I had been fighting with myself for many years. In life I am a man but in my dreams I am a woman, an unadulterated will woman. After so many years my marriage died, my kids did not want to talk to me, and my job transferred me to a small town where I took phone messages for companies worldwide.
Once I was moved I had three days that I did not have to work so I went into the small town to look around. There was nothing here, no theater, no big box stores, only a small restaurant, and a small post office and a very small corner store. If anyone needs anything they had to make the three hour drive to the city.
I sat in the restaurant drinking a coffee that was pretty good. I watched as people came and left and I noticed that most of the women looked like men and the men looked like women. As I watched the other one would ask to go into the back of the place and come out with bags of clothing. I did not say anything as I knew nothing. I went back to the house that I ended up buying and sat around til the next day. Again back to the restaurant and sit read the paper when a woman sat down across from me in my booth.
“Hello’ she said to me. Happy that someone would talk with me I introduced myself. As we talked she told me her name was Sue. As we talked I was told the low down of the town. It was a place for misfits. I was amazed when she told me most of the men were women and most men were women, including Sue. After a few glasses of wine Sue had me confessing my wishes as well.
‘I could not do what you do I don’t have the courage.’ I told her, and soon enough she had the local hypnotist sitting in my booth with us. He explained its accepting what we already have inside us. So I agree to try his therapy.
The next day a knock came at the door at six am. As I was not awake I wondered if something was wrong as I answered the door. He stood there with two cups of coffee and I invited him in. ‘The first thing you need to do is pick a name that you would like to go by.’ He said as we sat at the kitchen table.
‘I thought about that.’ I said. ‘Casey. It seems bubbly’ I said with a smile.
‘Ok the next thing you need to do is to think of what type of woman you want to be.’
‘What do you mean?’
‘Well picture yourself walking the street to go to the store. What do you look like?’ I had to really stop and think about this one.
‘Well a short dress with bare legs a nice bust, long brown hair and high heels. I would want to show some cleavage for sure.’
‘And what about sex?’
‘Oh I would want lots of sex.’ I said without thinking about it.
‘Would you want to be married?’
‘No not even again.’
‘Are you submissive or dominate as a woman?’ once again I had not thought about it but it appealed to me to be collared and serve a man or two. I told the guy this and he simply nodded his understanding. “do you want to lose you man hood altogether or just alter things from the way you are now?’
‘Oh I like what I have just alter I guess.’
‘Do you want breast implants?’ I thought for a second.
‘If I could not get what I want from medication then yes implants for sure.’ We had not even touch out coffees when he asked me for a spoon.
‘They never stir the coffee.’ He said so I got up and got each of us a spoon. I took a big drink of mine when he started asking more questions. ‘Have you ever sucked a cock?’ shocked by the question I decided to answer it.
‘Yes a few times.’ I wanted to try and put him off his game so I added to my answer. ‘I love the taste of cum.’
‘Ever been fucked as a woman?’ the questions became blunter.
‘Yes a few times.’ I answered but it was not concerning to me at all. I felt comfortable with him.
‘Have you ever dressed as a woman and gone out in public?’
‘No.’ I said simply.
‘Ever been with more than one guy at a time?’
‘Were you dressed as a woman?’
‘No it was in a locker room.’ He then put two pills in front of me, one blue one pink.
‘If you had to take one pill to make your fantasies come true which would it be?’
‘The pink one.’ He had me lie down and he talked in monotones, having me imagine me as a woman with breasts. He had me remove my shoes and socks. After talking for about four hours he said that would be all for today and he would be back tomorrow before I had to start work at eight am.
For the rest of the day I never wore anything on my feet, it just felt right. When I showered I even felt sexy for the first time. The next day he was at my house at six again with coffee. He gave me a pair of black lace thong and asked me to put them on and wear them for the day. I went into the bathroom and put them on without hesitation. He asked me to wear shorts for the rest of the day. It was easy knowing no one would see me anyway, so I did. I noticed that I crossed my legs more as I sat talking on the phone. That night I showered again and that sexy feeling came back. Each time he came to my house he brought me a coffee and something to do or wear. It was Friday after a long week and he arrived at six as always and asked me to shave my legs. I told him I would that night after I have my shower. That night I poured a bath and shaved my legs and then I shaved my public hair and all the hair on my butt. When I got out of the bath I could not help but feel extra sexy. I put on the panties and my shorts and went outside for a walk. It was the first time my running shoes felt weird on my feet and I had a bounce in my step. I loved the walk so much I walked until nearly midnight.
The next morning I was not expecting him when he knocked on my door at six in the morning. Still in my shorts and panties with a tee shirt on I sat at the table and drank my coffee. ‘This afternoon we will go to the city and do some serious shopping for you.’ My head propped up and I took note.
