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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

From: Luke [phantasmo2@hotmail.com]

My first time having sex was extraordinary on many levels. I had so many goals in life as far as sex is concerned. But in high school and through out college (before I got kicked out), my sex life was just short of yours. Many hit and miss attempts, sometimes coming VERY close, but never quite hooking the bean.

Well, a few years ago I got a job as a bartender at a local restaurant. I liked that job because I got to serve several hot women alcohol, but being a fancy place, most girls that came in there already had
boyfriends or husbands. About 2 months working there I was working at night when two bitches come in. They were travelling through the area and had all kinds of questions. They were cute and very talkative so I hooked them up with alot of alcohol for free. After a few hours of drinking they were too drunk to drive. I made them stay at the restaurant until my shift ended so I could give them a ride back to their hotel. We were riding in my car there and I asked them if they smoked the weed cause I was tired and wanted to get high.

One of them did occasionally and the other had never tried it. When we got back to their hotel I rolled a few spliffs and we got high as fuck. Then the girls start getting all flirty and shit. Since I'm a loser I didn't really capitalize on the situation immediately. One of the girls suggests that we play truth or dare and I figured why not. We get into it and I dare one of the girls to kiss the other. They do it then later on I dare the girl to finger the other. Next thing I know these bitches start going at it like they're fucking pros! After watching for a bit the girls start getting all on me.

One starts undressing me while the other is taking off my pants. I couldn't fucking believe it! I'm the same mother fucker that got caught jerking off in the dorm rooms three times my freshmen year! These bitches did whatever I asked them to do. I had a bitch licking my balls while the other was eating her out. We did it all. I finally busted a nut in one of them with her on her back and the other bitch on her face getting eaten out.

Not only is this cool for a first time, but it enabled me to accomplish three life goals of mine: 1) to lose my virginity, 2) to have sex with a black girl (I'm white, but I wanted some brown sugar at least once in
my life), 3) to have a threesome. For it to be any better I would have had to video tape it! Every since then I guess my confidence level has gone up because I've fucked mad bitches since then. So stick in there loser boy! There's hope for you yet STiLe!!!

From: XxTheHauntedxX@aol.com

I met some really slutty chick when I was in 10th grade, she was in 9th so I knew she would go for me because I was an older guy and she was not a virgin.

When I first met her I knew she was slightly retarded, so it wouldn't be hard to get her in the sack. She wasn't the hottest girl I have ever seen but that didn't really matter because I was young and only wanted to get laid. We "went out" for a couple weeks, then one day I persuaded her to come out to my grandma's house knowing that was where we would have the most privacy and I would try to make my move. We started out in my room just messing around but my grandma was being annoying so I told her we should go on a walk.

It was the middle of winter so it was fuckin cold out and it got dark very early, I planned to use this to my advantage. I took her to the playground outside of the school/church (sinse we were out in the country the area didn't have much money so they just made the building a school during the week and church on Sunday). Me being as Anti-Christian as I am thought it would be funny shit to have sex at a church.

I convinced her to take off her jacket and use that as the "sheet." I started thinking "holy fuck I am finally gonna get laid, this is the best day in my whole life." Even though she said she was so turned on we couldn't even get my cock in because she was as dry as an old prune. I thought I would just try to get her going by just playing with her. It worked enough to be able to force myself into her. After a few pumps into her she complained that it hurt to bad so I had to stop.

We walked back to my grandparents house and I was quite disappointed with the whole experience. A few days later we finally fucked where it wasn't so cold and uncomfortable but I finally saw how retarded she was and that I couldn't stand her so I dumped her. Even though my first experience wasn't that cool, I still like to remember that I lost my virginity on a church playground that kids still play on today . Little fuckers will never know. Oh yeah, this is the girl I realized cunt farts are real by too. The only thing Iever learned from a girl.

From: wally

whats up stile, let me tell you how this horny little jew over here lost his virginity. its the story of a devilishly cute 13 year old(me) and a semi ok 17 year old babysitter. and stile this was even better then the time you got me laid in vegas.

i dont know where to start but yes i did lose my virginity to my babysitter. and to make it worse we basically turned this into some kind of twizted relationship. it all started off the very first time she babysat me and my younger brother and sister. she came over watched us and while my bro and sis are upstairs watching tv she was showing me her tits and letting me play with them. this kind of stuff happened everytime she watched us and she watched us atleast 3 times a week. it started out like that and then it lead to her sucking me off and me fingering her snatch.

