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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

From: Martin

Stile, your site has kept me entertained through two years of college and I thought I would finally contribute in the only way I have thought of.

This is not a story about the first time I had sex, but rather the first time I had sex with an older woman and still the best sexual memory I have. I had recently graduated High School and had a girlfriend for most of it, so my sexual partners had been limited to only her and one of her friends who was a total slut and yet neither of them were very satisfying in bed for me. I started working at a local bar and grill as a busboy and although I was only seventeen at the time, most of the wait staff let me party with them
and took me out to get drunk at other bars in the area. During this time, I had hooked up with a couple of them and one of the girls who dated a cook at the place was really gorgeous, had really hot friends but she was late twenties, and I didnt think I had a chance.

One night during work, Ginger took me to a table to bus it and introduced me to a friend of hers. Her name was Sonya and she was better looking than anyone I had ever hooked up with. So I cleared off the table and went about my work when Ginger came back and told me her friend really thought I was a
good looking kid. I went back and asked her how old she thought I was, and she said 22 or so. I guessed her age around 26 and this seemed like a gap that could be erased with alcohol.

About a month later in early August Sonya began to work at the restaurant and found out how old I really was. I found out she was 30 at the same time, and I was pretty devastated, as I said before I didnt expect anything at this point because she was almost twice my age. She had told me it was a pity I wasnt even legal, and it was kind of an inside joke we had that we would fool around when I finally 'came of age'

My birthday is on the seventh of september and I hadnt yet left for school that fall, so I asked if she wanted to go out and drink for a while to celebrate and bullshit about whatever the day before, so I would be eighteen at twelve oclock, technically. Asking her out was pretty easy because I was the only busboy left and she had to talk to me to get her tables cleared. It was a sunday and she told me all the bars would be closing pretty soon, so she started ordering drinks to a fake table and we drank them behind the counter. When we finally got off shift I was pretty buzzed and we went down the street to some shithole that would serve anyone who could see over the counter. On this particualr night though, the manager who was a real asshole as most managers are, decided to card me so we couldnt get anything to drink. She told me to go wait in the car and she would be out in a second. Out she came with two bottles of wine and a big smile.

When we got back to her place, she told me she planned on getting pretty drunk and I might have to stay the night. I remember this being a most appealing prospect and told her I was game. We watched late night TV and drank both bottles. At this point its past 12 she asks me if I want a birthday kiss. My dick immediately wakes up from a long slumber and I tell her sure. She climbs across the couch on all fours and kisses me really deep, not a high school kiss I could tell I had a womans tongue in my mouth.
We sat and grinded on her couch for at lest half an hour, just kissing and me feeling her tits, which I didnt know the exact size then, but were larger than my hands. As I lay there groping her and enjoying the first couple hours of my birthday, her hand slides down my side and begins to grope my rock hard cock through my pants. She tells me Im so young and hard and she wants to have me inside of her and all I can think of is if I will be able to perform because like so many men I am afflicted by smallpenisitis.

We head into her bedroom and at this point I realize I dont have any condoms. Being a risktaker, I quickly ask if she is on birth control and she says immediately yes. Too drunk to argue with this and too damn horny to stop her from unzipping my pants she tears them off and begins to kiss all over my inner thighs and lower stomach. I lay back in rapture and begin to realize I hadnt had a good blowjob in a very long time. She engulfs my cock with her mouth and begins to jerk off the lower end of my shaft and cup my balls while she machine guns the top of it with her razor thin lips. Im concentrating on not blowing my load too fast because I still want to fuck the daylights out of this gorgeous babe who is now moaning she is wet and wants me fuck her.

