The Box

At this point I realized I didn't have a purse, so I just put my wallet, my lipstick, brush, and make-up remover into the overnight bag I had packed with my boy clothes. With one last look in the mirror, I strutted into the garage and climbed into my car. Fortunately it was late enough in the year that it was dark out so I didn't have to worry about my neighbors seeing me--nor Renee's neighbors once I arrived at her apartment.

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Renee lived in a four unit apartment building in a city neighborhood so my second challenge--the first challenge was adapting to driving my stick-shift car in heels--was finding a parking space on the street near her entrance. Fortunately, there was an empty space fairly close to the entrance and I managed to do a decent job of parallel parking, heels and all.

It took me about a minute after shutting off the engine to collect myself and give myself a pep talk that I COULD step out of the car and walk the 20 steps or so to Renee's entrance. I finally managed to open the door, carefully swiveling my legs towards the street, and trying to stand gracefully while simultaneously making sure the skirt of the dress didn't pull up. I didn't see any probing eyes on the street--lit by the streetlights--and locked my driver side door. I carefully walked around the front of the car, pulled my overnight bag from the passenger seat, pushed the lock down and shut the door.

To my amazement, my jitters seemed to instantly vanish. I was out in public in a dress--a gorgeous, sexy black dress with matching heels--and the sidewalk hadn't opened up and swallowed me whole. Something that I had imagined for years was actually happening--and I had this crazy dare from Renee to thank for that. Instead of rushing quickly to her entrance, I casually strolled the few steps, hearing the click of the heels on the concrete sidewalk.

Newfound confidence or not, when I rang the doorbell for Renee's flat so she could buzz me in, I was happy that none of her neighbors were at the door. I heard the buzzer, pulled open the door, and then began carefully climbing the stairs in my heels, holding a firm grip on the handrail. I made it to her landing on the second floor and knocked on her door.

Renee decided to yank my chain just a little more. I heard her voice in a sing-song tone say "Who is it?" and then nanoseconds later open the door. She took a step back from the door, looked me up and down, smiled, and simply said "Fabulous." I did a mini-curtsy and Renee invited me in and shut the door with a stupid grin on her face.

"I knew this dress would look better on you than it does on me. You do it justice. And your legs are just phenomenal. Turn around; I want to see the back" Renee said, and so I did. She clapped her hands and said "Marvelous. You look really good; better than I expected. Where is your camera? I want to take some pictures". I unzipped my overnight bag and pulled out my Canon SLR and flash and handed it to Renee.

Then she stopped, and said, "Hold it. You need accessories. I borrowed some from Pete; let me go get them" and she hustled off to a back room to get them. She returned with a fake pearl necklace, and had me turn around so she could fasten it around my neck. Next she handed me some black-and-white clip-on earrings and after several attempts I managed to get them on. Finally some gold colored bracelets for each wrist. Renee once again stepped back, eyed me, and said "Perfect. Come see for yourself" and led me to the mirror in her bedroom so I could have a look. I did, and came to the realization I was becoming a narcissist whose sole pleasure came from looking at him/herself in a mirror.

Back into the living room for a few photos, and then Renee announced dinner was ready. "Smells great," I said. I asked if I could help, and she handed me a bottle of wine and a corkscrew and said, "It's your job regardless of your attire" and also handed me some matches to light the candles on the table. I lit the candles, uncorked the wine, poured two glasses, and watched Renee bring our plates and put them on the table.

Renee then pointed me to my chair, and when I went to sit down, she said "Allow me" and then helped push my chair towards the table, like a gentleman would. I had noticed Renee was wearing a white blouse along with black slacks, flats, no jewelry, and minimal (if any) makeup.

Renee proposed a toast, "To your new look" and we clinked our glasses. The meal was excellent; baked chicken, broccoli with cheese, baked potato, and a salad. While we ate, we did updates on our recent goings on and then I asked, "What led you to do this?" and I pointed to myself.

"Well, I wanted you to have a memorable birthday. I also decided you needed a little nudging to discover your desire to dress; you did enough hinting to me that I could tell you were interested but hesitant" Renee answered.

I nodded and said "Yep."

