Worst Sexual Experience

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thk8plus4u's post sounds like a typical male.

But, anyway...

I don't have very many stories at all, but I can call one the worst of mine so far:

I was on AdultFriendFinder late one night, chatting in the local chat room. One of the more intelligent regulars and I got to chatting, took it to AIM, exchanged pics (I thought, "Hey, she looks cute enough, and looks like she knows what she's doing in bed.."), and decided to meet up. We met at a diner that was open late, and although she did indeed match her pics, I kinda cringed a bit when I saw her in person. We had a snack & talked, then went back to her place.

We soaked in her hot tub for a while (nekkid, of course), then went to her bedroom to fool around. Really, the whole place was a cluttered mess, looking like it was being rented out by some no-life college dropouts.

The kicker for me was as I was masturbating for her, I opened my eyes, saw her toothy grin, and almost completely lost my erection just because of her face.

I slept there, showered the next morning, and left, never to return. I decided the same thing as NIC, never to hook up with someone that I wasn't attracted to. Thankfully, it only took one mistake for me to learn.. lol
 
man, i've never had anything like all that happen to me.

the worst i've been through is probably masturbating too much and then having trouble getting a really hard erection for sex.

i've never even had a nightmare anal sex situation, although some have not gone that well.
 
Blocko wrote:
"I don't want to read the OP's mind, but you could be a little more sensitive when it comes to other people's *involuntary* sexual experiences."

Guilty on that one.

Somehow didn't focus on "It wasn't voluntary" and thought of
it as just an unpleasant encounter.

My bad.
 
LeeEJ... haha... one of the negative experiences I listed was also from AdultFriendFinder. I used to go there a lot, circa 2001... but I've decided that place is more or less a complete waste of time. At least for straight males.

How was this girl so much less attractive in person than in pictures if they matched up? I'm curious. I've had the same experience before.
 
I gave up on phone personals/sexually themed chatrooms/AFF a long time ago. I never once got what I was led to believe I was getting. I have gone on internet dating sites, but I'm a lot more cautious and now look at it as more of a chance to meet, as opposed to a chance to hookup.

And as for pictures "matching" the person, and the person still being unattractive? Well, sometimes the photos are a shade out of date... or they might be the best photo ever taken of the person in question. I've been there.
 
rob_just_rob said:
And as for pictures "matching" the person, and the person still being unattractive? Well, sometimes the photos are a shade out of date... or they might be the best photo ever taken of the person in question. I've been there.
Click to expand...

Yeah, that was probably it. The picture I remember most had her wearing a leather bustier/corset as part of her outfit. That, of course, emphasized her boobs and slimmed her waist.

And, honestly, her face wasn't much to look at, either. The "toothy grin" I mentioned reminds me now of Andre The Giant, only more feminine.

Just an uncomfortable night all around. Didn't catch anything, though (knock on wood!).
 
there was a guy that lived in my area... i went to his house one day to fool around. he'd done stuff with a guy before, but i never had... he asked me to make out with him but he was so ugly i refused. i went down on him for like 2 minutes but his dick tasted disgusting and had a funny smell. i fucked his face, came in his mouth and left immediately. i've never done anything with a dude since, and never will again. it more than let me know that i'm not that into dudes.
 
I was with a new lover for the first time. He and I were going at it furiously. Next thing I knew, he was balls deep in my ass. The pain was horrific--No lube, No warning and balls deep in one thrust.

I kicked him off me and ran to the toilet to throw up. That was our first and last sexual encounter. I was about 19 at the time. **shudders**.

