Chapter 1
A crazy idea

  It was the Friday before Thanksgiving. My wife had taken the day off as a personal day. She needed the morning to help her mother do the shopping for Thanksgiving dinner. The woman was in her 60s and still insisted that she host the family dinners. I kind of thought that after my father-in-law died a couple of years ago, that that chore would fall on Carrie and I, but no, she said she wanted to keep things as normal as she could, even with Frank gone. Charlotte and Ted, Carrie’s sister and brother-in-law, lived in Denver, so we did Thanksgiving and they got Christmas. With their two kids, it made sense to fly their mother to Denver rather than fly all of them into Portland. I have to admit that I was a bit jealous of Carrie. She’d be done by one and have the rest of the afternoon for herself while I would have to stay at the old nine-to-five for a full day’s work.

   “Hi Hon,” Carrie said when I came in. “You just missed Lisa. She’s been here since I got home.”

   “Oh? I thought she and Mike were taking a long weekend out of town for their anniversary.”

   “They were, but she was too upset and canceled the plans.”

  Now I was confused. “Dare I ask just what it was that upset her?”

   “She’s a bit pissed at me as well.” I looked at her, wondering where she was going with this.

   “Why is she pissed at you?”

   “She spent a couple of hours just trying to control her emotions. She had just shown up at the door saying she needed someone to talk to. Then she just started crying and mumbling that her marriage was over. Something about never being able to trust Mike again. It took me over an hour to get her to calm down and tell me what happened.

   “I thought Mike had been cheating on her, or something. It turns out she caught him wearing her clothes. She was ranting about him being gay and how his going out with the guys was obviously more than the typical male bonding.”

   “She’s nuts,” I answered. “I’ve known Mike since high school. Trust me, if anything he’s homophobic. He refused to go out for football; he said he didn’t want any guy patting him on the butt.”

   “Yeah well, whatever. I must have been about fourteen when I saw that show, I think, Phil Donahue did with the married cross-dressers. I kind of thought it was cool. I tried to tell her about it and that it wasn’t as bad as she imagined. It was then she spouted off about, ‘If it was your husband, you wouldn’t think it was so cool.’”

   “Well, she does have a point there. I mean, when it doesn’t affect you personally, it’s pretty easy to look at it objectively. But when you have to deal with it in your own family …” I shrugged.

   “OK, Mike’s your longtime friend. What do you think about him cross-dressing?”

   “It’s not that much of a surprise, really. Mike’s never been that much of a jock or macho type anyway. So, I guess if he has a feminine side, it could be easily understood. That plus the fact I know he’s not gay… OK, so if he wants to dress up in women’s clothes in his spare time, then who’s it gonna hurt?

   “You know, now that I know that, it kind of explains the times back in high school he took so long to answer the door when I came over unexpected and he was alone in the house. Sometimes it seemed like he’d take ten minutes to answer the door when I knew he was there. He must have been scrambling to get out of his sister’s clothes.”

   “I’d like to find out,” she replied.

  Now there was non sequitur. “Find out what?”

   “If I’d think it was cool if it was my husband.”

  I blinked at her. “…And how do you intend to do that? Divorce me and marry Mike? Granted, Lisa being pissed like she is, just might trade you straight across. However, I’m kind of partial to the wife I’ve got and I don’t think I want to take the time to break in another one.”

   “No silly,” said Carrie, smiling as she snaked her arms around my neck. She gave me a light kiss that was more than a peck, but less than passionate and continued, “It wouldn’t be the same if I didn’t already have feelings for him… and I have feelings for you, not Mike.”

   “Well, I’m not a cross-dresser, so how are you going to find out?”

   “You could be, you know.”

   “What!?” I asked in shock. “Just what do you mean by that?” I wasn’t sure if I should be offended or not.

   “Look, it’s not like you’re not all man, especially where it counts,” she told me as she rubbed her hips into me. “However, you do have… fine features and it wouldn’t be that hard to make you passable as a woman.”

   “You’re joking right? This is just some weird fantasy brought on by Lisa’s taunt about it not being your husband. You don’t really think you could make me look like a woman.”

   “Well, maybe not a hot, sexy woman, but a woman. I know plenty of women who look more masculine than you do without you trying to look feminine.”

