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I had only used tampons a few times at this point and put one in on a particularly heavy day. I put one in and when I pulled out the applicator, the string came out with it.

Spent several hours trying to fish it out with my hand. Not fun and totally disgusting but hilarious years later. I had been invited to a swimming party and I was probably only I was so upset about not being able to go so my mom offered to teach me how to use one… She got out a mirror so I could see what I was doing and it totally freaked me out.

There was a tampon in there that I had NO idea was there. I change my tampons regularly throughout the day, I am usually VERY diligent about taking care of myself in general.

I cannot tell you how embarassing and shocking this was that it happened to me. I was so embarassed that you ladies are really the only people I have ever told this happened.

As a man I have no need of tampons : hooray. She got such a bad yeast infection that the doc said when he went in to help her, it was like […].

Sign up for the Thought Catalog Weekly and get the best stories from the week to your inbox every Friday. You may unsubscribe at any time. Mistress Lexie deserves only the best, and as a slave i must strive to be the best slave i can.

Please forgive me Mistress Lexie, i am ready to take whatever punishment You feel is necessary. October 7th, , am.

I failed my Mistress by not buying the panties i was ordered to purchase. Mistress Lexie was not pleased and took it out on me in our last session.

I was made to whip my ass with a belt, i deserved every stroke and more for my disobedience. Once again Mistress Lexie used my ass as her toy.

I was forced to take ice cube after ice cube into my sissy ass. Afterwards Mistress fucked my sissy ass with a spatula, i had to ram it in and out as i sang Mistress happy birthday.

That reminds me if any of Mistress's slaves have forgoten her birthday make sure to get her something right away.

Finally, i have given Mistress control of my orgasims. I can no longer have an orgasm without first being given permission from Mistress Lexie.

Mistress has complete control of her sissy slave and i couldn't be happier. September 30th, , pm. I have become Mistress Lexie's sissy slave and i could not be happier.

The first time i gave myself to Mistress Lexie she used me like the sissy slut i am. Mistress had me on my knees putting ice cube after ice cube in my little ass.

It was so cold and painful but Mistress Lexie has such control over me that i continued to put ice in my ass, just happy to be pleasing Her.

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.

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 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. 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. 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. Mistress Rosemarie woke me up pretty early. 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.

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Well, I went back into our condo and… the tampon was gone LOL. Good thing it was our last day at the condo, because uh… some people were going to find a tampon in the water.

Well, one day I had my period and I always kept my tampons in the front pocket of my backpack. The guy pulled one out, thinking it was candy.

I felt a little embarrassed but not really. I started laughing my ass off by his expression. It took him a week to talk to me again.

I had tennis practice and I was wearing a tampon. We had an emergency meeting so I had to wear the tampon for a little bit more than 8 hours then I started to leak and my tennis pants had blood all over them!

I had to go to her class next day;. I was at a summer camp and we were going swimming and was bummed that I was on my period. Friend gave me a tampon and I was clueless.

That was an awful day—very painful. After laughing her ass off for like 5 minutes 15 year olds are so mature :P she told me what i did wrong.

January 22nd, , pm. Goddess was kind enough to mention me today in her blog. It is such an honor to have Your actions mentioned by Your supreme Goddess for all of the world to see, i am thrilled.

Thank You Goddess for this honor, and i just hope that i can stay in Your good graces and treat You as You deserve to be treated.

Thank You Goddess. January 21st, , pm. October 22nd, , pm. Mistress Lexie deserves my attention and admiration everyday. It was very embarassing having to take a pair of pink panties and a cami to the young female checkout girl.

But i knew that doing so would make Mistress happy. This is the last thing i have done for Mistress, and that was over a week ago.

There is no excuse for such behavior. I am nothing more than a piece of property to Mistress Lexie, and as such i should be available for her enjoyment every single day.

I know this and yet i have failed to be a good slave. Mistress Lexie has already made it clear that i will suffer for her the next opportunity i have.

Mistress Lexie has complete control over me and i will strive to become a better slave in the future. Mistress Lexie deserves only the best, and as a slave i must strive to be the best slave i can.

Please forgive me Mistress Lexie, i am ready to take whatever punishment You feel is necessary. 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. Mistress Rosemarie woke me up pretty early.

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. 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.

Your email address will not be published. Let us know what you have to say:. 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 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.

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