How I Became a Real-life Bridesmaid

My Superior, Mistress Myckie Jo Katzanburg (before she decided, which was my fault, to take a well deserved vacation) asked Mistress Amber to communicate with Mistress Rosemarie to suggest (supervise an assignment) that it was time one of my fantasies should become a reality. Mistress Rosemarie picked one of my many fantasies that was about dressing up and being asked to be a Bridesmaid in a Wedding. So …. That is what I am to become.

Mistress Rosemarie and I had just graduated from school and one of her friends was getting married and she was to be the Maid of Honor. The problem was that it was only two weeks before the wedding and one of the Bridesmaids had backed out of the Bridal party over some stupid arguments that girls always seem to have. She was now short one Bridesmaid. Her girlfriend knew about my Cross-Dressing lifestyle and they often talked, many times in front of me, about how I should serve Mistress Rosemarie. Well they decided that since I like to dress in feminine clothing, that I would make the perfect Bridesmaid.

After protesting l agreed to do it, if they would keep my secret. I really did not think they would expose me and they would let me off the hook as soon as they found a real girl to be a Bridesmaid. I was dead wrong and thus began the most humiliating experience of my life.

I was made to be her Bridesmaid and wear a Bridesmaid gown and I was exposed to the entire wedding reception. Mistress Rosemarie smiled for two weeks and as I was humiliated over and over again and finally walked down the aisle in the Wedding Party. I was exposed to all of her friends.

The greatest humiliation of my fantasy actually occurred the week before the wedding. It was the Bridal Shower. All the horror stories of a Bridal Shower that I knew of as a man was to come true. The theme of the Bridal Shower was “The High School Prom”. Each Girl that was invited to the Bridal Shower was very excited. Every Girl loves her Prom and her Prom Dress. I, on the other hand, was humiliated by the thought of wearing a Prom Dress and attending a Bridal Shower with a lot of Girls.

Saturday came and I was taken to the beauty parlor to have my hair “pouffed”. The women at the salon teased me the whole time I was there. Then it was on to the Nail place to have my nails coated in a pretty shade of pink. Finally we were back in my bedroom and the horror really started. First my sissy-clitty cage was put on me because Mistress Rosemarie thought I would get excited by a lot of girls in pretty prom dresses and that I would excite myself and have an orgasm. Then came red crotchless panties, Pantyhose, a big white stuffed Bra, a corset drawn snuggly, a big white and pink Prom Crinoline to make my dress look like a princess’s Prom Gown.

There were other accessories all to make me look pretty and to embarrass the hell out of me. Then the Prom Gown and I was ready for my first Bridal Shower. I was so humiliated, but here I stood in my Bridal Shower Prom Gown, complete with Corsage.

I was then led to the Restaurant and had to introduce myself to all these women and explain why I liked to Dress Like a Girl. The Giggling and Laughter was so embarrassing. Then Mistress Rosemarie made an announcement and asked everyone to help in punishing her sissy. I could have crawled into a hole. I thought it could not get worst, then it did. One of her girlfriends told her that she had just broke up with her boyfriend and that she was very “horny”. Mistress Rosemarie told her I could help and that I would be glad to provide some oral stimulation. I was then dragged to the Ladies room, led into a stall and after she had me help her pull down her panties and me on my knees, I had my head pulled under her Prom Gown and stimulated her to a point of orgasm as she moaned and groaned in the Ladies Room. This was followed by several other Ladies asking for the same favor.

In between servicing any Lady that took me to the Ladies Room, I was asked to dance continually. It was one humiliation after another as they would tease me as we danced and grab my crotch to feel my sissy-clitty cage which by now everyone knew about. Then Mistress Rosemarie made another announcement. She told all the other Ladies that apparently their affections for me had caused my sissy-clitty to enlarge and was throbbing inside its cage. She asked if they thought I should be relieved of this throbbing and all the Girls clapped and cheered. As two of the other Bridesmaids held up my Prom Dress and another pulled down my panties, Mistress Rosemarie undid my cage. She made another announcement that if I could control myself for 5 minutes, I would be allowed to shrink into the corner like a sissy wall flower. But if I could not and messed all over the floor that I would have to clean my mess up by using my tongue once again. She started Milking and I lasted barely 3 minutes.