Renee continued. "I also had some ulterior motives. I've been to a few drag shows with Pete and enjoyed seeing the drag queens. And, as I've told you before, I've been with women a few times. The idea of a woman with a 'surprise' is a turn-on for me."

I wasn't sure what I was hearing. "So seeing me dressed like this is a turn-on for you? You think I'm sexy dressed like this?"

"Well, I wasn't sure" Renee answered "but seeing you dressed this way is a definite yes. Plus, I am enjoying a bit of the dominance play, that you were willing to comply with my demands. You weren't far off when you accused me of being a dominatrix. I like that you are acting submissive--and I think you are enjoying it too."

"Yes, I seem to enjoy being told what to do. Maybe it's a defense mechanism. Boys aren't supposed to want to dress like a girl, but I'm not doing 'this' because I want to, it's because I'm keeping my word and going along with our agreement" I answered. I went on. "So if I'm 'caught', it's not my fault, I'm only following orders. But, we both know, I'm loving every minute of it, even though the shopping part was a bit daunting."

Renee then asked, "Do you feel sexy? Because you sure look sexy to me."

I answered as honestly as I could. "Yes, I feel sexy. The dress, the stockings, the heels, all of it. I love seeing myself in the mirror. I can't wait to see how the pictures turn out. On the other hand, I'm not aroused. Junior is behaving himself. The idea of dressing tonight has had me 'on edge' for the last week--and as you asked, I have not pleasured myself since the box arrived--but right now all systems are normal, so to speak."

I then had to ask, "So am I more sexy to you as a guy or a girl?"

Renee hesitated. "Do you really want to know the answer?"

"Yes," I said.

"Don't take this the wrong way, but definitely as a girl" Renee replied. "I hope that doesn't hurt your feelings?"

"Nope. After all, I'm only attracted to women, and it's probably not the optimal strategy to attract women by dressing as one, but the idea of dressing is definitely a turn-on for me" I answered. "I believe that all guys have a kink, and this is definitely my kink."

We finished the meal, had a dessert of ice cream with Hershey's chocolate sauce (out of a can, of course), and then Renee grabbed the camera again and took the rest of the roll of film, of shots of me in various poses, and a few of us together, using a tripod she had and the timer on my camera. We agreed that I would leave the film with her to have the prints processed, as that would possibly raise fewer questions and cause me less embarrassment.

Then the night took an unexpected turn, for me at least.

After the pictures, and sitting and talking while drinking a second glass of wine, perhaps with a few kisses thrown in, Renee threw me the curve.

"I told you earlier I've been to a few drag shows with Pete. Well, one more reason I asked you to come tonight is there is a drag show tonight at a gay bar about a block away. I'd like for us to go to the show. This is an ask, not a demand. I told you I wouldn't do anything that would make you uncomfortable, so it's up to you. There will likely be other crossdressers there so you won't be out of place.

But you look so great you ought to show yourself off to others. And.....and....if you do I will make it up to you after--hint, hint" Renee gushed with a big grin.

A slight--ok, major--panic settled in. I had long loved the idea of going out in public dressed but absolutely feared the reality of being out in public dressed.

"I have a major dilemma here. I need a lot more wine to overcome the fear of going out but I'm not sure that alcohol and heels can co-exist." I stammered. "How far is the bar?"

"About a block and a half," Renee answered.

"No torches and pitchforks once I step out the door?" I asked.

"Not likely, but always possible" as Renee chose to torment me.

"What if I need to use the bathroom?" I wondered.

"I'll come with you, silly," Renee laughed. She then added. "We don't have to stay long. The show won't start for a while, but we can have a drink and listen to the music from the DJ and maybe I can persuade you to have a dance or two. I want to see those damn fine legs of yours in action. We can stay for the start, then come back here for some more fun. Pretty, pretty, please?"

"Ok" I answered. "I'm excited and scared shitless at the same time. Who is always reminding me to expand my comfort zones? This is definitely going to be a walk on the wild side for me."

Renee just clapped her hands and smiled. "I promised you a memorable birthday, and the night is still young."

