The Castaway Hotel - 1 - 23. Chapter 23 - Private Lessons

I went directly to the parking lot, jumped into the van and drove to the nearest drug store. I carefully selected the items I felt would be appropriate to help them, paid the cashier and then drove back to the motel. A few minutes later, I returned, carrying a small bag.

The room was empty when I arrived, so I went out and stood on the balcony, as I had promised. I was scanning the beach for signs of all four of my charges, when I quickly spotted the older pair. They were already heading back in my direction. After looking more closely, I also located the other two, playing happily with a group of children. I was observing what they were up to, when the door to the room opened and the older two came rushing in.

“Did you get everything we needed?” Danny asked, breathlessly.

“Yes, right here in this bag,” I confirmed, while holding up the plastic sack. The boys immediately began trying to develop x-ray vision, so they could see what was inside.

“You’ll find out what’s in there soon enough,” I told them. “That is, if you two are still serious about doing this.” They immediately nodded their heads in agreement, but even with that affirmation, I could still tell they were a bit anxious about what they were about to do. The looks on their faces displayed an equal mixture of eagerness and trepidation.

“I take it Ricky and Jay didn’t see you come back here?” I inquired.

“Heck, the hardly even noticed we were there at all,” Brandon confirmed. “They’ve met some other kids who are here on vacation and have been doing things with them. They only waved at us when we first went down there, just to let us know they knew we were there, but they are too busy with their new friends to notice we left.”

“Okay, that will solve one of my concerns then, although I’m still going to lock the door and fasten the secondary lock, so we aren’t interrupted. You boys get undressed and then we’ll begin,” I advised them. “I won’t involve myself in what you’re doing, other than to give you instruction, guide your actions and monitor your progress. I think I may be crazy for doing this, but I’d rather help you myself, than let you turn to someone else for guidance or fumble your way through this on your own.” I’m sure they understood what I was implying and were appreciative about what I was willing to do.

“Thanks, Dad,” Danny said, as he was removing his clothes. “I knew we could count on you.”

“Yes, thanks, Pop,” Brandon added. “I thought Danny was nuts when he said we should ask you to help, but I should have known you’d help us out. Jay and I know we can pretty much count on you for anything, maybe even more so than with our own parents. I guess that’s why we both love you so much.”

That comment caught me slightly off guard. First of all, I’m well aware that boys this age generally aren’t willing or eager to share their feelings like this, especially when it involves the ‘L’ word. Stunned by the apparent ease and sincerity with which this was said, I didn’t immediately respond. However, after a few seconds, I regained my composure and looked into Brandon’s eyes.

“I love you, too, Brandon. In fact, I love all of you boys a great deal. After my wife died, I was extremely lonely and felt very isolated. When Ricky and Danny came to live with me, they brought a spark back into my life and rekindled emotions I had forgotten were there. You and Jay have only added to those feelings for me. No matter what else happens in my life, I would most certainly feel a huge void if you boys weren’t around. I want you to know, and I’ll tell Jay the same thing later, that you can both count on me to help you with whatever problems you might encounter and I’ll always be available to assist you in finding answers to all of your questions, if I can. Our home will always be your home and you’re welcome there as often and for however long you might wish to stay, with your parents consent, of course.

“You are both calling me ‘Pop’ now,” I continued, “and I want you to know I also think of you as my sons, as well, just like Danny and Ricky. I find it hard to accept that just a few months ago I was severely depressed about being alone, but now I have four wonderful sons who have brought much joy into my life, more than I would have ever thought possible.”

Suddenly, I found two naked boys wrapping their bodies around me, hugging affectionately and kissing my face. I guess this may be the closest I might ever come to being in heaven, without actually having to leave this world.

“Okay,” I announced, breaking the moment. “It’s time to get back to business. Who wants to do what first?” The boys looked at each other and silently reached an agreement.

“I guess I’ll let Danny do me first, Pop,” Brandon announced. “I suggested this, but it was Danny who was most concerned about having problems. If I go first and it hurts me, then I won’t make Danny do it.”

