Going Out of Business Sale

Story Info
A sissy now alone in life falls under the influence of a dom.
13.4k words
4.65
14.4k
24
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 am writing this account of my sissy slavery at the command of my Master. I have been very happy as Master's sissy, I am who I was meant to be.

One important note. During my initial training Master was very clean that I was his property and did not belong to anyone else. He could and would let others use me but only within the limits he set. Furthermore, the only one I was allowed to call Master was him. Sir and Ma'am were OK, but never Master or Mistress. I have followed these rules during the writing of this story.

It was the end of a really crappy month for me. My mom passed away early in the month. It was not a surprise as she had been sick for many years. The estate was settled a week ago. I was the only heir, so I got everything. It wasn't much. A small bank account, a small trust fund, a fully paid off house, an old car, etc. I also got her bills, they weren't too much either, mostly medical which the insurance and Medicare took care of most of. Her accounts were enough to handle the remainder with some left over. After I got out of school, I remained home and took care of her. I had a low-end job working odd hours. Mom insisted that I get and hold a job. She said to build up a work history and a little savings. She took care of the house, food and utilities. So, I had enough to go to college and get a degree and have a little fun. So, this month was a major downer and very busy for me.

It was just before lunch on Thursday when I was called into the head office. The general manager and the HR lady were there.

"Business has slowed down a bit and we have decided to lay you off. It is nothing personal. Your job performance has been weak this month. We are giving you 2 weeks' severance and a good letter of recommendation."

"I have worked very hard for you since I started here. You know that this month has been a very bad month for me. My mom dying and dealing with the estate have been quite trying with no support. Now you are just ripping away the only support I have."

"It's nothing personal."

I tossed my ID to the HR lady, grabbed the check and the letter and walked out of the office. Adding insult to injury, a security officer was waiting for me. He tried to prevent me from going to my locker, but I insisted. He went through my backpack before he escorted me to the back door. He stood at the door watching me as I got into mom's car and drove away. I went to my bank and deposited the check, keeping a couple hundred dollars in cash. Looking up the unemployment office on my phone I drove there to file a claim. It took me almost an hour to complete all that was required, after I had a good cry in the parking lot. It was just before 4PM, when I started for home. I wasn't looking forward to it. The house was empty and quiet. Last month, it was warm and inviting, despite mom's illness. Now it seemed so cold and empty.

I was passing by one of the strip malls that seemed to fill the area, when I noticed a going out of business sign. On the sign was a notice of being the last day. It was a women wear store. I don't know exactly what caused me to notice it.

When I was younger, right after my dad was killed in a at work accident. I would try on my mom's clothes. Mom was understanding about it but discouraged it. I eventually grew out of it. After her death, I slowly started to clean out her bedroom and started to pack away her clothing for donation. I would hold some of the items to my face and smell her. At night I would sleep in her nighties and imagine being a girl and having men use me. Soon they became black men in my dreams. I spent time on the internet learning about crossdressing and sissies.

So, I turned into the parking lot and walked into the shop. The only person I saw was an older black lady who appeared to be the owner.

"Hi deary, what can a help you with today? Looking for something for your lady, are we?"

"No, I am looking for some things for me."

"What are you looking for in particular?"

"I don't know. I am a beginning sissy. I don't know what I need or want."

"Tell me your story and maybe I can help you."

So, I told her everything. After I finished telling my story, she looked me over carefully.

"Not too bad, you're small enough that you won't look out of place. Your hair is a little long for a boy, but a little short for a girl. It will grow out though. You are not very hairy and with a small endowment. What are you looking for?"

"I am interested in being with men, especially black men."

"What kind of relationship? Loving, him dominating you, a mix, what?"

"Mostly him taking control and using me with a little bit of him guiding, protecting and nurturing me."

"Mostly a Master and a little bit of Daddy, then?"

"That sounds like it."

"What sort of clothing are you looking at?"

"As a girl, I would dress to please my man. But I do like the older styles. Dresses and skirts, especially long tight skirts. High heels. Love the look of corsets. I have tried on girdles and love the feel of them. Basically, a girly girl. Maybe slutty."

