Chapter Three: Breaking him in.
Sorry for the long delay. I wasn’t sure there was enough interest, but then I saw some comments requesting the story to continue. So I’ll give it another go. I have the whole story sketched out on my head, and it definitely gets wild. (Wait until Jakov enters the scene…) But I also want it to be a bit of a slow burn. So be patient. Please definitely leave a rating and let me know in the comments what you like and what you'd like to see more of. Thanks.
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Jake had just left Daniel’s room and was about to go to his own bed, wanting to process what had just happened. But he suddenly felt he should just get it over with and ask for the instructions from his boss.
Although it was late, Andrés opened his door still in his suit. “Ah, Jake. Everything ok, I hope? How can I help?” Jake said nothing and looked nervously up and down the corridor. “Do you want to come in?” asked Andrés. And quickly, Jake snuck into his boss’s room.
“Sit down. What can I do for you?”
“I’ve just been to see Daniel.”
“Ah, I understand.” Andrés chuckled to himself. “And you’ve come for the instructions?”
“Yes, please.”
“I have to say I am a bit surprised. Daniel hinted that he might try you, but I felt he would have a hard time convincing you. But then again, he’s quite persuasive, isn’t he?”
Jake nodded, and then there was a brief silence.
“Alright then. Let’s get to it.” Andrés stood up and opened a cupboard behind his desk. There were several boxes in it, and Andrés took out one of the bigger ones and put it on his desk. “Here you are: your starter package. Everything you’ll need is in here, and you are in good hands. I’m gonna walk you through the most important stuff now. Ready?” Without waiting for an answer, Andrés started.
“The most important thing is that your hole must be well prepared on the night. Which means two things: It has to be clean. And stretched. Forget the stuff you see in porn, where bottoms rip off their pants and take dicks just like that. That’s all bullshit, okay? For the cleaning, there’s a douche in here that you can use. And for the stretching, you’ll get four butt plugs and two dildos. Basically, you should start stretching tomorrow. You should wear a butt plug now every day, for at least four hours each day. Work yourself up from the small size to XL. You should definitely be able to wear the XL plug on the last day before the session, preferably sooner. The great thing is that you can wear them during work. So you’ll be paid for stretching.” He waited for Jake to laugh – but he just stared at the row of butt plugs in front of him on the desk in disbelief. “Anyway,” continued Andrés. “And then use your evenings to work with the dildos. Start with the smaller one, obviously, it’s about 5 inches. And then use the bigger one, which is just under 6 inches.”
“Wait. So why is the biggest dildo here still smaller than the smallest dick at the Big Boys Club?”
“Good question. It’s a bit of a thing for Daniel. He doesn’t allow bigger toys in here. He says he likes to see the surprise on the guys when they get stretched by one of their dicks eventually. He wants guys to prepare… but maybe not too much. I personally think it’s stupid. But I don’t make the rules,” he shrugged. Jake took the bigger dildo and reached his hand around the shaft with wide eyes. “So even bigger than that?”
“Much, yeah. This is why stretching is important, especially if you are not a regular at being fucked. All of these toys are new; they have never been used. But if it makes you feel better, you can use condoms with them. There are plenty in the box. You’ll also find a piece of paper in here with the login to a special website. The big boys have set it up for themselves, but there’s also a whole section for guys who will bottom for the first time. Lots of explanations on how to best use the tools, how to douche, and so on. There are links to really good explainer videos. And there are instructions for a diet that you should really stick to in the last three days before the session. It’ll make cleaning out much easier.”
“Sounds doable. I can follow an eating routine. I’m used to it from the gym.”
“That’s great. But really take the stretching seriously. Don’t wait until the last day before your first session. There are also links to a couple of porn videos from porn sites that will give you an idea of what it’s gonna be like. If you want to have a preview.”
“Might ruin the surprise…” Now, Jake was attempting to joke.
“I think there’ll be enough surprises for you, don’t worry,” replied Andrés, raising his eyebrows. “You’ll also find a jock strap and a harness in here. You have to wear those on the night. You’re not allowed to wear your own underwear. There’s also a mask in here, but that’s only an option for when you are being filmed. Hmm, what else?” Andrés was rummaging through the box. “Ah, of course, there are poppers in here and plenty of lube and a lube dispenser. You can squirt lube deep into your hole with that. Much better than just lubing up your hole from the outside. There’s also an explainer for that on the website.”
