tagTranssexuals & CrossdressersStep by Step Sissification Ch. 01

Step by Step Sissification Ch. 01


Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff.


It all started when I was shopping for new bras and I saw him. He was standing around the lingerie area but not like another bored husband. He was far too interested in the dangling panties on hangers, letting his fingers carefully touch their fabric while trying not to be seen.

I thought it was curious but hardly dared to hope that I'd at last found another of that most rare of species: the sissy man.

I found the bras I needed but I hung out longer to observe him. I needed to know one way or another. He made his way slowly through the racks, through the bras, the panties, the slips, and the sexier nightwear. He gravitated back to the panties and then stuck near a particular rack.

I think he saw me look at him and it almost scared him off but I bought my bras and pretended to leave the area. He waited and then I could see him fingering the panties and his face turning flush. In a jerking movement he grabbed a pair of hanging red satin thong panties and knocked three other pairs to the ground. I had to laugh softly as he hurried to put them up on the rack again, his face very red.

His courage hadn't left him and he went up to the counter to pay for the panties. The sales girl kind of glanced at him buying one pair of panties like that but she didn't really care. A sale is a sale.

He really did it, gripping his plastic store bag, and moving to leave the area. I saw his pants were bulging significantly and I made my decision.

I rode the escalator down and loitered around the bottom. I made sure my shirt was adjusted to show off 'the girls' just right. He came riding down about half a minute later.

"Excuse me, could you help me please?" I asked him, flashing him a smile and letting his eyes flick to my breasts.

"Uh, sure," he stammered.

"This will seem so silly but I hate to eat alone. I'll buy you lunch if you come eat with me. Won't take long." I groaned inside. It was a pretty poor proposition so I let my hand brush his forearm 'accidentally'.

"Yeah, for a beautiful woman like you, it would be my pleasure," he replied and my estimate of his smoothness rose immensely.

We went to the mall food court and bought some wraps. He insisted on paying for both meals which put the encounter into the realm of a date in my book.

We sat and exchanged pleasantries. I waited until his guard was down and then I snatched his lingerie bag.

"Oh, I loooove Macy's! What did you get?"

He tried to grab for it but it was too late. I'd pulled out the red satin thong and held it between my fingers.

"That is so sexy!" I enthused as his face went red again and he almost seemed like he was going to have an attack of some kind. "I bet they are going to look amazing on you."

That got him. His jaw literally dropped open as he stared at me. I put the thong back in the bag and handed it back to him.

"But they're not..." he began in sort of strangled whisper.

"Not for you? Oh please sweetie, it's obvious they are for you." I slipped a shoe out of one of my heels and snuck it up to rub his crotch. "You're so hard I bet you can't wait to put them on!"

That blew his mind. Here was this pretty stranger telling him that she knows he wants to wear panties and that it gets him very aroused. He looked like he would faint.

I slipped my foot back in my heels and took his hand in mind. "Honey, don't get so worked up. It's all right. Nobody else saw you and I'll never tell. It's perfectly all right. In fact, it's pretty sexy if you ask me."

"You think guys in panties are sexy?" he asked in amazement.

"Yeah, well, cute guys like you, in the right lingerie and acting like they should... yeah, very sexy." I bit my bottom lip for effect. Didn't take much effort, I really was getting turned on by this, by his sexual energies.

"What do you mena acting like I should?"

Ah, now we were in the negotiation stage. Priceless.

"Well, acting like they want to, embracing it and being, well, you know."

"Being a what?"

"A sissy!"

That got an angry look at me. "I'm no sissy," he hissed.

I thought, 'Good, this filly has some spirit left in her.'

"Oh, well, I'm sure your right then. You wouldn't be interested in wearing panties and showing them to me, in wearing what I told you and doing what I told you..."

He swallowed hard and looked around.

"Or would you?"

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by Anonymous

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by cdCindy105/07/17

I'm a CD sissy too

I too am a sissy who loves to shop for my own panties, bras & nighties. I love it when I'm shopping and the salesgirls or other women look over at me and realize that I'm shopping for myself. I wish someonemore...

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