Title

By Patricia Marie Allen

Chapter 5
Happy New Year

  As I got dressed on Monday, after four days straight of wearing panties, I almost automatically put on panties. When I realized what I was doing, I thought, ‘I’ve lost it, totally lost it. I’m choosing to wear panties because I want to, not because Carrie wants to know if she’d still think it’s cool when her husband’s a cross-dresser. I hope she does, because if she doesn’t, I don’t know if I’ll ever really be able to go back to wearing jockey’s full time again.’ It had only taken a couple of weeks to get me hooked on panties and sleeping in a nightgown. ‘God help me, I’m a cross-dresser. How long ’til I’m prancing around in dresses? ... Oh yeah, New Year’s Eve.’

  That thought sobered me and I changed back to my tighty-whities. It unnerved me to think that I was getting into this cross-dressing thing. I really needed to assert my masculinity before I lost that part of me. It was bad enough that I’d succumbed to sleeping in a nightgown. I wondered if Carrie was right; could I ever go back to flannel pajamas? But then the thought of just how good it felt snuggling up to Carrie in her nightgown jumped into my mind. ‘OK,’I allowed,‘I’ll give her that, but today I’m going manly.’

  I fished out one of my wife beater undershirts and quickly dressed for work. I went totally men’s clothes from the skin out. By lunch time I was regretting my decision. After four days of wearing soft women’s clothing, everything I had on seemed rough and scratchy. That was ridiculous. The clothes I had on were the same kind of thing I’d been wearing before and it was never rough or scratchy.

  Tuesday, I opted for panties. ‘God help me, I prefer women’s underwear to men’s.’

  As I mentioned before, normally, we’d spend New Year’s Eve with Lisa and Mike, and the visiting couple would spend the night to avoid all the drunks on the highway. It was our turn to host, but when Carrie called Lisa to coordinate the refreshments, she was informed that they would be staying home for New Year’s Eve.

  “Too bad, I was hoping we’d have a chance to let them see you completely cross-dressed. I kind of get a kick out of people not realizing you’re cross-dressed. Especially Lisa.

   “Oh well, we can throw caution to the wind and you’ll have a chance to wear your heels and the dress I got you for Christmas.”

  Nothing would do but that I totally cross-dressed starting with Thursday, which included the bra all stuffed out, all four days of the weekend. That bra really needed some help. Even with all my pecs pulled up and the straps as tight as possible it just didn’t quite look right.

  Thursday morning, I was told that I really needed a good, close shave each day over the weekend. I’ve got to tell you, standing in front of the bathroom mirror in a nightgown watching a woman shaving her face presented a totally incongruent picture. Carrie was in the bedroom when I came back in.

  “What would you like to wear today?” she asked.

  “I hadn’t really thought about it.”

  “How about one of my blouses and Capri pants or a skirt?”

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

  She laid out three blouses.

  “Choose one,” she said and went back to the closet.

  They were definitely from the feminine end of her wardrobe. One was pink, which I passed on immediately. I just couldn’t even consider pink. The second was a pastel yellow with three-quarter sleeves and an extra floppy collar. The third was white with a lace-trimmed collar and long flowing sleeves that had elastic at the cuffs which were lace trimmed. I’m not sure why, but I chose the white one. Based on color alone, I guess it was the least feminine.

  Carrie came back with her white capris. She looked down at my legs. “You know, you’re going to have to shave your legs. You don’t have much, but you’ll want to wear knee highs and what you do have will be very visible.”

  “But who’s going to see them? Just you and I, so no harm no foul.”

  “I’ll let you get away with it today, but when we dress up for New Year’s Eve, you definitely want to have hairless legs.”

  I let that part slide. I put on clean panties and pulled the carpi pants on before taking off the nightgown. I’m not sure why, but it seemed a bit unnerving to strip down and change panties while my wife was watching.

  Carrie then supervised me putting on the bra and putting in the filling. She did a much better job of shaping them than I did. On went the white blouse and capris. I wore my Christmas sandals.

