I had made a promise to pace myself with Lilly. That I would take my time and not overindulge.
But if you break a promise to yourself, does it really matter? At least that’s what I told myself as I moaned with satisfaction, my cock pumping a load deep into her warm, wet muff.
No roleplay, no buildup. I went home with schoolgirl Lilly’s amazing blowjob on my mind and just got hornier and hornier till I couldn’t stand it. And why masturbate when I could fuck?
I had entered her house before midnight, Lilly’s sticky plaid costume from earlier was piled on top of a laundry basket in the corner of the room. I had briefly considered ordering her to put it back on, but found my desperation had outpaced my kinkiness.
She had been reading another story in bed when I arrived. The charmingly titled ‘Toilet Slut’ brought a strange fantasy of pissing in Lilly’s hair. My short time with her had induced queer changes inside me. All these taboo sexual acts I would never have considered suddenly warranted reexamination when Lilly handed me her contract.
It seemed there was a lot I had written off in my mind. Yesterday I played a very dark role as the blackmailing teacher forcing his student to submit. A few weeks ago, I would have thought such fantasy with blurry consent and abusive power dynamics was… well… evil. Gross. Disgusting.
But I had liked it, I liked it a lot. It was something I probably always wanted, but my Catholic guilt wouldn’t let me admit it to myself. I would never have been able to ask a girlfriend for what I made Lilly do. Now, anything seemed possible because I’ve come to terms with a fact I’ve been denying my entire adult life.
I’m a sick pervert. Fucked up shit got me off. And now I need to look up this ‘Toilet Slut’ story and give it a read, because maybe I am into watersports. The only way to know for sure is to piss on someone.
No, not someone.
Lilly. My personal toy. My plaything.
That sort of naughty exploration was pushed aside for another day’s scrutiny. Now, I just wanted to fuck. I had simply grabbed her by the hips, bent her over the side of the bed, and pulled down her sweatpants. She didn’t even put her book down, not that I minded. She propped up on her elbows and licked her finger before turning to the last page of her story. I had blown my load incredibly quickly. Something about the way she didn’t even regard me as my sex dripped down her thighs was oddly satisfying, and I had already begun fucking her again.
Bracing herself for my erratic thrusting, Lilly closed her book and slid it forward before lying flat on her front. Her hands seemed to move with practiced precision as one went to her tits and the other slid between her thighs. She shut her eyes and began playing with her nipples. I felt her finger slide along my shaft, fingering herself at a much faster pace than the pounding of my hips against her backside.
That animalistic low growl of an orgasm started to build. I wondered if it had anything to do with me. Was she turned on by the way I screwed her, or was it the adventures of ‘Toilet Slut’ that was getting her off? I soon had an honest answer to that question. I came again, enchanted by the rippling of flesh when I slammed against her ass. Pulling out, I sprayed cum across her back. Lilly was unfazed by the sudden removal of my dick. She was more than content to continue her fingering and fondling just as she had when I was screwing her, proving my cock to have been an unnecessary element to her pleasure.
My drooling cock spent, I pulled up my pants and left her to her increasingly loud self-pleasure as I wandered back into her closet. I decided I would visit her tomorrow before Betty’s party. And I wanted to explore more of what she would do when playing out a role.
I found myself sorting the clothes, putting the outfits I preferred on the left and pushing the ones that didn’t quite strike my fancy to the right.
Adult baby, right. Nun, left. Stewardess, left. Army fatigues, right. Cop…
Hmm, the cop uniform had promise. And it would let me test out Lilly’s range. She had played such a good little schoolgirl, and this whole arrangement had seemed to indicate she enjoyed a submissive role. But what would happen if I wanted her to take the lead?
From her room, I heard the loud bestial grunting of her climax, followed by the diminished sounds of her growls winding down. Seemed like she had finished. I collected the uniform and headed out. She was still face down on the bed, my cum running down her back and slowly toying with her pink snatch. I tossed the clothes next to her on the bed.
