Humiliating Questions Only

[twinkabella]

Originally Posted by Guv'nor

How did it feel to lose men's underwear?

I actually went to sleep that night in the panties because I was drunk from the party and felt so ashamed the next morning. I didn’t really care about losing my underwear

[twinkabella]

Any more questions?

[twinkabella]

Originally Posted by twinkabella

1. I am not a virgin
2. A man online sent me a dick pic and requested I write him a few paragraphs describing what I would do to it to make it cum and he said I had to fill it full of detail and type as if I was a bimbo stripper and he was my Daddy and I had to use lots of girly slang. He told me first to dress up in lacy lingerie and a sheer kimono which he had made me buy the previous week while I typed it and he kept calling me a dirty slut and laughing at me and I was so turned on and was desperate to cum. But he made me wait until he had cum to my words and he laughed at me and called me names and then told me I could only masturbate if I masturbated to his cock while pretending a banana was his cock and I had to suck and lick it while on all fours in my lingerie which I did and I came really quickly as soon as I started and he told me to keep sucking and then I was told to then lick my cum up from my panties
3. I probably won't post them anywhere unless I was very confident I couldn't be identified.

Originally Posted by twinkabella

This is a little bit hard because I have some limits that might stop it so I would probably need loads of encouragement but I think the one I think about most is going on a girls holiday.

I would be made to get my hair and nails done before the flight as well as a temporary tramp stamp tattoo and my ears pierced with massive hoops and then I imagine turning up at the airport in a comfy travelling outfit like this
https://cdn-img.prettylittlething.co...g?imwidth=1024
and a suitcase like this filled with only girls clothes, shoes and makeup: https://encrypted-tbn3.gstatic.com/s...J3HD_&usqp=CAE

Having to explain to passport control why I look nothing like the man on my picture would be humiliating enough.

Then once we are through I would be made to spend my own money by going on a shopping spree. Buy some girly fragrances and clothes, a girly magazine for the flight, order some cosmos at the airport bar and try and flirt with some of the guys on stag parties.

Then once we landed we would squeeze ourselves into our tight bikinis (like this one: https://encrypted-tbn0.gstatic.com/s...iScgM&usqp=CAE) and order girly cocktails at the pool bar while sunbathing by the pool and reading girly magazines. The girls on the holiday with me would make me talk to them about which of the men at the pool I would most want to fuck me. I would be made to flirt with the lifeguards and establish myself early as the horniest slut at the hotel.

I would be made to eat just salads and fruit because I have to watch me figure, we would go to the spa and drink the girliest cocktails.

Then in the evening, we would squeeze into tight mini dresses (https://encrypted-tbn1.gstatic.com/s...R6H9M&usqp=CAE) and our highest heels (https://encrypted-tbn3.gstatic.com/s...Wau1Q&usqp=CAE) and go clubbing. I would be challenged grind up against as many men as possible and to get as many phones numbers as I can and invite at least one guy back to our room a night.

The guy would then use me as his fucktoy making me give him a lap dance and suck his dick and fucking me and in front of all the girls each night while they laughed.

There are so many barriers to this ever happening right now but it turns me on just thinking about it.

Originally Posted by twinkabella

1) The first time I wore panties was around a female friends house as a dare. I really wanted to go out with this friend on a date but she wasn't interested. She thought of me more as a friend. We were about to go to a friends party and she dared me to swap underwear with her. She said the challenge was essentially to get laid wearing what we were wearing underneath. I was hopelessly infatuated with her so said yes thinking it would show I was up for anything and maybe we could both win by getting together with eachother at the party. She put on my plain grey boxers and I put on her floral knickers that barely covered my ass because she was smaller than me. The rest was normal clothes. Neither of us got laid at the party or even close, a few weeks later she was dating a friend of mine.

2) Only very briefly at a time.

3) Only a pretty unisex looking jumper with a past partner which we would share

4) I enjoyed the fact I was being told to do it - it really turned me on.

5) It tasted kind of salty and harsh. What I liked about it was that I was doing this all because it got somebody else off and I humiliating myself - which turned me on too

I think these were the most embarrassing posts I made in this thread. Can anybody beat them with their questions?

[twinkabella]

Please humiliate me with more questions

[Beatrice.]

1. Describe the most humiliating orgasm you ever had.

2. Have you ever been caught crossdressing? How was it if so?

3. What are the slutiest clothes that you own? Pics would be nice. Just pics from the store are enough.

4. What size (diameter and lenght) was the biggest dildo you used for anal?

5. Have you ever done ass to mouth?

[twinkabella]

Originally Posted by SissySlut29

1. Describe the most humiliating orgasm you ever had.

So the one I discussed earlier in the thread is probably the most humiliating but I will tell the story of the second most humiliating as I have already told the above story.

I was chatting to a person online who made me masturbate with my legs above my head and mouth open but sucking on a banana as if it was a dick, wearing this Spice Girls fancy dress and with pictures of sexy firemen on my phone. I'm a straight man in real life so this was humiliating especially when my own cum started shooting all over my face and into my mouth and when I came I was so full of shame I immediately threw the dress away

2. Have you ever been caught crossdressing? How was it if so?

I once spent quite a lot of money on a dress similar to this and was excited when everyone in the house had left and I could finally get a chance to try it on. Unfortunately, someone forgot something and so I had to desperately hope they wouldn't come into the bathroom which didn't lock where I was as I had no time to get it off and into clothes AND hide it. They literally called my name and everything and I had to answer. Luckily, they never found out I was wearing the dress in the next room.

3. What are the slutiest clothes that you own? Pics would be nice. Just pics from the store are enough.

I recently purged which is why I asked for new clothing suggestions in my other thread. But one of these dresses are the sluttiest thing I've ever owned
https://www.boohoo.com/petite-chainm...html?color=105
https://m.shein.com/ca/SHEIN-Cut-Out...l1661419323162

4. What size (diameter and lenght) was the biggest dildo you used for anal?

I haven't really used dildos for anal but I use a loveegg vibrator

5. Have you ever done ass to mouth?

No

[bdsmlover24]

Describe the 3 most humiliating fantasms you can find that you could do with a lot of enccouragement but that scares you a lot too

[twinkabella]

Originally Posted by bdsmlover24

Describe the 3 most humiliating fantasms you can find that you could do with a lot of enccouragement but that scares you a lot too

The first one is the one I already wrote in this thread about a girls vacation. I think I could do a toned down version of that where I spend the whole holiday feminised with enough encouragement.

The second one:
One would be serving a dominant couple dressed up as a sexy bimbo. I would fluff the man to prepare him for sex with the woman and they would degrade and humiliate me.

The third one would be being made to serve a part full of girls as a slutty waitress, eventually being forced to strip and pole dance for them dressed a stripper.

[Beatrice.]

How do you remove the hair on your balls?

[twinkabella]

Originally Posted by Beatrice.

How do you remove the hair on your balls?

I mostly shave but I have waxed in the past

[blankblank]

are you sure youre not trans?

[twinkabella]

Originally Posted by blankblank

are you sure youre not trans?

I’m not 100% sure but the feeling of being emasculated *by others* is what turns me on and when I’m not horny I don’t feel like a woman

[twinkabella]

Most humiliating question before midnight UK time wins a picture

[twinkabella]

DESPERATE for more HUMILIATING questions

[Robyyn_ur_heart]

Whats your most humiliating memory thats not connected to your kinks?

Would you ever seek out a glory hole to suck dick?

Have you ever been out in full girl-mode? If you have been, what were people reactions to it, did you feel exposed or comfortable?