Chapter 9
Gaining a better look
  While I was preoccupied, she was looking ahead and making plans for me.

  “You really need to let your hair grow out some more, but in the meantime, I think we should get it styled. You know different parts of your hair grow at different rates and for it to look right as it grows out, someone who knows about such things should take care of it. Just a little trim about every two weeks, to keep things growing even.”

  I snapped back out of my wool-gathering. “What!? Are you suggesting we tell someone else about our experiment? …Or did you already talk to your hairdresser?”

  “No, but I was thinking I could tell her that you wanted to recapture your youth and grow your hair out, but that I put my foot down on you looking scraggly like some kind of 70’s hippy. Then I could ask her if she’d oversee your journey into the past.”

“I just don’t want to deal with another of your cronies knowing that I’m letting you feminize me.”

  “Oh Alex, I’m not feminizing you. I’m guiding you as you discover your feminine side. You know all men have a feminine side, just as all women have a masculine side.”

  “Yeah, yeah, we went through that before. Call it what you will, but all I know is I’m discovering a lot more of my feminine side than I could have even imagined was there.”

  “Ah… but the question is, do you like it?”

  I opened my mouth to deny it, but just then, my hand told me about the exquisite feel of the fabric. She had me, I did like it. I’d gone to wearing women’s panties and camis fulltime and even dabbled in wearing a bra for no other reason than I wanted to. That didn’t even take into account that these pants sent me into orbit.

  “Well? Do you?”

  “OK, OK, I like it. It’s just that you’re ‘guiding’ me a bit faster than I’m comfortable with.”

  “Look, I have an appointment with Janice on Monday. I’ll complain to her about you wanting to relive your long-haired student days. Then, at the end of the discussion, I’ll ask her if she’d mind overseeing your search for your lost youth.”

  That was that. A statement of fact; no discussion; a fait accompli. It was a done deal.

  “Come on, give me a hand with dinner,” Carrie told me.

  I spent the rest of the evening in that outfit and eventually got to where it wasn’t constantly the only thing I thought about. But there were moments, like when we were watching TV and I crossed my legs. I kind of lost track of the show as I rubbed my calf against my knee. Then I was taken with the fact that I hadn’t simply laid my ankle across my knee as I usually did, but instead, I had knee over knee and I pulled my ankle close to my calf for maximum contact.

  Then of course there were the trips to the bathroom. I couldn’t just go in and take a leak like before. I had to spend some time admiring my reflection. Carrie had done an excellent job of making me look like a woman. I don’t know if I could have admitted it to her at that time, but I doubted that anyone would have questioned me in any situation where I needed to be a woman. Not to mention, in keeping with the illusion, I sat. It just seemed the thing to do.

  When it came time for bed, Carrie had another idea. After I cleaned my makeup off, I reluctantly took off the blouse and the heavenly pants. As I reached around and started to struggle with unclipping the bra, she said, “Why don’t you leave that on?” as she handed me my… ‘oh God,’ my nightgown; the new one. I shrugged and slipped the nightgown on without removing the bra. I was going to find out what sleeping with boobs was like.

  Fortunately, I don’t sleep on my stomach, so lying on my chest wasn’t an issue; but still, the bra was a foreign feeling, especially when trying to get to sleep. That is, not to mention the nightgown. When I got in bed, it kind of swirled around me touching all parts of me at once. The feeling was surreal, something out of The Twilight Zone, like the show on the Sci-Fi channel. I could just hear the voice of Rod Serling saying, “...That's the signpost up ahead - your next stop, the Twilight Zone!”

  It got even more unreal when Carrie snuggled up in her own silky nightie. ‘Oh… my… God…’ I’ve got to tell you, if you’ve never tried it, you should. I mean, even if you don’t approve of cross-dressing, the sensation of nylon nightie to nylon nightie is worth setting aside your prejudices to experience it. I don’t think I can even begin to describe the tactile sensation involved.

  After a bit of snuggle time, Carrie kissed me and said, “Have a good night, I’ll see you in the morning. I can’t wait for the report of how you like your new nightgown.” With that, she just rolled over and dropped off to sleep. I, on the other hand, lay there taking inventory of where my life had gone in the last few months before I dropped into a fitful sleep.

  In the morning, I awoke confused. There was a strange feeling on my body. My legs were bare and something… something soft and silky was wrapped around my middle. When I tried to discover what it was, my arm ran into some bumps on my chest. I immediately became aware of the bra strap. Then the night before came flooding back into my memory.

