The Castaway Hotel - 5 - 15. Chapter 15 - Ending The Holiday Season

In a room down the hall, Shannon was also getting into areas new to him. Although he and Nick had been together before, they had never done anything anally, but that was about to change. Nick had already decided he was going to try to convince Shannon to move to the next level, so after the boys had undressed each other, he coached Shannon on how to prepare him for the deed. He figured if he let Shannon do it to him first, it might prove to be the quickest way to lower Shannon’s inhibitions and motivate him to return the favor.

Although Shannon wasn’t quite sure he was ready to move to this level, he did as Nick instructed, although a bit reluctantly. Shannon carefully loosened Nick’s channel by using his fingers, as Nick suggested, and lubed Nick’s chute with plenty of oil, before he allowed Nick to place a condom over his penis and lube that as well. Once he felt he was ready, Nick lay on the bed and pulled his legs nearly onto his chest, to expose his hole. He figured from there, Shannon would know what to do next.

After seeing Nick in that position, the reality of what he was about to do finally sank in and caused Shannon’s penis to fill with even more blood, so he was now harder than he could ever remember. Although he had idea about what he was supposed to do and how to accomplish it, it still took him a few, awkward seconds to figure out how to position himself, in order to make the penetration as comfortable as possible for each of them. Once he had that figured out, he put the tip of his penis against Nick’s opening, but then remembered Nick’s words of caution about entering slowly. This caused him to temporarily freeze in place and hold his breath, as fought to contain both his nerves and excitement. He still couldn’t believe he was actually going to f**k someone.

Once he’d regained his focus, Shannon started to slowly push his way in, but he wasn’t quite ready for how stubborn the sphincter could be, even when doing this with someone who had done it before. However, Nick encouraged him to press a little harder, while he also pushed out, and within seconds the head of Shannon’s penis had popped past the guardian. Upon breaking through the resilient ring of muscle, Shannon stopped abruptly, because he was worried he had done something wrong, but Nick quickly assured him he was doing fine and urged him to keep going. Feeling a sense of relief, Shannon continued to push deeper, although he moved VERY slowly, until the tops of his thighs were brushing up against Nick’s butt cheeks and his penis was completely encased by Nick’s velvety lining. After a little coaxing from an impatient Nick, Shannon began to rock his hips back and forth, sliding his dick in and out of the warm moist tunnel, while his mind was reeling from all of the intense sensations coursing throughout his body.

At first, Shannon was nearly lost in a sense of carnal bliss, while reveling in how great it felt to be buried inside of his partner’s love channel. However, once he began to focus on the wonderful sensations emanating from the middle of his body, as he began sliding in and out of Nick’s love canal, Shannon found he couldn’t contain himself any longer and eagerly made his dash toward the finish line. Since this was his first attempt at anal sex, it didn’t take him long to reach the point of no return. Upon sensing that familiar feeling of impending release, Shannon made his final thrust and seated his manhood as deeply inside of Nick as it would go, before spewing his molten cream into the tip of the latex sheath.

Drained of his juices, Shannon collapsed on top of Nick, totally exhausted by the culmination of the powerful explosive orgasm and the emotional letdown brought about from the conclusion of his initial experience with making love. Shannon remain unable to move and stayed like that until Nick gently rolled him off his body and kissed him passionately, to show his appreciation.

Nick was very tender and patient with Shannon. He not only gave him all the time he needed to recover, but he continued to stroke and kiss him as well, while waiting for Shannon to come down from his the lasting effects of his intense orgasm. As he did this, Nick also wondered if Shannon would be ready and willing to take his turn as catcher. He wasn’t sure Shannon would be, but still hoped he might.

After spending several more minutes like this, Shannon finally looked up and thanked Nick for the wonderful experience. After Nick told him he was welcome and agreed that he’d enjoyed it too, Shannon surprised him by announcing he was ready for Nick to do the same thing to him. Although he was excited by the prospect and eager to take advantage of the situation, Nick thought he recognized a hint of trepidation in Shannon’s eyes. Since he didn’t want Shannon to be scared his first time, he tried to reassure him he’d do nothing to hurt him, which brought a slight smile to Shannon’s lips.

