I promised a while back that I would tell the story of how I lost my virginity. People just love telling these stories anyway, but I’ve always found my initiation into intercourse to be particularly amusing.
To me, at least, and hopefully for some of you as well.
Somehow or another I got to be twenty-one and was still a virgin. How did it happen? Well, I didn’t want it to be part of the sticky 15-year-old fumblings in highschool, wanted it to be special and maybe even romantic but of course the older I got, the more special the guy had to be, because I’d waited so long. Basically, the task grew more arduous with every passing year, and before I knew it, it wasn’t something special, it was an albatross hanging around my neck.
About the virginity. I should explain. I think I may have made it clear above, but in case I didn’t we’re talking technical, coital virginity here. I’d been fooling around with boys for years, knew what a cock looked like and felt like and tasted like. Just hadn’t had one inside me before.
And then there was Marty. He and I had been good friends for years, hung out, had fun together. He was absolutely adorable to me. He was also bisexual.
Somehow I got it into my teeny little 21-year-old brain that a bisexual buddy would be the best man in the world to give my virginity to — he was comfortable with sexuality, he was comfortable around me, and he wouldn’t fall in love with me or want to go steady or anything. He’d also be careful with me because we were good friends. He even carried condoms with him. This was my logic.
So one night we’re hanging out at my place, talking, listening to music, drinking a little, and I ask him if he’ll do it. After some discussion, he says, “sure”.
We pull out the bed hidden inside my big L-shaped sectional, and lay down on it. Some kissing. Some dry humping. And we decide it’s time for the big moment.
We get undressed. We kiss a little more. He tells me it would be easier for me the first time to be on top, that way I could go as fast or slow as I needed, to control the pain.
So I get on top. And I’m just kind of straddling him, waiting, because I don’t really know what to do.
He tries to push it up inside me.
It hurts. It feels waaay bigger than I expected.
Turns out it feels that way because Marty has gone soft, and he’s trying to push it up there anyway.
Unsuccessfully.
It becomes obvious to both of us that this isn’t working. But we’re dogged kids in our early twenties.
Must be some way to make this work.
I lick and suck him, trying to make him hard. He’s just floppy in my hands. So much for my oral skills. 🙂
He starts stroking himself, but as soon as he removes his hand, he loses his erection. He digs in the pocket of his jeans and produces a cock ring (my thirty-one year old mind is saying cock ring? what twenty-three year old boy carries a cock ring in his pockets every day?). He straps it around himself, and starts jerking it again, trying to get hard. Somehow, the cock ring breaks.
Desperate, he asks me for a hair elastic.
Confused, still hoping to lose my virginity, I go get him a scrunchie, which he proceeds to wrap around his cock and balls, and tries again.
Nada. Zip. Zilch.
He decides that I should just get on top anyway, and hump him a little – should perk him up. So I do.
And once he’s reached semi-hardness, he grabs it with his fist and tries to shove it up there again.
Ow.
At which point—you guessed it—Marty loses his erection again.
By this point I’m pretty upset. And feeling more than a little foolish. I tell him to forget it, that it’s just not going to happen. We sit side by side on the bed for a few moments, not saying much. Which is when it hits him. Like a lightning bolt from the sky.
He’s not bisexual. He’s actually gay.
He never knew this about himself. It’s a revelation. Sure, sure, sorry about the whole losing the virginity thing, but Vikki, wow! He’s gay! What does this mean?
We wrap ourselves in blankets. I pour us each a strong drink, silently. And we head out to sit on my balcony.
We sit there all night. I don’t say much. He talks and talks about this wondrous discovery and re-examines every sexual and non-sexual relationship he’s ever had, looking at it through these new eyes. Till 5 am. My self-esteem slides down and ends up in a puddle at my feet.
In trying to lose my virginity, I helped a man discover his homosexuality. 🙂
It sounds sad, but honestly, in retrospect, it’s one of the funniest moments of my life. I run through the story in my head, and by the time he asks for the scrunchie, I’m in tears from laughing so hard.
