Sissy Boy, Mommy Helps Her Little Girlie Dress Part 2

I went into my sissy boy, Jordan’s room, and searched until I found his penny loafers. Those would have to do for the moment. I went back into my room and Jordan was standing there naked just as he’d been told. I sat him down at my dressing table and with cream and tissues, cleaned of the way too heavy makeup he’d slathered on. Then I reapplied a little light foundation and some mascara and finished with a faint pink lip gloss. I explained to him what and how I was doing the makeup. I told him that he was forbidden to use any more makeup than this unless I gave him permission. Then I had him dress in the clothes I’d picked out and from my closet and brought out a wig that I’d inherited from my sister. A little brushing out and it was perfect.

I stuffed his little bra with a couple of pantyhose and stepped back to admire my handiwork. “Come on,” I said, “we have some shopping to do.” There was panic in his eyes, but I grabbed his hand and pulled him out the door, snatching up my purse as we
went. Then it was down the stairs, out the door, and into the car.

I backed out of the drive with my pansy guy and headed back toward the mall. Jordan was slouching down, but I told him to sit up straight. I knew he was scared of being seen and would be mortified if anyone he knew saw him. This knowledge gave me a perverse thrill. I had complete control of his situation.

He would do anything now, and a lot of possibilities entered my head.

When we got to the mall, I wasn’t so lucky as the first time and had to park a distance from the entrance. Jordan was being reluctant, not wanting to go into the mall where he knew he’d likely run into friends from school hanging out. I wasn’t in the mood since we had only a little time before I had to pick up Amanda, so lifted up the back of his little skirt and gave him a hard swat on the bottom.

“You listen to me and you straighten up and be a good sissy boy! I swear mommy is going to pull down your panties right here and now and give you a spanking that you’ll not soon forget. ” I said it aloud. When I glanced around, I saw a man a row over who was smiling. He must’ve overheard the conversation.

Jordan was aware of that too and realized that I was serious and that having his bottom tanned in public would be far worse than whatever might befall him in the mall. We walked on and entered the mall. I had to tell him several times to straighten up and not slouch and lift up his head. The first shop we hit was the shoe store.

My pansy guy and I spent some time picking out shoes. I told the clerk that I needed to get my “niece” a few pairs of shoes. We got a pair of flats and a pair of Laura Janes and a pair of heels with demure one-inch heels.

We agreed was the best for a young girl to start out.

Then, we went into a department store and we picked out a selection of panties and bras, some socks; anklets, knee highs, and a couple of pairs of tights, stockings, a garter belt, and a couple of nighties. The clerk was very nice and she helped fit Jordan’s new bras. She reassured my niece and told her that she would be filling out in no time. Then we wandered over to the Junior Miss department to pick out a couple of outfits.

After having my sissy boy try on and model several, I decided on a simple school girl kind of outfit with a pleated skirt, white blouse and blazer, a more casual skirt and blouse, a dress with an A-line skirt. We stopped at the makeup counter and I had the girl there give Jordan a makeover and she was so happy to introduce this young girl to the joys of makeup. We bought a few things, foundation, mascara, eye shadow, liner, and lipstick. The last thing we bought for “her” was a purse.

Loaded with our purchases, we headed for the parking lot. With luck, the traffic would be with us and I’d be on time to pick up Amanda. As we were almost to the mall doors, I ran into a neighbor who lives a few doors down.

“Katrina!” she called.

“Laura. Hi. How are you?” I said

“Oh, good you know. Who is this?” she said in response

This is my niece, Sharon, my brother’s eldest, and she is staying with us for a while. Sharon, say hello to Mrs. Smith,” I said.

My sissy boy managed to get out a “Nice to meet you.”

“She’s very shy,” I said.

“Well Honey, that’s OK. You’ll have to come down and visit me, Sharon. We’ll have a girls’ afternoon of it and get to know each other.” Laura said to Jordan and then looked at me and said, “Sweet little thing.”

Check out my audio blog of

Sissy Boy, Mommy Helps Her Little Girlie Dress Parts 1 & 2

If you enjoyed this blog you might enjoy this one about Sissy Phone Sex!

Kisses, Katrina


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