• From: Billy Bob T.
• Subject: First-time story

Stile my brothah...

So here's yet another first-time sex story. I read all three pages you put up, and they are GREAT. So I figure you're still collecting more, and here's mine.

I was always a horny little fucking kid since I found my dad's Playboys way back when. I used to hump my pillow, pretending it was one of those Playboy girls. One summer, the night before going to summer camp, I even humped my pillow so hard I ripped the skin on the head of my dick! I bled all over my pajamas, and the next morning my mom saw me and wanted to know what the hell happened. I don't remember what I told her (shit, I was about 10 years old, and that was over 20 years ago!), but since we had to pack up and leave for camp, no one was interested in following up on that particular issue. Man, I wanted to fuck everything and everybody when I was a kid (and still do). I used to get raging hard-ons in CHURCH of all places! It was all that leaning up against the pews during mass. The problem was, I didn't know how to get any willing ass, even though it was all around me. It never occurred to me that I could get it to happen if I just asked...

So all that pent-up sexual energy finally got released when I was 15. The crowd I hung out with in high school, collectively known as "the freaks" included a rag-tag bunch of punks, new-wavers, preps, and even smart kids. Well, this one girl Jen (I'll withhold her last name, since she's now married, and she might just be reading this) was a really hot punk chick that we were friends with. She had the hottest hair... short and spiky, blond on top, black on the sides. And she just OOZED sexual energy. Well, one particular Monday she pretty much decided I would be hers, and started calling me at home. We talked about whatever two horny little teenage beasts talked about when they were not quite ready to say "Hey, let's fuck."

That Tuesday, while we're talking on the phone, she asks me what I'm wearing, and has me take off everything but my underwear. No more change than that... the conversation stayed the same, and we didn't talk about sex either. We were just talking on the phone in our underwear.

On Wednesday, it was the same story.. she calls, we talk, and then she tells me to take off my clothes... all of them, this time. Well, I get the feeling something is going to happen with this situation (I was pretty quick in those days, wasn't I?), so I tell her I want her naked on the phone, too. She tells me about each piece of clothing she's taking off, and then we go back to the regular conversation.

On Thursday she calls, and I take the phone into my room, and immediately take off all my clothes. She asks if I'm naked, and tell her yes, but she doesn't believe me because she didn't hear everything come off. I tell her I got undressed even before she asked, but she didn't buy it, so I got dressed again, and slowly took each piece off, announcing what each piece was and holding the phone so she could hear it fall on the floor. By this point in this whirlwind seduction, it's obvious that it's time to go at it.

The next day I see her at school, and she asks me to come over her house that afternoon, to "show me her room" or some such shit (as one of the other first-time story-tellers put it). Her parents were going on vacation, and the college chick who was staying with her while they were gone wasn't going to be there until the evening. SWEEEEEEEET!!! A 4-hour window! It was time to go!

Well, I get home, and my mom is home early that day for some reason, and now I have to come up with a story of where I'm going, since I didn't often leave the house in the afternoon, especially on a rainy day. Well, I make up some shit about going to see my cousin's soccer game, and that I wanted to ride my bike there (mom was going to give me a ride, but I had a different kind of ride in mind). I hopped on my bike and pedaled like MAD to Jen's house, a few miles away, in the rain.

I get there, she meets me at the door, and we start making out instantly. She showed me her alright room (a total MESS!!), and then she showed me her parents' room... it kind of stuck out of the rest of the house, and had huge windows on all sides and skylights in the ceiling. It faced the woods on their very private property. That room was BUILT for sex! So we start getting naked and do some humping and making out, when she comes right out and asks, "Hey, do you want to fuck?" SHIT-YEAH!!!!

I knew it was coming, so I brought a rubber I found in my dad's nightstand (Thanks Pops!). I threw that fucker on as soon as I could -- it was the first time I ever put one on, but I knew what to do (with that at least). I turned around to Jen, who was laying there on the bed, and I realized I had no idea where the hell to start!! I mean, I'd seen lots of porn mags before, and I knew where all the parts were, but I had little idea of how to actually do it (this was all before the internet and mpegs, you see). So in this new-found spirit of openness Jen and I had developed, I asked her, "What do I do now?" She told me to get close, put it in, and push. So I did... for about 45 seconds before I blew!!

She was really cool about it, and tried to get me hard and horny again, but I was so disappointed in myself that I wasn't up to it anymore. So we hung out around her house naked for a while, tried to make gin and tonics that came out WAAAAY too strong, and she tried putting some make-up on the HUGE hickey she gave me.

It was getting close to the time the "baby sitter" chick was coming over, so I had to jet. I got on my bike and pedaled my no-longer-virgin ass off through the rain. We both ended up at a party that weekend, but I didn't know what the hell to say to her, so it all just fizzled out from there.

