Garage Story Ch. 04

I took the folder and looked at the papers inside. On cursory inspection, it looked good.

"How long have you had this? I thought you forgot it."

"Our relationship is important to me. I want to start off on the right foot. I want to make this work. It is understandable that you want security. You're giving up a lot. I will treat you as a woman in all respects except sex. The prenuptial is a standard one. It gives you all the benefits a natural woman would get under similar conditions."

"Since I first met you, I have felt something for or about you. That evening in the car, and later dancing, I knew there was something more between us. Since we have been seeing each other, I have become more sure of my feelings about you. These past few weekends have confirmed what I first felt. Most of my life, I have been a loner because I could not connect with another person. You come along, and I feel an immediate connection. I don't want to lose that."

"You're not leaving me much choice, are you?" I said emotionally.

"I hope not."

"When do you want to start?"

"This weekend?"

"OK."

I gave my two weeks' notice to my old job. On Saturday, we moved most of my things to his home. Claude's things went into boxes that were stored on the upper shelves of the two-car garage. I took my (Susan's) things into the main house.

We agreed that I would have two weeks at my old job before starting work at Herby's company, ITEK2U. It gave me time to get used to the neighborhood, shopping, and the house. I kept my car and used it to go to work, shop, and do anything else I wanted. I was worried that my driver's license and appearance did not match. How would I explain it at a traffic stop?

Herby lived in a quiet residential neighborhood on a dead-end street. It was private enough that we didn't have to deal with other people if we didn't want to. When the neighbors saw that a woman was moving in with Herby, their curiosity was aroused.

Most of the neighbors thought Herby was a recluse. It was clear he had money, but it was not enough for the neighbors to want to meet him. Moving in with a pretty girl (me) made all the difference in the world for Herby. I was the key that unlocked everyone's interest in Herby.

Since the neighbors were not going to walk up to our door, they arranged an accident at the supermarket. While shopping, I found myself in the middle of a traffic jam of no less than 5 women. One thing led to another. After putting our groceries in our respective cars, we sat down for coffee at a nearby restaurant.

There were more questions than I would imagine anyone would have about a person they had just met. They wanted to know everything. They wanted to know about my family. Diverting their questions to other topics was easy. They wanted to know how we met, how long we were together, and if Herby was a good lover, what kind of person he was. I blushed when responding to many of the questions.

I felt pressured to invite them to our house. I was worried that Herby might object to my initiative with the women. It wasn't my house. Everything belonged to Herby. I apologized to him when I told him that I had invited several women over for "tea." Contrary to my expectations, Herby was thrilled. He felt that I was easing into my comfort zone, as a woman. He hugged and kissed me and told me to think of the house as "our" home.

When the women came over, I made sure to dress appropriately for the event. Deciding what was appropriate took a little research. They came over one evening, since I worked during the day. I wore a skirt, a loose blouse, and medium heels. I was a wreck before they showed up and kept asking Herby if I looked OK. He reassured me that I looked good and kept kissing me. It was annoying and comforting at the same time, since I had to reapply my lipstick each time.

The doorbell rang, and I rushed to answer it. Four women came in and reintroduced themselves to me. The last time we met was at the supermarket. Once we were seated in the living room, I introduced them to Herby. Herby stayed for a short time before leaving us alone. I knew I had passed visually. Under the watchful eyes of four women, I was insecure, nervous, and careful to act, move, and sound natural.

I tried to be a good hostess as we sat in the living room. I brought out finger food and drinks. We talked about the neighborhood and a little about Herby and my relationship with him.

I was relieved when the women left. I began cleaning up in the kitchen when I felt Herby behind me.

"You are one sexy broad," he said as I felt his hands encircle my waist. I was enjoying his physical comfort when I felt the warmth of his lips on the side of my neck.

"Herby, please," I said.

"OK, OK, I just want you to realize that they and I see is a very sexy and desirable woman. You have nothing to worry about."

I turned around and looked into his eyes. Once again, his lips were on mine. I returned his affection while wondering what it would be like if I was fully a woman. "Stop!" I said. "You know, I appreciate your attention, but there are limits."

