How did you choose who to lose your virginity to?

[Mickyb9669]

It was a boy I grew up with in my neighborhood. We were in a small group of neighborhood friends. We went to school together although he was a grade above me. As we got older we started discussing sex and learning about each other and our bodies. It eventually led to exploring. And sex a few times. I was 16.

Earlier than ma hehe

 

[ChloeOfCascadia]

I was waiting for the right woman. Asked many girls I adored out on dates, for years. No one clicked with me / said yes. I was a late bloomer.

Age 18, I was worried no one ever would, unwittingly got invited to a sex party, wore a condom, 3 women who had been having sex with random men all night, largely ignored me, they invited me.

Anyway. Guys left besides me, I made them all dinner, gave them massages. I'd been practicing to go to massage school.

It was way past midnight and the women were drunk and happy from all the sex, and enjoyed the chicken I cooked for them. 2 went to bed, they shared a house, only 2 bedrooms, I laid on the pull out sofa bed with the eldest woman, who was about 35 I estimate.

I laid respectfully after giving her a massage, where she took off all her clothes. She then asked me, you actually are a virgin, aren't you

And I said yes.

She figured it out because she gave her naked body to me to touch and I touched, I didn't try to take without permission or cross boundaries.

Which, btw, is an issue, but I digress. That shouldn't be the norm. It is trivial to ask first.

She asked if I was gay and I said no, I love women. I would like to have sex but no woman has said yes to me.

So she said I could touch her if I wanted to, and I said yes. I cuddled her, caressed her breasts and her nipples in particular, and then after a while she took my hand and placed it directly on her naked vulva and encouraged me to stimulate her that way, and I did.

I brought her to an orgasm by listening to her sounds and doing what she indicated felt good. I'd also been masturbating for about 8 years by then, so, I figured, what felt good to my body in terms of pressure and stroking rhythm, might feel good to women too, as a wild guess.

Just, different anatomy and positioning of my hand and fingers, that's all. And listening.

So, she came on my index and middle finger, her vagina squeezing me very tightly, so strongly it was cutting off circulation. She was very very right when cumming. My fingers were sore after taking them out of her. Good girl, I bet that feels really good on someone's cock.

Anyway, I asked her if I could give her oral sex and she agreed, grabbed my hair, and I stimulated her clitoris, which even though the internet sucked back then, in 2001, I still remembered where it was from fifth grade sex ed classes. I was always a nerd, I remembered the anatomy of a female, I'd never seen it, not even in porn.

Remember back then, it would take forever to download a still image? Yeah I was not getting video porn with my dial up internet. Not at all.

So, I'd never seen a clitoris, and it was trivial to find. I do not understand what the hell the problem is. Crack open a book, gentlemen. I know it's small, but, it takes 2 minutes to figure this shit out. I roll my eyes every time I hear "he never found my clit" BOY, IT IS YOUR ONE JOB AS A MAN.

I can't believe how often I've heard that fucking story. It's ludicrous. You don't deserve a tenth of the sex you've gotten in your life if you can't be bothered to ask your partner what feels good or look up her anatomy for 2 seconds. Libraries were free back then. Guess it's not important to you, but I am sure if she didn't suck you off, it would be a big issue right?

Anyway, flicking her clit like a cat drinking from a bowl of water for a while was all it took for this woman to grab my hair and buck and grab my head with her thighs. She came all over my face, and that was the best part of the evening, because now, it was time to put on a condom.

She handed me a condom and told me I could fuck her if I liked.

So I did, and I couldn't tell I was even in. The condom was tight, it was hot, there was no difference in sensation between having the condom on, and being inside her or not.

Couldn't feel a thing but 18 year old me could stay hard for hours.

I fucked her for a good hour, and she came a few times, vibrator and hand stimulation on her part, I'd like to think my cock was helpful too.

Anyway she told her roommates, because, they share guys. She said she took my virginity, which was true, and showed me off to her girlfriends aged 25 and 27 I think. Could be 28.

They saw me naked and rigid and invited me to bed one at a time.

I felt absolutely nothing each time. I didn't even come close.

I figured the experience would be helpful, since I wasn't having a romantic date.

And it was, I learned how to pleasure a woman with my cock, quite well, and I also learned how to give women orgasms with my fingers and my mouth, and most of the way with my cock, and also, got in plenty of massage therapy practice.

And I used that experience to pleasure future women who didn't insist on condoms, in long term relationships.

I actually had orgasms frequently in those relationships. It led to very nice things.

I needed to break the ice, being a virgin and nervous about acting on my desires to have sex with women, doesn't get you very far.

But, once the ice was broken I spent most of the next 24 years in relationships, and having lots and lots of sex and romance.

Things got much better.

