First Time


I stared at myself in the mirror, but it was not me looking back. The person looking back at me looked like a woman. She was pretty too and quite sexy. For a moment I was lost in her eyes. "Can this possibly be me?" I asked out loud.

"Oh, that's the real you honey. What do you call yourself? Your girl name?" asked Suzy, the proprietor of the Miss Suzy's makeover shop. She had helped me take that very big step.

Before that day, I had been a closet cross dresser. I had some stockings and lingerie that I had bought and wore when I was alone at home. I finally had grown tired of looking like a man in a dress with a hairy body and short cropped hair that I had all my adult life. At thirty-five, I decided that I should finally go for it. My fiancée had left me a few months earlier and I didn't miss her. I was glad that she left behind a few unwanted articles of clothing. The little black dress and the business skirt suit interested me the most. I would lay them out on the bed and wonder. Then I went shopping and bought lingerie and stockings in my size.

I was a fit man, former military, but I was short at five foot six, and not too heavy at one hundred and fifty five pounds. That was mostly muscle and mostly legs. I didn't have wide shoulders and my wrists and hands were small. I used to get teased a lot about that in the army. I was always fair skinned, blonde and hazel eyed so I did have a feminine look. I never considered myself pretty though. The haircut and facial hair usually had something to do with that. But my ex had always commented about how kissable my lips were. I guess they were quite plump for a man.

After I was on my own for a month, I began dressing up all the time when I was home alone. After a while I started shaving my legs and my body hair so that the silk and nylon would be smooth on my skin. Next I wanted to try makeup but was clueless. The internet was a new thing in the world, it was the year 2000. I had a home computer and started looking up resources on line. To my luck, I found a local shop that specialized in male to female makeovers.

I made my appointment with Miss Suzy who was a trucker named Al by day. From the photos on her web page, Miss Suzy cleaned up real nice. On the day of my appointment, I was nervous as hell. I had never let anyone see me before. I almost backed out a dozen times but when it came to it, I summoned up my courage and entered her shop with my bag of female goodies.

When I arrived, Suzy was already dressed up in a red dress, red high heels, big blond wig and exaggerated makeup. She made me feel welcome and comfortable. She poured me a shot of whiskey to ease my nerves and we got started. She was glad that I had shaved completely from my eyebrows down. She asked me what kind of look I was going for, what hair style I wanted, and many other questions. I had no idea how complex it would be. There was body shaping with a corset for the waist line and silicon falsies for breasts. Then there was makeup. I knew nothing but I got a lesson in the process; concealer, foundation, powder, eye liner, eye shadow, blush, lip liner, lip stick, false eye lashes, nail polish. After that I got dressed, I wore a white blouse and the grey pinstripe skirt suit. Suzy found a pair of black pumps in my size and I squeezed into them.

Finally she brought out a ginger redhead wig, just slightly longer than my shoulders, in a Rachel cut. "You said you wanted the femme fatale look. The best femme fatales are redheads. Try it on," she instructed. Once she finished helping me fit it, she lead me over to the full length mirror.

There I stood in amazement. I could not believe my eyes. The man was gone. I only saw a hot woman. "So, what's your girl name?" Suzy asked me again. I didn't know what to say. It only made sense to have a girl name if I was going to look the part. I started thinking about names I like and of inspirational women in my life. I remembered a teacher from my youth who was the definition of a femme fatale. She was aware of her affect on the boys in her classroom and flaunted it. She used to wink at me all the time. Her name was Mary-Margret O'Neil. I went to an Irish Catholic school.

"Mary-Margret" I finally announced to Suzy. That caught her off guard. She may have been expecting a Marilyn or Betty or some such name.

"Okay then, Mary-Margret, lets go out into the shop and look for some new clothes for you.," she instructed. She gave me a quick lesson in walking in high heels. It was trickier than it looked. I managed to not fall on my face as I walked out of the change room area and down the stairs into the main shop. I drew a breath as I noticed that there were half a dozen other people in the shop. They would see me. I froze in terror and wanted to run back up and hide in the change room.

