Learning By Experience is a work of fiction. All situations and characters are fictional. Any similarity to persons living or dead is purely coincidental. It is a copyrighted work by Caitlin Rose. It may be archived at any site that does not charge a fee for access. Please obtain permission from the author before archiving. All other rights are reserved. This work contains descriptions of crossdressing and some mild sexual situations. If you think you might be offended, go read something else.
Learning By Experience
by Caitlin Rose
Once upon a time, Br'er Rabbit said to Br'er Fox, "Pleeeese don't throw me into that Briar Patch."
"The temperature is supposed to hit ninety today. How 'bout a swim this afternoon?"
Carrie put down her coffee and looked hard at John. "John, look at me. Do I look like I'm ready to go swimming today?"
John looked at his lovely wife, as he used a piece of toast to mop up the last traces of egg yolk from his plate. "Carrie, you look as healthy and fit as ever. Don't you feel well?"
"Oh I feel fine. Look at my hair, silly. I have it up, in this fancy style that you seemed to appreciate so much when we were dancing last night. I'm not about to jump into a pool with this hairdo."
"Yeah, that was some party, and you certainly were fantastic."
John's eyes got dreamy for a second as he recalled how his wife appeared in her low cut gown, gliding gracefully on her tall pumps. He remembered holding his wife close as they danced. He remembered how the smooth sweep of her hair caught the light, how the delicate tendrils framed her face. Still, that was last night, and today was today. "But Frank and Carol's engagement party was last night, and you were a knockout. Now, the party is over. You don't have to worry about your hair anymore." "You just don't get it, do you? You are the perfect example of an insensitive, unfeeling, uncaring male animal. I spent most of yesterday getting ready for that party, while you just played a pleasant round of golf with your buddies. Much of my time was spent on this hairdo that you seem to like so much. Well, I'm not about to ruin it with a quick plunge into a pool. I wish I knew a way to make you appreciate my efforts."
Carrie took another swallow of her coffee and left the room. John sat with his own coffee and with his own thoughts. A tiny smile crept across his lips. Maybe this could work, after all.
He went outside to wax his classic MG midget, and to try, for the umpteenth time, to get those two little SU carburetors to work in unison. When Carrie called him for lunch, he hurried in from the garage.
Over lunch, John continued the conversation. "Well, I guess you're right about the swimming. What would you like to do this afternoon?"
"How about a little shopping at that nice air conditioned Galleria mall, followed by an early dinner and then a movie?"
"Okay, let's do it. I'm ready when you are."
"Ready? What are you ready for, a pickup softball game? What has gotten into you? Look at me. I'm wearing a skirt, a delicate blouse, hose, and heels. You're wearing a tee shirt, cutoff jeans, and sneakers. You still have grease stains on your hands. At least make an attempt not to embarrass me!" "Okay, I'll change."
John showered and changed his clothes. He put on chinos, a sport shirt, and loafers. He wished he also could be wearing a skirt and blouse. For John, you see, is a crossdresser. He has been one for at least 24 of his 34 years. He began with the smooth nylon panties he "borrowed" from his older sister. After college, while he lived alone, he had gradually acquired two or three complete outfits, which he wore in the privacy of his apartment, always accompanied by strong erotic excitement.
John was also heterosexual…emphatically so. He appreciated women and how they looked. You might say that he admired them so much, that he wanted to look just like one. The thought of being so beautiful, so dressed up, so carefully primped and coiffed, is perhaps the most exciting thing John can think about.
