An Eventful Halloween free porn video

"An Eventful Halloween" I looked at the calendar and noticed it would soon be Halloween once again. I took a deep breath and decided that this year I would have a little fun and go to the party as my alter ego. It was that part of my personality I always kept to myself but over the years when Halloween time neared I always got to thinking about what it would really be like to venture out into the world dressed from head to toe and from the skin out as a woman! This year I started early. I had been thinking and then planning for months. I'd made my decision. I was going out totally dressed to the company Halloween party! I figured what was the big deal, I mean really. It was Halloween and everybody gets a little crazy anyway and it's only one night a year I thought as I hit the shower with my shave cream and new Gillette razor. I pulled the curtain and dialed up the hot water and let the steam fill the shower. My mind was racing and my stomach was tight as I started shaving my legs, chest, underarms, everything. I looked into the mirror then realized the moustache had to go. I had to hop out of the shower and clip it short with a scissors first but was soon back in the shower shaving it off. I then lathered my face once more and gave the fresh blade another pass making sure my skin was as smooth as I could get it. I quickly dried my short hair and toweled down then noticed how different I looked without my moustache now. I thought it might be fun seeing what a face with makeup on would look like without the facial hair. It had been so long I could hardly remember. Once back in the bedroom I went to the back of the closet and took out what I would need. I had a complete outfit and didn't want to get too wild so I picked a vintage cocktail dress from the 1950's. I had a "housewife" type wig and all the lingerie I would need and even a new pair of seamed stockings! I selected my pearl earrings and matching necklace and grabbed the standard pair of black patent leather pumps with the five inch heels. Once I got everything laid out on the bed I set my makeup case and my mirror on the dresser and pulled up a chair. It was strange to think about what I was doing. I had done this many, many times before of course but only at home with the drapes drawn, and always by myself intent on having my pleasure while always keeping things low key. But Halloween was different, it was a pass. It was the perfect way to play my little game of dress up in plain sight of everyone and if I just laughed it off and only, only did it once and never mentioned it ever again I figured it could be the perfect plan! I whipped through the foundation, the eyeliner and eye shadow with practiced ease then noticed my pair of false eyelashes in the tray. Why not, I thought. If we're going to do it let's do it right and really impress them I figured. It took a while to get the lashes right because I didn't often wear them but I eventually had them combed in with my natural lashes and they looked pretty good and with all the other eye makeup they really emphasized my eyes. The lipstick and blush went on without a second thought then I took my best bottle of gloss red nail polish and quickly did my toe nails. I had a set of the glue on salon nails that were long and glamour length and the same color red so I decided to use them. It didn't take long until I was dusting my face with powder to set the makeup and then I put the dangle pearl earrings in my pierced ears and added the necklace. Once I slipped on my "housewife" wig I was pretty astounded at the results. Without the moustache I had worn for five years sitting below my nose like a bristle brush now I realized I didn't look half bad. In my excitement the dressing went faster than usual but I paid attention to detail like always. I tucked into the tight panties as the water balloons jiggled in my long line brassiere. The padded girdle and stockings were just right including the razor straight seams and the three sizes too small waist cincher over all that to pull my waist in nice and tight. The old fashioned lacy, white satin full slip followed and finally I slipped into the layered nylon chiffon cocktail dress and after struggling with the zipper finally had it zipped all the way up in the back. I checked my look in the mirror added some perfume then put a few things in my matching purse and finished by slipping into the five inch stiletto heeled pumps! I switched the money and the stuff in my wallet that I would need for the evening into the ladies pocket book which I kept in my vintage purse. Once I looked inside I even found a pair of white ladies gloves but with my long gleaming nails now in place I decided to leave them in the purse for an accessory only. I took a deep breath and excitedly headed for the garage and the car but once inside I realized it would be nearly impossible and possibly dangerous to try and drive with heels on, especially since I hadn't had any practice. I went back inside and grabbed a pair of loafers. They didn't match the outfit but they would work great for the drive over to the club. It was a long drive, pretty much all the way across town but I made good time. I was a block away from the place and could already see the crowded parking lot and people coming and going. Then I realized I was totally dressed like a woman! I felt the normal tension and apprehension of course but it was a bit more intense now because this was a new experience, I had never done this before. I pulled my car off to the side in the shadows and could feel my hands getting clammy and my heartbeat quicken. The company had rented the basement hall of one of those fellowship, member lodges that were a lot more popular in the old days but because of all the people the large space was needed. I reached for the door handle then took my hand away wondering why I got all dressed up like had. Was I taking too much of a chance? I thought further then remembered once again that this was the annual "Halloween" party. It could still work and if it didn't what was the worst that could happen. Yank off the wig light a cigar and sit at the bar having a few belts with the boys over a good laugh. I could still blow it off as a "zany" idea and then never mention it again. So here I was and now it was put up or shut up. I pulled the door handle and felt the cool night air swirling around my skirt and nyloned legs. I became excited then looked down and saw I was still wearing the penny loafers! I switched back into the shiny black stiletto heels then split the difference and decided to go around the back of the building to a quieter and darker entrance. It was much harder walking in the stiletto heels across the parking lot and even tougher walking down the gravel path to the back entrance and service door than it ever was in my carpeted apartment but I managed to get to the concrete sidewalk at the back door without falling. I looked through the small square window in the door to see the place was already busy. I took another nervous breath, checked my hair and smoothed my dress then reached for the door handle. But I froze! I couldn't do it! I let go of the handle then stood there satisfied for the moment to just look in on the party. I watched the parade of people as they mingled. There in the corner was Mr. Jameson in his tired old CEO costume again. A gangster pinstripe concoction from the 1940's that smelled like moth balls. There he was, still chasing Donna. He had the worst toupee I had ever seen, it never fit right and wasn't even the right color to match his hair and it wasn't part of his costume either. If he hadn't been the boss I am sure someone would have wised him up long ago. And there was Donna, trying to be polite but standing at an arms length. She could smell the moth balls too. There were the hooker babes, some which didn't look half bad! And there was Fred again doing his Pirate "shtick" as usual. He always took out his partial to display a missing