Sissy Shopping Stories

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A New Way Of Life Ch. 02

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

A Big thank you to Chris & Scott for the great eaditing job. This is the 2 part please read the firts New Way I looked at Everett, "Ok, are you sure?" "Yes, Carine. Now go get ready. I'm hungry." I headed off to the bathroom to fix my make-up and hair. Looking at myself, I can't believe what had happened. I was loving it! I had never felt so alive, tu...

Eating Cum for Her

by DarlenesToy on Sep 17, 2018
Loving Wives

My wife/Mistress directs me to write these stories for her and then we do them in reality. She always takes parts of my story but changes the reality to suit her needs. This was a story about eating another man's cum. It started innocently enough. You were allowing me to jerk off and lick my precum off your nipples like normal. Then you began whispering as...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Pinky's First Shopping Assignment

by Pinkytoes66 on Sep 14, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ***** I just got home late at night from a rough day of work. I tossed my jacket on the kitchen chair, kicked off my shoes, got a beer from the fridge, and decided to sit down at my computer to check my messages before tur...

A Deal Offered

by LockedSissySubmissive on Sep 25, 2017
Fetish

I was sitting in the kitchen drinking coffee wearing my dressing gown when Emma left for work. We'd had a pleasant morning chatting about the various inconsequential matters that married people chat about but she had to leave for a meeting and looked fabulous in a smart dress suit and jacket. Even after almost two years of marriage I was still totally smitte...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...