Crystal's StorySite


Amy's Problem

by Carlito Esperanza


Amy packed the suitcase carefully and when she was finished she closed and locked it and carried it to the car. There she placed it in the trunk and pushed it to the deepest part. The case wasn't large but she was sure it wouldn't escape notice by Jay as he loaded the car. She had already decided what she would say; "It has some things I may need." She hoped . . . No, she didn't know what she hoped, but the time had come to deal with the problem. This vacation, when they would have a week together far from work and routine, was the ideal time.

As they drove south toward the coast, Amy though about how their life together had begun.

"IT, this is Jay."

"This is Amy in Dr. Brian's office. My printer is jamming, and I've got a report I need to get out this morning. Dr. Brian needs it for a meeting this afternoon."

"OK, look on the back of the printer and tell me our company part number."

"There's a sticker with the company logo and the number 1077. Is that what you want?"

"That's it. I'll be down in about 5 minutes with a replacement." Jay looked in his data base and saw that number 1077 was an HP 4 with 8 mb of memory. He went to the supply room and picked up an HP4. A quick check showed that it had only 4 mb of memory. In the stock room he checked out an additional memory card and installed it. The he put the printer on a cart, checked his appearance in the mirror by the door, and headed for Dr. Brian's office.

Amy was surprised. The fellow from IT didn't look like a geek. He was wearing a tie and no glasses. As he unplugged her printer and replaced it with one that appeared to be just like it, he asked what had been the problem. She explained that although she had carefully removed all the paper the first time the printer jammed, it had immediately jammed again. "Hmmm. Sounds like you have a dirty feed roller. I'll take it and clean it."

Amy looked at Jay's company ID and said, "Jay, you're great." She placed her hand on his, looked him in the eye and said, "Thanks so much for the help." The touch didn't linger but it sent a thrill through Jay. Amy was not only cute, she was sweet. He would like to get to know her better. But Jay was shy. He didn't find it easy to meet people. And especially, he didn't find it easy to make small talk with girls.

Two days later Jay carried the cleaned and checked printer back to Amy's desk. When she saw him, her smile was like sunshine. He exchanged the printers without a word and placed the spare on the cart to return to storage. Amy looked at her watch and said, "Its coffee break time. Do you drink?" Jay startled. He thought she was asking if he drank liquor. Then he saw her grin and realized that she was suggesting they take the coffee break together.

He smiled and said, "I have to return this printer to storage first. I'll meet you in the break room in 10 minutes. OK?"

"OK, see you there."

Jay put the printer away and trotted down the stairs one flight to the floor of the break room. He arrived just as the elevator doors opened and Amy stepped out. This was the first time he had seen her standing up. She was wearing a navy blue suit. The skirt was straight and came just to her knees. Under the jacket she wore a white blouse with a tailored tucks and an almost masculine looking collar. At the collar she had a small navy tie that just crossed. Her hose were navy as were her shoes. With the 3 inch heels, she was just the same height as Jay.

They walked together to the break room door. Jay held it for her. She smiled and said, "Thank you." Lots of women would have just sailed through without a word. After all, it was their right they seemed to say.

Amy filled a mug with coffee and picked up non-dairy creamer and sugar. Jay filled a mug with hot water and picked up a tea bag. Then they sat across from each other at a small table. Amy smiled a Jay. Jay felt his face color. "Not a big talker, are you?"

"No, I guess I'm really not," he replied.

"Well, where did you go to school to get into IT?" Amy gently led the conversation, asking questions about Jay and telling about herself as she did. By the time the break was over, Amy knew enough about Jay to know that she would like to encourage the relationship. And she knew that she would have to take the initiative at least for the time being.

There was always coffee and hot water to make tea in the IT section. But the next day Jay decided that he would get his tea in the break room. He was disappointed when he arrived and the room was empty. He filled his cup and was looking around to decide where to sit when Amy came in with another young woman. Amy was wearing a tailored dress, black with white trim. The other woman, a light gray suit.

Jay smiled and said, "Hello." Amy returned a bright smile. Jay took a seat at one of the tables. The girls filled their mugs and then with Amy leading the way, walked over to where Jay sat. "May we join you?" she asked. "Please do" he responded. The two sat across from him. Amy introduced the other girl as Sue from the office across the hall from her's.

Sue studied Jay for a minute and said, "Well, you certainly don't look like the IT type." At that Amy poked her in the ribs and frowned. Jay blushed a little and replied, "I make a point of not looking like a geek. Its good for the department image."

Amy changed the subject and they chatted casually for about 15 minutes before returning to work.

The next time that Amy and Jay met in the break room, she was alone. They chatted about the current crop of movies showing in town. She was surprised that Jay didn't show much interest in the big action movies. He hadn't seen any of the Terminator movies or Men in Black. But he seemed more interested in what were often called "chick flicks", movies that usually appeal to the women. That was all right. Amy didn't care much for the violence of the action films.

When they met on Friday Jay screwed up his courage and suggested that they go to a movie. Amy agreed. She was pleased. Jay was perceptive. She hadn't had to ask him for the first date, just hinted that she would like to see that movie.

After the film they stopped in the food court of the mall and had a dish of ice cream. Jay was more at ease with Amy then with any girl he could remember.

