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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

From: Jay Man

Well as of pretty recently I was a virgin of age 20. I had only one girlfriend my third semester of college, but I never got any sex or blowjobs (just a couple of handjobs). But anyways, I have a thing for asian girls, hardcore. I don't know what it is about them, but I think they're the greatest. So I decide to go to an asian massage parlor. I wasn't sure what to expect, but I knew at the least
I'd get touched a bit. So I went to the ATM and pulled out what they charged for an hour's worth of massage, plus about 40 bucks (just in case). You have to be 21 to go to a massage parlor so I had to visit a couple before I found one that didn't think/care to check.

The eldery lady in charge assigns me a girl to give me a massage. She exactly my type. Thin, tiny, olive skin, slanted eyes. I try to make friendly conversation throughout the massage, but I find she speaks with an accent that I couldn't understand (I think she said she had been in America for only 2 weeks). So after the massage she asks me if I want "everything". At first I have could not even understand the word itself, then I got she was saying "everything", but I was not sure exactly what that meant. I ask "What's
everything?" To which she giggles and makes a humping motion. "Holy shit" I think to myself. I wasn't sure what to do, knowing it might be years until a regular girl would offer and this might be my only chance ever with an asian or maybe my only chance with a hot girl. So I said yes. She then tells me it costs $200.

Well, I didn't have that kind of cash with me (I had no idea, I thought $20 for a bj or something). She said I could pay with my credit card, but those are delivered to my house and my parents see them, and spending that kind of money is at a massage parlor is not what they want to see. So I try to use a check card and they say ok, but I need id. Which I am not yet 21, so I was thinking I was screwed, but they never said a word. Anyways, I forgot I had told the bank to nullify the check card option so that it was only an ATM card, so it didn't go through. There was, however, a bank with an ATM next door. Only my money was in a local South Carloina bank, and this was in Florida. The machine would not take my card. So I run across the street to a gas station in hopes that they would have an ATM, no luck. However, a bank was next to the gas station and this one took the card. So I get $200 and hurry back to the parlor, hot and sweaty from the run across the street in the Florida weather. She makes me cool off and catch my breath before we start.

So the time comes and she tells me to lay down on the table. She begins kissing my chest and my neck, which feels good so I am already hard as a rock. Then she starts licking down there, it feels so great. I start nearing orgasm, and then she decides she is going to get on top of me. Before she starts, she puts on the condom. Well, I was so close to orgasm that the friction of the condom being slipped on makes me cum at almost the instant I get in. She acts surprised and says "You cum?" I thought it was over, but she pulls up beside me and starts cuddling me. She tries to talk, but all she seems to say was "He he. That was fast" and something about "I woman, you man".

After a few minutes of cuddling and her fondling my penis, I get hard again. She says this time I should be on top. I start pumping away while she moans and groans (probably fake). I enjoyed it, but the way we were positioned was awkward. So I pull out and ask her if she'll do doggy style. She agrees and we begin to do that. The angle was much better, so I was enjoying this much more. I decided since this was a whore, I'd take advantage of the fact that I would probably never see her again, and slapped her ass a few times while riding her and saying crap like "You like that?". Well I came again, and it was over. She said "Thank you" (I wasn't sure what to say to that) and helped me get dressed and I left. So that night I lost my virginity to some
foreign prostitute who barely spoke English.

From: Joel [jlucas420@hotmail.com]

I've been enjoying your first time stories, so while this particular story isn't about my first time, it is funny and it involves the first girl I had sex with (so I still get partial credit).

Anyways, when I was 16 or 17 I'd been dating this girl Lori for a couple months. She was a year younger than me, and we popped each other's cherry in the back seat of my mom's car.

Regardless, we'd been dating for a while and now our biggest complaint was insufficient sexual contact... only 3 or 4 times a week when we were try to juggle "alone time" away from the 'rents to bang at her house or mine.

It was spring and I had just started lacrosse practice after school everyday, and now we were fucking even less. An acceptable solution had to be found. Luckily she really into art and spent lots of time after school in the art room doing art shit. So one day she proposes that we meet in one of the school dark rooms right after school.

What a fantastic idea. The thrill of fucking in school and fucking while other people are around, etc has my head swimming all day in class. Also, it was pretty safe since her being in this room after school won't arouse suspicion and the door locks authoratatively from the inside.

So, anyways, 3:00 that day I run up to the room on the 3rd floor to meet her. We go into the room and she locks the door. We start going at it like the horney teenagers we are.

Anyways, the one problem with the dark room is that it's really fucking dark (go figure)... I'm trying to prop her up on tables and against walls to find the ideal angle for me to really rail her, but am struggling. Finally, I just decided to bend her over the large table and do her from behind, since that's the only thing that seems to be working.

