Man to Woman

by Jane Futa

  I nodded to reassure myself. A sliver of sunlight peaked through the curtains and outlined Brianna’s body as she moved toward her closet. It was the first time I really noticed the shape of it and how similar looking to me she was. We were both slender with lanky arms and legs. She made it look cute, but I’d always looked a loser. Men were supposed to be built to be sexy. That’s why I never hung around jocks, though. I just had my gamer friends who were either thin like me or overweight. There were no expectations to be sexy with them.

  But I started to wonder what it would feel like to be sexy. I’d never been really confident in my looks before, but I always wanted to be. I only hoped that dressing like a woman wouldn’t set my confidence backward. Not that I could imagine it helping it move forward either.

  Brianna dug through her closet and pulled out a few things she thought would qualify for babysitting outfits. One outfit in particular was a polka dot sundress with a halter top. My eyes fell on it instantly and I realized I didn’t recognize it.

  “I’ve never seen you wear that one,” I told her.

  “Yeah, it didn’t really fit me right. I forgot to return it, but it’d make a great babysitting dress for you.”

  “I’ve never seen you wear a dress when you babysit.”

  “I don’t wear dresses much. But if you really want to be convincing, a dress could help you. Fortunately, I have a few wigs in here too.”

  I started to lift my t-shirt up over my head.

  “Oh, no! You pervert,” she teased. “Wait until I leave the room. I don’t want to see my big brother naked.”

  “You’ve seen me naked before,” I said.

  “Not on purpose. Okay, here are the outfits,” she said, pointing to the bed. “Try some on and make sure they fit. If you need a bra or something, feel free to look at the top drawer of my dresser. When you’ve got an outfit on let me know and I’ll help you with the rest.”

  “The rest?”

  “Yeah. You know. Shoes. Makeup. Hair.”

  “Sounds exhausting.”

  “Trust me. It’s a lot of fun.” She smiled teasingly but her eyes seemed sincere. I watched as she left the room and then I tossed my clothes to the floor. It felt strange to be standing in my sister’s room naked. It was even stranger to think I was there to put on some of her clothes.

  If you need a bra or something, I remembered her saying. A shiver went down my spine but my dick hardened. The idea of wearing my sister’s lingerie seemed so wrong that it was a turn on. I couldn’t ever let her know that I got hard thinking about her underwear.

  I walked slowly to her dresser and pulled out the top drawer. A rainbow of colors and variety of fabrics hit me like I’d just taken a ton of psychedelics. I nearly fainted from dizziness. How do girls keep up with all of this? I wondered. But I was immediately drawn in. I dipped my hands into the piles of fabric and felt the cool, delicate lace and satin around my fingers.

  I was drawn to the only yellow set she had in the drawer. I hardly thought of yellow when I thought of a woman wearing lingerie. It called out to me, so I picked up the panties and bra. The lace on the back of the panties was cut into a butterfly shape. The bra had a similar pattern of lace on the cups.

  I bent over and stepped into the panties. It felt wrong to slide such delicate fabric over my hairy legs. But the more wrong it felt, the harder my dick got until it was almost unbearable. I shouldn’t be doing this. What if our parents find out? Oh god!

  But I couldn’t stop. I loved feeling the lace and satin against my ass cheeks. The back of the panties cut along my ass so that the bottoms of my cheeks were exposed. I’d never felt sexier in all of my life. My cock strained in the tight panties and grew harder against the satin. I tried to ignore it. This is business, I told myself.

  I picked up the bra and slid the straps onto my shoulders. It took me several tries, but I finally hooked it in the back. Then I had a horrible thought. What if she didn’t want me in her panties? She only gave me permission to try on a bra. I quickly ran to the door and pressed my ear to it. I heard her in the distance talking on the phone to one of her babysitters.

  Fuck. I can’t bother her now. I decided to not tell her and hope she wouldn’t notice them missing. I walked up to her bed and picked up the sundress. I held it in front of me and studied it. It was green and the spots were a lighter shade of green. It really was a beautiful dress.

