My week as a free woman/ fairy princess

I recently had the most wonderful, crazy, rewarding week I've ever spent. I'm a 32 y/o man who has crossdressed since I was a kid. When I was 27, I became friendly with Ann, a 57 y/o woman who moved in next door. She had seen me as a 'woman' and was totally cool about it. We quickly became friends, and I felt extremely close to her [I have 'mommy' issues]. Ann encouraged and supported my crossdressing, which was all-out clothes, makeup, jewelry, and wigs. At a slim 5'7", I look good in drag. After 3 years, she inherited a nice private house and since we were very close and were BF/GF and BFFs I moved in with her(2 years ago). I'm in the best relationship of my life, I have the mother figure I needed, and she loved it. I do all the housework and chores. And, it is great even tho we had never been sexually intimate (I have my own room).

In July, Ann told me she wanted to vacation in Fire Island, where she had friends. We had vacationed together 2 other times, once bringing some female clothes for private dressup. I expressed the desire to be Carolyn [the name she gave me] for the week. We talked it over and she agreed. I was to bring NO male clothes at all -I would be 'female' 24/7 for the week. I got a woman's bathing suit too. It sunk in as I had to Nair my entire body. I had to pack outfits, makeup, jewelry, wigs and handbags, and only high heel shoes. We was ready.

I was freaky getting on the ferry in full drag, but the other passengers were cool [mostly gay & lesbian]. We checked into the hotel, and they didn't care that I was male. The reality really set in as I thought about not having any male clothes to fall back on. And after walking around for a while, I realized that heels all day was a tough deal. But it was so incredibly LIBERATING to walk in public dressed as a woman, being called Carolyn, and it was accepted. And I was in an almost constant state of arousal doing full drag with my GF. Of course tucking my ** back between my legs took care of any bulge!

Sleeping in little nighties, snuggled with Ann was awesome, even tho we weren't having **. And waking up knowing I was Carolyn. Going to the beach in a woman's bathing suit with no make up or wig. I had no choice but to be female for a week, and I saw it wasn't that easy, altho I was in heaven. By the 3rd day of wearing only 4 inch heels, Ann looked at me, smiled and said, "Well you wanted to be a woman for a week". Deep down I loved the discomfort. I even went for a pedicure.

On the 5th day, Ann looked at me and told me how proud of me she was. She noted that I acted like a perfect lady, even tho it was obvious that men were flirting with me all week. I got emotional with joy. That night we made love for the 1st time. It was BEYOND glorious. Ann and I were LOVERS! The soreness in my feet and calves was worth it! After vacation, Ann asked me to share her bed with her all the time. We agreed that I'd dress up 3-4 times a week (she does want a man some of the time!)

If this wasn't enuf, Ann opened up a wardrobe in the basement which was full of her clothes from the '70s and 80s. She was a bit bigger then, so when she had me try on one of her "disco" dresses, and it fit, I just lit up. The she said, "Carolyn, these clothes are now yours." I almost cried. 3 dozen outfits and a dozen pair of Ann's high heels!! Wear HER clothes makes me feel even closer to her. Her shoes are a size small, but I wear them anyway. I'm in love. I hope Ann is too.

Aug 20, 2014

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  • That is so sweet! You have the best BFF ever!

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