  “There,” she said, “fully cross-dressed. Shall we see what we can do with your hair and some makeup?”

  “You never wear makeup around the house.”

  “That’s true, but I’m not trying to look like a genetic woman. I am one. Cross-dressers on the other hand really want to look the part.”

  “I don’t know about that.”

  “OK, let’s compromise. Less is more. Lipstick and mascara and you put them on yourself.”

  So I found myself, mascara wand in hand, learning the fine art of darkening the eyelashes without poking my eye out. It only took me three tries to get it on the lashes and not all over the eyelid and I only poked myself in the eye once. Compared to that, lipstick was a breeze. I did have to negotiate with Carrie about the shade I put on. Somehow she had the idea that all cross-dressers would want dark red lipstick. I on the other hand would have happily gone without.

  I spent the morning taking in the feeling of it all. The top was a polyester blend and much lighter, that is, thinner than any of my shirts. Every time I looked in a mirror, I was taken with the fact I could see the outline of the bra. And the way my hair was tousled along with the mascara and lipstick… I doubted I could pass, but it was far from the androgynous look that I sported when we were last at the mall.

  Each day saw me fully cross-dressed. Of course you know she got lots of pictures. Most of them were candid. After the second day, I’d pretty much come to the point of being able to ignore the clothes and just do whatever I’d otherwise be doing.

  

  Then came New Year’s Eve. By then, Carrie had me picking out my own girlie outfit and just left me to it while she made breakfast for us. So I stood in my robe perusing her side of the closet. I thought about this evening when I’d be wearing that dress. I wasn’t really sure about how that would feel. It was bound to be a culture shock. I thought I’d try to mitigate that as much as possible. I picked out a lavender blouse with hidden buttons trimmed in lace. The hemline came down to just below my crotch. It had a thin belt that was supported with some thread belt loops. I didn’t pull it really tight, but just enough to make my waist look a little smaller. For pants, I picked out a slinky pair of black pullups. I put on some nude knee highs and those sandals from Christmas.

  In the bathroom for the second time; I put on some lipstick and mascara. I did much better this time. I got adventurous with the lipstick and tried the lipliner (I learned that’s what the colored pencil was called). I wasn’t really any good at doing my hair, so I just brushed it down over my ears and then fluffed it up with my fingers. Feminine? I don’t know.

  When I went into the kitchen, Carrie was impressed with my efforts and gave me a light kiss. “Don’t want to muss your lipstick.”

  We pretty much lounged around most of the day. Carrie got dinner a little early.

  “Isn’t it a little early for dinner?”

  “A little, but we’ve got to get ready for the evening. It’s a small party, just you and me, but I still want to make it festive. And remember, it takes women longer to get ready for dress-up events, and this year, we have two to get ready, and one of them,” she pointed at me, “doesn’t have a clue about how to do it, so it’ll take that much longer.”

  Right after dinner, I found myself in the tub in a bubble bath; the first I’ve had since I was five years old. The bubble bath was scented with lavender. Carrie encouraged me to just lay back and relax. I have to admit that it did feel nice. I don’t remember the last time I actually had a bath. The water felt… I don’t know… slippery?

  After a bit, Carrie came in decked out in some really fancy lingerie with a light robe over it. I was instructed to lift first one leg, then the other out of the tub as she shaved them to above the knees.

  After the bath, I slipped on a robe and met Carrie in the bedroom. On the bed was some more fancy lingerie. It appeared to be a match for Carrie’s but in a different color and obviously in my size. There in the middle of it all was a package of sheer smokey black pantyhose, queen size. Carrie didn’t wear queen size. She had obviously been planning this for some time and had surreptitiously purchased the array.

