Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Sissy Awakening Ch. 01

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sex Shop Glory Hole - "Hey baby, when are you coming home?" the text message buzzed quietly. Pulling the phone discreetly from my pocket, I type out, "Same time as usual, just after 5, why... what's up?" It's my lover Sarah, my best friend, and woman I'd known for over 10 years. We were dating and quite a serious item within months of meeting. Everythin...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

Sissy Slut Ch. 02

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

At first I was a little pissed she just discarded me like that so easily, but I quickly got over it, as I was now free. Thankfully there were no other houses nearby that I had to worry about being seen in all my naked glory. It took me a few minutes before I was able to drive away, as I had to get dressed first. I kept looking back at the house, as I wanted...

Neighbourhood Terror to Sissy Pt. 22

by Fibaro on Jul 6, 2020
Transgender & Crossdressers

Chapter 24 "Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it'th important to know how to apply makeup, it'th important to know how to remove it ath well. After all we don't want you developing a bad thkin cauthe of all the makeup you're uthing." Stephanie ordered not even giving Marcy a few minutes to deal with what had just ha...

Appointment by Card Only Ch. 02

by Sputnik57 on Sep 17, 2017
BDSM

Madam Ruth was more than pleased with her days work as she descended to the bed and stroked the soft white body of the helpless sissy, Poppy mustering a whimper as the dominant Madam. Cupped the soft pink scrotum and gently worked the dainty cock to an erection; she was scared but the surreal situation along with the gentle warmth of the two females, combine...

Abducted and Turned Out Ch. 03

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

...... So, he walked up and positioned himself at my cum soaked pussy and penetrated me, and as he did I couldn't help but moan and encourage him by saying, "Fuck my pussy". As he was pounding me relentlessly for the next few minutes, he began to tell me about himself. "I noticed you the day you moved in. I knew you were a slutty little sissy then, and I k...

BBC Worship Ch. 03

by CumSlurpingCuckold on Sep 18, 2017
Interracial Love

The time had cum to discuss the full implications of her pregnancy and ongoing relationship with Jerome, whom we both loved and worshiped dearly. Wasn't it time to admit to her family and a few other friends and coworkers who still didn't know? Didn't they deserve to know that the marriage that they had seen us commit to a few years ago was now a sham, that...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

The Making of an Angel Pt. 02

by AngelLawrence on Jul 29, 2019
Transgender & Crossdressers

This is the 2nd stage of my biography of how I went from vanilla male to shemale slut. All persons are over the age of 18. *** I gulped. The close proximity of the woman and all the pretty lingerie in front of me was making me feel light headed. "What size are you?" She asked. "28" waist 38" chest" I replied. "No silly! What girl size are you?" she...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...