“That’s very generous of you, Brandon,” I explained. “The ability to think of others first and put their welfare ahead of your own is what makes a true friend… or a lover,” I added, belatedly. “I’m glad to know that Danny has chosen his partner wisely.”

“Brand,” Danny interrupted, “if you’re doing this for me, then I’m going to do it for you, whether it hurts or not. I want you to have your chance to see what it’s like too.”

“That doesn’t matter,” Brandon countered. “You don’t have to do this unless we can do it without any pain. I mean that. It was my idea to try this, not yours. If it hurts me, then I’m just not going to do it to you and you won’t be able to make me.”

“We’ll see,” Danny interjected, looking very serious. I could tell that he just wanted to have the last word on this.

“If you boys are still in agreement about doing this,” I told them, “then we should get started, before the other two return.” Shocking them back to the present, they each nodded. “Okay, let’s go into the bathroom first. I bought an enema bag, so you could get cleaned out and make it a little more sanitary.” After seeing their puzzled looks, I quickly explained what an enema was and how it worked, before we proceeded. Once each one had relieved himself of the water and other things in his bowels, each boy finished cleaning up and we moved back into the other room.

“Brandon, I’ll need you to get on all fours in the middle of the bed,” I informed him. We waited, while he got into position, and then I continued. “Now, I’m going to show Danny how to loosen you up for penetration.” Brandon nodded his understanding, so I moved Danny behind him.

“Danny, this is a tube of KY jelly. I want you to put a dab of it on your index finger and then rub it into the skin of that finger. Once you’ve done that, I want you to put a big glob of KY on the tip of that same finger and rub it all around Brandon’s anal ring.” He looked up at me, with a questioning expression on his face. “Rub it all around and into Brandon’s butt hole,” I explained, more simply. When Danny was ready, I got on my knees beside Brandon, reached over his back, grabbed his ass cheeks and pulled them apart, so Danny would have better access to his target. Tentatively, Danny let his finger touch Brandon’s rectum and began to spread the gel all around the outside of the puckered opening.

“Smear some more KY onto that finger now,” I told Danny, “and, this time, you’re going to start to work it inside of the opening. Go slowly and give Brandon’s hole time to adjust to everything you do.” Now, I turned toward Brandon, to explain what he should do.

“Brandon, the first time Danny puts his finger into your butt, it shouldn’t be a problem, but if it seems like it doesn’t want to go in, then relax and push down on your ass muscles, like you’re taking a crap. Not hard enough to really expel anything, but that will open the hole up and remove most, if not all of the resistance. Do either of you have any questions before we begin?”

They both shook their heads, letting me know they couldn’t think of anything to ask. Danny still seemed a little reluctant and unsure about what he was supposed to do, so I took a hold of his right hand, positioned his right index finger so it pointed outward, and then moved it forward, until it touched Brandon’s pink rosebud. I worked his hand slowly, so his finger made tiny circles around the entrance. After doing that for a brief time, I placed Danny’s finger against Brandon’s untouched hole and gently urged him to push it forward.

I think Brandon began to push out, even though he probably didn’t need to, and Danny’s finger slipped in easily, up to the first knuckle. Brandon gasped. “Did that hurt, Brandon?” I asked, concerned about what had just happened.

“No, it didn’t hurt,” Brandon explained. “I guess it just kind of surprised me when it went inside, but I’m fine. Danny, keep going!” Receiving assurance that Brandon was all right, I put a little more pressure on Danny’s hand, pushing the finger in a little deeper. I made him wait for Brandon to adjust, before allowing Danny to twist his hand back and forth a bit, so his finger would twirl around inside Brandon’s chute. Once Brandon seemed fine with what was happening, I urged Danny to push his finger the rest of the way in. Once he had made full penetration, I made him hold his finger stationary for a few seconds, to give Brandon a chance to get used to it again. Once Brandon agreed he was doing fine, I had Danny pump the digit back and forth, slowly finger-f**king Brandon’s hole.

“How does that feel, Brandon?” I inquired, making sure he was able to handle this action.

“Good. There’s no pain at all,” he responded, letting us know this was going well. I let Danny continue this action for a while longer, as I watched him work his finger in and out more energetically, before I made him stop. He looked at me, wondering if he had done something wrong.

