How did you lose your virginity? Tell your story!

I was asleep and woke to a bright light in my face, and couldn't see anything. I heard a deep voice say "would you like to come with me?" shielding my eyes, I asked "who...what...are you?" "It doesn't matter," he said. "Your time has come, if you want it."

I was consumed with a sense of longing and I consented. The light enveloped me and I felt my body become weightless.

The next thing I remember, I was in a room with Jason Momoa, Channing Tatum, and the Ryans (Gosling and Reynolds). I won't get into the gritty details but, suffice to say, it was the best night of my life. I've been horny ever since.

_Melissa said:

I could be blind but I didn’t see any recent threads with this topic and I love these kinds of stories! It’s always interesting to hear how people break into the world of sex....
Worst of all the sex wasn’t that special and it wasn’t very exciting. It felt ok but it didn’t feel bad either. After we did the deed I left and was beside myself. This was what everyone has been raving about? Seriously? I didn’t cum and didn’t know how as if it were a switch you were supposed to turn on and off. He called me for days, weeks and then months trying to get back inside. It’s been approximately 8 years since we had sex and I still get texts from him from time to time lol

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Yair, um, sorry about sending those texts over these past 8 years. I'll stop now...

With mom and dad.

Although I hesitate to refer to this experience as "losing my virginity" because no penetrative sex occurred, my first sexual experience ever was with a girl who I wasn't really attracted to. At the time (just a couple weeks shy of my 18th birthday) I was foolishly desperate to lose my virginity and would've done it with just about any girl who was willing, as she was.

She had a really bitchy attitude. She was the sort of girl in high school that had beef with everybody and was always starting drama. This girl had serious mental health issues. Even then, I was surprised when she started bitching at me for an argument we'd had MONTHS prior.

It killed the mood for me completely and I just COULD NOT stay hard, even with her blowing me.

So fast forward about 30 minutes of us fumbling and trying, we called it quits. She jokingly remarked to me that I should see an escort to get some experience before trying to have sex with her again.

Months later, I did just that. Found some ebony Backpage girl (who, upon learning I was a virgin, said, "ok, I'll take it easy on you then since my blowjob skills are amazing") and did the dirty.

That was the beginning of a very expensive hobby. I never did fuck that original girl, but she gave me good advice :biggrin:

TLDR - Tried to lose virginity to a civvie, couldn't get hard, discovered Backpage a few months later, problem solved.

For me, I was about 28, STILL hadn`t got laid, so one evening, I took a couple shots of Jack, and called an escort service ad I saw in the newspaper, (yes, answering ads in the paper, anyone remember doing that? lol) Turned out to be my first `bait and switch`, the guy on the phone told my she was 25, turned out she was more like 35! But hey, turned out to be one of the best times I ever had! Discovered `older` women are awesome!

I used to play doctor with a couple of the girls in my neighbourhood. One was quite large and the other was tiny. I remember being in tiny one's basement. She was curious and wanted me to pull my shorts down. There I was, under the pool table, hard as a rock. She asked if she could touch it and I said yes. It felt strange as we fooled around for a bit, but nothing happened.

Fast forward a couple weeks and we were alone again, this time at my parents place. She wanted to see it again so we went into the washroom and locked the door. Pretty soon we both had our shorts and underwear off. She was face down, I was on top and started humping her. I tried to stick it in but she was really tight. So I put some Vaseline on my cock and tried again. This time I manage to get about half my cock in and humped away for a bit. It was causing her some pain so we stopped.

Here's the thing, I was fucking her in the ass. I didn't even know she had another hole, a vagina. We were only 11 or 12 after all.

_Melissa said:

I could be blind but I didn’t see any recent threads with this topic and I love these kinds of stories! It’s always interesting to hear how people break into the world of sex.

This is how I lost my virginity:

In high school nearly every one I knew was having sex except me. I was scared! I had a boyfriend between the ages of 16 - 18 and we never had sex. We fooled around from time to time, making out, dry humping, getting fingered or I would even get on my knees and...... but we never went all he way. When I turned 18 our relationship became very stale and we were lacking in communication so I broke it off with him. Later on,I was working at an after school program facility (won’t say the name) and was attracted to my coworker who was 8 years older and relentlessly flirted with me for the 2 years I was in a relationship. I was always faithful and never cheated on my boyfriend. But at 18 I was single and no longer a minor to my 26 year old coworker who was 24 when we met. I’ve always had an overly matured body (hit puberty early) and on top of that I’ve always been tall. So at first glance I looked like your average 20 year old. With that being said this guy never actually believed that I was 16 when we met. Anyway at the legal age of 18, I decided I wanted to lose my virginity and he was interested and attractive! So I told him what I wanted and he was excited. He booked a shitty motel for us but I didn’t care at the time because I was just so excited to be having sex for the first time! He turned on the tv and the very first position for my very first time he took me from behind. He didn’t kiss me at all, no foreplay of any kind! Worst of all the sex wasn’t that special and it wasn’t very exciting. It felt ok but it didn’t feel bad either. After we did the deed I left and was beside myself. This was what everyone has been raving about? Seriously? I didn’t cum and didn’t know how as if it were a switch you were supposed to turn on and off. He called me for days, weeks and then months trying to get back inside. It’s been approximately 8 years since we had sex and I still get texts from him from time to time lol

