Hallowiener Pt. 09

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Dani's long night is not quite over yet.
6k words
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Part 9 of the 10 part series

Updated 06/13/2023
Created 06/04/2018
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Making my way gingerly down the path, trying my best to keep my weight off my bad ankle, I reached the back door. Falling back against the wood, I sighed deeply. My head was numb, and my body was aching. My ankle throbbed, and my ass was stinging even worse. I could feel Officer Millar's thick cum leaking down my thigh. It had been the most intense night of my life, leaving me battered, bruised, and more alive than ever. I felt awake. Sure, I was exhausted, but I was so wired. My mind replayed my session in the backseat of the Police cruiser in excruciating detail. Every thick inch of pain still vibrated through my entire body. The sting of the Officer's hand on my cheek and the deeper sting of his words both hurt in glorious harmony. Above all else, my feeling of deep satisfaction in helping a man so thoroughly in need of relaxation was a thing of beauty.

If I were honest, the idea of what I was becoming, what Becca was turning me into, left me conflicted. On the one hand, I was a heterosexual guy, and although still a virgin, eager to expand my experience with women. On the other, I was a boy offering myself sexually to bigger, stronger, older, and sexier men. These alpha men needed a way to work out frustrations that could otherwise hinder their mental well-being. However, I felt that tonight's escapade was indeed the first time I was at peace with it all.

How would the world view Officer Millar if they knew he was struggling with the day-to-day toll of police work? Would they still respect him? Probably not. How long would it take until he snapped? Could tonight have calmed him enough to last another month, two, six, twelve? I guessed it would be impossible to tell, but I felt he was a lot better now than if he hadn't crossed my path this evening. So what if I had to endure taking his massive cock in my ass? I reckoned the trade-off was worth it.

I slid down the door panel until my butt hit the stone step. It was cold but soothing on my sore cheeks. The Officer's business card dug into my ribs, so I pulled it from the waistband of my thong and smiled as I read it. "Oh, I'm definitely adding you to my phone, Dad--" Before I could finish, I was startled by the sound of a boot on the deck. I couldn't stop myself from screaming. Just a short peep of a scream but a scream nonetheless. I saw a large silhouette framed by the moonlight. "Oh, Daddy, I told you if you want to fuck again, you're going to have to let my pussy recover from your--" The figure stepped forward, and I froze. "--cock."

"Excuse me, young lady?" The voice was deep and robust. It was a voice I'd heard all my life. "You should be careful whom you proposition in the dark; you may not like the outcome."

At first, I couldn't speak, I recognised the figure in front of me, but my voice wouldn't cooperate. "Mr--Barber, hi--"

There was a pause. I couldn't see the face in the gloom. On the other hand, the person standing in front of me could see me very well. The moonlight shining down from behind him framed my figure, and I could tell he was taking in the scene before him, trying to make sense of it. "I'm at a disadvantage. Do I know you? And why are you half-naked sitting on my neighbour's stoop?"

"I--" I tried to speak, but I was still stunned by the sudden fright.

"Are you here to see Daniel? Because he's not here, no one is. Daniel was supposed to see his parents off before their trip, but he hadn't arrived home yet. When I saw the cruiser pull up, I thought something might have happened, and it was Daniel being brought home. Finding you instead was a tad surprising. Mr Barber's tone slowed as he took in the image before him. "I've been waiting for him for over an hour, that's when his parents left, and I'm damn glad they did. I don't know what Miles would have said if he'd seen you wander by speaking like that."

All efforts to speak failed, so I simply nodded in response.

There was a pause as silence filled the space between Mr Barber and myself. "Daniels' parents were worried about him. Do you know where he is?" Mr Barber stepped closer, placing a foot on either side of my own.

Realising that my neighbour's mistake may save me further embarrassment, I chose to play along. "I don't know, Sir. I was nearby when I hurt my ankle and hoped I could stay with Danny for a while."

"With a Police escort?"

"Y--Yes, that was Officer Millar. He--he found me in the park and took care of me. Excellent care of me." My mind started to wander again and a familiar heat burned inside me.

"What about your clothes?"

"What about them?" I said quietly.

"They don't leave much to the--" Mr Barber cut himself short and cleared his throat. "--imagination." I glanced at him, and his eyes roamed over my curled-up frame. When his eyes met mine, Mr Barber turned his back to me but made no move to leave. "Office Millar, that's what you said, correct?"

"Yes, why?"

"No reason, just curious which of my former Officers had been enjoying themself this evening."

Oh shit! I'd completely forgotten that Mr Barber used to be this district's Police Chief. "W--what do you mean, Sir?" I stammered.

