Man to Woman

by Jane Futa

  “Well, go on,” she urged with a bright smile.

  I slid my arms through the straps and placed them securely on my shoulders. Then I reached each end of the clasp around my back and tried unsuccessfully to fasten it. Scarlet giggled and then walked over.

  “Here, I’ll help you. Turn around.”

  I rotated so my back was to her and saw myself in the mirror wearing the pink bra. The color brought out the rosiness in my cheeks and it looked like I was wearing makeup. Scarlet fastened the clasp and I ran a hand through my short, light brown hair.

  “I look hot,” I said aloud without thinking. Scarlet burst into a fit of laughter.

  “I told you. You’re such a girl!” she yelled as she shoved me playfully. “But now you have to show me the whole thing.”

  I turned back around and she resumed her place by the wall. Then I dropped my pants to showcase the pink thong from the day before.

  “Step out completely,” she said. I stepped out of my pants and kicked them to the side. “Now give me a spin.”

  I spun around and caught myself in the mirror again. I totally could pass for a girl, I thought. Scarlet gasped at my ass. I saw her reflection in the mirror staring at my lower half.

  “You ass is so cute and perky! I wish mine looked like that,” she said. Then she walked up and grabbed a handful and squeezed.

  “Thanks,” I said bashfully, making my cheeks even redder. Scarlet spanked my ass lightly and ordered me to get dressed.

  The pants were easy enough, but I struggled with my shirt. I tried a million ways to hide the padded cups of her pink bra.

  “No one is going to notice,” she said. “They’re all glued to their computers anyway.”

  “What if I pass someone in the hall?”

  “Trust me, they’re all too miserable to notice or care if some guy has breasts all of a sudden.” She giggled after she spoke, and I was starting to feel like we were good girlfriends.

  I finished buttoning my shirt and folded my arms across my chest. “Who leaves first?” I asked.

  “I will this time,” she said as she rushed to the door. “I want to see you strut your way down the hallway like the pretty girl you are.” She giggled again and unlocked the door. She peeked through the crack as she opened it and when the coast was clear, she ran out and down the hall.

  I waited a minute, admiring the feeling of a bra wrapped around my chest. For a moment, I almost felt like I had breasts, and I eagerly ran my hands over them. A tingle swept through my entire body and I felt like a real woman. I desperately wished I had a pussy to play with in the bathroom stall.

  I sighed with ecstasy and then tried to collect myself. I may be a woman in here, but out there I need to be a man still. I stood tall and lifted my chin high. When I left the bathroom, I walked as quickly as I could down the hall toward the cubicles. As I turned the corner, it seemed as if everyone was standing up and walking around. It was like a minefield and I feared I’d be discovered as a cross-dresser.

  I rushed past a few coworkers, keeping my head down until I finally reached my desk. The adrenaline pumped through me as I thought about how I had gotten away with it all. The thrill of almost getting caught turned me on, and it was hard to think about anything else.

  A few moments later, I overheard Scarlet speaking to Matt again. What is she going to say to him this time? I hoped it would be nothing, but if it was like last time I knew she’d try and draw attention to me. Then I remembered that if he spoke to me, he’d quickly notice the fake tits jutting out from my chest.

  I quickly slid my coat on over my shirt and zipped it up. I looked ridiculous wearing a coat in the office, but I figured I could play it off somehow.

  In the reflection of my dark monitor, I saw a figure come up behind me. Shit. I spun around to see Scarlet this time instead of Matt. I sighed with relief and she giggled as quietly as she could.

  “I told Daddy that you were helping me quit smoking for good. He wants you to come to our house this weekend for dinner. I think he’s going to give you a raise!” She smiled excitedly.

  “Why are you being so nice to me?” I asked.

  She leaned forward and whispered, “Because you’ve been such a good little girl for me. I really enjoy playing with you.” She stood back up and winked at me.

  The thought of dinner with my boss was terrifying. Especially with his daughter knowing my little secrets. “Tell him, I’d be happy to join,” I said despite every cell in my body telling me to decline.

  “Fantastic!” she said with the glint of a scheme in her eye.

