Gentlemen's Club Ch. 04

As Rochester complied, Westerly straightened up, his own boycock still hard and throbbing. "Oh, sir! Shall I really be allowed to put my prick inside of him?"

The headmaster squirted some grease onto his hand before reaching out to grip Westerly's eager young member. "Yes, my lad, you shall. And I expect you to give him a good seeing-to -- make him sorry he did not service you as well as I had, show him how it should have been done!"

"I shall do my best, sir, but I do not know if I will last more than a moment myself!" Westerly said, leaning against the headmaster as the man gently masturbated him with the lubricant.

"Now, Westerly, give me your hand," the headmaster said, holding up the lube bottle with his other hand and aiming a short squirt at the boy's offered palm. "Take some of that on your fingertips and press it into him -- even with a member as small as yours it is better to grease the opening and as much of the passage as you can reach, so as not to cause harm to your partner."

Taking the older man's words to heart, Westerly began to stroke lubricant into his friend, pressing a finger deeply into Rochester's backside before dipping his fingertips once more in the puddle of lube in his other hand and proceeding to feed one, two, and three fingers into the asshole before him, stroking the digits in and out slowly while Rochester let out a groan of appreciation.

"That's enough, I think! Now, let us position you so you may continue with your education!" the headmaster said, leading Westerly by his swollen cock to the ass which still contained his three fingers. "Pull those out now, my boy, so we can put in something that will feel so much better for you both!"

Westerly's introduction to the other half of penetrative sex went quite well, the boy allowing his headmaster to dictate the pace of his entry by holding him by the stomach in front and pushing against his lower back from behind, until he was fully sheathed, his lightly furred pubes pressing into the smooth cheeks he was embedded between.

The resulting fuck did not last very long, just as Westerly warned it would not. The boy tried to go slow, like the headmaster had done, but very quickly his passions overcame him and he began thrusting fast and hard, the headmaster having removed his hands from Westerly's body as soon as he thought the boy had developed a rhythm.

"Oh, how hot! How tight! Oh, the feeling -- it's even better than your mouth, Rochester! Oh, oh, I'm dying with the joy of it! Oh!" Rochester's rectum received its first cum-load of the night, Westerly's hips pumping furiously in fast, shallow thrusts as he came.

Next the headmaster took a turn inside Rochester, while Westerly climbed onto the bed and, at his friend's urgings, positioned himself under him, taking Rochester's leaking dick into his mouth and sucking an ejaculation out of him which he made sure to swallow before coming up for air. Seeing that the headmaster was still thrusting at a moderate pace inside his chum, Westerly then allowed Rochester to convince him to take his, Rochester's, prick up his back passage again. This was quickly accomplished and soon all three were crying out as two of them came inside a hot, young ass and Westerly shot off into Rochester's stroking hand.

For the next few hours every combination possible between three men was performed -- each boy fucking their headmaster while the older man sucked off the other boy; each of the boys taking center in a three-way copulation where the headmaster fucked their asses while they fucked the other boy or vice-versa; one of the three of them getting fucked and sucked at the same time; one of them sucking and fucking at the same time; occasionally one of them, most often the headmaster, would sit off to one side and watched while the other two took pleasure in each other orally or anally, waiting for his spent rod to recharge -- encouraged by the sight he was witnessing.

Every form of male debauchery was diligently taught to a willing and eager young Westerly, and demonstrations were repeated again and again, to be sure that he had taken it all in.

Finally, after his latest ejaculation up Rochester's willing backside, the headmaster had both boys lie on their backs, their well-juiced asses pressed together and thus their two young cocks aligned between them. Then, with great ceremony, the headmaster climbed on the bed and straddled Rochester's prone body, bringing his own cum-dripping ass -- he'd graciously allowed Westerly to throw a fuck into him while Rochester sucked on him earlier -- into contact with the boy's straining boycock. Reaching a hand between his legs, the headmaster grabbed both hard pricks in his large fist, squeezing them tightly together and making the two boys groan in pained pleasure -- by now they were both highly sensitive from all the friction their cocks had experienced over the long night. Keeping both slippery cocks pressed together, the headmaster inserted them into his waiting rectum, getting both cockheads in at the same time, to everyone's general satisfaction. Moving his hips up and down on the two impaling members, the headmaster bent down to whisper in Rochester's ear, "Well, done, my lad! This is the finest little stallion you've found for us to play with yet!"

* * * *

Lying on his side on the bed with one hand propping up his head while the other one was draped over the waist of his co-star, David, Kevin looked up at the director. Sitting beside the two young men on the bed was an older, much bigger man, also mostly naked and, like them, covered with spunk.

"Excellent, gentlemen! Very good!" the director beamed at the cast, his face flushed with pleasure at what he'd seen. "I must say, Kevin, I was worried about working with someone with no previous theatrical experience, but you've worked out very well! If you can deliver that kind of performance every time, we may even consider you as a permanent replacement for Jamie, instead of just covering for him until he gets back from his vacation." While the director beamed at Kevin his assistant, having swallowed the last mouthful of spunk to shoot from his boss' twitching dick, got up from between his naked thighs and began drying the director's bared crotch with the towel he'd been kneeling on.

Kevin's fine-boned face blushed with embarrassed pleasure at the complement. "Thank you, Jerome! You know, I was pretty nervous, too. For one thing, I'd never fucked an older man before starting rehearsals here with you -- you took my cherry, Mike!" he added, looking at the man sitting beside David's feet.

"No kidding! I'd never have known -- you ride like a champ, kid!" Mike said, smiling fondly down at the half-naked blond before getting up to get a cup of water from the water-cooler in the wings.

"Say, Kevin," David said softly, his dark eyes puzzled as he looked up at him, "I know you're into Daddy-types, but you're honestly saying that none of them ever lets you top? Not even your Thursday-night regular? 'Cause I gotta tell you, guy, the man doesn't know what he's missing!"

"That's actually one of the reasons I said yes when Mr. Filbert asked me if I'd be interested in doing this show. I want 'Daddy' " -- Kevin deliberately emphasized the word to show that he meant it in quotes, keeping the truth of the title to himself -- "to see what I can do. You know, see if a little demonstration might wake up his 'inner-bottom'," Kevin waggled his eyebrows suggestively. "That, and the plot gives me a certain sense of nostalgia -- I really did get my cherry popped when an older guy caught me blowing a friend, and he said that if I didn't put out he'd tell my old man."

"Wow! If your real father could see you now, man!" David shook his head. He found the story very amusing, thinking how unlikely it was that the ever-horny Kevin would be forced into anything sexual -- the little slut had probably set the older guy up to catch him in the first place, just so he could get himself fucked. "Wouldn't he be proud of his little whor..."

"OK, that's enough talking, people -- time's a-wasting. There's only have another three hours till the dinner crowd starts coming in! That run-through was good, but I'd like to go over the dialog at the beginning just one more time before we hand over the stage for the dancers to practice on. Kevin, David, put your PJs back on and get into position." Jerome's assistant also got into position, kneeling between his legs and licking at his quickly reviving cock.

"Action!"