The Garage Sale Pt. 01

The garage sale

First of all, this is a work of fiction. That being said, I would love to find a man who wants a 1940s/1950s type gurl to play dress up with. And maybe use me like real girls will not accept any more. If interested, send me a private message.

When this started I was a 26 year old white college graduate with a professional level job. Not married with no girlfriend, I lived alone in a 2 bedroom apartment. Since I can remember, I have been a secret closet crossdresser. I liked the feel of my mother's clothing. With my parents dying in a traffic accident before I finished college and with no brothers or sisters, I was alone in the world. Since I graduated college and getting this job, I have started gathering a small collection of women's clothing. Nothing fancy, just some panties, a couple of bras, a slip and a couple of nighties, all in pink, frilly and very sissyish. After getting home from work, I spent more and more time in my girl clothes, I would normally wear the nighties to bed.

It was spring time and garage sales were starting to appear every weekend. I was looking for a few pieces of furniture for my second bedroom. A dresser with mirror, lingerie drawers and maybe a full or queen size bed with a headboard and footboard. Plus I would my eyes open for anything else interesting.

I spent most of Saturday going from sale to sale and not finding anything interesting. It was almost 4:30 when I decide that after this one last stop, I would call it a day. I was feeling quite discouraged. The next house was in a very upper end area. Not someplace you would normally find a garage sale. It was a large two story house set back from the street. The yard was very well kept. In front of the garage sat an older gentleman dressed in what could be called business casual.

"Anything in particular, you looking for?"

"Not really, maybe some furniture for my second bedroom."

"I've got a couple of pieces inside that I will sell. I'm closing at 5, so I will show them to you after I put everything away. Until then, just help yourself and look around."

I proceeded into the garage and starting looking. There was some old tools on a work bench and some men's clothing. Nothing I was interested in, however there were several boxes on the long tables. I opened each of these up and found the inside of each box was stuffed with women's clothing. I started to check out the sizes and found that they were the same or close to the same size as the clothing I already owned. Three boxes were filled with just panties, all styles and colors, some plain others were quite frilly. There was a box of girdles, open crotch, panty and full length. Two boxes contained slips and another box was partially filled with nylons and garter belts.

I nearly jumped out of my skin when a voice whispered in my ear.

"See anything you like?'

"Just looking and seeing if there is anything my girlfriend would like."

"The styles are a little old for your girlfriend. Plus they are more your size than hers, aren't they? Do you even have a girlfriend? I bet these would be for you, aren't they? Don't worry, I don't care who buys them or what they do with them. I'm closing up now, so help me put the outside stuff in the garage and then we'll talk about the furniture."

It took only a couple of minutes, for us to put the stuff back into the garage. He handed me a couple of the boxes, they weren't that heavy and grabbed 3 more boxes. And into the house we went, It was very nicely furnished and well kept. Up the stairs we went and he stopped at a closed door, which he opened. Inside was a queen sized bed with a slat style head and foot boards. They were metal in light pink. There was also a set lingerie drawers and a full dresser with a mirror and padded stool. The man laid the boxes on the bed and motioned for me to do the same. Which I did.

"Like what you see?'

"Yes"

"You like the clothes also, don't you?"

"Yes"

"They're for you aren't they sissy?"

"Yes"

"I think we can work out a deal. Why don't you try some of these on, see how the fit."

I blushed but didn't say a word or even move.

"You're shy aren't you?"

I nodded.

"OK I'll make it easy. BITCH, STRIP!"

Slowly I started to strip. First my shoes, then my pants and shirt, followed by my socks. Finally all I had on were my underpants.

"I told you to strip BITCH. I mean naked."

I pulled off my underpants and dropped them on the pile of my clothes. The man gathered them up and tossed them into the far corner of the room.

"Let's take a look at you. Arms out and slowly spin around."

I did as I was told.

"Not bad, needs some work, but a good starting point. We will have to do something about that body hair. Light color and not much of it, but a lot more than most women. Stay right there."

He left the room and soon came back with a man's shaver. He removed the hair from my under arms and from around my cock.

"That's a better. We'll have to get you a body shave before we go too much further. Now let's start trying clothes on."

