How I became Wendy
Tw123443@yashoo.com
I live in a large apartment that provides more than enough space for a comfortable home. It has a large living room, dining room, open kitchen with sitting bar. It has three bedrooms with two adjoining bathrooms, and a common one. This spaciousness had a incredible effect on my life! A girl, Emily that I am friends with occasionally stays over. One of the bedrooms is hers for use. She is primarily a lesbian, and I gay, but we occasionally like sex together. Also we help each other out when a member of the opposite sex is needed for social events. Occasionally she brings her girlfriends over to use the bedroom.
On a recent visit she said she has a friend, who was being forced from her apartment due to a condo conversion, and asked if she could use her room until she found a new place. She says that the person has money, so providing rent would not be a problem. Not fully thinking about it, I said yes.
A few days later when I came home, I entered the doorway and heard voices in the living room. There I saw two ladies in lingerie, bras, panties, and hose. One was my girlfriend Emily, the other was an elderly woman, upon closer look appeared to be a cd. She appeared to be in her 50's , nice brown coiffured hair. Her boobs weren't busty, but were attractively perky. I said hello. Emily then introduced me to Karen, the lady who would be staying with me. Emily said that they put her luggage in the room she uses. I was then invited to join them. Karen said that her rented apartment was going to be converted to a condo and residents had to leave immediately. She thanked me for my offer to stay with me, and said she would be a minimal intrusion. As I was tired I went to my room and fell asleep.
The next morning as I was eating breakfast, Karen walked by, dressed in a business type dress. I asked her if she would like breakfast. She joined me and told me about her personnel referral business. She employed three others to recruit and find employment for job seekers. Her office was not far away, and this place was convenient.
That evening, when she came home, I was there and asked her to have dinner. She accepted and I was able to ask her a number of questions. I asked how she got involved in cross dressing. She said she was previously married to a lady who was a very good dresser, and that she admired the way she dressed. When they got divorced, her wife left a good set of clothes, and she began out of curiosity try them on. She said that she thoroughly enjoyed by dressing. She started to buy more and learn to apply makeup. She wanted to go out dressed, but was concerned about being recognized. So she sold her suburb home, moved to the city and opened her business.
When dinner was done, she asked if would be going to the store. When I replied I would be going this evening, she came up with a list of what she wanted and money to pay for it. As she was leaving she noted the breakfast items and told me to have them ready for her at 8 am. I was somewhat shocked at this direct statement, but didn't say anything, and dutifully had her breakfast ready the next morning. As she was finishing her breakfast, she said that I should prepare the meatloaf she saw in the refrigerator for dinner and have it ready at 6 pm. Also she said that she is very busy in the morning and would appreciate it that I would tidy her room and maker bed in the morning.
We started a routine of me cleaning her room and being the cook for our meals. After dinner we started to sit on the living room couch to watch tv, read, or listen to music. One evening, Karen said her legs and feet were stiff, and a rather direct voice she told me to remove her shoes and nylons. Slipping her nylons, I was amazed how smooth they felt. I eagerly rubbed her legs and feet; appreciating her approvingly smile. We continued my rubbing her smooth legs for a few days. One evening she said we need to be rubbing more. She took off her dress revealing her bra and panties and said that I should get naked. Being turned on by her lingerie, I quickly stripped. She had me rub her legs up to her panties. She pulled them down revealing her smooth cut cock. She told me to lick it, taking head into my mouth. She pulled her bra down and had my play with her perky tits. I lovingly sucked, alternating her cock head in my mouth, or cock deep in my throat, and licked until she spurted he cum into my mouth, and had me swallow it. As I was ready to go to bed, she opened a box and gave a female teddy and said I should sleep in it as it would make me comfortable. I slipped it on without any reservations and went to bed.
We lovingly played with each other for a number of days. One evening after I was in bed and nearly asleep, Karen entered my bedroom. She ordered me to get on fours on the bed. I felt her pull teddy over my back. A cool gel was rubbed into my pussy. I could feel her mount herself behind me. Then her cock slowly entered me. Rhythmically, she rocked back and forth. It felt so good. After what seemed like a pleasurable eternity, I felt her tense, and release her cum into me. She lay over me whispering in my ear, Good gurl she said; now you are my Wendy.
The next morning at breakfast, Karen addressed me as Wendy. I would speak to her as Mistress Karen; she said henceforth that in the evenings and weekends, I was to be in makeup, wearing a wig, bra, panties, hose, and heels, possibly a slip. She said she would be picking up these items for me. Also, I would start being her attendant, helping her shower, washing her hair, nail etc., as well as tidying up her room. As females were smooth, she would arrange for me to be shaved permanently.
That evening, Mistress Karen arrived home with a number of boxes. Opening them up, we found many sets of bras, panties, thongs, hose, and shoes. Mistress had me try some on, and model for her. She was pleased and selected a set I was to wear the rest of the evening. She also had me try on the shoes. I was a bit clumsy at first with heels, but she said I would soon learn.
After a while, Mistress said she was going to bed, but would visit me in the morning. I was lying half-awake on my stomach early in the morning. I heard mistress walk into the bedroom. I felt t her lift up the back of my teddy. Then she gave me a painful slap on my ass. I yelped! She told me to turn around. There she was naked, her perky tits erect as well as a very stiff clit. She told me to suck her clit, grabbing my hair and bucking me into her. Suddenly, she turned me over and told me to get on all fours, ass up. I quickly complied. I felt a cold gel being worked into my cunt. Then she rammed her clit deep in me. Oh, did it hurt. Usually she slowly and nicely fucks me, but this time she was fucking deep and hard. I screamed, begging her to stop, but she continued, until I could feel her cum, as did I. She lay on top of me panting, as I was. I tried to get up, but she held me down, I felt her cock inside me stiffen, and she started to pound me again. Quickly, she ejaculated inside me again. What an experience I thought.
Finally, she got up and told me to take off the teddy and follow her.
End of Part 1, more to come
Wendy