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.

[pete120]

Well, I am pan sexual submissive bottom vers, My first time was with my friend Joe. He was 6 ,and I was 7. He spent the night ,and I would ease the topic of erotic topics into his brain. Then slowly, he would want to try stuff with me. The first was when we were watching "New jack city". He liked black studs ,so I showed him even I could make him feel good. I locked my door and took off my clothes. He blushed and said okay yeah I have a hard on. We just had adolescent sex all night long. I still get aroused by his soft ,white ,peach fuzzy ,skin. His cock was a little smaller than mine. He had lots of peach fuzz around his cock too. I loved it. I shaved my whole body around the age of 6. After that first time, we had sex almost every week. I had more experiences with other fWBs too. From ages 6 all the way up to 65. I loved teaching them how to pleasure cock and ass.

[valleychrish]

My first time with a girl, it was my little sister. I was 12 and she was 10. Our mom came home drunk with 2 men. Me and my sister watched from her room as our mom was having a threesome. I got really horny and pulled my sister’s panties down and fucked her.
My first time with a guy I was13 and my sister was 11. It was another time our mom came home drunk with a man. They were making out on the couch and me and my sister were watching from her room. Our mom passed out and the man was just sitting there. I pulled my sister panties off of her and dared her to walk to the kitchen with just her shirt on. She did and the man got up and followed my sister to the kitchen. I waited a couple of minutes and peeked out of the room and there was my sister blowing the man. After they were done my came back to the bedroom and the man left.
Then a couple weeks later me and my sister were at the mall waiting for our mom to pick us up and we figured she forgot and as we were about to walk home. My sister saw the man she blew. She went up to him and asked for a ride. We got in his car, my sister sat up front and I sat in the back. As we left the parking lot he asked if he could stop at his place and we said yes. As he drove he reached over and started feeling my sister up. My sister spread her legs and he reached down her shorts and was playing with her pussy.
When we got to his place he asked if we could come in and we did. We got inside and he had us sit on the couch and he went into his bedroom and came out with some weed. He asked if we wanted to get high and we both said yes. He sat between us and lit a joint. We passed it around and got pretty high. After a while I looked over and he was making out with my sister. He pulled down his pants and his cock was hard. He had my sister give him a blowjob. I was just watching and he noticed and asked if I wanted to blow him and I don’t know why but I wanted to. My sister sat up and he pushed me down on him. I wrapped my lips around his cock and started going up and down. For the next couple hours me and my sister took turns trying to get him to cum.

[spunkluvr]

When we were both eleven, my cousin asked me what "wank" meant - he'd heard the word in the school playground but didn't know its meaning. So, as both sets of parents worked full-time and he lived nearby, I took him home and showed him. I laid naked on my bed and started to stroke my little cock and he sat next to me to get a closer look. He examined every millimetre of my tiny prick, especially when I peeled back my foreskin exposing my baby-pink knob - and it was at THAT moment I realised that exhibitionism was going to be my number one fetish, although I wouldn't have known the words at the time.

Happily, he joined in and as soon as I saw his hairless little cock, I knew it was going in my mouth - I'd been dreaming of sucking cocks since I started wanking, aged six. No spunk of course, but I didn't care - I actually had a cock in my mouth! It was only a week later that I sucked off a thirty-year-old neighbour and got my first mouthful of man-spunk. Once I got the taste I was hooked for life!

[spunkluvr]

. . . I had more experiences with other fWBs too. From ages 6 all the way up to 65. I loved teaching them how to pleasure cock and ass.

That's got my cock rock-hard!

P.M. me? (if you can)

[wanklover]

My first masturbation experience was when I was 13 and approaching my 14th birthday. I had been told nothing at all about sexual matters at that time but soon found out how to wank/jerk. An enormous shock but boy what a good one especially the throbbing of my cock at the end. My first proper ejaculation was about 3 months later. I was 20 before I ever touched a girl sexually. This happened whilst on a holiday with a young lady that I met. We found a quiet spot in a field one afternoon and I got my hand down inside her slacks and her knickers. I didn't really know what to do but penetrated her pussy hole and finger fucked her. She did actually cum although I didn't realise it at the time. She didn't touch me at all & I was too shy to say anything to her. I'm guessing she didn't know what to do to boys. I walked around with a stiff hard on for the rest of the day trying to hide it !! I was 23to24 before I lost my virginity and fucked a woman. She was a friend but not romantically linked to me. One night as we were chatting in my car after a night out she asked me if I fancied having sex. By now I was desperate to have sex so said yes. We drove to a quiet spot and fucked. Oh my god !! Cumming into a woman's pussy hole was sheer, total ecstasy.

[lnlgrl137]

In high school my very first girlfriend and I were able to have a lot of sleepovers because no one knew we were dating. Her grandma would bring me over and we would mess around a bit but not too much. Her family was super religious so we were usually scared to. One night grandma slept out at a friend’s house after going out for cards and left us at her home alone. That night was amazing. Megan undressed me and kissed me and touched me so gently. She laid me back on the edge of her bed. I still don’t know where she got it but she pulled out a dildo. It wasn’t long but it was very thick. I was scared it wouldn’t go in. She held it against her like the dick belonged to her and rubbed the massive head of the thing against my clit. All I could do was impatiently squirm and rock my hips up, trying to catch it on my entrance. Once I began begging she started to push it into me. It hurt a little to finally have my pussy stretched. I’m sure I winced because she leaned down and kissed my neck. She went slow so she didn’t hurt me any extra. Once it was in as far as I could take she would take long slow drags in and out of me. The head of the toy would come almost all the way out. I got this delicious tingle I’d never had before. It must’ve only been six or seven strokes like that. I remember thinking “oh my god that’s good”. Right after that my back was arching up off the bed and I nearly howled with ecstasy. I didn’t realize until much later that it was my first orgasm. I feel so blessed to have lost my virginity that way.

[wonderdick]

Beautiful story