I went about my business. The babydoll and panties were stunning and were clearly going in the Like pile. Since they were a matching set, I kept them together on a corner of the cushions. After I handed the items to Instructor Mike, including the heavy steel object, he grabbed a couple of small towels from the end table as I bent over in front of him, exposed and a little afraid as I shut my eyes.
“Good girl, aimee. Now you’re gonna feel some pressure, but just try to relax. This is called a butt plug and it’s a very small one. It’s part of what we need to do to feminize you. Once the plug is in, you’ll be wearing it like a good little sissy during your entire fashion show. It has a circumference of 4 inches which is a bit larger than your pathetic dicklet for reference. I’ve already opened you up a bit so it should go in pretty easy.” Suddenly I felt the tip of the metal object spreading lube on my sissy hole before quickly pushing its way in. It was almost feeling like too much when my boycunt sucked it in and it situated nicely. It felt a bit weird at first but I got used to it.
“SIT!” He ordered. I was worried what sitting on this thing would feel like, but I assured the position precisely, and thankfully my ample backside gave me enough padding to sit comfortably. Bless my girly ass.
“See, that wasn’t so bad. Now let’s get this show on the road. We want to find all of the outfits that will please Daddy. Let’s start with the matching panty and bra sets only. Proceed!”
As I bent over to grab the items from the suitcase, Instructor Mike began groping my cheeks and gently pulled on the plug handle a few times. The first set was a bright green, and after putting it on, we both agreed that the color didn’t work for me. Into the return pile it went. We tried black, white and yellow next but it was the same problem. Now I see why girls have so much trouble shopping! The dark purple was a perfect look but I was hoping brighter colors would work on me as well. Next we got to trusty pink and this did look good on me. It was bright and pretty and I felt really cute in them. It was weird putting on a bra with AA cups but wearing it made me feel like such a hot girl. He seemed to like this outfit as well.
“Come here so Instructor Mike can grope you.” I walked over gingerly as he stood up and started fondling me all over from above. The panties felt so smooth and his hand lingered for a long time rubbing my ass through them.
“I think we have a winner. They both fit and feel great. Place that in the good pile.” We went through 10 more sets of various colors and fabrics. Some didn’t look good, some didn’t feel smooth to him when he was groping me, but we settled on 5 more sets that were perfect. Next I stripped down and tried on all of the outdoor wear like bikinis, dresses, skirts, and tops and we went through the same process. It was very important that my ass was showing properly but not too much in the skirts, so length was key. Instructor Mike explained that skirts with no panties would be something I’d often wear in public, and the dresses were for more formal gatherings where I would have to be sexy but demure. The tops were mostly tied off exposing my midriff and neckline. The bathing suits were all skimpy thong bikinis except for one more modest one that we might need “just in case”.
We then tried on some more babydolls and settled on the ones with the perfect length to partially cover my ass. I really liked the babydolls because they kept me pretty warm while leaving me fairly exposed as well. Next were the sexy outfits which were my favorite. They were often elaborate, and involved a lot of proper fitting so it took a few minutes for each. The black and white french maid outfit with an ultra short skirt and no panties looked amazing on me. Instructor Mike stated that it would be my outfit whenever house duties were required of me. My favorite though was the asian schoolgirl outfit which went really well with my pigtails. With our ***********ions complete, Sir Mike ordered me to place the good items in an organized fashion back in the suitcase.
“I think the little faggot likes her gifts and should thank Instructor Mike properly.”
“I love the gifts; thank you so much Instructor Mike!” I exclaimed in my feminine voice with my hands together like a cutesy asian schoolgirl. Kneeling nude in front of the Daddy Chair and praying to Instructor Mike’s Powerful White Cock with a big smile on my face.
“Good sissy! You’re dressing and talking like a girl, now it’s time to learn to walk like a girl. Grab the brown shoes and put them on. With no clothes on, I’ll be able to monitor how your ass moves and ensure you are walking correctly. Remember to go heel-toe each step.” I made my attempt and stumbled a few times as I started getting the hang of it. After pacing back and forth about 10 times, I was able to tolerably walk around.
“Better, but now you also need to take your steps one foot in front of the other. This ensures that you ass sways in the way that will please your Daddy. Practice until you get it right.”
It took a good 10 minutes of practice and my feet were starting to hurt a bit from the tight shoes, but I finally got the rhythm down. I noticed each time I turned to face Instructor Mike as I walked down the sissy runway that he was enjoying my ass more and more.
“Well done, girl. Now switch to the next size up.” After doing so, I immediately had problems again, but overcame them more quickly. In a few short minutes, my ass was once again swaying hypnotically for Sir.
“My little sissy is a natural. Let’s try on the rest and then you can show me your room.”
We wrapped up with the wigs and other accessories, and figured out our keep pile. Once again, I loaded them up, this time in the second suitcase. Instructor Mike stood up and closed each suitcase before picking them up. I reached for one to help but he stopped me.
“Daddy carries the heavy stuff. Little girls sway their cute little butts in front of Daddy to please him. Pick up your doggy bed and you can show me your room. Hold it out in front of you so I get a good look at your ass as we head up.”
My ass swung lewdly before his eyes as we ascended. He placed my suitcases on the bed and opened them up.
“Nice room. I love the posters. You look very pretty with no clothes on aimee. A delightful treat for Daddy to use over and over again. Start organizing your clothes and accessories and then we’ll talk about the rest.”
I put all of the sexy clothes in the top drawers and on the most accessible hangers and the more reserved clothing farther back. The 4 wigs we settled on I placed on a stand next to the vanity, and the jewelry, hair bands, scrunchees, and other accessories went on top for easy access. It was really starting to look like a girl’s room as I placed the cute shoes in the closet.
“All that remains are an array of items related to your sissy pussy. You will place these lubricants and toys in your nightstand where every naughty girl keeps them. The enema is under the bathroom sink for use each time you come over. Finish organizing, then close up the suitcases and place them in the closet.