i'msobadatsex

My girlfriend and I were on a camp out with about 20 of our friends.  After she and I retired to the back of my car for the night, she asked me if I want to have sex.  This was our first time ever doing it, so I put on two condoms in order to numb the sensation and help myself last longer.  After I finished, I realized they had both come off and were inside of her.  She made me "retrieve" them.  I threw them out the door and went to sleep.  We were awoken by 20 people banging on my car, cheering.  The condoms hadn't made it all the way out the door and were hanging from the car, full.  I'm so bad at sex.

I spent all of high school absolutely in love with this cute, quiet girl who was spectacular. We were in different crowds, I played sports, she wrote for the school newspaper and was part of the Christian Book Club. Anyway, I spent all of grade nine slowly showing her how much I cared, and eventually in grade ten she agreed to start dating me. Everything in our relationship was dreadfully thought out and painstakingly slow, our first kiss wasn't until grade eleven and the thought of having sex with her was just absurd. In grade twelve I made this fabulous gift for her as sort of a graduation gift, and the idea of having sex was brought up. (NOTE: she was willing to have sex despite the fact her Lord and Saviour Jesus Christ would look down on her) So after talking about it for a while one night when my parents were out she came over with the expectation that sex would occur. We're about to have sex and she asks if she can put on a song, I say "why not?" She goes on my computer and plays "White Houses" by Vanessa Carlton and sets  it to repeat. I'm slightly freaked out, but whatever, as soon as I put it in her she begins to whisper the lyrics, her tone was so terrifying that I almost lost my boner, then as soon as "my first time, hard to explain, rush of blood and a little bit of pain," was sung she burst into tears. I pulled out, asking if she was ok, she said "you're my first mistake." We never spoke again. I'm so bad at sex.

I was 16 years old, and i was with this guy who has had a crush on me for quite a long time.  We went to my house after seeing a movie and we started fooling around.  He decides that it would be a good idea to have sex, so without any lube, he proceeds to put it in my bum...it hurt like a bitch and i finally had to tell him to stop even before he got it all the way in. He stopped willingly and we decided to just do other stuff, so he starts jerking me off (it usually takes me a VERY long time to climax) so he just keeps going and going and going. After about a half an hour or fourty five minutes he decides it would be more pleasurable for me to start going REALLY fast. I tell him that he doesn't have to do it so fast so he slows down and eventually gets tired and stops. He insisted on me finishing so he asked me to do it myself.  I was realizing that it was really painful to jerk off and I started to get worried.  We both passed out afterwards and when I woke up in the morning I had to take a shit so i went to the bathroom to quickly realize that there was HUGE friction burns all over my penis. I was really upset and so I just took a shit anyways, to realize further that there was a really big gash inside my ass.  I couldnt shit or jerk off for three weeks without being in immense pain and seeing blood coming from one end of me.  He's so bad at sex.

I was a sophomore in college, and before classes started my friends and I made a trip to a neighboring university to go party over there.  Much partying was done that night, probably a little TOO much partying.  At the apartment we were hanging out at, there was a big beautiful woman, probably 220-225 lbs., who constantly cheered me on as I drank and drank ("Who's drinks are these?" "YOURS! DRINK!"), jumped off of two story balconies, and other blatant acts of someone being near the point of blacking out.  I was getting tired when I collapsed on a bed, lo and behold it happened to be Miss BBW's bed.  My wingmen were nowhere in sight.  I am pretty sure she was not drunk.  Not really aware of what I was doing, we proceeded to make out, and then I went down on her.  She had a MASSIVE bush, kind of like her own Mini-Me, but all made up of sweaty, stinky pubes.  I was drunkingly all over the place in her vagina, and when I proceeded to whip my penis out when she said she didn't want to have sex.  I whimpered and said, "But I'm a virgin" (true at the time).  She then told me I should wait for someone special and began cuddling with me.  I was too pathetic, even for Miss BBW, to have sex with.  After a while of spooning (she was the big spoon) I went to puke in the toilet and I passed out.  Three hours later my wingmen woke me up and we left to go back to our school.  In the car, as I was still drunk, my uvula swollen as fuck, I wheezed out a breath to the driver and said, "You smell that? Smells like pussy!"Wow, taken advantage of while drunk and turned down for sex from a stinky pube girl.  I am so bad at sex.

