Garage Story Ch. 03

Garage Story Ch 03 of 05

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.

>>>>>

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

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

>>>>>

My name is Herby."

"Herby?"

"My friends' are Jill and Tom."

** END CHAPTER TWO

****BEGINNING OF CHAPTER THREE

I was silent. "What do you want?" I asked.

"To be honest, I couldn't get you out of my mind. I would have called sooner, but it took some effort to get your name and address from the Motor Vehicle Dept."

"You wrote down my car's license plate number?"

"Yes."

"What do you want me to say? You do realize I'm a guy, don't you?"

"I've no problem with that. I just want to talk with you."

"What do you want to talk about?" I asked.

"We got on so well over dinner and dancing, I thought we could become friends."

"You met me when I was pretending to be something I am not. Were you thinking of becoming friends with Claude or my alter ego Susan?"

"I don't know," Herby said. "I don't know if there is a difference. I thought we got along quit well, that evening. We could meet at a neutral location as and see how it goes. You can come as Claude or Susan, whatever you are most comfortable with."

"When we met, that was a one time situation for me. I have no intention of it going any further. Sorry if I gave you the wrong impression."

"I'm not talking about sex. I find it hard to be open and talk with people. It was easy talking with you. I thought you enjoyed spending time with me."

"Look, you're a nice guy. The circumstances of that situation was unreal. Whatever we had then we wouldn't have now."

"Maybe you're right. But I got this bug in my head. If we met, even at a neutral place, it would help me get over this."

"Look, I don't know. This is rather sudden. I'll have to think about it."

"OK. Do you mind if I call you tomorrow?"

"I cannot make up my mind that fast."

"That's OK, just to talk then."

"OK, if it is just to talk."

"In that case, till tomorrow, good night."

"Good night," I said.

Herby's call bothered me. Everything that happened to me the day we met was an unreal fantasy. Herby was making more out of it than it was, or maybe not. While talking to Herby, I looked at the woman in the mirror talking on the phone. Herby was offering me an opportunity to explore my desires to appear as a woman.

My next day at work was difficult. All I could think about was Herby's call the previous night. Was he really going to call me this evening? If he did call me, what would we talk about? My co-workers noticed that my mind was not on my work.

"Girl problems," they laughed. If they only knew.

Herby called that night. The conversation was awkward, to start with. After a slow beginning, we spoke about our interests. I was surprised that we had so much in common. We avoided some touchy subjects. The subjects we talked about were engaging. We spoke for over an hour.

After that initial call, Herby and I spoke every evening for two weeks. Herby finally asked to meet me.

"OK, where do you want to meet?" I said. We settled on a small bar about 15 minutes drive from my home.

"I'm a guy coming dressed as a guy, Claude" I said.

"That's OK," he said.

We met that evening. He was surprised at the way I looked, as Claude. I could see it in his face. I didn't ask him anything about my appearance. It was something I would have done as Susan. It was evident that he was having trouble accepting that Claude and Susan were one and the same.

It was an OK evening. Herby didn't pull the chair out for me or open the doors or anything else he would have done for Susan. He treated me as a guy. I could tell he was not comfortable with that. We spoke about "guy" things. That was in contrast to the subjects we spoke about over the phone. On the phone, Herby imagined that he was talking to Susan, even if Claude answered the phone. At the end of the evening we half-waved goodbye as we each got into our respective cars and drove off.

It was three days before Herby called again. "Hello Claude."

"Hello. What happened to you?"

"I had to think things out."

"Like what?" I asked.

"It's hard to explain. Talking to you on the phone or that time we first met was so much easier than our conversation at the bar. What do you think?"

"I don't know. I've been thinking about it."

"Are you dressed when we speak on the phone?"

"Yes, most times."

"Do you dress up often?"

"Most evenings when I am home."

"Why?"

"I'm not sure," I said

"Do you think that you are subconsciously more comfortable as Susan than Claude?"

"It could be. I grew up with a sister. I watched her talk with our parents, friends and neighbors. I remember how they interacted with her Vs how they did with me or other guys."

