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Seven Years of Cross Dressing - Some Thoughts When I Started  

ShaunaDorothy 55T
25 posts
8/23/2014 6:48 am
Seven Years of Cross Dressing - Some Thoughts When I Started

July 29th, 2007 10:51 am EDT

On the morning of 24 June 07 I placed a “t4m” ad on Craigslist casual in Boston. Over the previous weekend I had answered an ad I happened across on Craigslist “m4m” casuals. An ‘admirer’ had posted looking for ‘fem’ or ‘CD/TV’ s. I answered and sent a picture of myself nude with a little bit long hair, and a hairy chest and legs. I’m 5’5” and 155, so I can look gurlish in a way. He wrote back and attached some pictures of ‘girls’ he’d transformed. Nice looking Tgirls with sexy clothes and make up. He said I had potential, but that for one thing I had to shave the body hair.

I did a lot of posing in the mirror, and found different articles of women’s clothing I had put at the back of a closet, or were left behind by women moving out of my building. I picked some simple things and covered my hair with a danskin that covers arms and has a nice scoop neck that gives the impression of female cleavage without having any, I also found a sarong for a previous adventure in romance.

I took a few pictures of myself dressed, no make-up, I just combed my hair and faced the camera. I took six pictures and posted four of them on “Craigslist”

I got about twenty answers from ‘admirers’ and a few Tgirls over the next two days….

I answered every one, even the one liners…..

.................

August 5th, 2007 8:16 am EDT

On a lazy Sunday like today, I was meandering through the fantasy world of personal ads on Craigslist Casual Encounters – m4m, I answered an ad for a ‘Tgurl” six weeks ago and have been ‘dressing’ seriously since But there were other clues that I might like “dressing” a lot, as I think back….

When I was a little I got my big sister’s hand me down girls figure skates to wear for a couple of seasons on the frozen ice up the park. I was much more into figure skating than I was into hockey. I liked looking down as a slide across the ice and saw those streamline white skates. (I still skate almost every day…roller blades on the street, quads indoors, ice skates in winter…)

My first bike was my sisters girls Raleigh three speed. I figured what the heck, it’s probably faster and lighter. It was easier to get on and off with the lower bar.

I remember sitting in the kitchen in girls underpants when I was about seven. There weren’t any boy’s briefs in the laundry, so my mother gave me some of my sisters girls underpants.

Since I was in high school I’ve let my hair grow when I can. I always associated it with rock music, but secretly I always liked when I looked girlish. I wasn’t a “dresser” but I liked attracting men, and women, because they thought I looked a little ‘fem.”

And as I think back I was always more attracted to guys with girlfriends, or married men. I liked being with men who were usually with women.

..............

August 9th, 2007 5:26 pm EDT


"And the days dwindle down to a precious few, September, November..."

I've been calling this my 'Tgirl Summer' and as the boys of summer pass....

I missed my 'date' last weekend with my admiring 'boyfriend.' He was on vacation and I had a chance to catch my breath. I've only been dressing as a 'Tgirl' and dating a man for seven weeks.

I have a closet full of clothes, I have a couple of men who call me to chat, and might meet. I interact and flirt with women at work, but I haven't been making any effort to meet women to date.

I'm happy having sexual meetings with a man while I'm dressed as a woman.

It occurred to me the other day when I was asking myself how deep I was going to get into this as a 'lifestyle?' and I thought, "What the heck, this is Massachusetts, I can actually marry a man and be his 'wife' if I want to. Let's picture me as June Cleaver with pearls and a nice dress doing the house cleaning while I baked fresh bread for my man. I think I'd rather be the young bride in Hitchcock's 'Rebecca."


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