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Before we left, I did use the facilities, sitting (of course--it was a bit of an adjustment to sit down wearing heels as my derriere was a bit higher than usual) and I fixed, or at least tried to fix, my lipstick. I was happy my makeup was still looking reasonable; in one of our calls Renee had suggested I avoid touching my face, and I had done that mostly throughout the night. She handed me a black clutch purse that suited the dress and a black sweater, as it had cooled down somewhat outside.

In turn, Renee donned what appeared to be a men's black suit jacket that complimented the white blouse and black slacks. She was wearing black flats for something like a Marlene Dietrich look, sans the bow tie. With her short hair--short for a woman, at least--and black suit, and minimal (if any) makeup, it was clear that we were doing a role reversal, Renee as the man and me as the woman. I had no problem with that; wearing that black cocktail dress was a lot more fun than my normal suit. I was happy for her to be Marlene Dietrich to my Audrey Hepburn, though in my heels I towered over Renee by at least eight inches.

It was a short walk to the main street where the bar was located. I was adjusting to walking in heels, and having Renee with me and chatting while we walked calmed my nerves. When we reached the stoplight on the corner, Renee persuaded me to cross the street and walk the length of the block opposite, even though the bar was on the same side of the street as her apartment.

There were a few stores open, and we did a bit of window shopping. One of the stores was a woman's boutique, and Renee commented that a couple of the items in the window would look good on me. Fortunately--or perhaps unfortunately--the store was already closed, or otherwise I might have had to make a decision as to whether to enter the store or not. I wasn't sure I was ready for that challenge.

There were also others walking along the sidewalk, as this was a reasonably popular street on a Saturday night, with multiple bars and restaurants alongside the stores. It was nighttime, but light from the stores and streetlamps was fairly bright. As we walked along, I tried to avoid eye contact with the others walking towards us, but if they suspected something out of the ordinary, I couldn't see any outward evidence. All in all, it was probably only a ten minute detour to take the long way around to the bar, but I sensed Renee was doing her best to allow me to get my "sea legs" about being out in public.

When we reached the bar, Renee went first and held the door for me, and with a smirk she said "After you, madam." After we entered, she placed her hand on my back and nudged me towards a row of boothes to the left. We found an empty booth about three back and Renee said "Have a seat and I will go to the bar and get us a drink."

I softly said "You don't know what I want to drink."

With an evil smile Renee asked "Well, do YOU want to go up to the bar and buy us drinks?!"

After I shook my head no, Renee just added "You`ll just have to trust me then."

I managed to sit properly on the bench, reaching under the skirt of the dress to pull it under my butt, and gently sat down. I remembered to cross my legs, even though they were hidden under the table, and waited not-so-patiently for Renee to return with our drinks.

After a couple of minutes, but seemed like at least a decade, Renee returned with a draft beer and a mixed drink. Renee said "I got you a whiskey sour"; she had remembered a previous time when we had been out and I had ordered one, even though I generally drank beer instead of cocktails. I assumed her beer was keeping with the gender play, her being the man and me being the woman. She sat on the opposite bench, facing me.

Renee raised her glass and said "A toast. To new adventures!" We clinked our glasses and I echoed "To new adventures."

The bar was about half full and rock hits from the 60's and 70's were playing in the background, but we were able to talk easily.

"How often do you come here?" I asked Renee.

"About once a month, sometimes with Pete. It's usually pretty relaxed in here, except late on Friday and Saturday nights. But it doesn't get heated up those nights until around midnight" Renee answered.

"Do you usually take your dates here?" I asked with a smile.

"Only the ones in sexy dresses" Renee returned fire.

"So is the dress sexy or am I sexy?" I asked cheesily.

"Definitely both. You AND the dress. I can't say why but I'm feeling both" Renee responded.

"Are you trying to get me to go home with you?" I sang songed in a falsetto voice.

"Well you better, or you'll be going home in that dress, because your overnight bag is at my place" Renee smirked.

"Do you like your look, or is this just because you decided it was a nice contrast to my being dressed up?" I asked.

"To be honest, I've had some gender issues of my own. When I was younger, I was more of a tomboy. I questioned if I wanted to be male or female. Around puberty I decided I was more comfortable being a female, and I was attracted to males, although as you know I have experimented with women and I've enjoyed those times.

