An older story of mine. My attempt at romance. A young software engineer, meets up with an old friend from high school she’s a computer tech and at last the nerd finds a girl who he can talk to.
JAN COMES OUT TO PLAY
By Patricia Marie Allen
Jon finally graduated college. He had started at age 17 and by going non-stop, that is: all four terms carrying no less than 16 credit hours, he had achieved his masters in software engineering. He had done quite well and was the youngest master degree candidate in the school's history. Graduating with High Honors made it easy to land the best job. He had software companies recruiting him. At last he could move out of his mother’s house and have the freedom at home that he had while living off campus at school.
His scholarship had taken care of tuition and books. He had a part time job as a computer technician that easily took care of his studio apartment, which was some distance from school. Computer nerds were loners anyway, but he even shied away from other computer nerds as well, so he could take advantage of the liberal college town attitudes and wear what ever outrageous outfit he wanted. Of course he always dressed straight at school. He didn’t want to freak out his professors or develop a really weird reputation amongst the other students. He confined his unusual dressing to only around his apartment or an occasional evening walk or drive.
The holidays were a pain. Coming home he would have to curtail his activities. On very rare occasions, Mom would leave him home long enough to borrow some things and get his outlet. That’s where it all began. He had discovered her lingerie at about eight or nine and by the time he was in high school he was getting fully dressed in her clothes almost daily. Dad had died when he was young and Mom had worked ever since. As a latch key kid, he had the run of the house for about three hours a day. He discovered that he really liked homework when he was wearing Mom’s clothes. If he came home quickly and changed into her clothes, he could do a whole week's worth of homework in two days. The rest of the week was devoted to extra credit. When his uncle died and they inherited his personal computer, things really took off for Jon. He had been a good student in middle school but getting the computer as a freshman, he began to excel almost immediately. He was a natural with the computer. First he learned to operate the software that was there. He used the typing tutor to learn touch typing and then mastered the word processor. After that, homework was a breeze.
As a sophomore, he took his first computer science class and became the teachers pet. The teacher recognized his natural talent and did everything he could to promote his learning. All of that combined made him a straight A student. He had to choose between three full scholarships for college. He was also able to take advantage of a grant. Which was handy, the money could be used to up grade his computer equipment.
After graduation, he had moved back home but with his job at Cybertek, he didn’t get much time home alone and he had to keep his special clothes in boxes in the garage. So he began looking an apartment on the weekends.
This one he was moving into was perfect. It was across town from Mom’s house and was near work. Best of all, when he was looking at the apartment, they were in the process of replacing the hot water heater. It was behind an access panel in the bedroom closet. It only took up about a third of the space allotted to it. It would be a perfect hidden closet with just a little work.
He couldn’t remember the number of times he had to stuff his clothes into the computer boxes when Mom came to visit at school. She would always take it on herself to thoroughly clean his apartment. The slightest thing would have tipped her off. Once, she found some make-up in a drawer, in his bathroom. He was glad he had been there at the time and could claim it was something his study partner had left. He said that she had gotten ready for a date there after they got through studying and left it by accident and would pick it up next week.
When he moved into his new apartment, he quickly modified the access to the hot water heater. He moved the panel as far into the closet as he could and hinged it from behind so that it swung flat back to the rear wall. When closed, it was secured by push latches. Open, it added two feet to the length of the closet. With the addition of a shelf over the water heater, it made a perfect hidden place for his "special" clothes. Mom had already warned him that she would be coming over every couple of weeks to see that his apartment was cleaned right. Nobody knew about his "hobby" and he wanted to keep it that way.
Living alone had its advantages. He could spend as much time as he wanted in his "special" clothes. But he didn’t have to make it an every possible minute thing. He was still pretty much a loner but he did try to make some time for a social life. Something that he had not allowed himself in school. He made a few friends at work and at the lunch counter where he often had lunch. One Saturday afternoon that spring, while waiting in line for a movie, he ran into a girl from high school. She remembered him from one of his computer classes. She had been very shy and had talked with him only a few times.
She was going to a movie alone as well and just happened to be in line behind him. She recognized him first. She waited until they were in the lobby to speak. He was standing at the refreshment counter when all of a sudden, she whirled around and said. "You’re Jon Barton aren’t you?"
Surprised, (women didn’t just start talking to him as a rule) he blinked and said, "Ah, yes. Yes, I am. Do I know you?"
"You probably don’t remember me; we were in high school together. I wore glasses then and I’ve lost a lot of weight. I’m Alice Chaucker."
She was still a big for a woman. She was five eight and about a hundred and fifty-five or sixty pounds. Not overly fat, but not small either. She was big boned, as his mother used to say.
"Oh yeah, I think I remember you. You were in a couple of my computer classes."
It turned out they were going to see the same movie. So they set together. They went for espresso after the movie, just to catch up on old times. Alice was not as fortunate as Jon. She had to go to Junior College first and then to the State University. She landed a good job at Western Micro as a computer tech with just a bachelor's in computer science. She had worked there ever since.
"I’m surprised that we haven’t run into each other through our work. We buy equipment from Western Micro all the time. I was just over there a couple of weeks ago," Jon told her.
"Well I don’t get to deal with the customers much. I’m usually in the back configuring special systems or checking out the problems in returns. But I did see you last time you were in. I’m pretty sure I saw you about a month before that. I can’t be absolutely sure because you just walked by a door. That’s why I talked to you at the movie. I wanted to make sure that it was you. I hadn’t seen you since high school."
They spent so much time at Starbucks that they decided to go get dinner. After dinner it was dark and Alice had ridden her bike to the movie so Jon loaded it in his trunk and gave her a ride home. He helped her get it up into her apartment.
"Well, I guess I’ll see you sometime at work. Next time you have business there look me up," she told him.
"I will. I really enjoy this time together. It was almost like a date, and I don't do that much."
"Yeah, it was like a date except you weren’t pawing me in the movie, like most of the guys who ask me out. They seem to think, because of my size, I’ll be so grateful for their company that I'll put up with them getting fresh."
Jon blushed at that. "I don’t think your size is that out of proportion. You make a very good looking woman."
"You're sweet," she said and leaned forward and gave him a quick kiss on the cheek. "But, I’m big and I know it. It doesn’t bother me anymore.” Then she changed subjects quickly. "Look, you’ve got my number. Next time you feel like taking in a movie give me a call. I might just like to go with you. I had a really good time today."
They made their good-byes and Jon went home. He hadn’t intended to be gone so long. He had laid out a dress before for he left and had intended to put it on after the movie and have dinner while wearing it. By now it was nearly time for bed. He was typically an early riser.
Still he was glad to have spent some time with Alice. Not many women were comfortable with him. He had been out with some groups from work and the women were friendly enough, but they rarely spent the whole evening talking to him. In fact only two of them had consented to dates with him. Usually that consisted to a quick dinner, a late movie and straight home. Neither of them had invited him into their apartments. Alice seemed to be comfortable to have him in. Not only that but she had been really interested in what was going on in his life.
A couple of weeks later Jon had occasion to go to Western Micro. He remembered that Alice worked there and looked her up. She gave him the grand tour of the tech department. As it turns out she was the head technician with only the department head above her. She was pretty knowledgeable about computer hardware. She showed him some experimental stuff that Western Micro was working on. She could only tell him that it involved the use of some proprietary chips. It was supposed to enhance the speed and memory management of the system.
That Saturday morning, Alice called him.
"Hi, Jon. You were on my mind. After you came by work decided I’d take in a movie today. When I looked at the paper to see what was playing I thought of you and wondered if you’d like to join me. I’ll let you pick out the movie. We’ll go Dutch treat again. Oh wow, I sounded just like my mother. ‘Dutch treat’ that’s like a 1950’s expression.” She seemed a little nervous.
"Oh well, I was just going to hang out here today. I thought I might doodle around on my computer some. I kind of have an idea for some TSR’s that I was going to try out. But you know, a movie sounds good. What’s playing?"
They decided on a Si-Fi flick that was popular at both their work places. Jon drove over to her place and picked her up. After the movie she invited him to have dinner with her.
"It won’t be much. I was just going to do a Salisbury stake to use up some old hamburger. I could do some microwave baked potatoes and a canned vegetable."
"That sounds better than what I was going to have at home."
After dinner, Jon thanked her and headed home about 9:00. That was amazing. A woman invited him to her apartment and fed him dinner. What was most amazing was she didn’t look bored when he started telling her about his latest project a work. She seemed genuinely interested. All in all, it was a pleasant evening.
