Billy Historical Sex Story With Anal And Spanking

My boss, Henry Williamson, was invalided out of the Desert Campaign. The War itself was over before I was old enough to join up. So, I went to work on the Williamson farm. Now, at age 29, I ran the spread almost single-handed.

The 'almost' mentioned above was the Williamson's son, Billy. Although only 16 he was a very willing worker. Billy was small for his age which meant I did the bulk of the work.

I liked to be kept busy. Less time for thinking, that way. When I was 15 a rough, masculine shed-hand talked me into letting him up my bum. How I squealed when his hard penis opened my tiny sphincter and filled my chute. He pounded into me until his nuts erupted, spraying his spunk high into my bowels.

That shed hand did me every night for a week but, when there was no more work for him, the itinerant worker moved on to another farm. He left me both sore and lonely. There had been no one else after him. Most nights I jacked-off in my bunk. The tight, taut jeans-covered rump which flashed into my mind just before I ejacqulated, belonged to Billy.

Although I slept in the single men's quarters I always ate with the family. One Saturday, the Williamsons, normally very sociable folk, were silent. Old Henry sat in his wheelchair picking at the wholesome country fare. Mrs Williamson was sighing. Billy had the frightened look of a rabbit, caught in a car's headlights.

Mrs Williamson cleared the plates away and disappeared outside. Henry cleared his throat.

"Sean, sorry if we all seem a bit distracted".

"Thought something was up", I replied. "Anything I can do to help?"

"It's our Billy". The farmer looked at his son with both admiration and loathing. "He's only gone and knocked up the Prentice girl".

I glanced at Henry's son and heir. The youth did not look too pleased at the prospect of fatherhood.

"Suzy Prentice? The one with the big .."

"Titties". Henry confirmed.

We both thought about the teen who oozed sensuality from every pore.

"Sean, I need you to do something for me. It's personal". The farmer said quietly. His son seemed to shrink in his chair. "I need you to give Billy a hiding. Stripe his tail for him. Then maybe he'll keep his dick inside his jeans".

I looked at Billy.

"Guess I've got it coming to me", he said.

"Please, Sean", the farmer begged. "I'd do it myself, if I was able".

The thought of leathering Billy on the bare bum made me go hard.

"I have to check on the ewes". I looked at my pocket watch and then at Billy. "Come over to the quarters at 3 o'clock".

The youth nodded.

"Thanks, Sean". The boss sounded grateful...

...The time pips had just sounded on the wireless beside my bed. I looked up and Billy was standing in the doorway. I ushered him inside and closed the door. I motioned for him to sit down while I listened to the all-important weather forecast. Then I switched the wireless off.

"Billy. Did you really do it with the Prentice girl?"

"Uh, huh".

"How many times?"

"O-once".

He didn't sound very convincing.

"Are you ok about me giving you a hiding?"

"Uh, huh".

"Ever had one before?"

"Not with Dad being the way he is". Billy suddenly looked much younger than his sixteen years. "I got the cane a couple of times at high school. Hurt like Hades". The Prentices were religious folk.

I stood up and placed a pillow on the end of the bed. "Get your jeans and undies off and straddle that pillow".

Billy got undressed while I unlooped my thick leather work belt and doubled it. The youth got down onto the pillow, his glorious bottom sticking right up in the air. His legs were apart and I could see right inside his hairless crack. Its pink pucker looked like it was about to wink at me.

"Poke your nuts back under your body", I instructed. His left hand pulled them out of harm's way. His buttocks were exposed and waiting. How I wanted to make sweet love to that part of Billy's anatomy! Instead, I was required to hurt it. Sighing, I delivered a very hard lick of the belt. A broad band of red flooded healthy pink flesh. Billy squirmed.

Then I really let him have it. The youth was soon yelling after each hard lick. I took out a lot of my aggression and frustration on Billy's pliant buttocks that sunny afternoon. When his mounds were covered with angry-looking crimson welts, I coiled the leather on the small of his back and sat on the bed.

