I love hearing about how people lost their cherry...if anyone would like to respond here, or a message, I'll be glad to reciprocate!

I'll start. Anna and I were both virgins when we started dating. We were living about 4.5 hours away from each other, so we were limited to visiting in person about one weekend a month. about 3 months after we first met in person, we decided to have intercourse with each other. We had already been having oral sex and mutual masturbation.

It was the first time she came down to my town to visit, and I have to say for the first time and us not knowing what we were doing, it was a very enjoyable experience.

Nancy and I were both virgins, and she had gone out on a trip for a week, and we were just getting into heavy petting. Needless to say, I was building up fast! Then I received a letter, and she told me she thought if we cared about each other we should go ahead and try fucking...wow!

We drove together the night she got back, and found a place off the side of a deserted road. We stripped and admired each other, and lay beneath a huge oak tree on a bed of leaves. We fumbled and laughed a lot, but had a great time - and finally both discovered how cumming as we fucked was sooo wonderful!

My first partner was not a virgin. She'd been with another guy, but it sounded like her experience was not terribly pleasant. She had been after me for a while, so when the time came, we sort of planned it out so that it would be good for both of us. We spent the day together, going out to buy the condoms and lube. We fooled around some during the day, but waited until night to have intercourse. We went to my bedroom and slowly stripped and made out, kissing and caressing each piece of newly exposed flesh to build the excitement. We pressed our nude bodies together, her young breasts against my chest and my hard cock against her stomach. When she was ready, I slipped on the condom as she applied lube to her vagina. She rolled over and I climbed on top, gently guiding myself in. As that sweetness enveloped me, I kissed her. I savoured the new sensations as I gently made love with her. After I came, I fell motionless and remained inside her for another minute, not wanting it to end. When I regained enough strength to speak, I said "I love you". Afterward, we fell asleep in each other's arms.
In short, it was an absolutely amazing first time and truly a moment to treasure. I feel sorry for those people who tried to do it crammed in the back seat of some subcompact, out in the parking lot behind the 7-11.

well, it wasn't a compact behind a 7-11 but....the dude Aaron was weird. Picked me up from the club. Went back to his place and on the second date he was fucking me in his bed. it was mildly painful tho he didn't seem to care. what made it all the more freakish is that on his couch watching tv afterwards...he was petting and licking me, meow-ing like a cat.
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My gf and I were both virgins and we had been going together for a year or so. We were both 18. My cousin lent me his apartment and my gf and I spent the day there, first fooling around and petting naked for a long time. She was keen to 'do it' and I was timid but horny and brave enough to do it. With a raging hardon I carefully penetrated her a little at a time , and she then urged me to thrust in. It was a wonderful and warm sensation I'll never forget, and she held me tight. It was a very good experience.

Wow...great answers...Ladies, please let us know as well!

Nice!

I'd been over at my h.s. teacher's house several times, and the conversations had turned to sex, then swinging, and he told me about orgies and that I should join them.

Coincidentally, I had a date with one of the cheerleaders to take some pictures of her at the beach. We had a great time and were down to toplessness, but she said she had to leave to be somewhere. I told her I'd drive her.

Turned out, she was going to the teach's, and I went along with her. Turned out, also, she was there for an orgie (something she only suspected), and, after a little discussion, I was included.

About six minutes after we'd arrived, we were both naked with two older couples. The teacher's wife laid me on my back and mounted me and very gently and beautifully enjoyed me, while I was holding on for dear life trying not to cum right away! Finally she came (quietly) and I remember so well that first throbbing and pumping and then growing soft inside of her.

A couple of months later, I dated a girl who was a virgin, and soon we had sex. It was a completely different experience, very close and tender and we both cried.

Soon she came with me to swinging parties, and she loved fucking other guys, older men, and multiple partners. When we were alone together, we also had that very close, emotional, and tender kind of lovemaking.

There's a thread about it somewhere on the board...

I met a guy online early last year who expressed interest in me, and we eventually met up and got to know each other.
During the first few meets, we participated in mutual masturbation and oral sex, and after about 3 months, we had sex for the first time. We'd talked about it a lot, and I'd expressed quite how terrified I was. I will always remember him telling me that when the time came, he'd look after me and make me feel safe.

The guy I was with hadn't taken someone's virginity before, so he was actually pretty nervous himself.