Jon didn’t see her too much, but about once a month they would get together for a movie and dinner after. Jon also dated the waitress at the lunch counter a couple of times but found her too shallow and she always wanted to go a bar where they had dancing. Jon wasn’t much of a dancer. No sense of rhythm. He didn’t smoke and the atmosphere was disgusting. The women at work warmed up a little and he dated them some but none of them had any interest in him personally. They liked to be taken places and have him spend money on them but the relationships just never seemed to flow smoothly.
With Alice, they joked and laughed together. They could tease each other in a friendly manner. By Labor Day, he had just about forsaken dating anyone but Alice. They didn’t have any formal agreement, but he was sure that she wasn’t dating anyone but him. Alice’s family always threw a big barbecue for the holiday and she invited him to come with her. Her parents were nice. It turned out that her mother had divorced and remarried. Jon gathered it had been something to do with Alice’s real father not getting along with Alice’s grandmother on her mother’s side. He just picked that up through the day without meaning to. There was some reference to an "Aunt Jo" that Jon didn’t quite understand.
After that, they began to see each other more often, but it didn’t amount to an every weekend thing. They began sharing extended goodnight kisses. The only other girl who had thought that was a good idea was the waitress. She was interested in more than that as well. Jon had the idea that most of the guys who dated her received more than that as well. He wasn’t too sure that he wouldn’t come away without some dread disease if he took her up on the implied offer. That was a contributing factor in him breaking it off with her.
Jon and Alice were at her apartment on Saturday afternoon in October. They had rented a couple of movies and were watching them on her home theater.
"One of the drivers at work is throwing a Halloween party. He invited me and said I could bring a date. Do you want to come with me?"
"I’m not sure. I’ve never been one for thinking up costumes. What would you go as?"
"I’ve considered lots of things. I really don’t want to spend a lot of money on a fancy costume. I’ve kind of settled in on a Gypsy Princess."
"I wouldn’t know what to wear. I’d have to find a costume shop and see what I could rent."
"Your costume would end up too fancy if you did that. I’m sure we could come up with something original if we put out heads together."
"Well then let’s hear some ideas."
"How about you going as a Gypsy Man?"
"That would take black boots, some bloused pants and a fancy shirt. Not to mention a new hairdo, dye job and all. I never heard of a fair skinned blond headed gypsy."
"No. I guess not. A pirate maybe?"
I’d need a big hat, and eye patch. A scarf for a belt. But we’re back to the bloused pants. I don’t have anything but jeans and dress slacks."
"I guess you really don’t want to go."
"No I do want to go. I’ll tell you what. If you can figure out how to make your next idea work, I'll go for it."
After a little thought, Alice got an impish grin on her face. "Well, you’re about my size. I could loan you some clothes and you could go as a girl."
He looked at her and couldn’t tell if she was just testing him or if she was serious. "O... K..,” he said slowly. His heart rate picked up just a little. He had always wanted to try that, but had lacked the courage because he was afraid that someone might guess the truth about him. After some thought, he remembered how hard it was to get shoes in his size. He had to send for them from the "Old Pueblo" catalogue. Even then, they didn’t have much of a selection. He threw out a road block that would almost certainly put the brakes on this idea without making him look like he wasn’t willing to go along. "I wear a size 9 1/2 double E shoe. If you can come up with a woman shoe to fit that, we’ll do it."
Alice put her foot next to his. "I wear an 11 wide. It looks like they are the same size. Let’s see."
She went into her bedroom and brought out a pair of pumps with a two inch heel. Kneeling in front of him she slipped off his loafer and tried her shoe on his foot. No, go. She wouldn’t be daunted and took off his sock. The shoe would go on but the heel wouldn’t quite go down.
"Wait right there.” She went back to the bedroom and brought out a pair knee high nylons. Slipping one on his foot she tried the shoe again. This time with a little effort, she managed to get the shoe on. He winced a little. He knew that a 12 wide would be needed.
"It’s a little tight in the toe,” he said. "It was OK until you forced my heel in, but I’ll never be able to walk in them. I’d end up a cripple."
"I’ve got an idea.” She took the heels back into the bedroom and returned with a pair of sling backs that had a 1 1/2 inch heel. She loosened the heel strap and slipped one of them on and then refastened the strap two notches larger. "How’s that?" she asked. Jon lifted his foot and looked at the shoe. He knew by the way it felt that it would be just fine. He knew that she knew it too. He stood up and put some weight on it.
"I don’t know if I could walk on high heels, but it seems to fit all right."
"Try the other one on and see if you can walk.” He sat down and took off his shoe and sock while she adjusted the other strap. He put the other shoe and stood. His heart began to race. He made his left heel wobble on purpose as he took his first step.
"Whoa! This’ll take some practice. How do you walk in these things?"
"I’ll send them home with you and you can wear them around the house for a couple of weeks."
"I guess I’m committed to this ‘girl thing,' I just hope I can do some make-up that doesn’t make me look like a clown."
"Don’t worry; I’ll do your make-up. You’ll look like a real girl when I’m through."
He wore the sling backs the rest of the evening and took them home. It was decided that Alice would meet him at his place after work on Halloween. She called him the following Saturday.
"Hi Jon. I just wanted to check and make sure that you’re practicing in those shoes I lent you."
Jon had his special clothes on and was wearing her shoes at the time. "I’m wearing them as we speak," he told her. "As a matter of fact, I wore them all day last Sunday, and every evening since. I'm getting pretty good at it.” He didn’t tell her what else he had been wearing. He had gone through most of his wardrobe. Two feet of closet space didn’t give him much room for dresses. "I have to tell you though, that I'm still not sure about dressing up like a woman and going out in public. I don’t want anyone to think I’m queer, or anything."
"I won’t think your queer. And I’m the only one who’ll see you whose opinion will count. Besides, it’s Halloween; everyone will expect to see people in strange outfits."
"I hope you’re right."
"Well I have to run. I’m meeting Mom at the mall. She always want’s my advice when she goes shopping. Be sure to keep practicing in those shoes. I’ll see you a 5:30 on Friday."
"I’ll be expecting you."
All that next week, Jon stayed home and "practiced" just as if he needed to. After work on Halloween, Jon came home and put on Alice’s knee highs and shoes and waited for her. She showed up at 5:30 just like she promised. She looked every inch a Gypsy Princess. Her long dark hair and dark complexion combined with her outfit perfectly. She had on a bright silk scarf tied like a cap so that her bangs and hair showed from underneath. Her gold jewelry set it off perfectly. She had a big pair of hoop earrings, two gold chain necklaces and three rings on each hand. Her costume was made up of a white peasant blouse and brightly striped skirt, which was hiked up on one side to show a white petticoat another silk scarf tied around her waist. Her shoes were sandals.
She carried and overnight case and a garment bag. Jon knew it was to be his costume. All at once he was concerned. He had agreed to this idea without even considering what kind of dress she would pick for him. The garment bag looked a little full. Maybe she had brought several to see just which one would be right.
"Well look at you. You’re walking like you grew up in those kind of shoes."
If only she knew. "I’ve always been sort of agile. It’s like ice skating. Training the ankle what to do just takes practice."
She marched straight into his bedroom. She unzipped the garment bag and opened the overnight case. The case contained a bra and a new pair of pantyhose. There was also an over sized pair of falsies. "Take off your shirt she told him.” He obeyed. She slipped the bra straps over his arms and stepped around and fastened it behind him. She then put the falsies into the cups. Reaching into the garment bag, she handed him a slip. "Here, put this on.” He did. "Do you think you can figure out how to get these on?" she said handing him the pantyhose."
He shrugged his shoulder. "I think so,” he said.
"Well put them on and meet me in the bathroom.” She picked up the overnight case and left.
He took off his pants and changed his underwear. He put on a pair of men’s bikini briefs they differed from the ones he took off only in that they were cotton and not nylon and the waist band was a little wider. He took his time putting on the pantyhose. It wouldn’t do to be too good at it. He decided to put the shoes back on. It turned out he needn’t have taken so much time with the pantyhose. It took plenty of time to get up the courage to go into the bathroom wearing her slip and nylons.
"I was just about to come in and help you," she told him. She had all kinds of cosmetics laid out on the bathroom counter. "Did you shave this morning?"
"No, I waited until I got home. Being a blonde, I can get away with shaving every other day. That is, so long as I’m not planning to rub cheeks with anyone."
