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How I became a Sissy

when i was in jr high and hs i used to get turned on and masturbate to girls in tights, frilly dresses, pinks, purples and fantasized about having sex with them. pretty typical boy. my life changed when i decided to see how i looked as a girl. my older s*s was my size and i snuck into her room while she was away one afternoon. as soon as i opened the panty drawer, my cock got hard and i was hornier than i had ever been.

i sorted through all of the panties: boy shorts, lacy thongs, pink, light blue lacy, tight black hip huggers and chose a lacy pink thong to try on. i slid it over my legs and over my cock and immediately leaked pre cum....soooo aroused. i looked at myself in the mirror; skinny boy with no body hair and perfectly fit panties.. my cock was throbbing. i had never been so turned on.

i then moved on to the bras: strapless, pushup, frilly, sport all in pasteles, many with lace. her boyfriend was soo lucky ;) i chose a matching lacy pink pushup, slid it over my skinny smooth torso and chest, clasping the back. i shivered as i saw myself: the b cup pushing up my pecs into little A size tits....i let out a high pitched giggle.

next, my favorite fem piece of clothing; the lingere/tights. no boy clothing was anything like the nylon sheer skin tight lingere/ pantyhose that girls got to wear and i was always aroused by them more than anything. with my cock peaking through the top of the panties, i pulled out her pantyhose; white, black, nude, rubbed them on my face. then her ballet tights, leotard: soooo cute. finally at the bottom of the drawer was hidden pair of pink lacy stockings with pink bows on the top. they perfectly matched my bra, panty combo. clearly were hidden and only forher boyfriend's eyes ;)

i took one of the stockings and slid it slowly up my leg, adjusting the lace, bow at my thigh. i did the same with the other. i let out another giggle, moan as i slid my hand up my legs, leaking some more precum on the panties. i was almost shaking i was so aroused. i immediately slid on a pair of her black heels and paced slowly in front of the mirror.

i couldnt stop there. i next picked a tight black prom dress that came down and expanded into frills below the knees with spaghetti straps: low cut with lace over the cleavage.i walked around the room with the dress flowing with each step: the silky material rubbing on my nylon legs, one heel in front of the other. i felt like i had never before....i.felt...sexy. sitting down at her makeup stand, i applied the brightest pink lipstick, smacking my lips, applied black eyeliner and eyeshadow and some foundation and makeup, a touch of blush. i put on a pink hair band with a bow pulling back my medium length hair.

i then went back to the mirror.......i couldnt recognize myself. i stared into my own made up face, lips shimmering pink, down my chest, admiring how the dress fit, my pink legs and feet fitting perfectly in the heels...i knew my life had changed forever. i never felt so aroused and.....different....all my life i had been getting off to women dressed just like this, but what i really wanted, needed was to be one.

i spun around, dancing around the room then layed on her bed, slowly removing the dress, stockings one by one, stuck my hand down the panties rubbing myself both on my cock and for the first time, rimming myself with my finger, enering gently, immediately spraying cum all over my chest, moaning, whimpering...i was always meant to be a girl..... to be continued.....




Published by sissydanny21
10 years ago
Comments
40
Bi-sub_n_son 1 year ago
to jayymie : I wore mommy's underwear and used her dildos many years till i moved out
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Kryfos 1 year ago
Beautiful!
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Sweetreet
Sweetreet 2 years ago
What a delicious story! <3
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julie166
julie166 2 years ago
we all started like that !!
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jayymie 3 years ago
Sissy bliss! I started the same, wearing my sisters panties, bras stockings & progressed from there <3
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phosebitigercd
phosebitigercd 3 years ago
So Hot and Sexy!
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SissyChloeCocksucker
Wonderful story. People always talk about becoming a sissy and it’s an easy phrase to use but the truth hours being a sissy was always inside of us. We just needed something to bring it out. You lasted much longer than I did. I started in panties and the first time I put thigh highs on I filled my panties with sissy cream
Reply
dearandy
dearandy 4 years ago
Hab auch so angefangen , heimlich mit den sachen meiner mutter. Sie hatte einen grossen busen und herrliche hueften einen koerper auf den die kerle geil waren zum besteigen. Ich genoss es heimlich ihre heisse waesche zutragen und dabei dieses spezielle gefuehl zuentwickeln das bis heute haelt
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bintuman22
bintuman22 5 years ago
That first pair of panties covering your boyish arousal is such a delicious image x
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leslie14
leslie14 6 years ago
mmm more plizzzz
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billyboy215 6 years ago
so hot!!!!!
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foxesman 6 years ago
we all did this when our sister out of home 
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oldmanray57 6 years ago
Woman inside me
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oldmanray57 6 years ago
Those were wonderful days,i didnt have sister but my mom had some wonderfully sexy girdles and bra's and slips, 50 years later i still dress to please thd
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oldmanray57 6 years ago
Oh thoss
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billieearls 6 years ago
Lovely
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camisolej
my sis turned me into a sissy
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MPLSbiGUY
MPLSbiGUY 7 years ago
A boy is so cute and sexy when they dress. - Dave
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RodanPolansky
RodanPolansky 8 years ago
Ooh, a cliffhanger! I love cliffhangers...
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twitchums
twitchums 8 years ago
Nice memory. Thanks for sharing
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wixxman 8 years ago
very hot.. loved it
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kenwhoo 8 years ago
Hot story!
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leslie14
leslie14 8 years ago
love it more plizzz
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simno00
simno00 8 years ago
I get exactly the same feeling when i shimmy a pair of stockings up my legs
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colourfast 9 years ago
Lovely story mmm
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Sluttish
Sluttish 9 years ago
Loving your page.We seem so similar that it's almost eerie. 21 in San Diego myself, we were prolly wearing our sisters panties at the same time once, ahaha x) Please keep making content and writing stories, I will always be looking <3
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leslie14
leslie14 9 years ago
sweet
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jaygomez1958 10 years ago
some of feel that right off others like me take thrity years to understand Jay good for you
Reply
biboisean
biboisean 10 years ago
mmmm so hot... i haven[t tried all my sisters clothes... mostly luv panties sexy short shorts and bathing suits. i just get so turned on watching myself in the mirror
Reply
bggb29 10 years ago
how delightful for you
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