Garage Story Ch. 02

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 than have to re-edit.

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

I'll post the other chapters, after the editors complete their remarks.

The total story fits many 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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"How about going out? At least I won't have to cook. With enough noise in the place I won't have to listen to him."

"Well, OK. But the three of us going out is awkward."

Jill thought about that then looked at me.

** END CHAPTER ONE

"Oh no! There is no way I am doing that! This is getting way out of hand," I said. "I came here to buy clothes, and now I am wearing them. Look at me. You've turned me into a woman! This is so much more than anything... "

"Why not? You look fantastic and natural. What have you got to lose? You don't know anybody here. You'll never see the guy again. You'll never see any of us again, unless you want to! Besides, we'll go to a fancy place, and you'll get a great meal out of this."

"This is too much for me. I can't handle it."

"Look, Herby is a real schmuck," Tom Said. "He's naive and not very discriminating. He wants to show off how well he is doing. If he bugs you too much, tell him you're a guy!"

"You expect me to go with you like this, as a woman? And, if I don't like him, I should tell him I am a guy? Are you serious! I could never do that!" I said.

"This is a one-time opportunity. Isn't this about the biggest fantasy you could have? Come on, you'll never have the chance again," Jill added.

I stood there as they both looked at me. In all the time I dressed up, going out as a woman was only a fantasy. Now I had the opportunity to make my fantasy a one-time reality. Their arguments were persuasive. If this Herby found out that I was a guy, how bad could it be? Would Jill and her husband protect me. It was my decision. In the end this would be a dream, except that I would have a closet full of women's clothes.

"OK, but you have to protect me if Herby get violent, and you can't abandon me!"

"It's a deal," both Tom and Jill said.

Jill took me back into the house to freshen up. She changed her clothes and applied a new face. While at it, she touched me up as well. After making ourselves presentable we sat in the living room. Jill explained what I should expect from the evening. Tom joined us as we waited for Herby.

I wanted a clearer explanation of what I might have to do. Tom kept looking at my legs and asked if I was sure I was not a real girl. On one hand it made me uncomfortable that Tom was looking at me with lust. But it was complimentary that he thought I looked that good. The conversation remained pleasant as the discussion turned to many other things.

"Would you like to "freshen up", Jill asked. I looked at her and wondered why she would suggest it since I just redid my face.

"What I mean is, would you like to go to the bathroom before Herby gets here?"

"That sounds good," I said as I stood up and went to the bathroom.

I was nervous and didn't realize how bad I needed to go. Once in the bathroom I began struggling to lift the skirt. The padded pantyhose and thighs made it difficult. Then while holding the skirt up, I pulled the pantyhose down to my knees, then pulled the padded panties down. With my hands still holding the skirt it was near impossible to piss the normal male way. Chugging my feet around till my back faced the toilet, I sat. Even then there were problems, my legs were held together by the pantyhose. I had to pull them further down, so I could open my legs. I was beginning to understand why it always took a woman so long to go. My attempt to dress myself was no less complicated.

Once I was dressed, I looked at myself in the full length mirror. I needed to confirm that I did not forget anything. I also needed to build up my courage for the evening. I was very nervous as I looked at myself. To my male-self I saw a good-looking girl. Could I mentally stay in character? Could I act the part for the whole evening?

The doorbell rang while I was still in the bathroom. I heard conversation as I closed the bathroom door behind me. I entered the living room and saw Jill, Tom, and another man. "And this," said Jill, "is Susan."

As I approached the three of them, Herby extended his hand for me to shake. He took my fingers in his hand and gently squeezed them. When I entered the room his eyes scanned me from head to toe. He took an extra second looking at my chest then legs. As he held my hand, he looked into my eyes. It felt as though he read my thoughts and thus knew the real me.

Herby was thin and tall, taller than I. I could see why they did not like him. He was "geeky" looking. He dressed as though from the fifties. He had a pencil or pen sticking out from his shirt pocket.