I'd been told scary stories by my older sister that the first time would be unbearably painful, unsatisfying, and generally not very nice.

Instead, I was taken to one of my favourite places that morning, treated very nicely, and he was caring, tender and gentle when we finally made love. He didn't hurt me, and he made me feel special...
I'll never forget looking into his eyes, and I'll never forget our long cuddle when it was over.
I will always be able to look back and know I had a good first experience

Well, I was only 14 and have been masterbating for some time and enjoying it. I had fantasy's of my next door neighber. She was 32 and very sexy. I would sneak over to watch her swim and then lay in the sun at her pool. I masterbated while watching and loved cumming thinking of fucking her right there. Well one day she saw me watching her and masterbating, I was so scared and she knew it, so she said that she wouldn't tell my parents if I masterbated in front of her and cummed on her. I was like excited and nervous, but did what she asked, jerked off in front of her and she took her bathing suit off and I lost it almost right away when I saw her naked body. She laughed and took my hand and put it between her legs and felt her wet shaved pussy and that got me all excited. She then took my cock in her hands and got down and started sucking on it and that was my first blow job and when I was about to cum she stopped and layed me on my back and sat on top of me rubbing her pussy up and down my cock. We were kissing and she then said she wanted to fuck me and if it was ok, I said I never did this and she kissed me and told me to fuck her. Grabbing my cock and then sitting down onto it, I watch it going inside and it wasn't 1 minute of her fucking me and kissing me that I fucking came so hard inside of her and she had an awsome orgasm just after that. She said I was the first young boy to fuck her and that she want to fuck me at least once a week. So that is my beginning of fucking, was an older woman and was so fucking good.

I was 13, and in the 7th grade, and me and a friend were over his house and I don't remember exactly how it happened, but we ended up fooling around and my first ever orgasm was while I was fucking his ass. I had done it a few times before but nothing ever really happened. This time, it was different. I enjoyed it and next thing I know I'm pounding away at his ass and I feel like I'm going to pee but I can't stop fucking him. I remember yelling out, "omg I'm peeing, why am I peeing?!" and he yells you're cumming don't stop.

Back in high school, my two friends bet me $50 each that I wouldn't be able to fuck this girl at a party. I don't remember the details because she and I were heavily intoxicated, but I was $100 richer by the end of the night.

I lost my virginity at 17 yrs old,one night in the woods,one of my ex school teachers got me on my knees and slid his big cock into me!!!!,i can still feel it going in,him thrusting,then feeling it start to jerk then feeling the heat of his cum!!!! I was 13 when i lost it to a woman,she was in her 30's,she and her husband planned and seduced me big time!!

Guess I was a late bloomer, lol! I dated a lot through HS, finger-fucked a number of girls, but was still a virgin until I was 19 and selling books door to door in California. I met a 30-something good looking woman sitting on her front step, and we talked and flirted for a long time. Jackie invited me back to her house later that afternoon, and when I returned, it didn't take long to end up in bed with me rubbing that fantastic womanly body. When I got my cock in her, I know I couldn't have lasted a minute. She was pretty understanding and we laid there kissing and making out. I was hard again in a couple of minutes, she pulled me on top and DAMN! I couldn't have lasted a minute that time either. I enjoyed it a lot more than she did, I'm sure.

A better experience for me was the first time I fucked my GF soon to be wife. We'd been engaged for a couple of months, and going "parking" in my car regularly with heavy petting, kissing, occasionally her jerking me off but "saving ourselves for marriage". We were parked in a city park one really cold night and had the windows really fogged up, had been making out for about an hour. She had been playing with my cock and I had her pants off and fingering her for a long time. It wasn't real unusual for us for her to rub my cock up and down her lips and slit but not put it in, and she started doing that. After a little while, my sweetie raised up a little, shifted my cock a little and the next thing I knew, she had slid me inside her. She was so wet, so hot and tight, and it was the most unbelievable feeling I had ever had. We stayed that way, just barely moving until I felt like I was going to cum. She pulled me out and finished me up with her hand. Even though I had lost my virginity before, this was a lot more memorable and emotional for me.

What's funny, is we've been married for nearly 35 years and I think her pussy feels even better now than it did then. We've had our ups and downs with frequency of sex due to pregnancy, menopause, weight gain and loss, and I've fucked some other women (mostly of the professional persuasion), but I can truthfully say that my wife's pussy feels better than nearly any of them.