Have you ever fucked someone you despised?

When i was 21 I worked at a warehouse for a retail store. My supervisor got her position by just working at the place for so long and was incompetent, to say the least. I couldn't stand her but she always made little comments to me.

We had a little bar in town that would have 25 cent draft night on Thursdays and most of us would go. The bar couldn't keep that up so they announced their last night of that and all of us decided to go. The supervisor caught wind of it, her husband was out of town anyway. She had her mom drop her off at the bar, with no ride home planned. I guess she assumed she could make one of us do it. After a dollar twenty-five of beer, she was getting out of hand. For some reason, I got nominated to take her home, mainly because she was short and fat and I had a lifted truck and we all thought it would be entertaining to see her get in.

When we finally hoisted her into the truck and got moving, she went after my cock like a hungry dog. Her shirt and bra came off letting her fat floppy tits hang. She would grab my hand and try to stick it in her pants to show me how wet she was as I tried to shift gears. I was somewhat turned on but more annoyed because I really didn't like her as a person.

When we got to her driveway, she open the door, threw the clothes and shoes she had removed into the yard and demanded i come help her down. I helped her, kind of hoping she'd fall on her bitchy face but she didn't. She complained about my truck and how the driveway hurt her feet as she stumbled to the door. I just wanted to get back to the bar but she couldn't find her house key and I had to help her look for the spare. I open the door, helped her up the steps and into her kitchen. She unbuttoned her jeans and dropped them and her panties right there. Naked, she went into her living room and flopped down on the couch. She shouted, "come here and let me suck that cock some more!" Well, even though I was annoyed, my dick led itself to her mouth. True to herself, she couldn't stop bitching. "Don't gag me, don't move, I'll do it, blah blah." I had enough, I rubbed her pussy which she enjoyed, she quit sucking layed back and smiled so I gave her fat pussy a smack. She started to say something but i shoved my dick in her mouth, I fingered her roughly and face fucked her. Her protest stopped, bitching was replaced with moaning.

She ended up being the first woman that I ever fisted, the first I ever went back and forth between pussy and ass, first ass to mouth and the first woman I pissed on. I didn't make it back to the bar and she didn't make it to work the next day.

I never had any trouble with her at work anymore. She wasn't nice but not as mean as before. Nothing was ever said about it until the day i left that job. She told me she needed to thank me, that she confessed everything to her husband a couple weeks later and after a few rough days their relationship and sex life got better than it ever was. Ten or so years later, I took my wife and kids camping. After we had got our site set up another family started to set up in the next site, man, woman, teenagers. It was her. They were about 20 minutes into setting up when she realized it was me. She made them put up everything and leave.
 
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yes , my wifes friend i fucking hate her, my wife knows this and said well hate fuck her then.
I'm more into seeing my wife get pleasured but i did it and my wife took pictures so her friends mouth didnt run off with itself.
Not my proudest moment
 
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Early 80s I was 21. Worked at a car lot, a Dennys type place next door, we had lunch there often. Waitress were all young and cute, I got with quite a few.
Hostes was very hot but an absolute bitch to me. She knew I was doing the servers and hated what i was doing, she told me that many times.
One day I was paying my check, she was cashier also. She says something like... who's you date tonight? I said I didn't have one, she says let's meet for a drink, I declined. She said the offer was open.
About a week later I go in for lunch, same deal from her....who you going to f**k tonight? in her usual bitch attitude.
We ended up hooking up several times. She fucked me pretty good but never stopped bitching about how I was doing the other girls.
When she was horny she was great but after we had sex she ass back to her usual self.