"Did they treat you better or worse?"

"It was different. Girls were kinder with each other. They were more nurturing and sympathetic. Girls got the same responses from guys that they got from other girls. Guys are more distant in their relationships. Guys are aggressive, macho, or tough physically and mentally and that creates distance."

"Did you have a good time that first time we met?" Herby asked.

"Yes, once I got over the shock, of being outed," I responded.

"We could have a similar good time, if Susan and Herby met again. What do you think?"

"Are you suggesting a date between Susan and Herby?"

"Yes, why not?"

"Do you realize that Susan has never been out of my home?"

"So Susan dresses almost every day after work, but never goes out?"

"That is about the size of it."

"Don't you think it is about time that Susan goes out and enjoys herself? A date with me would not be the first time, would it?

"You're asking a lot of me. Everything that happened that day was unreal. After getting home it was as though that day was a dream. I was only looking for clothes that would fit me. Jill talked me into trying on her aunties clothes in the bathroom. At first, it was only her aunt's skirt and blouse. As I was looking at myself in the mirror, she knocked on the door. She suggested additions that would make the clothes fit better. Each time she knocked on the door she gave me something else to make me look authentic. Before I knew it, I was looking at a woman in the mirror. Then she offered to give me more clothes for free if I helped her with the garage sale, dressed as I was. When Tom came in and didn't recognize me, that convinced me that I passed. I spent that afternoon helping her, as Susan. I was so removed from any reality, that I got into the character. It was sort of fun, but that is all it was. I was sure that once I drove away, I would never hear or see them again. As we were cleaning up, you called."

"When she heard you were coming over, she convinced me to be the fourth person for dinner. She convinced me that since I passed while helping her with the garage sale. So, I would pass and enjoy myself over dinner. In effect, I was your date. She also promised that you would never know my true self. I was shocked when she outed me. I wanted to bury myself. I don't know that I could go through it again," I said.

"Once I understood that they were telling me the truth and not playing a joke on me, was I anything but a gentleman to you?" Herby asked.

"No. You were great. I can only thank you for the way you treated me."

"Did you feel, at any time, that anyone treated you as anything but a woman?"

"No."

"Once you got over your initial concerns, didn't you have a good time?"

"Yeah, I did have a good time. You were great. Even Tom and Jill accepted that we were having a good time."

"Isn't it worth another try? I am a known quantity. You know how I will treat you. Don't you want me to treat you the way I treated you that night? At the very least you deserve the chance to see if you are comfortable in public with me."

"So you want me to become Susan again? You want to date me as Susan? You realize I have the same equipment as you. I am not gay. I have no interest in the male body, that is not my own."

"I was thinking about two individuals with different perspectives, having a good time. Nothing sexual, just enjoying each other's company."

"Do you think that as a woman, my whole personality will change? That it would affect my attitude, character and relationships?

"Yes, I think so," Herby added.

"I've got to think about this."

Over the next few days we discussed the subject many times. Every day after work, I became Susan. Was Susan different from Claude? There was no doubt I felt different when dressed as Claude Vs Susan. Herby's argument was getting through to me. I owed it to myself to explore my feelings more. I was scared. What if I was more comfortable living as Susan Vs Claude. Would that mean I wanted a sex change?

What if it was true that my brain chemistry changed when I dressed as Susan. What did that mean for my future? It is one thing to pretend to be someone you are not where no one knows you. It is another thing to pretend where people know you.

"Suppose I pick you up for a regular date. I will treat you like I have with other women. I will come to your apartment bearing flowers and plan for an interesting and varied evening. No one will question what or who you are. If at any time you feel threatened or insecure about your standing, I will immediately bring you home."

"You actually want to come to my apartment and take me out as though we were going on a date?"

"Yup."

"How much would this cost me? Where would we go? Would you be a gentleman all the time? Sex is off the table!"

"I am the guy in this relationship. I pay for everything. Your payment is a kiss on the cheek when I bring you back. That is the only thing you owe me, and that is on condition that you have a good time. Sex is not included. Neither one of us is gay. Suppose I come by late one weekday evening. There won't be a lot of people coming or going."

