True Stories: My High School Sex Stories

by Small Penis


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By penisjester

 

1.) Childhood Sweetheart

I think I was 13 when I lost my virginity. I lost it to a girl who I was seriously in love with, I think we both were. We met in grade school and were just really good friends. First time we had sex it was awkward. I remember I had this condom that was way to big, because at the time I had no idea about condom sizes and all that. My penis was also really small, it must have been below 4 inches and really skinny, not the 4.5 girth I have now. It did occur to me my penis was small though because I had seen porn kind of regularly starting around 11 in magazines, the internet, and one of my older buddies had a VHS collection, but there was so much going on in my life I never really thought about it, but I did have a slight fixation and puzzlement as to why it didn’t look like the guys in pornos. I was intact, and everyone in the magazines and movies was cut and huge.

I didn’t really know what the hell was going on and either did she. Neither of us orgasmed, at least I don’t think she did, and I know I didn’t. Plus we were so young, too. My penis did penetrate her though, but I know now that it didn’t break her hymen or anything. But a lot of girls don’t even have them, broke it in themselves, or don’t bleed when it tears. Her vagina was extremely tight, and I remember not even being able to fit my index finger without a little force. We did laugh and we were both horny, and close, really physically close. We were rubbing on each other; hot and sweaty, and really connected and kissing, but we were also afraid and embarrassed. I was insecure about my penis, but I didn’t deal with that hard hitting truth until later on.

I hated this girls parents because they had a lot more money than mine did, I grew up pretty poor. One time they went through her computer and found these emails I sent to her saying how much I hated them, and other emails asking her for a blow job and talking about how I fingered her, and how we had sex. They said she could never see me again and sent her to a private school, and I went city public so I never really saw her again after that. It was really hard on the both of us. I was sad as fuck. I still miss her, and I saw her at parties sometimes and that connection was still there. I still think about her to this day sometimes. She never said anything about my penis, and I never felt anything about it from her.

*****

Locker Room Experiences

I went onto high school and I started to get insecure about my penis a little more when I was a freshman. People were starting to talk about sex a lot more, but I was also one of the few guys I knew to actually have had sex before high school. And I could tell everyone was full of shit most of the time. Anyway, I felt like my penis should’ve been growing more than it was. I played hoops, and football too so I started to realize that it was a little on the smaller side. But I did see other dudes with a small flaccid like mine, but I also started to see other guys who were a lot bigger than me. In the locker rooms we teased back and fourth but it was never a thing as long as you owned it. I was good at sports and I was respected and popular even though everyone on my teams must have known I had a tiny flaccid penis, so It never came out of the locker room. There was like a code all of us followed and I liked that.

It was never really a thing. One time my boy heard about me and Sarah and we were all in the showers and he said something like “I don’t know what he’s gonna do with that little thing,” and everyone was like ooooooooh shit, and I was like, wait until you see it hard as a fucking rock, and look who’s talking you virgin ass ugly mother fucker or something like that, and then I remember everyone just laughing. If I would have let that get me everyone else would have saw it and it would’ve been different I think. Shit happens differently when you own things. But I was a force on the team and me and him were stars so to speak so it was like a showdown. Sometimes we joked and I would just say something about them if they said something about my dick. We laughed about things and we were all pretty cool. I never really yearned for a bigger penis or anything yet.

*****

2.) The Crazy Gypsy Girl

My second girlfriend was named Lindsay, and she was huge bitch to everyone but me. She was really hot, and looked like an evil sorceress gypsy, and had this mentally challenged sister, and a family that was in the middle of falling apart. She latched on too me hard, and I didn’t feel the same way about her. We had sex for the first time at my friends house after a little get together. This was the first time I actually had ‘real sex’ so to speak, or at least something like you would imagine it to be like. I was probably about same size then as I am now. I had regular Trojan condom; it was loose but it did the trick because when your with a woman for real, I feel like you get so much harder than when your alone, especially wider. It’s like there is this magnet that pulls all the blood to your dick, so I was like wow I’m I actually got some dick to fuck with right here. So it got hot and heavy, and I didn’t like kissing her for some reason, so I moved to her breasts, which were smaller, firm and perky, and then too her neck. I was just trying to avoid her mouth.

