Paying Rent Ch. 03

Story Info
Mike becomes Michelle.
1.9k words
4.39
160.4k
33

Part 3 of the 3 part series

Updated 11/02/2022
Created 12/24/2004
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I woke up in the morning, still on my mattress on the floor. My boy pussy was on fire and my panties were soaked with lube and cum. I went to our cell's toilet and let out a stream of my new master's cum. I couldn't believe I still had that much in me! I looked around for Jermane, but he wasn't in the cell. I figured he must have gone to his job in the kitchen and I'd finally have some alone time to contemplate my new life. Before I could get too deep in thought, a crackle came from the metal speaker box. "Tier time ladies. The nurse is here to see you."

All of a sudden the lock on my door popped and it cracked open. I quickly put on my top and pants and shoes and opened up my door. As I glanced around all I saw were the other "bitches" walking out of their cells. I then knew why the Deputy said "ladies". I went and got in line to see the nurse. When my time came, she handed me a pill and a paper cup of water. I asked her what the pill was and she just grinned. One of the other "bitches" tugged on my shirt arm and told me I was being given female hormones. She saw the look in my face and just laughed. "You will like it girl! You will get used to it, and the changes are so much fun to watch!" I then really looked her up and down and noticed she had some breasts! What will I tell everyone I know when I finally get out?

I left the line to the nurse and started to head back to my room when the Deputy called me to the Deputies station. I sulked over there and the Deputy said, "Jermane told me to tell you to take your shower now cause he will be off of work in an hour. Also, commissary dropped something off for you. It's in that bag over by the sink. Do not open it until you get to your room. Understand?" I nodded, and he winked at me. I kind of smiled and he just chuckled.

I grabbed the bag and headed to my room. When I got to my room I shut the door and opened the bag. Inside were a blonde wig, a black bra and matching black panties, a pair of black thigh highs and a slinky black silky gown. My little "clitty" got excited and I started getting hard. My speaker crackled and a voice told me to hurry up and shower.

I grabbed my towel and hurried to the shower. I lathered myself up again and started to shave my body smooth again. I soon was silky smooth again and quickly washed my hair. As soon as I was done, I toweled off and quickly put the peachy smelling lotion all over my body. I got dressed in my outer clothes only and hurried back to my room. I stared at my new clothes and again I got excited. I slid the panties up my skinny legs and over my small ass. There was a small bulge in the front so I decided to tuck my tiny "clitty" between my legs. I then put the bra on and it fit much better than the plain white one the jail gave me. I then took each thigh high and rolled them up my slender legs. I took the silky gown and slid it over my body. My skin was on fire from the silky fabric running over my smooth feminine skin. I put the wig on and then stared at myself in the mirror. I gasped. I actually looked womanly!

As I stared at myself in the mirror the speaker once again crackled and a booming voice told me to get ready because Jermane was coming in to get more of his "rent". I knew exactly what that meant and I went to my mattress on the floor. I got on my knees and waited for my master.

Jermane walked in and smiled. "I knew you would be a hot bitch for me. That's why I picked you. From now on when you are in my room you will be dressed like this. When you go out on tier time you wear the non-sexy shit. This sexy shit is all mine and I will say who gets to see it. Got it?"

As I started to nod, Jermane walked over to me and grabbed my chin and tilted my head up so I could make eye contact with him. I saw a giant bulge in his pants and it was growing bigger. I knew what to do, so I grabbed the waistband of his pants and slid them down. There staring at me eye to eye was his gorgeous massive black cock. I licked my lips and immediately wrapped them around his massive cock head. Jermane let out a groan and he started thrusting his large cock deeper into my throat. I relaxed my throat and more and more of his cock went down my throat. I actually started moaning as his cock slid on my tongue and over my lips. His cock tasted so good and I knew that no matter what my brain said, this is what I wanted to be.

Jermane's cock kept pumping in and out of my mouth and my dainty hands were rubbing his massive black balls. Jermane kept groaning. I thought Jermane was going to give me another batch of cum to swallow but all of a sudden he grabbed my head and took his massive cock out of my mouth. A long rope of spit still connected my mouth to his beautiful big cock. I looked up and into his eyes and I knew what he wanted. I turned around and stuck my ass up in the air. I wiggled my ass and said, "Please master. Please fuck my pussy and make me your slut again!"

I felt my gown slide over my ass and up my back. I felt my panties being slid down my tiny ass. My ass cheeks were spread and I felt something warm on my sissy boy pussy. It felt so good and I started to moan out loud. I turned around and saw Jermane licking my tiny boy pussy. I got so hot; I started moaning louder, begging for more. His tongue flicked my tiny bud and started to probe deeper and deeper into my boy pussy. My body was shuddering from the excitement. Soon I felt a lubed finger starting to be inserted into me and my body started to spasm. Another finger went inside of my boy pussy and my little "clitty" couldn't take it any longer and started to spew cum all over my mattress.

