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Monday, April 29th / 2002
First Time Sex Stories: Part 10 (9:15PPM EST) by: Stile
 

Got a great first time story? Send it in...

part 1 - part 2 - part 3 - part 4 - part 5 - part 6 - part 7 - part 8 - part 9

From: Your pal, Lulu

I've noticed that the majority of the stories sent to you are from guys, well i'm a girl and i'm gonna add a twist to it. Let me tell you about my no EX-bf's first time. This guy was fucking hot, gorgeous, rock hard body and massive cock. i knew from the very beginning that i was gonna get him in the sack, even though i played innocent for a while. Asian girls like me do that often cuz its easy to pretend to be an angel. So after a couple weeks of dating, he brings me to his house. We get up to bat, and before you know it we're rounding 3rd base. WOO HOO. and i tell him to fuck me.

He takes off his little preppy shit and what a great torso! I swear, to this day i'm still in love with that six pack and broad shoulders. Here the comedy starts... He runs up stairs into his dad's drawer and grabs a condom. I get undressed and wait, 2 minutes later he comes back down and he puts the rubber on...its too small. His once beautiful penis looked like the funniest thing. Like linked sausage...AHAHA It took everything in me not to laugh. so ok, i can let that slide. Well then i discovered that he had trouble keeping his boner. He says it was cuz he came already during a blow job 5 min. ago...ok i understand. I smile and we wait for his linky member to get ready and made awkward conversation about random shit. i'm losing the momentum already. he's finally ready, and i start riding him. I was starting to really get into it and until it goes soft again...And i will never forget those words "uuhh...i definately came already" OH OK! so that was the shortest fucking i have ever had. i was just getting started and he's already done.

What a damn shame, i had a gorgeous two-pump chump. That was his first time...apparently it was good for him. But i felt cheated, as if i only got half of a Happy Meal (TM). *Sigh...and then two weeks later he dumps me cuz he's too busy for a relationship due to sports at school. Oh well, i hope sports can entertain him now, cuz he was a waste of my time. Remember boys, its not the size that matters, its what you do with it....and for the girls, a dildo never gets soft.

From: William Hawking [whawkking@yahoo.com]

Stile,

Waddup man? I saw these stories and thought I should throw mine on the pot. Not too weird, but fun nonetheless:)

My junior year of high school I had already dated half of the girls in my school and was tired of all of them. I was looking for something different (not like Cruel Intentions or something, I was still a virgin) and started asking my little brother (sophomore) about some chicks he knew. Turned out he was having regular sex with his current girlfriend, much to my chagrin. I don't know if he knew I was still a virgin (kind of hard to believe since I was so dating-ly active), but it didn't really matter. He hooked me up with his girlfriends older sister, Karen, and we went out until the end of the school year. That summer I got REAL active in my pursuit to get it on, and was doing more with Karen, more often. I didn't think she was a virgin, but she acted like one. She would let me get to her tits and if I touched her pussy, she would end it right there. After a month of handjobs, I was done. I asked her if we would ever move beyond this, using some "we are ready for the next level" speech to try and get her pussy. She was offended, and dumped me.

The next night, my brothers girlfriend, who I must say was a sexy little (talking 5'2" little) thing for a 16 year old, came over to see my brother. He decided to go out with his pals, and left her behind. She was going to leave, but after a month of handjobs, I needed some pussy BAD. I took her to my room in the basement and gave her some drinks. She was quite a lightweight, and she was quickly sloppy-drunk and all over me in no time. I tore through her clothes and she started fingering her. Laura, we'll call her, was moaning in pleasure, but I thought "what the fuck am I doing?" and lowered her head to my dick. She was drunk, and her BJ was sloppy, but I came in her mouth all the same, and she slurped every bit of it up. She got sick soon later and started puking, but I knew I had a prime opporunity in my hands. I told her to puke all she needed to, and while her head was in a trashcan, I fucked her from behind. I blew my load in her pussy this time, and we fell asleep together. My brother never came home that night, and so, after telling Laura how I had "taken care of her when she was drunk", we fucked again.

