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

How do you know they are vanilla? Maybe they are thinking that you are.

 

What was the prize for the 'winner'? A cum-filled kiss does not count

 

I figure the ladies thought it was an excellent prize?

 

This is the funniest - sweetest thing I've read on the entire site, You Rock Mrs Bennett !

 

She loves to tell her friends about my micropenis. All of them know and I have a collection of pics of them making the small pee pee sign

 

That is so awesome! Just the thought of that makes me so horny. I would love for my wife to humiliate me like that.

 

About a month ago agoinafu gave me this A, B or C dare,

NURU MASSAGE: Go to the Nuru Massage place 20 minutes down the street locked in chastity wearing a thong under my street clothes. Give the masseuse the key and get a massage teased to the edge over and over before she locks me back in chastity and puts the key in an envelope and seals it shut. No happy ending just denial and frustration.

My Femdom Roommate scheduled the massage with the masseuse who has done these dares a number of times before. She scheduled it for 8:30 that night. At 8:00 PM my roommate locked me in this cage.

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Then she slipped on these leopard print and lace crotchless panties.

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I put on my street clothes and she handed me the unsealed envelope with the key to my chastity cage in it for the masseuse, Linda. It is a 20 minute drive to the massage parlor and I got there at 8:30. Linda had done these dares before and charged $80 plus a tip for the hour.

It was a great NURU massage and she teased and edged me intensely with her hand but knew just when to stop. I asked her to please finish and let me cum. How would my roommate know, I would tip her well if she would just please let me cum. Finally I couldn’t take it anymore and I grabbed my cock and started rapidly jacking off to cum when she slapped hand and grabbed and squeezed my balls to make me stop. Then she then locked me back in the chastity cage, put the sissy panties back on and told me to get dressed that my hour was up. I was frustrated and pissed. I got dressed and started to walk out when Linda said, “What about my tip?’ I replied, “No cum. No tip.” I left and got in my car when I realized I hadn’t gotten the key from Linda. I went back in and asked Linda for the key and she gave me the sealed envelope which she kissed on the seal leaving her lip marks. She said, “I sealed it with a kiss in case you tried to open the envelope on the way home so that you could jack off.”

When I got home 20 minutes later, I gave my roommate the envelope. She opened it and took out a penny and a note but no key. The note said, “HERE’S YOUR TIP CHEAPSKATE. IF YOU WANT THE KEY BRING ME THE $50 TIP I EARNED. WE OPEN AT 10:00 AM AND CLOSE AT 10:00 PM SHARP.”

It was 9:55. No way was I getting the key tonight. So I stayed locked up in my panties until the next day. My roommate told me at about 11:45 the next day that Linda had an opening at noon. With traffic and everything I got there at 12:10 PM. Linda walked me into a room and made me take off all but my shirt. She said she wanted to make sure I was still locked up in my crotchless panties. Then she took my clothes and said someone had come in for an hour appointment when I didn’t show up and to wait there for her to finish with her appointment. Like where was I going to go?

About 50 minutes later there was a slight knock at the door and Linda opened the door and was with her client. She said, “Al didn’t believe me.” The guy started laughing his ass off. He said he wouldn’t have believed it had he not seen it for himself. Then he took out his phone and said he had to get a pic of this. I said no face so he took a close up pic and laughed some more He was still laughing when he left.

Linda asked for her tip and I took a $50 bill out of my shirt pocket and gave it to her. I asked for my pants and she said $20 more. I told her I left my wallet in the car because I figured she would ask for more. She said, “No $20. No Pants.” So I covered myself as much as possible and went to my car which was locked of course and she knew the keys were in the pants she had. What she didn’t know was that I had a hide a key under the bumper.

I brought her the $20 and watched her drop the key in the envelope and seal it with a kiss. When I got home my roommate opened the envelope and handed me the key. As I was unlocking the cage my roommate held up her phone for me to see and said, “Al takes a nice picture, don’t you think.” BITCH

 

I can see why you remember every detail,

 

She is a bit of an exhibitionist and loves to be that way on vacation where no one knows us. She really enjoys pegging me on our hotel balconies. We’ve had a few times when She has done this and people watch us.

At home, we have a very private yard and She enjoys having me outside caged and plugged and will whistle at me hoping a neighbor might peak over the fence and see me.

 

Ruining myself on her feet and then lapping up my mess.

 

LOL, that's actually my KH's favorite - timed just as she orgasms with her wand.

I'm getting to be quite turned on by it also

 

Most humiliating:

I lost a bet to her I'd beat her at a sport we both play.

