Man to Woman

by Jane Futa

  Part of me felt a little threatened and another part of me felt exhilarated. It was obvious from the moment he lifted his eyes to me that he desired me sexually. He invited me to sit down at his desk, and as I walked toward it, I felt like I was walking into a completely new life as a completely new person.

  I handed him a fake resume, but he didn’t seem to bother himself with it. Instead, he placed his folded hands under his chin and scanned my body up and down with his eyes. “You’ll do quite nicely,” he said. “I only have one condition.”

  “What?”

  He reached toward a bottom drawer and pulled out a maid uniform. It was tight and revealing, not unlike a Halloween costume, but a little thicker. “All of my maids have to wear this.” I gulped and stared at the outfit. The skirt was only about 5 inches long. The top was a tight, short sleeved jacket covering a black brazier. “So. Do you want the job?”

  I looked toward the door as I tried to think. Outside of that doorway was my old life. But I wasn’t much of a fan of my old life, or my old clothes at this point. I turned back to him and said, “Yes. I’d love it.”

  He slapped the desk and laughed with enthusiasm. “Excellent!” He reached across the mahogany wood and handed me the uniform. “Go ahead. See how it fits.”

  “Here?”

  “Melody. Baby. We’re going to be seeing a lot of each other. After all, you live with me now. So, go on. Better to get it over with now than be awkward with it all later.”

  I gulped again. What if he sees that I’m not a woman? What if he sees my little cock hiding in my mom’s panties? I was absolutely terrified, but I didn’t have a choice.

  I reached for the zipper of the emerald green dress and slid it down slowly. I saw Wyatt lick his lips as he leaned back in his chair. I suddenly felt like I was a stripper or a prostitute, rather than an employee. But despite my nerves, the more skin I showed the more excited I became. My body tingled and my cheeks flushed. I turned my back to him as I slid the dress slowly down my body. I could feel his eyes following the fabric down my back and over my ass until it dropped lifelessly to the floor.

  I looked at him over my shoulder and he was leaning forward on the desk. His eyes were nearly bulging out of his head and his smile was thin and wide. “Go on,” he said. “Spin around for me.”

  It was the moment of truth. I was about to spin around and be completely found out as a fraud, or be desired even more. I took a step slowly to the side and shifted my hips until the entire front of my body faced him. My eyes were closed tightly as I waited for his horrified reaction.

  “Mmm, baby. Don’t be scared,” he said. I slowly lifted one eyelid and saw that he wasn’t upset in the slightest. He was actually licking his lips again and scanning my body. I looked down at my panties and saw that my cock wasn’t noticeable. I breathed a sigh of relief and reached around my back to unhooked the bustier I was wearing. Then I slowly dropped it to the floor and watched again for Wyatt’s reaction.

  “It’s ok, baby. I like titties of all shapes and sizes.” I blushed and reached for the maid uniform. “Hang on there, sweetie,” he said. “Why don’t you run your hands over them for me first.”

  “Over what?”

  “Don’t play coy with me. Over your cute little tits.” My cock hardened and my legs quivered. I reached my hands up for my chest and let them glide over my pecs and nipples. He moaned as I touched myself and it only turned me on more. “That’s real nice, baby. Okay, okay. You can put the uniform on now.”

  I slid the bra out from the jacket and fastened it. Then I stepped into the tiny skirt which barely covered my ass. Then I slid my arms through the jacket and fastened the single button attached to it which landed just under the bra.

  “It fits you perfectly,” he said.

  “Thank you.”

  “Now. On to your first chore. See that duster across the room?” He pointed to the opposite wall. I nodded when I saw it and listened for further instructions. “Start by dusting the shelves in here. I’d love to have a pretty little distraction in here while I work.”

  I nodded and felt my body quiver again. The thought of him watching my ass poking out of this tiny skirt as I dusted his shelves was almost more than I could handle. I walked over to the duster and began flicking my wrist with it in my hand. I turned over my shoulder every few minutes and I always found Wyatt staring at my ass.