"OK, your correct," he said. "One day you might not want to stop."

"If that happens, it will be my decision."

It didn't take long for us to be invited to a neighborhood barbecue. The women I befriended made sure Herby was introduced to others, and that he was comfortable. It was good to have a social circle. It was good to see Herby developing relationships as well. But, sometimes too much, is too much.

For my part, I was living a woman's life, a married woman's life. It consumed me. No matter what I was doing, in the back of my mind, I thought about my appearance and the impression I made. I was always worried about a slip-up. It is like what biological women do, but for a different reason. Makeup was a part of my daily ritual. I always wore pantyhose or stockings. I wore skirts or dresses with at least two-inch heels. Flats and sneakers were for outdoor activities. Herby rarely saw me not made up. I was overcompensating for my special situation.

My female friends asked me why I was always concerned about the way I looked. I explained that, "A man who is not sure what pleasures will meet his eyes looks forward to finding out." In other words, keep a little mystery in the relationship to keep the relationship. The men never had the same questions. Based on the way they looked at me, I think they appreciated the way I dressed. I know that Herby was thrilled with the way I looked and enjoyed having me by his side.

The only obvious problem I had with Herby was the way he dressed. I dressed to look good, and I wanted Herby to dress in a manner that complimented my look. Herby was not a slob, but he was a nerd. He absently put pens or pencils in his breast pocket. That made him look like a nerd. I wanted my man to be as fashionably dressed as I was. It was a point of friction between us.

I worked two weeks at my old job before starting work for Herby's company. I was going to work at a different location from him. I was introduced as a woman with a referral from "the big boss." Herby prepared false identifications for me. It legitimized my work situation and other aspects of my life. In a way, I was living my dream. Sometimes reality is in contrast to one's dreams. I felt comfortable as a woman.

I was in a strange environment as regards the activities that were normal for my situation. Herby never made a lot of demands on me. My social position dictated that I do the shopping and food preparation. Even though I had part-time domestic help, it still took effort to keep the house clean and orderly. That was my after work job. Several of the other women I was friendly with were in similar situations. We had a lot to talk about. I had it easier than they did, since I didn't have children to take care of.

Whether it was me or my presence, I don't know. But the perception people had of Herby changed. The end of a lonely street became the center of activity. Herby enjoyed his new-found attention. Herby enjoyed having me around to magnify the attention he got. I was his prize. He never hesitated to show me off. I could tell some neighborhood men wanted to do more than look at me. After a while, I was spending as much time in their houses with their wives as they were spending in mine.

Every day, I was morphing into the perfect little working housewife. Dressing and getting it right was an obsession for me. Changing to "higher" heels before going out was my right as a woman. Herby encouraged and watched me take part in life as a woman, as his woman.

Herby gave me an allowance of money to buy new clothes for myself. I felt guilty since I kept thinking of myself as Susan with a penis. Herby didn't want me to wear what I bought at the garage sale since I was no longer that person. I was, and still am, his woman. This new status included the clothes I wore. My adventure was all consuming. There was no end to it.

Herby insisted on accompanying me for most of my clothing purchases. No matter how I felt, he was never happy unless I tried on many clothes, shoes, or anything else. On occasion, he even entered the woman's dressing room to see how the underwear I was about to buy fit me. It was embarrassing. Everyone thought my husband was deciding on my underwear.

It took a few weeks to replace the clothes I bought at the garage sale with new ones. Herby approved of most of the new clothes I bought with his money. At first, Herby's opinions of what I wore, eclipsed mine. I was tired of trying new outfits, one after the other, to Herby's satisfaction. I didn't begrudge Herby a say in what I bought or wore, but I had to make my own decisions. I hesitated at first, since I was not sure what my "husband's" reaction to my independent decisions would be. I was happy when we got home. Herby accepted my right to decide what I wore, despite our differences of opinion.

It didn't take long after I moved in with Herby for me to accept feminine movements as my new natural. Herby appreciated how I looked, walked and moved as I swayed my ass, jiggled my boobs, and teetered on high heels. The clothes I wore forced me to move femininely. Herby loved it. Seeing him enjoy it, I enjoyed it.

