First times and experiences

[mash2014]

I have a memory of a girl from my neighborhood who was 13 at the time and I was 8. She came over to my house, I believe to keep me company since I had been sick and my parents had to go somewhere. Anyway, she started to show me hers I showed her mine. I remember she even took my penis and inserted it into her pussy. I don’t remember how far it went but I do remember going inside of her. I must have been placed at that age, and I don’t recall any orgasm.
Then, when I was around 13 my mom sent me to a tailor to get some dress pants and he was gay. I clearly remember as he took measurements he’d put his hand on top of my penis and rub it. A cop joke of time he’d touch my ass and he took his fingers and went from top to bottom through my crack and I felt his fingers make a stop at my asshole and tried to push his finger in. Somebody walked in and he stopped and shortly I left. I remember that night I was so turned on because it was the first time someone had touched me intimately.
They, when I was 14 I went to this guy's house and we started to drink. Suddenly he had his hand rubbing me. He opened my pants and I allowed him to touch me, although I was highly intoxicated. We ent down in each other.
About 1 year later I had my very first M-F intercourse experience. I had my orgasm almost instantly but I kept thrusting to make her think I knew what I was doing.
I revive these memories when I masturbate and I don't regret anything. There have been many events that I do masturbate as I remember, but these are my first experience.
Do tell your first time.

[goodniteswearer89]

My first time happened when I was 16 it was with the neighbor girl who was 13 getting ready to turn 14 at the time. We had been dating for about a year and had done a little fooling around a few times before we decided to go all the way. After being together for about a year decided it was time to go a little farther than occasionally kissing and holding hands. Unfortunately due to her parents being kinda strict we couldn’t do much at her house and with me having 3 younger siblings it was hard to find alone time at my place so we would tell her parents we were going for a walk and would walk to our other neighbors house and they had a trail that lead into the woods not to far from their house and we found a good place to make out and one day after some intense making out we decided to go a little farther and she let me feel her boobs and I let her feel my dick. A few days later we were again making out at our spot and we decided to go even farther and we both stripped and she gave me my first hand job from a girl and I got to finger my first girl. It felt so great to have her hands on my dick and her pussy felt so good. We stuck with doing this for a little while longer until we both felt like we were ready. After deciding that we were ready we made a plan to sneak off to our make out spot and I grabbed a condom that my parents gave me and we went to our make out spot and proceeded to make out and eventually have sex.

[tryagain]

Mine was with my best friends bro
We'd been showing each other for a while.
On a sleepover she was asleep in the next bed and he snuck in.
I got onto the floor and let him do it.

[goander]

My first time was in a friend's twin bed with a group of virgins listening to us through the door.

[mournmane]

My first time was when I was seventeen. I was at my friend's house, and she was sixteen. We were looking at <a href=https://www.dickhardon.com/big-dick-pics/>big dick pictures</a> for jokes, and we started to kiss. It was accidentally, but I began to enjoy it. I knew that it would be my first sex, and luckily I always had a preservative in my pocket for such cases. The following day when I was going home, I was so happy that I had my first sex in life. But now I understand that it was awful because I had multiple couplings with that girl again, and I understood how terrible that sex was.

[rathb69]

For a long time I looked back at my first sexual experience(s) being when I did things with girls in my teens, finally leading to going all the way with my girlfriend in my late teens.

Now I look back and realize my first semi-erotic experience was actually with another boy, groping/fondling his erect penis when I was 13 and he was 14.

[wankwank]

the first time i got fucked i was about 11 he was about 13. we had been wanking together since i was about 8 and he was 10. i actually taught him how to masturbate. we use to sneak off onto the factory roofs and wank together looking at porn mags.

all i remember was it hurting and wanting to stop but he said just a bit longer and then he came inside me. i wasnt too into it but every now and then i would bend over for him.

the first time i fucked someone i was 14 and the guy was in his late 40's. we started out masturbating together but i would push for more. i wanted to know what it felt to slide my cock into a hole. i dont think i made it much past 10 pumps and i shot my load.

[wheelboy2]

My first time experience was when I was 13. I'd been experimenting with masturbation for a year or two. One day I had visited a school friend, a bus ride away, and a heavy fog descended and all buses were cancelled. To return home a took a short cut over a deserted hilly area hoping the fog in the next valley would be clear.
As I stumbled down a trail, someone passed me, an older man, walking faster than I was. I took no notice of him. He changed direction and went down another trail. I carried on.
Suddenly he was behind me, having doubled back. He grabbed me by the shoulder from behind and he told me to stop and put my bag down. Then he said, "Reach behind and play with me like you play with your own cock." I reached behind and felt his large hard erection. "Play with it" he urged. I knew enough to start jacking his cock. He undid my pants and felt my cock and balls but I don't remember getting an erection. I jacked him steadily as I'd done with my own cock many times.
Eventually I could feel him thrusting slightly against my stroke and I figured he was ready to come. With a few harder thrusts and a groan he came.
Then he just said, "Ok walk away and don't look back". And he was gone. I walked off and then stopped to fasten my pants properly and I felt his semen down the back of my jacket where he had shot it. I cleaned it off the best I could and carried on. I guess it was total sexual assault but it really didn't bother me and I never said anything about it to anyone. It was the first and only male cock I have ever felt. A friend and myself masturbated together a year or two later but we never touched each other. I'm not at all gay but I would like to feel another male cock - both soft and hard. I would like us to masturbate each other.

[gregg99919]

My first time was when I was 15, my brothers girlfriend who I think was 21 then, was left alone with me while he went and picked a friend and would be back in about 30 minutes. She talked and teased me, and then got serious and asked if I ever had sex, I told her no, no way I ever had yet. She tease me for a few more minutes, next thing I knew she had my pants down and push me back on the couch and was fondling my cock and balls and got me worked up with a couple of strokes. I got so hard and she proceeded to pull off her slacks and panties, I couldn't believe it. After telling me to never tell anyone, not even my brother, and she would make me feel so good, She pulled a condom from her purse, ripped it open and pulled it up over my cock, I never even seen a condom before then. She straddled me and work my cock in her. I dont think I lasted more than a couple of minutes before I cum and it was over. She was something else. I still think back about it often.

[b11s10]

That is a dream come true for most young men. Awesome! Thanks for sharing.

[lexington]

My first time I couldn't find her vagina, and pretented to massage her. She eventually said "lower, lower". I could not believe it was that low!

[maturebator]

My first masturbation experience went as follows: It was a sweltering August day and I was sweeping out the garage, wearing just cut-offs and sneakers, when in walks the kid who lives next door. He was a few years older than me. I was 12. He waltzes right up and asks me if I knew how to jack-off. Being yet naive, I had no idea what he was talking about. He was more than willing to give me a demonstration and he urged me to take out my cock as well. I did as he suggested.

Using what I call a "pencil grip" (thumb atop penis, index finger wrapped under, other fingers tucked in), he began stroking his cock, which became immediately erect. I copied his style and shortly I had a nice, tingling boner of my own. It felt fantastic.

Then, I head my mother calling from the back door, about lunch. I asked the neighbor kid what to do next and he replied,"Just keep on doing that, you'll find out." And I went in the house for lunch.

At bedtime, I kicked down the covers and went to work on my young cock as I had been shown earlier that day. Again, an immediate, tingling erection. I began pumping it, going faster and faster. Oddly, my legs extended, my toes pointed down, my butt clenched and I experienced my very first "dry" orgasm. It was like a mystic experience. I felt like I'd opened a door to another dimension. One I had ever intention of visiting and exploring, again and again. I wasn't much on style, of course, but heavy on intensity and frequency, as I imagine most of us were.