Annie Holder's House Pt. 05

Story Info
An old man punishes an older woman and a young man.
4.1k words
4.43
32.6k
7
0

Part 5 of the 8 part series

Updated 06/08/2023
Created 10/31/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
maximpact
maximpact
34 Followers

Recapping on the account of my time at Annie Holder's house, Annie was a widow in her late 60s and Eddie, her neighbour, was in his mid 50s.

I had been a bit of a nuisance to them both when I was younger, and now at 19 they had the upper hand on me.

Through their own network of contacts and by telling over-inflated stories of my harassment they had made me consent to being punished by them in return for their silence.

The punishments had been largely of a sexual nature. In addition, Annie had progressed to having me serve her own sexual needs. Eddie's role in my punishment had been in assisting Annie. He was eager for his own form of retribution.

Throughout all this, tensions had risen between the two of them. On this particular Saturday morning I was in an outbuilding in Eddie's garden, strapped naked to a wooden bench so that he could punish me himself.

"So, when am I supposed to keel over? About now or do you reckon it will take a bit longer?" " Eddie asked, adding, "Well, answer boy, it's what you planned so when is it supposed to happen?"

"I, I don't know what you mean." I stammered.

The door creaked open, and in walked Annie, her face like thunder. "Right on time," laughed Eddie, "He was just telling me he knows nothing about why I should be on my back holding my chest by now."

"He's played you for a fool, Annie. He thinks he's got the upper hand as usual. I told you, give him enough rope and he'll hang himself and he has."

Annie turned to face me, "Eddie said you were just waiting for the chance to get back at one of us. I didn't want to believe him!"

"You'll bloody well believe me now, Annie!" blurted Eddie, "Go and find his clothes and go through them. You'll see what I mean!"

Annie left to find my clothes. I knew what she would find and her reaction to it.

When she returned her face was ashen and she looked down as she approached Eddie. She spoke with her voice quivering, "I'm so sorry Eddie. Believe me I had no part in this. She produced Eddie's pill bottle that she'd found in my trouser pocket and passed it to Eddie.

Eddie produced the pill bottle I'd swapped from his pocket. "Mrs Holder's name is on this. It came from her bloody medicine cabinet and you swapped it for mine!" He opened it and shook out a few tablets, palming them then putting them in his mouth and seemingly swallowing them. He spat them out into his hand and showed me. "Did you think I was too stupid to spot you swapping my tablets for bloody amphetamines? I caught you out big time, boy!"

"Your fingerprints are on both bottles, you little bastard. I've got you bang to rights. All I have to do is fake a heart attack and I've got enough evidence for you to go down for a long time!" He took a small polythene bag from his pocket and put both bottles in.

Annie looked resigned as she spoke, "I'm sorry Eddie. I should have trusted your judgement and not let him fool me. You'd best go ahead with what you want to do with him."

"Oh I will, and you'd better change your attitude too Annie! What with your fingerprints on both bottles, and the question of how you've got them. There's going to be some changes, big changes! We'll deal with that later, won't we?" snapped Eddie.

Annie stammered, starting to answer but deciding not to. She looked sheepish as she eventually gave a resigned answer, "Yes, we can talk about that later." Eddie's tone was much more malevolent towards her as he responded, "Good, because you've tried to brush me to one side on this and make it all about you. I can make trouble for you too. You'll not be trying to cut me out in the future will you?"

Annie looked shocked at his outburst and replied meekly, "No, and I wasn't trying..." She was interrupted sharply by Eddie before she could finish., "Save your breath, Annie. You're best to just go along with what's coming and accept what's due!"

Annie walked over to the front of me. She put her hand under my chin and grasped my lower jaw pushing it up so I looked upwards at her.

"You've had me fooled but not Eddie. You were just waiting for a chance to have a go. You've shown me up and now we'll both pay Eddie back. You'll wish you hadn't done this!" Annie spat in my face as she finished the sentence.

Annie stood next to Eddie and spoke to him. "If you don't mind I'll watch you birch him, Eddie. I won't interfere."

Eddie laughed, "Oh yes you're going to stick around for everything I've got in store for him, then it's your turn!"

Annie looked aghast but didn't speak, perhaps too shocked by what she'd just heard. Eddie continued, "I'll deal with you after him then I'll be telling you what to do to get things sorted out for tomorrow. I said there's going to be big changes and they start now, so come and stand here!"

