The Garage Sale Pt. 02

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A sissy boy is outed at a garage sale.
8.2k words
4.76
21.7k
10

Part 2 of the 3 part series

Updated 06/11/2023
Created 04/07/2022
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I left work at 3PM and went I directly to 'Nails by Kim'. I entered the front door and asked the receptionist for Ms Kim. A attractive Asian woman about 5'4" and 105 pounds, walks up.

"You must be John's friend sissy. Come with me."

She led me into a back room and shut the door.

"Strip down to your undies dearie, we have lots to do. Don't worry, you don't have anything I haven't seen before."

Once I was down to my panties and chemise, she looked me over and pressed a buzzer.

"I can see what Master John sees in you. You make lovely girly for him."

I sat in the manicure chair and she started to work on my fingers. She trimed my cuticles and cut my nails. Then in walked another woman. I was shocked as this was a private room.

"Hi Bobbi, this is the gurl that Suzie is training. What do you think?"

Bobbi pulled down my panties and lifted my caged clit.

"Good thing this is locked up. No self-respecting woman would have anything to do with something that small. I've seen bigger clits on real women. She'll make Master John a good slut. That's all she's good for."

Bobbi then proceeded to start working on my toes.

Kim finished with my nails and began to stick false nails on my fingers, using nail tapes. The first set, she painted a dark red and then had me stick my fingers under a nail dryer. Once they were dry, she removed them and replaced them with another set of false nails. These she painted in passion pink. While they were drying, she removed the tapes from the first set and placed them in a small ziplock bag. When the second set had dried, Kim removed them and placed a third set on my fingernails. This time she didn't use nail tapes, she used nail glue. It was a type of super glue.

"Gurl, when you put your nails on, be careful. Use only one small drop of glue. If you use more, they will never come off without destroying both nails, the false one and your own. There is a glue release solvent. Use a toothpick and 1 drop off the solvent between your nails and the false ones. Wait a couple of minutes and they should come off with a little pressure. If not add a second drop."

Kim painted this set a bright red. The same shade that Bobbi painted my toenails. When my nails were dry, Kim handed me an envelope. It was from Master.

'Sissy,

Tip Kim and Bobbi as you have been taught and then come directly to my house.

Master'

I showed the note to Kim as I slowly got to my knees.

"No thank you, I am well taken care of at home. Bobbi?"

Bobbi stepped in front of me, slowly unzipped her slacks and dropped them and her panties to the floor. Out popped a cock that wasn't much smaller than Suzie's. What is it with these Trans girls and their huge cocks?

Obeying Master's note I went to work on Bobbi's cock. It wasn't long before she began to pump her juice into my mouth. Finally, she pushed me away.

"Damn, this slut can suck. Suzie was right."

"Get dressed, its time for you to get home to your Master."

With these new nails, I had a very hard time dressing. The pants and shoes weren't the problem. The buttons on my shirt were impossible to do. Ms Kim had to help me while showing me several tricks that women with long nails use to do things. It wasn't long before I was headed out the door to my car and on my way to Master's house. While I walked out the door and down the street, I kept my hands in my pockets. I thought everyone knew I was a long-painted nail sissy slut.

It was just after 5 when I arrived at Master's house. I found the back door unlocked, so I entered and walked up the stairs and into 'my' room. On the bed were a Lilac blouse and a long pink leather skirt. Also, there was a set of lingerie and a black box with gold lettering. I had stripped down and was preparing to put the corset on when Master entered the room. He stopped me.

"I have something for you."

He hands me the black box. It was heavier than I expected and almost dropped it. Upon opening I saw it was a new breast form. It was not the type that I put in a bra. It was the partial body suit that I put on. The breasts were huge.

"They're size S. I like my bitches well endowed. Put it on."

I quickly read the instructions, then rubbed baby powered on my body and inside the form. It was like trying to squeeze a 3-inch pipe through a 1-inch hole. I finally got it on. I felt like I was going to fall flat on my face, I was so front heavy. Master handed me a lacy pink bra which a put on, it didn't help at all. All I felt was more pressure on my shoulders. Then I put on the pink leather corset which was on the bed. I tightened it up as much as I could. At the banister, master tightened the laces until I felt like I was being cut in half. After knotting the laces, he measured my waist.