We were both only 15 I think. We were freshman in high school. So I tried to stick it in and I felt like i wasn’t getting the proper penetration with me on top in that position. I was hard as all hell though, and she moved on top real quick and sat on it and I nearly died. It went in and I could feel it penetrate her, but at the same time I wanted to get rid of the stupid fucking condom immediately. I hated it. She was moving on it while I looked at her body, and by then I really forgot about not wanting to kiss her anymore and we were in each others faces and fucking like rabbits, or at least she was fucking me, rubbing up and down on me. Not two minutes went by, before I started to come. She didn’t stop, and just looked at me and I came in the condom while it was inside her. I was worried about the condom leaking because it got all wrinkled inside her but it all stayed in there, but it was all over the place.

It didn’t stay in the top like it was supposed to or whatever, but condoms never work exactly right when your fucking another person. After that she laid down next to me and said we better get the fuck out of here, and I look down at my pelvis and its soaking wet, and so is this like half bed couch thing in my buddies basement. We got up and left, with the whole thing stained with sex, and went pretty steady after that for like 6 months, and all the good stuff in between. She never said anything about my penis’s size. One time I remember she went aww, its so small shriveled or something one day when I could’t get it up, but I didn’t take that the wrong way. She was obsessed with me, and it was an observation.

*****

3.) Kim

Third girl I started seeing was named Kim and she was a cheerleader, but I didn’t even know that. I played basketball and football and didn’t even know because I never really paid attention. Anyway, she was known as like one of the hottest girls in the school and I thought so myself. She had a really big head though, but it was offset by this super hot body, with insane amazing hips and booty. I was on it hard. Problem was I was in the middle of breaking it off with Lindsay who was a sorceress with evil powers and had her ways of making my life hell. She never said anything about my penis during the break up, but I was expecting her to because she could be mean as fucking hell. She would continue to be around even after I graduated and went on to college. She would just linger and become friend with whoever I was hanging with at the time.

Anyway, me and Katie were cool together. All she did was laugh and say funny shit, do funny shit, and she was really athletic too. Of all the guys she could’ve been with she was with me, but part of that was because I pursued her and grabbed her up because I wanted her. She was seeing this guy Jeremy but I guess it wasn’t serious or something. First time we were sexual was at my best friend D’s house. He was already getting it on with this girl Kelly, and me and Katie we’re like what the fuck. We left the room and went into his basement and I remember there was this huge aquarium with no fish and we were looking for some fish and I started laughing because there were no fish in it, and it was this huge 300 gallon tank. And then we both started cracking up and I started kissing her. As soon as I did that this chick nearly destroyed my face, and I was like damn, slow down.

I remember this really well because the next thing I did was pull her shirt off over her head and she was the cutest thing I ever fucking saw. I went nuts on her, I could hardly contain myself. She had this like sports bra on that was beyond my sophistication, and ability to remove and I couldn’t get it off of her, and I remember it being so tight. So i tried to pull it over her head. When I pulled the bra up and over her chest these two big breasts popped out that I hadn’t even realized were there. My dick was about to explode because I was astonished, and I had never seen anything like that. The bra got stuck in her hair. She untangled it and and we laid down and I went to town on her tits. I was a young freshman high schooler with two awesome jugs in my face. Everything on this girl was as hot as you could imagine. I went to pull her pants off, which were these tight ass jeans and I remember wondering how she even got them on. She had these blue, white and black striped panties or something like that.

I froze because I didn’t know what to do for some reason. I didn’t know if I should take her panties off in my friends basement where someone could come down, as well as me just no knowing where was it was going. I drop my pants and my dick is hard as all fucking hell and she grabs it and starts rubbing me off, and then stops and goes “wait, what’s going on down there or something like that. And I’m like what the fuck, oh my foreskin.” I was like oh, you’ve never seen a real penis before. She wasn’t grossed out or anything, but she was a little puzzled I think. I said watch this, and I pulled my skin back and fourth like I was masturbating and then without even saying anything she grabbed my dick and started messing around with it. We sat down on this couch and she sat next to me playing with my penis and doing whatever with it, but her touch was light. I told her to grip it with her hand and go back and fourth, and showed her how.

