Most Humiliating Dare

[IAAS]

I'm very into humiliation and embarrassing tasks, and I know many others are also. So I'm curious: What's the most humiliating dare you've ever received (or perhaps given)? Something that really made you feel naughty.

[Postevak]

I was told to integrate a function f(x) = e^-x^2. I had been trying to do that for many days, using many different methods, until I found out that it is not possible! It was very humiliating.

[smallonem]

although you might say that is not humiliating, and I agree.

I felt humiliated and very horny, was online and a Master asked me to ride a bottle, I had to put the bottle on the floor and riding it for some time, it felt so humiliating but good at the same time.

I had my full body showing while I was going up and down being fucked by a bottle, and it was quite a large bottle as well.

[Lovestorun]

give a blowjob in the nude at a party

[horserider]

Wetting my pants at my horse riding stables so it looked like I wet myself and letting a group of girls see it.

[rhode64]

I don't humiliate easily but I have done a lot of dares that really turned me on that were pretty public and I got seen . The one that always come to mind was when I was about 19 and doing paper rounds for extra money and got dared to do it nude it was a real rush .

[ooo]

So far the worst I've done is putting on my sisters tight pink bikini (rode up my ass and made it look so feminine) and twerking for girls on omegle watching them laugh was brutal but I loved it

[JennnB]

The worst (most humiliating!) dare I did that I'm willing to admit to was going outside nude and playing with myself until I orgasmed! Luckily it was dark so no one could see me, but I'm sure I could be heard.

[The Slutty Princess]

A member on GD had dared me on my thread to ask a cute neighbor for sex toys. I carried out with it and it was certainly a humiliating experience!

[happytosubmit]

Licking the toilet seat in my hotel room. As well as licking the soles of my shoes completely, whilst I was naked and on my knees with my mistress (that time) on cam.

[natethegreat]

It's a really hard question to answer for me as I have been giving/receiving dares since a very young age. Having to show new people my small penis is probably the most humiliating thing I think about until they have seen it.

I am assuming people want to hear about things given and received online, via getdare for example. That is a bit easier to answer, I would say, having naked and humiliating pictures posted online, forever, on tumblr being spread and exposed.

[Scrap]

Back before I truly started accepting my feminine side, I was dared to go to the gas station as a girl. I had to wear a thin, short, white sundress, thong panties, and heeled sandals. They put make up on me, and did my nails. Then they locked a chain-type dog collar around my neck. The task was to make a purchase from the clerk, prepay to fill up the car, then come back in to get the change.

It was about 10pm on a Friday, and in a fairly conservative town. The station was kinda busy with bar traffic. I got a lot of cat calls, and the clerk asked why I was dressed like I was. I answered truthfully, and added that I would get extra points if I came back with cum on my face. There was a lot of laughter at that as I went out to pump gas.

When I came back in to get my change, there were three guys standing next to the counter, grinning. They said they were volunteering to get me my "extra points". I cursed myself, but could not back down. We went into the restroom and I sucked off all three, accepting the loads on my face, chest, hair, and some in my mouth. They snapped pics, and I asked for them to send them to me (which they never did).

I walked out to the car to even more obscene remarks and calls, and headed back.

[zephyrnem]

Hard to say. I love humiliation.

My favorite would be, probably, the first time I had anal.

I pushed this guy...and he kind of responded...

I drove a half hour wearing only a long t shirt.

Met him at a Walmart parking lot. He got in the car, and to check he jumped in my car and grabbed my balls. I felt very nude.

He then had me follow him to his house. Had me stand around in just my shirt.

I had said I was a slut and was dying for action.

He rammed his large cock in my mouth. I gagged. I couldn’t handle it. I tried my best. It was long, and I was inexperienced.

He kept trying...then took me downstairs.

He lubed me, which made me feel...cold, exposed, stupid, now

He then penetrated me...the feeling I hadn’t expected. Intense burn. Urge to pee.

He showed me the blood on the condom.

I was so thin, he had me sit on his cock, and made me watched as is poked my stomach out. He laughed. I was limp.

I was cold, in pain, exposed as a bs slut. I let him ram me.

I finally got bored.

Drove home with my shirt. Feeling like an idiot slut boy, but then turned n by it.

Wish he’d have taken my shirt...or showed me off the way he said he would.

So many confusing feelings.,.and turned on on top of it.