Also, having 3 women in 1 night could be fun, it really could be. I would recommend 1 woman you have chemistry with and can have a safe time without a condom, or, if you can have fun with one on, feel free.

It's not hard, some women have sex with random strangers and share men.

It's a sex party, they happen, Live near a major city and some women somewhere will be having fuck parties.

It's not difficult, I stumbled in to being in one by pure chance.

You can do it too if 3 women is your dream.

It was my first experience and it was educational and not even remotely pleasurable and everything after that was a billion times better.

But if multiple women is your thing you gotta have before you die, they have to advertise their risky sex with strangers parties somewhere.

*Shrug* have fun. Not the usual first time story and no, I don't care that you don't believe me. Told my construction worker buddies the next shift and none of them believed me.

They probably could have still smelled these women's vaginal secretions on me. I don't care. I was there, I know what happened.

It wasn't difficult and I wasn't even trying to have sex until it happened.

I also found the clitoris three times in a row. It's easy.

Its right above the place where you wanted to put your penis. Go north like 1 inch, you found it.

Wow, mysterious.

(I have told this story a lot, and guys never have anything worth hearing as a response, and women tend to identify all the markers where it was obvious I really was a virgin, so, they tend to buy my story. Plus, they probably know some girls who fuck random guys, so, they know that happens a lot)

Whereas some men do fuck random women but their game is being tall and attractive and then women agree to take their clothes off, and that's fine.

But they have one move, which is shoving their dick in, and that's why they have no idea where the clitoris is.

And they can't please 3 women in one night because they cum in 5 minutes from their one move.

I know, women have told me this all their lives. It's sad.

I am an average looking person of exactly average height, and women generally held on to me as long as they possibly could, because everyone else they fucked was so pathetic at it.

They boasted being taller, and that was their only advantage, and eventually women desire something more, for obvious reasons.

A sturdy dildo easily replaces them, costs less, is easier to manage. My advantage is I can cook and identify a clit and give women orgasms.

I can also keep up a conversation.

This is really sad that this qualifies as a brag, but I also wash my dick, gentlemen.

What the fuck is wrong with some of you....

So yeah, first time was unsatisfying yet educational, and after that, I was in a lot of long term relationships with women seeing only me, one at a time, and having lots of actually satisfying sex.

I am a quick study. I'm a nerd. It has advantages.

 

[liqueur]

I'm still a little mystified by this notion of choosing who to give your virginity to. in the world I grew up in, it was usually something that just happened. You played around and you played around, exploring further and further, until one fine day (night) you “went all the way.”

The idea of choosing someone sounds so... adult!

 

[SweetCuriousDarling]

I’m sad to see so many people - mostly women, it appears - relay the too familiar story of not having a choice. I can relate to that due to childhood abuse - I stand with those survivors.

It does seem we’re defining lost virginity as ‘PIV’ sex, however. I suppose, when it comes to that, I did ultimately get the opportunity to ‘choose.’ It was my first serious boyfriend. He was 6 years older than me. We’d been together a few months and he had told me he loved me - the first man to ever say that to me. He’d been pressuring me to have sex, while insisting he wasn’t trying to pressure me - you know how it goes. Anyway, I had a lot of confusion and hang-ups due to my past and felt like maybe I needed to prove something to myself so eventually I relented.

We were in his room at his parent’s house. It was afternoon. I think the house was empty. We were on his bed and he was kissing me and taking off my clothes. He went to the dresser and put on a condom. I was so tense. He was very eager. It hurt - a lot. I remember just lying there and wanting it to be over.

After a very brief time, he stopped and looked frustrated. He told me that the condom broke, and he didn’t have another one. I was just sort of stunned. Well, that was that then. But he wanted to keep going without it so he could finish. I told him no way - we’d had that discussion. But he knew I was on the pill and didn’t understand why I was insisting on using a condom, too. He got mad, and I ended up crying.

In short, it hurt, we didn’t finish, we ended up fighting, and it ended in tears. Not a stellar experience.

 

[LFM90]

I didn’t get to choose my aunties took it upon themselves to bring me into my manhood

 

[Ssbbw4u1974]

It was my choice to get devirginized, I had been tired of hanging around girlfriends who talked about fun with their guys, and I had zero idea what they were experiencing.

One night, at a party, I was wasted and told my BFF at the time I was ready... So, she disappeared for a few and she came back holding my hand in hers, she led me to her bedroom...

Waiting inside the room was her BF..

I just went with it...I learned a "cliff notes" way of giving him head, before we exchanged sexual positions..

I loved her as my best friend, so I trusted her... And it was the best sexy night of my life!!

