Sissy Couple Stories

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From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Prankster Ch. 08

by Paris Waterman on Sep 15, 2017
Group Sex

Late the next afternoon, Tony met with Barely to set things up for that evening's session at Crazy's place. "You know," Barely said, "I came across something last night when I was editing the tapes." "What was that?" Tony asked. "It's best I show you, then you tell me if you want it back in. It was me, I'd keep it out. I just don't feel comfortable with...

Linda

by ofloveandlust on Sep 16, 2017
Erotic Couplings

"How old were you at your first?" "Oh my god, you don't ask a woman something like that!" Linda elbowed him in the gut. It was flat and hard as a rock and she was probably more turned on by it than he was injured. "Vut? I can always Google it." His accent wasn't all that thick but from time to time it would be noticeable. That turned her on too. If they ha...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

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...

Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...