"Don't play coy with me, girl." Mr Barber looked over his shoulder at me with a crooked smile. "I know how a girl like you gets grass stains like that on her knees."

I clamped my hands over my knees and ducked my head. "It's--it's not what it looks like." I don't know why but I began to tear up as I spoke, the fright of the evening's events finally catching up with me.

"Feeling guilty now, are you?" Mr Barber said, turning to face me again.

"I'm so sorry. I needed help. There was a gang. I hurt my ankle, and then Office Millar found me. I was grateful, very grateful. I won't do it again, I promise." I clambered to my knees and clasped my hands together as if about to pray.

Mr Barber paused. I still couldn't make out his features, but I could tell he was giving me one of his familiar sceptical glances. "A gang?"

"Yes. In the park. Six of them. They had me on my knees like I am now." I lowered my eyes and focused straight ahead, realising where I was staring. I quickly looked away.

Mr Barber's voice dropped to not much more than a whisper as he spoke. "I'm not surprised. The way you're dressed?"

"They made me, Sir," I said, snuffling through each word.

I'd known Mr Barber for years. He'd been friends with my parents long before I was born. This man had been a part of my life for as long as I could remember. As time passed, I became more aware that I needed to make amends. Although Mr Barber didn't know it was me, as I knelt in front of him, I only wanted his forgiveness. "They made me dress up."

"In that..." Mr Barber's voice trailed off as he waved a hand in my direction, "...lingerie?" We fell silent for a moment. "Do all girls your age wear such revealing lingerie?" Mr Barber's voice increased in volume. His tone had changed from judgemental to inquisitive.

"Sometimes--" My cheeks were burning, and I was embarrassed. Being illuminated as I was and my inquisitor being in darkness made this questioning more intimate than I had expected. "--when I need to."

"When you need to?" Mr Barber stepped forward once more. He was so close I had to crane my neck to look up at him. "Why would you need to wear lingerie like that at your age?"

"When my friend needs something," I said quietly. No one was in earshot of the two of us, but I still felt nervous that someone might overhear. "I do favours for her, to help her and--"

"And?"

"--Men."

Mr Barber paused for a long time. He cleared his throat before speaking. He, too, dropped his volume and whispered hoarsely. "Did you help that gang tonight? Is that what Officer Millar caught you doing?"

"No," I said louder than I meant to, clamping my hand over my mouth. "No. The gang forced me to get dressed like this. I think they were going to do things to me. But Officer Millar arrived before they could--get started."

"Get dressed? So, you were naked in front of all six of them?"

"No, I--I just put on the skirt and heels, but--" I caught myself, but I'd already said too much.

"But, what?"

"I was already wearing the lingerie."

"Oh, I see. Well, that ensemble suits you." Mr Barber coughed and took a half step back. My heart was racing as the silence pressed down around me. "I mean to say that they probably thought that, and that's why they wanted to make an exhibit of you...of your beauty."

Did he just call me beautiful? "T--Thank you, Sir." I was so thankful that the moon cast everything in a white light because my face must have been a bright crimson.

"I guess it was lucky that Officer Millar arrived when he did?"

I began picturing all those hard cocks and the exhilaration that ran through my body. I didn't consider it lucky at the time, but now, perhaps it was. "Yes, I guess so," I replied quietly, bowing my head.

"Do you know what they planned to do with you, Girl?"

I paused and swallowed slowly. "Yes."

Mr Barber placed a hand on my head and gently stroked my hair. "Tell me."

"They said they wanted me to," I looked up at Mr Barber, and he flicked his head to spur me on, "suck their cocks. Sir."

"That must have been very scary for a good girl like you. Perhaps they were teasing you?"

Oh god, Mr Barber just called me a good girl. "I--I don't think so, Sir." I was embarrassed and tired, and my butt was getting cold. The inquisition was starting to upset me, and my outburst surprised me. "They had their cocks out, okay, Sir. They weren't teasing. They were going to make me suck them off!"

Mr Barber paused and smiled. "Sssh, it's okay little one." He began to stroke my hair, "You're safe now. Officer Millar saw to that."

I was holding back my tears as I nodded. "Yes, yes, he did."

"He's married, you know?"

I didn't answer. I just looked up at Mr Barber with a quizzical look on my face.

"Officer Millar. You fucked a married man tonight."

I opened my mouth to speak, but Mr Barber placed a finger to my lips to stop me.

"You thought it was Officer Millar, didn't you?" Mr Barber said.

My brow furrowed and I tilted my head with Mr Barber's finger pressed to my lips.

"You thought it was Officer Millar tonight in the garden before you realised it was me? He was the 'Daddy' you were talking to, wasn't it?"

