Hi, my name is Lee Ann. I was not always Lee Ann, I was born Curtis Davis. I recently went through my transformation to a woman and became Lee Ann.
I suppose I should start from the beginning. When I was a child I always felt something not quite right about myself. I tried to figure it out for a long time but I never could. I vary rarely felt that I was really who I was supposed to be. I went all through grade school, college and through a failed marriage that ended 10 years ago feeling that way.
About 2 years ago I started to cross dress. I first started to wear panties but soon worked up to bras, dresses and skirts. In about 2 months I had started a nice woman's wardrobe. I could not believe how fun it was to shop and try on things at the store.
Well now comes to the present time. I am currently in therapy looking to go forward to transition all the way. I stated the therapy about 2 months ago. I see a local therapist, a Doctor Williams. She specializes in people who are transgendered. She is a great therapist and has helped me so much to be the woman I want to be.
When I first made the appointment to see her, I told her assistance I was a male who was a cross dresser and wanted to talk about the options that I have as a transgendered. "She will be more than happy to talk to you Mr. Davis," her assistance said politely. "I can make an appointment for next Thursday at 3:00 if that works for you." I told her it did. "Be sure to dress female, she will want to see that side of you." I told her I would.
That Thursday I took off work so I could take my time getting ready for my session. I took a nice bubble bath and tried to look for the perfect outfit. I picked a black skirt, red blouse, a pair of pink panties and a pair of high heeled boots. I picked out some nice stockings also. I then worked on my face. I out on some makeup I bought from MAC cosmetics (I always say why not go for the best lol). I put on a nice pink shade of wye shadow to accent my blue eyes. I applied a nice dark shade of red lipstick. I put some mascara and blush and I was done.
I left my apartment around 2:30 and caught the bus downtown. I arrived at the doctor's office about 20 minutes later. I was nervous when I walked in the door and about did a 180 when the assistant said "Don't be shy or nervous sweetheart."
I slowly walked to the desk and said "My name is Curtis, I have a 3:00 appointment to see Dr. Davis."
I still was feeling nervous and the assistant saw that. "I told you to relax sweetie. We also need to know what your female name is, that is how we will address you around here."
"It is Lee Ann," I told her trying to relax. "I am here to talk to her about the options I have as being a transgendered person."
The assistant gave me some paperwork to fill out. Some of it was the usual insurance and health stuff, but at the end it had questions about why I was there. It asked things like how often do I cross dress, do I wish I was the opposite sex and if I ever had sex with a person of the same sex and stuff like that. I answered that I cross dressed as often as I could and yes I often wish I was a woman. As for the sex stuff I had never been with another guy but admitted I always have wanted to.
Once I finished the paperwork I gave it back to the assistant. She pointed to a door and handed me back the paper work. "You can go through that door, the doctor is in there and she will see you now."
I did as I was told. The office I entered had a desk where the doctor sat behind. There were a few chairs in front of the desk and behind the desk there were two doors that led to other rooms. "Hello Lee Ann, I am Dr. Williams," the lady behind the desk said. "So you have some here to see about what options you have?" I shook my head yes. "Well you have a few of them, but first we need work on what options will be suited for you." She took the paperwork I had filled out and started to scan over it. "It says you are basically a cross dresser but never had sex with another man, I think we can help you in that regard. I have three male assistance that have helped ladies, such as yourself, try sex for the first time as a woman." She continued to scan over all the paper work.
I sat feeling nervous again. I was not sure how far I wanted to go with it all. "Well honey, the first thing we need to do is get you in one of the examining rooms. Follow me." She got up from behind her desk and entered one of the doors behind the desk. I followed her in. There was a small bed in the middle of the room. "I want you to take off your clothes except for your bra and panties." She opened up a closet and took out a nightgown. "Place this on and get on the bed. I will be back with one of the assistance." She left the room.
I took off my skirt, blouse, shoes and stockings. I took the nightgown and tried it on. As I out it on it felt so nice and was a perfect fit. I placed my butt on the bed and waited. A few minutes later Dr. Williams came back in with a nice young man. He was completely naked. His cock was soft but when he saw me it started to get hard. He was very cute and I felt myself getting horny as well. "Charles, I want you to meet Lee Ann, she is a new patient that needs to have some of her ambitions removed." Dr. Willams sat on a chair at the foot of the bed.
