The substitute health teacher looked at his class full of rowdy freshmen boys and sighed. Only half of them were in their seats, even though the bell had already rung, and the volume level was such that they were probably disturbing the class next door. What looked suspiciously like a paper airplane slid to the ground under someone’s desk.
The teacher cleared his throat roughly, pointedly, and banged against the blackboard with his fist. Suddenly noticing his presence, the kids quieted and the displaced half moved to take their seats. That was more like it. He could feel them appraising him, as all classes did with subs. He let them look; he was young, probably closer to their age than any of their usual teachers, and handsome enough: brown hair with a slight red tinge that he had tried to comb into some semblance of order, and a lanky frame that looked slightly out-of-place in a suit jacket and tie.
“My name is Mr. Darmon,” he said, writing it on the board. “I’m going to be your sub for today. So let’s get started, shall we?” He leafed through the papers their regular teacher had left on the desk for him. “According to your class schedule, you’re in the middle of sex-ed.”
“We just finished it,” one of the kids in the front row said.
“Really?” Mr. Darmon looked surprised. “You’ve covered everything? You’ve done the anatomy of the genitals, male and female?”
Some kids nodded, and there were one or two semi-coherent “yeah”s from further back in the room.
“You’ve covered safe vaginal intercourse?” More nods. “How about oral?” More nods. “Well. I see your teacher has been quite thorough indeed. What about anal?”
This time there was silence. Mr. Darmon nodded. “I thought so. A lot of teachers leave that out, but it’s very important. It’s not just for gay men, you know. If you have a really open-minded girlfriend, you might have anal sex with her someday too. It’s a good thing to be able to do, and do safely. Alright then.” He scanned the room until his eyes settled on a boy all the way to one side. The boy had a book in front of his face and was studiously staring at it, a faint blush on his cheeks, as though he wanted to be anywhere else. “You there,” said the teacher, pointing at him, “you with the red shirt. Yeah, you. Come up here.”
The boy looked startled, but did as he was told, putting the book down on his desk and moving cautiously towards the front of the room. Mr. Darmon smiled at him as he approached and the boy smiled shyly back. “What’s your name?” the teacher asked.
“Davie,” the boy said quietly.
“Right. Davie. Okay Davie, please stand here and face the class.”
Davie stood very still, looking uncomfortable under the gaze of so many people, while Mr. Darmon moved back to the desk, clearing off the papers, the pencil mug, the framed photo of their regular teacher’s dog, until one end of the desk was completely clean, exposed down to the smooth, dark wood. Then he moved back to stand behind Davie.
“Now,” he said, “today we’re going to learn about anal sex.” Without warning he reached around Davie from behind and swiftly, nimbly unfastened first his belt, then the button of his fly, then his zipper. He hooked his fingers under the waistband of the boy’s underwear—tighty-whities, he noted, how adorable—and yanked it all down to the boy’s ankles, leaving him exposed. Then he grabbed the boy’s shoulders and maneuvered him over to the desk, bending him over it until his torso was flat against the wood, turning his head to make sure he faced the class.
“Alright,” he said, reaching down next to the boy and grabbing up his briefcase. He plopped it onto the boy’s back and unfastened it, lifting the top. “The most important thing you need to remember about anal sex is that it’s all about preparation. Without the proper preparation, it can be very painful.” He reached into the suitcase and drew out a box of condoms and a tube of lubrication, which he set next to the boy before closing the briefcase once more and replacing it on the floor.
He held up the tube of lubricant. “I have here a tube of KY jelly. Who knows why this is a good lubricant?”
A few kids raised their hands, and one boy on the right side called out, “It’s not oil-based.”
“That’s right,” said Mr. Darmon, spreading some onto his fingers. “Although please raise your hand, Sir, and don’t call out. But yes, KY is a water-based gel. Oil-based lubricants can weaken condoms and cause tearing, so it’s best to use gels like this. If you’ve been with someone long enough and are sure that neither of you have any diseases, and you decide that you don’t want to use condoms, then you can switch to an oil-based lubricant, such as massage oil, or whatever you please.”
He screwed the top of the tube back on with his still-dry fingertips, then finished rubbing the lube over his fingers. “Now, you want to use two or three fingers. If the idea of sticking your fingers in someone’s ass grosses you out, you can stick them inside a condom first, but remember to lube the outside of the condom, if it is not pre-lubricated. Start with one finger.”
He grabbed Davie’s butt with his free hand, spreading the cheeks open, and slowly pushed his pointer finger into the boy’s anus. “Go slowly,” he told the class. “Do it gradually.” He worked his finger into the boy up to the first knuckle and wiggled it around a little, then pushed it in all the way. He felt the way the boy’s body tensed under him, rigid, clenching around the intruding digit.