On Saturday morning Jay did what he had done for many Saturdays, he showered and dressed - panties, pantyhose, bra, falsies, slip, and a casual dress. His shoes were a pair of low heeled sandals that he had found at an unclaimed baggage store. Then he set a wig that he had bought over the Internet on his head and applied lipstick to his lips. He wasn't really satisfied with the appearance but it was the best he had managed. Getting makeup right had always eluded him. Once dressed he set about doing the weekly chores around the house. He put clothes in the laundry, washed the dishes, made a grocery list, made the bed, and vacuumed the apartment. Then he sat down to read the current issue of Vogue magazine.

After a light lunch, Jay washed his face carefully to remove any trace of the lipstick. Then he changed into male clothes and went grocery shopping.

Weeks passed and Jay's relationship with Amy progressed to a point. They had dinner together frequently. They went out with friends. They went on a picnic at the lake. In everything they did, Jay was a perfect gentleman. His kisses were warm and gentle and his hands well behaved. He never tried to grope her. Amy sensed that he loved her and that he respected her. But she was about to decide that she would have to propose marriage to Jay because he seemed to be afraid to take that step. Yet she was afraid that if she tried to push him, he might drop her. She had probed gently to see if there was something in his background that made his shy away from marriage. But he gave no indication of any unhappy previous relationship. Still. . . something held him back.

Finally, one Friday evening after dinner, Jay said, "Amy, I love you and I want to spend the rest of my life with you. Will you marry me?" Amy squealed with delight and accepted immediately. The next morning they went shopping for rings. By this time Amy knew enough about Jay's finances that she knew they couldn't buy anything expensive. Still, Jay steered her to a beautiful set of rings that didn't seem outrageously expensive.

That afternoon Jay went home to clean house. He loaded all his feminine clothes, makeup, shoes, wig, everything, into a large garbage bag, tied it securely and put it in his car. He drove an office complex far from where he worked and put the bag into the dumpster. As he drove away, he made a promise to himself. He was through with wearing women's clothes. He would never do it again. Amy would be the only woman in his life. He was relieved but somehow he felt sad.

The following weekend Jay and Amy drove east to a small town near the state line to meet Amy's family. Mr. and Mrs. Buckner received him warmly. They seemed so very much like his own parents. They had lived in the town many years and had lots of friends. Mr. Buckner was a mid level manager in a local manufacturing plant and looking forward to retiring in a couple of years if the plant didn't close due to foreign competition.

On Sunday they attended church and Jay was on display for all the town to see. He had expected that. He knew Amy's turn would come when he took her to meet his parents. That afternoon they returned to the city.

Six months later they were married. The wedding ceremony was beautiful. The only thing that spoiled it for Jay was a twinge of jealousy because Amy was radiant in her wedding dress and he really would have liked to wear it, too. Jay hastily put that thought out of his mind. He was through with dressing up. Amy was the only woman in his life. Period.

At work, both Jay and Amy were promoted. Jay became head of Information Technology for the company and a few weeks later Amy became an administrative assistant. With the promotions came significant increases in pay as well as additional responsibility.

They managed to schedule their vacations to coincide. It was their first since their honeymoon a year earlier. Their new positions entitled them to use the company owned condo on the Gulf coast. They were fortunate that no one with more "rank" wanted it the week of their vacation.

They crossed I-10 and continued on south to Panama City then turned west following US 98. The beaches were beautiful and the surf exciting as they drove toward Destin. The Florida coast was a great place to be in June.

They spent their first day at the coast exploring the town, playing tennis, swimming in the Gulf and lying on the beach. Jay sensed that Amy was nervous about something but he figured that when the time was right she would tell him what was bothering her.

The balcony of the company owned condominium overlooked the Gulf of Mexico. It was a great place for their first vacation together. The building was turned so that their balcony got only the morning sun. As they sat on their balcony in the late afternoon of the first day, Amy looked over at Jay sitting on the deck chair beside her. His slight build didn't bother her. His gentle manner had captivated her from the first time they met. He was reading a technical magazine and occasionally watching the people on the beach below. She loved him. She knew she loved him and she thought that he loved her. The first year of their marriage had been good. There had been the usual struggles as the two adapted to each other but everything seemed to be working out fine. Everything except one little detail.

And that one little detail had almost sent Amy into a tailspin. At first she was angry, then hurt, then confused. Then she alternated between anger and confusion. Finally, she had gone to a counselor. Now she was about to put his suggestions into action. She remembered that he had emphasized, "Don't be afraid of silence. Be patient."

She reached over and took Jay's hand. She studied the long fingers with their well cared for nails. They were not perfectly shaped but with a coat of nail polish they would pass for a woman's nails. She looked at his arm and noticed that the hair was fine and almost blond, hardly noticeable. His face was almost beardless. She knew he shaved only once or twice a week. His hair was light brown with streaks of natural blond. Jay turned his head and smiled at her. She forced herself to smile back. Her heart was pounding. Then she looked straight ahead and asked, "Jay, what do you know about transvestites?" She didn't want to look at him. She was afraid of what she might see. She felt his hand flinch slightly.

He responded, "You mean men who wear women's clothes?"

