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I can pinpoint the day this all started. It was a chilly, Sunday afternoon in early December. A light rain was falling outside and Carol (my wife) and I had built a cozy fire in the fireplace. She was sitting on one of the couch, her legs curled up beneath her reading and sipping a glass of wine and I was sitting at the other watching the Giants begin to give away a 21 point lead to the Eagles.
Carol stood up and stretched, heading toward the kitchen.
“Get me a beer, hon” I called after her.
“What’s the magic word?,” she asked with a twinkle.
I just wasn’t in the mood for this. I’d had a bad week at work, the weather was making me miserable and the Giants weren’t helping. “Just get the beer, alright? I don’t feel like playing games.”
She brought the beer and gave it to me without saying a word. When I opened it, it exploded all over me. “What the big idea?”
She giggled to herself, “You really should have asked me more politely. I’m not your maid, you know, I’m your wife.”
“Yeah, well right about now I think I’d rather have a maid. At least a maid wouldn’t go shaking up my beer.”
She turned to me. “You’re serious, aren’t you?”
I didn’t replay, but just stared at the tube.
“Look at me when I’m talking to you.” I dismissed her pique with a wave.
“OK, have it your way. I have a wager for you. Interested?”
I was, and turned around to face her. “Go ahead. What are you suggesting?”
“You want a maid so much, here’s your chance. If the Giants win today, next week I’ll be your maid for the game. I’ll get a sexy little maid’s outfit and I’ll serve your every need all through the game, and who knows, maybe after. How’s that sound?”
It sounded great. Carol is a beautiful woman and the thought of her in a tight, short maid’s outfit was something I’d fantasized about many, many times. On the other hand, it sounded a little bit too good to be true.
“And if they lose?”
“Nothing too drastic. Instead of me reading and you watching the game, we’ll rent a long, romantic movie and watch it together while we talk like a couple of long, lost girlfriends.” Her eyes twinkled.
That didn’t sound too bad. The Giants were playing the Lions next week and that didn’t exactly come off as the game of the century. “That’s it?” I asked.
“That’s it. You just have to dress the part.”
“Dress the part?”
“Yes, dear, are you having trouble hearing?,” she asked. “My girlfriends don’t wear jeans and flannel shirts when visiting.” She smiled a great, big smile.
“You want me to wear a dress?”
“A dress, or a nice skirt, or whatever you please. Just no pants.”
I thought about this for a minute. The Giants were leading by 21 late in the third quarter. The upside was having an amazing fantasy come true. The downside seemed a little silly, but how bad could it be? If this was a bad bet, I couldn’t see it.
“Honey, you got yourself a bet.”
Carol leaned over and pecked me on the cheek. “That’s nice dear,” she smiled. “Let me know how the game comes out.” With that, she got up off the couch and headed for the kitchen to begin dinner.
I returned to the game and was a little surprised to see that the Giants lead was down to 14 points during the commercial break between the third and fourth quarters. About four minutes into the quarter, the Eagles returned an interception 63 yards for a touchdown to bring the score to 28-21. On the kickoff, the Giants fumbled and the Eagles recovered. Two plays later it was tied at 28. After the two teams traded unsuccessful drives, the Eagles drove the ball to the Giants 20 where they scored a field goal with less than two minutes left to give them a 31-28 lead. The Giants did nothing in the remaining 90 seconds, giving the Eagles the win.
I sat there stunned. Carol won. No maid. No football next week. And I had to wear a dress. When the news came on after the game, Carol poked her head in the living room. “How did the game end, honey?”
“The Eagles won.”
“That’s wonderful, honey, we’re going to have such fun next week.” She was grinning from ear to ear.
“You’re serious, aren’t you?”
“Absolutely, dear, absolutely. You would have been if you won.”
“I guess. Where am I going to get a dress?”
“You know, sweetie, I think that’s your problem.” I could swear she was smirking as she returned to the kitchen.
I couldn’t imagine how I was going to get a dress and thought about little else for the next couple of days. I finally got up my nerve to go to the shopping mall on Wednesday evening, but when I saw one of the neighbors in the atrium I got scared and left. When I got home, Carol noticed that I was a little late. “Doing some shopping dear?,” she asked innocently.
I said nothing and ate my dinner in silence.
A couple of times during the week Carol mentioned how much she was looking forward to this Sunday and asked what movie I wanted to see. I just grumped about and refused to get pulled in, and I think that made her even happier.
It was on Saturday that I finally got up the nerve to get my dress, because by then I thought up a plan. I drove out to the mega-discount store a couple of towns over, where no one was likely to recognize me. Once there, I got a shopping cart and picked up some duct tape, some athletic socks, a couple of big bags of potato chips, some windshield washer fluid and one of those big ugly flowery housedresses that zip up the front, the kind my grandmother used to wear all the time. I could play this thing for laughs, couldn’t I?
I had to push that damn cart around the store a half-dozen times before I found them, but I did. I picked out the biggest one I could find after I realized I had no idea about sizes, so I got the biggest they had, which was a 28 and quickly jammed it into the cart. When I got to the checkout, the girl rang up the housedress just like everything else, no bells and alarms went off, and she bagged my purchases and I drove home.
On game day, I got dressed as usual, had breakfast, ran a couple of errands and generally puttered around the house. Carol did the same thing, but there was a real bounce in her steps, where I was dragging. She kept looking at me and smiling and it was getting on my nerves.
About ten minutes before kickoff, she asked “Aren’t you forgetting something, dear?”
I grumbled and shuffled off to the bedroom where I got the housedress out of my closet. I stripped off the jeans and flannel shirt and put this monstrosity on over my T-shirt and boxers. Zipped that sucker up and then put on a pair of white sweat socks. I glanced in the mirror and from chest level down, I could have been my grandmother.