I reluctantly and embarrassingly got down on my knees and proceeded to lick up my own cum. This was a Bridal Shower that I will never forget.

Treatments Completed During This Assignment


This is a table showing the extra treatments that I subjected myself to for failing to finish this objective in a timely manner.

Day Daytime Nighttime Date
7 November 22
8 November 23
9 November 24
10 November 25

I have completed my posting of my fantasy and listed the Treatments. I also must acknowledge that I was not completely successful in my treatments.

Day 7 – Sunday Night – I wore my Nightgown for most of the night, but could not sleep and took it off in the middle of the night.

Day 8 – Monday Night – Again I could not wear my Nightgown for the entire night. I was so tired.

Day 9 – Tuesday Night – Once again I was unable to wear my Nightgown for the entire Night.

Day 10 – Wednesday – I was supposed to wear my Bra during the Day. I was afraid to wear the Bra to work worrying that someone might see it. When I got home I immediately put the Bra on and wore it for the rest of the Day.

I did not ignore any of my Treatments and tried to do each one, but did not complete them completely as I was afraid of exposure. I accept that I did not complete the Treatment and expect additional punishment by My Superior, Mistress Myckie Jo Katzenburg and Mistress Amber as is convient for them.

I will stop the treatments at this point until notified of my punishments for this.

18 thoughts on “How I Became a Real-life Bridesmaid

  1. Wow, sounds like you had quite the humiliation, when is the wedding,and do they need another bridesmaid? Nah i couldnt be made to do such a thing. anyhow what is that false vagna on the table about you dont mentionit in the report. also your pictures arent there for the added items duriing the week. I t you are wishing you never told this fantasy to anyone, I have to be glad i dont reveal i like such things to, and that i havent any one actually working on me in person. Take care and enjoy the wedding.

  2. Hello sissybabyjamie. This is one of my fantasies, so they do tend to be exaggerated, but are certainly real in my mind. Being a Bridesmaid or a Bride was always one of my fantasies. The wedding is sometime in the future I am first a Bridesmaid (future episodes of my dreams) and ultimately the bride. The vagina is just a simulation of what it would be like to satisfy all the women at the Bridal Shower. Certainly a lot of work. My tongue and lips were tired. Revealing one’s fantasies is humiliating in itself as I am sure we all have private and secret fantasies. Some day I do hope to enjoy the Wedding. sissy billy

  3. Ah i understand, none of this really happened then. i mean the going out to the reception and all. Sounds like the kind of fantasy i have had, though in mine i am always the floewr girl in the cutest dress, and thick diapers. I would love to be that in the wedding of your dreams hehehehe.

  4. My assignment from My Superior, Mistress Myckie Jo Katzenburg was, since I had seemed to have so much fun making love to my sissy-clitty as I had fantasized and written in my Diary, to reenact my fantasy as best as possible in real life. I do not have the opportunity nor the courage to actually appear like this in real life in front of other women. In the Privacy of my house I did what I could with the girlie clothes that I have and I dressed up in a Prom Dress and made believe I was going to a Bridal shower. I forced myself to stand up in high heels for an hour and had cocktails like at a real cocktail party. I do understand now why a girl is always complaining about her feet hurting. My feet hurt a lot in high heels. I did sit at the table and have dinner all dressed up.

    I also, using the vagina shown in the picture, simulated pleasuring several girls by licking the vagina for several minutes at a time and several times fantasizing each was a new girl at the Bridal Shower.

    I then milked myself fantasizing that it was being down by the other Bridesmaids and trying to hold it for 5 minutes which I could not. I then, like in the Kara Play that I performed, did get done on my knees and lick up the mess that I made. As before, it was discussing and humiliating doing this.

    Soooo … parts of my post were very true and only the fact that it was done at a restaurant in front of other guests of a Bridal Shower is exaggerated.

