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A Boy's Big City Adventures
Part 2

by Y Lee Coyote

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Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 04 Sep 1997

This story is all the product of my imagination (i.e., totally fictional). This is a sequel to "A Boy's Big City Adventures" which should be read first as the characters are introduced there. Feedback greatly appreciated.


It was a couple of nights later when Tom and Kris met again. They had an early dinner and then went to great Broadway show. He was anxious to return to the Castle as he had told Tom the night before. That experience in the Castle with Tom had changed Kris. He felt very special with Tom, almost as a young boy with his favorite uncle who took him to wonderful places - even places mother wouldn't approve. He also had that same feeling when he saw his bare crotch getting dressed back in his hotel or even when he just felt it when he reached into his pants to pee during the day.

After the show, Tom suggested that they go to the Castle and play a game. Kris was over joyed and enthusiastically agreed even before Tom had finished. As they headed for the Castle, Tom told Kris what game he had in mind. Kris would be a twelfth century English lad. A young serf who had been caught in Sherwood Forest and had been taken to the Castle of the most dreaded SHERIFF OF NOTTINGHAM! Kris's mind thought about the possibilities; he just knew that the Sheriff would not be inviting him to high tea (nor, for that matter, even low tea if such even existed).

As they walked through the park, suddenly Tom grabbed Kris. Then as he tied Kris' hands behind him, said, very sternly and menacingly: "The Sheriff wants to see you, lad. Which was it that you were doing here in Sherwood: poaching the King's deer or consorting with Robin Hood and his band of evil outlaws?"

"But I was not doing either, Sir." pleaded Kris playing his role to the hilt. "I was just returning from seeing my uncle in town where my father had sent me on an errand, Sir."

"That's not what I want to hear, lad," said the arresting officer. "The Sheriff has many ways of making a lad like you tell all he knows," he growled menacingly with an evil chuckle. Kris felt cold shivers creep up his back as they approached the Castle gate. It was exciting. His boy-tool was hard and pressed against his britches in anticipation.

The key was put into the lock and the gate was opened. They went in. The gate was then slammed shut with a crash - an ominous crash. And then the bolt snapped into place with a loud clink - menacingly sealing him inside. The captive was led deep into the Castle and down into the keep. He was made to strip and then taken down to the dungeon. Only a small candle provide a little bit of light.

Attached high in the wall was a iron ring from which hung some rough ropes. Kris' wrists were lifted up and securely tied above his head with them. Before he left, the guard groped the helpless lad both fore and aft. "You'll be fun," he hissed wickedly, "lots and lots of fun!" and left the lad hanging naked and alone to await the fiendish Sheriff. The guard took the candle when he went upstairs. Now Kris was alone in the dark for the only light was that which trickled down the stairs from the guards' hall above. It was silent for some time and Kris soon felt as if he was in a real twelfth century dungeon as his face and body pressed against the rough stone wall he was bound to.

Suddenly, the silence was broken. He heard the SMACK of a heavy leather strap hitting something or SOMEONE. And then a blood curdling SCREAM. Kris cringed in fear. Then there was a second STRIKE of the strap followed by a second SCREAM of agony. "Tell us who your partner was, lad," snarled a menacing voice to some other unfortunate prisoner. Fearfully Kris turned to try to see but the blackness gave not a clue. Even a moonless night was brighter then the Sheriff's dungeon.

"I did not do it. I swear, I did not do it, Sheriff; I swear; I swear it." squeaked a frightened boy's voice from some other cell. There was another WHACK followed by a half a scream. By now Kris was in a cold sweat.

