Sissy Secretary Stories

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Orientation
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Infinite Scroll

Outed and Married Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

The head of his cock pushes hard against the back of my throat. I struggle not to gag. I struggle to control my gag reflex. I feel my throat spread open as he pushes his erection all the way into me, pushes deep into my mouth. It never gets easier no matter how many times he's done this to me. I feel that brief flash of slight pain as he deep-throats me. Fro...

Confession of a Total Sissy

by meeah soo on Sep 13, 2017
Fetish

Somehow this was the most difficult thing I'd had to do since becoming my wife's full-time sissy. Across from me sat my best friend Jack and he was waiting for an explanation. Well, what kind of explanation could I possibly give him? Here I was, his co-worker, his buddy since college, the guy he shot pool, played cards, watched the Knicks with at the Garden,...

Her Friend Came To Visit Ch. 02

by Dewmyne on Oct 13, 2020
Transgender & Crossdressers

When I woke up in the morning, Meg had left for work and Larry had gone to his meetings. I was laying naked except for my bra and one stocking and had dried cum all over me and a terrific headache. I stumbled to the kitchen for a big glass of water and Ibuprofen. Laying on the counter was a note saying "You had quite a night girl and we thought you needed th...

Cum Addicted Husband Ch. 06

by Subone1 on Dec 9, 2019
Loving Wives

The big day finally arrived - my final exam! If I make it through the party tonight, I will get to be my wife's cum slave forever. I wouldn't have to settle for "left over cum", I would be entitled to eat it directly from her freshly fucked cunt whenever it was available -- A treat I relish with delight! I took the day off work at Karen's direction - she m...

The Beach Trip

by wifestoy on Sep 13, 2017
Transsexuals & Crossdressers

We were saying good-bye to the boys and readying for our beach trip. Renee was going to explain the facts of life to Ms. Anastasia Elizabeth Messier. Good bad or indifferent the rules and life plans were going to be laid out in this chapter. We were getting ready to explore another side of our growing relationship. We will be enjoying some well-deserved time...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Stuart's Secretary

by justincbenedict on Sep 17, 2017
BDSM

Stuart thought dreamily of his days at the firm in Chicago, and the two male Masters he'd lived with... One of them deaf. The rich 26 year old Stuart had loved and feared the two men. Now he watched BDSM porn... The way that model has his cock whipped reminds me... Of the day Master Pietro caught me with the Frederick's of Hollywood catalogue that I'd...

The Doctor's Appointment

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

My wife Jo had been suffering with a bad back for weeks. She works as a doctor and many of the procedures she has to carry out on patients require her to stand up for hours at a time. A couple of moths ago she fell off a horse on an activity holiday we were on. And she's never fully recovered. Urged on by my insistence to get her back checked out properly...

Cocktale

by DeborahC on Jun 18, 2019
Transgender & Crossdressers

Lawrence was my friends' boss. He was a former theatre director who was now running a successful online store selling showbiz memorabilia, my friend David was his 'assistant', delivery driver, storeman, auction attender, diary secretary and from time to time guinea pig. Lawrence loved to mix cocktails and on occasion would invite a few associates of his to...

Devoted Husband Dominant Wife

by keptsissy on Sep 17, 2017
Loving Wives

PART FOURTEEN: He does whatever he likes with her, whenever he wants to. I remember one night she spent so much time getting ready to go out with him, spent at least and hour alone doing her makeup. She said he was taking her to a business dinner. My heart froze when she told me that. I knew about the dinner and I knew his secretary would be there. I said n...