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part 1 - part 2 - part 3 - part 4 - part 5 - part 6 - part 7 - part 8 - part 9
part 10 - part 11 - part 12 - part 13 - part 14

From: Pyromaniac Guy

i got my cherry taken freshman year at uni. i was with a bunch of geeks at an academic conference in toronto. As part of the deal us students had to do the AV stuff during paper presentations for a waiver on our registration fee. i was heading back from the last talk of the day from a remote section of the basement level of the toronto convention center and noticed debbie, this 5'10" blond supermodel looking geeky girl walking my direction, clearly having been crying recently.

"deb, whats wrong?" i say - and without a word she takes me by the hand, leads me into a restroom (without even checking to see if it's empty), heads to the last stall (handicaped) and starts taking off my pants. I'm totally shocked to the point of total speechlessness. I was a late bloomer (go figure) and only got to second base previous to this moment. and now a girl - no a woman - who could give cindy crawford a run for her money was busy undoing my pants. so she gets on top of me while i'm sitting on the john for what i hope was at least 5 minutes of doing the nasty. she finishes up and simply says 'thanks, i needed that' and leaves me to clean up.

later that night i found out that her bf stood her up (he was to be joining our group after everyone else got there). she decided after that not to look for romantic entanglements but we immediately became (i assume) mutually exclusive fuck buddies. As there was a housing shortage at my school she had an off campus apartment. all we did was sex sex and more sex. my fondest memory was of using a cucumber on her as a dildo, then having her cut it up - without washing it - and using it in a salad we ate for dinner with a couple she was friends with (along with spaghetti and garlic bread) later that night.

From: Plumprooster

I was 23 :-/ and she was 29. We met on CL and she said she wasn't in the mood the first time we met; she just wanted to talk. I had other ideas though. I started fondling her right as she got in my door, then kissed her and wrestled her onto my bed slipping my finger first into her pants, then dipped into her snatch and guiltily pulled right out as if she had teeth. It was warm, mucousy, and had slippery ridges of flesh, and I tried to hit her g-spot like some video I had watched instructing you on how to make a woman squirt. I pulled down her top and wrapped my mouth around her pink nipples too.

It didn't take long before she got into the mood and said "we're fucking." I pulled out my cock and awkwardly crammed it into her snatch w/ a condom on first. I couldn't feel anything because I followed my friend's advice: he had told me to beat off two or three times so that I didn't prematurely ejaculate. It worked too well and I couldn't feel a thing since my dick was raw from the frequency of and my rather unique technique of masturbation (a story for later perhaps.) Anyway, the only thing I did feel was that she was incredibly tight and congested near the entrance and it slipped in more easily further on. I explored w/ my fingers which turned her on more than my awkward fumbling with my cock and she leaned more and more over my shoulder moaning more loudly the harder I rubbed her, her pussy was really squeezing my fingers. Very hot. She let me pull off my condom to finish but I never did. My dick was way too sore that night and I expected more from a real living vagina that I should have. She was upset that I didn't, but I did eat her out to great effect, suckling her clit like a nipple which I got me a second chance, and several more after that. It was very hot, but I never got off.

From: Vzenuh

I was 16 she was 15. Really not to much to brag about except for the fact that I didn't learn about the fact that you should spit on your dick or at least get some spit on her pussy first. Needless to say it wouldn't go in and all I managed to do was make her pussy start to bleed. I didn't know this at first till I decided to lick her pussy to see if it would help out. Needless to say I went down there saw blood and my dick went limp almost instantly. I was lucky at the time though cause she had some big ass tit-tays and after playing with them for a bit I was able to get hard again. Needless to say I didn't cum the first time. For some reason everytime I got close I started having visions of her bloody pussy.

From: Babyshaker4000

I was 16, she was 15. We went out a few times, spent a lot of time just hanging out, watching movies, talking. Mostly about other movies and music (She was pretty sheltered, and I grew up with a sister who was 9 years older than me, so I had a head start in the first place as far as all that goes.)

Anyway, we were just hanging out in her room, started making out, then she leaned in and asked if I was ready. Of course I said yes, slapped on the condom that had been in my wallet for months and months, and awkwardly pumped away on her super creaky bed for about 5 minutes.

Didn't realise how loud her bed was until I noticed that her grandma never looked at me the same again when I would come over.

From: Focusinc

I spent most of my time in high school playing jedi knight 2/full force/ctf/sabers only. I asked the Brazilian exchange student to jr prom when I was 17. She was on the track team and the soccer team. This girl was absolutely gorgeous, she had a flat stomach and big hips. I got pretty lucky needless to say. She showed up to prom with a flask of tequila and I had a bottle of vodka in my car. The chic got completely waisted and told her exchange parents prior that she was going to spend the night at a friends house.