"Good! Sit here,” she said indicating the commode. He sat down and she began to work magic with his face. She applied a foundation and a mat powder to set it. Then she put on mascara and eye liner, followed by eye shadow. Next came blush and lipstick. With the make-up complete, she started ratting his hair and using hair spray. When she was through she stood him up so he could see the mirror. He was amazed. It sort of turned him on to see that woman wearing only her slip.
"Now come back in the bedroom.” She took out a dress from the garment bag and a nylon petticoat. The dress was full skirted and had long loose sleeves. She had him put on the petticoats' first and then the dress over his head. She zipped the dress up the back and adjusted the bra and slip straps so that they didn’t show under the scoop neck line. She took him to the kitchen where she had him sit at the table. Taking each hand in turn, she put fingernail polish on each finger. While they waited for that to dry, she produced a tiara. She placed it carefully on his head and sprayed him with perfume.
"You're a princess and you have to smell the part,” she said.
It had just gotten dark when she brought him a black rain coat that must have been in the garment bag as well. With a little trepidation Jon followed her out to her car. It had been raining and there weren’t any people in sight. For that, Jon was thankful. He got into the passenger seat and Alice headed out. Jon kept his eyes straight ahead. He didn’t want to make eye contact with anyone while in traffic. They reached the party in about half an hour. There were many cars already lining the streets. They would have to walk almost a block the house.
Jon looked both ways before he opened the door and then only after Alice had walked around the car. She had parked right under a street lamp. Standing up, Jon found his knees a little weak. The neighborhood was quite and he was acutely aware of the sound of his petticoats rustling and the clack of his heels as he walked. Without warning, some kids dressed as ghosts and carrying heavily laden sacks came running from behind. Jon froze. They ran right past without pausing. Well apparently he looked OK from behind. The kids darted up to a house on the right. Just as they were coming to that house they reappeared with empty sacks and came laughing and giggling down the walk and turned to walk right past Jon and Alice again. Once again, they didn’t give him a second look.
Finally, they reach the party house. It was all decorated outside. Alice rang the bell and was greeted by a vampire. A rather convincing vampire, blood stained fangs and all.
"Mike! Your costume is so good!" Alice told him.
"Ah yes. Count Durrracula often enterrrtains the Prrrincess of the Gypsies. Come my child and brrring yourrr frrriend with you,” he said in thick pseudo accent clumsily rolling his R’s. Mike took Jon’s hand, kissing it, and said, "Who is this charming lady? Of royal blood... no doubt,” he said eyeing Jon’s neck.
Alice laughed. "This is my friend Jon. I know him from high school."
"Him! Oh my God! I’m glad you told me," Mike said, dropping his accent. "Jon, nice to meet you. I thought you were a woman. You had better make sure to let everyone know the dress is just a costume. If you don’t, you’ll have guys hitting on you. It’s really convincing. I don’t think that’s because I’ve had a few drinks either. Well come on in you two. Mingle. Enjoy.
They went in and helped themselves to mixed drinks from the open bar. Alice seemed to know several people there. Alice introduced Jon to a rather shapely harem girl.
"Michelle, this is my friend Jon. Jon, this is Michelle. She used to work at Western Micro."
"Hello Jon? Nice to meet you. You're a little tall, but you could pass on the street. I know a couple of women who are taller than you."
Jon nodded his head and smiled. Michelle turned to Alice and said. "You know what we should do? We should make-up some girls name for Jon and see if he can pass."
"Yeah. I know, we'll call him ‘Jan.’ Just to keep the guys from hitting on him we’ll spread the rumor he’s a lesbian."
"OK!"
Without his consent, Jon became Jan that evening. Soon every one thought Jon really was a woman and very shy because she wasn’t used to being at a party with straight people. Jon played along, talking softly when necessary. Being a loner at heart, he didn’t mingle much anyway. Alice on the other hand, was very gregarious. She was all over the party, drink in hand. By midnight, she was roaring drunk and the loudest laugh in the place. At one point, someone put some violin music on the stereo and she danced an imitation of a Gypsy dance, pulling her skirt well over her knees and flinging it around.
The party began breaking up about 1:00 and Jon helped her on with her coat and took her to her car. He took her keys and drove. She was still giggling as he helped her up to her apartment. Inside he took her straight to the bedroom and tried to get her to lie down. She put her arms around him.
"You know, you’re good looking. Both as a guy and as a girl.” She kissed him. It was a very long kiss. Jon found himself kissing back. "I’ve never kissed a guy who was girl before. Or it that a girl who was a guy?" she said and kissed him again. "Either way, it’sss kinda neat."
"You need to go to bed," Jon told her.
"Naa, I wanna kiss you some more.” And she did. A very passionate kiss. As she was kissing him she reached around and turned out the light. "Kisses are better in the dark,” she told him during a pause and kissed him again. Before Jon knew it they were laying on the bed locked in passionate embrace.
In the morning Jon looked around. They were under the covers. He was still wearing the bra and slip. From the exposed shoulder, Alice was at least topless and maybe nude. It was obviously late. As Jon pulled the covers back to get up, Alice rolled over and squinted at him.
"Oh!" she said. "I got very drunk last night.” She concentrated on him for a moment. "I seem to remember attacking you last night. I see I was successful. You know, I don’t usually do that kind of thing. I hope you don’t think I’m loose now."
"Oh, no. You just got drunk. That’s all,” Jon said standing. He looked down at himself and shrugged. He turned and walked toward the bathroom. He looked a fright. Opening a drawer he found her cold cream and took off his smudged make-up. When he came out he was at a loss for what to do. He paused at the bedroom door Alice had put on a robe and was pulling her Gypsy skirt off. She looked up and nodded toward the bed.
"There’s a robe if you want it.” Jon stepped in and picked up the robe. It was a blue satin not quite as long as the slip. He put it on. "Hungry? She said.
"Ah, yeah. I guess so."
"Let’s see what we can find to eat around here.”
Alice led the way the kitchen. She made some fried eggs and toast. They sat at the kitchen table eating.
"You know," Jon said, "this presents a dilemma."
"What?"
"My intention was to drop you off last night, go home and bring your car and clothes back this morning. I don’t have any of my own clothes here. I’m going to have to wear your clothes to get home and I don’t relish the idea of going out in a dress in broad daylight."
"Well, it look’s like I’m stuck with you all day then doesn’t it? I’ll drive you home after dark."
After breakfast, Jon volunteered to do the dishes. Alice went in to the bathroom and then the bedroom. Jon was just finishing up when she came out. She had redone her make-up and put a skirt and blouse.
"You won’t want to wear that robe all day. I’ve laid out some things you’ll have to put on sooner or later. You might just as well put them on now."
Jon went into the bedroom and found some clean panties, pantyhose and a dress on the bed the sling back heels he had worn last night were neatly placed at the foot of the bed. He shook his head and put on her panties. The only time he had worn someone else’s panties they were his mothers. What’s more, she didn’t know he was wearing them. There was something exciting about wearing her panties. It was mostly that she knew. He pulled on the pantyhose and the dress. Slipping on the shoes, he went into the bathroom and brushed out his hair.
"You should have called me to do your hair,” she said as he came into the living room. "Here come on back here.” She led him back to the bathroom and set him on the commode again. After she ratted and spayed his hair she started in on make-up. "If you’re going to wear women’s clothes, you ought to look like a woman. Besides, you’ll want this later. This will just save time when we get ready to take you home," she told him. For no apparent reason, she sprayed him with perfume again.
They spent the afternoon watching old movies on cable. Alice fixed them some dinner about 7:00. And Jon volunteered to do the dishes again. When he was through, she gave him a rather amorous kiss.
"I like having you around. I should invite you to dinner every night. I’d never have to wash dishes again," she smiled.
"It’s the least I could do. After all, I am an uninvited guest."
"As far as I'm concerned, you can invite yourself any time you want. I’m sorry we waited so long to get to know each other. We should have done all this while we were still in high school."
"Including last night?" he asked, immediately regretting the words.
"I wouldn’t have been the only girl in school to have done that,” she said lightly, taking no offense.
"What time do you want to take me home?" he asked, changing subjects.
"Well, you know, you don’t have to go home tonight if you don’t want to. I mean... after last night... I... I just... kind of want a clear memory of my first lover since college.” She finally blurted out. She looked down. Jon stood stunned. Then she looked up and searched his eyes. "Unless, you don’t think I’m interesting enough for that kind of relationship."
"Oh! Well, ah, you are certainly interesting enough."
"In college, the guys would get me drunk and seduce me. The only one’s who paid attention were the ones that wanted sex. I got to where I just quit dating all together because I’d wake up with a hang over and my underwear on inside out.
