I was 9, she was 22 and a model

Posted elsewhere:

To add to that, I was 16, he was 25. I don't think I was too young for sex, and I'm kind of glad that I missed the stereotypical high school bullshit that accompanied some of my friends' first sexual experiences. I do, however, think I was too young for the relationship that ensued. I played some pretty cunty mind games that I am NOT proud of, and didn't have the maturity to deal with the fallout when it all went to hell.

 

I waited until I was eighteen. My boyfriend was a hot musician, and a sweetheart. I knew I wasn't in love but he was a good friend and I felt safe with him.

I was never afraid of sex or anything, just hated most of the males in my vicinity.

 

It's okay, don't blame yourself. At 25, he didn't have any maturity either.

Focus: I lost my virginity, the Halloween before my 21st birthday, in the backseat of my parents car. I so drunk, I could hardly walk and I'm fairly impressed that I even managed to get it up. It was an awkward event, me being 6'4" and trying to unsuccessfully lay down in the back seat of a Nissan Altima. It was kind of nice, as all I needed to do was pull up my pants and drive her home - it almost makes me want to buy a caravan.

Boy, that car brings back memories.

 

I was 16 and we were at my boyfriend's house working on a school project. He was my first love and all that, so I'd say it was well worth it. We dated for 2 years and the emotional fallout was ridiculous. However, I'm glad it meant something to both of us and I didn't lose it to some horny frat boy in college.

 

18 in a Holiday Inn with my then girlfriend who was less than 10 days older than me and also a virgin. It was awkward as hell, we had no idea what we were doing and it ended in blood and crying with neither of us approaching an orgasm.

Still though, it brought us closer together and emotionally and we had lots of great sex later, I'd say it was a good experience overall.

 

I was 18 and a freshman in college. It was pretty early in the year on a Friday, when my friend went to smoke a cigarette and asked if anyone wanted to go hang out outside for a bit. I went with him and we started talking with these other freshmen girls who wanted a cigarette (oral fixation yay!) and after two hours of sitting outside talking one of them mentioned virginity which led my friend to mention me. I saw her eyes light up immediately and knew that I was going to lose it that night.

8 shots later we had sex.

Still three years later she was the only girl to give a blow job with a tongue piercing. I make it a goal to look for tongue piercings when I go out, because that felt amazing.

 

I waited until I was 18 too...."waited", yeah, that's it!!

Lost it about 2 weeks after my 18th birthday, to a girl from northern Virginia who I'd met a month or so earlier at a model UN thing in DC (yes, I was a nerd, but it helped me get into college plus there was a ton of hooking up at every model UN event I went to). She said it was her first time too, although in retrospect this was not the case*. I'd driven down to DC to hang out with her a couple times but the opportunity never presented itself; finally we just told her parents we were going out to a movie, drove off to the woods somewhere, I put the driver's seat of my VW GTI all the way back, and she climbed on top and went to town. I actually lasted about 10 minutes with no unusual performance one way or the other, so I was pretty happy with that.


* - I base my years-later conclusion that it wasn't her first time on a few independent facts, none of which is conclusive on their own but together make it pretty likely she'd had at least one dick in her before me. First, her cherry was already popped (she had been a competitive figure skater until a few months before we met, so nothing suspicious there). Second, most 15-year-old virgins (she was 15 and I was 17 when we met but turned 16 and 18 before we had sex) don't blow guys they just met 3 hours earlier. Third, after we broke up a year and a half later and I started fucking other girls (none of whom claimed to be virgins), I realized she was WAY too good to have been a virgin. Fourth, she was batshit crazy and a compulsive liar.

 

I was 22 and a senior in college. The only reason I can really give for why it took so long is that I have very bad luck. In my entire four years of high school, I had one summer romance and no boyfriend. My summer romance was my co-counselor at the camp i worked at the summer before my senior year of high school. He was weird, awkward, and highly medicated for emotional issues. We didn't get past kissing.

In college, I almost had an affair with a married man, but his wife caught us before I could even get my shirt off. I regretted even starting this, because his wife and I have mutual friends and even today, if there is a social event with this group of friends, I have to either arrive before the wife and leave before she gets there, or wait until she leaves before I can arrive. This all happened when I was 19.

At 21, I moved out of my parents house and into student housing. I spent that entire year as far away from the apartment as possible because my roommate was extremely overweight and dating a guy who was bigger than her and the two of them REALLY liked to fuck. That was also the year I wasted dating a closeted homosexual. I have no idea why I stayed with him for the entire school year, but I was (am) weird and awkward and too lazy to find something better.

I finally lost my virginity during Spring Break. On a surfboard in a sun room at the house we rented, nearly blackout drunk. I was 22, he was 20. We ended up being FB for the entire spring semester. From what I remember, the sex was pretty good. He apparently lost his virginity at 16 to a friend of his mother's who taught him well, so he really knew what he was doing.

As for whether I think I was the right age, absolutely. Maybe I was a year or two too old, but at least I didn't have to deal with the high school bullshit.

 

I've posted this before but can't find it so...

I was 16 and he was a couple years older. We weren't a couple, just good friends.* He told me hit wanted "to hit it doggy style" and after I assumed the position, he stuck it in my butt. No lube, no warning - I honestly, to this day, believe it was not intentional. About the second stroke I said I wanted to change positions and we switched to missionary on the floor (why not the bed? no idea). Obviously, the butthole part was terrible but the rest wasn't bad. Several weeks later the topic of butt sex came up, how he'd never done that etc etc and I told him what he had done that night. He was shocked and apologized but the damage had been done (so to speak) and we never slept together again. People ended up hearing the story and thought it was hilarious that anytime they said "Timmy D" I would turn 3 shades of red.

