Girl's Night Out


It was shortly after I had returned from a trip to Las Vegas. I had not seen my good friend Matt in over a month so I called him up to talk to him about the trip and show him some pictures. Although we still trained together weekly for karate we hadn't been out for a while and wasn't sure if the "thing" we had was bothering him or not.

The "thing" was a night a little more than a month ago when Matt found out that I was a crossdresser. He had found some stockings of mine in my bathroom that I had neglected to hide before he came over for a drink. Curious, he had slipped into my bedroom which is adjoined to the bathroom and took a peek in my closet and drawers, finding more evidence that I had a number of female garments.

Matt had brought out the nylons and handed them to me. I tried to imply that a girl left them behind but he quickly stopped me and told me that he had seen my closet. I was busted so I had no choice but to come out to my best friend about dressing up like a girl. It was very tense because he was silent for a while and looked like he wanted to hit me. The tension was biting me. Our friendship was on the line. I was hoping that our friendship was strong enough to get thru that moment.

He asked, "Are you gay now or what?" He knew I had been with a lot of girls so he must have felt stupid for asking that.

"It's not like that at all," I answered. "It's more like I love everything about women so much, I want to be like one myself," I added. It was more or less true. I didn't need to tell him more than that at the moment. I didn't know at the time that it may not have been the answer he was looking for.

He thought about it for a few minutes then broke his silence with a surprising statement. "I want to see what you look like dressed up," he said very seriously. There was another long pause as I judged my friends honesty. "Would you do that for me Marty?" he continued.

"What, right now?" I asked in astonishment.

"Yes, now, why not?" he asked, very casually.

I considered for a second. My face was still smooth from a late shave, my legs were smooth under my jeans. I downed my glass of scotch and told him, "It takes me about an hour to get made up."

"I'll just wait here then and watch TV," he answered.

"Okay then," I said with a deep cleansing breath and turned to go to my room but paused to return and take my stockings from Matt.

I was shaking. It was important to get through that awkward tension and it all might have hinged on that moment. Matt was my only close friend since college. We hung out, talked and were genuine friends. I didn't want to scare him off. I went through my makeup routine. I always start with my false eyelashes then put on my foundation. I then add powder before working on my eyes. Eye liner is followed by brow pencil, then eyeshadow. Mascara is the last item. I then add blush but hold off on lipstick until I get dressed.

At twenty -three years old, I was fit, lean and in my prime. My fair, blond hair and self-made smooth body made me look more feminine then most guys and a lot of girls. I helped it along by regular eye brow plucking, and leg and body shaving. I had light green eyes which I felt were my best asset.

I started with the corset, the black one, then pulled on panties, garter belt and a bra, all matching black lace. I stuffed my bra with the silicone falsies I owned, giving me a good 'C' cup rack. I went to my closet and selected a short hem black dress with a pleated hem lime, silver front buttons and translucent fiery sleeves. I pulled up the black stockings and fastened them to the garter straps. I selected my silver loop earrings and some silver, bangle bracelets. I grabbed my blond wig and shook it out before pulling it on. I gave it a quick brush. I heard Matt call from the other room, "Aren't you ready yet? What's taking you?"

I was putting on my brightest red lip gloss and stopped myself from yelling back. Looking into the mirror, I could not make myself yell back in my masculine voice. I grabbed my open toe, four inch sandals with stiletto heels and thin black ankle strap and carried them out of the room. It had been just over an hour but it always felt much faster. Time flies.

I had come out and began putting on my shoes as Matt stared at me with an open jaw. As I finished strapping them up, I did a pirouette then stood posing in front of my friend. His light brown eyes were watching me intently.

"Wow! you look really good as a girl," Matt said to my astonishment. "I never would have guessed," he added.

His words and smile were encouraging so I sighed relief and began flittering about and posing. That seemed to impress him even more. "Are you sure you haven't turned gay on me?" he asked again. In truth, I had sucked off two different cross dressers that I had met at different times but I decided not to relay that information at that time. I didn't really consider it 'gay' anyway as they were more like girls to me, but that would require a longer explanation to my friend. Instead I just reaffirmed my previous plea. I nervously strutted about the room while my best friend checked me out like a piece of meat.

