What is the most humiliating thing your wife has ever made you do?

Most humiliating thing she has me ride my suction cup dildo while she watches. I funny for her to see the precum dribble out while I ride

 

That must be a very humiliating site, you riding your dildo and Mr Limpy flapping up a down with the extra weight of you princes wand as you slowly dribble

Wonderful

 

The thing that come to my mind, is when my Wife told her younger sister of our lifestyle.

 

When I was sent to a bridal shop to find out what size dress I was. The girls had a lot of fun

 

@maid julie That's a good idea a friend of mine works in a bridal shop I thinks I will send my Jeanette for a fitting.

(Jeanette's Wife/Mistress/KH replying)
Hope I haven't broken the T&C's

 

There is a post on here about my experience and there was also a maid dress involved

 

My wife has made me do plenty of humiliating things when we role-play in the bedroom. However, of the more daring and exhilarating incidents actually happened in public. There was a general BDSM meet up advertised on Fetlife so we went to the local adult sex toy store just to see what it was like to meet others in the kinky lifestyle. While there we started chatting with a group of ladies who were dominant like my wife. They were dressed in leather and very attractive and around our age. She told them she keeps me locked 24/7 and the women were really interested and their eyes got wide eyed as she explained more about how long she keeps me locked, etc. Then my wife instructed me to unzip my pants and show them my cage. I was in a Mature Metal 1 3/4" Jailbird and pink lace panties. I got the butterflies when the women looked at my situation and then the one woman said "You go girl" as they looked at my wife like she was a goddess. It was very hot. The only other time that I know she told someone else about our FLR was when she told a co-worker years ago at an old job. The friend was having trouble in here marriage and my wife was describing how our playtime has increased the spark and intensity .

I don't know why but the exposure is a huge turn on to me. I would love it if she had a female friend to watch or join us but sadly all our friends are vanilla and we have no one single to share our secret with.

 

Not my wife, but a former Mistress.
She had me have sex with her husband's blowup doll while they watched. Then I was to lick the doll clean.

It was both humiliating and very erotic at the same time.

 

That would be hot!

We have a half torso with a fake pussy built in. My wife loves to unlock me and make me pleasure myself by humping it. All the while she tells me how I'm not worthy to have her pussy. Usually after I get going she will take her hairbrush and go to work on my ass cheeks. She knows that I go limp once the spanking gets to a certain level and she uses that to tease me. She'll tell me I better hurry up and cum or else I'm going back in the cage until next month. Depending on how long it's been since my last release determines if I can orgasm. If I can I have to pull out and cum on the pussy and clean it up. If I go limp from the paddling (which is likely always her goal) I have to lock my cage before cleaning everything up. It's very frustrating to be trying to fuck the pussy while my body lets my dick go limp from the distraction of the paddling. Of course she spends the next days reminding me why caged boys don't deserve real pussy.

 

Looks like I'm in for a fitting for a wedding dress.

As its our 50th wedding anniversary next year, it would be nice to wear a weeding dress to celebrate.

Any of you Gurls got any suggestions for the most elegant style for a 70 year old Sissy Slut?

 

It was summertime, we like to spend the weekends out by our pool. Since its nice and secluded, we are naked the majority of the time. That is except me, I have this metal shinny thing surrounding my testicles and hanging around my penis. My wife Shannon was lounging in her chair naked and reading and I was finishing up some yard work so I still had on shorts, shirt, and trainers. My wife's GF Julie showed up unexpectedly and a little pissed. A short time later, I found the 2 of them naked and in the pool and my chastity was known only to another couple at this point. It seems Julie's husband went golfing again and blew off a promise he made to her. She was pissed and wondered how my wife has me so attentive and running things past her before going out for my own fun.

My wife calls me over and tells me to strip naked. I hesitate and she warns me to do it now or face the consequences. I immediately pry off my trainers, pull off my shit, and drop my short and underwear to the ground. Julie was amazed and could not believe what she was seeing. The ladies exited the pool and my wife grabs me by the cage and walks me over to the chairs. Once seated she has Julie examine my cage, the first time another woman outside our intimate circle sees my cage, never mind the first time another woman is touching it. Julie is built and beautiful and having an effect on me. My wife explains to her I was the same way and awarding releases helps with my behavior. A week or 2 being locked up without sex or a release has me the model husband.

I spent the rest of the day serving them food and drink and even watching them pleasure each other. Julie was amazed on I waited on them hand and foot and their pleasure had me dripping and no release was in the offing. Before she left, Shannon had me get my old cage out and bring it down to Julie. My wife unlocked my cage and had me masturbate in front of them and I shot off immediately. After my erection subsided, my wife had Julie practice locking my cock up with the spare. Julie left and the next day her husband was introduced to chastity.