'Down 2 and a half inches. That's a good start."

Back in the bedroom I pull on a pair of nylons and was preparing to step into the gossamer pink lace panties, when Master stopped me. He handed me a pair of pink pumps with an ankle strap and 5-inch heels. Then he had me knee before him. Once on my knees, Master picked up a collar from the bed. It was an inch and a half wide in chrome steel with a very large ring in the front. Master placed it around my neck and secured it together with a set screw. While it was not super tight, I could feel it around my neck and feel its weight. He stood me up and grabbing each of my wrists, he placed large, chromed steel cuffs on each wrist. These also being secured with a set screw. He then secured the wrist cuffs together with a large quick link. Turning me to face the footboard of the bed, he bent me over at the waist and tied a piece of 550 cord to the quick link and then pulled me forward over the bed by securing the other end of the rope to the headboard.

When Master finished securing my wrists, he placed and secured an ankle cuff on each of my ankles. They were of similar design and construction as my wrist cuffs. Using these cuffs, he secured my ankles to each footboard post using the same 550 cord as my wrists.

"Why are you doing this Master?"

Master then fitted a large dildo gag in my mouth, buckling the leather strap behind my head.

"Bitch, I am disappointed in you. You are a disobedient whore that needs to learn obedience. You have tried to pleasure yourself without my permission. You have tried to get off. You disobeyed me, your Lord and Master. You belong to me. For that you need to understand the penalty for that."

"Master, I couldn't help it. The chastity has me so horny and need to get off. My cock hurts so bad I had to do something. I'm so sorry Master, I will try to do better."

"Whore, you will do a lot better. First you don't have a cock. Only real men have cocks. You have a sissy clit. It is there to frustrate you. To punish you and so on. Your body isn't yours anymore. It belongs to me. I will decide if you get relieve or pleasure or pain. You have NO rights, you only have what privileges I allow you. You are not a person, you are a domestic animal. You are property, my property and I will control you how I see fit."

I could hear Master whirling something, when the first strike hit my ass. I turned my head and saw Master using a multi tail flogger in leather. It was fairly soft leather, but it still got my attention. Master started to work my thighs and ass with the flogger until they were cherry red. My eyes were teary and my sight was blurry. He stopped and I heard his zipper open and his pants hit the floor. I felt his hands on my hips and he laid his cock on my ass crack. Master then pressed my ass cheeks together and began to hump my ass. Before I could hear his breathing change and with a grunt, he pumped his seed all over my ass. He massaged his essence into in ass and cleaned his hands on my thighs. Pulled up his pants and then left the room, turning off the lights.

I had lost track of time, when the lights came back on and Master reentered the room. He announced himself by resuming the flogging of my ass and thighs. Soon my ass was on fire. But at the same time my sissy clit was leaking and my ass was raising up to meet the swing of the flogger. Finally, Master stopped flogging me and put it down.

"Damn you're one kinky, horny slut whore. I didn't understand how submissive you really are. This will be interesting. Won't it cunt?"

He released me from my bondage, leaving the collar and cuffs in place.

"Get dressed and come to my office."

It took almost an hour for me to clean up, straighten myself up and finish dressing and preparing myself to serve Master. When I finally walked into the office, Master stood up and walked toward me. He latched my wrist cuffs together behind me and attached a leach to my collar ring. Walking around me, Master inspected me. Then he led me to his chair and had me kneel before him.

"Your makeup is improving. Still needs more work and practice. But it will come with time. The level of your submissiveness surprised me, but also excites me and beckons toward a few different directions in this relationship. We will need to explore that more. I have talked with Jerry and Suzie a few minutes ago. Suzie will stop by later this weekend with some training disks for you to listen to while you sleep. And Jerry and I will discuss a new project. Now since you haven't eaten this evening, I guess I'll have to feed you."

Pulling down his zipper, Master pulled out his manhood and allowed me to suck and worship the symbol of his manhood. When I was finished, he tucked himself back into his pants and pulled the zipper up. It was getting late, so Master led back to my bedroom, released my wrists and directed to prepare for bed. Removing my outerwear, I stripped down to my bra and corset, leaving the breast form in place. I removed my makeup and put on the baby doll that was sitting on the bed. A pair of slippers with 4-inch heels were next to the bed. When I walked into Master's bedroom, he was already in bed. He motioned for me to enter his bed and lay next to him. I did so. He rolled me on my side with my back toward him and he wrapped himself around me, pulling my ass into his crotch. I could feel his manhood getting harder and harder. Between that and the large breasts, I didn't get much sleep.

