The Castaway Hotel - 4 - 23. Chapter 23 - The Fickle Month Of May

May started with a flurry of activity, much of which turned out to be mixed blessings for the family. Shortly after Frankie and Dustin were notified they had been accepted into their primary college of choice, Sammy informed me he needed to talk to me – alone. I wasn’t sure what was up, but agreed to do as he asked. However, I was busy fixing dinner and it was something I needed to stay with and keep an eye on, so I asked if I could do this after we ate. He agreed, but I could tell he wasn’t happy about it.

Sammy seemed a bit testy for the next couple of hours, until I finally met with him in my bedroom after dinner. As I closed the door behind us, I was wondering what this was going to be about.

“Dad, do you think I’m dumb or something?” he asked me, quite seriously, as soon as I turned around.

“Of course not, Sammy,” I told him, slightly confused as to what he was getting at. “You’re a very bright young man.”

“Then why do you treat me like a dumb little kid?” he shot back, yet still I had no idea what he was talking about.

“What do you mean? I don’t do that, at least I don’t think I do,” I told him.

“Yes, you do,” he insisted. “You act like I’m too dumb to know what the other boys are doing and no one treats me the same way they do everyone else.” Suddenly, I knew where this was heading and hoped I hadn’t already blown it for him.

“I hear other boys in my school talk about things they do,” he continued, “and I see the way my brothers spend time with each other at night. I know about sex, but nobody will do anything with me because they said you told them Andrew and I can’t be included. Why not?”

“Well, that was before, when I thought you weren’t ready for such things,” I admitted. “I know you’re growing up and maturing, and I’ve even noticed that your penis has grown longer and some hairs are sprouting above it, but I didn’t want the others to push you into anything until you were ready for it.”

“Well, I’m ready and I don’t want to be left out any more,” he demanded. “Actually, Andrew and I have been trying things on our own, but I guess you didn’t know that.”

“You have?” I asked, amazed. “No, I didn’t know that either. I was hoping to keep Andrew from getting involved in this too, since he’s still quite young and I’m worried there might be other issues he’d have to deal with first, like what happened to him in Houston. So, when did you two start fooling around and what have you done together?”

“We started a little while after that guy did those things to Andrew at the Space Center,” Sammy announced, surprising me even more. “At first we just rubbed each other’s wiener, but lately we’ve also started sucking on them too.”

“Is that all?” I asked, to make certain I knew what they’d been up to.

“Yeah, we haven’t done anything else,” Sammy confessed.

“Does Andrew feel the same way you do, about being able to do things with the other boys?” I pressed, to determine how I should proceed from the point forward.

“I don’t think so,” Sammy responded. “He doesn’t seem to care if we do anything or not. I think he just does it because I ask him to, but I don’t think he would have done anything if I hadn’t wanted to do it first.”

“Well, I can tell the other boys it’s okay to include you in their activities, if that’s what you want,” I agreed, “but I think we should still try to leave Andrew out of it, at least for the time being.”

“That’s okay with me, but Andrew and I are together a lot, so it will be hard,” he admitted. “Won’t he get suspicious if I suddenly start spending time alone with the other boys?”

“Yes, I suppose he will,” I concurred, “but it’s possible I can get some of the other boys to do non-sexual things with Andrew, whenever you get a chance to do something with someone else. Would that be okay with you?”

“Yes, Dad, that sounds great,” Sammy replied, suddenly glowing and looking much less angry than he had a few minutes earlier.

“Was there anyone in particular you were thinking about doing things with?” I asked, in order to get a sense of where he might be headed and whom he might be attracted to. This simple question, however, caused Sammy to turn a bright shade of red and look down at his feet, before he started moving his right foot nervously, from side to side, while balancing his weight on his left leg.

“Well, I was kind of hoping that Brent or Nick might want to do things with me,” he admitted. I chuckled and Sammy looked up at me, with a quizzical expression on his face.

“I’m sure you won’t have any trouble convincing Nick,” I told him, “and I think Brent might be interested as well. Do you want me to explain anything to you first? I guess I probably should have done that already.”

“Well, there are some things I want to know,” he admitted, without telling me what they were, so I was left to pry that information out of him.

