Got two that might qualify for mistakes, but they turned out okay in the end.
During a night of barhopping I hook up with a customer of mine from the bar that I worked at. We went to my place and had sex for about 3 hours. Afterwards, without cleaning up, I took her back to her car at the bar and said good night (she had to get up early the next day). I then went to the bar that I worked at to have 1 more beer and then back home. I ran into a woman that not only was a customer but a regular sex toy of mine. We talked for a while and then went to her place. She changed into some lingerie (she should have been in Victoria's Secret catalog) and came out to the living room and started to give me a blowjob. Afterall a couple of licks she realized that I had sex with somebody else very recently. She asked me if this was the case and I just about lost it but my mouth just went before my brain and said "Yes.". I thought that this was either going to end badly or I was going to have to take a shower first. She then asked who it was and once again the mouth and brain lost connection and I told her that it was another customer from the bar that I work at. She knew the woman and just said "Okay." and went back to sucking my dick.
About a week later I'm at work and both of them show up at my bar. They talked about what happened the previous week and smiled. The next night I was scheduled off and the three of us ended up in bed together. The best part was the lingerie show that both of them went through to each find the perfect outfit.
Next up was the time I was living with an older woman (19/36). She had never seen a porn movie so instead of going to see 'Rocky Horror Picture Show' because the line was too long off we went in search of XXX. We ended up at a movie house, book store and toy store. Everything under one roof. We go and watch a movie for about an hour we she gets worked up enough to have sex but she didn't want to do it in the theater. She identified too many perverts in there. And the one next to her. So we go and on the way out I asked her if she had ever seen a peep show. She said no so I got a fist full of quarters and back in we went.
We're in the booth and I start undressing her from her jeans to do a standing doggie. She is leaning on the door and I'm thrusting away when the door pops open and she almost falls out but I did manage to pull her back by grabbing her hips and maintain balance. I reached out for the door handle, closed the door and made sure all of the slide bar locks were engaged. However there is more to this. So that the door doesn't fly open again she is now leaning her head and shoulder on the plexiglas screen cover. After a few good thrusts from me she is pushed into the plex and it cracks in several places. This happened right as I came and she had pulled away and stood up straight. I shot my wad and we thought that it went on the floor. However we came to realize that my wad was on the leg of her jeans as we walked out of the building.
Needless to say she didn't want to go there again.
* This post has been modified
: 19 years ago