Losing the Cherry

Losing my cherry was a memorable experience, I paid off a tanker in Singapore, I was an 18 year old Cadet at the time and had to wait for another ship. We all went up to one of the bars for farewell drinks and naturally some of the bar girls came over. The one sitting next to me started to slide her hands up the leg of my shorts, being shy and inexperienced I calmed my hand down on my upper thigh to prevent further progress.The others saw what was happening and were laughing and saying cherry boy. anyway I rleaxed my hand to get my drink and the girl took advantage of it and hand her fingers clamped round my dick which reacted in the normal manner for an 18 year old. The girl announced to all "he very stiff"
Hoots of laughter. My shipmates decided it was time for me to lose my cherry , they would pay but they would watch. We proceeded in a noisy procession to the girls room where she stripped off and spread out on the bed while just stood there like an idiot. The girl got up and basically stripped me to much laughter form my so called friends. Ther I was with percy pointing at the ceiling still not quite knowing what to do. The girl pulled me onto the bed and guided me into her and in 30 seconds falt I believe I had shot my load. That was it my friends went back to the ship, I went to the Officers rest Home to wait for my next ship which did not I am glad to say appear for 3 weeks.

 

My first time was particularly romantic and special: It was a spontaneous snogging session with some fat chick I never saw again, on a hay-stack in an abandoned industrial warehouse in the run-down part of Miami, Oklahoma (which is pretty much every part of Miami, Oklahoma FYI). Ahhh, sweet young lust

 

My first time with a guy was at a birthday party for a friend. It was with a guy I had known for a long time and we were close friends not really dating or anything but we were really close and I knew he was wanting to lose his cherry, he wasn't really very popular but he was kinda cute. He didn't ask me or even hint that he wanted to with me but some guys were teasing him about never kissing a girl and I got kinda mad so I kissed him In front of them and took him into the bathroom. We had sex in the bathtub and everyone know it.

 

My first time was in 1975 (I was 19 at the time), in one of the rooms in the NYC Statler Hilton, during a Star Trek convention. The girl and I were both on staff for the convention, but she lived on the east coast and I lived on the west coast (I flew back east to work each convention.) Each convention was basically a five-day weekend with virtually no sleep. The girl and I had gotten to know each other over the previous four conventions that we'd both worked and we just sort of gravitated towards one another. By convention #5, we were up to a fair amount of deep kissing and groping under/inside clothing. When the events finished up on the second evening of the con (which was actually our third day together), we both stumbled upstairs to my room, locked the door, and clumsily undressed each other (first time we'd seen each other nude, but we were too tire to pay much attention.) We climbed into bed, kissed for a little bit and then, without any further ado, I rolled on top her and in between her legs, but before I could move up into her, she slid down under me and sort of "grabbed" my cock with her pussy. I blinked and I was all the way inside her! We just lay there for a moment or two, not speaking but just kind of considering oh, so that's what it feels like! Then I started thrusting and she pushed right back. We didn't last very long, but she came before me.

We both slept really hard that night and, when we fucked again the next morning, we lasted a lot longer. Afterwards, while we were getting dressed, she confided that she'd wanted me to fuck her since the first day we met, over a year ago. I asked her why she didn't tell me back then. She looked me square in the eye and replied, "Could you have?"

Could I? Probably not.

 

My first time unmentionable...

My first time as a willing participant was memorable in its own way. We had been dating for just over a month and being the geek I am we had been roleplaying at a friend's house and it was his 16th birthday. *blush* I was 15 and scared excited as we both knew what we were up to. We climbed the mountain (large hill lol) in Corvallis Oregon. It was snowing and the air felt sharp, dangerous, and clear. We were pretty well versed in making out by then, and he laid his his heavy wool trench coat on the ground for us. It hurt a lot, and I've no idea how long it lasted, but it was a magical sort of pain. I cried a little and other than our breathing those were the only sounds in that cold still night. We made our own heat and it was an exhilarating experience to share with another human being. I bled which really surprised me (and ached for days after) but was still very glad we had started that adventure. Then we put our disheveled clothing in order and hand in hand walked back to our friend's house to continue our AD&D game.

We're still close friends and I look back on those memories with smiles in my heart. <3

 

I didn't lose my virginity until I was 30. I can't say that my first time was super-memorable, but I will say that the 20 minutes leading up to it were unforgettable!

For starters, I had been dating my girlfriend for about 10 months before she let me have sex with her. (no, not making that up- guys like me have extremely limited options) When the Big Night finally came (which is more than I can say for myself) my girlfriend said we needed birth control.