  I struggled out of bed and quietly slipped into the bathroom. With the long nightgown, it was just too much trouble to hike it up and keep it out of the way, so I just dropped my panties, hauled it up behind and sat. I was a bit groggy anyway, so I’d have probably made a mess and Carrie wasn’t too happy when that happened. Splashes, you know. ‘Hum,’ I thought, ‘maybe I should just sit all the time. What the heck, I do it all the time at work to avoid using the urinal and risking someone getting a look at my underwear. … Yeah, Carrie would like that. The seat would be down all the time and cleaning the bathroom would be easier. … Besides, with the way she’s feminizing me, it just kind of fits. …’

  ‘You know, Alex, you’re flippin’ crazy! What the hell kind of man would be trussed up in a bra, with fake boobs, wearing a nightgown, sitting down to pee and thinking it would be good to do it all the time? Oh crap! I forgot to add that the crazy SOB likes it all…’

  ‘Yeah, what kind of man?’ … That really rattled me, I just realized I really did like what Carrie was doing to me, or to be more fair, with me. I mean, she was guiding, but I wasn’t resisting and I even struck out on my own a tiny little step. Problem was, I let her find out and she ran with it. That’s why I’m wearing the bra with the fake boobs.

  Having finished my business, I stood and looked at myself in the mirror. My hair was a mess. ‘Yeah, time to do something with your hair.’ I picked up Carrie’s hair brush and ran it through the rat’s nest and somehow, though I brushed it every day, I was taken with just how long it was getting. It was well over my ears on the side and reached my collar in the back. I pulled it all back and discovered it was long enough to pull into a high ponytail. Not a very long ponytail, but it looked feminine enough. Especially when I tied it off with one of Carrie’s scrunchies.

  I don’t have a very dark beard nor does it grow very fast, but it was just visible enough that it spoiled the image. So I lathered up and shaved. Now there’s a sight, a rather plain-looking woman in a nightgown with a face full of shaving cream, stroking a razor over her face. It brought to mind a scene from an old movie about the circus. The midway barker inviting people to see the bearded lady, only the bearded lady wouldn’t be shaving.

  It was kind of a downer when I realized that it was Monday, a work day and I’d have to go all masculine again. ‘Where did that thought come from? Since when do I feel bad about being masculine?’ I studied my reflection in the mirror. Not as good as it was last night, but with the boobs and my hair pulled back it was feminine enough to call into question whether I was male or female.

  I quickly took my hair down and stripped for a quick shower. In thirty minutes, I was ready to head out the door. I surveyed myself in the hall mirror and found myself wishing I could actually push the envelope a little for work. ‘Oh well, underdressing will have to do.’ As I realized I was disappointed, I quickly thought, ‘Alex, my boy, you’ve gone around the bend. You’re completely, stark raving mad.’

  I took a break about ten and got myself some coffee in the breakroom. Alone, I brought my hand up to my chest and cupped my pectoral. I was sorry I wasn’t wearing the bra with at least the little stick-on boobs I started with. ‘Please tell me I’m not considering doing that… wearing the bra and booblettes to work,’ I thought, as if I was somehow talking to my own psyche.

  I pondered that for a while and had to admit to myself that I kind of wished I had worn the bra. Upon further reflection, I decided that I was looking forward to the bra that Ann was ordering for me

  It was Thursday afternoon when Carrie called. “I just got a call from Ann. You can stop by and pick up the bras tonight if you want. She’s open until seven.” Wouldn’t you know it; it was a day I was underdressing, but then that was pretty much full time these days.

  My pulse picked up a bit. I was of two minds about it. On the one hand, going to a lingerie shop to pick up a bra for myself seemed a bit over the top. On the other hand, I couldn’t wait to see what a bra that was my size would feel like to wear. … ‘Wait, she said “bras,” just how many did she order?’ I couldn’t concentrate; after an hour, I made an excuse and headed out, only a little early.

  “Hi Alex,” Ann said cheerily as I entered the shop.

  I couldn’t believe it. I was going into a lingerie shop to pick up some special order bras for me… FOR ME!

  “Ah, Carrie said our order was in.” I couldn’t bring myself to say “my bras” or “my order.”

  “I’ve got them in the fitting room. You should try at least one of them on to make sure that it fits right. I’ll give you a little tutorial on adjusting the straps.”

  “Do you really think that’s necessary? You did the measurements,” I said, wondering again just how many bras Carrie had ordered.

  “It’s always a good idea. In fact, it’s my policy for special orders. I can send them back if there’s a screw-up, but only if they’ve not been worn.”

