Actually I recorded it.  Nothing out of the ordinary though.  See

http://www.youtube.com/watch?v=Lgswr7fN3wI

Well she wanted to do role playing.  So I got my Spiderman underoos and she brought these.

http://24.media.tumblr.com/tumblr_m4ps0m1UZr1r53fvao1_500.jpg

The most embarrassing thing about my first time? I've never had one.

I was 15 and after me and the girl I was kind of seeing went back to my house after a school dance. She had a lot more experience than me. Well I was very awkward about it and of course first time didn't last long. But after I was done I asked her if she enjoyed it. I still remember the absolute look of contempt  on her face when she said "of course not are you fucking serious."

This is what I imagine a few of you like.
 Semi NSFW (David Tennant with a stress ball that looks like a breast.)

http://media.tumblr.com/a20dce3b4618faba230c748f2c351914/tumblr_inline_mg8gigSJZ41qlsa5w.gif

No need for a complicated set up. It was with a Filipino girl that spoke English ALMOST well enough to sound like a native speaker, like the Family Guy joke. So... she leaned in, and seductively... I guess... tells me "I want your fenis" I obliged, but she kept saying "fenis" it was HILARIOUS.

My first time was like most... a failed entry the first few times (though I thought I was in), before finally getting it right. But it was the "before" that I remember the most.

I had to buy a condom so I went to the store and looked at the display for what seemed like an hour. I was trying to make sure I picked out the right one. I read the packages and tried to discern which one would give us the best experience. Then, after making my decision, I was about to go the counter when I suddenly was hit with a fear of looking like a pervert. So I started grabbing a bunch of other items to "hide my shame". Then, in true "coming of age movie fashion", my chosen condom wasn't in the system and they had to send a runner to get a manager so they could figure out the price. This happened with three other people in line behind me, all looking at this nervous kid who was now spending about $50 in groceries to hide his condom purchase.

I was 15 and was the victim of Girl on Guy rape...which sounds awesome, but let me explain. I had just had reconstructive nose surgery and was discharged from the hospital, and I was brought home by my parents and put to bed. While asleep, a girl that I had been "dating" for maybe a week came to visit me. So, long story short, I wake up cumming with her riding on top of me. I worst part is that when I woke up it scared both of us and she head-butted me right in the nose. So in the fun mix of semen, blood and tears, I had to walk downstairs and have my parents drive me back to the hospital. As I was being put back under for surgery, my dad turns to me and says, "Your face looks like a road map to Uruguay, but at least you got laid"

Age 15, my friend and I stopped by a girls house where my girlfriend was. After some nervousness, my girlfriend and I finally made it back to a bedroom. The elation of the first time being fully naked with a girl is still fresh in my mind to this very day. After some foreplay, we were getting ready to seal the deal. That's when the screaming from outside the bedroom happened.

My friend came yelling at the door that we needed to get out of there. I could then here the girl that owned the house screaming at him like a banshee. We got dressed fast as hell and came out to find my friend running around the house waving the girls giant dildo above his head. One swift shove by the girl sent him over a coffee table and the dildo across the room. We made a break for it out the front door - - then she came running after us -- the dildo flailing above her head in a death grip.

We made it into the street, still running when the dildo came flying past us after she hurled it. And that's how my attempt a losing it ended. A 10" dildo bouncing down the road. My girlfriend and I later lost it in all of the 2 minute glory I gave it.

College Halloween Anime Club Party, me and my girl got wasted and woke up in each other's costumes (she went as Revolutionary Girl Utena and I was Sanji from One Piece), but the embarressing thing is that there was a Sakura costume (from Naruto) on the floor of my apartment.  Now neither of us owned this costume and when we nor any of the club members remember (or at least admits to) knowing anyone who went as Sakura to the party.  The costume was well made, but it couldn't have fitted someone larger than 5foot 3.  Weird really...

My first time was when I was 19 years old with this incredibly beautiful girl who lived an hour away from me. I got lost on the way up there and got pulled over and given a ticket for a busted tail light but nothing could stop me. When I finally got there, I was so nervous that I went in her closet to put the condom on which she found HILARIOUS. So hilarious in fact that I couldn't finish and ended up humping on her for almost 2 hours. The first hour she kept laughing and the second was spent yelling at me to hurry up...... She ended up being my girlfriend after that and we dated for almost a year. (she was crazy.)

The first time I had sex was with an exteremly hot girl so it was pretty embarassing. Luckily she was a virgin too taking away a  tiny bit of the embarassment. Well anyways I lost it in a camper and I had my best friend in the other roomtslking to me, trying to motivate me, because of how nervous I was. Luckily I didn't shoot off insanely quick like everyone was telling mewas going to happen. That would have been so much worse than it already was.

