Stiletto Bluff

Two years ago, everything changed on a blustery October night. I host a monthly poker game at my house--it's mostly a few coworkers, some guys from the neighborhood. Around eight people. For Halloween, we decided to do a costume party theme, and four of us made a pact to have a drag contest. It was a little selfish on my part, because it's a thing I've been doing for a few years. Since my divorce I'd been in a huge house all alone. It started innocently enough--Curiosity and boredom. But I got a huge thrill out of it. There was something so transgressive, so forbidden about it. I posted some pics anonymously on message boards here and there, and I was shocked at the level of enthusiasm for how I looked. All of it motivated me to dress more and more often, to perfect my "look." By the time the night of the game rolled around, I had a pretty good understanding of how to pass as a woman.

After I got the house ready, slid an enormous bowl of candy onto my porch, I took a long, luxurious bath. I shaved my entire body, with a glass of merlot to keep me company in the steaming waters. I walked into the guest closet I pretended was full of my ex-wife's stuff. Silk panties, garters, black stockings. Black silk gloves. This part alone filled me with so much excitement, sometimes I had to masturbate, if I hadn't already in the bath. I had petite breastforms to give the illusion of a little something. Then, the dress--a slinky black number that covered my arms and down to mid-thigh, barely covering the stocking seams. A chunky red belt. Then the makeup--a simple yet elegant process that accented my lips and cheekbones. The wig, a long, straight brunette one went on here. Almost done.

All except the final, and best step. Five-inch patent leather stiletto pumps. As I slid them on, I felt myself settle into Melanie, my alter ego. I created an entire backstory for her. I could pretend she was a distant cousin, housesitting and hosting the poker game in my absence. It made me so hard to look at myself in the mirror, but it was getting late, and people were no doubt on their way over. I promised myself afterward I'd have an extended wank session, with some of the toys I'd recently been experimenting with.

The game had been going great. After a few hours, I was up about fifty bucks in chips, and two guys had already busted out, playing PlayStation on the other side of the room. Melanie was a huge hit--I'd even practiced a feminine voice to stay in character. Frank, one of my coworkers, brought a friend named Adrian. Some kind of mid to upper-level manager type. He'd made a few comments about my appearance--very complimentary. I found myself blushing once or twice. Adrian had a way at staring at me at the table during hands. I'd look up and catch him. There was a coiled intensity coming from him that I wasn't quite prepared for. At the halfway point, we took a twenty-minute break, and I walked to the study on the other side of the house to refresh my whiskey. I was surprised to see Adrian there, looking at my books with a beer in hand.

He looked me up and down for a long moment as I entered. "Nice outfit, Melanie," he said.

I smiled. "It's an imaginative costume."

"That's not a costume."

"Excuse me?"

He stepped closer to me, and I found myself backing up a step, until my legs brushed the bookcase behind. Adrian smelled of a cologne I couldn't place but smelled exotic. "That's not a costume," he said, his face inches from mine. "That's your alter ego." He casually moved a stray piece of the very expensive wig hair out of my eyes. "Isn't it?"

I stared at his lips, heart pounding in my chest.

"And I'll be willing to bet that you're hard as fuck right now, thinking that some of the men at this party think you're hot, aren't you?"

I looked away, and I knew he could read the truth in my eyes. "I'm not gay," I whispered finally.

"Never said you were. But you're planning on jerking off tonight, thinking about all the attention you're getting." He stared down at my groin, at the barely detectable bulge there. Adrian walked off to the far side of the room and perused my books, back to me, next to the bar. I felt a twinge of disappointment that he walked away, even though inside I was flipping out at the thought of kissing another dude.

I exhaled raggedly and took a healthy slug of my whiskey. Liquid courage. I walked past him to the mirrored bar, and he turned to face me.

I gasped as I saw that he'd pulled his cock out. Eight inches of hardness, pointed in my direction. "The ah, the bathroom is... down the hall," I husked out, eyes transfixed on his manhood.

He watched me with that predatory intensity I'd glimpsed at the poker table. "I want you to touch it, Melanie. Have you ever touched a man's cock before?" Adrian stroked himself lightly as I watched.

I swallowed heavily and shook my head no.

"Good," he murmured. "Good." He beckoned me over with a hand.

I found myself moving, stiletto heels clicking on my wood floor. Like a tracking beam had me in its clutches. Boom. Boom. Boom. Echoing in the space.

"That's a good gurl," he said softly. I should get back to the game, be a good host.

I swallowed heavily, heart pounding. I reached out, slid my gloved fingers around his shaft. Even through the dark silk, it was hot to the touch, and I almost recoiled. But something made me keep it there.

Adrian shuddered. He bucked his hips forward, just slightly, moving his manhood in and out of my hand. "Oh god, that's it."

I found myself making a little tunnel for his cock to move in and out of, rasping my nails over the veins that bulged from the rigid surface.

His breath grew ragged, and then I felt him pulse in my hand. Semen shot onto the hardwood floor, dangerously close to my stockings and stilettos. With a final groan and buck of his hips, he pulled out of my hand and put himself away. "Thank you, Melanie. That hit the spot nicely."

