“You’ve done this before, haven’t you, Jessie?”

“Yes,” Jessie Evans whispered and then gasped and clutched up as Aaron Taggert pushed the bulb of his cock inside the fourteen-year-old boy’s tight hole. The thought of the pain to come had Jessie close to hyperventilating. No, Jessie had never done this before, although he’d contemplated doing it almost constantly for the last year of change in his physical and emotional development. But the last thing his performance arts teacher, Sean, said to him before he left his classmates and went with Aaron Taggert, which had led up here to his New York hotel room, was “Just say yes to what he asks. It’s time for you to move ahead in this business.”

So Jessie said “yes” in Taggert’s hotel room and tried to follow the man’s guidance when the English clothing designer then told him to relax and take it. The boy controlled another gasp and groan as the shaft followed the bulb inside his hole. The feeling of stretching to the filling was alien, painful, and he whimpered and groaned at the invasion. But there was exhilaration too as the thought that he was doing it. He’d been thinking about doing it. Now he was doing it.

“Is it OK? Can you take it? Relax and it will be easier.”

“Yes,” Jessie whispered through clinched teeth. “Do it. Do me.” But he did try to relax, and it did help. It was still painful, but not as much. He still felt filled, but there was arousal in that feeling.

The English clothes designer probably realized then that even if the fourteen-year-old boy had done it before, it hadn’t been frequent or a great success. That didn’t stop Taggert from fucking Jessie, but it prompted him to go slowly, to take care, to savor every moment of taking this luscious boy.

“You do want this, don’t you?” He paused, a good four inches inside Jessie’s channel and holding the boy’s hips steady by clutching Jessie’s slender waist between his hands.

“Yes,” Jessie whispered. And he did want it. He’d thought about doing it for a year and more and wanted to get on with it. “Yes fuck me,” he murmured.

Taggert sank his cock another inch and a half inside boy. Jessie groaned, arched his back, and dug his fingernails into the man’s shoulder blades. His butt was on edge of the foot of the bed, his back on the mattress, and his legs drawn up with his knees almost pressing into his pits. Jessie, fortunately, was flexible to the max, which was really turning Taggert on and which probably was part of the arousal of a forty-five-year-old man fucking a fourteen-year-old boy.

Jessie was a dancer and gymnast, so the position itself wasn’t taxing. The throbbing shaft inside him definitely was, though. The Englishman was standing on the carpet and leaning forward over Jessie’s body, reclining into boy, his fists buried in the mattress on either side of the naked boy’s biceps and his eyes staring down into Jessie’s eyes, reveling in every effect reflected there of what his cock was doing inside the tight ass of the boy.

Taggert began slowly to pump Jessie’s channel, and the boy writhed under him, the fingers of his hands digging into Taggert’s shoulders opening and clutching unconsciously to the developing rhythm of the fuck. Taggert liked this, the sensation that slowly the boy was surrendering to him—and to the fuck.

Aaron Taggert was tall and thin, an elegantly handsome man in his mid-forties. He moved with grace and cut quite a figure of slender, but hard body in the nude. Jessie had no way at that time to gauge a man’s relative equipment other than that he was thinner but longer than Jessie was in erection, although after this first encounter with a man, Jessie found that his erection was longer and thicker in actual sex with another man rather than as a solo act.

Jessie almost hyperventilated at the thought that the Englishman intended to sink all of that into his ass, and, although the boy had tried, I hadn’t managed to get much of it down his throat when he had given Taggert stumbling head before the man had raised the boy up, lowered him on the foot of the bed, sucked his cock while opening him up with his fingers, and then begun fuck him. Jessie was later to realize, when he’d gone with other men, that Taggert wasn’t appreciably long at all. But this was his first time and he felt what was inside him was a baseball bat.

Taggert stopped pumping and held when it seemed he had pushed into Jessie’s intestines, giving the boy time to adjust to him and to stop his trembling. Jessie did manage to bring that under control, although he shuddered and moaned deeply when Taggert put his hips into a slow motion, moving the cock in and out of Jessie’s channel, starting up the rhythm of the fuck again.

Jessie moved his hands to the man’s slim sides, squeezing hard, pushing on him when he drew back, really wanting him to withdraw and then groaning and squeezing when he pushed in again. Jessie knew there was a grimace on his face, although he was trying to bring his acting lessons into use to give the impression he was enjoying this.

Jessie had said “yes” to this.