eye tooth and he always had that stupid cardboard sword that was made to look like metal by wrapping tin foil around it. Ethel was doing the "dykes on bikes" leather look, wonder what that's about. And there was Phil, the former college linebacker already half way through his third drink weaving across the dance floor and headed for the bar. I was wondering if he would make it before his glass ran dry! Then I noticed he had come in drag along with a couple of other guys. He had on his football jersey with what looked like oranges stuffed under his shirt to simulate breasts. He had his hair pulled into tiny spike like pig tails that were held in place with little girls pink plastic berets and a shade of pale pink lipstick that didn't match his three day growth of beard. His grass skirt swung as he walked revealing his khaki dockers rolled up at the knees displaying his hairy legs which terminated in rolled down sweat socks and dirty sneakers! Phil was getting a lot of attention and most of it was laughs as everyone watched him weave towards the bar doing his impression of a hula dance. I felt the cold chill of the wind as it swirled around the back entrance then looked down at my legs as my skirt fluttered in the breeze just above my knees. The nylons gleamed in the light on my smooth hairless legs that stood perched atop the shiny black stiletto heels. I could smell my perfume and feel the makeup on my face and felt the purse I was holding in my hand then noticed my feminine appearance as I caught my reflection in the window of the back door. But it was too much! This wasn't going to work. If I had tried to "camp" it up like Phil or a few of the others or even look like a couple of the guys who tried to get the look down but missed the boat it might have worked. But I knew now that over the years I had gotten way too good at my hobby. My throat tightened and became dry as the nervousness returned. There was no way I was going in there now, no way. I cringed as I imagined pulling the back door open and then clicking in on those heels wiggling my hips and giving everybody a wave looking like the homecoming queen while that floaty nylon chiffon cocktail dress swung and twirled around my legs as I made my way to the bar to order my pink lady. The band would stop, people would turn and look and then glare at the guy, or think "is that a girl coming in?" While still others would drop their drinks to the floor! They'd look for a moment longer, their brains scrambled in overload and then they would notice my missing moustache and then the eyes would widen and the talk and laughter and the finger pointing would start as they figured out who it really was. I looked far better than any of the other guys who came in drag. But I had done too good a job. Someone on the edge of the dance floor looked towards the back door but luckily they turned away. Then I heard the metal rod door opener being jiggled and tapped from the inside! I quickly clicked on my heels around a wood sided shed and hid in the shadows. The door then opened, I could hear the band playing and the people inside. I then heard someone moving down the little sidewalk and looked out of the shadows to see it was one of the cooks taking out a box of trash. He dumped the box then dropped the lid on the dumpster with a "clang" and then quickly went back inside. Well that was it I thought. I stayed in the shadows a moment longer then quickly made my way up the gravel drive, across the back of the asphalt parking lot and got back into my car. I took off the heels and set my purse aside and put the loafers back on. I then took a cigarette out of my purse and lit it, then cracked the drivers window to vent the smoke and took a break to think. Even though it was getting late people headed to the party in costume and those in standard formal attire were still coming and going from the club upstairs. Thankfully I hadn't been seen. I finished my smoke then decided to call it a night. I had been driving only a short while and tried to make sense of the evening and how stupid I had been to go to the party all decked out like I did. I watched as the street lights flickered past the car and how the light would cause the chiffon of my cocktail dress to shine. I noticed my gloss red manicure as I held the wheel and could still smell the perfume and figured that although it was a waste of effort it was better this way. But still it was Halloween and I had always wanted the chance to go out just once where others could see me. I was at the stop sign just about to hop the freeway for the drive back to my side of town when I saw what appeared to be a friendly bar. It wasn't too big, and wasn't too crowded but the people coming and going looked like they were enjoying themselves. I then saw a couple of women dressed doing the hooker bit with a small man who was dressed as a pimp walking along in the middle. They seemed to be having a fun time. The costumes were really well done too. I looked further wondering why the girls were so tall and why the pimp was so short and then it dawned on me. The girls were the guys and the pimp complete with sideburns and moustache was really a lady! I watched further as she poked at her moustache with her fingers to keep it in place. That was one of the giveaways I recognized. But still it was an amazing costume! The clock on the dash said 11:30 p.m. now and as I looked at the bustling freeway I decided to take my chance. I turned the car drove down the block and pulled off to the side in the bar's parking lot. I put my car keys in my purse, checked my look in the mirror then switched shoes. I could feel the air swirling around my nyloned legs and how it swirled my skirt as I left the car and crossed the parking lot. I continued to the sidewalk in front of the building and was then awash in bright neon light which gave me no place to hide now. I clutched my purse and continued on to the front door where I met a large guy in a suit who turned out to be the door man. "Good evening ma'am!" He said as he swung the door open for me. I smiled silently and then entered the crowded bar with my heart in my throat. I could feel my heels clicking with my short mincing steps and feel the garters on the stockings pulling as I walked. I could smell my perfume and could feel my water balloon boobs as they jiggled in the brassiere I had on under the chiffon cocktail dress. I saw an empty bar stool near the edge of the bar and thankfully noticed it was a bit darker over there. I turned and made my move for the empty seat. I took a few more steps. "Nice legs sweetie!" a female voice rang out in my direction and then "Damn! Check out the legs!" I heard some guy say as I wiggled along then turned to see a group of folks all decked out for Halloween night as a couple of them pointed and one guy raised his drink in a "hey, pretty good look" salute as he smiled at me. Did he read me as a guy? In the dimly lit bar and with the booze flowing and the loud music I wasn't sure, but they must have known. But nobody was hassling me. I continued to the bar and took my seat as I continued to relax and get into a ladylike posture that fit the clothes. I felt like a beer but ordered a martini instead then opened my purse and took out another cigarette. It relaxed my nerves to take the first puff and as I blew the smoke away over the bar I looked to see my red taloned nails holding a cigarette that now had a red lipstick imprint on the filter. And still nobody was bothering me. I started to relax and ordered another drink then watched the band and a few of the party goers. It was nice that most of them hardly paid me any attention and was most likely due to many of the younger guys in drag that looked pretty good. My look was more old fashioned but so far I was doing alright and best of all hadn't seen anybody that I knew. I could have a couple drinks, relax and then head home after I was satisfied I'd had enough of this Halloween night. I ordered another martini. It wasn't