Annie moved to where Eddie pointed, directly in front of me and stood, looking quizzically at Eddie.

"Right, now strip!" Annie looked aghast at Eddie's demand, "Come on, don't take all day about it, strip yourself naked! Don't make out you're shy because I know for a fact that he's seen you naked so get your clothes off, now!"

Annie looked scared and bewildered as she took off her coat and looked around for somewhere to put it. Eddie handed her a plastic coal bag. "It's clean enough, put everything in this!" he ordered. She folded up her coat and pushed it in the bag to the bottom. She reached down and pulled off one of her black slip-on shoes. "Put them in the bag and stop wasting time," said Eddie.

Annie looked as though she was going to question him but didn't and placed the shoe in the bag then did the same with the other one.

She unzipped her dress behind her neck and looked at Eddie as she exposed one shoulder, bare except for two off-white straps. "Please Eddie don't do this." she pleaded, "Please don't make me."

Eddie laughed, "You should have thought about the consequences when you were having your fun at my expense, Annie. We haven't got all day so get your kit off and in the bag!"

Annie shrugged both shoulders out of her green and black dress and let it drop to her waist. Her off-white slip covered her bra. She pushed the dress down and stepped out of it, folded it and placed it in the bag beside her legs. She pulled the slip over her head, folded it and bagged it then rolled down her tan tights, balled them up and placed them in the bag too.

Her wrinkled belly flesh hung over the waistband of her big off-white panties, matching the wrinkled flesh of her cleavage. She gulped and averted her gaze from both of us as she reached round and unhooked her bra, taking it off quickly and placing it carefully in the bag while her wrinkled breasts swung.

She stood up straight again, her nipples pointing downwards and her bare breasts like globes hanging in wrinkled bags. She pushed her panties down by the waistband past her knees then stepped out of them and pushed them in the bag, which was now quite full.

She hunched herself forward, naked with her grey bush prominent between her legs. Resigned to her fate, her arms hung by her sides.

"Right then, you can learn to stand properly. Get your back straight, head straight forward, tits pushed out, your feet shoulder width apart and your hands behind your neck."

He paused a couple of seconds, "Well fucking do it, then!" Annie moved herself into the stated position with a few shoves and pushes from Eddie to get her posture correct. "Now get up on your tip toes!" He ordered.

She reached up unsteadily on tip toes. Her breasts rose and fell with her breathing. Eddie grabbed her nipples between his fingers and lifted her breasts up before letting them drop to slap against her chest.

"Still got a fair pair of knockers on you Annie," he chuckled, "Sagging a bit now but still a fair set of hangers!"

He pinched her nipples and lifted her breasts again, stretching the wrinkled skin of her chest as he tugged on them four times. Pain showed in her face before he dropped her breasts. They slapped against her chest as they fell and bounced into their hanging position again.

Eddie's tone changed to serious and annoyed now as he spoke to her, "You've betrayed me. Tried to cut me out and gone behind my back for your own gain, and your own pleasure. I could have been dead or at least badly ill because of your carelessness. I expect to be paid back for that!"

Annie gulped, her breathing got noticeably heavier as Eddie paused before addressing her again.

"I want the truth from you now, don't try to lie to me, Annie."

Annie shook her head.

"I know you wanked him off so that's for certain. Did you suck his cock?"

Annie nodded, closing her eyes. "I want to hear you say it!" snapped Eddie

"Yes I did." Stammered Annie. Eddie nodded, "Okay, and did you let him fuck you?"

"Yes but it wasn't like that," Annie started to explain but Eddie cut her off, "I'm not interested in the whys and wherefores, Annie just the facts!"

"Did you have him fuck you up the ass?"

Annie looked resigned and nodded softly before almost whispering, "Yes I let him do that."

Eddie nodded, "Then here's what's going to happen. You'll continue to punish him at your house, but..." he emphasized the last word and paused before continuing, "you'll be doing it only when I'm there and under my instruction. Is that clear?"

Annie nodded and spoke, "Yes Eddie that's clear."

Eddie carried on, "You'll also continue getting plenty of cock, but it will be mine! I'll have unlimited access to your fuck holes, your mouth, your tits, everything. Whatever I want, whenever I want! Now is all that clear so far?"

Annie nodded, "Yes Eddie, that's clear." She continued softly, "But what about Dot?"