"Don't be scared Mary-Margret, everyone is a friend here," she reassured me. I continued until I was nervously amongst the other shoppers. Two were young men in men's clothes. There was one couple, clearly a man and his wife. He was burly with a moustache and over six foot tall. She was tall but thin and one hundred percent real woman. There was one person who was clearly a cross dresser shopping for shoes alone. The other person was the old man working the cash register who was a friend of Suzy's.

Right away the old fellow looked at me and whistled. "Wow! Who is this beauty?" he asked. His eyes were bulging as he stared at me. That made the others turn and look at me. The two young men looked longingly at me too and came over for a closer look.

"This is the fabulous Mary-Margret" Suzy announced. I blushed and gave a polite wave. "She is new to this and a little nervous, so make her feel welcome," she added.

"She's gorgeous!" one of the young men declared. "We do shows at the Cabaret down the street on Fridays. You should come some time. Do you know any routines?" he asked. It was clear that the two men did drag shows.

"Routines? No, I am new to this, just trying to be a woman," I answered nervously. I found myself talking lighter, higher, trying to sound more feminine. "Thanks though, I should come by and see the show sometime," I said.

After that, I went around the store and shopped for some new clothes. I picked out a couple dresses, a few skirts, some tops and two new pairs of high heel shoes and a pair of boots. I bumped into the cross dresser as I shopped who told me that I looked "Amazing!"

Miss Suzy had a photo studio in the shop and had me pose in my outfits as she snapped pictures. The photos would be my souvenirs of the experience. The couple had come over to watch me pose in my new outfits. I was really getting into it and feeling like a gorgeous woman. Both the man and the woman were watching me closely and smiling at me. They both were giving me sexy eyes. At the end of the session, Suzy introduced me to Kate and Paul. I gave my best feminine "Hello" as I attempted a curtsy. I was blushing.

Paul spoke up as Kate stared at me with sexy brown eyes. "We have a party at our house once a month for invited guests only. It's every first Saturday of the month. Suzy usually shows up. We'd like it if you would join us. It's a good crowd, very friendly. I am sure everyone would love you," he invited.

I hesitated. I wasn't sure what to make of it. I looked to Suzy. She smiled and said, "They are fun parties. You should come. It would be a good reason to wear that new black dress."

"Please come Mary-Margret. You must. I promise you will have a good time," cooed Kate as she batted her bedroom eyes at me.

"Okay, alright, I guess I might ," I managed to say to the couple's pleasure. I was gaining confidence with all the positive attention that I was getting. I didn't know what kind of parties this couple threw but I was getting a sexy vibe from the two of them. They left right after that. As they walked out the door, Kate looked back and hiked the hem of her dress up to her waist to reveal her very naked bum. She smiled and laughed as they left the building straightening her dress before going onto the street.

"Feeling more confident now Mary-Margret?" Suzy asked me. I nodded in truth as I really did feel not only like I could pass as female but was pretty too. The smoky eye shadow, the pointy eye liner, the big lashes and the bright red lips framed by the long red hair encouraged me. Suzy could see it in me too. She said, "Good, let's go for a walk down the street to the coffee shop then."

Sucking up all my courage, We went out onto the street into the real world and walked the two blocks to the coffee shop. I was waiting for passers by to harass me or shout mean things but I didn't get a second look. If anything, a couple of men eyed me like a piece of meat. I turned to see one of them staring at my ass. I blushed and walked on. Even the girl at the coffee shop asked, "What can I get you ladies?" My confidence was boosted again.

I drove home still in my female attire with all my new purchases. Since I didn't have to go back to work for two days, I stayed in my female persona the entire time. I practiced my walk in high heels until my legs ached. Even when I sat on the couch at night watching TV, I stayed in nylons and a satin robe with my wig and makeup on. I took off my makeup before bed and put it back on in the morning, using what I learned from Suzy. I used my mirror more in two days then I had in the past year.

I talked to Suzy on the phone a few times over the next three weeks. She reminded me of the party at Kate and Paul's place which was coming up. She gave me the address. I was a little scared and thought about chickening out but each weekend when I dressed up, I saw the hot woman in the mirror and knew that Mary-Margret needed to get out there.

