Sissy Shopping Stories

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Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Sissy's Shopping Trip Pt. 01

by SissyFaye on Jul 13, 2020
Transgender & Crossdressers

"You finally got paid, Sissy!" my mistress says with excitement. "Yes, I did, my love," I say. "Well, I think in celebration of your first paycheck from this new job, we need to go shopping!" she says. "Oh really, shopping for what? I ask. "Clothes for me, and maybe some for you," she says. "Mmm, sounds like fun!" I say with excitement getting hard...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy Boy Secretary Ch. 02

by Hotenuf4u on Sep 19, 2017
Fetish

I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked l...

Subliminal Obsessions Ch. 04

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

*Before... I open my mouth and pump the last bits out of him and show him and Sarah's sort of become invisible as she recorded all of this. Alberta's standing and staring from the doorway and I show her too and her wide eyes widen more and then I swallow it. I rise up to standing and deeply kiss Leon. "That was perfect, worth all those years working for...

Pinky the Sissy Maid

by Pinkytoes66 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ;) This is part 2 of my current series. Part 1 was "Pinky's First Shopping Assignment". I've yet to decide on a title of the series and am open for ideas. Thank you. *********************** A few days after I completed...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...