He handed me a leather underbust corset.

From the videos I had watched I knew how to put it on. Once I got it on, he pushed from the room and to the staircase. There he had me wrap my arms around the floor to ceiling balustrade, then he started to tighten the corset. He tightened it a little bit at a time. Letting my body adjust between each tightening. Finally, I had a hard time breathing and I was begging him to stop. He put his hands around my waist, seemed satisfied and tied off the lacings.

Back in the bedroom, I was handed a pair of nylons and instructed to put them on. Which I did. I had watched enough dressing videos to know that there was a proper way to put them on to prevent laddering. Once on and attached to the corset's garters, I was handed a pair of panties. There were hot pink with lots of frilly lace. While I was pulling them on, the man went to the room's closet and rummaged around a bit and came back with a pair of sling back shoes in black with 3 inch heels. They were a little small, but the open backs allowed me to wear them. I was then handed a pink laced bra, which I put on. He looked at it and reached into the stocking box and pulled out 2 handfuls of stocking, which he stuffed into each cup.

"That will do until we can get something that looks proper."

By now my sissy stick was hard and drippy. Seeing this, the man reached into another box.

"That will never do. Bulges don't look proper on women. This will fix that."

With that he pulled out a girdle. It was a short, pink open crotched girdle. I pulled it up my legs until it's was around my waist. It gave me a flat tummy. He then handed me a full slip in white that stopped mid thigh. Back in the closet, he was searching for something. Finding it, he pulled a white long sleeve blouse in silk from the closet, along with a long pink pencil skirt in leather. After buttoning up the blouse, I wrap the skirt around my waist and pull the zipper down toward the hem. I am only able to get it a little ways past my butt.

"You are still missing a few things."

He pulls a blonde wig from the closet The hair is long with bangs in the front. He then opens a bottle and with the attached brush, smears some sort of paste inside the wig. He places the wig on my head and adjusts it.

"It's not the right shade, but it will do for now. The wig hold glue will hold it in place until removed properly."

From the top drawer of the lingerie drawers, he pulls a set of large gold loop earrings. They are clip-ons, which he places on each ear.

"Pucker your lips."

When I do so, he takes a tube of lipstick and paints my lips a bright cocksucker red color.

"Now it's time for you to pay for these clothes."

I tried nodded and then tried to move toward my male clothing to get my wallet.

"Oh no you don't. You're going to pay for them like any girl pays for clothing a man gives her. I know you want this. Your pitiful excuse for a cock is stiff and leaking."

He placed his left hand on the top of my head and pushed me to my knees.

"You know what's expected, so get to work."

"I have never do it before."

"I got a virgin. This is a surprise. I will have to teach you the proper way to service your man. Now pull down my zipper and gently pull out my cock."

I do so. It wasn't too long about 7 1/2 inches uncut with a large mushroom head.

"Now kiss the head."

I planted kisses all over the head of his cock.

"Now lick my cock like a lollipop. Get it nice and wet."

I licked his cock like an all day sucker.

"Open wide bitch."

He pushes himself into my mouth and begins to pump as I work his cock with my lips and tongue. Soon, he is holding my head between his hands and starts to fuck my mouth. It isn't long before I hear his breathing change to shorter and labored breaths and his cock begins to pulse. Then I am tasting his essence in my mouth.

"Not bad for a first time, bitch. You'll get better with practice. It's late and at least I need something to eat. Let's go."

He led me to the kitchen.

"It's Saturday night, unless I am going out, I don't usually eat very fancy on Saturdays. Besides, I don't know how well you can cook. Grab a large can of soup from the pantry and warm it up. I need something to eat. You not so much, but you still need something besides straight protein."

I found a can of Campbell's soup, 'Home Style Vegetable Beef', opened the can, pour the contents into a pot and placed it over the gas stove. When it was warm enough, he directed me to pour some into a bowl and the majority of it into a larger bowl. While I had be cooking, I had placed a tablespoon and a teaspoon on the dining room table. Once I had pour the soup, I individually brought each bowl into the dining room and sat them on the table. I still wasn't steady enough even on 3 inch heels to do it in one trip. The large bowl was first and set at the head of the table. Then the small bowl which I set where he directed which was next to his seat.