“I’ll be coming back in the morning. I want you to be wearing that, and then let’s do a little cop and criminal roleplay.” She didn’t look at me, nor did she stop playing with herself. But my question at least warranted enough interest for her to lift her head and look over what I picked.
“What crime?” Her voice was low, breathy as she rolled onto her back and lifted her bare feet and planted her heels under her ass. Her toes clenched the sheets, and she didn’t wait for me to express my confusion. “You said criminal. Robber? Stalker? Peeping Tom? Or… worse?” Her dark eyes flashed accusingly at me.
“No, not… jeez. Just a burglar, robbing an empty house. And you’ll come along to stop me.” I shouldn’t have been stunned by how dark her mind went, but the accusation was still unnerving.
“Power dynamic. Who’s the dom?” Right to the point.
“You’ll be fucking me. I want you to be caught, used for sex, and let go.” I smirked, watching her push a second finger into her pussy. She was never sated, always wanting more long after I was done with her. But was it that this conversation made her more horny, or was it simply incidental?
“How long have I been a cop?”
The line of questions, like before. It was part of her process, and it turned out so well last time that I was thrilled to answer. In fact, her questions were becoming part of the fun. I decided to treat it like word association and just give her the first answers that came to my head. “Five years.”
“Have I fucked prisoners before?”
“Yes.”
“Have I ever gotten in trouble for it?” Questions like that made me wonder how the answer would change the roleplay. Maybe I’ll do the same roles again sometime, changing my answers to see how it alters her character.
“No.”
“Do I regularly abuse my power?”
“Of course.”
“Am I violent?” I couldn’t help but chuckle. Lilly was at least a head shorter than me. She was also so complacent. The thought of this slight, quiet woman being a brutal cop was ridiculous. All the more reason I wanted to see how it played out.
“Yes.”
“Sadistic?” Again, I laughed at her.
“Yes.”
“Will you be willing?” Now that was interesting. I’ve never once considered myself submissive. But the thought of being taken and fucked against my will, that made the hairs on my arm stand on end. That, or it was the way Lilly ground her bushy cunt into her hand.
“No, I won’t be.”
“Sure about that?” Her fingers stopped, her dark eyes opened, burrowing into me like she might find an answer by staring into my mind. I worked hard to suppress my amusement. Was she worried about me? Or did she feel as ridiculous about pretending to be this sexually deviant police officer as she should?
“Yeah, I’m sure.”
Her dark eyes widened. “Really?”
“Fucking yes! Really! I didn’t see the part in the contract where you try to talk me out of what I want.” She nodded, and her fingers resumed squelching into her cunt. Her dark eyes closed, and suddenly it’s like I wasn’t even there. With that, I left her alone.
——————————————
I got home and grabbed my phone from the charger. I could smell Lilly’s sex all over me and knew I would never be able to sleep until I had taken a shower. I went to turn on some music to help calm me down before I scrubbed her from my skin, and noticed I had several texts from Betty.
‘Better be coming tomorrow.’
‘No flaking.’
‘Tits and music.’
‘Don’t be a bitch.’
‘Bring cups.’
I texted her back, ‘Red Solo cups, heard. I’ll be there.’
Why was I keeping Lilly from her? As the hot water ran over my tired body, the question was eating at me. At first, I was just embarrassed. I thought Lilly’s contract had to be part of some obvious scam that I was too dumb and horny to see. But now that I knew it was real, why was I really keeping it from her?
Then I thought of yesterday. The way she teased me. I thought of the feeling of her nipple piercings against my chest. Or how she ran the stud in her tongue up my fly just to watch me squirm. The answer was quite obvious; I liked the attention. I liked the way it was driving her up the wall. And for once, Betty was absolutely crawling all over me. Hell, I found my hand grasping my cock as I thought about her, instinctively fondling myself as the hot water poured into my hair.
She had been an obsession for years, this sexy metal head who should have been too fucking cool to even talk to me. We never would have met if she weren’t stuck with me eight hours a day. And the stories she carelessly shared were stuff I would have never imagined anyone really doing. She was an absolute slut, ready to fuck anything that interested her.