The next thing I know I realize the whole situation and see her tits and her face and her body and I come all over her hand, and into the air, and all over the place. She messed around before so I guess she had experience and expected that too happen, but she was a little taken back and grossed out about it, and screamed something and I think some semen got on her face or something I dunno. She ran to the bathroom. She never said anything about my penis and seemed thrilled to be playing with it.

The first time we had real sex was at my house. I stole condoms from this grocery store I was working at and I was ready to put those shitty, stinky latex bombs to use. They were called Trojan thins or something which I thought meant they would be smaller than usual or something. They were a better fit, but they were a really thin material, like skin. Anyway, after we were hanging with some friends for a while This girl Kelly, who lived right next to me would let Katie pretend she was spending the night at her house when she was really spending the night at mine. My parents didn’t really care; I guess they were laid back that way.

So later that night we fucked, and this was some of the best sex in my life for different reasons. We both were just together, young, attracted to each other and it felt good. She never said anything about my penis ever, and the way she acted about it made me feel good. That night we did things we never did before. For one, she told me she was a virgin, and two, she was just cool as hell and I miss her, but anyway. After kissing and touching each other, I picked her legs up onto my shoulders and pushed my dick in her as far as I could get it to go with me on top of her putting my weight right on her vagina and pelvis. This hurt her, and she pushed me back with her legs. We took it a lot slower and I did the same thing.

I noticed earlier on with my first and second girlfriend that certain angles were better for penetration than others. When a girl is laying just flat on her back without tilting up her pelvis and vagina I can’t get all the way inside her like I can when I come at a certain angle. Like when I lift her legs up over. Be careful though because this extremely hot and sexy as all hell. It squeezes her vagina between her thighs and it just looks to hot to believe and you’ll come just looking at it if your not careful. Anyway, this was the girl that sex became super real with, and where I began to form an emotional connection with her to the core. We both were serious and I was with her for the rest of my freshman year, all summer, and all of sophomore year. She told me she orgasmed for the first time with me. We both learned about sex with each other.

*****

4.) Ashley

Me and Kim died out because I was going through shit. I didn’t feel anything for a while or something. I hurt her, and I regret it to this day. I was going through shit and I didn’t have the emotional energy anymore to give her anything back. She started spreading rumors about me that I was crazy, but she never said anything about my penis.

Ashley was a cool girl and we fooled around once because I was at this little lame ass party and she asked me if she could give me a massage, and then I gave her one and I remember asking her if her parents were home because she lived right next to the house we were hanging out in. We went to her house and fucked. I didn’t really feel like my dick did anything for her, but she seemed to be enjoying it, but at the same time, a lot of these girls were just going by the motions, like its what they were supposed to do or something. Some people are just like that, I dunno, just whatever. Ashley and her crew weren’t my kind of crowd.

They weren’t athletic, smoked a lot, drank a lot and got high. My boy rolled with them so I rolled with him sometimes. She never said anything about my penis to my face, or made any kind of sign she was disappointed in my penis. But I think she told some of her friends I had a smaller penis or something. Because one day I was hanging with them and started to talk shit about some girl and stupidity and she said something like she prefers big dicks or something, but it never phased in the the slightest. I was a thousand times better than her in every way and so were so many other girls I knew.

*****

5.) Tamara

This Katie was troubled. I was going through shit and I was rolling with some different crowds. She was easy, affectionate and slutty. Her dad was a cop, or a sheriff or something like that. She had an amazing ass, like one of the greatest, but she wasn’t very smart, and she always seemed sad and fleeting or something. Dazed and confused. First time I got naked in front of her she laughed about something but I don’t really know if was about my penis because she always laughed at things that I never really understood what exactly it was she was laughing at. I did like being with her though, but I never fell for her or anything. Sexually she was kind of docile and distant, but she would say things like “that feels good” and stuff and it seemed real enough. She was taller than me, and had fingers as long a fucking ruler. My dick was tiny in her hands.

