A Jailers Captivity

The following story is dedicated to Lisa, who encouraged me to submit this story for you to read.

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I had always considered myself a rather macho type man. I'm 45 years old, weigh 225 pounds. I'm 6' tall, and in good shape, not overly muscular, but well toned. My profession requires that I maintain myself in good physical shape. I've got naturally curly brown hair, and a very hairy chest and stomach. I've been in law enforcement for twenty-two years, not as a police officer, but within the jail setting. We are trained to rely more on our physical abilities, than our patrol counterparts since we carry no weapons on our persons while on duty.

I was living in a second floor apartment in a complex of approximately 600 units, while attempting to rebound mentally, as well as financially, from a rather messy divorce. The midnight shift pays an additional bonus due to the hours, and since I was looking for the extra money, that's when I worked.

I had just come home on a Friday morning, and didn't have to report for duty again until the following Sunday night. Entering my apartment, I realized that I had neglected to dispose of my trash the night before. Still in my uniform, (the only difference between my uniform and a patrol officer's uniform is that I don't wear a tie, and I've got short sleeves), I grabbed the plastic trash bag, tied it, and proceeded down the stairs to the garbage receptacle located about twenty yards from my apartment. As I swung my arm up to toss the bag into the container, I was attacked from behind. What seemed to be a pillow case was placed over my head, blinding me. My first reaction was to reach for the covering with my hands. As I did so, a noose fashioned from linens enveloped my hands and was drawn tight about my wrists. Realizing I was almost immobilized, I swung my right leg around, in an attempt to upend my attacker. A forceful knee to my groin dropped me to my knees, gasping for air, and writing in pain. Another piece of linen was tied tight over my mouth, rendering me mute, except for a low groan.

I was then made to walk, and after proceeding about ten yards or so, I was spun around repeatedly, which completely disorientated my sense of direction. I knew I was near the center of the apartment complex, but had no idea of which direction I was being led. After walking perhaps fifty yards, I was led into an apartment on the ground floor. How no one saw what was occurring was beyond my belief, as this was about 8:00 in the morning. Once inside, the door closed behind me, and was locked.

I was led into what must've been the living room area. My uniform shirt was ripped open, and removed to the point where my wrists were tethered together. My boots and socks were removed. My belt unbuckled and whisked from my trousers belt loops making a slapping sound. My pants were then opened, and dropped to my ankles.

Then, there was no movement for thirty seconds or so. I stood there, hooded, unable to speak or see, my wrists bound in front of me, with my uniform shirt dangling from them, and my pants at my ankles. I heard some whispering, and knew that there were at least two captors. I felt, and heard my own hand-cuffs snap around my left wrist. The linen manacle was removed, and before I could attempt to swing my arms, they were forced behind me, where the other hand-cuff was snapped tight over my right wrist.

A chop to the back of one knee instructed me to raise one leg, and then the other, while my uniform pants were removed. I was now naked, save for my underwear, and hand-cuffed from behind. My own belt was made into a choker, and placed around my neck. As the pillow case was being removed from my head, a hand pulled my head back, by the hair, and the belt tightened. A ball-gag was forced into my mouth just as soon as the linen gag was loosened. The hood was completely removed, and a blinding sleep-mask placed in it's stead. My eyes hadn't had time to adjust to the light, let alone catch a glimpse of my captors.

I was led into a closet, and was forced to sit in a wooden chair which had been placed inside, and tied to it. The closet door was closed, and I was left to sit, and ponder my fate. As I sat, bound to my chair, I heard muffled voices. They were female! Simultaneously, I began to feel ashamed as well as slightly aroused. Ashamed at not being able to defend myself with two females, and aroused by the unknown.

Hours passed, and I had fallen asleep, (don't forget, I had been awake all night, at work). I awoke to the sound of the door latch opening. I was untied from the chair.

"Stand up, Worm."

I slowly rose from the chair, but couldn't respond, due to the ball-gag.

"Walk, worm.", she ordered. I slowly proceeded forward, her voice guiding me into the living room's spacious area. 'Crack!' my belt came crashing across the backs of my thighs. "Mmmgh" was all I could utter.

"When you're told to do something from either Marcia, or myself, you'd better be quick about it."

