Man to Woman

by Jane Futa

  Is this really turning me on? I couldn’t believe it, but it was. I was wearing something forbidden and alien to my body. It heightened every nerve ending in my body. And this was one piece of fabric. There were more pieces to come. I exhaled again, this time a small moan following it.

  Fuck it, I said. Then I reached for a bra. It didn’t quite match, so I dug around in the pile. My fingers sank into ripples of silk and satin. I felt like I could dive in and be swallowed by the softness. I closed my eyes for a moment as I let my hands wander.

  A few moments later I found a bra that matched. It was black with lace attached to the cups. Fortunately, my ex had a small chest, so the bra would look convincing on a man. I slid the straps up my arms and clasped it behind me.

  Then I felt a transformation. As the cups hugged my pecs and the panties wrapped around my cock, I couldn’t help but feel feminine. I’d never been a muscly manly man, but I’d never really felt feminine either. Now it couldn’t be helped. I suddenly wanted to be bent over the bed and fucked from behind. It was as if the delicate fabric held some sort of magic power over me. It turned me into a seductive slut who just wanted to be taken advantage of.

  Woah. This isn’t what this is about. I tried to get ahold of myself and move onto the next essential piece. I found a dress that wasn’t too revealing but was still sexy enough. It was black and tight and perfect for an interview.

  Shit, the interview. I knew I had to get my feminine alternate personality hired. My sister, I thought. I’ll say she’s my sister. That would at least get her pushed up on the line. A name. I need a name.

  As I deliberated about the name, I slid the dress over my torso and down my hips. It hugged tighter than anything I’d ever worn before, and I felt magnificent in it. I suddenly wished I had long, flowing hair that I could flip behind my shoulders.

  Tanya. Her name will be Tanya.

  I zipped up the back of the dress and smoothed the fabric over my body. I looked down and my head started to spin. I saw a pair of women’s hips and legs jutting out from a black dress. Is this really my body? It was like being transported somewhere else. I felt like I might faint.

  I sat on the bed to maintain my composure. I looked down again, this time at my chest. The padding from the bra pushed my chest out an inch or two. I ran my hands over my breasts and my fingertips went numb. I couldn’t decide if I was feeling my own body or not. I was disoriented and lost, but my cock started throbbing. It was the only sign that I was still a man under all those delicate layers.

  This is insane, I thought. Yet, I wasn’t ready to take it off. Instead, I lay back on my bed and focused on the soft fabrics that caressed me.

  I placed my hands on my chest and slowly slid them down my torso. They roamed over my hips and to the tops of my thighs. My palms grasped the hem of the dress as it pressed against my thigh. I moaned with both surprise and ecstasy. It felt as if I were rubbing a woman’s legs. I pulled the dress up slightly and slipped a hand between my thighs. Chills crept up my spine like someone was dragging a feather along my back.

  I turned my head to the side and gasped when my fingers found the black panties. First, they touched my balls, pushing the soft fabric lightly into the skin. I bit my lower lip and let my fingers trail up the length of my shaft which was stiff already.

  I let my other hand caress my neck and my chest. I imagined there were small breasts under the bra. It was as if I’d stepped out of my body for a moment and was groping another’s. I was a woman and also touching a woman. It sent my head spiraling. I became lost in a frenzy that was seemingly alien.

  I caressed my cock more, only over the panty fabric. I imagined myself as a man, flipping over myself as a woman, and fucking her from behind. As I watched myself pound the creature I’d become, I stroked my cock up and down.

  The unthinkable nature of the situation made it that much more erotic. It only took a few minutes before I was shooting cum across my stomach, soiling the perfect dress.

  It’ll wash out, I told myself, completely unabashed by what had just happened. I released a long breath as my head returned to earth and back into my body.

  These clothes turn me into someone else. What surprised me was how much I enjoyed being someone else, even if it was a different gender.

