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I was 16 and she was 18 (and not a virgin)....we were sort of seeing each other for the most part and I think she was turned on to be my first....it was physically amazing, I had two orgasms (PM me if interested in details)...emotionally I wasn't really ready though

I was 16 he was 18, my boyfriend. It was the first time for both of us. It was great for him but horribly painful and a bloody mess (literally) for me, and I did not have an orgasm. I was young and stupid and thought I was in love with this guy. I regret now that it was him that I lost my virginity to as I spent many years with him and he turned out to be a very abusive individual

I was 20 she was 19. She wasnt a virgin and I preferred it that way. She showed me the ropes and was very kind and patient. I got better with time. Sadly we didnt stay together... we still talk though. Its complicated lol

) How old were you? 2) Same sex or opposite sex? 3) How was it? 4) Why that person at that time? 5) Any regrets?

1) I was 29 almost 30. 2) Opposite sex. 3) It was ok. I really didn't know what I was doing. 4) I did because she wanted to and I wanted to make her happy. I cared about her, loved her but looking back I was not in love. 5) I wish I had spokend up and asked her to be of more help. She was not a virgin. I think she liked it as we did it a few more times, but I think it could have been better. On the plus side I did learn a thing or two.

Thank you for taking the time to respond.


22
opposite sex
oral and vaginal
nervous, was ok.
pretended like a porn star, been watching porn movies for educational purposes
loved each other.
she was a virgin.

I was 14 and he was 13. It was four months after we started to fool around. We both loved it and did it many many times after that. To this day, sex with him--anything with him--was the best I've ever had.

We were both exchange students in NZ, I (US) was 16 and she (JAP) was 17. Both virgins.

The first time was rough for her I think, but the next few were ok. I don't think she really liked it till the last few, and those last couple of encounters will be burned into my brain forever (1st doggy style, and 1st time a partner moaned and screamed a little).

Why her? We were "in love" for a couple kids anyway. She was a real sweat heart, away from home for a year, and I was a tall, handsome, american dork. Sex took us right past the language barrier (although, she actually spoke english well enough to communicate complex ideas, but it took a little work).

I tried my best at the time, and my only regret is that we got caught by my host parents (found condom wrappers in the trash). That spawned a whole Rotary Club ordeal, complete with interogations and counciling, and it put a real damper on a couple of teenagers' sex lives.

She made me a teddy bear when she had to leave NZ, and we both cried. I still have that damn bear, and my wife thinks its cute as hell that I keep it.

I was 18 she was 17. I pretty much came as soon as my dick came in contact with her pussy. I didnt even get inside till the second time, lol. We did it alot after that and both got a whole lot better at it. Now its funny when i think how long it takes me to cum now compared to how i was then.

1) How old were you? 18

2) Same sex or opposite sex? opposite


3) How was it? memory fails me.


4) Why that person at that time? She was my g/f and I was desperate to get my nob into someone.


5) Any regrets? nope.

Thank you to everyone that has responded. I hope others have found this as educational as I have. Hope to hear more.

1) How old were you? I was 18 he was 20 2) Same sex or opposite sex? Opposite yes! 3) How was it? It wasnt bad for the first time 4) Why that person at that time? We liked each other and stayed in a hotel together 5) Any regrets? I did regret sleeping with him for the longest time now im ok with it.

I think I've answer3ed this before, but I'm doing it again.

How old were you? 2) Same sex or opposite sex? 3) How was it? 4) Why that person at that time? 5) Any regrets

It was with KK. I was 17 and she was 14. I think she enjoyed it more than I did,. because noone was home but her dad who was asleep in the next room. I was scared he would wake up, especially since KK can't be quiet during sex. I don't regret it all. She had birth control, and I used a condom, so we where safe. My only regret is that we got freaky really soon, and we had experimented with all kinds of sex by the time KK was 17. I think that is why we got into swinging. we was still hungry for new sexual experiences.

1) How old were you? I WAS ABOUT TWELVE-SHE WAS THIRTEEN (SEE MORE TEENAGE ADVENTURES UNDER EROTIC STORIES)

2) Same sex or opposite sex? OPPOSITE

3) How was it? GREAT!! I WANTED MORE!!

4) Why that person at that time? SHE WAS OFFERED BY MY FRIEND!!(SEE STORY)

5) Any regrets? NONE WHAT SO EVER!! WE DIDN`T KNOW AT THE TIME HOW GOOD WE HAD IT TILL MUCH LATER AND SHE DIDN`T GET PREGNANT (BY US AT LEAST!!)