long until I needed to use the facilities so I started looking around. I saw the restrooms at the far back of the bar and with no choice I grabbed my purse and made no pretense at choosing the men's room. I used the stall instead of the urinal and was finished up in no time. I pulled my girdle up tight once again, checked my seams and then fluffed the chiffon dress back down. I stopped long enough to look in the mirror and saw that although I didn't look perfect, I didn't look too bad at all! Guys were coming and going and one did a double take as he saw me leave. "Man, you could get fucked looking like that baby!" He said as he moved inside and I left heading back to the bar without saying anything. But on the way back and with my nerve fortified by three martinis I took the chance and the liberty to swing it a little. I leaned back put my chest out and minced on the heels swinging my hips just like the lady I was pretending to be. I heard some gossip and a couple whistles but was soon back at the bar feeling a bit excited and heady from the experience. I was just about to grab my purse and leave when a guy in a Tin-Man costume stepped up to the bar. He ordered his drink and looked me over. "Hey Dorothy!" He smiled as he studied me. "Takes a lot of guts to try that look. Nice outfit though, nice legs too!" He said as the bartender brought his drink and he paid for it then quickly returned to his group at a corner table. I then decided I'd had enough and decided to finish my drink and then leave. I took out another cigarette and as I was holding it in my red lipsticked lips and was fumbling through my purse for my lighter a man sat down next to me. He then produced a gold lighter then held it in front of me and lit it as he offered me a light! "Thanks man" I said in my regular masculine voice as I took my first puff on the cigarette then closed the purse and slid it to the side and returned to my drink. He looked me over. He noticed the high stiletto heels, the shiny nylons on my shaved legs and noticed the old fashioned nylon chiffon cocktail dress and the vintage purse that sat on the bar. "I bet that if you tried that with a feminine voice you would fool a lot of people" he said as he started a conversation. "Ah, it's just a Halloween deal, you know?" I said as I fell into my standby explanation. Some of the guys in drag were younger and some looked better than I did but they didn't seem to have any real class though and there wasn't an outfit or hairdo like mine in the place. I looked like a classy babe from the 50's. The man motioned to the bartender pointing to the bar circling his finger as he ordered a round. I glanced over. He looked 10 maybe 15 years older than me, he must have been in his early 40's or so. But he looked kind and had a good look for his age, not that I notice guys but he seemed to have class. He wasn't in a costume and instead had on a tweed sports coat, a turtleneck sweater and a nice pair of slacks and dress shoes that seemed to somehow match the gold lighter he had lit my cigarette with. Then the bartender brought him his drink of whisky on the rocks and slid another martini in front of me. I hadn't ordered the drink and my cigarette was on the down side of being a red lipsticked butt in the ashtray. I told the man I didn't care for another drink and that I was just about to leave on my way home. "What's your hurry? By the way my name's Doug" he said with a smile as he shook my manicured, red nailed hand and noticed the red glossy salon nails. "Tim" I answered. He seemed to want to talk and when I turned to face him and crossed my legs he noticed the black patent leather stiletto heels and the shine of the nylons I was wearing and heard them zip as I crossed my legs and smoothed my dress out. " I haven't heard that sound in a long time" he said trying to hide his excitement. He went on to say how women these days had forgot long ago how to dress and even act like women. And I had to agree, I wasn't into the "grunge" look or the "tough chick" deal either. But strangely the conversation didn't turn to football, or race cars or anything manly in the least. He just kept on about how much he liked my outfit and how pretty and feminine my legs looked. I took a gulp of my martini and made plans to leave but Doug touched my arm to coax me to stay a bit longer as he felt the sheer chiffon of the long sleeve that ended in a triple buttoned satin cuff. "What's your hurry?" He asked, seeming slightly hurt at my imminent departure. I mentioned I had a bit of a drive and I thought I would get going. I then noticed as the bartender brought us another round! More small talk continued. I worked as an internal claims adjuster for an insurance company as a glorified files clerk. The pay was crummy and It was a dead end job. I learned that Doug had been a widower for almost 5 years. He didn't have any children and was just getting used to an early retirement. He'd had a good job and lucked out on a few stock deals and was now pretty well set but he was bored being alone. I told him I wouldn't mind being retired either at such a young age and not having to put up with a crummy job. We talked further about a bit of everything until I felt I just had to get going. I congratulated him on his good fortune and tried to be nice as I patted him on the back. "Nice meeting you Doug, and thanks for the drinks" I said as I grabbed my purse and swung off the bar stool then quickly stumbled on the stiletto heels. I looked to the clock and noticed it was much later now, then I realized I had just finished my sixth martini! I thought about switching to coffee but in looking at the clock I could see it would soon be closing time and I had a long drive through town to get back to my place. "Shit" I thought as I sat back down. "Is there a motel around here that is close by?" I said as I asked the bartender. Doug was listening. "Yeah, five, six blocks down the road past the next freeway exit" he said pointing his thumb in the direction. I decided to get going and drive as carefully as I could and then sleep it off. I was lucky it was Saturday night. It wouldn't be much fun checking in looking like a debutante but it couldn't be helped. Then Doug spoke again. "You can stay at my place." "No! no" I said. "I wouldn't want to put you out, it's too much trouble. I'll just grab a hotel room, I'll be fine" I said. But the conversation continued. He had a nice big house with plenty of spare bedrooms. He offered to drive me back to his place then return me to my car in the morning where I could get in and drive back to my apartment. "It's no big deal" he said with a helpful smile as he kept on. Somehow I couldn't help feeling I was being picked up! Finally I was too tired to argue and Doug seemed like a friendly, kind sort of guy. The bartender had known him for years as a fairly regular customer so in figuring there wouldn't be a problem I agreed to go back with Doug to his place. After a stop at my car we were on our way. "I'll brew up a pot of coffee and you can pick out a room, fair enough?" He said telling me to relax as I rode along with him in his new Lincoln town car into the suburbs. It was a quiet, older section of town, where some of the really nice homes were and where the "old" money was. The wide curved tree lined streets and the gated driveways offered seclusion from the city and were a far cry from my little apartment! It wasn't long until we were pulling through the front gate and into his driveway. I watched as one of the double garage doors nearest the house swung open. We were soon in the garage and the door was closing behind us. "You should have kept those high heels on. Those loafers spoil the look!" he said in a light hearted way as he noticed the loafers I was now wearing as we left the car and neared the side door to the house. Once inside we passed an entry room, a well appointed kitchen a large formal dining room complete with a chandelier and then we entered the large living room. "Make