‘Where? And for what?’
‘In the city there are a few store everyone shops at. I will take you and tell you what to buy. You will need about three hundred dollars.’ Lucky for me I had got a large bonus for moving out here. We went into the city and straight to a store called ‘Lucky Lady’. Once inside the windows were covered so you could not see in. He took me to the wig section and we talked about wigs with the sales lady. After that I ended up choosing one. Then we talked about style I will wear and we picked out a few dresses, short with a long ‘V’ neck so one could see my cleavage. Then we moved to lingerie. I could have bought the whole store but I was limited to three outfits the first one was a teddy I bought purple lace with stockings, the second was bra and panty combo black with a lace sides, the sales lady helped me with the sizing. Lastly was a bustier with open crotch panties all this for two hundred and thirty dollars. We stopped and picked up some makeup for me and I signed up for makeup lessons on how to apply it.
We went back home and I tried the stuff on again this time wearing it around my house. I felt great even after he left. The next day he did not come much to my surprise as I slept in my teddy. I got up just after eight and jumped into the shower shaving the hair on my chest and then my arms. I even ran it over my legs again to keep them smooth. Much to my surprise I changed into a dress instead of my regular clothing and walked around my house fully dressed on my tippy toes as I had not gotten any heels yet. The phone rang and it was him. “How do you feel?’ he asked.
‘Great but I forgot to get heels and what about my breast implants?’
‘Let’s take our time. I want you by yourself to go back to the city and buy a few girly things for yourself. Anything that will make you feel more sexier than you do now.’ I thought about going all dressed but no shoes so I got dressed as a guy and went to the city. I went back to the place we were before and bought some shoes three pair one stiletto, and two high heels one black one red. I left the place and wondered around for a long time and went into a sex store and ended up buying a butt plug set and a douching set. Then I went home, the long drive only made me horny. When I did get home I ran to the bathroom and put in one of the butt plug and changed into a thong and bra and a tight red dress. I put on my new stilettos that were black and a black belt I had all along. I looked great.
Monday came and went all day I was dressed with makeup talking on the phone with my legs crossed and plug inserted deeply. I even painted my nails while talking on the phone. But no hypnotist came that whole week. Then on Saturday at six am the knock came at the door and I put on a robe around my teddy that I wore and put on my wig and went down to answer the door. ‘Glad to see my hard work is taking affect.’ He said. We talked about what I was doing and wearing most of the time. I was kind of embarrassed to tell him about the plugs but her figure I was anyway. He had me lie on the bed and close my eyes as he talked about my breast growing. For months we did the same thing every morning imagining my breast growing until one day I looked in the mirror and could see a slight change. My nipple had gotten larger and a small breast could be seen. The next time he came he gave me herbless medications that I took three times daily, and then my breasts grew quickly.
Winter came and went and I was still wearing my summer dresses all year long. I had a great cleavage and now he wanted me to go to the restaurant for coffee dressed up. With little hesitation I agreed. We sat in the place me with my legs crossed and no one seemed the wiser. The next day he could not make it so I went for coffee sat in the booth when a man came over and asked he could sit with me. I agree.
Greg was passing through on his Harley and just stopped in for his morning coffee. After a hour he left but it left me so horny. I went home and then thought about the wig and if Greg wanted to come back and my wig falling off. The hypnotist told me I made some great head way but now had to decide to go all the way. ‘Please yes’ I begged. We once again went back to the first shop in the city we ever went to and the lady sold me some wig glue that would keep the wig on up to two weeks then reapply.
I went home and put on the glue with the hypnotists help and put on the wig, and boy did it stick. I could feel every hair in the wig and one could not pull it off. At dinner I was all alone and decided to go back to the restaurant. I sat in the booth and ordered a BLT with a coffee when Greg walked back in. he came straight over to me and sat down.
‘I’m looking for a place to stay the night know any?’ Before I could think it through I said.
‘I have a place.’
After dinner we went back to my place. As I walked up my front steps his hand was on my ass and he hurried me into my house. ‘Live here alone?’
‘Yes, just little o’l me.’ He walked around then said lets go up stairs. I was hesitating thinking he doesn’t know I am a guy. But he grabbed my hand and gently pulled me up stairs, once upstairs he had me show him my bedroom. He sat on the bed then said. ‘Why don’t you get on your knees.’ as he pointed to the floor. I got on my knees then he took out his hard cock. ‘Suck it’ was all he said and my mouth was on it before he could think twice about it. He took two large handfuls of hair and pulled hard making me deep throat his cock as he started to thrust. I could taste his pre-cum and it made me want more he pulled me up onto the bed pulled my dress up over my ass and moved my thong to a side and shoved his hard cock deep inside my willing ass all the time pulling on my hair. That night was the start of my new life as Casey.