The Castaway Hotel - 1 - 22. Chapter 22 - Virginia Beach

When we awoke from our last night in Williamsburg, we hustled to packed up our belongings and move on. We took a few minutes to grab something to eat from the continental breakfast and then we were off to our next destination. We traveled slightly more than an hour, before arriving at what was to be our home for the next five days – a motel on Virginia Beach. The boys cheered when I told them the news about how long we were going to be there, and I knew this would give them a chance to rest and relax after the hectic pace of the past few days. We were on the top (third) floor of the motel and our room was facing the beach. We had a private balcony, on which I could sit and monitor the boys, when I didn’t feel like joining them, but the motel also had a private pool we could choose to use instead. After unpacking, we spent the remainder of the day covered in sun block, relaxing on the beach and jumping in and out of the ocean. After an informal dinner, Brandon and Jay approached me, using Danny and Ricky as their back-ups.

“Uncle Josh, can we speak with you?” Jay asked, appearing a little nervous.

“You MAY. Fire away,” I told him. “Both of you should know by now that you can talk to me about anything.”

“We know,” Brandon replied, but then neither of them spoke again for quite a few seconds. Instead, they merely stood there, studying me, for what reason I wasn’t sure. Finally, Brandon found the courage to continue. “Jay and I have talked this over and we just wanted to let you know that after the last week or so, we feel really close to you now, even closer than before. Before, you were kind of like an uncle to us, but now you’re more like a second dad. You treat us just the same as you do Danny and Ricky, so we just wanted to say thank you for everything, especially for bringing us on this trip with you.”

I was flattered and pleased by his comment. “You’re very welcome,” I told him. “In fact, I’m quite honored that the two of you would think of me as a second father. That’s very sweet of you.”

“Maybe they should just call you Dad then, like we do,” Ricky suggested, trying to be helpful, but I gave him a stern look, to let him know he was going a little overboard with his suggestion. However, I didn’t have to, as Brandon spoke up instead.

“That wouldn’t be right,” he objected. “We both have our own dads, and besides, it wouldn’t be fair to you and Danny if we did that,” he added.

“We wouldn’t mind,” Danny told them, “but we can understand that it might be hard for you, because you have your own fathers. I didn’t have that problem, because I didn’t feel I had a father any more, except for Dad here.” At that moment our eyes locked and he flashed me a very special smile.

“Hey, some of my friends call their dads pa or pop,” Ricky offered. “How about using one of those?” Again, I was impressed by his seemingly simple idea, but once again I was concerned he might be pushing the others into something they weren’t ready for.

“I like the idea of calling you ‘Pop’,” Jay said, while flashing me a smile.

“Me too,” Brandon announced, seconding the idea. “Would that be okay with you?” he asked, looking in my direction.

“Don’t you think your parents would object to you doing that?” I asked, trying to explore what possible problems this might create.

“I don’t think so,” Brandon replied. “I know my parents really like you, because they say so every time you do something for me, like when you ask me to stay over at your house or take me to do things with Danny and Ricky. Even before we left, they kept saying how really wonderful it was that you included me and Jay on your vacation and what a great guy you were, so I don’t think it would bother them at all if I called you Pop. In fact, they most likely would think it was very considerate and really nice of me to think of it, even though it wasn’t exactly my idea.” He blushed after admitting that, because he was embarrassed he might be unintentionally taking credit for Ricky’s suggestion.

“I don’t think my parents would mind either,” Jay added. “They’ve always liked you a lot, even when you were just my principal.” I thought about this suggestion for a few seconds, before I responded.

“Are you sure this is what you want to do?” I asked again, just to make certain. They both nodded their heads vigorously, as did Danny and Ricky, even though I wasn’t asking for their input.

“I guess we could do it on a trial basis,” I informed them, “but if we get back and either of your parents object, then it’s back to Uncle Josh. Is that understood?” All the boys nodded their heads again, so it seemed this was how it was going to be.

“To tell you the truth,” I finally confessed,” I like the idea too. In fact, I’m even looking forward to it. I’d almost forgotten that my sons call me ‘Pop’ most of the time too, although I never figured out exactly why, but it would be nice to hear that name used more often.”

“Great!” they both exclaimed, before rushing over to give me a hug. “And thanks for the great vacation, Pop,” Jay added with a huge grin on his face, “even if you guys did tease me a lot about being clumsy.”

