First sexual experiences

[mash2014]

How was your very first time? With whom? Was it a “forbidden” partner? If you could go back in time, would you change anything?

[dlihret]

I was a bit of a late bloomer. Didn’t have penetration sex with a woman until 20. Wonderful feeling. I wrote story about it.
Jerked off with some buddies in jr high and high school.
Never had an orgasm I didn’t enjoy.

[wanklover]

My first sexual experience was masturbating !! Absolutely wonderful. My first sexual experience with a girl was masturbating each other also wonderful. First fuck was a disaster !! I was too excited & shot my load as soon as I penetrated her pussy. Wasn't a girlfriend as such either, just a good friend. Wrong girl, wrong place (Car parked up in a dark, dead end road) & pretty much regret it. I needed a really experienced older lady who I had some emotional attachment to, to help me along.

[ragnarl]

My first sexual experience was being naked with some of my friends at the lake where we swam in the summer. Exploring and looking.....first fingering was with my sisters.....first full penetration was with an aunt who was 3 years older than me.....she was 14.....we were a group of kids playing games on late summer nights, under the midnight sun.....and often ended up naked

[matureplayer]

How was your very first time? With whom? Was it a “forbidden” partner? If you could go back in time, would you change anything?

It was great … but took some tries to “master”. She was my college girlfriend of about a year and a half. She had been raised in a religious family and high school, and was still a virgin as was I. When we started dating it was weeks before she let me touch her breasts, and months before I got my hand into her pants. But once we got there she liked what we were doing. When I finally got her pants off I could finger fuck her, and suck on her nipples and could get her off every time. She would stroke my hard cock while I did that, and usually after she came and focused on me she would make me shoot. We did that often, usually in her dorm room or my dorm room with a towel under us to catch our cum. I didn’t want to pressure her for more, and was pretty happy with her skillful handjobs. Finally one weekend her roommate had gone away, and she took me back to her dorm room. She closed and locked the door, then just said “Let’s really do it.” She opened her nightstand drawer and took out a condom, holding it up to show me. Our clothes came off fast, we lay together and started playing as usual. Of course I had been hard from the minute we entered her room, but once she was wet she picked up the package, took out the condom and rolled it down my shaft. She laid back, spread her legs and guided me over her. She put the tip at the entrance of her pussy and I very slowly pushed in. I guess with using tampons and the finger fucking her hymen was not really a barrier. I groaned loudly, amazed at the tight hot flesh around my cock, so much more stimulating than a hand (hers or mine!). I started to thrust slowly in and out, but the excitement of finally getting real sex and the incredible tightness was too much and after about 10 strokes I moaned and filled the condom, prematurely. We lay together a minute, then I pulled out. She said not to worry, but I quickly got to work and masturbated her to orgasm as a consolation. We did it several more times like that, missionary style, and I got better at controlling myself, but she still wasn’t coming before I could not wait any more and filled the condom. Finally one night we changed things up, I was sitting at the head of the bed with a pillow behind me. She straddled me, and could control her movement against me. After a couple minutes I leaned down and started sucking on her nipples and after another minute bingo - she exploded in orgasm and I was not far behind! Her first fucking orgasm.

Would I change anything? Would try to get to the real thing sooner, and with hindsight could have made her first time better knowing what buttons to push so to speak.

[steelydon]

Vey hot matureplayer. You should make this into a story.

[wheelboy2]

How was your very first time? With whom? Was it a “forbidden” partner? If you could go back in time, would you change anything?

It was with my first g/f at age 16. We felt each other in a shop doorway one night. She had the biggest tits I've ever felt. I'm not a big tit person though. We first fucked in her aunt's house, playing Russian Roulette doing it bareback and withdrawing to come. I'd never heard of women orgasming then so she never did it with me around. I went out with her for 3 months. Sixty years later she's a facebook friend and we never mention the fucking we did.
Would I change anything? Yes I'd suck her cunt, make sure she orgasmed and I'd wear a condom.

[iamnaked]

I lost my cherry at 17 to a 27 year old chick. I became her, ‘Fuck stick’
She called me, we fucked a couple of dozen times but she only mounted me, never sucked or let me eat her.
She was in a lesbian relationship and her girl understood her need for a dick now and then.

My first do everything sex was with a 53 year old woman when I was 19
She made me do things til I got it right.