Carrie was beautiful and witty. John had fallen deeply in love with her, within weeks of their first date. Beautiful women had always fascinated him, by their clothes, their hair, and their makeup. He wished he could emulate their look and style. But with Carrie it was something more. She worked at her beauty, and enjoyed doing so. John would watch in fascination as she performed her beauty rituals. It was always such a turn-on to watch her. He only wished he could join her in the experience. But his crossdressing had become an exercise in imagination. The only visible thing he held onto was his long hair. It was shoulder length, and worn in a simple, low ponytail, tied with a thin elastic band. His crossdressing ended with his marriage to Carrie. Not that she had ever said anything. She didn't have to. It was more her attitude, and some general observations she had made about effeminately dressed men, that convinced him that his "hobby" would have to remain hidden. John thought about how much he missed his delicate clothing as he prepared for his afternoon out with Carrie. He carefully blew his hair dry, styling it into a simple center parted flip. He admired this girlish style at the mirror for a minute or two, before converting it into a standard "male tail." As he stood at the mirror, he remembered back when the reflection might have worn lipstick, or perhaps a head full of curlers. He began to form a plan.
"Okay Carrie my love, ready to go. Our chariot awaits." "If you mean that bottle-green beast you were fussing over all morning, then no way."
"Why not? If ever there was a top-down day, this is it. You can wear a scarf to keep your hairdo undamaged, if you want to."
"Oh sure, and get half a pound of dirt and bugs stuck to my face."
"Well, they do have ladies restrooms at the mall. You can wash up when you get there. Don't be such a priss!" "And I suppose you are willing to wait the 20 minutes while I put my makeup back on. Doesn't the effort I put into my appearance mean anything to you? Besides, see, I'm wearing a skirt and hose, and it isn't particularly easy to crawl in and out of that little car."
"Okay, we'll use the Toyota, then."
John had a curiously satisfied look on his face as he pulled out of the driveway. He turned the air conditioning on to full blast. After a few minutes Carrie re-adjusted the controls to a more moderate setting.
"C'mon dear, it's hot out. Don't stint on the A/C!" "Is that necessary? My legs are almost bare, and you seem to want to see them turn blue or something. You aren't happy unless you can see your breath."
"Oh come on. You're always telling me how warm and sticky those nylons get in the summer, now you're complaining about it being too cool. Make up your mind." "Well, nylons do get a bit hot sometimes. Now, you've made this car feel like a meat locker. My legs went from being warm and sticky to being cold and clammy with nothing in between, but I wouldn't expect you to understand that." John drove to the mall. The parking lot was crowded and the only available spots were far from the building. They stepped out of the car into a sea of steamy air, overheated blacktop, and scorching sunlight. John began to walk very quickly, almost run, toward the nearest entrance. Carrie tried to keep up, her high heels making a soft tapping sound on the heat softened asphalt.
"Come on, try to keep up with me! Let's get inside. It's broiling out here!"
"What's wrong, Mr. Outdoors? What's the problem? You wanted to come here in an open car, remember?" "That's different. This parking lot is just a couple of degrees short of a griddle."
He speeded up his gait.
"You think it's easy to run in heels? You have no comprehension of what it's like at all, do you?" John didn't answer. He slowed down just enough for Carrie to almost catch up with him.
John followed Carrie through J.C. Penny, Macy's, and three or four smaller stores, as she shopped for short sleeve blouses and a pair of culottes. He tried to pay attention when she asked him for an opinion, but he was distracted as he imagined wearing some of the delightful, airy, soft things, himself.
"Carrie, just select one of those blouses, and let's go. They both look very nice."
"I asked you to look and tell me if the yellow one pulled across the back, and you barely glanced at it. You don't seem to have any concept about what a woman looks for in clothing."
They quibbled their way through the rest of the shopping. They never quite reached the point of arguing, but they didn't sound particularly loving either. Finally it was time to choose a place to eat. John wanted to go to Fudruckers, while Carrie's choice was a quiet Italian place, about a mile from the mall. John gave in, and then slurped his way through a huge serving of spaghetti with clam sauce. Carrie quietly enjoyed her chicken Marsala.