He was the perfect gentleman, he pull out chair from the table and held it while I sat down. Trying to be a lady, I ran my left hand under me as a sat to smooth my skirt down. He then helped me move my seat to the table. We ate in silence. When we finished, I rinsed dished and placed them in the dishwasher.

"Come and help me move these boxes in the garage."

When I hesitated, he slapped my ass with a,

"Come on bitch. No one is going to see you and even if they did, at a distance you look enough like a woman to fool them. Get your ass in gear."

So into the garage we went. He loaded me down with 3 boxes. They weren't that heavy. He grabbed 4 and we went back into the house and to the bedroom. Twice more we made that trip until all the clothing boxes were in the bedroom.

He rummaged through a couple of boxes and pulled out some more panties, slips and bras. I was handed one of each and told to put them on. While I was stripping down to my corset, he went to the closet and pulled out a long tight satin dress in lavender. Putting each piece on until I finally got to the dress. Once on I couldn't zip it up. He as the perfect gentleman, do so. I was told to spin around and walk a bit. Handed more lingerie, I was told to put it on while he pulled another outfit out of the closet. This outfit was a black silk blouse with a long red leather skirt that went to my ankles. It was a hobble skirt. Fully zipped I could only take very short mincing steps. I tried on several more outfits before he announced that was enough for now. After putting on each outfit, I got on my knees and paid for each outfit like any other girl would.

"It is getting late. Let's go down to the living room and talk a bit."

In the living room I sat on the sofa, while he mixed us each a drink. My legs were crossed at the knees. He handed me my drink, sat on the chair across from me and we start to talk. Or more accurately, he would ask questions about me and I would answer. I told him about my life, my job, my family and all my sexual fantasies and desires. How I loved to dress up in women's clothing and my feeling and desires when I was dressed up.

Then he told me about himself.

"Girl, I was married for 26 years to one of the best women in the world. My world orbited around her. She was a 70's and 80's woman, could take care of herself and had many interests. Including a career. She died in an car accident a few years ago. I don't look that hard because I was always comparing her to my wife. But I am a healthy virile man and have needs. While rosie palm will do in a pinch, it is not a long term solution. I've tried Kept women and they have only one thing on their minds, what's in it for them. Call girls and hookers are only in it for the money and it shows.

As you can tell, I am a successful man. I could have a bigger and nicer home. But this one is comfortable and my wife and I were happy here. I feel no need to move. I was still looking for a solution to my problem. At one of my companies, I have a black man who served over 20 years in prison. So one day I asked Jerry how they handled having no women in prison. He told me that they could jack off and many did that. The more alpha men need more than that. The next choice was using one of the gay whores in the prison. That gets expensive before long. Not in money, but in canteen. The last option was a sissy. They were the best option. Jerry told me there 2 kinds of sissies. The first was a young slim inmate that couldn't protect themselves. He got a couple of sissies that way. You got them as a cellmate and you forced them to serve you. The best were the inmates that were already sissies. They submitted readily. Jerry told me the best blowjobs he ever got were from sissies. They could suck start a 747. The only want 2 things, cock and cum. In fact, he told me that when he got out, he found a sissy and made her his bitch. He has told me if I find the right person, he would help me train her. Jerry said the best things about a sissy are, it's never 'that time of the month,, they never have a headache and they don't get pregnant.

After considering all the options, I believe having my own personal sissy is my best option. I am not looking for a live-in sissy. Just every other weekend. I like what I see in you. Are you interested? I will not change you public life. Every other weekend, you will come here straight from work, change into the clothing I designate and become my woman until later Sunday afternoon. You serve me as I desire. You will do some cooking. I have people who do the cleaning. You will look pretty and take care of my needs. You will not be a modern girl, you will dress in 40's and 50's styles. You will wear skirts and dresses only, no pants or shorts. No flats either, only high heels. Undergarments will be stockings, no pantihose, bras, slips, panties, corsets and girdles. You will have long, painted nails and wear women's jewelry and makeup. And at night you will sleep in my bed.