“Ta Da!” I shouted as leapt into the living room.
Carol just stared at me. “You’re kidding.”
“Uh, no. You wanted me in a dress. I’m in a dress.”
“You missed the whole point,” she said quietly. “I wanted a quiet, intimate, warm, lovely, romantic day and you turned this into a joke. A stupid pointless idiotic joke.”
Now it was my turn to stare. “But…”
“I thought the clothes thing might be a little fun. Might shake you up a bit and suggest some stuff for later, but…I can’t believe you did this. You are such a selfish prick. Take that ridiculous thing off.”
I did as she asked. I really didn’t know what to say to do, so I just stood there while Carol stared at the fireplace. She abruptly got up and stalked off. About ten minutes later I heard her start the car and drive off. I got dressed again and turned on the game, but my heart wasn’t in it. When she came back an hour later, she glanced at me on the couch, beer in hand, Giants on the tube, snorted and walked straight upstairs.
For the rest of the day we didn’t speak and sleeping next to her was like sleeping next to an igloo. Our conversation for the next couple of days consisted of “Pass the salt,” “Have you seen the paper?” and “Can’t you even pick up after yourself?” accompanied by a pair of dirty socks hurled in my direction.
I was in trouble.
I was in trouble and the only thing I could think of to get me out of it was to turn the clock back a week. Some things were easy. I picked up Dr. Zhivago at Blockbusters, some cheese and crackers at the supermarket, a nice Chardonnay and an expensive champagne at the liquor store and a bundle of wood at the hardware.
Now came the hard part.
I thought that getting the dress would be the right place to start, but I came up against that size thing again. I couldn’t just walk into a store and grab something because I had no idea what size a thing to grab. I was going to have to have a salesgirl help me and I just couldn’t imagine how I was going to walk into a store and say, “I need a dress — can you tell me what size?”
After thinking about it for a day or so, I decided to tell the truth. I could walk in, look bashful and tell the truth. Then maybe the salesgirl wouldn’t think I was a pervert and might actually help me. What did I have to lose except my self-respect?
I traveled to a mall about 20 miles away so that I could be a little surer that no one would recognize me. I thought that it might be easier at one of the big department stores than a smaller store, so I went in to the Macy’s and headed for the dress department.
It was about 7pm on a Thursday night and not very crowded but I was a little intimidated as I walked through the women behind the cosmetic counters and past the women browsing through the shoes (I was going to have to get shoes, too!) and the hosiery. I didn’t know how I was going to do this, but I knew I had to.
When I came to the dress department walked around it a couple of times and then walked in timidly, looking utterly clueless. A very pretty, very young blonde came up to me and smiled. “Can I help you sir?,” she asked.
It was now or never. I cleared my throat. “Yes. I guess so.” I looked at her and then looked down. “My wife and I had a bet on last week’s Giants game and I lost. Now I have to watch this week’s game in drag.”
The salesgirl giggled and blushed, but she wasn’t blushing nearly as deep as I was.
“I don’t have a clue about sizes or anything, so I need all the help I can get.” I smiled bashfully.
“OK,” she said and giggled again. She pawed through a couple of racks and then looked at me and said, “I’m going to have to get my supervisor, sir. I’ve never fitted a man before. Do you mind.?”
I blushed and nodded no and tried to make myself as inconspicuous as I could. In a couple of moments, the girl came back with a woman in her mid-40’s with a brittle blonde hairdo and a brass nameplate that said Mrs. Kelleher. Mrs. Kelleher smiled at me and simply said, “Yes?”
I told her about the bet and my predicament. She never stopped smiling. “I’m afraid we can’t help you, sir.” She emphasized the sir. “You need to go the women’s department.”
I looked confused. “Isn’t this the women’s department?”
“No sir,” she explained, as if talking to a kindergartener. “This is the misses’ dress department. The women’s department is on the second floor. Or you might try one of the other stores in the mall that caters to larger sizes.” She smiled again and walked away. I could hear the girl giggle again from behind a rack of cocktail dresses.
I was unbelievably embarrassed at this point. I slinked out of the store, past the cosmetics ladies and back into the mall. I wandered around the mall a couple of times with my eyes averted until I stopped in front of a store called Laura Brown’s — A Shop for Women. A smaller sign in the entry way said clothes for real women in sizes for real women. I hesitated in the door way and then walked in, again trying my best to avoid eye contact with everyone.
After a minute or two, an attractive women in trim tan slacks, white blouse and navy jacket smiled warmly and asked if she could help me. Here we go again, I thought.
“Umm, yes. I know this sounds ridiculous, but I lost a bet to my wife on last week’s game and I have to watch this week’s game with her in drag.” I blushed furiously and looked away.
“Oh my,” she said, “you do you a problem. But who knows, you may come to like it.”
I just stared at her. I swear her eyes twinkled.
“Do you know what size you are hon’?” she asked gently.
“Umm no. I’ll need your help on that.”
“That’s no problem at all. I’m sure I can help. Did you have any idea of what you wanted?”
Oh my god. My brain just went completely blank My expression must have done the same.
“Well don’t worry about it, I’m sure we can pull something together.”
She pulled a tape measure out of her jacket pocket and told me to lift my arms. I glanced around and saw that nobody else was in the store, then lifted my arms. She measured me around the chest, then around my waist, then around my hips.
“OK, that’s done. Now, do you have any idea of what you want? A dress, suit, skirt and blouse, or pantsuit? Sexy or simple? Color, style?”
Oh my god. I hadn’t even though about that. Here I was in a store full of dresses and skirts and things and I didn’t have any idea. I just thought of a dress in the abstract. Now I had to pick one out. I almost fainted. “Ummm, no. I dress I guess. Something simple.”