I had not really noticed at first but Matt had paused the video tape machine during a a two girl scene in the movie. The frozen image on the screen was of two pretty girls in a loving embrace. He continued to say nothing but was smiling as I posed for him. I continued to grow confidence and was teasing provocatively yet I still did not render a comment from my friend.

"Well, fucking say something, will you?" I demanded nervously.

"I wonder what it's like?" Matt inquired.

"Wonder what, what's like?" I asked.

"Being a girl, I mean," he said. "I wonder what it's like to be a girl?" he went on.

"Do you really want to know?" I asked my friend.

"Think you could show me?" he blushed. Matt is fair, even freckled, and he was a shade of pink. His question was inspiring to me. He was about the same build as me, we were the same height at least. I figured I had some clothes that could fit him. I also had imagined him in a curly dark haired wig.

And so it began. I dressed Matt up that night, complete with makeup and wig. His feet fit perfectly

into a pair of my stiletto pumps. The pink summer dress I had looked so good on him with the curly brown hair. He seemed to take right to it. We spent the next hours looking into the mirror, painting our finger nails, and trying on different outfits. We snapped a few pictures of each other strutting around like sexy divas. I was amazed at how easily Matt slipped into a female persona. I never felt more comfortable with Matt.

We eventually returned to the living room and saw the frozen image on the screen of the two girls kissing and Matt let out a sigh. "That is so beautiful," he said in a soft feminine voice. I approached him, sensing what he wanted. He did not move as I approached and placed a soft, gentle kiss on my friend's painted lips. Matt did not respond at first and I feared trouble but soon he embraced me and we shared a delicate, tender kiss. Soft tongues were intertwined. It lasted a few minutes and our lipstick was a mess on each other's face. Matt backed away, and brushed his face with his arm. I wanted more but panic had been installed in Matt's mind. He went to the other room and washed up, returning to his male form. "I think I should be getting home," he told me nervously before leaving. Since then there has been some tension and we have both got tight lipped about it.

Our friendship continued somehow but I was afraid to bring up the topic of that night whenever we talked. Finally, after I had been away for a week in Vegas, Matt left a message on my answering machine. He said he was sorry for making me feel uncomfortable and that he was not unhappy about what had happed 'that night'. It was shortly after I had returned from a trip to Las Vegas. I had not seen my good friend Matt in over a month so I called him up to talk to him about the trip and show him some pictures.

Matt agreed to come over and when he arrived I poured him a large scotch on the rocks. We had some small talk about Las Vegas and then he asked to see the pictures I had of us from 'that night'. He was pleased to see them and I let out a sigh of relief as he exclaimed the beauty of my female image as well as his own. I made sure to compliment his images. I was truly impressed at Matt's alter ego and was no longer afraid to tell him so. He again apologized for his hasty departure and I was getting the feeling that he might want to play dress-up again.

There were some pictures in the bunch that were from other nights including a few from Vegas where I was in a bar and posed with some other girls, so to speak. "Have you been out in public a lot?" my friend asked. I felt some tension again.

"Yes, about five or six times," I stated with confidence. I didn't want to appear covert anymore.

"That must be fun," he went on.

"Yes, it's a real thrill," I said. "I've even been to the club here in town, the Rose club," I added.

"Easy enough I suppose, when you look as feminine and natural as you do," he stated with an inquisitive stare.

I smiled. "I think you looked far more natural than I did," I said. "If you were to go out, looking just like you did in those pictures, I am sure you would pass as a girl, easier than even I could," I implored.

"And you have no trouble that way," he asked.

Confidently, I smiled. "No, I have never had a second look unless it was a look that was checking out what a hot girl I was." "In fact it would be even easier for you," I added. "I have never seen a better natural," I flattered.

"It must be a huge thrill, being seen, I mean," Matt asked.

