Chapter 3
Blurring the edges

  Sunday morning, I usually fix a nice breakfast for us, so I just slipped on a robe and whipped up some microwave omelets for us. Carrie hadn’t bothered to get dressed either and we kind of kicked back in the family room to watch a little TV. Carrie picked a romantic comedy to watch as we sipped our after-breakfast coffee. I did notice that she kept looking at me and I could tell the wheels were turning.

  Once the movie was over, she stood and announced, “Let’s get dressed.”

  I followed her into the bedroom. After I’d changed my panties, she intervened. “You don’t have any work to do today, do you?”

  “No, I’m just planning on hanging around the house today.”

  “Good, I want to take another shot at seeing just how feminine I can get you.” With that, she produced another bra that I’m sure was new because she doesn’t wear underwire bras, and had me in it before I knew what was happening. Then she pulled a plastic box out of her drawer and stuck some cold silicone things in the cups. Even after she tightened the straps, the cups weren’t as full as you’d expect.

  “Not exactly what that bra needs, but we’ll try that for a while before we spring for something more in line with where a woman your size would be,” Carrie observed. “Let’s see if we can do something with your hair.”

  With my robe back on, she led me to the bathroom where she got out a spray bottle and wet down my hair. After brushing it out, she attacked it with a curling iron, followed by some brushing and teasing, finally spraying it down with a cloud of hairspray.

  “It’d be better if it was longer, but for now that’ll do. If you really keep this up on a regular basis, you’ll need to let it grow a bit or invest in a wig.” She eyed me a bit more and said, “I think I want to see just how much I can blur your masculine features.” She felt my chin. “Get a really close shave for me and I’ll be right back.”

  I usually use a Norelco cordless razor, but given the close shave command. I broke out the blade that I keep for backup when we go camping, in case the Norelco battery goes dead. When I finished shaving Carrie spread some green goop on my face with instructions to let it dry.

  While we waited she eyed my legs below the hem of my robe and glancing back to the razor on the counter making me uncomfortable as I tried not to think about what she was thinking. Seeing the look on my face she said, “You know of course when we get you into nylons, we’ll be shaving your legs.”

  “My pits too, I suppose?”

  “Oh most definitely,” she grinned.

  She put me back into the black loose capris and a blouse while we were waiting.

  It wasn’t long before the junk on my face dried and Carrie began pealing it off. When she was done, my face felt a bit tender and appeared just a touch on the pink side in the mirror. She then got out some moisturizer and rubbed it into my face, taking a tissue to blot up the excess. She then started spreading junk all over my face. She’d get some stuff on her fingers and daub it on me; on my forehead, each cheek, my nose and my chin. She even put a couple of spots just under my chin. She followed that up by spreading it around with a sponge.

  This was followed with a generous dusting of some powder, which she immediately brushed off. I didn’t quite understand the purpose of putting the powder on and then removing it??? Some kind of woman thing, I guess. She made me close my eyes as she outlined them with a tiny black brush. Then the tricky part… mascara. She warned me not to move suddenly, or I might end up with the wand in my eye. My lashes seemed to put on weight. I’ve never really been aware of my lashes before, except when one got bent back in my eye, but now, I could feel the weight of them when I blinked, as I did a lot just after she got through.

  This was followed by eye shadow. Not a simple process. Apparently, it takes three shades that have to be blended to get that sultry look that women seem to think they need. A touch of blush on my cheeks and lipstick. Again, lipstick seems to be a two-step process. She outlined my lips with some kind of colored pencil, one darker than the lipstick she’d picked, and then painted the lipstick on with a little brush. Don’t they just twirl it up out of the tube and apply it directly? What do I know, I’m a man. A thought I’d question shortly thereafter.

  She messed with my hair a bit more and led me to our bedroom, produced a pair of wedge sandals I’d never seen before, in my size no less. The heel was only about an inch and a half. The cowboy boots I’d worn when I worked at Camp Baldwin as a wrangler when I was in high school were taller than that, so I didn’t have any trouble walking in them.

  When she closed the closet door so I could see myself in the full-length mirror I indeed questioned that thought. The woman in the mirror was a bit skinny in the hips, thick in the middle and would have looked a little bit better with a longer hairstyle (I’ve never been fond of women with short hair) but there was no doubt in my mind that it was a woman… except… it was my reflection. I took a quick step and sat down on the bed still focused on the reflection. ‘Blur’my masculine features, hell, she erased them. Oh God can that really be me? I looked around to see if there was some way I was seeing someone else in the mirror. There was no one there except me and Carrie.

