Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below

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I Had been Married for about eight years when I discovered my wife Jen had been cheating on me with some guy she had met online. Once upon a time we had loved each other or at least I had thought we had loved each other, but how does your wife of eight years just decide to fuck some guy she just met online? There was a ton of yelling and insults and she decided to leave and stay with her sister for a while until we could work things out. Well that was six months ago an today we met with the lawyer's to finalize our divorce. Thank god for a prenuptial agreement we had in place, the proceedings we pretty easy and I was able to retain most of the assets I had. The now ex-wife wasn't all that pleased, but then again she was the one that decided to step out on our marriage so fuck her I suppose.

I was thirty two years old and newly divorced, honestly I didn't really know where to go or what to do with myself. For the next six months, I pretty much just worked my ass off to take my mind off things. The money was rolling in and things should have been great, but I was lonely and depressed from being alone in my big half empty house and I started to develop a porn addiction.

I had always jerked off, even when I was married, but since the divorce I had started jerking off a lot more and found myself watching a wider array of porn then I ever had before. A personal favorite of mine had become tranny, sissy, shemale porn, whatever you want to call it. I couldn't believe how a man could be transformed into such beautiful women. Hell half the actual women out there were not as sexy as these trans girls I was watching. After some time of jacking off like a damn spider monkey every chance I got, I started to have fantasies about what it would be like to have a girlfriend that had a cock between her legs. I started to want a sexy ass woman that nobody would ever suspect had a little secret in her panties.

Eventually, the porn wasn't enough, I wanted to get back out there and get laid but this time I wanted a girlfriend with a little extra. Where the hell do you even find a transsexual girlfriend anyway. I made an account on a couple online dating sites but the sites didn't really have many trans girls to chose from and the few on the sites looked like fake photos or something like that. I went to a gay bar two towns over so I wouldn't run in to anyone that might recognize me but, strangely enough, all I saw there were gay guys. I did get hit on by a couple of feminine looking gay guys, but as far as I could tell not a trans woman to be found. This was going to be more difficult then I had first thought.

Months went by and I continued jacking off to porn endlessly, I had recently started getting into stories and movies where some young impressionable guy was transformed by their girlfriend or wife or whatever into a crossdressing sissy. I started to think about what it must feel like to have enough power over someone to be able to transform them into something else solely for my own pleasure. In my marriage, I had never particularly been the dominant one, It was pretty much just a plain vanilla relationship, but more and more the idea of exerting my power over someone else and making them submissive to my will became a real turn on.

Slowly my plan started to hatch and I began to figure out how I was going to do this. I was going to find some one who was maybe a little crossdressing curious and guide them down a road that would lead them deeper and deeper into femininity and teach them to be my submissive little sex slut. Such a simple plan I suppose and not unlike the stories I read and jerked off to a hundred times, but how do you actually accomplish this when real people are involved? Is it even ethical to do something like this?

To put my doubts to ease, first I decided I would find someone that was maybe already interested in crossdressing and maybe a little light bondage, that way they already had a predisposition to this kind of thing and would possibly be a willing partner in exploration of enjoyable kinks. Secondly I decided that I wouldn't try to blackmail or threaten anyone like you see so often in the movies about this kind of fetish, I wanted my partner to make each and every decision that leads them into womanhood willingly. My goal here was to create a trans girlfriend that was devoted and submissive to my every desire after all, It seemed counterintuitive to make them hate me along the way.

Back to the dating apps and websites I went to find my special partner for this journey. I wanted my girl to be on the younger side, maybe 18-23 so the transition process would be as effective as possible and maybe they would be a little more impressionable. I didn't really want to find someone from one of the swipe right, swipe left sex apps so I decided to limit my search to the kind of sites that only had people looking for actual relationships. Unfortunately this didn't allow me to know their sexual appetites' in advance, I was going to have to do the work and get to know this person before proceeding. I focused my search toward profiles that were very thin and on the shorter side, ideally less then a hundred and thirty pound's and under five foot eight. After a couple days of searching for a partner I had narrowed the list down to about nine potential candidates. I sent off messages to my potentials and waited to see if I got any nibbles.

The next day I had a few replies waiting for my response, six in total. Of the six nibbles I got, two of them were gay guys obviously looking for sex as the dick pic they sent clearly let me know. The four other possible candidates I continued to communicate with over the next couple weeks. over that two weeks, two of the potentials started ghosting me as the kids call it, and I was left with two possible girls left in the running. Daniel and Jamie were their names and both looked like they could have a lot of potential. Daniel was a little older at only twenty, had light brown hair and was rail thin but a bit on the taller side at about five foot ten inches. Jamie had a medium length shaggy blond hairstyle and was only eighteen years old and really short at only five foot six inches. I continued talking to both of them over the phone and eventually the topic of sex came up and I revealed to both that I had a little fetish for my partners to be interested in crossdressing. Oddly enough, both thought crossdressing might be something they could try out. Daniel had never done it before but thought it might be kind of hot to try. Jamie reluctantly admitted that he had done it in the past with his older sister dressing him up for fun and that it had kind of turned him on. As the days went on, our talks turned more toward crossdressing. Daniel's interest seemed to wane but Jamie stayed in contact and wanted to meet up.