"I just want to make sure that... I mean you seem to be really interested in me. You’re the first one that the idea came to me first. You never tried anything, but always seemed to be genuinely interested in me.” She began to cry softly, her face in her hands.
He went to her. Holding her gently, he kissed her on the forehead. "I am interested in you. I’m surprised that you would be interested in me. I’m the geek, the computer nerd that all normal people avoid. I kind of thought that our relationship was based on a common interest in computers. I never thought you and I shared any common romantic feelings."
"I’ve made a complete fool of myself,” she said. "You’ll probably never want to see me again."
"Not so! I want to see you a lot more. I don’t think you’re a fool. You just were so mistreated by men in college, that you didn’t know how to tell me how you felt. And I'm so inexperienced with women, that I didn’t know how to tell you how I felt."
"Then, you’re not disappointed in me that I... well you know last night and that brazen invitation just now?"
"No, I’m flattered. I mean, I didn’t think any woman I could care about would really want me.
"Are you going to spend the night then?"
"If you’ll have me."
She kissed him passionately. "I must look a fright,” she said getting up to go to the bathroom. She came back shortly with fresh make-up. They spent the rest of the evening in front of the television. Jon was very attentive, getting her coffee adjusting the room temperature and giving her free rein to choose the TV program.
About 10:00 she got up and went to take a shower. When she came back, she was wearing a knee length nightgown. It was soft lilac with a vee neck and side slits that just revealed matching sheer panties. The nightgown itself was translucent and gave only a seductive hint of the body underneath.
"I’ve laid out a nightgown for you. You can change anytime you’d like," she told him.
He went in to the bedroom. The nightgown was a pastel blue and sleeveless. It had an empire waist and full skirt. The bust line was formed by two over lapping panels. There were matching panties laid next to it. He stripped, almost reluctantly taking off the bra, and put on the panties. He then pulled the nightgown over his head. He looked at himself in her mirror. The nightgown looked silly. His hair was still very feminine and he still had make-up on, but the bust line on the nightgown hung flat like pendulous boobs. Only they were much too flat.
After a time, he took it off and put the bra on with the falsies before putting it back on. He hesitantly walked back to the living room. Alice smiled and looked up. "That looks good on you,” she said. "I’ve dished up some ice cream for you. I hope you like chocolate.” He got his ice cream and sat next to her on the couch. When they were done, she collected the dishes.
"It’s 11:00, I’m going to bed. You can come in anytime you like. Even now if it suits you,” she said smiling.
"I have to go to the bathroom. Then I’ll be in,” he said standing. When he was through in the bathroom, he found the rest of the apartment dark except for a light coming from the bedroom. He went in and found Alice on the left side of the bed, waiting for him. As he climbed in, she turned out the light.
She scooted over to snuggle with him. There was something very erotic about being in bed with a woman while he was wearing a nightgown and she was snuggling up like that. After a few passionate kisses, they were lost in ecstasy.
Jon woke lazily about 8:00 a.m. His bladder was full. Must have been all the coffee he drank last evening. When he came out of the bathroom. Alice was up and fixing breakfast. She was still wearing her nightgown but she had a robe on. Alice may not be the slimmest woman in the world, but she sure looked good to him, standing at the stove. Glancing in the bedroom he saw the bed was made up and the blue satin robe was laid across the end. He went in and put it on.
"How do you like your eggs?" Alice called from the kitchen.
"Basted," he replied leaving the bedroom.
As he came into the kitchen, Alice stopped and poured him a cup of coffee. Handing it to him she, she gave him a light kiss and shooed him toward the table. Sitting at the table, Jon reflected on the weekend. Up to now, it had been heavenly and showed every promise of remaining that way. He wasn’t quite sure just how it had all come about. He really wished that he knew. He’d like to arrange it again. Fat chance of that until next Halloween. Breakfast was on the table before he knew it.
"Would you mind if I took a shower?" Jon asked
"Not at all. In fact I might mind if you didn’t, considering all the physical activity you’ve had in the last two days. There are fresh towels in the linen closet."
While Jon was in the shower, he heard the bathroom door open. "I’ve brought you some clothes to put on," Alice called over the noise of the shower. "Feel free to use my dusting power if you want. And be sure to call me before you put the dress on and I’ll blow dry your hair," she continued.
On exiting the shower Jon saw that she had brought everything he needed. Clean panties, a clean bra, pantyhose, a slip and a dress. She even brought "his" sling back heels. Toweling himself off, Jon noticed she had moved the dusting powder to a prominent place on the counter. He had never use dusting powder before so he patted some almost every where. He put on the panties, the bra with falsies, pantyhose and the slip. He stuck his head out the door.
"I’m ready to dry my hair," he called.
Alice came in and had him sit on the commode again. She got out the blow dryer and began working on his hair. When she was through with his hair she did his make-up again. Looking in the mirror, Jon was impressed with her talent. He really looked feminine. He could almost pass as a woman. He put on the dress and they made themselves comfortable in the living room. Alice had produced a Sunday paper from somewhere. Jon read the Sunday funnies. Alice read the supplement magazine and then they switched. Alice suggested that they play some cards. Going to the kitchen table, Jon realized that Alice had opened the shade. He sat with his back to the window. No one could possibly tell from behind that he wasn’t a real woman.
"Let’s play Gin Rummy. Instead of money we’ll play for kisses. After lunch we can settle up," Alice said with a smirk on her face.
Jon laughed. "OK, but that sounds like a win, win situation to me."
They played until lunch time. Jon was the better player. Alice owed him fifty-five kisses. They had tuna sandwiches and vegetable beef soup for lunch. Jon did the dishes again while Alice waited in the living room. When Jon came in, Alice patted the couch cushion next to her. When he sat down, she began making good her bet. It didn’t take long for them to loose count.
Jon found this very erotic. Necking with a woman while dressed as a woman really turned him on. They must have gone on for hours or so it seamed. Afterward, Alice needed to put on new pantyhose. Hers didn’t survive the unusual removal technique. Then she had to fix both their faces. The two of them had managed to smudge almost every thing except the eye make-up. Jon was surprised that Alice had been the aggressor. She wasn’t shy about doing what felt good for him. Of course he reciprocated.
After they cuddled up on the couch to watch an old move on television. Alice cooked roast for dinner and Jon did the dishes again. She waited until about 9:00 to take him home. She gave him the coat he had worn on Halloween. He put it on and they went to her car. She didn’t go straight to his house. She stopped off at the store to "Pick up a few things.” She left him waiting in the car for over half an hour. The parking lot was very well lit and he felt very conspicuous. People were coming and going all around but nobody paid any attention to him.
When she finally got him home, she kissed him in the car. "I’ve got ice cream so I can’t come in and wait for you to change," she told him.
"How are you going to get your clothes back?"
"You can bring them back on Friday. That’ll give you a chance to wear them later in the week if you want."
"Right,” he said thinking ‘maybe I just will at that.’
"Why don’t you bring them right after work on Friday and I'll fix you dinner."
"OK, you’ve got a deal."
"See you Friday,” she said driving off.
Jon did wear them later in the week. Every night as a matter of fact. There was something about wearing her clothes that he really liked. It was much better than his mothers' clothes or any that he had gotten out of the mail order catalog. Monday before going to work he washed out her panties and hung them over the shower head. He repeated this ritual every morning except Friday. That way he could wear her panties every night.
On Friday he was concerned because he had worn her dress to cook and eat dinner every night. There was a chance that he had spilled or splashed something on it. He packed everything in the garment bag that Alice had left and dropped the dress at a dry cleaner's near work. The sign in the window promised two hour service. When he asked about it he found there was an extra charge. He was glad to pay it.
When he got to Alice's, he carried the garment bag to the door and rang the bell. She answered wearing an apron and carrying a large spoon.
"Hi. Come on in,” she said, stepping back. Jon maneuvered the bag through the door. "Did you have fun wearing the dress through the week?" she asked impishly.
"Oh yeah. Lot’s o’ fun," he replied drolly, through his nose. Carefully not actually denying it, but also giving the impression that what she said was a joke.
"I thought you might have worn it over here. After all you made such a good looking girl," she teased some more. She apparently was having fun with this.
"I didn’t have any make-up or hair spray."