  What did I just agree to? I wondered.

  Chapter 3

  I nervously approached my boss’s house. I didn’t see his car in the driveway and figured it must have been in the garage. I swallowed hard and then knocked on the front door. When no one answered, I rang the doorbell. I heard what sounded like someone skipping and then the door swung open. Scarlet had answered in a tight, red, strapless dress.

  “Yay!” she cried while clapping. She grabbed my hand and pulled me into the foyer. I looked around and saw luxury furniture and artwork everywhere. The rest blurred by me as Scarlet dragged me to the stairs. “Let’s go to my room.”

  “What? No, no. I can’t be caught in your room.” Then I noticed how quiet the house seemed. “Did your dad forget about dinner?”

  “Oh no,” she said. “But I may have told you the wrong time to get you here earlier. My parents won’t be home for a couple of hours.”

  “Won’t they be upset to find me here?”

  “Oh we’ll finish early and then you can leave for a minute and come back.”

  “I don’t know…” I said, biting my lower lip.

  “Trust me. You’re going to have fun!”

  I reluctantly followed her up the stairs and to her room. Her bedroom décor was surprisingly mature. I wondered why it surprised me, since she’s never really acted like a child except for the giggling and the rebellion. Still, I couldn’t believe I was in my boss’s daughter bedroom. I could’ve been fired for much, much less.

  She had a full size bed that sat in the middle of the room. The sheets were a deep red and she had black and white art photographs on her walls. I noticed that she had a few outfits laid out nicely on her bed.

  “Were you picking something out for tonight?”

  “Yes, in a way…” she said, tilting her head to the side and smiling. Then her demeanor quickly changed in a burst of energy. “They’re for you!” she cried.

  “What?”

  “Well you’ve tried on my bra and panties…Now I want to complete the outfit.”

  “What if your parents come home? This isn’t a great idea,” I told her.

  “I already told you…They won’t be home for a few hours. I guarantee it.”

  Despite her guarantee, I didn’t quite believe that I wouldn’t be caught by my boss. At least I won’t be fucking her, I thought. But thinking of not fucking her made me glance at her chest again. Her dress was barely held up by her tits, and I had the perfect view of her deep cleavage.

  “Start with these,” she said as she skipped to her black dresser. She pulled out a matching white bra and pantie set. It was simple cotton with a layer of delicate lace on top. She skipped back over to me and held them out in her hands.

  I couldn’t hide my excitement to try on some new things. “Well ok,” I said with a smile which she reciprocated.

  I quickly unbuttoned my black shirt and tossed it on the floor. She watched eagerly, biting her nails with excitement. I slid the bra on, but this time I was able to fasten it myself which made me feel like a real woman.

  “Good job!” she said when she realized I didn’t need her help this time.

  Next, I unbuttoned my dress pants and slid them down. I kicked off my shoes and shoved my pants near my shirt. Then I slid my briefs down and Scarlet giggled again. I was amazed at how comforting her giggle had become, even if it was because I had a small cock or liked to dress like a
woman. Her enjoyment turned me on in a way that was completely foreign to me.

  I slid the panties up my legs. The cotton felt similar to my briefs but the cut of them was tight and sexy. The fabric wrapped nicely around my cock and balls. I felt delicate and pretty. I walked over to her full length mirror and posed like a supermodel. She giggled and I blushed. A warm tingle spread through my body and I suddenly wished I could know what it was like to be fucked as a woman. All of the sensual posing was opening up new desires to me. I wanted to be penetrated.

  “Ok, ok. Now put on the first dress.” She pointed to a blue and white floral sundress. I swayed my hips as I walked over to it. I picked it up by the straps and held it up in front of me, admiring it. I unzipped the back of it and stepped into it. I loved the cool fabric against my skin as I worked it up my body. I slid the straps onto my shoulders and Scarlet zipped it up for me.

  The skirt flared out and I felt more feminine than ever. I just wanted someone to bend me over and fuck me from behind while the dress was still on. It was the most erotic feeling in the world.