But not me. It was clear she didn’t see me as another fuck buddy. No, I was a toy she liked to wind up. Betty enjoyed the tease. She liked laughing at how ‘pathetic’ my love life was. She simply giggled as her lewd innuendo and flirtatious taunting made me so fucking horny it hurt. But something about the mystery of my free use contract was getting to her. I shook my head, realizing I was tired and I would be fucking Lilly in the morning. No need to push myself for another orgasm now.
I stepped out of the shower and started drying myself, noticing I had another text from Betty. ‘Feel free to bring the girl you’re fucking.’ The thought of poor, quiet Lilly being dragged into a crowded, sweaty room with painfully loud music pumping and a sea of people crushing into each other was comical. It would break my poor little shut-in.
‘What girl?’ I texted back, making sure to stoke the flames of her curiosity. ‘Thought you said there would be girls there.’
‘Oh, I’m sorry. My friends won’t fuck big lying pussies.’ I didn’t take her bait, though something about it burned me up. I set the phone down and set an alarm to make sure I didn’t keep Lilly waiting in the morning. I didn’t bother putting on pajamas, just crawled naked into the cool sheets. I closed my eyes, only to have my quick slip into slumber subverted by my phone vibrating with a new message. ‘Dirk says hi.’
It came with a video. I hit play, expecting to see Betty waving with her rocker boyfriend.
“Fuck, that’s a good bitch! Oh fuck! Fuck!” Dirk’s gravelly baritone voice was breathless. The image rocked as Betty looked up into the camera. Dirk’s large hand (the one not holding the camera) gripped her fried, bleached hair as Betty gagged and dragged her lips down an impressively large cock. Impaling her throat, she pressed her lips flush with the base of his knob. It sounded like she might throw up as Dirk repeatedly shouted, “Fuck!”
Betty pulled her head back, sticky strands clinging between her worn and smeared black lipstick. She looked up into the camera with a mischievous grin. And then, she spoke to me as Dirk convulsed and sprayed ropes of cum across her face. “James, don’t forget to bring my fucking cups. Dirk, say ‘hi’.”
“Ha! Bee, you’re so fucked up sometimes.” Dirk turned the camera to face himself. Neck tattoos, eyebrow and nose piercings, and a handsome, stubbled face. He looked every bit the rocker he was. “Yo, James! Long time, no see. I’ll catcha ya tomorrow, brother!” He threw up the horns and stuck out his tongue before pointing the camera back down toward Betty.
She was dripping with his cum, an absolute look of perverted bliss on her face as she took his balls into her mouth and coaxed more of Dirk’s mess to drip down into her ratty hair. She raised her middle fingers and flicked me off.
“Guess that’s B’s way of sayin’ see you then.” Betty’s teeth bit down on the skin of his scrotum, and she leaned back, stretching the thick skin as his dick shot another load of cum into the air. “OW! Fuck! You’re in for it now…” And the video went black.
Betty had made sure my satisfaction was thoroughly destroyed, and the hunger roared back. I thought of going to Lilly’s again. But I already had plans with her later. So instead, I watched the short video. Spitting in my hand and stroking my cock, I paused the picture on Betty’s semen drenched face and used that image to coerce a new load of spunk onto my belly.
Fuck, I wanted to be Dirk. I should have learned to play a guitar.
——————————————
Time for my little experiment to play out. I woke up early, my excitement making the alarm unneeded. Realizing I didn’t give her an exact time, I paced around my house to give her what I felt was a fair chance to get in uniform. But Lilly had a routine. She was up before I normally left for work and showered. So I took some time to prepare.
I went through my winter clothes and found my black balaclava. I was trying to decide what else I should bring. A large sack with a painted dollar bill seemed too on the nose. I considered what I would take if I really were to rob Lilly’s house. I kept thinking of things like a crowbar or a knife. Nah, all more trouble and danger than they were worth for this sort of game. So I just swapped into a pair of dress pants and a long-sleeve t-shirt, covering myself in black like a cat burglar.
