The Transition Ch. 02: Jamie

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My voice trembled as I forced out the words " Hey Mark this is Jamie, did you still want to hang out tonight?"

"Sure thing, I was thinking about seven o'clock you could come by my place. I should have everything ready by then, are you still sure you want to hang out?" Mark questioned.

I paused for a moment while my brain tried to keep up with what I was agreeing too. Did I really want to go over to this mans house and get dressed up like a woman and have sex? I could still just decide to stay home tonight and watch Netflix or something...

"Yes I think so, I think it might be hot to try it out." I replied voice cracking uncontrollably.

Mark gave me his address and I wrote it down on the back of the electric bill sitting on the counter. He said goodbye and I hung up.

What the hell was I doing, I had been talking to this man for a couple months now but did I really want any of this? I knew I was bisexual, that's how I found myself in this shitty apartment with a roommate that was only there because I couldn't afford the place on my own. When I came out as Bi to my family a year ago they were less then supportive of the notion, my dad had stepped out for the proverbial pack of smokes when I was six and never came back. It was just my mother and sister, and my mother was not supportive of my sexuality in the slightest, saying "If you are gonna sin in front of god, you are damn well not going to do it under my roof." this pretty much forced me to get out of the house as soon as I could, and as soon as I graduated I got my own place. I'm not sure my sister was in love with the idea but she always kind of knew I was different anyway I suppose.

I had only had sex with one person while I was in high school, and that only lasted for a few months as he was terrified someone would discover his secret. So here I was eighteen years old living in a cheap ass apartment that I could hardly afford and alone when Mark found my profile on the dating site and took an interest. I had had my profile up for three months and was about to delete it as I couldn't really afford the bill when Mark emailed. I wasn't much to look at really, always too damn thin and too damn small, my whole life I was picked last in gym class and when I sucked at whatever game we were playing the bigger boys would call me a sissy under their breath.

Needless to say I was surprised when Mark displayed interest in me, he was tall and muscular and handsome by any definition. Things started out well and he was texting me regularly over the past month. I had been pretty lonely and somedays, his text were the highlight of my day. Eventually he confessed he had a bit of a fetish for crossdressers and wanted to dress me up sometime. I'm still not sure how I feel about getting dressed up as a girl, to be honest, it is a little bit degrading as a man to be dressed up as a girl. My sister used to dress me up when we were kids since I was younger by two years and she always wanted a little sister. It was embarrassing but still a little exciting at the same time. Maybe it wouldn't be that bad to have Mark dress me up from time to time, it would be nice to have some company and maybe even have someone in my life other then my asshole roommate.

That settled my butterflies a little bit as I made up my mind I was going to meet up with Mark and that was that. I got ready and thought I looked pretty good. grabbing my phone, I typed the address into my phone for directions and saw it was in one of the subdivisions just outside of town, maybe twenty minutes drive from my dank apartment. It was a really long twenty minutes as my brain swam with doubt and fear over what I was about to do. I tried to reassure myself that people meet online all the time and this was perfectly normal and besides Mark seemed very nice. Turning the corner into the sub division, I realized that the all the houses on this street were incredible. I realized that Mark must have been loaded when I pulled into the drive leading to his house, it must have been a million dollar home. My heart sank as I thought to myself that someone like Mark would never really be interested in someone like me. Just like myself, my fourteen year old Nissan didn't belong here, my god the neighbors would probably call to have it towed if they were to see my shit box car in the drive. I sat in the still running car for a few moments before building up the courage to get out and ring the bell.

I heard footsteps on a wooden floor approaching the door, As the door swung open, it was Mark. Hulking beast of a man that he was, He must have been six foot three and outweighed me by at least eighty pounds of muscle. I thought to myself that this man could have anyone, why would he be interested in someone like me.

"Hello.. you must be Jamie! I'm glad to see you found the house."

Nervously I squeaked "Yea, I found the place... its some house you have here."

"Well come on in, lets grab a drink and talk for a bit."

