The Box

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I headed home, pleased with myself. I opened the bag of licorice and began pulling off strips and gobbling them down while driving. I pulled into my garage, grabbed the two bags, and headed to my bathroom, where I organized all the items on the vanity next to the sink. I was tempted to try it all then, but decided it could wait until that night. However, I couldn't resist opening the lipstick, twisting the tube until it popped out of the shell, and tried applying it to my lips. Loved the color, and realized I would need lots of practice to avoid looking like a clown.

I grabbed list #3 from the box and dialed Renee's number. I wasn't sure she would be home on a midday Saturday, and no answer at the other end suggested she wasn't. I decided I would go ahead and do this list solo.

I unfolded the list and read from the top.

"If you're wearing girl stuff on the outside you'll need to wear girl stuff on the inside.

First, you need to buy a bra and panties. You can either choose functional, like me and my granny panties, or you can get something lacier and more sexy. I think I know which one you will choose. As to sizes, we should be the same, to make it easier for you to know what size. I'm a 38C in bras, and a size 6 in panties. I think black would go best with the dress, but any color should work.

Second, I know you have a thing for pantyhose or stockings. I think nude works best with that dress, and you can decide whether you want hose or stockings. Personally, I hate both on me but I will enjoy seeing either on you (have I told you you have great legs?). You can figure out the correct size from the descriptions on the back of the package.

Third, as you will be spending the night, you can buy a nightie or negligee if you are so inclined. Your size is probably best an XL. If you don't, you can borrow one from me. But I think you'll want one for yourself.

Have fun shopping (I know you will),

Renee"

I guess I knew this list had to be coming, but I was still worried about being the lone guy in the intimates section of the store. After lunch, I would be making a trip to the mall.

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I thought about driving across town to another mall but I decided in the end to stick with the local mall. There were a couple of large department stores and other smaller stores so I would (nervously) have my choice of places. I was trying to decide what was the better strategy; buy everything at one place to pull the bandage off quickly, or spread out the purchases to reduce suspicions? I didn't have a good answer.

I'm sure it was just my imagination that all eyes were on me, and it seemed like every teenage girl from three counties around were circulating through the mall, but I managed to make my way to the JCPenney at the mall first, as it was the nearest entrance to where I had parked. I found the intimates department and began searching with my eyes of the racks where the bras were hanging. Fortunately, I didn't see any staff, nor did anyone approach me to ask if I needed help (answering my silent prayers).

There were racks and racks of different options, and with not a lot of experience of taking them off girlfriends, much less putting them on myself, I wasn't sure what I should be buying (and I sure wasn't up to asking). I was just trying to limit my choices to two options, size and color. Fortunately, there were some signs describing some of the differences, so I got a mini-education in bras that I never got from mom.

Then a surprise; rounding a corner of racks I found a section of padded bras, along with another sign describing the various levels of padding. Quickly deciding the best choice would be the maximum padding ("plunge push-up"), I began looking for a size 38 in black. For better or worse, I found one, a 38C. Looking first in all directions, and seeing no snooping eyes, I reached out and touched it, feeling the depth of the padding, and noticing a modest amount of lace.

Again looking around and seeing no one, I took it off the rack for a closer inspection. With one final look around, and seeing it was all clear, I put the cups behind my back and reached the straps around me to check the fit, and it seemed to be the right size. I wanted to avoid the misery of buying a bra, and then the embarrassment of having to return it and buy a different size.

Then I looked around one more time, and saw the sign pointing to the men's room. Bingo! Realizing I could surreptitiously sneak the bra into the restroom without too many prying eyes, I squished the bra into as small of a size as possible, and walked towards the door. I wasn't exactly sprinting, but let's just call it a brisk walk.

The men's room was empty and I headed to a stall and closed and latched the door. Off with my t-shirt, and arranging the bra cups along my back, I straightened the straps, and fastened the bra along my chest, and rotated the cups to the front, then put my arms into the armholes. I reached around behind to make sure everything was smooth, and readjusted the straps for comfort. It fit, and felt good, and looking down, looked good.

