Man to Woman

by Jane Futa

  But now I realized I’d been wearing the wrong clothes all the time. My body was made to wear dainty, frilly things. And my cock seemed to be enjoying it too.

  I ran my hands up the back of my thighs and over my ass cheeks. Then I gave myself a little spank, admiring the red splotch that formed after.

  I opened my mouth like a woman about to cum and practiced moaning with a higher pitched voice. I spanked myself again and moaned again.

  Then I came all over my new pink panties.

  Chapter 3

  It was finally time for me to go to Lyle’s. Even though I was convinced the panties were a joke, I washed them in time to wear them to the strip club. No one would have to know I was wearing them, and I loved having a little secret.

  I was surprised at how comfortable I was feeling dressed as a woman. I couldn’t help but smile at the thought of fooling a criminal like Lyle. Part of me wondered how it would feel showing up as a delicate, frail thing around Lyle’s big, masculine body. My legs tingled just thinking about it. Is this what women feel next to a big, strong man?

  I pulled up to the strip club in the late afternoon. There was a sign in the window that said, “Girls Wanted.” The parking lot was dusty and tree branches scraped along the roof of the building. The windows were dirty and the afternoon sun only made them look worse.

  I parked the car out of the way and stepped out in my black dress with matching heels. I had to buy the heels on my own since the chief failed to consider footwear. I also bought a matching pink bra to go with my panties. It had a little padding so that my chest would seem more convincing, or at least that’s what I told myself.

  I walked up slowly, careful not to trip or twist my ankle. My legs were freshly shaved and it was difficult to keep my hands from gliding across my smooth skin. I had a small barrette clipped into my hair to make its short length seem more feminine.

  I loved the way the black dress hugged my hips. It shifted when I walked, slowly riding up toward my ass. I loved thinking that someone could get a peek at my ass cheeks if they were staring hard enough. Oh how that would turn on the guys back at the office.

  I imagined them whistling and hollering as I walked past, all the while not knowing that I was a man. My cock hardened so I stopped myself before reaching the strip club door. Calm down. You can’t walk in there with a hard-on.

  I took a long exhale and surveyed the area around me. This place really is a dump. The trash was overflowing and the cracked cement steps smelled like booze. Strip club or not, there was no way this place brought in the money that Lyle claimed it did. It was too obviously a place to launder money, and I was going to bring him down for it.

  When I was finally ready to go inside I pulled open the door, expecting to feel a wave of A/C. Instead, more humid heat brushed my cheeks. I heard loud bass playing toward the back of the club, but there weren’t any strippers dancing yet.

  I saw Lyle drinking from his own bar and flirting with the female bartender. I stumbled forward but no one saw me. I looked around at the empty tables, dust settling at their legs. I moved toward Lyle and waited for him to notice me, but he never did. He either stared long at the counter or moved his gaze to the bartender’s tits. She didn’t seem to notice or care that he was ogling her.

  “Excuse me,” I said, sitting two barstools away from him.

  He turned a lazy gaze toward me and swirled his drink in a circle on the counter. “Yeah?” He cocked one eyebrow at me with angry confusion until he put together that I was a hot woman. Then he relaxed and leaned his elbow on the counter. “How can I help you, ma’am?”

  I stared at his bulging muscles as he tried to keep himself from falling off the stool. His legs were thick as tree trunks and his biceps were terrifyingly large and round.

  “I’m looking for work,” I said in a high pitched voice.

  “Is that so?” he asked.

  “Yes, sir,” I added, hoping to sound more country than I was.

  “Have you ever stripped before?”

  I shook my head.

  “Hmm. A virgin, yeah? Let’s go back to my office then and have a little audition.”

  He stood up too quickly and had to lean back on the counter. I stood up and followed him once he regained his balance. We walked down a short hallway and entered through the only door. He pointed to a chair sitting near his desk and I sat down, making sure to keep my knees together.