“Actually, hon, I’d recommend against a dress for you. The way that most of them fit, to get something nice that fits you here,” she explained as she touched my shoulders, “it would be far too blousy for your here” and she moved her hands down to my waist. “I think you might be better off with a skirt and maybe a nice blouse or sweater. Does that sound OK to you?”
I nodded.
“Alright then. And I think you probably would like something comfortable, not too revealing and probably more smart than sexy. Am I right?”
Again I nodded.
She leaned in to whisper to me. “You know, hon, you ought to relax. Wearing a skirt isn’t going to kill you and if you’re going to go through with this, you might as well try and have some fun doing it.”
For some reason, that really loosened me up. I actually smiled back at her. “I guess. You might be right.”
“Are you going to shave?”
The question took me by surprise and I reached up to my cheek.
“No dear, your legs. If you’re going to shave your legs, you could wear pantyhose and that gives us more to choose from. If you’re not, you’ll have to wear tights and while that’s OK, some outfits just won’t look right if you’re in tights.”
Again, I blanched. “I hadn’t even thought about that,” I blurted.
“OK, that’s not a problem. We’ll assume you’ll wear tights so you can make up your mind later.” She spun around and walked over to the other side of the store, looking around her as she went. I followed slowly, watching her every move. When she turned around again to face me, she held up an outfit and asked brightly, “Well, what do you think?”
The skirt was long and looked soft. It was mostly a dark brown, with a border near the hem that was sort of a paisley with swirls of gold, maroon and dark green. Above it, she held a light tan mock turtleneck sweater. “That looks great,” I said, relieved that this process was coming close to an end. I reached for my wallet and headed towards the cash register.
“I think you’re going to have to try it on.” I just stared at her. “I can only guess at your size, you know. We’re not going to know if they fit until you try them.” She held them out towards me and nodded to the dressing room. “Give me a shout if you need anything. I’m Catherine.”
The dressing room was just a few feet away but it wasn’t until I closed the door that I noticed the door not only didn’t go to the ceiling, it didn’t go to the floor. I wondered if anyone was going to notice my heavy socks and hairy legs under the door. I took off my shoes, jeans and shirt and let them drop on the floor. I stepped into the skirt, but it wouldn’t slide up past my butt. Then I noticed a zipper and after undoing it, I had no problems. I pulled on the sweater and everything seemed OK. I looked like hell in the mirror, but what did I expect?
“How are you doing in there hon?” I heard Catherine ask.
“Umm. OK, I guess. It’ll work.”
“Come out and let me see,” she replied.
“That’s OK. I’m alright.”
“Don’t be silly.” She opened the door to the dressing room and looked at me critically. I was absolutely mortified, standing there in a skirt with the door wide open for anyone to see (and by now there were about a half-dozen customers scattered about the store in additional to another couple of saleswomen).
“Well the first thing is that we ladies usually wear our zippers in the back.” With that, she grabbed the waist of my skirt and yanked it around until the zipper was indeed, in the back. That a couple of her yanks included my boxer shorts thus inducing a shocking rearrangement of things I thought was better left unsaid.
“That’s much better,” she said. Although I think this skirt is a bit big. It might look better one size smaller. “What do you think?” She didn’t wait for me to answer, but left to go to the rack for another skirt, leaving the door open. I closed it as quickly as I could but she was back in an instant to open it back up again.
“Here, try this one. Remember, zipper in the back.”
I closed the door, unzipped and dropped my skirt to the ground and put the new one on. Zipping up the back was a bit of a contortion, but I managed.
“All set?” Catherine asked. She opened the door just as I was finished pulling up the zipper. “Yes, that’s much better.”
Then she spun me around and unzipped my skirt. “I think that this would look nicer if you tucked in the sweater,” she explained as she smoothed the bottom of the sweater down around my boxers before zipping me up again. “Turn around.”
I did as ordered. “Hmmmm. Wait right here.” I wondered where she expected me to go, dressed like that.
She came back with a belt and a scarf. The belt was wide with a big brass buckle and the scarf was dark brown with a pattern that was similar to the one on my skirt. She wrapped the belt around me and fastened it in front, then spun the scarf a couple of time around itself and draped it around my neck and over my left shoulder.
“There! You’re perfect.” I turned around to look at the mirror in the dressing room and I have to admit it wasn’t all that bad. The sweater and skirt felt soft next to my body and I liked the way everything sort of flowed gently. At least from the calves to the neck. The legs and head certainly gave the lie to the prettiness of the ensemble and if you looked closely you’d notice that the sweater hung in a straight cylinder when it would have preferred nice breasts and a waist.
I shook myself out of my reverie in time to see Catherine grinning at me. “See, now that isn’t so bad is it?”
I smiled shyly back at her. “I guess these will do.”
“Not yet,” she said. “You’ll need some tights, shoes and underwear, maybe some jewelry, if you want to do this right. I’ll get your tights while you get dressed.” She began to walk away, but turned around. “Unless you want to wear those home?” Again, she smiled broadly as she walked to the hosiery racks.
I just scuttled back into the dressing room to get back into my clothes.
When I brought everything to the counter, Catherine gave me a slim box. “Here are your tights, hon. They’re chocolate brown, so they will complement your skirt perfectly.”
“Thanks,” I mumbled.
“I’d love to see you when you get everything together. I think you’d be a doll,” she said as she rang up the sale. The bill came to more than I expected (this wasn’t going to be cheap!) and I gave her my credit card. As she was processing the credit card, she said “There’s a store about five doors down called Under It All where you can pick up your underwear. I don’t think the department stores will have what you need in your size. And there’s about a half-dozen shoe stores and I’m sure you’ll find something nice at one of them.”