And so ends the tale of part one of losing my virginity. Part two soon.
That reminds me of how a friend of mine from college came out to me/discovered his homosexuality. No, no.. he wasn’t helping me lose my virginity. Stay with me.
Eric had been expressing frustration in his love life. He was having trouble maintaining interest in the women he was dating, and it was driving him nuts. He figured it was due to some emotional issues he had experienced throughout adolescence – he went through a long phase of “not feeling”. He figured that he still was not fully recovered, and that it was causing his trouble with women.
Eric had been storming around in a grumpy funk for weeks, because he was just getting fed up with it all. Then, one day he came bursting into my dorm room, all happy and excited. Our whole group of friends were sitting around, and as we looked up at him, the first words from his mouth were… “Hi guys! I just figured it out… I’m gay!!” He then sat down smiling, and didn’t utter another word.
While this wasn’t exactly a homophobic crowd, it was certainly not a group of guys who were entirely comfortable with the topic either. Everyone went “Well… that’s, uh, great!” or somesuch, and found that they had to be elsewhere.
I’d never met an openly gay man before, and was rather naive about the whole thing. So after everyone but Eric left, I turned to him and asked if he minded if I asked him something about it. “Please!”, he blurted, frustrated that his big news had cleared the room. “I’m dying to talk about it!”
So I said, “I’m not doubting you… I’m just curious, but what made you suddenly come to the conclusion that you’re gay?” He paused, and then said “well, I was standing there at work, and this cute guy walked by, and I got a hard on. And then I suddenly realized that men were the only ones that ever cause me to get a hard on.”
I paused, then nodded. “Yep,” I said. “I suppose that’d do it.”
Thanks for sharing, byr0n! I’m so glad that your friend managed to figure it out for himself… without the help of a woman. 😉
Makes me wonder if the girl who (nearly, or sort of) received my virginity thought I was gay. Truth of the matter was I’m just not a morning person. Good thing is though she left me right after that so I found out what she was looking for! I just hope not all women ditch their men if there not randy before the coffee.
Ok, I know this is sort of an old post to comment on, but I just discovered your blog so stick with me.
Your post reminded me of my first attempt at losing my virginity. While I didn’t help my potential partner discover any hidden truths about her sexuality, it was also a massive exercise in frustration.
I was in high school, and this girl and I had been messing around for a while. She was pretty kinky, for a teenager, and we had incredible phone sex all the time. She loved to give handjobs, and was on her way to developing a fine blowjob technique. We were both virgins and decided that it would be great to lose our cherry to each other. A friend of mine even volunteered his house while his parents were out of town. On the way there we petted heavily in the car so we were damn hot and ready to go when we arrived. We got the condom slipped on, then tried for over an hour to get penetration…. to no avail. She was just too tight, and I was far to inexperienced to know how to help her loosen up. Not to mention the fact that the condoms weren’t lubed….
We never went out with each other again after that night. Just too embarassing for both of us I suppose.
On the upside, that was the ONLY time in my whole life I have ever heard a girl say “you’re too big”!
That is funny.
What happened with part 2 of this story?
Will you also tell about the first time you gave a B.J.?
*laughs*
Honestly, SL, I don’t actually remember my first blowjob – I know it was when I was 15, and I know who it was with, but beyond that – no memory. Sorry!
But I do, at least, remember the second half of the “losing my virginity story” – I’ve posted it here:
https://www.herdesires.net/archives/diary/20040111_losing_my_.html
Enjoy!
Wow, hey, thanks! Part 2 was a good story too, not too much fun for you at the time but it at least sounds like you remember it fondly.
As for blowjobs, wow too, if I calculate correctly, you spent 5+ years giving them without having any intercourse. That’s kind of a fascination of mine, so if you’re taking requests, I’d love to hear some more about your sex life during that period. (I had a girlfriend at that age with a similar policy, which amazed me at the time, and I’ve never gotten over it). Cool!