He knew he’d enjoy it after the first couple of times. he wanted the man to think that he had experience, that he was beyond the first couple of times. But he wasn’t. He wanted to impress the man and obtain favors from him. That was the whole point of agreeing to be here with him—to let Aaron Taggert fuck him—now and again if Taggert wanted to.

“Am I hurting you, Jessie? You’ll tell me if I’m hurting you, won’t you?”

The boy couldn’t answer “yes” to that; Sean had said to only say “yes.” So, he didn’t respond directly at all. Instead he whimpered, “Fuck me. Be good to me.”

That sounded like everything was go to Taggert. He wanted everything to be go. Barring an earthquake splitting the room in two, nothing would stop him short of an ejaculation now. He was in solidly and hadn’t much more to do to bottom. The boy was a real honey. He had the skill of submitting like this was his first time. The acting classes were working out well. Best rent-boy Taggert had fucked. And just the age he wanted to get them too—fresh. No longer a boy, really, but not quite yet a man. He wanted them to be all innocent and let him do the driving. Sean had picked well for him.

In truth, there had been moments, including how tentatively the kid had sucked his cock, that Taggert had thought maybe this was the boy’s first fuck. He’d said it wasn’t, though, and either way it was too late now. Taggert had his dick inside him. The kid was fucked now. And he wanted something—his performance art coach wanted something for him too. He wanted help getting a part in the musical Taggert was doing the costumes for. He wanted help, so he had given Taggert what he wanted. He had to lift his tail for Taggert. The kid had said “yes.” He was fucked now.

Taggert set up a steady rhythm then, and it progressively got better for the boy. Aaron could feel the boy relaxing more, opening more to the stroking cock. Jessie even managed to put his own hips in gear and roll with the man’s stroking in waves of the in-and-out movement of his cock inside as the cock sank lower and lower inside the boy’s passage. As Jessie relaxed, he felt his channel opening to Taggert, the sliding of skin on skin making jessie harden up and feeling his own cum rise, making Taggert’s cock get bigger as he stroked, making Taggert tremble as Jessie was trembling, making the man whisper, “Yes, yes, yes,” just as boy was doing.

They had settled into a natural rhythm and had become one fucking machine, working together to a goal.

Jessie moved one of his hands between their bellies, grasped his hardened cock, and took care of himself in fewer than a dozen strokes. Taggert wasn’t too far behind Jessie in his ejaculation, jerking and releasing, jerking and releasing, giving the his warm flow deep up inside his channel.

They remained there, in position, panting, waiting for both of them to cool down.

“That was good,” Taggert whispered.

“Yes,” Jessie answered. And he had to admit that once they got into it, once Jessie got beyond this being his first time and the pain and uncertainty that was attached to that, it had been quite satisfactory. He hoped that the next time...

“You can use the shower and then leave, if you like,” Taggert said as he rose from on top of the boy. “Your coach says the hotel your classmates are staying at is just around the corner. Or you can stay for the night or for ever long into the night you wish. Sean has arranged for you to be in his room, and only you, so your classmates won’t know when you returned. If you stay, though, I’ll be ... again ... you’re such a sweet lay.”

“I’ll stay,” Jessie whispered. “And, yes, fuck me again.”

He did. Jessie experienced first doggie-position fuck, Jessie’s tail in the air, his chest on the mattress, and his arms extended wide, his fists bunching up the material of the bedspread, while Taggert crouched over him, mounted high, and fucked him with strong strokes. It was a much more assured fuck and it went easier than the first time. Jessie decided he could handle this. Just another tool on his skills belt now.

“That was better,” Taggert whispered in his ear when he was finished.

“Yes,” Jessie agreed. Just say yes, he thought, but it was true—that was better that time.

Aaron Taggert was in New York for a series of runway shows that included the fashions he designed in London. He did men’s fashions as well as women’s. He had some other irons in the fire while he was in New York. He’d done the costumes for a dance production and he was doing them for a Broadway revival of “The Sound of Music” musical too. This was what had piqued Sean interest and that then had led to Jessie’s run of “yeses.” There was a part for an early teen boy in the production, one of the Von Trapp children, Frederick. Sean thought it was time in Jessie’s training that he got on the Broadway stage and there weren’t many roles for a boy Jessie’s age. The role and the presence of Taggert made this opportunity to get his help fortuitous. Sean hadn’t given one thought to Jessie’s age or possible sexual preference. He’d seen where the boy’s preference was developing, and now was the time for him to grab his chance. Nothing was more important to Sean than seizing one’s chances to break into the theater.