Even though our street was pretty much dead, I still felt like everyone was looking out their windows watching me. This wasn’t a front door sort of game. I hopped over the fence separating our houses, finding her backyard as unkept and overgrown as her crotch. I fell into waist-high grass. It was deceptively tall, and I kicked a rock and tripped, letting out a surprised yelp and falling over. My criminal career was off to a pathetic and loud start. I stood up, blinded by a misaligned balaclava, which I straightened before stalking up the cement patio to the back door.
I slid the key to the house into the lock. I had thought about sneaking in through a side window or sliding down into the basement through one of the awnings. But I had pictures in my head of some random person driving by, seeing that, and calling the actual cops in to spoil my fun. So with a turn of the key and more effort than I was expecting to open the obviously long-neglected back door, I slipped into the house.
I looked around the kitchen, but there was no sign of her. I wondered how she would do it, if she would be just sitting there just waiting to catch me. Maybe I was too early, and she wasn’t even ready yet. I figured if I just wandered around a bit pretending to steal some stuff, it would give her time to figure it out. Couldn’t help myself, though. I peeked in her bedroom, hoping to catch a glimpse of her. There was a large lump covered in blankets, just like how I had seen her sleep before.
The sensation of stalking around the house in a mask, checking her bedroom, made me think back to Lilly’s suggested crimes. ‘Stalker? Peeping tom? Or… worse?’ An overwhelming dark urge gripped me. Taking her when she slept, cupping my hand over her mouth. It was completely within the bounds of the contract after all, so why shouldn’t I get a little nasty with it?
Maybe I could still change the script? I had been thinking of Lilly’s ass. I’ve never done anal before. Truth is, it made me a little nervous. But nothing shakes the jitters away like non-consensual consent. I felt myself bulging in my pants thinking of butt fucking Lilly. And I slowly cracked open the bedroom door and crept closer. Guess I had gotten here before she was ready. Too bad for her, she slept through her chance to play police. Something evil in me wanted a chance to come out, and I was going to take her just like this.
I realized as I got closer, there was a stillness to the mound of bedding. Too still, there wasn’t anyone there. Just clothes. So Lilly must be elsewhere in the house. But on the bed was her underwear. I couldn’t help myself. At first, the intense smell of her cunt had rattled me. Now I was quickly growing addicted to it. I picked it up, a few dark pubes clinging to the white cotton. I held it to my face and inhaled deeply.
“Freeze, fuckin’ scumbag!” Lilly’s voice made me jump out of my skin. It was loud and in an affected southern accent. I tried to turn around when something painful cracked off the back of my skull. My stomach sank, and my legs gave out. I would have dropped to the ground if Lilly hadn’t shoved me forward onto the bed. “Looks like I caught me a fuckin’ perv boy. You like stealin’ panties, you sick little cock sucker?”
“Lilly?” She was climbing onto my back, my head still spinning from the hit. I shook my head, trying to clear the cobwebs left by the blow. “Get off.”
She drove her knee hard into my back. I wasn’t expecting my scream, and I realized I was feeling legitimately scared as she slipped a tight pair of cuffs on one wrist, then the other. “That’s Officer Redwood, jerk ass. And ya done fucked up. You in here lookin’ for a girl? What were you fixin’ on doin’, boy?” I squirmed helplessly under her weight.
I tried to calm myself, realizing Lily was playing. She was following the script I laid out. So despite the fact that my neck was killing me, I joined in. “Fuck you, fuckin’ pig! Take these cuffs off, and I’ll show you exactly what I was planning!” She got the drop on me, but I thought since she was still much smaller than me, I might be able to turn things on her yet. I fought against the cuffs, hoping they were some cheap toy meant for kinky play. The chains held, and the metal dug into my skin as I struggled. They were real, and for my vain efforts, I was rewarded with a slap to the back of the head.
