Your first time

Hi, please share the details of the time you lost your virginity (including age).

I'll start: It was my Freshman year of college, I was 18 and had met a young woman named Michelle during orientation. We were all so horny - our first experience away from home and the rules imposed upon us. I was a decent looking guy with dark blue eyes and light brown hair and was in great shape. But I was SO shy with girls! While I had a few innocent girlfriends in junior high ( kissing only, no petting), I never even kissed a girl in high school. My only sexual experience was the summer before college when my best friend's girlfriend, Ashley, introduced me to a childhood friend of hers, Angie. Angie had moved away with her mom after her parents divorced when she was 12. She visited her dad in the summers and didn't know anyone anymore except Ashley who suggested I keep her entertained.

Given the opportunity to hang out with a pretty, sexy girl all summer was a dream come true, even though she had a boyfriend back in New Jersey who was a linebacker on their high school football team and who had a solid streak of jealousy. He made his displeasure of his girlfriend's platonic friendship with me known. I didn't know any better. I was afraid he'd show up one day and kick my ass!

Angie and I became close friends, spending all day every day together for weeks. She loved talking about having sex with her boyfriend and I had to admit I was still a virgin. I'm sure she could tell that I was being driven crazy by her openness.

During her last weekend in town I was invited to join her family for a weekend at their cabin up north. We managed to sneak up a bottle of vodka and got really drunk on Saturday night after everyone went to bed. It might have been the vodka, or her pity for me, or maybe she was pissed at her boyfriend for being such a tool all summer, but this night was going to be different than everything had been. Following a dip in the lake, Angie ran into the cabin and took a shower then joined me in the front room wearing only her robe.

As usual she was going on and on about how much she was looking forward to seeing her boyfriend and all the things they were going to do to each other and as usual I was tuning out while imagining what Angie looked like naked.

And this is where something happened. "You've NEVER seen a girl's naked body?", she asked. "No", I sheepishly replied. At this point Angie stood up and placed herself right before me, looking down at me with both her hands at her side. "Would you like to see mine?". Speechless, I reached out slowly toward the belt of her robe and pulled, causing the robe to open. I can still remember the sight vividly nearly 40 years later. Two beautiful, round symmetrical globes with a pink pencil eraser standing right in front of each one. Looking down, there was a full brown triangle of hair between her legs (this was the 1980s). I stared slack-jawed at her beautiful 16 year old body for at least two minutes before pulling her robe closed "That's all you get to see", she said as the show came to an end.

Fast forward to September and I'm in my dorm room with Michelle. I'm sitting back getting the first blowjob of my life. As I could feel the climax was imminent I whispered "I'm going to cum". Michelle kept sucking. Maybe she didn't hear? "I'm going to cum" I urgently repeated, louder as I continued barreling toward that cliff. Then it happened. I bucked and spasmed as I could feel the cum shooting out of me down Michelle's throat. I couldn't believe it. That was it for that weekend. Next weekend I found myself again in my dorm bed with Michelle. This was the night. I just knew l was going to get laid! Finally, the time came. I pulled my penis out of her mouth before exploding then clumsily mounted her. I fiddled with my throbbing erection, trying to get it into her every which way I could, to no avail. Eventually her hand found it's way down there. She placed my penis at her opening and told me "ok, push". As I started my first thrust into a girl I erupted like a geyser. I didn't even get it all the way into her. I pulled back watched my cum spray all over her thighs and stomach and into her pubic hair (again this was the 80s!).

That was the last time Michelle was in my bed. I finished the school year as I had started it. A virgin. The next summer Angie came to town and proudly announced she was no longer with her boyfriend. It was in the basement of her dad's house that I finally had sex with a girl. What a summer that was!

My virginity was taken at age 16 by a 32 year-old lady.

I was working as a lifeguard at a rural swimming pool, with not many houses around. However, there was one house close by where a couple lived with 1-2 small children (can't remember now - 50+ years later). She had been flirting with me for a few weeks. She would feed us lifeguards at her home, when we were on break. One day when I was on break at her house, she was wearing her bathing suit, and I was in my lifeguard swim suit.

Don't remember how it began, but she seduced me that day. Her husband wasn't home, and her kids were taking an afternoon nap. We both got naked, and she pulled a tampon from her vagina as she was having her period. I remember it vividly, as it slid our very easily and was coated in her menstrual blood. We kissed passionately, hugged tightly, and I penetrated her sticky wet vagina with my rock-hard, young penis. I didn't last very long, as my personal excitement, and her wet vagina, were just too much for me!

I am forever grateful to her for “showing me the way”!

Nothing fancy, had real sex with a call girl at age 21, while in the Navy in Bangkok, Thailand in 1970! Fucked her twice then sent her on her way.

