Man to Woman

by Jane Futa

  And maybe get a drink. I chuckled to myself and walked to the nearest available bar stool. The bar was no less elegant than the main lobby though its gold was muted by deep reds. Crystal and dark wood accented the walls beautifully. I ordered a drink and leaned forward on my elbows.

  I looked around, trying to guess how many others were here for important meetings. Everyone else seemed to only be here for pleasure, though. I shrugged it off and checked my phone for the time. There was still ten minutes until the meeting, but I was still surprised Cecilia didn’t try to show up early.

  She’s an important and busy woman, I reminded myself, still hopeful that she was going to tell me I got the role. Suddenly, I heard a familiar clicking sound coming from behind me.

  I turned around in my barstool and came face to face with the gorgeous Cecilia. From this distance I could see that her eyes were hazel, but no less intense.

  “Kevin,” she said with a strong voice. She extended her hand and I eagerly shook it. “You didn’t save me a seat?”

  Both seats next to me were filled and I stuttered trying to explain.

  “It’s okay. I’m only teasing you,” she said. “Let’s move to that small table back there.” I jumped from my stool, grabbed my drink, and followed her to the table she had pointed out.

  I watched her perfect ass sway in the same pencil skirt she was wearing earlier. Her heels clicked delicately against the hardwood floor and I found myself admiring their shape and color. I had noticed they were red before, but in the dark it was hard to pick up on the subtle pink shade that tried to pop through.

  Focus, I scolded myself. The last thing I needed to be thinking about was how stylish her shoes were…or so I thought.

  Cecilia and I sat across from each other. I had my drink but she refused to explain the meeting until she’d ordered hers. “So, are you from LA?” she asked me with one raised eyebrow.

  “No,” I admitted sadly. “But I’ve lived here for a few years.”

  “I could guess you weren’t from here. There’s something very unique about you.” She lifted her hands to her face and rested her chin on them.

  “Thank you,” I replied, hoping she meant that as a compliment.

  “It’s so nice to see fresh faces in a sea of plastic surgery,” she said. She did mean it as a compliment then, I thought. I felt giddy as a schoolboy but tried to maintain my cool, professional composure.

  I nodded in response so I wouldn’t put my foot in my mouth. She looked absolutely regal sitting across from me. Her dark hair curved perfectly around her face, accentuating her strong jawline. Her lips were full and seductive. If I wasn’t hoping she’d be my new boss I might have even considered hitting on her.

  Her blouse was lightly open at the top, showcasing the smallest hint of cleavage. I noticed, but never let my eyes linger for more than a moment before redirecting my gaze. The last thing I needed was her to notice me ogling her chest.

  I wanted desperately to know the intentions of our meeting, but I wasn’t brave enough yet to ask. Instead, I allowed her to make the necessary small talk. In any case, I knew networking with her like this could be a good boost for my career. Just don’t say anything stupid, I reminded myself.

  “You don’t talk very much, do you?” she asked me.

  “I can be talkative,” I said defensively. “I try to save it for appropriate moments.”

  “Well,” she said, leaning back in her seat, “it’s nice to be around someone who’s not begging me for a role, but I am desperate to learn more about you.”

  “Really?” I asked, raising an eyebrow in utter confusion.

  “Mmhmm,” she said in a sexy moan with her lips pressed together.

  “Where do I start?” I spread my arms out to the side with my palms facing up as I wondered what to tell her first. I lifted my eyes to the ceiling as I thought about how my entire life had been anticipating this very moment.

  “When did you know you wanted to act?” she asked me.

  “Ever since I first understood the concept,” I said excitedly. “Next question?”

  “Hang on a second,” she said, leaning forward again. “Let’s set some rules here. Rule 1: I lead the discussion and you follow what I say.”

  “Yes, of course,” I agreed, nodding my head. I tried not to scold myself for trying to lead the conversation. Instead, I focused on the next thing she wanted of me.

  “Good,” she said, pleased by my quick compliance. “Where are you from?”

