Chapter 7
Exploring my feelings

  On Sunday Carrie laid out some of her Capris and an honest-to-goodness button-up the front blouse and told me to get dressed while she made some oatmeal. The capris had an elastic waist and no pockets. The blouse was long-sleeved with a wide floppy collar. It was sheer enough to see the outline of my cami through it. I felt really kind of stupid. I mean, looking in the mirror I looked really dopey; a man wearing obvious women’s clothes.

   “Carrie, you can’t be serious. I’d die if anyone saw me right now. I look ridiculous.”

  She observed me with a critical eye. “That blouse hangs on you like a sack. You need some shape. I guess I didn’t think of everything. I didn’t get out your bra, but since it’s in your underwear drawer I thought you’d get it when you put on your panties and cami.” She indicated I should follow her to the bedroom. “Take off the blouse and cami, and let’s get you some feminine attributes,” she said as she opened the drawer.

  I was a bit nervous as I stripped to the waist. Carrie waited grinning. As soon as I was bare-chested, she slipped the bra over my arms and fastened it behind me.

  “I’d rather not do the big boobs from New Year’s,” I told her. She pulled a bit on my chest from inside the bra and tightened the straps. She frowned and as she put those silicone things in the cups. “If you were just a little pudgy it’d be easier.”

  “She prodded and pulled up my pecs and the bra down.

  “ “OK,” she said. “Put your cami and blouse back on.”

  “When I did, I was amazed at the difference a couple of inches of silicone made.

  “Monday was the start of a week like all the other recent weeks. By now, I was totally comfortable wearing panties and cami so I didn’t think about it anymore. However on Wednesday, I was in the restroom, which was the one place, I couldn’t ignore my underwear, and began thinking about just how comfortable I was. Strangely enough, I realized that I kind of missed the thrill that went along with the fear of discovery. That thought resurfaced several times the rest of the week.

  “Saturday morning when I got dressed, I put on one of the sets of androgynous clothes that Carrie and I bought; only this time, I put on the bra. I wasn’t gutsy enough to put those blobs of silicone in it. I just let the cups hang. I told Carrie that I had some errands to run and headed out. Normally, I would have been going to the hardware store or some other manly thing when I went out on a weekend. This time, while I was willing to risk discovery, I wasn’t willing to risk men like those I might run into at the hardware store being the ones to discover my unusual attire.

  “Instead, I simply went to the local Barnes and Noble, got myself a Mexican Mocha at the in-store Starbucks, and settled in with my Nook to read from their library for free. All told, I spent about an hour and a half in Barnes and Noble as people came and went. OK, so that wasn’t very brave. Most of the time I sat in an overstuffed chair with no likelihood that anyone could see anything. They never knew, but I knew I was wearing a bra.

  “Back home, Carrie asked me where I’d been.

  “ “I decided to try going out in my women’s clothes, complete with bra. I went to Barnes and Noble and read for a while.”

  “She smiled and rubbed a hand up my back and paused as it crossed the bra straps. She kept smiling and looked at my chest. She cocked her head, narrowing her gaze. She put her hand on my chest to cover the bra cups. “No boobs,” she said. “Oh come on, you can do better than that!”

  “With that, she hauled me into the bedroom and unbuttoning my top two buttons stuffed the blobs into the bra, sticking a hand inside to position and stick them to me. With some difficulty, she managed to hook the clasp. She smiled as she re-buttoned the shirt.

  “ “Come on,” she said, “it’s about lunchtime. Let’s go get something to eat.”

  “She had the bit in her teeth and I knew it was no use to resist.

  “I soon found myself at one of our favorite restaurants ordering a soup and sandwich from the waitress we liked best. All the while, I was self-conscious; worrying that she would notice the subtle bumps on my chest. All for naught. She never blinked and gave us her usual good service while engaging us in pleasant conversation.

  “ “See?” Carrie asked as we drove toward home. “Even with the bra and small boobs, she didn’t twig to the fact your clothes are women’s clothes. I bet you could wear those boobs to work and no one would notice.”

  “ “I don’t think that’s such a good idea. If someone did notice, there could be some serious consequences.”