Over the next forty minutes or so, I dragged many questions out of Sammy and answered them as best I could. After everything was out in the open, I also offered him a few words of advice. Once all of that was taken care, I also took a little longer to make sure his foreskin retracted easily, as I didn’t want him to get hurt if someone inadvertently forced it free. Things went fine, Sammy was happy and now I decided to fill the older boys in concerning this change in direction.

Before I did it, however, I sent Sammy and Andrew upstairs to get ready for bed, and then I rounded up the other boys for a quick briefing. I told them Sammy was now allowed to be included in their activities, but nothing anal yet. I told them if he brought that up, to tell him he needed to be prepared for it first and they could do some fingering with him to keep him satisfied. However, before they went any further, I wanted them to come speak with me, so I could sit down and have another chat with Sammy beforehand, to make sure he understood what he’d be getting into.

I also informed them that whenever they did something with Sammy, they would also have to find someone to occupy Andrew for the evening, so Andrew wouldn’t get suspicious about what Sammy was up to. I also emphasized that Andrew was still off-limits for the time being, but I’d let them know when that situation changed as well. They all said they understood, so I went to go back to what I was doing, but on the way out I decided to ask Nick and Brent if I could speak with them first. They followed me to my bedroom and looked worried they had done something wrong, but I reassured them quickly.

“I just asked you two to join me because I think Sammy would like to have his first experiences with one of you,” I announced.

“Awesome,” Nick cried out, almost immediately.

“Did he tell you that?” Brent asked, right after Nick’s shout of joy.

“Yes, he did hint at it,” I confirmed. “I think you boys are closest to his age and more or less his type. Just be gentle with him, as he’s new to all of this, and remember – nothing anal until I tell you differently. Okay?”

“Sure,” they both responded, and Nick walked back toward the family room with a huge grin plastered across his face.

Nothing happened with Sammy until that weekend, when Sammy was invited to spend Friday evening with Nick. Cole and Graham quickly volunteered to entertain Andrew, so everything was set. I wasn’t sure at first if it was wise to have Nick give Sammy his first experience, but he turned out to have been the perfect choice to teach Sammy the joys of boy-to-boy sex. I was to learn from Sammy later that Nick showed a tenderness that belied his promiscuity. Nick took Sammy to his room, both already naked after their showers, and stood and admired this young neophyte.

“You know, I’ve been eyeing you for some time now,” he told Sammy, which caused Sammy to blush.

“Really? How come?” Sammy asked, because he didn’t think he was very desirable. After all, his penis wasn’t very big and he didn’t think he was as handsome as most of his brothers.

“Because I’ve noticed that you’re growing up and parts of your body are growing too,” Nick informed him, which cause Sammy to blush slightly again. However, he was immensely pleased that Nick had noticed his blossoming maturity.

“Yeah, it has been getting bigger, hasn’t it?” Sammy asked, somewhat proudly.

“Oh, yes, and it’s very nice,” Nick confirmed. “I’m glad Pop said it was okay to do things with you now.”

“Me too, but I had to tell him I wanted to first,” he told Nick. “He still thinks of me as a little kid.”

“Well, we can definitely see you’re not little any more,” Nick told him, rubbing his hand over Sammy’s limp penis. The minute Nick touched it, it began to spring to life and slowly stiffen. Eventually, it worked its way upright, like an Indian fakir’s rope climbing skyward in response to the sounds of his flute. Before many seconds had passed, Sammy’s dick was as hard as an iron rebar and Nick was sliding his hand up and down the shaft, slowly working the foreskin back and forth.

The new and exciting feelings Sammy was now experiencing sent him into an almost trancelike state, as his very experienced partner demonstrated what he had learned pleasing the many partners he had previously encountered. Sammy’s mouth dropped partially open and his eyes closed almost completely, as his head tilted backward and began to sway from side to side with pleasure. Nick suddenly started to worry that Sammy’s legs might give out due to the stimulation and he might fall and hurt himself, so he guided him over to the bed and helped him lay down.

Sammy jumped slightly as his body began to tingle, when Nick fingers touched his sensitive glans, which had been sheathed by his more than abundant foreskin from nearly all outside stimulation before this moment. Now that it was suddenly exposed to all kinds of new sensations, it caused his young body to tremble, while Nick introduced him to the pleasures a simple touch could bring. Nick also slowly massaged his scrotum and then the full length of his shaft, and he rubbed his thumb over the exposed helmet and tiny slit each time his hand reached the tip. Sammy was now shaking with pleasure, moaning noticeably, and squirming beneath Nick’s expert ministrations. Just when he thought he couldn’t take any more, Nick delivered him to a new level of euphoria.

