"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you dressed."
I stood there in disbelief about what had just happened. I had said out loud, for the first time in my life that "I am a sissy." I was naked in front of this beautiful fully clothed and authoritative woman who was praising me for admitting that I was a sissy. Not only that, but my penis was throbbing at its full arousal length of just over three and a half inches. And now she was going to help me get dressed and all there was to dress in was very feminine attire. We would obviously be choosing panties, a bra, and probably breast forms from the bureau and one of the many outfits hanging in the closet, and shoes...well...today would be interesting.
"I see that you are aroused, Tom. It is a cute little thing you have and that little thing seems to be so excited that it will soon be covered by panties. But I am going to ask you to keep focused so that we can get you dressed. We are to meet Ms. Panington for breakfast in her office in just a few minutes. Now let's get started. I will select today's outfit for you, Tom, but in the future we expect that you dress yourself. After all, you are a sissy, not a child."
My face burned with embarrassment as Ms. Jensen brushed by me and opened the panty drawer. "I believe that pink will be the color of the day. It is, of course, the sissiest color of all and let's have you start off on the right foot," and she handed me a pair of the full-cut "Mommy" panties with lace around the waistband and leg openings. "Put these on, Tom. I will find a matching bra. Let's see, I think we will go for the largest cups today. I will need the DD cup and the largest forms. Here we go, a matching pink pocket bra." She took the bra from the bureau and some large silicone breast forms. "let me show you how to put the forms in the bra, Tom, because we will expect that you do this yourself going forward, and we will want your bra to match your panties." She sat on the bed and demonstrated securing the forms in the pockets of the bra. "Turn around, Tom. Let's get you some boobs," and she laughed as I put my arms through the straps and she clasped the bra across my back. "Va-Va-Voom. Look at those tits, sissy-boy!" and she laughed some more. "Now stockings; I think we will use thigh highs today. Since we don't have any in pink I think this nude pair will give a nice look," and she handed me an unopened package. "I know that I don't have to show you how to put those on, Tom. I have seen the videos of you masturbating wearing Kelli's things. While you put them on I will choose the dress you'll be wearing today."
I was feeling a profound embarrassment to be dressing in such feminine things in front of, and with the help of, Ms. Jensen. But this embarrassment was mixed with an incredible arousal unrivaled by anything I'd ever before experienced. And also mixed in was an overwhelming sense of relief that I would no longer need to hide my true self. On top of all that I remained a bit scared about what was ahead.
I sat on the bed, rolled up the each stocking just as I had watched Kelli do many times, and pulled up each one, noting their fine quality, and admiring how they enhanced my smoothly-shaved legs. Ms. Jensen emerged from the closet holding a tiny pink cocktail waitress outfit. The bodice was made of a PVC-like material, shiny and stretchy, obviously form-fitting. The long sleeves were a slinky nylon see-through mesh, as was the midriff which was attached to a a pleated PVC skirt with an attached tiny white lace apron across the front. "This will be perfect for today, Tom. It will show off your breasts and give us plenty of access to your little wee-wee," she giggled.
The underwear was a turn-on to me, but this outfit scared me, and I knew that I would look ridiculous. I started to protest, "But, Ms. Jensen," and I could feel my penis shrinking in my panties, "I will look awful in that. I will look like a man in a waitress dress."
"Yes, you will, Tom. I expect that you will find it deliciously humiliating, especially when we connect with Kelli on FaceTime later this morning. Remember what you are, Tom. Say it. I am not a real man, I am a ..."
"I am a sissy," I responded.
"Very good, Tom. You are a sissy. Look at you. Your tiny penis is being monitored 24/7 by women, you are wearing silky pink panties, a bra with DD silicone breast forms, nylon thigh highs, and you want to argue about what dress you'll be wearing? Please!" Ms. Jensen quite firmly reminded me of my status. Now slip this on, and I'll zip it up in back, and stop with such nonsense."
There was a bit of tugging and adjusting to get the stretchy bodice over my breast forms and to get the skirt to sit just right about mid-thigh, but all-in-all it fit just like it had been special ordered for me, which it had. "You may look in the mirror now, Tom," Ms. Jensen said.