“It’s time to go to the next level,” I informed him. “Danny, grab the KY again, but this time put it on both your index and middle fingers. Use a lot of lube and make sure you completely coat both fingers.” Obediently, Danny did as I instructed. “Okay, now insert those fingers the same way you did the first time.”

Cautiously, Danny lined up his fingers and then added a little pressure, until he was able to push them past Brandon’s resilient sphincter. Brandon gasped again, but quickly signaled he was fine. After giving Brandon time to adjust to this larger invasion, I had Danny begin twisting his fingers around again, gradually forcing Brandon’s gateway to loosen. Once I felt Brandon had adjusted to that, I indicated, by making a gesture that Brandon couldn’t see, that I wanted Danny to curl his fingers slightly and he nodded his acknowledgement. When Brandon moaned loudly, I knew one of Danny’s fingers had brushed against Brandon’s prostate. I was directing the action merely by using hand signals now, so I didn’t spook Brandon about what was going to happen next. After having Danny thrust his fingers in and out several more times, I signaled Danny to pull his fingers out completely, before indicating that I wanted him to lube up three fingers this time.

Brandon protested slightly, feeling empty once Danny’s fingers had been withdrawn, but I quickly informed his this was only a temporary situation, so Danny can add more lube. Brandon suddenly relaxed again, after being assured this activity wasn’t over, but we didn’t inform Brandon that this time Danny would be adding an additional digit.

Danny quickly finished carrying out my instructions and aligned himself to work three fingers into his partner. Although getting some mild resistance from Brandon’s back entrance, as it protested the larger girth being forced up it, he accepted it without much problem. Brandon did have to use my earlier suggestion, about pushing out this time, but he quickly adjusted to the thicker penetration. When I felt he was ready, I signaled Danny to twist those fingers around again, followed by an indication that he should also thrust those fingers in and out of Brandon’s butt, at the same time.

Brandon released a little groan as Danny did this, which caused Danny to momentarily hesitate. However, after Brandon let out a little sigh of contentment, followed by what sounded like an additional appreciative moan, Danny went back into action.

“How are you doing, Brandon?” I asked, just to make sure he was all right.

“I’m fine,” he told us. “The last time it kind of hurt for just a second, but not much.” I was about to signal Danny to stop, until Brandon said something else. “It’s beginning to feel real nice now,” he admitted. I figured this meant he was ready to advance to the next step, but there was another problem. Danny was completely flaccid. Considering this situation, I signaled Danny to stop what he was doing, so I could direct them as to what they should do next.

“Brandon, turn around for a minute and face Danny,” I advised, and then I waited for him to complete this maneuver. “Okay, now work on Danny’s penis for a while, until it gets hard.” Enthusiastically, he did as I told him. Once the problem had been rectified, I instructed Brandon as to how to put the condom on Danny’s rigid pole. He did encounter some minor problems doing this, so I had to assist him a bit, and then I had Brandon spread a generous amount of KY over the entire surface of Danny’s sheathed shaft. Brandon rapidly greased Danny’s pole and then both boys were ready to continue with their lesson.

“Great. Now, Brandon, I need you to turn the other way again,” which he quickly did. “Danny, now move back into position, on your knees behind him.” It only took him a few moments to do this. “Danny, I’m going to hold both of your hips and direct your actions for a while, so you don’t get too aggressive. Okay?” He nodded his agreement. “When I think you’re ready, I’ll let go and you’ll be on your own, just don’t fight me before that happens. Any questions?” This time they both shook their heads, to let me know they didn’t have any other queries.

Feeling confident they were ready for the next step, I put my hands on Danny’s hips and lined his penis up with Brandon’s anus. I gently pushed his midsection forward, until Danny’s spearhead was touching the bull’s eye, and then I added a little more pressure on the back of his hips, until the head of Danny’s penis slipped past the guardian. I held him still, once his cock head had completely disappeared, to make sure Brandon was all right. Hearing no protests and noting no problems, I gently pushed on Danny’s hips again, slowly guiding him further into Brandon’s depths, until Danny’s pubes were tickling the back of Brandon’s ass. Once he was completely seated inside his partner, I forced Danny to hesitate, in order to give Brandon time to adjust to the intruder, before we continued. This wasn’t easy, as Danny was now eager to let his instincts take over and do Mother Nature’s two-step.

