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    Bill W
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  • 5,046 Words

The Castaway Hotel: Next Generation Book 2 - 39. Spreading Their Wings

The following week passed by quickly, since Brandon and I were busy taking the boys to their practices and games, as well as muddling through our normal routines. Elliot spent most of his time with Ian, while Noah was hanging out with Adam. Noah had also asked Adam's parents to join us for the cookout, but they didn't give him an immediate reply. They said they'd talk it over and then let him know later.

Since Adam was at our house one night when we got home from work, I decided to ask him about his father. "Adam, I was wondering what your father does for a living?"

"He's a supervisor at the D.O.T."

"I see. Does he in work in the driver and vehicle section, or the highway group?"

"He's in charge of the guys that do the road work."

"Ok, I just wanted to know before they came to the cookout, because I thought it might give us something to talk about. Have they decided if they're going to join us yet?"

"Nah. I think Dad wants to, but Mom is letting her hang ups get in the way."

"Did you tell her that no one from our family or any of our friends would stare or saying anything while she was here?"

"I told her some of it, but I didn't want her to know that you guys all knew about her problem yet. I thought she might decide to stay home if she found out about that."

"Well, keep working on her, as we still have a couple of weeks before we get together. Maybe you could share some of this information with your dad and see if he can find a way to use it to get her to come."

"Ok, I'll try that."

Since Ryan was staying over at Owen's house this weekend, I didn't get a chance to find out where Owen's dad worked, but I still had time to do that too. I wasn't about to press the issue or push the panic button just yet, as long as we were able to discover the information before we all got together.

The following Wednesday we all went to see Ryan's team play Owen's team again. I think both boys were more intent on winning this game than any of the others, especially Ryan, since Owen's team had won the first match up. Owen was apparently hoping to make it a clean sweep, while Ryan wanted to even the record. I had never seen either of them quite this determined before, so I hoped it didn't result in a problem when the game ended.

Both teams played well and both boys were doing better than they had all season, so we were all extremely proud of them. The lead had changed several times over the first five innings, and the score was tied when Ryan came to the plate as the leadoff batter in the bottom of the sixth. He looked determined and I knew he wanted to get a hit, but the second pitch was wild and struck him in the side, putting him on first base. As he was trotting down the baseline, I saw him looking out to right field, and then he either said something or made some sort of a signal to Owen as he stepped on the bag. I wasn't sure what it was about, but I saw Owen shake his head vigorously before Ryan turned toward home plate and concentrated on the game again.

The next batter laid down a bunt toward third, but it was fielded by the pitcher and he tried to get Ryan out at second, rather than taking the easier out at first. Ryan had managed to get a decent lead before the pitch was delivered, and then he started running as soon as the ball left the pitcher's hand. Since he was also fairly fast, he was able to slide into second well ahead of the throw, which put runners on first and second with no outs. As I looked out at Owen, I could tell he was upset that his team had failed to record an out, but surprisingly he still smiled and gave Ryan a 'thumbs up' signal when he saw Ryan looking in his direction. I think he was letting Ryan know that he was happy he'd done well, even if it was to his team's detriment.

The next boy up laid down another bunt, but this time the third baseman fielded the ball. Since there wasn't much of a chance to get Ryan out at third, the boy threw the runner out at first instead. Now, there were runners on second and third with only one out, when there probably should have been two outs and just a runner at third.

The following batter stepped to the plate and hit a long fly ball to the outfield. The center fielder was able to run it down and make the catch, but he wasn't able to throw Ryan out as he tagged up and dashed to the plate. He scored easily, putting his team ahead by a run, but that would have been the third out if the pitcher had taken the out at first earlier, rather than trying to get Ryan at second.

After the third out was made, Ryan's team went out to their positions again, ready to protect their lead. They were able to prevent Owen's team from scoring and ended up winning the game. As soon as it was over, Ryan came running up to us with a huge grin plastered across his face. After we congratulated him, we went over to chat with Owen and his parents.

"Ok, we're even now," Owen conceded as we approached. "Our teams each won one of the games we played against each other, so I guess we'll have to wait 'til next year now."

"Yeah, but I hope next year we'll be playing on the same team," Ryan added.

"Yeah, I'd love playing on the same team with you," Owen agreed.

"If you don't mind the interruption, I'm curious to know what went on between you two when Ryan got on base the last time?" I announced as I looked from one face to the other. "I saw you doing something, and then Owen shook his head, so what was that all about?"

