Garage Story

A Synopsis:

A young man looking at a garage sale for women's clothing to wear.

He gets more than clothing. He gets a new life, slowly.

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There are 5 chapters to this story.

After every chapter edit I re-read the story and make more changes then have to re-edit.

After many many edits I've decided to post this first chapter.

Depending on how it is received I'll post the other chapters, after the editors complete their remarks.

The total story fits multiple categories.

Transgender & Crossdressers / Romance / Sex / Gender Bending /

There is some sex, not in Chapter One.

This is fictional, mostly.

The original of this story had pics. They required a lot of work, so I eliminated them

All Rights Reserved for this author

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I parked and got out of my car, then walked across the street to the garage sale.

"How much does this cost?" I asked while holding a skirt suit. The woman selling clothing out of her garage, looked at me.

"$20!"

I stood in place thinking. I was nervous that she might suspect me. She looked at me thoughtfully. She was trying to decide if I would really buy.

"I don't know. What if it is not the right size?" I asked.

"If you take it now, and it's not the right size, bring it back today, and I'll return your money."

"I'm not sure if she's coming home before seven this evening. Let me look around. Maybe I'll get the courage to take a chance."

She left me alone to take care of other potential customers.

I walked up and down the rows of clothing. I told the woman selling the clothing that it was for my live-in girlfriend. She didn't wear suits often, but needed one for an upcoming job interview. I was taking a chance on her fashion sense and size. I was trying to save her money.

Jill owned the house and managed the garage sale. She accepted my explanation or, she didn't care.

A few people stopped to look at the items on sale, then disappeared. When Jill was not busy taking care of potential buyers, she drank coffee and read a book. She looked at me every once in a while, but otherwise left me alone. I walked round and round and couldn't make up my mind. Finally, Jill came to me and asked if she could help.

"No, I can't decide," I responded

"Look, nothing personal, but would you like to try anything on?"

"What do you mean?" I said nervously

"I am not judging you. If you want to try on some clothes I am OK with that."

My mouth dropped open as I stood in front of her and couldn't respond.

"I am only guessing, but you look as though you wear a size 14 dress. I am not judging you. It's the same size as the clothing you are looking at. I think the skirt suit will fit and look good on you. It's your size. If your "girl" is that same size as you, or, if you want to try it on for yourself, that's OK."

My heart thumped in my chest. Did she understand my secret? I never accumulated many women's clothes. Most of what I have is from rare visits to discount or used clothing outlet stores. I never bought anything of my size. I didn't want to hint that I was buying the clothes for myself. Jill wasn't concerned that I, a guy, wanted to wear women's clothing.

"Look if you like the suit, you might as well try it on. If you keep hesitating it'll be gone before you get a chance to come back. Then you'll regret that you couldn't make up your mind."

She was right. It was hard for me to admit to anyone that I wanted to wear women's clothes.

Taking my hand, and the hanger with the suit in her other hand, she led me to the entrance of her house. "Take the suit into the house. On the right as you enter is a bathroom with a mirror. Try it on to see how it fits. Or, come right out. Whatever you want. Nobody will see you, nobody will know."

I didn't say anything. I took the hanger with the suit from her and walked into the house. Several feet into the house I turned right into the bathroom. Before entering the bathroom I looked back at Jill. She was already taking care of someone else.

The bathroom had a full-length mirror and was large enough for me to see myself from head to toe. I hung the suit on the back of the bathroom door. I stood about five feet from the door and looked at the hanging suit. I was trying to convince myself that since this is what I wanted to do, I should do it. I looked out a window that looked over the garage sale. Jill was helping other would be buyers. What she said was true, if I didn't buy now, it would be gone very soon.

I was alone in the bathroom. Everyone was busy outside. I stood looking at myself in the mirror. Did I have the courage to try the skirt suit on? I was alone and nervous. It bothered me that she "made" me. I held the suit up against my body and looked at myself in the mirror. Yeah, it looked like it would fit. The more I thought of actually wearing the suit, the more nervous I became. It was the type of suit that a woman would wear to the office. The jacket closed in front and tapered at the waist. The skirt looked straight, like a pencil skirt. To know for sure, I had to try it on.