We made small talk as Jill and Tom got our overcoats. Jill and Tom explained that I was a friend passing through the area. We walked out of the house towards Tom's car. I had on an overcoat Jill gave me. I carried a small pocketbook she found for me before we left the house.

Jill assigned the car seating so that I sat in the rear with Herby. Herby was a gentleman and opened the car door for me. He closed it after watching me slide my legs inside. It was a half hour drive to the restaurant. Jill, Tom and Herby spoke about things I was not privy to, so I was quiet. I sat and listened as I was not sure what I could contribute to the conversation. I was content to sit and listen when we hit a traffic jam. After a few minutes of inching along it was evident that Tom was upset. He blamed Jill for being upset at being stuck in a car with Herby.

After a prolonged period of silence as we slowly crept forward, the silence was awkward. I don't remember how or why but suddenly Jill casually turned back to Herby and mentioned that I was a guy.

Herby laughed at it. I was shocked. Jill really did not like him. Was she trying something to conclude an early evening? Did she hope that he would be disgusted enough to want to end the evening? Herby didn't believe her.

He kept on laughing and looking at me. I was still shocked and not responding. As he continued to laugh and look at me, it began to dawn on him that it was not a joke.

"You guys are kidding. Aren't you?"

Silence!

"You can't be real. She looks too good," he said.

Silence!

I realize that if I had spoken up he would have accepted the whole thing as a joke. Because I kept quiet, he identified my shame.

Herby sat back and looked into my eyes, then chest followed by my legs. One could see the wheels of his mind thinking. It made me feel very uncomfortable.

"You are a beautiful girl," Herby said to me. "You have an angelic face and kissable lips. Your legs are very sexy. Heels make them look hot. You'll have guys running after you in no time."

I blushed a few colors as Herby studied me. It was embarrassing to be evaluated like he was doing. I expected the worst possible reaction from him and wondered what I could do if he became violent. I wasn't big or strong to begin with. I was dressed in restrictive clothes. I was vulnerable.

"You know? When I think about it, what difference does it make? Herby said. "You are a good-looking woman! We are going to have a good time! We're not going to bed, and we're not getting married. This is a social evening. No reason why we can't enjoy ourselves. I hope the food is good."

Jill sighed. Her plan failed. We were going to be together the rest of the evening.

The traffic jam finally broke, and we shifted into high gear. A mile didn't pass before the banter was as lively as before. This time I was included in more of the conversation.

It took a while before I felt comfortable talking. We even managed to get into an argument about something political.

Herby wasted no time playing up to my appearance. "As long as you stay in character, I'll treat you as you deserve to be treated," he said. He treated me as a woman in everything we did. Getting out of the car he offered me his hand. I needed it. It was the first time for me to get out of the rear car seat with heels. Once out of the car, he gave me his arm. I froze with indecision.

It was a distance to the front door of the establishment. I had no idea how I would handle the distance in heels. His facial expression said, "take it." I sighed and took his arm. When we got to the entrance Herby opened the door for me and stood aside so that I could enter first. Once inside we followed the Hostess to our table. Herby helped me off my coat and checked it in. He even pulled the chair out for me. Each time he did something for me, I had to say, "thank you".

Jill and Tom looked at him sort of weird. He looked back at them and said, "this was your idea, and I'm playing along. Besides, she is a good-looking woman."

I was perplexed looking at the menu. Although many items were in English, I was not familiar with them. Herby saw that and asked if it was OK for him to order for me. I was OK with that. After water was brought to the table the waitress brought another set of colored drinks. I was told it was wine. The reason for drinking wine was to heighten the taste of the food. The wine was fuzzy, but otherwise good. I began to feel "good."

Waves of food came our way. It was too much for any of us to finish. Somewhere after the main course I heard music. To the far corner of the room there appeared to be a dance floor.

It was a bit awkward when Tom and Jill got up to dance. Herby and I were talking about something when we noticed they were gone. Our conversation dried up. After a long pause Herby invited me to dance.

"I don't think so," I said. "I've never been in heels this long. Then again I've never danced with a man before."