She rolled me on my back, my hands pinned underneath me. “Aw, come now, boy. Keep givin’ me attitude, and ya might find ya bit off more than you can chew.” Lilly had changed again. She wasn’t herself. And she certainly wasn’t the meek little schoolgirl who sucked my cock yesterday. No, she embodied her new role. As she snarled and smacked her palm with the large metal flashlight, it hit me. Lilly was one fucking terrifying cop.
The uniform was skin-tight on her. It was a costume piece, more fantasy than reality. The navy-blue jumper was low cut, the cleavage of her full tits spilling out, and the zipper couldn’t get over her full breasts. The hem was so high on the hip-hugging skirt that I could see the pubic hairs poking out from between her legs. She wore a policeman’s cap with a silver plastic badge that matched the one on her chest.
She had accessorized, too. Black leather thigh-high boots, laced all the way up, with the meat of her leg pouring from the top. A black utility belt with more handcuffs, a radio, a billy club, and a gun, which her hand slid down her side to. I nearly wet myself as she pointed it at me, the business end of the firearm making me forget this was supposed to be a fantasy.
It was only when the barrel was pointed square at my cock that I noticed the plastic orange tip to indicate it was clearly a cheap toy. “Now, am I gonna have to strip search ya, boy? I mean, you’re already breakin’ into a lady’s house and sniffin’ panties like a fuckin’ dog. Can’t right believe you to be a peaceful sort.” She reached for the balaclava and mercifully removed it. It had grown sweaty and itchy. “My, pretty little thing, ain’t ya?”
Fuck, this was working for me. Fear and sex, I’ve never felt them both before. “You… You can’t touch me, bitch! I know my rights!” I spit at her, a motion that agitated the aching pain on the back of my neck where she hit me, probably with the flashlight. She hadn’t held back. “I want my fucking lawyer!”
“A fuckin’ lawyer? Tender darlin’, they all’re fuckin’ lawyers. Livin’ their lives just lookin’ to screw ya up the ass.” She reached down and grabbed me by my shirt, pulling me to the edge of the bed in a sitting position. “But I don’t think you want that. I think you want me to let you go. Cause after all…” She reached into her belt and pulled out a baggy. It was full of white powder. Sugar, maybe flour? “I found all these drugs on ya durin’ the pat down. At least that’s what the report will say. That’s more than enough to put you away for a decade.”
Hell, she had taken what little I told her yesterday and formed an entire scene. I had given her time, and she planned this out. This wasn’t my fantasy anymore. It was hers, and I was just playing along. And damn, did I want to play. “That’s bullshit! You planted that!”
“And who do you think the judge is gonna believe, little man?” Lilly swatted at my crotch with the plastic gun, making me wince in pain. “But you’re a handsome thang, ya know that? Maybe we could come to a lil’ arrangement? You do somethin’ nice for me, and I let you walk out of here with just a hard lesson learned?”
There was something slimy about the way Lilly spoke. A flash of pure, cruel perversion in her eyes. I never would have thought a woman could make me feel this way, but I felt helpless and dirty. “What? No! I’m not going to fuck you! Fuck off! Just take me in, pig!”
I wasn’t ready for the hit. She reached across her chest and backhanded me across the face. With a yell, I tumbled to the ground. Lilly wasn’t holding back. “Wrong answer, shitbird. This is fuckin’ happenin’. Now let me tell you, you’re gonna feel a lot better when I’m done if you can tell yourself it was your decision.”
My stomach churned. I could feel my eye swelling. I remembered what Lilly had asked yesterday. ‘Sure about this?’ And suddenly I wondered if she really would stop if I told her to. Or if I begged her. Was she too deep in the character to pull back?
My body was shaking. My breath was choppy. “Lilly… fuck. I… I…”
“Darlin’, that’s Officer Redwood.” She bit her lower lip as her fingers began opening my pants. I helplessly froze up under her carnivorous gaze.