yourself at home" he said as I noticed the large fire place and the large opposed twin sofas with the large coffee table in the middle. This guy was more than just comfortable I thought as I took the place in. Doug then came near clasping his hands together in a hand shake seeming ready to be the perfect host "so, a pot of coffee? Or would you like another martini?" He asked as he motioned to a complete bar that was between the kitchen and formal dining room. I didn't want another drink but did notice it was easier to walk in my loafers. "Well, maybe just a small one" and with that he motioned me to the front of the little bar as he moved around behind and began mixing the drinks. The chat continued and it wasn't long until we had pretty much covered all the bases. Sports, politics, the state of the nation and everything down to the price of groceries and gas and even to the mentioning of my women's wardrobe which consisted of two dresses, one blouse, one skirt, a small selection of lingerie, one wig a bit of makeup, a bit of jewelry and a couple pairs of high heeled shoes. "I wish you would have left those high heels on" he said once again trying to be innocent and then chuckled to relieve the tension. "Halloween" I reminded him realizing that with yet another martini I was probably saying too much. So I went back into my story about doing the drag bit on a couple other Halloween nights but suggested I might try a pirate or some other character next year or drop the idea of costumes all together. We returned to the small talk. Without having to leave I ended up drinking two more drinks. Doug was noticing me looking around the place and at the staircase that separated the living room from the dining room that led upstairs. "Care for a tour?" He said as he came around the bar drink in hand then took me around through the kitchen and down stairs to show me his game and billiard room which included a hot tub and sauna arrangement. Then it was back upstairs taking another route where I saw his library, the den and then saw his home theater that was very nice. There were six full bedrooms upstairs. He told me I could take my pick so I chose the one farthest from the master bedroom at the end of the hall and the closest to the staircase just to play it safe. Doug then took me down to the end of the hall and flipped on a light switch to illuminate the large back yard. There was a large field stone patio out back with a complete barbeque arrangement built in for entertaining and even a swimming pool. The huge yard then filled in the rest of the lot to the tree line that bordered the property. It was pretty nice. We then passed the master bedroom which was large and spacious and then he took me into another nearby room. It wasn't as big as the master bedroom but it was still a large room. Doug then set his drink down on the dresser and moved to the closet. "Let me show you something" he said as he swung the doors wide open to reveal a large walk in closet. Then I noticed the closet was filled with women's clothes! After his wife had died he had moved all of her stuff into this spare room. "I guess I never got around to packing it all away" he said then continued "Hey!" As he reached for and grabbed up one of the several pairs of high heeled shoes that lined the floor under the racks of dresses, blouses, skirts and gowns. He brought them over to me "You're built kind of smallish, I will bet these will fit you!" He said, the whisky now having its effect on his voice. I began pulling away and moved towards the door but Doug continued innocently. "It's Halloween! C'mon Be a sport!" He said as he dangled the dark blue stiletto heeled pumps that matched the color of my chiffon cocktail dress. I didn't want to comply and should have left but Doug was in no shape to drive me to a hotel or even back to my car. And I didn't feel like driving either and for sure didn't feel like sleeping it off in my car back in the bar parking lot. "Alright, I'll do it." I said. "But this is a little too much and it's getting a little strange" I said. Soon I was sitting on the bed and slipping into the nearly new high heeled pumps. I then got the shock of my life to find they fit me perfectly!! Doug looked on excitedly "C'mon wear them back down stairs you can change back later before you go to bed" he said as he then led me back to the little bar just off the living room. My strolling gate returned to a feminine mincing one as I wiggled down the hallway then negotiated the staircase. Doug seemed excited at the effect. He put on some music "want to dance?" he said in apparent jest as he returned to the bar and made a final round of drinks. We talked about living alone, I was single myself and had just moved here two years ago and didn't have that many friends. I mentioned to Doug how quiet and lonely it must get living alone in such a large house and he agreed. It was a bit sad but that 's the way it goes sometimes I figured. We finished the drinks and while Doug shut the music off I slipped out of the high heels. We then went back upstairs. He showed me my room just off the stairway as he swung the door open to reveal a nice standard room that was as large as the others and as nicely appointed as well. "Oh" I said still holding up the pair of his wife's high heels "I'll switch these back for my loafers" I said with a slight chuckle. Doug followed me into the room with the well stocked closet and I noticed the doors were still open. I entered the walk in closet and found the empty space under a dress of similar color to the shoes then set them back on the floor. I then heard the swish of nylon and turned to see Doug taking a luxurious lace trimmed pink nightgown and robe off a hangar. He then held it up to me and said it looked like a perfect fit! It was too much. I backed away. "I think I'll go to bed now, thanks for the drinks and everything" I said as I moved out of the closet. "What are you afraid of?" He said. "You plan on sleeping in that dress? That's an old vintage style so I figured you're wearing it all underneath. I know you're wearing a brassiere and maybe a tight girdle too? That won't be very comfortable to sleep in" He said as he held the gown waiting. "This would be a lot more comfortable" he said with out batting an eye. "No, I...I just think I'll get some slee..." I said as he interjected "Is it that big a deal? It's Halloween! Relax" he said as he moved to the bed and draped the fluffy garments across the foot of the bed. "You can do what you want I guess. No big deal." I returned to the bedroom down the hall and after getting undressed I settled for sleeping in my panties. Then in the morning I got up early and quickly dressed but left the brassiere off and set the water balloons aside as I brushed off a mild hangover. Doug showed up at the bedroom door and noticed me putting the brassiere in my purse and he saw the water balloons. The makeup was washed off and the wig was already in the purse and in feeling my chin I noticed the start of my thin but evident whiskers. I mentioned that I should get going so I could get back home before too many people were out and about. Doug seemed puzzled by my look but seemed to understand as he motioned me out of the room and down the hall to the master suite. "Here, maybe it would be better if you wore these home" he said as he took a pair of sweat pants off of the shelf in his closet and grabbed a colored pull over sports shirt. I got out of the dress then slipped on the shirt and the sweat pants then noticed they were quite too large for me but I would make do. He offered me a pair of his tennis shoes but they were way too large so he quickly went back to the spare room and after rummaging for a bit returned with a pair of women's sneakers. I tried them and they seemed to fit just fine and although they had a pink, pastel stripe on them I figured they would go unnoticed if I just went straight home. Down in the kitchen on the way out I put the dress and my purse in a paper grocery