The Castaway Hotel: Next Generation - 19. Meeting the Family

The family began to arrive for Thanksgiving on Wednesday afternoon and everyone was in high spirits and happy to be home. We greeted them as they entered and then introduced each person to Elliot.

I think he was quickly overwhelmed with the number of people arriving and I noticed he was mixing up most if their names. No one got bent out of shape by this, they merely corrected his mistake and commiserated about how daunting the task was. He was repeatedly assured they knew it would take him a while before he could keep everyone straight and shouldn’t worry if he got it wrong for a while. Their calm and easy manner helped Elliot feel better about his difficulty, but that wasn’t all they did to make him feel better. Throughout the day, each of those returning gave Elliot plenty of attention and spent time trying to learn more about him.

Fortunately for Elliot’s short-term memory, not everyone was going to be here for the holiday. My older children and grandchildren weren’t coming for this celebration, because this year they were spending the holiday with their in-laws. This was expected, so I wasn’t bothered that they weren’t going to be attending. Besides, they had gone with us on vacation just a few months earlier and were also going to be joining us for Christmas.

As everyone arrived, we tried to get each one settled in as quickly as we could. With so many coming home having room assignments prepared in advance is the key to having a successful holiday. First, we tried to free up as much space as possible, so with that in mind, Jesse asked Elliot if he could stay with him while the others were here. Jesse figured this would be better than asking Elliot to join him, because he thought Elliot wouldn’t want to give up his bed, since he hadn’t been able to enjoy it for very long. Elliot quickly accepted Jesse’s offer, freeing up another room.

I was caught off-guard when I learned about this arrangement. Up until now, Jesse and Andrew were the ones who had always shared a room. I was surprised that Jesse was so willing to change this commitment, but it didn’t seem to bother Andrew. Once he discovered Jesse and Elliot were going to share a room, he agreed to bunk with his biological brother, Sammy, while he was home.

However, that wasn’t my only surprise. Since Cole and Dustin had their own places, a couple of the boys opted to stay with them, rather than at the house with the rest of us. Although Dustin and Cole each had a girlfriend, they also had a spare bedroom, so Graham stayed with his biological brother, Cole, and Pat decided to stay at Dustin’s place. They both said they were doing this to free up more space at the house for others and I appreciated their effort. Still, it won’t be quite the same without everyone under the same roof. The times they are a changing.

Frankie was also bringing his girlfriend with him, but because of his work schedule, they would arrive on Wednesday, but wouldn’t stay as long as the others. They would have to leave on Friday morning, so Frankie would be back in time for his shift. It wasn’t going to be perfect, but it was nice that he was going to be here with us, at least for a while.

Nick and Shannon will also be flying in from Atlanta, even though they had just been here to help me celebrate my birthday. Jake was thrilled we would be seeing them, even if it meant they would be spending Christmas with the Lawrences this year. In reality, Jake was planning to fly to Oklahoma and spend that holiday with them there. In that same vein, the Lawrences were going to be joining us for Thanksgiving, so they could spend a little more time with their son and his partner as well. I had reserved the guestroom for the Lawrences to use while they were here and Nick and Shannon would use their old room.

In addition to the Lawrences, the O’Haras would also be joining us for the holiday. They had originally planned to fly here to see Brandon and Danny, but now they were also going to get to meet their new grandson, Elliot. Although he is technically only their foster grandson at the moment, if Brandon and Danny get their way, they will eventually adopt him and Elliot will become their legal grandson.

When Elliot learned Brandon’s parents were coming, he insisted that I put the O’Haras in his bedroom. He said Jesse and he would share Jesse’s room instead. I think he felt this would give his new grandparents a chance to better appreciate his situation and maybe even ingratiate him, for allowing them to use his room.

After discussing Elliot’s offer over with Danny and Brandon, they both thought it was a good idea and a sweet gesture on Elliot’s part. With that in mind, Brandon said that he would make certain his parents understood this was totally Elliot’s idea and his welcome gift to them. It should help to give Elliot a leg up and put a positive spin on his inclusion into their family.

This left only Ricky and Little Ricky, who had decided to bunk in with each other. Little Ricky didn’t idolize Ricky to the same extent that he had in the past, but they were still very close and spent time together whenever they could. I was glad to see this bond had endured.

Once we got everyone settled in, they came back down and spent time with us. We began chatting with them and trying to catch up on what they’d been up to since we’d last seen them. Although we had been in touch with most of them during the interim, it was nice to have our memories refreshed. Besides, the boys have a way of making most of their experiences sound humorous, so we enjoyed many laughs as we listened to what they’d been up to.

