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How Frankie became Francesca

"A boy's journey into femininity."

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Ever since I was young, I was treated differently. My mom's friends would always comment on how pretty I was with my slender body, long eyelashes and bright green eyes. I spent a lot of time on my own growing up. My father left when I was a teen and my mom and older sister were always out of the house, which meant I spent a lot of time playing by myself.  

When I was seventeen, I noticed that my body wasn't changing as much as my friends. I seemed to lack any manly characteristics and my penis size never really seemed to get any bigger. I thought this was normal until I went into a men's changing room after swimming and saw the other naked men.

I remember how intimidated I felt, changing among all the real men, their huge penises hanging between their legs. Their muscly arms and hairy bodies, how big and strong they all seemed compared to me. When I returned home that day, I stood naked in front of a mirror for a long time, looking at my body and trying to understand why I didn't look like them.

One day while I was home alone, feeling bored and lonely. I decided to play a game. I thought it would be fun to pretend to be a girl. I'd always played these type of fantasy games, imagining I was playing the role of a character in a movie, but this time I wanted to dress up.

I snuck into my sister's room and started to go through her wardrobe. I knew she had a long satin ruffled dress that she wore to a wedding once when we were younger and thought it would make me look more realistic for the part. I remember the feeling of the soft silk against my skin as I pulled the dress over my head and down over my naked body.

The excitement I felt as I tried on my first pantyhose and silk panties, the thrill of sliding my feet into a pair of chunky heeled platform heels and trying to walk like a girl. I looked in the mirror and noticed how different I looked, how much better I looked and felt dressed as a girl.

This continued for a few years, secretly dressing up and role-playing by myself, doing chores around the house while my mom and sister were at work until I left for college. I spent the first few months trying to fit into college life, making friends and trying to put my past behind me.

I never really had a lot of male friends but girls seemed to love me and would always want to hang. I was told I was a 'pretty boy' by a lot of women, and I guess that made most men jealous of me, the fact I received so much attention from women. The weird thing was, I never really knew how I felt about it all.

My best friend Leanne was fascinated with me. She would always flirt with me and we had messed around a few times, but had never let it go very far. She studied psychology and loved to talk to me about all her theories on men, which sometimes got very detailed and dirty, Leanne loved to dress super sexy when she went out and you could tell she knew the effect she had on men.

After sleeping with a guy, I would always hear about it the next day. She'd describe what they did, how he was in bed, his penis shape and size. Every detail. I would sometimes sit on her bed while she told me, looking at her rumpled clothes on the floor, the stains on her bed and imagine the sex in my head. 

Leanne had no secrets with me and I knew everything about her. This only made my secret seem to grow even bigger, and made me feel really guilty about it. As time went on, I started to feel an overwhelming desire to dress again. I would watch Leanne get ready for a night out, picking out dresses and asking me which lingerie looked the most fuckable.

In my dorm room, I started to build a small collection of clothing I had "borrowed" from girls I knew, obviously without their knowledge. Leanne's friend Katrina once commented on how she seemed to have lost her favorite lace chemise and thought one of the other girls had stolen it. I just sat there, terrified that my secret might come out. 

By the end of the third term, I had begun to spend more time in my room, dressing regularly again. It was coming to the end of the year and everyone just thought I was busy studying. Instead, I was experimenting with different looks and had begun shopping for clothes online.

I had become obsessed with the female form, the way women looked in magazines and adverts, and started writing an anonymous blog about cross-dressing. I had found a new friend online who commented on everything I wrote, leaving words of support, encouragement and advice.

I was still hanging out with Leanne a few times a week and she was now getting more interested in studying sexual behavior. Her latest subject was BDSM and fetishism. She would dress like a dominatrix and go to costume parties, collecting studies on peoples reactions. 

She still told me everything that happened in her sex life, including the new experiences she was having which included threesomes, pegging and sex with girls. I lived vicariously through her for most of my college years, having only really had sex with a few girls my whole life.

She never asked me about my sex life but she always seemed to worry about me for some reason. Why I hadn't been dating anyone, if I liked anyone, what I was into? I always just told her I was fine and changed the subject to something else. Leanne was amazing, she always knew when not to push or pry and never made me feel uncomfortable.

My blog was becoming popular and I had built up a collection of photos of myself dressed en femme. I never showed my face out of fear I might be recognized, but even with just my body, I had built up a strong following of supporters. The best thing was that people seemed to love how I looked and would even send me messages asking if I was a real girl.

By the end of the year, I had moved on from just dressing like a girl, and was now spending most of my time alone practicing makeup and hairstyles, talking aloud in a female voice. I had learned how to move, how to walk and talk feminine. All the time alone had made me interested in sex as well.

I knew I enjoyed sex, and dressed as a girl, I would find myself more attractive craving to be more feminine. During my blog sessions, I would visit chat rooms talking about sex with people dressed as a girl! I went by Francesca online and people knew me by this name, which made me feel even more turned on.

During the day, I would wear lingerie under my boys' clothes and change back the second I was back safe in my room. I slept in silky gowns and baby dolls, sometimes with stockings wrapped around my legs. I began to explore my body further starting with my small finger slid gently between my legs, and slowly moving onto using my larger fingers.

I had made myself cum a few times from playing with me boy pussy, so the natural progression to masturbating with a vibrator didn't seem strange at all. After a while, the temptation mixed with the curiosity was enough to make me want to try sucking a realistic dildo, pretending I was giving a real blowjob.

I loved the idea of pleasuring someone in that way, the thought that I could be in control of the most sensitive part of someone. That I could be the sexy thing that made someone orgasm. I practiced sucking a dildo almost every night after that point, once again role-playing with my imagination.