  “The Midwest,” I told her.

  “How did you manage to get out here? How do you afford the high rent?”

  I eyed her suspiciously. What did these questions have to do with anything? Is she trying to pick apart my character before making a decision on the role? I shrugged it off as best as I could and continued.

  “I saved up every penny through my childhood and teenage years. Like I said, I’ve known this was what I wanted for a while. Then, when I was 18, I left home to try my hand out here. My mom was crushed and my dad was pissed, but this is what I wanted.”

  “Go on,” she said, flicking her wrist delicately toward me.

  “So I had some savings and traveled by car. I still have some savings left, but I work two jobs and try to work auditions around that. To say I was lucky to make it today is an understatement.”

  “Very impressive,” she said. Then the strangest thing happened. I noticed her biting her bottom lip as if she was aroused by my story. That can’t be, I told myself. But then, she started to shift in her seat as if she were uncomfortable.

  “Is everything okay?” I asked her.

  “It’s more than okay. I have one more question for you.”

  “Shoot.”

  “This role may require you wearing women’s clothing in a scene or two. How far are you willing to go to get this role? Would this be a consideration for you?”

  “I admit I don’t know too much about the script, but my character doesn’t seem like the type who’ll end up cross-dressing…”

  “Oh it’s for a frat prank early in the film. It’s just for fun,” she said.

  I thought hard about wearing women’s clothes. Of course I knew I’d do anything for a role like this. Then my mind flipped through all the actors before me who’d dressed as a woman the entire film. I knew it couldn’t be that big of a deal. “Sure,” I said finally. “No problem.”

  She leaned back in her chair again and surveyed me. “Excellent,” she said, folding her arms across her chest.

  “Does this mean you’re considering me for the part?” I asked.

  “What did I say about me leading the discussion?”

  I hung my head and looked down at my lap. “Sorry,” I said. Don’t screw yourself over, Kevin. Do anything Cecilia asks and you may just find the fame you’ve always wanted.

  “It’s alright, for now,” she said. Her tone worried me a little. “Anyway…I am considering you for the role.” She eyed me curiously.

  My heart leapt in eager anticipation. If that was true, I knew I’d do anything to secure the spot. I just had no idea how strange my night was about to get.

  “I know how badly you want this,” she started, leaning in close to me. She brought her hand up to her face and brushed the renegade strands from her eyes.

  “I do,” I whispered with a lump in my tightened throat. “More than anything.” I knew I probably shouldn’t have admitted that last part to her, but I was desperate.

  She dug through her purse and then laid a flattened hand on the table, sliding it toward me. When she removed her hand I saw a white card key. I looked at her suspiciously.

  “That’s the key to my room,” she said. “We can’t be seen going up together, but meet me there 15 minutes after I leave here.”

  “I don’t understand,” I admitted ashamedly.

  “You will soon,” she said. Then she grabbed her purse and stood up from her seat. She rested a hand on my shoulder and then gave it a squeeze before turning on her heel an
d strutting her sexy body out of the bar.

  After she had left my sight, I looked down at the key card. I picked it up quickly and tucked it in my pants pocket.

  I took one last innocent look around the busy bar as I wondered what I was in for and trying to prepare myself for anything. I had always known the film industry wasn’t the most shining example of morality, but I wanted in anyway. I mean, who wouldn’t want to be the next big celebrity?

  I checked my phone and when 15 minutes had passed, I made my grand exit. My senses became alive as I headed toward my new mystery. I couldn’t begin to imagine what I would reveal when I reached Cecilia’s room, and I didn’t dare try.

  I stepped onto the elevator alone. The walls of the small box were lined with mirrors. I adjusted my hair and clothes so that I’d be as presentable to Cecilia as I was in the bar. Then I heard a ding and my breath stuck in my throat. I stepped out and followed the signs to her room number.

  The halls were maroon and gold, with a fleur-de-lis pattern on the floor. The gold trim sparkled and I imagined I was on my first red carpet. The fame was so close I could taste it. I lifted my chin and charged to Cecilia’s door. I exhaled the breath I had been holding and knocked.