I’ve never truly felt like that before, helpless. No matter how I struggled, I couldn’t get out of the handcuffs. Lilly was taking this dead serious. Despite the pornographic outfit, she was committed to the role. I had started this. This is exactly what I told her I wanted. And now, it was happening. “Officer Redwood, please. Please…”
She pulled my slacks down. My cock had softened, but Lilly wasn’t going to let that stop her. “Oh, sweety pie. You cryin’? Don’t be like that.” She pushed the palm of her hand against my balls, her fingers lightly running up and down the bottom of my shaft as I began to stiffen. “There ya go. Deep down, all little boys want a good fuckin’. Yer cock knows it. Now, I’m gonna give you one more chance. Ya gonna give me what I want? Or am I gonna take it and then wind up arresting you anyway?”
She dropped to her knees, straddling me. Warm drippings of her sex fell from her wet pussy onto my dick, which she massaged it into my staff with her fingertips. She was right, no matter how frightened I was my body reacted longingly to her touch. And I was too scared to find out what would happen if I told her ‘no’. “I’ll be good, Officer Redwood.”
A sadistic smile spread over her face. “First fuckin’ smart thing you said, ya filthy little hooker.” Not content with just my submission, she wanted my humiliation too. She reached to the strained zipper between her tits and pulled it down to her navel. Grabbing me my hardening cock, she lowered herself down onto it. Pushing her shoulders back, her soft tits burst from the fabric as she grunted in pleasure.
The position was painful, I tried to flatten my bound hands behind my back as much as I could. As she rode me, each bounce sent a jolt of pain through my arms. “Please, this hurts.” I whimpered. “Can we get on the bed?”
She drew her hand back, and I flinched, ready for the next hit. Instead, she caressed my cheek and laughed. “Darlin’, beds are for respectable, law-abiding citizens. You’ll fuck on the ground like the dirty fuckin’ criminal you are. And keep those perdy eyes on me. I wanna see you lookin’ at me when you cum.”
Officer Redwood road me all the harder. I wanted to climax quickly, but the pain and the reluctance confused me. My mind spun in a tangle of conflicts. Her tits bounced and rippled as she bounced her hard on my cock. Slapping me, telling me what a lucky slut I was, made me thank her as she wrapped her hand around my throat. Lilly pushed the toy gun under my chin and made me moan and tell her I liked it. And I think I did. After all, I’ve never ejaculated that hard. Let alone from a confused, partially softened cock.
Triumphantly moaning as her ravenous pussy claimed my cum, she leaned forward, and her breasts dragged against my shirt. “Havin’ fun, little boy?”
Weakly, I nodded and squeaked out, “Yes, Ma’am.”
“Made an awful mess down there, didn’t ya?” She squeezed her cunt, and I squirted again inside her. “Why don’t ya clean me up, then I’ll send you on your way with a warnin’.”
Clenching her pussy tight, she stood up as my spent cock was squeezed out and pathetically dribbled. Officer Redwood dragged me to my knees by my hair and sat on the edge of the bed. Reaching for the police baton from her belt, she playfully slid it across my cheek. It wasn’t a wooden weapon, but a plastic prop. Part of me felt relief, but that look on her face still frightened me. Still wouldn’t let my body fully believe this wasn’t real.
“Remember slut, you better do a good job. ‘Else I’ll knock them fuckin’ teeth in.” With that, she spread her legs. I only had a moment to really look at it. My cum was like spiderwebs in tangled, dark bramble weed. It oozed from her slit. And all I could do as she jerked my head into her lap was shuffle my knees underneath me to maintain my balance.
I licked and lapped up my semen from her. She loosened herself as she pulled my face in close, spilling more seed out for my consumption. I was forced to reclaim my temporary deposit as her legs spread wider and dribbled into my mouth.
“Eat up, you dirty bitch. Every god damned drop.” I thought of how I made her suck my cock yesterday. How I had delighted in the way cum and drool ran down her chin and wondered how I compared to that now. Was this revenge? Tit for tat?
No, I don’t think Lilly’s mind worked like that. There was an practicality about her, she did what she was told. I couldn’t blame her for the disgraceful feeling of my own sticky juices running down my throat. Lilly even tried to warn me.