1) How old were you? 2) Same sex or opposite sex? 3) How was it? 4) Why that person at that time? 5) Any regrets?
1) It was the night before my 20th birthday 2) with my boyfriend 3) He was AMAZING! You always hear people say it hurt and they didn't enjoy it, but damn. Yes, it hurt at first, but he went really slow for me until I was ready for the rougher stuff. I climaxed twice, maybe three times. 4) He's my boyfriend and extremely important to me. As for the timing...It was the night before my birthday. He's long distance so it was the first time we'd seen each other since we started dating. Our first kiss together progressed to the point where we naked in his bed and I pounced. 5) None. I have no regrets about him at all! I couldn't have found a better guy.

1) How old were you? 18

2) Same sex or opposite sex? opposite

3) How was it? it was ok. very special location, but maybe a bit more of time would have been nice. did not come, but was pretty close

4) Why that person at that time? was not really a bf, but kind of

5) Any regrets? nope.

I was 15, he was 16. We were both virgins. It was awkward. We had only been dating for 3 months and were each other's first everything... we loved each other as much as we were capable of at that time, I trusted him, and we both wanted to. His parents were away for the afternoon, so I seized the opportunity and told him what I wanted to do. He barely got it in before he started to lose his erection, I suppose he was nervous at the time but it turns out that was a regular problem with him.
I kind of regret that we did it so soon, since it totally changed our relationship. We discovered that I was hypersexual and he was not at all... he also had weird issues with sensation and didn't like being wet which of course negates most forms of sex! I also regret that I stayed with him as long as I did. He was convinced that we were going to be together forever but he was not interested in my pleasure or my orgasm at all and all sexual contact had to be on his terms... but when you're that age I guess no one knows any better.

MF I was 13 she was 15, in the schools garden shed (who says romance is dead lol) Because of my then Rugby playing, I was a bit of a school celeb, before my Injurt, and so a lot of girls wanted to be with me, (jeez that sounds so conceited.)
this girl Amanda had done it before, so we shut purselves in and did the deed. I was terrible I came so soon.
MM I was 15 he was 18, at a Irish Schoolboys Rugby academy, he came into the shower when I was there, noticed me looking at him, so came along, and just grabbed my cock. Had my first anal experience then, didnt really enjoy it, and still dont although im Bi.

1) How old were you? I was 17, he was 18, he wasn't a virgin

2) Same sex or opposite sex? Opposite sex

3) How was it? Eh, so so, I was drunk

4) Why that person at that time? I decided I would lose my virginity on Senior Trip, I met him, he was cute, we hung out, so I went ahead and did it.

5) Any regrets? Nope

1) How old were you? 19 2) Same sex or opposite sex? Opposite 3) How was it? The comfort of being inside of her was probably the most meaningful feeling I've had in my whole life. 4) Why that person at that time? She was my first girlfriend. We loved each other. We became really involved as time progressed and experimented a lot of things before we both agreed we were ready to fuck. 5) Any regrets? Not really, it happened and it was time. We no longer see each other.

1) How old were you? - I was 12 he was 18
2) Same sex or opposite sex? - Opposite
3) How was it? - Painful and scary
4) Why that person at that time? - He was looking after me and had me alone for a few hours
5) Any regrets? - I wish I had known more about sex so it wouldn't have been so scary

1) How old were you? 2) Same sex or opposite sex? 3) How was it? 4) Why that person at that time? 5) Any regrets?

1) I was 17, he was 23 and not a virgin.
2) Opposite sex
3) Uncomfortable at first. He's still the biggest person I've ever been with in both length and girth. It wasn't something I wanted to have for the first time but it did end up bringing me pleasure that night. I didn't feel anything breaking .. I don't know if I was meant to and had no bleeding at all. I just constantly felt like peeing.
4) Looking back, it was naivety and really just to know what sex was like. We hadn't been dating for long and it wasn't serious. We ended up being together for 5 years.
5) Not really, probably would have preferred if it was "special", but eh.. curiosity.

1) How old were you?
15 almost 16

2) Same sex or opposite sex?
Same

3) How was it?
Very enjoyable.

4) Why that person at that time?
A sleepover at my house with a bunch of girlfriends. I awoke (between 2 and 3 a.m.) to find one of the girls between my legs and licking me fervently. I was very startled at first...but found it so enjoyable that I spread my legs as wide as I could (bit my lip to surpress my moans and groans) and allowed my "friend" to indulge herself without interuption
5) Any regrets?
Yes...wish we kept in "touch" with one another!!

1) How old were you?
25 years old.
2) Same sex or opposite sex?
Opposite.
3) How was it?
First two attempts were unsuccessful - my semen was thrown on my spouse's thighs and pubis. Only the third load of cum irrigated her womb.
4) Why that person at that time?
It was my wedding night with my spouse.
5) Any regrets?
No.

1) How old were you? 12

2) Same sex or opposite sex? same


3) How was it? great


4) Why that person at that time? He lived across the street and we had always hung around and were in the same school.