  Then I heard him lock the door behind him. My heart started pounding. Does he know I’m a man? A cop? Is he going to kill me? I kept my hand on my purse in case I needed to pull out my gun. Unfortunately, without it on my holster he could kill me before I had the time to draw it.

  I tried to steady my breathing and watched him walk around to his desk. He didn’t sit in his big office chair, though. Instead, he walked between me and the edge of the desk and he leaned against it. He folded his arms across his chest and looked down at me.

  I felt his gaze travel up and down my body. He was picturing me naked and possibly picturing fucking me. My cock stiffened at the thought. What’s wrong with me? I’m not gay. But something about having a guy objectify me like a woman made me really feel like one, and I couldn’t help but enjoy every second of it.

  “You’re hot enough to strip, at least,” he said with a slight slur.

  “Thanks,” I said meekly.

  “What makes you want to take your clothes off, baby?”

  I hadn’t been prepared for this question. “Because it makes me feel free,” I said, hoping it was convincing.

  He laughed suddenly. Shit. I fucked up. “Never heard that one before,” he said. “Usually it’s for the money. Most girls don’t actually like stripping. Sure, some of them come to like it, but that’s not the first reason they get into it.”

  “Well I’ve never done it, but I think I’d like it. The money is a nice plus, too,” I said. I looked up at him through the tops of my eyes and slid my gaze along his torso and to his crotch. I noticed a hard bulge pressing against his jeans. I bit my lower lip as I wondered if I’d caused it.

  “Well I like any girl who likes to strip. So then, why don’t you give me a little lap dance. A little preview of what you’ll be showing my customers?”

  I nodded with uncertainty.

  “Well, stand up,” he said, frustrated that I was still sitting. I stood up quickly and moved to the side. I watched him sit down in the same seat and slap his thighs. I wasn’t sure what I was doing but I thought back to the image of my reflection from the previous night. I used that as inspiration.

  He eyed me intensely and relaxed back in his chair. I rested my arms on my head and started to sway my hips. With each shift of my legs, my skirt rose a little higher. That’s where Lyle’s eyes were: on my thighs.

  His gaze was inches from my crotch and that excited me. I shook my hips in wider motions and then started to spin around.

  “No, no,” he said. “You got to dance on me, not over there.”

  My blood pounded in my ears. I stepped closer to him, watching Lyle lick his lips as I approached. I kept walking until one of my legs slid between his legs and I was straddling him. I shook my hips in front of his face and then he reached out his hands.

  He slid his palms against my thighs and moved them slowly up to my hips. He rested them there while I twisted, his eyes growing hungrier. His hands moved again, this time up to my chest. He grabbed my padded bra and massaged it.

  I leaned my head back and moaned as he caressed me. Then I turned around so my ass was practically in his face. He ran his hands from my back down to my ass and grabbed it.

  “Do customers normally get to touch the strippers?” I asked.

  “No, but I do,” he growled. Then he gave my ass a spank. “There’s also something else I get from new strippers,” he said.

  I stopped dancing and turned my head over my shoulder. “What’s that?”

  “Well, they’re usually dying to suck my big cock,” he said.

  “Is that s
o?”

  “Yeah. So how badly do you want this gig?”

  I turned all the way around and gazed into his wild eyes. Then I slowly dropped to my knees and watched a sly smile cross his face.

  “That’s a good girl,” he said, stroking the back of my head.

  I reached out and unfastened his jeans. He lifted his hips toward me and slid them down over his ass along with his boxers. I watched a near 10 inch cock slap back against his stomach, and he had the biggest balls I’d ever seen.

  “That impresses you, girl?” he asked. I suddenly realized my eyes were as wide as possible and my jaw hung open. I also realized he still didn’t know my name.

  “Don’t you want to know who’s about to suck your dick?” He nodded. “The name’s Tanya,” I said. Then I licked my lips and ran my hands up his thighs.

  I can’t believe I’m doing this, I thought. But I have to right? I can’t get the job if I don’t suck him off, and none of the other cops need to know.