  I felt really awkward being alone in the fitting room with Ann especially when she had me strip to the waist and would then be able to see what I was wearing underneath. I’ve got to give it to her, she was totally professional. She helped me on with it when it became apparent that I didn’t know the first thing about fastening a bra behind my back. She fussed with the bra, tugging at the flesh of my pecs and then adjusting the straps. The bra was amazing. The thing actually fit. It was in a pushup style so it wasn’t exactly without padding. The padding was in the bottom part of the cups to push up what was there naturally and once she got the straps adjusted, there was a modicum of cleavage showing. She went over what to look for when adjusting the straps. As she finished up, the bell on her door chimed and she left me to get dressed. I hesitated for a moment. I decided I wanted to see what it looked like under my work clothes. I wasn’t going back to the office anyway.

  I slipped the cami on first and looked at my reflection for a bit. There was just enough padding under my pecs to push them up and out. Combined with the padding there was undeniably something under the cami. I put on my shirt and stood sideways to get an idea how it would look from the most obvious view. Yeah, I could see the difference, but I think that was only because I was looking. Facing the mirror, I didn’t look much different than a lot of men. I was fit enough that the enhancement might have been well-developed pecs; like I’d spent some time in the gym. I tucked in my shirt, picked up the bag with the other bras, and went back out to the main part of the shop. Ann was just finishing ringing up a woman’s purchase as I walked up.

  As soon as she was out the door, Ann asked, “What do you think? Are they going to fit the bill?”

  I just had to get smart-mouthed. “I don’t know about Bill but they fit Alex.”

  She smiled. “Come back any time and tell your friends about the place. Word of mouth is my best advertising. Oh and when you’re ready for outerwear, here are some shops that offer the same kind of service I do.” She reached under the counter and produced a list. “The star next to the name indicates that you should call for an appointment. They prefer that cross-dressers come in before or after business hours.”

  I took the paper and nodded. “I’m sure that Carrie will be in touch if she thinks of anything else I need.”

Chapter 10
More exposure

  I’ve got to tell you, wearing a bra is a really different experience. Especially one that’s fitted to you and is a pushup bra. What I had worn before with the breast forms was different in a different way. That gave me a sense of what it might be like to have boobs. This one manipulated my pecs to make them look like I really did have boobs, albeit small, extremely small boobs, but boobs nonetheless. Looking down at myself, I could see the bumps, but I had seen other men with that kind of bumps under their shirts, so I hoped that so long as no one who knew me got interested in my chest they should go unnoticed.

  “Hi hon, did you stop by Ann’s?” Carrie asked coming to greet me. “Oh, I see you did,” she continued, looking at the bag I was carrying. She gave me a hug and a kiss. She pulled back, and looked down at my chest dragging her hand over my shoulder, found the bra strap with her index finger.

  She smiled and said, “Couldn’t wait to try one on, huh? What do you think?”

  “Actually, Ann insisted that I try it on for fit. She said if it wasn’t right, she could send it back, but not if it had been worn. Since I was doing that, I decided to see how it looked with my cami and shirt on. By that time, it was just too much work to take it off.”

  “Well, if that’s your story, just stick to it.” She grinned mischievously. “But you didn’t tell me what you thought.”

  “It’s different.”

  “Different, good, or different bad?”

  “Neither actually, just different.”

  She lifted her eyebrows. “Do you like it?”

  “Too soon to tell.”

  “OK, keep it on and maybe wear it tomorrow as well. Maybe by the end of the day, you’ll have an opinion. I’m betting that given how you got used to the forms in the other bra, you’ll not find it an unpleasant experience.”

  Getting ready for work on Friday was a struggle. While I had long since gotten used to underdressing and had really taken to wearing the nightgown after that first night, wearing a bra to work was a big step. I remembered how I’d fondled my pec and contemplated wearing a bra, even wishing I had.

  In the end, I did it. I just wore the one that Ann had adjusted for me. I’d wasted enough time debating whether I’d wear it at all and didn’t want to take time to adjust another one. If I did that, I’d probably end up having Carrie help me with it and I wanted to do it on my own. I was afraid that if she knew, she’d make a big deal out of it and then prompt me to do it again. This was something that I had to do all on my own. I rationalize that it wouldn’t count if Carrie was the driving force behind it.

  I was back to feeling nervous that someone would notice. To say I was distracted that morning would be an understatement. I fought the urge to hunch forward to hide my enhanced pecs. First of all, it would be out of character for me not to have good posture sitting at my desk. Secondly, since I was a suit coat kind of guy, but worked in my shirtsleeves, that maneuver would increase the chances of someone noticing the catch on the bra strap. I really didn’t get much work done until after lunch when I finally got into writing the report on the project that I’d finished on Thursday.

