Sissy Glory Hole Stories

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A Sissy's Lifestyle

by nancyvasquez on Sep 13, 2017
Anal

When I go out to the adult bookstore, I am always dressed as a woman. And not just as a woman, but a whore. I tease my hair up big and high, and will have either a dress, skirt, or butt baring short shorts; and, of course, high heels. It's a 15-minute walk from my apartment to the arcade, and my route runs me through an industrial area along a fairly wide av...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Memorial Day

by 9volt on Jun 9, 2020
Fetish

Memorial Day Weekend On Saturday of Memorial Day weekend I got up and went for a run. When I got back, Brandi was finishing up with breakfast for the kids and her parents were there to take the kids for the weekend to the family cabin on the lake. I grabbed a quick bite and headed to the shower after kissing the kids goodbye and wishing my in laws well. I w...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Neighbourhood Terror to Sissy Pt. 15

by Fibaro on Dec 23, 2019
Transgender & Crossdressers

Chapter 17 "If you don't mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don't trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great." Linda said to Lisa who was still getting her feet wors...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Sissification 101: Ch. 04

by silkstockingslover on Jul 14, 2020
Transgender & Crossdressers

Sissification 101 Ch 04 Summary: Eric sucks his first BBC in a threesome with Joan. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by his...

Caught by the Lodger Ch. 02

by SuzieR on Sep 13, 2017
Transsexuals & Crossdressers

Over the next few months Rachel continued my training. She was determined to transform me, in her own words, into 'the perfect sissy slut girlfriend', and I was only too happy to go along with it. There are a strict set of rules that I have to follow. I am allowed to wear my male clothes when I'm out of the house but must also wear a pair of panties undern...