   “Well that’s true enough. I’ve seen plenty of butch women, but I don’t think that I’m that fine featured. Those butch women still look like women because that’s what they are and no matter how you dress me, I’ll still look like a man, because that’s what I am.”

   “What? You mean that you’ve never seen someone and couldn’t be sure whether it was a man or a woman, until you took a good look and considered all their features?”

   “Well, OK, I guess I’ve seen a few of them. … Wait a minute! You’re not saying I’m like that? I definitely look male.”

   “Well sure… now. But, if we were to blur the edges, we could make you look feminine enough to make people unsure and if they’re unsure, it won’t take too much to make them accept on face value what you’re presenting.”

   “Whoa, wait just a minute. You’re not thinking of dressing me up as a woman and taking me out in public, are you?”

   “Well, not really, at least not until you’re comfortable with it. That will probably take a while… but maybe I’d tell Lisa that I still think it’s cool… that is if I still do.”

   “You know you’re crazy, don’t you?” I told her as I leaned in and kissed her. When I broke the kiss, she leaned back and nodded her head. “Now tell me. Is this just something you want to do to prove Lisa wrong or is this some deep-rooted thing coming out of your past because that TV show fascinated you so much?”

  She looked thoughtful and said, “Mostly it’s to convince Lisa that I meant what I said. But I guess if I was honest, part of it’s because I was taken by that show and, though it’s not been an intense desire, I’ve always wanted to see and experience a cross-dresser in real life. Mind you, I hadn’t thought of that show since high school, until Lisa told me about Mike”

   “We could always call Mike and invite him to introduce us to Michelle.”

   “I guess that would satisfy the experience it ‘in real life’ part, it wouldn’t do anything toward proving to Lisa that it doesn’t make any difference if it’s my husband.”

   “I’m not going to get out of this, am I?” She shook her head no. “So, OK, what do I do? Go in and find one of your dresses I can squeeze into and then call Lisa to come over or what?”

   “No, I don’t think dressing you up and showing Lisa would prove anything. One time does not a cross-dresser make. I guess you’d need to change your lifestyle a bit.”

  I could feel the dread building in me and I knew I should put a stop to this crazy idea. Then again, I’ve never been able to dissuade her when she gets some wild idea of what we should do in her head. I usually just end up going along. If I don’t, I have to put up with a pouty wife until I can come up with some really great thing to do that gets her mind off of whatever she’s dreamed up. Of course, if she really gets enamored with an idea it’ll just come back later in some disguised form.

  ‘OK, what the hell,’I thought. ‘It’s just clothes. No big deal, right?’

   “So exactly how do I change my lifestyle? I mean just what’s involved?”

   “Well, I guess you’d have to get used to wearing some different things on a regular or at least a semi-regular basis.” She was hedging. That couldn’t be good.

   “I’ll have to do some research. I’ll get back to you on it. You’re not going to renege now are you? You’ve committed to do this haven’t you?”

   “Maybe I should be committed, but yes, I’m committed. You wouldn’t let me change my mind now. Just don’t keep me in suspense too long, OK?”

   “Promise.”

  She busied herself in the kitchen getting dinner ready while I went to the computer to check my email. She served up liver and onions with fried potatoes and whole kernel corn; pretty nearly my favorite meal. If she’d topped it off with German chocolate cake with vanilla ice cream I’d have thought I’d died and gone to heaven. I know she didn’t plan that dinner, it was Friday night after all and the object of her taking the day off was to do all the Thanksgiving prep. So I’m pretty sure it was a reward for my agreeing to go along with her cross-dressing scheme.

  After dinner I plopped myself in front of the TV. Next Thursday would be all about the bowl games and Friday would be the civil war. Tonight I’d just look for a movie. Something with action in it and not some sappy countdown to Christmas special. There wasn’t much to choose from, but TNT came through with a John Wayne movie,

  It was Carrie’s turn to glue herself to the computer. Carrie waited until I paused the movie and stood to head for the kitchen and another cup of coffee. “Hold up a minute,” she said, tape measure in hand. She measured my chest, twice, my waist and then my butt and nodded. “Thought so,” she concluded and smiled at me. “Thanks,” was followed by a quick peck and off she went. She disappeared for a moment and then breezed in wearing her jacket. “I’ll be right back. I’ve got just enough time to get to the stores before they close,” she said and was gone before I could ask why she needed to go to the mall in the first place.