When the first Saturday of the moth rolled around I nervously got myself ready. I slipped on the black gaff that kept my male parts tucked up away so that they wouldn't show on the front of the dress. The breast forms were stuck on me with two sided tape. My cleavage looked great in the lacy black bra that I wore. The corset pulled in my waist and accentuated my hips and round ass. I also wore an old school garter belt with six straps on it. I wore a black slip over all that. I rolled on some vintage Hanes, black stockings with seems up the back. I fastened all the suspender belts. I then slipped into my black spandex dress. It was just long enough to cover the welts of my stockings around mid thigh. It had shoulders but the sleeves were wispy black, loose, transparent nylon. I put on some silver bracelets and a long string of pearls around my neck. I had done my makeup earlier and only had to touch up my lips and put on my red wig. I really did look hot.

I was nervous to the point of shaking when I arrived at the house, a large building that was nearly a mansion. It was near the university in a nice upscale neighbourhood. There were a dozen or more cars out front and I could hear the music and laughter inside through the door. I looked at myself in my makeup mirror which gave me confidence again. I drew a long breath and rang the bell. It was Kate who greeted me at the door. She was wearing a skin tight red mini-dress which hugged all her curves. Judging by the nipples straining the material and the lack of panty lines and her previous flashing, I assumed that she wore nothing underneath that dress. "Mary-Margret! You came. We're so glad. Come on in and meet everyone," she said enthusiastically as she grabbed my elbow and lead me in.

There were at least thirty people in the main room, dancing, drinking, eating hors d'oeuvres. I half expected everyone there to be a transvestite like me but as I scanned the room, I only noticed three others, and one was Suzy. The rest were an even mix of men and women. Everyone was dressed sharp and everyone was good looking. The ages were an good mix too. A couple of people looked over fifty but the youngest looked like university students. Kate pointed out all the activities including the bar, dancing, the hot tub, the bathrooms, and the five available bedrooms. I went straight to the bar for a drink. Kate was introducing people left and right and I could not remember any names in the flurry. Kate excused herself to her other guests and instructed me to mingle.

I watched the crowd and observed. I noticed two sexy ladies in long gowns dancing closely and sharing loving kisses with each other. Elsewhere I saw an older gentleman stroking a younger man's hair. One woman came down the stairs wearing nothing but her high heels and casually came to the bar. She smiled and said "Hello" as she picked up two glasses of Champaign and went back upstairs to one of the bedrooms. I noticed that three male and female couples were in the hot tub, all naked. There was a lot of kissing going on between them all. One of the men was eating a woman's pussy as she sat on the edge of the tub. "So this is what a swinger party looks like," I found myself saying to myself.

I was sipping Champaign when I noticed a young man standing next to me staring me up and down. He had to be a university student as he looked twenty at the oldest. He wore a modest outfit of grey trousers and a simple white shirt. He was shorter than me and he had to look up at me through big glasses. He had blond, over gelled hair and gave off a real nerd vibe. He was practically drooling on me as he stared at my cleavage. He was inside my comfort zone so I moved away from him. Not discouraged, he followed me and got close again. He said "Hi" to me so I returned his greeting without enthusiasm. I wanted to escape the little fellow so I made my way over to Suzy to chat.

Suzy greeted me warmly and introduced her friend who was the same older fellow who was working at the shop. He kindly hugged me and gave me a light cheek kiss. "You look fantastic Mary-Margret. I feel like a thorn between two roses," he said.

Engaging with Suzy and Fred did manage to get the young man off my case for some time. I pointed him out to Suzy. "Do you know that kid, he's stalking me?" I asked.

Suzy and Fred gave him a look over. They both shrugged and shook their heads. "No, never seen him before. Probably new from the school. There are always some college kids at these things," Suzy told me. "Why, don't you like him?" she asked.

I shook my head. "Not exactly my type I guess," Not that I had a type. I wasn't sure what I was looking for. I had only been with women before. I had been curious but I didn't fantasize about any men in particular. The thought of hooking up with a couple was appealing to me. I had fantasized about Kate and Paul since the shop. I honestly didn't know what I would do. I was a man underneath but I was being a woman. How would it work? Would I have sex as a woman? With a woman or a man? Would I take everything off and fuck like a man usually does? I hadn't thought too much about it.