When I was in Junior High a girl in several of my classes did homework together at either my house or hers. We were both fourteen and walked home together because we lived in the same area and were good friends. One afternoon while we were doing homework at my house, I noticed she wasn’t herself and asked, “What’s wrong.” She shyly said, “I started my period at school today and I’m having cramps.” I replied, “Oh.” Then she said, “I need to talk to your sister.” At that, she got up and didn’t return for an hour or so. When she got back, she was feeling better. So, we finished our homework, and I walked her home. As we walked towards her house, I asked, “Was my sister able to help you?” She replied, “Sure, I asked her to give me a couple of enemas.” I replied, “Really, does that help?” She replied, “That’s what mom does when I get bad cramps. But now that she's working, it’s difficult. It got so bad today, I had to ask your sister, if she wouldn’t mind doing it for me.” At that our conversation moved to another subject.

That evening after I returned home, and we’d gone to bed. My sister told me what happened and not to be surprised, if my girlfriend asks me to give her an enema in the future. I asked, “What did you two do, that makes you think that?” She giggled and said, “I told her about our activities since grandma taught us how to give ourselves enemas.” I replied, “You didn’t!” She replied, “Why not. She’s your girlfriend, isn’t she?” I didn’t have an answer for that, ending our conversation.

Fast forward a couple of months. And sure enough, my sister was correct, my girlfriend asked me to swap enemas with her during her period. The first few times we swapped enemas together were at my house. After that, the next three or four times were at her house, and it wasn't any different than being at my house. School was finally out for the summer, and we were alone at her house the day after her period stopped. So, following our normal routine when her flow stopped, we gave each a last couple of enemas until her next period. When we finished and went back to her bedroom to put our clothes on, we got to necking. After ten or fifteen minutes of necking on her bed, both naked, and my penis rubbing up against her pussy. She reached down with her hand and took hold of my penis and positioned it at the opening to her vagina. She didn’t have to say anything, I knew exactly what she wanted to do. So, I slowly pushed my throbbing member deep inside her as she let out a little yelp the deeper, I went. Once I was completely inside her, I stopped and didn’t move, while she became accustomed to me. After a minute or two, I slowly started to pull out then go back in, speeding up only a little bit. We continued like that until I climaxed deep inside her. That was my first time having sexual intercourse and it was her first time as well. Unfortunately, she didn’t have an orgasm her first time having sexual intercourse. But I was able to masturbate her too a good orgasm.

I never had sex in my entire live (I'm 38 ) and it'll probably never happen. I am ABDL, I have autism, and I never had a proper erection, not even once in my lifetime.

So having sex is literally impossible for me, wether I want it or not. Even paying for would not be possible because... I can't have any erection.

Mine is sad.

But you asked.

I had just began puberty around 11 and my dad became very ill. He was in the hospital for a long time and I had to stay with my aunt and uncle. My cousin, a linebacker for his college football team, was home when I would get to my aunt and Uncle's house until they got home from work.

The first couple days he was sweet and helped me with my homework and made a snack for me. All that changed the 3rd day. When I got off the bus and walked in the house, he was running around in his boxers and a tshirt. I went to put my backpack in my room and I heard the door close and lock behind me. He was completely naked. He came over and sat beside me on the bed with a shoebox. He raised my shirt and unfastened my training bra and took off my shirt. He worked his hand down to the button on my jeans and unzipped them. Next, he took my pull ups off. (I was having some incontinence trouble around that time though I later grew out of it only for it to come back with a vengeance later on) He began touching me. It did feel good. A couple years earlier, a cousin on the other side of my family had taught me how to masturbate and I had masturbated many times since. That felt good and so did what he was doing to me.

The next part wasn't good though.

He opened the shoe box and brought out a regular drinking straw. He spread me apart and forced it in my urethra. I was making a mess on my bed but I couldnt control it.

By this time his penis was big. He forced in into me. I cried and begged him to stop but he wouldn't. The straw had stopped dripping urine and was now dripping blood.

It hurt. He finished inside me and made me take a shower.

My first time was not good. My first time was rape.

Mine is sad. .... My first time was not good. My first time was rape.

@MissPuffyButt So sorry to hear about that experience. No words can express how awful that was. I experienced abuse / rape as a child, so know how devastating it is. Safe hugs to you and your younger self, if appropriate and acceptable. Take care.

I was in my teens, and I had an attractive girl who was a few years older, approach me at my summer job, and give me her phone number. I had masturbated, and fantasized about having sex, but nothing happened. This girl on the other hand, had plenty of experience, and she was very skilled sexually. The moment happened when we were out on a date, in one of our cars. Neither of us had a condom, and it was past midnight. She got on her stomach in the back seat, pulled her panties down, and smeared a huge glob of Vaseline on her anus. Then she slowly guided me in. I was incredibly nervous but turned on at the same time. I could hear her groan and sigh, and it wasn’t long before I shot a load of cum into her ass, with the force of a fire hose. We had anal and vaginal sex for the entire summer, and I was so happy. At the end of the summer, she dumped me like a hot potato, and ghosted me after that. I was heartbroken for a long time, but I later discovered that she was a player, and that she was juggling several guys at a time. I still think about her hot and sexy body to this day.

@JJM Wow! She had Vaseline on her? Sounds premeditated!

I suppose this was the 1970s, before fear about AIDS would make unprotected sex unpalatable…

Whilst it is only semantics I didn't loose my virginity but happily gave it away.