It came down to putting the suit on now, or forever forgetting it. Knowing that I didn't have the courage to follow through with what I wanted would haunt me. Taking a deep breath I stripped to my underwear. I looked foolish in the mirror with my socks and underwear on. I looked out the window again. Everyone was still busy. How long would it take me to make up my mind?

I still did not have the courage to put the suit on. I was in a stranger's house and this made me all the more uncomfortable. I knew she would be asking about me shortly. It was now or never.

At 5'7" I was the perfect height for these clothes. The shoe sizes I saw along with the clothing looked about my size. Under the worst case I could find shoes that matched the suit.

My slight frame allowed me to wear almost any dress. Padding was always my problem. I sympathized with big guys who wanted to wear women's clothing. Finding clothes that fit them had to be a real chore. My soft facial features coupled with lack of beard made it that much easier for me to "pass."

I kept debating with myself about what I was about to do. I didn't have an excuse. As soon as I took the suite from Jill I was committed. Even if I didn't try it on, Jill would think I did. There was no way I could avoid embarrassment, if I allowed myself to feel that way. It was best for me at this point to act as though everything was normal. Jill was acting that way. The house was quiet. There was some background noise coming from the street. I slid the blouse and jacket off the hanger and put them on the side.

Taking the skirt off the hanger I held it in front of me. I slid the skirt's zipper down. Standing on one foot I placed my other foot into the skirt opening. I repeated this with the other foot. With both feet together I slid the skirt up my legs and secured it around my waist. The waist was snug. The hip and rear parts of the skirt were loose as they flared out below my waist.

I walked over to the window and looked outside. Everyone was busy.

Taking the blouse I inserted each arm into the sleeves and closed the left-handed buttons. Then I tucked the blouse into the skirt and smoothed it out. I put the jacket on. It hugged my midsection and flared out above and below. Although I still looked like a guy, the suit fit well. I wondered why her aunt was giving up the clothing.

I walked back and forth looking at myself as best I could. I felt a restrained thrill as I moved about the bathroom. The skirt restrained my steps in a feminine way as I rushed over to the window to check on the garage sale outside. Seeing that everyone was busy I imagined myself in the living room fully dressed. A pair of heels would help complete the picture.

I forgot the time while daydreaming. I must have been in the bathroom a long time. The knock on the door startled me.

"Are you OK?" Jill asked.

"Yes."

"I hope you are not getting the clothing dirty?"

"No, just trying to make up my mind."

There was silence for a short time then Jill said, "I don't mean to push you, but maybe I could help."

"Huh...."

"I'm not passing judgment. But I dress this way every day. Maybe you need help with the fit of your clothing."

"Huh...."

"There is nobody else here now. I have the time to help. What do you say?"

I would never see her again after today. So what if I admitted liking wearing women's clothes. "After today we'll probably never see each other again, so what do I have you to lose?" I thought to myself.

What is the worst she could do? I unlocked the door and opened it a crack. "You won't laugh?" I asked.

"Absolutely not."

She came in, closed the door, and looked at me. I stood in front of her with my bare legs jutting from under the skirt. The socks I still wore destroyed any feminine image.

"What do you think?" I asked.

"It is definitely the correct size. It looks a little awkward because of the way you stand and your lack of figure. Suppose I give you a pair of shoes and something to fill in the other areas?"

"I guess so," I responded.

She left the room and shortly returned with a pair of 3" heels, panties, padded panties and pantyhose. "Please put the panties on before wearing the padded ones. It is hard to clean the padded one."

"OK," I said.

As soon as she left me alone I hiked my skirt up and sat on the closed toilet seat. I slid the padded panties up my legs over my boxer shorts and realized that it was very uncomfortable. I had no intention of wearing the panties she provided, but now it was obvious I should. I removed the padded panty and my boxer shorts. The panties she provided were the female version of the boxers I wore. I pulled them up my legs till they rested on my waist. Then I pulled the padded panty up over my panties.