"I know several Black Men that would love to have a sissy to play with. Women now adays are not women, they are females. They think and act like they are equal to men. A lot of real men like sissies because the sissies know they are not equal to men. They are submissive and compliant to men. Real men like that. Is that what you want? Do you really want to be owned and used by real men?'

"Yes Ma'am."

"Let's get started. Strip!"

I stripped naked, while she took pictures of me. She then took very complete measurements of me, including shoe sizes. Then she handed me a pair of panties and told me to put them on. Which I did. She took a few more pictures and then had me put my outer clothes back on.

"Three doors down is a hair salon. Michelle's. She is expecting you. Ask for Michelle, she already knows what needs to be done. Do everything she tells you. She will call me when you are done. I may send you elsewhere for other things. Now get going."

"Yes Ma'am." And out the door I went. At Michelle's I entered and asked for Michelle. I was directed to a very curvy black woman at the back. I introduced myself.

"I have been expecting you. Come with me."

I was led into a back room and ordered to strip. I stripped down to my panties.

"I said strip, sissy!"

I took the panties off.

"No wonder you're a sissy. Even little girls wouldn't get any pleasure from that."

She put on a pair of rubber gloves and spread a foul-smelling gel over my body and made me stand in a shower stall. A timer was started, and I told to stand still. It was about 15 minutes when Michelle turned the shower on. With the hand-held shower head, she got every inch of my body. When she was done, there was very little hair remaining. She put me over a table and shaved the hair from my gentiles and then spread more of the gel over the remaining hair. After 10 minutes, she rinsed the gel with my remaining hair off. I was given a towel to dry off. Once dry, she told me to put me clothes back on and took me out front.

Sitting me at one of the salon chairs, she began to cut and style my hair, while one of the other girls trimmed my nails, put long fake nails over them and then painted them in hot pink. When Michelle was done, my hair was in a basic unisex style, parted in the middle.

Before Michelle called Molly telling her I was done, she took pictures of me and my nails and sent them to Molly.

"Ms Michelle, how much do I owe you?"

"Ms Molly, is taking care of it. You are to go to the last store at the end of the building. Mr Robert is waiting for you."

"Yes Ma'am." And I left Michelle's and walked to the end of the building. This end of the building was a little dark and dingy. The windows were painted over and a sign at the door saying minors were not permitted inside. I opened the door and walked in. What I found was an adult bookstore with a video arcade in the back. At the counter were 2 older men. One white and one black. The white one spoke up.

"What are you looking for?"

"I am looking for Mr Robert."

"That's me. Molly sent you?"

"Yes Sir."

"Come with me." He led me into an office in the back and ordered me to strip. Once I was naked, he began to measure my neck, wrists and ankles. Then he measured my equipment.

'No wonder." Was the only comment he made. Ordering me to stay put, he left the office and was gone for several minutes. He had several boxes in his hands when he returned. When he opened each box up, I saw they contained chromed metal objects. He took each item out and tried them on me. They were 2 collars, one a half inch round steel collar and the other was a heavy 2-inch steel collar. And the other boxes contained heavy metal wrist and ankle cuffs. The final box had the title 'The Vice' on it. Mr Robert pulled it out and began to fit it on my cock and balls. Soon, it was secured around my equipment and he put a padlock on it and locked it up. I was then told it was a chastity cage. Even with my cock fully flaccid it was a tight fit.

Mr Robert pushed me to my knees and pulled down the fly of his pants. "Get busy bitch!"

I just looked at him dumbly.

"Have you ever sucked cock before, sissy?"

"No Sir."

"Well, it's time you learn. Get your whore mouth to work!"

When I hesitated, he slapped my face. Really hard.

"Leo, get in here and bring the flogger."

While waiting for Leo, Mr Robert called Ms Molly. "The little bitch is not cooperating. She is refusing to do her duty. Here she is."

Robert put the phone to my face in speaker mode. Ms Molly's voice came over the phone.

"Sissy, Mr Robert is being very kind to you. I understand you have never sucked cock before. But you want to be treated like a girl, you must thank men properly like all girls do when men do things for them. So, treat Mr Robert properly and he will teach you how to properly suck cock."

"Molly, the arcades are starting to get busy, would you like this sissy get some additional training? I have one arcade stall set up where I can strap her to the wall with her mouth over the glory hole. I can put a sign up and there will be a line out the door."