"There is really only one way to find out," I told him with a devilish grin. Matt smiled back at me and I knew we were in for a girl's night out. For this occasion I selected a pink and charcoal plaid miniskirt with pleats and a pink silk top for Matt. He would wear some charcoal stockings and black, bow tie, patten pumps. I squeezed him into a pink corset with six garter straps and laced him tight. I then showed him how to make cleavage with duct tape. I let him wear a pair of black lace tanga panties and showed him how to tuck in his dick so no bulge showed in front. The silk top clung tightly and the skirt made Matt look like he had a real female body.

For myself, I decided to go with a black and white hounds tooth miniskirt, and a black and white silk top. The body was black and clingy, while the collar, transparent sleeves and the buttons were white. I wore the black corset with six wide suspender belts and solid black stockings. My panties were black lace too. For shoes I pulled out a pair of lace up ankle shoes, in a black and white, penny loafer style but with four inch heels.

I made sure that our makeup was flawless, working every detail and contour so that the image of femininity was complete. Matt wore the curly brown hair again while I wore my long, flowing blonde wig. A touch of perfume made it just right.

Matt was practicing his walk in the high heels when I was finished getting dressed. He was getting pretty good at it by the time I got there. I reminded him to keep his weight on his toes and his shoulders back. "What about talking?" my friend asked. It did sound odd coming from the pretty girl I was looking at. The voice was too deep but Matt's natural voice was higher than most guys so he just had to soften up his words. I told him to breath his words in my own practiced feminine voice.

"Another thing girl," I said, "Is I can't call you Matt in public. We will have to come up with a more appropriate name for your new look."

"I was thinking Michelle," Matt confidently replied. There was some thought behind that after all. "What name do you use?" he asked in a coy, soft voice.

" I just go by Mary," I said. "I know, it's boring but it was the name of my first love, so I like it," I defended. Matt, or Michelle as she was now, giggled like a real girl and made me blush. I lit up a roach end of a joint to relax and offered some to my friend. Michelle shook her head. Matt had smoked pot before but didn't partake as often as I did.. I poured us both another scotch, which Michelle gladly took, to get our nerves calmed. We selected our jewelry and accessories while we sipped our drinks. I liked the big loop earrings and Michelle put on some dangling threads. I picked out two chokers for us, a white one for me and a black one for Michelle. We added bangles, ankle bracelets, and chains to our outfits. I made sure that the camera again captured the images of us two lovely ladies.

"I'm still nervous," Michelle confessed as it approached the time that we should be leaving.

"It's fine, the Rose club has girls like us in there all of the time, it really very normal," I consoled.

"It's getting to the place that scares me," Michelle said. True, getting down the hall to the elevator, down to the street, and the two blocks walking were not in the safety of the club and no doubt several 'normal' people would see us.

"Don't worry, look at yourself, no one will know anything," I stated. I went on, "Besides, no one can recognize you, even your own mother wouldn't know that Michelle was her son, Matt." There was still uncertain apprehension. I reinforced my certainty by displaying the proper attitude when passing some stranger. "Keep your head up, shoulders back, cock your hip, and always smile confidently," I said. I strutted around a couple of times to show him/her what I meant. "Your turn," I announced.

Michelle strutted back and forth across my beige carpet and mimicked my actions. "How's that," she asked with some real feminine grace.

"Perfect! let's go," I announced and dragged my friend by the arm. I really felt that Michelle needed a test to boost her confidence level. Halfway down the elevator ride from my twenty seventh floor apartment, the car stopped and an elderly couple entered. The old woman smiled politely and I smiled back. The man took a second look and almost began drooling while checking out the two hot young chicks on the lift down. It stopped again at a lower floor and a man about our age stepped on and his eyes almost bugged out of his head. He started primping his hopeless look. He was in a plain white tee shirt and faded jeans and looked generally unkept. He kept trying to steal glances at the sexy, leggy girls on the elevator. I glanced over at my friend and smiled a knowing grin and winked. She smiled back and breathed a little deeper. On the way out, the guy tried to smile and say hello. Michelle was half running for the door but I just smiled back and whispered a shy, "Hi." He was fumbling an attempt to introduce himself but I had to catch up with my girlfriend so I ran away too. I could feel his lustful stare on my ass as we strutted out onto the street.

