Worst Sex Experience????

I had a crush on this chick I went to school with from 6th grade through HS gradation, but always thought I was in the "friend zone." She was my class' valedictorian so she's super smart, is a really cool chick in general, and has amazing tits. Do want.
We kept in touch after high school, and would hang out over holiday breaks and stuff. We went out for a beer our Junior year, and I finally told her how I had a crush on her back in High School So then she said she did too, but thought I had put her in the friend zone. So i'm like well WTF? We both liked each other. So we spent a couple hours in the parking lot talking, making out etc. She had just had shoulder surgery from a rock climbing accident so we didn't bang cuz my car was super small and she woulda hurt her shoulder. We were both heading back to our different schools the next day but made plans to visit soon. Very soon.
A week later I drive up to UVM to see her. We go out to dinner, then hit the bars on Church street, hard. We get good and shit faced, then walk what seemed like 100 miles back to her apartment, and sneak in around 2am, trying not to wake her roommates up. Then BAM! Clothes off wild crazy sexy time. Very nice.
Call it a claim, but either I'm really great at oral or the chicks I've been down on are super easy to please. Regardless I've got her moaning and gripping the headboard til she shudders and curls her toes. Then she grabs me by my hair, pulls me up to her, and we go at it with 5 or 6 years of suppressed sexual desire.
A few minutes into it the condom breaks. No worries, I brought a spare. I change the flat in record time, and we're back at it for.... f.o.r.e.v.e.r. Because I was drunk I'm not sure exactly how much time went by but it was way too long. Whoever says that tantric sex shit where they do it for hours/days is amazing has to be on drugs because I'd been railing this girl for longer than it took me to take the SATs, and I'm getting bored. I'm winded, tired from propping myself up in weird positions, and I can tell she's wondering when the hell I'm going to cum. Evidently all that jack daniels has numbed my dink. What started out as an awesome crazy sex adventure turned into a chore, and felt more like exercise than sex.
I just couldn't cum... I didn't want to look bad, or at least any worse than I already did at this point so I did what I'm sure many a woman, but nary a man, has done before; i faked it.
And here's the clincher, as she's face down, ass up and i'm puttin on my pretend "O" face, she does some sort of ninja spin around, grabs my cock, tears off the condom and tries to spray me all over her tits. Only there was nothing to spray cuz I was faking it... she quickly caught on, gave some sort of disgusted sigh, then rolled over in the fetal position and starts to cry.
I'm left there on the bed, on my knees with a raging boner, feeling like a complete failure. I tried for a bit to get her to stop crying but I guess I was just making it worse, so I got dressed, and went down to her living room and crashed on the couch. Woke up mad early and drove home. And that, was my worst sexual experience.

 
hahahahah

"because I'd been railing this girl for longer than it took me to take the SATs"

that story was mad funny.

whatever happened to you two
 
With that post you sound like a total Frat bro... bro. So, shut up and leave and enjoy your multiple cases of seeping gonorrhea and the clap.
 
holy shit, thats insane.
The one sexual experience I ever had with a female was much like that. We made out all day, just chilling, talking, having fun. She gave me about 6 handjobs that day, no joke. Then we went down by the river, and rolled in the water and shit, and lone behold, I got *sorta* hard again. She took this as a personal invitation to give me head. I thought to myself "Excellent, Ive never gotten head from a girl!" So she got down on me... and sucked my dick for literally about 45 minutes. I had hickeys on my cock. Finally, she realized that she had spent all my juice on those six handjobs, and that I wasnt cumming any time soon. She rolled over and moaned "Uggggggggghhhh Im inadequate"
Because she was at my house and shit, I pretty much had to stay with her and watch her have this fit. What a terrible time
 
I saw this cool girl for about three weeks. She was an easy going girl who liked to party and drink, a lot, and she was also a couple years older than me and had an awesome flat in a great location. Of course, I assumed that she would be amazing in bed looking by the way she danced and moved and probably had some experience as well.

When I finally made my move (I was seeing two other girls as well, so I was in no rush) I started to get her undressed and she just went stiff and pale as a ghost. Carried her into bed and then I see she has a freakishly untrimmed bush. Then she goes: "...be gentle. I'm a virgin." I know it was a bit rude, but I actually semi-shouted/laughed: "Are you fucking serious?" Seriously unexpected.

Needless to say, it was the worst and most uneventful sex I've had and the blood just kept on coming. I gave her another chance but I could feel she saw me now as "The First One" and started being very clingy even during this one night and morning and I really don't want anything serious now. I haven't spoken to her or seen her since, and it kinda bothers me that she's on my Facebook. I'm gonna tell her why, but still haven't gotten to it.

