I met Jean at a local bar in a city where we both where finishing our last few months of college. By the time we both had our degree we had become very close. While knowing she liked to be dominant did not bother me. This was in fact a nice change from the other relationships I had.
When the time came to leave college we both decided to move in together in another large city on the west coast. Jean had landed a job there and we figured it would be a nice new start. I figured if we where going to make this commitment we needed to come forth with any thing we felt could change our relationship down the road. She admitted she liked to be in control. I however admitted I cross dressed a bit which caught her off guard. She asked to see my clothing because she did not believe me.
She told me that she had a boy friend once that was a cross dresser. Insisting on seeing my clothing I told her they where in a storage locker in my home town. She must have been really stewing about this because she asked that we take an extra day to detour to my home town so she could see my stash. I tried to avoid this but she insisted so I decided to make the trip. We could visit my parents who liked Jean and it had been five months since we had seen them. We spent the day with them staying the night. Before heading back home the next day we stopped by the storage unit and I grabbed a duffel bag full of my clothing and a few other items. Jill asked what kind of clothing did I wear. Not wanting to miss lead her knowing she would be seeing them anyway I told her slutty clothing.
Now even talking about this made me uncomfortable as it had been my hidden secret for years. When I told her I wore slutty outfits I felt my cock get hard. We had only been back home for several minutes before she insisted I model my outfits for her. I tried to putt it off with no luck. I took my bag into the bedroom where I striped as she watched wide-eyed. Taking a pair of panties out I explained the items I liked most was lingerie. Pulling on a pair of panties and then black short shorts and a pink tank top, I slipped on some three-inch black heels.
Walking around the bedroom for her to see me I had an obvious bulge in my short shorts. Point this out to me, she said I should tuck it under and with some makeup could pass as a girl. This made me tingle all over and my erection was throbbing now. She asked to see more so I put on some nylon bikini panties, mini dress, black lacy bra, and the same heels. How many outfits do you have Jean asked as she dumped out the bag on our bed. Seeing garter belts, nylons, panty hose, various panties, teddies, bras, short skirts, blouses, along with an array of other items.
Jean picked out a full outfit as she set it aside telling me to put it on. As she exited the room she told me to come to the den where she would make us both a drink. Still feeling very excited knowing some one was seeing me cross dressed I had butterflies in my stomach. I put on the items set aside which was a pair of pink string bikini panties with matching bra, white garter belt with light brown stockings, black mini skirt with a white blouse having ruffles down the front. I actually felt sexy after slipping on my heels and looking at myself in a mirror when passing by.
Entering the Den Jean said lets sit down and chat. We talked for several hours over a few drinks. The talk revolved around my cross dressing and her new job along with where we lived. She proposed that I stay home and take care of the house hold while she worked. I was told she wanted me to cross dress and be the maid. Her job would provide for both of us as it was well paying. Living in a new area no one would know us so it would be the perfect start. I would need to grow out my hair for starters. Reluctant at first the more we talked the more appealing it became. I was instructed to go take a bath as my transitioning would start immediately. When I was shaving my legs under her watch full eyes, I knew my fait was forever sealed.
I have been her a maid for the past three years and have my dresser drawers full of female clothing along with my closet. Jean has me wearing female clothing all the time and has plugged me. I have been threatened with chastity when she is not pleased with me. She has several dildos she uses on me from time to time. She really enjoys pegging me and now days I climax when she does it.