“Relax,” he murmured, stroking Davie’s back with his free hand. “If you’re on the bottom in this case, it helps to relax your muscles; it makes it less painful.” He felt Davie’s body slowly start to ease up a little as he began to move the finger slowly in and out of the boy’s anus.
“Why would anyone want to do that though?” came a question from the class.
“Hands please,” Mr. Darmon reminded them, then nodded at the boy when he raised his hand. “Yes?”
“Why would you want to be on the bottom of something like that?” the boy asked again.
“Well,” said Mr. Darmon, as he drew his finger all the way out, then pressed it and a second digit back inside, “it’s actually especially good for men, because the prostate gland is located inside the rectum, and stimulation of it causes great pleasure. Sort of like a male G-spot. In World War II, when soldiers had been on the front lines for a long time and had been sexually frustrated for too long, field doctors would perform a procedure called ‘milking the prostate,’ which was basically fingering, which allowed the soldiers to relieve sexual pressure, or ‘pelvic congestion’ as they called it.” He paused for a moment, and crooked the two fingers inside Davie, brushing against the boy’s prostate and causing his whole body to shudder. “There you see stimulation of the prostate in action,” the teacher said to the class. He paused and went back to working the fingers in and out, in and out. “When you get two fingers in like this, you can start to scissor them, to help widen the passage.” He demonstrated.
“If you kids want to come up close for a better view,” he said, “feel free. It might be hard to see for some of you in the back.” There was a scraping of chairs as the students left their seats and gathered in a semi-circle around the teacher and the penetrated boy. The teacher scissored his fingers a few more times for demonstration purposes, then withdrew them once more and added a third digit, pushing them all back inside, slowly. The boy on the desk whimpered, and Mr. Darmon patted his back once more.
“This is where you really start to feel the stretch, and you really have to force yourself to relax. But it’s important that we get his passage widened, or else it will be very painful when we insert the penis. Now, does anyone else want to try preparing him, while we’re focusing on it? I’ve already gotten him to this point, so you can probably just go ahead and stick three fingers right in.”
Half a dozen boys raised their hands, so Mr. Darmon had them form a line. “If you’d like a condom to do it with, they’re here,” he said, moving the condom box and the lube container to the edge of the desk by the line. “Remember to lube up your fingers first. It’s very important.”
He removed his fingers from Davie’s ass and stepped back, and the first boy in line stepped forward. He spread the lube onto his fingers, then handed the still open tube to the boy in line behind him. He took a deep breath as he made sure to cover every inch of the fingers he was going to use, then stepped up to Davie and, pressing a hand down on the small of the boy’s back to brace himself, shoved all three fingers roughly into the boy. Davie winced and hissed slightly. “Gradually,” Mr. Darmon warned.
“Right,” said the boy, and yanked his fingers out just as roughly. This time he placed them up against Davie’s anus and began to push slowly, watching as the boy’s asshole distended and swallowed the fingers, knuckle by knuckle, with wet, hungry sounds. Mr. Darmon moved to the other side of the desk and snagged a tissue from the box left there by the regular teacher, wiping off his fingers as he watched his students’ performance. When the boy had his fingers all the way inside Davie, he started to move them in and out as the teacher had been doing. He pulled them out with proper slowness, but he had a tendency to shove them in a little roughly, causing Davie to jolt forward.
“You can spread them too,” Mr. Darmon reminded him, and watched as the boy opened his fingers up and wiggled them around, as though trying to tickle Davie’s insides.
Mr. Darmon let the boy finger Davie for a few more minutes before he finally put an end to it. “Alright,” he said, “enough. Let the next boy have a turn.”
The second boy stepped up and repeated the first boy’s actions, placing his fingers at Davie’s entrance and pushing in slowly. He had an almost mean grin on his face, and fucked the boy with his fingers a little harder than was necessary. Davie began to grunt in rhythm with the thrusts of the boy’s hand, as they became sharper and sharper. When it got to the point where he was ramming his fingers into the boy’s ass, Mr. Darmon decided to end this session a little prematurely. “Enough,” he said. “Next.”
The boy looked a little miffed as he pulled his fingers out of Davie and grabbed a tissue. But he stayed close, his eyes fixed on the boy’s asshole, obviously not annoyed enough to stop watching the others.
Mr. Darmon could see by the shine of the third boy’s hand that he had lubed up his pinky finger as well. Mr. Darmon rolled his eyes; these teenage boys, always trying to outdo each other. But he said nothing as the boy placed all four fingers at Davie’s stretched anus and began to push in, moving gradually but constantly deeper and deeper in until his fingers were sunk into the boy up to his palm. Then he opened them and wiggled the digits inside Davie, apparently hitting his prostate, because Davie shuddered once more as he had before.