The end of the story was that losing my virginity wasn’t the greatest experience for me. However my second time having sex with another person was what made be become addicted. I look back and laugh at my first time because I was so naive and if I was as smart as I am now everything that happened for my first time never would’ve happened that way!. Ah well. The sex I’m having now adays is pretty damn amazing but sometimes I have to look back and laugh at how it all started!

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You guy was an asshole. You deserved better.

Escort on queen street, summer 1983.

gameboy27 said:

i used to play doctor with a couple of the girls in my neighbourhood. One was quite large and the other was tiny. I remember being in tiny one's basement. She was curious and wanted me to pull my shorts down. There i was, under the pool table, hard as a rock. She asked if she could touch it and i said yes. It felt strange as we fooled around for a bit, but nothing happened.

Fast forward a couple weeks and we were alone again, this time at my parents place. She wanted to see it again so we went into the washroom and locked the door. Pretty soon we both had our shorts and underwear off. She was face down, i was on top and started humping her. I tried to stick it in but she was really tight. So i put some vaseline on my cock and tried again. This time i manage to get about half my cock in and humped away for a bit. It was causing her some pain so we stopped.

Here's the thing, i was fucking her in the ass. I didn't even know she had another hole, a vagina. We were only 11 or 12 after all. :d

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lmao ��

I was 18 or 19. Met the girl friend of a girl friend of mine in a bar. She seemed to like me. At midnight she ask me when I would ask her home... My god I ask her to come to my place immediatly. She says go. I was so excited fuck. We are on the bed kissing. I touch her boobs she puts a hand down on my dick. My god can't beleive it will happen. I push her down quite hard so she could lie down on her back but I misjudge the distance with the wall and knock her head pretty damn hard.

The deed did happened later that night after some icetime and making sure she was all right

Cheers,

p.s. for those interested the actual penetration to explosion took 90 seconds. But it was 90 sescond quality time hehe

Lose???

I wont say the specific age as I was a teen, but a bit before the statistics that is average age

With a man (so penis in vagina) he was my bf and a basketball player. He was 6ft7 and I was 5ft2 at the time...lets say it was painful.
With a woman...giving i went to an all girls high school with nuns as teachers...we did do spin the bottle in sleepover but with sexual content. Now more than a decade later realize welll thats exhibition

steve bettman said:

Escort on queen street, summer 1983.

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Doesn't count as the 1st genuine experience if condom was used.

GameBoy27 said:

I used to play doctor with a couple of the girls in my neighbourhood. One was quite large and the other was tiny. I remember being in tiny one's basement. She was curious and wanted me to pull my shorts down. There I was, under the pool table, hard as a rock. She asked if she could touch it and I said yes. It felt strange as we fooled around for a bit, but nothing happened.

Fast forward a couple weeks and we were alone again, this time at my parents place. She wanted to see it again so we went into the washroom and locked the door. Pretty soon we both had our shorts and underwear off. She was face down, I was on top and started humping her. I tried to stick it in but she was really tight. So I put some Vaseline on my cock and tried again. This time I manage to get about half my cock in and humped away for a bit. It was causing her some pain so we stopped.

Here's the thing, I was fucking her in the ass. I didn't even know she had another hole, a vagina. We were only 11 or 12 after all.

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Great story and well told.

stevieray said:

For me, I was about 28, STILL hadn`t got laid, so one evening, I took a couple shots of Jack, and called an escort service ad I saw in the newspaper, (yes, answering ads in the paper, anyone remember doing that? lol) Turned out to be my first `bait and switch`, the guy on the phone told my she was 25, turned out she was more like 35! But hey, turned out to be one of the best times I ever had! Discovered `older` women are awesome!

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Wow, 28. I was 24 and very stigmatized.

I went to Europe that summer a virgin and vowed to come back home different, a man. The trip was almost over and my 2nd last stop was Paris, the city of love. I checked my tour book and found out where to go. It was an area near Montmartre, quite nice with cafes and cobblestone streets. After a bit, I saw a beautiful mulatto girl on a corner. I walk towards her and then walk past. Too nervous. I walk back and the same thing happens again. So I decided to go to a café and get some liquid courage, a bottle of red. 15 minutes later I had drained all the courage I needed and approached her. We went up to her place and did it, despite how drunk I was. I was verrry proud of myself.

