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What's the dirtiest thing you've ever done?

K9sully

Citizen of Zooville
So far:
Had a couple of very heavy petting sessions with my drunk mother (she was 39, I was 18).
Fucked my girlfriend on a pool table in a pub on my 21st birthday (the table was upstairs, various friends and strangers caught us, some stayed and watched).
Crossdressed in my mothers lingerie with the same girlfriend, she was in full lingerie too, a mutual male friend then fucked her and made me suck his cock and clean up her pussy.
K9 fun was on and off for years, oral only.
Later in life my ex wife and I got into the cuckold swinging lifestyle for a few years.
When we divorced I started meeting local guys for oral and watersports, crossdresser's, doms, married men, cottaging etc.
Now at 51 I have no sex life due to this damned lockdown!
Did mom remember your sessions after she sobered up? How was your relationship with her after that?
 

Bloeejoee

Tourist
When I was 17, my GF at the time was hyper sexual and very open minded. We were kind of each other's slippery slope into the kink world. Anyways we had sex all over the place. Next to buildings, in tents on family camping trips, blowjobs in my bedroom without a door, even a playground once. She loved the whole cross dressing thing and being dominant often. We went to different schools and for her Sr. Prom she bought a red lacy thong and had me wear it under my tux. We went to parties all over the place that night and when we got back she wasn't the one that got fucked... I was. I know it may not be the dirtiest but it was pretty kinky for the time.
 

Slugma

Tourist
So far:
Had a couple of very heavy petting sessions with my drunk mother (she was 39, I was 18).
Fucked my girlfriend on a pool table in a pub on my 21st birthday (the table was upstairs, various friends and strangers caught us, some stayed and watched).
Crossdressed in my mothers lingerie with the same girlfriend, she was in full lingerie too, a mutual male friend then fucked her and made me suck his cock and clean up her pussy.
K9 fun was on and off for years, oral only.
Later in life my ex wife and I got into the cuckold swinging lifestyle for a few years.
When we divorced I started meeting local guys for oral and watersports, crossdresser's, doms, married men, cottaging etc.
Now at 51 I have no sex life due to this damned lockdown!
The mother stuff sounds... interesting
 

Memprys

Tourist
I've been in a scat scene. A top did me anally without letting me clean out, and the shit ended up everywhere. He then had me lick his dick clean. It was a scene that I wouldn't want to repeat... except that being in a sex scene where I hated every minute of it was a thrilling turn-on in its own way. So yes, I would do it again, hate it again, and have great memories once everything is cleaned up.
 
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