  I slid it over my head and tied the halter straps behind my neck. The moment it hugged my waist, I fell in love. I shook my hips back and forth and watched the skirt twirl as I swayed. I thought about the yellow panties on underneath and sighed with pleasure.

  I don’t know what came over me, but a dirty switch had been flipped. I reached down for my thighs and slid my hands up slowly. I closed my eyes and imagined a man was touching me like his little virgin princess. I even heard his voice telling me to bend over like a good girl.

  I stopped for a moment and my eyes shot open. What the hell am I doing? What am I thinking? But the more I resisted, the more I wanted it. I slid my hands between my thighs until they grazed my hard dick over the panties. I pressed the fabric into my shaft and balls, loving the strange juxtaposition. They weren’t meant to be against a hard dick, and yet here they were.

  I imagined a man behind me, massaging my breasts. I bit my lower lip and moaned. I moved my hands to my ass and felt the panties hug my cheeks perfectly. My dick throbbed and ached to be touched. But first, I had to know what it was like to be fucked like a girl.

  I opened my eyes and looked around the room. I couldn’t believe I was looking for something to fuck myself with. On Brianna’s dresser, I noticed a small hairbrush with a silicone handle. My body tensed. I told myself over and over again that I could not use that to experiment, but my desire took over. I walked up to her dresser and grabbed the brush.

  I wrapped my lips around it and imagined it was a hard cock. I looked to my side and saw Brianna’s full length mirror next to her window. In the darkness, I hadn’t noticed it yet. I walked over to it and sat on the floor beside it. Then I watched myself suck off the handle of the hair brush.

  I still looked like a boy, but in a dress. But that almost made it hotter. I was a little femboy slut. I was going to get fucked like a little femboy. I circled my tongue around the handle and shoved it toward the back of my throat.

  It felt so good to be sucking on a fake cock. I’d never been gay, but this didn’t feel gay. This just felt right. Like I was meant to be a little sissy slut. And sissies get fucked by cocks.

  I slid the skirt up around my hips and turned my side to the mirror. Then I watched myself pull my panties to the side to expose my ass. I slid a wet finger along the crack until it reached my tight, virgin hole. I circled it and moaned. Then I thrust it inside.

  Oh fuck! I wanted to cry out. But instead I merely whimpered. I couldn’t let my little sister hear me fucking myself while wearing her clothes. I couldn’t let her catch me. I slid my finger in and out of my ass and felt it clench tightly.

  I dared myself to stick another finger in and a third, until I had the width of the hairbrush handle inside me. I thrust my fingers in over and over while I watched myself in the mirror. With my other hand, I shoved the hairbrush handle down my throat and I watched myself get double penetrated.

  When I was ready, I placed the handle of the brush at an angle between the floor and my asshole. I used my feet to keep it steady. Then I pushed my ass down on it slowly and felt it stretch me wide.

  I bit my knuckles to keep from screaming, but a moan still managed to escape. The further in it slid, the more I wanted to come, and it only took a few thrusts before I exploded all over my sister’s panties.

  I held up her dress so it wouldn’t get messy, but it was too late for the yellow panties. In the mirror, I could see a stream of white drip down my inner thigh and a stain formed in the crotch of the panties.

  I exhaled and pulled the hairbrush from my ass. I looked around desperately for a way to
clean it. It was the last thing I wanted to do, but I didn’t have a choice. I put it back in my mouth and cleaned away the scent of my ass with my tongue.

  It wasn’t as bad as I had expected. Everything in those few minutes turned me on more than I ever thought possible. I was starting to feel natural in a dress. I just had to hide the panties from my sister long enough to hide them.

  I placed her brush back and straightened my outfit. Then I stepped out of her bedroom and looked for Brianna. She was down the hall in the game room, still in the phone with a babysitter.

  When she saw me, she told her sitter that she had to go and a wide smile stretched across her face. “Wow, big brother. You almost look like a girl already!”

  I couldn’t help but blush.

  “Wait a second.” As she said this panic flooded my veins. Oh no. She’s caught me. “Do you like wearing my dress?”

