Sissy Boy, Mommy Helps Her Little Girlie Dress Part 1

I had no idea my son was a sissy boy until the day I breezed through the kitchen and up the stairs. As I got to my bedroom, I stopped. The door was shut. I never shut the door if I’m not in my room and I thought that this was very odd. I set down my packages and slowly opened the door, not really knowing what to expect. What I found was my son, dressed in my clothes, skirt, blouse, and heels. He was sitting at my dressing table, applying lipstick to his lips.

Then he saw me immediately in the mirror and jumped up, knocking over the dressing table bench. He was stammering and was a beet, beet red with embarrassment. Lord knows I was at a loss for words, but I had to say something. For want of anything better to say, I told him to pick the bench and sit down. I went out into the hallway and retrieved my shopping bags. I put them on the bed and then sat down on the edge of the bed facing
my son.

“How long have you been doing this Jordan? I asked.

“Um, well… for a while.” He mumbled.

“You like wearing women’s clothes like a pansy boy?” and felt immediately stupid for such a dumb question. Not waiting for an answer, I said, “Stand up and let me see

He stood, awkward and a little unsteady in the heels, but, I had to admit, he made a fairly cute girl. I had him turn and his legs I noticed were shaved and passably shapely in nylons, and he had a nice little butt.

“Lift your skirt,” I said in a tone sterner than I’d spoken to him before.

“But Mom…” he said in a whine. 

“You lift up that skirt sissy boy, or I’ll do it for you,” I said sternly in response.

Hesitantly, but by the tone of my voice knowing that he had no choice, he reached down and pulled up the hem of his skirt, stopping about mid-thigh.  “All the way,” I said. And he continued, exposing panties and garter belts. He had good taste in lingerie, he’d chosen a pair of sheer black bikini and matching lace garter belt and lace topped black stockings, all mostly new and expensive. It was the kind of “hither come fuck me” ensemble that I wore when I knew I was going to be having fun.

I noticed then that my little sissy boy had an erection. His cock, not very large, was stiff and straining the sheer black nylon panties. I reached over and pulled the panties down. Now he was standing there, panties about his ankles, his little hard cock exposed. I saw that not only had he shaved his legs, but he’d shaved his genitals too.

I looked at him scared, exposed, and humiliated. “Come here and sit next to me,” I said and patted the bed beside me. When he did, I made him keep his skirt hiked up so I could still see his little stiff cock. “Mommy isn’t mad about you wearing girls’ clothes, Sweetie, but Mommy is mad that you are wearing some of my best clothes. You’ve stretched out my bras and I had to buy new ones.

Now, if you are going to dress as a girl, then you are going to have to dress as I tell you and in the clothes that I tell you, is that understood?”

As my pansy guy sobbed, I asked softly, “Do you want to be Mommy’s little girl?” He sniffled out a yes, head down and his face red with shame. “Well then,” I said, “let’s take these clothes off and put you into something more appropriate.” I unbuttoned the blouse and slipped it off his thin shoulders, and unhook the black lace bra and slipped it off of him. When I had him stripped, I told him to fold and put away my clothes and when he was done, to stand there and wait for me.

I went into Amanda’s room and took a pair of cotton panties from her drawer. It was an old pair with a little flower print, and searching through her bras, found her old training bra, now outgrown by two cup sizes. A pair of white knee socks, a pink tee, and a little pleated skirt finished the outfit I had in mind, The only thing I didn’t have were the shoes.

Part 2 coming in 2 days!

Sissy Boy, Mommy Helps Her Little Girlie Dress Part 2

If you don’t want to wait to find out what is going to happen next, you can check out my audio blog Sissy Boy, Mommy Helps Her Little Girlie Dress Parts 1 & 2!

If you enjoyed this blog you might enjoy this one about Sissy Slut!

Kisses, Katrina


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