She tapped the club against my head. “Eyes on me, don’t you dare fuckin’ close them.” Grabbing the back of my head, she held me still as she ground against my face. My tongue and lips flailed desperately to bring her pleasure. Her dark eyes consumed me, her large thighs squeezing against the sides of my head. It was getting harder to breathe, and she only seemed more excited by my panic.
Finally, Officer Redwood erupted with a roar. She gradually released my hair, letting me gasp for air, but I didn’t dare stop eating her cunt until finally she drove her heel into my back. I collapsed back and sucked in air. “That’s a good lil’ fuck boy. Exactly what I needed.”
Something inside me felt like crying, and somehow that felt good. It was like a dam inside me burst. And what came out were tears of humiliation. But they weren’t just from what Lilly did to me. Shit I never knew was there bubbled to the surface and ran out and down my cheeks. And Lilly grinned. Watching me blubber at her feet till I could finally ask, “I did what you wanted. May I go, Officer?”
A sadistic pleasure was dripping from her voice. “I dunno, seemed like you enjoyed yourself too much for it to be a lesson. But I guess you’ve been a good boy. Bend over, I’ll take off your cuffs. Then you can get on out.”
It was harder to do than I realized. My body felt weak all over, completely spent. I could barely hoist my chest onto the bed. The second I landed in that vulnerable position, my ass exposed, I realized I had fallen for her last trap as her hand pressed down on the handcuffs and pushed them into my lower back, pinning me in that position.
“Listen here, cunt lick. This here is my town. And I don’t want to catch you breakin’ in no more lady’s houses.” I felt her grab my ass cheek and spread it painfully far apart from its twin. The end of the plastic billy club pushed hard into my asshole. “Consider this a preview of what pretty boy’s get in prison.”
I screamed, the foreign sensation rattling my senses. I could feel my treacherous cock swelling as she pushed the club harder and harder into me, forcing my tight anus to relent to the strain of Lilly’s assault. I tried to loosen myself, but my body fought against the intrusion. The pain was shooting through my back as I arched and tried to do anything I could to take it.
“Remember this, next time you’re thinkin’ of doin’ somethin’ unsavory. Your ass bein’ used every single fuckin’ day by all those fuckin’ horny prisoners. And you’re a crier. They like that, boy. Oh, they’ll use you till there’s nothin’ but an empty heap of fuck.” She pushed the club hard one last time. It penetrated me, and I felt cum squirt from my cock. My entire body was shaking as she lovingly gave me one last spanking. “Now, next time I catch you I won’t take it so easy.”
With that, she reached into her belt and finally took out the silver keys. She freed me, though I couldn’t move. She left the club in my ass, and Lilly walked around the bed. She was shedding her uniform and the sadistic Officer Redwood with it. There was needful urgency in the way she stripped. I couldn’t bring myself to move from that spot, my limbs barely moving as I tried to will myself up.
Her naked body hopped back into the bed. I turned my head to watch her. She spread her legs wide and brought a thick vibrating wand from under a pillow to her cunt. And I stayed right there, a hard piece of plastic jammed up my ass, bruises and red marks around my wrists, my eye starting to swell. Watching Lilly desperately grunting with a spastic combination of fingers and the vibrator.
Somehow, that brought me back through the confusion. And even though I wasn’t sure about it at the time, I knew now that I had liked it. All those terrible, weak feelings of being controlled and used excited me. The tears running down my face brought a cathartic relief. I reached behind me, pulling the baton out, and limped away from the bed.
Lilly was still masturbating when I shut the front door behind me. She enjoyed her role as well, it seemed. As the sunlight poured from the sky, I had a floating sense of satisfaction I had never experienced before as I gingerly walked to my driveway. Like something heavy had been burned out of me.
Then, to my horror, I saw the rusty old black van I knew all too well sat in my driveway. My instinct was to run. But it was already too late.
Click. Click. Click. She was sitting on my porch drinking one of my beers.
Betty, her hair freshly colored with sea foam green dye and laying messily down her shoulders, had her eyes fixed on me. She looked me up and down with a shit eating grin. “Rough night with your online girlfriend?”