She gets up from the position she was blowing me in and takes off her shirt with a smooth sexy lift and reveals to me the largest tits I have ever had real experience with. I later find out she has 34DD's and plans on getting a reduction, so Im one of the last men to have and hold them. She slides up on my very naked body and rolls her on top of me, grinding away at my pelvis with hers and urging me to get her as naked as I was. I slide down and unbutton her pants with my teeth, I made an attempt to unzip them buit this was just too difficult at this point. I finish unclothing her with my clumsy hands and now am not quite sure what she wants -- more foreplay or sex. I opt to warm her up a little and stick two fingers in her clit groove massaging it causing her to throw her head back and close her eyes in ecstasy. I fingerblast her for a while and nearly blow my load she is getting me so hot -- she keeps a hand on my cock while I pleasure her.

I still think this is the wettest girl Ive ever been with, she must have produced a pint of fluid while i fingered her. After what seemed like an eternity she flips me onto my back again and mounts me, sliding my cock inside her in one motion. She rides me for a while and her tits are bobbing up and down the whole time turning me on and providing visual candy when i cant grab ahold of them and really jam it in her for a few strokes. The arch in her back provides the best friction and this is how I end up cumming
with her almost in a strait line away from me, riding my little cock and loving every second of it and me thinking this is the best birthday Ive ever had and the sun hasnt even come up yet.

From: N.

My first time kind of sucked fat ass, so I'll tell you about the time that I subsequently de-virginized a friend of mine. I was 19, and had brought up the subject of casual sex a couple of times before to him, and he had always turned me down, although he said he thought I was hot and all. At the time I was 5'6'' blonde, blue-eyed, and had a nice, curvaceous body ... not fat at all, mind you, but not bony-assed-Calista-Flockhart-thin, either. I suspected that he was just afraid of it all, what with being a virgin and 23 years old.

Well, finally the subject came up again that we were both horny as fucking rabbits, and his hormones finally got the better of him and he let me kiss him. We were in my dorm room, and I got up from the bed and wandered across the room, coyly, and changed behind a door into red lace panties, bra, and a satin short robe. I came back from behind the door with a bottle of lotion in hand, and ordered him to put lotion on my smooth, freshly shaved legs. He complied, and the more his hands rubbed on my legs, the more I lost my ability for rational thought. I was so horny, I was fucking dizzy.

He stopped suddenly, and I knew what was coming next. He promised me that we would do it the next night, but he had to get back to his room and study for his exams. It was obvious that he was nervous, and I figured I had it in the bag, so I stood up and untied the front of my robe. I pressed myself against him and wrapped a leg around him and told him not to let me down. Then I kissed him long and deep.

At the time, he was seeing a counselor, and that next day this bastard told him that it wouldn't be a good idea if he slept with me, given that he had feelings for me and I, him. Of course, he told me this, and I was PISSED OFF. Here I was, walking around all day horny enough to fuck a parking meter, and he was telling me that his "shrink said no". I mean, what in the HELL could be wrong with a little nookie? I had only been with two other guys at the time, and I figured that I'd give him a nice long lesson about lovemakin'. But NO. I bet that smelly, hippie-assed counselor never got a piece in his damned life.

Shortly thereafter, he dropped out. He moved to a town not to far away from mine, and we continued to communicate via electronic means. I had pretty much given up all hope. Then one night over MSN he messaged me and told me that he had been thinking about me in "naughty ways" and he couldn't get me out of his head. Well, Stile, that just about floored me. He told me that he wanted to run his hands over my soft skin, and all that jazz. I told him to quit messing with me if he wasn't serious, and he said he was. So we actually set up a date! It was to be that weekend.

He came down as planned, and proceeded to spend about six fucking hours visiting his old friends in our dorm ... it was obvious he was stalling because he was nervous, so finally I pulled him aside at about 2 a.m. and told him that if he didn't get up to my room in ten minutes, then he should just go home. Ten minutes later, he entered my room to find that I was horny and waiting.

Stile, he was hung like a show pony. 7.5 inches long, and hella wide to match. I sucked him off for awhile; I really pride myself on my head-giving abilities, and had no problem deep-throating him. I decided that it was time to get the show on the road so I let him finger me through my white cotton panties (which he really liked) and then he went down on me ... both were fucking awesome for a first-timer.