  Chapter 3

  I went to my boss and told him about my “sister.” Fortunately, he said that he was hiring and set up an interview with her. I still wasn’t sure I could go through with it, but I figured it wouldn’t hurt to get the ball rolling. Each day of work that led up to the interview, Cindy brought in more and more money. It was starting to get hard to not dress up like a woman for better tips.

  But what if he recognizes me? I knew it was a risk. He could fire me for it and then I’d be worse off than before. Just be as convincing as possible, I told myself. I spent the next week trying to psych myself up for the interview.

  I cleaned the black dress and laid out all the items for the interview. I’d even bought a few simple makeup items and a wig to really make it convincing. I wasn’t sure it would work, but I was willing to try.

  I dressed myself for the interview and then headed to the restaurant. My nerves were on end. I had bright red lipstick on and fake eyelashes. I hoped between that and the wig my face wouldn’t be recognizable, and I was lucky I had such a feminine face to begin with.

  I walked into the restaurant, shaking my hands at my side to try and rid my body of the adrenaline. Cindy was the first person I saw.

  “I’m here for an interview,” I said in a girly, high pitched voice. She spun around and looked at me carefully.

  “Sure, this way,” she said. I followed her to the back room where our boss, Jeff, sat at his desk. Everything was familiar to me, of course, but I tried acting like it was the first time I’d seen any of it.

  “Jeff,” she said. “This is…”

  “Kelsey,” I said.

  “She’s here for the interview.”

  “Oh right. Rob’s sister?” he asked. I nodded shyly like I’d seen most women do. “Come in.” Just then, Cindy left and shut the door behind her. I sat down by Jeff’s desk and crossed my legs. I tried to keep my penis hidden as much as possible and so far it seemed successful.

  I noticed Jeff’s eyes staring at me differently than when I was Rob. They slid from head to toe, taking in my whole body. At first I worried that he was trying to decide if I was really a woman, but I soon realized that he did believe I was a woman. He was just treating me differently because of it.

  He leaned forward on one elbow. His royal blue eyes stared into me with a look I’d never seen. It must’ve been a bit of lust, but even lustful women didn’t have that kind of fire in their eyes. It was powerful and dominating. Like I’d just been spotted by a wolf. His dirty blonde hair fell over his forehead and I almost thought he might attack me. Instead, he clenched his teeth and breathed heavily through his nostrils. Then, as if catching himself, he straightened his back and broke our gaze.

  “So. Do you have any waitressing experience?”

  “Some,” I said lightly.

  “What hours are you available for?”

  “Any.”

  “Good,” he said in a seductive voice. “Very good.”

  I started realized how slimy Jeff was. Did he treat all the other girls like this too? Despite feeling bad for them, I enjoyed being objectified by him. My cock wanted to stiffen but I worked hard to keep it under control. He can’t see that I’m really a man.

  There was a long silence. As if Jeff was preparing to ask me something but didn’t quite have the courage. Then, all of a sudden, he jumped from his seat and walked to the door. I heard the click of the lock and then he asked, “How badly do you want this job?”

  His eyes had that fire again and I felt like this was more than your typical interview. He returned to his seat and leaned back. Then he placed his hands behind his head and sighed.

  I stood up and smoothed out my dress. “I’d do anything,” I said,
daringly.

  “Good girl,” he said in a slow exhale. I wasn’t quite sure what I was getting myself into, but his behavior was intriguing me. “Enough to get on your knees and beg?”

  My heart pounded quickly. Did he want me to suck him off? I quickly wondered if Cindy had to go through the same thing in her interview, or if I just seemed like the kind of girl who wouldn’t report him.

  I nodded and watched Jeff turn his chair to the side and spread his legs wide. I slowly walked around the desk, waiting for him to stop me due to miscommunication. He never did, though.

  I walked completely around his desk and then slowly lowered to my knees. He already leaned his head back and sighed as if I was touching him. Even the anticipation of getting a blow job was exciting him.