She bagged up my outfit. “Here’s a credit card application in case you want to open up an account and a 15% off coupon for your next purchase.”
My “next” purchase? “Ummm, thanks. You’ve been very helpful.”
“Why, thank you! Now you have a nice day, and hon — relax. You’re not the first man I’ve seen in here and you won’t be the last.” She smiled very graciously at me and I left, not knowing if I was supposed to be relieved or embarrassed.
I turned in the direction of Under It All and walked slowly in the direction, stopping before I reached the door. There were a pair of mannequins, one dressed in a very sexy burgundy bra and panty set and one in a teddy made out of the same burgundy material with some black lace accents. Through the glass I could racks of nightgowns, bras, panties, teddies, slips and god knows what else. The store wasn’t empty, either. There was a woman shopping with her teenage daughter, a couple of women in business suits, an older woman by herself and a young mother with a toddler in hand. I also saw a tall, trim, middle-aged woman in a flowery dress who looked to be running the place and a couple of girls in their 20s who were probably the shop assistants.
As I was standing outside the door, losing my nerve, the woman in the flowery dress poked her head outside the shop, glanced at the shopping bag from Laura Brown’s that dangled from my hand and said “You must be the gentleman that Catherine just called about. Come in, come in.”
I followed her as she walked to the counter at the back. The store was tightly packed and everywhere I went I plowed through wisps of softness. I felt like the proverbial bull in a China closet. A couple of the customers glanced at me but I couldn’t tell what they were thinking.
“Now then, how can I help you?”
I told her about the bet and that I’d already purchased a skirt and sweater and that I needed some underwear.
“Do you know what you’re looking for, sir?”
I just shook my head. “Not really, no. I guess I’ll need a bra and a pair of underwear.” I just couldn’t bring myself to say the word panties.
“Well that’s still alright. You probably don’t know your size, right?” I think she considered my blushing nod a sign of agreement. “I didn’t think so. Take off your jacket and raise your arms.”
I did as I was told and she took a tape measure and measured around my chest. I was glad my back was toward the store because I couldn’t imagine what anyone who saw this may have been thinking. “Looks like a 40,” she said to herself. Then she raised the tape measure up a couple of inches up and measured again, only this time she just wrinkled her nose and grunted softly.
“Were you planning on having breasts, sir?” she asked.
“I suppose I should.”
“Do you have any preferences — small, large?” Although she was trying desperately to keep a straight face, I could see the traces of a smile dancing at the edges of her lips. How could I possibly answer a question like that? I felt like every time I took a breath I was falling deeper and deeper into a hole.
“I don’t really know. I hadn’t thought about it. I guess I’ll go along with whatever you think is best.”
“I thought you were going to say something like that,” she said, almost to herself. The hint of a smile was working it’s way open now, too.
“I need to measure you again,” she said as she drew the tape measure around my hips and then again around my waist. “You’re a 7 or an 8 in panties.” She turned around to one of the shop assistants. “Linda, could you see if we have either ‘Lace Fantasies’ or ‘Pretty All Day’ in a white soft-cup, 40B and 40C and matching panties in 7 and 8 for this gentleman.” She turned to me and excused herself. “I’ll be back with you in a moment, after I help these ladies.” I saw the woman with her teenage daughter doing their best to stare at me without appearing to even look at me. I looked around for a hole I could drop into.
After a couple of minutes, Linda tapped me on the shoulder and spilled an armload of white lace on the counter, arranging it for me. “I couldn’t find a 40B in the styles Andrea asked me for, but I picked a few other things out. These are really pretty,” she said as she arranged one of the bras over one of the panties. She was right, they were. The panties had a delicate stretch lace V pattern in the front that was repeated around the legs. The bra had a matching pattern on the top half of the cups and I deliciously imagined Carol in an outfit like this. Linda smiled sweetly and said, “I’m sure whoever you’re giving these too is going to love them and…”
At that point Andrea returned, picked up the panties and held them in front of my pants to gauge the size. I could see Linda blush a bit and stifle a giggle. “Hmm I still can’t tell.” She picked up the other pair of the same style in a different style and held those up as well, then shook her head. “Well, anyway, you’ll need to try this on to check the size.” She handed me the bra and started to steer me to the dressing room.
Well this was going just a bit too far, I thought. It was bad enough that I was going to wear a bra with my wife in the privacy of my own home but in a store, in a mall? No way. I started to object, but Andrea would have none of it. “Don’t be silly, the dressing room is private. Use that one on the right,” she said as she pushed me towards it with the bra in my hand.
I closed the door behind me and took off my shirt and undershirt. I slipped my arms through the straps as I’d seen Carol do a thousand time but I was darned if I could reach behind me to hook it up. As I struggled, I heard Andrea explain to Linda what was going on.
“That’s so cute!” I heard Linda squeal. “So, he’s already got, like, a skirt and stuff?” I didn’t hear Andrea’s reply but Linda must have approved. “Oh wow, that’s so neat!”
I decided to cheat. I took the bra off, then turned it around so the hooks were in front of me. I hooked it up, then twisted it back the right way and started to try to get my arms inside the straps again.
“Y’know, though, Andrea, if he’s going to wear tights (how did she know that — did the saleslady from Laura Brown’s tell them what I bought?) these, like, pretty panties are going to be wasted. And since he’s a guy, he doesn’t have, like hips or a waist, right? Maybe he’d be better off with these?”
I wish I knew what Linda was showing her, but I was having a devil of a time on my own.
“I think you’re right, Linda. These probably would work better. I wonder if he’s having a problem in there.” I heard her muffle a giggle, too. “Maybe I should check.”