 

My Mistress and I are somewhat open about our relationship with a handful of very close friends, namely her former roommates. Let's just say both of whom know beyond a shadow of a doubt that my Mistress wears the pants. So the most humiliating, IMHO, is that I've been volunteered for my Mistress to demonstrate various kinky things upon, like bondage and shibari methods and flogging/spanking techniques, when her girlfriends are invited over for an evening.

 

Being required to expose yourself or do something feminine in public would be both humiliating and exciting. Just knowing the power of your Mistress to make you test your limits like that is special.

 

About 2 years ago (this was roughly 4 years into chastity/FLR) my husband started whining about the cage and getting a bit too big for his panties.
To humble him, I decided to tell my younger sister in front of him, and made him show her the cage.
Shortly after, I made him video me pegging him and had him send her the video.
Since then, she has watched in person. Has even actually pegged him a few times, and now holds the spare key as well.

 

Wow I can't think of much more that would top that! That would be a dream come true.

 

I'm not sure of the most humiliating thing she's made me do is.

One time I accidently ruined myself in a cock sleeve and she just laid there and laughed at me, that was pretty crushing.

One thing she does a lot is force me to kneel and ask for permission for stuff. I'll hear this "oh no no no, you can't just DO that! On the FLOOR!" and start pointing to the floor. I'll bow my head, get on my knees, recite my pledge, and ask her for permission.

Often times when she is tired, having trouble reaching orgasm, and I'm lamely trying to please her, I pull out the big guns. She will instantly orgasm when I start reminding her that I'm her Chastity Slave, I have no hope of escape from having my dick locked in her cage, she owns my ass, I'm pussy-whipped, etc. It makes her cum in no time flat lol.

 

My wife has never been heavy on any sort public humiliation, but likes to lightly humiliate me and I like it too. For instance, sometimes she’ll make it a point to be bossy with me or ask me something in a condescending way when someone is nearby if we are our shopping or whatever. My wife also has a lot of really cute feminine purses, many of them are made out of vinyl or leather and a few of them are rather loud. There have been plenty of times she has me hold her bag for her when we are out. I know it’s just a courteous thing to do and guys shouldn’t see holding their ladies purse as humiliating. However, it’s fun when it’s her hot pink vinyl Kate spade purse and she makes me carry it not because she just happens to be looking at something and needs two free hands but is making a point of me carrying it for her so others can see.

Another thing that she does when we are around friends and family, like dinner or a party, Is she’ll have me make her a plate and bring it to her where she is sitting then have me go make my own plate. Last week we had dinner at my parents, my sister and brother in law were there as well. We were having a lemon pound cake with home made whipped cream for dessert. My wife wanted more of the whipped cream and asked me to put more of her cake. She could’ve easily gotten up herself or asked someone to pass it to her, but I had to take her plate get up in front of everyone to go down to the other end of the table, add more cream to her cake, show her and ask her if it was enough then bring her plate back and set it down in front of her. Just some fun things like that, I’m sure she’ll become more bold with those kinds of things as time goes on.

 

I'm not really in to humiliation but my wife made me try on a nightie at a department store in the changing rooms take a photo and send it to her then purchase it ...doesn't sound to dramatic but for me it was very scary especially trying to hide it on the way into the changing rooms they always have someone there

 

The most humiliating? We are a younger couple in our 20's so she is loving the FLR and keeping me locked 24/7.
I think Either being sent into victorias secret about 7/8 times now to buy myself 5/30 panties to now have about 40 pairs in my "panty drawer" as she calls it would be up there.
The second tie would be telling her 2 best friends. Her 2 best girlfriends know about my situation and 1 of them constantly makes fun of me for being locked and wearing panties which adds so much humiliation to it. They both make fun of me so its actually a dream scenario lol.


I would love to develop into being a cuckold but she wont do that.

 

The most humiliating thing was my wife telling two people at a munch about certain things we do and that I have even without knowing others rather ambivalent feelings about.

 

Wish wifey would tell her sister or friends

 

Very exciting and humiliating, great

 

oooh if only that would happen to me

 

Two things come to mind...
When she tells me to clean the pre-cum off my penis and eat it(We haven't got to cum eating...Yet)
When she allows me to cum, almost all of the time she makes me masturbate for her so she can watch. This is basically my "sex life" now. Masturbating for my Wife(KH).