bag and soon Doug was driving me back to my car. "You did a pretty good job with that costume at the bar last night and even had the mannerisms down pretty good" he said as we continued driving. Once again I passed the comment off as no big deal and began counting the minutes till I was back at my car and on the way home. Then he spoke again. "If you had to, really had to, do you think you could pull it off and go out on a regular night?" He said as we continued on. I thought it was a strange statement and paused in thought then mentioned that although it would be interesting to try I told him I would be far too nervous to ever consider going out totally dressed for real. We turned the corner onto one of the main streets and I knew the bar and the parking lot was just down the road a bit further. Doug continued. "But if you were careful with your mannerisms, worked on your voice and practiced with your makeup a bit more I really think you could pull it off Tim" He said. I thanked him for his appreciation but didn't go into the subject any further. "What if you had let's say, a gentleman to accompany you. A nice, upscale quiet restaurant on this side of town maybe, where nobody knew you? Just a nice quiet dinner in a higher classed social setting." I tried not to answer but he looked towards me making me feel a bit embarrassed. "N...Naw, no. I don't think I'd dare try that. Doing the Halloween bit is one thing but doing it for real would be something else entirely." I said as we continued on. I could see the bar and the parking lot now and noticed my car parked off to the side. "There it is" I pointed as Doug turned into the lot and then pulled up to my car and stopped. "Are you sure you're not the least bit curious?" Doug said as he once again looked at me and continued. "I think you could do it. And if anyone figured you out what does it really matter? You wouldn't know any of them and they don't know you. Living on the other side of town you'd never run into them again anyway and I would be the one left to answer the questions. But I gotta tell you Tim I don't think we'd have a problem." He said with an almost knowing satisfied smile. I opened the car door and pulled up the loose sweat pants and thanked him for the ride as I moved to leave. Doug continued. "Would you consider trying it for say, $2,000.00 dollars?" The offer made me pause in disbelief. I then told him it was a bit weird even talking about the subject in the first place but he kept at it. He thought I was a nice person and he figured maybe we could get a friendship going. But he was way above my social class and he was older than I was even though we shared a few of the same interests. He knew I could use the money but I thought it best to just leave his plans out of the deal. "We could maybe get together for drinks sometime, shoot a game of poor or something" I said. But he continued. "$2,000.00 dollars isn't bad for a couple hours out on the town for dinner. Think of it as a challenge if you want" he said with excitement. "You could change at my place then we would go downtown for dinner and drinks and then you could change back at my place and we could have a good laugh at our accomplishment. Then you'd be $2,000.00 dollars richer. Simple as that. We can get you some real breast forms instead of those water balloons and get you a better wig and a few other things. You could come out to my place to practice or work on your look and mannerisms at home if you want." He had already surmised earlier probably back at the bar while looking me over that the "Halloween gig" was just an excuse to step out dressed. And he most likely knew that in my paying attention to detail and in my already somewhat practiced feminine mannerisms that the one night "gig" was actually an ongoing hobby or more honestly a fetish! He went on to say he wouldn't expose me because he had no reason to but he was still very interested in seeing whether or not I could spend an evening out as a woman. "I still bet that deep down you are wondering yourself if you could do it, really pull it off by spending the evening as a woman. And aside from the money I imagine there would be quite a level of excitement for you and afterwards back at my place over drinks quite a sense of accomplishment as well as satisfaction too!" He said as I began thinking his offer over. "One night out, nothing fancy" I said as I looked over. "Nothing fancy, just dinner and drinks and that's it" he said then reached into the pocket in his coat and took out business card. He wrote his name "Doug Tennant" and his phone number on the back then handed me the card. "Think it over then if you decide to give it a try give me a call" he said as I agreed to think it over. I took the card, gathered my things then left for my car. I got home and put everything away then stayed around the apartment the rest of the weekend noticing how small and well worn my place was in comparison to Doug's place. Then I got to thinking, one night out on the town where nobody would know or recognize me. I started another work week grind the next day with the thoughts of his offer still in my head and by that Thursday I took the card out from under the phone and called the number! He seemed excited at my agreeing to give it a try. And it dawned on me that I hadn't once thought of the money! I was interested if only to try it just once. I wanted to see if I could pass undetected in open society. "Let me get a few things in order and I'll call you when I am ready" he said. "Give me your number and I will call you back." I gave him my phone number then shortly after that we ended the conversation. I didn't have much of a wardrobe but while I waited for the phone call I worked on my look, my voice and my mannerisms and paid close attention to my makeup and my hair. It was a bit nerve wracking in realizing what I was planning to do and as the days passed with no phone call I began to think Doug had changed his mind. By the time a couple more weeks passed I was certain he had changed his mind but then the next evening I got the call! "Well Tim, ready to give it a try?" Doug said on the other end of the phone. "I'm still a bit nervous about the whole idea but yeah, I think I am ready" I said. "Why don't you come out this Friday, spend the night. You can show me what you've been practicing on and try on a couple outfits to get the look down and we'll go from there" he said. I agreed and then the following Friday I drove out to Doug's place. He buzzed me through the front gate and as I drove up the long tree lined drive I watched one of the garage doors open and saw Doug wave to me. I pulled into the garage and parked. "Come on in Tim!" he said as he took my coat and hung it up in the entry way. He then walked me through the kitchen and stopped to grab a couple beers out of the fridge. He handed me one pointing to the oven. "I've got a roast and baked potatoes going so we can have something to eat later" he said then continued "come on upstairs, I'll show you what I got and we can get started" he said as I followed him along past the dining room, across the living room and up the stairs. We were soon entering the large bedroom that had the closet full of women's clothes. The closet doors were already open and two evening dresses and one long evening gown that Doug had selected were hanging on the open doors. Matching pumps sat on the floor below the outfits. Then I noticed a tray containing a full variety of makeup had been set up at the vanity and I noticed an empty wig box and an expensive auburn colored wig already placed on a white Styrofoam mannequin head stand. I then noticed another open box that contained a very real set of silicone breast forms with a page of instructions sticking out of the box. Doug picked one of the forms up. "Jane was a 42 "D" so for you to fit her brassieres I ordered you the same size" he said as he continued showing me the form. "It comes with an adhesive, a medical grade adhesive spray that you spray