Craziest thing you've done!

[mouseisthedaddy]

An ex of mine from back in my glory days used to work in a novelty sex shop part time. Once i fucked her in the store room while the shop was still open and had people browsing. She was very petite so she stood on some steps and pulled her jeans and panties down just enough to give me access. I fucked her from behind with my hand over her mouth whispering how much of a slut she was. It was over pretty quick. I still think about it all these years later. Wish i'd used some of the toys from the shop on her.

[zucky]

When I was in college I had a girlfriend who used to LOVE watching me masterbate. Almost every day I would get naked for her, lie down on her bed in her dorm room, or my bed in my own dorm. Well, she told her roommate about it and this girl wanted to watch, too. I did it a number of times in front of both of them. One thing led to another and one evening about eight girls came in her room and I stripped naked and jerked off in front of all of them. It was the end of the semester and I wasn't returning the next year anyway. Having an appreciative female watching me jerk off intensifies the erotic turn-on for me. As long as the girl is willing to watch. I am not a flasher, nor into shocking or being offensive.

I've often fantasised about masturbating in front of several women - I'd love to do it! Naked in front onf them, but they must be dressed. Then cumming over myself and them watching - wow!

[HungBlkBottom]

I can't single it out, but the first 3 things to come to mind when I read this title was

1) Had sex with a pastor (not my personal one) in his church immediately before an evening service
2) Got DPed at a pool party in front of a group of people
3) Gave an Uber driver head in traffic on the freeway

[Diverse_desires]

I can't single it out, but the first 3 things to come to mind when I read this title was

1) Had sex with a pastor (not my personal one) in his church immediately before an evening service
2) Got DPed at a pool party in front of a group of people
3) Gave an Uber driver head in traffic on the freeway

Those all certainly qualify!

Well, here goes. I fucked my Sister. Multiple times. Now this requires some context.

We did not grow up together. She's 4 years my senior, and was put up for adoption by my Mom, who was single and young at the time and already had a son. When she became an adult, she found and reached out to my Mom. My Mom wanted nothing to do with her. But she also reached out to my Brother, who did. He flew out to meet her (all the way across the country) and they became close, though their relationship has been volatile over the years. In truth they're too much alike. Me? I was young and my Sister respected my Mom's wishes to stay away from me. We talked maybe once or twice over the years, with her still feeling awkward about meeting while my Mom was alive. I was Mom's favorite (I think she felt guilty about putting my Sister up for adoption, and as a result spoiled me rotten; more or less seeing me as some flawless blessing, which I certainly was not. At least not the former), and my Sister didn't want to try and have a relationship with me with that in the way.

Fast forward to my Mom's funeral. She had moved closer by this point, and she ended up attending. That was the first time we'd met. Strange place to meet a sibling, right? But it would be 10 more years before we got together under "normal" circumstances. Somehow a meet-up meant to begin the formation of a brother/sister relationship ended up with me cumming in her mouth. To say the least it was not what we'd had in mind when the day began. This kind of relationship continued for the next year or so, even after meeting her family. We became close and I became a part of their lives. Eventually it stopped. It wasn't some mutually agreed upon thing. It just... stopped. We have never discussed the whys, and I've remained a part of my new family and just recently returned from a stay over the Christmas holiday.

It's not something I'm looking to reignite, but honestly it's not something that I regret or am ashamed of either.