“And what am I expected to do right before the session?”
“Again, it’s all on the website. But on the day of the session, you don’t eat after breakfast. You clean yourself out really well, and then I suggest that you lube up your hole with the dispenser. You take a proper shower. They like their bottoms smelling clean and fresh. Put on your jock strap and harness. And then you are ready to go. A cab will bring you from here to the villa. It leaves at 9:30 pm on the evening in front of the hotel.”
“Okay, okay.” Jake exhaled. “That’s a lot to take in. Like… a lot has happened in just the last hour. It’s mental.” He suddenly looked overwhelmed.
“I understand. But I must add one more thing. I usually offer a special preparation for guys who have never bottomed. A solo live trial, if you will. If you want to take up that offer, then you can just come to me. But it’s not mandatory at all.
“You mean…?”
“Yeah. I know it must feel unusual. I’m your boss and everything. But it’s proved to be a helpful thing for guys in the past. Getting in some training hours, you know?”
“But Daniel said you guys weren’t allowed to go solo with a bottom before the group had a go. So how come you are allowed?”
“Oh, I’m not a member of the BBC.”
“You’re not?”
“No, just an inch or so short, I’m afraid.” And with that, he pointed to his crotch.
Jake was speechless.
“I know, it’s all a bit much. But I think you can do it. You can always come to me for questions in the next few days. I wouldn’t bother Daniel. Too much admin takes the fun away for him. And you can also speak to Stefano, as he will also be attending as a bottom this year.
“Stefano from the bar team?”
“Yes, he’s pretty much a regular. Has been coming here for years.”
Jake had spent a good amount of time with Stefano in the last couple of days. A good-looking stocky guy from Naples, covered in ink. He knew he was gay.
All this information was swirling around in Jake’s head when Andrés got up and handed him his starter package. “Time for bed now, Jake. And don’t forget to stretch,” he winked.
The next three days, Jake spent following his preparation regimen. But that was only to prepare his body. Mentally, he kept trying to get his head around the fact that in a couple of days, he would be fucked by a dozen bottle-sized dicks or more.
He had first logged onto the website to check out the rest of the material that Andrés had mentioned: thebigboysclub.com. He had expected the website to look like a porn site, but was surprised that it was almost empty, except for: Big Boys, Bottom Recruits, and Starter Package. Both the first sections were closed to Jake as they required an extra login that he didn’t seem to have. Only the Starter Package system was available to him. It had explainers on how to douche and stretch with lots of videos and step-by-step routines and video links that led to different sites. It all looked almost clinical to him, not seedy or dangerous.
The next morning, Jake wanted to start stretching with the smallest of the plugs. He stood in the shower, still dripping wet and positioned the lubed plug at his hole, gently trying to push it inside. But for minutes, nothing seemed to move, even as Jake shifted positions a number of times and raised one of his legs as far as he could to give more space to the plug that was now pressed between his impressive butt cheeks. But no, his hole wouldn’t give way. He remembered what he had seen in one of the videos: how the guy had been lying on his back to insert the plug. So he dried himself off and went to his bedroom, where he closed the blinds and spread a towel across his bed.
Jake lay on his bed the wrong way around, resting his feet above the headrest on the wall behind the bed, letting each leg tilt slightly to the side. Before even trying again, his body instinctively felt that this missionary position would be better for the exercise. He felt that in this position, his hole had less resistance to give, and was more vulnerable to pressure from outside.
Once again, he brought the plug to his hole and pushed. But this time, it snugged its rounded head slightly inside, just enough to give Jake some leverage to nudge his hole open wider. “Don’t go too fast,” one of the guys in the video had said, “or it’s going to ruin it. Slow in the beginning makes you go further in the long run.”
So he paused and waited for – though he didn’t exactly know what he waited for, he realised. But once he felt less twitching in the hot glowing spot between his butt cheeks, he pushed the plug further in. And then waited again. Only to resume the routine.
