Cavity search

"H-How do you plan to do that?" You ask between gasps.

Alessa leans down and breathes hot cinnamon in your face. "I'm going to play your body like a fiddle, prisoner. Starting with a cavity search." She grins. "Well, more like a probe, really."

Your eyes widen with a mixture of fear and excitement as she smiles down at you with a predatory look and pushes an index against your chest.

"Don't go anywhere," she giggles as she cuffs your hands to one of the bedposts and leaves the room.

It's a few minutes before she returns, and when she does, just the sight of her is enough to strike you dumb. She's tall without any extras, so the three-inch thigh-high black leather boots she's now wearing make you look like a dwarf by comparison. Add to that the barely thigh-length satin skirt, the elbow-length vinyl gloves, the blue uniform half-shirt that exposes her midriff, and the officer's cap on her head, and Alessa looks the perfect picture of a slutty prison warden. The part that concerns you most, however, is the dent at the front of her skirt.

Alessa sees how your eyes widen as she approaches and interprets it as fear, quite correctly. For a moment, she breaks character with a look that's part reassurance, part pleading, and before you know what's happening, you give her a small, barely-there nod.

"Now," she says, "I'll have to be quite thorough. No telling what you could be hiding, or what others could be hiding in you, so...this could take quite a while."

You gulp. "Okay, ma'am."

"I'm sorry," she laughs. "Did you get the impression you had a choice?" She grabs your left arm and turns you over with a burst of strength, your restrained arms stretched out in front of you and your ass stuck up in the air. "Don't worry though."

A familiar warm, sticky sensation washes over your cheeks before it slides down to your back door, coating the outside with thick globs of lubricant.

"I'll start out gently."

You practically moan, "Thank you, ma'am."

A gentle, probing touch slowly forces its way inside you, a flash of pain nothing more than transitory as she starts to dig around in your ass with her gloved finger, occasionally brushing your sensitive prostate and sending a jolt of pleasure to your balls.

Alessa chuckles a little. "Turns out this might actually be unnecessary." She abruptly pulls her finger out and smacks your ass with her other hand. "You're so tight I doubt you'd be able to fit a cigarette in there. Guess your cellmate is as straight as they come."

"No," you say with no small amount of malicious glee, "he's just too scared to try anything."

"Scared," she laughs, "of you?" Another laugh and smack of your ass and thighs. "I really can't imagine why."

You manage to look back over your shoulder at her with a cocky smirk. "That's just because you think you're intimidating."

Alessa gives you a fierce look and smiles dangerously. "Really? Well..." she reaches toward her crotch and zips down her skirt, "guess you'll have to learn just how intimidating--" another, harder slap of your ass, "--I can be." Slowly, threateningly, she pulls her skirt down and steps out of it, revealing a black rubber strap-on roughly the size of your own dick, if a little narrower.

Predictably, your eyes widen at the sight of it, and she laughs again, rather cruelly.

"Relax," she orders, "otherwise this is going to be a lot more painful for you."

"I don't think this is official protocol," you protest weakly.

"Trust the system, prisoner," Alli orders again, more gently this time, as she rubs more slippery liquid into your ass and her tool.

You get her hidden meaning, and relax correspondingly, turning your head forward as you put yourself in her hands--literally. Slowly, a firm, insistent push is felt at your back door as Alessa spreads your cheeks with one hand while the other presses down into your back.

"Yes," she grunts as she slowly but surely presses into you, "definitely not a great place to store contraband. You'd get caught before it ever gets inside."

You groan in pain and arousal as you're pinned to the bed by her weight, her rubber tool inexorable in its conquest of your last virgin part. Sure, she'd stuck a finger or two back there on the occasion, but never outright fucking you. And if a few brushing glances over that spot had felt that good...

A low moan escapes your lips as the head of her dick finally makes it past the tight ring of your rectal cavity. More warm liquid spills onto your hole and slides in as she pushes further into you. The rest of her tool follows not long after, and within seconds, you feel the latex of her belt pressing against your ass cheeks as she bottoms out inside you. Your breath is hitched and tight, primarily in pain, and she mercifully just leaves it there, giving you time to relax and adjust to its girth and feeling. Eventually, she leans down, grabbing you by the neck and whispering in your ear.

"Now, relax."