Although I was younger than probably should have done so (14) it was a boy I'd known for a very long time we were very close and I'd had considered my best friend at the time.

We had messed around before and clearly we both wanted it. We were home alone and really wanted to experience it.

Not an exciting or romantic story but that was my first time.

At 21 with a prostitute

My first try at sex was age 16 was a total disaster. She stunk and I went limp and couldn't complete the act. I left on the run wearing only my pants and carrying the rest of my clothes. I was being laffed at and mocked as I went out.

The first time was not a first time. I was 18, my girlfriend was 16, we were both virgins. We had been flirting for a few months and one day while we were in my room on my little bed, she took the initiative to make me understand that she wanted us to make love.

Taking off her pants and me doing the same I took a condom from a box that I had bought just in case. I was erect, I put the condom on and tried to penetrate her. I couldn't do it, I wasn't comfortable, the bed was too small for two, I lost my erection.

We stopped there, I was disappointed, she probably was too and while later my father took her home with me, she gave me a little piece of paper where it was written that she would like to start again. I was happy and we agreed to make an appointment with a gynecologist to get a contraceptive pill.

Before having our first sexual intercourse we will take the time to discover our bodies, to explore our sensations, mutual masturbation, cunnilingus and fellatio. The real first time, the first penetration will only be easier, I still remember when I was lying on my back she came to impale herself on me, and I came in her from the first centimeters, so happy to be a man now. That was 45 years ago.

We had 10 years of happiness, sexual exploration before she left me for someone else.

I was a late bloomer

I started dating a girl between sophomore and junior year of college.

We went to different colleges in separate states.

She came to visit me on her fall break - and we attempted to make love twice(on different nights). I would always start by going down on her (god I loved eating her out). We were both virgins - and when I would try to enter her, she would cry out in pain - and I would instantly lose my erection.

But we were determined to succeed. The third night we tried - she didn’t cry out in pain. Then after a few thrusts she started to really enjoy it (I did as well). We made love several times that night - and a few times in the morning before I had to go to class. I think we went through a few boxes of condoms that week. When she got back to school the following week - she went to her doctor and got on birth control pills. During Thanksgiving break we still used condoms to be safe - but by Christmas break - we were having sex without condoms - which we both loved.

I really loved that woman - I hope she is doing well.

The following summer was constant sex (best summer of my life).

I was a late bloomer

@Cnewman I have you beat. I lost mine at 21. My boyfriend, now my husband/sub, and I had our making out get to the point of no return. Thankfully he was prepared with condoms so we had protection. (I don't remember the specifics and an unable to give details.)

Sadly I scared him a bit afterwards as I was disappointed in myself for giving my virginity away so easily, we'd only dated a month. I remember I didn't explain that to him, but it didn't stop him from continuing to court me and ask to marry me. 39 years together this May.

Do handjobs or blowjobs count or only vaginal penetration?

Do handjobs or blowjobs count or only vaginal penetration?

@Jacana The topic is about vaginal penetration in this instance. Unless one is gay then they can post their first sexual cherry popping experience. Don't dilute the topic with other "first time experiences" in other sexual areas.

I lost mine at age 17 with a friend who was 16. She was not a virgin at this point. We were flirting in the back seat of a car during a high school driver’s ed class that afternoon and then she came to my house after school. She was going down on me and it wasn’t doing a lot for me (I never have liked to get oral sex that much compared to other activities.) She started getting tired and said, “You’re not going to come, are you?” I suggested we 69. She was hesitant — I think shy and self conscious about having her ass and pussy in my face after a long day at school. She went off to the bathroom and then came back and we 69ed for a few minutes, but then she said, “Why don’t we just have sex?” I agreed. I remember how much I loved hearing her breathe harder and faster as we went at it. I pulled out and came on her tummy. I’m slightly above average size wise I would say, but she told me I would make my wife happy someday because of my size. This made me giddy with happiness of course.

I put a condom on and went on top of her in the missionary position. Then, it did not quite work out: I was afraid of hurting her. I had tried to have sex with another girlfriend who had a kind of phobia of penetration by a penis and had this experience in mind. I suggested I would go on my back and she would climb on me and control penetration. That went better.

She explained to me that even though she was no virgin her sexual experiences had been limited and my penis was thicker than her previous boyfriends'. To summarize, my first time was definitely uneasy because of my inexperience (or, rather, my bad previous experience), her relative inexperience, and perhaps my above average (though not greatly so) erection size.

I was a freshman in college. When my gf came to visit, I saw that she had birth control pills, so once I knew she was on them I felt comfortable going forward. In those days we had bunk beds in the dorm rooms, so I got my roommate to sleep somewhere else that weekend : ) . I think my gf was not a virgin so she helped a bit with the entire process. I must admit that I've gotten a lot better with lots and lots of experience LOL!

I was 17 and my girlfriend at the time, who was 18 years old, was visiting her home. I stayed overnight and while lying close to each other I got an erection, he asked if I would like to make love to him, to which I said yes. She was scared of the pain because she was a virgin and asked me to give her a painkiller as a suppository. I gave him the medicine and after a while we started to try intercourse, it was great despite the first time