We then fucked like we'd never get enough. I rode him and it was like straddling a telephone pole. It felt so fucking great. We doggied, missionaried, spooned ... and here's the kicker, he went for THREE HOURS straight without busting a nut. I am NOT lying to you. I could hardly believe it myself. I guess it was because he was nervous as hell, and after masturbating for so many years, I guess you get used to a certain "feel" for things. I came about five times, and finally I told him to stop because he had fucked me ragged. So he ended up blowing his load on my tits, which was fine with me.

The next day I was walking bowlegged. I had never felt so well-fucked in my life. We proceeded to do it a couple of more weekends after that, but then he backed off because we didn't really want a relationship and we were becoming too emotionally involved.

It was the best sex I ever had in my life, and we are still friends.

From: Quan

Love your site Stiles !

My first time was when I was 17, she was 23. I had just fucked up my first year at college, was working at a coffea shop and bar hopping. Her friend had grabbed me at a club and asked me to dance with her, I was really drunk and made an ass of myself, I was grabbing her all over. I called her the next day and apologized, we went out for coffea a couple of times over the next few weeks during which I found out she had a rich boyfriend in some other province. By this time my friends had somehow found out I was still a virgin and were razzing me pretty bad. So I said fuck it, no more mr.nice guy, the next time I saw her I had the full court press on, all the stops were out !

We were at her work, a massage parlour, I was feeling her up and rubbing her down there and we had a few coolers each over the next couple of hours. Then she decided enough was enough and she wanted to drive home with me. All the way there we were kissing and I kept rubbing her down there. When we finally got there we wasted no time and went straight upstairs, she had a waterbed and proceeded to get naked in the dark and then got in her waterbed, she insisted that I get naked standing up and when I was done she asked me to do a little spin around and her show her the goods, being the horny kid that I was I didn't care, I was getting punati ! So I hopped in to bed and we went at it slowly at first with a condom and it was great, she was all wet from all the touching, I was more worried about how I was doing especially when after the first half hour she asked how many women I had been with (I lied and said two) we fucked for a couple more hours, midway through she was curious why I wasn't coming so she yanked off my condom. I still couldn't come so we gave up and the next morning we fucked again on
the floor and after a couple of hours I finally came.

That woman taught me everything about sex, she gave me my first blowjob, she was the only person
I did it anally to. Well long story short 6 years later after finding out what a complete fucking liar she was about practically everything we separated. We have a beautiful daughter that is biologically mine. I see her and her two half sisters both from different fathers every weekend and I pay child support till my ass bleeds and the money goes to her drinking/partying fund while my kid has old hand me down clothes from her sisters.

The moral of the story, don't let your dick do the thinking no matter how good the pussy is. Especially with a woman with kids from multiple fathers who is willing to fuck you while she has a boyfriend. Have fun and cut your losses, no pussy is worth fucking up the rest of your life for.

From: patrick

my first time was a threesome. so, me and my boy are up at my local fast food job waiting on my paycheck, and i'd just broken up with my girlfriend of over a year (and never hit it....i'm a loser), who worked there with me, when this hot little number who'd been working there for some time came up and asked to hang out with us this evening. sure....so we pick her up, and it was a shame because she had two really hot sisters who were grounded, would have loved to just stayed there that evening, and went out and got two bottles of aristocrat vodka, went to a hot tub at some random apartment complex, and gang banged her little ass in the tub. then we went out in the woods and hit it there, then over to my boys house and hit it again, then drove around and took turns on it. fucking unbelievable, petite little thing, long hair. mmmmm. the shitty thing was, she was supposed to be home at 10, but we just got her drunk and kept changing the clock in my car to keep her up for more. she left her underwear in my car, and when i found them the next day, they had fucking skids!! nasty little trailer park whore. and having other dudes there while you fuck is not cool. i rock.

remember asshole, no email address if you use this. and do a fucking update now and then, or i'll find a new pimp.

stile sux.

