Sissy Secretary Stories

20,580 results
Orientation
Length
Source
Infinite Scroll

My First Time as Sara... Pt. 03

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully. As Sara...

Steve to Stevie to ?? Ch. 09

by gbr2004 on Sep 19, 2017
Fetish

Steve had a very bad trip back to her apartment. First it was the black cop who stopped him and used him like his bitch. And, then before he understands all the implication, he has promised to be a sissy whore for him. Then the vice detective who has decided that he will make Steve suffer if he can't control himself and not be a whore. Then, so much worse at...

Financial Difficulties

by tazsis1 on Sep 12, 2017
Loving Wives

We got into some financial difficulty a few years ago. I'd borrowed a lot and Elaine and I spent too much over one Christmas on the kids and family. And then I lost my job. It was all very difficult and, as these things do, it affected our marriage profoundly. While we kept our troubles from the kids, Ellen and I talked about little else -- driving out all p...

Throne of Panties Ch. 02

by scur on Sep 16, 2017
Fetish

This story continues where "Throne of Panties" left off. A man made the mistake of allowing a stewardess to see him in panties and stockings and instead of getting a blowjob he was pushed to the ground and now another passenger becomes involved. I think both stories would benefit from being read in order. ***** "Oh really." the other passenger said. "Does...

The new "girl"

by BimboBarbie on Oct 3, 2018
Transsexual

You clutch your shoulder bag and look up at the tall, intimidation glass structure. The large blue sign over the revolving door reading "MFT". Short for Michael's & Fuller's Tech, a rather small but up and coming tech firm that mainly produced micro chips for home computers. Even with the relatively small size they only had a few firms and so t...

Open in Reader

Jack and Jill Pt. 03: Anna

by candyflosslover on Jul 13, 2020
Loving Wives

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...

The Transition Ch. 03: Aftermath

by Quantarx on Jul 6, 2020
Transgender & Crossdressers

Greetings and thanks again for reading my story. This is the third part of the story, so go back and read the other chapters if you want the whole story. As always I really appreciate any feedback you leave in the comment section down below. Be sure to follow me if you like the story so you don't miss any future chapters. *** I woke up in the middle of the...

Mommy Adriana Makes Greta Become...

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, it took me a while because reality caught up with me, but now the next chapter is ready. I simply hope you don't get bored and enjoy also the 6th installment of my little story. * Finally I lay in bed. I heard Mommy Adriana was sound asleep while I tossed and turned. I simply couldn't sleep after today's events. I would never be the same man...

Fringe Benefits

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Shawn showed his employee badge to the TSA agent and was waved through to the metal detector. He quickly slid off the lanyard placing it into small bin to take a ride down the conveyor belt. Once he was fully cleared, he collected his belongings and headed away from the security checkpoint to the Office of Physical Plant. He clocked in then spoke to his boss...

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...