We all laughed about that for a second or two, before I commented on what he’d said. “That reminds me, Jay. Please stay away from the balcony. I don’t want you falling off of it and then have to explain what happened to your parents.” He punched me playfully in the arm and then all of the boys jumped on me, pinning me to the sofa.

“Do you promise to leave Jay alone and not pick on him any more, Pop?” Brandon giggled.

“Only if the rest of you promise to keep an eye on him,” I replied.

“No problem,” Ricky shot back, “but the next time you tease him, we’re going to have to torture you. Do you understand?”

“Yes, Daddy,” I mocked in my best childish voice, which only encouraged a barrage of tickling and poking, before I heard one of them say, ‘Tell us you’re sorry.’ I wasn’t about to give in so easily, which caused a big wrestling match to ensue. I held my own for a brief time, but was eventually overcome by the quartet’s youthful endurance and my own poor stamina. Totally spent, I ordered a halt to the activity by relegating my companions to the shower.

The dynamic duo wasted no time in jumping up and running for the bathroom, shouting ‘we’re first’ as they went. Having gone several days with no sexual release, the buddies quickly agreed to do the ‘old hand jive’ for each other, which made them both feel much better. After they’d finished their workout, they came out into the main room to rejoin us, totally naked. They sat down next to me, one on each side, and we watched the Baltimore Orioles’ baseball game that Brandon, Danny and I had discovered, while flicking through the channels.

Brandon and Danny went next and I could tell by the expressions on their faces that they were both looking forward to this opportunity of being alone. After shutting the door and stepping under the spray, Danny asked the question that was on both of their minds. “What do you want to do tonight, Brand?”

Brandon hesitated about making his choice known, since he didn’t want to seem too eager or make Danny feel he was being pushed into anything. Brandon was concerned he might be moving too fast, yet felt he needed to let Danny know what was on his mind. Finally, he began to speak. “Have you… well, have you ever… kinda thought about… well, you know… doing it in… oh, jeez… in the butt?” Danny wasn’t quite as embarrassed by the idea as Brandon had been, but that didn’t mean he was ready to try it yet either.

“Yeah, I’ve thought about it,” Danny admitted, although his head was drooped and he was staring at the bottom of the tub, instead of his friend. “I’m just worried it might hurt a lot, so I’m not sure if I want to try it just yet.”

“Oh,” Brandon replied, a little discouraged. “I really want to try it, but only if we can do it without hurting either one of us.” Danny nodded in agreement.

“Dad showed me some stories on the Internet,” Danny told him, “but only two of them had the characters f**king. Both of those stories talked about the pain it caused the first time, but they also said the pain turned into good feelings, after a while. I guess it’s kind of good the pain didn’t last a long time, but I don’t know how I’d react, if it hurt at all,” he confessed, while studying Brandon’s face, to see if his buddy was agreeing with him or just thinking he was a big wuss.

“I don’t want it to hurt either,” Brandon admitted, trying to make sure the idea wasn’t dropped completely, “and I want to find a way we could do it and make sure it wasn’t painful,” he added, hoping they might still be able to do this yet. When he realized it wouldn’t be tonight, he decided to get something else going, instead. “What are we going to do then?”

Even though Brandon said this to mean, ‘what are we going to do instead of anal sex,’ Danny interpreted his comment to mean, ‘what are we going to do to have anal sex without it hurting.’ That’s why Danny’s response surprised Brandon at first. “I don’t know,” Danny told him. “Maybe we could talk to my dad about it.”

At first, Brandon thought Danny was suggesting they ask me what type of sex they should participate in tonight. “You want to ask him what we should do tonight?”

“No, silly,” Danny responded, “I meant we should ask him if he knows how to do it without it hurting.” This idea nearly floored Brandon, since he wasn’t sure he was ready to do something as drastic as that.

“Danny, I like your dad and all,” Brandon confessed, “and you know that’s true, but I don’t know if I’d feel comfortable talking to him about this. I mean, it’s pretty private stuff and he is, well, an adult.”

“Yes, he is,” Danny explained, “but he’s different than most grown-ups. He’s been really cool about things like this, so far. Would your parents have let us shower together or run around naked every night?” Brandon shook his head, indicating they wouldn’t. “Besides, I think he suspects we’re already doing stuff in here, so if we don’t ask him, who else could we go to?”

“I don’t know,” Brandon responded, after pondering Danny’s question. “I mean, don’t you think he’d get mad if we even asked him? I mean, he’d kinda know we’re planning on having sex then, so wouldn’t that freak him out?”

