I had always been curious about how it felt to be a woman, but it was only that, *curiosity*. I would’ve never said that I was transgender, or a transvestite, or whatever the hell the term is… Not that it matters now.
My name is, or at least, used to be Chris. I was an 18 year old young man, with my whole future ahead of me, I was about to enter college as a football player, I was young, strong, and athletic, all my friends said that I would eventually become a professional quarterback if I was lucky enough.
But yeah, there had always been this… itch… This curiosity to know what it’s like for a woman. I don’t know, ever since I was little, I saw other women of my life and looked up to them with some sort of jealousy, or admiration, or awe; especially the breasts, I always had wondered how it felt to have those orbs of flesh protruding from your chest, showing proudly with clothes, bras and necklaces that were eaten by the cleavage they formed.
So back to when I was a guy, the curiosity was there, always, but I knew it was only a fetish, for me at least, it excited and turned me on to think about it, to think about myself as a young woman, like the cheerleaders of my team, or like those hot teachers that were so effortlessly sexy.
And yeah, you’d maybe know that a person can be stupid while drunk or on drugs, but never… NEVER, a person will make more stupid decisions than when they’re horny.
This story is about a bad horny decision.
I was at home one night, alone. My parents were dining out for their anniversary, I had no siblings, and I was considered old enough to stop needing a babysitter. And well, alone and horny… You know… BAD CHOICES.
I did what I usually did while in those situations, I raided my mom’s closet, took her clothes, dressed in them, got some makeup on (I had gotten good at it!), filled her bra with my own underwear to simulate the volume of boobs slightly bigger than hers; I then put on my favorite dress, a soft, silky, blue sundress; and then, I sat on front of my laptop, opened Omegle, and started posing as a woman.
It was so… Alluring, to have this persona for my times home alone, they had been my best jerk offs of my life. My huge jock cock made a tent on my mom’s dress as I acted like Tara, my womanly alter ego.
After about half an hour of men jerking off to me, or being bigoted against me, or both; my chat got me to another woman, about the age of my mother, who smiled as she saw me.
“Hi!! Oh, it’s so nice to see another woman like me around here, it’s my first time on this page, and I would never have expected to see so many naked people! I’m glad to see there’s someone else who just wants to chat.” She said excitedly.
I couldn’t hold it, my mom’s panties and dress were staining with precum… She thought I was another woman like her! This looked like the perfect time to have a fun, alluring moment and set her off, how would she react when she hears my male voice and realizes that I’m a crossdresser?
“Hi!” I said, with my masculine, jock voice.
Her expression changed quickly, but it wasn’t what I expected, instead of a disappointed, mad woman, I encountered the face of a turned on and intrigued woman.
“Oh god, you’re a man?” She said, still so intrigued.
“Y-yes!” I continued, her reaction was intriguing me as well. “Do you like my costume?”
“I love it! How did you do it? How old are you?”
“I’m 18, and let’s just say I’m great with makeup and prosthetics”.
“Eighteen?! You look forty! Gosh, you look like you could’ve been my childhood friend!” That turned me on even more. I was feeling like a total MILF.
We kept chatting about me and her, about how I loved the idea of being a woman and… Honestly, I can barely remember anything else from that conversation, I can only recall that I was turned on, that I jerked off in the camera, and that before I came, she asked me:
"Would you want to become me?”
“YES!!! “ I said when I came in my mom’s clothes.
—
I stood in front of the address that she gave me. I was skeptical. Looking back, I probably should’ve gone away when I could, but then I started to think about what happened back then on Omegle, and I started to get horny…
And being horny, I made a choice, I knocked on the door.
She opened the door, she was naked… “Hello! Please come on in!” This was getting good! And so, I walked inside the house and she locked the door behind me. I looked at her in all her glory. She was definitely shorter than me, but as a quarterback, it would be rare to meet a woman taller than me. She wasn’t in shape, but she wasn’t fat either, she had great tits that I already knew she had from our meeting on Omegle the other night, and I couldn’t take my eyes off of her.
“Like what you see?” She asked. I could only nod yes. “I’m glad, she responded, “it’ll be all yours in the near future”. Of course, I thought she was playing.
She led me to her bedroom, where an outfit of hers was laid on the bed. “Take your clothes off, and put those on”, she pointed at the clothes on the bed. “I wore them yesterday, didn’t wash them”.
I did as I was told, at this point, I was thinking more with my cock than with my actual head. And so she could see as I took my clothes off, I was, again, rock hard.
I quickly dressed in the lace lingerie from those clothes. Silky stockings, panties, and bra. Then, I dressed in a skirt that was long enough to get to my upper knee, and a pink top. And finally, I put her high heels on.
I didn’t realize that, while I was dressing up as her, she was dressing up in my clothes. When I turned around and looked at her, I was even more turned on, to see our roles changed that way, but even more incredibly, I saw her body changing.
Quickly, her curvy, mature body morphed into mine, it almost looked like a balloon deflating and getting tighter around a figure beneath, my figure… And I started feeling changes too…
My skin got loose on my, my hair grew long until it reached my middle back, my eyesight became worse, my features overall became more dainty and feminine, but the worse part came when, I felt the fat coming in.
My hips, my ass, my arms, legs, belly and… My chest… They all filled with fat. And while my receding jock cock became smaller and transformed into a vagina, everything kept filling, and filling…
And filling…
I grew past her proportions, I knew this was her body, but… I was getting bigger, and bigger, slightly fatter, my tits bigger and saggier… And before I could do anything about it, I faded.
—
It’s been three years now, I’ve become her, but a more fertile, fuller version of her, every day I remember less about my past life, I can only remember that I was 18 and male and an aspiring quarterback, but even if I watch school sports on tv, I cannot recognize who is the one I used to be, who is the body she took from me. *A car arrives at home and the front door gets open.*
Well, time to go, my husband is here, and I need him to fuck me. I’ve realized that it’s the best way to just forget and move on…
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