The Box

Thanks to all who read, rated, and commented on my first story. That means a lot of pressure to produce a second story in a reasonable time frame (i.e, not five years like the first).

This one has been rattling around my brain for a long time also. It contains part real life combined with a large dose of fiction.

The real life part is Renee and her one time roommate Pete. Thirty-some years later Renee and I are still in contact, and for reasons best known to her, she loves seeing me dressed up. When I asked if I could write this story, her answer was quick; "absolutely."

Time to jump into the wayback machine. Hope you enjoy.

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Back in prehistoric times--i.e, the 1980's--there were no Tinders or Grindrs or match.com, because none of us were carrying cell phones around. Even desktop computers with bulky screens were just becoming popular, and AOL was still about five years in the future.

What there was were free weekly newspapers and those newspapers offered personal ads (the paper in question still exists today). They were usually in the back of the paper and had categories of women seeking men, men seeking women, etc. There were usually at least one hundred ads, so there were multiple choices. The ads had a short synopsis, generally the basics of the person posting the ad and what he or she was looking for. In other words, a prehistoric dating app, without fake pictures--because there were no pictures.

As I was between girlfriends--my main romantic interest was thousands of miles away in Melbourne, Australia--I decided to answer an ad and give it a shot. I don't remember what interested me in Renee's ad. Because this was before cell phones, I couldn't persuade her with a dick pic--I had to write an actual letter (the old type, with a pen on paper). I wrote a couple of pages, mailed it to the P.O. Box listed in the newspaper, and took my chances.

Sometime later Renee called me. We chatted and set a time to meet face-to-face. I assumed it was my astute writing skills that caused her to call me, but she later burst my bubble. She told me that as all letter writers had to pay $1 to forward their letters to her, they all deserved at least a phone call (except for one responder who sent his business card with a note on the back that said "I am confident that I can meet all your needs" and Renee was confident that he could not).

We hit it off reasonably well and began going out on occasional dates. It wasn't a torrid romance, but we enjoyed each other's company. We began to offer to cook dinner at our respective places, with the suggestion the invitee would be welcome to spend the night. In today's terms, we were "Friends With Benefits."

As we weren't that romantically interested in each other, we felt freer to talk about sex and try different things (all still pretty vanilla). For example, we would occasionally tie each other down--just the basics, nothing fancy--and please the other orally (although one night Renee fell asleep, so I ended up having my arms tied to the bed all night).

Renee had a lingerie collection, and I began to try on some of her items, which I obviously enjoyed, and which she encouraged. In clothing, Renee always preferred comfort over fashion. Because she was a professional working in IT, she often wore dresses, even though she would have preferred tops and pants. On more than one occasion, generally when we were meeting after work, she would tell me the dress she was wearing was Pete's, her crossdressing roommate.

Two events led to the rest of this story.

The first was an evening together and we were discussing clothes and dresses. Renee said that she had a black cocktail dress and that "I would like it."

I asked, "Like it on you?"

"No," she replied. "On you."

The second was a weekday night during the early summer. Renee came to my place after work (we lived about a half hour from each other) and brought her bicycle for a ride. I had two softball games to umpire, and while I umped my games, she would go riding, and we'd meet back at my place after both of us were done.

We had both arrived back at my apartment and were going to shower together. I'm not sure how we got to the subject, but I'm sure I might have been steering the conversation. I commented something like "My feet are too big for women's shoes."

Renee quickly responded "I can find heels in your size."

I said no and she said yes and I then said "If you can find heels in my size then one night you can dress me up."

Renee quickly agreed and said that was a deal.

About three weeks later, after she made a trip home to Cleveland, I showed up at her place and she had a pair of two inch black heels. Surprised, I tried them on--and they fit. Not surprisingly, I loved them. Renee didn't like heels--those heels might have been the last pair she ever bought.

As Renee had bought the heels and kept up her end of the bargain, you can be sure I was going to keep up my end of the bargain.

It took a while for our schedules to mesh but about six weeks later I came to her place for dinner and then get dressed up. I couldn't wait for dinner to be over so we could get to the main event.