Jermane took this as a good sign and stopped licking and fingering me. All of a sudden I felt a massive warm object at the door of my boy pussy and I knew this time it was my masters cock. He started to slide his slick cock into me and I winced in pain. Even though he had fucked me the night before, it was still not an easy task to take him into my boy pussy. He slowly inserted more and more of his cock into my little tight boy pussy. The pain was so immense! I grabbed my pillow and buried my head into it. I felt tears coming out of my eyes but I knew how badly I wanted this! I started to loosen up and soon I felt his massive balls slap against mine. I knew Jermane had finally done it and gotten all 11 inches into me! I let out a low guttural moan and begged for him to fuck me like a slut. He withdrew almost all 11 inches and then slammed all of it back into me. I let out a loud moan and spewed more cum into my mattress. He kept slamming his cock deep into me and with each stroke I moaned louder and louder. I begged for his cock to fuck me, make me his bitch.

Jermane soon started to fuck me hard, with fast deep strokes. My boy pussy felt on fire, yet it felt so good! Just as I felt like I was going to cum some more, Jermane pulled his cock out of my boy pussy. "Lick your cum up off of the mattress bitch", he said. I scooted down and greedily licked up every drop of my own cum. I tasted so yummy! Jermane slapped my ass and told me to get on my back.

I got on my back fast and hiked my gown up so he could have free access to my boy pussy. He grabbed my legs and put them over his shoulders. My slim silky thigh high-encased legs were now over his shoulders as I felt his huge hard cock enter me again. All 11 inches slammed deep into me again and my eyes rolled back into my head and more cum spewed out of my tiny "clitty". Jermane laughed, knowing I was his slut for real now.

He started to bend me over more and more as his cock slammed deep into my boy pussy. Soon my legs were by my face and his cock was pounding into me with an animalistic passion. I had a steady flow of cum dribbling out of my "clitty" and my moans were getting so loud. I started wondering who was listening to us fuck.

My head shifted and I looked at our cell door window and there was the Deputy watching us. I winked at him this time and this time he smiled. Our cell door swung open and he came in and shut the door behind him. He pulled out his big white cock and started stroking it hard and fast. This prompted Jermane to fuck me harder and I came hard and clamped my pussy down on his cock. Jermane grunted loudly and I felt shot after shot of hot cum shoot deep into my ass. Jermane shuddered and pulled his cock out of my boy pussy.

The Deputy was furiously jerking his cock and I was so horny watching him. Jermane slapped my ass and told me to get on my knees. I did as I was told. "Suck that Deputy cock until he cums and then swallow it all. Show him I know how to pick a good slut", Jermane said. I grabbed the Deputy's cock and put it in my mouth. He let out a loud groan as soon as my mouth engulfed all of his cock. I sucked it hard and fast. I used my hand and jerked his cock as I sucked and licked the head of his white cock. As I sucked his cock, I felt a flood of Jermane's cum drip out of my boy pussy and produce a puddle on my mattress.

Soon the Deputy grunted and shot a massive load of juicy cum into my mouth. I kept jerking his cock, trying to get every drop out of his balls. With one giant gulp I swallowed every bit of his delicious cum. The Deputy took his cock out of my mouth, zipped up, and left our cell. I stood up and noticed a puddle of Jermane's cum on my mattress. I smiled at Jermane. "Lick it all up slut. If you don't you wont be getting any more cock", he said. I fell to my knees and happily licked ever bit of his delicious cum up. I knew where it had come from, but I didn't care. I wanted more of his cock! He he

To be continued...................

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousalmost 10 years ago
Very Erotic and Sex

Had me hard and stayed hard. Very graphic and descriptive. I wanted to be the bottom for the big man.

Read "Giving is Recieving: A Bottom's Story" it is very sexy, too about a older man becoming the sex toy bottom of a well-endowed, handsome, large man. Lingerie and first time cock sucking, swallowing cum and anal for the luck bottom named, "Sweetie."

Great Story-HOT and HARD!!!!

SissyjaymieSissyjaymieabout 11 years ago

I loved it I wish I could find a Man like that. To mold me into the perfect sissy slut.

AnonymousAnonymousabout 14 years ago
Great story!!!

Hope for many more chapters!!! Love to see how this bitch develops into a hot shemale. i wish i were in her place, no chance to run, no chance to hide, being force feminized, oh that is such a turn on!!!

hugs and kisses, greta at yahoo dot de

AnonymousAnonymousalmost 15 years ago
PAYING RENT

THAT'S SO FUCKING HOT-WISH I WAS THE BITCH WITH BIG BLACK COCK MASTER SUCKING AND FUCKING WHOEVER HE TELLS ME LICKING HIS CUM OFF THE FLOOR THAT DRIPED OUT OF MY ASS VERY HOT I GOT A BIG HARD ON

sissycrissisissycrissiover 16 years ago
Got me hard and wet

Michelle is such a hot and horny little slut. I love her willingness to be used by her master and the way she's developed such an appetite for creamy cum. It's great that you now have her dressed. I could just picture the bitch all dolled up on the mattress in her cell, her legs in the air, her clitty always dripping her sissy cream. She's one lucky slut. Thanks for the read.

Share this Story

READ MORE OF THIS SERIES

Paying Rent Series Info

Similar Stories

Party Slut Never fall asleep at parties!in Transgender & Crossdressers
A Sissy's New Daddy Billie is forced to be a sub-sissy.in Transgender & Crossdressers
Black Man's White Sissy A white punk learns to be feminine to his black master.in Transgender & Crossdressers
I'm Finally a Girl for a Man A feminine guy finally meets a lover.in Transgender & Crossdressers
The Making of a White Sissy Slut Steven becomes transformed to Stacy.in Transgender & Crossdressers
More Stories