So, I rushed out the door to the nearest place to purchase a pack... which was the gas station 2 minutes from my apartment. I walked in and went straight to the counter, asking to buy some. The woman at the counter, who pretty much defined the phrase, "rode hard and put away wet", gave me a look that can only be described as lascivious!



I got my 3 pack and ran the hell out of there and back to my apartment. There, I quickly undressed and attempted to put on a condom, but since my girlfriend insisted on total darkness I couldn't see what I was doing- I ended up putting the thing on inside-out.

I recalled my sex education class in college, where we were trained to put on birth control devices on bananas, but we had the advantage of working in a well-lit area. On a side note, I was the only 20 year old virgin in a roomful of about 25 experienced people.


Being fearful of contamination (what the hell did I know? I was just being cautious!) I threw away the first one and tried again with the second one- same result. Finally, I excused myself to go somewhere else more illuminated to put the damn thing on. (It was the last one, and I sure as hell wasn't going back to that gas station!)

Eventually getting the thing on, I stumbled back to the bedroom and proceeded on the next nightmare, which was finding the proper hole in total darkness. It would have been nice if my girlfriend had lent a hand, but she lay there waiting for the action to happen.

After about 10 minutes of struggle, I managed to enter her and proceeded to have the second-worst sexual experience of my life. (I already covered my first worst in another thread and need not repeat it here)



Goddamn, did it hurt!

Every single thrust was a letdown. I carried on for... I don't know, 15 minutes? Presently I said "If you don't mind, I think we're done here." Didn't even have an orgasm. I started to contemplate the possibility that perhaps I should just stick to masturbating when this chick ends up dumping me.

I guess the joke is on me, though- she never dumped me. I ended up marrying her. And we don't really have sex anymore. (I was just getting used to it, too.)

 

It seems like most of you lost your virginity at age fifteen. I didn't lose mine until nineteen. I guess I didn't get the memo. Oh, wait. I DO actually remember getting it. I just always wondered why it was delivered by a Galápagos tortoise!

 

I lost mine at 16 to my future wife.
We had gotten pretty hot with heavy petting? a number of times before that with me giving her orgasms but not the other way round.
I explained that what she leaving me in a state of painful erection which wasn't very cool.
Looking back, that was an obnoxious way to get laid but I blame it on being 16 and really horny.

 

I got the memo "It's time to lose your virginity" when I was 15, and continued to get it until I was 18, at which point it started to read "Why are you STILL a virgin?", and each time I would angrily crumple it up and toss it in my backyard.

Well, you know it took an awful long time...

 

That's impressive actually.
When I was 16 I would cum if the breeze even blew just right.

 

I was 13, she was 14. We were at a friend's house for a party and one thing led to another and the next thing you know I was losing my virginity. I remember it yes but it was not her first time. While everybody was outside in the pool having a good time we were in my friends parents bedroom on their bed having sex. And everybody knew what happened because I couldn't keep my mouth shut and neither could she and apparently you could hear us outside. My friends parents were not home it was just one of those random parties on a weekend in the summer. Nothing romantic. But I smiled for a week straight. And we did it once a week for a year or so.

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Ladies, honestly.......how many of you had your hands down the pants of a 16 year old boy and DIDN'T end up with a warm sticky handful?

 

I was too. Lol. I didn’t write that bit down though.

 

I was 21, and by far the least sexually experienced among my peers.

A friend, D., decided to help me out.

She had joked about taking my virginity. When she was inebriated, she said, "Go ahead, ask me anything, I can't lie when I'm drunk."

I asked, "Were you serious about sleeping with me?"

She was.

We arranged to meet at her place the next night.

It went extremely well.

(In retrospect, though, she was very easy to please, compared with almost all the other women I have been intimate with since then.)

We knocked over and broke a lamp by her bed, but she repaired it the next morning.

I was walking on air for weeks afterward.

Very soon after, I got involved with J., the woman I had courted for a year, and thought was the love of my life.

About four years later, I went back to D. for a little while.

 

Despite all the advice I've given over the years, I was a late bloomer. My first time, I had gone down on her for the better part of an hour with great results, but once it was my turn I couldn't keep it up I got hard enough to get a condom on, then I got it in and went soft. I took a few seconds to come to grips with what was happening, grabbed her hips, and said "sit on my face and I'll make it up to you." Two orgasms later, we called it a night.

 

In terms of PIV, it was over 30 years ago. I was an 18 yo undergrad. I'd been seeing this girl for a few months and was totally besotted with her. She was a virgin as well, and the night it happened I had no reason to expect it... So much so, that I didn't even have a condom. After borrowing one, we did the deed. It was quite special to me.

I found out some years later that she hadn't been a virgin, as she'd been molested by an uncle and raped by her mothers boyfriend. She told me then, that I was her first with love.

I'll take that.