My parents had gone for the week out of the country. I saw this as a good opportunity to invite my girlfriend at the time to come over. We both wanted to lose our virginity to each other, so I went out, bought condoms, and everything was ready. When she came over, we went to my bedroom a bit later and started making out. I was so nervous and could barely get a hardon. Since her giving me a handjob wasn't doing the trick, I started awkwardly jerking myself off for a couple minutes. I finally got the condom on, and tried putting it inside her. I couldn't even hold it in; the friction of the tip touching her made me cum right there, before I even got to put my dick inside her. We never ended up having sex, and eventually broke up. Worst premature ejaculation, ever. I'm so bad at sex.

I was in grade seven (I was a pretty big vixen back then), anyway me and my boyfriend had discussed the idea of doing the nasty after school one day. I told him to meet me at my place around five o'clock, the dude was excited as hell to lose his virginity, and I was just sort of excited to lose mine to him. I  really thought he was in incredible guy. Anyway, five o'clock rolls a round and he doesn't show up, I wait, and wait... he never shows. Later that night I call him at his house and ask why he didn't show up, his response will cripple my ego until the day I die, he said, "Sorry, Dave (his friend) just got a first edition Zapdos card and I had to go see it." A Pokemon card, access to my vagina was less valuable to him than a Pokemon card. I'm so bad at sex.

It was my first... and last time doing anal. I had this idea that anal was going to be the bee's knees, but did very little research on the subject. After a long night of drinking, I coax a young lass into a late night cuddle sesh and it turns out she's into the art of the brown-eye. So, I try slipping it in and realize that its super dry - the pressure very quickly hurts my penis. I let out a small whimper, but it was too late - her ass had already taken hold. It must have been a combination of the booze, the lack of lube and the sheer embarrassment, because I started to cry. A few minutes go by of me pretending that I wasn't crying then she says, 'This is fucked' and left. I'm so bad at sex.

When I was in grade nine, I was absolutely in love with this girl in grade eleven. This girl consistently made me giddy with excitement. Anyway, I went to my first real high school party around Christmas and she was there, and I was there, and Jack Daniels was there. We both got very drunk. I had never had sex before, but my older sister told me that performing oral sex is something I should always do, so, I started with that. I had no idea what I was doing, I was nervous as hell and ridiculously drunk, when lifting my head up for air, I threw up a little in my mouth... not wanting to ruin the moment I continued to perform this hackjob of a blowjob. By some miracle, she came (or at least pretended to), when we turned on the lights however, it was evident that I did not keep my vomit entirely in my mouth. We never spoke again, that night is still in my mental spank bank. I'm so bad at sex.

When I was seventeen, my girlfriend and I decided to have sex for the first time (we were both virgins). We talked about it pretty openly one day while we were hanging out, and decided to do the deed the following night, when I had the house to myself. The next day, I was so nervous/excited that I had a pretty much nonstop erection. Figuring it would help to relieve the pressure I was feeling, I decided to masturbate. I ended up jerking off six times that day before my girlfriend came over, so when we finally ended up having sex, my penis was completely raw and my balls were empty. It hurt so much that I awkwardly faked an orgasm almost immediately after starting, then ran to the bathroom, turned the shower on full-blast, and sat on the edge of the tub weeping at my own stupidity for about fifteen minutes. I'm so bad at sex.

I was fourteen years old and about to touch my very first penis, and definitely didn't realize what REALLY happened when he was about to orgasm. He was lying down, and definitely finished - all over his stomach, face, in his eyes, and in his own mouth. I was left perfectly clean. Poor guy. I'm so bad at sex.