I was too shocked to respond.

He smirked triumphantly as he put himself away. "I knew you were a dirty girl. See you back at the table." Adrian walked out, leaving traces of his cologne in his wake, laced with the faint tang of cum in the air.

My mind spun in a vortex. I had just jerked off another man! I slipped a glove off and squatted down, put a finger in some of his spend on the floor. Held it to my lips. His seed tasted of salt, still warm from being inside his body. With my other hand I slid down, down, to where my own cock stood at rigid attention. What the hell was happening to me?

I took a shot of whiskey and spent some time composing myself. This is my house. I stared at myself in the mirror behind the liquor bottles. Dark, heavily made-up eyes stared back defiantly. This is my fucking house. I straightened up and walked out of my study.

"Raise--Two Fifty," Adrian said, smoothly stacking the chips and pushing them out into the center of the table. He stared across at me with a dominant smirk on his face. Everyone stared at me.

I was the only other player still in the hand. I stared back at him and looked away, while sliding one foot out of my stiletto pump. As my leg extended under the table, I matched his chips in the center. "Call." I glared at him while my toes quested for his groin, finding them. Finding the hardness there. Slowly moving my stockinged foot up and down.

He gave a little gasp and some of the other players made fun of him. "What's the matter? Scared of little old Melanie?"

Adrian swallowed heavily, as he opened his legs to allow me more room to work. The dealer played out the flop. Ace four seven, diamonds and spades.

My foot caressed up and down his jeans, tracing the contours of his erection.

"Ch-Check," Adrian muttered as he shifted in his seat.

While the attention of the table turned to me I felt him sneakily unzip himself, allowing his cock to spring free.

"Bet. Four hundred," I said as I took my other foot out of my shoe and put it in Adrian's lap. I glanced around quickly but no one seemed to suspect a thing. My feet closed in a vise around his manhood, cloaking it in a silken embrace. I could feel how tense he was through his shaft as my feet slowly moved up and down.

Adrian seemed lost in thought, doggedly staring at his cards as I slowly stroked upward on his dick. "Call," he said finally, raggedly exhaling.

The dealer burned a card and put the next one down. Four of spades. Three spades on the table now.

My eyes seared a hole into him.

Now it was his turn to look away. "Check."

I nodded imperceptibly. Below the table, I stopped stroking him. I felt Adrian buck his hips slightly, to keep the delicious friction between my feet and his manhood going. "Six hundred." I slide the chips into the center. Other players around the table murmured.

"You're bluffing, Melanie. All in." He put his chips in and stared back at me angrily.

I looked back, a Cheshire cat grin on my face. "Am I?" I matched my words with renewed movement of my feet on his cock and watched desire and pleasure flood across his features. "I call."

We flipped over our cards at the same time. I had Ace Four off suit, and he had the Ace King of spades. With one card to go, Adrian had a flush, while I had two pair. I could feel him begin to tense through my toes, and I watched his hands grip the table strongly.

"Haha, Melanie has A-4. The Tranny hand. Get it, because it looks like a pair of aces, and you're a dude dressed as a chick," my neighbor joked from a few seats down the table.

I smiled sweetly. "I always play A-4." My feet clenched onto Adrian's manhood in a vise. There it was. I felt his shaft begin to pulse, and he grunted, turned it into clearing his throat.

As the river card came down, what felt like a river of jizz splashed onto my stockinged feet. Hot, thick ropes of it erupted from the cock between my feet. The cock between my feet. I'd just given a man a foot job. I couldn't believe it. I glanced across at Adrian, who stared back with an exhausted shrug.

"I had the nut flush. I thought I was good."

"Oh, you were good, all right," I replied with a beaming grin. "Good for me." I stroked the last twitches out of his slowly deflating cock and put my feet back onto the carpet. I had to let them dry out a little before I put them in the heels.

Adrian waved a couple twenties in the air, not moving from his seat. "I'll take a rebuy, please."

The rest of the night was a blur. We played for a few more hours. I busted out towards the end, and Adrian actually had a great comeback, taking my neighbor out to win it all. I slugged a whiskey down as everyone got up to leave around midnight.

Unsurprisingly, I found myself alone with Adrian. He'd had a few hours to recover and nursed a beer while he looked at some of the art in my game room.

He wagged a finger at me playfully, as I walked up. "I was not expecting you to do that."

I came to a stop in front of him, gloved hand on my hip. "I hadn't expected to do it, either. Seemed like a good way to distract you."

He pounded the rest of his beer in one gulp. "It worked." He gestured at the table. "Want to play one on one? Heads up?"

I looked back at him. It was late, but I was intrigued. "Stakes?"

"Strip poker."

"You're on." I turned the lights down a little, put on some music, and refilled our drinks.

Thirty minutes later, I'd only lost my belt and dress. I still had my bra, panties, gloves, stockings, and stilettos.

