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How Did You Become A Sissy, Part 2

How Did You Become A Sissy, Part 2

Time For The Bra

“Can I try your bra?” I asked, going for broke.  She looked at me a second before opening another drawer and finding one that was a similar color to the panties I was wearing.  She had full, beautiful C breasts, so the bra cups were very loose on me, but I loved that she showed me how to put it on and how it should fit on my body.  We were both amazed just how well her bra fit me.  Well, with the exception of filling out the cups of course!

A Sissy Shopping Spree

“Now bras are expensive, so you can keep that one, but just that one.  If you want more, we’ll have to go shop for them.”  We had jobs by then but were still living at home so we had cash to play with.  I pushed and got her to commit to a sissy shopping spree that Saturday.  I begged for the other girls in the group to come along.

“You want all of them to know?”  I nodded.

“Are you gay?” she blurted out, her face turning red.

“I don’t think so. I don’t think about guys the way I think about girls, you know, _being_ with girls. But well, it’s complicated.”  I couldn’t get myself to confess that I did fantasize about cocks but never the guys they were attached to.

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Feminization Mistress Ms. Delia

“Do you think about Amy, Brenda, or Susan that way?”

I had had to be very careful but I also wanted to tell her so much.  “I think all the girls in our group are very beautiful and sexy.”  I let it sink in that I’d made particular phrasing to include her.  She gave me a Hmmm and thought about it.

Seems Everyone Knew He Was A Sissy

“What do you want me to tell them?”

That gave me a pause but the answer came. “Tell them I’m a sissy and I need their help buying pretty undies and outfits.”

She thought on that for a bit, nodding slowly.  “Do you want to BE a girl? I mean, get a sex change and the whole bit?”

“No…” I responded quickly and then thought more. “I have done some reading.  I’m not a crossdresser…”

“But, you’re wearing girls panties right now!”

“No, I mean a crossdresser doesn’t do it for sexual reasons, they do it to express their inner nature.”

“Oh, so for you it’s a sex thing?”

“Yea, I mean I think it’s just a sex thing.  I don’t feel like I want to be a girl but I do fantasize about being like a girl… It’s confusing to me and I’m living it.  I mean, I’d love to have pretty breasts like yours but not permanently.  Does that make sense?”

“Not really, but you can always talk to me.  If I can help you figure things out, I want to help.”

That’s when I hugged my friend just wearing her panties and bra and trying to keep the erect bulge in my panties from rubbing her as I enjoyed how good her body felt.

“Okay, let me call the girls and let them know what we’re doing Saturday.  I don’t think it will be a complete surprise…”

 

So, how did it happen for you sissy?  How did you become a gurl?  Maybe you haven’t yet, and just like my caller, you need a supportive, helpful girlfriend to lead you down the path.  Why don’t you give me a call?

3 comments to How Did You Become A Sissy, Part 2

  • Petey cream puff

    This is exactly what happened to me with my masseuse/mistress. We are planning a dress shopping trip along with myself getting makeover sometime in next few months.

  • Gem Sissy

    Thank you, Mistress, for publishing my little story. I hope the sissies and mistresses enjoy it.

  • sisecal

    Mistress made certain that, for me, being a sissy was knowing that I was neither a full fledged male or a woman, I was something in between. Even after her passing, I still wear panties and my only relief is masturbation. Mistress made certain that, as a sissy, I accepted being a cock sucker for her amusement and with enforced chastity she controlled my orgasms.

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