Sissy Bottom Prostitute

By John Nail

Published on Jan 29, 2009

Authoritarian

Well, a week went by and I was playing Grand Theft Auto and Andy came in and motioned me in and there was Mr. Coswell smiling at me.

My client called and said that he will be back from his business trip in a few days and he very much wants a date with you. That will give us time to get you ready now go with Andy and he will show you what to wear. I followed Andy and we went to this room and he opened up the closet and brought out this extremely short skirt this low cut blouse and low cut bra and these pads that looked like breasts and 4" heels.

Andy said," Put these on I will give you ten Min's. "

I said," Are you kidding? I am not going to be a transvestite."

Andy said," Put these on or Mr. Coswell will give you to the biggest perverts in the world. Believe me you don't want that to happen you won't be treated nicely by those guys. They will rape you on a daily basis and than unleash their mule on you and you will be that mule's bitch."

He left the room and I decided to put on the outfit I put the thong on and I hated the feel of the strip of cloth up my ass. I put the pads and bra on and than I put the nylons on and the 4" heels. He came back in as promised and showed me how to put the make up on. Than he told me to get up and start walking. After falling down several times he told me to sit down.

He said," You don't take long steps you take small steps and let your ass wriggle while you walk. You are no longer walking as a guy but as a girl got it."

I did as he instructed and after about a half hour i got the hang of it.

Mr. Coswell smiled and said," You are doing quiet well you will make my customers very happy and I think your new name will be Candy. You will no longer dress as a man but as a sissy-boi and you will do nicely indeed."

Our lesson was over but as I got to my bedroom inside the closet it was changed no longer were guys clothes but clothes that girls my age would wear designer jeans blouses skirts and such. Mr. Coswell came into my room and pinched my ass and was smiling.

He said," It is time to train you to suck dicks properly even though our client wants you to be a virgin he still wants you to have some skill at sucking dicks. I thought about you using a dildo but I love receiving blowjobs."

He went over and sat down on the bed and unzipped his pants and lowered his boxers. Out came out this hard 8" cut dick and he said for me to get on my knees and to not touch it. I did what he told me and he also told me to breathe through my nose.

First, I started to lick the head and the precum and surprisingly it wasn't bad. I opened my mouth and took a little bit at a time with Mr. Coswell reminding me not to use my teeth. I went down further and further down his shaft and than he pushed me down to his pubes. I sucked his dick for about 15 mins. and I felt his dick jerk and than I felt him cumming down at the bottom of my throat but he pulled it partially the way out. I tasted it it tasted partially bitter but not bad. He spurted about 5 times and than his dick started softening and than popped out.

He said," I didn't want to tell you that I was cumming because you might have tried turning from my dick and I wanted you to get accustomed to the taste of cum. By the time my client gets done with you, you will have plenty of cum in both holes."

He left and I realized what I was turning into a gay prostitute servicing men.

Those few days were a blur and the client called and I packed my bags and got in my short skirt and low cut blouse padded bra and 4" heels

Mr. Coswell said," You will be with him for about 10 days, don't worry his is the only dick you will see. He doesn't like sharing his sissy-bois but that boi-cunt will be more than satisfied have fun."

The limo pulled up and this tall lean man came out after the chauffeur opened the right door.

The man said," You were right she is a pretty one and we should have a delightful time."

He motioned me into the car and he gave Mr. Coswell a big bundle of bills and than he came into the limo and the door was shut and the chauffeur got in and started the car and we left.

He said," You can call me Raul and I think our time togather shall be agreeable."

He reached under my skirt and started playing with my ass and reached over and grabbed me and started kissing me and our tongues met. We just kissed in the trip to his house. About 20 mins. later we arrived at his house and guided me to the bedroom and he started kissing me more passionatly and started stripping me and I stood there naked and he pushed me onto his bed.

He took some lube and he started to lube my ass and his dick. He fingered fucked me with 3 fingers and it hurt me but as he started to massage my prostate I moaned in estascy.

He looked at me and said," It is time to deflower you sweetheart."

He stripped and I saw his very hard 8" cock and I felt an intrusion into my puckered hole. He started pushing it further down until I felt his pubes on my hips.

He started fucking me slowly at first as we kissed passionatly and we were entertwined. He was fucking me for about 45 mins. I can feel sweat rolling down my forehead and my dick getting harder every minute. I felt his dick twitched and than his dick gushed about 5 spurts and my ass felt so filled with his cum. And there was blood and cum mixing that leaked out of my ass.

He smiled and said," We have properly bred I think you have found your true calling."

About 15 mins. later his dick got hard again and he said it time for you taste my cum don't you think. I crawled up between his legs and I took his cock into my mouth licking the head and than working up and down his shaft and than I took his delicious balls in my mouth. Than worked my way back to his head and started sucking his dick.

I worked my mouth up and down his shaft and than about 15 mins. later his dick twitched.

He said," I am cuuuuuummmming sweetheart."

He flooded my mouth and throat with his delicious cum and I swallowed it all.

He said," It is time to go to sleep and we will sleep naked I want to feel my cock into your ass while sleeping."

Next: Chapter 3


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