She knocked on the door and walked in without waiting for me to answer. “Oh my, you seem to be having some difficulty. Here, let me show you. The first thing, is that you haven’t adjusted the straps properly. You’re going to need as much length here as you can get.” She fiddled with this little buckle-like thing and then pulled the cups down a bit. “That should be easier,” she said, as she helped guide my arms through the straps. “Usually, you’d put your arms in first and then hook it up, but I’ll bet you hooked it up in front, first, right?”
I just nodded. “I thought so. You’ll get better with practice” What did that mean, I thought? She smoothed out the straps, tugged on the cups, tugged on the back, ran her finger around the back. “This fits well here, so I think we have the right size. We don’t have this size in a smaller cup, though. What are you going to here?” she asked as she tweaked my empty cup.
“I’ll probably just stuff it with something,” I mumbled.
“Socks don’t work very well,” she said. “They get lumpy and they just don’t look right. We have mastectomy forms but they get very expensive.” I blanched. “What you can do, though, is to buy a pair of knee-highs and fill them with about a cup and a half of birdseed, or you could even do the same thing with a baggie and about the same amount of water. Both will fill these out nicely.”
“Stay right here. I’ll be right back.” She didn’t close the door to the dressing room behind her, so I lunged toward the doorknob, just as that teenage girl walked past me towards her own dressing room. I could have died. After a couple of minutes, Andrea knocked. “Are you decent?” she said, but she didn’t wait for an answer before she came in.
“This is called a waist nipper,” she said. “It’s a girdle with a high waist. Wear your tights under it and they won’t sag, but more important it will give you a little definition here (and she put her hands around my waist) and here (as she placed her hands on my butt). This is an XL and it should fit but I think you should try it on. You’ll have to leave your underwear on. Here.” She gave me the girdle and left, again without closing the door.
I was out of my league. Not only could I not figure out which end was the front, I couldn’t imagine how I could put these on over my boxer shorts. I just held them stupidly until Andrea knocked again and opened the door. “I thought you might have some problems,” she explained. “They go on this way,” she explained, showing me which way was the front. “Wiggle them up your legs and when you reach the top, pull up the waist. Then hook all these hooks and you’re all set. By the way, these will never work with the undies you’re wearing now. I brought you some panties. You’ll have to buy them but they’re on sale and I’ll discount them when we ring up the sale. Let me know when you’re all set.”
The panties were simple, white briefs, for which I was grateful. After she left, I slipped out of my boxers and put on the panties, which seemed to fit like a second skin. Then I slid the girdle up my legs, pulled up the legs and hooked the hooks, just as instructed. It took some effort to attach all those hooks, but when it was all done it didn’t feel all that uncomfortable. In fact, I was more than a little excited, and I’m not sure that this wasn’t obvious when Andrea came back into the dressing room, this time without knocking.
“I think this is just about perfect,” she exclaimed, as she tugged a little on the legs and then ran her fingers around the top band. “Don’t you think so?” I nodded mutely. “Oh don’t be such a fuddy duddy. This will give you a nice, girlish figure and, who knows, you may enjoy it! Get dressed and bring your things to the counter and we’ll ring you up.”
As soon as she left, I got out of those things as quickly as I could, which frankly wasn’t all that quick as I was still having some problems with these hooks and having the hooks in the back of the bra was an ingeniously torturous device. Eventually, though, I was back in my flannels and jeans and standing in front of Linda at the cash register with my new “treasures.”
She took the bra, girdle and panties from me and elaborately folded them while placing them back in their boxes. “Will that be all sir?” she asked.
“Umm, yes.”
“Would you like to join our bra and panty club.? Buy 10 panties or 5 bras and get one free?”
I just stared at her.
“It’s a promotion we’re running right now and I have to ask,” she said, with a conspiratorial air. “But it is a really cool deal if you’re interested.”
“I don’t think so,” I replied. She rang up the sale and handed my purchases. “Thank you very much and we hope to see you again soon, sir.” She positively beamed. I mumbled my thanks and tried to get out of the store as quickly as I could without knocking anything over.
I left the store and took a deep breath. While I felt some relief, I don’t know whether I was more relieved that it was over or that I didn’t die from embarrassment. I didn’t think I could do what I just did, but I did and Catherine, Andrea and Linda were all nice and my essential parts hadn’t dropped off when I tried my new skirt or my bra. This may not turn out to be as bad as I thought.
I assessed what I still needed to do. I needed shoes and I needed to do something about my hair and makeup. I didn’t remember if Catherine recommended any shoe stores so I just started to circle the mall. The first shoe store I saw was all athletic shoes and the next one had a clerk who looked like Al Bundy leaning on the counter. I just couldn’t see asking him for help so I walked on. A few more stores down I saw a store that looked promising. All the shoes in the window were women’s, both casual and dress, and both of the clerks were women in their 20s. One had short, black hair and the other longish, brown hair pulled back in a ponytail. There were customers in the store right then.
I went into the store and started looking around, while the two women continued to chat with each other. After what seemed like an eternity, the one with black hair asked “Do you need some help?”
I walked over to the counter. “I think I do. I had a bet with my wife and I have to watch this Sunday’s game in drag. Right now,” and I raised my two bags, “all I need is shoes.”
“Oh really,” the black-haired one said, raising an eyebrow. “This could be fun,” she remarked to her associate. “Do you know what you’re looking for?”
Why did everybody ask that question, I thought to myself. “Uh, no, not exactly. Whatever fits and whatever goes with what I’ve already got, I guess.”
“Can we see?” she asked.