The rest of the weekend was almost a repeat of the previous weekend. Lots of clothing changes, cock sucking and makeup changes. Plus, some bondage was added. Cuffs, chains, leashes, spankings, etc. Saturday morning Jerry and Suzie, stopped by. Suzie took me upstairs to 'my' bedroom and gave me a few more makeup tips and instructions. And she also inspected my body hair situation. Master and Jerry went off to discuss whatever project Master wanted done.

When Jerry and Suzie left, Master had me kneel before him in the living room. There we discussed our relationship so far and where we both wanted it to go. Master had me go first. I talked about my past experiences and what I liked and did not like about them and our relationship. Where I would like it to go. I also talked about my vanilla life, what was happening at work and how due to the new standards, I was being pushed aside, not because of my performance, but because I was a 'straight' white man. Master commiserated with me on that and discussed what he was looking for. It was comforting because our desires were quite similar.

I had also discussed my desire to get my MBA after I had paid off my student loans. He commented on my car, how old and beat up it was. With my loans I couldn't afford to replace the car that had gotten me through college. It ran but looked like hell and had a habit of breaking down on a regular basis for some of the most minor things. And me being the non-mechanical type.

All I could do was explain to Master my financial situation. How things were going at work. Without me realizing it, I had my face in my hands and was crying. Master pulled me into his arms and comforted me.

"There, there. Things will work out, you'll see."

I was sent out to fix my makeup and when I returned, Master starting asking about my vanilla life. My background, my family, my growing up and so on. He asked about work, the particulars of my job and my employer. I was very leery of telling him that. But soon I did. The look on Master's face when I told him who I worked for, was interesting. It was also confusing to me. But he didn't comment on that.

Later that afternoon, Master sent me to 'my' room to change. When I had stripped down to my undies, he entered the room and had me remove my bra and lay down on my back on the bed. Once there, he tied me to the bed with 550 cord securing each limb via the cuffs to it's respective bed post. He then strripped naked and straddled my body. Laying his cock between my breasts and using his hands to squeeze them together, he began to fuck by boobs. I could feel anything as they are fake, but the power of his actions was really turning me on. Finally, his cock began to pulse and streams of his seed shot onto my face and neck. Using his fingers, Master wiped his seed from my face and neck, and feeding it into my mouth and his is fingers like miniature cocks, fucked my mouth. I was really getting off on this. Master noticed that my sissy clit was starting to drip.

"So my slut is getting excited? I didn't give you permission. I will fix that."

He untied my ankle ropes from the bedposts and pulled them over my head and tied them to the top of the headboard posts. He then picked up the flogger from where he had put it the day before and began to flog my ass, thighs and balls. While it hurt, it also got my motor racing and almost immediately, my ass was trying to move up to meet the straps of the flogger.

"Sissy you are a wanton slut. I am going to turn you in to the prefect pleasure unit. All you will care about is giving that person pleasure. That is what you exist for. This is going to be fun. For me. May for you and maybe not."

Saturday night, between Master's cock against my ass, the floggings and the breast forms, I got little real sleep. But what dreams I had were very erotic. My cock stayed harder than steel all night and pressed against the walls of the chastity cage.

Late Sunday afternoon, Master had me get a small plate from the kitchen, released my chastity and had me pleasure myself before him. He had me keep doing it even after I had relieved the pressure and I actually orgasmed again. After I had cleaned myself and cleaned the plate by licking it clean, he relocked me in the chastity cage and pocketed the key.

"Sissy, in the near future, you will give me a key to your apartment. I will have unfettered access to your life. Do you understand, sissy?"

"Yes Master."

"Are you having comfort issues with that, sissy?"

"Yes Master."

"Let's get it straight. You are my property. We have an agreement. We both signed it. As you can see, I don't need anything you have, so I am not going to steal anything. I plan on leaving you things from time to time. And to check up on your life. Do you understand?"