"Dot's not been interested in sex for some years now, so it's nothing to do with her, " snapped back Eddie. Judging by how she flaunted herself in front of the window, I suspected that she just wasn't interested in sex with him, not disinterested in sex generally.

"After I've finished with him, I'll deal with you." He told her with authority in his voice. He moved behind her, his breathing heavy as he considered what he was going to say next.

"You'll be taking his place on that bench and by the time I've finished you'll be telling me every little secret you've got and more!"

Annie visibly gulped as he carried on, "You'll start by having your cunt fisted. I'll have my whole fist in and out of your cunt. We'll see if you want to talk then. If not it will be a fisting with a cricket ball in my hand. If you still aren't singing we'll move on to your ass hole and you won't want to know what I'm going to get up there!"

Annie gasped, her eyes widening as she listened to Eddie continuing, "I'd spend the time while he's being birched and fucked to think about telling me everything. If I think you are holding back be sure that I won't be."

Annie slumped slightly as Eddie finished. He noticed and tapped the underside of her breasts. "Keep up, Annie and get used to your tits hanging because you'll not be wearing any underwear at all from now on. That's my third condition. No bras, no knickers, nothing!"

He squeezed her breasts in his hands as he looked in her face and continued speaking to her, "When you are punishing him you'll wear one thing and I'll decide what. When you are serving me you'll be naked unless I tell you different."

He let her breasts drop and stood back a pace, "We'll have that thatch of pubes shorn off too. I want to see where I'm sticking my cock in your cunt. Now you can drop down off your toes but keep your back straight and head up!"

Annie rested her feet flat on the floor but maintained her posture. Eddie strutted in front of me, " Right boy, time for some proper punishment. A birching followed by a hard fucking!"

Eddie's birch rods sat soaking in a metal bucket of brine. He took off his shirt and singlet and began stretching his arms and manipulating his shoulders. He picked up the collection of six birch rods and a thin strip of leather that hung nearby. He began to wind the leather round the dry ends of the rods to make a handle.

Finished, he waved the completed birching implement around, making swishing sounds through the air. He stood in front of me and spoke, "You will come here once a week and be strapped to that bench for either a birching or some other punishment I devise. If Dot's away it will be on a Saturday morning like today. If not I will tell you when."

"A severe birching is twelve strokes, so every time you are birched you will be taking eighteen. There is no end to this. It will continue as long as I say it will."

"In addition to this, every Sunday from now on you will go to Mrs Holder's at one o' clock and she will prepare you to start paying me back. That starts tomorrow. The rest of our arrangements stay the same. If you see your panties in the window you get yourself to Mrs Holder's sharpish to be disciplined"

He swished the birch through the air again. He paused and shuddered slightly, savouring his next statement, which he spoke clearly and slowly, "After you've been birched today I'm going to fuck your ass and I won't be fucking it gently either!" He paused to let the statement sink in.

He tapped the birch against my buttocks. "You'll count the strokes, boy and say thank you for each one."

He raised his arm and thrashed down with his birch, hard on my buttocks, following the stroke through. The sting was brutal and intense, like a slice through my buttocks. I tensed against the straps fastening me to the bench.

"One Sir, thank you Sir," I gasped. As I finished he struck the second stroke. Again, pain roared through me, up my back and down my legs as the birch bit into soft flesh. "Two Sir, thank you Sir."

Annie watched without emotion as each stroke struck me, causing me to cry out and tense against my bonds. At ten strokes Eddie spoke to her, "He's feeling sorry for himself now, Annie and he's still got another eight to come."

I was sweating, gritting my teeth and grimacing as I awaited another stroke. Eddie laughed, "This little bastard deserves his eighteen strokes at least! You should see from back here, Annie. His ass hole flutters when the birch hits him." He poked my anus with his finger. "It'll flutter some more when I fuck it later, boy!"

He struck the birch against my buttocks again as I cried out, my body on fire with the pain of the strokes. "Eleven Sir, thank you Sir," I croaked.

At seventeen strokes my buttocks felt like they had been flayed. The taps that Eddie gave the birch to aim it were only light touches but seemed to burn like hot pokers.

"One more boy then I'll be ramming my cock up that shitpipe of yours!" laughed Eddie. "Then it's your turn on the bench. Are you ready for that?" he asked Annie.

She sniffed, nodded and replied quietly, "I'll tell you everything anyway. No need for you to do anything. I'll talk, I promise."

Eddie laughed, "No you don't get away that lightly, Annie. You'll feel my fist up your cunt at least. I want you to know who is in charge now."

