Slave - 01 - The Beginning

Author's note: All characters over eighteen and written purely as fantasy.

This is the first story in a series that I am in the midst of writing. While I initially planned to release it in one entry, I decided that I should post something now.

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2008

My parents would have been horrified if they saw me. Their son was dressed in a blond wig, beige trench coat covering up this tight black mini dress and while I had sneakers on, I had my favorite pair of fuck me heels in a bag slung over my shoulder and of course, sunglasses despite the sun having gone down already.

When they named me Ryan, I am sure they didn't intend on me being a slutty, crossdressing hooker but to be fair to me 'Ryan' was kind of an ambiguous sounding name when it came to gender and as for the slutty part, years of Catholic school did that.

As for the hooker part, I only fucked this one particular old guy for money. He just so happened to live five houses down from my parents and I had known him for years. I told him that I was just doing it for the sex but he insisted on paying me anyway. Being a broke college kid it went towards buying booze and other things I didn't want my parents to know about.

Avoiding detection by my neighbors lest a scandal break out in the neighborhood, I slunk out through the back, weaving through the neighbor's darkened backyards only going back to the sidewalk after three houses.

Walking up to his house, I quickly switched into my heels. I loved all of this sneaking around and playing dress up to boot made me feel like an honest to goodness whore.

To be fair, I thought all of this was a little silly but I loved dressing up and I loved getting fucked. My heels clicking up against the ground I walked up to the door; took a deep breath suppressing how giddy I was and presented my straight, serious face and I rang the doorbell.

When Hal answered the door he had this creepy fucking grin on his face, "Good Evening, love."

I brushed past him without saying and took off my trench coat, showing him my dress and then took it off and tucked my sunglasses away.

I was midway though hanging up my coat when I felt him walk up behind me. As he pressed up against me I could feel that he was already rock hard.

"You are so beautiful Ryan." He kissed the nape of my neck.

I still didn't say anything, simply just standing there as his hands began to feel me up.

They worked their way down until he reached my hips and then very carefully lifted up my dress and took my now hard cock into his left hand. His right lifted up and his cold calloused hand wrapped around my neck giving it a light but firm squeeze.

I gasped just ever so slightly at my breath being restricted and let out a little moan to excite him.

He grasped tighter and then let go. Shifting positions his right hand went over my mouth while his other arm wrapped around my neck and squeezed. I flopped like a fish as I tried to pull his arm away but being in my heels, I was easily knocked off balance. Hal may have been old enough to be my dad but he was still much bigger than me and a lot stronger.

I passed out, falling limp in his arms.

When I woke up, it took me a few moments to remember where I was last and a few more moments to realize that I had been moved.

I was strapped down to a gyno chair, my arms tied above my head and my legs spread apart and a dental gag keeping my mouth wide open. Curiously, I was still in my dress.

"Oh good. You're awake." Hal's voice rang out, taking a seat down next to me "You know, I do enjoy seeing you like this, so helpless, so vulnerable." He traced his finger along my neck, "I have always fantasized about how you would look at the end of a leash."

I lay there looking up at him, cold. I wasn't about to give him anything he was looking for.

"I see then that's how you want to play it." He turned away and with a pair of shears he cut away at my dress till it was nothing more then shreds, falling off to the sides of the chair.

I could see him drop his jeans and then take off his shirt, stroking his own cock to get himself hard and I assumed lubed up.

I clenched my eyes shut and waited for the next part and sure enough his manhood was finding it's way up my ass. Contented he began thrusting back and forth in a rhythmic motion. I cried out, moaning in a combination of pleasure and pain.

The whole chair shook as he fucked me until he stopped suddenly and held himself still. He pulled out and walked around and stood directly next to my head. I watched him intentently as he finished himself off with his hands. Gobs of hot, sticky cum hit me in the face, some of it making it into my mouth.

With his finger he scooped up the cum off of my face and wiped it off into my mouth. Looking up at him he was having a grand old time.

He leaned over and took out the gag and then went back to between my legs. I swished the remaining cum around in my mouth, savoring every last morsel before I swallowed it and the next part of our night started.

"Oh fuck." I moaned, the whir of a hitachi vibrator being pressed up against my erect cock had started.

I could hear him giggling, laughing as he stroked me off, watching with delightful glee as I twitched and spasmed.

"Please, I want to cum," I begged, gasping at the sensation of being toyed with.

"No, not yet."

He only made it worse from there applying pressure, building me up and then suddenly letting go, denying me release.

"Please..." I begged, half crying from the hormones, "please let me cum."

"If you insist."

It was a moment of pure bliss as my own cock exploded and I could feel the thrust of my hot cum shooting out of my cock and landing back on top of my cold bare skin.

"Fuck..." I cried out in blissful orgasm.

I let myself relax, letting all of the tension go. It was a few moments and Hal reappeared in front of me.

"Did you enjoy yourself?"

"Yes, yes I did." Trying to catch my breath, pulling up against the restraints, I asked "Care to untie me now?"

"What, can't I keep you like this?" He laughed as he undid the restraints.

I stuck my tongue at him, "In your dreams you pervert."

We both laughed.

I stretched and hopped back onto my feet. "How late is it?"

"Nearly ten."

"Damn, I gotta go. I promised some of my friends I'd help them with a project tomorrow.

We walked upstairs. "It's too bad that you have to go back to college." He mused.

"Yeah, I am great, aren't I?."

Luckily I had some boy clothes that I packed, Hal did love tearing clothing. While I was pulling my t-shirt over my head, he had four hundred dollar bills in his hand waiting for me.

"For your dress."

"Thank you."

"How long until you'll be home again?"

"I'll be back for Christmas break, I'll give you a call when I plan to be back." I gave him a peck on the cheek. "Thanks for the good time tonight."

He opened the door and I walked back home, my ass sore but happy.