Feminization stories are like butterflies: they are all unique and have beautiful markings that define your journey from beginning to end. Check out Sissy C.’s inspirational journey. I’m sure life has many amazing things in store for her!
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“For me, it’s crazy to think of the journey of how I became a sissy. Looking back on it all, it started before I even knew I was a sissy. What I thought was just fun and games turned into 19 years of me wanting more, craving more, doing more, and to do this day fantasizing about doing more.
It all started when I was about 11 years old. My parents were divorced and I had chosen to live with my dad instead of my mom. Since my father worked 12 hour night shifts and my older brother was away from home while working a job of his own my grandma was left in charge of babysitting me. And that when it all started. Things started to get boring. Spending all but 2 nights of every week with my grandma was getting lame for the both us. That is until the Avon lady started coming around more and more. After one of the visits, in which my grandma had acquired a ton of new products consisting of lotions, makeup, and jewelry, she convinced me to be her guinea pig. Day after day, she applied her new makeup products on me as well as her clip on earrings. Then one day I informed her that I didn’t want to be her guinea pig anymore. I could tell she was disappointed by my comment but that didn’t stop her from taking no as an answer. That was when she told me that she was having fun making me look pretty and that it really meant a lot to her because she didn’t have any granddaughters. I actually felt bad for her. She had 7 sons and all of her sons produced sons. So, I allowed her to continue but things slowly progressed over the next few years. She no longer removed the makeup and earrings right after she was finished but began painting my fingernails. Each evening a different color of varnish was applied to my nails and only after I spent a few hours of playing card games with her would she remove all the feminine products off of me. Somewhere during that span, I became fond of our new routine and with her recommendation my toenails were also polished and she even taught me how to do them myself. “It was something I could hide easier and could keep on longer”, she said. Since her reasoning made sense, I went along with it. The last touch she was able to add before her time as my babysitter concluded was shaving my legs. One day after she finished dollying me up and we were about to play cards, she proposed a bet. Looking back on it, it was a one sided bet as there was no consequences for her if she lost but in the end I had lost and an epilator was used removing all the hair from my legs. 2 weeks later as the hair started to grow back I was then taught how to properly shave my legs.
Entering high school, I was now old enough to stay at home on my own and that was when I not only shaved my legs but other body parts also as well as continuously experimenting with different colors on my toenails. Ever since the divorce of my parents, I was court ordered to spend every other weekend with my mom. After enduring the experiences with my grandma, I became intrigued by the dresses and skirts that were stored in my bedroom closet at my mother’s house. And every other weekend I would try on something different all while keeping my toenails done and my legs smooth.
Eventually I got a part time job and no longer went to my moms every other weekend or had my grandma to babysit me but the feeling of those happy times still didn’t stop as I experimented more and more.
Since the day I had money of my own, I have boughten, purged, boughten again, and purged again about 4 times over but in time have slowly accumulated some of my favorite articles of clothing consisting of a few pairs of panties, a garter belt, stockings, 1 bra, and a couple pairs of heels. Yes I still shave and keep my toenails painted, which makes the whole experience even better. Honestly, I have a hard time thinking of a better feeling than that of sliding a pair of stockings up my freshly shaved legs. It makes me feel so feminine!
Over the years, I have publicly humiliated myself by going to the salon to get waxed as well as getting acrylic manicures and pedicures. As humiliating as that experience was for me the attention my fingernails and toenails had caused was even more embarrassing. Maybe if more socially acceptable, I would rock the acrylics more often while showing off my pretty toes. For some reason, I am fascinated with the fake fingernails.
If I were born a female, I would’ve probably ended up in the profession of cosmetology. Then again being a sexy secretary or maid doesn’t sound that bad either! That’s also what I envision myself being if I were to transition.
I really do believe I’d make a better woman than a man. I really do believe that’s what I should’ve been. The professions of cosmetology or being an office secretary sounds much more appealing to me than the typical jobs of a man. I actually orgasm so quickly during sexual encounters that I feel less and less of a man. My penis is an embarrassment and maybe it would be better off gone!
I wish to transition and often dream about it. The thought of a sexy and powerful woman taking my hand and helping me transition would be a dream come true. I have the want to and the need to but have been too scared to follow through with my dream in fear of losing my loved ones. But why? Why must I burden myself like this?
If I could transition, I’d think of myself as more of a lesbian than a cockslut but would definitely be open to experimenting! I’ve played with dildos and butt plugs before and have locked myself into chastity a few times, but if I wasn’t the keyholder? What if I was forced to take hormones while living daily as a woman? What if my shrinking penis stayed locked away and I could never have a male orgasm again, only being able to cum like a woman? What if I really became a woman? All these questions in my head…What if? What if?
P.S. thank you for taking the time to read my story!”