  On went the panties first. Then Carrie tutored me in the art of putting on pantyhose. There is quite an art to it. They don’t go on like socks or pants or even like knee highs. You have to coax them up each leg slowly. Once on, I was amazed at the feel. My freshly shaven legs were sensitive to the gentle caressing of the shear support fabric. The bra was new as well and matched the panties. Carry had made some falsies out of birdseed in knee highs to fill it out with. Then came the slip. I knew I was in deep trouble once it settled around my torso. The bubble bath really made my skin soft and the silky nylon of the slip slithered its way to just above my knees.

  Carrie grinned as I looked down and smoothed my hands over the fabric. After a time, she took my hand and guided me back to the bathroom. Where she went to work on my hair, which I could see was getting way too long. Soon it was going to be a problem keeping it looking neat and tidy. Somehow, she managed to make it look really feminine. Then came that full makeup she’d done before. Soon the mirror showed that sister I never had.

  Back in the bedroom, she helped me on with that dress and into some heels I’d never seen before; not the clunky heel, but not spikes either. But real honest-to-goodness high heels. She put on her own dress and had me zip it for her. Donning her heels, she anounced, “Time to party.” And we went to the living room.

  The table was spread just as if we had company. Chips and homemade dip, little smokies in barbecue sauce and a bowl of home made eggnog. I got a few lessons in ladylike behavior. We sat on the couch and watched old-time movies in black and white. Feasted on the snacks and eggnog. Carrie introduced me to girl talk. We noted the style of dresses the women in the movie wore and compared them to modern movies. We discussed current fashions.

  Come the witching hour, we tuned in to the Time Square ball drop, delayed for our timezone and counted down the New Year. She grabbed me and we kissed. Not the usual New Year’s kiss that we’d have done if Mike and Lisa were here. No, this one had some fire in it.

  After some very vigorous bedtime activity, we slept in in the morning.

Chapter 6
Putting it to the test

  A week from that Friday, Carrie and I had planned dinner out with Mike and Lisa that evening, and I hadn’t confirmed those plans. On the way home, I remembered and wondered if those plans were still on. And if they were, had Carrie said anything to Lisa about her experiment.

  “Hi Hon,” I said as I came in. “Are we still on with Mike and Lisa tonight?”

  “Yeah. She wanted to cancel, but I talked her into trying to maintain the normality in their marriage.”

  “I was wondering if they were going to be OK. I haven’t had a chance to talk with Mike since this all started. Has she softened her stance on his cross-dressing?” I asked as we went to the bedroom to change.

  “You haven’t had a chance to talk with him because he’s not allowed to be alone with any men. So, no, she made him promise to stop and even made him purge.”

  “Purge?”

  “That’s what CD’s call it when they throw out all their femme clothing. It’s usually an effort to ‘cure’ the cross-dressing thing. From what I’ve found out, it’s a waste of money. They always end up going back to it. I’ve tried to talk to Lisa about it, but she says until it’s my husband, I don’t have any room to talk.”

  I noticed that she was putting on a cami that I’d not seen before and remembered that she said I’d be wearing camis next. She caught me looking.

  “See something you like?” she smiled wickedly

  “Sure do.”

  “Me or my cami?”

  “You in your cami.”

  “Speaking of camis, I bought you some when I bought your panties. Wanna try them out? They really feel nice against your skin,” she said, rubbing the material against her stomach.

  Somehow I was unable to speak. It was like all the saliva had been sucked out of my mouth. I mutely nodded. She smiled, walked to her closet and retrieved a shopping bag from a lingerie shop.

  “I didn’t give them to you that first weekend, though I was tempted. I didn’t want to overload you at first. I think you’re ready now. You’ve already worn the panties under your work clothes, so this weekend you can add these.”

  She dumped the bag on our bed.

  “You didn’t tell Lisa about your experiment, did you?”

  “No… I didn’t think you’d appreciate that. Besides, unless you really cross-dress because you like it, it wouldn’t mean much. Right now, you’re… we’re just experimenting with it.”

  “Right now? Do you think I’m going to become a full-blown cross-dresser?” In truth, I was working real hard to convince myself that I was only experimenting with the cross-dressing.

