A Trip with my Mistress

I made a big mistake at the end of last year. A sissy does not have any rights and only has the obligation to please her Mistresses. She is a sissy and should be kind and sharing with all and therefore has an obligation to other sissies also. She should be honest. But most of all she has an obligation to perform her sissy duties without prodding or insistence from her Mistresses.

Simply, she should Volunteer.

I did not and therefore I am where I am now. I am sorry Mistresses and other sissies. The correct thing to do would have been to show everyone how excited I was over my presents from Mistress Rosemarie and to share this excitement and tell everyone what I got. I was too embarrassed to do this and now I have to physically wear and show everyone my new things.

It is our Anniversary and Mistress Rosemarie decided that we should take a nice trip and that my main purpose was to pleasure her enormously. I was also to bring my presents because she intended to make good use of them. I packed my Suitcase including my very pretty negligee I received from her for Christmas, several other negligees so that I would look pretty for her each night and of course the new two quart enema system, new pink soap, condoms, a Bridal Magazine and of course panties, bra and pantyhose that I would wear full time for the weekend. She examined my suitcase, found it complete and off we went.

Packed and the suitcases loaded in the car we drove off on Day 1 of our trip. Mistress Rosemarie drove as she is a much better driver then a sissy could ever be. She began to explain what would happen on our trip and I began to blush and worry already. She decided that my humiliation should start now and she had me put on a pretty women’s kerchief and tie a bow at my chin. When we passed cars I was to look directly at them. We were away from home and little chance of exposure, but it was humiliating and Mistress Rosemarie even slowed up sometimes so they could get a good look. It was humiliating. This was just the start.

Day One:

We arrived and checked into a motel. The scarf had been perfumed and I swore the receptionist could smell the feminine perfume. She smiled at me several times, but I was not sure. More Humiliations. We went to the really nice lobby bar and sat for a long time and talked. I was only wearing a fairly thin man’s knit pull over (It was to hot in the Hotel and she made me take off my bulky sweater) and I could swear you could see my bra through it. She delighted in this.

After eating a nice dinner and listening to a band in the bar we went to our room were I knew I would soon be punished. The last two days before we left I had been feeling sorry for myself and on several occasions had talked back to Mistress Rosemarie. She told me to stop once and when I did not, she told me I would be punished. On the trip she had told me I had a filthy mouth and probably caused by a filthy inside. I therefore would be given an enema before I went to bed and would have my mouth washed with soap. This would occur in the morning also before we went out. I almost cried. Enemas hurt me so much and I could already taste the soap.

So I went to the Ladies room to put on a pretty negligee and then lay in bed knowing that I soon would be punish.

I heard her in the Ladies room filling the enema and then she called. I, of course, obeyed and went to the Ladies room immediately.

I laid on the cold tile flooring with my tummy bursting and wanting to cry. Mistress Rosemarie removed the enema and before I had a second to catch my breath I was told to stand in front of the sink and watched as she prepared the soap to wash out my mouth. Tears were coming to my eyes, but I knew it was useless to beg for mercy. I had been disrespectful and I deserved every punishment I was getting.

I stood there in horror as Mistress Rosemarie prepared my mouth washing. I had applied lipstick many times and then washed my mouth out with glass-fulls of soapy water several times so it was moist and then it happened. She told me to open wide and shoved the soap in. She let it sit for a few moments and then shoved it in and out and around till my mouth was soapy enough for her pleasure and revenge. Then in went my penis plug. I was gagging.

I then sat on the toilet as Mistress Rosemarie set the timer for 10 minutes. It seemed like forever as my tummy was cramping really bad and the soap was gagging me. Finally the penis gag was removed and I could spit out whatever soap I could, but then it was directly to bed for me with a soapy taste in my Mouth.

Day # 2:

Saturday Morning and we were continuing our trip. It was a short hop in the car this time to a town we had often visited. Lots of stores for shopping and some really good restaurants.

As directed, I was wearing my panties and pantyhose and a big white bra which I hoped would not show through like yesterday. I am not a real shopper, but Mistress Rosemarie is and she made the most of her new found power over me. We shopped for hours, but then we had a really nice lunch and then more shopping.

We checked into the Hotel and after a light dinner, my nighttime punishments started again to her delight and pleasure.

I wore the very frilly, lacy sexy Red Negligee that Mistress Rosemarie had bought me for Christmas. I also had brought along the Pink frilly lacy sheer Peignoir Robe in hopes of really looking pretty for her. I did, but this did not put off my prescribed punishment.

I came out of the Ladies Room and hanging on the door was my punishment cleansing enema. Into bed I went and a full enema was given to me. Oh my gosh, it hurt a lot and I could hardly keep it in. My tummy was swollen and cramping.

The day ended well though. I had been very polite all day and did whatever Mistress Rosemarie wanted. She decided that I did not need my mouth washed out with soap. I was so happy, even if my tummy hurt.