After dinner, she sat me down and started doing my makeup. She explained the various steps but I was so excited--emotionally, not the "other" type of excitement--I couldn't really concentrate and learn. After the makeup, she gave me pantyhose, panties, and a bra to put on, along with a white floral two piece suit.

This was my first time since Halloween as an 8th grader to dress up. I was in heaven. We didn't have a wig, but that didn't matter. Renee said I looked better in her clothes than she did. I took it as a compliment. She had a light porn movie (a DVR tape, and I can't for the life of me remember the name) that ran for an hour or so, and I sat on her couch next to her and we watched it. I'd like to say we screwed wildly on the couch, but we didn't. Afterwards, she cleaned off the makeup, and as it was late we went to bed, did the deed, and slept.

That was the last of it for about the next three months. I went on vacation, and Renee went on vacation and traveled for her work, and although we talked occasionally, we didn't get together.

Then one day I came home from work and there was a box on my doorstep, a package from Renee. On the outside of the box, written on the side opposite the address, were the words "Call me before you open."

As instructed, I did. She answered.

"Hello Renee, it's Dave. How are you, and why do I have a box here with a request I call you before I open?"

"Hello Dave!" she gushed. "I'm busy but good. As to the box, isn't your birthday a week from Sunday?"

"Yes, that's right," I answered. "I'm surprised you remembered."

"I wrote it down a while ago, and as you are turning 29, I decided I could try to make it memorable. First, do you have plans for the Saturday night before your birthday?" Renee asked.

"No, I'm free. I'm going to my parents on Sunday but I have nothing planned for Saturday" I answered.

"Good. I'd like to have you over for dinner, say 6 o'clock. Would you like to come?"

"Sure, sounds great. It will be good to see you. Do you need me to bring anything like wine or beer?" I asked.

"No" she answered "I've got it covered."

Renee then paused and added. "As to the box, you have a choice. There are instructions in the box, and if you choose to open the box, you are obligated to follow the instructions in the box, or from me. If you don't want to play along, the offer for dinner still stands."

"Have I ever told you that you are a devious person?" I said with fake disgust. "Either all or nuthin', huh?"

"Yep" Renee gloated. "What's your answer gonna be?"

"Any hints?" I begged.

"Nope, no hints" she smirked. "Take it or leave it."

"Exactly when did you become my dominatrix?" I spit out.

Renee laughed. "You haven't agreed to the deal yet." Then she added what we both knew to be true, "Besides you are loving the idea of this." And the final truth, "Sometimes you have to get out of your comfort zone. But I promise three things. First, I won't embarrass you. Second, I'll make it worth your while.

"And the third. You don't have to call me Mistress Renee--unless you want to" she laughed softly.

"Ok, Mistress Renee," I joked. "I want to know what's behind Door #3. I agree to the deal. Do I get to open the box now?"

"Yes!" Renee exclaimed.

"Do you want to stay on the phone?" I asked.

"Absolutely!"

I was excited--and worried--I had agreed to something I would find difficult to do. I cut open the packing tape and found a note on top, and underneath three sheets of paper, folded in thirds, with the numbers 1, 2, and 3 written on them.

I picked up the note and began to read out loud.

"Happy 29th Birthday! Here is what I expect you to wear when you come for dinner. I am dying to see what you look like in my black cocktail dress. I hope it fits. I've also included the black heels I bought you. I asked Pete if I could borrow a wig that you could wear to dinner, and he said yes. I picked one that I think will suit you, plus a wig brush to comb it with."

I picked up the dress, unfolded it, and held it to my chest. "Nice dress," I told Renee.

"Try it on" Renee answered "I want to know if it fits".

I told her I was going to put the phone down while I tried it on. Shirt and pants off, unzip dress, step into it, pull up on shoulders, reach back, inhale, zip up halfway, scrunch dress up, reach from top, inhale again, stretch as far as I can for zipper, barely grasp it in my finger tips--and start to pull it up. It's tight--but it zips all of the way up.

I pick up the phone. "It zips".

"Yea!!!" cheers Renee.