From: Melissa

Hey Stile,

Thought I'd add to the collection of First Time stories. When I was younger, I felt like I could hold out until marriage. That way you "know" if the other person loves you and whatever. As soon as I realized
that wasn't going to get me anywhere in life, I decided to go to NYC and meet this guy I had talked to
online before. He seemed like a cool guy because he was in college and a few years older than me. He had been to different places in the world like England, other parts of Europe, and India. So he seemed smart and like someone who had a lot of experience (not just sex).

This was maybe the second time I met him in person. It's always weird meeting people from online in person because you have this idea of them but that doesn't necessarily hold true in person. Upon meeting him, I thought he was skinny and short and totally not attractive but since he had a dick, I could deal with it. Besides, what did I know, I was a virgin.

So anyway, the first thing we do when we get to his tiny apartment is kiss and take each other's clothes
off. We're in his parents' room because they are out and their bed is huge. I always thought that was kind of weird - having sex on your parents bed. He gets on top of me but not IN me and everything feels right. I also had a crush on this guy so it seemed so perfect. Anyway, it was agreed that he was gonna fuck me and the first time is supposed to hurt like hell, isn't it. Except it's not this scraping your knees on the pavement for a half-mile kind of pain that this classmate of mine said. It was quite bearable and all
I could think of was that I'm finally getting laid. With a guy I liked.

We tried a bunch of positions and I kept track of time because there was a huge alarm clock by the bed. It lasted twenty minutes but I believe that included foreplay. Since I was spending the night, he had to
be nice to me. He offered me stale Doritos and flat, room-temperature Coke. Man, I was such a winner.

After all that, I thought I had to be some sort of responsible housewife and clean up after my mess.
There wasn't a whole bunch of blood at all. Only a spot on the sheets and I started freaking out and
tried to get the bloodstain out. Although, in retrospect, why the fuck should I care. I never asked
him what he was going to do about it after his parents came back. I figure he was smart enough to get them new sheets.

For the years after that, we used each other for booty calls from time to time. When I was in-between
boyfriends, I found out that the reality is that this guy was an awful lay. He did everything too fast and
he lasts less than a minute. I guess when you start out at the very bottom, sex can only get better for
you. Now I have this awesome boyfriend who can last forever and we fuck like mad rabbits everyday.

Love,
Missy

P.S. Stile sux!!!

From: Wil

been into yer shit for a while mr stile, and i figured i would share me first time.

it was 17 years ago. and i was 12 ....how fucked is that?

i lived in a shitty seaside village in the south of england where there was fuck all to do, you know the usual, and i was hanging out with these two girls on the beach, laura and katheryn, they were in the same year as me in school.....how fucked is that?!!!

anyway, it was a boring saturday in the middle of summer and we were just sitting around for the day, usual bullshit, annoying the old people blah blah fishcake and i got curious as to what it would be like to fuck someone. in a heartbeat, katheryn goes 'Will, i will fuck you, meet me here later on' FUCKING JESUS SHIT THE BED! so i whizz home, grab a sandwhich for lunch, fucking shaking like a twat.

i cycle back to the beach and shes there! fuck, thinking about it cracks me up! we were so young, and she was cute too, you know, like first crush cute....

anyway, we snog on the beach for a while, feeling her boobs, well, what she had for boobs, and we decide to go and find somewhere to do it....unbelievable! this is my first time, she had done it before, the slut, but that was good...

we walk up the beach to this holiday park called Holbourne, cause there was some empty chalets, complete with beds, that us little kids used to hang out in sometimes...bingo.

we get in, locate the bed and strip. shes lying there and im fingering her when i see a large cut at the top of her pubic hair. it happens she was going to cut a swastika there!!! what the fuck!!! she was crazy!! anyway, this finger fucking goes on for a while and she says i can fuck her when im ready.