  “Well, so far, wouldn’t it be fair to say the experience has been pleasant?”

  I didn’t know just how much I wanted to admit, so I tried to think of how to shade the truth without resorting to a lie. In the end, I had to allow it was. “Yeah, I guess so.”

  “Well then, people who do things that are pleasant tend to keep doing them.”

  I was wearing pastel green panties, and I knew I had a green sport shirt that I could wear, so I picked up the matching cami. “I guess I’ll wear this one. I did the underdressing thing again today you know, just to keep with the spirit of your experiment, and I chose the green ones that match.”

  Carrie grinned. “You just stick to that story. Don’t let anyone persuade you otherwise. But if you’re going to shower before we go out, you probably want to wear clean underwear… I know I did.”

  “What story?”

  “That you’re underdressing ‘just to keep with the spirit’ of my experiment. Just as you’re wearing them all weekend and changing into them in the evening was keeping with the spirit of my experiment. Underdressing was frosting on the cake and really wouldn’t have to come for maybe a year or more if you were the average cross-dresser. Most cross-dressers have been at it for years, even more than a decade or two by the time they reach your age. The only explanation for you underdressing without being prompted to would be that you got some kind of benefit out of it. That is the first time was ‘pleasant’ enough to repeat the act.” She had the most self-satisfied grin on her face as she explained her logic to me. “But put that all aside and stick to your story that it was ‘just to keep with the spirit’ of my experiment.”

  I knew better than to pursue that… If it came to a debate, I was short of good logic to defend myself. I just shook my head and undressed to take the shower she mentioned.

  When I came out of the shower, Carrie had laid out an outfit for me to wear. I wasn’t sure about it. Some of it was new things I’d never worn. The blue cami and panty set was to be expected, but there was a slightly darker blue shirt and light grey close-knit pullover sweater I’d never seen. The pants I recognized from some that she had looked at when I was with her. They looked a lot like my charcoal grey slacks. Also, there was a pair of black dress socks. Not that I don’t normally wear black dress socks, but these were a lighter weight than any I’d ever had before. She completed the outfit with my “Italian” loafers.

  I figured that it was pointless to discuss what she’d laid out. I pulled on the panties. I was used to them enough that there wasn’t any kind of shock, though I still kind of liked the feel of them. When I slipped on the cami, I kind of felt a little naughty much like with the slip on New Year’s Eve. The feel of nylon draped across my naturally hairless chest was a thrill. ‘I can’t let Carrie know how great this feels,’I thought as I quickly donned the pants. I put the socks on and I was taken with how light they really were. Aside from the ribbed knit and opaque black color, they could have been women’s knee-highs. That was the first time I wore the “Italian” loafers and they felt good on my feet. Much lighter than my others and really comfortable.

  I was good with it all until I put on the shirt. If possible, it felt more luxurious than the cami. It had the feel of silk. I took it off and checked the label. Sure enough. 100% silk, size 14. ‘What the hell kind of size is that? … Oh well, it feels great, especially over the cami.’

  I slipped it back on and fumbled with the buttons. What the hell?

  “Carrie,” I called out as I went in search of her.

  “In the family room,” she called back.

  “What’s with this?” I asked holding out the front of the shirt.

  “They’re called ‘buttons’,” she told me as she walked up and took one in her hand and buttoned it. “They go into the button holes and keep the garment from gaping open.” She finished buttoning me up and grinned.

  “I know they’re buttons but why are they on the wrong side?”

  “They’re not on the wrong side. See? They’re the same as mine,” she said as she unbuttoned one of her buttons.

  Suddenly I got it. I was wearing a blouse. “This isn’t a shirt, it’s a blouse!”

  “Well, yes, cross-dressers often wear blouses.” She stroked my chest and rubbed the combined fabric of the cami and the blouse together against my skin. “Doesn’t it feel luscious?”