After a little coaching about what to expect, Nick greased up his fingers and began to loosen Shannon up. As he did so, Nick worked as gently and carefully as a parent tending to an injured child. Shannon hardly felt the first finger as it entered him, but he did react slightly when Nick added another. However, since Shannon didn’t complain or raise a fuss about it, Nick continued his effort and eventually added a third digit. As he did this, Nick noticed Shannon wince a bit, so he stopped all movement and asked how he was doing. Shannon quickly told him it had hurt momentarily, but he was fine now, so Nick continued slowly and watched for other signs signifying Shannon might be having difficulty. Even though Nick was excited about doing another virgin, he still didn’t want to make this a bad experience for Shannon. Nick actually hoped he might get other chances to repeat this activity with him in the months to come.

Finally, after a brief delay, Shannon announced he thought he was ready, so Nick rolled him over onto his belly and placed a pillow under his hips. This lifted Shannon’s butt into a position that would allow easiest entry for complete penetration. Slowly, he moved in between Shannon legs, slid on a rubber and slicked it up. When he had completed his preparations, he lined up with his target, but continue to talk to Shannon the whole time, in order to make sure the first-timer didn’t panic and understood what was going to happen next, before he began his entry.

Once he was convinced Shannon was ready for what was about to happen, Nick carefully prodded at Shannon’s opening, while advising him to relax and push out, which would make it easier for both of them. Nick added a little more pressure until he felt the head of his penis pop inside the muscular guardian, which had been resisting his efforts at first. Now that he was in that far, he paused and gave Shannon time to adjust, before he continued going deeper. Once he had Shannon’s assurance he was okay and ready to continue, but pushed a little deeper, only to be stopped by Shannon’s slight protest.

“Nick, get off of me, I feel like I have to take a dump,” Shannon told him, while looking over his shoulder, concerned.

“No, you just feel that way because my dick is inside you,” Nick told him. “Your body just feels as if a big turd is in there and wants to get rid of it. It doesn’t understand the difference yet.”

“Are you sure? I really feel like I have to go,” Shannon advised him, “and I wouldn’t want that mess all over us.”

“No, it’s alright and we’ll be fine,” Nick assured him. “It’s only my dick in there that makes it feel like you have to shit. You’ll get used to it and realize I’m right.”

“Wait, I’m just not sure,” Shannon whined. “Get off of me and let me go to the toilet to make sure. Please?”

Hesitantly, Nick slid out of Shannon’s chute and Shannon immediately raced off to the toilet, only to discover that Nick had been right all along. As Nick had explained, Shannon really didn’t have to go at all, it just felt as if he did. As he made his way back to Nick’s room, Shannon apologized and announced that Nick had been correct, before getting back into position. This time when Nick’s penis entered his body, it felt the same as it had before, but Shannon accepted it as being part of the activity and not a call of nature. Relieved, Nick continued his penetration until he was completely embedded inside of Shannon’s tight channel. Once he bottomed out, Nick paused briefly, to give Shannon a chance to get used to their new connection.

Once Nick had been assured that Shannon was ready to continue, he began to slide his love muscle in and out of Shannon’s virgin hole, gradually building a rhythm, as he gave Shannon his first ride. After a few moments of feeling awkward about what he was doing, Shannon began to enjoy the sensations building within his body, especially when Nick’s penis hit a certain spot inside of him. Whenever that happened, it felt as if little jolts of electrical current were released to travel along his nerve synapses and Shannon’s entire body would begin to tingle.

Nick was obviously enjoying the activity too and slowly began to increase his pace, as he felt his own release building. This was brought on even more rapidly than usual, due to the tightness of Shannon’s rear entrance. Even though he had done this many times before, and with other first-timers, Nick never tired of the overwhelming feelings and the enjoyment he received from this activity, so he eagerly plunged on.