[ragnarl]

I lost my cherry at 17 to a 27 year old chick. I became her, ‘Fuck stick’
She called me, we fucked a couple of dozen times but she only mounted me, never sucked or let me eat her.
She was in a lesbian relationship and her girl understood her need for a dick now and then.

My first do everything sex was with a 53 year old woman when I was 19
She made me do things til I got it right.

Lucky boy. I have always enjoyed older girls and women. But I often find myself masturbating to images of younger ones…..

[mash2014]

I've always liked older women. One of my early fucks was with a woman who was in her 50s. I don't deny that some young ones get me really hard but there is something about a mature woman that excites me more. I find myself masturbating thinking about older women and very few times I do it thinking about young ones.

[mash2014]

I masturbated for the very first time at age 12. My first fuck came a couple of years later. I inserted my cock into her pussy and I guess not even 1 second had passed when I came inside her. I kept thrusting until my cock went limp. A week later we did the whole 9 yards and this time I managed to control myself and it was partially because I went down on her. Ever since I go down on any woman I have sex with.

[spunkluvr]

Wanking at six, sucking my cousin's cock at eleven.

[iamnaked]

Lucky boy. I have always enjoyed older girls and women. But I often find myself masturbating to images of younger ones…..

Yeah those young bodies sure are cute. No doubt !

[svengalideck]

...
My first do everything sex was with a 53 year old woman when I was 19
She made me do things til I got it right.

Such a pig! You messed up and got a reward!! WTF

[iamnaked]

Such a pig! You messed up and got a reward!! WTF

I never thought if it that way !
Hahahahaha

[rathb69]

I was a somewhat late bloomer and I didn't jack off to orgasm until I was 18. Although I played around with girls in high school (mostly intense petting, no orgasms), my first fuck to orgasm was in college.

Even though nothing really happened, I now consider my first sexual experience to be when I was 13 and played with a 14 year old friend's erect dick when he pulled it out to masturbate. I had no idea what I was doing, but this brief experience was definitely sexual.

If I could go back and change something, the first thing would be for me to know more about sex and what I was doing.

So then, I would have continued to stroke my friend's penis when I was 13 until he ejaculated since the reason he pulled it out was to "show how he made white stuff come out". I also would have done a lot more exploring with another friend during sleepovers since we slept in the same bed.

When I fucked for the first time (my new girlfriend in college), I was rock hard and penetrated her, but although she had an orgasm I did not that first time. If I had to do it again, I would have kept going until I also had my first orgasm inside her (that would come a few days later).

[topcat]

How was your very first time? With whom? Was it a “forbidden” partner? If you could go back in time, would you change anything?

First proper girlfriend when I was 17 (she was 18). Used to spend most weekend nights at her parent's house. One weekend her parents were away, we spent the night making out on the couch. I finally found the courage to touch her breasts, she helped me take her bra off to witness naked breasts for the first time. Later on, I encouraged her to touch my penis and she gave me my first ever hand job. It was over in seconds.

I wish I had paid more attention to her body and known how to bring her to orgasm, although she taught me that in the coming weeks. I wish I had suggested sex, although being young and immature I wasn't totally sure what to do. I guess she would have helped, although I think she was a virgin too.


First intercourse was with my best friend on a summer home from Uni. Drunken night out, crashed at a friend's place and forced to share a bed. Kissing led to touching led to masturbating each other and finally intercourse. Wasn't much to write home about but it got that monkey off my back

[jemstone]

Love these testimonials-- or teste-monials-- about first sex. I first played with another cock at age 14, he 13-- my "Scout Grope" story here on ST-- but I was a virgin when I got married at 21. Started dating my wife in our sophomore year, lots of heavy petting, sometimes even naked, but no penetration-- so worried about pregnancy. On our wedding night I FINALLY was going to slide my hard cock into her warm, wet pussy and I came almost immediately! Waited so long for that. It was our honeymoon so I had more chances (but still never lasted long).

[agentoffortune]

How was your very first time? With whom? Was it a “forbidden” partner? If you could go back in time, would you change anything?

My first experience with mutual nudity and then sexual exploration was with a neighborhood girl when we were in our mid-teens (the redhead from my "Strip Poker" story I posted here). It was clumsy and awkward, as you might expect, but also hugely exciting for both of us.

It was 'forbidden' only in that we weren't as careful with birth control as we should have been. Thankfully. there were no unexpected surprises.

No, I don't think I'd change a thing about it now that I look back on it.

[casefyykins]

as I recall, it was a friend of my mother's