  I moved along the entire bottom shelf in that room and wondered how I would reach the others. That’s when I noticed a long, rolling ladder propped up in one corner of the office. From up there, he’ll definitely be able to see my ass under this tiny little skirt. I smiled at the thought and started to climb.

  When I looked over again, Wyatt was surprisingly invested in his paperwork and I couldn’t help but feel a tinge of disappointment. Eventually, he even left the room, and I didn’t see him again until that night when I was falling asleep in my new bed.

  Chapter 6

  The room I was given was larger than I expected and full of expensive furniture. The closet was filled with sexy little outfits. I called my mom before going to bed to let her know I had the job and would be living there from now on. I heard a hint of sadness in her voice, but she told me how proud she was of me and that my room would always be available if I came back to her.

  It felt strange to call her from the room of that big mansion. It was the merging of two lives and two people that didn’t seem to fit into one person. I hung up the phone, found a nightie in the closet, and crawled into bed. As I started to fall asleep, I couldn’t help but think about Wyatt and the way he looked at me. My body tingled like it had earlier and I could almost sense someone watching me at that very moment. I shook it off and closed my eyes again, trying desperately to get some sleep.

  A shot of adrenaline raced through me and my eyes opened wide. I heard a soft creaking coming from inside my room and the sound of short little pants. Someone was inside, breathing quickly. I tried not to make any sudden movements. Instead, I lay quietly and listen. The breathing sounded sexual. I listened harder.

  “Oh yeah,” someone mumbled under their breath. “That’s a good little slut.” I was certain it was Wyatt’s voice, and he sounded like he was rubbing something furiously.

  I couldn’t help myself. I rolled over and came face to face with his huge cock. He was standing beside my bed stroking it to the sight of me in one of his little nighties. My eyes widened in disbelief, but my body wanted more.

  He didn’t stop stroking even when I caught him. It almost seemed to turn him on more. I stared up at him while he stared down at me, his cock inches from my face. I moved closer to it, and when he didn’t pull away, I opened my mouth.

  “Ohhh,” he moaned as I wrapped my lips around his bulging head. He dropped his hands and let me devour him. I wasn’t really sure what I was doing, since I was a virgin, but I knew how I liked my cock touched so I mimicked that with him. I slid my tongue along the underside of his shaft and tried to swallow as much as his thick cock as I could.

  “Yeah. That’s my good little slut,” he said louder. He leaned his head back and closed his eyes. I reached around to his firm ass and pulled his hips toward me. I forced his cock down my throat and tried to keep from gagging. The further down it slid, the more my eyes bulged out of my head, and I felt a few tears stream down my cheeks from the pain.

  But I absolutely loved it. I was a dirty little slut to this rich billionaire. He hired me because he thought I was a sexy little girl and he wanted to have his way with me. I slid my mouth up and down his cock and felt it pulsing against my tongue. My own tiny little dick was growing hard and my legs shook with anticipation.

  Wyatt lowered his head back down and gazed at me. He ran a hand through my hair and held my head to his cock. Then he started rocking his hips back and forth, thrusting his head forcefully toward the back of my throat. Once he’d seen how much I could take, he bravely pushed his limits with my mouth. I felt my jaw stretching and my throat widening to ac
commodate him. It felt so fucking good to have his cock thrust in and out of me. It felt so good to be dominated like a little teen girl.

  Before I knew it, my little dick was cumming inside of my nightie. Fortunately, it was dark, and Wyatt had no idea what I was hiding. I felt his legs tense and his bulbous head grow, stretching my throat wider. Then he grunted and shot his load into my mouth. His cum was pungent and salty. I swallowed every drop of his large, white pool.

  When he was finished, he pulled his cock from my mouth and stroked my cheek. “Let me see that cute little pussy of yours,” he said. My heart beat faster. I don’t have a little pussy.