"That's right."

"Just that. They like to wear women's clothes."

"Are they homosexuals?"

"I understand that some are. Some are not."

"What about you? Do you like to wear women's clothes?" She felt his hand tighten in hers. She still had not looked at him but she knew that he was looking at her, trying to read her thoughts, to see where she was going with this line of conversation.

"Why do you ask that?" His voice had just the slightest edge to it. He was trying to stay calm. He was still sparing. He wasn't ready to confess to anything just yet.

She turned and looked at him. Their eyes met. She could see the terror deep inside him even though he was trying mightily to control it. "Well, you have been wearing some of my clothes. I figured you must like it." He blushed deep red. He was caught and near panic.

"I, ah . . ."

He stopped. He didn't know what to say. Amy put her other hand on his and said gently, "All right, Jay. Now its out in the open so we can talk about it."

Jay looked at Amy. She was not visibly angry but he could not decide just how she felt. He didn't know what was coming next but he was afraid it wouldn't be good.

After a long pause Amy continued. "We have talked about everything that is important to us. I thought I knew you well. But when I realized that you were messing in my clothes I didn't know what to do. I got some of the security people at the office to loan me a miniature camera and a recorder. I caught you on tape. At first I was terrified. Then I was angry. Then I was confused. I didn't know what to do. Finally, I talked to a counselor. He suggested that we get the matter out in the open and deal with it."

Jay was breathing again. He took a deep breath and then said, "Yes, I have been wearing some of your clothes."

"Why? What do you want? Do you want to be with another man? Do you want a sex change? What's going on? Why do you do that?"

"Slow down, please. You're asking a bunch of questions and I can't answer them all at once. I'm not even sure that I can answer some of them at all." Jay was still afraid. He didn't want to loose Amy. He didn't want to hurt her. He was afraid that whatever he said would be misunderstood and worsen an already bad situation.

"All right. One at a time, then. Are you homosexual? Do you want to dress to attract another man?"

"Absolutely not. I love you and I don't want anyone else, man or woman."

"Then why?"

There was a long silence then Jay said, "Let me start from the beginning, or as near to the beginning as I can remember." Amy nodded. She was still holding his hand in both of hers and studying his face intently. "I really do not remember when I became fascinated with girl's clothes. But when I was about ten or eleven I remember that I asked my mother if I could go trick or treating that Halloween dressed as a girl. 'That's a funny thing for a boy to want to do' she said. But she borrowed some of my sister's clothes and dressed me up from the skin out - panties, slip, a pretty long pink dress with a full skirt, socks and shoes. Then she combed my hair into bangs and pinned on a fall so that I had long hair. I think even she was amazed at how much I looked like a girl. I put on a Cinderella mask, went out and had a good time except for the teasing that I got from some older boys. I learned then, that no matter however much I liked to wear a dress, it wasn't acceptable to do it in public. But that didn't change my desire to wear the dress."

Jay paused and thought a while. That also gave Amy time to think about what she had heard. "After that, I sneaked my sister's clothes when I could or dressed from the dirty clothes hamper. I really wanted to have some clothes of my own but I didn't have any place to hide them. Besides, I was too embarrassed to go out and buy them for myself. As long as I was at home, of course, I could use my sister's or my mother's clothes. My sister said something a time or two that let me know that she knew I was wearing her clothes. But she never made a scene about it. And I imagine that Mother knew too, although she never said."

"During college the only time I could dress was when I could arrange to be home when no one else was there. Several times I almost got caught.

Living in an all male dormitory was the pits. Some of the guys made remarks about me being effeminate but I was dating girls and not doing anything that might cause anyone to think I was homosexual. I wasn't interested in boys and I certainly didn't want to be labeled.

"When I finished college, I got a job and an apartment of my own. Finally, I screwed up my courage and bought a few things for myself, usually at a thrift store or at the unclaimed baggage store. And I ordered some things from catalogs. But that got me on mailing lists and more catalogs and advertisements came to my apartment addressed to 'Miss Carol Brown.' I figured that would get me in trouble so I stopped that as soon as I could."

"Then I met you. When our relationship got serious and I began thinking about marriage I threw everything out and swore, 'Never again.' "

Jay paused. Amy gently rubbed the back of his hand. There was no hurt or anger that he could read on her face. "The promise was made with all good intentions but I just couldn't keep it. Pretty soon, whenever you would be away from the apartment, I was into your things. I just couldn't resist. I can't explain it. I don't want anyone but you. And I do want you desperately, but I just can't overcome that desire to wear women's clothes."

Amy was caught up in Jay's emotions. She reached over to pulled him toward her and said, "You poor dear. I don't understand. But I do believe you. I love you and I want you, too." Their eyes were wet with the tears forming in them.

Finally Amy said, "Well, all this squares with what the counselor told me and with what I have read about transvestites."

"What are we going to do now?" Jay asked, dreading the answer.

"I thought we would see if we can adapt to a new reality. You have done everything I could want to make me happy. Now, let me try to make you happy. Please get that suitcase that we left in the car. I think I need it now."