  I was surfing the channels on TV when Carrie popped her head back in and asked, “Done with your movie?” I nodded my head and she came over and gave me a quick kiss. She was in a very good mood.

   “OK, what’s with this?” I asked Carrie as I leaned into the bathroom, holding up a pair of panties I’d found in my dresser drawer. It was one of about a dozen in various pastel colors.

   “Well, I think you need to ease in to the cross-dresser thing slowly. You can start by wearing panties on the weekends,” she smiled.

   “Panties on the weekends?”

   “Well, yeah. That’s where most cross-dressers start, with panties or lingerie of some sort. I just can’t see you wearing a slip just yet. I think you can get away with under-dressing, even at work, once you get used to them. Though after you get to liking the panties, you could start wearing camisoles instead of your wife beater under shirts.”

  ‘Liking the panties?’ I thought. ‘Yeah, sure.’

   “Don’t you think, what, a dozen pairs are a bit much?”

   “Oh no, that’s bare minimum for a woman and many cross-dressers have lots more than that. A dozen is just a good starting point. Once you get into it, you’ll probably have a dozen each in three or four different styles.”

   “I’m going along with this, but just so you know, it’s only until we get Lisa to give Mike a little slack, OK.”

  So I got dressed putting on the plain white pair that could almost pass a men’s underwear, except that the waistband was too thin and there was no Y-front opening. And then there was that little bow in the middle of the front. That bow was the only thing that made it easy to tell front from back. Oh yeah, thin nylon…soft, silky nylon.

  I’d never worn anything like them. I never had on anything made of nylon before. Their feel was absolutely sensuous. I noticed my heart rate pick up and my breathing got a little shallow as well. I took several minutes to regain my composure and finish dressing. I can never remember being aware of my underwear before that day, but I was aware of the panties all day long. Every time I sat, stood, bent, twisted or just about any move I made, the panties let me know they were there. I’ve got to tell you it was really distracting.

Chapter2
New sensations

   “You're wearing your panties?” Carrie wanted to know over breakfast.

   “Ah… yeah.”

   “So what do you think?”

   “They’re different.”

   “You like them?”

   “It’s too early to tell. I’m still getting used to the different fabric and the fit.”

   “They should fit you fine. I measured your hips and waist. I bought them to fit your hips, because the waist is forgiving. It has to be because women retain water during their time of the month.”

   “Well, yeah, they fit fine, but they don’t fit like men’s underwear.” She looked at me like she was waiting for me to expand on that statement. “Men’s underwear doesn’t ride as high on the hip and there’s a bit more room up front for the equipment, if you know what I mean.”

   “Oh, I could have bought you hip huggers, but I wanted to start you out on full briefs, as that’s what most cross-dressers started on. I’ll be glad to get you some others, if you don’t like these, only underwear can’t be exchanged, so you’ll get a head start on your panty collection.”

   “I don’t think that’ll be necessary. I’ll get used to these. It’s not as if they’re uncomfortable, or anything. They’re just different than I’m used to.”

  She smiled a wicked smile and asked, “Did it turn you on a little to put them on?”

  I wasn’t sure how to answer that. Yeah, I felt a little stirring down there, and the heart rate-breath thing I mentioned earlier, but I didn’t want her to think I was some kind of pervert who got off on wearing panties.

   “Well, it’s not exactly a turn on, but it is a bit exciting… you know the forbidden fruit thing.”

Her smile got bigger. “So you do like it.” I blushed and she stood and came over to hug me. “It’s OK to like it. If you didn’t like it at least a little bit, I’m not sure the experiment would really give valid results.”

   “I’m not sure that I’m really comfortable with liking cross-dressing.”

   “Oh that’s just your macho upbringing. You’re afraid that it detracts from your masculinity. Trust me it doesn’t. There’s something masculine about every woman and something feminine about every man. I haven’t noticed your feminine thing yet. Maybe it’s clothes and you’ve never had the opportunity to discover it. But now you have. Give it a week or so and then we’ll step it up a bit.”

   “Step it up?”

   “Yeah, you know add the camis to your wardrobe.”

   “You don’t expect me to wear the panties every day, do you?”