"Talk to me Billy". He looked up at me through tear-filled eyes. "What REALLY happened between you and the Prentice girl?"

"Like I said", he mumbled.

"The hiding will get harder and harder until you tell me the truth".

I picked up the leather and wrapped the buckle-end around my fist. Again and again I laid into Billy's defenceless hemispheres. The end of the belt punished the very tender flesh on the side of the youth's mounds. His yells were high-pitched, desperate for the terrible hurt to stop.

"The truth, Billy?"

He shook his head. I used the buckle-end of the belt on his orbs until pinpricks of blood dotted the punished flesh. I re-looped the belt and sat on the bed.

"You're a very brave young man", I told him, admiration in my voice.

"Is it over?"

"Yes, Billy". I tousled his blonde hair. "I don't have the stomach to inflict any more hurt".

"They made me say it". His voice was barely a whisper.

"Who made you say what?"

"Suzy and Mickey Doolan".

"That the young guy who works as a farm-hand for the Prentices"?

Billy nodded. "They said that if I didn't take the blame they'd tell everybody I was a shirt-lifter". He spat out the hated words.

I got a wet towel and gently placed it over Billy's tortured flesh. He sighed his appreciation.

"Suzy and me were fooling around this one time", he continued. "But my babymaker refused to go hard".

"That often happens the first time". I tried to sound consoling.

"Then Mickey got on the bed with his big dick. Pushed me aside. Said: 'Let a real man get on with the job'. Billy's voice was bitter. "When I saw his bum thrusting into her THEN I went hard. Of course they saw what had happened. When Suzy got pregnant they blackmailed me into saying I was the father otherwise they'd tell everyone I was nothing but a dirty poofter".

I put my arms around his thin shoulders and held him tight for a very long time.

Late in the afternoon I paid a visit to the Doolans. Mickey was there with a tribe of younger children. Danny the father looked me up and down.

"I've just had to bloody young Billy Williamson's arse, at his father's request", I told Danny. "Because the boy insists he is the father of Suzy Prentice's child". I looked at Mickey. "While I was giving Billy the hiding I noticed his nuts haven't dropped yet". Mickey shuffled his feet, listening to my lie. "A simple operation and he'll be intact but there is no way Billy could have fathered any child, in his condition".

Danny glared at his son.

"Have anything to say, Mickey?" I challenged.

"Yeah". He looked defiantly at his father. "That sprog Suzy's carrying is mine".

The story about the blackmail came out.

"What are you?" Danny roared. "Just seventeen years old and already a blackmailer, fornicator! I'll teach you a lesson you won't forget!"

Danny shooed the children inside and threw his pocket knife at Mickey.

"Cut a switch", he said grimly and watched as his First Born hacked off a length of whippy willow.

"You'd better witness this", Danny Doolan said to me, taking Mickey by the scruff of his neck and marching him into the barn.

Inmide the quiet space the youth undressed. His father gently tapped Mickey's uncut dick with the switch. "That's what I should be whipping, Gawd help us".

Mickey cowered.

"Get your good-for-nothing arse up in the air".

The youth bent over a table covered with bird droppings. His splendid buttocks were clenched tight. His father kicked one leg and then the other, pushing his son's crack open, and revealing a none-too-clean-looking orifice.

The switch whacked against Mickey's bum. The white line it left in its wake immediately swelled into a raised purplish-red weal. His father really got stuck into him but Mickey never made a sound. Raised on switchings his firm flesh seemed immune to pain. That was until Danny aimed the stick so it lashed the youth's tender thighs.

"Not my legs, Daddy", Mickey screamed. His father lashed them even harder. Blood dotted the punished flesh.

"That's enough Danny", I said and the stick clattered to the ground.

"Get dressed", Danny told his son and strode out of the barn. Alone with Mickey, I examined his prominent anus.