  I shook my head, but I was nervous. All I wanted was to please him, but I wasn’t who he thought I was. He looked confused and frustrated. He leaned into me on the bed and kissed my lips. He smelled like his mahogany desk and his old books. His tongue slid into my mouth and circled around mine. His hands caressed my small tits and lowered toward my waist. The adrenaline started to race again. I couldn’t stop him. I didn’t want to stop him. But he was going to find out my little secret.

  His hand slid under the covers and down my thigh. He reached the bottom of my nightie and lifted it slowly. Then he pulled away from our kiss to get a look at the pussy I didn’t have. I watched his face change from excitement to surprise as he lifted the fabric to my waist.

  “What the-“ he started when he caught sight of my tiny dick. I leaned back on my elbows, waiting to be punished or thrown out, but he just stared.

  “I’m sorry,” I said, suddenly worried about my new job. I remembered what my mom told me about keeping my room available. I knew I wouldn’t be out on the streets, but if I had to go back home, I wouldn’t be any closer to Theresa.

  Wyatt’s thoughts were spinning and processing what he was looking at. Then he reached down and brushed his knuckles against my dick.

  “Ohh,” I moaned. He kissed me again, plunging his tongue deep into my mouth. He grabbed my hips and pulled me into him. Then he pulled away quickly and flipped me onto my stomach.

  “Looks like I’ll need a different hole then,” he said. My face was pressed into the covers and he lifted my nightie up over my ass. He spanked it and spread my cheeks wide.

  Oh my god, oh my god. I’m about to get my little asshole fucked for the first time. My head was spinning. I never thought I’d have a cock in my ass, and I couldn’t decide how I felt about the idea. But there was no time to figure it out. There was no time to protest. Wyatt was already spitting on it and his cock, preparing to thrust it in.

  And when he did, when I felt the head of his cock split my hole wide open, I loved every painful and pleasurable sensation that swept through my body. He thrust it deep inside me and I gripped the sheets and moaned. He huffed and grunted over me. He reached for my wrists and held them while he fucked me. I was his little slut, and I was getting what I deserved.

  He thrust in and out of me, pounding his hips against my ass. His balls swung against mine and I felt my cock harden again. He moved faster and deeper until we were both cumming together on the bed.

  When he was finished, he collapsed and gave me a kiss. Then he pulled his cock out and said goodnight. He left the room and he left me on the bed with my bare ass still exposed and his cum dripping down my thigh.

  Chapter 7

  The next day, I put on my little maid uniform from the day before and fixed my makeup and hair. I had a big smile on my face as I headed downstairs to do my chores and please Wyatt. I couldn’t wait to have his eyes scanning me up and down again and to feel his cock that night in my throat and ass. When I went after this job, I had no idea how much I would end up enjoying it. It even provided a distraction from trying to find Theresa. But the distraction didn’t last long.

  “Hello, Wyatt,” I said, peeking my head into his office.

  “Melody! Just the girl I wanted to see.” I stepped in, already preparing myself to get fucked when I noticed a new girl sitting at Wyatt’s desk.

  “What’s going on?” I asked, trying not to sound threatened.

  “Melody, this is Justine. She’s going to be replacing you.”

  “What?” My heart sunk. Had I disappointed him? Was he done with me now that he came in me?

  “Don’t take it personally, but I had very specific requirements for who I hired. And as we both know,” he said, lowering his eyes toward my groin, “you don’t meet them.”

  “But I thought-“

  “Look. I had fun with you yesterday and you did a really great job. But you just aren’t right for a full time position here.”

  Tears fell down my cheeks. Before he could say another insulting word to me, I ran upstairs to grab my things and quickly fled the mansion. I didn’t even bother changing out of the slutty maid uniform.

  Once I was in my car, I peeled out of the driveway and parked down the street so that I could burst into tears. I should’ve known better than to get my hopes up. When my eyes finally dried, I started my car and left Wyatt’s neighborhood. I knew the only thing left to do was to go home, but I had one more stop along the way.

  I pulled up slowly outside Theresa’s house, gazing upon it in awe and envy. I couldn’t believe the fabulous Theresa was inside, and she didn’t even know who I was.

