Most humiliating real life thing you have done..

While my wife and her best girlfriend were drinking wine when I got home, her girlfriend measured my small white penis. Although at the time it was humiliating, I now like small penis humiliation. Phil and Nicole

View attachment 2610597
My ex wife would have me strip down for her friends as well to show them why we would share her with another guy (preferably well endowed)
 

Attachments

  • Screenshot_20250403_004249_Messenger.jpg
    Screenshot_20250403_004249_Messenger.jpg
    99.8 KB · Views: 40
  • Screenshot_20250403_000729_Messenger.jpg
    Screenshot_20250403_000729_Messenger.jpg
    139.8 KB · Views: 27
  • Like
Reactions: Wantsomefunto
I absolutely love CBT and castration play. We have discussed castration a few times but it always comes back to the necessary sacrifice of no more ball beatings if they are gone, and we both love that, so it usually ends there, but it remains one of my strongest fantasy desires.
Fortunately (for me), we don't engage in play that would directly result in injury... certainly CBT, castration play and similar fun has some inherent risk. However Krista is interested in some pretty extreme things.

It is exceedingly erotic, and simultaneously humiliating to be put on display to anyone whom Krista feels like showing me to. Especially when she's engaging in emasculating verbalizations and role-play.

castration_play_0.jpg
 
Fortunately (for me), we don't engage in play that would directly result in injury... certainly CBT, castration play and similar fun has some inherent risk. However Krista is interested in some pretty extreme things.

It is exceedingly erotic, and simultaneously humiliating to be put on display to anyone whom Krista feels like showing me to. Especially when she's engaging in emasculating verbalizations and role-play.

View attachment 2613156
Lot of us cucks would be proud to have your cock.
 
By far at least for me, the most humiliating thing that has happened between me and my wife was me entertaining her family while she snuck out of the house to her boyfriend‘s house to get a train run on her. I have a hard time thinking that her family didn’t know something was up. They flew eight hours to visit us and there she was wearing lingerie and a slutty dress and I distinctly remember her telling her sister that she had something to go and take care of and that I would be there tour guide. I remember her sister asking her why she was so dolled up and she giggled and told her that I would explain knowing full well I was too embarrassed and then I would have to pull an excuse straight out of my ass. It wasn’t an outward humiliation like I don’t really think she was trying to do it. I think she knew she had some really good cock lined up and just didn’t give a fuck about anything other than that. But I don’t think I’ve ever felt like more of a cuckold than I did it that moment.
 
Wifes BF bi and I straight so the two of them seem to play on that or least he does ? jesus this summer we have a pool , summer kitchen they will hang swim and fuck ill watch and make lunch or dinner time? etc they keep me hard the whole time one or the other i prefer her :-( any how one day they done we eating he puts suntan lotion in her hand and tells me to fuck it ? LOL I'm so worked up at this point I'm game he starts grabbing my ass running his finger up and down till I'm pushing back i just close my eyes thinking of her? LOL fuck just his tip of his finger and her hand back and forth till im panting....he stops her!!! pushes her away and makes me put my cock in his fucking hand LOL its way harder and he squeezes tight a few stroke then loosens up again over than over till panting now finger so much deeper in my ass! touching me where i want to fucking cum put cant each time you have no idea what its like so am pushing back on his finger god lol at same time frantically trying to hump hi hand to get off on either side and he just playing me like an instrument Jills laughing hysterically telling me i look like the energizer bunny and to wiggle my ass more? and he drawing it out as long as possible .......most humiliating yet best handjob ever
 
Wifes BF bi and I straight so the two of them seem to play on that or least he does ? jesus this summer we have a pool , summer kitchen they will hang swim and fuck ill watch and make lunch or dinner time? etc they keep me hard the whole time one or the other i prefer her :-( any how one day they done we eating he puts suntan lotion in her hand and tells me to fuck it ? LOL I'm so worked up at this point I'm game he starts grabbing my ass running his finger up and down till I'm pushing back i just close my eyes thinking of her? LOL fuck just his tip of his finger and her hand back and forth till im panting....he stops her!!! pushes her away and makes me put my cock in his fucking hand LOL its way harder and he squeezes tight a few stroke then loosens up again over than over till panting now finger so much deeper in my ass! touching me where i want to fucking cum put cant each time you have no idea what its like so am pushing back on his finger god lol at same time frantically trying to hump hi hand to get off on either side and he just playing me like an instrument Jills laughing hysterically telling me i look like the energizer bunny and to wiggle my ass more? and he drawing it out as long as possible .......most humiliating yet best handjob ever
So you are also bi then!
 