Come over here and sit on my lap."

Like I was in a trance, I got off the sofa and walked over to him and sat on his lap. He pulled the hem of my dress up and pulled up the hem of my girdle. Through the panties, he started to fondle my cock. It was rock hard and I could feel it dripping.

"Jerry told me that sissies were very submissive. I didn't believe him. He was right. Your excuse for a cock is rock hard and leaking like a sieve. You're enjoying this. You don't just want this, you enjoy and absolutely need this, don't you?"

All I could do is nod my head.

"Your submissiveness adds another dimension to this. I will have to give it some thought. You will spend the night. Why? For one thing you have been drinking and the police are cracking down on drunk drivers. Second, I want to give you a taste of what this relationship can become. It's time to go to bed. I have some nighties for you to wear. You will sleep with me. You know you want to. Off we go."

He led me up the stairs and back into the bedroom. He reached into another box and pulled out several nighties and nightgowns. Holding each one up in front of me, he considered each one until he picked a filmy pink one, which he handed me.

"Strip down to you panties, bra, and corset, then put this one on."

I quickly did so and then started to get down on my knees.

"You will pay for these tonight." He then led me into the Master bedroom.

Once in his bedroom, he turned around to face me.

"One of your duties when you are here is to prepare me for bed. It is quite simple as I sleep in the nude. Undress me."

I slowly undressed him and hung up his slacks and put his shirt and underwear in the clothes hamper. He lifted the bed covers and motioned for me to get in the bed and he then followed me on to the bed. He wrapped his arm around my waist and pulled my back into his front. I could feel the hardness of his penis pressing into my ass. Although I was in a strange bed with a man I really didn't know, I felt comfortable and protected for the first time in a long time and I quickly fell asleep.

I was awoken as he rolled me onto my stomach and began to forcibly rub his cock against my pantied ass. With a grunt, he emptied his balls onto my ass. He pulled me out of the bed and onto my knees. I opened my mouth and accepted his cock into my mouth. He pump a fresh load of warm man cream into my mouth and pulled out. He had me remove my panties and he stuffed them into my mouth and he told me to clean them with my mouth. I knelt there sucking the cum out of the panties as Sir walked into the master bath and showered and prepared for the day. He puttered around in the bathroom for a few minutes before coming back into the bedroom. He pulled the panties from my mouth and tossed them on the bed.

"You will rinse them out today when you get home. Now got to the bathroom and clean up. You will not shower, you will take a bath. Use the produces I have left out for you. My wife used them. Use the bubble bath. Put the shower cap on your head. Do not get the wig wet. They are a pain to dry. I have left a razor out for you. Shave your face as close as possible. When you are done, go to the other bedroom and dress in the clothing I will leave out. You know the order it has to be done. When you get the corset as tight as you can, call down to me and I will come up and tighten it properly. When you are done dressing, come downstairs. I will be in my home office. Now get going, bitch."

It took almost an hour for me to finish cleaning up, before I walked naked across the hall to the other bedroom. Once there I put on the corset and snugged it up. it was a beautiful under bust model in pink satin brocade. I carefully pulled the nylons up my legs and attached them to the garters. As soon as I pulled the panties on, I went to the baluster and called down to him. He was soon there and started to work on the laces. My breath got shorter and shorter. When he finally stopped, I felt like the corset was cutting me in half. With a smack on my ass, he told me to finish dressing.

Back in the bedroom, I put on the black lace bra and stuffed the cups with nylons. Followed by a black silk chemise and half slip. The outfit he had selected was a black silk blouse and a red leather pencil skirt that reached my knees. After putting my shoes and jewelry on, I left the bedroom, walked down the stairs and into his home office. I found him sitting at the desk, working on his computer and talking to someone on the phone.

"Bitch, make breakfast. I'll take 3 eggs over medium, with a small bowl of oatmeal with 3 spoons of brown sugar. I'll also have 2 slices of wheat toast lightly buttered. Make yourself a bowl of oatmeal with no sugar and a slice of wheat toast, dry. And bring 2 glasses of orange juice. Get going."