First attempt at 17, Julie, a complete and utter failure and despite having my cock nearly in and cumming I don't class it as losing my virginity.
My true virginity was taken at 20 years old by Mrs X, a 39 year old tutor at university ...... she didn't teach any of my classes but God she taught me a lot ...... thank you Mrs X.

 

Oh wow look at that another thread that boils down to 'how old where you when...?' And look eight pages, don't these normally get deleted when someone mentions their first time was pre-legal age?

 

No I don't. I was 17, she was a woman in her early 20s I barely knew. Spoke to her once after that but the most we would have ever been was FWB.

 

I was 20, she was my girlfriend and it was the first time for both of us. Neither of us had a clue what we were doing to be honest. It wasn't bad but it wasn't good either. Things kind of went downhill in our relationship after that.

 

No idea. It was a complete stranger

 

Oh Re'ne. My first time, her 2nd. in the woods...

 

Being a shy kid growing up I didn't lose virginity until early twenties. Girl from a night club friends and I use to hangout at in Pa. She was a excellent teacher. About a year older but certainly experienced. I learned a lot and still have fond memories. But alas life moves on.....

 

No one took it. I gave it away. I was 19 and thought all my friends had already done it. I went on vacation to a Club Med in Mexico. Met a guy in his mid 20s and we started hanging out. One night we were walking on the beach and saw an abandoned beach towel. We laid down on it and started making out.

At some point he unzipped his fly. I had never even touched a bare cock before. I realized it was going to happen. My jeans ended up down around one ankle. He entered me and it stung for a bit but then it felt good. He realized he had popped my cherry and was very sweet afterwards.

We hooked up every night for the rest of the week. He asked me to suck his cock, which scared me more than fucking. But he told me what felt good and let me control the depth etc. I made him cum the second time I did it, so I guess I was a natural - LOL.

 

We were both virgins. She was living in a neighborhood and we were good friends. We still talk sometimes. She is married now. Still a hottie

 

Yes it was my cousin and we still fuck from time to time still

 

older Landlord

 

grownup in a farm,
with the owner of the nearby farm.

 

We both worked at a mountain resort and both in our mid-late teens. I remember a whole bunch of fumbling and hushed tones as her roommate was in the room as well(not included)! We hung together for a bit but then drifted apart. It was through repeated attempts with older women that i became proficient with "straight" sex. My first male was a wonderful loving man that took a weekend to showcase how man to man sex is a beautiful thing, and am still following his lessons.

 

Not having a girlfriend as a teenager because of insecurity, but so horny and wanting to fuck a girl for a first time, I went to the red light district of Amsterdam. She was young, beautiful and had patience with me. When I wanted to 'visit' her again a few weeks later, she was not there anymore.

 

I want to tell the world...but not allowed here

 

Cathy was the gf of a friend who was mostly an acquaintance at that time and more my younger brother's age but we became closer friends as we got older. Id didn't know who she was when I met her but she obviously didn't respect her boyfriend so much since she came home with me.

I was working at the mall and this other girl, Kay, used to come in everyday and me and my co-worker used vie for her attention but she was more interested in him. So one day she comes in and brings this girl for me to meet. I was drawn to Cathy immediately. We chatted then she ended up coming back to my house where we did the deed.

She eventually married another friend of mine and he knows I fucked her. Ironically he's the first person I told when it happened. Truthfully when I see her now, I kind of want a do-over. Not with her but another girl lol.

 

I was in college in New England and our fraternity had a weekend away at a large resort in New Hampshire. I invited a prep school hottie from Pittsburgh who I knew to be my date. I cannot believe her parents let her go. We shared a room, bed and each other. The following year she went to the University of Chicago, became radicalized and went her own way. I was a mechanical engineering student. We got to together once or twice but our life views were very far apart. I have seen her profile on facebook but did not contact her nor will I. Fond memory but that is all.

 

Ma mère

 

it was my moms younger sister I was 14 and went to her home to help with the yard work and stay the weekend. Really learnd a lot my first time there with her Her husband was on a business trip and she invited me into her room as she was dressing and she took all her clothes off and saw I had a boner and felt it. we started that night and it was wonderful she instructed me the entire time how to pleasure her and I was shooting cum every 5 or 1o minutes and shw would hold me into her and bath in the cum I was releasing. she told me she loved the warm wet sticky feel of my multiple releases and her husband was a one time shot during evening of sex. She loved how we did sex for hours with me continuing to release cum shot for like 4 hours she had me to her self that weekend totally and I was her sex toy and loved her warm full breasts and pussy. I am hard on now telling this.
If youlike to hear more PM me

 

my first husband before we got married. i was either already knocked up or it happened on the wedding night and when he found out he took off and haven't heard from the asshole since and that was 34 years ago.