It took Jake a full ten minutes, but suddenly, when he wanted to give up because he thought that he had reached the limit of what he could take, his hole suddenly opened one painful millimetre more – and swallowed the plug in one hungry move, sucking it inside and locking it in place. Jake gasped. He waited to see what the feeling was like, what his filled hole felt like.
It was a strange sensation. Poured over the relief, that the pressure from the last ten minutes had subsided, was a new sensation: a pressure from within, stemming itself against his inner walls. It was a sensation that he first couldn’t pin down but then suddenly recognised. He let his head fall back on the bed: “Man, this is weird.” If this was meant to give pleasure, Jake thought, then why did it feel like he needed to take a shit?
Still, over the next three days, Jake quickly perfected his technique, and he was wearing the plugs as often and as long as he could. He had felt shy about secretly wearing a plug in public. But on the third day, he had already worn the plug while going to the beach to swim. Jake knew this feeling from swimming: boundaries and pushing through the pain, the resistance. Making your body do what you wanted it to it. While it had felt uncomfortable in the beginning, he now sometimes caught himself feeling weirdly empty when he removed the plugs before going to bed.
But he hadn’t conquered all his challenges. He had lain on his back and tried to push the bigger of the two dildos into his hole. And while he managed to bury a third of it inside, he wasn’t able to go further than that. It just seemed impossible, not just because of the pain but also because there just seemed to be no more room. It had started to worry him. The whole exercise felt robotic and fake to him.
Two days later, Jake lingered in front of Andrés office again. It was just after 11 pm. His shift had ended an hour ago. The whole day, he had worn his XL plug, and he felt like his body had learned to accommodate it.
Andrés opened the door. He had left his shift earlier today to go to the beach and meet with friends. He had just gotten back and wasn’t wearing his suit but a pair of shorts and a low-cut tank top. Jake was surprised by what he saw. Though he had suspected that Andrés kept himself in good shape, he only now saw how athletic and trim his boss was underneath his perfectly tailored suits.
He was a bit shorter than Jake and definitely less muscly. But his arms were long and defined and had strong veins running elegantly along them. His tank top sat tightly on what appeared to be a defined and toned upper body. And his chest and legs were generously covered in trimmed dark hair, with just a sprinkle of grey in them. A runner built through and through. His friendly face was covered by a crown of thick curly hair, which made him sometimes appear ten years younger than he really was.
He looked questioningly at Jake. “What can I do for you? It’s late.”
Not waiting for an invitation, Jake came inside.
“Okay… come in, I guess.” Andrés closed the door.
“Are you having second thoughts? It’s normal. Don’t worry. But you can cancel if you want to. Daniel wouldn’t be happy, but there’s nothing forcing you to do it.”
“Well, I do kinda need the money.”
“Okay… So what can I do for you?”
“Look, I’ve followed the routine and everything, and I think I’m doing really well with the plugs. I’m up to XL already.” Jake hesitated. “But I’m having less of a good time with fucking myself with the dildos. It just doesn’t work or doesn’t fit, I don’t know.”
Andrés was sensing where this conversation was going, and he felt a low buzz in his balls. But he knew Jake had to get there by himself, so he waited for him to continue.
“And so I thought… I just thought maybe your offer for training wouldn’t be such a bad idea. I just think the dildos don’t feel like the real thing, and I’m sure I can do better with your thing.”
And with that, Jake had passed yet another threshold, and Andrés knew it.
“Sure, buddy. The offer still stands. What about tomorrow after your–“
Jake cut him off: “What about tonight? Like now.
“Oh ok. Well… I guess there’s no reason why not. I just came out of the shower, so I’m all fresh for you. But have you cleaned out?”
“Yes, I have. And I’ve been wearing the XL plug the whole day.
“Okay, okay. I can see that you’ve got it all thought through. Let’s go then.” He turned around and grabbed his set of keys from his desk.
“Are we not staying here?”
“No, I have a special place for the training. More secluded, you know.”