Following Mark I was given the dime tour of the house as we made our way over to the wet bar off the Livingroom where he poured me a glass of wine. Looking around, I tried to take in the place without looking too overwhelmed by how big the place was. Growing up poor as hell, I had never been inside a house like this in my whole life, it looked like something out of a movie. I didn't really drink much and when I did it was cheap beer and not wine, but I thought to myself that I needed all the liquid courage that I could get so I downed the glass of wine quickly.

"Easy there, you are going to want to slow it down on the drinking or you are going to be fucked up before we have a chance to say hello.. lol." Mark laughed.

I felt like a fucking fool, the wine was probably two hundred dollar a bottle wine and here I was chugging it like it was a miller light.

"Sorry, I guess I'm just trying to settle my nerves." I said sheepishly.

"Well you don't have to be so nervous." Mark reassured. "This is supposed to be a fun time, why don't we just talk for a bit and hang out and see where things go. Nothing needs to happen tonight, we can just have a few drinks and shoot the shit if that's all you want to happen."

I felt comforted a bit at the thought that I was in control and wasn't obligated to do anything if I didn't want too. For the next hour we finished off the rest of the wine bottle and got to know each other a bit. Mark was a software engineer apparently and had his own development company in addition to working remotely for one of the big tech companies doing something or other. I felt like a loser when I told him I worked as a cashier and made eleven dollars an hour.

"Well, you are still young, you have plenty of time to do whatever you want with your life, When I was eighteen I was in college and had four roommates and worked on campus as a dishwasher." Mark confessed. "Look we are at different places in life, I'm aware of this, but you don't have to feel weird about what you are around me."

Another glass of wine and we were loosening up and having a good time talking. Eventually I built up the courage to ask what was the deal with the crossdressing thing. Mark was silent for a moment as he thought of how to respond.

"Well..." He slowly responded. " I guess I just think it is sexy as hell to see a beautiful woman that is actually a man, Its kind of kinky but at the same time it just seems right that a man should be able to be whatever he wants and be with whoever he wants. If I want to be with a man who wants to be a woman or just likes the feeling of dressing up in sexy things then what is wrong with that?"

"I suppose that makes sense... but I don't really want to be a woman. I've never thought of myself as trans or anything like that before, but the thought of wearing sexy things does kind of make my dick hard." I blurted out.

It must have been the wine talking because that was something I would never have said to another person before.

"Well would you like to try some sexy things on for me?" Mark questioned

Again the wine answered for me and I replied with a low "Yes..." as my voice trailed off.

I was caught up in the moment, but I did want this, I wanted to let lose and try on some sexy outfit and have a little fun. I wanted to feel lace and silk on my skin like I had before with my sister. Mostly, I wanted to feel desired and I didnt want the night to end and go back to my apartment to jack off when I could be getting laid.

"Follow me if you want to feel sexy." Mark said calmly as he took my hand and started leading me down the hallway. I was being lead down the hall to get dressed up as a woman and probably fucked by this man and my cock was turning to stone in my pants with each step. This whole thing was fucked up, I shouldn't be doing this. the whole evening was sublime, I shouldnt want any of this, but since I started chatting with Mark the though of crossdressing had kind of become a fantasy. I was realizing that I did want this, well my cock wanted this at least.

Mark lead me into the master bedroom at the end of the hall and I noticed it was bigger then my entire apartment. The bedroom itself was huge and filled with some of the most beautiful furniture I had ever seen, the kingsize bed had carvings on the posts and across the headboard for christ sake. On one side of the bedroom was a spacious bathroom, and on the other side was a huge walk in closet that was easily as large as my bedroom back home.

"My ex wife used to really enjoy shopping, we had to have plenty of closet space. I actually only use a small part of the closet." he said "I took the liberty of picking up a few things I thought you might like and put them over here."

On the right hand side of the closet was a grouping of built in drawers with one drawer open and a black dress on a hanger.

"look... if you want to be my girl tonight its up to you, Im going to give you some privacy. If you want this, I will be across the hall in my office.... if you decide this isnt for you, then I'd be happy to call you an Uber to make sure you get home safely.