I threw my t-shirt over the bra, and left the stall and walked to the sink, or more accurately, the mirror behind the sink. I checked the door, hoped no one would walk in, and lifted my t-shirt to my shoulders so I could have a look in the mirror, or at least a peek. I quickly raised the shirt, looked for a few nanoseconds, and pulled the shirt down again. Popping back into the stall, I reached around my back and unhooked the bra, remembering what a former girlfriend did, took the straps off my arms through the armholes of my t-shirt, then removed the bra. Now I just needed to summon the courage to walk to the checkout counter and buy the damn thing.

There were several options regarding service desks, and I wanted the one with the shortest lines and the most amenable checkout clerk--although I had no clue how to judge who that might be. I didn't even have a good cover story as to why I was buying a padded bra. I was also hoping my face wasn't fire engine red.

I walked to a service desk with only one customer, and as I approached, it appeared the clerk was finishing up with the sale. The prior customer departed, and the clerk, a pleasant woman who appeared to be in her 40's, asked "Can I help you?"

I muttered "Thanks" and placed the bra on the counter. The clerk said "That's a pretty choice" and I managed to utter "I got pretty specific instructions--but just in case, what are your return policies?" I asked. The clerk smiled and said "thirty days with the receipt" then rang up the sale on the register and said "with tax that will be $22.49." I handed her a twenty and a five, she counted out my $2.51 in change, put the bra in a bag, handed me the bag and receipt, and said "have a nice day!"

"Thanks" I answered and floated away, amazed I was able to escape so easily.

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I knew from past reconnaissance missions--i.e, doing some perving in the intimates section of the Famous Barr department store in the mall--that Famous often had clearance sales for panties. They would have large boxes with signs taped onto them with sizes, and lots of different styles haphazardly strewn around in the box, from customers sifting and sorting through them to find something they liked. Usually the panties were on sale for at least half off the regular price, and sometimes more.

With my JCPenney bag in my hand, I walked through the mall towards Famous. I was almost having Edgar Allen Poe images in my head that all the people I passed along the way knew I had a bra in my bag, but I knew in reality they didn't.

I arrived at the intimates section, and first browsed through the rack of the clearance items for nightwear, but there was nothing in my size that appealed. Then I saw the clearance boxes for panties, and slowly creeped toward the box with the large handwritten "L" sign taped to the side. Fortunately, no one else was fishing for panties, so after a quick look around to see if anyone--or more embarrassing, anyone I KNEW--was spotting the guy who was shopping for ladies' intimates, I walked up to the table.

My quick guess was there were fifty to seventy-five pairs in the box, all shapes, sizes, and colors. Most had red "50% Off" stickers attached to the price tag, and the marked down costs were mostly in the $3 to $5 range. I began fishing through the box, looking for something that was practical but still sexy (no "granny panties" for me!). My preferred colors were, of course, red and black--but if the style was suitable, the color didn't really matter.

I found a pair of pink lacy boyshorts that I thought looked cute and would likely fit me. I put them aside and kept panning for more gold. Next up was a pair of black hiphugger panties, the same size as the boyshorts. Now I had two in my pile; in for a nickel, in for a dime--as long as I was buying one, I might as well buy a couple of pairs.

Near the bottom of the box was a real find; a blue pair of panties with four attached garters. Quickly I checked the size, and it was the same as the other two pairs I had chosen. Renee had given me the choice of stockings or pantyhose, and finding these panties made the choice for me--stockings.

Gathering the three pairs I had chosen from the box, I went looking for the hosiery. It was a few aisles over. I began reading the packages on the back for sizing information, looking at the intersections of my height and weight. There were also more options for colors than I would have guessed. I decided on getting two pairs, one in nude and one in black, so I could try on each and see which color went best with the dress. Once again, I surveyed my choices of checkout counters and found one once again with only one customer in line. Bolstered by my previous purchase, I waited my turn, placed the items on the counter when it was my turn, and paid for my new items with only a tinge of red on my cheeks.