Jay went to the car and got the single suitcase that had been left in the trunk. In the bedroom Amy worked the combination and unlocked the bag. But before she opened it, she turned to Jay and said, "Why don't you use some of my bath oil and take a nice tub bath. Shave your legs, too. There is a razor in the medicine cabinet. Oh, and don't forget to shave under your arms."

While he was bathing, Amy rapped gently on the door and then entered the bathroom. She took away the jockey shorts he had brought with him and left in their place a pair of beige nylon panties. She smiled at Jay as she did.

When he came out of the bath he saw that Amy had laid out a wardrobe for him. He looked at it but did not recognize any of the pieces as being anything from her closet. Hesitantly, he picked up the bra. The cups were lace all over. He fastened the hooks, turned them to the back and put his arms through the straps. The cups were empty. But there on the bed lay a pair of falsies. When he picked up the first one he realized that they were not ordinary falsies. These were soft, yet heavy. He inserted first one then the other into the bra cups. Immediately he felt the additional weight on his shoulders. Amy had watched this. She smiled when he placed his hands under his ersatz breasts and jiggled them slightly to seat the breast forms just as she did to seat her own breasts.

Jay was nervous. Here he was doing things he had done many times before, but always when he was alone. Now Amy was watching. He sat at the dresser stool and began to put on the pantyhose. He smoothed out the hose, enjoying the silken feel under his fingers and admiring how his now hairless legs looked. Then he picked up the full length beige slip, ran his fingers along the wide band of lace on the bodice, pulled it over his head and tugged at it to get it down over his breasts. He looked at the dress with its long zipper down the back and said, "I think I'm going to need help with this."

"That's all right. You have zipped my dress enough times. I can zip yours" giggled Amy. Jay unzipped the dress, ran his arms up through the skirt and into the sleeves and slipped it over his head. He smoothed the dress down over his body and reached back to close the zipper. At that moment Amy stepped over and ran the zipper up for him. He turned and kissed her on the lips just as she had kissed him many times after he had zipped her dress. Amy smiled. The dress was of a satiny material and had a fitted bodice with a flared skirt. It was almost snug around his torso and emphasized his now very feminine silhouette.

Then Amy set out a pair of medium heeled sandals. Jay sat on the dresser stool and put them on without difficulty. He was amazed that they fit. He knew that Amy's shoes were too small for him. And he realized, too, that a dress that fit like this one would have been too large for her. He and Amy were very nearly the same size but not that close. She must have bought these clothes just for him.

He stood and gave a little tug as his skirt. "Very feminine," Amy thought. Then he looked at her and asked, "Now what?"

She responded, "What do you usually do at this point? Do you put on make-up?"


"Sometimes I try a little lipstick but because of time and the fear of getting caught, I usually don't do anything more with make-up. I just parade around the house trying to look and act feminine."

"OK, what do you say we take the next step?" With that Amy opened a small sack and spread on the dresser a variety of make-up items. "Since you haven't done this before, let me do it the first time and show you how. Sit here at the dresser again."

As Amy worked, applying foundation, powder, blush, eye shadow, eyeliner, mascara, and finally lipstick she explained each step. The smell of the make-up and the taste of the lipstick were very exciting to Jay. Amy explained not only what she was doing but why. When she was finished with the make-up she went to the suitcase one more time and returned with a wig that looked very much like Jay's hair might if it were shoulder length and wavy. She placed the wig on his head and after adjusting it, pinned it in place. Jay was turned sideways to the mirror but he had been sneaking peeks from time to time. He was impressed with the changes he saw taking place. When the wig was in place Amy gave him a nudge and he turned to face the mirror. He was startled. The woman he saw was not a beauty queen. But she was acceptably pretty and decidedly feminine. He studied her for a moment and then smiled. She smiled back at him. Then Jay turned to Amy. She was smiling. He stood and hugged her. Then he kissed her on the mouth. Finally, he said, "Thank you. Thank you for this." Amy grinned and said, "Now you need to check your lipstick to be sure you didn't smear it."

Amy picked up a pair of dangling loop earrings and clipped them on Jay's ears. Then she put two bracelets on his arm.

"One more thing. Give me your left hand." Jay extended his hand. Amy took his hand and removed his wedding ring. Then she reached into her pocked and produced a diamond engagement/wedding ring set that was similar to her own. She slipped the rings on Jay's finger and said, "They're only zircon but they look very real, don't you think? You may be wearing a dress, but remember, you are married to me." Then she kissed him on the mouth.

"What's your name? Did I hear you say 'Carol'?"

"Yes, that's right. Carol."

"All right, Carol, we have pretty well killed the afternoon with this little project. Let's go fix something to eat." Amy turned and started to the door but she stopped to watch Carol who wasn't very steady yet, on her high heels. "Are you all right? Can you handle those heels?"

"Oh, I'll make it. Its just that I haven't worn heels since my feet got too big to fit my sister's," she grinned.

Amy picked up the apron she had worn earlier and put it on. Then she looked in a drawer and after a little searching came up with a frilly cocktail apron for Carol. Carol started to tie it on but stopped, backed up to Amy and said; "You tie it please, so that the bow is pretty and not crushed." The two worked together as a team just as they had many times before. Carol set the table while Amy fixed the salads. Then they sat to eat. Carol realized instinctively that her portion was smaller than Jay would normally have received because, as a woman, she was expected to eat less. There was little conversation during the meal. And in a few minutes they cleaned up the dishes, again working as a team.