  I wrapped my fingers around his hard shaft and leaned in. Then I slid his head into my mouth.

  “Ohhh,” he groaned, leaning his head back. I sucked my cheeks in and slid further down. Every inch that entered my mouth made him groan again, and my own cock was getting harder and harder by the minute.

  I managed to fit the entire thing in my mouth by sliding the head partly down my throat.

  “Damn, baby,” he said. “No one’s ever tried that before.”

  I could understand why. He was fucking huge. I slid it back out my mouth to catch a breath and then I sucked it in again. I felt his hand on the back of my head pushing me down. He rocked his hips back and forth while I bobbed my head up and down.

  I flicked my tongue along the underside of his shaft and massaged his balls. He groaned and growled like a wild animal. It took everything in me to keep from cumming in his office and revealing my true gender. That was a risk I couldn’t take.

  I slid up and down on his cock faster and faster. He stroked my cheek with his thumb and looked at me with fire in his eyes. I could tell he wanted to fuck me, and that only turned me on even more.

  He pushed in and out of me and occasionally I would gag on his large cock. My own dick was throbbing against my pink panties. Lyle reached a hand down to my chest and massaged my bra again. I moaned with his dick in my mouth.

  “Oh fuck, baby, I’m going to cum!” Then his legs tensed and his cock swelled in my mouth. Soon my throat was filled with his hot white semen and I struggled to swallow every drop.

  I had never tasted anything like it. It was salty and slightly sour. Knowing it was Lyle’s though made it hot. I sucked his cock clean and then stood back up again.

  “So. Do I have the job?”

  “You bet your sweet ass you do. Can you start tonight?”

  I nodded and then left the office. Got you, I thought as I rushed to my car before anyone noticed I had an erection underneath my dress.

  Chapter 4

  Since I was a new stripper, Lyle was kind enough to let me watch and just bus tables for my first few nights. I was relieved since I could try and get information without risking revealing my male genitals on stage. I tried to cozy up to a few of the girls to no avail and I was starting to wonder how I would get any of the proof that I needed for the investigation.

  I brought some dirty glasses up to the bar where Angela was working. “Everyone is giving me the cold shoulder,” I told her.

  “They always do that with a new stripper. They think it cuts in on their tips.”

  “Does it?”

  “Probably,” she said as she wiped a glass clean. “Especially a fine little thing like you,” she added with a wink. I felt my cheeks flushed and was grateful that someone finally opened up to me.

  “I’m honestly surprised this place is still running much less hiring. Doesn’t seem like many people come in here.”

  “Yeah. To be honest it probably won’t be running for very long. He shouldn’t be hiring but the jackass can’t keep from trying to find new meat to fuck for himself.”

  “Oh,” I said with wide eyes, pretending to be ignorant.

  “Oh don’t tell me he didn’t have you suck his cock. Well don’t feel special, we’ve all done it.”

  “Really?”

  “Yeah,” she said with a scowl. “After that he’s good unless he really likes you.”

  “Then what?”

  “Then he wants a fuck, obviously,” she said with a laugh.

  My heart nearly stopped. He can’t try and fuck me. Then he’ll know I have a dick for sure. But part of me was excited by the prospect.

  “Want to know a secret?” asked Angela, sneakily leaning across the bar and shifting her eyes around the room in search of Lyle. When she didn’t see him she resumed. “This place only succeeded because Lyle’s partner was laundering money through it.”

  Bingo!

  “Oh?” I asked, trying to sound dumb but intrigued.

  “Yeah. But when Lyle found out he chased his partner off. So now this place will probably go under. They never did the marketing or hiring they needed because Lyle thought they were making a killing off doing hardly anything. Now he’s just a sad drunk with a failing strip joint. I’ve already applied to a different bar in case this place fails sooner rather than later.”

  I was disappointed. I had my information but Lyle was no longer our guy. I dressed a woman for nothing! Then I thought of sucking off Lyle. I didn’t want to admit that I enjoyed it more than I should have. Maybe it wasn’t for nothing...