I was 19, and in love. Then she bled on my penis.

I charged a guy $600 and he still have the credit card receipt.  Visa I believe.  ☺

So I meet this guy at a bar (I know what you're thinking, and you're probably right...) he looked pretty decent... and the fact that we were staring each other down from across the bar gave me some confidence. I walked over, he smiled and said, "Let's go." as if he knew what I was thinking all along. We leave the bar to his Chevy, and get down to business. For some reason he didn't want me pulling down his pants, so as a joke I pulled them down anyways. I regret to say that I have never done anythingnow with a man... only a transvestite. And a very convincing one at that.

So it was spring break. I was at her house that she shared with her mother. I was 22. We did the deed upstairs in the afternoon. After we finished we realized her mother had come home from work for lunch. Despite being very safe, she panicked and told her mother what had just happened. Her mother convinced us to go get plan B and take it immediately. I then returned and ate dinner there. Very awkward.

on the advice of my lawyer i will not enter this contest :)

I had a Chris Elliott moment on the drive back to my house afterwards . I called my best friend (who lives in Hollywood) and told him, "Art... these pipes are clean."

My, my, my. It seems as though I'm the only virgin here. You know what that means? In case we're ever atacked bu Unicorns, I'm our only defence. "Timely-Tardis Lego: The Last Unicorn Tamer"

Everything I was told were lies the hundreds of hours I spent masturbating did nothing NOTHING, to prevent me form the calamitous event that occurred the first time I made the beast with two backs (insert premature ejaculation joke here). Also this would later be the source of much amusement to my friends.

The first time I had sex I was so scared... I was all alone....

Since my first time with another person was perfectly fine and did not involve payments of any kind, I'll offer the true story of the first time I self-pleasured.

I didn't know anything about jerking off.  I also was just at the point at realizing girls didn't do it for me and I liked guys.  But I had no clue what they did together, or how anything worked.

So I was alone in the bathroom, getting cozy with the rug.  I had imagined a handsome guy.  He was just standing there, looking pretty, but that was enough.  Something was happening, at any rate, and it felt good.

At the moment of orgasm, Mr. Perfect vanished, and I saw before me Aslan and all the characters from the Narnia books, in their new perfect world seen at the end of The Last Battle.  They were all waving goodbye to me.  Like Susan, who had grown up, I was no longer welcome in Narnia.  For a moment, I could see them all clearly, waving sadly, and then my POV camera backed away from the scene and they shrank into the distance.

Some people call out "Jesus" when they come.  Not me.  It was an unintentionally spoken "Oh, Aslan."  I laugh about it now, but there was a definite sadness and loss there, no doubt brought on by years of Catholic catechism.

This in no way dissuaded me from chronic masturbation.

I NEED DIS. GOOBY PLS.

I was much much younger than I am now, it was dark and neither of us knew what we were doing.  He nervously started to talk so I gently covered his mouth with mine. Then as our mouths parted I fumbled my fingers to his lips and whispered, "dont say anything." The silence didnt last long. It was the first and best I ever had. I remember his last words to me as I left the room "My name is Teddy Ruxpin and I want to be your friend"

IT'S REAL TO ME DAMMIT!!

(ok, maybe not)

I was 10; she was 9. We did it in her garage. The ground was gravel. I felt like I was picking rocks out of my ass for a week. 

I was pretty heavy into D&D growing up, and for me that was as REAL as anything. (much like Tom Hanks in "Monsters and Mazes")

So one average teenage summer afternoon I began a new quest in my buddies basement - that's the basement of his house, not a metaphor - along with a few other friends.

I was a dwarf. A strong, proud, virgin dwarf.

Shortly after I began the quest I took refuge at a tavern and a local wench caught my fancy. I decided to drink heavily to gain confidence. I wanted to give her the ole "sword in the stone" if you know what I'm saying ;)

The Game Master made me roll to see if I would score. I rolled...poorly.

Long story short, after a series of terrible, terrible rolls, I became very drunk, got my dwarf dick stuck in a tree and eventually starved to death.

But hey, I didn't die a virgin.

I've often said that because of the different ways society views virginity in men and women, that chicks lose their virginity while guys get rid of theirs. I had to pay someone to help me get rid of mine.

I had originally written a long explanation, but lets leave it at the short story.

My first time was broadcast on the internet to a regional swingers group (unknown to me in the moment), and I was recognized at a bar a little while after as "that guy from last week's cam show who whines like a dog when he gets off"... by a woman I was hitting on.

"tell me (and the world) the single most embarrassing thing about your own first time"  and  "Enter as many times as you like" 

 I don't think someone can tell you their single most embarrassing thing about your own first time and get to enter more then once?

All and all it went decently normal.  Damn my luck.