  By the time I went home, I was pretty sure that no one had twigged to the idea that I was wearing a bra. I was a bit giddy as I drove home. When I got there, I feigned needing the bathroom and quickly changed into my casual clothes, which turned out to be those women’s jeans, a woman’s tee, and a woman’s flannel shirt, so that Carrie wouldn’t realize that I had worn the bra to work. To that end, I changed bras. I spent a long time adjusting the straps.

  “I was about to organize a search party. What took you so long?” Carrie asked as she handed me my usual cup of coffee.

  “Oh well, I was adjusting the bra. Ann adjusted the one I wore home, and she told me how to do it, but it’s not as easy as she made it look.”

  “Did you get it adjusted OK?”

  “I think so. It feels right.”

  She stepped closer and hugged me, running her hand up my back so she could feel the bra strap. She smiled and kissed me softly.

  “Dinner will be ready in about half an hour,” she told me.

  I went to the office and checked my email. I also surfed some cross-dressing sites. If I was going to be joining the club I thought I should familiarize myself with what other cross-dressers thought.

  I got lost on the computer; there was just too much information. Carrie came in and told me to get to the table because dinner was getting cold.

  “Oh, I talked to Janet. She has an opening on Saturday, at 10. She’s penciled you in. If we don’t cancel, she’ll expect you then.”

  “OK, just what did you tell her?”

    She shrugged, “Just what I said. You’re feeling a bit old these days and longed to recapture your youth. That you had it in your head to let your hair grow out and it was working on becoming unkempt. I also told her I thought that it was because the company had hired some younger guys that were wearing their hair long.”

  She was right, the company had hired in a couple of twenty-somethings that sported longer hair. The company dress code was nearly non-existent, so as long as it was neat and kept clean, they wouldn’t object. So if I was going to let it grow out, Carrie’s idea of keeping it trimmed up was good.

  “OK, I don’t know about going to a salon to get my hair cut, though.”

  “Not cut, dear, styled.”

  “Hi, I’m Alex Douglas; I have a ten o’clock appointment.”

  “Oh yes, Carrie’s husband. She told me you’d decided to let your hair grow. I can see,” she said, studying my hair, “that she’s right. You do need something done with it. Right this way.”

  I was self-conscious. Not only was I in the quintessential women’s territory, but I was wearing those androgynous clothes that were really women’s but didn’t really look like it, complete with the “Italian” loafers and trouser socks. What’s more, I was underdressed to boot including one of my new bras.

  She led me to a chair and draped a pink polyester cape over me. She started off by running her fingers through my hair. I was glad I’d washed it that morning. It can tend to be greasy. She hummed a bit and lifted first this part and then that part.

  “You know, you’re not the first man I’ve had in here wanting to grow their hair out. Most of them are a little older and are fighting a receding hairline and some even male pattern baldness.”

  “Yeah, well I’m hoping to avoid that baldness thing. My dad and my uncle both had a full head of hair into their eighties.”

  “Maybe you’ll get lucky. We’ll start off with a quick wash and condition. What have you been using to wash your hair?”

  I was a bit embarrassed to admit it, but the tone of her voice told me she’d figured out that it wasn’t a real shampoo.

  “Ivory soap.”

  “I thought so. You should use the Paul Mitchell products that Carrie uses. It’ll make your hair look a lot better. That’s important if you’re going to wear it long.”

  She washed, conditioned, and combed it out. She then pulled up different sections of my hair and clipped it off with some big plastic clips. She did all the cutting with scissors whereas my barber used clippers almost exclusively. But then Joe, starts at the scalp in the back and clips up pulling away from the head as he goes and trims the hairline close on the sides. He does finish off with scissors on the top of the head.

  Janet simply snipped the ends a bit in most places. The longest piece she cut off couldn’t have been more than a quarter of an inch or maybe a little more. Joe went at a haircut like it was a production line, whereas Janet was an artist, paying attention to detail. When she got through with all the sections she leaned the chair back again and washed and conditioned it again.

  “Your hair is in pretty bad shape,” she told me as she was blow-drying it. “I’m going to recommend Paul Mitchell Super Skinny Hair Serum. You should use it for a while. That Ivory soap is good for washing hands, but it definitely did a number on your hair.”

  She brushed my hair out and then hit it with some hair spray. I almost objected to the hairspray, but then I thought about the cross-dresser angle. I remembered some of the info I found on the internet some cross-dressers talked about the “salon experience” and hairspray played a part. So I just rolled with it.