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My last stop was the Frederick's of Hollywood shop, located along one wing on the second floor of the mall. I comforted myself that at least while shopping for a nightie or babydoll I would have the excuse of buying it for my (imaginary) girlfriend. I also knew their selection was likely to be a little more risqué than the department stores at the mall. I figured the more "out there" Renee would appreciate it more--and so would I.

With my other bags in hand I walked into the store. There were various fun and sexy items on the walls and hanging on the racks; nighties, negligees, baby dolls, and other skimpy pieces of clothing I had no idea what they were named. Once again, I was thinking red or black--or maybe a combination of both.

I saw a rack of something called the Lara May Lace Babydoll and began flipping through the racks, checking on sizes, wondering if it would fit (and how silly I would look in it). I liked the look and figured I'd need an XL. I found an XL in black and pulled it from the rack and speculated on whether I could squeeze into it. With this, I couldn't sneak it into the restroom and try it on, and I sure wasn't going to try it on in the changing room.

While I was holding the babydoll the clerk, a young woman, strolled over and asked "Do you need any help?" I answered by asking my own question, "Is this a popular item?" The clerk, whose name tag said "Sally", said, "Yes, one of our best sellers. Who are you buying it for? Wife? Girlfriend?"

"Girlfriend" I lied, then added, "well, I want to see how she'd look in it, so maybe I'm buying it for myself!", and Sally laughed and said, "All guys think alike!". I thought to myself, not all guys think alike, because I wanted to see me in it, and I wanted Renee to see me in it, and not the other way around--and I wanted to look sexy in it.

Not exactly the standard model for attracting a woman, but for reasons I could never understand, it was my model.

Checking back into the real world, I asked Sally, "What are your exchange policies in case this is the wrong size?" which, for once, wasn't a lie. "Thirty days with a receipt, and the tags attached" Sally answered.

"I'll take it" I said (before I changed my mind).

"I hope she likes it," Sally added.

"So do I" I answered "so do I."

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I stopped at the supermarket on my way home for some groceries and a six-pack of my favorite beer, and then a second stop at a burger place to carry out my Saturday evening meal--double cheeseburger, fries, and a large chocolate milk shake. I knew that after dinner I would be doing a practice run; makeup, clothes, heels, nails, wig, the whole nine yards. I wanted the beer to make sure I had enough liquid courage.

After arriving home and eating my meal before it got cold (and my milkshake melted), I called Renee. When she didn't answer, after the beep I said, "Hello Renee, it's Dave. I have completed my shopping missions. Soon I will be doing a practice run. Not sure how it will go, but excited about it. Hope you're having a good weekend. Bye!"

I spread all my new clothes on my bed and mentally planned my evening. First a close shave of my face, then shower and a body shave, makeup, get dressed, wig, mirror. I also decided I needed to keep track of the time, so I would know how much advance time I needed next Saturday.

After shaving my face--a balance between getting it close and not cutting myself--I jumped in the shower and shaved my arms, legs, and chest, cleaning up what I had missed a few days before. Satisfied, I climbed out of the shower, feeling pretty smooth, and dried off.

Time to find out whether the babydoll fit. I strolled naked into my bedroom and fished into the Frederick's bag and retrieved it. Unfolding it from the tissue paper it was wrapped in (it was for my "girlfriend" after all), I raised it above my shoulders and let it slide down my chest. It was a bit snug, but it fit. One small victory. The babydoll came with a g-string panty so I put that on too; it didn't quite cover everything that needed to be covered but it was a fun and sexy feeling. A look at the mirror confirmed that it fit reasonably well, but would likely look better with makeup and the wig rather than the guy me.

Leaving the baby doll on--I decided it would be more fun doing my makeup wearing it--I returned to the bathroom and began removing the makeup on the counter from its packaging. With the note from Pete as my guide, I began arranging the various items in the order I needed to apply them.