    Fantasies are great in bed, but not as much fun when physically enacted even in the confines of your own house.

    sissy billy

  5. On this day after Thanksgiving, you should be very thankful sissy billy that you can milk yourself. i’ve been in my chastity device for over 1 week. i’d give anything or do anything to be able to milk myself. So count your blessings you lucky sissy.

    • You may be able to remove your chastity once you become a full member. But several days ago you indicated you would be working on your next assignment, and I have heard nothing of it. And complaining about your condition won’t make it go away any faster.

  6. i’m sorry that i complained about my condition. It’s an honor to serve Mistress Amber and as such, i should not be a complainer. It will not happen again. Please forgive me, Mistress Amber.

  7. Hello Monique Qua. I am happy to see that another sissy client is trying to join the “The Institute for Cross-Dressing Punishment”. It is easier to serve Mistress Amber when you know there are other sissies in the same “proverbial” Boat. I am thankful on these days after Thanksgiving, but everything comes with consequences. Without getting into a long story, you might want to go back in my History and find a Post about being careful what you wish for. Sometimes you get more the you wish for. It is also in my nature to complain and whine, even though I try hard not to, but trust me, every complaint and whine just adds to the tasks that you complain about to start.

    On a happier note, Welcome Monique Qua and good luck on your assignments.

    sissy billy

  8. I would like everyone to know that having witnessed sissy billy’s fantasy being played out, she really did enjoy it. I think she enjoyed it so much that I may have to accept sissy billy as being ready to become my Bride. Perhaps, Mistress Amber, I should have sissy billy start planning our wedding. I am sure she would love doing all those girlie things. Maybe I should have her go online and join one of those wedding planners. In fact the next time you go to the store sissy billy, I want you to buy a Bridal Magazine. How embarrassing buying a Bridal Gown Magazine dressed as a boy. Enjoy the humiliation.

    This could be a lot of fun and so embarrassing for sissy billy. Maybe I should make her make a monthly post of all the sissy girlie things she is doing as a Bride. I will have to confer with Mistress Amber and Mistress in Training Myckie Jo about this.

    In the meantime sissy billy, maybe you should not enjoy your fantasies so much. They may become reality.

  9. I’ll have to admit, at first i was thinking no way some bride actually like a sissy come to her wedding like that..unless he was the bride. Now that said, i love your storytelling in this post, and wow, even acting it out must of been a thrill/ horribly humiliating time for you. The closet I’ve come to actually having a real woman act out a fantasy with me is when my first girlfriend poped a pacifire in my mouth when i was fighting with her and told me to be quiet or she’d spank me. She was of course, just playing on my fetish to make me stop, but wow.

  10. Hello Sissy_misty. I do like story telling and I do get excited telling a tale. This was fiction as noted in the heading. I do not have the courage to actually do this, but in my fantasy life and, Oh how I wish, I would love to find someone to make me do this in a far away place that I did not know the people. I would absolutely love to be the Bride or even a Bridesmaid. I do have a rich and exciting fantasy life.

    sissy billy, a want a be Bride

    • I also love to dress up in my prom gowns and fantasize slut_tricia, but I learned that wearing a pretty prom dress all night long for the prom can be tiring and not as much fun after the initial excitment and fantasy wears off. Being a girl for long periods of time are not as much fun as one would fantasize.

      sissy billy

  11. I suppose, Sissy Billy, it depends like everything else about how much practice you have had and how often you do it. I wore my pretty prom dress all afternoon and all evening. When I got home I didn’t want to take it off. Life is more fun if you don’t fantasize, just do it. Hugs

  12. Hello slut_tricia. I first must comment that I am not worthy of having my name capitalized and as a sissy do not deserve to. I must admit that I do fantasize too much and do not live out my fantasizes. I have always dressed and then got quickly tired of being a girl and then undressed. I try, but while I love to dress-up, I do not have the desire to follow through. However, I am being helped in this failing by the Mistress’s of “The Institute for Cross-Dressing Punishment” through prescribed activities and punishments. I am sure they will also help you in your failures by assignments and punishments.

    sissy billy

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