I saw her again a year or two ago at a taco joint. She used to be the lesbian girlfriend of the woman of the couple that owned the place. Strange, huh? But she's doing well, and I've since figured out how to fuck like a porn star.

Oh, and please don't use my e-mail or name on this one.

Peace Stile...

• From: Future Father
• Subject: losing virginity = worst day of my fucking life

It's 2 in the morning and my face is illuminated by this cathode ray tube. I'm doing the usual... chatting it up on IRC... well... the ones who have no party life like I do. I used to drink and smoke drugs and all that shit. Then I made the crazy decision to become a cop. I figured I might as well give it up now while I'm not screened for it. But that's beside the point.

So yeah, this girl and I have been really chatting it up over the past weeks and tonight out of nowhere she's like 'Wanna fuck?'. I'm not going to lie to you.. I'm a fat semi-popular guy who is always 'the best friend'. And because of this i jumped on the opportunity to hump. I met her at the corner of her street (how appropriate) and we started driving around. I was gonna steal my mom's van but I wussed out and decided to tell her I was picking up one of my friends at a party who got stranded.

She, although reluctantly, allowed me to take her van to 'pick up my friend'. So we're driving around and we goto this dead end road on the outskirts of town. We sat there for what seemed like an eternity and she told me to finger her. I've fingered a girl before but all I had to do was touch her and she was shaking and shit.

This was a different story. I didn't even make her flinch. It was horrible. I pulled my fingers out and was like 'what can we do?' She's like 'well i did bring a condom'. i'm like 'lets do it up'. so we hopped in the back seat of the van and i strapped it on. i layed back and she strattled me and went to town. I suprised the shit out of myself. I really did. I went for so long compared to what I thought I would. I finally reached my breaking point, grabbed onto her ass and humped for dear life. I dropped seed for what seemed like an eternity only to be brought crashing down to earth when I heard the 5 words that will be burned in my fucking mind forever.

'I THINK THE CONDOM BROKE'.

If you could imagine the look on my face it would have been of sheer terror, disgust, dismay, hatred, pain, agony, and above all 'god-just-do-m e-in-now-cause-if-you-dont-my-mom-will'. I wanted to cry.. I really did. A 6'5 260 lb 18 year old wanting to cry. Fuck. I'm a disgrace. I should kick my own ass.

Anyways, When I pulled the remains of the dome off all the spooze fell out onto my BLACK pants. As if the night couldn't have gotten any worse. I drove her home and told her to check to see if she could see any jizz as soon as she got in the door and to come on IRC and tell me. She came on and told me that there wasn't any she could see. This made my spirits raise and almost brought a smirk to my face. I don't think I've ever slept as good as I did after hearing that...

Then the next morning came. My mom confronted me about the white stain on my pants when she went to wash them. I told her I tried to spit a ball of phglem out the window and it came back and landed on my crotch. I don't think she fell for it, but whatever... that's not the worst part. I had to drive my mom to work a half hour after the confrontation about the pants incodent in the same vehicle I lost my virginity in only hours before.

Now Stile.. I know you don't get much but you know enough that the smell of sex is the WORST smell to remove from anything. Even if you KNOW it's gone it's still embedded in your nostrils. I got in the car and the smell hit me like a ton of fucking bricks. I looked at my mom.. She looked at me. Reminded me of the stare downs from those cheesy old John Wayne western movies. She just shook her head and looked out her window.

At that point I was willing to face castration by rusty grapefruit spoon if it would allow me to go back in time and not lose my virginity. Ugh. I'm feeling light headed as I type this going over the events that took place mere hours ago. Since it's December 23rd now I changed what I want for Christmas. I want Santa to erase my mom's memory and to make me sterile. That way this kind of problem won't happen again. Besides, I think making me sterile would be the best thing. That way there won't be more little me's running around making the same mistake I did. Fuck. *shakes his head*

• From: Arius
• Subject: Damn The Hot Sluts (my story of the hottest slut I've ever known/fucked)

What's up Stile,

I was reading your Virginity stories, cause with this ghetto dial up shit, its the most entertainment for the time spent loading. Well anyways its not a virgin story, I don't even remember the first one( when your with a chick for a few years it all seems to be the same), but this chick was the hottest, but most used chick I've ever fucked.

I had been friends with this chick for quite a long time, since like 8th grade since the discovery of my fathers huge amount of marijuana made me popular. but anyhow I knew she was a total slut, but despite her low self esteem she was fucking smokin'. So one night we went to the movies with a bunch of friends and I sat next to her. Before I knew it we were holding hands, who would have thought, I was good friends with her for a long time, and here we are holding hands. At 19 I knew I was getting laid, like I said before not for the first time, but I knew this chick pretty well, and I was getting it that night.