"Mmmgh."

"He's a nice specimen Gloria, I think he'll do fine", Marcia spoke as she gently explored my chest, stomach, and ass, before coming to a rest on the bulge on the front of my briefs. I couldn't help but feel some stirring in my balls as Marcia's fingers outlined my cock through my briefs. "Yes he is. He'll do us well.", Gloria replied.

What in God's name were they talking about? Do what fine and well? What was in store for me? Fingers quickly grasped my briefs and pulled them down, exposing me in front of these two women.

"Look Gloria," Marcia laughed, "he's getting an erection! He must think he's gonna get lucky."

"We're the ones who're gonna get lucky this weekend", Gloria giggled.

My wooden chair was brought from the closet, and placed in front of me, with it's back facing me.

"Lean forward, Worm." Gloria commanded.

I did as she instructed, the chair's back making contact with my stomach. My legs were spread and taped to the chair's legs. A hand reached under and caressed my scrotal sack before slipping some kind of rubber band around my balls.

"Marcia, you can warm him up." With that, I heard footsteps and heard a 'whooshing' sound.

'Whoosh-Smack!'. A wooden paddle came crashing into my bared ass.

"Mmmugh!" was all I could say.

'Whoosh-Smack!' 'Whoosh-Smack!' 'Whoosh-Smack!'

One after another after another the paddle struck both of my ass' cheeks, and around the back of my legs. The pain was intense. I hadn't been paddled this severely since my sixth grade art teacher found my collection of erotic drawings depicting her and the school's principal. Had it not been for the sleep mask, tears surely would've flowed from my eyes.

Marcia wielded the paddle repeatedly, with no pause in her rhythm, for what seemed like hours, but in reality was twenty-five wallops. She stopped and I felt a hand on my sore, hot ass.

"Ooh, feel the warmth. You've done a fine job."

"Thanks, Gloria." Marcia replied, as she too, placed her hands on my ass, feeling it's heat.

"Will you give him a caning now?"

"Soon enough, but first I want him to learn how it feels to be treated like a piece of meat."

Gloria sounded angry, as I wondered what was in store for me. I felt someone kneeling behind me, and felt breath on my semi-erect cock. In an instant, my cock was enveloped in the warm mouth of one of my captors, her tongue expertly licking me in just the right way. I grew rock hard in an instant as she continued sucking. Then her mouth released my cock, and began flicking about on my asshole. Had it not been for the binding tightly secured around my nuts, I surely would've cum right then and there. But, there was to be no release for me.

A greased finger impaled itself into my anus, and began tickling my prostate. Then I heard Gloria's voice.

"Marcia, move over while I take him."

Take me where? What was about to happen to me?

"Wait Gloria, I want to hear his reaction."

The ball-gag was removed from my mouth just as Gloria's hands grasped onto my hips, and I felt something hard push slightly against my asshole. Oh my God! She's wearing a strap-on!

She pushed against me, and my virgin asshole offered resistance. Suddenly, the resistance gave way, and about two inches of dildo cock rammed into my ass. I screamed in agony, and was sure that my ass had been ripped open, and was bleeding all over the carpet. Marcia placed her hand behind my head and guided my face forward. I smelled her lust before I felt it's stickiness. My nose became buried in pussy. This was an attempt to get my mind off of the extreme pain the dildo in my ass was causing.

Gloria's hand began slapping my already red ass, as she forcefully withdrew and re-entered my stretching ass, inching more of it into me with each thrust. Her ire raised, or her patience exhausted, but Gloria dug her fingers into my hips, and slammed the dildo cock all the way into me! I thought I would black out, the pain was so intense! Marcia was rubbing her sex against my face, tickling her clit with my nose. Gloria began long-stroking my ass with her strap-on.

"How's it feel to be treated like a fuckin' whore, Worm?" Gloria demanded to know, while fucking my ass.

"Ah, Ah, Ah" was all I could muster as I fainted from the pain.