The O’Haras were the last to arrive and Brandon greeted his parents at the door. He kissed his mother, shook his father’s hand and then called Danny over to do the same. Then they took Brandon’s parents into the rec room, where they knew they would find Elliot hanging out with Jesse. Brandon called Elliot over and introduced him to his parents.

“Elliot, this is my mother and father, your new grandparents,” he began, as Elliot gave them the once over.

“Mom and Dad, this is your grandson, Elliot,” he added, proudly.

Elliot reached out to shake Brenda’s hand, but she stepped forward and embraced him tightly against her bosom.

“Welcome to the family sweetheart,” she gushed, as she squeezed him, energetically.

After she released him, her husband shook Elliot’s hand, but then pulled him in close, so he could give him a squeeze too. He also welcomed Elliot into the family.

“He’s such a handsome little fellow and what beautiful eyes,” Mrs. O’Hara told Brandon. “I think he’s a keeper,” she teased.

Brandon knew his mother would have preferred for him to start out with a younger child, maybe even a baby, but she didn’t show any signs of disappointment. Brandon knew his mother would still be very good with Elliot and welcome him into the family with open arms, although he was fairly certain she would have liked to have known Elliot when he was younger.

Elliot blushed at this affectionate greeting. I’ve noticed he’s generally shy around strangers, until he’s had a chance to warm up to them. The smile on his face, however, suggested he liked the idea of having another set of grandparents and I suspect he’ll warm up to them quickly. I predict this visit will go extremely well.

Now that everyone was here, Jake and I took the entire group out to eat, to save us from having to fix so many big meals during their visit. I had reserved one of the smaller banquet rooms at our favorite restaurant and we had to drive several vehicles, as we made our way there to dine. Elliot was somewhat overwhelmed by the size of this gathering, so I can’t wait to see his reaction tomorrow, when the extended family shows up to join this crew.

Once we returned home, everyone went off to do his own thing. I guess it might have been wise if we’d spent more time preparing Elliot for this experience and warned him to be careful of trusting some of his uncles. It wasn’t as if they would be mean or hurt him in any way, but he might become the target of some of their jokes and pranks, as they initiate him into the family.

Elliot had just grabbed a drink and was headed for Jesse’s room when he had his first run in with their friskiness and jocularity. It happened almost as soon as they were out of earshot of the rest of us.

“Jesse, what’s up with this?” Andrew teased. “I go off to college and you replace me as your best friend?”

Elliot looked apprehensive and was beginning to think he had done something terribly wrong. He knew Andrew was referring to him and suddenly remembered that Jesse told him he started speaking again when his new brother, and best friend, Andrew got hurt. Elliot didn’t want to cause a problem for anyone.

“No, bro, you’re still my best bud,” Jesse assured him, “but Elliot’s my good buddy too. Right Elliot?”

“Um… yeah… Jesse and I have become good friends,” Elliot stammered, “but I don’t want to cause any problems. If you want to stay with him while you’re here, I can sleep in the room you were going to be in. Or I could even go downstairs and sleep on one of the sofas.”

Suddenly, Andrew felt bad and looked slightly worried that he had just hurt Elliot’s feelings.

“No, you’re okay,” Andrew assured him. “I was only teasing. Jesse and I will always be best friends, but we’re close to most of our other brothers too. I just want to make sure we also become close to you. You’ve got to learn not to take things so seriously while you’re living here, or you’re going to have your feelings hurt a lot. We like to joke around and pick on each other, so you’d better start getting used to that.”

Andrew laughed after saying this and Elliot looked somewhat relieved. Now, he turned to Jesse, hoping to get more clarification.

“Elliot, these guys like to joke around and have fun, so don’t take anything they say too seriously,” Jesse advised him. “I had some trouble with it at first too, but you’ll soon learn to do the same thing to them, instead of just taking it.”

Elliot took it in stride. It reminded him of his first few weeks at boarding school. You just needed to go with the flow.

“So, are you guys messing around yet?” Little Ricky asked next.

Jesse’s eyes suddenly shot wide open, as he stared at Little Ricky. Elliot, on the other hand, had a questioning look on his face.

“Messing around?” Elliot repeated. “What’s that supposed to mean?”

Before Jesse could say anything to stop him, Little Ricky continued.

“You know, jerking off or sucking each other?” Little Ricky clarified.

Elliot turned beet red and nearly choked, as he attempted to keep from spitting out his drink, when Little Ricky cleared this up.

“Uh, Elliot’s had a lot to deal with since he got here,” Jesse tried to explain, “so he’s been spending most of his time dealing with his problems and concentrating on his schoolwork.”