Amy noticed that by the time they finished with the dishes, Carol was, indeed, doing well on the heels. She was taking smaller steps and putting the ball of her foot down first. This was not the first time she had worn heels.

As they left the kitchen Amy asked, "Now what?"

"I've never been able to stay dressed for so long. I don't know what to do."

Amy smiled and said, "Then let's go to the living room and talk. Let's get acquainted." She led the way and sat on one of the stuffed chairs. Carol followed and sat in another. She took care to smooth out her skirt before sitting and sat with her knees together in a ladylike manner. Amy thought, "She is working hard at being a lady."

Then Amy realized just what she had thought, "She's..." "Yes, she does look and act feminine. There are some rough edges but the basic things are there: posture, walk, and manner of sitting."

Amy shifted and pulled her feet up on to the chair, partly under her and partly beside her. Carol asked, "How do you do that?" Amy giggled and repeated the motion so that Carol could observe better. Then Carol tried to do the same thing. Her motions were not as natural as Amy's but she got the same results and ended by giving a tug at the hem of her skirt.

They talked for a while about Jay's experiences with dressing and his fears of being caught. After some time of such talk, Amy moved to the couch and patted the seat beside her, signaling Carol to join her. She did and Amy took her hand. "Tell me, what do you really want from this?"

Carol was silent for a long time then she said, "You know, I really don't know. I have always had to sneak around to wear these clothes. And I was always afraid of getting caught. When I was dressed I fantasized about looking like a woman and being able to go out and do things like shopping or dining. And I have fantasized about you making love to me when I am dressed as a woman. But I never really had any goals." She paused for a long time then continued, "Tell me, now. We have talked about me. How do you feel about all this? We're in this together. You've been very sweet and gracious but it is not just me we have to be concerned about. You have feelings and rights, too. You didn't just run out and buy this dress when you found out. How have you been handling all this? "

Amy was surprised by this turn of the conversation. It was her turn to be pensive. Finally she said, "Frankly, it was hell at first. I was, and still am, frightened. I was hurt. I was angry. I was confused. I finally decided that I couldn't handle it by myself so I went to a counselor. He helped me a lot. Through some things he gave me to read and some research I did on the Internet I got a better understanding of transvestites. But then, each one is an individual. It is hard to make generalizations. The counselor suggested that we get things out in the open and that I do it by bringing you those clothes."

Carol put her arms around Amy and held her close. "Oh, darling, I don't want to hurt you. And I certainly don't won't to loose you." Carol kissed Amy on the neck, the cheek and finally very tenderly, on the lips. The kiss lingered. At last, Amy began to return the kiss. She opened her lips and invited Carol's tongue into her mouth. Her hands began to explore Carol's body, sliding across the satiny material of the dress and down the skirt. Carol cupped one of Amy's breasts in her hand and began to roll the nipple gently between her fingers. It grew large and hard. When the kiss broke at last, Amy stood and offered her hand to help Carol up.

"Come on, let's go to bed. I have another surprise for you."

In the bedroom Amy unzipped Carol's dress, then began to undress herself.

Amy was casually dressed and quickly changed into a very sexy shear white gown. Carol undressed more slowly, almost reluctantly. When she had removed all her clothes except her bra and panties, Amy said, "Look what I have for you." Carol turned and saw that Amy was holding out a gown that was very similar to the one she was wearing. Carol took the gown from Amy and holding it in front of herself, turned to the mirror and swayed back and forth. "Go ahead and put it on, Silly."

Carol slipped the gown over her head. Then she turned and took Amy in her arms. She felt their bodies pressed together, breast against breast as they kissed. The feeling of the soft gown between their bodies was exciting. Then she kissed Amy again, on the neck and ran her tongue into her ear. That brought a shiver from her. She kissed her on the mouth and pushed her tongue into Amy's open mouth. The kiss was long and passionate. Amy was excited and felt the hard excitement of Carol as she pressed her body against Amy.

When the kiss finally broke, Amy pulled back the covers and they climbed into bed and into each other's arms. "Make love to me," Carol said.

The next morning when Jay awoke he wondered for a moment if he had dreamed the happenings of the day before. Then he felt the soft gown against his body and knew that it was true. He turned and looked at his wife lying on the pillow beside him. "She's some fantastic lady," he thought as he slipped out of bed, took off the gown, gathered up his jockey shorts and went to the bathroom. It had been a day like no other. Amy had accepted his dressing up. More than that, she had actually helped him. He had never imagined that it was possible. But he certainly didn't want to push his luck. Today he would wear his male clothes and wait to see what would happen. If this were really real, there would be other times. He wouldn't have to force things.

He didn't hear the bathroom door open and close as he showered but as he dried off he noticed that the shorts had again been replaced with nylon panties, this time, white. He slipped them on and then shaved before he opened the bathroom door.

As he stepped into the bedroom, Amy met him and put her arms around his neck and looked into his eyes. "Hmmm, last night was fun. I hope you enjoyed it as much as I did."

"Oh, I did, my love. I did", he replied. Then she kissed him.