on the forms and then spray on your chest. You wait a minute for the glue to set up then attach the forms and you're all set, instant lady" he said. "They are guaranteed to stay put and feel lifelike and won't come off until you use this tube of solvent" he said as he pointed to the spray can of adhesive and the little tube of solvent and the brush that were set by the box. "So, I guess you can do your thing" he said with a smile. "The bath is through that door there and the lingerie is in the dressers. I'm sure you can find what ever you need" he said. "I have some letters to look over in my den and some bills to pay then I'll check on dinner. When you're done I'll meet you downstairs" he said with a smile as he looked me over and then left closing the bedroom door behind him. Even though Doug put me at ease I still felt a little strange in what I was doing but in looking over the dresses and in rummaging through the well stocked lingerie drawers at the dresser I decided to relax and enjoy the experience as best I could then headed for the bath. After a hot shower I opened the large bottle of Nair and began covering myself with the pink gel. I had learned that if I didn't do it too often that I could Nair my entire face as well and it always left me far smoother than shaving. Soon I was standing in the empty bath tub covered from head to toe in the stinging, pungent pink lather while I waited for the depilatory to do it's work. Then after about fifteen minutes I took a wash cloth, turned on a hot shower and began removing the lather and watched as all of my body hair swirled down the drain. I then filled the tub and took a hot bubble bath and used the floral smelling soap that was there. Finally, I opened the drain then got up and took a large pink bath towel and dried off. I found an electric trimmer and went over my eyebrows to shorten them up. I was now pink skinned and totally hairless as I then made my way back into the bedroom and to the vanity. I switched on the lights that ringed the mirror of the vanity and found a pair of tweezers then carefully began thinning and shaping my eyebrows. I decided on doing my best effort and it took a few minutes longer but I soon had them plucked them into a high and feminine arch. I then found a bottle of red nail polish and after a quick pedicure I applied the toe spreaders and did all my toenails. I then found some glamour length salon nails and after a bit of filing my nails with an emery board I had them shaped and then glued the nails in place. After they were set I finished by applying two coats of the red polish and one coat of the clear gloss. Then while my nails dried I looked over the paperwork for the breast forms that sat nearby. I had never tried these before and once my nails were dry I noticed it felt strange holding the jiggly, flesh colored form in my hand as I applied the adhesive to the back. I then applied the adhesive to my now smooth and hairless chest and waited for the glue to set up. I then picked up the form and centered it over my right breast then pushed the form to my skin. The silicone flattened a bit like a real breast as I worked it tight to my chest. I could feel the adhesive heating up and tingling my skin a bit and then as it started cooling off I could feel the adhesive set up and pull the form tightly to my skin! I then let go to see a perfectly formed breast size 42 "D" jiggling out in front of me with its large pink areolae and a large semi erect nipple jutting out in front of me! I then quickly repeated the process on the left side and soon was using the solvent to work around the breasts to remove any excess glue. I then put the solvent and adhesive back in the box along with the paperwork then sat back on the little vanity chair and marveling at my new look I couldn't believe the change in my appearance! I continued with a body splash and finished with a dusting from a large floral scented powder puff. After wrapping my towel around myself I continued working through the makeup tray. I found a set of false eyelashes and managed to find the little tube of glue and then get them into place perfectly after a couple of tries. Once they were firmly set I took a little brush and worked them in with my own lashes. I started with a smooth light colored liquid foundation and dabbed it on several places on my face then worked the it in until my entire face was in a smooth, soft uniform shade. I found a liquid eyeliner then being careful not to over do it lightly lined my eyes. I looked at the wig and at the dresses hanging on the door then in deciding on the black dress I picked a smoky gray eyeshadow and carefully applied it. I found a wide makeup brush and then dusted my cheeks with a noticeable but muted rose colored blusher. I then took a red lip lining pencil and lined my lips then finished by rolling up an expensive tube of matching red lipstick and then applied it carefully in broad heavy strokes. I then dabbed the excess with a tissue and finished with a light coating of clear lip gloss. I then found a bottle of perfume and sprayed myself on the neck, a bit on the wrists and then added just a bit behind my knees and at my ankles. It was a good thing I had pierced ears because in looking through Mrs. Tennant's expensive jewelry collection I noticed most of the earrings she had were the pierced style! I took the little crystal stud out of my right ear and the little gold hoop out of my left ear and set them aside. But before doing the hair and jewelry I thought I should get dressed first so I got up and began searching the dressers. I found a lace edged pair of white nylon panties and set them on the dresser then went to the bathroom where I had seen a package of pads. I took one then applied it to the panties having learned that it held a tuck much longer and it gave the appearance of a better shaped female mound. I then stepped into the panties and after tucking myself tightly I smoothed them out and went to the bed with a pair of nude colored support pantyhose. It was a bit of a chore as the stockings were firm control and very tight but I needed the look and with sheer nylon stockings on over them it really gave my legs a nice feminine sheen. I smoothed the pantyhose out and pulled the control top high up on my waist then quickly returned to the dresser for a panty girdle and a pair of taupe colored nylon stockings. The white lycra spandex panty girdle was heavy and I noticed how the wide satin panels gleamed in the light as I struggled into it working it up my legs. But soon, when I had the girdle nearly all the way up I sat back on the bed rolled the lace trimmed cuffs of the legs up to expose the three metal garters per leg then took a new pair of the reinforced heel and toe stockings out of the box. I rolled up the first stocking and fit my foot into it then began working and smoothing the nylon up my leg. I felt the cool, smooth sensation as the stocking slid frictionlessly up my leg. I heard the soft zipping sound as the sheer glassy material became snug and then gleaming tight as I hooked them to the garters of the panty girdle. I then put the other stocking on and once I had that gartered securely as well I stood up and pulled the panty girdle up high and tight on my waist with a wiggle to make sure it was all the way up. I felt the stockings pull tight at the garters then smoothed them out once more before pulling down the lace trimmed leg cuffs of the girdle tightly over the widest part of the stocking welts. I then pulled the girdle up high and tight once more, watching with satisfaction as the padded hips of expensive, tailored garment shaped me and widened my hips while at the same time the gleaming white spandex crotch panel pulled up and back tightly forcing my tucked equipment into a tight vaginal shaped mound! I then selected the black patent ankle strap Dorsay pumps with the four inch heels and buckled myself into them I was feeling quite excited at this point and had never worn such elegant lingerie