As he had been saying this, Jesse was giving Little Ricky a look that told him to shut his mouth and let this drop. The problem was, Elliot wanted to ask more questions.

“You guys really do that?” Elliot asked, just as soon as Jesse stopped talking. It was almost as if he hadn’t heard Jesse’s reply.

“Uh, well… only if the guys agree they want to um… do things like that with each other,” Jesse explained. “Uh, nobody has to do that stuff though, so you don’t have to um… worry that anyone is going to make you do it.”

The fact that Jesse was stumbling over his words made it obvious that he was finding this topic difficult to discuss in front of Elliot. He hadn’t talked about sex with him before, because he was worried about how Elliot might react. Even though he seemed okay with the gay relationships around him, Jesse wasn’t sure how he’d react to being confronted with it personally. Elliot might respond the exact opposite of how he’d been up to this point, if he thought someone was trying to persuade him to do those things.

“Hmmm. What if I wanted to try something like that?” Elliot asked.

Little Ricky and Jesse weren’t sure how to respond to his statement and it hadn’t occurred to Jesse that Elliot might actually want to get involved. Little Ricky was also a little scared that he had just let the cat out of the bag and worried that I wasn’t going to approve of Elliot knowing about what the boys do in private. He knew it was something he should have to run by me first.

“Um… have you done anything like that before?” Jesse asked.

“No, but I’ve thought about it,” Elliot responded. “I’d heard rumors about it when I was at Ben Rush, but that’s about it.”

“Are you gay?” Little Ricky followed, more directly than he’d intended.

Jesse was glaring at Little Ricky now. He didn’t want to scare Elliot off by using labels. Elliot hesitated briefly, but then he answered.

“Probably… maybe… I don’t know,” he responded. “I think it’s possible, but I’m not really sure. I know I really want to try doing things with guys, but I’ve never had the chance. When I was at boarding school I saw other guys naked in the showers and stuff, and I liked looking at their bodies. I had to be careful about doing it though, because getting caught would have been like getting an invitation to a regular ass kicking. I always hoped I might find someone who wanted to experiment a little, but that never happened.”

Now, it was Jesse’s turn to be surprised. Elliot was eying him as if he were asking why he hadn’t told him this before and Jesse was trying to come up with an adequate response that wouldn’t upset his newest friend.

“I never knew you felt this way,” Jesse told him. “I didn’t think you’d be interested, so I never brought it up.”

“I’m pretty good at hiding it, but I have checked you out a few times,” Elliot admitted, with a blush. “I tried to see what you had when you were getting changed or getting ready to take your shower.”

“Damn! If I’d known that, I wouldn’t have tried to be so modest,” Jesse laughed. “Normally, we don’t care if the others see us naked. We even like to go around the house without any clothes on. We haven’t done that since you came here though, because we were worried it might upset you.”

“Oh, I’m not sure I could do that,” Elliot confessed, “but I wouldn’t mind being naked with a guy when we were, you know, together. I just don’t think I could go naked in front of a bunch of other people. Besides, isn’t that a little unsanitary.”

That comment caused Jesse to put an arm around Elliot’s shoulders and burst out laughing.

“What has it got to do with germs,” Jesse teased. “I’ll bet you’ll change your mind, once you’ve been here for a while.”

Elliot didn’t think so. He couldn’t picture himself ever being comfortable with strutting his stuff for the entire household to see. Now that this topic had been broached and discussed a bit, the boys came downstairs to join the rest of us.

“It’s too dark to go outside and do anything, so does anyone have any ideas?” Ricky asked.

“I guess we could get some games going,” Trey suggested. “Anyone up for that?”

“I’ve got it,” Frankie told them, before anyone answered Trey. “How about a little nickel-dime poker?”

Quickly, several of the boys said they were in, so Frankie, his girlfriend, Dustin, Pat, Cole, Nick and Danny moved out to the rec room and started a game.

“What about the rest of you?” Ricky challenged. “Anyone else have an idea?”

“We have several Uno decks,” Jesse offered.

“That sounds like fun,” Elliot chimed in. “I’ll play, if you do that.”

Before long, Jesse, Elliot, Andrew, Sammy, Little Ricky and Graham sat down and began playing Uno in the dining room.

“Are any of the rest of you up for a little Trivial Pursuit?” Ricky wanted to know.

After talking it over, Ricky, Brandon, Shannon, Kevin, Vinnie and Trey were choosing partners and heading into the living room, so they could participate in this activity. Since they didn’t feel they had enough, they came into the family room and dragged the O’Haras, Lawrences, Jake and me out to join them a few minutes later.