By this point, both boys were panting and moaning, thoroughly getting into the action. Nick kept pounding away at Shannon’s butt, sending them both into a sexual frenzy. Although he never expected it to happen, Shannon’s body suddenly stiffened, as a result of Nick’s erection constantly brushing against his prostate, and he ejaculated, without either of them having touched his cock.

When Shannon climaxed onto the bedding, his rectum tightened around Nick’s penis, and this added pressure sent Nick over the edge, forcing his hot juices to erupt and accumulate inside the prophylactic. Nick thrust weakly a couple of more times after that happened, until he drained the last of his seed from his dick, and then he collapsed on top of Shannon, causing both bodies to drop onto the mattress.

Even though the physical act had been completed, they remained coupled together a while longer, lingering in the sexual afterglow this experience had produced. They also enjoyed the feel of each other’s body, as they remained connected in such an intimate way, and their continued physical contact seemed to magnify all of the pleasure that had just consumed them. After remaining like this for several minutes more, they finally separated, but only so Nick could rid himself of the condom, and then they lay side-by-side and held each other in their arms. Since neither of them wanted this feeling to end, they remained secure and warm in each other’s embrace until morning.

Kevin, Vinnie, Nick and Shannon weren’t the only ones to spend their evening making love. Danny and Brandon and Dion and Trey also went to their rooms with plans of pleasing their partners, while little Andrew spent the evening sandwiched between Sammy, Graham and Cole. The four of them spent the night moving from one to the other and giving each other pleasure, and it was nice to see the two sets of biological brothers so close to each other. Of course, I think Cole would have preferred spending time with his girlfriend, but since she had gone away with her parents, it wasn’t an option, so he made the best of his situation and still had a good time.

Jake had become a little anxious when he saw Shannon going off with Nick, so we discussed the situation in some detail. Sensing Jake’s doubts, I assured him that Nick had many fine qualities, such as being a very patient, sensitive and experienced lover, so Shannon was in very capable hands and had nothing to fear. Other than Nick’s promiscuous nature, he was a wonderful young man and I hoped he would someday outgrow his need for multiple partners and be able to settle down and find true love.

After we finished our conversation and Jake’s concerns had been addressed, he started feeling a little frisky himself and began to attack me, in hopes of sating his own desires. I won’t go into great detail about what we did that night, since I don’t feel anyone except us needs to know all of that information, but I will admit we were reaching a level of bonding that few couples ever achieve. Maybe I should take a moment to explain what I mean by my comment.

Jake and I had learned over time that we had a great deal in common, which included the types of activities we enjoyed, what we liked to eat and even the different ways we sought to please each other. Over time, we had also grown to love each other deeply and were committed to our family, which had a far greater meaning than just biological relationships, but equally important was our time alone. Our lovemaking was also bonding us in such a way and so tightly that I highly doubted anything could ever separate us. I must admit it is truly a wonderful feeling to know your relationship is sincere, deep and boundless, not to mention passionate, and the satisfaction you receive from just being together seems to never end. I was truly a very fortunate man and I sincerely hoped that Jake felt the same way about our partnership.

After our lovemaking, I found it difficult to fall asleep, as my mind was awash in all of these wonderful thoughts and feelings. As I lay there considering the current state of affairs, I heard the rest of the boys arrive home sometime after three. After Frankie had ended his date, he drove over and picked his brothers up from their party, dropped their dates back off at their own homes and then returned my brood to their own beds. Although these young men would be sleeping alone this evening, I think they had more than enjoyed themselves earlier and the thought of not having anyone to share their bed at that moment didn’t ruin the night.

I didn’t hear Mark come in until almost eight, so I wasn’t certain if he had just finished partying with his date and was returning home, or if he had slept at her place and just recently slipped out to rejoin us. He was old enough that I didn’t have to question what he was up to, but he did tell me later that they had only partied until around two and then he spent the night sharing her bed. I guess they were getting pretty serious about each other.

New Year’s Day was a jumble of activity. Ricky and Jay were actually the first to stumble downstairs, so I offered to fix them some breakfast, but not merely for humanitarian reasons. I figured it would also give me the opportunity to press a bit and see if I could learn anything about what they had been up to the previous evening.

