Free Shoes


"Lift your leg up on the sink and pull your panties down again. I like to watch you submit," the voice behind me commands. I didn't intend to go this far. It was supposed to be harmless fun. But as my throbbing cockhead rests against the cold of this stranger's bathroom sink and I can see my high heel dangling off the edge of the counter, I find myself helpless to say no.

I suppose it all started with my last business trip. Some crappy little hotel in the middle of nowhere with no Wi-Fi, no porn, and a constant business associate in a shared motel room. Back to jerking off in the bathroom twice a day like I'm a teenager again. Things internalizing, twisting, growing.

Three weeks on the road and something snapped when I finally got home. The comfort and freedom of being alone and safe in my own apartment combined with a stack of cash and nothing to do. A few celebratory drinks and a dig through the toy box for 'one last time.' Fresh ice, another pour of bourbon and I'm on CraigsList trolling through 't4m'.

The ad I placed was simple, "Free Shoes to a Willing Playmate." I kept the text of the ad short as well. "Getting away from crossdressing. If one of you gurls is willing to play with me for a short while, I'll give you my size 14, five inch stilettos, my thigh highs, dresses, etc. Not looking to top or bottom, just into a bit of safe, sane play. Email for details".

I don't know why I even bother because I always end up chickening out. It's a small town. I don't want to give away my name or face. I don't want to wake up dead in someone's trunk. I don't want to keep wearing women's clothes and whoring for cock.

But yet...

I checked my email over and over again. A reply appeared. "Would love some shoes. What kind of play?" It was signed 'Debbie'.

"Hi Debbie. Simple deal. I like the feel of a high heel in my ass. A cupped hand spanking my balls. I like my nuts squeezed hard while my ass gets toyed with my big vibrator. Not a big pain freak, just like the humiliation. I'm willing to return certain favors if it suits you... happy to degrade you if you like that or fuck you with your toys. But not looking for anything unsafe. Whadya say? Want some new shoes?"

The reply was quick. "How about I turn your little sissy balls black and blue and then make you lick your own cum off of my clit?"

A warm hot surge flowed down through my body. My knees became shaky and my cock pushed hard against the thin fabric of my panties. I was wearing my favorite outfit. The black stilettos with the little strap around the ankle, white thigh highs and panties that crawled up the crack of my shaved white ass. I hadn't bothered to put on the black velvet dress that stopped just above the elastic top of the thigh highs but it was hanging on the bedpost behind me.

I took a gulp of the whiskey and replied with trembling hands. "Shall I come to your place?"

I hit 'send' and felt my eyes glaze over in zombie like lust. My heart was racing and my teeth chattered slightly as the adrenaline tore through me. The reply came quickly. "600 South 9th. Door's open."

I walked shaking over to my jeans and pulled them on over the sheer fabric of the stockings and panties. My dick resisted as I pushed all 8 inches of it down into my pants. A t-shirt, shoes, coat and a grocery bag filled with the heels, toys, lube and condoms and I'm out the door.

As I drove, my mind was blank save for the images of high heels, mouthfuls of cum, cocks hanging in front of my mouth, asses in the air with panties pulled down. My hands shook on the wheel, my balls ached for release.

I parked on the street. A porch light illuminated a small shotgun house on a dark street. I texted a friend of mine who knows what I do and sent her the address. 'Have fun and be careful,' was all the reply said.


I took my bag and walked to the front door. I turned the handle and as advertised, it was open. On the couch sat a thin man with a wig and hollow cheeks. He wasn't passable but he wasn't awful either. It didn't matter what he looked like actually; the more horrible the better in a way. He was dressed in a similar fashion to me. A clear plastic stripper platform heel dangled from his stocking covered foot. The black stockings disappeared in a pile of sheer black material that covered black lacy garters, panties and bra. He smiled broadly and stood to greet me. He shoved a hand forward, "Hi. I'm Debbie, won't you come in?"