So I start remembering all the days in High School Skipping and Snorting pills, Smoking the killer, and For a split second I thought about screwing up the friendship, but you know as well as I do, when facing a hottie friendship becomes a small matter.

So anyways I KNOW I'm getting laid, which is cool cause I was homeless at the time (I fuck her, I sleep in her bed), but she makes it clear when we leave the theater that she want friends with benny's, nothing more. This is great, cause I could keep sleeping with this fat ass bitch (great in bed though) and catch her bed a few nights a week and sleep with this new hottie a few nights a week, leaving me only a few nights in the car.

Sorry, getting off track, so any who, we drive back to this bitches place, but her roommate was up. Trying desperately to not seem like the dirty slut she was she sits me on the couch and puts her feet on my lap and tries to play it off like she was going to make a blanket bed for me on her floor, she wasn't fooling anyone. (to say the least) Thankfully she sat so I could play with her twat relatively easy as to not be seen....

Finally we went off to bed, good goddamn I fuck her like it was the only pussy I would ever get, and she was so agreeable, I say doggie, doggie it is, I say ride my cock, she's a cock cowgirl, damn although you could def. tell she was used and abused I wouldn't trade it back for shit. That bitch could fuck! The sorry part about it was I never got her off, that's important for me, I got a pretty big dick and all, about 7-8 inches, but it's more the width than the length, but she just wouldn't get off, a little too much experience for her own good.

Now I don't know if you'll post this or not Stile, but I'm sure if you do there's some mother fuckers out there that are laughing, saying this Chump couldn't get the town bike off, all bragin about his big dick and shit, but to all you out there, all I tell is nothin' but the truth. I've got nothing to hide. :) Anyways, although a slut, I wouldn't trade those couple of weeks fuckin' that bitch for much, 110 pounds, 36c tits, and she did her damnedest to make it fun, moaning my name and the whole nine yards. I didn't make her cum, she was the first that I couldn't, but like the classic blond joke says (she was a dyed blond from a light brown shade)....HOW DO YOU KNOW WHEN A BLOND CUMS? WHO CARES?

P.S. Stile, I've been visiting your site for years long before you went big, and I think I am mentally damaged because of it... I mean I've seen shit on your site that people never ever ever should see, the vid way back of that dude getting his throat getting cut out with that dudes foot on his head, damn, I still get nightmares from that shit....

Your Fan, (you sick fuck)
Arius

• From: Hans
• Subject: first time sex

Okay, I've been reading all the other first time experiences, and felt compelled to share my own, you might get a kick out out it, looking back I know I did. During senior year of high school I wasn't dating much, in fact, I had only gone out with 3 other girls (all very short term things) in my life. I had a serious crush on this gorgeous girl that had the coolest personality in the world, I wanted to ask her out sooo badly, but of course, figured she'd never say yes.

She was far too hot to go out with a guy that was still a freaking virgin for god's sake. Somehow, I just always had this paranoia that women could automatically tell whether a guy was a cherry or not. Okay, well it must have been obvious I was madly in love with this girl, but the most I'd ever do was say "Hi" and smile, I was living in hell, and too much of a pansy to do anything about it.

Xmas break was coming up fast, and I thought I could muster the balls to ask her out, which of course, I didn't. Instead, I put a little Xmas card thru the vents in her locker, and then spent the next two weeks completely freaked out over it wondering if she got the card, what she would think, would she tell her
friends, would she laugh at me.The first day back from school I was a mess, I took the long way to each
class, hoping not to see her, just before lunch she spotted me, I can't imagine how I must have looked, she asked me if I gave her the card, and I managed a strangled "yeah.." and she smiled, and told me it was nice, it was the only card she was given from school.

After that, it became so much easier to talk to her, it took me another week, but I asked her out, and we
had several dates, I was over the dilemna of asking her out, but now, how would I ever be able to make a move on her? It was like some sick joke, I started freaking because I figured if I didn't ask her out, nobody would know, but NOW, if I didn't make a move, she'd think I was gay and that would probably end up common knowledge, and I'd never have sex for the rest of my life.

During our 4th date, I decided I was going to make my intentions clear, she was going to either say yes or no, but there would be no question about me being gay. I jerked off three times before going out with her, hoping that it would prolong what I knew would only have been mere seconds of teenaged, awkward sex, I had 3 condoms in my pocket, I intended to use them all. But I think many guys will agree, plotting your first sexual conquest will guarantee it wont happen.

