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Guys, what`s the most Outrageous or Immoral Sexual thing you did ?

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The Book of Genesis in the Hebrew Bible tells the story of Moses receiving the Ten Commandments, one being “Thou shalt not commit adultery.” My understanding is that adultery includes a married man bedding a woman who is not his wife.
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Adultery, to be sure, mostly with escorts (women) or guys off CL (men). I guess some would say paying for sex, too, though I am of the mindset that if both parties are consenting to the transaction, it should be treated as just another business.

* Part about consent bolded because, at least around here, there's a lot of trafficked women who are forced into it. That's both immoral and illegal. I've always stuck to indy escorts who are clearly in it voluntarily.
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Recently? Not particularly outrageous, but my friend & I had a threesome with a transgendered woman.
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I used to ho over to my buddies house every day after school and trade blowjobs with him. I had a huge crush on his dad. One day I made sure his dad caught me right in the middle of swallowing his son's load

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I secretly filmed a sex session I had with a work colleague, I keep it for me and me alone.

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Sex with a second cousin who was the hottest woman I have ever seen and a maniac in bed.

Living bi-cariously through Lush
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Sucking another guy off through a gloryhole. Despite my stories, nothing else I’ve actually done comes close.

My Dirty Talk competition entry: No-Dating Policy

I get dicked by a federal agent. My top-ten Noir competition entry: Dick Job

My alliteration-addled Free Sprit competition entry: Buff Bluff in Banff

Card catalog? Hard catalog! My library

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I picked up a wo.an I the Philippines and her daughter. It started harmlessly, ut developed from there.

After some chat, I got both of them ba k to my hotel. Hotels in Phil can be quite prudish, but this hotel was not. After buying food for them both and a small money transaction with momma, I had her sucking me off with her daughter watching. The daughter carried on watching me fuck her momma and then she was horny enough to let me fuck her too.

I'm really not too sure whether I was using them or they were using me. I guess a little of both.

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Blindfolded my wife when she had been drinking and had taken her nightly benzos, I put an ad on Craigslist and let three strangers jerk off on her body, two blew their loads on her ass and slightly exposed pussy and one blew his load in her hair. After they were all gone I used the cum from her ass to finger her and then fuck her. She still has no idea.

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Pressured my partner into sex a lot after we were married. Was younger and had a lot of false ideas about sex being like a negotiation from TV and movies.

My partner was abused when she was young and had trouble telling me flat out no. I didn’t understand how shady consent was in this sort of relationship and she couldn’t communicate how it made her feel until almost 10 years into our marriage.

With my boys I work very hard to teach them about proper consent and will talk about things we see even in kids media that I find problematic. Stuff like a girl character telling a boy to leave her alone and him pestering her every episode can really muddy what actual consent is for boys.

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Quote by Longinmat
The first time I told my wife I wanted her to fuck my best friend, it was sort of role playing in the bedroom. The more we did it, the more real is was becoming. Then, one weekend, while on business, he stayed at our house. It started with a few drinks, then the hot tub, then she sitting on his lap, suddenly, I was sitting on the other side of the tub, watching him fuck her. Part of me was wondering what was wrong with me, the other part was how totally aroused it made me. I knew it was wrong, but I could not control myself. The strange thing was after he was done with her, how weird it was when I took my turn. Going inside her and feeling the presence of another man was unexplainable. The warm, wetness of it, feeling his cum ooze out as I went into her. Now, a year later, two more of my friends have had her! Surprisingly, our sex life has been energized!

Can I be your friend too? (jk).

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Outrageous is not the same as immoral. Outrageous is a bit easy, i had DP Vaginal only sex (no anal) with my friends (now wife) and him. The best part about this was the friction inside her as we moved together, we were so in sync that we came at the same time as she did and it was perhaps the single most gratifying experience ive ever had.

As for immoral, ive had sex with two different sisters, and there mother, all at different times all within 48 hours. None of them found out for weeks as I kept pulling this off. I am NOT proud of this, but we were all young and dumb at some point and that was one incredibly sexy family.

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I felt up my first wife’s youngest sister

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I played with my 'girlfriend's' pussy, (she doesn't wear underwear), while in a bar with my wife sitting beside me and her boyfriend sitting beside her.

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I gave a blowjob to the head usher at Church a half hour before the service

Living bi-cariously through Lush
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To the point that outrageous and immoral are two different things, the gloryhole incident was the most outrageous thing.

The most immoral thing I've done was to leave a woman's apartment right after having sex with her on a (really great) first date. To this day I think we could have had some sort of relationship, even if not necessarily long-term, but I blew my chances and hurt her.

My Dirty Talk competition entry: No-Dating Policy

I get dicked by a federal agent. My top-ten Noir competition entry: Dick Job

My alliteration-addled Free Sprit competition entry: Buff Bluff in Banff

Card catalog? Hard catalog! My library

Advanced Wordsmith
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Setting up my wife and my friend without her knowing it. She ended up just letting me fuck her while she let him suck on her tits.

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Fucked in a church? Got caught by the preacher and she slammed the door in his face. Does that coint?

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Quote by danl2019

s for immoral, ive had sex with two different sisters, and there mother, all at different times all within 48 hours. None of them found out for weeks as I kept pulling this off. I am NOT proud of this, but we were all young and dumb at some point and that was one incredibly sexy family.

I would be proud. I tried to do the same thing, actually.

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I was married. I fucked a married woman in her marriage bed while her husband who couldn’t get it up was playing video games in a room 2 doors down the hallway. He never knew what was going on. We had fantastic bareback sex, especially as she hadn’t had cock for so long. 18 months later She had divorced her husband of 30 years and I My wife of 33 years. A further year later we married. We have great love for each other and a fantastic sex life.

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I'm not too wild or depraved in general, but I once went to a public beach, swam out a little distance so the water was up to my neck while my feet were touching the bottom, and masturbated in secret below the water with a bunch of other people (strangers) swimming around me. The exhibitionism was a bit of a thrill and still serves as fantasy fodder, even if the resulting orgasm felt a bit rushed and less than satisfying. Haven't done anything like that since.

Don't believe everything that you read.