While still seated I tried on the shoes she provided. I still had my socks on. The shoes were pretty tight. I knew from experience that stockings or pantyhose would make them fit better. I took my socks off, then

slipped each foot into the pantyhose legs and pulled everything up tight as I stood. While standing, I pulled my skirt down.

Sitting again on the closed toilet I slipped my feet into the shoes. The skirt was too tight to raise my foot and slip each shoe on. The only way to get the shoes on was to bend my legs to the side so that I could reach my feet.

Jill walked into the bathroom as I was slipping on the shoes. "You do that very well," Jill commented. "I do it the same way."

Standing in front of me she placed tissues into the breast pockets of the jacket. It gave me more shape. She then stood back and looked at me. We were about the same height. That meant that her auntie was the same height as her.

"That looks a lot better. Actually you could make a fairly convincing woman with a little work."

"Look I don't want you to think I do this all the time. It's just that sometimes I get this urge..."

"That's OK. We have friends with children that feel the same way. Sometimes it is a passing fad, other times it is more permanent. I am not passing judgment. I'm giving you my opinion. If you are still unsure, we could do a little more work to get a more realistic picture."

"I should forget this," I said hesitatingly.

"Why? You're embarrassed in front of me? I am not judging you! This is your chance. Most probably you'll never see me again. This is the perfect situation to go for it. I'm not judging your lifestyle. Live any way you want. Dress any way you want. I have my own fetishes. When you leave, the most I will remember is that I sold my clothing."

With a heavy sigh I said, "OK let's go for it."

Let's go upstairs. Don't worry, there is no one in the house now."

My clothes remained in the bathroom since there was no one else in the house.

Dressed in the suit with 3" heels, I followed her out of the bathroom down the hall to the foot of the stairs. I had never walked upstairs in heels before. It was an unusual feeling. I needed to lift a leg for each step, but the skirt was too tight.

As she started climbing the stairs, I hesitated. She looked back and saw me taking off the shoes. "You don't need to take off your heels to come upstairs. Women do it all the time." It was obvious she expected me to put the heels back on. I put the shoes on and while holding the railing. Jill saw that I was trying to take a step up but that my skirt prevented it. "Try standing to the side and lifting your leg'" It was a little awkward but it worked.

Taking each step at a time I followed her up the stairs. Then with small steps, I followed her down the hallway.

"See, I told you, you could do it."

I smiled weakly as she led me into a bedroom on the right.

"This was my aunt's bedroom. She died about a year ago. It is her clothes we are selling."

I felt a little awkward wearing a dead woman's clothes in the room she lived in. Then again, she would not be needing them.

"What happened to her?" I asked.

"She died of breast cancer. It spread throughout her body. It was a good thing she died. She suffered terribly. At least she has peace now. It took me a long time to agree to sell her things. But life continues."

She was so right.

Since I was already wearing everything a woman wears below the waist, Jill gave me a bra to put on. I took the jack off, then the blouse. I pulled my undershirt off over my head. I picked up the bra so that the back clasp was in front. After closing the clasp, I rotated the bra so that the cups were in front. Once I had the bra on, Jill turned to look at me.

"We need to fill your "C" cups. I have just the right thing," Jill said as she rummaged through some dresser drawers. "Ah, I was right. I thought I remembered that she wore these."

"What are you talking about," I asked.

"Remember I told you she died of breast cancer?"

"Yeah, so?"

"After her operations she wanted to keep up appearances, so she bought these," Jill said as she raised a closed box.

"What's in the box?"

Jill pulled out two silicone breast forms attached to a silicone breastplate. You put it on like an undershirt. I removed the bra I had on.

I struggled to get my head through the opening of the breastplate assembly. Stretching the material off to each side, I put my arms through the openings. Once supported by my shoulders and held in place around my torso, I had breasts. They were fake breasts on a silicone breastplate. They hung like real breasts and swayed when I moved too fast. There was no way I could move freely with them swinging from my chest. I put the bra back on and adjusted my new breasts in the cups. Jill adjusted the bra straps so that my new breasts sat at the right height on my chest.