I wouldnt call it humilating but I lost a bet to my ex girlfriend.
We were fucking for this guy on ... and I bet her she couldnt get the guy to come over to our hotel room.
If she won, she can do whatever she wanted with the guy, If I won I got to stick it in her ass
Guy came to our room with 45 minutes and before ex got started she says "My boyfriend said if you come over he wants to suck your dick and I want to watch. If either of you back out, neither of you get any pussy tonight"
Guy looked at me and unzipped his pants and said "cmon man, dont fuck this up for the both of us, start sucking...."
I opened up and he shoved his cock in my mouth
 
I shared my 32 year old second wife at my 35 year high school reunion with my 53 year old hung classmate and let him cum in her while I called her a dirty whore.
 

Attachments

  • video-1484336572 - frame at 1m10s.jpg
    video-1484336572 - frame at 1m10s.jpg
    6.4 KB · Views: 24
  • video-1484336572 - frame at 1m11s.jpg
    video-1484336572 - frame at 1m11s.jpg
    6 KB · Views: 27
  • video-1484336572 - frame at 1m16s.jpg
    video-1484336572 - frame at 1m16s.jpg
    5.3 KB · Views: 26
  • 20151227_101503 (2).jpg
    20151227_101503 (2).jpg
    86.3 KB · Views: 28
I wouldnt call it humilating but I lost a bet to my ex girlfriend.
We were fucking for this guy on ... and I bet her she couldnt get the guy to come over to our hotel room.
If she won, she can do whatever she wanted with the guy, If I won I got to stick it in her ass
Guy came to our room with 45 minutes and before ex got started she says "My boyfriend said if you come over he wants to suck your dick and I want to watch. If either of you back out, neither of you get any pussy tonight"
Guy looked at me and unzipped his pants and said "cmon man, dont fuck this up for the both of us, start sucking...."
I opened up and he shoved his cock in my mouth
Gee, from your POV, did you truly lose?
 
Watching the wife in person was beyond humbling and humiliating
She’s dated for years before that and saw photos but fuck the time watching her was beyond degrading
She made out with him and he fucked her and came in her
Hearing her making noises I never heard before and her cumming so hard when he fucked her
Add to the fact she gave him a blowjob and all I saw was her big ass bent over and him moaning
 
By far at least for me, the most humiliating thing that has happened between me and my wife was me entertaining her family while she snuck out of the house to her boyfriend‘s house to get a train run on her. I have a hard time thinking that her family didn’t know something was up. They flew eight hours to visit us and there she was wearing lingerie and a slutty dress and I distinctly remember her telling her sister that she had something to go and take care of and that I would be there tour guide. I remember her sister asking her why she was so dolled up and she giggled and told her that I would explain knowing full well I was too embarrassed and then I would have to pull an excuse straight out of my ass. It wasn’t an outward humiliation like I don’t really think she was trying to do it. I think she knew she had some really good cock lined up and just didn’t give a fuck about anything other than that. But I don’t think I’ve ever felt like more of a cuckold than I did it that moment.
Show me and tell me everything Give her to me completely she’s Incredible
 
I’m new to this, but the first time my girl sat on a really thick dildo and had her first internal orgasm….she stopped. I looked at her in the eyes. And she just gave me this smile….like “yeah, that just happened”…I’ll never forget it.
 
She masturbated for a group of men outside of her motel room. The next day she went to breakfast and they were all there. Kept talking about her and laughing at her. She said she felt so humiliated that she went back to her room and mistreated again