Day 3:

I was sleeping soundly on Sunday Morning and did not even hear Mistress Rosemarie get out of bed. Then I had a very very rude awakening. Mistress Rosemarie had shove an enema Nozzle up my sissy vagina and before I could say a word, the cold water was gushing into my insides. I was startled and the cold water caused me to have instant cramps. It hurt and I cried and whined and begged her to stop. What a horrible way to wake up in the morning.

My whining and crying was not good, but I could not help it. Finally I was allowed to relieve myself and I was about to climb back into bed next to Mistress Rosemarie when she got out of bed and said we needed to get dressed and move along on our trip. I had to go and sit next to her in the Ladies room and on the toilet. She soaped up the pink smelly soap, washed my mouth out until the suds were overflowing. As she did this she explained it was because I had whined so much. When I started to explain (never a good thing) she shoved my penis plug in my mouth and I sat there as she showered, dried off, got dressed and applied her makeup. It was a long time.

I was allowed to get dressed and we were on our way.

Today was Sunday and the football games were on. Thank Goodness Mistress Rosemarie also likes football and she was very kind and allowed me to watch also. I thanked her profusely and tried to be extra special good all day. We got back to the room late and she was tired, so she asked if I would like to put off my last night of punishment until next weekend. I immediately thanked her and said yes and we both went to sleep.

Day 4 – which became the following weekend.

Sunday:

Mistress Rosemarie woke me up pretty early. I like to sleep, but she is an early bird and she was “horny”. She told me to get under the covers and pleasure her and to keep doing it until she was satisfied. My tongue was throbbing and I was exhausted when she was finally satisfied.

I then put on the very feminine pretty negligee, as today was the Day 4 that I had put off. She smiled and reminded me how quickly I had accepted last week to put it off, but then reminded me that to put off a punishment is often tougher then at first. I knew I was in for a long morning.

I was dressed and then had to fill my own enema bag with lots of warm water. I also had to take a picture with several of my Christmas presents that I was ashamed to do several weeks ago. My enema, my inflatable sissy vagina plug and a box of tampons. Then for good measure she took out the pink soap, soaped it up good and stuffed it into my mouth till my mouth was totally soapy. Then she said that since I would probably cry and whine she was going to insert my penis mouth plug and she did before I could even cry. I was sufficiently prepped.

Then the fun (her fun, my humiliation and discomfit) began. With my Head stuffed in the toilet, the enema was released and with my sissy vagina squeezing, the warm water gushed into me. Oh my Gosh, It hurt. I could hardly stand it and Mistress Rosemarie was kind and went slow. She would stop the enema and let it settle. Then she would snap the clamp open and with a gush I would jump and squirm. Oh how it hurt. Finally after what seemed like forever, I was stuffed and it was empty. Then she pulled out the feminine douche nozzle and stuffed in the inflatable plug (my horrible Christmas present) and pumped it up. Out came my penis plug, but I was not allowed to spit out the soap. She took my hand and led me to bed.

We laid in bed as my tummy hurt and I had terrible cramps. I cried and she smiled and told me it felt just like her cramps when she had her period and it was about time that I also experienced what it was like to have a period. All those years I had not had any sympathy for her, maybe I would now. She told me the next lesson I would learn in the next few weeks was that I would be having my first period and that was what the Ladies Sanitary Napkins and Tampons were for. She smiled and a feeling of dread came over me. She also reminded me that it was Sunday and time for another of my relief fantasies. She told me what to fantasize about and then to write it in my diary. (Later)

Then as I was finished and starting to clean up, I found out why I was saving my sissy milk in Condoms. I had been so glad that I was not slurping it anymore, but this was not much better.

Into my panties she dribbled the sissy milk and after inserting a tampon to help control the remainder of my enema that was still leaking, I would wear these sticky soiled wet panties for the rest of the day.

My Trip had come to an end and most of my Christmas presents had been revealed. Some day I will learn to do as I am told and to be more sharing with my humiliating experiences.

A tired and humiliated sissy, sissy billy

3 Comments

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Oh Sissy Billy, you almost make it sound like we did not have a lovely time. I certainly did. Maybe for you it was a little uncomfortable at times, but you most admit that you did deserve it. You looked so lovely in you Nightie’s. You should model them more often so the other Mistresses can see how pretty you are when you dress up in your finest lingerie. You should not be embarrassed. You are what you are, a cross-dressing sissy.

Now, my sweetie, what would you like for Valentines Day. I hope you are thinking about looking pretty for me. Maybe this time you will not be so shy in showing and telling your sissy friends how pretty you look.

You should also enjoy this restructuring and down time at the Institute. I do have to communicate with your Mistress Myckie Jo and plan some activities to keep you on track.

Happy Valentines Day to all you other Sissies. Make sure you tell your Mistresses how much you love and appreciate them.

Mistress Rosemarie

Oh Mistress Katzenburg, I wish to be a very obedient sissy and would request you do this punishment to me please!

sissy alison – it was not as much fun as you may think or it looks. The only good thing was dressing up in my pretty Negligees. Wishing and doing are two different things. sissy billy

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