  I lay my hands on his thighs, again waiting for him to stop me, but to no avail. I slid my hands from his knees up to his waist and found his belt buckle. I slowly unfastened it and started to pull his pants down. He lowered his head and his hands and helped me.

  He lifted his ass out of his chair and slid his pants and boxers to his knees. He had a small gut, but other than that looked pretty well built. When he released his cock, my eyes widened from how big it was. It was already rock hard and throbbing with desire.

  I took his shaft in my hand and licked my lips. “Yeah baby,” he said when he saw my eager expression. “Show me how badly you want this thing.”

  I nodded and then parted my lips. I was close enough that my breath rolled down the length of his shaft and he exhaled. His hands returned to their spot behind his head and I watched him staring at me.

  I lowered my mouth over his bulbous head and he groaned. I couldn’t believe I was so unrecognizable that he believed he was getting sucked off by a woman. And with his dick in my mouth, I felt pretty womanly.

  Once my lips were wrapped completely around the head of his cock, I felt one of his hands behind my head, weaving his fingers through my hair. A wave of panic swept through me when I realized he might pull my wig off. Fortunately, I had secured it enough to hold tight.

  As he pushed on the back of my head, I lowered more of my mouth down his shaft. Eventually, I had the whole thing in my mouth and his head hit the back of my throat. I gagged a little and watched him tense at the sight.

  “Fuck yeah,” he said with wild, rage filled eyes. He held my head down for a moment and then pulled his hips back so his cock slid mostly out. Then he pushed back in and held it again. He began rocking his hips and fucking my face. I gagged each time he hit the back of my throat, but he didn’t seem to care. He just kept pushing deeper and deeper. I kept my hands on his thigh to brace myself, but there was no escaping his grasp.

  “Oh yeah. That’s a good girl,” he repeated as he thrust in and out of me. He couldn’t see, but my cock stiffened each time he referred to me as a good girl. Despite the discomfort of his forceful grasp, I was enjoying being fucked like a girl.

  He pumped his dick in and out, eventually bringing both his hands to my head to hold it in place. It was as if I was his doll or toy and he could fearlessly have his way with me.

  I felt the head of his cock swell and his eyes rolled in the back of his head. I prepared for his splash of cum but was unprepared for how sensual it would feel as it spilled toward the back of my throat.

  I swallowed as much as I could, but some drops crept toward the corners of my mouth and dripped down my chin.

  His groan was stronger but muffled. He knew people were just outside and might hear us. When he finished cumming, he pulled out slowly and wiped his thumb across my chin. Then he held his cum covered thumb to my mouth. I leaned down and sucked it clean.

  He pet my hair and called me a good girl again. Then he pulled up his pants and turned back around.

  “So…do I have the job?” I asked.

  “Sure do,” he said, suddenly completely disinterested in me. He looked down at the scattered papers on his desk. “You can start tomorrow,” he said.

  I nodded and left the room. On my way out, I passed Cindy and caught her gaze. She suddenly gave me a look of pity and I gathered she understood what went on in our interview. I pitied her in return and then left the restaurant.

  Chapter 4

  The next day I dressed myself for work at the restaurant. “Rob” called in since we had been scheduled similarly. Jeff didn’t seem to mind since Kelsey was coming in to work. I dug through the pink suitcase for something similar to what I wore to the interview. The restaurant had a bit of a dress code, but as long as we stuck to neutral colors we were golden. I found a navy blue dress that flared a little. I figured the flare with the apron would help keep my manhood hidden.

  I added the wig and makeup and returned to the restaurant. On the drive over, I kept thinking about how it felt to give my first blow job. I couldn’t help but chuckle at the fact that Jeff had no idea a man had sucked him off.

  When I walked into the restaurant, Cindy was working again. She was designated to train me which I knew would be easy since I already worked there. I shadowed her throughout the day and got to hear how she approached customers. She didn’t do anything special, so I was more convinced than ever that it was her hot body that made her more money.