  I contemplated my visit as I drove home. All in all it wasn’t what I had feared when Carrie brought the idea up. Janet didn’t act like there was any more to my growing my hair longer than what Carrie had said she told her. ‘Seems like Carrie’s stuck to her word on this part of the adventure. I’m glad I didn’t just roll with it and let her repeat the scenario that happened with Ann.’

  “How’d it go?” Carrie wanted to know.

  “OK, I guess.”

  “Your hair looks great. It’s a lot neater. What’s in the bag?”

  “Oh, she sent me home with some kind of hair treatment. She said that my ‘Ivory soap really did a number on my hair’.”

  Carrie took the bag and looked in it. She nodded.

  “Well, I’d use it if I were you. Janet knows her stuff and if she said you needed it, then I’m sure you do. When your hair is short, it really doesn’t make much difference but when it’s longer, it needs to be healthy so it doesn’t break off. That’s what causes split ends.”

  “She said that I should quit using Ivory soap and switch to your shampoo and conditioner.”

  “I’m not surprised. I just replenished my supply. Did she say how often she wants to see you?”

  “Yeah, every four weeks. My next appointment is March 20th. She said that she’ll just make it a standing appointment, so the next one will be the 17th of April.”

  “With both of us using it, we’ll need more just after your appointment. Maybe we should buy it in the jumbo size. Usually, only salons buy that size. But in the long run we’d save money.”

  ‘In the long run? How long does she think it will be before I give this up and go back to … back to what? Can I even go back?’

  “What is layering?”

  “Why do you ask?”

  “Because Janet said that by April, she expected my hair would be long enough that we could do some layering.”

  “Oh good. Layering is like my hair. The top and sides are cut shorter than the bottom and the back. It makes it easy to care for and style. The longer hair makes it look like long hair, while the shorter hair gives it volume when it’s teased a little, but it blends in with the longer hair and gives the illusion of it being all one length. You’ll love it.”

  “I’m not sure about it on me, but your hair always looks great.”

  The second time I went to see Janet, I wasn’t as nervous. That was for a couple of reasons. The most obvious was that Janet and the salon were known commodities. The second reason was by then cross-dressing had taken on a familiar air. It no longer felt foreign or strange. In fact, I looked forward to the weekends when I could get out of bed and have my outerwear match my underwear. That and I’d grown to like the feel of those special-order bras. Much to my surprise, I had thought how nice it would be to have a little more to put in the cups. I had experimented with the small gel boobs that I started with. I had to readjust the straps, but with the things stuck to my chest just below my pecs, they combined with the gel pushup pads to really show some cleavage. They did add to the size of the boobs as well, but all my shirts were loose enough that even Carrie didn’t notice that I’d added them to the mix.

  “Hi Alex, come on in,” Janet said as I stepped through the door.

  “Hi Janet.”

  I walked in and sat in the chair. She repeated the process from my last visit.

  “Your hair looks a lot better. You’ve obviously been using the products I recommended.”

  “Yeah, the stuff does make a difference. I was concerned that my hair might be a little hard to manage, but the stuff seems to have made my hair thicker, and that repair stuff makes it kind of stay where I put it. Oh, before I forget, Carrie says with both of us using the shampoo and conditioner, we need some more.”

  “Not a problem, I’ve got plenty in stock.”

  We continued to chat as she washed, conditioned, and clipped little bits of hair. It wasn’t the kind of conversation I’d get at the barber shop. It was more along the lines of what techniques I could use to style my hair. When she was through snipping, she brushed it out and turned me toward the mirror and demonstrated some of them. Somehow this time my hair looked totally different than it had before. It was noticeably longer and fuller than ever before; even counting my student activist days. Then it was long, but it just lay flat on my head.

  “Now, if you were a woman, at this point we’d be looking to give you some bangs.” She brushed the hair on top, forward and then off to one side.

  I felt a cold chill go down my spine as I looked at my reflection. That simple move gave my androgynous look a solid push toward the feminine. If I had been wearing any woman’s top other than the nondescript polo shirt I had on, all I’d have needed was a little mascara and some light lipstick and it would have been complete.

  Next she pulled the hair back and tied it off with a scrunchie. Not the low ponytail you’d expect on a man, but high at the crown. It was just long enough to support the idea of a ponytail without looking odd. That combined with the bangs she’d created turned that cold chill into a cold sweat.

  “Too bad you’re not a woman. That look is totally you.”

  She took out the ponytail and moussed my hair, and styled it with the hair that had made up the bangs brushed back and off to the side, giving my hair a more masculine cant. The sides were styled back, just over the top of my ears, concealing a little less than half of them.