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Who is a person you have had sex with, but probably shouldn’t have?

Where it cost me something ( not money ). A coworker, cost me a job or two. I’ve mostly been in FLRs with fetishes involved. Both times I dated a lady who was a boss. Once to me directly and another indirectly and I had to go. They made me miserable.

The other was a friends mom. The friend was kinda odd but we all have odd friends. He lived at home still so I’d go there and hang out. I ended up hooking up with his mom secretly. We humped like rabbits. The last time we were in the garage where the laundry was, there’s 2 doors into it one from the house and one from the side with boxes and stuff on that side of the garage. The laundry machines are going she’s holding on to the washer skirt up I have no pants on just pounding her. She’s cumming and getting noisy which excites me and I start to cum. A stack of boxes falls startling us. She stands up pulls her skirt down I’m in the middle of shooting my load and I shoot all over her skirt. We look over at where the boxes fell and there’s her son dick in hand still beating it then pulls his pants up and cums in them. His mom runs in the house and I’m just standing there with him. We almost always hooked up in the garage there was a big comfy sofa if you turn the machine on it was noisy, you can just throw the cum rags into the laundry it kind smelled like bleach out there anyway. So it turns out he’s known almost the whole time. I ask him how, And told me he would tell his mom that he got off later than he did in hopes to watch. Then he started telling me about it in a excited way and that the first time he saw us we were on the couch I was leaning back with my eyes closed and he walked into the garage noticed what was going on and hid behind the boxes. He’s watched as his mom sucked on my dick then after a little bit she took her skirt off and she got on the couch and “ you put your penis in her” he tells me. Then he talked about his mom making noises and after a bit I took my dick out of her and started cumming and brought it up to her mouth and while still cumming she opened her mouth and I put it in. I totally remember this it was like during the first week and we’ve been having sex for awhile now. He also told me he had moved the boxes a little so he could watch and not be seen and that he had recorded some of it. Even crazier while he was telling me he was asking questions. It was the only time in my life that I really thought this is surreal cause I was answering his questions.

It was like he was excited about getting caught and there was nothing odd about it. So his mom was just mortified and freaking out and I didn’t tell her about half the shit he told me. Really crazy is except for the weird being watched stuff this was probably the most normal sexual relationship I’ve ever had.
 
I usually try to avoid messing with anyone from the job. Especially someone I supervise. This particular woman, when I interviewed her, I knew would be a problem. Wasn't my type but for some reason. I was very attracted to her. Her boyfriend worked at the same facility. So I figured that would keep things from happening. Dude got transferred to another facility. After that, it wasn't too long before she stopped by my house one afternoon. We had sex and it was good. Fucked her a few times and enjoyed it. The shouldn't have part comes in when she would be at work. Basically doing things to give others ideas that we were fucking. Sitting on my desk, always standing very close to me or wanting to walk arm and arm. A few times she wanted to have a conversation about moving in with me and starting a real relationship. No telling how much pussy I missed out on because of her.
 
GoGreenGoWhite said:
I’ve only had fantasies so far but would love to hear some real stories!
Click to expand...
I would have to say, my oldest Uncle. He has such a big hard cock and is such a great lover. He only comes to my town for a family reunion, at Christmas, and I have let him fuck me the last 3 years! I feel so naughty for doing that, but the good feeling afterwards makes it well worth it
 
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