"Yes Master."

"Now Suzie will at your place next Sunday late afternoon. She will finish your face and do some touch ups on your body hair. You are not to shave your face after Friday morning. Understand?"

"Yes Master."

"Here are some CDs that Suzie left. Do you have a CD player with ear buds?"

"No Master. Sorry."

"No problem. I understand your situation from what you told me. Here is a portable player with earbuds and AC cord. You are to listen to the disks each night while you sleep. You are to set the player to repeat when you play it. You will play a different disk each night, in order. They are numbered, so even a scatter-brained sissy like you can do it. When you are done the set, start over. Bring them next time you come here. Understand?"

"Yes Master."

Master had me kneel before him and he removed first the wrist cuffs and then the collar. He had removed the ankle cuffs the night before. He had me kiss each one after he had removed them.

"Excellent. Go clean up and change. Take the extra cookbooks with you when you leave. Have a good week, sissy."

"Thank you, Master."

I changed out of my girl clothes, leaving my panties and nylons on. It took a little effort to remove my nails and clean them and my real nails up. Cleaned my face and spent the next hour putting the weekend's clothes away and rinsing all my lingerie and hanging them to air dry. Finally, I dressed in my street clothes and left for home. Master had had me prepare a few menus for the next 10 days, so I stopped at the grocery store on the way home to purchase what I needed for these meals.

Once home, I put the groceries away and changed into my required attire. Spent the remainder of the evening preparing for the week. Doing some laundry and some food prep. Before I knew it, it was time for bed. I changed again and put the earbuds in my ears and turned the cd player on and went to bed. The cd wasn't loud, I could barely hear it.

The next morning, I awoke feeling more refreshed than I could ever remember. Got ready for work and left my apartment. The day went like usual, me working on another project. At lunch time, I walked over to a locksmith shop and had a key made for Master.

On Tuesday, our paychecks had been deposited into our accounts. So, after I had changed and eaten dinner, I started to work on my personal accounts. As I started, there was a knock on the door. Checking the peephole, I saw it was Master. I opened the door to let him in.

"You told me today was payday and you would be working on your bills. I decide to stop by and see what you have and maybe give you a hand."

I had my bills and checkbook on the dining room table. Master looked through the accounts, there were not that many. College loan, electric bill and a credit card bill. Looking through my checkbook, he saw what I had in my account. And my pay stub showed him what I earned.

"For your experience and seniority in the company, they don't seem to pay you that much."

"The company seems more intent on promoting minorities than on skills and experience. Plus I am assigned to assist lead project managers and they change my figures and time lines and when it goes to garbage, they blame me. Which gives them another reason not to promote me. I'm thinking on going with another company. I've be giving it some thought. I would have to move though."

"Your car doesn't seem too reliable. Why not get something better?"

"It got when I went to college. It was my mom's car. It got me through college and my job here so far. But it is old and it's getting unreliable. But I can't afford another payment right now, especially considering my work situation."

"That is a stiff college loan. How much longer do you have to go?"

"It depends on the loan amount. Mine is setup for 20 years. I've been paying extra when I can, so I have about 9 years left. I would like to pay it off sooner, but it doesn't look that that will happen."

Master and I discussed my financial situation in more detail and left.

The rest of the week went by like normal.

Friday morning, I shaved my face for the last time for that week. I was feeling more and more comfortable in my girl clothes. This weekend, I spent the time practicing my girly skills. Walking, sitting, hand and arm movements, etc. On Sunday morning, I got a text from Suzie. It said that she would be there about 4PM and that we were going to have dinner together, so I was to prepare a chicken disk for 2 unless I want to go hungry that night.

At 4 there was a knock on my door, it was Suzie. The chicken was in the oven and the white wine was open on the counter breathing. The sides were ready to cook. Suzie entered, put her pot on the stove and warm it up and sent me to the bedroom to strip and shower. When I came out of the bathroom, she had me sit on the bed and did a wax job on my face, just like the last time. When the wax was dry, she pulled it off and with it most of the remaining hairs on my face. It still felt like my face was on fire. Suzie checked my face and with tweezers, removed several of the remaining hairs on my face. She then inspected my body for hair and used the wax to remove any she found.