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part 1 - part 2 - part 3 - part 4 - part 5 - part 6 - part 7 - part 8

From: Ashriel28 [ashriel28@hotmail.com]

Hi Stile, here's another first time story to add to the collection.

I was 20 years old when I lost my virginity, I had a few girlfriends before that, and had gotten pretty far with some (fingering, hand jobs, blow jobs), but just never had sex for some reason. I guess I was too caught up in being a "good" kid or whatever. Anyways, on to the story, so I was at a party at a fraternity on another college's campus, and not really getting anywhere with anyone, so I went to a quiet area to relax a bit. I noticed one of my friends talking to a little asian girl on a couch and I figured I'd go over and help him out, maybe see how things were going for him. He probably wanted privacy, but I was drunk, ok?

He didn’t look too interested anyways, and after a little bit of talk, he left me to talk to her. I found out she was a freshman, 18, from the east coast (we both go to midwestern schools). At one point it seemed like she wanted to kiss me, but at that point I was still trying to get her interested in my friend. So anyways, a little while later, I got dragged away from the party by my friends who wanted to leave, but not before getting the vital information, her number. A month goes by and I finally decide to call her, on my friends suggestion (he wasn’t that interested). Turns out she had never been to the city, where I went to school, and she'd like me to show her around. So we schedule for her to come up the following Friday. Now I barely know this girl, and she's coming up to stay with me for the weekend, but I didn’t bother analyzing the situation at the time. Friday rolls around and she misses the bus we planned for her to take, and she had to catch a later one, she got to the city around 10 PM. So, instead of going out like we planned, we ordered some chinese delivery, and put in a movie. Risky Business, you know, the one with tom cruise getting it on in the subway.

After we ate, we were sitting on my couch, and she started to sit closer and closer to me. By the end of the movie, we had kissed a couple of times and she was damn near sitting in my lap. I suggest that we make her bed (my couch folds out) and in the process quietly close the door to the dorm room. So we end up making out on the newly folded out bed. Clothes start flying everywhere as we were going at it, and soon enough, both of us were completely naked. Now, I've known this girl in person for maybe 4 hours, max, and here we were completely naked, this was a new situation for me. She asked if I wanted to fuck, I said sure (what, turn down sex?), and proceeded to break out my reserve condom, you know, the one every guy keeps, even if he isnt getting laid. We ended up fucking for like 5-10 minutes or so. I guess its not a long time, but I was just happy not to pop right off the bat. Later on, I told her that had been a virgin, and she was surprized, which was a big compliment for me.

So I ended up taking her out on the town the next day, and we fucked several more times before she went back to her school on Sunday. One time we even fucked with my roommate sleeping on the top bunk in my dorm room. She came back a month later to stay with me for a week, and all we did was have sex in my dorm. She couldn’t get enough. It was during this week that I found out that she lost her virginity about 3-4 months earlier, and she had been with 6 other guys in that time. What a slut!!! To top it off, one of the times we were having sex, she screamed out. "I want your baby!" That was it for me, I dumped her a couple of days later, happy that I always used protection. But anyways, whenever I look back on losing my virginity, I always laugh and think about how the movie risky business got me laid.

From: Adrian [awhofman@dingoblue.net.au]

Dear Stile... God hates me. He must. This is the conclusion I've drawn after recent events. I'll explain why in this first time sex story (which isnt really a first time sex story, but more of a "get really fucking close to sex and then have your entire world come crashing down" story).

I was 18, in my last year of high school. An old friend had asked me to be her partner at her graduation (she went to a different school), and I accepted. At the time the thought of screwing her didn't cross my mind, I just thought yeah, what the hell, why not. She wasn't that bad looking, in fact I thought she was gorgeous. Its just we were friends and nothing more at the time.

Over time in the lead up to her grad I actually became closer to her and started liking her in a different way. Then I started thinking about screwing her and what an opportunity the grad date thing was gonna be. I could hardly contain myself. I went out and bought a suit, bought flowers, etc etc. Unfortunately I also met one of her friends. This fat fucking slut who was a friend of hers met me and we had only talked for an hour before she decided she wanted to fuck me. Everyone told me that she was gonna try and get on to me on the grad night. I wasn't gonna touch the stank ho because a) she was fucking fat b) she had a bit of a town bike reputation and c) I was certain I was gonna pick up with my partner anyway. So right there, I passed up a prime opportunity to finally lose my annoying virginity.

Anyway, on to the grad night in question. She looked stunning. Good food, good company, good wine, good time had by all. Then on to the afterparty. We were getting along very well at the grad and yes, we ended up getting together. It was marvellous. But I had only been kissing her for about 5 seconds before a huge ex boyfriend rocked up with his 5 huge mates and stood around me. I knew this guy, and his reputation for flying off the handle every now and again, so needless to say, I took my fucking hands off her in a second. Not to worry, as all was not lost - we kept in touch after the grad and a month later we were dating. I thought "fucking yeah, shes 18 and a virgin, she's GOT to be wanting to fuck me real soon". This was actually about the time you started running your first time sex stories, and I was thinking about how I was gonna write in and stuff. Not so.