Mr Barber moved his finger and held my chin between his thumb and forefinger. "Yes." My voice turned to a barely audible whisper.

"Okay. Well, whatever happened between you, Officer Millar, got you here safely. We can both be thankful for that. Would you like me to call your parents or someone to let them know you're safe? It's a little cold to be walking around town dressed like that, judging by how you were hobbling earlier. I'm not sure you'd get far." His hand didn't leave my chin. He held my head still, my eyes locked with the darkness surrounding his face.

"They're all...away, Sir." I tried my best to act the part, something I was becoming increasingly good at I'd learnt. "I have no one to call," I said, adding a little sniffle.

"Well, we can't have you staying out here all night. God knows when that useless boy will turn up." Mr Barber's hand left my chin and cupped my cheek. His hand felt so warm that I couldn't stop myself from closing my eyes and burrowing into his palm a little. "Let's get you inside. I think I've got some hot chocolate in my kitchen. You can get warm while we wait. Sound good?"

It did sound good, except I knew Mr Barber would figure out who I was the second we got into a lit room. And I certainly wasn't in the mood to try and talk my way through everything with Mrs Barber. There'd be no hiding my secret if she found out. What would my parents say? "W--wait!" I exclaimed, grabbing the back of Mr Barbers' legs and shuffling myself forward. "I am a little chilly, but I'm happy to stay out here...just a moment longer. If--if you'd like?" I added extra emphasis on the last word and squeezed the back of Mr Barber's ample thigh. God, did this man ever stop working out?

I remember seeing him one summer in his garden. He'd stripped out of his shirt and continued working in a mottled old pair of trousers. He was almost seventy, but he was more jacked than anyone I knew. Although, that wasn't the first thing you'd notice about Mr Barber if you saw him shirtless. My dad had told me that when Mr Barber was a rookie officer, he had gone undercover with a biker gang. Back in those days, there were no such things as temporary tattoos, and to prove his loyalty to the gang, Mr Barber had covered the entirety of his upper body. I often wondered why Mr Barber wore such high collars and long sleeves, even in the summer, but after seeing him in the garden that day, I understood.

I wasn't opposed to tattoos, quite the contrary. I thought, on the right person, tattoos looked fantastic. Mr Barber wasn't the exception to the rule. His chiselled back was exquisitely detailed with every form of a naked woman, about twenty. Each lady was laid out in a circuit from his waist to his shoulders and back down, perfectly framing a large busty torso cupping her large breasts. As a kid, I loved the imagery for many reasons, but until this very moment, I hadn't considered there to be a different side to Mr Barber that I hadn't counted on.

"Oh...I see." Mr Barber turned to face me again and replaced his hand on my hair. "You know, you remind me of someone. Someone very dear to me."

I didn't speak, but my head shot up, and my eyes searched in the dark for his. I remained silent as he stroked my hair whilst I clung to his legs, kneeling.

Mr Barber shuffled his feet a few times, and I felt him getting nearer to me. "Cassie." He whispered. "Such a pretty young girl."

It took me a moment, but the second I realised that he hadn't said my name, my heart burst with relief. It felt as though I'd been holding my breath for hours. "Cassie, Sir?" I didn't need him to answer. I knew exactly who he meant. I think every eighteen-year-old boy in the neighbourhood knew her. She was Mr Barber's twenty-year-old daughter and the subject of many late-night fantasies in my bedroom. Not with her, of course, just me and my hand. But yes, I knew Cassie very well.

"My granddaughter. You have the same colour of hair. At least, it appears so in this light. You're certainly as pretty as she is, that I can say for certain. Although, her tits are bigger. Much bigger."

Listening to Mr Barber speak about Cassie like that turned me on. Something about the aura of dirty older men did something to me. "My ass is bigger, though," I whispered.

"What was that, Sweetheart?" Mr Barber said, hooking a finger beneath my chin and lifting my head upwards.

I didn't speak; I couldn't. The intimidation I was feeling was too much. I crouched forward onto all fours and pushed my butt out, catching it in the moonlight. "My butt. Is it bigger?"

A low, drawn-out guttural growl emanated above me, serving as my answer until he spoke. "On that, you have my Cassie beat." Mr Barber reached down and pulled at one of my skirt pleats with two fingers. I felt the cool air caress my cheeks. "You'd have most girls beat with that peachy ass."

The slapping sound was sharp and loud and took me by surprise. The pain tingled through my numb cheeks as Mr Barber clamped a hand over one orb of my ass and squeezed roughly. After the echoing slap was gone, the only sound that remained was light squelching, followed by my unrestrained moan. "S--Sir, p--please."