While I mused on the subject, Suzy and Fred had made their way to the dance floor. That left me open to little guy again. As if right on queue he approached me again. "Would you like to dance," he asked politely. I almost felt bad telling the persistent admirer "no." Still I refused him. I then excused myself and went for a walk around the house.

I had just entered the kitchen where I noticed the host, Paul in a tight embrace with a young blonde woman. His hands where all over her as they kissed savagely. She wore a short white dress and Paul had pulled the hem up over her ass and was squeezing her bare cheeks. Her strap was down on one side and her bare breast was exposed. She seemed very eager and wrapped a leg around his waist to pull him in closer to her. I left the married man and his conquest in search of his hot wife.

I caught sight of Kate who was going up the staircase pulling a young black man by his hand to come with her. She looked pleased with her choice and was giggling like a school girl. She paused for a second when she noticed me staring. She smiled back at me and winked. Laughing, she continued to pull her new found lover to the upstairs bedrooms. I was a little confused. I wasn't sure if the wink was meant as some kind of invitation or not. Did she want me to join them? Feeling a little bold and daring, I decided to go and find out. I tried to move quickly but the high heel shoes limited my speed as I was still a novice in walking in them. The stairs were even harder.

When I made it up to the top floor, I came upon a hallway with six doors. One door was open. I approached it slowly but to my dismay, it was empty upon inspection. The other doors were closed and I could hear moaning and panting coming from the other sides. I had no idea which room they would have went into. I thought about knocking on each door but realized how rude that would be, especially if I picked the wrong door. Apparently, interrupting was frowned upon. As I stood there, one of the doors opened along with the sound of flushing. A lone elderly man was departing the room and noticed me.

"The bathroom is free now, sorry if I made you wait Miss," he said. He hurried off down the stairs. I blushed because he called me Miss. I loved the feeling of being treated like a woman and not like a man in a dress. I entered the bathroom to wash my hands. I felt like I had to go through the motions like I was actually waiting for the bathroom instead of explaining why I was standing in the middle of the hall like an idiot.

I took a moment to collect myself. I even fixed myself up in the mirror. I still looked really hot. I felt desirable. After a deep breath, I decided to rejoin the party for a little longer. I felt out of place and didn't know many people so I figured I'd give it an hour to seem polite then excuse myself and head home.

As I opened the bathroom door, the young nerdy guy was standing at the door smiling at me. "Shit, will this guy never give up?" I thought to myself. It was obvious that he wasn't waiting for the bathroom by his posture and look. He squeezed his own crotch and massaged his member through his pants as he licked his lips. I thought about how to handle the guy. I didn't want to get violent but he wasn't taking "No" for an answer. I decided to just ask him to step aside so I could pass by.

As I worked up my voice to be courteous but forceful, he began unzipping his trousers. I was shocked and realized that I would have to resort to getting physical in order to get it into his head that I wasn't interested. I put on a stern face and approached him. As soon as I was in front of him, he pulled out his cock. I froze in my steps. I wasn't sure what I was expecting but I wasn't expecting the hammer that was in his hand. The kid, although a university age boy was small in stature, about five foot three and maybe one hundred twenty pounds. His outrageously large cock, a good nine inches long and as thick as my wrist looked so disproportional on him. I had never seen one so big. It was certainly larger than my own, much larger. The veins pulsed on it angrily as he squeezed the stiff erection. His hand stroked the circumcised monster making it grow even more. I couldn't believe my eyes.

I don't know how long I had been staring at the young man's erect penis nor did I realize that my mouth was hanging open and I may have been drooling. The kid however did notice and began snickering at me. The confident little bastard seemed to know me better than I did myself. He knew if he persisted that I would cave. All he had to do was pull out his ace. I couldn't break the trance that I was in. I couldn't take my eyes off of it. I kept saying, "It's so big!" over and over again subconsciously. It was like a magnet to me. I got closer and my knees felt weak suddenly. I let them go and found myself unable to fight it as I knelt in front of him. My face was only a couple inches away from my obsession. I was actually drooling.

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bytgirl_Mary© 5 comments/ 33087 views/ 36 favorites

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