 

[Mickyb9669]

I didn’t get to choose my aunties took it upon themselves to bring me into my manhood

Wow 2 of them what an experience

 

[UtilityCurve]

I chose? No it would be the first that would let me.

Yeah, at the risk of painting with a brush as wide as half the world's population, I think virtually all males either don't let the first pair of spread legs go to waste or are pounced upon by a female. The very idea of picking and choosing made me laugh out loud at the question.

It's the rare female privilege and I am quite cognizant that some are denied it (custom, violence, incapacitation). Living in that minority (TBH, while the majority of females do get to chose, I have yet to meet one who wasn't conflicted or uncertain or downright scared at her first time, so even getting to exercise her privilege was not all sunshine and unicorn farts--too the dissonance between her caution and his hell for leather enthusiasm must not be pleasant for her) must feel horrible as it is a signal moment and being stuck with a bad memory for a lifetime cannot be reversed. I know: My wife was in that minority. I was with a girl in the majority. The fit never quite fit to my eternal sorrow and I curse "him" for stealing it from us years before we met.

 

[hrdmngd2find]

Well, my answer will be as rare as a blizzard in Panama. I lost my virginity to my wife on our wedding night when I was in my late 20s. Why did I wait? It wasn't because I didn't have an insane sex drive, because I did. Religion is the short answer. As a single guy, I had masturbation binges when I would cum over 15 times in the same number of hours. When I was in high school, I used to get a raging hard-on every morning when we stood up for the pledge of allegiance. It wasn't patriotism, it was the ass on the girl in front of me and the fact that it was still morning.

Anyway, I can attest that waiting til the wedding night didn't work out well in our case. I'm sure there are couples who have that work out great, but not us. We divorced after 10 years because I was too much of a "pervert," even though I had never cheated on her. Those ten years, by the way, were not exactly fun either. She considered masturbating to be cheating. So in her mind, I was cheating, and whenever I masturbated, if she found out, she would withdraw and withhold sex for weeks & months at a time. The last two years, we had sex 0 times, but honestly, it was already over by then. I did try not to masturbate, though, without having sex either. My record for abstaining from all sex- masturbating or her- was just over 100 days, and by that point, I had so much pent-up fucking sexual hunger, the whole world became sexualized. It was like all the women around me were nude. I'm not normally a rubber-necker, but after 100 days???

The divorce turned out to be a huge blessing, because I was fortunate enough to end up in relationships with women who loved sex. I didn't go crazy and fuck every woman after that divorce, but the women I dated, they felt all that pent-up energy- every day and night, sometimes many times a day.

 

[OtherwisePrint6210]

I didn’t get to choose my aunties took it upon themselves to bring me into my manhood

So, was it a good or bad experience?

 

[jakinov]

Landlady. I was 19 and making my way in the job market in Toronto. I rented a small studio apartment from a woman in her 50s, married to some guy who was always on the road. Two weeks into my tenure she knocked on the door about 10 at night and asked if there was anything she could do for me? I asked her in and she totally took command, necessarily so since I was a shy, virgin lad.

 

[Sweetnsassy417]

How did you choose who to lose your virginity to?

I was… young.
We were living in the projects (low income housing) and there was this one guy who knew I was a virgin and didn’t feel I should be one and made his opinion very clear. Unfortunately I didn’t have the voice to speak up to any adults. Like I said I was young.
There was a boy I liked (4 years older than me, so not a boy exactly) and he treated me well. He was my first kiss and my first everything. He still holds a very special place in my heart.
And then about a year later, the original guy took what he wanted from me.

 

[LFM90]

So, was it a good or bad experience?

The best ever. I learned to serve and be obedient to them

 

[Jimmy_Butler]

It was my girlfriend at the time. We had progressed the usual way for the time, but this time it was different. I noticed she was unusually turned on when others were around (closet exhibitionist?), and we were at a drive in double dating with a couple of friends. We were in his van and we were going hot and heavy next to them, semi-unclothed, and when she was on top grinding on me, she shifted and took me all the way into her. We didn't get to our climaxes that time, but it was the first time for both of us.

 

[UtilityCurve]

I noticed she was unusually turned on when others were around (closet exhibitionist?)

Not an exhibitionist per se, but there is a very sexy vanity girls/women have that craves being craved by as many men as possible, I believe. I'm not going to take a side on whether that is how and what females compete for.

But to do something that would have every cock within sight hard while still remaining safe behind you would be irresistible to many like her. I've not had the good fortune to observe a couple playing in a porn theater (always dreamt of it) but that is the pinnacle of this desire: It goes without saying that they would only be there if and do only what she wanted, but she would know perfectly well the effect she'd have on the solo men in the room.

 

[Jimmy_Butler]

My only threesome was with a couple I met in an adult theater. I watched them and once we made eye contact, moved closer to them. The lady invited me closer, and we began to touch. I ended up on the floor eating her.