"Well," she said, "next time we’ll just have to make sure you have make-up and hair spray." She went back to the kitchen to stir the sauce. "You know where to hang it up. Unless you want to wear it again.” She looked at him coyly in a sideways glance. He ignored the remark and took the dress to the bedroom. As he unzipped the garment bag, he heard her call down the hall. "You needn’t feel like I'm pressuring you to wear that dress. You can wear any dress you want.” He chuckled to himself a little. She certainly was having a good time with this. If only she knew how tempting the offer was. ‘If only it were serious.’ "Call me when you’re ready for me to do your make-up," she called again.
"It sounds as if you liked me wearing your dress all last weekend."
As he put the hanger on the closet rod, Alice appeared in the doorway. He turned to face her. She stepped up to him and asked. "Did I do anything to make you think I didn’t?"
"Well, no. I guess you didn’t,” he said.
"I was sure that by Sunday, you were really into it.” She put her arms around him and gave him a passionate kiss. "Now tell the truth, did you wear the dress through the week?” Lost in her embrace, he nodded yes. She stepped back and smiled, "Well then," she said turning back to the kitchen, "let me know when you’re ready for me to do your make-up."
Jon stood, watching her leave. He was unsure he wasn’t dreaming. He looked at the closet… then at the door she just exited. He looked again at the dresses in her closet. He noticed an outfit with a lightweight sweater top and a short jumper that would strike him about four inches above the knee. He had always wished he had something like that. She had a short bra-slip hanging near it. He held the bra-slip up to himself. Finally he took the outfit off the hangers and laid it on the bed. He opened her lingerie drawer and got out some white pantyhose. Stripping down, he put everything on. He fished the sling-backs out of the garment bag and put them on. He put away the rest of the things from the garment bag and stepped nervously out into the hall. Alice was busy at the stove. He took a deep breath. "I... I’m ready,” he said.
Alice came and ushered him into the bathroom. She ratted his hair and did his make-up. Stepping back she looked him up and down. "I could never get up enough nerve to wear that out fit in public. If you like it I guess we can consider it yours.” She smiled at him. "Come and sit at the table. Dinner’s almost ready."
She served spaghetti and meat balls. After Jon washed the dishes and they settled into an evening of watching television. Alice cuddled up next to him while they watched TV. Once, she got up to bring them coffee. When she came back, she leaned across him to put the coffee on the end table and paused long enough to kiss him gently. He turned his head and kissed her on the head.
About 10:00 Jon took his coffee cup to the kitchen. Returning, he said. "It’s getting late. I’d better change and get going. I... I..." (He was struggling for word when she interrupted. )
"Get going? Aren’t you going to stay the night?"
"Well, you know where that will lead."
"Sure. I was sort of counting on it."
"You really want me to stay the night?"
"Look on my bed."
Jon stepped into the hall and leaned around the corner. On her bed were the nightgowns they each had worn last weekend.
"I thought the blue one looked so good on you, I've set it aside for your exclusive use when you are here,” she said standing behind him.
Jon turned and saw the love in her eyes. He took her in his arms and kissed her. When he was about through, he realized that she was just getting going. After a lifetime, they broke their embrace.
"I guess you really want me to stay, huh?"
"I sure do. If you must change, change into the nightgown.” She stepped passed him to the bathroom and closed the door. Jon went into the bedroom and lost no time putting on the nightgown. This time he didn’t agonize over the bra. He left it on. He put on the robe that matched and went back to the couch. The toilet flushed and Alice took some time getting back when she appeared, she was wearing her nightgown. She opted not to wear a robe. He sure enjoyed looking at her in the nightgown. She came and snuggled up again.
At eleven Alice gave him a big hug and a kiss. "Want to go to bed?" she asked.
"OK," he replied.
"Come on in the bathroom. I’ll help you take off your make-up."
After she finished with their make-up removal, they went into the bedroom together. She took the left side and after taking off his robe he took the right. She turned off the light and immediately cuddled up.
When Jon woke in the morning he could smell coffee brewing and bacon frying. He got out of bed and slipped on his robe. He went to the bathroom and brushed the tangles out of his hair. When Alice saw him coming, she stopped and poured him a cup of coffee. He sat at the table and watched as she finished cooking their breakfast. The thought occurred to him as he sat, sipping his coffee, ‘I could get used to this. Spending the night in a nightgown; Alice fixing breakfast, it was like a dream come true. I suppose that this is just a fancy. She couldn’t put up with this on a continuing basis.’ He found himself lost in thought. ‘Why do you suppose she teased me into wearing a dress last night? She could have gotten me to stay the night without that. Is this something she wants to hold over me? Does she have designs on me as a sex slave? She doesn’t seem to be that kinky.’
"Penny for your thoughts."
Jon started. Alice had just put his breakfast in front of him. "Oh, I was just thinking about last night."
"What about last night?"
"Well, it was certainly a surprise that you invited me to spend the night. I mean, I’m not such a hunk that women usually lust after my body. Then decide all on their own that it would be a good idea to have me in their beds."
"Well, I told you last weekend, that the idea of sleeping with you was a novel one for me.” She leaned over and kissed him lightly. "It just turned out, that when it happened, I liked it."
"So you wanted to try it again to see if it was a fluke?"
"You could say that. I just recreated the weekend, without the booze. I wanted to make sure that it wasn’t just my inhibitions being lowered."
"You ‘recreated the weekend’ costumes and all?"
"Well, just yours, not mine."
"And, what’s the verdict? Fluke, or no?"
"No fluke. I liked it and I want it to continue."
"Costume and all?"
"You seem to like the costume. At least, you’re very responsive to me and you haven’t complained."
He was beginning to be a little concerned. Not sure that the costume thing was a good thing to bring up. He kissed her and began clearing the dishes. "I’d better get these dishes washed before the egg yolk dries on them,” he said.
Alice watched him fill the sink with dish water and then went toward the bedroom. After a minute or two, she came out wearing a dress and went into the bath. When Jon finished with the dishes, he drained the water and cleaned up the sink. He looked toward the bathroom. He felt like he should do something, but was uncertain what. Just then, Alice opened the door.
"Oh good. You’re through. Come in, I’m ready for you,” she said. Jon walked into the bathroom, not sure of himself. There was something unreal about all this. Seated on the commode, he submitted to her make-up artistry and hair styling. "I’ve laid out some clothes for you she told him."
He went into the bedroom. Sure enough, there was everything he’d need. Panties, pantyhose, a slip and a dress; they were neatly on the bed. The sling backs on the floor in front. Reality was beginning to set in. He was sure that this would all come crashing down on him soon. However; he resolved to enjoy all of this while he could. He just hoped that she wouldn’t make too much of a stink when she got tired of him wearing her clothes. He put it all on and went out to the living room.
"You look gorgeous. I like that dress better on you than I do on me,” she told him.
Alice had brought in the paper and they spent what was left of the morning in light conversation and reading the news. Alice fixed a light lunch and Jon washed the dishes. Alice turned on the movie channel and they cuddled up on the couch and watched a movie on TV. When the movie was over they began channel surfing and while they were pausing on a local channel an advertisement for a current movie came on. It was beginning its run at the local theaters. Alice absently picked up the paper and turned to the entertainment page.
"Oh look. That’s playing at the Newberg drive-in. We could go see it tonight."
"I guess we could. It would be the first time I saw a move on the opening weekend."
"I think it’s a good idea. Last weekend we were kind of cooped up in the apartment. That is after Friday night, anyway. I mean, what’s the point of being all dressed up and having no place to go?"
"You mean, I should go dressed like this?"
"I don’t see any reason to change. We’ll be in the car the whole time."
"Aren’t you afraid your neighbors might see me dressed like this?"
"No. You really look like a woman. Besides, it’ll be getting dark when we leave and it’ll be really dark when we come back. No one will get a good enough look at you to even pass judgment."
They continued to discuss it the rest of the afternoon. Jon really wanted to go. It had been a fantasy of his for a long time. He was hesitant about the idea. The only time he had gone out before was at college, and then only late at night. He couldn’t bring himself to agree to the idea outright.
As he was finishing up dinner dishes Alice brought out two coats.
"We’d better get going, if we want to be there before the movie starts."
The die was cast. He put on the coat, stopped by the hall mirror to check his make-up and followed her out the door. They got to the drive in just as the light was failing. It was already dark when they joined the long line of cars waiting to get in. Alice stayed to the right so she would handle the money transaction. She parked way in the back of the theater, just as the feature was beginning. She hung the speaker from the window and snuggled up close.