  “ “Still, I think it’s time to step up the pace. You’re obviously feeling the need to do more, since you went out with a bra on. Hmmm,” she pondered a while.

  “I kept my mouth shut. I didn’t want to fuel the fire any more than I had.

  “After a time, she said, “I think two things are in order. One, we need to get you a bra that will more or less fit you without any additional padding. That could be a trick. The other is, it’s time to get you another nightgown. The question is what kind? Something feminine, that’s for sure. Waltz length, knee length, or baby doll… I’m not sure.”

  “Abruptly, she turned a corner and in a few blocks we were in a strip mall parking in front of a business named, “Ann’s Lingerie and More.” As we walked in, Carrie said, “Ann went to the same high school as I did. We’ve kind of lost touch since then. I kind of ran into her when I was researching local lingerie shops.”

  “ ‘Oh great, one of Carrie’s high school friends. I hope she doesn’t let on we’re shopping for me.’

  “ “Hi Carrie,” a bit more than pleasingly plump blonde called out as the shop bell chimed. “I wondered when you’d be coming in.”

  “ “Hi Ann,” Carrie replied. “This is my husband, Alex. Alex, this is Ann Murdock. I know her from high school.”

  “ “So you’re Alex. So nice to meet you, Carrie’s told me all about you. What can I do for you guys today?”

  “ “We’re looking for a nightgown. Something really feminine, but not necessarily sexy, if you know what I mean.”

  “ “Well the sleepwear is over here,” she said turning to walk across the shop.

  “ “What does she mean, ‘Carrie’s told me all about you’?” I hissed at Carrie as we followed.

  “Carrie scowled at me. I grabbed her by the elbow and pulled her to a stop, raising my eyebrows.

  “ “Don’t worry,” she said, “Ann’s shop is trans-friendly.”

  “ “‘Trans-friendly?’ What’s that?”

  “ “That means she’s happy to have business from the Trans community and is discrete in serving them.”

  “ “You’re talking in riddles. When did you ‘tell her all about’ me?”

  “Well, your panties and camis came from this shop.”

  “So you told her about your ‘experiment’ when you bought them?”

  “Not exactly. I did tell her about Mike and Lisa and how I wanted to find a way to help them.”

  I looked up; horrified that Ann had walked back toward us. Carrie saw her too. “I’ll explain it to you later.”

  “Is there something wrong?” Ann wanted to know.

  “Oh, no. Alex is just a little intimidated with being in a lingerie store, that’s all.”

  “Don’t worry Alex. I get lots of men in here. Some are buying for their wife or girlfriend, and some are buying for themselves. Some even come in dressed as women. I just treat them as customers. No one really pays them any mind,” Ann smiled.

  I began to wonder what that was all about. Why did she feel the need to tell me about guys coming in dressed as women?

  Just then, the shop bell chimed and a tall blonde walked in. Ann looked over. “Perfect timing,” she mused. “You two go on, I need to talk to this customer.”

  “How did you find out about all this?”

   Carrie began perusing the nightgowns. “One of the transvestite sites I discovered maintains a list of trans-friendly businesses and they rate them. She’s on the top of the list for our area. Really, I needed someone with an inside track on cross-dressing and what it was all about. When I saw the name, I realized I knew her and called her. She said if I could come right down, she was closing in half an hour and she’d be glad to talk to me over a cup of coffee and I just ran out to do just that. Well, it became hard to ask the questions without explaining why I wanted to know. So I told her that Mike, your high school friend, was a cross-dresser and his wife had just discovered it, and I was trying to make sense out of it so I could help his wife, who happened to be a good friend of mine.

  “In the process, I told her how long we’d been married and that you were interested in helping Mike as well.”

  “That’s all?” I questioned.

  Just then, the blonde breezed over and started going through the nightgowns. “Doesn’t Ann stock the most gorgeous nighties?” she asked in a soft, husky voice.

  Carrie smiled, glanced at me, and said, “I was just thinking the same thing.”

  The blonde pulled one off the rack and held it up to herself. “This one’s lovely. Do you think it’d look good on me?”

  “I think so. Alex, what do you think?”