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Towards the end of the year, Leanne had stopped hanging out with me as much and was going to lots of parties. I hadn't seen her for a while when we bumped into each other between classes and she seemed excited about something. She was working on her thesis and wanted me to come to a party with her.

Her study was on behavioral responses and as it was Halloween she wanted to see how people would react to a few different themes. One of these 'themes' she said, was to see a boy dressed as a girl! My face must have changed color when she said the words, and I felt a rush of hot blood go to my head. 

Leanne asked me if I would help her out by letting her dress me in a girly outfit so she could gauge the responses of people that I met at the party. My immediate thought was to run! The thought of anyone seeing me dressed like a girl scared the life out of me. I knew that people had seen me online, but that was different, they didn't see my face, they didn't know anything about Frankie!

I mumbled incoherently, jabbering about nothing as she waited for me to answer. "Please," she begged. "Please help me with my work!"

I only remember blacking out as I mouthed the words 'ok' to her. The next thing I recall was standing naked in her room, covering my small crotch with both hands, nervously shaking while she pulled out outfits and threw them on the bed behind her. When she turned around, she could see my fear and quickly picked up a satin silk thong.

I lifted my legs one by one as she slid them up my thighs noticing how hairless I was. As the thong reached my hands she gestured them away, my tiny shriveled penis barely dangling between my legs. She softly pushed it back between my legs and tucked it away, pulling the thong up over my ass. 

"There, no one will ever notice," she said softly.

After a few delicate moments, adjusting breast forms, applying makeup and styling my hair, she stood back admiring me. There I stood arching my back on tiptoes, in a tiny thong with my perky little A-cup breasts in a push-up bra. She looked at me, almost mesmerized by how girly I looked already.

Next, she picked out a flirty air hostess costume dress with short sleeves, necktie and belt, black satin ribbon stripes and gold button accents. The final touch was a pair of knee-high black PVC boots with matching gold buttonhole eyelets. We both stood in front of the mirror and see how I looked.

"Oh my god!" she said. "I'm well gel. You look even sexier than I do in that dress. This is going to be great!"  

We walked out of the dorm together holding hands, and started to get reactions from people, mostly from men who were wolf whistling and talking loudly to their friends about us. I heard one guy tell his friend how he would pay to fuck a girl as hot as me!

When we arrived at the party I was so nervous I was shaking in the taxi. Leanne held my hand tightly, looked me dead in the eye and told me not to worry. She told me how sexy I looked, how no one would ever recognize me and how amazing the party would be. Her words mirrored the encouragement I had got on my blog and were literally the only thing that could have made me leave the cab.

As we stepped into the apartment where the party was already going off, the music boomed and I noticed how dark it was with just a few lamps dotted around the place for mood lighting. Leanne was saying hello to everyone, and I was clinging to her hand while I followed her sheepishly around the room.

I kept getting looks from people and was feeling really self-conscious. The moment someone said hello to me, I freaked out and hid behind Leanne. She laughed it off and told them I was just shy. I jumped suddenly as a man snuck up right behind me grabbing my hips and shouting, "what's up baby!" in my ear.

Leanne quickly pulled me behind her and stepped in front to defend me. The guy just apologized and asked Leanne what my name was. She looked back at me, a blank and puzzled look on her face.

"Francesca!" I shrieked back in my best female voice. Leanne smiled and pulled me away to another part of the room so we could dance. While we swayed our bodies to the music, I noticed people were still eyeing me from across the room and asked Leanne why.

"Oh honey, it's nothing, they're probably jealous of how sexy you look, or they wanna fuck you because of how sexy you look. Basically 'Francesca', you might actually be the hottest girl at this party!"

I suddenly felt incredibly relaxed and a little horny. I thought about all the times I had looked at myself in the mirror and worried about how I looked, how slender my body was, how small my penis was. Suddenly none of that mattered to me. In fact, I realized that all of those things are what made me special.

After several hours of fun drinking and dancing, flirting with both men and women, I started to become Francesca more and more. I came out of myself completely and felt like I no longer had any inhibitions. I was a sexy girl and I loved it! People wanted to be around me, wanted to dance with me and get close to me.

One guy asked me to dance and began rubbing himself against me while I did my best attempt at twerking for him. I remember his strong cheekbones on his beautiful black face, his large hands holding my hips and could feel his massive erection growing hard in his jeans.

Another girl stopped dancing with her boyfriend and ask if I would like to make out with her. The crowd went crazy as our mouths pressed together, our tongues licking and sucking, the men cheering at the sight of 'two girls' kissing. I realized that no one knew Frankie anymore. No one could even see him, he didn't exist. 

As the night drew to an end, Leanne came to rescue me from a couple who wanted to take me home. The girl had been begging to "eat my pussy" and the guy had already pulled out his cock to show me how big it was, and it was actually fucking huge! We quickly exited and headed back to our dorms.

Leanne was happier than I had seen her in ages and kept saying how proud she was of me. When we got back, we decided to sit and talk for a while before going to sleep. We talked about her studies and what we were going to do after college. She asked if I had any interest in writing, which I thought was strange as I wasn't even studying writing. 

The night was clear and we could see the stars from the window, I looked over at Leanne and thought about our friendship, how important she was to me and knew I had to tell her.

"Leanne," I said softly. "I have a secret to tell you. This isn't the first time I have dressed like this. It started a few years ago..."

She stopped me, putting her finger on my lips. "I know," she said, "I've been following your blog since the beginning. Who do you think it was leaving all those words of encouragement? I mean, I thought you would have figured it out by now. L.J? Leanne Jennings!"

I stared at her, my eyes starting to well up and fill with water, "thank you, thank you so much," I cried out, hugging her under a blanket of stars. Everything in the world finally seemed ok.  

Published 
Written by MirandaGreen
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