“Sure, I suppose.” I gave her the bag from Laura Brown’s. She pulled out the skirt and held it up against my waist. I wasn’t expecting this. There were no racks to hide me, just a big, wide glass store front that was open to the entire mall. I quickly backed away but she reached out and put her hand on my shoulder.
“I’m sorry, I didn’t want to embarrass you. I just wanted to see what we have to work with. OK?”
I nodded.
“That’s a pretty skirt and we’ve got lots of things that will go well with it. What else are you wearing.?”
I pulled out the sweater and the brown tights.
“Oh that’s very smart. You’re gonna look great honey. Don’t you think he’ll look cute, Suzy?” She asked her partner.
“Absolutely.” They were talking to each other as if I weren’t even there.
“What do you think — penny loafers might work, or faux alligator loafer, maybe.” Suzy picked up a couple of shoes from the display and held them up for my approval. They both looked fine to me, but what did I know?
“They’re a little plain, Suzy” the black-haired woman said. “I think an outfit like that needs something with a little more character.” She turned to me. “Why don’t you have a seat, sir.”
As I was doing what I was told, she reached into a little box on the counter. “Take off your socks and these on or we’ll never get a proper size.” She handed me a couple of little balls of nylon that I found out later were called peds. It took me a second, but I got them on. I felt like an idiot.
By this time, Suzy had gone off to help another customer (who was looking warily at me). My saleswoman squatted down with that contraption they use for measuring foot sizes and after fiddling around a bit told me I was a 9 and that she would be right back and that I should relax (how many times had I heard that today!).
Just as promised, she came back with an armload of shoeboxes. As she tried on shoe after shoe on my feet, she kept chattering away at me and I didn’t hear a word. I was frozen with fear that someone I knew would see me trying on women’s shoes over ped-covered feet in this glass enclosed shoe store in the middle of a popular mall. She tried on big heels and little heels and shoes with straps and shoes that covered my toes and shoes that didn’t cover my toes and some of them fit and some of them didn’t but at this point I was dazed.
“So, what do you think?” She was expecting me to make a decision and my mind was absolutely blank. I looked down at my feet and for reasons I’ll never understand, like a bolt out of the blue, what I saw made sense. I was wearing (left foot only) a 2" clunky heel with a big brass buckle and an open toe and I liked the way it looked and I liked the way my foot felt in it.
“I think those will be fine, ” I squeaked.
“I thought so. These will look really nice with your outfit. They really do go together.” She put the other shoe on and told me to stand up. I did, and shook a little when I got upright, but then felt fine. I thought the shoes looked great and my feeling of weirdness completely disappeared, until I saw one of Suzy’s customer’s grinning at me. I sat down in a hurry and my black-haired saleswoman smiled and said, “Don’t worry about anything. You’ll never see her again, and besides, you’ve chosen a really great pair of shoes.”
She took off the shoes and put them back in the box and headed back towards the register. I couldn’t figure out what to do with the peds, so I put my socks on over them and followed her. After she rang up the sale, she asked “Will there be anything else — ooops — sorry — force of habit,” took my credit card and finished up.
I thanked her and as I was leaving, she gave me a wide smile and told me to “have a real good time, OK? By the way, we’d love to have a picture if you’re OK with that.” I must have blushed a dozen shades of crimson as I walked out, but to tell the truth, I wasn’t sure if I was blushing because I was embarrassed or because I was beginning to realize that I starting to like the idea of what I was doing.
The last thing on my list was hair and makeup. I knew that if I went into the local drugstore and bought a bunch of stuff and did it myself that I’d look more like Bozo the Clown than anything else, but I had no idea of what else to do. I knew I needed help but a beauty salon? The idea seemed ridiculous but having already tried on a skirt, a bra and 3" heels how much more ridiculous could I get?
On the ground floor of the mall near the offices and near the parking garage (thus on the way out) was a shop called Rita’s, written with big, curly script across the windows. Underneath, in smaller, but equally florid type it said hair — cosmetics — nails. I figured that this was the kind of place I needed, so I went in. Fortunately, there was nobody in the place except for a tall, big-haired redhead sitting in one of the customer chairs and a forty-ish woman with short, black hair sitting behind the cash register sipping coffee and reading Vogue.
I paused in front of the register. “Melpyu?,” she said, without looking up. After a second, it dawned on me that this was a contraction of “May I help you?”
“Yes, I hope so.” I launched into my sad story. “I’ve lost a bet with my wife and I have to spend this Sunday with her in drag. I’ve got the clothes (and I waved my bags at her) but I’m going to need help with my makeup and hair, I guess, but not today, first thing on Sunday. Or right after you open, because you probably don’t open until noon. Can you help me out?” I was babbling and she was staring at me but at this point my mouth stopped.
After a couple of seconds, she reached out and took hold of my chin and moved it to the left and then to the right. Then she stood up and ran her fingers through my hair (which is fairly long for a man’s but not real long) a couple of times. Then she sat back down and exhaled loudly. “Lemme see what’s in the bags.” I gave her the bags and she poked around a little, then stared into space for a couple of seconds and turned back to me.
“Y’know, the girls I usually have working Sunday would probably get you arrested but for something like this, I’ll come in myself.”
Then I exhaled.
“What I want you to do is this,” she said to me. “I want you to shave real close as late as you can Sunday morning. And I want you to wear something that ain’t too male or too female. Jeans and a T-shirt would be OK, but you ain’t gonna look like a girl coming in and you ain’t gonna look like a boy going out, so you gotta straddle. And you prob’ly oughta wear a baseball cap or something with a bill that you can pull down over your face when you leave, ’less you think you can be comfortable being seen in eyeshadow ’n shit. You think you can do that?”
“Yes” I replied with more confidence than I really thought.
“Alright, then. We open at noon, but if you came a few minutes early I’d let you in. And honey, one more thing. You forgot jewelry.”