Jill gave me the blouse to put back on. Once I closed the buttons I had to open the back of the skirt to slide the blouse back into the skirt. Closing the buttons was not as simple as it had been before. I had to look over my new breasts to see what was going on below them.

Jill then gave me the jacket to put on. My new breasts made everything feel "different." The lower part of the jacket was snug around my midsection. My "new" breasts moved but were contained so that it was not too uncomfortable.

"You'll have to do something about your bulge." Jill said.

My face turned red. I hadn't paid attention to my excitement. Snaking my hand under the skirt, padded panty & panties I pushed my manhood back between my legs. It was difficult as I still had an erection. As my erection softened, it became more pliable. When I was finally soft and folded backwards, I pulled my panties up. Then I pulled the padded panties and pantyhose up to hold everything in place. Jill watched quietly.

With the "flat" look in place I withdrew my hand. There was no chance of an obvious erection.The skit was snug on my waist and tight down to my knees.

"All these clothes belonged to Auntie," Jill explained. "We did everything we could for her so that she could look in the mirror and see herself as she was before she got sick. By the time she finished dressing each morning she looked the same as she always did. Since you are about her size, everything you have on, should work for you just like they did for her."

It was an odd feeling standing all dressed up in front of a "stranger." Every move I made, my chest made a delayed move. I felt the weight of the forms on my chest. I moved from the left to the right shaking my new chest. It felt odd. There is very little control over their movement. They moved independently as an afterthought. The same was true of my hips and rear, though to a lesser amount.

In the mirror my body looked feminine from the neck down. Standing to the side my chest protruded as my ass did in the opposite direction. I stood straight and looked into the mirror. I had hips that prevented my arms from hanging straight down.

I stood up and asked, "now what?"

"Auntie Jan was very vain. She lost a lot of weight because of the cancer. But when she went out she insisted on looking her best. Towards the end we bought her padded underwear to fill in the places where she lost weight. After they removed her breasts, she used prosthetics."

There was a noise from downstairs. " Wait for me," she said to me as she left the room to go downstairs."

I stood in her aunts room dressed in her aunts clothes. I had her aunts figure which made me feel odd. I walked around the room while looking at pictures of her aunt with other people. In several picture her aunt stood next to a much taller man. Maybe it was her husband?

I heard some talking. It sounded as though there were a few people. Finally, I heard her come back up the stairs.

"What do you think of my aunt? Jill asked as she saw me looking at the pictures.

"She was a good looking woman," I responded.

"Well, you have her figure. With a little more work, you can also be a good looking woman."

I didn't know how to respond. I was wearing her Aunties clothes and with her shape-wear I had her aunties figure. I wondered if after Jill did my face and hair, could I live as her auntie? It was a ridiculous thought, or was it? Could I really take over a woman's life and live as her? My imagination was getting the better of me. Jill broke into my thoughts.

"It's my husband and friends from next door downstairs. Nothing to get upset about. I told them about you. They only asked if you were going to buy, in the end. I hope so. Well, let's take a look at you."

She walked me up to the mirror as we stood side by side, I am little taller than her. What we saw were two women standing side by side. Up to the neck, that is.

"Well, what do you think?" I asked.

"You look very good. You're very lucky. You're the same size as my auntie. Her shoes even fit you. With a little work you could easily pass as a woman. Tell you what I'll do. Suppose you help with the sale. Afterwards you can take all auntie's clothes that remain for $100! That includes her shoes, underwear, everything. It's a bargain you'll never see again."

"What will I do with all those clothes?"

"Do what you want to do. Wear the clothes or give them to charity. It is up to you, so long as you take them from me."

At that moment there were footsteps coming down the hall and a head popped into the room.

"Jill, Oh, hello there. Hey, you're looking real good. That outfit really fits you. We'll be glad to get rid of it. Jill, look we don't want to hang around while you're having this sale. Suppose we come back later? OK with you?"

"Sure, I think I got somebody to help me for the rest of the day. Yes?" Jill said as she looked at me.

"OK," I said, as I looked back at her.

"OK, see you guys later," Jill said.

With that, the footsteps went down the stairs and out of the house.