I had to mop the kitchen-diner floor naked except for cage, plug, tiara and "Kitchen Bitch" apron. During the cleaning she attached various items of 'flair' (like TGI Friday) to my cage belt e.g. small soft toy rabbit, some stationary (paper clips, notepad & pen) for her amusement.

 

I have a rule that the keyholes out there might like.

Every now and again I'll let my husband cum. During the tease session I will ask him "do you want to come" and if he tells me he does, I will make him cum and then collect it in a syringe and squirt it down the back of his throat.

He is always restrained when I do this which is important because once he comes, the idea of eating it isn't as appealing anymore.

I have had this rule for years and it's one of my absolute favourite ways to humiliate him.

 

My mistress prefers I lick it up. you get the full taste on the tongue, and probably miss that if it goes straight down your throat. She doesn't always want to watchmen do it though

 

When my wife first told her girlfriend about our lifestyle and made made me show her my cage.

 

I can only imagine. Has not happened to me, but as I just posted, y wife is anything but a girly girl . Pretty, looks all woman, but has no girlfriends. Much prefers male company. Always has. Ironic that while she was always pretty, there were lots of women I knew way back when , plus actresses y, who were stunning or beautiful. 50 years later, and my wife looks better than all of them. Many of them look down right rough. Not her. She has aged flawlessly, rarely worn make up all her life, . Just a natural beautiful farm girl.

 

My K/H new favorite is to have me locked wearing skimpy panties in front of her girlfriends. Then she has me take off the panties and removes the cage. Each girlfriend gets to set a kitchen timer that I can't see. I am allowed to jerk off until the timer goes off. Then I have to stop and stand with my hands at my side and beg the next girlfriend to please give me more time as my cock goes limp. This goes on until they are roaring in laughter and my K/H locks me up totally frustrated and humiliated.

 

I can’t even imagine how embarrassing this is, I’d love to hear more details.

 

I think they must have had a side bet as to which one could get me the closest to cumming. My Femdom K/H had a fly swatter that she would swat the tip of my cock with with if I tried to stroke after the timer bell. They intentionally set short times forcing me to stroke faster and faster to no avail.

 

Not bad.

 

I would be so incredibly humiliated to be required to jack off in front of a strange woman. I think i would cum almost immediately.

 

Goddess recently elevated things to a level W/we have never done before. She told me that because i had been so good She was going to let me out for a full day but only while i was at work and on a day i had meetings all day so She knew i could not cheat. She left for work before me without leaving me the key. She then texted me and said She dropped the key off with my secretary and i was to ask Her for it. Goddess did not tell Her what it was for, only that i needed it and left it at home. i then had to ask my secretary if Goddess (who i obviously refer to by name at work) dropped off a key for me. My secretary did not know what it was for, nor did She ask, but the secret thrill was terrifying and exciting at the same time. The “best” (?) part was when i tried to use it i realized Goddess intentionally gave me the wrong key. i was caned harshly when i asked Her about it because i did not abide by Her 2nd rule - only Goddess can remove the device unless She specifically directs otherwise. Basically, it was Simon Says and Simon did not say i was to try the key.

As an aside, W/we NEVER involve vanilla people - particularly at work - in O/our kink. This was innocuous because i routinely forget my keys so my secretary would not think anything of it.

 

Humiliation is something we’ve agreed upon as a punishment. It’s not something I crave at all, but I can tolerate as punishment for bad behavior. It’s proved a great deterrent. She’s promised to take me shopping on leash and collar if I ever give myself an emission. (That’s along with a harsh paddling). I’ve yet to commit that sin.

The most humiliating thing she’s actually done to me is to make me strip naked in a crowded campground. Then she proceeded to cane me really well. This was a punishment for me looking at a woman’s ass earlier in the day. I don’t know if anyone saw or heard us but I was humiliated nonetheless.

Also, back when she would allow me to cum on occasion, she loved to make me swallow it. Usually she would ruin me into a glass, and make me drink it, or she would ruin me into her hand and feed it to me. Sadly, she forbids any emissions anymore.

 

You were punished for looking at a woman’s ass. Just out of curiosity, what was this woman wearing that attracted your disrespectful leer? Not that it justifies it, I’m just curious why you looked.

 

We've been at this in one fashion or another for a long time now. I don't know if it's humiliating or embarrassing, but over the years I've had to show myself to one of her friends and one of her sisters. Nothing wild happened with her friend really. It was the old CB6000 cage, she drummed her nails on the cage, tugged the lock a little bit and it was over.
Her sister has known for some time and would do little things like tell me to fetch her shows for her. No please or thank you, just a pleasant sounding command, all with that little smile. Eventually on her last visit all was revealed to her, for like ten days. She's in love with the idea but her husband won't have anything to do with it.