With that, Mark left the closet and walked out of the bedroom leaving me to decide what I was going to do. Slowly I walked over to the open drawer. Peering in, I saw a colidescope of colored panties filling the drawer. Mindlessly, my hand slipped into the drawer, the feel of the panties made of their silkey fabrics sent lightning into my fingertips. I thought back to the times my sister would dress me up in her old things and how that same lightning would light up my senses when the fabric had touched my skin. My rock hard cock was a testament to my real feelings.

My hand lingered in the drawer a bit longer untill the lacy fabric of a pair of panties caught my attention. Black panties with a blood red panel in the front and the backside was all mesh. I pulled them out of the drawer to get a better feel. they weighed nothing, the fabric was impossibly thin and so delicate, so silky and devine feeling. Seeing that there was a matching set, I retrieved the matching bra and garter belt from the dresser drawer and gently laid them out on the dressing table in the center of the room. Was I really going to put on these things and parade around in front of Mark. My hands continued to feel the silky fabric as my cock grew ever harder. I was intoxicated by the evening, the fancy house, Mark and the booze. I guess I figured that nobody would ever know so what was the harm in just trying on some sexy stuff.

I slowly undressed, laying my own clothes on a shelf beside the dresser full of sexy lingerie. I reached for the sheer backed panties first, sliding them up my legs and trying my best to tuck my raging hard on into the front of the silky material. It felt incredible having the girly material encasing my naughty bits, I ran my fingers over the material and was in heaven. The matching bra proved to be a bit difficult to get latched and I had zero boobs to fill it out, but it felt sexy to wear it. To finish up the look I added the matching garter belt from the dressing table and a pair of black stockings from the dresser. Standing in the huge walk it closet wearing nothing but a lingerie felt bizarre and exciting at the same time. I walked over to the mirror in the corner of the room swishing my ass as I walked to feel the fabric against my skin. Seeing myself in the mirror, I only partially saw my own reflection looking back at me, sure I was there, but there was a girly image overlaid on top of my own reflection. I thought I would look like a fool prancing around in this stuff, but I felt kind of sexy instead.

Mark was waiting for me in the other room, I suppose I should go show him how I looked before he starts thinking I died in here or ran out a window or something. Walking across the bedroom to the door, I felt my stocking covered legs brush up against each other which was a feeling I was unprepared for and is hard to describe to someone who has never felt the sensation. I paused at the door long enough to let the butterflies in my stomach settle down before opening the door.

"Mark... I'm all dressed if you would like to see." I croaked out timidly.

I could hear him get up from his chair in the other room and walk toward the hallway. Mark appeared from the door across the hall and he began to slowly work his eyes over me as I stood there bared to the soul in front of him terrified that he would think I looked like some kind of fucking idiot or silly or god knows what. My heart raced as he stared at me silently with an odd look on his face, I could feel the blood rushing to my cheeks as I started to bluff and feel like a fool. Just say something dammit, I wanted to scream.

"Damn baby girl, you look better then I could have hoped for." Mark said approvingly. "You took so long I was afraid that you were going to freak out and run away or something. I'm so glad you decided to be brave and go with it, I think we are going to have a lot of fun."

I was so glad he approved, for some reason just feeling sexy to someone felt really good at this stage of my life, and it didn't hurt that this man was so damn good looking. I never really thought someone like him would be attracted to a scrawny little fuck like me. The girls back in high school that I liked never really paid any attention to me, and I only had one boyfriend in my life and that relationship wasn't worth a shit either. Now, here I was standing if front of this guy that was way out of my league and I could tell he thought I was sexy as hell. It was honestly a kind of sexy to turn someone else on like this, I'm not sure anyone had ever looked at me and been turned on before in my life. Filling with confidence that he really liked what he saw, I gave him an approving smile as he led me back to the vanity.

"Now why dont we finish up the look and get you fully dressed. As sexy as you look in your bra and panties, I think you should see the completed look."