Two days later, Karen came back and said she was sorry, and that she was being selfish in caring only about her needs and not mine. We fucked that night, and it was ten times better than Laura. I continued to fuck Karen (she was a good, good lay) for the next year and Laura went crazy, thinking that I was using her as a blackmail tool. She was afraid that if she didn't do whatever I wanted, I would tell my brother. To be honest, I was never thinking that, but it led to Laura fucking me on a regular basis as well. She was scared, so I could pretty much do whatever I wanted to her. I never got crazy, but I introduced her to anal and haven't stopped with her since. When Karen "caught us", it turned out she knew, and that she wanted in. It was a bit weird to me, but when two blonde cheerleader-looking sisters want your cock, you have no choice but to give it to them. My brother and I eventually had a threesome with both of them (he, Karen and I, then he, Laura, and I) before ending up fucking in groups often. It was always a bit weird, but I got used to the idea of my brother and I filling both ends of two hot girls.

I eventually broke it off with Karen and went to college. Laura still visits, and all of the guys on the floor get a turn with her. She knows most of them by name now (if they are on my good side), and we fuck 2 times a day, 4-5 days a week. When she comes for breaks, she fucks around the clock. Why she keeps coming back, I don't know, but she is a way better lay than her sister now......

-Will "Hawk King"

From: WebJacker

Hey stile, i thought i'd share my 1st, (and second kinda) sexual experiance, since its 3.30am, and im fucked on skunk.

Well, i'd been into pr0n for many years, (since about 10) and needed something to stick my cock into. Stuffing shit in my ass was another pastime, and a variety of vegetables, and aerosols were choice tools. (Now about 13 years old). This continued for years, my parents would goto work, i'd drag a towel and a banana into my room, and do myself.

Eventually (around 16), i got bored of this, and began to suspect the only thing in my house which wouldnt talk. So one day i enticed the dog upstairs. It's a big german shepard, and about 2 years old. I slipped on a rubber, and got Sally to jump onto my bed, and lie on her back (as i rubbed her belly). Then i licked her belly a little, before dipping my tongue into her crack. I dont advise this. Kinda turned me on tho, so i pulledup my cock, realised it was about 3 times the size of her crack, and tryed to shove it in. She wouldnt sit still, so i let her stand, and got behind her, got my tip in, and pushed, my god it was good. To this day i prefer sex with animals. She didnt resist, just swayed back and forth, as i shoved my cock into her litle canine back end.

My 1st experiance with a human was a year later, when i figured women wouldnt fuck me, so i went to a gay club in the city, after lieing to my parents about some party, and picked up two butch guys in a chillout room. I was kinda small, skinny, and fit (17 remember), so they thought it was great. Went to one of these guys houses (told my parents i was staying at a party i was going to), and these two guys started with turning down the lights, and music and shit.

Then the one (for this we shall call them P and R), R, who is sat on the sofa, ask me to come over to him, so i do, i sit down, and instantly he has his hand down my pants, feeling my butt cheeks. Several drinks later, and both P and R and in the bedroom, with me led naked on R's bed, with them both feeling my body, and teasing me cock. Somehow, i end up sat on R's cock (i kinda got a loose ass remember!), licking P's assring, cos P has his cock in R's mouth. After a while, they both jumped up, left me sat on the bed, and said to suck them both.

Now 2 guys, both like 20 something, is a lot of cock, and i had trouble. In the end P spood his goo on my chest, and R shoved it in my mouth. I was almost sick, but didnt stop. I hadnt come yet. P siad it was safe, and i didnt need a rubber, and he squirted a bucketload of some slippery shit on his hand, and rubber it round my cock, then round his ass, he put some on my right hand, and told me to press it into his ring, i did as told, and found a nice suprise, 2 fingers went straight in. he got on the edge of the bed, and R helped me get into position, before helping slide my cock into P's arsehole. I thought this was great, i was getting some hole, and had two big horny guys helping me. Then R decided it';d be fun to have a 'sandwhich'.(Turns out R really had a thing for me.) In which, he poured my slippy shit over my already dripping hole, and poked back in. Then they both started moving back and forth together, crushing me. After i came, i had to wait for R to fnish, before i could get out, i got out, passed out, and woke up the next morning to R, apperently, P had gone home. R was hard again, and wanted more of me. I darnt say no, so iy went on for another 4 hours.