"I just asked him if he told his pitcher to throw the ball at me," Ryan admitted before giggling.

"I probably should have, but I didn't," Owen joked in return.

After saying goodbye to Owen and his parents, after we told Owen we'd see him on the weekend. We also reminded his parents that we'd see them at the cookout the weekend after that, which prompted Terri to respond. "We're looking forward to it. Can we bring anything?"

"Just yourselves and a healthy appetite," Dad responded before I could.

Benny and Joshie had a practice the following night and a game on Friday, which was their last game too. It appeared as if things might calm down a bit after that, at least until school started again, and we were looking forward to being able to catch our breath.

Benny and Joshie were really psyched for the game, although they were also slightly disappointed that their season would be over after this game. They both played hard and did quite well, but they lost. Their team ended the season above .500, though, so they weren't too upset, but I'm sure they still would have liked to win their final game.

Terri dropped Owen off at the house after we got home from the game, and once we were inside, I decided to ask Owen a question. "Owen, where does you father work?"

"At Sun Trust."

"Oh, what does he do there?"

"He's the manager of the local branch office. Why?"

"I was just curious, since I wasn't sure what he did."

"Oh, ok," he replied, and then he moved a little closer so he could whisper something to me. "Ryan said he told you about what I wanted to do, so will it be ok if we try doing it tonight?"

I was hoping he'd forgotten about this, but I should have known better. Since I didn't want anyone else to hear what we were talking about, I pulled him away from the others.

"Look, let me ask you some questions first. Have you ever tried putting anything up there?" He immediately blushed, while at the same time his head drooped slightly toward his chest and swayed slightly from side to side until he answered.

"Uh huh," was his very brief and timid reply. I understood he was slightly embarrassed, but I wanted to know this information.

"So what things have you used when doing this?"

He hesitated for a few seconds before he looked at me and answered. "A magic marker, a big one, not one like a pen, and I've used the handle of a hair brush and a small flashlight too."

"Did you use anything to make those things slide in easier?"

"Yeah, I put some baby oil in my butt first, before I used any of them."

"And did you have any problems when doing that?"

"Nope. I even liked doin' it and thought it felt good. That's why I want to see what it's like when Ryan does it to me."

"He's a little bigger than any of those items you've mentioned."

"Not much bigger, so I don't think I'll have a problem with him doin' it to me either."

"I have to admit that you've done more already than I'd expected, but I'm still worried about you boys trying this. You're both still quite young and there will be plenty of time to do this later, so maybe you should just stick to the things you've been doing."

"But I'm ready to do this - I know I am - and I want Ryan to do it to me. I won't ask to do it to him, cuz I know he's not gay and doesn't want to try it, but please let him do it to me." I thought about this for a few seconds before I answered.

"You're absolutely sure then?"

"Yep. Totally."

"Ok, just let me get some lube for you boys to use then. Go get Ryan and I'll meet you up in his room in a few minutes," I told him.

I then went to my bedroom and retrieved the container of Glide before heading up to Ryan's room. While I was there, I wanted to tell both of them a few more things, before I allowed them to do this.

"Ryan, I want you to put some of this on your penis before you do this, but first I want you to put some of this on your index finger and then slide it back and forth in Owen's rectum. After you have done that for a while, I want you to lube up your index and middle fingers and then insert them at the same time so you can repeat what you just did with one finger."

"Ewww, that sounds gross!" Ryan complained.

"Wait! Stop and think about this for a moment. You've been teasing me to let you put your penis in there, so why do you think it's gross to put your fingers in there?" He looked at me pensively for a few seconds.

"Yeah, I guess I never thought about that. Ok, I'll do it then."

"Owen, after Ryan loosens you up, you might want to suck his penis and get it good and hard before he puts any lube on it. Then, when you're ready, it will be easier if you get on all fours and let Ryan enter you from behind.

"Ryan, I want you to add more lube to Owen's rectum and your penis once he's in position, and then take your time inserting your penis. Don't just ram it in. Take it slowly, and Owen you might want to push out slightly with your anal muscles, because that will make it easier for Ryan to slip inside."

"K, we'll do that."