  I listened for her heels, the clicking sound muted by the carpet. I heard a hand rest on the knob from the other side. I imagined she was looking through the peephole to make sure it was me. The knob started to turn and then there was Cecilia in a transparent black negligee.

  “Welcome,” she said, stepping to the side and allowing me to slide in through the crack of the door. When I’d heard it shut, I turned around to face her.

  “You did say 15 minutes, right?” I was worried I’d disturbed her. Was the negligee for me? But I’d had no idea.

  She laughed. “Yes, you’re right on time,” she said. I had an idea of where this was going, so I sat on the edge of the bed. She walked toward me and leaned over me. She rested her hands on my shoulders and moved in for a kiss. Her short hair draped around us like a private curtain and her dancing tongue was the show.

  Her hands slowly slid in toward my neck and I put my hands on her waist, hoping I wasn’t being too forward. Then I laughed at myself. If anyone was forward here, it wasn’t me.

  With her tongue down my throat, Cecilia slipped on knee on the bed beside me. She pushed against it and climbed onto my lap, placing her other knee next to me. I grabbed her ass to keep her steady and she pushed her body against me. I lay down with her above me, tongues flicking wildly.

  She pushed her breasts against my chest and moaned into our kiss. I felt my cock harden and begin to rise. Was I really about to have sex with the producer? Did I really think this would secure me a role? Conflicting thoughts and emotions raced through me. What was I doing here? But I knew very well what I was doing…everything that could be done to land me that role.

  She pulled her mouth from mine and stared into my eyes. She was beautiful as she bit her pouty lower lip. After all that kissing, there was no smudge to her makeup and it almost made me wonder if she was just naturally that gorgeous.

  “What is it?” I asked her, sensing she wanted to talk about something.

  “I have a request for you.” She was trying to play the nervous vixen but I saw through that. She was the dominating type, all the way, and this was her way of taking control.

  “Anything,” I said, my eyes darting quickly across her face, searching for the slightest change in her expression for a hint of what she wanted me to do.

  She climbed off of me, sitting on her knees beside me on the bed. I raised myself up on my elbows as I waited for her request.

  “See that changing screen over there?” I nodded. “I have a few…outfits.”

  “You want to model them for me?” I asked.

  She laughed. “Not exactly. I want you to model them.”

  I was surprised that she had a few male outfits lying around but if she wanted a fashion show, who was I to complain?

  “You said you were alright with wearing women’s clothing, right?”

  I could feel my jaw drop but I tried to pick it up quickly before she could tell. I had thought she meant for the role…not for the bedroom. My heart raced as I tried to decide what to do. I couldn’t leave without risking losing the role, but wearing women’s clothing? And what kind of clothing? I wondered.

  “I did say that,” I replied as slyly as I could.

  “Great,” she said, clasping her hands together and flashing me a bright smile. “Behind the screen, I have three outfits laid out on a small table. You should be able to figure it out pretty easily.”

  I swallowed hard. Was I really about to cross dress for the first time in front of my potential new producer? And at her demand, no less. I knew there wasn’t much time to think, unless I wanted to give the impression that I wasn’t interested. Even if the cross dressing was strange, if it led to getting to sleep with Cecilia, I was game.

  To kill a few minutes, I figured I’d give Cecilia a little strip tease. Maybe if she saw me naked she wouldn’t want to ruin it with a few ladies’ outfits. I stood by the bed, facing her, and slowly unbuttoned my shirt.

  “Woo!” she cried when she realized what I was up to. I unfastened the first button, then the second, moving all the way down until my entire torso was visible. I slid the shirt from my shoulders and then swung it above my head like a lasso. After a few spins I tossed it in her direction and she reached up and caught it in her delicate hands.

  I unzipped my pants and slid them off as gracefully as I could, kicking them to the side with my shoes. Since I was wearing briefs under them, there was no hiding my hard-on from Cecilia. I caught her staring right at it with a raised eyebrow.