Im now 19, and still endulge in both when im not with my g/f. Well that it, my 1st experiance at all, and 1st with a human, i might send in my 1st with a girl one day! Your sicker than me man!

Andy 'the whore'.

From: Waitingroom [waitingroom@gmx.net]

Hi Stile.

It was with a middle aged colombian whore, I was 25 (I'm still 25). At first when I got to touch her tits I had a boner, from there it went downwards. I licked her pussy, which tasted extraordinarily good, considering she was a filthy whore. I didn't worry about any kind of herpes she might give me, life can't suck anymore anyway. So after licking her pussy for a while I tried to fuck her but went limp. Well so he jacked me off for a whole 15 minutes before I came on my own fat belly. That was it. I visites her a few more times and it got better. I came in her mouth a few times when we did 69. I never asked her to swallow my man juice, but she did it anyway. Some extra service for a special customer who paid good money, which she wanted to keep on flowing I guess. The first real fuck with grand finale took me a little more time and experimentaion with different types of whores. A Thai did the trick with a real good back massage, I was so relaxed I could really enjoy banging her tiny asian pussy, that was really good.

No girl would touch me if it wasn't for money, I'm too strange and fucked up.

A little more personal details about me. I'm almost bald, pretty fat and my shizo mother abused me sexually when I was a little toddler, she still tries to kiss me tongue when I visit her in the mental ward.

I didn't make this up, I should kill myself.

bye

From: Tomcat~ [raidertc@attbi.com]

Stile,

This is the story of my first time. This was not the joyous and fantastical thing it should have been as you will soon know. I was 15 that summer and I got a call from my ex-girlfriend from the 6th grade. See, we went out for a little over a year. we went out the entire 6th grade year and most of that summer. We hung out at my house most of that summer getting naked in my room and messing around. She never let me fuck her and she never made me cum but we did everything else. Lots of touching and kissing etc. This was great for a 13 going on 14 year old, don't get me wrong, but I wanted to close the deal. We never did. at the end of the summer she moved to the next town over and it made it really hard to see her since all I had was a bike and the bus. She ended up meeting her neighbor who was a sophomore while we were going to be freshmen and she dumped me for this guy. She even called me one day to tell me that she fucked him and it was great. I was fucking crushed and I decided that she was a total bitch and moved on.

So I spent my entire freshman year a virgin. That summer she calls me out of the blue and I was really surprised to hear from her. I hadn't even thought of her in like 6 months. My buddy and I are there getting stoned and she tells me she wants to come over my house and having been hurt by her and being suspicious I was like "why?" she told me she wanted to come over and fuck me because she never had the chance before. She said she broke up with her boyfriend and she was horny and she always regretted not fucking me when she had the chance. I thought about it for a second and thought, well no matter how mad at someone you are that just sounds great. So I told her to come over. She showed up about an hour later and she looked pretty good. She said "hi" to my friend Jim and grabbed my collar and pulled me into my room and shut the door leaving Jim out in the living room to fend for himself. Not my problem.

So anyway I was really nervous not only because I was about to get laid and didn't know what I was doing, but because I was really hung up on this girl and she snapped my heart like a twig. she tells me to get naked and gets down on her knees and starts sucking my cock. I had never had this happen before but it helped relax me a little. She got me hard and took off her clothes and sat on the bed. She told me to lay down on my back. I did as she said and once I was on the bed she straddled me. She told me to bend my knees and put me feet flat on the bed so that I could pump her harder. I did as she told me and fucked the crap out of her. I was a little turned off that she had become this seeming sex expert in the year since we went out and it wasn't me that taught her, but I soon got over that and blew my wad like I never thought possible. she got up and got dressed. Kissed me and said "That's for always being so sweet to me." and left the house just like that. I was in shock. My buddy Jim, who was also a virgin told me I was the luckiest guy in the world.