"Look, you're a nice looking woman. Stay in character and nobody will think anything else. You want to continue sitting here while they are dancing? If we don't get up to dance, one of the many men who have been looking at you will ask you to dance. Come on, it'll be OK, let's enjoy ourselves. We have the rest of the evening."

"Well..."

He stood up and took my hand. Before I could raise any objections, he pulled me up to stand next to him. Then with my hand in his he led me to the dance floor. When he stopped, I stopped, almost running into him. We looked at each other. It was obvious that I did not want to dance. There was no way out of it without drawing attention to myself. With a sigh I put my right hand in his left hand. His right hand wrapped around my waist. He moved slowly so that I could catch up to his moves. He was the leader, I was the follower. It was a forced dance.

At first, I kept a distance from him. It was awkward following him. He was stronger than I and soon gave me enough direction with his hands that I was able to relax. Herby kept assuring me that I passed and that once I forgot my circumstance I would have fun. I felt compelled to follow his lead. When the band played a slow dance, Herby pulled me into him. I tried pulling away, but he was much stronger than me. I looked to the side in embarrassment as my breasts were poking his chest. He leaned over and put his face in front of mine. "If you don't relax and start enjoying yourself, I am going to kiss you in front of everyone."

My mouth dropped open in shock. Would he really do that? We were still moving as his lips got close to mine. "OK, OK, I'll relax. No kisses though," I said. I let him hold me the way he wanted. I moved as he directed me even with his hand on my ass. It took me a while to understand his hand directions. Once I got the hang of it, I easily followed him. We danced everything from fast to slow. We went back to the table several times for a sip of water.

The sensations of dancing, as a woman, with a man was very different from anything I was prepared for. My jiggling chest and swaying hips were erotic. My small steps in high heels exaggerated my movements. Once I got the hang of my added appendages I began to feel comfortable. I think the wine had something to do with it.

After what seemed like forever, we were both sweating and ready to sit down. The heels hurt my toes and calves. On our last dance I leaned my head on his shoulder. My chest was against his. I felt the two globes of warmth on my chest as they pressed against him. His movements changed a little as I felt his protrusion against my stomach. It bothered me at first, but then I thought about his reaction to my mammaries against his chest. "Let him suffer," I thought to myself.

"You two look real good together," Tom said as we walked back to the table. We sat down. Herby did everything a woman could want. He paid me the greatest compliments and attended to my every want. This was a date I would not forget.

We were about to leave when Jill suggested I join her in the ladies room. We were drying ourselves off and reapplying makeup when Jill asked, "tell me the truth, has it been so bad?"

"No, not really. Actually I am having a wonderful time."

"And you want to tell me you've never done this before?"

"Never did!"

"You're going to do it again?"

"I don't think so. I won't have the nerve to do it on my own."

"You can always call me. You're having a good time. I am sure you are going to want to go out again. I don't know you very well, but you look like you've flowered this evening. It seems natural for you."

"I don't know. We'll see."

I felt tired, but exhilarated as we sat together in the car on the way back to the house.

I was sitting next to Herby. His arm was around my shoulders. I felt his body heat. I was relaxed. Jill looked back and smiled.

"Did I miss something?" Tom said. "Susan is a guy. Did somebody not understand that?"

"I've got no problem with that," Herby responded. As long as she looks like this, I'll treat her as a woman. "Susan, you look lovely tonight. Would you consider marrying me?"

I already knew enough of Herby to know he was joking. "Next time you're in town," I answered while thinking to myself that I was comfortable where I was.

"Well that's settled. You folks are too stiff. You've got to relax and enjoy life a little," Herby said.

Back at the house we sat and talked a little more before I got up to go home. Jill remembered a coat of her auntie's she hadn't given me." Here, wear this home and stay warm. You've been a real sweetie. Too bad you don't do this more often."