"Completed look? What do you mean by completed look?" I asked unsure where this was going. Mark put his hand on my shoulder and leaned in to kiss me gently. It was electricity and my penis twitched as if shocked. "I know you dont know me well, but I need you to trust me... can you do that for me?" Mark whispered, his face still inches from my lips. I nodded yes, wondering just what he had planned. Mark smiled and got to work producing a bunch of makeup and brushes from the drawers of the vanity. He intended to have me wear make up tonight, it was a little much, but I was really enjoying all the attention as he tried to explain what everything was and how to use it correctly. I finished my glass of wine and was working on another when Mark stepped back and declared that his work was done.

"Not bad for a first attempt I guess. You will be able to do much better then this after some practice."

"Can I see what it looks like?" I asked, eager to see what I looked like made up to be a girl.

"Not just yet, we are not yet done." Mark retrieved a long blond wig and carefully placed it on my head before reaching over and handing me the black dress from a hanger. I unzipped the back of the dress and stepped one stocking clad foot, then the other into the garment before Mark zipped up the back of the gown.

My transformation was complete, I was dressed from head to toe as a woman. Earlier today I thought I was just going to be playing around with some panties and maybe wear a bra during sex and now, here I was completely made up to look like woman, how the hell had all this happened so quickly? It was like Mark had some kind of power over me or something. Was it just mark, or was it more, he had been encouraging me to dress up for him sure, but I couldn't lie to myself, I had liked the feeling as well. The panties, the stockings, even the feel as he applied the makeup to my face all had an intoxicating effect. As I walked over to the mirror to get a better look, I almost didn't see myself in the mirror. The small pathetic guy I was, didn't show in the reflection, instead a pretty girl looked back at me.

"See babe... I was right, there is a beautiful woman inside you that wanted to get out." Mark said as he walked up behind me and placed his hands on my hips.

Seeing him standing behind me in the mirror, was a stark comparison to my own reflection in the mirror. We looked like man and woman, I certainly did not look like a man standing next to him, that was for sure. Mark began to rub his hands over my body. His touch felt amazing, being dressed as a woman had every nerve ending in my body electrified. I could feel when his hand would brush over a strap from my garter belt, I could feel when the hem from the dress would slide up my stocking covered legs. It was all so erotic to me, my cock was standing straight out making an unsightly bulge in the front of my dress.

I had to fuck, I was so fucking horny from all this that I simply had to have sex. I took Mark by the hand and lead him into the bedroom. Something had snapped inside me, I was never the type of man that would take charge like this, but as a woman, I felt free to let him know that I wanted to fuck. Besides, this is what he wanted, the whole point of tonight was for him to fuck me like a woman, so why not get into it and play my part.

I tugged at his belt and got his pants and underwear off in a few seconds. Marks cock was standing fully erect and dwarfed my own cock. "That's it baby, be my sexy little slut tonight... suck that cock baby girl." Mark almost whispered at me encouraging me to let go of my inhibition's and enjoy myself. Little did he know that I had already decided to play my part in this performance. That was kind of how I was looking at things, it was all a show and I was playing my part as a sexy young woman.

I lowered to my knees and took a deep breath before bringing my pink lips to the tip of his cock. It was dripping precum from the tip and looked a little imposing at first. I had only sucked cock two times in my life and that one was smaller then this specimen I had to try to satisfy now. I worked it in and out of my parted lips the best I could, leaving my lipstick on his shaft reminding me of my current feminine state. Somehow his cock became even harder and more difficult to accommodate in my throat. I gripped the shaft with my right hand and started to pump slowly, using my saliva as lubricant as my mouth continued to eagerly suck on the tip. Marks hand came to the back of my head as he start to gently face fuck me. He didn't last long as I felt his cock start to tense up in my mouth and he shot rope after rope of his load into my slutty mouth without warning. I had never actually had a man cum in my mouth before and It kind of took me by surprise, I tried to swallow it like I had seen in porn a million times, but a good bit of it leaked out of my mouth and got all over the front of my sexy black dress.