   “Not to start with, but wear them as much as you can bring yourself to. I’m betting after you get used to them, you’ll feel funny when you’re not wearing them. You know, I got you a nightgown as well. Wait until you sleep in that. The way you seem to like the feel of mine, I’m sure you’ll love yours. I’m betting that regardless of what else happens, you’ll never go back to PJs again.”

  Well that night I did find out what it was like to sleep in a nightgown. The nightgown was every bit as luxurious and silky feeling as the panties. It was made of a satin finish nylon in a pastel green. The neckline was square cut with lace and ruffles the sleeves were extremely short, cap sleeves, they almost stood straight out from the shoulders. The hemline hit me a little lower than mid-calf.

  At Carrie’s insistence, I kept the panties on. Looking back, I somehow think that Carrie was conditioning me, because she was pretty amorous over the weekend. Two days and three nights of that and I have to admit that changing back to tighty-whities Monday morning was a bit of a come down.

  Monday night when I got ready for bed, I looked for my PJs and found my nightgown hanging from the hook behind the closet door. My nightgown somehow I never thought I’d ever think about a nightgown like that. ‘Oh well it was pretty nice over the weekend, so why not?’

  When I crawled in to bed, Carrie snuggled up and immediately noticed. “You’re not wearing panties. Don’t you remember, I told you that you should wear them with your nightgown?”

   “Well yeah, but when I wear PJs, I don’t wear underwear.”

   “That’s typical male thinking. Think like a cross-dresser. It’s all about the clothes. A cross-dresser wears whatever they can whenever they can. Put your panties on. You liked the feel of the combination over the weekend, so why not continue? You have enough panties that you can wear them every day. I made sure of that.”

  I don’t remember that I said anything about liking the combo but I couldn’t deny that I did like it, so I got back out of bed and put on a pair of panties. I wasn’t sure just how amorous Carrie was going to be but she did have a point, with the two of us encased in sensuous nylon was a great feeling. Even if she just snuggled up close for a time that was encouragement enough for me to sign on to the idea. Let’s just say she gave me plenty of reason to enjoy the feeling.

  That set the pattern. I simply put a pair of panties on when I got ready for bed. It didn’t take long for me to do it without thinking about it. It’s just what I do to get ready for bed. Take off my clothes, put on the panties and nightgown, drain the bladder, brush my teeth and climb in bed to a loving wife who was always grinning.

  I have to admit that changing back to tighty-whities to go to work, seemed a bit silly, I mean, I was putting two pairs of underwear in the hamper every day. But come Thanksgiving that changed. No tighty-whities.

  Well, I wore panties all four days of the long Thanksgiving weekend, day and night. Even over to her mother’s on Thanksgiving. I was a bit nervous. I was sure that somehow I’d be outed and have to explain to my mother-in-law why I was wearing panties, but the day went off without a hitch.

  To my surprise, it did feel a bit strange when I first put on my jockey shorts on Monday. After wearing panties over the Thanksgiving weekend, I’ve got to admit that I was looking forward to it the next Friday just a little bit. I expected Carrie to make a big deal out of my wearing panties, or at least to ask me about them again, but she didn’t. It was like I was on my own. Here I was in panties for the third weekend in a row and she’s ignoring it. I’m sure that she was aware of it, at least after the fact when she did the wash on Saturdays when seven pairs of panties and five tighty-whities showed up in the hamper.

  And of course every day I was reminded of the weekend when I got into my underwear drawer. Come the next Saturday I acquiesced and wore panties only over the weekend.

  Carrie didn’t push me about the cross-dressing thing, but it was on my mind every waking hour and I’m sure in my dreams. On Friday night I had have more information.

   “So just how do we progress with this cross-dressing thing?”

   “What do you mean?”

   “Well, I’m sure that Lisa won’t be impressed with me wearing panties. To make the point, I’m going to have to wear more than underwear.”

   “True. I’m thinking that we’ll pick up some outer clothes for you and some things that are women’s clothes that don’t necessarily look like women’s clothes. You know that there’s really only small differences in women’s and men’s jeans. There are other things as well.

  Let me tell you about Saturday. That was the day that Carrie was in the bedroom when I got dressed. Just after I put on the panties I’d chosen for the day, she interrupted my routine.

   “Let’s get a little adventurous.”