Reminding myself of the old adage that goes "How do you eat an elephant? One bite at a time", I began with the foundation. Slowly, step by step I progressed, trying my best to get it right and not overdo things. After about a half hour I had done my face, except for the lipstick. I decided to hold off on the lipstick until the end and started in on my fingernails.

I did somewhat ok painting my left hand, only using the remover once when I painted more skin than nail. Using my non-dominant left hand to paint the nails on my right was a challenge, a version of paint, remove, paint, remove. They were reasonably satisfactory by the time I was done, realizing in the end only Renee would be seeing them next week, so they didn't have to be perfect.

I thought about doing my toes but decided no one would see them anyway, so I passed on them.

After the nails dried, it was back to my bedroom to get dressed. Off with the babydoll and g-string, on with the panty with the attached garters. I opened the sleeve with the nude stockings and carefully removed them. Rolling them up, I stuck my right toes into the first stocking and rolled it up my leg. I savored the sensation of the nylon against my bare leg. I fiddled with the fasteners at the end of the garters and somehow managed to attach the stockings, and then repeated the process for my left leg.

Next was the padded bra. Fasten in front, spin around, arms through straps. Remove, adjust straps on both sides to lengthen a bit, try on again. Look in the mirror. Smile big time.

Removing the dress from the hanger in the closet, I unzipped it and stepped into it, pulling it up my chest and over the bra, putting my arms into the armholes and adjusting the straps on my shoulders. I reached behind my back for the zipper, zipped it half-way up, then struggled to zip it the rest of the way, but I finally managed. Tight, but it fit. Next, sit on my bed and don my black heels, and once again head to the mirror for another look. Getting there.

I grab the brunette wig from the box along with the wig brush and begin combing through it, then multi-task by walking into the bathroom while putting the wig on my head. Reaching the mirror above my vanity, I brush the wig to even it out upon my head. Satisfied with how the wig looks, I uncap the lipstick and gently apply it to my lower lip, and then overlap my lower lip on my upper lip, transferring the lipstick. I fill in the missing places on both lips, and finally admire the smiling image that is staring back at me.

Not exactly Audrey Hepburn in "Breakfast at Tiffany's"--no diamond necklace nor the black gloves--but the look of the dress made me feel sexy. I knew I needed more practice with make-up, but Renee was right; I liked the dress.

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I spent the next week with a little more time at the YMCA and simultaneously watching what I ate, discovering my girl side was vain. I mentally counted down the days, practiced getting made up twice more, and tried avoiding getting too "stimulated", because I had promised Renee. We talked twice--she was out of town doing what she called her "corporate clone" routine, and was returning Friday night--but she said she was looking forward to Saturday night.

Ditto.

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My college football team was the featured 2:30 game on Saturday afternoon which made for a good diversion for my nervous energy. I had worked out that it would take me about an hour and a half to get ready, and a half hour to drive to Renee's, so to make dinner at 6 I would need to start prepping at 4. The first half ended around 3:55 so I turned up the sound and wandered to my bathroom to get started.

With the week of practice, I had a routine. Shave my face twice with a razor, shower, shave my body. After the shower, a third shave with my electric razor, then lotion on my face. Next were my fingernails, trying to get them decent. Then the make-up, starting with the foundation, moving onto my eyes, and finally the lipstick. I was finishing up the make-up about 5 when the phone rang, so I went and answered it.

I said my normal hello and I heard a cheerful Renee on the other end ask "How's it going?", and my answer was "getting there."

She teased me "Not beautiful yet?" and I answered "I don't think I'll ever be beautiful" and Renee's quick retort was "I'll be the judge of that." Then she said she would let me finish and was anxiously anticipating how I'd look, and before I hung up I said I might be a few minutes after six, because this "getting pretty" stuff took longer than I planned.

My outfit--I internally laughed at the thought of my outfit--was laid out on my bed. Like the week before, panties, stockings, bra, dress, inhale, zip up dress, finally heels. My final touch was the wig, which I brushed out, put on, and brushed again. A look at the full length mirror, then a stroll into the bathroom to get a close-up view of my face, and I decided my look was as good as it was gonna get.