tagTranssexuals & CrossdressersStep by Step Sissification Ch. 02

Step by Step Sissification Ch. 02


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.


"Oh, well, I'm sure you're 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?"

We lapsed into silence at that plastic food court table. I'd basically asked this stranger, the man who'd bought himself a red satin thong, if he wanted to be a sissy or not.

I picked up my own Macy's bag.

"I love their lingerie," I said casually while he agonized and his mind raced over my question. I pulled out two bras, each in rich satiny nylon, demi-cut. "I wish I had a 'girlfriend' that would tell me if these looked good on me or not..."

I know it was cheating, but that's what you have to do with reluctant sissies. Tempt them with something sexual to get them to tell me the truth. No... to get them to admit the truth to themselves.

I held the pink one up against my chest and looked at him. "A sissy is like a girlfriend. I could try on lingerie with a sissy and talk girl talk..."

He almost groaned at that.

"But, you aren't a sissy, are you?"

I slipped my foot back up to his crotch and fondled his raging hardon with my stocking-covered toes.

"Hmmm, seems like the jury is still out. Come with me."

I stood and gathered my purse and bags. I started walking away and let him catch up. We returned to the Macy's lingerie department and I was glad when he stayed with me the whole way. I went to the sales girl.

"The underwire on my bra just broke so I want to change into one of these new ones. Can we use the dressing room?"

She nodded with a plastic smile, only her eyes giving away the mention of the man accompanying me.

We headed back and picked the largest changing room. I pulled the curtain shut behind us and began to take off my shirt. I faced away from him as I did so, letting him watch me unhook my bra and take it off as well. I covered my breasts with my hands and turned to him.

"If only you were a sissy, I'd let you see all this," I teased, letting my hands drop as I reached for my store bag. His eyes practically widened looking at my breasts which pleased me. They are pretty full and luckily they haven't really fallen on me yet.

I slipped into the pink bra and hooked it in back. I looked in the mirror, adjusting it this way and that until it fit just right.

"How does it look?" I asked him at last, turning to face him fully. He jerked his hand away from his bulging pants but not before I saw him. I didn't mention anything, but I let him gaze on how the bra lifted my breasts and gave me nice cleavage. I placed my hands on the bra and gave the girls a little squeeze.

"I love how the demi-cut shows off more of my breasts. Do you like that?"

Now he nodded his response, unable to get out an articulate word.

I took off the pink one and tried on the green one, following the same routine. I eventually put the pink one back on and then pulled him to his feet.

"Your turn. We'd better make sure your thong fits just right."

He hesitated as I sat there in my bra and skirt.

"Come on, unless you'd like me to leave."

He didn't want that so he picked up his bag and just sort of played with it.

"Oh, please, girlfriend, drop your skirts and try them on!" I chided.

He pulled out the thong and held it in his hand, the price tag dangling. Time to play hard ball.

"Okay, you proved your point. You're not a sissy and I should go now." I grabbed my shirt to put it on.

"No, don't," he blurted. "Please, stay. I'll... do it."

I sat down and got comfortable, my smile relaxed. I waited.

Finally, he unbuckled his slacks, took off his shoes and slipped off the slacks. I grinned when I saw he was already wearing bright yellow panties with lacey edging. Perfect!

"Those are adorable! And so sexy!" I enthused, reaching out and caressing his hip and bottom. They were satiny and shiny and the lace was thin and soft. "You look very cute in them!"

This encouraged him and he took off his shirt too.

"Now try on the thong."

He hesitated and then pulled down the yellow panties. His cock was impressive and very hard. I giggled and winked at him. He fished out the thong and slipped it on. It didn't cover his cock much at all and he struggled to make it fit right.

"Well, now that won't do..." I said softly. I grabbed his yellow panties and carefully wrapped it around his cock. I gripped it and started to stroke him.

"Sometimes girlfriends have to help each other out," I explained softly. He stood there stiffly as I jerked his cock. It was less than a minute before I felt it throb and then the panties were filling with cum, lots of hot cum.

I cooed, "Good girl, that's the way." He groaned softly. I slowly milked him and wiped it clean.

"There you go," I said, taking away the panties from his soft cock and tucking the cock into the thong.

"It's very pretty," I said, giving him a critical look over. "A basic of a sissy wardrobe..."

I slipped the cum-filled yellow panties into his bag, put my shirt back on and put my other bras in my bag.

I pulled a slip of paper from my purse and wrote my phone number on it.

"If you call, you'll have to tell me that you're a sissy and then we can go from there. If you aren't a sissy, don't call."

And I left him there, standing in a women's changing room wearing nothing but his socks and a red satin thong...

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by Anonymous

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by pamcd02/18/18

So hot

I had similar experiences when buying panties and hoses. A lady came up beside me and said can I help you? I turned around shocked. She said stop I know what your doing. I said What? She said your a sissymore...

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