"I was never really happy having to wear dresses, especially when my mom tried to make me wear them. I probably like them even less now, as they are part of the corporate world and it's expected. I prefer casual clothes and tops and slacks. The suitcoat was to be a little more 'mannish' tonight, for my date who happens to be wearing MY dress at MY request.

"So my outfit tonight probably reflects mostly the real me, comfortable being somewhat in between" Renee concluded.

"Well, even if you didn't want to wear the dress, at least you have good taste in dresses, because this one is damn cute" I said.

"Just because I don't want to wear them doesn't mean I don't know what looks good," Renee continued. "But it sure looks better on you than it does on me."

A DJ then started his set and the rock numbers were replaced by electronic dance music at about twice the decibels. Renee and I finished our drinks and he headed out, with her holding me as I adjusted to the effect of alcohol on walking in heels. The cooler night air helped me clear my head a bit on the short walk home.

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After we made it back to Renee's place I asked her "Could I use the bathroom to freshen up a bit?" and Renee said sure. I told her it would be a few minutes and I grabbed my overnight bag and headed to her bathroom. She told me when I was done I should come to her bedroom.

I did my business and brushed my teeth and redid my lipstick. I then pulled the babydoll out of my overnight bag, along with the g-string panty. I managed, with some difficulty, to reach around and unzip the dress, let it down, and step out of it. I unfastened the snaps on the garters, and took off the panty, leaving the stockings on. I then put on the g-string, trying to hide Junior the best I could. I then put on the babydoll over the bra, so I still had some bumps. I had left the heels on so I took one last look in the mirror, liked what I saw, switched off the bathroom light and strutted towards Renee's bedroom, my heels clicking on the hardwood floor.

I made it to the doorway to her bedroom and tried my best imitation of the femme fatales from black and white movies of the '40s and '50s. I leaned against the doorway and tried my most sultry pose, racking my brain for a suitable movie line and coming up empty. I also discovered while I was doing my prep, Renee was doing her own prep work, lighting about a half-dozen candles around her bedroom. She had changed into a white t-shirt and black shorts, and was sitting on the side of her bed, watching me.

"Oh. I like" she said. "Come closer"--so I did, and--"turn around" and I also complied.

Renee then exclaimed "Gotta have pictures" and rapidly proceeded to the living room for my camera. She came back with it and handed it to me so I could turn on the camera and the flash, and then I returned it to her. She took pictures for the next 10 minutes, using different poses, standing, sitting in a chair, lying on the bed, with Renee extremely enthusiastic about the shots.

The photo session ended when the roll of 24 pictures ran out. She handed me the camera, I rewound the film, opened the back, popped out the canister and handed it to her. As we had agreed before, she would get them developed and give the prints to me the next time we got together.

It wasn't quite midnight, but in a seductive voice Renee asked "Do you want your birthday present now?" I wasn't about to say no, but it wasn't really a question anyway. She sauntered up to me, put her hands around my neck, and said "I've wanted to do this all night" and then did a massive liplock on me.

During a pause in the action I said "I wouldn't have minded" but Renee simply responded "I didn't want to mess up your makeup and lipstick."

I just laughed and asked, still in slight disbelief, "So this"--pointing at myself in my babydoll, stockings, g-string and heels--"really turns you on, huh?"

Renee chose to let her actions answer. She gently pushed me backwards toward the door leading to her walk-in closet, kissing me with each step. When my back contacted the door, she put her fingers across my lips to silence me and said "Raise your right arm" and I did. I watched her bend and reach to her left for a two-step step stool and she placed it next to my right leg. She climbed the two steps and reached for a strap--I found out later it was a man's necktie with a knot at the other end that was trapped by the closed closet door--and tied my right arm in the air at my wrist. "Does that feel ok?" she asked, and I merely nodded.

She climbed down from the stool, repositioned it next to my left leg, and said "Raise your left arm" and while I did she climbed the two steps again and tied my left arm at the wrist with a second strap. This time she simply asked "Ok?" and again I merely nodded.