"Damn, this one's fainted. Let's try the other one," growled a harsh voice. The candle light returned and Kris felt rough hands feeling his back and butt. The hand squeezed his butt checks very hard and even probed between to feel his butt-hole. The lad had not been touched there by anyone since he had been in three-cornered pants. Then his behind was slapped sinisterly. It hurt. But surely not like that leather strap must hurt. The hands then turned him around so that he could see his jailer in the poor light. Of course, it was Tom but he was now dressed in a tunic so that he now looked the part of the Sheriff of Nottingham. The Sheriff now took the opportunity to feel the lad's front side. He ran his hands all over the lad. Every time he felt the pectorals he also tweaked the lad's nipples in one way or another. Kris felt pain but it was also strangely erotic. Then he let his hand wander down to the lad's crotch. He grasped the sensitive gonads and squeezed them very firmly until Kris yelped in pain. He then felt the lad's hairless pubes with his other hand and said: "You're still just a little boy and you will stay a boy if you don't confess lad, emphasizing his meaning with another squeeze. Just like those male piglets on your Lord's farm that never become boars after just one little cut of the knife." Chuckling, he gave the lad's balls a hard pull to emphasize the point. Kris yelped again and realized how helpless he was. But he was still very excited and there was some very hard evidence of this fact.

The Sheriff turned the lad back to face the wall. He then picked up a leather paddle and tapped Kris' butt with it. "Let's see how you like my little friend, lad." He brought the paddle back and swung it hard against the lad's behind. Kris managed to kept from yelling but he had tears in his eyes. "What were you doing in the forest, lad?" the Sheriff demanded. Kris repeated that he had just been doing an errand for this father. "And seeing Robin Hood on the way too, eh lad?" The Sheriff added and applied the paddle to the lad's bottom another three times and repeated his question: "WHAT WERE YOU DOING IN THE KING'S FOREST, LAD?".

"Dad send me to ask his brother for the loan of two silver pennies to pay the King's taxes next week," Kris whimpered.

The Sheriff snorted: "You were penniless when you were arrested. Who were you hunting the King's deer with?" He then gave Kris several more blows with the paddle.

"Uncle promised the money at the next market day, Lord Sheriff," Kris cried. Again the paddle kissed the boy.

"We have questioned your uncle and he said he had not seen you for three months. What were you doing in the forest, lad?" And still again the paddle spoke directly to the boy and he started to cry.

Between sobs, the boy confessed: "I went to the forest in hopes that Robin Hood would give me some food. I had heard talk that he gave to the poor. I don't know where he hides. Really Great Sheriff. Please don't beat me any more. I don't know anything. Really, I don't. I'm just a poor serf's son." The Sheriff gave the lad another couple of heavy swats and the lad just cried more.

Stepping back a bit the Sheriff removed his tunic. Tom slipped on a condom and put some lube on his hand. The Sheriff approached the crying boy and applied the "grease" to the boy's crack particularly the unprotected hole. The grease made it easy to slip his fingers into the helpless boy. "Please Great Sheriff, don't fuck me; please. The priest teaches that it is a great sin. Please, Sir, don't fuck me." Kris could hardly say the words for he longed for it to happen so much. He had long fantasied being a prisoner being raped by guards. How could Tom had known, he wondered. When Sheriff Tom decided that prisoner Kris was sufficient relaxed, he replaced his penetrating fingers with his rigid man-shaft. It slipped easily into the now well lubricated hole and he quickly fucked the boy long and hard. As he fucked he also jerked Kris so hard that the lad came first, spraying his spunk on the stone walls. He let go the lad's cock and began to play with his nipples. While he did so, he fucked the lad with every greater force. As he rammed into the boy again and again, the boy was thrust hard against the wall. Then he too came, explosively in the hot hole of his prisoner.

They cleaned up and went up on to the roof of the Castle. As they enjoyed the view Kris told Tom how wonderfully he had come in his fantasy of being a medieval prisoner and that the 'torture' rape really enhanced the scene. Later, as they walked out of the park, Kris said that he hurt. Tom inquired if he had used the paddle too hard or fucked too roughly and Kris said those were not the problem. "It is my cock that hurts. When you were playing with my tits and fucking me so wonderfully hard, it kept rubbing on the stone wall. So now it is sore."

"Life is tough, kid," replied Tom, slapping him hard on the butt.

-- End of Part II --

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