5) Any regrets? No

I lost my virginity in a whore house. Went to La Grange, Texas which was about an hours drive from home when I was 16-17. Went with several other guys and was scared shitless! Finally chose a nice looking woman and back we went. She asked what I wanted and I told her it was my first time and just wanted to fuck. She took me by the hand and lead me to the bed and told me to strip. She stripped at the same time and I guess that is where I got my hairy pussy fetish. She then led me to a wash stand with a big bowl of warm water and took my cock and balls and slowly washed them. That was one of the big deals about the Chicken House. We then went to the bed where she massaged my back and kissed me all over the back and neck. She rolled me over and did the same to my chest and belly. She then told me it was time to feed her kitty. She had me get on my knees between her legs and get as close as I could to her kitty with my cock. She reached down and guided my cock into her and told me not to move but just enjoy her warm wet kitty. She squeezed her pussy on my cock and about the fourth time she did I shot my first load in a real pussy! She told me to just lay on her and enjoy. My cock stayed hard the whole time. She did let me fuck her and shoot another load. She then took me to the wash stand again and cleaned me up, saying she didn't want me to go home and my mother smell her. My cock stayed hard the whole ride home!

Is was 13 and she was 13 too, or possibly 12. She was one of my sister's friends. We actually went out for a bit, I used to jump out of her window when her mum came home. As for any regrets? Well I used to hide the the condoms sometimes so I could fuck her ass, which was a bit underhanded. And I was still hung as a kid so I should have been gentler.

1) How old were you?
I was 19

2) Same sex or opposite sex?
opposite sex

3) How was it?
Fun. She had more experience than I did, and we were both super horny.

4) Why that person at that time?
She wanted to, and I wasn’t going to say no.

5) Any regrets?
None what so ever.

I was 19 and in college; he was about my age or maybe a year or two older. He was coming down to visit me and I just decided that it was time that I lost my virginity. It was a little uncomfortable but not painful and I didn't have an orgasm. As a matter of fact I didn't have an orgasm from sex for the next four years - all through college. Missionary and doggy just didn't do it for me. I didn't have an orgasm until a guy whom I met on vacation in Europe went down on me. That night I learned what orgasms were all about !! I still need talented tongues to this day.

This may sound weird, but I won a contest to be the first to lose my virginity. I was 14 and at a friend's house. It was a different era and I lived in a small town, so parents weren't afraid to leave their young children alone at home with friends. There were 4 of us guys and the local, "promiscuous" girl. She was basically a slut and would fuck just about anyone. Her fetish was "deflowering" virgins. No matter what, she was planning on doing all of us, but she told us we had to decide in what order. She told us she was going up to the bedroom to get ready and to send up the first virgin when ready. We decided to cut cards to see who went first. I got a 9 and was really worried, but luckily everyone else got lower cards. I was scared and not really sure that I wanted to go first, but I had won and I couldn't chicken out now, especially in front of my friends. I would never have heard the end of that.

I walked up to the bedroom and opened the door. She was lying there on top of the covers, completely naked. My cock started getting hard immediately. All my fantasies were about to come true. A beautiful, naked girl was lying there waiting for me to fuck her and wanting me to fuck her!!! She told me to undress. As I was undressing, she spread her legs invitingly, giving me a clear view of her pussy and beckoning me to come and take her. I pulled down my pants and out popped the biggest, hardest erection that I had ever had. It felt like my cock was going burst from the pressure. I crawled onto the bed and laid on top of her. I reached down and grabbed my cock to guide it into her, but I was shaking so much that I missed. My cock slid underneath her and between her ass cheeks. She noticed my inexperience and offered to help. She reached down, grabbed my cock and guided it into her warm, moist pussy. I knew that blowjobs felt great, but I wasn't prepared for how wonderful and amazing it felt sliding my cock into a pussy for the first time. I was in heaven and needless to say, I didn't last very long. After cumming in her and dismounting, she told me to send in the next in line. She ended up doing all of us twice.

It was clumsy, quick and my inexperience definitely showed, but I still loved it. My only regrets are that I didn't last longer and I wish I wouldn't have fumbled around like an idiot.

The why was because I was a teenage boy and some beautiful teenage girl was offering me her pussy. I would've been crazy to turn it down!!!

I was 12 he was 22. At a party my older sister was having. He asked if I would take a ride on his motorcycle. I was a little scared but a little alcohol and next thing I new we arrived at his place. He introduced me to his roommate and his girlfriend and then took me to his room, told me he was going to fuck me. He removed my jeans, laid me on the bed, slid off my panties, spread my legs , fingered my pussy then slowly worked his large cock into my tight pussy. He pulled out, came on my tits and tummy and we returned to the party. That was how it happened for me. No regrets, he knew what he wanted and made good on his promise!