“I don’t think so,” Danny confessed, “and I’m sure he’d rather have us learn from him, than try it alone and possibly hurt each other.”

“So, you really think he’d be willing to help?” Brandon wondered, although he was still uncertain about following through with Danny’s idea.

“Yeah, I really think he would,” Danny replied, confidently. “He’s helped me with so many other things, including gay stuff, so I don’t see why he wouldn’t help me again.”

“Jeez, this just seems so weird,” Brandon countered.

“I know it does,” Danny concurred, “but I don’t see any other way. If you really want to do this, I think we’re going to have to ask Dad for help. Otherwise, we’ll just have to wait until we find some other way to discover how to do it without hurting each other.”

Brandon thought about it for another minute, while struggling with his desire to do this and the idea of involving me in the process. There was a lengthy pause, before he finally responded. “Okay,” he consented, “but you’re going to have to be the one to ask him.”

“All right, I can do that,” Danny agreed. “We’ll have to get him to stay behind tomorrow, after Ricky and Jay go down to the beach, so we can talk to him alone. Do you think that sounds okay?”

“Yeah, I guess,” Brandon told him, even though he still didn’t sound totally convinced this was the best move. In order to be certain Brandon wasn’t going to change his mind and back out later, Danny thought he’d better confirm their plan.

“Then tomorrow we’re going to ask my dad to help us and you’re not going to chicken out, right?” he asked, while studying Brandon’s reaction to his query.

“Yeah, I won’t chicken out,” Brandon confirmed. He even appeared a little more certain now.

“Then we have a deal?” Danny prodded, one final time.

“Yeah, it sounds like a plan to me,” Brandon replied. “But how about a blowjob tonight then, just to tide us over? It’s been so long since I’ve cum that I feel like I’ve got bowling balls between my legs.”

“You’re on,” Danny agreed, smiling, “and I know how you feel. I have to cum so bad that my gut hurts.”

After reaching this agreement, the two of them quickly proceeded to suck each other to a quick, yet satisfying orgasm. It had been a few days since they last enjoyed a sexual release, so it didn’t take long for their juices to come to a boil and erupt, quite forcefully. After they recovered and dried off, they came out to join the rest of us and watch the end of the game. They knew they would have to wait until the morning for their opportunity to get me alone with them, but hoped I’d be able to come up with a plan to help them solve their problem.

After breakfast the next morning, we all came back to the room to change into our swimwear. Danny and Brandon took their time, while Ricky and Jay sped around, eager to get going. The older duo had just finished undressing, as Ricky and Jay grabbed their towels and headed out the door. The younger pair was eager to play in the surf and soak up some rays in the process. I had changed too and was getting ready to follow the dynamic duo out the door, when Danny spoke to me.

“Dad, we need to talk to you,” he informed me. “Would you mind staying here with us for a little while?” I was puzzled, but agreed, so Danny began to tell me what he wanted. “This isn’t going to be easy to ask you,” he began, “but Brandon and I need your help.” There was a lengthy and uncomfortable silence after he made that statement, leaving me to wonder what was on their minds. Finally, he continued. “I guess there’s no easy way to ask you this, so here it goes. Brandon and I want to have sex by… well, you know… by sticking our dick up the other one’s butt, but we don’t want to hurt each other,” he confessed. As an afterthought, and not necessarily speaking to any of us in particular, he added. “There, I said it.”

“Yes, you did,” I agreed. “But what is it you want me to do for you?”

“Brand and I kind of hoped you could show us how to do it, so we didn’t hurt each other,” he explained, while both of them looked at me quite expectantly. However, I had to think this over carefully, before I responded. I knew that if I agreed, not only would I be teaching them the mechanics of the act, but I’d also be implying my consent for them to have sex. Carefully, I organized what I wanted to say in my mind.

“First of all, I’m not sure you’re emotionally ready to take such a gigantic step,” I admitted, but I could read the disappointment on both boy’s face. “Do you both feel this is what you really want to do?” After looking at each other first, they nodded simultaneously toward me.

“Well, I can see that you’re really eager to try this, but I hope you’ve both thought about it carefully, ” I added. Again they nodded their heads in agreement. “I always told my children that sex was an act of love, not merely a physical release. I also suggested they should have strong feelings about the person they were involved with and avoid merely doing it because someone was cute or convenient.”