i remove my pants and she guides my tiny 12 year old cock into her, i cant feel much, and do the 'fucking' movements....its a hot day and im sweating my ass off. this lasts for ages as Im too young to cum *ha ha, thats the best part!!!* so she asks me too stop when ive had enough.

when we're done we kissed like kids and i cycle home for my tea.

oh happy days

From: Skye

I fucking love your site and I was reading a few of the First Time stories and decided my wouldn't be too bad next to a few of them, so here's goes whatever. I had just turned 15 and had met this older guy (I'd say he was in his 20's) at a local grocery store, we talked for awhile, obviously attracted to one another, then exchanged email addresses, a few days later, after talking for hours on end each night, we decided to meet again. I told my parents I would be at a friend's house for the night and left around 1am with him. The guy would stop at every light to reach his hands into my pants and brush his finger over my clit, being sure to keep me nice and wet until we returned to his parent's place an hour away. We crept into the basement, trying desperately not to awaken his family and as soon as my foot hit the bottom step, my clothes vanished and he was rubbing over my nipples and pussy.

We made it to his simple matress laying on the floor before he began to eat me out roughly, then turned to the wall and began to beat off quietly, telling me how sorry he is for being a hornball. I didn't know
what the hell to do at that point, it would be kind of hard to go home and kind of pointless to just lay there, so I told him to fuck me. He rolled over and pressed into me hard, suprisingly not hurting me at all, pumping swiftly before becoming sensitive and withdrawing. Then curling up in the corner, almost crying, then turning to me and pressing into me again, fucking me hard, pressing against my chest to hold my body still. He became sensitive against and drew out, beating off again, then layed on his back and looked over at me, caressing over my cheek and telling me how he loves me before pulling me onto of him and letting me ride him to my heart's desire, just as I'm getting into it, the phone rings. We both look over at the damn thing and immediately draw away from one another, the next thing we hear is his mother screaming down the stairs "There's some man on the phone that says who have his fucking daughter, what the hell is the matter with you?" He throws a blanket over me and pulls a pair of boxers on, running to retrieve the phone from her and telling her that he has no idea what he is talking about, my father tells him that if I don't show up by morning, he's calling the cops and then listens to the guy's bullshit story before hanging up.

I go hide in the closet while the guy fights with his mom and his mom takes away his car keys. Let me tell you...sitting in a dark cold closet half naked is no day at the zoo. So I get dressed and call a few friends
(its 3am, so no one is awake of course), and as I'm talking to the one person that answers the phone, this guy is kissing along my belly and fingering me. Finally, we just steal his sister's car and get the hell out of there before his mom can catch us, he's on fumes so I pay for gas, he drops me at my grandpa's apartment complex and gets the hell out of there. To say the least, it was the best time of my life...sex, adrenaline, who wants more?

From: Matthew

This is the story of how my sex life came to be. Unlike what seems like most of your readers, I did not lose my virginity to something fat, dead, or other than a human. My girl was actually skinny, hot, and sought after by many.

When I was about 16 and a half, I impressed this girl that was a year older than me (let's call her J, for the sake of the internet) with my nineteen foot woody, yup, my station wagon. We started seeing each other around school for a little bit and then it progressed into the weekend. Not more than two weeks into the realtionship I had this girl butt-ass naked in her mom's basement. I was naked too, but who cares about that? Before she got naked though, we were talking about sex and what each other would like to do (both of us being virgins). I asked if she were shaved and she said yeah, so I told her I'd like to see her naked. She complied and got undressed in the basement. I then found out that she mustn't have understood "shaved." The front was all clean, but nothing but hair all around the clam. Whatever, my dream at this time was just to eat a chick out. So I did, and I really liked it. We didn't have sex that night, but that led me to be able to considered such a great guy since I went down on her and didn't make her do me in return (though I am a little bit above average, I am uncomfortable with my size).