Adrian, however, wasn't so lucky. A run of bad cards had left him clad only in his boxers. I finally busted him out when my inside straight beat his trips on the turn card. With a sigh, he shucked off his boxers and set them in the pilot of garments on the table.

"Oh well," he said, with a smile. "At least I won the main game." He stood up and walked over to the sofa, sitting down, completely naked.

I got up and walked to the wall, pretending to examine a picture, before turning back to regard him.

He sat in a relaxed pose, legs spread open. Adrian's groin was completely shaven, and his cock stood erect, eight inches of steel pointing skyward as he watched me. With one hand he lightly touched his manhood, while the other held his drink.

"I guess I didn't tire you out," I said lightly, eyes transfixed on his shaft as he massaged it back and forth.

"Oh, no." He took a final sip of the drink and set it down. Adrian beckoned me forward with a hand. "Come here, Melanie. Something about the confident, commanding way that he said it.

I found myself walking towards him, staring at myself in the mirror behind him on the wall as I approached. I set my drink on the coffee table.

He took my hand gently. I stared down into his eyes, my heart pounding in my chest. "We're not done, yet, sissy, are we?" Lightly, Adrian exerted the slightest downward pressure on my hand.

Slowly, I sank to my knees on the carpet before him.

"You've never sucked a real cock, have you?"

I shook my head, staring at the head of his dick like it was the barrel of a loaded pistol. "I'm not gay," I asserted for the second time that night.

He stroked my hand softly. "Good. I'm not either. I like hot women." Adrian guided my hand to his dick. He closed his eyes in pleasure at my touch, eyes rolling backward.

Wow, I was really doing it for him.

"Come on, sissy," he said softly.

I felt an intense desire to please him. Slowly, I stroked his shaft up and down. Leaned closer. Closer.

I stared up at his face over his manhood. I kissed the shaft. Dragged my lips upward.

"That's it, Melanie," he murmured, cupping my face with a hand.

I felt the power through his fingers, the strength of his desire. I put the tip of his cock in my mouth and listened to him exhale roughly. One time, I'd sucked on my ex-wife's dildo, just to see what it was like, but this was totally different.

He pulled me up onto the sofa next to him, and I nestled my head in his lap. With one hand he guided his manhood to rub up and down on my lips, and the other one stroked my head gently.

I felt lost in his musk, his hardness, feeling the thrill of submitting to his dominance. His urgent need. A need that I had the ability to satisfy. Something turned off in the higher, rational part of my brain. I took him in my mouth. Up and down, up and down, tongue swirling around the edges of his shaft, the head. I felt him slide a hand down my bare back, and his fingers quested for my ass through my satin panties. As I sucked him, he slid a finger slowly inside me. Initially it felt uncomfortable, but soon he landed near my prostate. I'd only heard about male anal orgasms before, never experienced one. I stared into his eyes with a mouth full of his manhood.

He slid his finger out and guided his cock out of my mouth. I felt a twinge of disappointment that was short-lived, as he spun me around to face the wall.

Face to face with myself in the mirror, he roughly spread my stockinged legs apart. I tottered on my heels on the thick carpet as he nestled his cock in the cleft of my ass. He massaged my groin through my underwear.

Adrian stroked himself, spreading precum and saliva around his shaft. We made eye contact in the mirror, as he slid into my ass. The pain was intense, and I mewled softly. A tear slid down my face at the burning sensation, making a mess of my mascara. Slowly, slowly, he moved in and out of my ass.

After long moments, the painful sensation began to transform into something else. A fullness that was something like pleasure. I found myself arcing my hips back slightly, giving him a better channel for his manhood.

"You like it, don't you? You like getting fucked, sissy." His gaze went straight to my soul.

I gave a little nod, holding one hand on the wall and reaching back with the other to caress his flank.

He pulled my head back roughly and kissed me hard on the mouth. Our teeth clacked together, tongues exploring with excitement.

"Say it." Adrian commanded, as he increased the speed of his thrusts. I could tell he was getting close. I was, too. His panting and groans of bliss grew more and more out of control.

"I like it. I like getting fucked by you." I felt something inside me unlock as I said the words into the silent air. My complete and total submission to him must have been the final straw that sent him over the edge. He pistoned in and out of me, pressing my face to the mirror. I stared into my own eyes as a wave of sheer bliss unlike any I'd ever felt began to build. My cock erupted, coating black satin in sticky seed. At the same time, his manhood began to quiver. I clamped down with my sphincter on him. Adrian roared in pleasure and pulses of cum lanced into me, filling my insides with warmth.

It seemed to go on forever and ever. At last, we both seem to be done. He shivered slid out of me, sat on the sofa and pulled me into his lap.

He exhaled. "Damn, that was good." He stroked my wig as he looked down. I felt his slowly deflating manhood beneath me. "You know, there's a ladies only tournament next week at the Casino. I bet you'd be a really strong competitor."

I stared up at him. "Are you going to come as my manager?"

Adrian smiled at me. "Of course. We'll get a suite, make a weekend of it."

"I do have some new outfits I've been wanting to try out. And shoes, of course."