Maybe too proud because the kicker to the story is that as I am walking out the front door she calls after me. Idiot that I am was about to walk out without my shoulder pouch which contained my money, passport, Eurail pass and airplane ticket. Thank god for honest escorts.

anon1 said:

Lose???

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i was loosing my patience one day, when i was lost somewhere in my thoughts. So i decided to lose my virginity, but have lost it again each time i find someone on TERB. But all good, no loss

love that GIF picture

malata said:

i was loosing my patience one day, when i was lost somewhere in my thoughts. So i decided to lose my virginity, but have lost it again each time i find someone on TERB. But all good, no loss

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I think a better question for this board is how did we lose our SW virginity. My first experience with a SW was a spa in Mississauga. Can't remember if it was Blue Lagoon or Soft Hands or another spa at the time. We're talking late 1990's. Anyways got in didn't see any lineup paid my money to reception and waited in room. About 5 minutes later a black girl walked in. She had a nice body, was thin and naturally busty. She had some bush and facially was meh. Anyways it was strictly nude hand release service. I don't think bodyslide was offered back then. I couldn't finish only getting semi-hard.
About 2 weeks later my buddy and I went to another spa. This time I got a facially cute white girl in her early 20's. I was so excited. But she was a total dud in the room. She even refused to spit on my cock to lube it up. No tit sucking allowed. No touching down there (she had almost full bush). Attempted jackhammer finish was unsuccessful. Strike 2.
Fast forward a few years to mid 2000's when I found this board. Did a walk in at SRM and got a tall slim French Canadian brunette. Much better service. Had full erection within 5 minutes. Body slide then hand job with gentle prostate massage. Felt amazing and finished all over her chest at around the 15-20 minute mark. Since then I was hooked.

I was 17.

It was maybe April or May. I had been dating this girl in my highschool for a while (who claimed to be a virgin) and we used to go out "parking" on virtually every one of our dates, however, we never went, "all the way". Usually kissing literally for hours, rubbing, petting, she would give me head from time to time. It was the first time in my life a girl had ever touched my cock and I found it quite thrilling. I remember having blue balls so badly in those parking sessions that I couldn't walk. I didn't have my own car at the time because I was poor, so I would borrow my parents car. But I digress.

She and I talked about "going all the way" and she was up for it, so it was very much planned. It would occur at her parent's house when they were both at work. I was to buy condoms (I ended up stealing one because back then, there was no such thing as free condoms any where.) We walked over to her parent's house and went into her bedroom. I was TERRIFIED that she would get pregnant. We did our usual necking thing to the point where the big event was supposed to occur and I put the condom on. I clearly remember being absolutely convinced (with my luck) that the condom would fail and I would be a teenage statistic.

She climbed on top. It slid into her wet pussy and voila, I was no longer a virgin. (As an aside, though she claimed to be a virgin, pretty much every woman I ever told this story to laughed and said, "she was not virgin". No virgin climbs on top and it just slides in. (And having had a couple of virgins later on, I can a test that it is really hard to break through the hymen with just your cock. REALLY difficult. But again, I digress.))

So anyway, she's riding away and I'm not sure what to think. (Though I definitely knew what to do. I'd watched a lot of movies!) Again, the terror of getting her preggers took over and I stopped it before I came. Condom or no condom, I didn't want to cum inside her. I have no idea how long it was. Definitely not long, it could have been 30 seconds, or 2 minutes, I don't remember.

I do remember walking home to my parent's house with my head racing and just thinking, "there has to be more to this". I was quite disappointed. I had been looking forward to that moment since I was about 10 or 11 and had figured it out. But this was a let down. (Fortunately, there IS a lot more.) I remember wondering if people would be able to tell that something in me had changed.

To be brutally honest, I did not really fancy her all that much. She was just a curiousity. A very simple down home girl who didn't have much to intrigue me other than she was a girl with a decent look to her. I had never had a girlfriend before, never had any kind of real sex play, and I finally met a girl who was willing to indulge me. We were very different to say the least. We ended up sort of on and off (as she found a job in the military that took her out of town) and I think we may have had sex 5 or 6 times over the course of a year and half (IIRC). We finally broke up when I told her some stupid lie just to get rid of her. (Pathetic but true. I didn't want to hurt her feelings.) I did not love her. I did not even really like her, though I certainly did not dislike her. She was just sort of there and she was willing. I have no idea what became of her. Sometimes I wonder though....

All of that changed when I found a girlfriend in university that I was madly in love with. I would have taken a bullet for her and the sex was everything I had ever hoped for. God, I wish I could be 20 again. (But that's a sob story for another day.) Is there anything as sad as a 20 year old boy in love?