[Paladintwk]

These two happened on back to back weekends

FEMDOM ROOMMATE SURPRISE: My roommate likes to check out my T or D account to see what kinky things I am doing. She saw that I fantasized about gloryholes and decided to surprise me with this dare. I was given a Strip Club Dare from my PMs. She locks me in my CB 3000 metal cage and slips on my black and neon pink lacy thong, tan short shorts, a black shirt with a black light print and sandals. She says to bring this toy and maybe she will unlock me and we can play “Red light Green light” on the way to the club. https://www.getdare.com/bbs/picture....ureid=58887She grabbed a canvas bag by the door and said “Lets go”.
When we drive by the strip club she says surprise and pulls into an adult store. She grabs our stuff and drags me into the gloryhole booths. She sees two guys cruising and gives each of them a note and they nod yes and smile. We go in a booth and they go in to the booths on either side of us. The notes read “My friend is straight but has fantasized about gloryholes for years. I recently discovered tons of gloryhole porn and secret gloryhole sexual fantasies that he wrote and sent to his friends on T or D, We will help you get good and hard and stay that way the whole time you watch me make him give me an awesome squirting orgasm. The whole time you will help me humiliate him by making him my sissy sub. You will have some say in what I am doing and feel free to make suggestions. For the finale I will have him jack you off while I tease your balls until you blow your load all over his face. The one with the biggest load wins $50”.
So we go in our booth and they go in theirs and we all lock our doors. She strips me naked and I see large cocks poke through the gloryholes on either side and the guys faces watching from the larger top holes. I am thinking hot damn a gloryhole gang bang just like one of my favorite jack off videos:
Before I know it my roommate has taken wrist and ankle cuffs from her bag a has me bound with my hands be hind my back. Then she pulls out my chastity cages and the three of them decide they want to use the one that makes my cock totally inaccessible. https://www.getdare.com/bbs/picture....ictureid=59900 and these sissy panties: https://www.getdare.com/bbs/picture....ictureid=65798
Next she tells them she is going to insert a ten function prostate vibrator in my lubed ass and has them pick one. They choose this one. https://www.getdare.com/bbs/picture....ictureid=63015 and she puts in a new battery, slips the cock and ball rings on, takes her time inserting it my ass pushing it in and pulling out while trying different functions. When she is sure my ass has it held snug against my prostate she turns it off. Since my cock is starting to swell from her anal foreplay she quickly lubes my cock, slips on the chastity cage and locks me up. Then she reaches in her bag and pulls out two new of these and offers one to each guy if they want to join in the fun. https://www.getdare.com/bbs/picture....ictureid=58888 and they both take them. Last since I am her sissy sub they pick the most humiliating sissy thong she has in her bag. I am now in the booth wearing only the black sissy panties with my bright shiny metal cage hanging prominently through the crotchless bottoms and a black prostate vibrator in my ass with its cock ring stretched tight on the base of my cock and its ball ring strangling my balls.
https://www.getdare.com/bbs/picture....ictureid=63617
https://www.getdare.com/bbs/picture....ictureid=59900
https://www.getdare.com/bbs/picture....ictureid=64181

She reaches in her bag and pulls out a black slave collar and leash to match my black sissy panties and puts it snuggly around my neck and attaches the leash. https://www.getdare.com/bbs/picture....ictureid=65471
She takes off the ankle cuffs, pulls up her skirt, slips off her panties and pulls me to her crotch and says,” If you want out of that cage anytime soon so you can cum again you will start licking my pussy and after I am aroused you will lick my ass”.
After she is good and wet she stops me. She says she knows this was a surprise and is my first time at a gloryhole so she won’t make me suck their cocks. But she says, “It is rude of me to make them watch you licking me like this.” She reaches in her bag and pulls out sanitary wipes and proceeds to clean their hard cocks. If we are going to do this again sometime you need to know the feeling of a hard cock on your tongue. She pulls me by the leash up to the first hard cock. She tells me to first lick his balls for a minute and then just the tip of his cock for a minute. Then she pulls me over to the second hard cock and I do it again.
See she says, “That wasn’t so bad”. “Now back to me” she says. When she is wet and aroused she stops me, reaches into her bag and puts on this mouth gag dildo. https://www.getdare.com/bbs/picture....ictureid=58893
“Now face fuck me to an earth-shaking orgasm”. Her orgasm climaxes with her squirting her pussy juice all over my face, chest and crotch.
“We are almost done but in order to remove that chastity cage and that pink thong, I promise these gentlemen that you would give them a handjob”. “On second thought they would probably prefer that I give them a handjob but you can watch up close and personal”. She pulls me over to the first cock and has me lube him up. “I forgot” she says. You felt their cocks with your hands and tongue but I forgot what guys who come to gloryholes love the most is your ass. Good thing I put that prostate vibrator in your ass and she turns it on. I believe that sliding their hard cocks with your vibrating ass crack should bring them right to the edge for me”.
I feel his hard cock sliding faster and faster in the vibrating crack of my ass when suddenly she flips me around, pushes me to my knees and jacks his huge throbbing load all over my face and into my mouth as I gasp in surprise. She yanks my leash over to the second guy who is horny as hell from watching his friend across the booth. This guys load is huge and splatters his cum not only on may face and mouth but soaks my chest and crotch.
Just when I think it is over she pulls me back to the first guy and asks if he recovered enough that he could hump my ass crack and cover it in cum too. .No sooner then I feel his cock stop throbbing his cum down my ass crack his friend is yelling that it is his turn. My roommate pulls me over, backs me up and makes me bend over and grab my ankles. At first I wondered why until his river of cum ran down my back and on to my face again, It was clear the second guy won the $50 prize. She told them that she planned to add this to my PM Dares 3 or 4 times a year. “Maybe next time I’ll get 4 guys to play”.
She unlocked me as she promised and helped me clean up with sanitary wipes and towels. As I get dressed she says, “You have been such a good sport about this how about I go into the booth next door and give you an unforgettable gloryhole blowjob. She rushes to the next booth, looks through the hole and I drop my shorts to my ankles and poke my hard-eager cock through the gloryhole. She strokes and teases it right to the edge and then licks and sucks the head of my cock driving me crazy Finally I can’t take it any more and just as I explode my booth door opens and there stands my roommate recording me on her I Phone with my shorts down and my cock in the glory hole. I am being sucked totally dry squirming and begging whoever it is as I endure 3 long minutes of post orgasm cock sucking.
When it is over and I am pulling up my shorts she gives me a fifty dollar bill and says, “The guy that won the cum load prize said he would give me the $50 if I let him suck your virgin gloryhole dick”. “Come on you look like you could use a drink”.