"I was afraid to drive over dressed," I stammered. Should I introduce myself? Should I give him/her my real name or gurl name or what? My face flushed red and the shaking became worse. "Should I go in the back and change?"

"Whatever you like dear, just make yourself comfortable," she said and returned to her seat. The back of the house was dark. I didn't want to go back there. "Can I get you something to drink?"

"No, thanks," I said and set the bag down on a chair. "I've got my play clothes on underneath. I'll just change quickly."

"Fine, fine," Debbie said. While she spoke, my eyes locked on her erection. It was as big as mine and slightly thicker. "What shall I call you?"

"Whatever you like," I told her as I pulled my shirt off. I kicked my shoes off quickly and began undoing my belt. "I've always liked the name Stacy. But if you want to call me something else or just slut or slave or..."

"Mmmmm," Debbie cooed. She took a sip off of a drink and rolled her head slightly as I dropped my pants. The small lace panties couldn't even begin to hold my erection back. I laid my clothes on the chair and quickly pulled out the dress. As I pulled it over my head, Debbie sat straight up on the couch and declared, "I will call you cumslut. And probably faggot. And sissy. And cunt." As she spoke, her voice grew more feminine and my cock twitched so hard I thought I was going to shoot.

I sat and pulled the heels on. They jammed my toes into the pointed end and my fingers could barely manage the strap around the ankle. "You will call me Mistress tonight and we will have much fun."

I finished with the shoes and stood to present myself. "Yes, Mistress. How shall I serve you tonight?"

Debbie giggled. "I like your attitude."

I had meant to lay out the ground rules, the boundaries, the safe words. Let her know what I wanted, what I needed. Make it quick, make it fun, get out and never look back. But my mouth had gone dry and I was ruled completely by the hot chemical lust rolling through my veins.

She patted the couch and said, "Sit slut."

I walked across her living room and let my hips swing slightly back and forth. I folded my hands in my lap and stared at the ground for a moment. I didn't know what to do next. Debbie's hand slid calmly to my knee. Her hand rode up my thigh and like the whore that I am, I moved my hands and parted my legs. "Good little slut," she whispered.

Her hand disappeared up my dress and headed straight for my constricted balls. Her fingers danced against the lace and I concentrated hard on not cumming. Without a word she grabbed my sack and squeezed. Softly at first but with ever increasing pressure. My breathing became shallow and fast as the pain and pleasure fought up my spine and exploded in my brain. Her painted fake nails began to dig into the skin of my scrotum and she was now squeezing quite hard.

"Mmmm," she said again and let them go. "You know, I like that little dress but it is in the way. Take it off. Now."

I slide the dress off and sat there in my panties, stockings and heels. Mistress Debbie told me to spread my legs again and I did as I was told.

She patted my balls before giving them a little tap. My legs twitched and the head of my dick hung obscenely over the stretched waistband of the panties. She slapped my balls again, harder and harder. She poked a fingernail into the tender flesh of my inner thigh and drug a red mark all the way to my knee before bringing a cupped hand down hard on my crotch. I sat up in pain and closed my eyes. My hands covered my balls and I thought I might pass out from the intensity of everything.

"What does it say?" she asked.

"Thank you, Mistress," I told her with my eyes still closed.

"Such a good little faggot," she told me. I felt her fingers tracing the bottom of my chin and I relaxed at her touch. The fingers slid up and around my neck until they found the long dark hair on the back of my head. The fingers tightened into a fist and I opened my eyes to see her holding her cock in her other hand. My mouth hung slightly open and the skin over my heart pounded with every beat. "Now why don't you lean over and put my little clit in that hot wet mouth."