It was a relief to get home and not think about going out again to buy something. While the heels caused sore feet, Herby insisted that I always wear heels. So even indoors, I wore heeled mules or slippers. That reinforced my feminized image of myself. Herby liked it. I loved it. And for whatever reason, we were both different because of it.

With all the new clothes I bought, Herby insisted I get rid of the clothes I got from the garage sale. A garage sale was the answer.

I advertised our own garage sale in the local newspaper. Most of what I had to sell were clothes. The neighbors may have wanted some of them, but they said nothing.

The day began quietly. There weren't too many people. Some cars drove by, stopped as eyes peered out, and then continued. There were times when eight or nine people walked through the racks of clothes. Sometimes the men would follow their women.

I noticed one young man who didn't appear to be with a woman. When he noticed me, he walked off down the street. I noticed him walking by the house two more times. He looked to be about my size. The third time he was about to walk by my house, I engaged him in conversation.

** Garage Sale

"Well, are you going to buy it or not?"

"What do you mean?"

"This is your fourth time coming around. I am interested in making a sale. If you want to buy it, let's talk. "

"Well, I was thinking of something for my girlfriend."

"Like what?"

"What about that beige dress?"

"$10 for you."

"What if it does not fit her?"

"Bring it back anytime today, and I'll give you your money back."

I could see he was having a hard time making up his mind. I took his hand and pulled him to the rack. Taking the dress off the rack, I held it against my body.

"Well, what do you think?"

"It looks about right."

I was a little taller than the boy, but then again, I was wearing heels.

"How tall is she?"

"About your height."

"Does she also have my figure?"

"It looks about right."

"Well, are you going to take it?"

"I can't make up my mind."

All right? "Tell you what, come back after five, and if it is still here, I will give you an even better deal.

"Huh, OK."

The rest of the day was slow. Most of the clothing would still be available when the young man came by again.

At five o'clock, he showed up.

"What's your name?"

"Jimmy."

"Well, Jimmy, help me move these things back into the garage, and we'll get the dress out for you."

Jimmy helped me move the racks into the garage. With one door closed and the other open, I took Jimmy over to the corner to pick out the dress.

"What do you think?"

"It looks nice. I'm still afraid it may not fit. "

"Look, your girlfriend is about your size, correct?"

"Yes."

"If it fits you, it should fit her."

"I guess so."

"Well then, try it on, and we'll both know."

"I can't try on a woman's clothes."

"Why not? They are just clothes. "

"I don't know. I just can't. "

"I knew a guy who said the same things you are saying. When he tried on the clothes, he actually looked pretty good. "

"Well, I won't look too good."

"Why not?"

"A dress is not going to make much of a difference."

"I understand what you are saying. In that case, why not let me fix you up. If I do a good job, then you'll know. If I can't do it right, nothing is lost. "All right?"

"You mean dress me up?"

"Yes, nobody will see. My husband is away, and the house is empty. "

"I don't know."

"Don't be so bashful," I said as I pulled him into a small room off the side of the garage. He provided token resistance.

"Here, put this on," I said, as I handed him a pair of panties.

"Well, go on, put them on!"

He took off his clothes, turned his back to me, and pulled the panties up his legs. Then I gave him a pair of pantyhose to slide his legs into.

I wrapped his waist in a bra, clipped the back closed, and pulled his arms through the straps. He didn't react fast enough to realize what I was doing and stop me.

"Not too uncomfortable, I hope?"

"It's OK," he said as he blushed.

I used pantyhose to fill the bra cups. I pulled a full length slip over his head and slid it down his body. Before he could object, I had his arms through the straps of the slip.

"Still feeling OK?" I asked.

Jimmy was preoccupied with his new feelings and couldn't respond to my questions.

Soon he was standing on his stocking feet with the dress zipped up in the back.

"That looks pretty," I said as I stood him in front of a mirror.

"Here, try these on," I said, while helping him slide his feet into two-inch "heels".

