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This is a question The worst sex I ever had

OK, enough of the fluffy.

What's the worst sex you've ever had?

(, Fri 15 Jun 2007, 10:41)
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Young, lonely and ridiculous
I still psychically cringe from this memory.

I came out of a 4 year relationship having been cheated on and immediately went on the lookout for rebound sex, there weren't many options to be fair. By chance I struck up a conversation online with a woman who worked remotely for the company I worked for and we got talking for hours, thus begins the online relationship cliché. One thing leads to another and she arranges to get on a train and come down for a day to "see the sights".
I was 18, lonely and looking for easy sex. She was a 27 year old married mother of one looking for a divorce. What could go wrong?!

I arrive at the train station and she is too frightened to come over to my car. 10 minutes later and an awkward hello and we're on our way to the hotel. We arrive and settle down on the bed and begin but things rapidly start to disintegrate:

1. During making out, she suddenly gets up to go to the bathroom, being a smoker she is extremely self-conscious of her breath, she's going to brush her tongue.
.....Ok. I can deal with that.
2. She settles back down yet any attempt to fondle her bits is followed by a firm forceful push away. WHAT THE HELL? She insists we carry on, she's just not used to intimacy and is too ingrained from pushing her husbands hands away.
3. Her kissing is awful, I'm beginning to lose interest, no tongue and no passion. Time to get these clothes off.
At this point it just becomes a battle, she clearly has huge issues with intimacy from her failing marriage and I'm as flaccid as a popped balloon. I still want to screw so I push on.

I end up naked, she has most of her clothes on. Clearly an eating disorder and gravity has taken it's toll, she hid it well until now.
She's still hitting my hands away every other minute but I eventually get her stripped down and begin pleasures of an oral nature, hell she evens start to get into it, moaning, moving, the works - that is until she's about to cum! I can only describe it as a punch to the face. I'm beginning to lose patience. I'm no longer turned on.
We revert back to making out and I finally get to feel her boobs and I'm disgusted. This is awful, they feel like plastic bags filled with 3 parts water, 1 part sand. I'm ready to leave.
I'm pretty much flaccid, I'm feeling annoyed but I'm still kinda horny so let her go to work but to no avail. No amount of hand or mouth action gets me started. We even try some sex. No, that didn't work, it felt like I was thrusting into an open space, either she was too loose or me too flaccid. That's it, I'm mentally scarred.

We give up, I had to entertain her for an entire day after that and it was the most uncomfortable experience of my life.
We didn't re-attempt anything of a sexual nature. The way those boobs felt was so wrong, the way she pushed my hands way made me feel like a rapist.
How screwed up is that?
(, Mon 18 Jun 2007, 6:06, Reply)

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