  She had me there. It did feel great. “But a blouse… with the buttons on the wrong… other side. Isn’t that kind of noticeable? It’s not like the panties or the cami. They’re under other clothes.”

  “The buttons will be ‘under other clothes’ when you put the sweater on.”

  I went back and put the sweater on. I was doubtful that it would look alright, and was prepared to veto the whole idea. I stood before my wife’s full-length mirror and critically examined my look.

  Personally, I thought the whole thing looked a bit femme.

  “Ah, just the look I was going for,” Carrie said as she walked into the room.

  “You don’t think it too femme?”

  “Not femme, androgynous.”

  “Androgynous?”

  “Yeah, neither masculine nor feminine, but something in between. You see it as being on the femme side because you’re used to being definitely on the masculine side.”

  “I’m not worried about how I see it; I’m worried about how others will see it.”

  “I think it’s just enough to put questions in Lisa’s mind without shouting ‘Hey look, I’m cross-dressing’.”

  

  I had that nervous thing going as Carrie and I walked into the restaurant to meet Mike and Lisa. The girls did the hug thing while Mike and I nodded. “Hey, long time no see,” I said.

  “Ah… yeah, me and Lisa’s been a bit busy lately.”

  Dinner was a bit stilted. I was on edge because I was wearing women’s clothes. On the way to the restaurant, I’d figured out that the socks were women’s trouser socks and the sweater was a woman’s sweater as well. It just felt too soft to be a man’s. When I confronted Carrie, she caved right away and seemed really pleased with herself that she’d got me to wear it. That left only my shoes and slacks. I knew for a fact that the shoes were women’s, and the slacks as I said, looked like some she’d been examining in that woman’s casual clothes shop, so I was sure they were women’s as well. That meant that I was wearing all women’s clothes… out in public.

  Funny thing was, no one, not the hostess, the waitress, or the cashier at the restaurant, not Lisa, nor did Mike acted even a little bit like they even noticed. At the end of the evening that was kind of a thrill.

  I asked Carrie, on the way home, “Do you think anyone had any idea what kind of clothes I was wearing?”

  “Nah, they were all too caught up in their own personal thing to even give it a thought. Now if your top had had ruffles at the collar or the cuffs or maybe if the sweater had been pink instead of grey, then they would have at least done a double take. But so long as the clothes you wear are from the masculine end of women’s clothing, you can wear pretty much anything without anyone paying attention. I’ll have to see what I can do to get you some more pants that are really women’s but don’t necessarily look like it.”

  Saturday morning, after a husband wife kind of cuddle, I went to take a shower. Carrie stuck her head in the door and called over the roar of the shower, “I put some things on the bed. Try them on and let me know what you think.”

  Coming back into the bedroom, what I saw were some shorts and a polo shirt. The shorts were tan and knee-length; I hadn’t gotten around to getting any for myself. Carrie had some and had said I should get some so we could match, so I guessed she got tired of waiting for me and bought them herself. The polo shirt was black with no design. A while back, I’d bought some Crocs; their Prepair™ II Slides. Carrie had them out as well. OK, so it was a warm day out, well warm for January. We’ve always joked that when the temps got above 60, Oregonians broke out the shorts and sandals. Looks like it was a reality today. My matching navy blue panties and cami were there as well. As I got dressed, the only odd thing I noticed was the fly on the shorts was a little short. I’d have to lift things a little when I took a leak.

  I found Carrie in the kitchen. She poured me a cup of coffee and asked, “What do you think about the outfit?”

  “OK I guess. A little early in the year for shorts, but I guess it’s warm enough to get away with them. It’s supposed to be 72̊ today.”

  She smiled as she flipped the hot cake she was cooking.

  We ate breakfast as she outlined her plan for the day. “Today, I want to take you shopping. It’s time to buy you some things you can wear that no one would notice, but are women’s clothes.”

  “You’re not going to have me trying on things in the women’s department are you?”