As he saw Sammy begin to quiver in enjoyment and anticipation, Nick lowered his head and guided Sammy’s rigid dick into his mouth. As he began to suck on Sammy’s bone, he also let his tongue roam freely around its surface. As Nick did this, Sammy’s body went rigid, his cock swelled and then it twitched, as he experienced a very powerful dry orgasm.

Nick picked up on this immediately, but noticed that Sammy’s little pole never wilted, so he continued to suckle and bathe it with his saliva. This caused Sammy to thrash around beneath him even more, with his young body now on complete sensory overload, as he enjoyed every moment of what was happening to him. Nick continued teasing him in this fashion, sliding his lips up and down his rigid pole, letting his tongue toy with the flesh within his mouth and adding even more suction, which caused Sammy to begin squirming even more. He continued this way for a few minutes more, until Sammy’s testicles drew closer to his body, his penis expanded and he experienced his second dry orgasm of the night. After this, Nick lay next to him stroking his chest, kissing his face and allowing him to enjoy his first real sexual high. After a few minutes of remaining like this, Sammy finally turned toward Nick and spoke.

“Wow, that was super,” he gasped. “Andrew and I have tried things a few times, but he never made me feel like that. Thanks, Nick, that was really great.”

“I’m glad you enjoyed it, but we’re not done yet,” Nick advised him.

“We’re not?” Sammy asked, startled.

“Nope, now you get to do it to me,” Nick quipped, which caused Sammy to smile. It wasn’t until then that he realized he’d forgotten about returning the favor and thought only about the pleasures he had just enjoyed.

“Yeah, I knew that,” Sammy acknowledged, somewhat guiltily. “I guess I thought you meant you were going to do even more to me.”

“Oh, I will,” Nick boasted. “Maybe not all tonight, but there’s a lot more we can do together.”

“Wow, I can’t wait,” Sammy gushed. “This has really been awesome and I really want to do it to you too. I’ve never touched a wiener that wasn’t like mine before.”

“Hold on there, Sammy. From now on, it’s not a wiener,” Nick advised him. “That’s what little kids call it. Now you call it a cock, or a dick or penis. You’re grown up now, and you no longer have a wiener or weenie.”

Sammy blushed at the mild scolding, but he understood what Nick was telling him. “I’m sorry,” he apologized.

“No, you don’t have to be sorry, we’ve all done the same thing,” Nick told him. “It’s just that if you want to be treated like a man and not a little boy, then you have to start talking like a guy in high school, not a kid in grade school.”

“Oh, okay. I see what you’re saying,” Sammy agreed. “Maybe that’s why Dad didn’t think I was ready for this yet. I guess you’re right, Nick, and I’ll watch what I say from now on. Thanks.”

“Hey, that’s okay. That’s what big brothers are for,” Nick told him, before giving Sammy a hug. Both boys smiled at each other and then hugged again. “Now, why don’t you try doing the same things to me,” Nick coaxed him.

Sammy didn’t need any further invitation and slowly reached over and started touching, then holding and finally rubbing Nick’s limp penis. Nick watched him closely and got a kick out of Sammy’s fascination with his slightly larger and cut cock, noticing how the younger boy stared at it, ran a finger across the slight scar from his circumcision and then stroked his finger across Nick’s less sensitive head. After a few minutes of continued investigation, Nick finally urged Sammy into stroking his now hard member and Sammy eagerly jumped to the challenge.

Sammy began by letting his small hand glide up and down Nick’s longer and thicker shaft for a few minutes and then leaned forward, so he could lick the mushroom head. After he did that, he looked up to see the older boy’s reaction, only to discover that Nick had his eyes closed, but there was a satisfied smile on his face. Finding this enough encouragement to continue, Sammy bent back over the rigid pole and opened his mouth as wide as it would go, so he could take Nick’s stiffy into his hot little opening.

This penis was much larger than Andrew’s little prick and Sammy gagged, as he tried to take too much, too fast. He pulled back a little and then began again, until he was bobbing up and down on Nick’s firm member, doing his best imitation of what Nick had done to him. Being inexperienced, Sammy let his teeth scrape against the sides of Nick’s dick now and again, but Nick decided not to say anything to him about it, as he didn’t want to stifle his enthusiasm or make him feel he was doing an inferior job. He’d wait until later, when they did it again, before he offered him any tips on how to do a better job.