I was awakened by the feel of my cock being sucked. Marcia was licking me again. She seemed sympathetic towards me. My ass felt sore as hell from my fucking. She again positioned herself so that her pussy was in front of my face. I don't know why, but I wanted to pleasure this woman with my tongue. I extended my tongue and began to taste her charms. She shuddered and moaned, and I tasted her cum within seconds. I kept my tongue active, and gently nibbled on her clit. This caused her second orgasm. Her body remained tense and convulsing. Her hands firmly grasped the back of my head, and held my face to her sex. I lapped eagerly at her honey-pot, tongue fucking her, when...

'Ssschwipp-Thwack!' A thin cane seared across my poor worn out ass.

"Having fun, are we, Worm?" Gloria had returned and had her cane with her.

"Are you ready for your caning, Worm?"

"Please don't..."

'Ssschwipp-Thwack!'-again! I felt a fresh welt rising with each impact of the cane on my cheeks. After ten lashes, she paused and inserted a smaller vibrator-cock into my ass, and turned it on. My opening having been stretched by her strap-on earlier, this smaller one slid in effortlessly. Then...

'Ssschwip-Thwack!' again, and again, and again. I was crying like a baby, only the mask preventing the tears from rolling down my cheeks. As Gloria thrashed my ass, my ass' muscles held the vibrating dildo in place. Finally, Gloria's arm tired, and my whipping ended. I was untaped from the chair, and placed on the carpeted floor. My fully erect cock saluting my two captors.

Gloria positioned herself so that her pussy was now on my mouth, and her asshole at my nose. Marcia climbed onto my cock, and her pussy swallowed it up. I pleasured Gloria's sex with my mouth, causing her to climax several times. She tasted delicious. Marcia, in the meantime, was riding me like a bucking bronco in a rodeo. All the while, the vibrator was buzzing up my asshole!

My captors changed positions, and each had at least one more orgasm. My balls were aching to explode, but the band around them prevented that. They both rose up off of me, and I felt my blindfold being loosened, and then removed! It took a couple of seconds, but, when my eyes finally focused, I was gazing up into Gloria's freshly fucked pussy, just as she began to release a warm stream of urine all over my face, and into my mouth. I coughed as I accidentally swallowed some and heard Marcia giggle. Then, I felt a second stream flow over my stomach, cock, balls, and run down into my ass. I can't explain why, but, I was very excited by all of this. When they both had finished, I was finally able to see my captors.

Gloria stood about 5'7'', with large firm breasts, and a wool covered bush. Her black hair was almost waist length. She had long slender legs that went all the way up to her perfect tear-drop shaped ass.

Marcia was shorter, about 5'4", with plump tits, and a clean shaven pussy. She had red hair, about shoulder length, and was a little on the chubby side.

I begged them to release my restraints, but "not quite yet." Marcia rolled me onto my side and began slowly fucking me, by removing and re-inserting the vibrator that, until then, had been still buzzing up my ass. I moaned, and pleaded with them to at least remove the tether from my balls, and allow me to cum. Again, "not quite yet."

Marcia removed the dildo from my ass, and turned it off. With Gloria's assistance, she placed me in the wooden chair. Once again, I was taped in place, but this time, I was able to speak and see. My captors embraced each other, and after groping and caressing each other, settled into the 69 position with Gloria on the top. I watched as these two women loved each other, bringing each other to multiple orgasms. Once they had ceased, they rose, and left the room. I heard the shower run, and had to sit there with aching balls straining against the rubber band restraint, begging for release.

After about thirty minutes, they re-entered the room. Gloria attired in a black Dominatrix outfit with red, fish-net stockings. She carried a riding crop that had at least ten different leather strops attached to it's end. Marcia wore nothing but a bath towel around her.

"Marcia seems to be attracted to you Worm. Would you like to fuck her?"

I don't know why after all I'd been through but, I was shocked by the bluntness of her question. Before I could answer, she reached out and pulled away the towel from Marcia's body, leaving her naked before me, her clean shaven sex pouting invitingly.

"Can you be trusted, Worm?"

I assured Gloria that I could be trusted, and that I'd really love to fuck Marcia. Marcia walked up to me, removed the tape that secured my wrists and ankles to the chair, but instructed me to not touch the band around my balls. She leaned forward and lovingly kissed me on my lips, then stood erect, turned around and bent down on the floor on her hands and knees, her plump ass staring me in the face.