"I've laid out clothes for you. I hope you don't mind."

Along with the bra and breast forms Jay found pantyhose, a half-slip, a light blue sleeveless blouse and long denim skirt that buttoned down the front and was open the last several inches. The medium heeled sandals were again beside the bed.

After Jay put on the clothes Amy looked at him and said, "I think you are going to need some help with that skirt. Take off the skirt and hose and put on this padded panty girdle. It will help hide that bulge and add some width on the hips. Jay did as he was told, tucking his manhood away.

When he was dressed again he noticed that the front of the skirt was indeed flatter and fit smoother around his hips and across his bottom. He sat at the dresser as Amy applied make-up and placed the wig on his head. He was still wearing the rings from the night before. Carol was back. She stood and hugged Amy.

After a quick shower, Amy dressed similarly to Carol, a beige sleeveless top and mid-calf length denim skirt. She wore low-heeled shoes. Carol had a hard time not having unladylike thoughts as she watched Amy dress.

As they moved toward the kitchen, Carol put her hand on Amy's butt and rubbed gently. "None of that now, or we will not get anything done today," giggled Amy.

After a light breakfast Amy said, "Let's go shopping."

"You're teasing. Someone will realize that I'm not a woman and then we will be in trouble." She could just imagine the headlines in their city, "Local man arrested dressed as a woman."

But Amy said, "No, I serious. You look good enough and handle yourself well enough, no one will notice. All you have to do is watch your voice. Just speak softly. Oh, and take off your hose. In a beach town like this, no one wears hose just to do a little shopping."

Amy drove to a mall and they began a morning long expedition of looking at and trying on clothes. Carol bought two bras, some panties, a slip and two half slips as well as several pairs of pantyhose. As they turned away from the cashier Carol said, "No more wearing your stuff." She grinned at Amy and Amy smiled back. Then Carol saw a chiffon dress in coral pink with a ruffle neck. It was "A-line" style with empire waist. To her it just shouted, "feminine". "Oh, I've got to try this on," she said. They went to the dressing room and she changed into the dress.

"You look great in it," said Amy. They bought the dress. In all their shopping, no one gave any indication that they though Carol was not a woman. At noon they had a salad at a restaurant and discussed the morning's finds. Before they left, Carol said, "My legs ache, my feet hurt, and my shoulders are tired. I think I've had enough for today." Amy just smiled and they headed back to the car.

As she drove back to the apartment Amy teased, "Don't you want to be a woman full time? That way you could wear heels and have a bra pulling on your shoulders all day."

Carol laughed and said, "Well, I have certainly gained a new appreciation of what it means to be a woman. I enjoy dressing up but I don't think I want to do it on a full time basis."

When they arrived at the condo, they carried their purchases inside. Carol took off her skirt and blouse and hung them in the closet. She removed her wig and placed it on the wig stand. Next she took off the girdle and bra and changed her panties for Jay's jockey shorts and the rings on her left hand for Jay's plain gold band. Under Amy's tutelage Jay cleansed his face. Then he put on a tee shirt and shorts and slipped his feet into a pair of sandals.

Amy said, "I think we need to talk."

Again they sat facing each other and Jay wondered what was about to happen. Surely, Amy was not about to take away the acceptance she had given him.

Amy asked, "Well, what do we do now? How much do you want to continue to dress? Will this be an every day thing?

Jay thought a while before he answered. Finally he responded, "No, it has never been an every day thing. And as much as I enjoy it, I don't think it is something I want to do every day."

"Well, would you be comfortable defining some limits? Something so that I can know what to expect."

"Honey, I don't want to do anything you are unhappy with. What sort of limits are you thinking about."

"Let's say that you limit it to weekends. And you will need to buy your own make-up in the proper shades and do it yourself. I can't do that for you every time. Besides, you will enjoy doing that. Now, what about going out?"

"I was scared to death this morning. But by lunchtime I was beginning to get used to being out, and even enjoying it. But I haven't really thought about making a habit of going out."

Then Amy surprised Jay. "I know I said just on weekends. But we are here for the week and last night and this morning were so much fun, I think you could dress up all this week, if you like."

"I would like that, but I don't think I could take those heels all day," Jay grinned.

"Then in the morning we will go shopping and get you some flats. Let's go swimming now and maybe play some tennis later. Then after dinner you can dress up again and work on your make-up, OK?"

They were finishing up the dinner dishes when Amy said, "You go ahead and start getting dressed. I need to run an errand." Jay couldn't imagine what she needed to do but since she didn't offer to tell, he didn't ask.

Carol was struggling with the zipper on the back of her dress when Amy returned. She giggled and then finished zipping the dress. "Thanks, dear. Shall I start my makeup?"

"No, on second thought, I need you to undress." Carol looked puzzled but obediently turned her back so that Amy could unfasten the zipper. Then she slipped out the dress. Amy nodded and signaled for her to continue so she removed her slip and then the bra and breast forms. At that point Amy signaled for her to stop.

"Lie on the bed and close your eyes. I have a surprise for you." Carol obeyed, wondering what was about to happen to her.