this was all very weird because we were more worried about her boyfriend finding out then anybody
else. soon after my parents invited her to go with us and babysit while our family went on vacation. well we get to the hotel and my whole family wants to swim so they go to the pool while we stay in the room and start fucking (actually this was the first time i got to penetrate) and wouldnt you know it less then 2 minutes after i got my little noodle wet...knock..knock. it was my step dad. so she went into the bathroom and pretended she was puting her swim suit.

after that just the look in his eye, he knew what the fuck was up. but it must not have mattered to much because she still babysat every weekend and we probably fucked again 50 times after that. now that i look back though i dont know how or why she never got caught because everyone of my friends in junior high knew what was up, hell a lot of times they would watch, i bet if i looked hard enough i still have the video we made. well i made, she never knew i was doing it. but everyone of my friends saw it and i
tell you stile there was some serious peter north-ron jeremy shit happening. i mean i made the faces i even spanked her a few times. oh how i wish i had a babysitter again. stile sux. wally.

From: Tyler [youwillbepunished@mail.com]

My first time was when I was 16, and my girlfriend was 15. Right from the start of our relationship it was obvious to me that we would end up losing our virginity to each other, but it took some time for us to work out the logistics.

Not wanting to be caught off guard I went down to the gas station on the corner and bought a pack of Trojans. The guy who worked the counter gave me a look which I took to mean he was half-approving of me about to get some, but half-jealous because he himself wasn't anywhere close to getting any. Anyway, we tried first in the park on a blanket, in this secluded area by a stream hidden by trees and bushes, but people kept coming by and they could have heard us, so we chickened out. Later that week we went and parked late at night in this empty commercial park/development type thing that was under construction and had lots of empty vacant lots, but my car was too damn small for us to fit comfortably, so we just ended up doing oral and stuff like we always did.

A couple of nights later we were at her place watching TV. It was late on a Saturday night, and as usual her parents were upstairs in their bedroom, presumably sleeping, but who knows? I think her stepfather was really keeping one ear out for signs of any mischief. The main problem with her house is that it was so wide open, you could pretty much hear anything that happened anywhere in the house, unless you were in the bedrooms upstairs, but they both shared walls with her parents' bedroom, so we didn't even take a chance with that. Plus there was no basement either.

Eventually we left the TV on for background noise and went into the bathroom downstairs, which had a door we could close. We were making out and I asked her if she wanted to fuck, and she agreed, so I finally put the Trojans to good use and took care of business. We had stolen cushions from the sofa to make a bed on the bathroom floor, so it was sort of awkward, and I had major floor burns on my knees from slipping off of the pillows, but I was so focused on the sex that I would have put myself through all kinds of pain to make sure I came.

It lasted about 10 minutes and I was nervous as hell afterwards that her stepfather would come downstairs and beat the shit out of me. Her parents never made any noise that night, but I got the hell out of there pretty quickly. After that I always thought that her stepfather looked at me funny, but he never said a word to me about it. Still, I think he knew what was going on. And he had reason to be suspicious...she was always horny and would invite me over when her parents were away so we could go fuck in their big bed. Sometimes we'd meet on a school night at like 1 or 2 AM to have sex down in my basement. She was a natural, too...I ended up cheating on two of my girlfriends with her after she and I had broken up, and even later when I would come home from college we'd hook up, no strings attached.

And the guy at the gas station always gave me the same look every time I'd go in to buy more Trojans. I don't know where she is now or what she's doing, because we both moved away and have since lost touch, but I have to tip my hat to her, because those were some happy times and made for good memories.

From: Phil [pwetz@skylands.net]

I decided to write this down now because today, June 17th Is the anniversary of this event. This happened 8 years ago today, in 1994. I was a late-bloomer and didn't get to do anything until I was 24 years old. I met Dawn through a newspaper personal ad and we talked about our lives for about a week, so she knew that I didn't have any experience. She was 23 and VERY experienced. At the time, I worked as an overnight janitor in a nursing home in Sparta, NJ. The place was a former motel and I had the place all to myself at night.

Well, for our first meeting, we decided that she would go to work with me for the night. I picked her up and we went to my job, where we spent about 2 hours talking after I did enough work to keep from getting in trouble. Finally, we started making out and I inched my hand into her bra where I got to touch her nipple for the first time. We were sitting on a couch but eventually moved down to the floor. We kept making out and eventually took our tops off. I worked my hand down to her crotch and started rubbing her, eventually slipping my hand into her pants and underwear. My hand was massaging her and I was surprised at how good her pussy felt and how easily my fingers slipped into her. As I moved my fingers in and out, she started massaging her clit wth her own hand. I was so excited when she started moaning and had an orgasm, all this was new to me. After she was finished, I gave her time to catch her breath and then I asked her if she would do something for me. She began to massage my chest and worked her way down until she was rubbing me through my pants.