“So, how was your party?” I asked them, after they told me what they wanted to eat.

“It was okay,” Jay replied, deadpan.

“Not really,” Ricky corrected him. “If we didn’t have our dates with us the party would have really sucked,” he continued.

“I’m sorry to hear that,” I told him. “Why was it so bad?”

“To begin with, the music blew big time, because they had some freak picking the tunes.” As I looked at him, Ricky face seemed to contort a bit, as he thought back upon the previous evening. “They had hardly anything to eat and what there was tasted worse than dog food, so I went off with my date and we made our own party?”

“Oh! And what does that mean?” I prodded, raising my eyebrows and giving him a questioning look.

“Wouldn’t you like to know,” Ricky replied, as his way of blowing off my question.

“The party wasn’t that bad,” Jay corrected. “The pizza was cold…”

“And was like eating cardboard!” Ricky interrupted.

“Oh, Mister High Standards,” Jay mocked. “You didn’t seem that fussy when you were eating pussy…” Jay stopped abruptly and began turning crimson, now that he realized he’d probably said more than he should have. Ricky just glared at him for a second, before he tried to slip out of the embarrassing situation gracefully.

“I wish,” he joked back, but his voice lacked the sincerity to make me believe otherwise. “But you’ve got to admit the music sounded like a cat fight,” he added, trying to change the subject. Jay didn’t bite this time and started filling his mouth instead, so he didn’t have to speak again. Ricky soon did the same, so I left them alone and walked out of the room. Once they thought I was out of earshot, I overheard Ricky chastising his best friend.

“You dumb ass,” Ricky snapped. “That was a great thing to say in front of my dad.”

“Come on,” Jay whined, “he knows what you do and doesn’t mind, as long as you’re careful and don’t force anyone. Just think of the shit I’d be in, if something like that was said in front of my ‘rents.”

“You don’t have to worry about that,” Ricky teased. “You girl doesn’t like oral, either giving or receiving.”

“Shut up! She does it sometimes,” Jay challenged, but only half-heartedly. “Besides, she does enough, or I wouldn’t still be with her.” Ricky merely laughed and I moved on, although I was still debating if I wanted to hang around to hear what they might discuss next.

Jake was already in the family room, so I went in to join him and we spent the remainder of the morning watching the various parades being shown on television. Once the rest of the boys had risen from the dead and filled their grumbling tummies, some of them even came in to join us. Although it wasn’t their favorite activity, they did like seeing some of the floats and it gave them time to thoroughly wake up and come to their senses before we got to the meatier part of the day. I think the biggest reason they were willing to sit and watch the parades was so they could check out the eye-candy on the tube. Although it was still pretty cold at some of the parade locations, which meant many of the spectators and participants were bundled up so you couldn’t see much more than their faces, the boys didn’t seemed deterred. Even though it wasn’t perfect, everyone enjoyed pointing out various persons of interest, and yes, different family members happily pointed out both guys and gals and no one drooled so much that I had to make him wear a bib.

Over the course of the day, I overheard more tidbits about what had happened when I wasn’t around, both at our house and at the party. I actually gleaned sufficient information from the various participants to be able to piece together enough to let me know that no one had done anything too drastic and given me a fair idea about what had transpired. I also learned that most of my straight and bi boys were quite attached to their current girlfriends and wanted to be with them for more reasons than just the possibility of having sex, which impressed me and spoke volumes about their level of maturity.

Mark and Frankie happily admitted they’d had a much better time than the others, although they weren’t together at any point. Mark and his girlfriend had gone out to dinner and then to a club to dance, while Frankie took his date out to dine at a different establishment, before stopping in to check out a few parties they’d been told about. Although, they didn’t stay at any one place for the remainder of the evening, Frankie claimed both he and his date had enjoyed themselves and they would be seeing more of each other in the future.

