by
Sissyhalo
on Sep 13, 2017
Transsexuals & Crossdressers
Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room.
And my luck turned around after I won money.
Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...
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by
Sissyhalo
on Nov 25, 2017
Transsexuals & Crossdressers
They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it.
It's somewhere in between and none of it either.
It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass.
It started for me...
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Transgender & Crossdressers
Chapter 15
Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...
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Transsexuals & Crossdressers
Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...
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by
maturesubmale_for_F
on May 12, 2020
Transgender & Crossdressers
1. Miss Stern delivers both punishment and pleasure
I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...
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by
Sputnik57
on Sep 15, 2017
Transsexuals & Crossdressers
Pepper returned to the room and sat on her new bed as she unpacked her things; Marie helped her stow things in a wardrobe and chest of draws allocated to her. The blonde smirked at the new girl as she blew on the brunettes nails she'd just completed; she would enjoy painting Pepper's nails. Pepper bounced softly on the large double bed; the plug felt so nice...
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by
Sissyhalo1
on Dec 16, 2019
Transgender & Crossdressers
It was one of my first lessons as a sissy that I learned on my own.
New girl only appealed for some men.
And there were all sorts of hotter sissy girls there just working it in the food hall and other places.
With real breasts or close enough, with great asses that were getting attention.
And as femmed up my brain was there was still this sort of competi...
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Transsexuals & Crossdressers
With great care I slowly pulled the 10 denier black nylon stocking up my leg. I had other pairs, but these were my best and today it was important to have the best. Cautiously I rolled up the second one and with the same deliberation pulled it onto my other leg. The feeling, of soft nylon sliding over my naked skin exquisite and exciting as always, but today...
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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...
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by
Sissy_Chantel
on Sep 14, 2017
Transsexuals & Crossdressers
Chapter Seven: Another Day in Chantel's New Life.
It's 7:30am and the alarm clock goes off. I awake to my first morning in my new sissy slave home and life as a sissy maid and slut. I get out of bed, stretch and strip nude for my enema and shower. My butthole still hurts from last night's gang rape session, but I won't protest, nor do I really wish too. In...
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