  “Well, what do you think?” Carrie asked.

  “I think that can’t be me,” I replied touching my face, marveling that the reflection copied my move.

  “Well girlfriend, we’ve wasted the morning making you beautiful. Let’s get some lunch. I’m starved. It’s a lot of work making a silk purse out of sow’s ear.”

  With that, she led the way to the kitchen where she maneuvered me into heating some soup at the stove while she made sandwiches.

  “Smile,” she said. I looked up and the camera went, “click.”

  “You didn’t smile.”

  “You took a picture.”

  “Well yes. I want a record of the first time you really went all out.”

  “I didn’t exactly go ‘all out.’ This is all your work.”

  “Semantics. This is the first time you actually are fully cross-dressed to the point that you could pass. I wanted a picture to remember it by. It’d be better if you smiled like you were enjoying it.”

  “Who are you going to show that picture too?”

  “Well, possibly Lisa, if we can get that far of course if I show it to her, I’ll likely show it to Mike as well. Now come on smile so I can get the one that looks nice.”

  I closed my eyes and shook my head. If she’s planning something dastardly she’s already got one picture, what’s another? I took a deep breath, turned and put on my best photogenic smile. “Click” went the camera and Carrie’s smile was more genuine than my own.

  That wasn’t nearly enough for Carrie. She had me all around the house posing, looking like she’d caught me in candid shots doing ordinary things. It’s not that I never did the laundry, or vacuumed, but not usually on Sunday. I helped around the house but, if she was around, those two things were normally Carrie’s domain. I mean, she worked part time, not because we really needed the money, but because she wanted to, and had more time for such things than I did. OK, truth is, I don’t fold the laundry to suit her nor am I thorough enough when I vacuum. She always feels like she has to do touch up when she gets home. I did do more cooking, so that first picture wasn’t really out of line. She also got real candid photos of me doing more typical things. I watched the game and she caught me with the remote pointed at the TV. She also managed a picture of me at the computer checking my email.

  Strangely enough, by dinner time I’d gotten used to the clothing. Long before that day it’d become common place to feel the panties. While I was aware of the panties, they were no longer a distraction and the wedge sandals only took an hour or so before I ignored them. It was the bra that was most distracting. Although, there were times through the day that I failed to notice it, but it seemed that if I moved my shoulder or my arms, I was immediately aware of it again.

Chapter 4
Santa Claus is coming to town

  The following Monday I had an odd thought as I was getting dressed. As I was about to change my panties I thought, I wonder if I could get away with wearing them under my work clothes. In answer to that, I tried it. I had on a pastel yellow pair with some lace on the side. I was as nervous as a long-tailed cat in a room full of rocking chairs. But to my knowledge, no one noticed. I was on a kind of adrenaline high all day; absolutely euphoric by the time I got home. Carrie noticed.

  “What’s with you?” she asked. “You seem all… I don’t know, excited doesn’t seem right, but it’s something that got you keyed up a bit.”

  I was torn. I wanted to deny everything, but I never was a good liar, not even as a kid, so I just ’fessed up. But I wanted to down play it a bit. “I decided that in keeping with your experiment, I should try the under-dressing thing you talked about. As a result, I’ve been on edge all day. I was scared to death that something would happen and someone would notice.”

  “And did they?”

  “No.”

  She smiled. “…And you’ve been excited all day over it?”

  “Excited? I… I… … I was just nervous… I’m just relieved to have gotten away with it without anyone noticing.”

  “When you were at work was it an objectionable feeling or did you kind of enjoy it?”

  She had me there. I’d decide about lunch time that it was kind of cool to have a secret like that. I mean I kept wondering, what would so and so think if he, or she, knew what kind of underwear I had on.

  I looked down. “I kind of enjoyed it after I became convinced that no one was going to catch on.”

  “So? You gonna do it again?”

  I shrugged. “I… I don’t know. I’ll see in the morning.”

  Well, I decided not to push it and went to the office in my regular underwear the next day. It was a bit of a downer, but I could concentrate easier. However, in the slack times, I kind of missed the thrill of the secret. Carrie was inquisitive when I got home.

  “Well?”

  “What?”

  “Did you do it again?”

  “No, I decided against it.”

  “OK, just wondering. … You know, most cross-dressers start out only doing it at home and take a while to do the under-dressing thing full-time. You could change into your panties when you come home. The only thing missing for you is you don’t have to sneak around to do it, like Mike. It would make sense considering you’ll be putting them on when you go to bed anyway.”

