wittlesissybaby

The Boss' Baby Part 8 - Busy Day

It was a busy day.

My morning started with Dave from IT emailing me to come down to his office. I knew exactly what that meant.

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The Boss' Baby Part 7 - Terms and Conditions

“So what’d she say?” Stephanie asked as she applied mascara and eye shadow to my eyes in Charles’ office.

“Who?” I asked. Pl...

New Stories are coming!

Hey guys! Thank you all so much for your patience as I get this site up and running. It has been a bit of a nightmare navigating all the different rules, regulations, and guidelines. I am trying to not get taken down like my Tumblr did. Boss Baby ...

The Talk

I felt like his mother. One that was casually minding her own business as I searched for a Doctor in the area. But as soon as I typed in the l...

The Boss' Baby Part 6 - Using the Restroom

“On the floor.” She commanded. Her voice was almost as stern as Charles’.

“But this is the women’s restroom!” I pleaded. “What if som...

The Boss' Baby Part 5 - Pampered

“So...what did you do to earn this?” The secretary Stephanie asked. Holding the very large diaper in her hand as she stared down at me over her black...

The Boss' Baby Part 4 - The Mess

Good morning, Tom!”

“Good morning, Dave!” I said as we passed each other. Dave was the IT guy that Charles had used to find the in...

The Boss’ Baby Part 3 - Getting Off Early

There are a few things I wished I could get rid of that day:

The first was the taste of my Boss' cum lingering in my mouth.

The second was th...

The Boss' Baby Part 2 - The (Blow)Job

I could feel His hard cock between my asscheeks as I gave Him a lap dance in His desk chair. I’d be lying if I said I hadn’t noticed the b...

The Boss’ Baby Part 1 - Bad Marks

Tom, can I see you in my office please?

It was the Boss’ voice over the intercom. I looked up from my computer and...

Bound for Release

 “What’s happening?” I asked as she tightened the bonds on my wrists and ankles. “What are we doing?”

Usually when she strapped me to the bed spread-eagle like this she would have me face-up, not face-down.

“Were you t...

Sissy School - Chapter 7 - First Day of School

"Wake up, Fairie! Wake up!" Bryan called, leaning over my crib like a Mother would to her Toddler. "It's our first day! It's our first day of SCHOOL!"

I did not share Bryan's/Brianna's —whatever you wanted to call her— excitement.

I had s...

Hoetel Bimbo - Chapter 1 - The Client

I wheeled the cart around the corner to Room 257. My heels thunking against the carpeted floor. The frills of my slutty maid outfit swishing as I walked. 

Mistress made it clear this was a very important client.  All clients were ‘impor...

Sissy School - Chapter 6 - The Sorting

Like a toddler on a trip to Disney World, I was stuffed in a 1950’s style stroller and led into the gigantic castle. The difference being that most kids would kill to go to Disney World, as i’m sure most of the sissies like Bryan would too. But n...

Sissy School - Chapter 5- The TuTu Train

The Train Station was only a few miles from Guyagon Alley, but a walk like that in heels made it feel like we were going across the country. The locking straps of the heels were the only thing keeping my ankles from snapping every time I rolled them....

Sissy School - Chapter 4 - The Makeover

The Sissy Salon looked just like any other on the inside. As we walked in there were sissy's in chairs getting perms, highlights, haircuts, etc.  We were greeted by a beautiful woman in a sexy black dress with fishnet stockings undernea...

Sissy School - Chapter 3 - Guyagon Alley

I was locked in the trunk of Tyrone's car, bouncing down the road in pitch black. I was still cuffed and gagged from before, but thankfully I no longer had the used condoms still in my mouth as they had made me chew them like gum until I could swallo...

Sissy School - Chapter 2 - The Bouncer

BOOOOOM!!! BOOOOOMM!! BOOOOOOOOOOOOMMM!!!

There were 3 huge knocks on the door. So loud and hard it knocked dust off the underside of the staircase onto my face.

It was the morning of August 1st, the day after I was supposed to repor...

Sissy School Chapter 1 - Accepted

I woke up to the sound of them fucking in the room above me.  The rumbling of the bed was causing the dust from the ceiling above to fall on my head with each thump. At first it was hard to think of my wife, Sherry, with another man, but ...