It was not too busy so I reassured Michelle, "You see, already, three strangers, and no problems. I even think that we broke that guy's heart." We giggled and I could tell Michelle was getting into it. Her brown eyes were aglow in the night lights of the street. She took my elbow and we began marching down the street towards the club. Not even half a block down the street, a car passed with its windows rolled down. I could hear the whooping and whistling before they were even beside us. A car full of dudes out cruising the streets, making asses of themselves. We both knew better than to encourage them but I could not resist the urge to flip them the bird as we marched along the concrete sidewalk.

"Do they really thing acting like that will get a girl to like them?" Michelle asked.

"See, now you sound like a real girl too," was my only reply as I held in a burst of laughter.

The next part of the walk was the trickiest. There was a popular dance club, a primarily straight bar, called the Front Stage which we would have to walk past just before getting to the Rose. It was a Saturday so the Front Stage had a line-up in front which was typical. We would have to walk past the line-up to get to our club. I was closest to the crowd while Michelle was on the street side. I avoided making eye contact and sprint by the line-up as quickly as possible in high heels. We could not avoid inevitable comments and cat-calls just the same. We heard, "More legs than a bucket of chicken," from one creative guy.

"Hey girls, you can get in line with me," from a few guys closer to the front of the line.

"Fucking bitches, think that dressing like sluts gets them in without waiting in line," from some dull looking, no makeup girl wearing jeans and a tee shirt. I was pretty sure she was saying it to her equally dull looking friend but intended for us to overhear. We got past the Front Stage with its long line and came up the Rose which had no line-up. I was relieved to finally be there and could sense the same from my friend. The problem was that when we tried to go in, the door was locked shut. I couldn't figure it out. I pulled and yanked at the doors but they were solid. Then there was the recognition that we could hear no loud music coming from inside, just silence.

"Marty, check this out," Michelle called to me.

"It's Mary, bitch! While I'm dressed like a girl, I expect you to address me as one. I do for you," I snapped.

"Sorry, Mary," she emphasized. "Read this notice over here," she said pointing to a bill posted on the wall where the marquis usually was. It stated that the Rose was temporarily closed for a liquor licence infraction. They were notorious for letting underage patrons in and it must have finally caught up with them. So we were faced with a dilemma. The Rose was the only gay and lesbian bar in town where it was always safe for cross dressers to go.

"Sorry to disappoint you Michelle, your debut will just have to wait for another night. We better head back to my apartment," was all I could say. I could see the disappointment in those brown eyes. Her adrenaline must have been pumped up from the parade in public and her confidence high.

"There's no other place? Really?" she asked with bemusement. I just shook my head. It was a bit uncomfortable just standing there so I prompted Michelle to turn around and head back to my place. Reluctantly, and with a sigh, she came along. It made me think what all the other usual patrons of the Rose would do with their club closed. No doubt many of the gay boys and lesbians would try out the 'straight' places where they would be safe if they kept low key. I wondered how many would try to get in next door at the Front Stage.

As we approached the Front Stage I tried to prepare myself for getting past the gauntlet again. This time Michelle was on the inside, as we walked with our arms locked at the elbow. At the front of the line, a brush cut behemoth was holding the velvet rope. A few steps from the entrance, someone whistled a loud wolf whistle at the two approaching girls. It made the burly doorman turn his head and raise his eyebrows. Instinctively, he opened the velvet rope not to the next in line but to us. "Ladies, you can go in," he said in a polite manner. The people at the front of the line began giving the doorman grief with insults of unfair preference.

I was very flattered at the gesture and felt my own confidence boosted by the act but had no intention of going in. It was just too risky. I was ready to smile and carry on past but Michelle had stopped me. Our elbows were locked and I was being pulled toward the door. Michelle had gathered up more courage then sense and was dragging me in with her. I wanted to protest but it would have made a bad scene in front of the bar and I wasn't about to abandon my best friend to her own devices. I just had to follow her in. I was beginning to mutter a soft 'Thank You' to the big cropped haired bouncer when I suddenly recognized his face. I stopped after only the 'Thank' came out.

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bytgirl_Mary© 17 comments/ 115446 views/ 31 favorites

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