When it came time to choose a movie, John hastily suggested that they see one of the two big action movies showing at the ten-plex. Carrie wanted to see the one period drama that was playing. John finally gave in to Carrie's selection. He might have even enjoyed the "chick flick," were it not for the sudden allergy attack he suffered. At least that was the excuse John gave for all the sniffling he did during the film. Things continued on about the same way between John and Carrie for the next few weeks. They got along okay. They even made love a few times. But, little by little, Carrie was becoming convinced that John needed to become more sensitive, more appreciative of the effort she put into being a beautiful, sexy woman.
One Sunday evening, Carrie was at her vanity, preparing to change her nail polish, for the workweek ahead. "John, did you do something with my nail polish remover?"
The bottle is empty, and I just bought it last week."
"Uh…I just used a tiny bit. I needed to get some touch up paint off my hand. It worked great."
"And you left the cap loose. And it all evaporated. And now I have none when I need it. Come on. Get in the car. The mall is still open for an hour. You need to learn something. I'll drive."
Carrie walked to the car with John following. Even in her somewhat pissed-off state, there was music in the flow of her hips. Her long blond hair swung gracefully as she entered the car.
"I need nail polish remover, and you need to learn something.
We're going to do some shopping for you too this evening. Now, I know you appreciate certain things about me. You certainly react when I dress up, when I try a new hairstyle, or when I change the way I do my face. But, there are times when I think you just don't care about the effort it takes. It is one thing to appreciate the results, and a very different thing to respect and be supportive of the effort." "Err…sure dear."
He answered almost distantly, as if he'd barely been listening.
"John, listen to me, and listen carefully. It takes me a significant amount of time, money, effort, and even a bit of discomfort to maintain my appearance, an appearance you seem to enjoy. You seem to acknowledge that, but I don't think you really understand what I'm talking about."
"Well, what do you expect me to do?"
"I expect you to learn what it takes to be pretty, by experience."
His heart leapt!
"I'm not about to dress up like a girl, if that's what you're thinking."
Once they reached the mall, Carrie led the way into Cosmetics Plus. She got her nail polish remover and then selected some foundation makeup. She beckoned John to join her in a quiet corner of the store.
"John, let me try this on the back of your hand. I need to see how it goes with your complexion."
"Are you nuts? You aren't getting me to wear makeup!"
"John, just cooperate. We'll talk later." It was her "no nonsense" tone that got John to quietly put out his hand.
Then his heart leapt. Could this really be happening? He began to feel the beginning of an erection, as Carrie tested the colored lotion on his hand. The feeling intensified as he watched her select blush and lipstick, and test each on his hand.
"You don't expect me to wear this silly stuff, do you?"
"You seem to like 'this silly stuff' on me though, don't you?"
"But that's different. You're a girl!"
"Is it so different?"
The next stop was JC Penny where Carrie quickly scooped up a package of panties, a bra, pantyhose, a long black skirt with a bright floral pattern, and a pretty, round-neck blouse that buttoned up the back. The blouse was a cream color with short, puffy sleeves.
John could see that all were in sizes much larger than Carrie wore.
"I won't ask you to try these on here. You can always bring them back and exchange them for your own size, if they are wrong. We still have to stop in the shoe store." John was about to protest again, but he was afraid that the excitement he felt might do something to his voice, so he kept his mouth shut.
In Payless Shoes, Carrie consulted a chart that showed equivalent men and women's shoe sizes. "Size 9 Men's…looks like a size 10 or a 10 ˝ Women's should fit. Here, try these."
She walked him to an empty aisle and handed him the black pumps. They were simple, with a blocky three-inch heel. It was hard work to control his growing excitement as he tried them on.
"These shoes are kind of tight."
"Well, they're probably right. Remember, you won't be wearing them with those heavy socks." "Remember, I won't be wearing them at all! You're the girl. I'm the guy. You get all prettied up. I look at you with awe and love you to pieces."
Carrie just smiled.
"Don't complain about the heels, either. They're high enough so that you'll have to learn to wear them, but they're not killers."
