Would love to hear your stories about sexual encounters that you knew were a bad idea, but went ahead with it anyway.
Sex That Should Never Have Happened
- Thread starter STEVIEG55
- Start date
Finally fully seducing the biggest crush of my life, making my feelings even more intense for her, but she's married and there's little chance she will leave him (but she's got it cushy where she is, it's basically all just for her kids). But the sex was better than I thought it would be! Especially when I went down on her, which apparently no-one had done to her in forever.
After years of fantasizing about my cousin I helped her home one night as she was wasted...and 22 at the time...she was being very flirty and I actually got her naked on her couch and ate that tight like southern pus... grey tasty..then as I started to stick it in her she kinda sobered up and said your not in I cant feel it..after another try she pushed me off and grabbed my dick to look at..she started laughing saying this is as big as it get I fucked bigger on freshmen in hs...she laughed and said your oral is good but you cant please a woman with that... this was way before I knew what cockholding was. She ended up for 2 years or more..till she moved awsy... ruining ever date I ever had...telling my dates how tiny I was. It was hot but frustrating...I miss her
A friend of my brother was visting him a couple of weeks ago. I called my brother because there were some works in my building and I would have no water until the following day, so I could not take a shower. My brother told me that I could go to his house and have a shower after work, so I did. However, I did not know that his friend was there. When she opened the door, she told me that my brother was in the gym at that moment and he would be back later. I just told her that I would have a shower and leave. She said it was ok but smiled and asked whether she could take my suit off and help me have a shower. I thought she was kidding, since she is younger than me and I think she is having sex with my brother. Besides, I do not like her. When I was about to got to the bathroom, she insisted and took her t-shirt and bra off. Then she came to me and kissed me and we finally had sex before I entered the shower. She had condoms, so I assume that she had them to use them with my brother. She also told me that she wanted to swallow my cum, so I took my condom off before cumming in her mouth.
I finally had a shower and she went to the living room. She has been texting me for some days now but I do not want to have sex with her again.
She saw something like this.
I finally had a shower and she went to the living room. She has been texting me for some days now but I do not want to have sex with her again.
She saw something like this.
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No, she is not ugly. In fact, she has a nice body but she is my brother's friend with benefits and I do not want to interfere.
Hmmmm.
For me. Well not sure if it shouldn't have happened but had sex with a married pregnant coworker whose husband wasn't interested in her pregnant body. She was in great shape though, just had a baby bump and her ass had gotten rounder but not huge.
Fucked my married boss in her family van outside the restaurant where we had our dept Xmas party. She was drunk, she was pissed her husband was not there. She did have rules though, no kissing, oral was allowed. No fucking her pussy. Anal instead. Seems to her no kissing no allowing her pussy to be fucked made it slightly less cheating. She was weird to me for months after, kept trying to get me to transfer out, until she finally did.
For my wife, she sort of feels guilty about in the past fucking a few of her friends husbands/bfs behind their back. Even one friend stop for coffee complaining her husband might be cheating because she was pretty sure she tasted pussy in his cock and not her own. (Yes it was my wife's).
Looking back she says it was fun but having sex with her best friends father and 3 of his friends when she was 18 was not a good choice. Nothing bad happened but looking back the risk of something bad happening was high.
For me. Well not sure if it shouldn't have happened but had sex with a married pregnant coworker whose husband wasn't interested in her pregnant body. She was in great shape though, just had a baby bump and her ass had gotten rounder but not huge.
Fucked my married boss in her family van outside the restaurant where we had our dept Xmas party. She was drunk, she was pissed her husband was not there. She did have rules though, no kissing, oral was allowed. No fucking her pussy. Anal instead. Seems to her no kissing no allowing her pussy to be fucked made it slightly less cheating. She was weird to me for months after, kept trying to get me to transfer out, until she finally did.
For my wife, she sort of feels guilty about in the past fucking a few of her friends husbands/bfs behind their back. Even one friend stop for coffee complaining her husband might be cheating because she was pretty sure she tasted pussy in his cock and not her own. (Yes it was my wife's).
Looking back she says it was fun but having sex with her best friends father and 3 of his friends when she was 18 was not a good choice. Nothing bad happened but looking back the risk of something bad happening was high.
I re-connected with an ex-gf from my early 20s, she was now in her early 40s, married w/ 2 kids, still had an OUTSTANDING body. Flat tummy, breasts still pert. Couldn't believe it. Uncovered a hugely submissive side that I didn't know she had when we dated, made her my slave for a while. The "bad idea" part wasn't all that bad, I just always wondered what her state trooper hubby might do if he found out. 
Never did though.
Never did though.