"Not today, Robert. She is just starting out."

"OK, I'll just punish her a little bit."

"That works. Goodbye,"

"Leo, warm this little bitch's ass up a bit."

Leo left the office and soon returned with a leather flogger, which he used on my ass. It didn't hurt as much as it stung. Soon my ass started to warm up and then began to rise up to meet the flogger. While this was happening, Robert held my head still and began to rape my mouth. It didn't take too long before my head began to bob up and down on Robert's cock on its own.

"Look the bitch is getting it."

Finally, Robert emptied his balls into my mouth. He firmly held his cock in my mouth, so I had no choice but to swallow his 'gift'. He then pulled out of my mouth with a

"Lick me clean, bitch."

When I finished, Robert handed me my bags and sent me to the Dancing Shoe and to ask for Ms Susie. It was just the other side of Molly's. Once there, Ms Susie measured my feet and went into the back and came out with a small cart with many different shoe boxes. Pushing me into a chair, she removed both my shoes and socks and placed nylon foot stocking on my feet. Then she began to put shoes on my feet. Instead of the normal procedure of only one shoe, if the shoe seemed to fit, she put the matching shoe on the other foot and had me stand up. It didn't take too long and I had a small pile of shoe boxes on the chair next to me. The last pair I tried on was a pair of high heel slippers. These were furry with 3 and a half inch heels in pink. Ms Susie put the shoe boxes into 3 large bags. There 2 pairs of 3 inch pumps, 4 inch pumps 5 inch pumps. One pair black and the other pink. There were 2 pair of ankle strap pumps, one 5 inch and one 6 inch heels, each with a lockable hasp on the ankle strap. And the pink mules. Ms Susie, directed me to return to Molly's.

Entering Molly's, I saw that she was dealing with a woman customer. This customer looked me over as I entered the store.

"Molly, do you actually let this kind enter your shop and do business here?"

"Mrs Worthington, Their money is just as good as anyone else's. And this is the last week I am open, so I need to sell as much of my stock as I can."

The lady paid Ms Molly, took her purchase and left. I was directed to enter the back office. I stripped as directed and Ms Molly spread baby powder on my upper torso and pull a skin toned rubber apparatus from a desk drawer. This she placed over my head, then pulled my arms up through the top hole and pulled it down over my chest. It was a set of Roanyer breast forms in size D. I now had boobs, big boobs. A pink satin corset with white lace trim was placed around my waist and Ms Molly began to tighten the laces. She pulled the laces tight, loosely tie the laces and then do other things. First time she pulled a pair of suntan nylons up my legs and fasten them to the garters on the corset. Then she would tighten the corset some more. Next, she pick out a pink satin unpadded bra and placed it on me, fastening its hasp behind my back. She tightened the corset again followed by placing the 4 inch black pumps on my feet and placing a small padlock on each ankle strap. Ms Molly tightened the corset one last time. I felt I was in a giant vise cutting me in half.

"How are you doing dearie?"

"It is so tight, I can't breathe. I feel like I am being cut in half."

"Don't be silly, girly. All women go through this to look sexy for men. Besides you are talking and complaining so you are able to breathe."

I expected Ms Molly to put a pair of panties on me next, but instead, she made up my face. It was put on heavy almost slutty. As she was finishing a tall, large black man entered the office. He was about 6'5" and 240 pounds and looked about 45 to 50 years old.

"Just in time James. What do you think?"

"It appears to be pretty much everything you told me over the phone."

"That it is. It is very fresh meat. It sucked its first cock less than an hour ago. Less than 3 hours ago, it walked into my shop as a normal boy, now look at it."

It was disconcerting being talked about like I wasn't even there. Like I was a thing, a piece of property. The man walked around me checking me out carefully. He grabbed my chastity and inspected its size and security.

"Molly finished dressing it. It is acceptable."

Molly then put a pair of pink satin panties on me, they had a great deal of pin lace on them. A white satin blouse was next to be put on followed by a pink leather skirt that went down to my knees and zipped up the back.

James sat down on the desk chair and had me knee before him.