  I took that as a hint and went straight to our bedroom and changed my underwear while I changed into some casual clothes. That became the norm for that week. Of course over the weekend, I wore the panties day and night.

  Saturday morning, I was getting dressed when Carrie interrupted. “Wear something nice. I want to take you out for a while today.”

  That put me on high alert. “Just what would I wear that was ‘nice’?”

  She went to my closet and came back with a lightweight pullover sweater with a V neck and handed it to me along with a black, turtle neck dickey. I didn’t own a dickey and I recognized it as one that Carrie wore on occasion. This was obviously a first go at wearing some women’s clothes out of the house. I hesitated while she went back to closet and began rummaging through it. At least she was looking on my side.

  Finally, I decided to put it on and see if I could tolerate the combo. Once I had it on, I looked in the mirror over Carrie’s dresser. I ignored the fact that I was wearing nothing but panties below the waist and concentrated on the sweater and dickey. It wasn’t my usual kind of fashion, but I had to allow that I’d seen men wearing a turtle neck tee-shirt under sweaters, so I decided to go along with it. I wasn’t too sure just where she wanted to go “out” - but I supposed it couldn’t be too bad.

  As I was looking at myself, she came over with a pair of cotton/polyester blend slacks that I didn’t wear much since the summer I bought them. They were a kind of throwback to the leisure suit era. I pulled them on and stepped to the full-length mirror on the closet door.

  Yeah. The outfit screamed androgynous. It made me a little uneasy, but I couldn’t articulate just why. Maybe it was because I knew that the dickey was Carrie’s. Anyway, she upped the ante when she handed me some black socks. Not just any socks, but a pair of her trouser socks. Biting my tongue I put them on and slipped into my loafers. I did a quick mental calculation. I was wearing fifty percent women’s clothes. That meant I was half cross-dressed and she had plans to take me out in public.

  Well, at least everything of hers was not outerwear and someone would have to be studying me pretty intently to notice, I thought. It turns out she just wanted to do some window shopping at the mall. I was nervous as hell the whole time. I could just see her hauling me into a store to try on something.

  When I asked why we were at the mall, she said, “Cross-dressers often just go to malls and walk around when they’re all dressed up. Of course, that usually means a dress, but you’re not ready for that. I know that the pants are men’s, but I didn’t have any that would look right, except shorts and it’s the wrong season for you to be wearing shorts.

  On Monday I seriously considered panties, but in the end, I opted for jockey shorts.

  By the next weekend, if I could be honest with myself, I’d have to admit that the panty wearing was growing on me. I came to enjoy the soft slightly supportive fit of them. When I thought about it, how my tighty-whities felt restrictive and rough; how I felt just off when I was wearing them, it scared me a little. I mean, I’ve worn jockey shorts all my life since I was potty trained. Now a few weeks, part time, in women’s briefs and I actually looked forward to being able to wear them. And yes, I did more underdressing than not at work. I really was trying not to do it. After all, this is a temporary thing; just until Lisa lightened up. I vowed I’d go back to just wearing them when Carrie wanted me to; weekends and evenings.

  Christmas fell on a Friday, so I had Thursday, Christmas Eve off as well. By Wednesday I was getting impatient for the weekend and wore panties to work again. I found it easier to ignore the panties and the fear that I’d get outed. I still got a bit of a thrill about having the secret and I found myself looking at the women in the office a little differently. Instead of the typical enjoyment of considering what parts of the body were their best features, I was taken with the fact that we shared something in common… i.e. underwear. I found myself wondering if any of them were wearing the style, or color I was.

  As I got dressed Christmas Eve there was a small feeling of elation. I’d have four days straight to wear panties with no worries as to who might notice. As I got dressed, I picked out the most feminine pair there was. They were a pale purple with a slash of lace running from the middle of my belly to the leg band on my right hip and on the left, was an embroidered rose in high relief.

   Christmas day found Carrie and I still in our nightgowns opening presents. (Did I mention that I started wearing the nightgown the same weekend that I first wore panties? When I went to panties in the evening, I wore the nightgown every night.) I got Carrie some nice jewelery, a cashmere sweater and a $50 dollar gift card from Barnes and Noble so she could load up her Nook with books. When she handed me my presents, there were two shoe box size gifts and an obvious shirt box. I opened one of the shoe boxes first. Inside was a pair of loafers. They were cordovan, one of my preferred colors. They seemed a bit lighter than the shoes I usually buy.