or gone to quite this extreme length to make everything just so but I wanted to appear perfect when I gave my demonstration to Doug and I wanted to be totally sure I could pull off the look and appear in every way possible as feminine and ladylike as I could. Because if it didn't work I wouldn't be daring to brave the outside world no matter how much money was involved! I then moved back to the dresser and selected a white, long line brassiere then noticed as I opened all the hooks that it was indeed a size 42 "D!" I encircled my chest with the brassiere and pulled it around to begin hooking up the many hooks in the back. But with the new breast forms I was having trouble and didn't want to tear anything open with my struggles then realized I would need a bit of help. I went to the door and called for Doug. He arrived a minute later very impressed with my look and was soon helping me into the brassiere. I gathered the brassiere once again and slid my arms through the straps and then leaned forward and felt the weight and the jiggle as my pendulous breasts swung out in front of me. I then eased them into the cups and as Doug pulled the brassiere around my chest and started doing the hooks up. I felt the strange sensation as the brassiere began supporting the breast forms and holding them out as they filled and then brimmed at the feminine lace trimmed cups! I then adjusted the straps until my new bust line was standing straight out. Then before Doug left I had him help me into one of the white, back lacing waist cinchers I had found. It wasn't as long as a corset but I thought it might improve my look and give me more of an hour glass shape. After putting the bottom cuff of the long line brassiere under the waist of the girdle I pulled the girdle back up high and tight then wrapped the cincher around my waist and hooked the front and then centered it. "I haven't done this in a long time" Doug said with excitement as he gathered the laces and began pulling them tight. I could feel the garment become snug and then tighten up as it began to shrink my waist. "I think just a bit tighter" I said as he continued. I heard the white silk laces whistle through the stainless steel eyelets at the back and watched as my waist pulled tighter still until I was satisfied with my now feminized shape. "That should be enough" I said as I teetered on the gleaming black stiletto heels. Doug paused for a moment as he looked me over and smelled the feminine perfume in the air. He the then tied the laces off into a tight bow in back. "You look very nice!" He said with excitement in his voice. "Way better than at the bar the other night. It's just, it's just astounding!" He said then continued "I don't think we're going to have any trouble at all in going out to dinner." He said as he looked me over a bit more with growing satisfaction then mentioned how excited he would be to see the finished look then as he left the room he said he would meet me down stairs as he closed the door behind him once again. I minced back to the dresser feeling the tightness of all the foundation garments with growing excitement as I felt my breasts jiggling in the cups of the brassiere and as I heard my gleaming nyloned thighs zip past my thighs with each wiggling mincing step. I found a black full slip in the dresser that went with the black evening dress and noticed it was tailored with a long zipper that ran up the side. I unzipped it and after gathering it up I pulled it over my head then fitted my arms through the straps and after getting the cups over the brassiere I let the lace trimmed garment fall to full knee length with a silken swish. I zipped the gleaming black satin slip up and felt it grow snug and form fitting as it followed my now feminine curves! I felt my knees shaking a bit as I unzipped the black dress and took it off the padded hangar. I then carefully stepped into it. The black acetate satin lining swished frictionlessly as I worked the dress up over my hips and put my arms through the short flutter sleeves. Then with a little work I managed to zip it all the way up in the back and hooked the clasp at the back of the neck. I took a deep breath at being almost done then returned to the vanity and found a pair of chandelier earrings then put the posts through my pierced ears. Then once they were securely on I hooked a simple but elegant pearl necklace around my neck. I could tell the pearls were real and that Mrs. Tennant had fine taste in jewelry. I then took the wig off the stand and after I adjusted it I fluffed it out then put it on over my short blonde hair. I pulled and tightened the wig until I couldn't tell it was a wig at all! The wig was average in length but was cut and arranged in an unmistakable soft and feminine style. I quickly combed the soft curls so they framed my now very feminine face and my neck then stood back and looked into the nearby triple fold floor length mirror to stare in disbelief at my accomplishment. I had never dressed so completely and totally in such elegant clothes. And with the large array of cosmetics I was able to go far beyond what my look was like on the night of the Halloween party. It took a moment to take it all in! I quickly added two thin gold bracelets and then finding a gold ankle chain I sat down and clipped it around my right ankle. Then I found a black sequined clutch purse that went with the dress. I added a pad, a compact, perfume, a lipstick and other makeup and some Kleenex then clicked the purse shut and made my way to the bedroom door. I shut the dresser drawers and turned out the lights then took a deep breath as I stood by the bedroom door. I smoothed my dress then left the bedroom and made my way downstairs. Doug was behind the bar mixing a before dinner drink. I could feel the skirt swishing around my legs as I minced on my heels and wiggled in my most ladylike fashion as I moved to the bar and took my seat. I then looked into the dining room and noticed he had set the table for two, complete with candles! Doug was awestruck. He came around the bar and had me stand back up and give him a twirl in the center of the room. "I just can't believe it!" He said as he took in the full view checking every nuance looking for any traces of masculinity but he found none. "It's perfect, your look is flawless!" He said as he then seemed to get an idea. He went behind the bar. Downed what was left of his drink and slid a pink lady up in front of me. "Have a drink, I won't be a moment" he said as he scurried into the kitchen and then back into the dining room where he blew out the candles. He then switched the music playing on the stereo off then trotted upstairs. "Where are you going?" I asked. "Won't be a bit!" He hollered excitedly as his voice trailed off and he disappeared up the stairs and moved off down the hall. I thought it was a bit strange as I waited there watching the last of the smoke from the candles at the dinner table drift away. I then took a sip of my drink and waited for what must have been twenty minutes. I was just about to go looking for Doug when he suddenly appeared coming down the stairs excitedly while he buckled a gold watch to his left wrist. I then noticed he was wearing an expensive suit! "You don't mind if I call you June when you're dressed do you?" He said as he quickly approached then picked up the phone and dialed. "I guess it fits the look" I said as he waited on the phone. "Renee, yes, Doug Tennant calling. Could I change that reservation for next Saturday to tonight? I have had a change of plans" he said as I tried to ask what was happening. "You do have an opening, yes, that will be fine. Nine o'clock then party of two, we'll be there!" He then hung up the phone and went quickly to the closet and grabbed an overcoat and what looked like a woman's mink wrap! "What are you doing!?" I said as I pulled away and stood up when he started wrapping the mink stole around my shoulders. I told him I wasn't ready but he assured me that in seeing me coming