The third boy began to fuck him with four fingers, moving his whole hand in and out up to the palm. It was gradual, but large, and Davie whimpered again as his asshole was spread wide. The boy behind Davie nudged Davie’s legs open (stepping on Davie’s pant leg and shoe and lifting the leg until they came off) so that he could stand between them and have a better angle from which to spear him with his fingers. Mr. Darmon noticed that the other boys still in line had grabbed up the lube again and were covering their own pinkies, not to be outdone. A couple of snickering boys at the end covered their whole hands, thumbs, palms and all. Mr. Darmon didn’t stop them, but warned, “be careful when you do that, okay? You’ll have to be really gradual.”
He let the third boy go on a little longer than the previous boys had, and the fourth one—who was also using four fingers—as well, to make sure that Davie would be fully ready. As the fourth boy was jabbing his fingers into Davie, Mr. Darmon warned the last two, “lube up your wrist and forearm a little bit too. You’ll be surprised at how deep it goes in.”
The two boys did so eagerly, and when the first boy’s turn came, it was obvious he was almost too eager to contain himself. But he obeyed the teacher and did it slowly, perhaps not wanting to get cut off early the way the earlier boy had. He positioned his hand like a spear, and pushed. Davie cried out as his asshole distended further, widening and widening as it hit the boy’s thumb and kept going, swallowing him knuckle by knuckle, until finally, with a plop, it slid around his ball joint and down to his wrist, surrounding the boy’s entire hand. The boy pushed his hand in a little further, forcing in another inch or so of his wrist, then pulled back up to the ball joint, then pushed forward again, and began a series of short, sharp thrusts of his hand. Davie writhed on the desk beneath him, especially when the boy opened his hand inside Davie’s passage. Mr. Darmon could tell when it happened, because Davie’s eyes popped wide open, and he gave a little squeal.
Mr. Darmon didn’t let it go on too long, eye on the clock, before telling him to pull out. Davie groaned when the boy’s thumb widened him again as it was pulled out. Mr. Darmon called up the last boy. This boy was obviously too excited and impatient from having been in the back of the line. He stepped up to Davie and simply plunged his hand into Davie’s ass, making the boy cry out, then roughly yanked it out again and began to jam it into Davie over and over, making the boy’s asshole stretch over his thumb and knuckles every time, passing the maximum width of the boy’s hand. He’d gotten at least seven sharp, solid slams of his hand inside the boy before Mr. Darmon collected himself and stopped him. Davie’s body slumped against the desk as he was released.
“Enough,” he said. “If you’re not going to do it right, just stop.” He handed the boy a tissue, and made him take a seat along with the others.
“Alright,” he said. “Now that he’s all prepared, and a bit more than necessary,” he added pointedly with a glance in the direction of the end-of-the-line boys, who merely grinned, “he is ready for penetration by a penis.” Mr. Darmon reached over to the box of condoms, pulling one out and unwrapping it. He unzipped his fly and pulled out his penis, hard from watching the boys finger Davie. He rolled the condom on and slathered it generously with the KY jelly.
“Now,” he said, positioning his penis at Davie’s hole, “do it slowly. Like with the fingers.” And he began to push his penis into Davie. “If you’ve done the stretching right, then there should be almost no pain for your partner at this point.” He kept pushing, one fluid motion, until he was pressed all the way inside the boy. “Now you can fuck him,” he said, and with a sharp motion of his hips, began to do just that.
The boys watched with rapt attention as Mr. Darmon swiveled his hips in quick jabs and shoved his penis over and over into Davie’s well-prepared asshole. Davie was grunting again, but it didn’t sound pained as it had before, more like an acknowledgement of sensation as his hips were slammed repeatedly into the side of the desk.
Mr. Darmon came inside Davie just as the bell rang. No one in the class moved from their seats. Mr. Darmon took deep breaths for a few seconds, still lodged as deep as he could go inside Davie. Then, with a grunt, he pulled out, taking off the condom and tying it off before throwing it in the waste bin. “Sorry,” he said, “I’d hoped we’d have enough time that you could each have a go at fucking him, but it sounds like that was the bell.”
He glanced at his watch. “I think I have a free period next though, and there’s no class in here, so if anyone wants to stay, I can give them a late pass for their next teacher. Depending on how many people want to stay, if we go later, we’ll have to find a new room, but I have lunch after that, so I have time.” He patted Davie’s back. “Davie, I’ll give you a pass anyway, for helping with the demonstration, so you can get a chance to go get cleaned up. So, does anyone want to stay?”
Every single boy in the class raised his hand.