Eddie didn't give her chance to reply again. He went to another of his boxes and produced a jar of Vaseline. He addressed Annie from behind, "Lube him up for me first. That way I won't ruin his ass hole for anybody else." He put the jar down next to Annie.

Eddie sized up the last stroke and gave it all his strength, cracking the birch against my backside for the eighteenth time. "Eighteen Sir, thank you Sir." I cried.

Eddie motioned Annie to move behind me to view my birched backside. Annie picked up the Vaseline, walked around and examined my buttocks.

Eddie took her place in front of me, undressing. He already had his shirt and undershirt off and was undoing his trouser belt.

He dropped his trousers and removed his shoes. His pale blue briefs bulged, showing the outline of his erect penis, a small damp patch at its tip.

His body was very hairy, dark hairs all across his chest, torso and legs. As he pulled down his briefs his pubic bush was even darker, a dense, untrimmed mass of hair around the base of his penis, which he now held in his hand, erect and with its glans glistening as he pulled his foreskin back and forwards over it.

It was larger than mine, a little over seven inches in length and thicker than mine too. His balls hung low and bobbed in time to his manipulation. "Take a good look, boy! This is going up your shitpipe in a minute and I'll be pounding it until it's raw before I cream your bowels with my spunk!"

I gulped and tensed involuntarily as Annie probed my sphincter with a finger greased in petroleum jelly. "I'd loosen up a bit if I were you." joked Eddie, "My cock is a lot bigger than Mrs Holder's finger!"

She probed again, this time with two fingers and a lot of the Vaseline jelly. She twisted her fingers around inside my anal passage before withdrawing them.

Eddie had kept his dark grey socks on but nothing else. He positioned himself behind me as Annie took up her position in front of my face. Annie proffered the jar to him. He took it and placed it down, whilst addressing her. "Back in position now, Annie." She moved herself and took up the same stance as before, legs apart, head up, and her hands behind her neck.

Eddie poked my sphincter with the tip of his penis. Even after being penetrated in Annie's broom handle torture I didn't realize how big a deal this would be. I was overcome with sudden panic and my eyes widened as I tugged on the straps restraining me.

Eddie put his hands on my back, thrust his pelvis and slid his penis inside me, up my slick lubricated anal passage. I gasped and groaned. My anus was pulsating independently as I tensed , delirious with the discomfort of such a large visitor inside me.

Eddie left his penis pushed so far up my anus that his pubic hairs prickled against my inner cheeks. My sphincter spasmed, opening and closing. My rectum following suit, squeezing then releasing Eddie's penis as he sighed with pleasure.

"The boy's got a good ass!" he exclaimed before slowly withdrawing his shaft, leaving the tip of his penis inside.

I shuddered as Eddie thrust his penis hard up my anal passage again. It felt twice as big as it had looked. I imagined that I could feel it high up in my bowels as he forced it inside me. He withdrew to its tip again quickly, starting a rhythm of penetrating me firmly and steadily as he gripped my waist with his hands. "Keep it tight, boy or I'll get a rope on your neck and choke you tight!" he snapped at me.

I tensed my sphincter against his shaft as he reamed my anal passage with his penis. He paused a few seconds before thrusting harder, withdrew then thrust hard again, making me gasp as my anus struggled to cope with its violation. The agony was much more than when I had been penetrated by Annie's broom handle toy. I felt like he was splitting me in two as his shaft ground roughly along my tender anal passage.

Eddie speeded up again, settling into a hard, fast rhythm and pulled on my shoulders as he thrust, speeding up before slowing and thrusting harder and with more determination as he gripped my shoulder flesh tightly.

My anal passage was being rubbed raw as his penis forced its way up, then down again, each time causing my eyes to bulge and my mouth to drop open with the force and speed of his pounding.

With two long, hard thrusts he grunted and sighed. I felt the warm spurt of semen flow deep inside me, once then again. Eddie grunted several times as he ejaculated, the third spurt smaller and the fourth barely perceptible.

He continued to slide his penis up and down my anal passage, now coated in his semen as well as the vaseline. He flopped down onto my back, his chest and stomach warm and sticky with sweat on his body hair.

He stayed like that for a minute or more, his penis still inside me but reducing in size and stiffness, his breath on my neck as he spoke to Annie, "That was a good one. I haven't cum that much in a long time."

maximpact
maximpact
34 Followers
12