About two thirds of the way through the movie they began to neck. It was a strange and exciting sensation, as Alice took the lead. She started by caressing his back as she kissed him deeply. Soon her hand moved to his hip. At last, she had her hand on his leg. By now, she was kissing his neck and chest. She began to rub his leg slowly. Each stroke saw the hand going lower until it slipped off the skirt. Here she paused to tantalize him with a circular motion before beginning to explore his leg under his skirt.
He felt like a high school girl being seduced. He was lost in the ecstasy of her love making. Before he knew it they were making love on the front seat of her car with total abandon. When they were through, she struggled to put her pantyhose back on. It took a while for them to catch up on the story line.
They went back to Alice's after the movie. They removed their make-up and put on their nightgowns. They climbed in to bed and snuggled up for a restful night's sleep.
Jon woke lazily to the sound of the shower. He looked around the room and noticed that there were two dresses laid out. There was also a pair of panties, a slip and pantyhose. He wondered absently, "Why two dresses and only one set of lingerie?" Presently the shower stopped and, after a few moments, he could hear the blow dryer. He sat up in bed and scratched his head. Swinging his feet out of bed, he reached for his robe and got up. In the kitchen he found the coffee pot full and poured himself a cup.
As he drank his coffee, Alice appeared in the hall wearing a slip and panty hose. She waved and blew him a kiss. As he was finishing his coffee she reappeared in one of the dresses. She was carrying the slip, panties and hose. After a short stop in the bathroom, she came into the kitchen minus the lingerie.
"Your turn in the shower,” she told him. "I’ll get some pancakes going for breakfast," she continued as she leaned down to kiss him.
He smiled and headed for the bathroom. As he went through the door she called to him. "My dusting powder is out. After you get your slip on, call me and I’ll come help you with your hair."
He showered, using her shampoo and conditioner. He used her moisturizing body wash that smelled faintly of lilacs. He noticed that she had a razor in the tub. He decided to shave his legs. It was the first time he actually did it. He had thought about it many times but decided against it. He was concerned about the chance of finding a lover and her wondering why he had no hair on his legs. When he was through, he shaved his arm pits.
Getting out of the shower, he slipped into his panties and bra. Drying his hair with a towel, he looked into the mirror. He took up the razor and shaved his face. He pulled on the pantyhose followed by the slip. He opened the door and leaned out. "I’m ready for my hair,” he called.
Alice came in and fixed his hair and did his make-up. This time she had him stand in front of the mirror so he could see just what she did. She pointed out little secrets like just where to start the eye liner and the proper use of multiple shades of shadow and blush. When she was through, she gave him a love pat on the rump.
"Go put your dress on. Breakfast is ready."
Jon went into the bedroom and did as he was told. Coming into the kitchen, he noticed Alice watching him as he walked down the hall. She was sitting at the table and her look was a mixture of pride and love. "You look so good. It’s hard to believe that you ever looked like a man. ‘Jon’ isn’t the right name for you dressed like that. I’m going to call you ‘Jan’, from now on.” Jon... that is, Jan blushed a little as he sat down to breakfast.
Jan felt he should be absolutely honest with the woman he decided he loved. He was afraid to be honest but knew he had to risk it. "Alice," he began shakily, "you have been wonderful to me. You have opened up a whole new set of opportunities for me. You’ve allowed me to share in a world most men never even dream of. I have to tell you something about me. I hope we can continue with our weekends after I tell you but you may as well know now. It might come out later and I'd rather I tell you then to have it be a surprise to you later.” She took his hand in hers.
"Jan, nothing you could tell me about yourself could change the way I feel about you. And as for our weekends are concerned, you would be better to be concerned about what would happen if they didn’t continue. I really like having Jan around. ‘Hell hath no fury like a woman scorned.’ Wasn’t it Shakespeare that said that? A very wise man. You just try and get out of one of our weekends without a good excuse. Now what terrible thing do you have to tell me?"
"I allowed you to believe a lie. Halloween wasn’t the first time I wore a dress. As a mater of fact, I had to force myself to wear men’s underwear that night. You see, I have a large woman’s wardrobe at home. I didn’t need to practice wearing your high heels. I’ve had lots of practice over the years."
"Over the years?" she asked quizzically with a grin on her face. "How many years are we talking about?"
"I, ah, I started... well, I discovered the feel of lingerie before the fifth grade. And I was totally dressing in my mother’s clothes before I got to high school."
"So you why were you so reluctant to be dressed up like a woman on Halloween?"
"I wasn’t sure how you would take it if you knew I could supply my own costume. You have to admit, most women would balk at the idea have any kind of romantic involvement with a man who regularly wears dresses."
"Well I think you should take me to your house and show me what kind of wardrobe you already have. I wouldn’t want to buy a duplicate dress. You know how much women hate to wear the same dress as anyone else.” Then she began to laugh. At first Jan was afraid then when Alice hugged him he began to laugh too.
Jan and Alice got on famously. All of Jon’s fears proved groundless. Alice never tired of having Jan around. She encouraged him to come more out of the closet. Jan appeared at Alice's every weekend. Going to a drive in movie became blasé. Soon, she had him going to indoor theaters. It was just evenings at first, then matinees. After he became accustomed to the matinees, she added a stroll through the malls to do some window shopping.
The first store she got him to go into was a self-service shoe store to buy more shoes for Jan. After that, she got him into a second hand store to buy a couple of dresses. He refused to try them on first. He discovered that was a disaster. Neither of them fit. The second time around, he tried the dresses on. After having so much success, she got him into the fitting room at a small boutique at a strip mall. After much persuasion, she got him into another boutique for lingerie.
Soon, they became regulars in the department stores. They could be found going through the dress racks of six or seven major and not so major department stores. Sales clerks, as they learned the girls' tastes and sizes, began to set aside outfits for them to try on. Jan's wardrobe grew, until she had almost as many dresses as Alice. Not that it mattered, they were so close in size, that they wore each other's clothes interchangeably.
They began going out to dinner before catching the late showing of movies. At many of the restaurants, they were on a first name basis with the maitre d’. Some even held a "usual" table for them when they made reservations.
Jon discovered that he began to hate Sunday night. At first, he thought it was that he had to take off the dress. So he began being careful to be sure to wear one of the dresses they bought for him on Sunday, so he could wear it home. After all, they were his; he bought them for himself. Still he dreaded leaving. Their goodnight kisses drug out longer and longer. A couple of times, he almost didn’t leave. What clinched it each time was that he didn’t want to go back to work wearing the same clothes as he left in Friday night.
On one particular Monday, he found himself distracted. He was day dreaming about Alice. He made a decision to make a decision about their relationship. By now they called each other every night to talk. On Thursday, he told her he was sorry, but he would have to be gone for the weekend.
"You won’t be coming over this weekend?" she asked
"No, I’ve got an important project I have to crank out. I think it’s best if I cloister myself and not surface until it’s done."
"When will I see you next?" the disappointment dripped from her voice.
"I’ll take you out to dinner as soon as I’m through. I should be finished before Monday."
"Jon, there’s nothing wrong, is there?" she asked apprehension in her voice. "I just feel like there’s something you haven’t told me. You can be honest with me. You know you can tell me anything. I haven’t made you feel like I've taken over your life or anything, have I?"
"Alice, believe me when I say, ‘Before you, I didn’t have a life.’ I just can’t have any distractions while work this out. Don’t worry, I love you. Don’t be gone from your phone for very long."
Friday night was sheer hell. He put on his best dress and went out for a drive and a movie. He walked out, halfway through the movie. He didn’t go directly back to his car. Instead, he walked through the mall. Every time he caught his reflection in a window, he became aware of the lack of Alice's reflection beside it. He finally went home and got ready for bed about 11:00.
To spite the fact that he always was in bed by eleven, he tossed and turned without getting any sleep. It wasn't until he was sure he could see the light of dawn creeping in under the shades that he dosed off. Then, somehow, he managed a few hours of fitful sleep. He awoke with a start at about 9:30. Something was wrong. He looked about wildly. It was as if he expected to see a burglar, or evidence that one had been there. His eyes were burning and his stomach and nerves told him he had better not drink any coffee this morning.
Dragging himself out of bed, he forced himself to get into the shower. Cranking up the heat, he stayed under the jet of water until he noticed it getting cold. Wiping the mirror, he stared at himself in the mirror. His eyes were bloodshot and there were big puffy bags under them. Pulling on his robe, he went to the living room and turned on the TV. He had fifty-nine channels. Not one of them had anything remotely interesting on them. He ended up watching the preview channel scroll by.