*****

6.) Tia

This girl was fun as shit and I miss her for numerous reasons. She was loud, and a sometimes people told me she was ugly, but I knew better and she wasn’t. She was sexy as fuck, but crude, and I was afraid she was going to say something about my penis because this was one of those girls that made dick jokes. I remember this one time she was making fun of my dude for wearing his pants all low and she said something like “yeah it’s because all you guys have to keep your tiny ass boners down.” And she made other random comments sometimes about how all of us had little dicks, because were little boys or something.

But I still got with her and she was with me, and she fucked me and acted like she liked it. She was tight as fuck, so a big ass dick would have killed her literally so I always knew she was full of shit. But she was really smart, top of the class, went to U of Chicago. Damn. She had the nicest tits to this day and she loved it when i played with them. She loved her tits. She was pissed when I stopped getting it on with her, but she let off and was cool. I miss her. She never talked about my dick to my face, but I have a hunch she went and found herself a big one.

*****

7.) Brit

Brit was cool. She was laid back and smoked like snoop. She had the best weed of all time and smoking with her made me nervous. This one time I had ball and she wanted to get high as shit and drop me off and I was like no way, but I did it anyway. I went to practice to high that I had fucking panic attack and I felt like forgot how to play ball or some shit. Brit was sexy, I don’t think I ever had sex with someone who I thought wasn’t. Brit straight up told me one day I had a little dick, but it was like in a way that was just the truth or something, like…. it ain’t big or anything so what the fuck.

I just said so the fuck what. But I don’t think it mattered to her as far as just being with me and fucking each other went. She was the one that turned me on to sex and weed and damn I never went back, but shit though, weed slowed me down in the head, and on the field and court. We did some pretty sexy ass things with each other. She was the first girl to swallow me and that was insane. She let me bend her over and smell her ass, come on her face or breasts, but I never liked coming on faces its fucking degrading as shit in real life if you ask me. People who do that are on a power trip or on a submission thing because to really come on a girls face is whack in reality.

Shits fucked. I’m not going to act like sex wouldn’t have been better with a huge dick with her though, because for some reason I could tell she would have been all high and worshipping a huge anaconda, but whatever ain’t my life. We just faded out eventually because I was done with the weed and shit honestly, so no hard feelings or anything.

*****

8.) Phillis

Phillis put me right because she was so serious about sports. She ran track and was good as hell. Talented and smart. She got a scholarship. She wore her in locks and her head to weight 20 pounds easy, and was still the fastest. I don’t know how this happened but we hit it off, I don’t know why. I think it was because rumors had it that I was all deep and cool, but we always knew each other from middle school and would always talk and in the hallways. One time I remember she injured her leg or something and she was on crutches and I always helped her because I had this art class right next to her locker and I would pop out and help with shit, good ol’ days, damn. This girl had thighs on her like a stallion man, and her ass just wasn’t even on the scale, it was ridiculous as hell. She was about as tall me at 5’11 man, and she was just a hardcore person, like on every level. Raised on solid shit all the way through and things with her were for real.

I’ve had enough sex by then to really not care if “my dick was suitable” or whatever, and even then, getting to know someone shouldn’t be based on your penis. Plus, on a shallow level I did think about that and after a while you just get better at handling sexually awkward situations. Phillis wasn’t just going to lay it down either, no fucking way. We hung out all senior year for real, and I was getting ready for college and so was she we were both helping each other out on multiple levels. We were never really super super exclusive or anything but people knew we were “together” so to speak but we both knew it was never going to go past the end of high school because of other things, but I did miss her and liked her a lot.

She was beautiful. We had sex in the summer just before we all went off to college. She was going far as fuck down south to college. That stuff about women who are bigger being loose or whatever is a fucking sham because this girl was tighter than all, and it wasn’t some perfect vagina either like we all see in porn by the way. It was this little thing in between all this thigh and ass. She was muscle. When I saw that I remember thinking maybe size don’t matter all that much after all because like i mentioned before the thing was small. Sex was cool, but she was just so much thigh and booty that I don’t think we would have been a good match.

Like it wasn’t because my penis was too small for her vagina or something, it was just body to body incompatibility. What she needed was a long, skinny, rock hard dick to get in there. We both seemed to have a good enough time, but maybe she did feel like it was bit anti climactic or something I don’t know. It makes me sad sometimes to think about that. But I got over it fast because we were more friends than anything else.

The End.

 

 

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