John was trying to hold back a major erection now, as he thought of wearing those pretty shoes with smooth nylons. They left the mall with the last of the late-evening shoppers. John carried the packages. He had seen the clothes only briefly, but he could tell that would feel delightful against his skin. Carrie had such wonderful taste, and these were like things she would wear herself.
John got into the driver's seat for the trip home. "You don't really expect me to dress up as some poor imitation of a girl, so you can try to teach me a lesson, do you?"
"Oh, who said anything about a poor imitation? Besides you haven't heard the alternative yet."
As he drove, Carrie began to slide her hand over the top of John's thigh, and pulled down his zipper. She caressed John as she spoke softly. The combined effect of Carrie's touch and his own thoughts had him fully erect within seconds. "John, I think you need to learn something about what a woman goes through, to be attractive. And I think you're going to cooperate, or you'll find yourself without one of your favorite activities."
"Oh babe, you wouldn't do that, would'ya?"
"I'm very serious about this."
"Wait a minute, you think that by getting me all dolled up, with some kind of beehive hairdo or something, a skirt, and high heels, that I'm going to become more sensitive?" "Oh no, not a beehive. That style went out years ago. But why not heels? You seem to like when I wear them, then you expect me to run across a hot parking lot in them. It'll be fun to see you try to walk in them, no less run. I've seen that admiring look when I wear a long pencil skirt. Only as soon as I put one on, you suggest a ride in that ridiculous MG Midget. Am I supposed to beam myself into the passenger seat?
I don't plan on having you look ridiculous, but I do plan on you learning how much work I go through, to nourish your fantasies. They say a picture is worth a thousand words, but an experience is worth a million pictures." "I always thought you enjoyed getting all dressed up." "Oh I do. I love looking pretty and feminine. But I don't enjoy it when my efforts are taken for granted." They rode home in silence. Once in the house, Carrie led John into the bedroom.
"Now, take off all your clothes, right down to the skin."
"Sweetheart, that's a request I'll always comply with."
He put his arms around her.
"Not now. Just get undressed. You have all that nice masculine body hair, but I'm afraid it just won't do on a pretty girl. Besides, I have to get rid of the little body hair I have, and it's no great pleasure for me either. I'll do your back and chest, but you'll have to do your legs and pits." "No! I like my chest hair."
"Would you rather have Big John down there spend his evenings alone?"
She spread the Nair cream over his back and chest, then handed him the bottle.
"Come on. Do your pits, then your legs. All the way up. Don't get any of this stuff on your really sensitive parts. I don't want you to get a rash or anything. Don't forget your arms."
John spread the cream on as Carrie had directed.
"Now what?"
"Now you give it time to work, then shower away all that nasty hair."
John stood and waited while Carrie changed her nail polish. Soon the itch began, then the burning sensation that he had read about, so many times, on the web. Carrie asked him to use a tissue and try to wipe away a spot of hair on his chest. He did, and the hair came away, leaving smooth skin.
"Ok. You can shower off now. Be sure to use the Buff Puff. You can scrub a little if you want, but most of the hair will just fall off."
John came out of the shower feeling a little like a peeled potato. His skin was smooth and hairless, and slightly raw. Carrie was waiting for him with a large plastic bottle. Together, they applied the floral scented lotion wherever the depilatory had been. After Carrie took her shower, they took turns applying fragrant bath powder to each other. Their lovemaking that night was a new and wonderful experience, as their smooth bodies slid over each other, and their growing warmth intensified the feminine fragrance that surrounded them. Carrie was a bit surprised at how great it was.
The next evening, right after dinner, Carrie insisted that John try on his new outfit.