I noticed that while playing Uno, Elliot would listen to the trivia questions and absent-mindedly share the answer with the other boys at his table. I was glad that Brandon had teamed up with Kevin, rather than his son, because they would have given Jake and me a run for our money. The educator in me was impressed by the vast amount of knowledge Elliot seemed to have, particularly for a freshman. He has, on occasion, demonstrated an intelligence he attempts to keep hidden. I suspect he does this to fit in with his peers, because no kid ever wants to be tagged a geek or a nerd. I’m looking forward to seeing his first report card and I’ll be surprised if it isn’t all A’s.

Our Trivial Pursuit game turned out to be a rousing, and highly competitive event, but Jake and I ended up winning and dazzling the others with our knowledge of minutia. Since we were finished, I got up and made a detour to the family room, before I walked back to the dining room.

“Okay, who won at Uno?” I asked.

My voice surprised a few of the boys and caused them to jump, because they hadn’t seen me come in.

“Graham won a game and Little Ricky won the other,” Jesse announced.

Seeing Elliot was busy chatting with the others he’d been playing the Uno game with, Jesse got up and followed me, as I headed toward the rec room to check on the poker game.

“Dad, I need to talk to you,” he began.

“Okay, what’s up?” I wondered.

“Little Ricky let it slip in front of Elliot that we did stuff,” Jesse admitted. “I think Elliot is interested now, so I wanted to check with you first, in case Elliot says anything or asks if I’ll do something with him.”

He looked at me, waiting for my answer.

“I don’t think there will be a problem with that,” I advised him, “but you’ll have to ask Danny and Brandon about this. Elliot is their responsibility, so they’ll need to make the final decision.”

He hadn’t thought of that before, but realized I was correct. For that reason, Jesse followed me, as I went into the rec room.

“Okay, who’s winning the poker game?” I asked, as we walked up behind the others.

“Frankie won the most and Dustin and Danny are the big losers,” Cole informed us.

“It’s okay,” Nick chimed in. “They can afford to lose a few bucks.”

“Hey, Danny, maybe Elliot will give you a loan,” Brandon teased his partner.

The other poker players chuckled at their comments, but no one really lost or won very much. They had participated in the game primarily for the camaraderie and challenge.

While everyone was joking around, Jesse asked Danny if he could speak with him alone. He agreed and walked with him to the foyer.

“I think we should get Brandon too,” Jesse urged.

Danny looked puzzled, but decided to do what Jesse wanted. He went and got Brandon and brought him back to the foyer, before they went upstairs for some privacy.

“Okay. What’s up?” Danny asked, once they were all together.

Jesse quickly explained the situation to them and then asked what they thought. He told them this all came up by accident, but he had a feeling Elliot was going to ask him to do something eventually. Danny and Brandon discussed this situation briefly, before they gave Jesse their answer.

“As long as Elliot is the one suggesting it, then we feel it will be okay if you do something with him,” Danny explained. “I don’t think he’s ready for anal yet, but the other stuff should be fine. We trust your judgment, since we know Dad trusted you with Jordan and Nicky.”

Jesse blushed slightly, since he didn’t think anyone else knew that he had messed around with his other nephews. I guess Danny and Brandon felt adding one more nephew to that list would be okay, as long as it was Elliot’s idea. Jesse thanked them and went back down to the dining room, where Elliot and the others were still playing.

“Where have you been,” Elliot asked, as Jesse walked back into the room.

“I had to go to the toilet,” Jesse replied. “Why? Did you want to join me?”

The other boys chuckled and Elliot let the subject drop.

At bedtime, Elliot did exactly what Jesse was expecting. Rather than put on his PJs, he stripped down to his underwear instead. When he was ready to hop into bed, he mentioned his interest again. Then, he tried to see if he could get Jesse to help him participate in another new experience.

“I can’t believe you never told me you did anything with your brothers,” Elliot said.

“I wasn’t sure you’d be interested in hearing about it or trying anything yourself,” Jesse replied.

“Well, I am, so do you want to do something tonight?” Elliot asked, hopefully.

“What did you have in mind?” Jesse wondered.

“I don’t know. Anything would be a change of pace for me,” Elliot told him, but his response didn’t give Jesse much information.

“Have you done anything before?” Jesse asked Elliot again.

“Well, I’m in a pretty serious relationship with my right hand, but that’s about it,” Elliot joked.

“HAHAHA. That’s all right,” Jesse laughed. “Would you like to jack each other off then?”

“Okay! That sounds good,” Elliot agreed.

“Do you want me to do you first, or do you want to do me?” Jesse asked next.

“I’ve never touched anyone else’s cock before and no one has ever touched mine either, at least not, you know, sexually,” Elliot confessed.