As far as the boys who had spent the evening at home, I heard them discussing enough with their brothers to discover most of what happened, so I could relay their stories to you earlier. Seeing it was just family involved, and they knew I had few restrictions when it came to their activities with each other, they didn’t have to try to sneak around to share this information with each other. They pretty much chatted openly about these things and didn’t seem to care if Jake or I heard what had gone on – well, except for Shannon. He didn’t seem to mind if I heard about what he’d been up to, but he seemed to get embarrassed if anything was said in front of his father. Personally, I found it quite ironic that he didn’t mind my knowing, but preferred his father not be aware of what he had done.

Even if they hadn’t said anything, I think I would have figured most of what had happened just from just watching how the various pairs interacted and looked at each other over the course of the day. It seemed to me that someone was always flashing a coy smile or giving a seductive wink to their other half, and the other person might possibly even blush a little when he thought back upon why his partner was doing it or what he might be hinting at. It was very cute watching them play these little games and I felt confident that everyone had enjoyed himself and was happy with the way he had brought in the New Year.

At lunchtime, I let everyone fend for himself, because I felt I deserved a chance to relax too. Some of the boys were obviously unhappy about my announcement, but I didn’t think I had to worry about any of them starving. However, I was impressed when some of the boys offered to fix something for their brothers, as well as themselves, and this solved their dilemma. I was also pleased that Danny and Brandon not only made grilled ham and cheese sandwiches for each other and a few of their brothers, but they also brought some in for Jake and myself as well. Pleased by their thoughtfulness, we each thanked them, although the boys sloughed it off as not being a big deal. Once we’d finished our meal, we eagerly settled in for the start of the first of the bowl games.

Since I knew not everyone would be into this activity, I wasn’t surprised to hear some of the boys talking about going into the living room to watch some DVDs. We certainly had a large enough collection that they should be able to find something to entertain themselves, but later I heard that while they were debating what to view, one of the other boys discovered that one of the channels was running a Queer As Folk marathon. Happily, they agreed to watch that instead and spent the next few hours hunkered down with the QAF cast. I wasn’t sure if they grew tired of it or if it had ended, but when I went past there on my way to the toilet, they were watching a movie.

For the most part, we spent the rest of the day either watching football or movies, except for Dion and Trey, who spent their time with their noses buried in books. They were happy doing this and I was pleased to see they were enjoying what was a lost art to many, and their brothers were smart enough to not bother them after they had gone off on their own.

Mark had opted to join Jake and I as we watched the football games and sat leaning up against me on one side, as Jake cuddled against the other. I must say it was a very nice way to spend the day and our closeness was only interrupted by toilet breaks and quick dashes to grab snacks or drinks. At halftime of the third game, Jake and I began to feel guilty about ignoring the boys’ needs, so we went out to prepare dinner for everyone. We certainly didn’t want anyone complaining to their friends or other members of our extended family that we had tried to starve them. However, we did go back in and rejoin Mark while it was cooking, and once that game ended, I summoned everyone into the dining room, so we could enjoy a family meal.

As I sat there looking at my boys, my mind began to race over everything that had happened to us over the past year. In doing so, I discovered I could now empathize with Queen Elizabeth II, when she declared 1992 as her ‘annus horibilus,’ or horrible year. I could totally empathize with how devastated she must have felt after having lived through the rash of terrible events that had encompassed her family during the twelve months preceding her comment. The past year had been like that for us, as well. We had endured much together, such as losing Brent, my heart attack and the terrible events of 9/11, but if you looked back at it honestly, there were some positive moments scattering throughout the year too. During that same time span, we had reveled in the birth of a granddaughter/niece and the announcement that another baby was on the way, besides gaining another son/brother. However, no matter how special those things were, I was forced to admit that for the first time since I had begun this adventure of assembling a second family, the negatives in our lives had far outweighed the positives. I silently prayed we wouldn’t have to go through anything like this again, at least not in the very near future.

As I broke away from these not so pleasant thoughts, I went back to thinking about my family again, which included my older children, grandchildren, new sons, almost sons and my lover. This was enough to suddenly lift my spirits and make me forget about everything else, as I acknowledged how lucky I really was.

After everyone finished their meal, we happily went back to resuming the activities we had been involved in earlier, and that remained unchanged until bedtime.