  “No. No. I hate it,” I lied, trying to sound convincing.

  She burst into laughter. “Oh my god. You love it! You love being a little sissy femboy!”

  “No I don’t!” I cried out. But it was no use. I did love it and I couldn’t lie about it.

  “It’s okay,” she said, walking toward me. “I won’t tell anyone your little secret. Especially not if it’s going to make us rich.”

  It was the first time in thirty minutes that I had thought about the money. I was so pleasantly distracted by cross-dressing that I had completely forgotten why I was even doing it. Suddenly, money didn’t seem so important. Not that I was going to turn down an easy gig.

  “Yeah. For the money,” I added quickly.

  “Ok. We have some more work to do,” said Brianna. Let’s find you a wig, do your makeup, and shave those horribly hair legs of yours.

  “Shave?”

  “Yes. Every girl has to shave her legs. I mean they shouldn’t have to, but it would be more convincing if you did.”

  I exhaled and nodded. She walked back into her room to look for a wig and some makeup. “Hey. Did you take my yellow panties?” she called back.

  I blushed. “Yeah. Sorry.”

  “It’s okay. I hated that yellow color anyway. You can keep them.”

  I couldn’t help but smile. I would have my very own bra and panty set. I would have my very own little secret. I followed her in and waited eagerly for her to finish transforming me into an innocent little babysitter.

  Chapter 4

  A few days later I had my very first babysitting gig. Brianna helped me get dressed again since I was still new to everything. She pulled a blonde, wavy wig from her closet and attached it to me head expertly.

  “Why do you have these things, anyway?” I asked her as she slid bobby pins through my hair.

  “For fun, of course.” I couldn’t help but laugh. Girls went through so much work for fun. But I was starting to understand the appeal. Especially when I saw my reflection in the mirror. The blonde hair made me swoon and I no longer saw an ounce of boy in me.

  I almost didn’t even need makeup. It was already so convincing. But Brianna insisted on some just to be safe. I closed my eyes and let her brushes dust my face. She drew on a thick, winged eyeliner across my top eyelid and gave me rose pink lips. She layered the lipstick with a slick gloss which felt strange at first until I imagined wrapping my lips around someone’s cock.

  The gay thoughts were starting to confuse me. I’d never wanted to be with a man until I had dressed as a woman. Something about wearing short skirts and wigs made me want to be submissive to some masculinity. I enjoyed the conflicting thought even though I knew I’d probably never act on it. Hell, I couldn’t act on it, even if I had the opportunity…right?

  Brianna told me to open my eyes and when I saw my reflection again, I couldn’t believe it. I wasn’t just convincing…I was hot. I felt the urge to fuck myself again while watching my reflection. Hell, I wished there was a girl as hot as me for me to fuck as a dude. But the strangest thing was how great it felt underneath all of that makeup and in my sister’s clothes.

  “You’re all set. I can’t believe how gorgeous you look! I’m jealous, to be honest,” said Brianna as she checked me out.

  “You’re beautiful too, don’t worry.” She stuck her tongue out at me playfully and we both laughed. I couldn’t believe how much we were bonding over this. Maybe she just wanted an older sister all along…

  “Time for you to go to your first gig. You ready?”

  I opened my mouth to speak and then closed it again. My heart was pounding in my chest at the thought of showing my new feminine side to a total stranger. I shook my head to let her know I was still pretty insecure about the whole thing.

  “You’ll be fine. You’re hot, but not too hot. Just don’t be a dick to them and they’ll love you. Then we’ll make tons of cash together this summer.”

  I exhaled and nodded. She picked out a purse for me to carry and a pair of flat dress shoes. I was wearing the dress from the day before with her yellow lingerie. So far, she had been incredibly helpful. I thought she would’ve only made fun of me but I felt closer to her than ever. I started to feel grateful for our silly little bet.

  The purse was more like a big leather bag that she put supplies inside of. There were toys and books since the kid I was going to babysit was a toddler. “Doesn’t he already have that stuff?” I asked.

  She nodded. “It makes us look more professional though. Now get going before you end up late to your first job.”