"Looks like your backdoor's been well-and-truly opened".

There was a silence while Mickey painfully pulled on his clothes. Then he unburdened himself: "I let men up me, for money".

"That's your business but if I ever hear so much as a whisper about Billy being a shirt-lifter .." I left the sentence unfinished.

"I won't", he promised.

Much later Danny, Mickey and myself called on the Prentice family. Suzy finally admitted Mickey was the father of her child. Mr Prentice then insisted on accompanying us to the Williamson's farm where the truth was finally told to a very relieved Billy snd his Dad. I apologised for the unfair hiding but my employer just smiled and said: 'The end justified the means'.

The next day I was snoozing on my bed after a particularly delicious Sunday roast when a shadow woke me up. It was Billy.

"Can I talk to you Sean?"

"Course".

He came in and closed the door.

"About the blackmail. What Suzy and Mickey were saying .. well .. it's the truth. I AM a shirt-lifter". He looked at me, perhaps expecting to be thrown out the door.

"So am I, Billy".

"What? But you're so masculine".

I told him about that itinerant farm-hand.

"You're lucky. I never did it with anyone except in my head".

We stood up, awkwardly. I put my arms around him and we kissed. His tongue tentatively touched mine.

"Let's get undressed", I said. Billy needed no second invitation. His clothes joined mine in an untidy heap on the floor. We got on the bed where I tongue-bathed Billy's virgin fundament. I don't believe he had ever imagined such a thing was possible. I reached under the bed and found my trusty tub of petroleum jelly and coated my finger.

Billy gasped as my finger penetrated him. His sphincter was so tight I had to push hard to gain entrance. Billy's bum-muscle spasmed around my finger.

"Do me", he whispered hoarsely.

"Someday Billy, I promise. You're so tight back there I'd only hurt you". I looked at his badly bruised buttocks and shook my head. His bum-muscle closed tight after my finger was withdrawn.

"You can bum me if you want", I offered. Billy greased up his six inch penis and then I knelt on the bed. His knob pushed against the lips of my anal opening. He thrust until it was it was inside me.

"Am I hurting?" Billy's voice was anxious.

He was but it was the sweetest pain. "No", I lied. "Put it right in". Soon, his fleshy love-pole was fully inside my hot, tight chute. His nuts brushed against my arse-cheeks. I guess lovemaking is inate. Growing up on a farm Billy must have seen procreation happening all around him. He thrust into my hole, slowly at first and then faster, until I felt his wetness splatter my rectum.

He pulled out of me and I cleaned both of us with a damp flannel.

"That was awesome!" Billy said. "I never imagined it would feel so good". We cuddled, my erection pressing against his bum crack. "You're still hard. I wish you'd do me".

So, I lay on my back, allowing Billy to grease my big pole.

"Squat over it. Lower yourself down onto the knob". He followed my instructions, grimacing as gravity forced the mushroom-shaped head into his incredibly tight, virgin chute. I held his bum-cheeks in each hand as he lowered himself, inch-by-inch, until I was fully inside him.

Billy's inner muscles swirled around my pulsating shaft.

"Are you OK?"

"Yes! I want you to be inside me like this, always".

He bent down to kiss me and I wiped the sweat from his sweet forehead. Gently I used my hands to move him up and down. His face mirrored the new sensations.

"Harder!" he whispered.

He started moving of his own accord and soon my nuts exploded with a rainbow of an orgasm which coated the walls of his bowels.

Reluctantly, Billy climbed off my now deflated organ. I cleaned us both up and then we got dressed again.

Mrs Williamson had prepared a splendid high tea, her way of saying 'thank you' for my having rescued Billy from the blackmailers. If she had known her son now carried my seed inside him, and that his was in me, the good lady might not have been so grateful. As for Billy he had a grin from ear to ear. Even old Henry was his usual cheeful self again. I smiled with pleasure. All was right in my small world.

Become a Patreon to support Taletopia!

written by moonspender2