About 11:00, he made some oatmeal and toast. That, at least, sat well on his stomach. By 1:00 he was dressed and walking trough the neighborhood. He discovered at 4:00 he was lost. "This is crazy. How do you get lost in your own neighborhood?” He found a through street. It was at least fifteen miles from his apartment. Reversing his course, he started for home. He tried to keep track of where he was going but discovered he again had no idea where he was until he found another through street. At least he was closer to home. He altered his course to get him more on course. When next he became aware of his surrounding, he recognized the area and was able to make to his apartment without getting distracted. It was 7:30 before he managed to get inside. He was hungry, but his stomach was too upset to eat anything. He settled on cooked cereal. At 9:00 he found himself channel surfing again. He bogged down on a grade B detective movie from the 40’s. He didn’t even recognize any one in the cast. The acting was bad and the script poorly written. At 2:30 he went to bed. Waking every hour on the hour; he drug himself out of bed at 10:00 and showered for an hour.
While in the shower, he decided. Still dripping, he called a jewelry store to make sure they were open on Sunday. They were. He called the most prestigious restaurant in town to make dinner reservations. Then he called Alice.
"Hi Alice. I finished up that project. Can you meet me down town in front of the Bancorp Tower at six?"
"Sure. I was hoping you would call today."
"Wear that black satin dress with the pearl necklace, will you?"
"OK."
"I gotta run. See you then. I love you."
He dried off and got out his best suit. The one he had worn for his final interview with Cybertek. He was at the jewelers before 1:00. A nice young lady greeted him as he walked up to the counter.
"Good morning sir. What can I show you this morning?"
"I’d like to see something in a woman’s wedding set. Something that will let her know I’m serious. It should tell her at a glance that I’m willing to give her all I own or ever hope to own."
"A very special lady, no doubt. A very lucky lady as well," the clerk said as she took out a tray of wedding bands."
Jon spent three hours in the store. He picked out a very traditional set with a 1.4k center stone and a 2k total diamond weight. He arranged to have it sized and ready for pick up by 5:00 PM. His next stop was a tux shop.
"Yes sir. May I help you?" the young attendant at the shop inquired.
"I need a tux for tonight. What do you have in stock that could be rented right now?"
"That’s very unusual. Our tuxes require at least a three day lead time for alteration."
"I see. Maybe I should go to a fine men’s shop. Sorry to have bothered you."
Turning on his heel he found a Nordstrom’s and went to their men’s shop. A very professional looking older associate offered to assist him.
"Can you do same day alterations today?"
"There may be a possibility. Is it really that urgent?"
"Yes, I’m afraid it is. I need a tux. After a week’s deliberation, I've decided to propose to a very special lady today. I don’t want to delay it even one more day."
"Let me make a phone call. Perhaps I can arrange something. What time will you need the tux by?"
"If I can change into it here, I could pick it up as late as 5:45."
"I’ll be just a moment. In the mean time, why don’t look through this rack and see if there is anything you like."
Jon looked at tux jackets and tried a few on. The sale associate was back by the time he had tried on the third jacket.
"I’ve spoken to our tailor. He is sending someone over now. There will, of course be an extra charge."
"Of course."
"That jacket is one our more popular models. However, for a man as youthful as yourself, might I suggest a double breasted model,” he said taking one from the next rack. Jon tried it on and walked to a mirror. The fit across the shoulders and around the chest was perfect. He had to admit that the double buttons made him look great. It made his shoulders look broad and waist narrow. The associate took some measurements and rang up the sale. "This will be ready at 5:30 sir. Will you be needing any accessories?"
"I'll need shoes, a shirt, studs and cuff links."
"Right this way."
Jon selected a shirt and a stud and cuff link set in pearl. His shoes were a black oxford. Almost as an after thought, he bought a pair of men's nylon dress socks. He asked if they could keep these things for him to pick up with the tux. The associate was happy to accommodate him.
Jon found a hair styling shop that was open and encouraged walk-ins. After a short wait. He was escorted to a chair. He was pleased find out it was a full service shop and would be happy to shave him as well as wash and style his hair. He opted for a manicure as well. Sitting in the chair he realized he hadn’t eaten all day. He went by the food court and treated himself to a salad bar. He didn’t want to spoil his appetite for dinner. It was nearly 5:00 as he headed for the jewelry store. He picked up the ring and headed for Nordstrom’s.
He went into the changing room and put on the tux and the rest. The associate bagged his old clothes. He was in his car by 5:30 and headed for the Bancorp Tower. Alice was in the building lobby as he went inside.
"Oh Jon. Look at you.” Then lowering her voice, she whispered. "I thought I might be meeting Jan."
"This is a special night. It had to be Jon."
"Oh and what makes it special?" she asked with a sideways glance.
He guided her into the elevator. "You’ll see,” he told her.
The view from Atwater's was magnificent. While they were waiting for the desert, he reached into his pocket and produced a small box.
"I got you something. I hope you like it."
She took the box and opened it. She was stunned. "Jon, does this mean what I think it means?"
"Will you marry me?"
"Oh Jon, they’re magnificent."
"That’s not an answer. I guess I'll have to take them back."
"Oh no you don't. You’ve asked. You can’t get out of it that easy. Of course I'll marry you."
He took out the engagement band and put it on her finger. Alice leaned across the table and kissed him. After dinner, Jon followed Alice back to her apartment. Then taking Jon's car, they went to a local club and danced for a couple of hours. Reluctantly, Jon left Alice at her door around 12:30 am. Monday evening, Jon called his mother.
"Hi Mom."
"Well hello Jon. I was beginning to think something happened to you. It’s been a week and a half since I heard from you. I’m used to having you call at least once a week."
"I’m sorry Mom. I had something I had to work out. I’m afraid I didn’t call my girlfriend either."
"She sounded like such a nice girl. I hope there is nothing wrong between you two. You know before you started dating her, I was afraid there was something wrong with you and women in general. I mean, you never dated in high school and with your study load in college, you didn’t have time. I never even heard of you having a crush on anyone. Will you be making up with Alice?"
"Mother, you’re so dramatic. First of all, there were women in my life before Alice. It’s just that none of them meant enough to me to share my experiences with them. And secondly, there was nothing to make up between me and Alice. I was just working on something that kept me busy all week. I made it up to Alice last night and I think what I have to tell you will make it up to you."
"What you have to tell me? Don’t keep me in suspense what is it?"
"Last night I asked Alice to marry me and she accepted."
"You’re getting married? Jon, you didn’t even bring her to meet me. You never even hinted that you were thinking of getting married. You have to bring her to dinner at my house Saturday. I’ll expect you two at 4:30 and I won’t take no for an answer."
"Yes mother, we’ll be there. Alice will be thrilled to meet you."
He called Alice and told her that they had a command performance at his mothers on Saturday. Jon spent his usual Friday night as Jan at Alice's he did stop by home and pick up an extra change of clothes for Jon. They spent their accustomed Friday night and Saturday morning. At 2:30, Jan began the transformation back to Jon. Jon and Alice arrived at his mothers at 4:15. They knocked on the door and Jon's mother answered.
"Hello Jon, and you must be Alice. I’m Jon's mother, May. Come in; come in both of you. I’m so glad you could come."
The dinner went off without a hitch. Jon's mother and Alice got along famously. Jon's mother solicited a promise that they would get together for lunch real soon. "Just us girls."
Jon got ready for bed as soon as they got back to Alice's apartment. Alice combed out his hair and they settled in for the evening. On Wednesday evening, Jon called Alice as usual.
"Oh hi Jon, I just got off the phone with your mother. The phone was ringing when I walked in the door."
"She didn’t waist any time calling you, did she?"
"No, she wanted to know if I could take a long lunch on Friday and meet her."
"What did you tell her?"
"What could I say? She’s going to be my mother-in-law. It behooves me to keep on her good side. I said ‘yes.’ Besides, what makes you think I wouldn’t want to go to lunch with her? I really do like your mother. What’s more, she seems to like me."
"Why wouldn’t she? First of all, you’re very likable. Secondly, she’s really glad I've even got a girlfriend, let alone a fiancée. To tell the truth, before we got involved, I think she thought I was gay."
"I can testify that you’re anything but gay."
"You’ll have to fill me in on your lunch with Mom."
"That depends on what we talk about. You know that not everything a mother-in-law tells her daughter-in-law should be repeated for the common man in their lives.
"OK, OK. I’ll give you your little secrets. But I expect to know if it was fun or were there some serious things discussed. Will you give me that much?"
".... OK, but I'll decide the details."
Friday evening, Jon became Jan as usual. Over dinner, he asked Alice about lunch. "Well, how did lunch go? Did she give you the impression that you were ‘good enough’ for her son?"