On a semi-related note (blood) I had a one night stand and before getting down to it, she told me that she has this condition (can't remember medical term) that causes her to be very dry, and that it wouldn't be because of me. I just shrugged it off and boy, was it crazy. Really. No lubrication and I didn't feel like spitting or anything. She said it was hurting a lot but told me to keep going. After I was done, there were huge amounts of bloods from friction all over the sheets, our legs, everywhere. Almost like a horrow movie. I hope they find a cure or good help (other than lube) for that condition, it's feels sad that someone can't enjoy sex fully because of it.

Other than those two cases, nothing bad I guess.
 
dated this chick from 8th-10th grade
never had sex, god knows I wanted it.... oh well
11th grade didn't talk much12th grade had a class, became friends again summer after graduation chilled a bunch, fooled around a bit, still no sex
so beginning of freshman yr at college she surprises my at my appt for my birthdaymy roommate left, the place to myself for the night.... woo. She come downstairs wearin one of my tall tees, and that's it. she says, "lets watch TV" anyways, it was winter and stormy and about 15 min into some show the power went out
showtime. Turns out, the girl I'd wanted to have sex with for 4 years, my first love... etc has a bigger bush than me, assumes sex is just her laying there, and also has dick sucking phobia. BIG disappointment
 
not bad just weird. so pretty much, freshman year of high school. its probably like 2 months in, and im a new kid. im on the bus home oneday and this junior girl starts talking to me. not great looking, but im like sweet, this girls a junior. so pretty much, she calls me that night and i go to a junior party with her. hy peer tutor (all the new kids get them) is there and hes shitfaced. so me and this girl go into a bedroom and start hooking up. one thing leads to anther, and i conince her to fuck. i was a virgin, so i sucked. i was so nervous i couldnt get my dick in her for ike a reallyyy long minute.i finally get it in and start doing it and my peer tutor walks in, and sits down right next to me, and seems to think its his job, as a peer tutor, to walk me through my first time. for some reason the girl is cool with it, but im bugging out. im losing my virginity to some girl i didnt know and some guy i diddnt really know was walking me through it! he pretty much half narrated it half gave me tips, and then thrrew in some "goods" or "nice technique." i got a double awkward monday.
 
Ehh we talk once in awhile. Mostly me occasionally commenting on stuff on her facebook. We've only see eachother face to face once since that happened, and it was a bit awkward but not too bad. Mostly I feel bad cuz I think she wanted us to like start dating, and instead I kind of just showed up, banged her and didnt talk to her much after. Oh wells
 
k so me n my girl meet up at like 12 at night and go to the middle school 2 blocks from my house, we sit down at the steps hookin up then wip out my dick, then starts givin me a handjob. i bust, then she asks me if i am done and i said "no keep doing it".
 
This isn't too bad but one time I was at camp and I was going to meet up with a girl at like 3:30. I woke up, roamed around the cabin looking for the time and then I finally find an ipod. I look at the time a it says 6:15. I was pretty pissed
 
lets keep these coming!! havent had sex honestly not goin to lie so cant post a story..but some of these are soooo whack mostly the bush ones and periods eeeehhhhh..
 
awwkwarrd. reminds me of that joke where the kid goes to the pharmacist to buy condoms, because he was going to his gfs house to meet there parents. Guess who's the dadddy?

I couldn't imagine shit like that
 
Ok this just happened to me and even though its not my worst experience im still pissed. My girlfriend and i have been together about a month and a half and lets just say shes not quite as experienced as me. So tonight was our first time and i wanted it to be a positive experience but instead it just ended up taking to long to get going because it was hurting her and then by the time we were actually going she just ruined it by talking and making everything awkward. And during the thing i had to turn off the tv because apparently carlos mencia is more interesting than i am. But to top it all off she decided it hurt too much and made me stop halfway through. I think next time i just going to say fuck it and get a blowjob. End Story.
 
Not bad, just really fucked up:

So I was texting one of my fuck buddies and he asked if I wanted to have a threesome with him and I'm like, sure why not? I go over to his house and we start drinking and I ask who the third is. He tells me its his MALE COUSIN. WTF but im already over and its too late to back out.

So the cousin comes over, things pick up, blah, blah, blah and they go to put condoms on, but my fuck buddy was too smashed to get the rubber on. I end up fucking his cousin while he sits beside us and jerks off.

/end story
 
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