"Oh my, it sounds like Officer Millar really did have some fun tonight. Is that all his?"

"Y--yes, Sir."

Mr Barber's hand squeezed my cheek a few more times before stopping. When I expected him to straighten up, I felt a thick, calloused digit slip beneath the strap of my thong and run between my cheeks. The tip of this finger slipped inside my well-used hole with ease and was removed just as quickly. Without a word, Mr Barber lifted me back to my knees and presented his finger to my lips. I could smell the musky cream, and without provocation, I enveloped his finger in my mouth and sucked the dollop of cum clean down my throat.

"Now that's a slut." Mr Barber stood and wiped his finger on his trousers. "How old are you? Eighteen?"

"Yes, Sir," I said, suddenly feeling awake. As if Officer Millar's cum was some form of energy drink.

"Do you think Cassie is as much of a slut as you?"

I didn't know what to say to that. I didn't know her well enough to judge, but what I did know was where this conversation was leading. "Perhaps...with the right tutelage, she could be perfect, Sir," I said, hoping not to have crossed a line.

I was rewarded with another appreciative growl.

"I mean, all us girls need is a big, strong man to teach us how to be good. Isn't that right, Sir?"

Again no response was forthcoming. Mr Barber shuffled forward a few strides.

"I'm sure your Cassie wouldn't refuse a kind man who was only willing to teach and train her properly." I pushed myself up, placed a hand on Mr Barber's thighs, and stared into the dark again. "Wouldn't you like to teach and train a sweet, innocent little girl, Sir?"

I glanced forward at his crotch as he raised his hand and caught his zipper deftly between two fingers. I gasped as he dragged the little metal tab down. I could feel every corrugated notch vibrate through me until he reached the bottom.

Neither of us spoke for a long time. Our breathing, broken up by the occasional car passing by or the hoot of an owl. Mr Barber was stroking the back of my head as I bowed before him. Each time his hand reached my neck, I shivered. I closed my eyes and listened to the rustling of the soft corduroy of his trousers. His tone was finite, irrepressible. Soft but unnegotiable. "You're a sweet, innocent little girl."

The matter-of-fact way he spoke sent a sudden shiver down my spine. Was this his plan all along? What if I'd complained or screamed or fought back? I was suddenly conscious of the size of his hands and that although kneeling, my head only reached his mid-thigh. I knew Mr Barber was a large man. I just never really took notice of exactly how big he was. "Yes. Grandpa." Mr Barber's hand cupped my cheek and gently pushed a rogue hair curl from my face.

"There's my little Cassie."

Even though I'd said it, I was caught off guard. I'd never considered the pet-name Grandpa before, but Mr Barber calling me Cassie sent a jolt down my spine. "I've wanted this for a long time Grandpa. Do you think Grandma will mind?"

Mr Barber smiled and stroked my cheek. "Your Grandma doesn't need to know, little one." Mr Barber said, throaty and hoarse. I opened my eyes and saw his trousers' outline move. "She can't handle me anyway, never really could." I continued to watch dumbfounded as Mr Barber worked his belt. The catch sprung loose, and the belt splayed open. Inside his trousers shone a pair of bright, white shorts. His trousers, like always, were a loose fit, and they immediately fell to the floor.

My mind was racing far too fast to solidify a coherent thought. I watched on as Mr Barber's large meaty hand pulled at the elasticated waistband of his shorts. My throat was dry, but I tried to speak, stopping a second later when my vision was filled.

In one fluid motion, Mr Barber yanked down the cotton front of his boxers, spilling the contents out in front of my face. I gasped loudly and put my hand over my mouth, accidentally nudging one of his balls. The instant my knuckle came into contact with his sack, I could feel the weight of it. It was heavier than anything I could imagine. As the thought permeated my brain, I immediately pulled my hand from my mouth, and reached out to cup one of his testicles. "Oh god!" I said flatly; The weight was unreal.

Mr Barber laughed and stroked my cheek, moving his hand to the back of my head. A move I was all too familiar with by now. I wouldn't usually put up a fight, but I fidgeted for just a moment, and my resistance was all too obvious. No matter, Mr Barber's strength was too much to struggle against, and in no time, my nose was being tickled gently by his pubic curls. His scrotum's soft, crinkled skin gave way, and the instruction began. "Cassie, stick out your tongue for Grandpa. There's a good girl." I did so without hesitation. As much as I knew Mr Barber was a man of principle and law, my fate was sealed. What was going to happen this evening was now inevitable. I wasn't going anywhere. I didn't have a choice. And as the musky scent of his privates filled my nostrils, I was not sure I cared.

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