“You don’t have to worry about us,” Danny assured me. “I think Brand and me are boyfriends for life. We just have so much in common and love being around each other. We don’t just like each other because of the sex, but that does make it even better.”

“Yeah, Pop,” Brandon chimed in. “Even though I did mess around with a few boys before I met Danny, this is different. I really don’t want to be with anyone else now. Danny’s right. I think we’re going to be together for a long, long time.”

“So that means I have a son AND a son-in-law now?” I asked, trying to lighten the moment. The boys looked at me oddly, before blushing and then smiling.

“I guess you could look at it like that,” Danny replied, after a brief delay. “I mean we aren’t married or anything, but I don’t think that really matters. I guess it’s a good way of looking at it, though, right honey?” he asked Brandon, while kissing him, playfully, on the cheek.

“Yeah, I guess that’s kind of the way it is,” Brandon answered, before his face took on a devilish grin. “Some day Danny will be my wife and I will be his husband, and then you really will be my pop.”

“Hey, you’re going to be the wife,” Danny shot back, while mischievously punching Brandon in the shoulder. “Besides, you’ve got the long blond hair and know how to cook.”

“Hey, I learned how to cook in the Boy Scouts,” Brandon countered, trying to justify his domestic talents, “but my mom taught me some things too. She said I’d need to know how to fix my own meals when I went away to college, so I might as well start practicing now. She said it would be cheaper for me, than eating out all of the time.”

“She’s right,” I agreed, “but I think we should get back to the matter at hand. I can see you boys are committed to each other, so that hurdle has been overcome. However, if I agree to help you with this, it doesn’t mean you can have sex any time you want, though. Is that clear?” They both nodded their heads again.

“Well, I haven’t had any personal experience with anal intercourse,” I advised them, “but I have been sexually active in other ways. I have also read accounts explaining how painful penetration can be for both males and females, and have learned some ways to avoid such problems. If I agree to do this, then you’ll have to trust me completely and promise to do whatever I tell you. Okay?” They both concurred very quickly, even before I had a chance to finish speaking.

“Before you make up your minds, though, you’d better hear me out completely,” I warned them. “If I agree to help you, I’m still concerned that just telling you what to do and then leaving you alone to do it might not prevent the problem completely. If either of you were to hurt the other while trying this, it could evoke some uncomfortable questions from medical personnel tending to you or from Brandon’s parents. Therefore, if I agree to help with this, I want you to understand that it means I’ll be staying with you through the entire experience, so I can observe what you’re doing and make the comments necessary to guide your actions.” The boys were looking uneasily at each other and then at me, but I didn’t stop.

“You’ll have to be comfortable with the fact that I’ll be right beside you while you’re making love for the first time, before you make your final decision. You can change your mind about doing this, if you want, because I know this will be very awkward for all of us, but it’s the only way I’ll agree to help. It’s not because I want to watch you make love, but since we are all inexperienced at this, it’s the only way I can be sure you won’t accidentally hurt each other when your hormones begin to kick into overdrive. If you decide to say ‘no’ to my offer I’ll understand, but the final decision is up to you. Would you be comfortable doing this under those conditions?”

The boys looked at each other, before Brandon used his head to motion in the direction of the bathroom. It was his way of letting Danny know he wanted to discuss this in private first, before agreeing. Danny took the hint and they both stepped into their former playroom, so they could discuss this alone. When they emerged a short time later, I tried gauging their expressions, but couldn’t read what they had decided. Finally, one of them spoke.

“Brandon and I have talked it over,” Danny began, “and we’ll do it your way, as long as you are the only one in here with us when we do it. We don’t want Ricky and Jay watching us and making jokes about what we’re doing.”

“No, it would be just us,” I confirmed, to their great relief. They then began to undress, until I interrupted them. “Hold your horses, my eager young riders. It’s not quite time to saddle up yet. I will need to run to the store first, in order to pick up a few items you’ll need to do this properly. Do you think you can wait until I get back?”

“Yeah, but hurry,” Danny told me. “We don’t want Ricky and Jay getting suspicious and come back here looking for us.”

“Well, you could go down to the beach while I’m gone and then come back up here when you see me return,” I advised them. “I’ll stand on the balcony to let you know I’m ready for you, just in case you don’t see me drive in, but I’m sure the other pair will be having too much fun to even notice we aren’t around.” They nodded their understanding and put their swim trunks back on, while I dressed more appropriately to make the necessary purchases.

“I’ll be back shortly,” I assured them, as I grabbed my keys and left.