"Just stop if there are any problems or if Owen feels any pain. Ryan, since you're the one inserting your penis, you'll need to be considerate about how it's affecting your partner, because you'll want him to enjoy this as well. That's why you don't want to just shove it in and possibly hurt him or do damage." It was obvious Ryan understood what I was saying, since that had happened to him with the trucker, and then both boys looked at each other and back at me before nodding their understanding. "If you have any questions, I'll be waiting in my bedroom until you're done."

"Thanks for letting us do this," Owen said as I was leaving the room.

I then found Brandon and explained the situation to him next, and then we both sat down on the bed and waited to see if the boys needed anything. Before long, they both came bursting in the room, still totally naked and with huge grins on their faces.

"It didn't hurt at all and I really liked doin' it," Owen gushed.

"And I slid my dick in and out of him until I shot my stuff in his butt."

"It obviously didn't take very long, but I'm glad it worked out and you both enjoyed it."

"So can we do that from now on?" Owen wanted to know.

"I don't think you'll need to do it every time you want to get off, because there are other things you can do that will accomplish the same results. I suppose we could allow you to do it once each time you're here, and I'll even let Ryan keep the lube in his room so you'll have it to use."

Brandon and I then walked the boys up to Ryan's room and tucked them in. I had no idea how long it was going to take for them to fall asleep, because they were still caught up in the euphoria of having tried anal sex for the first time.

The following morning, Ryan and Owen were still all smiles as they sat down at the table to have breakfast with the rest of us. Brandon and I noticed this, although everyone else seemed to be oblivious to their current, upbeat mood.

After they finished eating, the boys went to play video games for awhile, and then they came out to ask if they could go in the pool. We all agreed it would be fine, but none of us went out with them this time. They were all capable swimmers, so we let them do it on their own. A little while later, Ryan came in and asked to speak with me alone.

"I told Owen I needed to pee, but I came back so I could ask you a question. I know he's not pushin' for me to do the same thing he did, but I can tell he wants to try doin' it too. Do you think I should do it for him?"

"Ryan, that's up to you, but I'm really surprised you're even considering it, especially after what you went through."

"I know, but he really seemed to enjoy having me do it to him, and he's a lot smaller than the guy who did it to me before, so I thought maybe I should give it a try. I just want to do it for Owen, so he can see what it's like too."

"I'm pleased that you're willing to consider his feelings too, but are you sure you're ready to do this?"

"I think so, cuz I want him to be happy too. I'm afraid if I don't do it, then he'll want to find someone else to do it with, and then he might start doin' everything with that other person, and not with me any more."

"I suppose it's possible that might happen, but if you're not gay, then why would you care if he does that with someone else?"

"Cuz I like what he does to me and how it feels, so I don't want him to stop. He makes me feel really good, so I want to keep doin' those things with him."

"I can't see him stopping completely, even if he does find someone else to do that with."

"Maybe, but I still think I should do this for him. That way he won't have to think about doin' stuff with no one else."

"It's up to you, but if you decide to do this, then you should have him try using other things on you first, like he did to himself. If you really want to do this, then I've got some items you can use to get ready, but I also want to talk to you about some other issues as well. Ok?"

"Yeah, ok, but why do I need to do this? I've already had something up there before."

"Yes, and you said it hurt like hell, so I want you to be ready this time. Besides, that was quite a while ago and I'm sure your opening has adjusted back to its normal size since then."

"K, I'll talk to Owen about this later then and see what he thinks."

"Ok, just promise you'll let me talk to you again before you try anything."

"K, I promise."

Ryan then took off before the others figured out he was doing more than just using the toilet. However, when the boys came inside later, he and Owen came over to see me, rather than going to the family room with the other boys.

"We're coming to you, just like you said," Ryan began.

"Ok, follow me up to my bedroom."

When we got there, I had them sit on the bed while I retrieved a few things. When I came back, I had several additional items with me. "These are called dildos, and as you can see they come in different sizes. Since Ryan wants to do this and hasn't prepared himself like you did, I want you to use the smallest one on him first, and then work your way up through the larger ones. Just promise that you'll stop if Ryan feels any pain."

"K, but where did you get these?" Ryan wanted to know.

"Let's just say that you're living in a household that has had many gays, so these are toys we've had to play with."

"Are they clean then?" Owen asked, making a face.

"Yes, and I'll show you why." I then pulled out a small box of condoms and a tube of lube. "We always put one of these over the dildo before we used it, to keep it clean for everyone else. I'll show you how to put one of them on the dildo, but you'll also be using them on yourselves, if you start doing things like this with anyone else. Once the condom is in place, just add some lube to it and you'll be ready."

