Caught By My GirlfriendAfter my first wife and I divorced, I thought I would be single forever. I would never meet another girl, mistress, like her who wanted me dressed most of the time; a girl who totally believed in feminization and domination and gave me hormones, clothing and men. Of course she had a bunch of men too. I moved away from the city and lived alone so I could have more freedom to be me. I like women and dated several but I like men occasionally and dated them too when I would meet one who liked crossdressers. I was alone for almost three years when I met Lisa. We dated for a few months and I really liked her. She was beautiful, sexy, little, and loved sex. She wanted sex all the time, everyplace, any position, and no inhibitions. I wanted to tell her about my crossdressing but thought I should wait a while longer until I knew she liked me more. I did not want to freak her out and have her leave yet because the sex was too good. We dated a couple times a week and in between I crossdressed and had a few meetings with men.
One saturday I had nothing to do and as usual when it's a lazy day, I dressed nice just for me. I was wearing a cute short skirt and lacy top I just bought the night before. I did my makeup and hair, and was relaxing on the back patio with a glass of wine. Just then Lisa came walking around the house with her girlfriend and saw me sitting there. At first she said "who the hell are you"? Then she realized it was me and said "OOOH MYYY GOD, Tyler? Why are you dressed like that? What's going on?" The girlfriend giggled and walked away. They started to leave and I stopped her and asked her to please sit down and let me explain. She stood there looking furious saying nothing for a second and said that I embarrassed her in front of her friend and had to take her home. I apologized and asked her to come back after she dropped her off. She finally agreed to come back, but just to find out why I do this.
After she left, I could not decide if I should change my clothes or stay dressed. I decided to stay dressed because this is who I am and she will either accept it or not, and if not, this is the time to find out.
A couple hours later she came back and when I answered the door in my dress, she saw me and started to leave. I grabbed he arm and asked her to please come in and hear what I have to say and then I won't stop you. She came in and sat down with a big frown on her face. She said that when she left, she wasn't going to come back but on the way to taking her friend Kate home, she confided that her husband sometimes wears her clothes. Kate said she doesn't really understand, but she lets him because he is such a great guy in every other way, and when he dresses up, he likes to cook dinner and clean up afterwards. She enjoys the break. So Lisa came back to try and understand before she made a decision to stop seeing me. First, I told her that it's not just me but that millions and millions of men are just like me. I gave her my life story starting from 5years old. I told her about dressing with my sister, my teen years, my twenties and my first marriage. She wanted to know all about me crossdressing with my first wife and I told her all about the things we did, the places we went, and the fem-dom type of marriage we had. I let her know I did not own any men's underwear but wore panties every day no matter where I went, and I wore women's nightgowns to bed every night. I told her about the ********** and sex with other men. I could see that Lisa was really starting to get interested in what I was telling her, especially the things I did with my ex-wife. She eventually started to smile and several times commented on how great I looked as a girl and would have never known I was a man had she not known me. She said that while we were talking she watched how convincing I was in my female role, the way I walked and sat with my legs crossed naturally, my figure, and even my voice changed. I told her I was wearing hip and butt pads, waist cincher, artificial vagina, had voice training and my female name is Tina. She wanted to see my female wardrobe, so I took her to my closet and she was surprised how many things I had. I showed her my lingerie drawers and she said I had more dresses, skirts, panties, and nightgowns than she did. After a few hours of explanation, we were hungry and I said to just relax and I'll make us something. She came in the kitchen and sat while I put on an apron and made a nice dinner. I cleaned up and did the dishes when we were done, while she just sat and talked. I made us a couple drinks and we sat back in the living room and talked all evening. She enjoyed watching me do everything for her while she just sat and did nothing. It was getting late and Lisa wanted to spend the night. When we went to bed, she wanted me to wear a nightgown. She never had sex with a guy in a nightgown before and she loved it.
When we got up the next morning, I put on a robe and fuzzy slippers, put my hair in a pony tail and made breakfast. When we finished, she said she had to go home and do a couple things but wanted to come back in a little while. I told her OK, I would dress as myself and she said "NO, don't you dare, I think I like Tina, and want to get to know her better. I like how you do everything so well and wait on me while I relax. Dress how you would for your ex, and lets have a day the way you did with her. I want to know more." I was totally shocked. She came back a couple hours later and we had a great day together. Lisa was intrigued by the submissive role I accepted previously, and wanted to learn more about the mistress role. She wanted to know everything about a fem-dom lifestyle and said she wanted to try it for a while to see how she liked having a male girlfriend. She was a quick learner and as our relationship continued, it resembled the one I had with my ex. We were very very happy. About a month later she moved in with me and wanted me always in the fem role unless I was at work or in the yard in the daytime.
I'm glad she caught me dressed and liked it so much, because I didn't have to find a way to tell her and wonder if she would accept it or not. Eighteen months later we got married, and continued our fem-dom lifestyle. As time went by we did a lot more girl things. We went out as girlfriends, we had **********, and other encounters with additional men and women. We picked up guys in bars, and more but I'll tell you about that stuff later.