  “I can’t wait to see that thing in some ladies’ panties,” she said, sending a strange chill down my spine. Something about the way she desired to see me cross dress made me feel sexy, but it was a completely new thrill to me at the same time. I was filled with hesitation and desire and I wasn’t sure which to act on. “Don’t remove those just yet,” she told me when my hands moved to the waistband of my briefs.

  “Ok,” I said, standing awkwardly. I waited for her next direction.

  She waved her hand, flicking it at the wrist and said, “Go on to the screen, now. Try on your first outfit.” I turned around and headed slowly behind the screen, worried about what I would find.

  When I finally reached the hidden table, I saw the three outfits. One was a simple red silk bra and pantie set with a pair of black stilettos next to them. The next was a black see through negligee, similar to the one Cecilia wore, but with a pink trim. The last outfit was a completely white lace lingerie set, complete with stockings and a garter belt. I had no idea how to even use a garter belt, so I decided to start with the simplest: the red bra and panty set.

  I exhaled and slowly dropped my briefs to the floor, kicking them to the side. I heard Cecilia moan when she saw my briefs slide out from behind the screen. I wondered if she could see the outline of me changing or not. I ran my hand across the red silk fabric to get acquainted with it. It felt smooth and cool against my skin, and knowing Cecilia was waiting for me got my dick hard.

  I picked up the panties and held them up in front of me. Here goes nothing, I thought as I lowered them to the floor to step into them. The feeling of sliding that cool silk up my long legs was incredible. It was luxurious and forbidden, and my cock hardened more.

  Then I felt ecstasy as the red silk grazed against my cock and balls. I secured the waistband around my torso and let out a quiet moan as it hugged my rock hard dick. I reached down and traced the outline of my cock through the panties, pressing the silky fabric against my skin.

  Fuck this feels good, I thought to myself. I couldn’t believe how good it felt. It was cool and soft, and something about pressing the fabric to my cock gave it a completely new sensation. I felt sexy and pretty, and I liked it.

  I heard Cecilia clear her throat from the other side of the screen and remember
ed that I was doing this for her. I turned around and picked up the bra, sliding my arm inside each strap and placing the straps on my shoulders. I had never fastened or unfastened a bra from this perspective, so it took me a few minutes to figure it out. Eventually I pulled the clasp around to the front of me to get my fingers in the right position and then hooked it in back.

  I moaned as the silk caressed my chest, and I loved the feeling of cool fabric against my nipples. I ran my hands up and down my body, over the sensual fabric. I was having the time of my life, but the thought of exposing myself like this to another human being was frightening. What if I was absolutely humiliated? My heart began to race as I put the black stilettos on. They were a size or two too small but I made them work.

  Suddenly, I felt completely transformed. I couldn’t have felt more like a woman than if I had a pussy and two breasts. I let out a long exhale and slowly stepped out from behind the screen, one leg at a time. I heard Cecilia whistle when I revealed my first long leg and stiletto heel. Then, I revealed my whole body to her, despite my heart pounding in my chest.

  “Mmmm,” moaned Cecilia, rubbing her hand along her neck. “You like being my bitch?” she asked. I was thrown off by the harshness of her question, but I was enjoying the game. I nodded in reply. I kept my head down low from embarrassment, but my cock was harder than ever.

  “Mmmm,” she moaned again. “Look at the outline of your cock in that beautiful silk. Does it feel good against your dick?”

  Again, I nodded.

  “Good boy,” she said. Then she patted the area next to her on the bed and I walked over to her. “Crawl on your hands and knees,” she told me. I leaned my hands on the edge of the mattress and then crawled next to her. When I had both hands and knees on the bed I felt her hand whack against my ass. It was a rough spank but it turned me on like nothing else.

  “Fuck!” I cried from the sting.

  “You like being a little sissy?”

  “Yes,” I said.

  “Yes, ma’am,” she corrected.

  “Yes ma’am,” I replied.