I'm almost done and she tells me she wants me to come in her mouth, a service which I'm more than happy to provide. I finish up behind her and spin her around. She grabs the base of my cock with her hand and shoves the rest of it into her mouth.

I began having what started out to be a great orgasm, but sort of finished on a sour note... there's some sort of weird pain down there that I notice about halfway through my orgasm.

I finish and she stands up, and I kind of stand there for a minute to try to figure it out... it doesn't feel like I got scratched with a fingernail... it had begun feeling almost burning instead of painful. Whatever it was, I knew it was getting worse fast.

I remember saying something like "what the fuck's happening?" while I was standing there with my jeans around my ankles. It was now getting REALLY painful (this is about 30 seconds after my orgasm) and I didn't know what to do... I wished there was a light in the darkroom so I could look and see what the problem is.

As I was looking around for this mythical lightswitch (which didn't exist), I was taking a good look around the darkroom for the first time. In the pale red light of the darkroom I noticed that the table Lori had been bent over was the one with all the photographic chemical baths on it, and that a bunch of them had half spilled out onto the table, right where Lori's hands were while I was doing her from behind!!

It suddenly clicked in my head that this was a horrible chemical burn caused when Lori grabbed my dick after accidentally getting these chemicals all over her hands.

I immediately sprang up onto the other counter top in the darkroom where the sink was and cranked the faucet on, rinsing off my painful cock-burn. At this point Lori also figured out what happened and muttered something like "So that's why it tasted so weird", which did little to console me.

The aftermath wasn't so bad... I had a tender pink chemical burn over the base of my cock that was quite painful for about two days before it cleared itself up without medical attention (thank Christ... there's a talk with my doctor I didn't want to have). Me and Lori never, ever, ever had sex in the darkroom again.

From: JIZITUP@aol.com

I'd been seeing this girl here and there for a few weeks at school, we are informed of a Minimum day and we decide to get together that day because she has to be home due to strict parents. We are supposed to go to her Best friends house which is about a 5 minute walk from school, her best friend is this raging BEAST whos uglier than a wrinkeled rhino's cock and more insane than Chuck Manson hopped up on PCP. Earlier that day I get asked out by a girl I knew who I wasn't all that interested in, and I guess I didn't make it clear enough that I didn't want to go out with her (I don't know how "Get away from me you devilish little troll" doesn't seem to work) so this little gnome thinks we're together. She manages to find out that I'm supposed to go out to the ugly girls house with my girl (her name is Mandy, the ugly hoebag was Ashley and the little gnome was Reina).

We show up to Ashleys house and immeadetly go to her room, and upon entering Mandy whips out a bottle of Tequila and all the girls procede to get drunk, I wasn't up to drinking so I only had like 4 shots. Reina Mentions that she has a bunch of special perscription pills, she doens't know what they are and all she knows is that "they make your body go numb." Ashley thinks "hot shit!" and downs one. Some how we start playing truth or dare which was the worst because I couldn't do anything with either girl. If I did something with Reina, Mandy would get jealous and we would have sex. If I did anything with Mandy, Reina would freak out (because she still things we're going out) and woudl ruin my chances of getting laid. I don't know how I got out of that situation but I managed to stall till Reina had to leave. Once she left it was all down hill.

By this time Ashley is really fucked up and is speaking incoherently (she normally did, but this time I knew it was the drugs) and was talkign about how she couldn't feel anything and wsa poking herself and stuff.Mandy and I see our opportunity and get down to it. I eventually have her on Ashleys bed completely naked except for her tall leather boots, I gotta tell you it was a sight to behold. I go down on her and Ashley comes over and starts sucking on her tits, Barked at her and scared her off into the other room. I put on a condom, and we get to it, nothing special. I cum and when I pull out, I notice that the condom has conveniently ripped and I've spooged inside her. I freak out, Mandy is calm but I'm going apeshit. We get dressed and come to the side of the house to smoke, Ashley shows up half naked Lighting her hair on fire saying "Look! I can light my hair on fire and I can't feel it! This is great!" Right when we walk back inside, Ashley has compleely stripped and is dancing around the Living room Lighting her hair on fire, and her father comes in, I look at him Stunned.

Rush to Ashleys room, and try to clean up fast, shoving Coronas under the bed, trying to hide the big cumstain on the bed and get me and Mandy dressed. Ashley gets the rest of teh alcohol and puts it in a bag and we all run outside, Ashley is making stupid lame excuses and her father is following us. As we are walking down the street he starts following us in his car, this scared me SOOO bad. We eventually lose him and I start walking to my friend Reillys house, they go elsewhere. I get to Reillys house and all I want to do is relax, I tell him my story and I think everything is over for now, but his stupid ass brother overheard us and bursts in and Starts yellin shit like "MATT can I be the god father to your kid? Mabey your gonna have twins!!!" What a way to cap all that shit off!

