Sissy Pussy Training Stories

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Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

Master Gene's Email Response

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Back at home that night I kept thinking of what had transpired that morning with Master Gene while still wearing my cum stained panties as Master had told me I could only remove them to shower. Otherwise the pink thong panties that had been soaked in cum would remain on at all times until I was told I could switch to other panties of mine. Was this a sign Ma...

Behavior Modification Institute Ch. 10

by NancyPan on Sep 12, 2017
Fetish

Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series. ***** I was standing with my petticoat and the skirt of the maid's uni...