  I figured it would be my last night there though. If I was going to impress my precinct, I had to catch the guy responsible and Lyle wasn’t it. I leaned up against the bar lazily, watching one of the strippers dance for an audience of 3.

  Then Lyle stepped out of his office and scolded me. “What do you think you’re doing, Tanya? Get to work!”

  I snapped out of my daze. I was about to tell him I quit when his hard-on caught my eye again. Maybe I could play along for a little longer…

  I continued bussing tables, making sure to bend over seductively as long as Lyle was still out in the main room. I turned my head over my shoulder a few times to see him staring at my ass. This is a bad idea, I told myself. You’re just going to make him want to fuck you and then what?

  I had no idea how right I was.

  “Tanya!” he called. “I’d like to see you in my office for a moment.”

  My feet froze into place. I looked over at Angela who shrugged at me. Her eyes were full of pity. I knew I could leave at any moment and it was a risk to follow Lyle to his office, but my curiosity got the best of me. I slowly followed him down that hallway for the second time.

  When we were in his office again he locked the door like he had before. Shit, shit. “You needed something?” I asked him.

  He walked up behind me and put his hands on my ass. Then he rested his lips to my ear and whispered, “I need a good fucking from your sweet ass.”

  My cock stiffened instantly. I felt Lyle’s hands run up my thighs again, pulling the bottom of my skirt up over my hips. Shit, shit!

  But he didn’t notice anything yet. Instead, he ran his fingers along the string of my thong. I heard his breathing grow heavier and his lips smack together. He gave me a quick spank and then bit me on the shoulder.

  “You know you’re the hottest little girl here, right?”

  Being called a hot little girl nearly made my cock explode. I wasn’t gay, but what could feel more womanly than being dominated by a huge cock?

  Maybe if I can just keep it in my ass, I thought. Wait! What are you thinking? Getting fucked in the ass by a huge cock? What’s happened to you?

  But I knew it was the clothes that did it. I was a completely different person in a dress. Oddly enough, I actually liked myself more in the dress than out of it.

  “I don’t know about that,” I said, trying to be shy for him.

  “Mmmm. Well allow me to show you just how much you turn me on,”
he said. He reached around for my hand and brought it behind my back. Then he slid it along his pelvis until my palm came in contact with his hard cock.

  “Wow,” I said playfully.

  “Yeah, baby. You want this hard cock to fuck you real good?”

  “Mmhmm,” I said, still hoping I could keep it in my ass.

  “Where does a hot little thing like you like to be fucked?”

  “My ass,” I said, grateful for the opportunity to direct him.

  “Oh yeah. I bet you like getting your little asshole stuffed full of cum.”

  “Yes, sir,” I said in a high pitched voice.

  Lyle pressed his bulge against my ass cheeks while he massaged my “breasts.” I leaned my head back and moaned while he kissed my neck. He rocked his hips against my bare ass over and over, rubbing the underside of his shaft against me.

  I reached behind with both hands and unfastened his pants. I slid them down and found his hard cock jutting out. I stroked it while he massaged me. He moaned in my ear.

  “That’s my good little slut. Stroke that hard cock for me,” he said. I moaned with delight and started to stroke him.

  Lyle slid the top of my dress down and ran his hands over my bra. Then he unclasped it. When the band was loose, he moved his hands around to my chest and slid his fingers against my nipples. He tugged on them and rolled them in his fingers.

  “Ohh,” I cooed as he played with my nipples.

  “You’re lucky I’m an ass man,” he said. “I don’t mind that you don’t have any tits.”

  I couldn’t help but smile. He was about to fuck a dude and didn’t even know it. I moaned again and his hands slid down to my hips. He grabbed tightly and rocked my hips back and forth against his cock.

  Then he moved his fingers to the strap of my thong and pulled it down just under my ass cheeks. He walked me slowly over to the desk, kicking off his pants and boxers along the way.