Three months later. I'm still with her. I fell in love with her. She fell in love with me. Both still virgins. We had pretty much done everything except for fucking. But whenever we get together she would always say "sorry but Im not going to have sex with you tonight". I was confused, as she never told me why, but being as loyal as a dog I didnt question it. Then she finally told me why. She was in tears. Apparently she is one of the one in a thousand people born with some fucked up condition, that for one reason or another, prevents them from ever being able to have sex. I was gutted.

I reflected on grad night. I had a choice - I could have gone with the girl who would have fucked me at the drop of a hat.... but instead I went with the girl who could never fuck me at all. Im telling ya, God fucking hates me.

I don't believe you. I've never heard of a condition which makes sex impossible. Bullshit I say!

From: Ben Freeeman [mayoisgod@hotmail.com]

Well I have read storys about boyfriends with girlfriend storys. Well i have read them all and I have not seen one with MY story.

One night this girl, ill call her jenny, walked to my house from her 3 mile away residence. This girl worshiped me, wrote her name all over her clothes and books and house. Jenny thought I hung the moon so when she came over whatever I said goes.

After some small talk jenny took her jacket off and looked me in the eye. At that moment I figured out beside her friend she is the ugliest thing to ever walk around in salvation army clothes. She then came over and started rubbing all over me. In most cases you are suposed to be grossed out and say "No whore no penis for you silly bitch" ......but I gave in.... She said she liked pain and she wanted me to hit her. I hestated a little bit then I nailed her in the face.

She was so happy after that... after a few moments of slapping and punching I took her pants off and started fingering her. She ate it up so i started doing it really hard with 3 fingers, I pounded and pounded and then I felt my fingers rip thru, to the nuckle of flesh. I pulled out and Jenny smiled and said "Master why did you stop?" at that moment I looked down she was bleeding all over my bed sheets. Apperentally I ripped thru her walls into her rectum.The smell of period and shit filled my room, and then she begged for more. Felling sorry for her I went down stairs to get a towel when I came back she had made a massive puddle on my floor. "Get on the towel I said" she did and I pounded her some more. She moaded and goared and all of a sudden ,"Master!! I cant hold it!!!" *plop plop* two pieces of shit splattered all over the towel. I was furrious I said ,"Jenny clean it all up and when your done leave my house!". She clenaed it up but the smell was there. After she left I sat and thought about what happened. Maby I was too hard on her, but then again she was asking for it.

Another bullshit story. You sick fuck.

From: Bracey Miller [proj3ct@msn.com]

So there I was, I was 15 and I had been dating this chick for about 7 months. No sexual or physical contact whatsoever...and at the time I didn't care, because I was "in love" with her. Now I hope she dies via some sort of accident involving her ass and a professional glass-blower, but that's besides the point.

So on to the story. It was getting to be about 7 or 8 o'clock on a hot summer day. We were upstairs in my room. (Back when I lived with my parents.) We had talked about having sex but never got to the point of doing so, not even close. Well, this was different. She finally said "ok", and mind you, she was NOT a virgin...I was. Anyhow we got situated on the bottom bunk of my bunk beds, and since I was new at this I wanted to be safe. I asked her if she could stick it in for me. She obliged, and grabbed my penis and whole-heartedly rammed it in. Or so I thought. It went in about 1/2 the way, and she screamed like a fucking banshee. She gets up, walks a few feet, and falls on the floor out cold. I was shaking her and trying to wake her up, which she did a few minutes later.

I asked her what the problem was, only to hear her say, "What the fuck? Do you want me to go home and shove a cucumber up my snatch so I can fuck you?!" Well, I was thrown back. I had no idea what way to take that. As a guy that seems to be quite the compliment. (Later on I found out I have a small one.) So anyhow, She called her mom and got taken home. I didn't know what the hell to do. So I said "The hell with it." and went to bed. I got a call from her early the next morning to hang out, and I was happy she wasn't mad. Well, later on that day we ended up back in the exact same place. Her trying to shove that shit in there. She screamed again but I said "Hold on...just trust me." and eventually I rammed her the beef. All was good sailing...for about 15 minutes. I hear the doorbell ring downstairs, and I knew who it was: The Pizza Hut Guy! Well, since I was out with her all day I didn't get a chance to eat yet so I just calmly got up and walked out the door. As I came back in, (pizza box in hand) she didn't say a word. There she was, in shock, and laying there naked and confused. I finished up my pizza and jumped right on her. Surprisingly, she was willing. I guess she wanted to get this over with. So off we went!