"I think I've done enough already. After all, I removed all my body hair. I won't even be able to go to the gym until it grows back. And if that wasn't enough, I can still smell that lotion and powder. I think a guy gave me a funny look in the elevator this morning, when he smelled it too." "Don't be a crybaby. I see all those commercials with beaches full of hairless guys. It doesn't seem to be such a big deal. Besides, I think I like you better, nice and smooth like this. Let's go. Try on the clothes. Start with the panties." "No…It doesn't make any sense. Panties won't take any longer to put on than Jockey shorts will. They don't seem to take any special effort or skill. I won't learn anything by wearing them."
"Maybe, you will, maybe you won't. One thing is sure. You won't feel very comfortable wearing panty hose over Jockey shorts. So, put on the panties."
John tried to look uninterested as he unwrapped the package. The three pastel colored panties were trimmed with small lace borders around the waist and leg holes. John thought the pink ones were the most attractive, but chose the green to hide his enthusiasm. He hadn't worn nylon panties in years. The material felt smooth and cool as he pulled them up onto his legs. The old excitement threatened to return full force, as tucked himself into the delicate nylon. "See, that's not so bad, is it? Now put on the pantyhose.
Take your time with them."
John made a point of fumbling a bit with the hose. He let Carrie "teach" him how to gather them in his fingers before pulling them up. He deliberately got them well twisted while pulling them up. Carrie took them back and gathered them up again.
"Here, I'll help you this time, but pay attention." The tan nylon slid up his smooth legs and over his butt. He reacted as he always had before. He became erect as soon as the nylons were in place.
"See? You touch me and I get hot for you. I'm a guy. Now, can we stop this silliness?"
"No we can't! Take them off, very carefully, and put them back on!"
John eased the hose off and re-rolled them. He smoothed them back up his legs.
"You did that very well."
John tried to read the look on Carrie's face. Had he shown too much familiarity with this very feminine skill? Carrie handed John the bra.
"Do I really need one of these?"
"The clothes won't hang right on you without it." John took it and began to put it on. He made sure to act as if he had no idea how to fasten it behind his back. Carrie showed him the "put it on backwards" trick and made him do it. She stuffed the cups with tissues.
"This thing is uncomfortable."
"Ah. See? You're learning already. Imagine what a bra with an underwire feels like. Then imagine what it feels like if you have to wear it all day. Women often put up with some discomfort just to keep you guys interested." "Hey, that's not fair. I'm not one of those guys with a boob fixation."
"Still, I think you need to learn about it. In fact, those tissue filled cups are just too easy. You need some weight in there to get the idea. I'll have something more realistic for you to use, by the weekend."
"Wadda ya mean, by the weekend? Do you expect me to do this more than once? Be reasonable!"
"Now, put on your blouse."
The blouse was a delicate cream color, with a pattern of tiny eyelet work around the neck opening. John tried to do up the little buttons at the back of his neck.
"I'll help you with that."
Carrie lifted his ponytail and buttoned the blouse to the top.
"You may need help getting this off too." The blouse was so pretty! The very inconvenience of it only made him feel more vulnerable, more feminine. He had to force his mind to think about something else, something less exciting.
The skirt didn't fit. It was a bit too large and John just didn't have the hips for it to hang on.
"You can take this back tomorrow on your lunch hour and exchange it. You might want to try on a couple, to make sure you get a good fit."
Carrie used a safety pin to temporarily fit the black, floral print skirt, and had John try on his pumps. Now, with the whole outfit on, she had him walk around the bedroom. "Wait…one more detail."
She took the elastic off his ponytail and let his hair fall on his shoulders. It was then that John stopped in front of the full-length mirror and took a good look at his feminized image. He could feel his penis straining against his panties and his pantyhose. He was lucky that the generous skirt hid the bulge.
"Okay, that's it. I'm done, right? You have me in girl clothes, right down to the shoes."
"Oh…You're not done by a long shot. Tomorrow you exchange the skirt, remember. Then we can go on." John rarely wore pajamas, usually preferring to sleep in a pair of boxer shorts. That night, he slept in nylon panties. But only until Carrie got them off him.