*He did sing this song to me all the time though.

 

I was 14, pushing 15. She had just turned 18. We were each others first everything, and it was a mutually enjoyable experience. And we had been together for almost a year before we took that step. Looking back 14 probably sounds a little young for loosing your virginity, but I'm glad it happened with love, and mutual trust and respect.

I to this day get along wonderfully with the woman in question, in fact she even made the trip down to Lackland A.F.B, with my parents, for my graduation from basic training. (Which really pissed the Wife off.) And every time I make my way back to Oklahoma we usually make it a point to hang and catch up. (Non sexually.)

All in all, best step sister ever.

 

We were both 18 the first time we had sex. I was a virgin, she wasn't.

Afterwards, we were both virgins.

 

I was 15, so was she.

We had been dating for about a year (we were that couple in high school) and she came up to me one day at lunch and made the declaration that she was ready.

I bought condoms and went over to her house one night when her parents weren't home. She had bought candles and a new matching bra and panties set. When the time came to seal the deal, I started in and you would've thought I jammed a fire poker into her--she clearly wasn't relaxed at all, which I can understand. We kept trying to no avail. It was torture for her, so it ended with each of us completely unsatisfied.

The next time was better, as we were both drunk and if it hurt her, she either didn't notice or didn't care. There was never any blood either time.

 

The person to whom I lost my virginity (18, freshman year of college, as far as I know she was unaware that I was a virgin) died less than a year later. That always made me feel a bit weird.

 

Because of my moral superiority complex I waited until I was 20 to choose the lady I would allow myself to be with. Of course I chose a 26 year old single mother, who lived with her mom and like to hump random dudes she met at country bars who gave her a ride home after buying her a few beers.
It was very quick, and uneventful.

 

I was 16, he was 15. We both were virgins. First guy I did EVERYTHING with...He took almost every first you could think of...Anyways, being the good little Catholic school girl I was (not)-it took quite some time before he took my V card. I always thought "planning" on losing your virginity was a weird thing for a girl to do. The whole candles and sexy outfit was just ridiculous to me. I always kind of thought "if it's right-it's right". I had almost lost it on Valentine's Day-but that was just way to cliche for me. I still remember that night and thinking-damn, I want to do this. But the whole retelling of when I lost my virginity was just too girly for me. It was over the summer and I can remember the date because it was the day before our 8 month. We were in his room-his dad was grilling food for us outside. And I remember we were naked under the sheets-foreplay-and I brought his head to mine and whispered "I want you to put it in me" in his ear. He was in shock because it was kind of out of nowhere. We got interrupted by his dad yelling downstairs to us the burgers and hot dogs were ready. So we got dressed-realized that he was going to have to change his sheets-and went outside to eat. I remember eating that hot dog and thinking "Wow, I can't believe that actually happened". Went back at it after lunch. Hurt like hell for the next 3 times we did it.

In the long run. He ended up being a douche after awhile. And we dated longer than we should have and I certainly wasn't ready or mature enough for the emotional toll that relationship took on me. Took me awhile to get over that but in the end I am very grateful for that relationship as a whole because it taught me a lot about myself and what I want in a guy. And I never regret how I lost my virginity because I knew I did it when I was ready. No plan. Just raging teen hormones.

 

I was 19 almost 20. I was living with a girl I knew from high school (No she wasnt the one it gets better) because she needed a roommate and I figured fuck it its 2 minutes away from work. It was a bunch of duplexes run by by some bitchy old land lord lady. I guess the landlords daughter had noticed me for awhile and made it a point to meet me at work and "help" her mom with the place next door. Well one night I get a knock at my door, its her(Bangable) and her friend(Wouldn't do her alone). So I have them come in introduce them to Dane Cook (This is before he really became the ass hat he is today) take a couple shots. Next thing you know I am making out with the landlords daughter and her friend. Her friend whispers in my ear "Taste the rainbow" I shit you not. So yeah my first time was a threesome. My friends bring it up and say how the fuck do you do that? Honestly I don't know. I just wish her friend was hotter and not a dirty ginger...being as they don't have souls and all.

 

We were both 15 and had been together for about 5 months. He was a virgin too so it was awkward and painful. He had no clue what he was doing and pretty much just shoved in and went to town. Horrible experience. I had nightmares about that pain for weeks afterwards. Found out later that because of how much I bled and the amount of pain I described I may have had an extra thick hymen ... not sure but all I know is that my first time sucked.

 

I've posted mine before, so I won't go into the gory details, but it involved period blood and a missing condom.

I guess I'll be the lone prude here. It all seems consensual and you seem cool with it, but that shit ain't right.

Also, "cunty" doesn't even begin to describe what my reaction would have been had I been in your shoes.

 

I was 16, he was 18 and my first serious boyfriend. We had been dating for two months and were both virgins. We were at a, um, Beltane festival and had gotten separated and I was smoking with some friends. It was reallysuperstrong and by the time he found me again I was hallucinating. We went to leave, and on the way home pulled into this parking lot by the river to make out in the backseat (of his van, hot). I don't remember how the decision was made, but at some point we decided to go for it. A few minutes in, I thought I heard him change his mind, so I got off, curled up on the floor of the van and started crying. (I couldn't tell you why.) (Oh wait, yeah I could, because I was really freaking stoned.) He thought I was freaking out about having sex, but I was freaking out about not having sex, and once that got sorted out we continued. Then on the way home I kept yelling because I thought people were jumping out of the woods in front of our car. It was, overall, a weird experience.

And then later he accused me of lying about being a virgin because I didn't have a hymen at the time of boning. Stupid.