From: mike [mccarmike@hotmail.com]

hey stile! thought i should add my 2 cents to your first timers. i was 16 at the time and i met this chick at some party. i was prity out of it then and this chick kept coming up to me say she wanted a hug and shit, so i went along with it. we end up getting naked and that was about it for the night -- she went home and i spent the rest of the night stealing cars and shit like that.

we talked on the phone the next night and and she tells me shes going off to camp in a couple of days. well, being the nice guy i am i see her off at the train station. she kept asking me to come with her... i didnt i went to school and got throught half the first class before i msg her asking her where she is going and how to get there. she replys teling me how to get there and that if i come i can sleep in her bed. life sucked at the time so i took off from school and left for the night. i hoped on a train which takes 3 hours to get to a little hole called otford and all i had on me was my knife which i was very grateful for.

so i m walking around at 1.40 in the morning in a little town with nothing more than a train station a couple of house and youth center. eventually i end up finding her and she takes me back to her cabin where there are at least 6 other girls. we fool around in her bed for about an hour while i watched her rub herself and play with me cock while we made out. the other girls were sitting around chatting and shit like that. eventualy she asks me if i want to fuck... and i ask "what? right hear and now? in front of everyone?" and she says
"yeah" and that she couldnt care less. so why the fuck why not?

i grab a condom, throw it on and fuck for about 5 min with her friends all gigling and taking pics. it was prity embarising for me losing my virginity for the first time in frount of 6 other chicks and we stopped after a few minutes.... i got off, im not to sure if she did though she was prity loose. i stayed the rest of the night and got out of there at about 7 in the morning. we broke up a few days later. not such a
bad thing.

From: Ian

My first time was with a prostitute, some might think "Fucking loser", but fuck them, I certainly don't regret it.

I was 19, felt like a peice of shit and was going through a time of my life when nothing seemed to be going right, and on top of that I still hadn't got round to fucking anybody. To tell the truth, I didn't know anybody to fuck, I knew no girls at all, the only people I knew were a bunch of blokes in a similar situation to myself, i.e. miserable, aimless, drunken fucks.

Anyway, I'd been around the red light district where I live a few times and noticed some pros hanging around and I had thought of picking one up before but I'd never seen one that looked like my type. One night, when I had nothing better to do but go out and try to loose my virginity, I spotted one I liked, short black hair, tall, nice figure and picked her up. It wasn't quite as easy as that mind, I was as nervous as fuck, first time picking up a pro and first time shag. My throat was dry and my heart was racing before she got in the car.

She told me where to drive to and we ended up at a car park behind some houses. I'd told her it was the first time I'd picked someone up, didn't mention it was my first time ever (I didn't want to look like a complete fucking loser)and she told me how much. I decided to go for
the full monty, a bit of oral then sex. I got my cock out and she put her hand around and said "Fucking Hell, I don't need do much for you" seeing as it was already half hard, she put a condom on it and started sucking. I asked her to get her top off and she did, she only had small tits but they were a nice shape, and she carried on sucking me off. After a couple of minute she said "You want sex now?" and a lay back in the passenger seat, I asked her to go on top, but she said it made her bleed so I got over to her side and tried to poke it in.

I kept aiming too high so she lifted up and when I'd got it she told me to push. She made a sound when it went in, but I think she did it to make me feel good, it was only half hard at that point. I started going at it and came in about a minute, pretty quick for me, as I was used to taking my time wanking. She knew when I'd come even though I didn't shout or anything, womens intuition maybe. She asked if I liked it and I gasped out "Yes" (dry throat again, still nervous as fuck after I'd finished). I dropped her off and went home and got pissed on cider. I saw her a few times after that, my 2nd and 3rd times were with her as well and were much more enjoyable, wasn't nervous those times.

Some people will probably think it's fucking pathetic losing your virginity to a prostitute, but I couldn't give a fuck. Maybe she suspected that was my first time but if she did, she never said. Thankfully, life's got a bit better since those days and I no longer have to pay for it. Anyway, that's my fucking story, make of it what you will.

From: amitai

Hi Stile! I thought you might want to hear my first time sex story. This story could also be appropriately named my most embarrassing moment. I was a complete gawky loser until I was 15, almost 16. Never kissed a girl, asked out a total of 2 girls... one just rejected me and the other laughed in my face. But enough bitching. I improved and got some girlfriends, and by the time I was 17 had done everything but have sex.