  One of the gardeners noticed me watching and I ducked my head. He came up to my car window and tapped on the glass. Shit, I thought. I rolled down my window and waited for him to lash out at me.

  “Good, you’re finally here,” he said. “Maids pull around back, here’s the gate code.” He handed me a slip of paper and waved me on. I couldn’t believe it. He just gave me a full access pass to Theresa’s house.

  I followed his instructions and pulled around back and parked near the other cars. She had a mini parking lot full of workers’ vehicles on a large cement driveway. I walked up to the back of the house almost completely oblivious to the fact that I was still wearing a very revealing maid’s uniform.

  I opened the back door and saw a house few other maids cleaning various rooms. One of them spotted me from the kitchen.

  “What on earth are you wearing? Are you trying to get fired?” she asked as she looked me up and down.

  “Oh…um…sorry.” I was flustered but she quickly dropped the questions and gave me instructions.

  “My name is Maria,” she said.

  “Melody.”

  She shrugged her shoulders and continued cleaning the kitchen. My task was to straighten the bedroom. I walked to the front of the house were a spiral staircase circled the foyer and I started to climb. I followed Maria’s directions to the bedroom and when I entered, I realized it was Theresa’s bedroom. I recognized it from her videos.

  “No fucking way!” I cried. I quickly threw myself on the bed and rolled around in her sheets. They smelled of pine and cinder with a hint of vanilla. I could’ve lay there all day, but I wasn’t willing to take this new opportunity for granted. I was given another maid job, even if by accident, and I intended to keep this one.

  I still wasn’t really sure how to be a maid, or what to clean first, so I did the best I could. I’d always watched my mom clean the house and it never looked that hard. I started by making the bed and putting the laundry away that sat in a basket on the floor.

  I started with the delicates which lay on top. I pulled out the top dresser drawer by instinct and started to slide them in. That’s when I felt it. A long, thick, silicon toy. I pulled it out and saw that it was shaped like a large cock with veins and ridges. My mind flashed back to the night before. My ass was still tingling from being stretched so wide.

  I licked my lips as I looked at it and then I held it to my nose. It didn’t smell like Wyatt or his cum, but instead had a distinctly pleasant odor. I stuck out my tongue slowly and licked along the shaft. My cock hardened. I was in a trance. I practically forgot what I was supposed to be doing. All I wanted to do was suck this long, pussy drenched, dildo.

  I knew I had to be alone with it so I wouldn’t get ca
ught. I looked around the room and spotted a large walk-in closet. I remembered what had happened at home with my mom and decided against it. Then I saw the master bathroom. Of course! Certainly the help is allowed to use the bathrooms. I ran inside and locked the door.

  I looked at myself in the mirror in the maid uniform. I was sexy from head to toe. I couldn’t believe I had let Wyatt’s rejection affect me so negatively. He didn’t know what he was missing. I parted my lips and watched the dildo slide deep into my mouth.

  My cock hardened again, but I couldn’t see it through my uniform. In my reflection, I was a full woman sucking on a hard cock. I closed my eyes and slid it in and out of my mouth.

  I heard a knocking on the door. “Hello?” I heard a young woman’s voice that sounded strangely familiar. I opened my eyes in a panic. It’s Theresa.

  “I’m just using the bathroom,” I defended as I searched for a place to hide the dildo.

  “Maids aren’t allowed to use the master bath. Didn’t anyone tell you?” I heard her scold from the other side of the door.

  “Just a minute!” I shouted, my heart beating faster. And then I froze. There was a key wiggling into the lock on the outside of the door. “Just a minute!” I cried again in desperation.

  But the door swung open and there stood Theresa with her mouth hanging open. I was crouched down in my skimpy maid uniform holding her dildo in my hand.

  Chapter 8

  Theresa was as beautiful as ever. Her green eyes sparkled in the sunlight and her long brown hair fell perfectly around her shoulders. And her breasts were even better in person than on camera. Despite the compromising situation I was in, my eyes traveled her delicious curves. She wore a sheer white sundress and I could almost make out where her nipples were through it.