Without further warning, she pulls back just a bit and thrusts back in. Then she does it again, and again, the distance between start and end of each thrust getting larger each time. More warm lubricant coats your asshole and washes in, filling your insides with slippery heat as you become more and more accustomed to the foreign object sliding in and out of your ass. About a minute in, Alessa pulls out almost completely, just the head still inside you.

"Ready, Mr. Tyreson?"

Your entire body shakes in arousal and fear and mild hysteria as you reply, "Yessss--AAAAGGGGH!"

With one smooth, powerful thrust, she bottoms out inside you, the thick rubber head not brushing, not stroking, but slamming your prostate on the way in. Your head whips upward, eyes flying wide open as all the breath leaves your lungs at once. Without giving you time to recover, she does it again, each thrust becoming easier and easier as you accustom yourself to her anal piercing. About a minute in, she stays buried to the hilt in your ass, surprising you a little when she loops both arms around your waist and bodily lifts you off the bed. Your restrained arms catch on the bedpost, causing her to growl and reach forward to uncuff your hands, then recuff them as she carries you--on heels--toward another piece of furniture in the room, a wooden bench with a frame to support your body while leaving gaping holes to allow access to your important bits.

A wide slot in its lower half permits your dick and balls a relatively safe, if exposed, resting place as you're laid face-down and you feel the strap-on in your rear move around a bit. Alessa's gloved hands come down to the sides of your hips, gripping firmly as she growls deep in her throat. And then she starts fucking the living hell out of you. Fast, powerful strokes drive your body into the bench over and over again, rocking the entire structure as she furiously pounds your rectum. Breathing is next to impossible for you at this point, and between the shock of the impacts and the absolutely brutal slams against your prostate, coherent thought is all but absent at this point.

All you can think about is the heat and pressure building in your body and the insistent, possessive grip at your hips that you're now reasonably sure has nothing to do with the fantasy and everything to do with the woman who's willing to fight and _kill _for you. Everything that's happened over the course of the day and the incessant thrusts against your prostate build up something breathtakingly powerful inside you, and before you know it, your dick is spasming and your body seizing up as it expels a load like a shotgun. Your breath is completely stolen, and for all your gasping, it doesn't want to return as Alessa keeps pounding away at you like a jackhammer.

The second orgasm follows rapidly on the heels of the first, and you manage a loud moan that takes all of your remaining breath. Much as your manhood is enjoying the absolute brutality of the situation, you're rapidly becoming aware that you need oxygen to live, so you try to suck in breath. It fails when Alessa grabs the shaft of your once-again hard dick, squeezes, and pumps it in time with her rapid, hard thrusts. You practically shriek when your third orgasm hits, a shrill noise coming from your throat as your eyes bug out and lungs empty completely for the umpteenth time. Genuine panic starts to hit you as your mind begins to cloud with the combination of **** pleasure and oxygen deprivation.

"Ah! Alessa," you gasp, breaking character. "I can't--can't b--"

Your breath is stolen once again as she releases your dick and grabs you by the neck, pulling your torso up and turning your head to claim your lips with hers, her hips never slowing down a bit. She kisses you hard, almost angrily before pulling away to hiss into your ear, her fingers firm but gentle around your bruised neck as her thrusts become ****.

"You--are--"

Alessa gasps hard, slamming inside you and reaching down with both hands to fondle your balls and rapidly pump your hard length.

"--miiiiiiine!"

You both scream in tandem as your swollen purple cockhead erupts for the fourth time in less than five minutes, and you feel a hard stream of warm liquid completely soak the back of your legs as Alessa squirts all over you and the bench. The combination of the brutal ass fucking, your helplessness, and Alli's possessive aggressiveness causes a hundred mini orgasms to occur as her hips spasm against you haphazardly over the next minute, both of you slowly coming down from your peaks in a boneless pile of sweat and sex. You're trembling all over as you feel her arm loop around your midriff, gently removing the strap-on from your ass and pulling it off as she uncuffs your hands and half-carries you to the bed.

You're still blinking back stars when she settles on top of you, naked save for her boots and hat and gripping your shoulders almost tightly enough to hurt. You hold her back firmly, willing yourself to become anchored in her reality and wishing this moment would never end.

The last thing you're aware of before you pass out is a tender joining of lips and tongues, and a firm, solid presence settling inside your chest.