He wasn't responding to me. He was looking at himself in the mirror.

I pulled him to the side and told him to sit so that I could fix his face. He tried looking at himself in the mirror as I worked on him. I made sure he couldn't see himself until I finished.

I took out some makeup and applied it to his face, then lipstick and blush. Earrings dangled from his lobes as a necklace hung off the protrusions on his chest. When all was just about right, I fixed an old wig on his head. After combing it out, I stood him up and walked him over to the mirror.

He stood unmoving for several minutes, looking at himself. Slowly, he began to move, relating each movement to himself.

"You look beautiful."

"Do I?"

"You do. More than that, there is no doubt you pass as a girl. "

"I don't think I could go that far."

"There is one way to prove it."

"Yeah, how?"

I gave him a pocketbook and pushed him out of the garage. The heels kept him off balance. Although we were about the same size, I was used to dealing with the restrictions of feminine clothes.

"You have no choice in the matter. Walk to the end of the block, make a right turn, and keep walking till you go around to the corner on the right. Then come back to me. If I see you coming back from the right side, I'll know you did not walk around the block. Now off you go! "

I could see he was about to cry.

"If you cry, you'll spoil your makeup, and then everyone will look at you. Don't look anyone in the eyes. Look as though you have a purpose. Look at the lamppost or traffic light at the corner. Swivel your hips a little. It will make walking in heels easier. "

He began walking towards the corner. At first, he walked hesitantly. Then he tried walking without striking his heel on the pavement and making noise. He was halfway up the block when it became too difficult for him to continue that way. Soon he was walking with his heels clicking against the pavement. I heard the clicking diminish in the distance.

I ran upstairs to look out one of the windows to see if he really walked around the block. He did.

As he walked, he began shifting his body to make it easier. Soon he was walking with his back straight, ass out, and chest protruding forward.

About midway through his walk, a car pulled over next to him. It followed him for a bit. It looked as though the driver was trying to pick him up. Soon he was walking alone again. He was more certain of himself. By the time he got back to me, he was walking casually, except for the aching feet he must have had.

"So, how did it go?"

"I think, OK."

"Do you want to stay in that clothing, or change back?"

"I'll stay in these clothes, if you don't mind."

"It's my present to you. How far do you have to go? "

"I parked my car around the block. I passed it now. "

I gave him a bag for his clothes and some extra clothes I had. With everything packed, he shook my hand and said, "Thank you."

He came as a guy and walked away as a girl.

Jimmy came back a few times after that initial meeting. Each time, I gave him some more clothes and helped him perfect his feminine appearance.

Herby spared nothing. I was surprised by the accommodations Herby made for me. I lost track of our time together until one day, when Herby suggested I move into the master bedroom with him. Up until then, our only physical contact was hugs and kisses. I was on alert that Herby was proposing a more intimate relationship with me. If he was, I still had my apartment and a prenuptial agreement.

"I am not proposing what you are thinking," Herby said to me after suggesting we share the same bedroom. "I only thought that since we are sharing everything, why not the bedroom as well. Notice I didn't say anything about the bed. "

"So why?" I asked.

"We have people over. We visit others. Even in casual conversation, it is obvious that we are not sharing the bedroom. Couples talk about the annoyances of their spouses. We have nothing to say. Sharing the bedroom means that we have to interact more with each other. That's a good thing. "

"If I agree to this," I questioned, "will this mean anything more than two guys sharing the same room?"

"That is not my intent. It is that, living the way we are, and as close as we are, we are still strangers to each other. You are very important to me. I want to be part of your life as much as possible. "

"If this is a ruse of some kind, I'll be gone faster than you can blink your eyes."

"How long have we been together? Have I ever said or done anything that you objected to? I thought you thought better of me than that. "

"Your right. I'm sorry," I said. "It's that this whole situation is still unreal to me. I could never have imagined this situation as a reality. Give me a few days to get my head around this. Are you going to give me the privacy a woman needs?"

"Such as?"

"Bathroom, shower, dressing, or undressing?"

"I thought that since we are two guys, that would not be a problem."