"But we didn't use one of those when Ryan did it to me," Owen stated wide-eyed.

"As long as you aren't doing things with anyone else, then it should be all right to do it without one. However, if either of you start messing around with other boys or girls, then these will become necessary."

I then showed them how to properly slip the condom on the dildo, while making sure they also realized it was the same procedure they would use when putting one on themselves. Once I was certain they understood, I let them go up to Ryan's room carrying the items I'd just given them.

When they came downstairs again before dinner, I didn't notice anything unusual about them, so maybe they hadn't tried doing anything after all. If they had, it must have gone well, because I didn't notice Ryan walking funny, but I was convinced they'd let me know about whatever went on later. At least I hoped they would.

After we ate, I decided to take the boys out for a walk. Benny, Ryan, and Owen hadn't been given a tour of the property yet, and there were still a couple of hours left before it would start getting dark, so I asked if they wanted to do this. After they all agreed, I had them dress appropriately first, because I didn't want them to get scratched up by the briars we might encounter while we were out there.

It was a nice outing and I pointed out several features to them as we circled around the property before returning to the house. It was something different from the things we normally did, and I think the boys enjoyed spending time outdoors and getting to see how much land we owned. When we got back to the house, I sent them all up to take their showers, while I sat down to talk with Brandon and the others.

"Did you show them the ravine?" Dad asked.

"No, I stayed away from there, but I'll do that another time. The daylight was starting to fade when we got near there, so I felt it would be better to do it when the sun was brighter and they could see the ravine clearly."

"So none of them complained that doing it was boring?" Trey followed, as he flashed me a sly grin.

"No, surprisingly they didn't. They were actually very good about it."

As soon as we heard the boys finishing up, we gave them a few more minutes before we went upstairs to tuck them in. When we got to Ryan's room, Owen had something to tell us.

"When we left your bedroom and came upstairs, I told Ryan he didn't have to do it, but he wanted to try, so we used the dildos you gave us. I put each one up his butt, and he was ok with it."

"And how did you feel about it while he was putting those things in you?" I asked Ryan directly.

"It was ok and it didn't hurt at all, so I think I'm ready now."

"Are you sure about this?"

"Yeah, I want to do it for Owen."

"Ok, just heed the same warnings I gave you last night and stop if there's any pain at all. We'll wait in our bedroom again, if either of you needs anything."

"Ok, and thanks for letting us do this."

Brandon questioned me about this, once we got to our room. "Do you really think this is a good idea, after what Ryan has been through?"

"Yes, because he wants to do it. Since they used the dildos to get him ready, and seeing he didn't have any problems with those items, I felt we should let him give it a try."

"So you don't think his being raped will make it difficult for him or cause him to mentally balk?"

"There wasn't much scarring around his rectum from when it happened to him, and he hasn't had any problems with bowel movements, so I think he'll be fine physically. He also has expressed a desire to try this, so I doubt he'll change his mind in the middle of things, but we'll wait here, just in case. I don't expect any problems, though."

"Ok, you're the doctor, so it's your call."

We hadn't sat there for very long after we'd finished talking when two naked boys came bursting into the room. "I did it and it didn't hurt at all," Ryan boasted.

"Yeah, he didn't have any problems and I really liked doin' it to him. I liked it a lot."

"How about you? Did you enjoy it too, Ryan?"

"Not like I did last night, but it was ok. I didn't mind doin' it for Owen, since he did it for me."

"As long as you're both ok with it, and I'm glad neither of you experienced any pain."

"Maybe there was a little, but not very much," Ryan admitted, as we walked them up to his room. After tucking them in, we went to our bedroom again.

"I'm glad it went well," Brandon said after we shut the door.

"Yes, they both seem happy and neither one had any problems."

"But does it mean they're going to be doing this all the time from now on?"

"I told them I thought doing it once each time Owen stayed over should be enough for now, and they could satisfy any other needs by doing the things they'd been doing before."

"Ok, I just hope they stick to that."

When we were getting ready for church the next morning, I was curious to see if Ryan or Owen would have any qualms about joining us today, after the things they'd done over the weekend. Neither of them seemed fazed in the slightest, though, as we walked to the main entrance of the church and separated to go to our Sunday school classes.