"Hi Lee Ann," Charles said. "You look like a very lovely young lady." He sat next to me on the bed. He took his arms around me and gave me a kiss on the mouth. I opened my mouth to let his tongue inside. I could not believe I was letting a man kiss me but it felt so natural.
"Charles is going to introduce to you how is feels for a woman to have sex," the doctor said after we had kissed for a minutes. "So what you need to do first young lady is to give him oral sex. I know it may be hard at first. Just put your lips around his cock and slide it in and out OK?"
"Yes Doctor Williams," I said. I stood up off the bed then got on my knees. I took his cock by my hand and first explored it. It felt very nice and hard. I placed my mouth gently on his cock and started ot suck the shaft. I could hear Charles moan softly. I worked it some more.
"You are doing a very nice job Lee Ann," Charles said. "Give it a few more minutes then I will enter your pussy." I was sort of nervous again and the doctor could tell.
"Stop for a bit Lee Ann," the doctor told me. She got up and left the room for a bit. When she came back she had a funny looking cigarette. "This is some medicinal marijuana. I want you to smoke it to help you relax."
I took it from her. She took a lighter she had in her pocket and lit it for me. I had smoked marijuana before but it was back in my first year of college. I took a couple of drags. Dr. Williams sat back down. "Take the whole joint and smoke it. It will help you relax and let you enjoy what you are about to do."
I soon was feeling very lightheaded and started to laugh a bit. "Wow, I feel so relaxed." I smoked it until it was all gone. The next thing I know I was laying on the bed. The doctor opened a drawer up and took out a vibrator and some KY Jelly. The vibrator was about 6 inches long and very slender. Before I know what I was doing, I had my panties off, my ass nice and greased up with the vibrator inside me. I was feeling so relaxed and high it was not funny. I soon was bucking my hips wildly as I felt the vibrator moving inside me. "Wow, that feels so fucking good!" I shouted.
Charles was next to me on the bed playing with my breast forms. It felt so wonderful and I prayed the feeling would last forever. After about 10 minutes of bliss with the vibrator the doctor said "OK Lee Ann, that is enough of the vibrator. It is time for Charles to fuck your little hole. But first, what do you think of the vibrator, do you like it?"
"I fucking love it," I giggled. I still was feeling very high from the weed she had given me to smoke. I slowly and reluctantly took the vibrator out of my man pussy. "That felt so good." I was still giggling.
I soon felt Charles get on top of me and had my knees spread open wide. I laid back and enjoyed the feeling. Soon I felt his cock at my door. It was soon sliding in and out with ease. "She feels very nice Doc," Charles said. "I think she will make a good woman for a lucky guy." I soon felt his mouth kissing mine. Soon we were both hitting an orgasm. I never know a guy could have an orgasm from his ass but I learned that one can.
"Shoot that love inside me," I said. I felt the cum shoot my walls inside me. If felt just fantastic. I soon was shooting myself without any stimulation on my cock.
"How was that Lee Ann?" Doctor Williams asked as she stood up.
"It was great Doctor Williams," I said. "I did not believe it was possible for me to have an internal orgasm like a woman but I felt it."
"Well, get dressed and then come back to my office and we will have a little talk." She looked at Charles "Thanks for helping Lee Ann find another part of womanhood that she needs to have before she makes a decision on what she needs to do." She and Charles left me alone a I got dressed.
When I entered her office, Doctor Williams pointed to one of the chairs on the other side of her desk. "Sit down honey." She took a long look at me. "You seemed to have enjoyed what you just did. It is a good sign that you are on the right track for you to consider transforming. There are several other things we will have to do before we come to that but today is a good start."
"Thanks doctor," I said. "I did enjoy what I did. I have not had sex in a long time and I have never had sex with a guy. To me it felt so natural for me."
"Well, let me ask you a question or two." She gave me a very deep look. "Have you ever been out as Lee Ann other than today?"
"I have been out once or twice to a club on the other side of town," I answered. "It is very friendly for transgender people."
"OK, is that all?" she asked'
"Yes it is," I said
"OK, this weekend I want you to wake up early, get all pretty and go out shopping." She could tell I was a bit nervous. "Look, you make for a very pretty young lady, just act like a lady and you will be fine." She looked at her appointment book. "I want you to come back next Thursday and we can talk so me more."
I soon left her office still feeling the effects of the weed and a strange feeling in my bottom. I know it was from the great sex I had just had.