Andrés led Jake down the staircase into the basement. They walked down to the end of a corridor, where Andrés opened a door with his keys and led Jake through to the second part of the basement, which had two doors in it. Jake started to get worried, but he had gotten himself into but had no time to think any further as Andrés unlocked the first of the doors and ushered Jake in. “Welcome to my play den,” he smiled.
They were standing in the first room of what almost seemed like a small apartment of two connected spaces. The concrete walls and ceiling in the first room had been painted a matte black, giving the spaces a borderless, floating feel. There was no direct light anywhere, just faint indirect lighting coming from behind a cornice on the ceiling.
There was a small mirror-clad bar on the far-right corner and a large comfortable lounge area with a dark navy sofa and two chairs. It looked cosy and relaxing, Jake thought as he was processing his first impressions of this place. Not at all seedy. As Jake was looking around, Andrés drew a thick curtain across the door and walked over to the bar, mixing them both a drink. “Gin Tonic is fine?” Jake nodded.
He turned his head around the corner to look into the next room, which was larger than the first and also had a black ceiling. In the centre of the room stood a large King Size bed, which was covered in a black sheet and black pillows. The walls were covered in a thick, dark curtain, immediately changing the sound in the room as Jake stepped in. Behind the bed hung a large floor-length mirror, slightly tilted towards the bed. In the corner hung a large love swing on which somebody had left a towel. And on the left stood a long, low cabinet made from steel. On top of it were dozens of dildos and other sex toys. There was a large bowl filled with condoms and a collection of countless bottles, some small, some large. So this was what his boss was doing in his free time, thought Jake.
“Alexa, play the Fuck Me Daddy Playlist”, Andrés said in the other room, taking Jake out of his thoughts. “Let’s get ourselves in the mood, eh? Come get your drink.” A low, urgent club music was starting to play from speakers that were hidden somewhere. Jake stepped back into the first room just as Andrés had placed the drinks on the sofa table and sat himself down.
“So this is where… where what happens exactly?”
“It depends.”
“On what?”
“On what my guests want.”
Jake thought for a moment. “I think I want to get it over with.”
Andrés looked at him and, without breaking eye contact, reached inside his pants and pulled his soft dick over the rim of his shorts. “Let’s start here then, shall we?”
Jake looked hesitantly at Andrés’ soft dick and didn’t move.
“You can skip that part if you want”, said Andrés. I’ll get hard anyway. Just thought we’d ease into it. And they’ll be expecting it of you. But totally your choice.” Andrés got up and took off his underpants. He was now only wearing his tank top. His soft dick swung between his tanned legs.
Jake still didn’t move. “No, I think I’m good. I think I can manage to suck a couple of dicks. I mean, lots of girls have sucked mine, and I have watched them do it, so…” Andrès scanned him for a second. The boy didn’t know what he was in for. Sucking dick at the BBC meant deepthroating 8+ inches of thick dick for hours and being facefucked until your face was covered in tears and slime. At least if some of the wilder tops attended on the night. But it was his choice. “Ok, totally fine. Then get on the bed and lie on your stomach. I’m gonna start by rimming you for a bit. It will relax you, okay?”
Jake looked at the bed and thought of all the times that he had gone down on girls. Now his own hole was going to be licked like it was a pussy. It felt strange to him. He decided that he didn’t like the thought. “Can we skip that as well?
“Why? That’s gonna be the best part for you here. I’m excellent at rimming, chico. Plus, it really helps you to open up down there. Don’t you want that?”
Jake said nothing.
“Listen, at the end of the day, this needs to fit in your hole.” And with that, Andrés grabbed his dick, which had now gotten hard without Jake even noticing. It was probably 6.5 or 7 inches and straight like an arrow. The skin looked smooth and tanned like Andrés had soaked his dick in the sun all day. Jake noticed that it wasn’t as thick as he had worried it would be. It looked solid… but soft and somehow… manageable.
“I think I can take it.”
“Okay, your choice.” Andrés smiled a smile of surrender. He wouldn’t try to force anything on the boy. And it was kind of sweet how Jake wanted to appear all tough and strong. Andrés dick twitched slightly. “Okay then. Take your clothes off and lie down then.”
