My roommate and I were sharing a house togather sharing the rent and what not. We live in an old house just outside of town, here in Cody, Wyoming I am a basic laboror and he before his transformation is a cook at Granny's Kitchen.
I was helping with the construction of a barn got home and was enjoying the warming weather. I brought home some beer and was going to kick back and watch some T.V.
My roommate Jammie came in and said," I brought some dinner home. Are you hungry?"
I said," Yeah I am what did you bring home?"
Jammie said," I brought home some chicken, egg salad and green salad from Albertson's. I hope you like it."
I said," I am not picky and it smells good."
Jammie said," I also brought home some blue cheese dressing and I also brought home some dinner rolls."
We sat down and ate and I noticed he was growing his hair longer and was styling it different.
Jammie was never what u would call masculine. He stood about 5'3" weighed about 125 lbs and didn't have hardly any hair didn't really have any facial hair to speak of.
He only shaved about every 3 or 4 days and on that 3 or 4th day he had hardly a stubble. I had to shave at least every other day or u would see that 5 o'clock shadow and I also had a mustashe.
I said," Jammie I noticed your hair is different."
Jammie said," Yes, I want to do my hair style differently do you like?
I said," Well it does look nice on you if you like it that is what counts."
He said," Thank you I appreciate that you noticed."
We got done with dinner and I helped him clean up and after that I went out side and saw the Cody Enterprise was on our doorstep.
After finishing reading I caught a glimpse at Jammie and thought to myself Jammie would definetly make a pretty girl. If he has breasts and he would make a pretty girl.
Now I am a straight guy mind you, Jammie and I have never had sex and at the time he and I were just roommates and friends.
Jammie said," John it is Friday night what you say we go out and have a few drinks."
I said," Sure, I will go in and change into my good Wranglers a good shirt and my dress boots and wear my good hat."
I changed and came out in the hallway and Jammie came out of the bathroom naked and he said he forgot his cologne. As he was walking into his bedroom I noticed his ass for the first time it was a perfect bubble just like a girl's. I also got a quick glimpse at his dick if u could call it that. His dick in my estimation was maybe an inch long and it was only partially soft. I started thinking he is truly feminine.
I went back to the livingroom and started thinking he really isn't a man now my dick isn't really worth bragging about but I have never got any complaints from any woman. My dick is about 7" I think never measured it and I stand 5'8" and weigh about 170 lbs.
I started thinking he would make somebody a beautiful girlfriend if he was to be put on estrogen treatments. The one thing I do know is he has a real tendency to open up after a little bit of alochol under his belt tonight might be an interesting night.
Jammie decided we would ride to together so we took my Toyota SR 5 4x4 pickup. I love this truck. We got to Whiskey River, we sat down at this one table for 2 which was perfect. I had bourbon and water and Jammie ordered Jose Cuarvo things were going to go really well. I was still sipping on my bourbon and water 20 mins. later I was going to stay sober and Jammie was ordering another Jose Cuarvo and coke. It got here and he downed another. After he drank 5 of them that was when he was loose enough to talk.
Jammie looked down at his feet and than at me and said," I can no longer hide under this pretension. I know I am not a man, I am male but not a man, look at my dick it isn't bigger than 2" hard. I can't grow body hair and as for my facial hair the most it grows is a shadow. I am more woman than man, and I am ready to quit this pretension and I know it will take time."
I felt a stir in my pants, I am straight but I have fantasized what he would look like as a woman and he was fine in my fantasies..
We talked some more and I had one more bourbon and water and talked until closing time. Jammie was plastered and I helped him to my truck and nobody even gave us a second glance I was just helping a friend who had too much to drink.
On the way home I started planning on how to pull this off and once done to make sure Jammie was going to be mine.
I started talking to him I suggested he start hormone treatments and we do this slowly and after everything is developed I can say you moved out and a lady decided to take up the rent. As I was talking he started smiling saying how much he liked it and how he wouldn't have to quit his job just his job would keep the male identity private.
We pulled up to the house and I helped him to the house and to his bedroom and he passed out in his bed and I quietly closed the door.
As I made my way to my bedroom I started snickering loving how this was coming out. I haven't been with anybody for a while and I was going to like this. This isn't going to be like S&M I just thought that Jammie was going to be a great lady and a great girlfriend.
Any way this is going to be phase one just getting him to talk about it and phase 2 was getting him started.