Thanks for sharing your story. It’s one of those remarkable moments in every persons life that never quite goes out of memory – no matter how lame or forgettable it was.
I was 16 although I had been telling my buddies for a couple of years that I been to the show – everybody seems to lie at that age.
My girlfriend was from another town and school about 15 miles away. We met each other in CCD. She was a terror sexually at her tender age of 15. Her biggest thrill in life was giving blowjobs which she regularly begged me to cum in her mouth which for some reason I could never do. She was like a gem of a find looking back on it!
We had been ‘going together’ for about a month and still hadn’t ‘done it’ yet. So, we head to a budddy’s house who’s parents were boozing it up somewhere and wouldn’t be back until morning. We drink a couple glasses of some liquor concoction, head up to my friends room (I can still picture the ‘Dallas Cowboys’ comforter he had), and proceed to get naked. I had a condom which I wasn’t sure how to put on but managed to do it. She was no virgin so she lined me up, grabbed my ass and pulled me in.
So I had long expected a series of fireworks to go off or something. Hey, there’s a lot of build up to this event. So, while we had a good time while it lasted (I might have been a 20 pumper on that one), it was no earth shattering experience. I needed more time to learn.
Missy and I broke up a month after. Now I appreciate what a sexual dynamo she really was at such a young age. I guess I couldn’t appreciate it because I didn’t know anything.
Luckily I met a 22 year old divorced love goddess the next year who taught me all about that little spot she called ‘her peanut.’
Wonders never cease.
Hmmm…
I learnt a big lesson in losing my virginity and that is, NOT TO LIE!!!
From a young age I felt like I was pretty good at charming girls into getting in bed with me. I’m not the most handsome chap or anything, just a bit conniving. It always worked and from the age of about fourteen I found I was able to get myself into a number of situations with girls the same age offering their virginity to me.
However, I always did the right thing and never took things all the way, often settling for naked kissing and humping.
While on the one hand I did really want to sleep around and be a stud, I was nervous about the deed and desperate to lose my virginity in a meaningful special way.
But my big mouth got me in trouble, I used to brag that I had slept with girls when actually I had chickened out at the last minute.
For example I used to meet this girl from school, we’d go to eachothers houses and listen to music while kissing in our undies. One day she started to remove hers and mine. I cant remember how I got out of the situation. In the end she stopped seeing me and shortly after lost her virginity to a real asshole who treated her really badly. I felt like I was partly to blame, that if I had taken things further it would have been very special and loving.
This same set of events occurred over and over with different girls until I was eighteen. By now my big mouth had given me a studly repertoire with my mates, who knew that I had been in bed with these girls naked but not that I had failed to go all the way.
Anyway, I was seeing a lovely girl, who was a friend first which developed into a real high school romance. We truly were in love, and took our physical relationship really slowly.
Our leaving ball was approaching and she booked us a room at the hotel it was being held at. We both were anticipating what would come. I knew she was a virgin, but she thought I was a really experienced ‘deflowerer’ when in fact I was a complete novice when it came to penetrative sex.
I was so nervous and wrecked two condoms before getting the third on, we were both shaking and sweating. I told her it was the first time I’d made love instead of just having sex.
It was a very special night for me, but I feel like I let her down. I couldnt hide my inexperience and I think she was expecting a lot more.
She split up with me when we went to university and I havent ever seen her since. It pains me to think that she thinks of me as someone who simply popped her cherry as I had done a dozen other girls.
I wish she knew the truth, that it was the first time for us both, and that it meant so much to me.
My darker side always pains me as well when I think of the list of girls whos cherrys I could have popped. If only I knew then what I know now!
Me and my big mouth!
INTERESTING STORY BUT LET ME TELL U MINE ME AND THIS GUY WERE DATING 4 ABOUT 8.mnths and i told him that i was expreienced when it came to sex so he told me that he was also. we then decided to have sex I had no clue that it was going to hurt as much as it did. it was hell and come to find out he wasn’t as expr=erienced as he said he was because he came ssooooooooooo fast until I was actually laughing