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How I became a Sissy

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
9 years ago
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54
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to jayymie : I wore mommy's underwear and used her dildos many years till i moved out
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Beautiful!
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Sweetreet
What a delicious story! :heart:
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julie166
we all started like that !!
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jayymie
Sissy bliss!

I started the same, wearing my sisters panties, bras stockings & progressed from there :heart:
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phosebitigercd
So Hot and Sexy!
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I feel sexy just reading this, great job :smile:
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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
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dearandy
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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very beautiful story.  Thanks for sharing
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bintuman22
That first pair of panties covering your boyish arousal is such a delicious image x
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leslie14
mmm more plizzzz
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like to hear more. 
u open to suggestions?
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so hot!!!!!
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we all did this when our sister out of home 
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Woman inside me
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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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Oh thoss
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Lovely
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my sis turned me into a sissy
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wish there was a hidden camera video of this
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MPLSbiGUY
A boy is so cute and sexy when they dress. - Dave
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thats how it happend for me
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RodanPolansky
Ooh, a cliffhanger! I love cliffhangers...
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sweet
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twitchums
Nice memory. Thanks for sharing
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very hot.. loved it
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Hot story!
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leslie14
love it more plizzz
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lov it
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