  I couldn’t believe we were the same size. She was so tiny, and I was by no means very bulky or masculine, but I still would’ve guessed I’d be bigger than her. I walked back over to the mirror and couldn’t believe my eyes. I looked exactly like a young female with short hair. My hair was even long enough to pass for a feminine haircut.

  “Stunning!” she said next to me as she looked at my reflection. I posed a few more times and the giggling resumed. I felt like a young girl trying on her best friend’s clothes. I had almost completely forgotten about how I could be fired for this.

  “Next outfit!” she cried.

  I unzipped the dress and slipped out of it. I laid it back in its place and picked up the first piece to the next set. It was a black mini skirt and a red halter top. I pulled it up my hips and fell in love with the way it hugged my ass.

  Next, I untied the halter straps and slid the top over my head and down my torso. The padded bra I was wearing really gave this top some oomph. I tied the straps behind my neck and then turned to face Scarlet.

  “Hot!” she cried. “I kind of want to bang you in that!” Her words sent a chill down my spine. I also want you to bang me, I thought. My legs quivered as I thought of being an object of sexual desire and being taken like the slut I was becoming. I pranced to the mirror and my jaw drop.

  I could go out to a bar now and convince someone I was a hot chick. I posed like a badass looking for a good time. Scarlet came up behind me and spanked my ass playfully, but it left me wanting more. My cock was fully erect but you couldn’t tell even through the tight skirt. It was the only part of me that reminded me I wasn’t actually a woman.

  “Ok, last one,” said Scarlet, spanking my ass again. I walked back to the bed and stripped. It felt just as nice taking off the feminine clothes as it did putting them on. I’d had no idea how powerful these clothes were or how powerful they could make someone feel. I felt like I could seduce anyone and get anything I wanted. Oh the idea!

  I saw that the next outfit was just a hot pink bikini. I slid the bottoms on first, the slick fabric sending shivers up and down my legs. Then I put the top on and realized it, too, was padded. I loved feeling like I had breasts to go with these sexy clothes. I pranced back to the mirror and adored what I saw.

  I’d never liked how I looked before. I was too scrawny to be a real man, and men’s clothes didn’t bring out my confidence, but I was a completely different person in these outfits. I felt sexy and perfect. I felt fuckable and desirable. I started to wish that I could wear this stuff all of the time. Being a woman seemed so much more fun.

  I looked to Scarlet in the mirror’s reflection and noticed she had moved over to a small vanity table. “Come here,” she said, waving me toward her. I did as I was told and sat down in the chair she’d pulled out for me. “Time to give you a little makeup,” she said.

  “I don’t know. How will I get that off when it’s time to have dinner with your parents?” I asked, looking up at her with big doe eyes.

  “Makeup remover of course!” She seemed so confident and so far I hadn’t been fired. I started to feel like I could trust her. After all, she was introducing me to a completely new lifestyle that made me feel complete.

  “Ok,” I said and waited for her to primp me.

  She reached for a small cylinder and I quickly realized it was bright red lipstick. She twisted the base so that the rouge rose up slowly. I relaxed my lips in preparation. She pressed the stick to my skin and glided it from one corner of my mouth to the other.

  “Now press and rub your lips together.” I did for a few seconds and then relaxed. “Hot!” she cried. I blushed and smiled. I looked back into my reflection and loved the way the red complimented my skin tone. I looked like an edgy fashion model.

  Then she grabbed a second tube and pulled out a black wand. “This is mascara. Keep your eyes open and just trust me.” I nodded and relaxed my face. She moved the want toward my eye and brushed it upward in soft strokes. “Ok, now let’s do the eyeliner.”

  She grabbed a thin black pencil and pulled the cap off. I closed my eyes this time and felt her fingers tugging at my skin. She swept the pencil from the inner corner of my eye to the edge. She did it again on the other side and then blew a soft exhale across my lids. “Keep them closed. I’m going to put on eye shadow.”

  I waited for her next move and soon felt a weird brush sweep across my lids. I had no idea which color she’d chosen, but I was eager to see the completely look. Next, I felt a big makeup brush sweep across my cheeks. “Ok. You’re finished.”

