Sissy Thong Stories

50,082 results
Orientation
Length
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Infinite Scroll

Letters from my Mistress 01

by Slava28 on Sep 16, 2017
BDSM

I text you to tell you that I am on my way and to be ready. You trim, you shave and by the time I arrive and let myself in, you are kneeling in the middle of your bedroom, head down, like a good slave. I go to your closet and go through your clothes. I pick out a tank top, a thong, a skirt and a pair of heels and tell you to dress. As you start to put on you...

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...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

My Husband's Submission

by pamcd on Sep 16, 2017
Fetish

Last night as I lay in bed, I was surprised when the man next to me wasn't my husband. The bedroom was dark except for the little light coming in through the small opening in the curtains. The man says wait wait a minute, as I was getting out of bed. I said who are you and what are you doing in my bed? He said I am a friend of your husband and your husband t...

Step by Step Sissification Ch. 01

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- It all star...

A New Way Of Life Ch. 02

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

A Big thank you to Chris & Scott for the great eaditing job. This is the 2 part please read the firts New Way I looked at Everett, "Ok, are you sure?" "Yes, Carine. Now go get ready. I'm hungry." I headed off to the bathroom to fix my make-up and hair. Looking at myself, I can't believe what had happened. I was loving it! I had never felt so alive, tu...

Chrissy's Trip

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: Trouble in Paradise It has been seven months since Chrissy and Miriam had their memorable first date, and things are going well. Every night Miriam is in town she falls asleep with her giant futahood buried in Chrissy's cum filled ass, and most every night she is away Chrissy heads to Futanari Palace to sate his hunger for cock and hot futa juice....

Jacki's Journey into Sissyhood Pt. 02

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. ***** I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from unde...

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...

First Time Bi

by First_time_bi on Sep 16, 2017
Transsexuals & Crossdressers

I never thought that I'd be in this position. I am a 40 year old married man, 5'9" 185 lbs and try to work out regularly to keep in shape. The problem is that I travel constantly for work. It takes a tremendous amount of willpower to avoid the junk food and commit to a workout schedule when I am on the road. For the past 3 years, I have been the leading sale...