  “Thanks, they’re very nice, but I’m not due a new pair of shoes for a while.”

  “As I remember, I promised to get you some shoes that no one would notice were women’s.”

  I gave her a wide eyed look. I looked at the shoes again with a critical eye. The vamp was a bit shorter than usual and the sides weren’t as wide, or is that as tall, as usual, but other than that, they looked pretty much like men’s. I checked the size and sure enough, size 12W.

  “You really think that no one will notice? Now that I look at them, they do look like women’s flats.”

  “They also look like what is known as Italian loafers; very continental.” I raised my eyebrows. “Be honest, when you first looked at them, you thought they were men’s shoes, didn’t you?”

  “Well, yeah, but I was expecting them to be men’s shoes and didn’t look all that closely.”

  “What kind of shoes did your boss wear on Wednesday?”

  “I don’t know. I don’t pay any attention to his shoes.”

  “Exactly. When you’re wearing them everyone will expect them to be men’s shoes. What’s more, they won’t really be paying attention to your shoes.”

  I shrugged in aquesence and opened the second shoe box. Of course they were shoes again. But these were light tan with a narrow almost pointy toe and an inch and a half bock heel and a sling back strap.

  “Well these are women’s. I can’t wear them without anyone noticing.”

  “No, but you can when you’re around the house dressing femme like you were when I loaned you my pants.”

  The third box was a dress. Not just any dress but a rather fancy cocktail dress. My heart stopped; well at least shuddered. It was a gorgous teal and shinny. I sat looking at it with my mouth open.

  “I think that will be a good color on you.”

  “Why did you get me a dress?”

  “Well I talked to Lisa about New Year’s Eve. It was supposed to be our year to host. She told me that she and Mike would be staying home. I guess the waters are still a bit troubled over there. So I thought since it would be just you and me, we could dress up.”

  Sunday, Carrie gave me a new pair of jeans and a pullover sweater.

  “Here,” she said, “put these on. We need to do some shopping.”

  “What’s with the new clothes? I’ve got plenty of jeans already and I’ve been shopping plenty of times in my flannel shirts.”

  “Humor me. You’ll figure it out soon enough.”

  After I was dressed, she hustled me out the door.

  “What about breakfast?” I wanted to know as we climbed into her car.

  “We’ll grab some coffee at Dutch Brothers and get something when we get to the mall.”

  That meant The Cheese Cake Factory. Who knew they did breakfast? I was a tad bit nervous. I’d never been anywhere when I wasn’t in full male mode and in charge of the situation, well except for that trip to the mall, but we didn’t actually go in anywhere. Oh and I was convinced that the jeans I had on were women’s. There were subtle differeces. The fly was shorter and the pockets smaller, though the fly wasn’t on the distaff side.

  Not wanting to call attention to myself, lest anyone examine my clothes too closely, I let Carrie do the talking. The hostess found us a nice table for two, it could have been for four, but it was set for two. Normally, for breakfast I’d have ordered a big omelet, or maybe the breakfast burrito, but that day I settled for two eggs, over easy with toast and potatoes. Carrie on the other hand did have an omelet.

  Turns out that shopping doesn’t necessarily mean buying. At first, it was more like mall walking like we did last time. They advise seniors to do that for exercise. Window shopping, Carrie called it. We did go into a couple of stores, but mostly just browsed the racks in the women’s department. There I was pretty aprehensive. I was praying Carrie wasn’t thinking of having me try anything on, especially since she was looking at dresses.

  I was worried for nothing. We didn’t even talk to a salesclerk. Back out in the mall, we wandered down the concourse and into another store that seemed to specialize in casual wear, albeit women’s casual wear. There were a lot of trousers and jeans. A selection of pullover shirts, or I suppose tops. It seems women don’t wear many shirts, only blouses and tops, or maybe sweaters but they can all be called tops. Carrie was really interested in the slacks, only the ones she was looking at, I knew would never fit over her curves. The styles didn’t seem to me to be the kind of thing she’d really wear. Just a little too androgynous, or perhaps butch. She was a girlie girl after all.

   We wandered around a bit more. A little later, we stopped for an Orange Julius and sat at a small table as shoppers walked past in both directions. As aprehensive as I had been about this little adventure, I was pretty calm at this point. No one, and I mean no one seemed to notice or care what I was wearing. In fact they seemed to look right past me.

  Sometime after one, Carrie said we should probably head out and get some lunch on the way home.