Cross Dressing Stories

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Orientation
Length
Source
Infinite Scroll

More Tales from the Guilds Ch. 03

by voluptuary_manque2 on Apr 10, 2019
Sci-Fi & Fantasy

In some place that had not existed before, and only existed now for this very purpose, there stood a large, gleaming vat. "Ten thousand gallons of delicate fondant sugar cream infused with essence of violets and stirred into dark chocolate," said Chaos. "There are also strata of hazelnut praline in rich butter cream, and areas of soft caramel for that espec...

Copswap2030 Ch. 06

by DonScott on Feb 10, 2020
Transgender & Crossdressers

"I have someone different for you today," Jacob told me as he fitted the helmet on my head. "Why?" I asked, "don't you think Rik has any more info to give?" "Rik has gone back to the hospital, he took a turn for the worse." "Oh," I said, disappointed that I would not be sharing his memories and feelings, "he will recover though, won't he?" "I expect so."...

No Going Back!

by allourdesires on Jun 11, 2019
Transgender & Crossdressers

You had a lot on your plate that day: a huge backlog of work to complete, a number of clients to contact, and far too many petty, in-house meetings to attend. A duvet day was exactly what you needed. Let's face it you weren't feeling the best anyway; maybe some kind of low-grade, background fever. You couldn't risk passing it to your colleagues. The company...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Sunday

by fewella on Nov 19, 2018
Erotic Couplings

Larry's eyes were closed as he listened to the pastor finish his sermon. His face and body relaxed as the words washed over him. "Amen," he murmured and his eyes flitted open. As he waited in line to speak to the pastor at the door of the chapel his thoughts turned to today's sermon. The pastor had talked about acceptance and tolerance of others and it had...

A Halloween Treat to Remember

by fantasylover 43 on Jul 14, 2020
Romance

"Trick or Treat!!" Dozens of times I've answered that call of the doorbell, to be met a vast array of little monsters, ballerinas, and soldiers. I really get a kick out of Halloween, all the excited little faces, and the chance to be a kid again, dressing up to fit the occasion. I have a hidden motive , though, I have to admit. I like dressing in a costum...

The Punishment Room Pt. 02

by J_Birkenzweig on Aug 24, 2020
BDSM

Part 2: Learning the Implements "This is the room," his hand encompassed the whole room with a semicircle " where I can tame unruly women really well. I'm going to try some positions on you now." Claudia looked from the bench to the trestle, to the X-frame and then to all the punitive instruments. He led her to the punishment horse. "Lie over it." She be...

Your sammich maker; my fuck-pig!

by Wank_Gough on Jul 14, 2020
Fetish

Wank Gough, aka 'The Goughster' here, with some guidelines to help all you WASPs (White Ango-Saxon protestants) out there fulfil your cuckold status. Now, as I'm all about the love, here's a little warning: tetchy WASPs who don't think they're natural and willing cuckolds might want to stop reading here, as you're likely to not be able to cope with ideas w...

A Halloween to Remember Ch. 03

by jealouscuck on May 7, 2019
Fetish

I didn't want to get totally involved in Sonia and Keith's sexual fantasy, but I had shared that Jeff had cum in panties more than once. According to her, Keith was in a new world dressing regularly. He had a drawer full of bras and Sonia was going to purchase some breastforms for him. I wondered if we might end up having a little party in the future with Je...

Power

by TruePoly on Dec 30, 2019
Loving Wives

5:30pm She picks the hotel room and checks in, a nice suite at Holiday Inn Express with the living/lounge area separate from the bedroom. In this case it wasn't separated by far, with only a half-wall between them. You couldn't sit on the couch in the living area and see into the bedroom, but if you stood in front of the couch you could see at least the low...