“Oh, my God,” Danny gasped. “It’s so hot in there and it feel sooooo good.” I was encourage by his words of appreciation, but was still concerned about how Brandon was doing, but not for long.

“Yeah, you feel great in there,” Brandon gushed. “You made my whole body tingle, as you worked your way in.”

Having my concerns negated, I allowed them to move to the next step. Now, I encouraged Danny to begin a slow rocking motion with his pelvis, by pushing and pulling on his hips with my hands. As his penis started sliding in and out of Brandon’s tunnel, guttural noises began emerging from both young throats. I tried to keep Danny using a nice fluid motion – of long, slow strokes – but gradually he began to fight me, as he tired to increase his pace, like a runner eager to begin his sprint toward the finish line. Once he looked like he was totally into what he was doing, I whispered into his ear and released my grip.

Danny continued with all the confidence of a pro, working Brandon’s virgin ass, as he continually increased his speed. He did this instinctively, as he felt his seed begin to churn and boil in his scrotum, and before long, he was pumping hard and fast, as he neared his climax. Both boys were now moaning appreciatively and excitedly. Danny had switched to using short, quick strokes, when he suddenly arched his back and drove his penis all the way home, completely up to the hilt. He swooned and moaned audibly as his cannon exploded, releasing five creamy ropes of semen into the sheath in Brandon’s cavern. Brandon was also moaning and grunting, as he let himself enjoy the feeling the stimulation and ejaculation had created within his bowels during his virginal experience. Once Danny’s dick had been drained, he collapsed on top of Brandon’s back, completely spent. Brandon was too weak to hold them both up, so he rolled onto his side, taking Danny with him, but Danny’s prick remained steadfast, in the confines of Brandon’s deflowered channel. They stayed like that for several minutes more, before either boy commented or moved.

“That was wicked,” Danny began. “I’ve never felt anything that awesome before - ever. It was like a hundred lips were wrapped around my dick and they just sucked everything out of me. I knew it would be good, but never thought it would be that great.” He looked at Brandon and smiled. “How was it for you?”

“Nice, really nice,” Brandon confessed. “You kept hitting something in there that just sent tingles all through me. It’s hard to explain, but it felt really terrific.”

“Did it hurt at all?” Danny asked, a little concerned.

“Only a little, but it didn’t last very long. After that, those tingling things just made me forget about any pain, since it made me feel so good inside. It was really nice.” The two boys were hugging each other and then they began to kiss, as their way of thanking the other for that special moment. Without warning, they stopped making out and then Brandon turned toward me.

“And thank you, Pop,” he told me, “for teaching us how to do it so well.”

“You’re welcome, both of you,” I replied, “and once you’ve recuperated and are ready to switch places, we’ll get you boys set again, but this time I’ll teach Brandon what he needs to know.”

It wasn’t long before they were ready to go in reverse, so I had Danny get on his hands and knees on the bed, so we could begin. While Danny was getting into position, I had Brandon lube up his fingers, and then I worked Brandon’s hand, as we probed Danny anus with one, two and, finally, three digits. I made Brandon work them all around, so he would completely stretch Danny’s tight chute, and we continued this way until I felt Danny’s hole was ready for the real thing.

Since Danny was ready, I had him work on Brandon, to get him hard and then I had him slip on the condom and grease up his pole. When they were in position to continue, I held on to Brandon’s hips and led him through the same beginning process I had put Danny through. As his confidence built, I released my grip on his waist and he continued the process on autopilot. The instincts that nature had given to all of its creatures soon took control and Brandon’s thrusting increased in pace, as he drew gradually closer to his orgasm. His last several strokes were fast and hard, before he sank his muscle deep into Danny’s cavern and filled the condom with several blasts of his warm boy juice. After this consummation had been completed, they became one giant, panting heap of spent boy flesh on the bed, lost in the afterglow of sexual bliss.