“Okay, then I’ll do you first, since you’ll probably cum quickly,” Jesse suggested, “and then you can do me.”

Elliot didn’t have a problem with his suggestion, so Jesse told him to pull his underwear down so he could get at his penis. Elliot was already hard, so it appeared that just thinking about doing this was enough to stimulate him. Seeing that, Jesse concluded this might not even take as long as he first thought. Jesse reached over to the nightstand and grabbed some lube, which he spread on his hand. Then he wrapped his fingers around Elliot’s four-inch cut pole and began sliding his fist up and down the shaft.

Elliot began to moan immediately and his breathing became quick and shallow, almost like a pant. At the same time, his body began to squirm beneath Jesse’s experienced grasp. Jesse had only pumped a few times on Elliot’s dick when he began to notice Elliot’s testicles were beginning to draw up closer to his body. That was another sign Elliot was very close. Jesse merely stroked him a few more times, and then Elliot gasped, his body tensed and drops of his pearly seed exploded from his cock. First one, then a second and finally a third spurt catapulted from his cock head, and then his body collapsed. He was now enjoying the wonderful feelings of afterglow that enveloped his body, as he recovered from his first boy-boy sex.

Jesse waited a minute and didn’t speak, but once he saw Elliot begin to move about and come to life again, he confronted him.

“Did you enjoy it?” Jesse asked.

“Hell, yes!” Elliot replied. “It was great.”

“I’m glad you liked it,” Jesse told him. “Are you ready to do it to me now?”

”Totally,” Elliot agreed, excitedly. Jesse quickly removed all of his clothes.

“Go ahead,” Jesse urged. “I’m leaving it up to you to get me hard.”

Tentatively, Elliot reached over and rested his hand on Jesse’s warm belly. He stroked the soft flesh gently and then cautiously brought his hand down, until it touched Jesse’s dick. Fortunately, Elliot was ambidextrous, except for writing, which allowed him to do this without too much difficulty, since his right wrist was in a cast. Elliot was very gentle as he touched Jesse’s penis, which almost made it appear as if he was afraid he was going to break it. Carefully, he ran his fingers over Jesse’s cock and testicles.

“Go ahead. It’s not going to bite,” Jesse teased, and Elliot cautiously wrapped his fingers around the expanding shaft.

“Damn, it’s big,” Elliot gasped.

Jesse’s penis had now reached its maximum stature of 7.5 inches of fairly thick meat and Elliot’s comment caused Jesse to giggle.

“It’s a decent size. I’m pretty proud of it,” he concurred, as Elliot began to slide his hand up and down on Jesse’s sausage, “but you should see some of my brothers. They’re even bigger yet.”

Elliot couldn’t even begin to imagine that.

“Here, use a little of this,” Jesse advised him, while handing him the lube.

“What is it?” Elliot shot back.

“It’s stuff to make your hand slippery,” Jesse explained, “so it will slide over the skin easier. I used it on you. Didn’t you notice?”

“I did, but I just didn’t know what it was,” Elliot admitted. “It did feel good though.”

“Yeah, I know,” Jesse confessed. “That’s why I want you to use it on me.”

Elliot stopped what he was doing and applied some of the substance to his hand. After spreading it around, he grabbed Jesse’s cock again and began stroking it. He was amazed at how much better his fist slid over the surface.

Elliot continued to pound away at Jesse’s dick and realized this was taking longer than it ever had taken him when he jerked off. He felt his fingers begin to cramp up slightly and the muscles in his arm were starting to burn.

“Are you almost ready to shoot?” he asked, as he looked up at Jesse’s face.

“Yep, just about,” Jesse agreed.

Elliot kept pumping, while hoping it wouldn’t take much longer. Even though his hand and arm were hurting, Elliot wasn’t about to give up. He wanted to give Jesse as much pleasure as Jesse had given him.

When Jesse finally arched his back off of the bed and let those creamy drops erupt from his penis, Elliot felt a sense of relief and accomplishment. Elliot kept stroking him until Jesse told him he could stop, and then he began rubbing his left arm as best as he could with his right hand, kneading his aching muscles.

“Well, did you like that too?” Jesse asked, a few seconds later.

“Yeah, I did,” Elliot confirmed, “but that was a workout. My arm was getting tired.”

“Oh, you’ll get used to it after a while and that won’t happen any more,” Jesse explained, much to Elliot’s relief.

He was beginning to think that maybe this wasn’t such a good idea, if his arm was going to feel like this afterward. However, now that they had both gotten off, they cleaned up and went to sleep. Elliot was more than satisfied with his first experience and eagerly looking forward to doing it again.