  I was more than uncomfortable. First, I wasn’t through interrogating Carrie about just what she told Ann, and second, I didn’t feel comfortable judging what some woman, other than my wife, would look like in a nightgown. “Ah… yeah, I guess.” The nightie in question was a pastel pink, a bit on the see-through side, and about knee length with ruffled flounces around the neck, arms, and hem.

  “I think I’ll try it on, to see if it fits,” she smiled as she scurried off toward the opening marked, “Fitting rooms.”

  Carried held up a long powder blue nightgown that was also see-through and had delicate ribbons woven into the lace over the bust line and said, “This one would be a nice one for you. What do you think?”

  “Sure, that one’s great,” I agreed, just wanting to get out of the store.

  “I’m not sure of the size. Maybe you better try it on.”

  “You’ve got to be kidding. You can bring it back if it doesn’t fit. Even if I wanted to try it on, there’s a lady in the fitting rooms. She’d be a bit upset if a man went in to try on something while she was there, no matter how ‘trans friendly’ this shop is.”

  “Oh, Drew wouldn’t mind,” Ann said startling me. “Drew’s a regular and whether she’s Drew or Andy at the time she wouldn’t care if a man was in the next cubical.”

  I whirled to face Ann then looked back and shot daggers at Carrie. I was furious; Carrie must have seen Ann approaching and still talked about the nightgown being for me. Then it sank in what Ann had said. “Drew or Andy?”

  “Sometimes, during the week, Andy comes in in drab to pick up something for Drew.”

  My brain wasn’t quite wrapping itself around what she was saying. “Andy? Drab?”

  “Drab (DRessed As a Boy) Andy. En femme or drag (DRessed As a Girl) Drew,” she smiled. “Drew is an officer in one of the local cross-dressing groups.”

  “That’s… Drew is a guy?”

  “Yeah, married with two kids. You couldn’t tell?”

  “No, but now that you mention it, she, er he…”

  “She when she’s en femme,” Ann interrupted.

  “… She did have a rather husky voice and maybe not as much shape as she might, but not out of the ordinary for a woman. Maybe a bit on the tall side, but still not that unusual.” Then I remember why I’d shot daggers at Carrie. I turned three shades of red. “Oh God!” I looked angrily at Carrie again. “Carrie told you about our experiment, didn’t she?” I demanded. “That’s what you meant when you said she told you ‘all about me,’ isn’t it?”

Chapter 8
On the fast track

  “Experiment? … Ah… OK, I think I know what’s going on now. You aren’t a cross-dresser, and Mike really is your friend and, ah … Liz, right?” she looked at Carrie.

  “Lisa,” Carrie corrected.

  “Lisa,” Ann continued, “really is a friend who really did discover her husband cross-dressed. God, I’m sorry Carrie. I thought your story was a thinly disguised ruse about you and Alex. I mean, you bought a dozen pairs of panties and camisoles to match. I thought you were trying to put up a brave front in an effort to accept your husband’s unusual hobby. But what’s this experiment?”

  I looked at Carrie panic-stricken. “I think we’d better explain. She’ll piece it together now anyway.” I closed my eyes and nodded. “You see when I tried to console Lisa, she said, if it was my husband, I’d not be so ready to accept. So Alex has agreed to experiment with cross-dressing, so I can convince Lisa that cross-dressing can be accepted in a marriage.”

  Ann smiled. “You’ve never entertained the idea of cross-dressing before?” she asked. I shook my head. “Well it’s very commendable of you Alex. Mike must be a true friend or, rather, you’re a true friend to him. You’re my kind of man. So how’s the experiment going? I take it the panties and camis were for you and you’re wearing them.”

  I turned really red, so much so I could feel the heat in my scalp. I looked down and worked my mouth, but couldn’t make any words come out.

  Ann put her hand on my shoulder. “No need to be embarrassed Alex. I take it you, kind of, like it? And this nightgown is the next step?” I nodded.

  “Well,” Carrie said, trying to smooth out the conversation, “Alex, why don’t you slip in and try on the nightgown? Ann knows everything and obviously, Drew’s not going to object. I think you’ll just love sleeping in it tonight.” She handed me the nightgown.

