Gay Historical Sex Stories

Meet at the Rise of the Moon

Just two more places to go, and then he'd be done with his round. He slowed down. Listening intently, he continued at a crouching walk. "Pssst! Sean! Sean O'Farrell!" In a flash, he was over by the person who had hailed him. "It is tonight, then?" asked the young girl. "Aye!", said Sean. "Captain's orders: All must be ready at the rising of the moon. " "Ah. The old place by the river?" "The same.
3.7

Lord And Squire

To one side of the circular room was a bed of great size heaped with thick skins and furs; Sir Gawain and I smiled at one another, for we knew we had found a place to fend away the cold. There was also a great fireplace which to our fortune was supplied with firewood alongside, and I immediately busied myself in building a fire. While I was thus occipied my lord was skirting the room, examining the tapestries, armaments and other devices which were hanging on every wall. When I completed my task and came up behind him, he was examining a small tapestry on its own, which hung from a simple leather strap. Though somewhat faded, it clearly depicted two comely men embracing in a Greek manner.
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Gay Anal Experience during the Night Shift

The year was 1946. Colin was a fresh-faced 21. Sid was ten years his senior and a veteran of the Desert campaign. They worked the night shift at a small railway station in a former colony of Great Britain.
3.5

Authoritarian Boot At Folsom Street East - Historical

A guy from the crowd who was wearing 30 hold black Ranger boots stepped up to Lars and asked: "Is this your bootslave?" Lars replied: "I haven't collared him yet, but if he does a good job on my boots, he will be. Hey, the slut seems to be slowing down. Would you mind kicking his arse a few times with those heavy duty Rangers?" With that the man took two steps back and kicked Pete's ass with his powerful right boot. The force of the kick sent Pete's face flat against Lar's boot shaft. "Harder!" Lars commanded the onlooker, who then let fly with a powerful kick that made Pete grunt. A few guys in the crowd shouted encouragement as he kicked poor Pete three more times. Everyone had a good laugh as Pete intensified his bootlicking.
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Fergus And Tom - Gay Male Historical Anal Sex

My knuckles whitened and I grimaced at the pain as his big baby-maker invaded my brown-hole. I yelped after each hard thrust and squeezed my stretched sphincter around his fleshy monster in a vain attempt to make him spunk. He just pounded my arse even harder, his manly thighs slapped against my boyish-looking buttocks.
3.3

Ancestor's Sex Diary

"My name is Oliver Jefferson, the fourth. I write this diary for no one other than myself. I am 69 years old, set to turn 70 in just a few days. I often think back on a time in my life when I was the happiest, yet at the same time it was a very sad time in my life. I try not to think about a certain person I knew, but if I were to be honest with myself I think about him every day, many times a day. If I could see him today I would tell him that I don't regret knowing him. Yet, I am full of regret. Regret for not being stronger, regret for not being a real man, regret for letting him out of my life.
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Historical Sex Story Above Athens

We liked having sex, in the vestibules of town houses, in the public baths, next to the statues of naked gladiators with their idealized body parts, better-looking than us, no pimples, but we were alive and could do what they could't, what they would never do.
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Cousin Will

She flung my suitcase in the boot of the Hillman and we drove along the winding gravel road to the farm. I collected my suitcase and followed Auntie Dottie inside the farm house.
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Encounter With A Slave

"He went into town, he just left." When he stood I saw the size of him, and I felt a little scared. He walked over to me, and I stepped back. "Well, he ain't here right now is he?" he said. "Gives me just enough time to work on you." He grabbed my arm and threw me to the ground. My heart started racing, imagining what he was going to do to me, I had no idea. He looked down at me and started untieing the string he had on his pants to hold them up. He untied it and let his pants fall, and revealed his enormous black cock. I had never thought of being with a man before, but I was mesmerized by his beautiful dick. It dangled down almost to his knees. He walked towards me and his meat bounced back and forth on his legs. He grabbed me by the hair and forced his big black cock in my face.
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Adventures of gay Robinson on the Island

He already knew these men were cannibals and therefore he had to be very careful! What if the guy he chose and finally seduced ate him after they had finished making love? But then he was so desperate he didn't much bother about that part of the scenario yet. Again maybe, he could save one of those prisoners. Surely those guys weren't cannibals?! As he thought all these things he climbed to the top of the little hill above his 'fortress' and saw thirty men dancing around a fire down below on the shore. Something was cooking in a huge pot, but Robinson couldn't be sure what it was or whether it was indeed human meat. As he watched the lean and strong figures of the dancing men his cock hardened with his long pent-up lust and he slowly pumped his hips into the ground.
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