   “How so?”

   “As you observed, Lisa’s not going to be impressed with underdressing. So, I was thinking that maybe you could try on a few of my looser fitting things to get the idea of what it’s really like to cross-dress.”

  I studied her for a moment. I could tell this was another time when I’d just as well acquiesce.

   “OK, just what do you think I should wear?”

   “Let’s try a top.”

  She opened her closet and got out a blouse. It was certainly loose enough. I went to put it on, but Carrie stopped me.

   “To look good, that top needs something.”

   “What?”

She tapped my chest and said, “A bustline.”

   “Well, as you can see I’ve got nothing to offer in that department.”

   “Let’s see what we can do about that.”

  She laid the top on the bed and dug through her drawers. After some time, she came up with a strapless bra and after some more digging in a smaller drawer, she came up with a small thing that looked like it fell off of a bra… like bra hooks on a piece of elastic. She clipped that to the bra and wrapped them around my chest. Then from my sock drawer, she got three pairs of wool socks that I used to wear when I went hunting. Using three socks in each side, she stuffed the bra.

   “We’ll have to get you something better. This is pretty crude, but according to my web search a lot of cross-dressers use this kind of thing; at least to start.”

  She helped me on with the top. Then she got out a pair of loose white pants that I always thought were just a little baggy on her, but, being a wise husband, I’d never said it to her. I put those on.

  She studied me for a bit and said, “I think we can do better than that.”

  Next came a yellow tunic that struck me just below the butt and she paired that with a pair of black pull up loose leg capris.

   “That’s better,” she said and handed me a pair of knee-highs.

  I took the hint and pulled them on, calling on the many times I’d seen Carrie do that to know how to manage the fragile material. When I pulled the last one up, she dropped my Crocs in front of me.

   “Your Crocs will have to do. They’re not exactly winter shoes, but you’re not going outside. I’ll have to see about getting you some shoes to go along with your new lifestyle.”

   ‘My new lifestyle? Like this is going to persist. I’m going to have to find a way to tone down the money she’s thinking of spending.’ I had a feeling that if I let her run unchecked that we’d have to budget for three wardrobes rather than two.

  I stood and looked at myself in her full-length mirror. Aside from my hair, which was already a little longer than I usually wore it, I did look a bit feminine; certainly not masculine.

   “So, what do you think now? Don’t you think with some make up you could pass for a woman, at least from a distance?”

“My hair’s a bit short.”

   “A little time and that will grow out. What do you think of the clothes?”

“Aside from the pants being a little high water and the top a bit on the long side they’re not really that much different than what I normally wear.”

   “Let’s push the envelope a bit more.”

  She went back to the closet and came back with what I took to be a long skirt.

   “I don’t think I’m ready for a skirt, just yet.”

   “It’s not a skirt, silly.” She held them in front of her and kicked out her leg and the skirt separated in two. “They’re palazzo pants. They’re more for summer, but they are delicious to wear. Cross-dressers don’t really care too much about the season clothes are meant for, at least until they start going out. And, they’ll go better with your sandals. Try them on.”

  OK, so off came the black capris. The fabric of these new pants was indeed delicious. It was soft and silky and, while I couldn’t tell her, I loved the feel of them on.

   “What do you think? Nice huh?”

   “Yeah, kind of nice.”

   “Why don’t you keep that outfit on?”

  I couldn’t do that. The feeling from the pants were about to overwhelm me.

   “The bra’s a bit tight. It kind of pinches.”

   “It’s the most forgiving bra I have. It’s a bit stretched out; so much so that I can’t wear it any more. It tends to sag on me. We’ll have to see about getting something that really fits you.”

  If I ignored my head, I didn’t look bad. Not the kind of thing that would catch a guy’s eye, but not exactly flat chested either.

  I quickly changed back to what I was going to wear; jeans and a tee-shirt, but kept my Crocs on. Carrie called me a spoilsport in a good-natured way. I told her I needed to do a quick tune up on my car. I’ve always done my own mechanic work and with modern cars, it was super easy compared with what I learned from my dad. I just needed to replace the sparkplugs and ignition wires. I rotated the tires while I was in the garage. Carrie did allow that she was glad that I wasn’t wearing her clothes when I was working on the car when she left for some unplanned shopping trip.

  To be continued…