First she felt something cool being rubbed on her chest and she smelled alcohol. Then something else was rubbed on that had the smell of ether. Finally, she felt something heavy being placed on her chest. "Breast forms" she thought. She started to open her eyes but Amy said, "Not yet. I'm not ready yet." And once more Carol felt Amy's fingers rubbing on her chest. When, at last, Amy said, "Stand up" Carol stood and felt a new weight pulling at her chest. Then she opened her eyes and looked down to see that she had breasts. She couldn't even see any seam where what she knew had to be the forms ended and her chest continued. Her face beamed and she said, "Wow! I've got boobs that look real." Amy helped her fasten a new bra. It was a dimi-bra that really showed off her new cleavage. Carol turned and hugged Amy tightly, feeling breast against breast. It was an exciting feeling.

Carol went to the dressing table and sat to begin her make-up. Instead, Amy pulled up a chair and began to work on her fingernails. After some preparation she began to glue on long shiny red nails. "Don't worry. We can take these off at the end of the week", she said. Then she painted Carol's toenails to match her fingers. After her fingers dried, Amy showed her how to pick up small things like coins with the balls of her fingers instead of her fingernails as Jay would have done.

Under Amy's careful tutelage Carol applied her own make-up, smoothing it evenly with the balls of two fingers. She almost poked her eye a couple of times while putting on the eye shadow. All that took a very different touch than she was used to because of the longer nails. When she finished the make-up she settled the wig on her head. Then Amy brought out one more surprise. She handed Carol a new beige colored blouse. It had short sleeves and a deep scoop neckline. When Carol put it on she saw that it plainly showed the tops of her breasts even without her bending over. Carol then put on a half slip and one of the new skirts she had bought that morning.

They spent the rest of the evening working on what Amy had called "some rough spots", things like what to do with her hands when she wasn't using them, how to look at her nails (with fingers out straight and palms down instead of palms up and fingers curled), walking, stooping and bending, and eating without smearing her lipstick. All little things, but things that women do differently than men.

The next morning Carol and Amy went shopping again, first for some low heeled shoes that wouldn't tire Carol so much. The Amy suggested that they buy a bathing suit for Carol. She said, "You probably don't want to go in the water with your wig on, but you will want to lie on the beach." After some shopping they found a nice blue one piece suit that showed off Carol's cleavage nicely and had a kind of skirt that would hide any inappropriate bulge.

Amy then steered Carol into a store that sold an expensive line of makeup and offered makeovers. She said to the saleslady, "My friend Carol here needs a makeover to help her choose the best colors for her." Carol started to protest but decided better and sat in the place indicated before the lights and mirrors. The saleslady introduced herself as Evelyn. Then she worked with the lights for a few minutes changing their color to simulate daylight and evening. Next she produced an array of bottles and tubes. She explained that she would do the evening makeup first, remove it and then do the daytime makeup so that Carol could leave the store wearing it.

As Evelyn began to cleans Carol's face in preparation for applying the makeup she noticed that Carol was wearing a wig. She said, "It would be easier to work and less risk of getting makeup on that fine hair piece if you took it off." She reached under the counter and produced a wig stand.

Carol paled and Amy spoke up, "We would rather not do that. You see, Carol is a man and if we remove the wig then everyone who passes by will notice his hair cut."

Evelyn smiled and said, "Well, she sure had me fooled. But here's what we can do. Put the wig on the block and I'll put it under the counter so that no one will see it. Then we will cover Carol's head with a turban so that her haircut won't show. OK?"

Amy and Carol agreed and the makeover continued. Evelyn explained each step as she worked. And because she was a good saleswoman, Evelyn always referred to Carol and "she" and "her" and never with the masculine pronouns. When the evening makeup was complete Evelyn pulled the wig from under the counter, removed the turban and quickly placed the wig on Carol's head. After she had adjusted it, she turned Carol to the mirror to see the results. Carol caught her breath. She never imagined that makeup could make such a difference in the way she appeared.

Evelyn removed the wig and placed the turban on Carol's head. Then she cleansed and moisturized her face before starting on the daytime makeup, explaining as she worked. When she finished she brought out the wig, placed it on Carol's head and pinned it in place. When Carol looked in the mirror it wasn't the surprise that the evening makeup had been but she liked the look very much.

As Amy and Carol left the store carrying a bag loaded with makeup Evelyn thought to herself, "Well, you see all kinds in this business. But that was a first."

That evening Carol tried out the new evening makeup. As they were waiting to be shown to a table in a restaurant Carol turned to Amy and whispered in horror, "Do you see the way that fellow is looking at me? I think he knows I am a man."

Amy smiled and replied, "No, dear. He is just checking you out. He likes the way you look. If he hasn't seen your wedding rings yet, he may try to hit on you."

When Carol remembered the rings she raised her left hand and brushed an imaginary hair away from her face, making sure that the rings would be visible to the man as she did.

As they were walking back to the car after dinner Amy said, "Look, there is one of those 'Glamour Foto' places. We ought to get some glamour photos of you." The shop was still open so she pulled on Carol's arm and led her into the studio. They discussed the prices and Amy ask if they furnished costumes and or wigs. "We're here on vacation and didn't bring any fancy clothes for this sort of thing." The lady who spoke with them assured her that the studio furnished both clothes and wigs if the customer desired.