Gloria folded her arms across her chest, still holding the crop. "Fuck her now, Worm." I rose from my chair, totally naked, and for the first time in roughly ten hours, I was untethered. I walked the few steps to Marcia unsteady, and dropped to my knees. Placing my hands on Marcia's hips I swiveled my hips, positioning my cock's head towards her glistening honey-pot.

'Schwoosh-Schwaack!'

"Not so fast, Worm. Before you fuck it, you've got to kiss it...and not her pussy!"

I obediently backed away and lowered my face to Marcia's asshole, breathing in her scent. I lightly kissed her about her ass cheeks, and methodically worked my way to her brown eye. As my tongue touched her opening, she moaned, but maintained her position. I ran circles around her hole with my tongue, causing her moaning to become quite loud. I thrust my tongue into her and felt her tense. Her ass' muscles clamped around my tongue as she came. Weakened, she dropped down onto her elbows, which placed her in an even more inviting position.

I stood on my knees and, rubbing spit onto my penis, placed it's head at her asshole's opening. With one forceful plunge, my cock was buried in her ass. She pushed back, meeting my thrust. I began pumping in and out of her, each motion countered by motions of her own. Her ass seemed to be clinging to my cock for dear like, each time I pulled away. Again, my balls were aching to cum.

'Schwoosh-Schwaack!' 'Schwoosh-Schwaack!'

Gloria began strapping my ass as I fucked Marcia's, but this time it seemed to heighten my pleasure. I felt fingers grabbing under my ass on my balls. In one motion, the band was removed from my sack.

Almost instantly, I came. Spurt after spurt of cum pumping into Marcia's willing ass. I grabbed her hips and slammed into her, my balls slapping against her. Finally spent, I fell forward onto Marcia's back, my quickly shrinking dick easing out of her ass.

'Schwoosh-Schwaack!' again, as the crop sliced into my ass again.

"It's my turn now, Worm. And you'd better have saved some for me!"

I looked behind me to see Gloria positioning herself on her back on the carpet, her vinyl suit having been removed, and her wooly pussy glistening with moisture. My dick once again sprung to life and I crawled over to Gloria. I started at her feet, licking her soles, and sucking on each toe. Kissing and licking her ankles up to her knees. Discovering how sensitive she is behind her knees. Up her thighs. Purposely avoiding her mound, I continued up her body, exploring her with my tongue. Her belly button, her fingers, arms, neck, and breasts. I gently bit her nipple, which caused her to cum instantly. I straddled her, my knees at her rib-cage, my now fully erect cock about to enter the gully between her breasts.

I slowly slid between her tits, and she responded by squeezing them tightly together. I began a rhythm between her breasts, and each time my cock's head would poke out from between her tits, she'd flick her tongue at it. She sensed that I was getting close, and pushed me back, wanting to be fucked in the conventional manner. I obliged her by spreading her legs wide, placing the backs of her knees in the inside of my elbow joint, and boring into her until our pubic hair intertwined. Again, I began a slow, long-stroking rhythm. Marcia crawled over and, with her back to me, sat on Gloria's face. I could see my own sperm oozing out of Marcia's asshole as Gloria licked Marcia's pussy. I started to cum again. My load being pumped into Gloria caused her to cum too, which caused her to bite hard on Marcia's clit, which caused her to cum, as well.

Spent and exhausted, we all just laid on the carpet, panting, not saying a word. Gloria was the first to rouse, crawling out from under me, and going behind me. I felt fingers caress my ass cheeks, tracing the welts now well risen from the brutal assault I had endured, but still soothing, with a cool to the touch lotion.

"You'll think of this day, each time you sit down for at least a week, Worm.", she whispered as she playful slapped my tender ass. The pain I felt as she touched my ass led me to believe that she was telling me the truth.

Standing up, Gloria led Marcia and me into the shower, where we spent the next half hour or so, lathering each other's bodies. I fucked Gloria in the ass while in the shower, while Marcia soaped our bodies.

After drying ourselves off, Marcia fetched my uniform, and handed it to me. I dressed, and was led to the door.

"We'll see you again." Marcia said as the door closed behind me.

"I'm sure we will..." I thought, as I realized that the apartment I had been held captive in all day, was the apartment directly below my own!