Oldest loss of virginity

[RjThoughts]

I was 18 and a freshman in college but he hurt and didn't know what he was doing. I had a few boyfriends but never orgasmed and honestly didn't really enjoy sex. I was married for 18 years and never orgasmed. Sex was obligatory (heavy pressure to produce grandchildren to his parents) and was always about his pleasure, not mine. It was awful. I got divorced after his parents died and was alone for 4 years and didn't miss sex at all. Then I started getting horny all the time- like ALL THE TIME. I met a wonderful man and the first time we made love I was wetter than I'd been in decades and I came all over his cock. I cried (I know.... ) out of joy. Now I'm horny all the time. I want to fuck him every time we are together and I can't keep my hands out of my pants or off his cock. I'm finally allowing myself to explore my bicurious thoughts and desires and he supports me. I haven't found a way to make it happen but I desperatly want to have sex with a woman. So I consider my first good sex happened a month ago- at age 47! Yeah me!!!

My mother's bestie was like this. She left her ex for the same reason: Gave his parents grandchildren then he didn't give a shit! She was over at my apartment once a month when she learned my mother kicked me out, using the excuse that she was lonely - he had the kids. Then that turned into knowing when I'd be home studying. She would sit on my lap, especially when I was just out of the shower and in my tiny running shorts - the early '80s!

She scratched the bicurious itch with my female roommates, having been with both of them numerous times "just to make sure LOL

 

[Stephie02]

I was 18 and a freshman in college but he hurt and didn't know what he was doing. I had a few boyfriends but never orgasmed and honestly didn't really enjoy sex. I was married for 18 years and never orgasmed. Sex was obligatory (heavy pressure to produce grandchildren to his parents) and was always about his pleasure, not mine. It was awful. I got divorced after his parents died and was alone for 4 years and didn't miss sex at all. Then I started getting horny all the time- like ALL THE TIME. I met a wonderful man and the first time we made love I was wetter than I'd been in decades and I came all over his cock. I cried (I know.... ) out of joy. Now I'm horny all the time. I want to fuck him every time we are together and I can't keep my hands out of my pants or off his cock. I'm finally allowing myself to explore my bicurious thoughts and desires and he supports me. I haven't found a way to make it happen but I desperatly want to have sex with a woman. So I consider my first good sex happened a month ago- at age 47! Yeah me!!!

I'm not here to answer the question, I was young, for both; I'm bi and long story short always have been and definitely prefer women. I wanted to comment on the crying part, it sounds like you're embarrassed by that; don't be. I'm 23 but cried the first time with a guy because it hurt, but emotionally overwhelmed? With my current girlfriend; she bought a strap-on and we were missionary. It was amazing. Gentle, slow, looking in her eyes, it was a lot and it was definitely overwhelming. Don't be embarrassed, it was your moment and I hope you have more just like it.

 

[AZMod]

I was 19 when I finally lost my virginity. I had made out with boys on dates, been felt up during those sessions and given a few hand jobs and a couple of BJ's but never any vaginal penetration

 

[WanderingSarah]

22 - I grew up in a fairly repressed household (majorly into the Catholic guilt and shaming) and had a boyfriend. I enjoyed it at first, but he wouldn't make me orgasm, said it was too much work. He was also deeply offended by the idea of me using a vibrator to orgasm.

He cried after because we shared a piece of ourselves with one another. Honestly, I should have run right then. I later realized, he was several walking red flags.

 

[RjThoughts]

22 - I grew up in a fairly repressed household (majorly into the Catholic guilt and shaming) and had a boyfriend. I enjoyed it at first, but he wouldn't make me orgasm, said it was too much work. He was also deeply offended by the idea of me using a vibrator to orgasm.

He cried after because we shared a piece of ourselves with one another. Honestly, I should have run right then. I later realized, he was several walking red flags.

Catholic guilt is real, having suffered from it for years. My sisters did not suffer from the body shaming, thanks to our Polish great-grandmother but I witnessed it it far too often at church and church-sponsored events.

My VERY Catholic first love did not have an orgasm the first time we made love, but she was "Let's try again" until we get it right.

 

[ericalauren]

22 - I grew up in a fairly repressed household (majorly into the Catholic guilt and shaming) and had a boyfriend. I enjoyed it at first, but he wouldn't make me orgasm, said it was too much work. He was also deeply offended by the idea of me using a vibrator to orgasm.

He cried after because we shared a piece of ourselves with one another. Honestly, I should have run right then. I later realized, he was several walking red flags.

I’m glad that you left him. You deserve better. I’ve heard of people (especially cis men) being offended by sex toys. That’s a huge red flag to me. I remember my cousin telling me that her now-husband had forbade her to have a bachelorette party. His rationale was that she would get sex toys as gifts and then leave him. So weird!