Jake turned around shyly and started taking his pants and underpants off, revealing his strong legs. As he was undressing, he tugged at his own dick, trying to get some blood into it. But it remained much smaller than what Andrés had to offer. He quickly got on the bed and lay on his stomach.
Andrés continued to walk him through everything: “On the night, you should pre-lube yourself pretty heavily. Use the lube dispenser that was in your starter package. Get a good amount in there. Have you done that already today?”
“No, I thought we could just lube your dick and my hole when we get to it?”
“You can do what you want on the night, guapo. But right now, we are going to prepare you properly, okay?” Andrés walked over to a cabinet, took a dispenser from a tray and filled it with lube. Each movement looked effortless, like he had done it a million times. Although the whole situation was mind-blowingly weird for Jake, he suddenly felt a sense of calm, like he was in expert hands here. The music filled the space with dark and urgent sounds. Jake's head was spinning slightly.
Andrés walked back over to the bed and kneeled behind Jake, who was spread out in front of him. He had left his T-Shirt on, much to Andrés’ disappointment. He loved seeing the back muscles of a bottom twitching when he fucked them.
“Now what’s that?” Andrés looked down at Jake’s hole and saw that he still had the XL plug inside, one piece of black rubber sticking out of the tiny, hairless hole.
“Oh yeah… It’s still in there. Should I take it out now?” Andrés wanted to offer to take it out for him, but stopped himself. I would be much hotter to see Jake removing it himself. “No, you go ahead.”
“… okay.” Jake clearly hadn’t expected this answer. He waited for a second for Andrés to change his mind. But when nothing happened, he reached back with his two hands. With his left hand, he was spreading his left cheek to make space for his other hand. He grabbed the black piece of rubber and slowly started tugging at it. Andrés watched as the tiny hole in front of him started to widen bit by bit to reveal the massive butt plug. It was strange to think that such a small hole could be made to swallow an object of that size. He felt weirdly proud of Jake. He had done well! Jake stopped tugging at the plug for a second and let his hole adjust for a moment. Then he resumed the extraction again. He continued like that for a while, soon forgetting that Andrés was watching him silently from behind. He fully concentrated on getting the whopper of a plug out of him, without tearing his hole apart. And just when Jake thought he could never set his hole free again, the plug shot out of him like the massive fuck bomb that it was.
Andrés smiled. “Well done, guapo. We’ll continue right away. No time to waste. He pressed the tip of the dispenser softly against Jake’s slightly puffy pinkish hole. Andrés wondered what it would be like after ten guys had rammed their meat through his rear gate for a full night. “Open up.” And the nozzle disappeared. “It’s gonna be a bit cold, maybe”, said Andrés. Jake felt the slightly chilly lube being pushed into his insides, slowly coating his inner walls.
Andrés turned around and lay flat on the bed. “Let’s get to it. You want me to wear a condom, right?” Jake nodded. From a box on a small bedside table, Andrés grabbed a condom, tore the wrapper open with his teeth, took out a bright red condom and rolled it quickly over his perfectly shaped cock, which now stood fully erect. It wasn’t a major cock as far as cocks go. But he was an expert at making it go a long way. He took a bottle of lube and lathered himself with a good handful of the thick liquid.
Andrés moved to the headrest, propped himself against it and spread his legs wide open, with his dick sticking out from a cropped bush of dark pubes that had sprinkled some grey into them. “All set. Now sit yourself down on my dick. It’s the best position to start with for a bottom. Take your time. My dick stays hard forever.”
“I’m not sticking my ass down on your dick… that feels… weird. Like I’m fucking myself on your dick, or something. Like … as if I really want that. No, it’s weird. I think I’m okay with… like taking it… but not with riding a dick like that.”
Andrés looked at Jake for a moment, considering whether he realised what he was in for. Andrés knew from the stories he had heard from one of the bottoms that some of the Big Boys enjoyed leaning back and watching a bottom impaling himself on their dicks for hours. That’s what some of them considered as taking a break from the “proper” fucking.
“Okay, no problem. Then get on all fours and arch your back down.”