I agreed to meet up with Jamie, but told him I would only agree to a meet up if I was allowed to dress him up as a girl if we were too have sex. Oddly enough, he agreed to my demand rather quickly. I was beginning to think I had found my girl, she must want to feminized after all, what kind of real man would agree so fast to being dressed up as a girl and fucked like one? It was all settled, Jamie would come over to the house this Saturday night which gave me five days to get everything ready for our little adventure together. I was really excited, it was going to be fun helping this feminine girly boy transform into the woman I had been fantasizing about, the perfect submissive girl, obedient and beautiful.

I jumped onto the internet and got a really nice mid lengths blond wig, lace front real human hair and expensive as fuck. I could almost see Jamie having similar hair to this somewhere in the future if I could coerce my pet to grow out her hair. The thought of what Jamie might become for me, made my cock swell in my pants. Next I stopped by Victoria's secret and purchased a small collection of bras, matching panties, and sexy lingerie to get Jamie started out on the right foot on the trans road.

Then it was off to the makeup counter the get the supplies needed for a girl to look her best. I told the sales girl working the counter that my daughter was just getting into wearing makeup and I wanted to surprise her with a set to get her started out right instead of the crap from Walmart she had been buying. The sales girl was really sweet about helping build a set of supplies to get a girl everything she needed, brushes, pallets, a couple shades of foundation. close to seven hundred dollars later, I had what I needed and Cindi the makeup girl even gave me a couple vouchers for free makeovers since I spent so much money. The makeovers might come in handy if I could convince Jamie to get one since I didn't know much about makeup and he would need to learn.

At work the next couple days I must have had an erection a dozen times thinking about the weekend and trying to imagine what Jamie could become with some gentle nudges in the right direction. We texted all week and Jamie seemed to be looking forward to some kinky fun as he called it. Friday after work I went shopping again and found a really pretty little black dress that I was hopeful would fit. That night I watched makeup tutorials on YouTube for several hours to familiarize myself a bit with how to do makeup correctly. I was hoping I would be able to do a convincing enough job to show Jamie the girl inside that I could already tell was there waiting to be set free.

Saturday had arrived and I was as nervous as I had ever been about a date. Back in college, I had a few bisexual experiences with my girlfriend at the time Candice and a gay friend of hers Steven. He was always hitting on me and clearly liked me and she was always telling me how she thought two guys having sex was really hot. With her encouragement and a lot of alcohol I let him suck my cock in front of her which made her wet as October as she worked herself over with her fingers. After that she couldn't get enough of Steven and I and wanted him involved every chance she could get. It started with a three some where he sucked me to get me hard before I would fuck Candice as she sucked Stevens cock. I don't know if I really looked at it as gay sex at that point, it was just a blowjob but Candice and Steven kept telling me how hot it would be if I fucked Steven.

Well long story short, one night we were all high as fuck and drunk and I guess I decided it wasn't that much of a jump from letting a guy blow me and just fucking him so I went for it. Candice was over the moon when I told Steven to get on his knees with Candice and they were both going to get me hard before I would bend him over and fuck his ass. They both eagerly crawled over and worked their tongues over my cock until it was hard as ice then Candice handed Steven the lube as she pounded my cock in and out of her eager mouth.

When Steven was ready, Candice grabbed my cock and positioned it against his waiting hole. I could see in her eyes that she wanted nothing more then to watch me fuck him in front of her. Slowly I inched forward until his hole tight around my cock and I was inside him. Candice had her hands all over my body as she begged me to make Steven my bitch and breed his ass. I probably should have been freaking out at this point, but it honestly didn't feel any different then the couple times I had fucked Candice in the ass before. I figured if it was weird later, then I could just blame tonight on being high and decided to just go for it. Slowly at first and then faster and faster I drove my cock in and out of his willing ass. I felt kind of good to have this kind of power over Steven, It's an odd feeling to make another man your bitch and fuck him like one. Candice was playing with herself like I had never seen before and at this point both were begging me to cum in his ass. It was all too much and I went over the edge and pumped every drop of cum that I had into his dirty hole before collapsing on top of both of them. This went on for the next several months, the three of us getting fucked up and having sex, but eventually Candice and I broke up and that was that.

After we had broken up, I kind of told myself it was just being drunk or high and that it wasn't anything I would do again, but here I was after my marriage of eight year to my beautiful albeit unfaithfully wife Jen had fallen apart planning to have technically gay sex again, sure I was gonna throw some makeup and a wig on Jamie but he was still going to be a guy underneath it all. I could see Jamie becoming a sexy trans girl with a little work but what if the thought of fucking him was just a fantasy and I wouldn't be able to go through with it.

The phone rang, breaking me out of my thoughts, and snapping me back as I realized it was Jamie calling. We had never talked, just emails at first and then tons of texting to get to know each other a bit before we were too hook up. My god, hookup was what this was, I was about to hookup with a man. My mind raced for a split second, I could just not answer, I could ghost his ass and move on and forget about all this shit. The idea was insane anyway after all, who looks for someone to transform into a woman, maybe it wouldn't work anyway and it would all be a waste of time. I could just move on and find a new girlfriend and forget about it, I could if it wasn't for my already turgid cock as I swiped the phone and brought it up to my ear and heard myself say

"Hello, this is Mark".