The next day he exchanged the skirt. Carrie made him show her how the new one fit. It was perfect. "I tried it on at the store. I didn't even make up some lame excuse about a losing a bet, or going to a turnabout party. I just took three skirts into the changing room and tried them on. See, I've learned my lesson. Can we stop now?" "No, we can't. This isn't about shopping. It's about you learning to appreciate the work involved in being attractively dressed, coiffed, and made up. This evening, you're going to learn to do your face."
John had almost no experience with makeup. He'd tried lipstick, mascara, and foundation when he used to dress, but not often enough to get good at using them. "Start with the foundation. First, make sure your hair is all brushed away from your face. Shave, then, wash and dry your face and neck. You want to work on a clean, dry surface."
"You sound like the instructions on a paint can."
Carrie stifled a laugh and continued.
"Use that little sponge to apply the foundation. You want to get a nice even coating. Don't use too much, and try to feather the edges a little."
John did as he was told.
"Now I'm going to clean up your brows a little. Don't worry, I won't make them too thin."
John winced a little at each pull from the tweezers. "Not too much fun, is it? See, even a little detail like your eyebrows requires work, and sometimes a bit of discomfort. But imagine what a pretty girl would look like with wild eyebrow hairs sticking out in all directions. You'd notice that quickly enough.
"
John held still for the light shaping of his brows. Of course, he wished they could be done as high thin arches. Carrie then showed him how to use eyebrow pencil, mascara, eyeliner, and a tiny bit of eye shadow.
"I'm only showing you how to do a very basic job here. There are a whole palette of eye shadow colors alone, and you can blend them together to make thousands of combinations. Sometimes a woman will want to match a piece of clothing, or an accessory, or even a mood, with her eye lid color."
Carrie supervised as John practiced with the sponges, brushes, and pencils. She had him completely make up his face and wash off the results four times before she was satisfied with the results. John made sure to complain enough to be convincing, while actually enjoying every minute of the session. After all, how often does a crossdresser actually experience, in real life, the fantasy of being instructed in the art by a beautiful woman; indeed, by one who will accept nothing less than perfection? "Well, you actually look pretty good. Think you can remember how to do this for a couple of days?" "Whaddya mean?"
"I mean that tomorrow evening, you'll learn how to do your hair and nails, and Saturday is your final exam. You'll have to start from scratch and get ready, just like you're preparing for a fancy dinner out."
"I guess there is no way to talk you out of this, is there?"
Carrie just shook her head.
They had some ice tea and cake and went off to bed. Carrie had always felt some slight aversion to guys who looked a bit too fem, but as soon as their lips met for a good-night kiss, she realized that John seemed both hotter and more gentle than she had ever experienced him before. It wasn't long before they were both feeling pleasure more intense than they could remember. They both wished they didn't have to sleep at all, but there were two more workdays to the week. John got home before Carrie on Thursday evening, and found a note asking him to set the table. 'Dinner was in the Crock Pot,' it said. John did as the note asked and when Carrie arrived, they shared an excellent, wine flavored, pot roast and tossed salad. As soon as the dishes were cleared away Carrie directed John to shower and shampoo his hair. "Condition it, and leave it wet. You're going to set your hair, and do your nails tonight."
Now, John had set his hair more than a few times, back when he was actively crossdressing. He was quite familiar with the steps involved. In fact he was afraid that he might say or do something that would reveal his knowledge, and blow the whole game. On the other hand, there was no mistaking the mutual pleasure they had shared over the last few days. He sat at Carrie's vanity and began by combing his hair smooth. He carefully read the label on the bottle of "Roller Juice" before applying it. Then slowly, but competently, he rolled his brown hair onto almost two dozen plastic rollers. He fastened them with the large bobby pins Carrie used, though he would have preferred the plastic picks he used to use.
"Do I get under the dryer now?"