I was already rock-hard.

She reached down my pants and rubbed my cock for awhile, then she moved down lower and pulled my shorts down. I started to get nervous. As I said, we had talked on the phone for hours the week before and she told me that giving head was her specialty. I said "Are you going to do what I think you're going to do?" She said "Don't worry about it!" She used her hand on it some more and then I could feel her tongue licking the end of it. Then she stopped for a second and said "just let me know when you're going to cum." I got so nervous I said 'Wait". She said "What!" in an irritated voice. I replied "Nothing". At that point, she wrapped her lips around it and took it fully in her mouth. It felt so good I felt like I was on another plain of existence. Just the sucking noise was enough to make me pop and after a couple minutes of her head bobbing up and down, I told her I was coming and she stopped and pointed my cock away from her and I shot my load on the rug.

After that, we cuddled a little bit and then got dressed since it was almost daylight and I needed to finish my work. Things didn't work out for us and we broke up the following December, but we have stayed friends to this day and still fool around sometimes. I have made up for lost time, as far as sex is concerned, but she still gives the best blowjob that I've ever had.

From: Kevin

Stile… I love your website, and I have read all the first time sex stories. I was wondering if they were really real, so I thought I would write in with mine and see if it shows up…

So, anyway, I was 17 and my girlfriend was 16. We were really in love and very physically in tune with each other, but she always said she wanted to wait. I wasn’t going to pressure her cause I figured I had waited this long, and I was getting good BJs and hand jobs and stuff anyway. I also LOVED going down on her, so I had that to satisfy me. One time, before we’d had sex, I gave her her first multiple orgasm by simultaneously licking her clit and fingering her with my index and middle fingers. When she was done quaking, (that’s the only way to describe her reaction), I asked her how many she had. She said she couldn’t tell for sure, but thought she’d had 20 or more (oh to be a woman)!

Anyway, after about 3 months, she told me she was ready to have sex. We always went back to my house after school, because there was about three hours between school letting out and my parents getting home from work. So, we were messing around as usual, and I was eating her out and gently playing with her nipples. Apparently, this is a magical combination, because she screamed out “I am ready! I need to feel you inside me! I can’t stand it anymore!” I told her I didn’t have any protection, and she said it was ok cause she had just gotten off her rag a couple days ago. So, wanting to make sure she was really ok with it, I asked her about 4 times if she was sure. She just said over and over that she knew it was right and she needed to feel my cock shoot off inside her. I could tell by the look in her eyes that she was sure, so I didn’t argue any further. I spread her legs apart and got on top. It took a couple tries to get in, and I remember worrying that I wouldn’t be doing it right or whatever. Once I got it in, I almost came right away.

That feeling was amazing! It was so wet and warm and tight. It was heaven on earth! I had to stop right away so I didn’t waste my load. I kissed her briefly, and the feeling in my cock subsided. She tilted her hips up more, and hooked her feet around me to pull me in close. I remember her saying that she wished the feeling could last forever. Then, I started pumping slowly, and the feeling started to build again. There was no avoiding it. I was going to shoot unless we stopped. I didn’t want to pull out or stop again, so I just went as slow as possible. I was driving her crazy teasing her anyway, so it was a good thing. After about two minutes of trying like crazy not to cum, I couldn’t hold it anymore. I whispered that I was going to cum. She said that she wanted to feel my cock throb inside her. So, I shot what felt like the biggest load of my life! I swear it was probably about 12 huge streams of hot sperm! I was kind of disappointed that it went that fast, but she said it was incredible to feel that close to me.

It was so hot that we just kept right on messing around, and about 5 minutes later, I was hard again. So, I got back on top of her, and we did it again. This time I lasted about 10 minutes. I remember, because it was getting close to the time my parents would be getting home from work, and I kept glancing at the clock.

After collectively losing our virginity, we fucked like rabbits. We did it everywhere. My bed, my car, my basement (there was a spare mattress downstairs that we would pull out and fuck on when my parents were upstairs), parks (day or night, didn’t matter), once on the beach during the day, once in a lake by her best friends house, and once in her aunt’s swimming pool. Basically, if we thought we could fuck before getting caught by family or cops, we’d do it. We were bold and had no shame. It was great! We never did get caught by any family members, either. That was the most amazing part!

After about 2 years, we broke up. We started to realize that all we had in common was sex. I think we both got too hung up on it. But, DAMN, it was great. And, I have no regrets now, because I know for damn sure that I’ll never, EVER, get to stick my cock in a 16-year-old’s sweet wet pussy ever again.