That Saturday I woke up around 5:00 AM. I took a nice long bubble bath. It felt so good to relax in the tub. I shaved my legs, arms, underarms and my pubic area. I washed my body all over and made sure I scrubbed everywhere.
When I got out of the tub I picked out a cute outfit, a zebra print skirt and a brown blouse that went very well with it. I re-did my toenails with a fresh coat of polish. Then it was on to the face. I made my face like I had done when I went to the doctor. I put on a blond wig. I looked at myself in the mirror and could not believe how well I looked. It was the best I think I had ever looked dressed as a woman.
Around 9:00 I went to the market I go to about a block away from my apartment. I walked passed a man that was the manager of the store. "How are you today ma'am?" He asked. I nodded and said I was fine. I went to the deli and bought some fish for dinner. I also picked up some fresh vegetables. A few of the stock boys smiled at me and asked if they could help with anything. "I am fine, thank you," I said.
When I got home I could not believe how great I felt. I also started to feel some excitement down in both my cock and man pussy. I wanted to take care of them both but I did not have a vibrator. So I caught the bus downtown where some adult stores were located. I went into one that did not look too seedy. "How are you today young lady?" the salesman asked. I nodded that I was OK. "Can I help you find anything?"
"Yes," I said. "I am looking for a play toy I can use to help me with masturbation. Can you recommend anything?"
"Have you ever used a vibrator before?" the salesman asked.
"Once about a week ago," I answered. "Never before then."
"Well I think I can help you," he smiled at me as he took my hand. "There are some nice starter vibrators here that will help you. Are you interested in also anal penetration?"
"Yes I am." I could not believe he thought I was a real woman. I smiled.
"Well this little number is called `The Starter'. Many women have told me that it worked very well for them when they started to use one." He took it out of the box so I could see what it looked like. It looked very much like the one the doctor had me use.
"Yes, that looks like it will do nicely." I took a hard look at it and could imagine myself using it. "Do you also have some lubricant?"
"Yes we do." He again took me by the hand and led me to the cash register. He took some KY Jelly from the back of the counter. "You also need some batteries. The KY Jelly is on me, as well as this little gift box we are giving away with every purchase." He put everything in the bag. "That will be $41.95"
I quickly paid the bill and soon was headed back to the door. I took the next bus back to my neighborhood. Once I got back to my apartment I quickly stripped. I opened up the gift box and there was a package of rose pedals, a candle and a card with the website address of the store. I placed the rose pedals on the bed, lit the candle and soon was rubbing my man pussy with the KY Jelly. I placed the batteries in the vibrator. I slowly inserted the vibrator inside me. I could not believe how good I was feeling again. I soon was having an orgasm in my man pussy and my cock. Afterwards I feel asleep.
That Thursday I arrived at the doctor's office, dressed in a black dress and open toed shoes. The assistant told me to go ahead and enter the office. I opened the door and Dr. Davis was sitting behind her desk. "Hi Lee Ann, how are you today? Please sit"
"I am fine," I answered as I sat down. I felt a little bit more at ease than last time.
"Well it looks like you are feeling better than last week." She took a file from her desk drawer. "I have started a file on you so we can watch the progress you make on your road to womanhood." She made a few notations. "Did you do as I told you to do last weekend and go out shopping?" I nodded. "That is a good girl. How did it feel? Did anyone give you a hard time?"
"It felt wonderful," I said. "I went shopping at the local market and I think the manager and stock boys think I was a real woman. I also went to an adult store and bought me a vibrator."
"Wonderful," Dr. Williams said. "Today we are going to go in the other examining room. I am going to give you a physical and check everything out. So follow me." She got up from her desk and opened the other door behind it. It had a small table with stirrups. It also had a toilet in the back of the room and a funny looking machine in the corner.
"Please undress and get on the table." I did as I was told. She went to a drawer and pulled out some marijuana from it. She rolled up another cigarette for me to smoke. "Here, smoke this to relax you." I accepted the joint. She lit the joint and I soon was puffing away. "I will be right back honey, I am going to get a nurse to assist me." She left the room. It was then I noticed that there were two sets of handcuffs at the head of the table. I assumed I would soon be put in theme.
When she came back she had a young nurse with her. I was feeling very good. I was just finishing up smoking the joint. "Nurse, please put Lee Ann in the restraints." The nurse placed my hands in the handcuffs and my feel in the stirrups. I did not seem to care what they were doing. The doctor checked the nurse's work. "That is prefect."
"What are you going to do?" I asked as I giggled.
