ONE TRAPPED SISSY: From Crossdressing Voyeur to Transgender Slut

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I looked up at her with my carefully made up eyes in the mirror, asking for explanation without a word.

I replied, "Well I suppose they would not really like the idea, my mom might be a bit sympathetic as she has said she wish she had a girl also, I have two brothers." Carolyn said, "Well you should just enjoy the feelings your clitty gives you” I replied, “My clitty, oh you mean my penis. That’s a better name for it and I love it when my clitty gets excited by my frillies.” Carolyn praised me, “Ooh yes honey that’s perfect. You look so precious, Honey. You've made Mistress very happy.” There my Master sat, smiling as he faced the door. In front of him was a wide variety of sex toys, arranged from smallest to largest, and also a few glasses arranged in size with what looked like the familiar contents of cum sitting inside them. As I approached, he spoke. It seems it's definitely against the rules to allow ladies inside the grounds,” and with a gleam in her eyes added, “and as cute as you look, sweetheart, I'm afraid that applies to you, too.”

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You don't know how happy it makes me to see Madam smiling again,” she went on. “I'm sure she'll really hate to see her little girl go once the weekend is over.” Looking out to the car, the old priest smiled and waved to what appeared to him a pretty young girl. “Oh, I'm afraid that's not allowed; the academy is cloistered to women.” Aunt Mary said, “We are so glad you are enjoying it my darling. We still have lots in store for you.” Carolyn will you please go and get the things we are going to dress baby Chrissy in?” It seems that this day she was taking her little baby girl; all dressed up cute, and adorable, in her best party dress for a special ride. They ended up at this well to do townhouse complex. She stopped the van in the drive way out side of a nice looking townhouse. She beeped the horn twice & the garage door opened so she could pull in. once inside the garage door closed behind her. She got out and came around to the side of the van to open the sliding door and released her new baby from the car seat. She whispered a word in his ear, and he started to act like a 2 -year-old little girl, who talked with a really bad lisp. As she got her baby out of the car seat he grabbed his dolly and asked mommy, do I look really cute mommy? His mommy told him oh yes dear you are the cutest baby girl ever. To which the husband, who was now acting like a little 2 year-old-girl giggles and clapped her hands happily. The wife had her new baby turn around so she could attach a long pink leash, as she let the baby out of the van. She reached over and placed his large adult size penis pacifier hanging on a ribbon from his dress in his mouth. Then she had him walk over to kitchen door entrance in the garage and ring the bell.

The tasks became continually harder to accomplish, but eventually I had made it all the way up to the largest for each set. These were too large to be able to do simultaneously, so I approached each individually. Carolyn said, “Chrissy my darling are you up to appearing in public dressed as a girl? We wouldn’t want you to give yourself away.”I was more confidant of going out to eat with my two kind hosts. Carolyn told to me to sit down at the vanity bench and I did so gracefully and in a girly manner. How was this possible?” I thought to myself. As I turned to see the reflection from another angle, it hit me. As the layers of taffeta swished about my nylon-covered legs, there was no mistake. This was no dreamlike image - this was I! I could have remained before the mirror for hours had the two women not awakened me from my reverie.

We drove on, heading down the shaded boulevard toward the academy. “I'm sure we'll find your suitcase, but it will be so much of a shame; you look so pretty as a girl.” Aunt Mary said, "Ooh my baby Chrissy looks like you love your clitty ejaculations." I heard what she said and thought how lovely it was. This was so heavenly to me and I began to think of what else the women had in store for me. I was willing to go along with anything they would like to do.

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Yes, Ma'm, she'll be right down.” With that, Carolyn called up the stairs, “Come down, and Honey, we're ready to leave.” I told her of the movie that was due to start soon. She said, “It’s interesting you chose that particular movie, I know of the movie, a man dressing in woman's clothes." She continued, "Well Chrissy my dear girl how you are enjoying your stay here with us?" I replied, "Very much Aunt Mary, the clothes you have put me into are so wonderful I wish I could always dress this way." Aunt Mary replied, "We are glad you enjoy it so much. We want to give you a taste of what it will be like as a girl from earlier in your life, we have a surprise for you later." I was wondering what it could be and looked forward to it as I was sure it would be good. Horror Writing | Screenplay Writing | How To Write | Write Books | Read Write | Writing Tips | Writing Tools | Writing Community

As she slid the silky panties up and down along my member, I began to shudder, “Yes! Yes! Make me your little girl!!” With that, my shaft erupted into the delicate little panties and I collapsed down onto the vanity seat. At this point I considered myself to be a girl. Overall, I think Stacey won't be a toddler for long, and his mother will have some explaining to do when the authorities find out exactly what she's doing to her son. Lois said this while she was giggling & laughing again. She then looked at Jane and they both giggled. Lois then said to Jane. I’m so glade I called you that day, but I just knew I had to call, as soon as I found out he was married. He had told me at first that he wasn’t married, but when I found out I was really mad. So I broke it off with him right then & there. You have to understand I honestly didn’t know that’s why I decided I had to call you. I wanted you to know what he was up too, and that he was cheating on you. I figured maybe you could save your marriage. I didn’t want to be the cause of a marriage breaking up, with me in the middle. I can see now that you have everything under control, and that makes me glade that I did what I did. My Ex husband cheated on me, and I know how it feels. That’s one of the reasons why I called right away, but I must say that you did a great job on Little Pricilla here. I bet she won’t be fooling around on the side any more. They both laughed at that, and Jane said I’m sure about that. I am so glade you did call. Now like you said he is never going to be fool around on me again. Little Pricilla will be safe at home behind her crib & playpen bars. This way I know exactly where she is. Lois then said that she should of done something like this to her Ex., maybe they would still be together if she did. Not liking that option, I did my best to force out a whorish moan, the kind I'm used to hearing come from one of my dates, not from my own cum covered mouth.Caroline got toilet paper and began to wipe me. She got me to roll over on to my stomach so she could get to my rear. I did not lie flat on the table as my clitty was making that difficult so I had my rear in the air. It was good as Carolyn wiped me. Carolyn said, “Just hold that position while I go get a cloth and some water. As I waited there with my rear in the air I wondered what the ladies had in store for me today. I began to grow uncomfortable as my felt my bladder fill up and Carolyn, taking notice asked, “Is there something wrong, sweetheart?” Still blushing, I took my seat, as Carolyn's eyes met Aunt Mary's and the two women shared a knowing smile. We all make "judgements" every day, and there's nothing inherently wrong with doing so. Rather, I submit that it would be wrong - to one's own self - to fail to do so. Yes, that's much better, sweetheart,” answered Carolyn, a knowing smile crossing her lips. “Sit here and I'll start your bath water,” she said, turning and entering the adjacent bathroom.