From: Joseph

Dude. Figured I'd send in a first timer for you. I was 14 or 15 on a band trip. That's right, a fucking band trip. I had really big feet proportionately at that time so I figured I'd talk shit about having a big dick. I really had no idea if my dick was big or not. Anyway, this girl heard me talking on the bus and decided she would see for herself. When we got back to town after the trip, she took me to a baseball dugout, fuckin' sleazy I know, and proceeded to suck my young dick. She tells me that, 'yes, you do have really big dick' and that we should fuck. I agree, why not? Well, I was new to the game, had never even kissed a girl so I failed miserably. Couldn't even achieve penetration I was so inept.

She said she would tell everyone in the school that I had a 'small limp dick that I couldn't even get
hard' if I didn't fuck her right, and soon. So a few days later, we went to a fellow band mate's house with the intention to fuck. She put on the CD, "Have a merry mother fuckin' christmas, and have a fucked up New Year," to get us in the mood or something, I dunno. I didn't want to do it, but she said I had to or she would tell everybody how pathetic I was, and she was way popular because she fucked a lot of guys, so people would believe her. When you are 15 or so you worry a lot about that kind of shit, especially in a small town.

So anyway, I proceed to put a condom on and fuck this girl. I wasn't into it at all so I never got to
cum or anything, but we fucked for like an hour until she was all sore and bruised up. The girl and her friend let everyone in town know we had fucked, but at least she let everyone know she was
sore afterwards and that I had a big dick. It was later I discovered that my dick wasn't really that
big, and she was just saying that shit to flatter me into fucking her. It was hell having to try to live up to the "big dick" rumor for the rest of my highschool days, luckily I lived in a stuck up farm town and most the girls didn't know what big was, so believed me when I told them I was big. Sweet.

From: Jonathan [divine69@rogers.com]

What's up Stile? i just read a whole bunch of your first time stories and thought that i should throw mine in just because. A few years ago when i was on vacation in the Dominican Republic, i fooled around with this girl from Winnipeg. Nothing serious but for only knowing the girl for 2 days, a hanjy and sucking on some titties wasnt bad.

So anyways, fast track 2 and a half years later and after fucking around with this girl by talking to her on the computer about us meeting up again, she springs up on me that she is coming to visit me. Since the last time i had seen her, she had gotten a boyfriend and was with him for over a year and he was fucking the shit out of her and a daily basis, so i knew that when she came in, i wasnt gonna let this opportunity go to waste. One week before i knew she was coming in, my dad died suddenly, and i was having the worst week of my life. I was supposed to be getting braces that week but i told my dad that i had to get them switched because i was goign to be getting "Guaranteed Poon" when this girl came in.

So the week goes by and we had just finished our one week mourning period and she comes to sleepover at my house with her cousin. We watch a movie and are fooling around under the covers when we go upstairs and start fooling around. I immediately take her to my waterbed and the nakedness ensudes. When i tell you this girl is sexy, trust me when i tell you she is the head cheerleader at her school and has DD titties. So i eat her poon and she gives me head for about a half hour untill she is on top of me and tells me to fuck her.

So i slap a condom on and get right to the fucking. So we are going at it in the missionary untill she asks if i want to do it in any other position. i say whatever she wants and she replies by telling me that because its my first time, she'll do it any way i want. So she gets on top of me and starts riding my cock untill i flip her over and start banging her doggie style. So i fuck like an animal and go 45 minutes untill i bust inside of her. Afterwards, when we are still both buck naked and looking for our clothes, she points out the fact of how tight she is, to which i replied, "Well you know, tighter the berry, the sweeter the juice."

We both start laughing, she gets dressed and goes back to sleep, and the next day was on a plane back to winnipeg. I didnt think there would be any way i could get out of my sadness from loosing my dad, but there was one way, my daddy made sure that i still got my "Guaranteed Poon."

From: John Ballin' Gangsta [johnm@upo.com]

Wassup Stile, I just finished reading the 9th version of these stories, and 3 or so seemed to be made up, so I decided to send in my story, 100% REAL.

So I had turned 17 like a month before, and all my friends had been telling me that it was my last year to get laid before I became a virgin for life, so I was like fuck I gotta fuck some pussy. So I turn to yahoo messenger. I do a search for females in Miami, and boom I got a list of 500 pussies and e-mail addresses. I sent the same e-mail to EVERY FUCKING HOE that had Miami in the location area of their profile. Here is the e-mail I sent.