Jake did as he was told. His pale ass was now high up in the air, and his forehead pressed down into the mattress. He had seen some of the porn, Andrés thought. Jake felt Andrés moving around on the bed, positioning himself behind his ass. One of Andrés's hands took hold of his hips. He started rubbing the firm head of his dick against Jake’s hole. “Don’t hold your breath. That doesn’t help you relax. Take a deep breath, then exhale. And when you exhale, push out down there. And then I’ll go in, okay? Don’t clench your hole, it’s only making it painful. Push out, and I can slide in. That’s the trick.” Andrés dropped a thick wad of spit on Jake’s hole. “For good luck”, Andrés said with a cheeky smile in his voice.
Jake hesitated for a moment. This was really just about to happen. He was getting fucked by his boss in a secret sex room to get loosened up for a crazy sex party with lots of monster dicks. If he wanted this to stop, he should do it now. Otherwise, he would be too far in.
Suddenly, Andrés lightly patted the side of his bum as if to hurry him along. “Come on, handsome. Your hole is as ready now as it is ever going to be.” Jake drew the blinds on his thoughts, inhaled, waited for a second, and exhaled while trying to push out something in his hole that wasn’t there. And as he did that, he felt his boss's dick at his entrance, the cold wet of the lubed condom against his soft flesh. He moved his ass forward just an inch, away from the fleshy pole that was about to fill him, but now Andrés was grabbing his waist more firmly. His boss took a large pillow from the side and placed it under Jake’s crotch. “Stay here with me. Bring your ass back again.” Andrés brought Jake’s ass back and pushed further in, alternating the pressure with pauses, waiting for a few seconds to let Jake get used to his dick. “I’m no bigger than the biggest plug, so you can do this, okay?” And he pushed again. “On the night, you’ll be lucky to be treated like that. Enjoy it.” And further in he pressed. He had almost broken the young man’s seal when Jake stirred.
“Stop. Get away.”
“Are you sure? We are halfway there.”
Yes, I’m sure.”
“It feels like I’m about to burst. Can you get off me?”
“Not yet. You need to get used to it. Trust me. If it feels uncomfortable, relax your ass.”
Jake groaned. “Shit. Why am I doing this?”
“Relax. Feel the pleasure behind the pain.”
Andrés pulled his dick away from Jake and sat back, looking at Jake’s body below him. His ass was still raised in the air, and his hole was sticky with lube. Andrés rolled off the condom and tossed it aside.
“I’m sorry that didn’t go to plan. Is there anything I should do differently? We can wait a bit and try again later?” Andrés waited for a reply.
Jake was still lying on the bed, his face flat on the mattress. A few seconds passed until he managed a reply: “No, thanks. I think I’m just going to have to grin and bear it on the night, you know. No point in stressing my hole out now. It’s just making it worse, I think. I’ll be fine. I’ll wear the butt plugs for longer in the next few days. It’s going to be fine.” He was speaking to himself now, thought Andrés.
A few moments passed.
“Right?” Jake asked into the silence of the room.
“No. I don’t think you’re right here, Chico. I think you'd better go through with this now. If you haven’t been fucked at least once, you shouldn’t be joining the Big Boys tomorrow. They will rip your hole apart.”
Jake was thinking.
“I think you can do this, ok?” As Andrés was saying this, he moved his right hand between Jake’s butt cheeks and placed his thumb on the young man’s hole. He started to rub the pinkish opening, first softly, then with some pressure. “I can feel you are ready for it. Let me try again.” Jake didn’t say anything but slightly raised his ass and put his head back down again, as if to put himself into position again.
Andrés now moved with expert choreography: With one hand, he was rubbing his thumb over the hole, trying to loosen and relax it further. With the other, he was rolling a fresh condom over his rock-hard cock, which he had just ripped from its wrapper with his mouth. The lube was too far away to grab, and as he didn’t want to spoil the moment, he dumped a generous amount of spit onto Jake’s hole and then another on his dick. “Stay still for me now”, said Andrés.
The tip of his boss’s cock pushed against Jake’s hole. Slowly but steadily, Andrés increased the pressure, guiding his dick towards the warmth of Jake’s insides. Jake moaned but stayed perfectly still. Andrés felt the young man’s last resistance giving way, his anal ring slowly losing its will to fight. And suddenly, the tip of Andrés's cock disappeared with one forceful leap. It had Jake gasping, his head raised in alarm. But he let Andrés go on.