"Do you really want to do that on such a warm night? Besides, I'd think you'd look cute, sleeping in rollers…if I even let you sleep! Better use this though. I wouldn't want all your hard work to get hopelessly tangled up." She handed him a large, pink, triangular hairnet and helped him fasten it around his head. Then she watched as he filed his nails and applied bright red polish. She wouldn't let him leave the vanity until his nails were dry. "You can remove the polish in the morning." They got to bed early that night, eager to resume where they had left off. Carrie found that there was something very special about this delightful man of hers. He was as strong and sexy as ever, but he was more attentive, more considerate. Was the secret of great sex to get your man to wear panties and makeup? Or was it something else? On Friday morning, John unrolled his hair and Carrie watched him brush it out.
"John, you look really cute!"
"Fine, can I wash the curls out and get ready for work now?" "Sure, I guess. Could you just try something though? Just brush your hair back and tie it into your usual tail. I don't think anybody will notice that you have a couple of extra waves and curls today."
"Everybody at work will notice."
"No they won't. If you don't do anything to call attention to it, no one will notice a thing."
John brushed his hair back into a tight ponytail. Sure, it was a bit curlier than usual, but it wasn't all that noticeable. He almost forgot the nail polish, but remembered just before he walked out the door.
Friday was John and Carrie's usual night to eat out at a local place and take it easy. John wasn't sure what to expect this time. As it turned out, Carrie decided to give him the "night off." She didn't mention John's 'assignment' until just before they were ready to get to bed.
"Well, tomorrow is your 'final exam.' I want you to go through the whole routine, from Nair to Aquanet. I want you to look dressy and sexy when you're finished. How long do you think it will take you?"
"Oh, a couple of hours, I guess. But why should I do it all? I already know how much work goes into makeup. I know that tweezers hurt. I even know how to put on panty hose. What's the point?"
Carrie didn't even address his comment. "Tell you what. I'll give you three hours. I'll make us a nice late breakfast at about 10, and at 11, you can start getting ready for our date. Better be ready by two. Now, since we both want to look our best for each other tomorrow, let's put on some moisturizer before we go to bed." John imitated Carrie's technique, and rubbed the fragrant cream into his face and neck. Once again, the feminine activity excited him. Carrie was ready for him when they got into bed. They had another very delightful night. Carrie wouldn't let John begin until the stroke of 11. Then she waited until John had applied depilatory to any bits of body hair he could find. When John finally went into the bathroom to shower, Carrie scooped up some of her own clothes, some makeup and hair supplies, and retreated to the spare room.
"John, you're on your own now. See you at two." John finished showering and powdered himself before leaving the bathroom. He knew his hair would take a while to dry, so he figured he should start with that. "She wants 'dressy' huh?" John thought. "Let's see what I can do."
John worked setting lotion into his hair, and then pulled it into a high, tight ponytail. He set the ponytail on about eight rollers, and added a hairnet. Then he turned up the air conditioner, and got under the dryer. He spent the next half hour carefully doing his nails. He couldn't see a clock from where he was sitting. By the time his nails were dry, it was 12:15. Time flies when you're having fun! John took a break from the dryer to put on his panties and pantyhose. He moved slowly, savoring the smooth feel and the slight compression of the hose. He ran his hands over the smooth nylon. He loved the feel and look of his smooth legs, now encased in sheer hose. This time he actually had to return to the bathroom and relieve his excitement, before he could continue. He decided to wait before adding the skirt and blouse.
At 12:45, he unrolled one roller and found his hair to be dry. He re-rolled the curl and turned off the dryer. He would let his hair cool while he did his makeup. John had shaved twice while in the shower. Now, he applied foundation. When he was satisfied that he had covered his face evenly, he began to do his eyes, then his lips, and finally added a bit of blusher to the tops of his cheekbones.
He checked the mirror and discovered that his lower lip was asymmetrical. There was more lipstick on the left side. By the time his makeup was finished, it was 1:30. Just a half hour to go!