After prom she came back to my house and we watched some scary movie. My dad found out she was there and made her sleep in my sisters room. So it was like 2am and I was playing JK2 -- she walks in my room. She lays on my bed and said that the upstairs was scary and she wanted to sleep down here. I said "fine" and continued playing JK2, lol. She was staring at me pretty intently and realized I was being kind of rude.

I hopped into bed with no clue where to begin--I kissed her then she pretty much took control. This girl was like far more experienced than I was. There were some awkward moments, but it was really nice and she was very giving. I was no natural at all and it wasn't that spectacular. However, the coming months we practiced almost everyday until she went back to Brazil 8 months later in the summer of 2002.

From: Clark

I was 17, a girl at work asked if I'd like to "do it" I said hell yes. I drove my car to a hilltop dead end and she got up on the center console and the car started rockin. It was a small car, and I wanted to go outside but she wouldn't since it was daylight. She was a hot little puerto rican with big boobs. I never even kissed her, except for her tits and neck, since she was pretty slutty.

The next day, her older brother came with her to work, she pointed at me and said "that's the guy" and I about shit a brick! turns out he was interested in buying my car, I think I mentioned to her while I was driving that I might sell it. I thought I was in for a beat down.

From: Freev

She was fat and made me turn the lights out first thing.

Being an overexcited virgin my cock was hard to numbness and I couldn't feel shit.

We fucked until tired and breaked, and I think somewhere during the second session I shot my wad on her stomach and she was like "what are you doing?"

The next morning I avoided her mother by climbing out the window.

From: Amazing_Ri

My first time was actually pretty darn good. I was 17, and my girlfriend had just got back from a trip out of the country. We were fooling around before then, but only to third base. We discussed how we might eventually need to pick up condoms if we were going to continue fooling around like that about a week earlier, so she had got a few from her mom (They were open with each other about sex and what not).

So were were fooling around on my bed, and I asked her if we should get one out, just in case. She stopped, looked at me, and asked "You tell me," she said. I paused, told her, "I want you," and she replied "Get my bag." She dug a condom out, and I slapped it on.

I was going to get on top, but she said wait, and to lay down. So I did, and she sat on top of me and rode me for I can't remember how long. I held off as long as I could, but eventually came. She kept riding me for a bit, then suggested I get on top. Well, of course my dick went limp after she got off because after coming that way, the only thing keeping me hard was the continued stimulation...

I felt bad for a minute, and she could tell something was wrong, so I told her that I felt like she was cheated since she never got hers. Silly me, turns out she was a quiet one, because she got off twice on top of me.

And she really did, as it turns out. Three years of fucking her has shown me that she really did get off twice that day. She is just really quiet when she comes. Easy to get off, for sure, but really quiet.

So yeah, my first time was in a loving, secure relationship with a girl I cared about and who cared about me. So I guess I was pretty lucky.

From: Don Slice

It’s pretty sad that I remember this, but it was June 17th, 2001- the summer before my senior year of high school. I would have just turned 17 that April.

My best friend’s older sister had a pretty good looking friend that I had been crushing on since 7th grade. She was a little older than me (two years, I think). She was a redhead with pale skin, big tits, was a little on the chubby side, but made up for it with a really cute face. Any time I had mentioned “us”, she just brushed me off, uninterested.

One day (June 16th, actually), she showed up at my house. We sat and talked on my front porch about stuff. My main question was, “Why’d you stop by here?” Her response, “I don’t really want to go home and have nowhere else to be right now.” Thanks, bitch.

After it got darker, she made a move on me and took me by surprise. We started making out on my front porch. After a few minutes, we moved into her car. She put my hand on her tit. I remember squeezing it (first evar). It felt really nice, but I was scared and took it off. She put it back on and I just left it there, not squeezing. Ten minutes later, we stopped. She gave me her number, told me to call her the next day, then left.

So, the next day I called her. She told me where she lived (incidentally, the same guy’s house where I took guitar lessons in 6th grade), and I headed over. We were alone and she put a movie in (Saving Silverman) and some popcorn made. We sat down on the couch and started making out. “Let’s go up to my room,” she said.

Up in her room, she laid me down on the bed. For some reason, I’m scared shitless. I’m stiff as a board (not my cock, but my posture). She asked me if it was my first time. I blushed and said it was. She smiled and got that “I knew it!” look.

She started unbuttoning my shirt. With every button, she stopped and asked “Yes?/No?” Every button, I said “Yes.” The next thing I remember is her riding me and me just lying there motionless- maybe a thrust every now and again.