Andrés continued sinking the first few inches of his meat into Jake’s hole, bit by bit. It took a good five minutes of pushing and waiting until, finally, he had totally buried himself in the untouched depths of the young man. Jake let out a deep groan as he felt Andrés had fully arrived inside himself, his bosses’ balls touching his rock-hard ass cheeks. He felt a physical pain unlike ever before. But there was also a sense of humiliation that rose in him.
Now Andrés began to move out and back in ever so slightly, making sure not overdo it again. He looked at his own dick as it was moving in and out of the perfect round opening that he had conquered with patience and technique. Jake moaned lowly. “Please… I think this is too much. I think I can’t take it anymore.” Andrés pushed in. “Shh. Concentrate on opening up. Don’t clench your little hole.” Jake’s moans and his continued pleading were soaked up by the curtained room as Andrés went ahead with his fuck lesson.
Once he felt that Jake had adapted to the movement, he gradually moved into a quicker pace of fucking. It once more brought Jake to the brink of giving up, as he was biting the bed sheet below him. Every one of Andrés strokes felt like a rod of glowing fire being pushed inside his guts. Every time the 7-inch cock pulled halfway out and back in again felt like being ripped open once more, like being owned more fully. Each stroke confirmed that his hole had surrendered to a new dark pleasure.
The plug had felt different, thought Jake. Yes, it had perhaps filled him out more. But it had all been on his own terms. Now he was lying in this strange, darkly lit room, being submitted to the rhythm of his boss's fucking. For a second, he dared to raise his face to look up at the mirror above the bed’s headrest. He could see his own body lying on the bed. His long, muscly legs are spread wide open. His bulging glutes glistening with sweat and spit and lube. And he could see the athletic, tall figure of his boss above him, pushing himself onto this surrendered body, the dick sinking inside of him again and again. He could see the pleasure in his face, eyes closed, mouth wide open. He could feel the slimy skin of the condom moving inside him, perfectly enfolding the warm flesh of his boss’s dick. For a moment, Jake wondered what Daniel would look like on top of him. He was shocked by where his mind had taken him.
Normally, Andrés would have changed positions many times now. He loved to fuck his bottoms in every possible way, loved to explore what gave them pleasure, and in which position his dick would hit their prostate best. But right now, he didn’t want to rock the boat and kept fucking the groaning hunk beneath him for twenty minutes straight. His dick moved in steady strokes, clearly stretching the hole but just stopping short of overpowering it. The bed lightly moved under them, Andrés slender, hairy figure grinding his dick into the pale ass with rolling wave after wave.
At the end, Andrés was pushing in and out in a steady beat. He had slowly accelerated to the speed at which the big boys would be starting to fuck him, he guessed. Jake's hole still felt tight around his dick, and he could feel that the young hunk wasn’t totally relaxing into his first anal fuck session. His muffled, pained groans were testimony to that. But he was managing, thought Andrés. Quite well, actually. Jake had accepted his dick; his hole had been turned into a pussy for the first time. He had been broken in.
Andrés pushed in deep once more – and stopped. He felt that Jake had enough work to do in the next couple of days. “I think you are ready now. We can stop if you want.”
Jake raised his head. “Wait, did you come? I didn’t notice.”
“No, no, I haven’t. But this is not about me or my fun. It’s just for you to get used to getting fucked. And I think you are. I can feel it. So we can stop if you want to.”
Jake was surprised and hesitated. He brought his concentration to his body, down to his hole. It felt beaten and stinging. But as he was screening his body for pain, he could suddenly fully feel the long warmth of Andrés lingering inside of him, causing not just pain but… He quickly pushed away his conflicting thoughts.
“Yeah, ok, you’re right, we can stop. I think I got the hang of it. Thanks.”
“Great, you’re good to go then, champ. All ready for your big premiere tomorrow.” And with that, Andrés brought his dick out of Jake’s hole for good.
As Jake was getting dressed, he felt like he had achieved a major mission. And yet, it strangely felt like something else: unfinished business.