When she came they invited me to follow them to their hotel room. Her SO (husband? boyfriend?) and I took turns pleasing her. No anal, but there was spit roasting along with watching and wanking as we shared her.

 

[JackWilson0715]

I guess it was just expected. We had after all gotten married the day before, lol

 

[Mickyb9669]

Well, my answer will be as rare as a blizzard in Panama. I lost my virginity to my wife on our wedding night when I was in my late 20s. Why did I wait? It wasn't because I didn't have an insane sex drive, because I did. Religion is the short answer. As a single guy, I had masturbation binges when I would cum over 15 times in the same number of hours. When I was in high school, I used to get a raging hard-on every morning when we stood up for the pledge of allegiance. It wasn't patriotism, it was the ass on the girl in front of me and the fact that it was still morning.

Anyway, I can attest that waiting til the wedding night didn't work out well in our case. I'm sure there are couples who have that work out great, but not us. We divorced after 10 years because I was too much of a "pervert," even though I had never cheated on her. Those ten years, by the way, were not exactly fun either. She considered masturbating to be cheating. So in her mind, I was cheating, and whenever I masturbated, if she found out, she would withdraw and withhold sex for weeks & months at a time. The last two years, we had sex 0 times, but honestly, it was already over by then. I did try not to masturbate, though, without having sex either. My record for abstaining from all sex- masturbating or her- was just over 100 days, and by that point, I had so much pent-up fucking sexual hunger, the whole world became sexualized. It was like all the women around me were nude. I'm not normally a rubber-necker, but after 100 days???

The divorce turned out to be a huge blessing, because I was fortunate enough to end up in relationships with women who loved sex. I didn't go crazy and fuck every woman after that divorce, but the women I dated, they felt all that pent-up energy- every day and night, sometimes many times a day.

Sounds like my marriage at least you got out and found what you wanted.

 

[JackWilson0715]

Sounds like my marriage at least you got out and found what you wanted.

Sounds exactly like my marriage except for the leaving part.

 

[MilkyMarshmallows]

I was young. We did it because we were dating across country and I didn’t know when I’d see him again. It was not great sex. I didn’t cum. I didn’t see him again after I had to go home. It was a, let’s get this over with kind of thing. By choice, but so lame.

 

[liqueur]

When I was in high school, I used to get a raging hard-on every morning when we stood up for the pledge of allegiance. It wasn't patriotism, it was the ass on the girl in front of me and the fact that it was still morning.

Yes, those asses when we were in high school! Other guys went on and on about girls’ breasts. I never saw them, because me eyes were glued to the girls’ asses. I became an expert at adjusting my constant hard-on to keep it hidden. I thought. Looking back, I bet every girl around me knew.

The divorce turned out to be a huge blessing, because I was fortunate enough to end up in relationships with women who loved sex.

I'm glad it worked out well in the end. Those intervening years sound like hell.

 

[Leaderoft5b]

I was quite a late starter at 23 so was desperate to have my first fuck with anyone (female) who was compliant. I had a friend who's girlfriend's cousin was single and we went out as a foursome for a few drinks one weekend.
After the pub we ended up in the lounge of the house belonging to my friend's girlfriend's parents.
I finally did the deed on the lounge floor with the cousin when we thought my friend and his girlfriend had fallen asleep on the sofa.
The next morning I was giving my friend a lift home and he confessed that he hadn't been asleep and that he'd seen and heard everything!

 

[RedmanReaction19]

The divorce turned out to be a huge blessing, because I was fortunate enough to end up in relationships with women who loved sex. I didn't go crazy and fuck every woman after that divorce, but the women I dated, they felt all that pent-up energy- every day and night, sometimes many times a day.

We actually had great sex while we dated and even through the first 3-4 years of our marriage. I've had a high sex drive since puberty, and she matched me fuck-for-fuck and suck-for-suck. I taught college, and seeing the young coeds in their shorts and midriff shirts and especially the oversized tee shirts they would throw on over their bikinis when they came to class straight from laying out made it easy for my drive to stay high, but for whatever reason, my wife's slowed down dramatically.

We were separated the last two years, and when she filed for divorce, she actually used as one of her reasons the truth that I was continuously wanting sex, craving it, and that my need created an irreconcilable problem.

Eventually, I realized that other women, particularly black ones, didn't have a single problem with my cock constantly calling for their attention, and I've had both singles and doubles in some hot-as-hell encounters.

My ex and I still might hook up a few times a year, even with her seeing someone, and we've even added a girl friend of hers, something she would never have done while we were married . . . and it's amazing how much sex can be improved when resentment is part of the motivation.