After some kissing, and brief fondling, she stopped me, and I saw my plans falling apart, I started to
panic and she said "not like this, saturday my mom and dad will be gone all afternoon, come over then." I had the most difficult time in the world for the rest of that evening, and then the following 2 days. I'd been given notice "you will have sex on saturday." Having that knowledge does strange things to you, for the next two days I did nothing I didn't HAVE to do, I went to school, and not much else, I was convinced I'd be hit by a car and hospitalized, or cut my finger off with a steak knife at the dinner table,
or choke to death on my cereal in the morning, the two longest days of my life.

Saturday arrived, I woke at 8:00am and started jerking off, I needed to be able to last more than a few seconds, by 11:00am I had developed several friction burns around the edges of my dick head, I figured I'd better stop before I broke something, or made it so bad she'd think I had some strange disease. 1:00pm I was at her house, and more scared than I had been in my entire life, we were both (thankfully) nervous, but we started watching some TV and she got close, soon we were kissing and rubbing against each other, I could feel my dick pounding against my jeans, and worried that all the jerking off had been in vain, it felt like I was ready to bust a nut on the spot, she said she had to use the bathroom, and that I should wait for her in her bedroom.

I was sitting on her bed and she came in wearing a long t-shirt, she knelt in front of me and started kissing me and trying to undo my jeans, I stood up and helped her get them off, and we crawled into bed, sun streaming throw the window, she took off her shirt and I could see her beautiful body, to this day, the most beautiful ass I have ever seen, long, slender legs, and perfect tits.

Well.. perfect except for the extra nipple.. Maybe that's too harsh, I don't know if it was a *nipple* but there was *something* extra on her left tit, below the normal nipple, there was a smaller, dark thing that I think was a nipple, about half the size of the normal one, I have to give myself credit, I didn't stand there staring at it blankly, I just smiled and told her how beautiful she was, there wasn't much more foreplay, and I moved into position, and hoped she'd help out, thankfully she grabbed my dick and guided it in, and I started moving slowly, she started making noises and that was really putting the whammy on
me, and I knew I wasn't going to last, but then I started thinking about that extra fucking nipple, and realized I could keep going, it was truly an epiphany!

I was fucking like an old pro, and anytime I got close, I'd start thinking of that martian nipple, and I'd be good for a couple more minutes, I'm pretty sure she came several times, I decided it would be fine to cum at this point and remember getting off so hard everything went white for a second or two. After that first time, I felt so much lighter, so much less freaked about everything, we used the other two condoms that afternoon and dated for the rest of the year, and into summer, when she went to college. I knew it wouldn't last after that, and have no regrets. I never talked to her about the nipple, and to this day, I don't know if thats what it really was, but I'm sure it did far more good than bad, at least for me.

• From: Jewls
• Subject: Reader_Mail ( First time lesbian experence)

Hey stile, I've been reading your first time sex stories and I decided to write and tell you about my first time with a girl since its much more interesting.

I was nineteen and it was on my birthday. We were totally smashed and Sitting listening to music in her room. I asked if she had something I could sleep in as I was going to stay the night so she handed me a T shirt to throw on. I peeled off my shirt and bra and was standing there bare breasted when I noticed her staring at me. She walked over to me and told me I had beautiful breasts we started kissing like wild women and ended up on her bed. I was so scared until I felt her lips softly sucking my nipples...it was one of the most erotic things I've ever felt up until then. Anyway's we explored each others bodies for a while but nothing really happened below the waist sadly.

Anyway's to all the woman out there I highly suggest having a passionate affair with a woman, Get over your homophobia and enjoy yourself.

Sex Dwarf.
xxx

• From: Conpedro
• Subject: first sexual encounter

Stile,

I was 20 the first time I had sex, and it was with the young girl from where I worked at the local Subway
sandwich shop. She was in charge of mayo refill while I donned the most important manager paper hat. She was quite the most attractive womens in the Subway, and we shall call her Not Helen O'Brien. Anyway, it was the late night one night when me and Not Helen O'Brien are closing the Subway shop, when she starts to do the flirting with me. Surprise, yes no? I knew she liked me, how could she not? But still, it was quite the surprise!

Anyhow, after some more of flirting, we do the kissing and I touch one of Not Helen O'Brien's hoots, and soon we are making the love on the back counter (that part behind the glass sneeze-guard). So then in three minutes we were finished with the nasty deed and we cleaned up and I went home and Not Helen O'Brien stayed to clean the rest up. Anyway, the bad part is when I come in the next day, I hear we were robbed and someone tooked all the money, and I suddenly knew it had to be the Not Helen O'Brien porque she did not come into work that morning and she stayed quite later after me!

And the worst is, to find out who stole the money, the district manager (my boss) reviews the video tape
cameras of the night before (I didn't even know they had cameras there!) and to his surprise, you can guess what he saw. And yes, that bitch did steal the money. She is the gringo whore. And I got quickly fired. Thank you.

Conpedro Vytenis