"Herby, I don't know. This is getting scary."

"Come on Susan, if it's so terrible I'll never ask it of you again. You're dressed anyway, might as well go out and have a good time."

Silence.

"OK," I said. "What are we going to do? What should I wear?"

When I got home that Tuesday evening I had to decide on what to wear. I wanted to look as authentic and classy as possible. With my slender build, the prosthetics gave me a typical hour glass figure. Wearing of the waist nipper every day compressed my waist naturally. It made the clothing I wore fit better. I was comfortable wearing feminine clothing. Unfortunately all the clothing I owned originally belonged to Jill's aunt. She was older than me, so her clothes were not fashionable for my age.

Based on what Herby told me we were going to do for the evening, I thought a black dress would be appropriate. With the prosthetics and my small waist I could wear a tight-fitting dress that hugged my padded body. Short sleeves would expose my arms ending with red tipped nails. The dress had a low cut neckline that exposed my chest above my breasts. I wore a necklace with matching earrings. The necklace would lay on my exposed chest. Black mesh stockings in 3" high open heel and toe slippers completed the vision.

Unlike the first time I met Herby, my hair was now my own. I wore a fall, so my hair framed my face down to my shoulders. Since the day I first met Herby I practiced applying makeup daily. I was looking for a "look" that matched the way I felt. I wanted to look cute, sophisticated and mature. That meant that I used very little makeup in a sparing manner.

It took me more than an hour to get ready. When I finished I looked at myself in the mirror and ran my hands down my sides. I felt sexy and feminine. I posed sexily as I looked at myself in the mirror. I wanted a "look" that removed any doubt about what I was. I wanted to enjoy this evening. Feeling sexy and feminine insured that I could move freely. I was excited with the way I looked. I wondered how my date Herby would see me.

The doorbell rang. I had butterflies in my stomach. In my best feminine manner I sashayed to the door and opened it. Herby stood there with flowers in hand and didn't say a word.

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

"You're beautiful! You look like a different woman than the one I met at Jill and Tom's house.

I blushed, "come in."

"These are for you," He said, handing me the bouquet of flowers.

"Thank You," I said then took them into the kitchen and put them in a vase. "They're lovely."

Herby stood in place looking at me as though it was for the first time. I smiled as I teetered on my heels while getting ready. Coming back towards him, he looked uncomfortable. I turned away for a second and peripherally noticed Herby adjusting his crotch.

"Am I making you uncomfortable?" I asked.

"What makes you say that?"

"Claude frequently adjusts his crotch under certain conditions. It is a compliment for a woman to know that she affects a man that way. Am I affecting you that way?"

Herby looked very uncomfortable and didn't respond to my question.

"I think you look very handsome," I said to Herby, as I sashayed closer to him.

I was about six inches from his face and looked straight up into his eyes. Then I said, "I've spent a lot of time looking at myself, preparing for this evening. I know what I look like. If I was a guy looking at a girl like me, alone in her apartment, I know what I would want to do. I feel feminine and sexy standing next to you. What would you like to do, before we leave?"

He was frozen and tongue-tied as I baited him. I moved closer pursing my red lips as I looked up at him. My breasts finally made contact with his chest. I put my hands on his sides and looked up. "I am going to go crazy if you don't do what I think both of us want."

I stood on my toes and reached for his lips with my own. I felt his labored breath on my face. I tilted my head to the right and waited for his next move. My heart was beating, and I wasn't sure how much longer either of us could do nothing. Finally! His lips devoured mine. His arms encircled me pulling me in to him. His body warmth was mine. I moved into his embrace. It felt good. I wrapped my arms around his body and pulled him into me as much he pulled me into him. He felt my breasts against his chest, while I felt his rock hard manhood against my stomach.

It felt as though we stood in place feeling each other for an hour. It was probably less than a minute. We were humping each other when I thought about my make and the dress I wore. Finally, I pushed him away with some difficulty. "I need to repair my face before we leave," I said breathlessly.