Amy was about to make an appointment for Carol when she spoke up and said, "Make two appointments. You should have the photos also." After some discussion about the cost and whether they could afford two sittings, Amy agreed and the appointments were set for the next morning.

The next morning Amy and Carol dressed in clothes that would be easy to remove to change into the costumes furnished by the studio. Both carefully did their makeup. "I'll bet they will want to re-do the makeup" said Amy.

"You're probably right. And that means that we will go through that same routine of taking off the wig as we did yesterday."

"Yes, but this time we will be inside a studio away from public view."

At the studio they were greeted by Misti who steered them into adjoining cubicles and said, "The makeup artist will be with you shortly."

In a couple of minutes a slightly built man appeared and introduced himself as Rick. He asked, "You two are together? Who what's to go first?" Amy pointed to Carol.

Rick stepped into the cubicle with Carol and studied her face for a few seconds. Then he adjusted the lighting with a knob on the wall and looked again. Finally he said, "Your makeup is well done. We'll do the first couple of frames with it as it is. Then we will come back and change it to something more dramatic. Martha left a note saying that you would want to use our costumes. Let's see. You must be about a size 10. Come over here and look through these. Pick out one to start."

Carol began to look through the dresses while Rick returned to start work on Amy. After looking at several she chose sweater and scarf set that she thought looked good for daytime wear. When Rick returned he looked at her choice and said, "Going pretty casual for this first shot then." He indicated a dressing room where Carol removed her blouse and put on the sweater. She was tying the scarf when Rick returned. He looked at her an instant and said, "That sweater would be fine for wearing on the street but we want something tighter here. Let's see if we can find something similar in a smaller size." They returned to the clothes racks and in a moment Rick held up a sweater that was the same color. "This will be 'too tight' but for the pictures it will be just what we want." Carol returned to the dressing room and changed sweaters.

Beverly was the photographer. She adjusted the scarf and put Carol in several different poses, all that emphasized her breasts. Then she said, "I think you would make a great cheerleader. Go tell Rick you need a cheerleader outfit and a ponytail."

Carol returned to Rick with the message and added, "But there is one problem. I am wearing a wig and I don't think it will do to make a ponytail."

"Yes, I notice the wig when I was checking your makeup. Take it off and let's see what we have to work with underneath."

Carol sighed and as she took off the wig said, "I'm a man."

"Good for you deary. Don't worry. I like to dress up sometimes too. I see you are wearing rings and you came in with Amy. Are you two married?"

"Yes, we are."

"And she's OK with your dressing?"

"Yes, we've only dealt with it this week but she seems to really accept it. She has helped me a lot with clothes and makeup."

"That's cool!"

Rick looked at Carol's head with its masculine haircut. "This will be easy," he said. "We won't have as much hair to deal with as we often do with GG's." Then he went to another room and returned with a wig different that any Carol had seen before. "This is a theatrical hair piece. You probably couldn't wear it in public without being noticed but it will do fine for a picture." The wig had what appeared to be about quarter of an inch of skin out from the hair line.

Rick then showed Carol several cheerleader outfits and let her choose one. When she was dressed he began to prepare her for the ponytail wig. First he put a wig cap on her head. He placed the wig on her head and glued the "skin" to her own skin. Finally, he used makeup to hide the seam where the wig ended. Carol looked in the mirror and was amazed. Her now very blonde hair was pulled back snuggly into a ponytail that sat high on the back of her head. Rick picked up a scrunchy that matched the outfit she was wearing and put it on the ponytail.

"Now, go give us the old school yell," he said.

Carol returned to Beverly and did several poses like a cheerleader.

When they finished Beverly sent Carol back to choose a dress for evening. She chose a black dress with a very low cut "v" neck line formed by material that came from the shoulders and crossed at her breasts. It showed a good bit of cleavage. When she was dressed she returned to Rick. He removed the ponytail wig and cleansed her face before applying evening makeup. Then he produced a wig that was closer to the color of her own hair but the style was an upsweep from the sides and back with bangs in the front. "This will show only a little hairline," he said. He glued down the tabs of 'skin' at what would have been sideburns and covered them with makeup. Carol looked in the mirror and knew she was ready for a truly glamorous photo.

The rest of the week the two girls shopped and dined out. They relaxed on the beach and just enjoyed each other's company. The days were uneventful.

Sunday morning Carol and Amy attended the early service at a local church and then returned to the condo. They spent time cleaning the apartment and doing the final laundry of sheets, towels and the like. Then they packed their suitcases. When all the cases except one were packed and closed, Carol sat at the dressing table and removed her wig. She cleansed her face to remove any trace of makeup. Amy helped her remove the fingernails and clean her toenails. Then Carol undressed and placed her clothes in the suitcase.

Jay took a bath and dressed in a tee shirt and Bermudas for the trip home. Amy check him over one last time to be sure that they had not missed any signs of his week en femme. When she finished they loaded the car and locked the apartment. As they headed home Jay reached over and took Amy's hand and said, "You are some fantastic lady. I love you."

Amy leaned across and kissed Jay on the cheek and replied with a grin, "You are some lady yourself and I love both of you."

The end.




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