"Ayo Girlie was tha deal, this a tru down south chico bout to holla at cha for a minute. If you and a friend wanna ride out to some gangsta azz hip hop wit 2 down south dick em down type niggaz than holla back at me baby. We funna ride, smoke the fuck out, watch some surround sound DVD and tear that pussy up, ya heard."

Anyways I got mixed replies. Some chicks caught me at my own game by having more than 1 profile under different names, so they bitched me out, but at least 12 bitches responded that they were down. So of the 12 bitches, one lives kinda close, and I call her up. She arranges to meet me the next day. Anyways I tell my Mom to take me over.

She's waiting for me at her pool when we pull up, and right off the bat I thought she looked a little stank, but I was like what the hell, I'm not an asshole whose gonna just drive off after seeing her, so I get out and tell my mom to come back in two hours. We walk into the pool area, and mind you this is a public pool used by all the people who live in her complex, so we sit at a picnic table and talk for about an hour. She asks me if I wanna swim. I'm like "I don't give a fuck" and I jump in with just boxers on. Soon as her cloths come off, I'm like this chick is pretty hot. I mean she wasn't ugly but she had a few acne scars like I did and she wasn't the fine ass hoe that I had hoped for, but she was decent and I was a virgin.

So she tells me she likes what she sees, and I tell her i like what I see, so we start making out in the corner of the pool and she starts grinding against me. My dick gets hard and we start talking about fucking. She asks if I'm a "rough ridah" which means that I do it without a condom, I'm like no never. So she asks if I have a condom. I'm like shit, no I don't. The fact that she asked me if I fuck without condoms seemed questionable to me, so I wasn't about to slip my jimmy into her without protection. So pretty soon my mom pulls up and I jump out of the pool with wet boxers and a fucking hardon pitching a tent.

About 20 people in the pool all stare at me as I walk to my cloths with my cock sticking out of my boxers. I grab the hoe's towel and dry off, and walk over to my moms car. I'm like "can you take me to go buy condoms?" She's like sure, no problem. So I tell the hoe I'll be back, and off i go to buy condoms at a K-Mart with my mom. I buy the cheapest pack they had, fucking bankrupt ass company. I come back after eating some KFC for energy, and ask her if she is ready to do this. She says she is, so I head off to the bathroom to put the condom on so it is water tight when I jump in the water. You have to keep in mind that the pool was packed with housewives and thier kids, and that I had just met this girl 2 hours before.

So I go into the bathroom and wack off till my dick gets hard, then I slip the condom on. Now I have to make it to the pool without my dick going soft, so i run out pitching a tent again and all the people staring, and hop in the pool and swim over to our corner.

I sit on the metal steps and grab her. She was thin and meaty, and her body felt tight in my hands. I pulled my trunks down and pulled her bikini over to one side. She slides it in easily and starts slowly fucking me in the pool, so as to not make it too obvious. I can't take it anymore, so I start pulling her down on me faster and harder, making it extremly obvious that we're fucking in the pool. Some ladies start pulling their kids out of the water. After 20 minutes of fucking like this, she tells me their is a jacuzi right around the corner.

I'm like stupid bitch, couldn't you have told me this before? So I hop out of the pool with my hard on again, this time not concealing it at all, and calmly walk to the stank ass jacuzi. The water was stagnant. There is all types of stuff floating, bugs, dead leaves, hair, and the ever questionable, everlasting foam. Fuck it. I jump in, lie down, and whip it out. She pulls her bikini to the side again and sits down on my piece, riding me in the damn stank jacuzi.

The nosey ass lady that I guess wanted my cock comes over and peaks over the bushes that were hiding us from the pool area. She sees my cock going in and out of this hoe with no shame. She gets scared and walks away. I hear some cuban guy yell in spanish "Thats how you do it!" so I know the word got passed around. So I fuck her like this for awhile and then my mom comes back, and I am happy to take my cock back. So I came back and fucked her in her room about 4 more times over the next 2 months, but then one day I was fucking her with a condom on and I began to feel this wetness on the head of my dick.

I just thought that i was finally getting in the zone with this hoe. So I fuck her some more, finally starting to feel good. When I pull out, I turn away from her and look at my dick and the condom was broken! I had fucked right through it. I calmly slip it off without telling her that it had broke, and I high tail it out of there. That was the last time I ever saw her. A few months later I was horny again so I called her up, she told me that she had quit school and moved in with her girlfriend. I was like shit, why didn't you tell me you were bisexual? So I didn't hook up with her again, but at least I'm not cursed to be a virgin for life. I never told her that she was my first, so lynette, if you are reading this, thanks for popping my cherry.