  I sighed and hugged her goodbye. It was the first time I had hugged my sister since we were kids. I ran down the stairs and hopped into my car quickly, hoping to leave before my parents came home. I’d be in so much trouble if they found me dressed like a girl!

  I plugged in the address to the GPS on my phone and drove to my first gig. What if they can tell I’m really a boy? What if they think I’m some sick pervert? The closer I got to the house, the more anxiety I felt.

  I finally walked up to the front door and knocked, preparing myself to be called out as the sissy that I was. As the door swung open, I closed my eyes tightly and waited for the screams.

  Instead, I was greeted with a pleasant, “Hello! Come on in.” I opened my eyes slowly and saw a tall, brunette woman with short hair. She had a friendly demeanor but a jawline that made her look strict. I couldn’t get a clear read from her. She seemed welcoming but skeptical. When our eyes met, she was warm and friendly, but out of my peripheral, I caught her eyes narrowing at me.

  She’s going to figure it out. Oh my god, oh my god. I can’t do this. This is crazy. What did I let Brianna talk me into? I have to go home. I have to go home before anyone finds out.

  Then her husband came out and my mind stopped racing. He was so beautiful I could feel my jaw hanging open. I’d never thought a man was beautiful before, but standing in their foyer in my dress, I felt like a total woman.

  He had a strong build and blue eyes that made the feminine me swoon. I reached out my hand quickly to introduce myself. I quickly tried to think of a name for myself and spit out the first one I could think of. “Nicole,” I said.

  That’s when I noticed the mom lighten up a little. She seemed convinced by my sudden interest in her husband that I was really a woman. Her husband smiled and showed his dazzling, white teeth. “Chester,” he said.

  “And I’m Monica,” said his wife who stepped quickly to his side. “Are you ready Chester?” He looked at her lovingly and nodded.

  Monica ran over a few instructions for me, but the job seemed easy enough. Her kid was easily distracted by Netflix and toys. All I really needed was to make sure he didn’t swallow any poison or anything.

  “Thanks so much, Nicole,” she said, wrapping her arm around her husband’s arm. I watched them walk through the front door, but before Chester had stepped out of the house, he turned back to look at me. I’d never been checked out by a man, but that’s what he must’ve been doing. I felt so dirty and naughty after he looked at me. Like he was picturing the things he’d like to
do to my femboy body.

  Chills ran down my spine as they left and I couldn’t stop thinking about him. I tried to distract myself with the cartoons that their kid was watching, but all I kept picturing was the hairbrush handle sliding in and out of my ass. It took all the restraint in the world, but I was a good little sissy and stayed put on the couch until they returned from their date.

  I couldn’t believe how easy it was to babysit. I didn’t lift a finger the entire time and then got a wad of cash for it. Monica thanked me again and I went back home to my sister. She texted me when our parents were asleep so that I could sneak in unnoticed.

  “How did it go?” she asked enthusiastically while helping me to take off my wig and makeup.

  “I can’t believe how easy everything is! You get paid that much money to do nothing?”

  “Pretty much,” she said with a laugh. “People pay a lot who want someone trustworthy. But you pretty much just sit there most of the time. Older kids, however. Older kids can be harder. They love to push all of your buttons. Don’t worry, though. I’m giving you the easy gigs. The last thing we need is some lame kid revealing that you wear a wig or something.”

  “Oh god.” I hadn’t even thought of that. Brianna’s confidence started to quell my fears.

  “So I have another gig for you tomorrow. The lady is a single mother who has work meeting to go to. If she likes you, you’ll probably get a lot of gigs out of her. It’s also super easy because the kid will be asleep most of your shift.”

  “You get paid even while they sleep?” Brianna laughed at me.

  “Get some rest, now. We have to do this whole thing again tomorrow.”

  What used to exhaust me now excited me. I suddenly felt naked without my wig and makeup. I missed them and I couldn’t wait to decorate myself again the next day. As I lay in bed, I thought of Chester and the way he had looked at me before he left.

  Then I tugged on my hard, sissy cock until I came.