Regardless of the minor flaws in his technique, Sammy was soon bringing Nick to the brink of orgasm. Realizing that Sammy was new to this, Nick decided it might be best if he didn’t shoot into Sammy’s mouth the first time. Therefore, he looked down at the younger boy and spoke to him in raspy breaths.

“I’m gonna shoot…” he warned him. “Pull off… use your hand to pump it… if you don’t want a mouthful.”

Somewhat confused by the request, Sammy pulled his mouth off of Nick’s organ and used his little fist to pump it up and down. Just a few seconds later, strings of cum exploded from Nick’s penis and covered his chest. Sammy was in awe, as this was the first ejaculation he had ever seen.

“Wow, that was great,” Sammy gushed. “How come I didn’t do that?”

Nick was out of breath and didn’t answer right away, but when he did, he tried to be tactful about it. “It’s because you’re body is just starting to go through the big change,” he advised him. “You’re cock has started to get longer, you getting a few hairs over top of it and soon you balls will start producing sperm, like mine do.”

“So that’s what sperm is,” Sammy mused. “I’ve heard other boys talking about it and about shooting, but I never understood what they meant. Heck, I didn’t even realize it would be white or shoot out of your dick in spurts like that either. I though it would be clear, look like pee and come out in a small stream.”

Nick giggled inside, but made sure Sammy didn’t pick up on his amusement concerning his sexual naiveté. “Nope, it’s kind of a pearly white for almost every boy when he shoots, maybe sometimes a yellowish white, but you’ll be seeing a lot more of that now. When you first start shooting it can be clear for a while, but eventually it starts looking creamy.”

“I think it’s pretty neat. Can I touch it?” Sammy asked.

“You can touch it, play with it or even taste it if you want,” Nick told him.

“Taste it!” Sammy replied, startled by the pronouncement. “Have you ever tasted it?”

“Sure, all the time,” Nick giggled, while running his finger through the sticky liquid and gathering up a small amount, so he could stick it in his mouth. “Every guy’s cum tastes a little different, you know,” he added.

“Really? How come?” Sammy wondered.

“I guess it has to do with what he eats, drinks and even if he smokes,” Nick told him.

“You mean you’ve tasted other guys’ stuff when they shoot too?” Sammy asked, totally astounded.

“Of course,” Nick chuckled. “It’s also called cum or jizz. The guys I’m with usually just shoot it into my mouth when I suck them off and then I swallow it. I’ll do the same for you, when you can shoot too.” Sammy nodded his understanding and then placed his own finger in the small pool on Nick’s stomach, scooped up a sample and stuck it into his mouth. He made a little face, but didn’t seem to mind the taste too much.

“Well, what do you think of it?” Nick asked him.

“It’s okay, a little bitter, but I don’t mind it,” Sammy replied.

“Well, maybe next time I’ll just shoot it in your mouth then, if you want to try that?” Nick encouraged him.

“Yeah, that would be okay,” Sammy said with a grin, and then thought for a second before he spoke again. “How come you didn’t do that this time?”

“Well, I didn’t know if you were ready for that yet,” Nick confessed. “I didn’t think it would be fair to do it to you unless you told me you wanted me to, and we’d never talked about it before.”

“Yeah, I guess I would have been surprised if you did that,” Sammy admitted. “Thanks for letting me make the choice.”

I understand it only took them a few more minutes before they decided to do everything for a second time, except this time there were fewer surprises and more enjoyment, at least for Sammy. Nick did him first again, in order to give his own body a chance to recuperate, but this time Nick did a whole lot more to the novice, such as sucking on his nipples, sucking his testicles and licking his thighs and perineum, before giving Sammy another blowjob. Once again, Sammy had a dry orgasm, but they both realized it probably wouldn’t be very long before Sammy was able to shoot his own load.

This time, when Sammy returned the favor, Nick let his ejaculation go into the younger boy’s waiting mouth and Sammy swallowed all of it, enjoying the slightly sweeter taste of this thinner and less voluminous second offering. After their final encounter of the night, they went to sleep, entangled in each other’s arms and lingering in the memories of this very special time together.