I dared him to fuck me until he came. He agreed and got the Vaseline for lube. His cock was thick and about 6 1/2 inches and curved up. I lay n my stomach, naked, as he rubbed the Vaseline on his cock and my asshole. Although I was nervous, I was also excited as I felt the warm head of his cock press against my asshole. I grunted a little as he entered me and had a sensation of feeling full, once he was entirely inside. As he picked up the pace, I moaned louder and louder as he fucked me. Before too long, he stiffened and came in my ass. As he pulled out, I had a feeling of wanting more, but he was done. By the time I got some tissues, the come was leaking from my ass. I’ve never had another man come inside me, but it is one of my go to fantasies.

That's an awesome experience. My first experience was with my best friend also. We started in middle school.
Back rubs lead to "tickling". Which lead to stroking and rubbing each other. Eventually, we experimented with trying anal.
This took place over the course of a few years.
They were some fun and exciting times.

[wonderdick]

My first time was almost with a friend of mine penetrating me in my ass after we had made a pyramid of our empty beer cans on the coffee table. He asked me if I had ever been butt fucked and how amazing it felt. I was willing to give it a try. But I was so afraid of of being homosexual at the time and had never been with a girl and so I was unable to relax my asshole and he finally gave up. It really had me bent out of shape for a while, questioning my sexual identity as a teenager who achingly wanted to have sexual opportunity with a girl but was afraid and didn’t know how to make it happen.

My future girlfriend who befriended me and was very kind and patient, allowed me to work through my fears before I was ready and we finally had happy sex. We had a rocky sexual life after that and she had her own issues. She was like my practice marriage. We’re still friends many years later … she’s with another man and I’m with a woman who has always enjoyed sex and we entered the relationship without the hangups I and my first wife had had in our relationship.

[iamnaked]

My first time going all the way was with a much older woman, a widow.
I was 17 and she was close to 60.
I was on a service call fixing her yard sprinkler system. She flirted a little and I asked her if she wouldn’t mind if I stopped by after work on my way home to check the sprinkler system out when the timer turned it on.
She smiled and said yes.
Once there she told me to come inside when I finished for a glass of tea.
I purposely got soaking wet so she calmly told me to strip and give her my clothes so she could wash and dry them. I stripped in the garage and she threw everything in the washing machine and did not offer me a towel. I took a shower and when I came out she was naked.
I came out of the shower hard as a rock. We fucked and I lasted a whole three minutes. She was happy and we chatted and petted for an hour.
I got hard again and lasted twenty minutes.
I came over many times that summer.
I lost track of her and she moved away.