I felt her push on the back of my head. Still holding onto my aching balls, I leaned over her stocking covered leg and took her cock in my mouth all the way down to the base. I felt her stomach muscles tighten as she let out a low moan. The hand holding my head pulled and I rose up off of the stiff dick in my mouth. The taste and warmth flooded my mouth along with saliva. Mistress pushed my head down again and I opened wide. The back of her cock hit my throat over and over again as she fucked my mouth. I slid off the couch and onto my knees in front of her. She pulled me around directly in front of her and slid her foot up into my crotch.

I swirled my tongue all around her shaft and head as both hands pushed and pulled my head. I dry humped her leg and could feel a climax building in my own sissy cock.

Debbie pulled her cock from my mouth and held it up out of reach. "Lick my balls," she said. Her voice was husky and low like a woman who had smoked all of her life. I stuck out my tongue and licked her balls ravenously. As I alternated between sucking her testicles into my mouth and licking her sack, she began to rock her hips forward and push my head down. My tongue danced across the small patch of skin between her balls and asshole. She pulled her panties to the side further as I flicked across her puckered rose bud. She suddenly pushed my head back.

"Lay on your back, faggot," she told me. I laid back on the carpeted floor with my knees propped up. The heels accentuated the shape of my calf muscles and my cock throbbed in time with my heartbeat. Mistress Debbie stood and removed her black panties. She smiled down at me and walked slowly back and forth beside my submissive form, savoring the moment. She stuck her foot between my legs and I spread them wider to offer her unhindered access. She pushed on my balls with the clear plastic sole of her heel. "Are you going to be a good little cumslut?" she asked as she played with my totally vulnerable balls.

"Yes, Mistress," I answered in a whisper. Any ideas I had of keeping this tame and controllable were long gone.

"Good. Because if you don't, you'll be punished." With that, she popped me in the balls with the top of her foot. The slap was loud but the pain was minimal.

"Thank you, Mistress," I told her. She laughed.

"You pathetic little sissy," she said and moved towards my head. One heel touched down on one side of my head as the other turned to position her ass directly over me. Her knees landed under my shoulders as she squatted down over me. Without being told, I immediately shoved my tongue into her as soon as I could. I ccould feel the vibration of her moan.

I began to fuck her ass with my tongue, slowly working it in and out, around in circles and then in again. I felt a hand on my cock. It slid down to my balls and gathered them up into a bunch. A hard, flat hand landed on them and my whole body jerked. I tongued her ass deeper and harder. I opened my jaw as much as I could so that I could get more of my tongue into her asshole.

Another slap and I worked harder. Her balls hung on the end of my chin and the blows began to reign down harder and faster. I placed my hands on her ass cheeks and shoved for all I was worth as she finally stopped the assault on my balls. Her body leaned forward and I felt something hot and wet around my cock. Her cock slid back and up onto my lips. I opened and took her into my mouth again. As I tasted the salty, swollen purple head, I could hold back no longer and came long and hard into Mistress's mouth. Her fingernails dug into my hips and her head remained still. She took every drop as I writhed beneath her, her cock still in my mouth.

Her hips rocked slightly up and down and I felt her legs shake in my hands. She pulled up to the edge of my lips and something warm and sticky and salty shot into my mouth. Squirt after squirt filled me and I swallowed and flicked the sensitive head with my tongue. It was a large load with clumps of sperm and I did what I could to swallow it all.

Without speaking, she rose up off of me and moved to my mouth. Her lips were pursed and she grabbed my nose with two fingers. I opened my mouth as she leaned forward and spat my own cum into my mouth. I swallowed the sticky, slobbery load along with the rest of her cum.

"Get me hard again," she said and straddled my head. I took her half hard cock into my mouth and ran my tongue along the bottom side of the shaft. She moaned and flinched, jerked and shivered. Her hand reached back and squeezed my nuts again as I moaned into the head of her dick.

She was quickly hard again and stood up. "Get in the bathroom, slut," she said and pointed towards the dark hallway. I stood on trembling legs with the taste of ass, cum and cock in my mouth. I was already getting hard again myself.