Everyone walked me out the door. Tom moved his car, so I could drive out of the driveway. Before Herby helped me into my car, he gave me a kiss on the lips. It wasn't a touch and go kiss. It was a solid arousing kiss. I was so shocked that I didn't respond. As I stood in place wondering what happened, Herby gave me his business card with his phone number on it. "If you want to do this again, call me."

I was still frozen in place when I said, "Thank you. This is an evening I won't forget. You'll be a real catch for some lucky lady."

Herby closed the door after I swung my legs in. Waving goodbye, I drove off.

The night air was cool as I drove through the evening. The streets were empty. I was thankful for that. I didn't want the police to stop me for any reason. I had about an hour drive to get home. I kept thinking about what happened to me since I stopped at the garage sale. It was like an unreal dream, except that everything about my current state told me it was no dream. Every time the car hit a bump in the road, I felt my chest jiggle. The pantyhose and restrictions of the heels kept me feeling feminine. I may be a guy underneath everything I had on, but to the outside world, I was a woman. I kept asking myself if this was something I always wanted. I've had occasional desires to wear women's clothing. Did that mean I wanted to be one, or do it on a full-time basis? Was I comfortable this way?

Overhead passing streetlights lit my legs that protruded from under my skirt. My heels forced my foot forward so that my toes pressed on the accelerator or brake.

It was about two AM when I got home. I parked in the underground garage. There was always a chance that I might meet someone that knew me. I was nervous.

I pulled into my parking space. There was no one else in the garage, so I opened the door and swung my legs out. In the silence of the garage I felt vulnerable. Holding onto the door to help me stand, I looked around. The thought that I might meet someone or be seen made me nervous. The coolness of the garage floor caressed my legs and made me shiver. The warm coat wrapped around me kept me warm.

It would take a few trips to bring all the boxes upstairs. In the trunk was a small airline travel cart. I got three of the boxes on the cart and started walking towards the elevator. In the silence of the garage my heels echoed every step. I tried walking on my toes so as not to make too much noise. I had never spent much time in heels and not outdoors on a concrete floor. It was difficult maneuvering in heels. I had to pull an airline cart with boxes of clothes. I tried pulling the cart like a guy. That didn't work too well for me. I didn't have the strength and leverage a guy has. I was off balance in heels, so I took a different tack to pulling the cart. I felt more feminine and moved as such. It took longer.

The elevator took too long to arrive, or I was too anxious. When it finally came, it was empty, and I was relieved. It did not stop on its way up to my floor.

I made it into my apartment without being seen. After dumping the boxes I considered how to go downstairs. I had the option of dressing in male clothes.

"What the hell," I said to myself, "there's no one here. Might as well stay the way I am till I go to sleep." I made two more trips to bring the boxes up. On the last trip an old lady just returned from walking her dog. She was someone I didn't know, so I smiled and got off at my floor.

For the next week after work I dressed up daily. My closets were now divided between male and female clothing. There was a lot more women's clothing than I thought I brought. Jill had included more items from upstairs that I was unaware of until I got home.

Jill's auntie was a real dresser. She had everything. Jill had even packed in some jewelry. I assume it was fake. Besides, it added to the image I could portray.

For the first two weeks after the garage sale I became Susan after getting home from work. I dressed differently each evening. I tried imagining myself in different feminine roles. Of course, I had experience dancing with a man. I parlayed that experience into other imaginary situations. Initially, each evening I only intended to dress femininely. When fully dressed I felt there was something missing. To complete the image I fixed my hair and put on makeup. I stopped when I looked at myself in the mirror and only saw a woman. I cannot explain why I had the urge to appear as a woman.

Once I was dressed and completed the image, I thought about going out. Spending evenings indoors as Susan, Left me feeling that I was missing out on the experience. I wanted to go out and experience my femininity in the company of others. That made me think about the evening I spent with Herby, Tom, and Jill. Somehow I never got the courage to go out by myself.

The weather turned colder, and I was able to wear some of my woman's wardrobe under my coat when I went outside. On occasional evenings I wore a bra and the prosthetics under my guy clothes. Only the coat prevented anyone from seeing my extended chest.