  At the end of the day she set me up with my own table to waitress. It was a group of young frat boys who flashed me the same hungry, wolf gaze that Jeff gave me the day before. I flirted with them by batting my eyelashes and twisting my hips anytime I was around their table.

  They called me things like “Honey” and “Sweetie.” They even occasionally cracked jokes about me coming back with them to have a little fun. I couldn’t help but smile at their naivety and hoped they’d leave me a wad of cash.

  When they finally left and I picked up the bill fold, it was full of twenties and one of the guy’s phone numbers. I rushed back to Cindy and showed her.

  “Damn, girl. Good job,” she said as I flashed my cash toward her.

  “Thanks. I guess it’s easier, being a woman and all,” I said, hoping to crack into some secret information with Cindy.

  “There are downsides too,” she said.

  “Like with Jeff?”

  She nodded. Then she turned to look at me and for a moment her expression changed. She almost looked horrified and I wondered if she recognized me. She shook it off and then changed the subject, letting me handle the next few tables on my own.

  When it was time to cash out, I had made almost as much as Cindy in half the time. I couldn’t believe how many people I’d fool, especially men. It was a turn on to have this little secret and be desired the way women were desired.

  Cindy seemed flustered by the amount I’d made, and I tried to console her. “You made out good still, though.”

  “Yeah. But you’re new. I can’t believe you made more than me.”

  I tried to help her shrug it off. “Probably just my lucky day.”

  She looked at me questioningly. Her eyes surveyed my face as if they were looking for something new. Then she opened her mouth again. “Would you like to hang out tonight? Maybe exchange waitressing tips?”

  I looked at her suspiciously but by now her expression was completely open and friendly. I didn’t think it could hurt to hang out with the gorgeous Cindy for a bit after work. “Sounds great,” I said.

  “Alright, follow me to my place when we leave.” I nodded and the rest of us finished closing up the restaurant.

  I followed Cindy as she requested and wondered what I was getting myself into. We pulled up to a dark house with a single street light outside. She stepped out of her car and I couldn’t help but stare at her long, slender legs. Her breasts bounced as she walked toward my car and my cock stiffened.

  “Just in here,” she said through my window after I rolled it down. I stepped out of my car and followed her into her house.

  When we were inside, I heard the click of her heels against the tile in the foyer. She flipped on a light and revealed a very modest living room, with a kitchen to the rig
ht.

  “Do you want a drink?” she asked, already heading to the kitchen.

  “Sure.”

  “Ok. Go ahead and have a seat. I’ll bring us something.”

  I moved toward the couch and took my seat. Soon, Cindy turned the corner to join me, flipping on a lamp on her way in. She set two screwdrivers on the coffee table and sat next to me. She was close enough that I could smell her lilac perfume.

  I looked at her nervously, wondering how much longer I could keep up the charade of being a woman. Little did I know, Cindy was about to call my bluff.

  “You did really well today,” she said, tucking her soft hair behind one ear.

  “Thanks,” I said, picking up my drink and taking a sip.

  “I was really impressed,” she said, resting her hand on my bare thigh. Thank god I shaved, I thought. Then her hand slowly moved up until it was resting just at the hem of my dress.

  “Cindy, I think-“

  “Shhh,” she said, leaning into me. She placed her soft lips on my neck and kissed me gently.

  Holy shit! Cindy is a lesbian! I felt her tongue stretch out past her lips and lick along my neck. My cock stiffened. I wasn’t sure how to put a stop to the situation, but I knew she couldn’t find out I wasn’t really a woman.

  She pulled her lips from my neck and whispered, “Much better than you usually do.”

  “What?” I asked, pulling away from her.

  “Don’t fuck with me,” she said angrily.

  “I don’t-“

  “Rob,” she growled.

  “Fuck.”

  “You really thought I wouldn’t notice?”

  “Cindy, I can explain…”

  “No need. I know you just wanted in on some hot girl cash.”