When we all met up again for the service later, Owen made sure he sat beside me. I wasn't sure why he did this, because he didn't say anything, although I hoped he'd explain it to me when we got to the house. I wanted to know if there was a particular reason he had done this, or if it was purely coincidental.

After church, we went out for brunch before going home. As soon as we reached the house, the boys began asking if they could go swimming.

"I don't have a problem with that," I agreed.

"But we want you guys to do it with us this time," Owen insisted as he looked at the rest of us hopefully.

"Ok, I'll go in the pool with you then," I agreed.

"And so will I," Brandon added.

Before long, everyone had agreed to take a dip in the pool too. This time we went to our rooms to undress first, and then we carried the clothes we were going to put on afterward when we came downstairs again. At least that's what the adults did. The boys all paraded downstairs totally bare-ass, as we headed toward the backdoor.

"Thanks for doing this with us," Owen said as we were walking toward the pool.

"It's not a problem, and I know how much you enjoy seeing the rest of us like this too."

"Yep, especially you. I'm really happy you let Ryan and me do those things we wanted to try."

"I'm sure the others would have let you do it too, but since I'm the doctor, they leave those decisions to me."

"I'm gonna have my mom start bringing me to see you when I get sick or need a doctor from now on. You can even give me a physical."

"Well, I've seen everything already, so I'm sure you won't have a problem with anything I'll need to do."


We spent about an hour in the pool with the boys, and then the rest of us got out, dried off, and returned to the house. Most of the boys stayed in the pool, and we didn't have a problem with that, but Wyatt was getting tired. So Dion and Trey made him come inside with us.

When the boys came in around 3:00, I asked Owen if he was ready to go home. "Uh, me and Ryan want to go up to his room and do something first," he replied, before the two of them darted up the stairs.

I didn't question what they were up to, but after we'd dropped Owen off at his house, I decided to ask Ryan about it. "Owen wanted me to do it to him again before he went home."

"Just don't overdo it and start acting like a couple of horny newlyweds."

"Ok, we won't."

"So you were ok when he did it to you?"

"Yeah, it wasn't anything like when the other guy did it to me. Owen was really gentle and kept asking if I was ok. I thought it might bother me once he started, but I didn't mind it at all."

"If you thought it might bother you, then why did you want to do it with him?"

"I told ya. I don't want him to start messin' around with no one else."

"So you were willing to do something you didn't really want to do, plus you were willing to possibly endure some pain so Owen wouldn't find someone else?"

"That was part of it, but I wanted to do it for him cuz he was letting me do it to him. I didn't think it would hurt like it did with the other guy, so I wasn't too worried, but I just wondered if I'd feel bad afterward, cuz I'm not gay. I never even thought about that when we was doin' it, though, and it even felt kinda good. It doesn't mean I'm gay, just that I don't mind doin' it with Owen."

"Would you have a problem if it turned out that you were gay?"

"Not really, it's just that I don't want to have more problems like I had with those other boys. I still want to try stuff with a girl too, but I don't mind doin' this with Owen."

"Ok, and that's fine. There are other guys that don't mind doing those types of things with either sex as well, which means they are bisexual."

"Yeah, maybe I'm one of them, then."

"You might be, but you're young and are still trying to figure things out, so there's no need to label yourself. What you should be aware of, though, is how you feel about the other person. Do you have feelings of love for him or her, or does he or she feel that way about you? Are you doing this because you really care about each other, or is it just for the good feelings you get from having sex. That's what will decide if you're gay, straight, or bisexual."

Copyright © 2017 Bill W; All Rights Reserved.

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Great chapter Bill. Ryan and Owen seemed to have taken a big step. Keep up the awesome writing!

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Thanks, Dahawk.  It may have surprised some that Ryan was doing this, but he doesn't feel forced or pressured, and he made up his own mind. 

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6 hours ago, Dewilmnative said:

Great chapter Bill, I like the way you are building the relationship between Owen and Ryan. 

Thanks, Jon.  The two characters just seemed to come together and hit it off. 

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i think Ryan and Owen have some Butterflies in the stomach. Another great Chapter Bill, Thank you.

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24 minutes ago, Stix said:

i think Ryan and Owen have some Butterflies in the stomach. Another great Chapter Bill, Thank you.

Don't we all the first time?  I'm sure they'll get over it.  Thanks for the feedback, Stix. 

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