"Excuse me, I'm putting down the phone again, because I'm vain and I need to look in the mirror," I explained. All I heard from Renee is laughter.

I walked into my bedroom where I had a full length mirror and had a look. I walked back to the phone and quickly said, "Just a sec." I reached into the box, grabbed the heels, walked back into my bedroom, sat on the bed, took off my socks, put on the heels, and strutted to the mirror again.

The "click, click, click" of the heels on my wooden floors pleased me as I walked back to the phone.

Picking up the phone, I hear Renee on the other end say "Well?"

"Am I allowed to say I love the look?" I asked.

"Goody!" answered Renee.

I picked up the note and continued reading out loud.

"As you are coming to dinner fully dressed, you are going to need to go shopping for the other items you will need." Ouch, I thought. "I have made three lists for you. Do them in order I have suggested. Have fun. Good luck." I finished.

"Like the surprise?" Renee asked.

"I love it but I'm scared to have to do the shopping." I answered truthfully. "And I will have to drive to your place dressed up, and I've never been outside dressed, much less dressed myself."

"You can do it. Expand your comfort zones. Pete says he never had an issue and he's got tons of girl stuff. But if you get stuck, I can arrange a time to go with you" Renee added.

"I will put on my big girl panties and go shopping," I answered. "I assume panties are on one of the lists?"

"Absolutely" Renee said with glee.

"OK, I think I have my marching orders. Do you want progress reports as I go along?" I inquired.

"Yes, please," Renee answered.

"I will call once I've done Step 1. Agreeable?" I asked.

"Yes," Renee answered.

"Thanks. This sounds like scary fun. Definitely EXPLODING my comfort zones. Good night, Renee" I concluded.

"Good night Dave" Renee said, then paused for a couple of seconds, and added "One more thing. No masturbating from now until our dinner. I want you on edge until then."

Ouch again.

I heard the click of her hanging up.

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I opened up the folded paper with 1 on the outside and read the instructions.

[Grooming. You will need to shave (or use Nair) on your legs, arms, and chest (the areas not covered by the dress). You may find it easier to shave in your bathtub while you have a bubble bath, or you can do it in the shower. You could also use Nair, assuming you don't have a bad reaction to the Nair. You can use the Nair to remove most of the hair, and then clean up the rest with a razor.

After you shave, I recommend using lotion on your arms and legs.

But I want you hair-free when you come to dinner].

I'd never had the courage to shave my legs before--in part because I spent a lot of time at the YMCA in athletic shorts--but I was curious as to the look and feel.

I walked to my bathtub and began running the hot water.

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It took about an hour, and topping up the tub a couple of times with more hot water, but my arms, legs, and upper chest (just below my nipples) were hairless. I drained the tub, watching my discarded hair circle down the drain, and turned on the shower. The hot water on my bare skin felt sensuous, and then I remembered Renee's last command, and I told myself, "Down, boy, down!" I picked up the razor and cleaned up a few more strays.

Shower finished, and after drying off, I applied lotion to all my shaved areas--and then stepped into my bedroom for a look in the full length mirror. "Not bad" I thought.

Back on went the dress and the heels. The dress felt smooth against my skin, and the heels enhanced my bare legs.

Step One was a winner.

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I decided I would wait until after work the next day to open Step Two. I wasn't sure I was building up the suspense or trying to avoid freaking out for the day about what I was going to have to do. I held off until after dinner, and then picked up the paper with Step Two--and the phone to call Renee.

"Hello" Renee answered, and I responded "Hello Renee, it's Dave. I wasn't sure if you'd be home, but you wanted progress reports."

"Yep!" Renee enthused. "Report away!"

"I shaved last night. Felt different against my sheets and against my suit pants. I went to the Y this morning for my usual 6 AM game and nobody seemed to notice.

"Now I'm ready to open Step Two and figured you'd like to hear the Big Reveal, although it's not a reveal to you, because you wrote it."

"Yes and no," Renee replied. "I know what it says but I didn't write it. Pete did."

Now I didn't know what to think, so I opened the paper and began silently reading.