  “No, but I do want you to see what I’m buying. We have to agree that you could get away with wearing them without comment.”

  Off we went to the mall where we hit the women’s department in several major stores. I ended up with four shirts where the only giveaway was the buttons on the wrong… OK, other side. And four pairs of slacks, all with the fly going the other way. I was a bit hesitant about them, but Carrie assured me that no one would pay enough attention to pick up on the subtle differences. One of the stores we were in had unisex changing rooms where she did have me try on one outfit, just so I could see how it did look. To cover up my nervousness, I also took in a pair of men’s slacks and a shirt carefully placed over the women’s things as camouflage. I had to agree that with the shirt tail out, it would take an extraordinarily observant person to notice anything. Carrie wanted me to wear the outfit home, but I refused on the grounds that while no one looking at it was likely to notice, the cashier surely would realize she was ringing up women’s clothing that a man was going to wear out of the store.

  We got home with our purchases and Carrie sprung another surprise on me.

  “So how did you like your first time?”

  “What do you mean, my ‘first time’?”

  “Well, today you went clothes shopping fully cross-dressed… 100%.”

  “What do you mean? Cross-dressed 100%?”

  “Those are my shorts and polo shirt, and of course, your panties and cami.”

  I was stunned and looked down at my clothes. It was then I could see the buttons on the polo shirt were on the wrong side marking it as a woman’s and that being the case what does the short fly on the shorts say about them?. “But what about my shoes? These are my Crocs.”

  “The Crocs are unisex. Look on the bottom where the size is marked.”

  I looked; there were two circles. One had a 9 in it, the other had an 11.

  “The nine is the men’s size; the eleven is the women’s size. Those could be women’s as well as men’s.

  “The only thing missing was that you weren’t wearing a bra. Maybe we’ll see about getting something that can be overlooked, and after you’ve worn it around the house for a while, you can wear it under that kind of outfit. But it’ll take a while before you feel natural in one.”

  I sat dumbfounded staring at the bottom of my shoe. I guess I knew when I bought them they were unisex, but I never really gave it any thought. They were my sandals and therefore men’s sandals. I’d worn them maybe a hundred times and never gave a thought that women could be wearing the exact same shoe.

  “Now that you’ve been out of the house shopping fully dressed in women’s clothes, it shouldn’t be that hard to do again. I think we should get you out at least once every weekend just for you to get the feel of it.”

  “What? Are we on some kind of schedule? Is there a time limit for me to become a full-blown cross-dresser?”

  “Ah… well, Lisa is kind of simmering while she tries to come to grips with Mike being a cross-dresser and she’s going about it all the wrong way. She’s in denial and making Mike miserable. I guess, since you’ve shown promise in the cross-dresser direction, I’d like to put you on a fast track. I mean, you don’t have the obstacle of a disapproving family or wife or whatever to hold you back. So why not push the envelope and progress as fast as you can stand the pace? In the end, it’ll really help Mike and he is your best friend.”

  “Well, let’s not rush things too much OK? I may have the blessings of my wife to pursue my feminine side, but I’ve got twenty-eight years of 100% male thinking to overcome. If we jump ahead too fast, I think I might just freak out.”

  “Don’t worry hon. We won’t take you out in dresses any time soon. For that part, we’ll wait for you to want it. I will, however, push you a little to experiment with the next level as soon as you’re comfortable where you’re at. Part of the object of this experiment is that at some point Lisa knows and can see that I’m cool with it. And so far, I love it.”

  “I can’t believe we’re standing here discussing me becoming enamored with women’s clothes to the point that I’d want to wear a dress… outside the house even. At this point I’m not even sure that wearing one in the house is something I want to do.”

  “Are you forgetting New Year’s Eve? You enjoyed your evening if I’m any judge.”

  “Ok, ‘again’, but that was different. That was something special. I can’t see doing that again any time soon.”

  “All in due time, my dear, all in due time,” Carrie grinned.
  I kept Carrie’s clothes on the rest of the day.