"First we are going to clean your pussy out with an enema. Then we are going to place a camera in your man pussy and take some pictures of it inside. Then we are going to take some pictures of your cock and other parts of your body. Like I said, we are going to start tracking your path from being a man to being a woman." She took an enema from a box and inserted into my back door. I felt the juice pump it's was in. When I had it all in the nurse undid my restraints so I can go to the bathroom. I soon felt the liquid wanting to come out so I expelled it. I wiped my bottom. I felt so clean on the inside.
Doctor Williams had me get back on the table. She rolled me another joint before I was placed back in the restraints. I smoked it and soon was feeling the best I ever felt. When I had finished the joint, Doctor Williams took the machine from the corner. I noticed it had a small tube attached to it. I assumed correctly where it was going to go. I soon felt it enter my body. I tried to fight it a bit as there was a bit of a pain. That was why I was in the restraints I thought.
Doctor Williams looked at the monitor that was on the machine. "It looks very good so far," she said as she entered the tube further into me. "Nurse, I want you to see this." The burse placed herself behind Doctor Williams. "See how clean she is on the inside." The nurse nodded. The doctor looked at me and said "She is a new nurse and needs to see how things are done here."
I soon felt the tube slide really deep inside me. The doctor took many screenshots of the inside of me. "You seem to have a very clean and healthy man pussy. Don't you think do nurse?"
"Yes I do," the nurse said. "I also see that this young lady is getting a little excited." She was refereeing to my cock which indeed had grown a nice hard on.
"Well we cannot worry about that right now. We have to slowly extract the camera." The doctor slowly worked its way out, again taking pictures of my insides. Soon the camera was outside me. I was soon relaxed again. "OK Lee Ann we need to take pictures of your body, stand next to the wall." She unfastened the restraints.
I stood next to the wall. The doctor took a camera from a drawer and started to take many pictures of my body. She took out a tape recorder from her pocket. She turned it on. She also gave the nurse a tape measure. "Please measure Lee Ann's height, waist and penis length." The nurse did so reciting the measurements. "Subject Lee Ann is 5"6, with a waist of 34 inches and a penis size of 4.5 inches." She soon had the nurse measure the chest. "The subject currently has a 36 chest size. We hope that once we star hormone therapy that the waist size will move further down and the chest size grows to wehre she will soon start to have to wear a bra."
The examination went on. The doctor probed and felt all around my body. She took notes and spoke into her tape recorder all though out the exam. Once we were done the nurse looked down at my cock. "She still needs to be taken care of her condition down there."
"Well take her cock and jerk Lee Ann off over the toilet," Doctor Williams ordered her to. "Once you are done Lee Ann, come back to me office. You are not to get dressed though." She left the office to let the nurse take care of my cock.
"So you want to be a woman?" the nurse asked me while she started to rub and jerk me off.
"I am thinking about it," I said. "I am not 100% sure I want to but I am thinking more and more that it will be the right thing to do."
"Well I hope you will be happy with it," she told me. "Being a woman is not all that it is cracked up to be. You have to wear bras, makeup and put up with the sexual advances of men."
"I know, but I enjoy all that," I said. "I love putting makeup on and making myself up pretty and driving the men wild." I laughed a bit. "It sounds silly."
"No it does not," the nurse said. "I think you should do what makes you happy." I soon felt my orgasm start. A load of juice shot out of me. I cleaned myself off and went back to the office while the nurse cleaned the equipment off.
"Lee Ann, I just want to ask you a few questions, sit." I did as I was told. "How do you feel sitting here naked in front of me?"
"I sort of feel that I should be dressed and act as a proper young lady."
"OK that is a good answer, modesty is important." She wrote something in my file. "Do you want to start taking hormones to make your body more like a woman's body?" she asked. I nodded. "OK I am going to start giving you shots of female hormones. After a while you will fell your breast grow and other parts of your body change. Once this starts you cannot go back. Your moods will more likely be less assertive. You will also notice that your skin may dry up. After we have you on hormones we can start getting rid on your cock and placing a clit there instead. Are you sure you are up for all this."
"I am doctor," I answered. "I have never felt so positive about anything in my life."
"Good, now go back into the examine room and get dressed. Then we can give you the shots. You will be taking them twice a month." She wrote some more things down.
When I came back she had two shots ready for me to take. She inserted the hormones into my body. Afterwards she gave me a hug. "Welcome to the start of your journey to womanhood."