  I looked toward the fitting rooms just in time to see Drew come breezing out. “Good thing I tried it on, I’ll need a size larger and I think I’ll take in a couple more styles in as well,” she said with a smile, as she picked out three different nighties. “Are you going to try yours on?” she wanted to know.

  I looked at Ann and Carrie who both nodded their head yes. I shrugged and followed Drew to the fitting rooms. “It’s great to be able to try on before you buy, isn’t it?” Drew observed. “I bought too many things hoping they’d fit. It was always harder to bring them back than it was to buy them in the first place. But with places like this, no need.”

  In my own cubical, I stripped to my lingerie. Now there’s a phrase I’d never thought I’d use… “My lingerie,” not to mention, “My nightgown.” I slipped the nightgown over my head and luxuriated in the feel of the material. Carrie was right; it was going to feel great sleeping in this even more than the first one. Thinking about that, there was a question I needed to ask Carrie. ‘Just why do I need more than one nightgown?’

  It took a few minutes to become objective about the fit. It was good across the shoulders and came nearly to my ankles but it seemed to just kind of hang down the front. It was obviously intended to have a bust line under it and the little things inside this bra weren’t cutting it. But I liked it just the same. Almost reluctantly, I took it off and redressed. I was amazed at how easily I managed the reverse buttons on the shirt, OK blouse or top or whatever.

  “It fits fine for length and across the shoulders, but it kind of hangs on my chest,” I admitted to Carrie and Ann, who had obviously been talking while I was in the fitting rooms.

  Ann smiled. “Well, we could fit you for a pair of forms, to improve the drape,” she offered.

  I looked at Carrie. “That’s an option. You’d get a chance to find out what it’s like to sleep with boobs.”

  I made a face. “I don’t think I’m ready for that. That’s a pretty big step. I bet those things aren’t cheap.”

  “OK, soon though I think. But there is something else we need. Ann is there such a thing as a 38 double A or triple A bra? I think he’s ready to wear a bra full time, but he’s concerned about there being noticeable bumps under his shirt.”

  “I can order them. I don’t get enough call for them to stock them. Let’s go back to the fitting room and I’ll measure you Alex. That way, I can be sure that the fit is right.”

  With that, Ann turned and headed for the fitting rooms. “You can come too, Carrie,” she threw over her shoulder. Carrie stepped up behind me and with a hand on the small of my back gently urged me to follow. Ann led the way to an oversized fitting room.

  “Alright,” Ann said, “take off your top.” I complied blushing as she would see I was indeed wearing a cami and bra. She took a measuring tape off a hook on the wall. “Arms up.” I lifted my arms and she wrapped the tape around just under the boob bumps. “OK, now strip to the waist.” At her insistence, I even peeled the enhancers off my chest. When I was bare, she prodded my chest, using the flat of her hand to lift the little bit of flab. Then she measured right across the nipples. “I’m going to recommend a 36,” she said. “You’re just barely a 38 and bra bands are forgiving. The 36 will make the most of your natural shape. It will give you a little cleavage without being noticeable when you’re in male mode.”

  “OK, I guess.”

  “Now while I’ve got you here, why don’t we experiment with something the majority of cross-dressers go for.”

  “Ah, what’s that?”

  She smiled and looked at Carrie. “Breast forms.”

  “Yeah,” Carrie said enthusiastically. “Let’s, I really want to see what he’ll look like with a real bust line.”

  Ann trotted out of the room leaving Carrie and I to ourselves.

  “Breast forms?”

  “They’re manufactured for post-mastectomy women, but cross-dressers use them to give a realistic bust line. They jiggle just like the real thing and pretty much have the feel as well.”

  “I don’t know…” I started.

  “Look, just try it, OK? We don’t have to buy them today. But I think you should see what there is to offer.

  “I wonder what’s taking Ann so long,” she continued, stepping out of the fitting room.

  I felt really stupid, standing there bare-chested in a fitting room in a women’s lingerie shop. There on the little bench lay my cami, bra, and booblettes. It seemed forever before Carrie returned carrying several boxes.

  “She’s ringing up Drew’s purchases. She’ll be right in.”

  “What’s all that?”

  “Breast forms.”

  “Why so many?”

  “Got me. Ann had them on the counter and told me to bring them in here.”