So the next weekend comes by and we're at her mom's house again. We were watching some movie in her room when we decided to go at it. IT WAS SO FUCKING TIGHT THAT IT HURT. I didn't know if that was how sex was supposed to be, but I didn't really like it. I couldn't finish because it hurt that bad. Let me get one point across, I had never orgasmed in my life at this point. I never got a blowjob, never got a handjob, never masturbated (yeah, I rubbed myself while looking at porn, but I didn't know how to make myself cum); only thing close was one time I woke up during a wet dream and actually got the feeling of cumming instead of just waking up in the shit. Well the next weekend has the same scenario; her mom's in a band, that's why the house is always empty. Same thing, I COULD NOT CUM. The tightness, plus being about 25 degrees in her room, wasn't really that good for me. But the next week was when it finally happened. I told my parents I was staying at my friend's house. At about 1 am, I snuck from his place and she snuck from her dad's place. We met at an Eagle grocery store which was in the middle of the houses.

We walked back to her dad's house and I was so fucking nervous. We get into the back room and immediately start fucking. It was great. We were manuevering ourselves in plenty of positions and she kept using a pillow to stop from screaming. She was a dancer for 12 years, so pretty damn flexible. The ending position that made me cum was with her rolled onto the back of her neck with her ass straight in the air. I pounded right down in her pussy and came. I just slumped over her like I had been shot and killed. It was so good, I coulda just fallen asleep right there. While we lay there gasping for air, I finally rolled off of her. My condom was gull of clear and white liquids. We fucked three more times that night, each ending in a spectacular orgasm. It was a good thing I worked in a pharmacy and could just steal the condoms I needed, otherwise I woulda spent a lot of money on condoms up 'til she got the pill. We left her dad's house so I could get back to my buddy's before dawn. Since we couldn't leave the condoms there at her house, I took them with me in a plastic cup. On the way back, one of her ex-boyfriends' cars was parked on the road, so I emptied all of my cum over his windshield and door handle. I draped the used condoms over the antenna and laid the rest on the windshield.

Well, I finally convinced her to shave and can now get her to do almost anything I want. She's actually turned into quite the freak, doesn't bother me as I'm the only one that gets it. We've tried anal once, as that's the new kick I'm in. She didn't like it cuz it hurt, so I only got one thrust before she pushed me out, and said maybe I'd get more if she were drunk. Well, I think I'm gonna take a bottle of Cap back this weekend when I go home ; )

From: Matt

Hey Stiles, heres my first time sex story.

I was 15. Most of the girls who I had relationships with come from psych wards, and are usually really screwed up. Well I met this girl in an inpatient group, and we became friends. She was some weird punk cutter suicide girl. Basically I asked her for her AIM name, and we got to talking and after about 10 minutes she told me how she was a horny virgin and really wanted someone to fuck. So I asked her if I could come over, and she said I could, so I came over that weekend.

We basically just made out and i shoved my finger in her mouth and she gave my finger a blowjob for a little bit until her mom walked in and she got really embarassed and started crying. Well, I really wanted to lose my virginity so she came over the next weekend and we were,"watching a movie" (making out and shoving my finger in her mouth). And basically I had stolen some condoms from the convenience store in the mall, so I asked her if she wanted to fuck, and she said yes.

Sex was nothing like I expected, it totally fucking sucked, I just sat there staring at the wall waiting for it to be over. She was really horny and rode me for about an hour until she had to leave. I was pretty disappointed because I had imagined sex to be some grand euphoric thing, and It absolutely sucked. Btw, I dont have any strange past sexual history.

I fucked her another time just to be sure, and yes, the sex sucked. So, my sex life still sucks to this day. Now I'm dating(fucking) a psycho girl that I met from a girl in the psych ward, and it still sucks, but atleast I', getting laid.