"Yes she did. On the contrary, she seemed concerned if you were ‘good enough’ for me. The one topic that we discussed on the serious side was how well I knew you. If I thought you had any secrets from me and did I love you enough to stick it out with you after the honeymoon stage. That is, when your deep dark secrets finally surfaced."
"Well, do you?"
Alice looked him up and down as he cleared the table. "What more deep dark secrets could you have besides the one I can plainly see now?"
"I hope you didn’t tell her that. She doesn’t know about this you know."
"No, I couldn’t resist a grin as I told her that I was sure that nothing about you could change how I felt about you. I told her that I had decided to marry you and to love you the rest of my life and I was going to stick to that decision even in the face of hell itself. Then she gave me a strange look and said she hoped I really meant that."
When Jon got home from work on Monday, there was a message from his mother on the answering machine. She wanted him to come to dinner. Jon called and said he’d be right there. His mother greeted him at the door. After their usual hug and kiss, she escorted him to the table. Dinner was already on the table.
They dished up and began eating. "Jon," his mother started. "I really like Alice."
"That’s good. She’s going to be around a long time."
"Well, I hope so. But I'm concerned about something. I've never discussed it with you before. I thought if you wanted my input on it you would bring it up. You never have so I've held my piece about this. But now I think it will affect your happiness and the happiness of that sweet girl. That said, I'm going to stick my nose into your business. I don’t know how to bring this up delicately, so I’m just going to say what I think.” She paused and looked at him. There was a hint of pain in her eyes. It was obvious that she didn’t like the position she felt herself in. "Jon, you have to tell her about what you have behind the panel in your closet. It just isn’t fair of you to marry her and hope she won’t find out about it."
Jon stopped mid chew. He swallowed with difficulty. "You know about the panel in my closet and what’s behind it?"
"Yes, I was putting something in your closet and bumped it. It just kind of swung open."
"Kind of a shock, huh?"
"No, not really. Although I wondered where you were keeping that sort of thing these days."
"These days? You knew about them before?"
"Well yes. You used to store them in your computer boxes at college. Before that you used to hide a few things in the attic access in your closet. Of course you didn’t need much. After all you had the run of my wardrobe in those days."
"How long have you known about... this?"
"Well, I began to suspect when you were in the sixth grade. My closet seemed to get rearranged from time to time. My lingerie drawer as well. Then, when you were in the eighth grade there was a broken zipper on one of my dress that wasn’t broken by me. I almost confronted you about it then. I was angry that you hadn’t told my you broke it. But then, I realized that you couldn’t tell me without admitting everything else. I figured that you weren’t ready. It was then that I started putting my really good clothes in the garment bag to "keep them fresh" you remember.
"But back to the point. After all this time, I'm sure that you are into a life time habit and you won’t be able to stop just because you get married."
"Alice already knows. I wouldn’t have been able to ask her if she didn’t."
"She knows? How long has she known?"
"Since last Halloween."
"Last Halloween? You guys weren’t even serious about each other then, why did you tell her then?"
"She got me to go to a party dressed as a woman."
"What did you do? Just blurt out what a good idea that was?"
"No, I let her persuade me. I thought it would be a one time experience. But she came to my apartment with my costume and drove me to the party. Well it’s a long story."
"I'm really interested. I'd love to hear it."
"Well, she had too much to drink. I drove her home and helped her into her apartment. I had planned to take her car home and bring it back in the morning. But when I tried to get her to lie down on her bed, she began to get amorous and one thing led to another. When I woke up in the morning I was still there. I ended up spending the weekend. Her waist is too small for me to wear her pants so I wore her dresses all weekend. She said that if I was going to wear her dresses that I should look like a girl and she fixed my hair and make up, both Saturday and Sunday. Then she drove me home Sunday night. She wouldn’t wait for me to go in and change so she could take her dress home. She told me to bring it on Friday and she would fix me dinner.
"I couldn’t resist wearing the dress again through the week. I figured ‘what she didn’t know wouldn’t hurt her.’ When I took the dress back she teased me about wearing it through the week, but I was noncommittal about that. Then she teased that I might want to wear it again. I teased back a little and she took up the game seriously. She said. ‘You needn’t feel like I'm pressuring you to wear that dress. You can wear any dress you want.’ After that she got me to admit that I had enjoyed myself the previous weekend.
"She came and kissed me very passionately. While my head was swimming she asked me outright if I had worn the dress through the week. I was under her spell. Without thinking, I nodded my head yes. She just smiled and went back to fixing dinner and said, ‘Let me know when you’re ready for me to do your make-up.’ I had to believe she was serious, so I took a chance. I put on another one of her dresses and she did my hair and make-up again. Since then I've dressed up almost every time I’ve been with her."
"And she thinks it’s OK?"
"Oh yes. She has gotten me to do a lot more then I ever did on my own. She even decided on her own that I needed a female name when I'm dressed. She calls me Jan."
"Well, I guess the only thing to decide is which of you is going to wear the wedding dress."
They both laughed at that.
When they told Alice’s family, her mother asked. "Which one of you is going to wear the wedding dress?” Jon's mouth dropped open.
"Oh Jon, I guess I should have told you that my family knew about your hobby."
"And, you guys don’t have a problem with it?"
"Not after ‘Aunt Jo.’"
"Who is Aunt Jo?"
"My real father. He was a cross-dresser. He was very sweet to me. After he and Mom divorced, I would spend my summers with him. Aunt Jo would take me to movies and later shopping and buy me very nice clothes."
"Just so you know, Jon," her mother said, "his cross-dressing had nothing to do with the divorce. We actually divorced because his career took him to Seattle and mine kept me here. We tried a long distance relationship, but as you might expect, we just grew apart. We are the greatest of friends. We just aren’t in love with each other any more."
"Well back to the question at hand," Alice intoned. "I, personally, would like to see ‘Jan’ as the blushing bride and I'll wear a tux."
The wedding was small, but very elegant. Jan wore his mother's wedding dress and she cried tears of joy as he walked down the aisle. Aunt Jo attended in a beautiful gown.
Comments
Sweet story.
Would never have happened in my youth but these days, things are considerably easier.
Thanks for the delight.
Bev.
xx
Sometimes it works out
Jan and Alice seemed to manage more common interest than just computer technical input, output. A girl geek and a boy geek hitting it off and becoming normal people rather than recluse geeks. Sweet.
Hugs Patricia
Barb
Life is meant to be lived, not worn until it's worn out.
Oklahoma born and raised cowgirl
Most enjoyable
Well rounded story with no nasty attitudes. Thanks for the treat!
Glenda Ericsson
Sweet & well told
Thanks for very nice story. If wishes were horses, we'd all live in stables.
More like this would be wonderful.
>>> Kay
The mention of TSR's...
dated the tale. Those were often a real PITA back in the day.
Lovely tale.
Samantha
As I said, it was an older story
Not sure what to replace TSRs with, so I just left it. Back when I wrote it, I dabbled in some programing and did some "shareware" (another dated idea), but got away from it and did more a mundane line of work.
Hugs
Patricia
Happiness is being all dressed up and HAVING some place to go.
Semper in femineo gerunt
Ich bin eine Mann
Alice is a real keeper
A guy should learn on in his life that mom knows everything about him. What he does, what he tries to hide, what he thinks, and every other thing that never escapes her eye.
Jon is very fortunate to have a family that knew his secret but kept that fact to themselves. That they didn't feel it necessary to correct Jon's behavior.
Then enters Alice, a person like Jon, more a loner than someone wanted for the person she is.
Halloween will always be special for the couple, bringing them together because of the "costume" Jon wore. And leading him to admit something later in their relationship he thought he'd been hiding
Jon is slow on the uptake, after telling Alice about his dressing then thinking their relationship was over because she'd be upset. Jon deals with computers, electronic logic machines. Yet he couldn't reason that if Alice liked having Jan around, she wouldn't be repulsed by Jon dressing.
And it seemed no one else did, since Jan turned out to be the blushing bride at their wedding.
This is a cute story, bringing two people together who needed each other.
Others have feelings too.
Love your work
Another example of great work by you. Thanks for sharing this with us.
Your friend
Crash
Wonderful older story,
I rarely read anything shorter than a novella, but I'm glad I gave it a try. My only complaint is that it was too short, I would have loved a more immersive version or to have it continue - although this one came to a pretty definitive conclusion.
I feel sorry that Alice's
I feel sorry that Alice's parents split up.