down the staircase and in crossing the room he didn't have any doubt whatsoever that I could indeed pass for a total female! "But I'm not mentally prepared, it's a big step!" I said starting to argue about being rushed. "It's just a quick dinner 'June,' that's all and by the way since it's a bit of a short notice let's make it $3,000.00 dollars for the evening shall we?" He said with an excited smile as he finished putting on his overcoat and then held the mink stole open for me. My mind was in a whirl as he wrapped the mink around my shoulders then led me to the car where he opened the door for me. Moment's later the front gate was closing behind us and we were on our way to the supper club! He could hear my breathing as I gasped through my glossy red lips trying to relax at the suddenness of everything. It was a bit overwhelming. "You just relax June, you are going to do just fine. Think of it as an adventure, just imagine how exciting it will feel going out with no one having the slightest inkling of suspicion that you are really a man named Tim! I think we're going to have a lot of fun tonight. Go with it" He said. "I think you'll end up really enjoying the evening once you've have a couple cocktails and relax a bit and start to enjoy the game." And with that we continued towards the club! We pulled up in front of the building where a uniformed valet for the restaurant was waiting. He opened the door for me. "Good evening Mr. Tennant, good evening ma'dam" he said as I took my clutch purse and held my mink stole then exited the car with him taking my hand as he helped me out while I made sure to stay in as ladylike a character as I could muster. I watched as Doug left the car running as he got out then came around offering his arm to escort me inside. "Shall we go dear?" He said as I took his arm and we moved inside. I watched as the valet then took the car to the restaurant's private parking area. We then crossed the long gleaming tiled floor and headed for the bank of elevators. Doug had been right about one thing. I was more than certain I wouldn't be seeing anyone I even remotely knew, not here. This was the top of the mark. I watched as people came and went from the elevators and noticed the ladies in their evening gowns and the men in either very expensive suits or in tuxedos. I was still a bit flushed and breathless but did my best to calm down as we made our way to the elevator. I could hear the click of the heels and feel the swish of the skirt as it fluttered around my legs. I could feel the garters straining as they held my stockings tight and felt the tops of the satin paneled girdle legs as they rubbed and pulled, cinching my crotch into a tight, "V" shaped slit! I felt the amazing sensation of the silicone breast forms that had now fully warmed to body temperature. They felt even softer and more pliable now as they jiggled like the real thing as they sat snugly in the lace trimmed brassiere cups and all the while I could smell the subtle yet feminine scent of the perfume as it floated around my head like an invisible cloud. I was still nervous however and felt on the verge of a panic attack. I mentioned to Doug that I was feeling a bit overwhelmed by everything and felt a need that I had to return to the car. I didn't care about the money and apologized but just didn't feel I could pull this stunt off. I felt my throat click a dry swallow and could feel my heart pounding as we slowed but continued on. "I feel faint. I...I think we'd better call this off Doug" I said. He could sense my weakness as I swooned a bit then wobbled on the heels. He felt my trembling arm as I clutched him nervously then patted my hand as he continued leading me along. "You're doing fine, just fine. You'll see." He said. But I wasn't! I was a man in a dress wearing more clothing, more lingerie and more makeup than I had ever worn before at one time. It wasn't Halloween any longer and I wasn't going to a party for just a few laughs. This was the read deal! I was totally made up, totally dressed and now going out for dinner in the very real world with a man while dressed totally as a woman! And now, as we neared the elevator the traffic increased. "Good evening Doug you're looking good!" A man escorting a woman said with a wave as the couple passed by going in the other direction. As Doug greeted the man I gave my sweetest feminine smile but felt my heart in my throat as I watched the man's eyes scan my face, then move to my jiggling breasts and down to my wiggling hips. He then gave a quick glance as he surveyed my smooth shaven legs and how they shined in the nylon hose and checked the high heels over, taking me in like I was a visual feast and all the while not letting his wife in on what he was doing. The lady glanced at me then smiled pleasantly at both of us while nodding and looking at Doug. And all of that only took a second. They were soon moving away and gone. I took a deep breath at what had just happened. I had indeed "passed." The illusion it seemed was now complete. The look of the dress with the matching heels and purse was flawless,. The perfume, the sway of my earrings as they danced and brushed my neck as we walked and the "tinkle" of little gold bracelets on my wrist added yet another fully convincing feminine nuance. The little black satin bow at the trim waist of my dress shined in the light while the chiffon folds of the skirt swept over my womanly hips and fell to my knees in a graceful effect. The curves were in all the right places exactly where they were expected to be. The feminine moves and jiggles were there as well sending out the signal that I was a woman. It was working, I was working and having an effect on everyone who looked my way on a subconscious level. Every nuance of femininity had been carefully planned, gone over and was now being implemented. I had passed the test and it went without mention now and with a few interested glances from other men who saw us that I was indeed a lady! I took another nervous breath but strangely began to calm down a bit. "See? You're doing fine" Doug said with a smile as we waited at the elevator. Then as the bell "dinged" and the doors opened we stepped inside. There were several couples as well as single men that were taking the express elevator to the restaurant on the top floor. I concentrated on remaining calm as the door closed and the car started its ascent. I could hear the music in the back ground and hear the hum of the machinery and the sound of the men and women's voices in the car as they chatted casually. Then as we waited I noticed several of the men glancing my way, checking out my curves, noticing my dress and my shapely, nyloned legs as I stood perched on the high stiletto heels. Then we reached the top floor and the door opened to the din of the busy restaurant. And as we entered I could already hear the glasses tinkling, the quiet crowd talking at their tables and the band that was playing on the little stage to the side. "May I take your wrap Miss? Miss?" The coat check lady said catching me off guard as I turned to her then slipped the mink off my shoulders and handed it to her while Doug took off his coat. After Doug collected the tickets we moved to the entrance of the restaurant while we waited to be seated. A few men noticed us and waved at Doug and he returned the wave with a smile. The head waiter then arrived. "Good evening Mr. Tennant, table for two, right this way" he said as he led us to our table then held out my chair just like I was a lady. I set my clutch purse on the table then gathered my chiffon skirts under me then sat down in a ladylike fashion. Menus were brought over and Doug ordered me a small steak with a salad while he ordered the lobster dinner with a salad for himself. "And for cocktails?" He asked. "I'll have a double bourbon on the rocks" he said setting down the menu "and the lady?" The man asked. "The lady will have a frozen pink Daquari." Doug added. "Very good sir" the waiter said as he ga