Why And How I Started Being A "cd" Crossdresser

I had my first CD experience when my mother punished me by dressing me in my older sisters outgrown party dress , along with
her panties (no bra I was 4yo) but it buttoned up the back, and I was aware tht I could not take it off without help . The lacy socks and maryjanes completed the outfil I was to wear all day,
but  besides my mother and sister were my older sisters 2 little friends looking and laughing at me

Fast forward 9 yrs I am in a new city and a slightly overweight 14yo oversexed boy, a very pretty woman in her 30s a MILF comes up to me at
a party puts her cleveage in my face , her hand on my arm and whispers in my ear (I could smell her perfume) and tells me
"your **** are as big as mine, U should be wearing a bra honey"

So a week or so later , i am home alone and see my older sisters black lace underwire brassiere on the floor and picked it up
it was a minute later I had it on and adjusted (like I had seen my mother do it) and I almost feinted from the wonderful sensation of having my **** shaped and held. That bra fit me like I ahd been measured for it and I had beautiful breasts, a 36B underwire.

Soon I was stealing my mom s and sisters lingerie , and being caught by my mother several times with a huge erection that she always stared at. Finally she asked her gay friends what to do , they told her to buy me my own lingerie. Then my mother had her gay friends talk to me about sex so I wouldn't get hurt . When we had the talk the older man in the relationship had me take off my shirt and shorts

(I was wearing panties when I went to his home), and put on an underwire bra and panty set he bought for me . Then he asked why I liked wearing a bra so much (he could see I really liked wearing a bra) and we chatted while he held me on his lap and he teased my nipples and made me squirm it felt so good.

He and his partner explained that quite often some young boys like to be femme and sissy like gurls and that it is OK, and that many men like them , He asked if I wanted to stay with them and be their "sissy niece" and start at a different school in the fall, my family was moving and he said it would be wonderful experience for me  and less strress for my mother, i would have my own bedroom , but really I would be in their bed every nite.

I would dress as a gurl every day, attend a special school for gays and lesbians ,and meet lots of important people at their "weekend houseparties" in their
mansion downtown that they operated their very sucessful design and decorator studio  and services , they were in great demand.

Not only did I enjoy feeling his very wet hard **** , it was exciting being wanted , so I knew what he was getting at , and I could feel it between my asscheeks and I realized I wanted to stay but I was afraid about being a "sissy boi"  and being called a "****** and queer" so I moved with my family an

never saw them again , and always dreamed of the two men who wanted me as a sissy , , and to cultivate me like a flower.  Later i did go an spend a few weekends  as a "sissy princess" with them enough to know I missed a great opportunity .
tammyie11111 tammyie11111
46-50
1 Response May 16, 2012

Ah yes, opportunities ... some found, like your Mom dressing you in your sister's party dress with panties, and some lost, like the gay couple who wanted to adopt you as their niece. Great story, Tammy, and thanks for sharing.