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I was when I first started dressing in my mother's and sister's clothes.
My dad left when I was an infant and I was never exposed to many guy
things. I was always fascinated with womens clothes, especially panties,
and finally tried on a pair of my mom's panties when I was in the
basement laundry room. I started doing it almost every day after that for
nearly a year and no one knew it. I advanced to putting on bras, slips,
pantyhose, and dresses. I loved it.
Then one day, unbeknownest to me, my mom had called her brother, my Uncle
Ray, to come over and fix a leaky pipe. I was busy dressing up and
oblivious to anyone coming downsatirs. I looked up and there stood my
uncle staring at me wearing a pair of my sister's black lace panties and
matching bra and black pantyhose. I was stunned and did'n't say a word.
Ray starred at me for a moment then turned and walked away. I was really
scared that he would tell my mom, so I changed back quickly and went
upstairs to my room. Ray fixed the pipe and then I overheard him asking
my mom if it would be ok if I spent Saturday with him. She said yes, that
it would be good for me to have some "guy" time since I did'nt have a dad
around.
Saturday rolled around and I was nervous about seeing my uncle. My told
me to pack an overnight bag in case I spent the night. We arrived at
Ray's early and mom and Ray chatted in the kitchen a few moments then she
left. Ray led me to the living room and sat me down next to him on the
couch. He asked me if anyone else knew about my dressing as a girl and I
told him no. He put his hand on my leg and promised that he would never
tell anyone. He said I looked pretty in lingerie and that I shouldn't be
embarrassed about it. He took my hand and led me to a bedroom where his 2
daughters stayed on the the weekends he had custody. Ray was 38 and
divorced. His girls were 12 and 14. They had a room where they kept lots
of girl things as well as quite a few clothes. Ray told me I could stay
in there and that I could wear anything I wanted. I could'nt believe it.
Ray told me to change into something prettier and closed the door. I
stood and looked at the pink walls and lace bedspread and felt scared and
excited. I opened some drawers and found their panties and bras. I sifted
through them and chose a pink lace pair with a bra to match. I disrobed
and slipped on my new undies and stopped to see myself in the mirror. I
then opened more drawers in search of hose and slips. I picked a pair of
white pantyhose and a white half slip. I moved to the closet and looked
through thir dresses and skirts. I found a cute white and blue summer
dress that must have belonged to Angie, the older sister. Fortunately I
have always been small and have never had difficulty fitting in womens
clothes. I buttoned the dress up the front and chose a pair of white
heels.
I noticed a makeup case on their dresser and opened it. There was
lipstick, eyeshadow and mascara in there so I tried for the first time to
put on my face. I did ok for the first time then Ray knocked on the door
and asked if all was ok. I opened the door with my knees knocking I was
so nervous. Ray stood and admired me in my new outfit. He said I looked
beautiful and asked me to do a turn for him. I spun around and as he
stepped into the room and took me into his arms. I let him hold me as he
took my face into his hands and told me that from now on I was Lisa and
would be his to play with. Then he kissed my lips. My head was swimming.
Not only did I look like a little girl but now was being treated like a
girl. He slipped his tongue into my mouth and I gave him mine. Ray was
not tall and with my heels on I stood at his chest. We kissed a while as
he ran his hands around my tight little ass.
After he stopped kissing me he asked me how I felt. I told him I was
nervous but it felt good. He promised that I could come over often and
that he would teach me how to be a girl. He then told me he had a suprise
for me and took me to his room. He opened a bag and pulled out a wig. It
was blond, like me, and shoulder length, curled on the ends and very
pretty. He put it on me and turned me to the mirror. I looked like a
pretty girl, there was no way to tell I was a boy. He also pulled out a
garter belt and some stockings and told me he prefered that his women
wear them. I lifetd my dress up and slipped off my pantyhose. Then he
hooked up my new lace white garter belt. I pulled on the silk hose and he
attached my garters to them. I was complete.
He asked me if I wanted to go shopping for more girl stuff and I squeled
yes. We climbed into his car and headed off the local mall. I was scared
that I might see some people I knew but we went in and started shopping.
First we went to Macy's for lingerie. He always called me Lisa and held
my hand and sometimes kissed my cheek. People smiled at us thinking I was
his little daughter. He picked out several bra and panty sets and sent me
to the dressing room to try on. I was about to die as I entered the
ladies dressing room. An older woman smiled at me as she adjusted a bra
and I tried on all my things. I told Ray I loved all of them and we
bought them and headed to the girls dresses.
Ray told the clerk that I needed some cute summer outfits, but that I had
plenty of shorts. She led me to the skirts and dresses and soon I was in
the dressing room trying on short outfits and dresses. The clerk helped
me and was suprised to see me in garter and stockings. Ray bought me 2
dresses and mini skirts we headed home. As we drove home Ray slid his
hand under my dress and rubbed me through my panties. I felt a rise and
he took my hand and placed it on his lap. He was hard and he told me to
rub it.
When we got home Ray took me straight to his bed and laid me down. We
started kissing and he lifted my dress. He went down on me and kissed my
panties then pulled my lttle dick out and sucked on it. Soon I came and
he drank all of it. Then he undressed and I saw his cock for the first
time. It was about 6 inches and he put it in my face and I started
licking it. He moaned and told me how beautiful I was and told me to put
it in my mouth. I opened wide and he fed it to me. I choked at first but
slowly I was sucking on it. He held my head and was pumping his cock in
my mouth. He shot off in my mouth and I gagged. I t tasted good but I was
just suprised. He laid down on the bed with me and we kissed more.
Ray called mom and said I was going to stay over. I slept in a sheer
nightie and Ray and I had sex all night. He put a vibrator in me and I
loved it but he said he would wait a while to fuck me. We waited about 2
months before he fucked my tender ass but after that he had it all he
wanted.
For the next 6 yearsI stayed at Ray's every other weekend and even
vacationed with him. I always dressed as a girl when with him. Ray moved
away and I have sinced moved in with an older man and live as his
mistress. More to come!!
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