The following weekend:
My femdom roommate loves to barge in when I am playing T or D. especially when I am in the middle of a dare. She caught me on my knees doing my Gloryhole Role Play PM Dare a month ago and was intrigued. I got a Chastity # 2 Dare and she was to pick everything. She said come on lets buy something new at the adult store for the dare. When we got there, she grabbed a bag from the back seat. As soon as we walked in she took my hand and made a B line for the glory hole booth room and bought a handful of tokens. Once in the booth she stripped me naked, slipped on, inserted and turned on this prostate vibrator, https://www.aliexpress.com/item/10-S...27424c4ddqK5jb
locked me in this pink sissy cage,
https://www.aliexpress.com/item/2016...203f3c007YyKY0
put on these sheer panties https://www.aliexpress.com/item/Siss...5d963c009gQxcJ,
this mini skirt https://www.amazon.com/Avidlove-Plea...f=cts_ap_1_vtp ,
this top.
https://www.amazon.com/Avidlove-Slee...f=cts_ap_1_fbt
and these stockings
https://www.amazon.com/ToBeInStyle-W...CXNEW7BW6HPJ9Z
Then she handed me a dozen neon pink 3 by 5 cards that read, “I am locked in a pink sissy chastity cage with a 10-function prostate vibrator running in my ass. In order to be freed I must pay 3 men $20 each to let me give them a hand job through a gloryhole and put their cum on this card as proof.”

Then she grabbed all my clothes and pushed me out of the booth into the hall and said, “Cruise Sissy, I’ll be in the car waiting. You have an hour and then I will leave. I am sure one of these gentlemen will give you a ride for a blowjob.”
I was lucky and finished in 45 minutes, only because I ended up sucking the last guys tip a few times because the clock was running. When I got to the car she gave me the keys and told me to finish the dare by going through the drive thru on the way home. At the drive thru she introduced me as her Sissy Chauffeur and ordered a plain hamburger for me.
When we got home she released me and had me play this Cock Hero game until I blew my load on my plain hamburger that I then had to eat or be locked up again for the night.

This weekend:
For me: From my albums pick what I should wear as a Femdom sissy slave. Pick from my Chastity Device Album a chastity cage to be locked up in. Pick a prostate vibrator to insert and any toys or bondage gear to be available. I will show my femdom roommate your choices and she will put it all in a tote bag to take to the site of your choice where she and her kinky femdom friends will take off all my clothes off and dress me in your choices. They take my clothes and tell me I will get them back when I get home. This dare will occur this weekend. Should they:

A. Take me to a nudist resort night club and have me dance on the stage and swing on the striper pole.

B. Take me to a sex club and put on a femdom show taking turns with me with their strapons and having me service them with my tongue or the penis mouth gag. For the finale they will take off the chastity cage and hogtie me with my legs over my head so my cock is hanging over my mouth and face. They will take turns edging me until my roommate jacks a huge load of cum in my mouth. After I cum they will each tease and stroke me while I squirm from the post orgasm torture.

c. Take the adult store with gloryhole booths. They will strip and dress me and lock me in the cage you picked. They restrain me in a doggie position and invite men to come in the booth to watch their femdom sissy slave strapon show with the promise that the finale will be them squirting all over me first after which they will jack the men off and make them cover me in cum. The guy that blows the biggest load will win $50.

[subs]

Doing jumping jacks naked on the balcony during the day.

Another one actually really humiliating was licking the toilet in a hotel room...