The next 30 minutes or so were bliss...and I had never had an orgasm like that in my whole life. But oh, the fun's not over yet. As I pulled out and laid back, she sits up and says, "Hey...umm look." while pointing at my crotch. I didn't have the condom on. This wasn't good. So I said "Well, go in the bathroom or something and yank it out...it probably got stuck in there somehow." She insists that I was the one that GOT it there, so I had to fish it out. (No pun intended) So I reached and snagged it after about 5 minutes, threw it away and took her home. (My mom found it later and now I shall never live it down.) So that's why I no longer use condoms anymore, and what I think might be an interesting first time story for you to read through. Oh by the way, fuck the times we're in. Now because I don't use them I can't EVER seem to get laid.

From: CNUFootball@aol.com

I was 15 years old the first time I had sex. It was during winter break like a few days before christmas. I got some dude to buy me a bottle of MadDog 20/20 and I got my neighboor chic to stay out late and drink it with me inside my dads car while everyone was asleep. Sooner or later we were kinda wasted and started to mess around. We started to do it in the car but it was too small. We didnt care how cold it was outside but we got out of the car for more room besides it didnt last long anyway. After we were done she went home and I passed out on the couch in the house. The next morning I got up to get the newspaper and I noticed I left a jizzsickle on my dads hood.

From: Danielle Kirtley [scarlett_kiss@hotmail.com]

Okay, i have read quite a few of these first time stories, and i have decided to share my story as well. But this time it's told by a girl! It was a few months ago actually, my first semester of college, and i was 18 then. i was getting stressed in my new college life, my friend from high school invited me to come stay at her campus for the weekend, just so i could get away. so i said what the hell, packed up my stuff and went down to see her....

I had a blast getting to know all of her new friends she had met in college. Especially one girl, who i was totally diggin from the start. (we'll just call her Lisa.) One night there was a huge campus party, and Lisa was looking fuckin hot in a pair of leather pants, and a backless leather halter top. At the party, i noticed Lisa was getting pretty drunk..... i never drink, so i think i was the only sober person in the room.... Throughout the night Lisa began coming on to me, and grinding with me on the dance floor.

Close to the morning, Lisa and I crashed in the lounge of the dorm, and she wanted me to stay awake with her while she sobered up before she went to bed, and we decided to pass the time giving eachother messages. i rubbed her all over her nody with my very capable hands, (so i've been told) and then Lisa began to give me one as well.i began to be totally relaxed, when we heard a couple having sex in a dorm room nearby. i was kind of shocked to hear such a thing going on, but it got her totally hot. and she began touching my breasts, and kissing me... needless to say, i had to tell her i had never done any thing like this before...she grabbed my hand and took me to her room.

The two of us, now alone in her room started going at it hot and heavy. She whipped out a ten inch, blue strap on, and she began to slowly fuck me... it was incredibly good, (since i had already popped my own cherry before) and i came twice before i stopped her. I told her i wanted to fuck her now. Lisa was shocked at first, then smiled and strapped me up. i pounded her gorgeous lesbian pussy for hours on and off, till the morning. And every now and then she would beg to eat my pussy till i came in her face.

I left the next day saying goodbye to all of them, and i havent seen Lisa since, but i do know that she has moved back to her hometown in Alaska, and is going into message therapy.... ironic huh?

From: eat poo [skrog@onebox.com]

Hi, Stile.

This is about the first time I have ever fucked a girl up the ass. Well I just broke up with my girlfriend. So I figured I would go out and look for some new ass. Why not a better place then AOL chat rooms. Hah. I was chatting away to this chick. We traded pictures. So I said what the hell. She was not that far away from me. So I ended up talking to her on the telephone. A couple days later, I asked if I could come over. She gave me the directions. I got my ass over there. No one was home. We had the whole house to ourselves. So we started fooling around in her bedroom. The usual kissing and feeling up. I worked my way under her shirt. And her hands ended up on my meat whistle. So we ended getting totally naked under the sheets together. Few minutes later we decided to give it a break. So I decide why not take a tub with her.

Keep in mind that I only known this girl for a few days. And I am buttnaked with this chick about to get in the tub with her. So we jump in the together. We start fooling around again. By this time I am extremely horny and so isn't she. But that bad part I had no condom. And I didn't want to get her pregnant. So I ask her if she has ever tryed anal sex. She replies by saying "No". So I was like would you ever try it? She said "yes". So I was like all right. We hopped out of the tub and dried off. And made our way back into her bedroom still fully naked. So I was like want to have anal sex. She replies by saying, "Why not?". I have her bend over and begin to get her ready. By slowly shoving my index finger into to her ass. It pretty fucking tight. I have my finger all the way in. She seems to like it.