  I opened my eyes and looked into the mirror. I was shocked at how feminine I looked now that I had a full face of makeup on. “Wow,” I said. I leaned forward and gently touched my face, exploring the delicate details she had added.

  “I know right?” She was as excited as I was and I felt incredibly happy by it. Then my heart sank.

  “Was that a car I just heard?”

  “Shit! They’re not supposed to be home…”

  “No, no, no!” I cried. I jumped up frantically and ran to the window. The garage door was open and my boss’s truck was parked inside. I saw him walking around the back of it and look up toward me. I stepped back quickly. “Do you think he saw me?”

  “Don’t worry. I’ll get rid of him. Here...jump in my closet really quick.”

  “He’s going to see my car,” I reminded her.

  “Oh yeah.” Her eyes shifted back and forth as she tried to think of a solution. “I’ll tell him you showed up early but I wouldn’t let you in so you went for a walk.”

  “He’s not going to buy that,” I said.

  “It’s our only shot,” she said, looking up at me with a serious expression. I knew she was right and darted in her closet as quickly as I could.

  Seconds later I heard Matt yell up to her. “Scarlet? Is anyone else in here with you? You know my rule about men in the house when I’m not here!”

  “It’s not what it looks like, Daddy!” she shouted from her doorway. I heard his steps stomping up the stairs until he was standing just outside of her room.

  I could see a little bit through the Venetian slits in the closet doors. My heart was racing and despite the fear of getting caught, my cock was still hard. I saw Scarlet back up as her dad walked toward her. He looked around the room curiously.

  “See, Daddy? I was just playing dress up. No one is here. Steve showed up but went for a walk when he realized you guys weren’t home.”

  “Why would he show up this early?”

  “It was my fault, Daddy. I told him the wrong time.”

  He huffed like an angry bear and said, “Well, ok.”

  “You and Mom couldn’t possibly be done grocery shopping already, though.”

  “We aren’t,” he said in a low tone. “Your mother forgot her grocery list.”

  “Of course!” she cried. “That makes total sense.”

  I sa
w Matt step toward the closet, but Scarlet quickly intervened. “You better get going if you want to be back before Steve gets back.” She grabbed his arm and twisted him back toward the door.

  “Yeah, I guess you’re right,” he said. “Don’t let him in until we get back.”

  “You got it, Daddy,” she said. Then she shut her door and locked it behind her. She ran to the closet doors and slid them open. “It’s safe,” she whispered.

  “He’s still here, isn’t he?”

  “Not for long.”

  I stepped out of the closet and we both walked to the window. We stood to the side of the glass to make sure we were out of sight. We watched Matt get back in truck and pull out a minute later. I exhaled the biggest sigh of relief. “I can’t believe we got away with that.”

  “I told you I’d take care of Daddy,” she said with a wink and a smile. She was so beautiful and clever. I was suddenly painfully grateful for my new friendship. She was transforming me into the kind of person I always wanted to be but didn’t think I could be.

  “Now, what is there for a pretty girl like you to do?”

  “I guess I should remove everything and leave until your parents come back.”

  “Oh I’m not letting you leave yet!”

  “What do you have in mind?” I asked. I was confused at what more she wanted from me.

  “You are a girl virgin. You need to get fucked,” she said.

  “What? No, no, no,” I said. “This was fine because we weren’t fucking. I can’t fuck you or I’d be just like the guy they fired.”

  “Oh, you won’t be fucking me. I’ll be fucking you,” she said. Then she walked back to her dresser and dug through the piles of panties. She slowly pulled out a long, silicon dildo and turned back to me. She waved it in my face playfully.

  “What are you going to do to me?”

  “I’m going to fuck you like the little slut you are,” she teased. “Now, open your mouth.”

  I kneeled on the floor and relaxed my lower jaw so that my mouth opened. She traced my lips with the head of the dildo and then shoved it in. I could see myself in the full length mirror. I looked just like a little slut sucking a big, hard cock. I jumped into the role easily and started bobbing my head back and forth along the shaft.