Then there was this girl Candy. So this girl was gorgious. I had met her a few times two years earlier, at age 15 through some friends but we never got real close. Then I didn't see her for two years for whatever reason. We met again (age 17) at a party and started to talk. really well. I had never done so well in fact. She had just decided she wanted to break up with her boyfriend, and we ended up hanging out a lot. Two weeks later we got it on after watching "The Breakfast Club" (I will be forever in debt to that movie) ... And just one week later it happened. We had done everything but sex, and she was giving me a blowjob for a long time. Keep in mind that she did not know that I was a virgin (I don't think) So this blowjob wears on and I ask "Are you on the pill" she said yes and before anything else was said we assumed the position.

ONE THRUST!!!! ONE!! FUCK ME MAN ONE FUCKING THRUST!!

It took about 3 seconds and I blew inside of her. I wanted to fucking die. Her reaction was a surprised one. We talked for a few more minutes and I decided to wrap up the night. If I had a knife in my hand at the time I would have cut my own fucking balls off. I know that first times for guys are usually short but ONE FUCKING THRUST!! We are still good friends and we still go at it a lot so it turned out OK but that is still the most embarrassing moment in my whole fucking life. Everyone laugh at me.

From: Simon

I was about 16 at the time, and i was staying with my cousins' house, which is a few hours away from my own. Anyway, my eldest cousin was a bartender at the time, and he decided to have a classy evening, where everyone would get dressed up, and he was gonna make cocktails and shit. Anyway, it was then when i got introduced to my new-found friend, companion, and all around shit stirrer : tequila.

Anyway, we were hitting the shots... I think they were called Blue Poppers or something. I don't really know my shots. Anyway, after a fair few of those, and some nice bourbon and cokes (that wen't down extra nice, due to the fact that I had only had canned shit before then, which, in my opinion taste like shit). Anyway, it was all my cousin's friends there, they were all like 19-20s, very trendy characters. Anyway, I'm walking around, and i start talking to this older lass. She was about 20, perhaps a bit chubby, fair big knockers. We'll call her Anne for references sake. Anyway, we part ways, and I go on drinking.

Later, I'm in my eldest cousin's bedroom, hitting the 64 for a bit of drunken NBA Hangtime (which was all the rage back them), and three girls walk in, including Anne. Anyway, we start chatting again, and I must have mumbled something about playing guitar. Anyway, we walk into my other cousin's bedroom, where my guitar was, and i start some drunken strumming. Anyway, somehow, we start kissing. She was the type who like to use the tounge... a lot.

Anyway, we get onto the bed, and I remember how with my old girlfriend that I never just stuck my hand down her pants, when I really should have. These thoughts soon turned to actions, and my hand was soon down there, examining her hairy crotch in the darkness of my cousin's crap-laden bedroom. I fiddle around for a little bit, and finally find a hole, and have a poke around. Anyway, my mouth starts to wander down to her breasts. She's moaning quite loudly by this stage. Anyway, I undo the bra, and start sucking on her nipples for a while.

I decide I wanted to get down to business anyway, so i try to undo her skirt and get those panties off. Anyway, after a few tries, she tells me to stop, and gets up and pulls them off. And assumes the position that we were before. Anyway, I start going further down, towards the pussy area, and start licking her thighs. She's getting pretty wet by this stage. I hadn't eaten a girl before, but wanted to give it a shot. Anyway, before I could start anything, she grabs my head, and pushes it deep down into her pussy. It was great.

Then, horror. I hear a "Simon!" from outside, followed by the door opening. It was my Aunt! "Fuck!" i think. I fall against the door before it gets fully open, and wonder what i'm going to do next. After a few seconds of knocking, for some reason, my Aunt decides to go away. I didn't think twice about it, and proceeded chowing down on delicious pussy.

Anyway, after a little bit of that, she gets up, and turns the tables. I can't really blame her, I was so drunk that I probably was just slobbering over her crotch and flayling my tounge around aimlessly.

She starts to pull my pants down, and I get rock, rock hard. She gets my boxers down past my ankles, slips on a rubber and guides my cock into her pussy. I dont think she was a virgin, and my 7 inches went in pretty easily. She starts riding me like crazy... pretty darn active for a big girl! Anyway, she rides me until I cum as hard as I ever have. It felt like my ass was going to cave in! She gets off, pulls my pants back up, and walks out, leaving me there on the bed, just fucked and nicely toasted. I fell asleep about 30 seconds later, and woke up about 13 hours later. My aunt didn't mention anything afterwards, but my cousins sure as fuck did. My brothers never gave me weirder looks after I got home.