I put my purchases in the trunk and drove right home. I was so relieved to find that Carol’s car wasn’t in the driveway. I hauled the bags upstairs and hid them in the corner of my closet, underneath the luggage. I then poured myself a stiff drink and sat on the back steps, watching the late afternoon sun while ruminating on the day’s experiences. I couldn’t quite reconcile the embarrassment I felt with the image of my in my new skirt, sweater and shoes, with curves in all the right places. In a way, I couldn’t wait for this Sunday to come.
I didn’t get any work done on Friday because all I could do was think about those bags lurking in my closet. I left the office as early as I could and headed back to the mall, where I picked up a pair of clip-on earrings, gold colored with an imitation opal in the center and some gold-colored bangles. I marched right into the store, right over to what I wanted, made my selections and brought them right over to the counter. I was so proud of myself.
Carol was in the kitchen when I got home so I had to sneak the bag past her, but she still wasn’t talking to me or paying any attention to me, so I didn’t have to sneak too hard.
Saturday was awful. I still couldn’t quite figure out whether I was terrified of getting all dressed up on Sunday or I couldn’t wait to put on my new skirt. I couldn’t concentrate on anything else and all day I kept bumping into things and dropping things. I was a mess. The only thing I did successfully all day was make my breasts out of baggies and water, the way the woman at Under It All instructed. I was amazingly precise when doing that.
Finally, Sunday morning arrived. Although I hardly slept a wink, I stayed in bed until Carol went downstairs around 9:30. I went into the bathroom and took a long look in the mirror.
“Here goes,” I said to myself and began to shave. I usually use an electric razor but I bought a safety razor for the occasion to get a closer shave. I was extra careful and took a long time and hoped that Rita would approve. As I stood there washing my face, I decided in an impulsive moment to do my legs as well and put the razor and shaving cream in the shower. After wetting down under the hot spray, I foamed my legs, took a deep breath and did it! There were a couple of moments when I felt like a pretzel (ever try to shave the tops of your feet?) but I did it. As I toweled off, I couldn’t begin to describe the feelings I got as I rubbed my smooth, now hairless legs.
Back in the bedroom, I got my bags out of the closet and found the tights. I’d watched Carol putting on pantyhose before, so I bundled up each leg in a ball and then sort of rolled them up my legs, then tugged the top up to my waist making sure that it was snug where it ought to be snug. So far, so good.
The girdle was next and I pulled it on over the tights and then spent an agonizing couple of minutes hooking all those damn hooks, but when I was done I glanced in the mirror and to my surprise, I had a waist, I had a butt and I didn’t have much in the front. Now it wasn’t much of a waist and it wasn’t much of a butt, but it was a whole lot more that I had about three minutes ago. The bra was next and I put it on just like Andrea at Under It All had showed me. I didn’t put in my baggie/falsies yet. That would come later.
Then I put on my new sweater and a pair of jeans. A big, gray sweatshirt over the sweater, a pair of dingy “white” sweatsocks over the tights, my sneakers, a light jacket and my Giants cap and I fairly streaked out the house to the car. I told Carol as I was leaving that I had a couple of errands but I don’t know if she heard me or if she cared.
As I pulled out of the driveway, I realized that I had at least an hour to kill before Rita’s opened so I just sort of drove around aimlessly once I got out of my neighborhood. At first, the tightness of the girdle and the bra and the feeling of material hugging the length of my legs was a little disconcerting but not unpleasant. But the more I drove around, the more pleasant it became. I don’t know if I could ever get used to having a bra stretching across my chest and over my shoulders, but this rest of this wasn’t turning out to be too bad at all. Realizing that made me more confused than ever.
I pulled into the mall parking lot around 11:30 and just sat in my car gathering courage. After a few minutes of deep breathing, I opened the door and marched out towards Rene’s. I went straight up to the door and Rene was there to meet me. She grinned a bit and said “I wasn’t sure you’d come.” She beckoned me towards one of the chairs towards the back.
“Have a seat, hon. My name’s Adelle and you’re…?” She looked at me expectantly. I looked at her with confusion and then looked at the sign on the window. “I bought this place a couple of years ago and it seemed stupid to replace a perfectly good sign. You still haven’t told me your name.”
I did and then she tied a bib around my neck and adjusted my head to and fro until she was satisfied. “I want to start with your hair because I want to try something and I won’t know if it’ll work until you’re ready to leave.”
I mumbled an “OK.”
“I think I might be able to use your own hair so you won’t need to wear a wig,” and she grabbed a couple of brushes and a comb and started attacking my hair. Attacking was the only work to use. She brushed it this way and that, pulled it up and brushed it down and just did all kinds of things to it. When she was finished, instead of sweeping across my forehead my hair fell in bangs. Instead of being parted on the left and swept back, it fell evenly from a part in the center. She picked up a brush that looked like a vicious drain cleaner and curled the hair that now dropped below my ears around it and then sprayed some stuff on it. When she unwrapped the hair from the brush, it held a little of the curl inwards. She did this all around the bottom.
When she picked up the scissors, I almost panicked. “Don’t worry hon, I’m not going to do anything that anyone will see when you comb it back into your boy style.” What she wound up doing was evening my bangs and trimming some rebelliously uneven strands from above my collar.
“There,” and she showed me her handiwork in the mirror. It was definitely a woman’s style and I thought it was fine but that I looked silly in it.
“Great,” I said, but I don’t think I sounded real enthusiastic.
“I want to see how this holds up while I do everything else. If it’s still there when I’m done, I’ll show you how to brush it to keep it fresh and you’ll be all set. Then, if you want to, you can comb it back to your boy style. Now let’s do your nails.”