John found that Carrie had left a note with his bra, along with two small party balloons, filled with birdseed. "John, use these to fill your cups. They'll look best if you put the neck of the balloon up front. Be sure to make the straps nice and tight, so that everything stays where it belongs."
John put on the bra. He had to tighten the straps to hold in the balloons. The weight was noticeable as he stood or walked. He slipped on the blouse, but decided to wait for Carrie's help with the buttons. Don't girlfriends do that stuff for each other?
John took the rollers out of his hair and slightly loosened the curls. He pinned them into place, completely hiding the pony elastic. It took several attempts and four "rear view" inspections before he was satisfied with his "curly bun." He finished it with a liberal dose of spray.
He put on the skirt. It fit perfectly. The hem fell around his ankles and the material flowed delightfully as he moved. When John put on his pumps, the clock was showing 1:55. He made a quick circle of the room, to make sure he could navigate without falling on his face. The old skill returned quickly. He took small steps, using a modified "tightrope" gait.
He added a touch of Obsession, the fragrance he preferred on Carrie, and made his entrance to the living room. "Oh my god! You're gorgeous!"
Her hand shot to her mouth.
He walked across the room and sat opposite her, taking care to sweep his skirt as he sat, knees together, and demurely crossed his legs.
"I don't think it's fair to call you John right now. Would you mind 'Joan?'"
"No, that's fine."
"Did you get in some extra practice? I expected you to fall all over yourself and flop into a seat, but you move so well. I'm impressed."
She paused to button his blouse which further enhanced the appearance of his new bosom.
Carrie was dressed much like John. Her skirt was also a floral print, but the background color was a rich burgundy. She wore a pure white blouse, with little pearl buttons. Her hair was in a low, intricate looking chignon . A gold wire clip decorated the back of her head.
"You're quite a treat to look at, too, you know." "Listen, I have something to tell you. When I first thought up this 'lesson' for you, I was planning for you to walk in here and find me in jeans and a Tee shirt. If you looked even half presentable, I was going to insist we go out for lunch, and that we use your MG to go to that "beer and burger" spot you like so much. You know the place, down by the shore, the place that always smells a little like a bait locker. I really wanted you to feel like I've felt. I wanted you to know how it felt to be dressed like a lady, and to be treated like a fishing buddy."
John swallowed hard.
"I have to tell you what changed my mind," she continued.
"Please do."
"Well, I know you've been trying some very unusual things this week. Maybe it was the newness of the experience, or maybe it was something else, but I've seen a real change in you. At first I thought you were just less confident, more tentative. But it was something more than that. It was something positive. You were more caring, less selfish then I ever remember you being before. Now, I know I've made a lot of snide remarks about "femmy guys" over the years. When I made those remarks, I believed them. But now I think I've learned something. That stuff I've heard about guys 'getting in touch with their feminine side' isn't just new-age baloney. There is just no getting around it. Your fem side is wonderful."
"Carrie, there is a bit more to it. This isn't all completely new to me. Actually, I've crossdressed before. In fact, before we met, I used to dress fairly frequently. I always found it to be a marvelous, sensual, and sexy experience. I stopped, 'cold turkey,' a few weeks before our wedding. Then, barely a month ago, you made a remark about 'getting me to appreciate your efforts.' Well, I didn't know what you had in mind at first, but hope springs eternal…" Joan winked at Carrie, exposing a delicately shadowed eyelid.
"You little vixen! Are you saying that you maneuvered me, into putting you into a skirt?"
"Well…"
"Well nothing!"
Carrie paused. Joan held her breath. Carrie smiled while a tear formed in her eye. When she spoke, it was almost in a whisper.
"This week I've experienced warmth and love that I thought only existed in romance novels. I want to discover more. John, can Joan…Can you both…?"
"Can you forgive me for what I did?"
They met in the middle of the room and held each other closely, while tears of joy ruined two very carefully applied faces. Life had never been better.
-fin-
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