"Sissy, I have been looking for a sissy to be my slut. My wife of many years passed a while back. I am a very sexual man and need relief on a regular basis. Real women come with a very high price tag. They see me and dollar signs. I have found that all sissies want is my cock and seed. This weekend you are auditioning for the position of my sissy slave. If you work out, we will work out a schedule for you to serve and service me. Molly tells me that you are basically a virgin. That status will not last long. Basically after this weekend you will no longer be a virgin. I will not take you anally, at least not immediately. Sometime in the future, yes. But not right now, you will have enough to process. I am drug and disease free, safe and sane. I will not cause you any permanent marks, scars or injuries. I will insist that you are obedient and submissive. When you are with me, you will dress, act and behave as a submissive female.

You will call me Master, except when we are around people who do not know your true status. It that situation, you will call me Sir. In a few situations, I may have you call me Daddy. I will tell you when those are. I will call whatever I want. You may be called slave, slut, whore, cunt, cumdump, cocksleeve, bitch, etc. From here, I will take you to my home where you will stay until Monday morning, since you have no reason to be back at your home to go to work on Monday. I will bring you back here on Monday morning when I go to work. Are you ready to begin your trial weekend? Do you have any questions?"

"Yes Master. What about my car? I drove here. I am not too worried about it being stolen, but if I leave it here it will probably be towed as an abandoned car. I realize it is a old car, but it runs well, it's paid for and is low mileage. I can't afford to get another car. I just have the minimum required insurance."

"I understand your concerns, sissy. Molly, do you have any suggestions?"

"James, that car is so old that any wannabe car thief wouldn't bother taking even a look at it. Towed as abandoned is a real possibility. My son Leroy will be here in a few minutes to take me home. He could drive it to sissy's home and leave it and I can pick him up."

"Does that work sissy?"

"Yes Master. Ms Molly, I will turn my car key over to you before I leave. Please just put the car in the detached garage and leave the car key on the floor. After closing the garage door, leave by the side door and lock it. I have the key to the side door on my keychain. My address is XXXXXXXXXXXXXXX. Thank you for your assistance and understanding."

"You're welcome, sissy."

Master James motioned me to crawl closer.

"Sissy we have a few things that need to be done."

He reached into one of the bags and pulled out the heavy steel collar, which he placed around my neck and fastened it. He checked its security by tugging on the collar ring. He followed by placing and securing the wrist cuffs on each of my wrists. These he fastened together behind my back with a snap ring. His right hand went the zipper in his pants and he slowly pulled it down, it wasn't long before his penis was free of his clothing. Oh God it was a beautiful big black cock. Over 12 inches long, a good solid 2 inches plus in diameter, uncut and hard as a steel rod. Master then put his right hand behind my head and began to pull my mouth toward his magnificent example of manhood. On its own accord, my mouth opened and allowed it to enter me. I began to lick and suck it as Master began to pump my mouth up and down his maleness. This went on for a short time. About this time, Ms Molly's son, Leroy entered the office.

"Ready to go mom?"

"Just finishing up a project, Leroy. It will be a few minutes. James, do you still have the maroon Mercedes?"

"Yes I do. The keys are in my right pants pocket."

"Leroy, there are several bags by the front door and a few in here. Please gather them up and put them in the trunk of Mr James Mercedes. Here are the keys. When we leave, I have to take a car from here to my other client's house and leave it there. It is an older car, you will drive and I will pick you up. Now get started."

It took Leroy under 5 minutes to finish that assignment and he reentered the office and watched as Master James emptied his balls into my mouth. He then directed me to lick his penis clean. When I finished, he pulled them up and fastened them. As I knelt there, he stroked my hair and patted my head.

"Not bad at all. All you need is more practice and some training. That can be accomplished."

Master then stood up and directed Leroy to sit in the chair that he had just vacated.

"Sissy, thank Leroy for taking care of your car for you. Get busy, I don't have much time."

Leroy lowered his jeans and BVDs and I when to work. He wasn't quite as large as Master James but was still larger than I could totally handle. Leroy don't manhandle me like Master James did, so I could work his cock with a little more finesse. While I was working away, Master and Leroy talked a little bit. Like I and what I was doing was unimportant and irrelevant. Later when I had time to think about it maybe that was really the case. I was just a toy for men to play with and a tool for them to use as needed.