She reached into a small tray and dabbed something on the index finger of my left hand. “This is an adhesive that will hold your nails in place. Your wife will know how to take them off,” she explained as she finished with the glue and then placed a long, sculpted piece of plastic over my own nail. It looked to me to stick out about six inches from my fingertip but subconsciously I knew I was exaggerating.
She finished the rest of hands, then spent a few minutes with a nail file sanding, poking and pushing things around until she was satisfied. Then Adelle sat back and took out some nail polish and began to paint. The color was a deep, rich reddish/brown that reminded me of mahogany. When she was finished, I couldn’t describe how amazed I was at how they looked or how strange they felt.
“Now keep your hands still so they’ll dry properly and I’ll get to work on your face. You’ve already shaved, I hope?” I nodded. “Good.”
With that, she started to work. By this time, another couple of her assistants had come in and glanced at us, stifling giggles but not saying anything. I began to wonder how I was going to get out of here since the mall was going to be open.
She applied a creamy kind of thing all over my face, smoothing it out first with her fingers and then with a cotton ball. When she lifted my bangs to cover my forehead and they fall back into place, she smiled.
Some powdery things followed. First one that was applied all over the creamy stuff she just applied, then a couple of different ones just to my cheeks. I just stared off into space. I was afraid to glance at a mirror.
“Now I want you to hold perfectly still,” she said as she pulled out the mascara (I knew what this was, because I’d heard Carol call it that when she used it). She leaned in real close and began brushing my eyelashes, upper and lower. Then she reached for a couple more different things and began to brush my eyelids and the area under my eyebrows.
“Your brows are a little thicker than I’d like. You want me to thin them out? They’ll probably grow back.” My eyes must have registered major alarm, because she shook her head and said “I didn’t think so. I’ll just try to shape them a little.” She took a tiny comb and began to comb my eyebrows.
Then, after she was done with that, she stepped back and looked at me. I was so self-conscious I was sure I was blushing furiously. She touched my chin and moved my head a little this way and that and then spent the next few minutes dabbing and poking at my with various things.
“Blink.” I did. “Shake your head.” I did.
“Well, I think I did a pretty good job — how ’bout you hon?” She made me look into the mirror and what I saw shocked me. I looked good. I looked very good. Staring back at me was the face that could have belonged to a successful businesswoman. Short, no-nonsense haircut, dark eyes touched with shades of gold and brown and flawless skin with a touch of color on the cheeks. The only thing missing was lipstick (even I knew enough to know that lipstick was missing.
“I didn’t put the lipstick on hon, because it would show up too much when you leave. If you pull your cap down low, most of your face will be hidden and folks will probably not notice that you’re wearing makeup. Put on the lipstick now and they’re gonna know.” I silently blessed her. “So what I want you to do is to pay real close attention when I show you what to do and you can put it on yourself when you get home.”
She showed me what to do and then gave me the tube. She also showed me what to do with my hair. “After sticking it under that cap and driving home, it’s going to need a touch up.”
When it came time to pay her, I had the hardest time trying to get my wallet out of my pants with those nails. When I finally succeeded, I realized I didn’t know what the tipping conventions were in a place like this. I gave her a big tip anyway.
“You’re usually not supposed to tip the owner,” she said. “But in this case, I think it’s appropriate.” She smiled. “Have a good time today, hon.”
As I opened the door to leave, I heard Adelle call after me. “Hey hon?” I turned around. “Hands in the pockets until you get to your car”
I drove home as fast as I could, making sure to keep my hands on the bottom of the steering wheel. When I got home, I headed straight upstairs, catching a glimpse of Carol sitting on the couch reading a book. I took one of her brushes and brushed my hair back into condition. Then I took out my lipstick and carefully applied it to my lips exactly as Adelle had instructed.
Off came the sweatsocks, the jeans and the sweatshirt (I should have waited to fix my hair, I said to myself). I took my skirt out of the closet and put it on, pulling the belt tight to emphasize my waist. I knotted my scarf and draped it around my neck and over my left shoulder. Next came the earrings and the bracelets.
I started to bend over to get my shoes, but about half way down I thought that bending over wouldn’t be very ladylike so I squatted down and then sat on the bed to put them on. As I stood up I didn’t know what to expect, but when I straightened up and looked in the mirror, I felt and looked simply wonderful and I was amazed at myself.
A quick check in the mirror made me remember that I forget a couple of very important items and I got my “breasts” from the drawer and put them in place. Readjusted the sweater and the skirt. Rebrushed my hair, squirted on a little of Carol’s favorite perfume and then walked down the stairs as quietly as I could.
In the kitchen, I placed the video, two glasses and the bottle of wine on a basket. One last glimpse in the downstairs bathroom mirror and I was ready.
I peeked into the living room and said “Ta da,” in as quiet, breathy and romantic a voice as I could muster. Then I swirled into the room, placed the tray gently on the coffee table and spun around in front of Carol.
The expression on her face was priceless. Surprise gave way to shock which gave way to a couple of lonely tears running down her face and then the widest smile I’d seen on her in years. All the money, time and embarrassment of the last few days was worth it just to see the smile on her beautiful face.
“Honey, I love you so much,” she said as she stood up and hugged me. Our breasts pushed together and as we kissed and hugged with a deep, loving passion.
“I love you too Carol and I’m so sorry for the way I’ve acted.”
I’d tell you the rest of this story, but there are some things between a husband and a wife that must remain private.
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Web Page Copyright © 2002 contact00@RealSissySchool.com; story courtesy ladycynthiak
Last Updated: October 24, 2002
Created: October 24, 2002
Author of Watching Football in a Dress story: ladycynthiak; reprinted with permission.
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