  Ann bustled in carrying three or four bras. “OK, sorry I took so long. Had to make a sale. Here, let’s get this bra on. It’s an ABC cup, so we can experiment with cup size to see what really suits you.”

   She helped me on with a bra that had thin stretchy cups. Then she opened a pair of boxes and pulled out some really huge false boobs, complete with dark nipples, and dropped them one by one in the cups of the bra.

  “We’ll start with the largest, just so you can get an idea what Dolly Parton works with.”

  The boobs were so large that they really didn’t fit in the cups and the weight almost made me bend over. I had to tighten the muscles in my back to keep upright.

  “Those would actually be a D cup on you. The bra isn’t really built for them, but I thought it would be fun to see what they looked like. Most CD’s want really big boobs. It’s a man thing, I guess.”

  I looked in the mirror. They looked grotesque.

  “I don’t think that’s what I want. I don’t have anything that would even go over that much boob,” I told her. Carrie just smirked.

  “OK,” Ann grinned, “just thought I’d give you a look at the extreme. These are the largest I can get without special order.” She fished two ludicrous appendages out of the straining bra and replaced them with a slightly smaller version. “These are about a C cup on you.”

  I really didn’t see that much difference other than they didn’t overload the bra. They were still quite heavy and not something I’d want to have hanging off my chest.

  “Try your top over that.”

  I obediently put my shirt on and found it hard to button and not just because of the buttons being on the left side. I shook my head no and said, “Look, let’s cut to the chase. If I’m going to wear these things, I want something that looks natural. I doubt I’ll ever go out of the house wearing them, but on the off chance that I do I don’t want them to call attention to me, OK?”

  She smiled. “OK, we won’t go down to A cup size, because that would be noticeable enough for people to realize you have breasts, but not enough for your chest size and that would make you stand out as the underdeveloped woman. I assume you want to avoid undue scrutiny.”

  She put another pair in the cups and while they were still on the heavy side, they didn’t look that much out of proportion and when I put my shirt on over them it hung naturally, though didn’t do anything to disguise them being there. I studied my reflection for a time. “OK,” I said finally, “if we get some, these are the ones I would take.” I took off my shirt and pulled the forms out of the bra.

  Ann took them and set them in the box, but didn’t bother to put the lid on the box as she had the others. “The good thing about these is that they could be glued on, so that if you felt like it you could go braless. That would be a great asset if you wanted to wear a backless dress.”

  “I’m not sure I’d want to wear a backless anything or go braless for any reason.”

  “Well, there’s always the swimsuit issue.”

  “Swimsuit?”

  “Well, they do make swimsuits that have mastectomy pockets, but they tend to be pretty much granny style.”

  “I’m not likely to go swimming in a women’s swimsuit anytime soon.”

  “Perhaps, but the forms will last a long time. You may, sometime in the future.”

  I unclipped the bra and Ann said, “Why don’t we get a look at them in a good bra?” She held up another bra that looked a bit more like something I’d like to see Carrie wearing. I looked at Carrie who was nodding vigorously and shrugged. Ann fastened the lacy bra around me and dropped forms in, one by one. Then she fussed with the straps a bit and turned me toward Carrie. “What do you think?”

  “Nice,” she replied.

  “Let’s try them under the camisole,” Ann suggested, picking it up and helping me on with it.

  I looked in the mirror and, if I ignored my face, I thought they looked pretty good. I turned for a profile, first right then left.

  “Looks like he likes them,” Carrie observed.

  “Think so,” Ann agreed.

  “What?! Why would you say that?” I wanted to know.

  “The look on your face. That silly smile says it all. What was it the boys used to say in grade school? Your face says, ‘Hubba-hubba, ding-ding, baby you’ve got everything’,” Carrie giggled and Ann joined in, while I blushed. They were right, I was grinning like a Cheshire cat. “Put your top on,” Carrie continued.

  I complied and again studied my reflection. While I was occupied with that, Carrie retrieved my old bra and booblettes. “They look great. We’ll take them,” she said as she exited the fitting room. Ann scooped up all the boxes and followed her.

  It took me a moment to catch up with what was happening. “Hey,” I called out as I stepped out of the fitting room, “don’t I need a box to put these in?”