Renee ended the silence. "As you know, I don't use a lot of makeup; never have, never will. But Pete does, so I thought he would do a much better job of listing what makeup you needed to buy."

I started to read from the top, out loud for Renee's benefit.

"This is a list of what I use, that I have discovered through trial and error. Yes, it's a bit daunting to buy makeup as a guy, but I have found the checkout staff don't really care. I usually shop at Walgreens and I have found all these products there.

1. Maybelline liquid foundation, medium beige

2. A stipple brush to apply foundation. Squirt foundation on the back of your hand, then apply to your face using the stipple brush.

3. Maybelline makeup powder.

4. A powder brush to apply the powder. Use a brush to apply powder to your face, covering the areas where you applied foundation. The powder helps the foundation set and takes off some of the sheen.

5. Revlon brow powder and brush kit. I use the brown two tone powder kit that comes with two brushes. Use the lighter color on the inner portion and the darker color on the outer portion.

6. Revlon dual color blush with brush. I mix the two colors together and apply to my cheeks. A little is enough.

7. Mascara; any brand works. Use the brush to apply to your lashes, brushing upwards.

8. Eye shadow. There are many colors and brushes to apply, but I can never get it to work right, so I generally avoid using eye shadows.

9. Silver and black eye pencil. One end is silver, the other black. I apply a light coating of the silver below each eye, and a little bit of the black on the waterline below my pupils. Once again, a little goes a long way.

10. Lipstick. So many choices, so just choose a color you like. I have found if I apply the lipstick to my bottom lip, and then close my bottom lip across my top lip, that does a better job of outlining my lips than when I try to do something more sophisticated. I then fill in a little more on my top lip to even things out.

11. Nail Polish. I use Sally Hansen quick drying polish. I use a clear coat first, and then whatever color I've chosen (for me, some shade of red). I usually try to make only two or three strokes with the brush.

12. Nail polish remover. Better to buy now than after you've done your nails!

13. Makeup remover.

I would practice a few times before the big night. The more often you practice, the better you get. I have found less is more. Shave well, make sure the beard and mustache areas are covered, and do the other basics listed above. Relax, and have fun.

Now take this list and go shopping!"

I finished reading and said to Renee, "I guess I could cry uncle and ask for help, but you know about as much about makeup as I do." Renee laughed and said "I told you I outsourced the job and Pete was a much better option--but the offer still stands, I will come with you if you like."

"Maybe I can get Pete to come with me?" I joked. Renee laughed and said "I could ask him."

"No, I will manage. You gave me this challenge, and although I'm nervous about this, I keep hearing your words in my head about expanding my comfort zone."

"Good girl!" Renee exclaimed. "I think you'll enjoy buying the makeup more than I ever will. I consider it something I have to do to fit others' expectations; you will consider it something you want to do to fit YOUR expectations of how you want to look."

I was silent for a few seconds while I thought about what she said. I finally said, "I guess you know me better than I thought you did. Thanks, I think."

Renee chuckled and said, "Good night, Dave."

"Good night Renee" and I hung up.

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Saturday morning I took the list and headed to the nearest Walgreens. The store fortunately was mostly empty. I didn't spot any apparent mind readers amongst the other customers so I figured my inner thoughts were safe. I walked the makeup aisles, finding the items on the list one by one, adding them to my basket, and checking them off with my pen.

The last two items were the hardest to select; nail polish and lipstick. Too many choices, and I wanted the two to match as closely as possible. I knew they had to be a shade of red, but there were 23,000 shades of red (maybe a slight exaggeration). I found a color named "Midnight Red" and a reasonably close shade of nail polish--and to keep with the theme, I headed to the candy aisle and threw a bag of red licorice on top of all the makeup into my basket. I walked up to checkout and hoped my face wasn't a matching shade of red.

The cashier was a middle aged woman who had the air of someone who had seen it all before. She emptied my basket, rang up and bagged all my items, told me the total, and took my credit card. She wrote up the slip, I signed it, and gave me the two bags, accompanied by the obligatory "have a nice day."

I walked out the door, let out a breath of relief, and broke into laughter. Two down, one to go.