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wittlesissybaby

wittlesissybaby

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The Boss' Baby - Epilogue

The Boss' Baby - Epilogue

Author’s Note: I started this story over two years ago. It started out as a small little idea about a man that gets dominated, sissified, and cuckolded by his Boss. I thought it would be a fun little chapter or two to add to my blog. I had no idea it would become so popular. People were...

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Meet the Parents - Chapter 2

Meet the Parents - Chapter 2

“What about your Step-Dad?” Phil asked as he attempted to fix and reapply his lipstick. It had gotten a bit smeared when Jan was grinding on his face earlier. “Will he be at dinner?”

“Oh, he’ll be there…” Jan said curtly. There was dripping disdain in her voice at the mentio...

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Teddy Time (Custom Caption)

Teddy Time (Custom Caption)

As Teddy sat and played with his toys, gently sucking his paci, he reflected on his day. He had gotten all his chores done–well, the ones he was still allowed to do for his ‘age’. He spent the whole day crawling around on his hands and knees, wiping the floors with his cleaning mittens and ...

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What's Your Favorite Phrase For "Making a Dirty Diaper"

Just for fun, just to see what you think.

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Go Ask Alex Collection 2


Day 3

Day 3 of sobriety is always the hardest. I get itchy, I get chills, I get lethargic, it feels like my head and body are being stabbed by 1,000 tiny needles, it...

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Feels like the First Time


“So have you ever done this before?” I asked.

“Well...I have…” Emma replied nervously, “Just not...with someone his age before.”

“It’s simple.” I repli...

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Discussion Time

As I've begun to get more acquainted with you guys and fielded some of the things you like/dislike when it comes to captions and story content, I've gotten the impression that something a lot of you seem to want more of is what I would call "gentle femdom". As in,  you like to see a more car...

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Sorority Boys - Chapter 1 - The Panty Raid


The mission was simple: infiltrate the Theta Iota Theta sorority and get out with a pair of one of their panties. Bonus points would be given if you found a dildo/vibrator.

Caleb scaled ...

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Go Ask Alex (Collection 1)

Day 1

They told me I had to write in this stupid journal every day. Something about how it will “help with the treatment process”. They can try whatever they want. I’ve b...

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Practice Makes Perfect


“Can I stop now?” I asked. Gasping for breath.

“Did I say you could stop?” She snapped, barely looking up from her phone. Swiveling around in her chair.

“My cheeks burn a...

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Meet the Parents

Jan pulled up in front of the estate. It was a nice, secluded house that had its own dirt road and white picket fence going around the perimeter. She put the Jeep in park and turned to her boyfriend Phil...

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Introducing the New Golden Goodnite Tier!!

I'm happy to announce that my Patreon will now offer a new Gold Tier Package! Subscribers to this tier will receive:

1 Custom Caption for Every Month Subscribed

Abili...

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You Should Smile More


It was a crowded club on a Saturday night. The music was blaring. A little too loud and a little too poppy for my tastes, but I nodded my head along as I watched my girl friends make drunken f...

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Weekend Services (Day 2)


I don’t know of any better way to start the day than to be awoken to the feel of your morning wood in someone’s mouth. I woke to the sound of the little slut sucking and slurping and moani...

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DREAMS Daycare

I pulled the Range Rover up to the roundabout behind the line of cars. I put the car in park and pulled out my phone while I waited. It was 3:10, they wouldn’t let out for another 5 minutes.

I al...

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The Boss' Baby Part 15 - Pressing Matters


“Wahhhh!! Ahhh!! Ahhhh!!” The baby cried. Amy rushed down the hall and into the baby’s room.

The nursery was painted pink and decorated like any baby girl’s room. The baby was on...

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Monitored

 


We collapsed on the bed. Panting heavily. Our naked bodies glistening with sweat.

“How many was that?” I asked between breaths. “Two? Three?”

“Four.” She heaved. ...

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Weekend Services - Day 1


The knock finally came.

I had been pacing back and forth ever since he texted “omw”.

I opened the door to see him standing there in the prissy maid outfit, wig, and flawless ma...

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The Boss’ Baby - Part 14 Desperation


1...2...3…

Jesus, how many times did they do it last night?! I contemplated sorrowfully as I squeezed the contents of the 4th used condom into the tiny bowl.

It had been...

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Road Trip


We were barreling down the highway at 75 mph. It was a flat, open stretch of land somewhere between Texas and New Mexico.

Roy was at the wheel with his arm around Sandy. Not a care in th...

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The Boss’ Baby - Part 13 Dinner


I was sucking and licking every part of his cock. Head, shaft, balls, the space between, and the space underneath. Anything to see if I could get a hint of a taste of my wife’s pussy on his ...

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Play Date

The doorbell rang, and Jessica sauntered over to open it.

“Hiiiii!” Both girls said in unison. Chr...

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The Boss’ Baby Part 12 - The Night Out


“Enjoying your cartoons baby?” Amy asked. Kneeling down next to me and smiling.

I had spent the last hour on the floor of the living room inside the 18-inch walls of the “playpen...

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The Hunt - Chapter 1


“Come on, man! It’ll be fun!” Chris had said. “Just a week away from it all. Out in the great outdoors. Enjoying the thrill of the hunt. It’ll be super relaxing!”

Well it was...

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The Boss’ Baby Part 11 - The Replacement


“Hi honey!” Amy said as she came through the door to the house, carrying several large shopping bags in each hand. She was bouncing and smiling as if she’d just won the lottery.

I ...

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What do you like to see the MOST in stories?

Hey guys! Please answer the question below. I'm curious to see what you want to see the most of in my stories so I can make them better for you! Feel free to elaborate in the comments below! I love hearing from you!!

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The Boss' Baby Part 10 - Office Christmas Party


It wasn’t held in our office building. The company spared no expense as they rented out the ground floor and grand hall of an expensive hotel. Everyone I worked with was congregated around a...

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The Baby Shower


“Did you remember to get the diapers?” she asked.

“I did.” I said, “I didn’t realize how damn expensive they are!”

“Well that’s the cost of having a bABy!” she ...

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The Boss’ Baby Part 9 - The Shift


You know how when someone tells you not to think about something, that something immediately becomes all you can think about? Like, if I say ‘don’t think about the color Red’, which colo...

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Sniper Diaper


Attention: 5 squads remaining. Came the announcer's voice.

“I’ve got eyes on one of them.” Aaron’s voice chattered through the mic. “Looks like they’re ...

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