  Carry and Ann just kept walking toward the register. I sprinted after them my ersatz boobs bouncing so heavily that I slowed to a quick walk. I caught up to them as Ann was starting to ring up our purchase.

  “Don’t I need boxes to put these in?” I asked.

  “Oh sure,” Ann said patting a bag with two boxes, and went back to ringing the nightgown.

  As I reached for the bag with the boxes, Ann put the folded nightgown in with them. “Ah, why’d you put the nightgown in there? I was going to go back to the fitting room and put them in the box.”

  “No need, dear,” Carrie said. “You can just wear them home.”

  “I thought I was just trying them on and we’d buy them some other time.”

  “Well, that was the idea, but you looked so good in them and seemed to like them so much, I thought it would be cruel if we didn’t get them tonight.”

  As we were talking, Ann swiped Carrie’s card through the machine and tucked the receipt in the bag. Carrie put her card back in her purse and headed for the door. I started after her to protest, but Ann grabbed my arm and thrust the bag into my hand.

  Totally confused, I hurried after Carrie. She was getting into the car. I opened the passenger door and demanded, “You need to wait while I go remove the boobs! I don’t want to wear them home.”

  “Oh come on, Alex. Who’s going to see you? You’ll be in the car all the way home and we have a garage door opener that will allow me to close the door before you get out of the car.”

  “But…” I then realized that it was useless to argue, she had already started the car. In a snit, I climbed in and slammed the door.

  “Buckle up,” she said, putting the car into gear.

   “There, was that so bad?”

  “What’s with these? I didn't think we were going to buy them. You said we’d be getting a nightgown and a bra that fit without additional padding.”

  “Look, we were going to buy them eventually anyway. And as I said, you seemed to like them, so we just bought them ahead of schedule.”

  “We didn’t even buy a bra, well except for the one that’s holding these,” I said, indicating the lumps on my chest.

  “Ann will have to order those. She said you can pick them up sometime next week. Meantime, you can experience breasts.”

  “Yeah, well, these are not subtle little enhancements, like I was doing before; these are in your face boobs! I can’t go anywhere with these; everybody will notice.”

  “Oh, I don’t know. I think I could fix you up so no one would notice them particularly.”

  “What do you mean, ‘fix me up’?”

  “Come on I’ll show you.”

  In a flash, we were in the bedroom and she got out her make-up. “Wait, I remember this.”

  “Yeah, well this time, you’ll have the figure to go with it.”

   “Now that we’ve got the make-up right, let’s get you into something that will complement it,” she said as she opened her closet. “Take off your shirt and put this on,” she continued handing me a blouse with a built-in lace-trimmed ascot.

  The buttons were hidden behind a placket making it a bit hard to button, but I managed. When I looked up, I saw what looked to be a long, pale blue skirt in her hands. I recognized them from before. The palazzo pants. I remembered the sensual feeling of that gossamer fabric rubbing my legs.

  With some misgivings, I removed my pants and took the dubious things from her. I was again taken with the fabric. The blouse I had on was silky, but this… this was… well chiffon. So light and so fine it might just have well been woven spider webs, only not sticky, but slippery instead. They were lined with silky polyester that made the blouse I was wearing seem like burlap. With shaking hands, I donned the gossamer garment. I trembled, hoping she didn’t notice, as I slid them up my legs. I don’t know why women don’t always wear these kinds of pants.

  In a moment, I was lost. The feeling was like nothing I’d ever experienced wearing anything else. It was like being wrapped in a bit of heaven. My breathing instantly became shallow and my pulse rate raised by a magnitude of ten. I felt lightheaded, as if I might just float away.

  “Earth to Alex! Come in Alex!”

  So much for hoping she didn’t notice how the pants affected me. “What? Oh, I… I was noticing how soft and slick the fabric was. I’ve never worn anything like it.”

  “Like I said, ‘scrumptious,’ huh?”

  “Ah… yeah, scrumptious.”

  “Put your sandals on and let me fix your hair.”

  She had my Christmas sandals on the floor in front of me. I slipped my feet into the shoes and sat at her vanity while she fussed with my hair. The whole time, I lightly rubbed my legs with my hands, lost in the feel of the fabric.