So I go to take out my finger. And bam low and behold my finger is covered in shit. I got pretty mad but I ended running to the bathroom to wash it off. But I was like fuck this I am not backing out. So I go back to the bedroom. And proceed to stick my cock up her ass. As it was moving in. She started get mad and forced me off her. She said no way are you sticking your cock up my ass it hurts way to much. But I did receive getting head from her before I went home. And I never have spoken to her again.

From: Escox2@aol.com

I was reading your sex stories and I find them hilarious, so I figure I would leave a few.

For a while, I was obsessed with getting my girlfriend up the ass. But she wouldn't let me try it. I tried and tried to convince her for about 2 months straight but she wouldn't budge. Finally, one night when were in my car messing around (and she was extremely drunk), she started to give me head. Before you know it, I had her buck naked in my car 69ing me. I figured, what the hell, she is drunk, so i'm gonna go ahead and try something. While she is sucking me off I went and stuck a finger in her ass. She actually enjoyed it! She got really into it after that, but I couldn't handle what happened so I blew my load pretty quickly. The next day when I confronted her about it though, she vehmently denied that I ever had a finger up her ass, and that she enjoyed it.

She kept saying that even if i did, she was too drunk to know, and that was disgusting and she would never do that type of thing. So another month passes by with no anal sex. Finally new years eve rolls around, and guess what, my girlfriend is drunk as hell again. I tell myself, thats it, i'm getting anal tonight. After the ball drops, we go to my room and start fooling around. Since she is good and drunk I just outright say to her "can we finally try anal sex tonight". After enough coaxing she finally gives in. So here is my big moment. I run in the bathroom, get some lube, come back, and proceed to start. I get my dick not even half way in her ass, and she starts to scream out in pain. She tells me to stop, runs out of my room, goes outside, and proceeds to puke out some nasty pasta that she ate earlier. So basically I ended up getting no anal, just a girl bitching that her ass hurt, and a shitload of puke all over my driveway. Eventually she did let me try it again and now she loves it (only when she is drunk though...).

Another time when my girlfriend was drunk, we were laying in my bed, and she was giving me a blowjob. Unfortunately she was feeling sick, and she gagged on my dick, and proceeded to throw up all over my dick, myself, and my bed. Short story but it was definitely disgusting. My friends like to call me
puke-dick and poop-dick now. Oh well, atleast I can say that I get anal.

From: Father Tesla [divorced@mail.com]

OK maybe my first time isn't with some whale whore or disease ridden skank but it was FUCKING GREAT. It was almost like something from American Pie where the not so popular guy hhoks up with a sweet peice of foreign ass.

I was 18 and in high school but the prospect of getting laid was looking very dim. I had a chance I guess with some dumb redneck bitches but was more than happy to settle for blow while I waited for someone decent enough to stick my dick in. Anyway, my senior year my school was overrun with exchange students from everywhere on Earth but no one wanted to give them the time of day. Then one day this fucking amazing tight bodied blonde comes walking through the hall and every guy almost bust nut right there. The second I saw her I wanted to fuck her brains out no matter what but hell why would she screw me. Well, skip ahead a few weeks and she is now good friends with every girl I knew and they were trying to hook us up!!! So finally we were out with some friends and she asked for a ride home and I jumped at the chance. Luckily we lived close to each other so she decided to just walk me home and then she asked to see my room.

I didn't think anything would happen but as soon! as we were in my room she fucking sticks her tongue down my throat and garbs my dick. She gave me 2 or 3 of the best hand jobs of my life and then said she was heading home. This continued for 2 months. She was jerking me off 3 or 4 times a day and blowing me just as many times, my happy dick never got a seconds rest. Then one day everyone was gone and were lying in my bed, my head spinning from another great blow job, when she said she was ready to fuck me. I almost died, I HAD NO CONDOMS!!! I broke the bad news but she said who needs them. We fucked 5 times that day and every damn after for almost a year.

She was fucking amazing. We fucked at public pools, parks, in the woods, football fields, everywhere. Eventually she went home and it took almost a year before I found another sweet peice. Oh yeah, she did give me syphillis and herpes but who cares!!!!!!!

From: jeremy 10121 [anti10121@hotmail.com]

Hey Stile

Ok my first time. I was 14. I was a freshman and she was a senior, and she was the first girl that i met that would do anything i wanted. so i her and i went over to our friends house for a halloween party (this house was the shittyest place i have ever been to) and the whole night she was trying to convince me to fuck her. like i said i was 14 and was kind of a pussy so i just kept trying to avoid the subject. well that night she went into the bathroom and motioned for me to join her. no one else was looking so i was
like 'what the hell' and followed her in. she then went down on me and i fucked her without a condom. a few months later i stopped talking to her and she told me that durring our 'relationship' the cheated on me with this guy that had AIDS several times. i freaked out. i had it all planned out to execute her in front of the whole school. well i have been tested every six months for the past 4 years and all the results are negitive. there ya have it stiles