Hugs and Kisses,

Kamen
 
Worst was with a woman about 5 years older than me (I was 25 at the time), a blind date at a party arranged by a friend. Unfortunately he forgot to tell me she was under 5' in her heels, and generally tiny, and I am over 6'. Nonetheless we got into the mood at the party and back to her place 'for coffee.' Now kissing, tit and pussy-fondling on the sofa is fine no matter what your respective sizes, but once we were stripped and on the bed, with my 7.75 x 5.75 as hard as it comes, it was one hell of a task getting into her pussy. She wasn't interested in any position but missionary - doggy style would have been fine - and just lay back while I eased it in and tried to work up a good stroke, not easy with her face level with my chest and her doing absolutely nothing. I came after about thirty strokes, rather quicker than usual, pumped out my balls into her and withdrew. Her only response was 'thanks.' I left. End of story.
 
A while back, I got busy with a semi-atractive woman. I was all ready for foreplay, but instead, she got undressed and told me I should also get out of my clothes. Nice.

Then, she pulled on my cock a few times. I was barely hard when she got on her hands and knees and told me to fuck her. I did for a while then she flipped over on to her back, then after a few minutes we stopped and she went to the bathroom for lotion to finish me off with a handjob. I touched her nipples once, a soft pinch and was told not to do that. I touched her pussy and was told not to do that. I was fingering her but was told to be gentle because she was sore (lovely) and then she would just pull away when I fingered her. I kissed her back and she hit the roof like I had stabbed her and said ouch.
 
I was at a party, and was talking to a fellow who was sort of... lets just say not the most attractive fellow in the world. Well we got on the topic of being gay, and him being gay, and him being attracted to me, and i was a little drunk and he kissed me, and i thought "what the hell, lets give it a try," so i kissed him back. Well, If i didnt know i was gay before, i sure knew then. It was like kissing a fat pair of worms, did absolutly nothing for me, sort of grossed me out, well grossed me out alot. Anyways, he wanted me to blow him, but i politly declined.
 
I can't pick just one. Here are three:

1) Being walked in on by my girlfriend as I was taking her younger sister's virginity

2) A condom breaking and me getting my (different) girlfriend pregnant.

3) My first experience having another guy fuck me. He wasn't that big but was not at all gentle.
 
Several come to mind but...

Was at a school dance (all dressed up)...a girl was hitting on me- went back to her dads truck, lots of flirting, necking... she pulled my cock out, was so excited I came all over my suit and her dress..(she was wearing blue chiffon). Tried to clean it up/off and I woudn up cuming again (ah to be young and well- she had GREAT tits...what can I say)...

The whole experience only made me hornier- and was in an ill fitting suit with no way to hide a 1/2 hard all night.

Nothing like trying to walk back into a dance with large 'wash stains' on her dress and all over me (I shot like a cannon...god what a mess). Really wish the bathroom had a 'blow dryer' hand dryer... I had gotten a ride with a friend so no way to simply leave...

Was miserable... had drying cum all over the inside of my pants... and no way to do the 'shirt tail trick'.
 
Not really one time in particular but my last bf was not too fun to have sex with. He was really obsesssed w/getting me to orgasm by going down on me which I just can't. It got to be a big deal and it was all this pressure instead of being fun.
 
tiff86 said:
Not really one time in particular but my last bf was not too fun to have sex with. He was really obsesssed w/getting me to orgasm by going down on me which I just can't. It got to be a big deal and it was all this pressure instead of being fun.
Click to expand...

Aww, poor dear... Choose me instead, I'll take off the pressure -- I won't try to make you orgasm at all.

:wink: :biggrin1:
 
A long time ago, was seeing an older woman from work who started crying the first and only time we did it.

That does nothing for your confidence!

She was older by about 8 years, I was 19 (iirc) at the time.
 
chrstphrrr said:
I was very drunk and going down on a guy I barely knew and barely liked in the driver's seat of his dad's pick-up truck. :blowjob: He kept forcing me down past my comfort zone (he's got a fairly long, thin dick) and my usually well-suppressed gag reflex kicked in, aggravated by the half a bottle of tequilla I'd consumed and...upchuck! :684: He was not cool about it. :zx11pissed:

This was hysterical. I had a similar thing happen (I was getting sucked) and it took all the fun out of getting a blow job.
Click to expand...
 
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