Mistress Debbie turned on a light and lead me by the dick to her bathroom. "Lift your leg up on the sink and pull your panties down again. I like to watch you offer yourself to me." So here I am, beyond the point of return. The predilection I was looking to leave behind has swallowed me whole.

I offer her my ass as I am told. I hear the click of a plastic cap and the cold drops of lube pouring down over my asshole. A finger inserts itself without warning and slides all the way in. I let out a girly moan and arch my back a little.

The finger withdraws and I can hear Mistress lubing up her cock. "I like it a little different," she tells me. A hand clamps down on my balls hard and pulls them down, "You wanted a high heel up there but you're going to take this like the little faggot cunt that you are."

I nod my head yes and wait for whatever 'it' is. I feel her push against me and do my best to relax. She slides easily into my slut ass. I feel her balls touching mine and I give her a squeeze with my sphincter. But instead of fucking me, she waits. Her hands hold my hips and we stand there motionless for many seconds. And then I feel it. A hot, fast flowing stream pouring into my bowels. I hear her giggle. "I need to pee after I cum."

I close my eyes and my legs shake so bad I think I might fall down. My dick spasms as more and more of Mistress Debbie's piss fills my bowels. My stomach begins to ache and my ass is stretched with her wide, long dick. After she finishes using me as her toilet, her hands tighten around my hips and she begins to slowly thrust into me. Piss leaks out of my ass with every stroke and she begins to fuck me faster. I moan and slosh around inside as she takes me from behind. Faster and harder, each stroke punishing me.

She pushes up over me and leans so that her chest is touching my back. A hand comes off my hips and grabs my cock head, twisting it painfully. As she abuses me, she shoves hard and cums again, filling my ass with her sperm.

"Don't move," she tells me and pulls out. I clinch my asshole shut to keep from pissing everywhere. I hear the clink of the toilet seat. "Sit," she say and I back up on her toilet and sit down.

I still have plenty of Mistress's piss inside of me and start to release but she stops me. "Would you like to release Mistress's load from your fuckhole?"

I nod yes.

"Then you better open your mouth," she tells me and holds her limp dick up. I look at it and the broken wheels inside my head spin without contacting. My bottom jaw drops open as she slides the filthy penis into my already cum coated mouth.

I lick ass, piss and cum off and release the contents of my bowels into the toilet. "You may relieve yourself with your hand if you like. But if you cum, you have to cum on my asshole."

I start stroking myself furiously as I suck her stiffening cock. She runs her hand through my hair and talks to me in baby talk. "Let me know when you're cumming. I'll bend over and you can spray it all over my little puckered asshole. And then, you fucking little slut, you're going to lick it all up."

Her words tear through my brain and down to my cock. I stand quickly as she takes my place at the sink. My second shot is more juice than seed but there is plenty of it as I paint her ass crack white. She shakes back and forth and pushes the stray drops of cum towards the hole.

"Lick," she says and I drop to my knees. My cum tastes sweeter than her cock just did and I lap it up to get rid of the bitter taste of my own ass. Her heel comes back and kicks me lightly in my balls. I stick my tongue further into her ass.

She turns finally and sits on the side of the sink. "You're a good little slut," she tells me.

I feel like passing out. I want to go home now as the reality of it all washes over me. "Would you like your heels now?" I ask her and start to unbuckle an ankle strap.

"Oh no, no I would not. You keep them my pet. You'll be coming back here to service your Mistress again."

"But," I start but she shushes me with a finger over her lips.

She points to the camera mounted in the upper corner of the shower. "There are three more in the living room. Unless you want to be the next internet sensation, you'll do as you're told."

Panic spreads through me. My neck burns hot. I don't know what to do, think or feel. Her hands slides down over my cheek lovingly and I look up at her with pleading eyes.

She smiles at me sympathetically. But the smile changes into something menacing as she grabs her dick and looks me in the eyes. "Now open that little mouth again slut, I told you I have to pee after I cum."

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