After twenty minutes of that, she asked me to be on top, so I did. I put it in her (with her help) and just started thrusting. Moans and “Oh God! Oh Don! Oh GOD! YES YES YES FUCK ME HARDER” filled the room. “SHUT THE FUCK UP!” filled my mind.

About ten minutes of that was enough and I asked her to do doggy style. That failed miserably as I couldn’t even get it in, so I asked her to give me a blowjob (first evar!). It started going good until she went hoover on me. It started hurting really bad, so I told her to stop. I tried going down on her, but the taste of salty sweat mixed with crotch juice just… ugh.

We stopped all sexual action, put our clothes on, and cuddled for a bit. Then, the million dollar question: “Don, do you think I’m easy?” She caught me off guard and I said, “Uh, yeah.” I got called a creep, jackass, fucker, etc and she kicked me out.

The next day, she called me and I didn’t pick up. This went on for about three days until she finally just showed up at my house and yelled at me for “using” her. I didn’t say anything and just walked back into my house and she broke down crying on my deck.

From: Indirect0

She was deeply religious, heavily overweight, and extremely self-concious. I was wearing a desensitizing condom. Because of her self-awareness, all the lights were off. I just remember sticking it in and pounding for what seemed like 20 minutes. She made some noises. I was still a bit nervous and turned off. I came to the reluctant conclusion that if I wanted to get off I would either have to find a different girl, or I would have to close my eyes and think about Allie Sin. She claimed to have a vaginal orgasm which I would come to find highly unlikely with subsequent sexual experiences with more evolved females. In summation, I thought I was gay after several subsequent sexual encounters with my overweight girlfriend. Come to find out, I just needed the right girl. Cheers.

From: Think Pink

The first time I had sex I was 16.. or 17, can't really remember the age. Anyway, I was dating a 15 year old girl named Sarina, one of the many local whores. We went to a movie and dinner or some shit, double-date. We left the movies and drove to my buddy's girlfriend's house, a little outside of town. Well, my buddy and his chick, Jessica, have been going at it in the back seat for about 25 minutes, and me driving with Sarina in the passenger seat. She starts giving me road-head. IT was absolutely fantastic head, too. I busted a nut straight down her throat.

So we get to the other chick's house, and decide we should go in. Well, the girls told us to wait for a second, to make sure the coast was clear. My buddy and I sneak into this girl's house. First, through the entry way and the kitchen, wood floors and about ten feet from her parent's bedroom door. A ninja would have made that floor squeak, as did we. Right as we are passing the parent's door, her dad gets up, we can hear him pounding towards us, as the bathroom was right across the room. We booked it downstairs, as quietly as possible, and hide in the laundry room. He must have heard us, because he came downstairs and knocked on the girl's room to ask her what the sound was. She covered pretty well, all the while, my buddy and I were crouched behind the fucking dryer. I don't think we breathed in or out for about three minutes.

After her dad went upstairs and back into his room, we stealth rolled into the room ala Sam Fischer from Splinter Cell. By this time, my adrenaline was going pretty good, and I'm sure my buddy's was too. We pretty much got down to business within two minutes. I was on the couch in the room, my buddy on the bed. The lights went out after that, and we pretty much went by touch. It was fucking hot. By the time we actually got down to the sex part, I was a redwood. She slid on my dick, slow like, in the cowgirl position. Fucked like that for about 20 minutes. She switched it up a couple times, reverse cowgirl, doggy, missionary. After about an hour and a half of fucking, back in the cowgirl position, she came. She came, and passed out on top of me. Not resting, no, that would be normal. No, she went unconscious on top of me. Now, being the gentleman I am (read: I used to be a gentleman, now I'm a bastard), I gently lay her on the couch, and cover her with a blanket. Unfulfilled, balls and cock raw, to the point of bursting.

Now, unbeknown to me, we were making quite a bit of noise. Shortly after I lay her sleep, my buddy and I are conversing. From the top of the stairs, "WHAT THE FUCK IS GOING ON DOWN THERE!? WHO'S DOWN THERE!?" Luckily, there was a window in her room. One window, about 3' X 3', six foot off the floor. He starts barreling down the stairs, and my buddy and I book out the window, with the help of the couch. The same couch Sarina was sleeping on. We got out of the window, but not before we drug the couch across the floor, stepped on Sarina, and broke the screen. I guess Jessica's dad got a nice shot of my white ass going out the window, too.

We sprinted across the driveway and hopped in my car. As we wee speeding away, I see Jessica's dad running behind us with a BB gun, firing 4.5mm BB's at my car.

After I dropped my buddy at his house, I went home. Four o'clock in the morning. I realized as I was walking into my house, how much my balls hurt. They hurt like I just got kicked in the jubblies. So I spanked it.

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