Herby stood in place and looked at me. "What just happened?" he asked.

"I am sorry. No, I am not sorry! I got caught up in my character. I feel so sexy and feminine, and you look so handsome, I wanted to feel authentic for a short time. I wanted to feel that you want me as a man wants a woman. Did you want me? Do you want me?"

As I walked towards the bathroom Herby said, "Oh yeah. For a short time all I could think of was that I wanted you body and soul. I don't think there is a man that wanted a woman as badly as I did you for that short time." I turned and looked at him and said, "Does that mean I pass?"

"I need to use the restroom when you are through," he said.

"Did you wet yourself?" I yelled from the bathroom.

"Yeah. You did a job on me. How are you holding up?"

"I am unfortunately confined. I'll masturbate when I get home later tonight. But, I'll be remembering being held by a big strong man who was passionately kissing me."

"I think there is more Susan in you than Claude. So maybe my instincts were correct."

"Is this going to ruin our evening out?"

"No, not at all. It just makes me appreciate you more.

I finished repairing my face and exited the bathroom. "Your turn," I said.

Herby awkwardly approached the bathroom. He closed the door. I could hear the water running. "Do you have any paper towels?" he called out.

I went to the kitchen and grabbed a roll of paper towels he could use. Knocking on the bathroom door I handed them to him. When he finished in the bathroom, he joined me in the living room. We stood about three feet apart looking at each other.

"You know that I'll never be able to think of you as Claude again. No matter how you are dressed or undressed you'll always be Susan to me."

"I guess that is good since your relationship with Claude was not great to begin with. Now that we have established a new relationship, are we still going out. I am hungry."

"It is my pleasure to spend the evening with you. I want you to be happy."

"In that case, am ready if you are," I said. I went to the entrance closet to get a coat. As soon as Herby understood what I was doing, he jumped in front of me. He asked what coat I wanted to wear, then took it off the hanger and helped me on with it.

"Thank you," I said as I looked up into his eyes.

I grabbed a pocket book I had prepared, and swung it over my shoulder. He opened the door and I stepped outside. The coat gave me a little security going outside. Herby locked the door and gave me the keys to place in my pocketbook. We walked towards the elevator with my arm in his. Herby pushed the call button. The elevator took a long time to come. We stood silently looking into each other eyes, while waiting for the elevator.

"You are making me feel uncomfortable, staring at me like that," I said

"Sorry. It is that of a dream I had come true."

"Herby, don't forget who I am," I admonished him.

While we waited for the elevator Herby came closer and closer to me. I put my hands up to block his kiss.

"Good girl," said a woman walking by. "Never let them kiss you on the first date."

We looked at her as she continued into her apartment. When the door closed we broke out laughing.

The elevator door opened. Herby stood aside and let me enter first.

"You were going to kiss me," I said.

"Sorry. I don't know what came over me. You are beautiful and sexy. I lost it for a moment. If that woman hadn't disturbed us, would you have kissed me back.

"I don't know. I feel very feminine and sexy, especially when you look at me. Please don't put me under pressure. This is not a romantic date. This is a platonic date, and nothing more."

"So what happened in your apartment?"

"It was the female in my character that got out of control. That is all."

The elevator arrived at the ground floor, and the door opened. Herby stood aside to let me walk out first. Once out of the building, he led me to his car. His car was a lot nicer than mine. He remained a gentleman. I liked the way he treated me.

We went to a late night movie, then had a small snack at a nearby diner. The conversation and company were pleasant and inviting. We laughed and talked about everything. I couldn't have had a nicer time.

The night air was brisk and slightly cool. We walked arm in arm, before going back to the car and driving home.

Herby got me back to my apartment around two in the morning. "Had a good time?"

"Very."

"We gonna do this again?" Herby asked.

"Is there any doubt?"

Herby put his lips to mine and we kissed. It was a small kiss, between friends. As he held my arms for the kiss, I put my hands on his waist. With my eyes closed I felt his lips. It was a good kiss. One we would repeat many times over.