At the time I thought he was right. that was until about a week or so later when I discovered little critters on my pubes and in my bed and stuff. Then I noticed a slight burning sensation a day or two after that. So having this problem I went to the local free clinic and they told me that slut gave me crabs and Chlamydia!! That fucking bitch ruined my first fuck. I called her when I got home from the clinic and told her that she had those things and she was like "oh, ok, thanks for telling me." No "I'm sorry" or anything. Anyway I went on to fuck the hottest girl in shcool and she ended up with 2 kids by the time I graduated and 4 by the time I was 21. I think I got the better deal.

Tomcat~

From: tom naked [sux@email.com]

First let me say that I'm a big fan of your site and whenever I get the chance I tell friends about your site. Anyway here is my story. (which has a fucked up ending)

My family is very much into religion. I went to a catholic school until I was in the 6th grade...went to church every fucking Sunday...etc..etc... When I was 15 years old I decided that I was going to get a fucking hooker. I wanted to lose my virginity to a fucking hooker. I was kind of the role model for many kids out there. good grades, responsable you know...the big shit. My parents were so proud of me. Anyway I saved up $100 and one Friday evening I went to the local "red line" street. I found this chick who didn't look like a hooker, very nice clean girl and I told her that I was 15 years old and a virgin. she looked like 18 years old so I figured that I could taked her home and just tell my mom that it was a friend from school. Besides, I didn't have an extra $25 for the Hotel. My mom fucking believed it!!. We went to my room and well...I've never had my fucking dick so hard before. She suck and suck until I was ready to cum...she asked me if I wanted to cum now or to fuck her...I said "well.... I'll fuck you" She slapped my dick a couple times and she started to ride me. It felt like heaven. then doggie style and finally she asked me if I wanted to fuck her ass and of course I said..."Fuck yeah" I think I came like 4 times. She really knew how to do her fucking job. After one hour we came down stairs and my dad was home. We were walking to the front door and my dad asked me to come to the living room and to introduce "my friend", when my dad saw her, he jumped out of his chair and scream at me. You little devil...she is not your friend..she is a prostitute!!! my mom freaked out and we just ran out of house. After 2 or 3 hours I came back home knowing that I was fucking doomed...but feeling like a fucking Bull!! the fucked up part is that when I came back home my mom and dad where screaming at eachother. I thought because of me... but...it wasn't... My mom had asked my dad how did he know that the girl was a hooker. Well...the end of the story is that my dad, being a well respected person at church and ever ything....had paid this same hooker to take him to heaven. My parents divorced and I'm still calling the same hooker every now and then for a blow job. As I said...she knows how to do her fucking job.

From: tom D. [stonerfoot@yahoo.com]

my friend and i were sitting around smokin pot all day, and it was some pritty good shit too. it was
gettin pritty late, and we had smoked so much that we were to the point of drooling on ourselves. we were sittin on my bed, in my room, and we started talking about chicks, he suddenly said, "hey, roll over." I didn't know what to think, and told him no. i was way way to stoned to even remember my own name. eventuly we got tierd enough to go to sleep, but sence he was staying at my house, and my parents, and sister where home, he had to sleep in my room. he had a sleeping bag, right next to my bed to. he started to wack off, i didn't think much of it. the next thing i know, he was on my bed, and asking me to roll over and pull my shorts down. i kept sayin no, but i was so stoned that i eventuly gave in. i just rolled over, he got some lotion from off my shelf, and began to fuck me in the ass. at first it sort of hurt, but i began to enjoy it. after about 45 minutes of hard and deep fucking, he blew his load in my ass. there. go ahead and lafph, but iam not gay, i get more pussy than alot of guys i know. that was the one and only time. it was like 5 years ago though.


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