The Castaway Hotel - 7 - 25. Chapter 25 - Who Needs Mistletoe

After everyone left on Christmas Eve, the boys helped clean up before they headed to their rooms. Some of them were disappointed they hadn’t been able to open any presents tonight, even though I knew some of them would be exchanging their personal gifts before they went to sleep, especially my committed partners. Realizing this, I knew they wouldn’t all be going to bed unhappy. In fact, from what I learned later, it was more than just my couples that had fun, because some of the other boys were quite agreeable to spreading a little good will and good feelings to their fellow man.

Although Danny and Brandon, Trey and Dion, and Kevin and Vinnie stayed with their own boyfriends and enjoyed a night of unbridled passion, I also heard that Andrew and Graham got together, as did Cole and Sammy. However, my biggest surprises came when I learned that Ricky and Pat had hooked up for some fun as well. That was due to the fact that, as of late, both of them had shown more of an attraction to females than anyone else. I guess it is possible they merely wanted to give their brother a little special attention and enjoyment for the holiday or they might have just felt bad after seeing everyone else pairing up for the night. It could also be they had just gotten horny enough that it didn’t matter, since they were desperate to get their rocks off and didn’t care who helped them. Whatever the reason, they all had a little extra fun.

I was also astounded to learn Shannon had asked Peter to spend the night with him. I knew Shannon had been missing Nick, but I think he had also learned Nick wasn’t being faithful while he was away. I’m not sure if this was for his own pleasure or a means of getting back at Nick, but Peter accepted his offer and went off with him. Once they reached Shannon’s room, things got really interesting.

“What would you like to do?” Peter asked, once they were alone.

“I don’t know,” Shannon responded. “If Nick were here, we’d have made love to each other tonight.” Shannon stopped after saying this and Peter didn’t press him for more, since he could tell Shannon was missing his partner. Eventually, Shannon broke the silence and spoke.

“I guess since Nick isn’t here to do it,” Shannon began, “I’ll let you make love to me tonight instead.” Peter’s eyes nearly popped out of his head and his mouth dropped open.

“You mean you’re going to let me shag you?” he asked, to clarify what Shannon had said.

“I don’t understand,” Shannon replied, confused. “What does that mean?”

“You know…” Peter began and then he made an ‘O’ with one hand and then poked his index finger in and out of it, to show what he meant.

“Oh, I get it,” Shannon replied. “Yes, that’s what I mean.”

“Oh, well, uh…” Peter stammered, before he found his tongue. “I’ve never done that before… especially with a bloke.”

“You’ll do fine and I’ll tell you what you need to know,” Shannon informed him. “Unless you don’t want to do it.”

“Oh, no, I do,” Peter insisted. “It’s just that I’ve never done it before.”

“You’ll be fine and your instincts will take over after a few seconds,” Shannon explained. “I know that’s what happened my first time.”

Peter nodded and smiled, and then both boys tore off their clothes. Once they were naked, Shannon fondled Peter until he got an erection and then he slipped a condom over it. Once it was in place, Shannon smeared some lube on it, before he reached behind himself and did the same to his rectum. Now that he was ready, Shannon turned to Peter and spoke.

“Do you want to do this doggy-style, with me on all fours, or do you want us to be facing each other, with me on my back.”

“What do you think?” Peter counted. “You’ve done it more than me.”

“Well, if you don’t mind,” Shannon told him, “I’d rather see your face and you could even kiss me, if you wanted. You don’t have to, but you could and I wouldn’t mind.”

Peter looked as if he was thinking it over, as Shannon got into position. Seeing Shannon laying their with his legs pulled up to his chest, Peter got the idea of what he was to do next. He moved up until his rod was near the correct opening and Shannon grasped it and guided him in. Slowly, Peter entered a love canal for the first time.

“It’s so tight and warm,” Peter moaned. “I didn’t know it would feel like this. What do I do now?”

“Just like you did with your finger in your other hand,” Shannon told him. “Just go in and out, but not too fast.”

Peter did as he was told and slowly began to slide back and forth in Shannon. Peter was grunting and groaning as he did it, so those in the adjoining room were probably able to hear this. Seeing it was his very first time, he could feel he was building to his crescendo quite rapidly and doubled his pace. Before long, he was spewing his creamy reward into the tip of the condom. After releasing several forceful volleys, he collapsed, while still embedded in Shannon’s hole. As he began to recover, he looked into Shannon’s eyes and reacted. He began kissing Shannon passionately, much to Shannon’s surprise. Once their tongues stopped dueling and their lips pulled apart, Peter spoke.

“That was absolutely fantastic,” he gushed. “I didn’t know shagging a bloke could be so wonderful. I can’t wait to try it with a girl, to see if it’s this good with them too.”

Peter bent forward and kissed Shannon again, as his penis lost it’s firmness and slipped out of its sheath. A few seconds later, Peter was lying on his back, with his knees drawn up to his chin, looking at Shannon.

“It’s your turn now,” he stated.

“You don’t have to,” Shannon informed him. “I’ve heard you say you’re not gay and I know you’ve never done it. Hell, you’ve probably never even thought about it before, so it’s okay.”

“I might not have done it,” Peter replied, “but Andrew used his larger dildo on me after his birthday party. It wasn’t bad, so I’m willing to try. Just stop if I tell you to, all right?”

“Sure, if that’s what you want,” Shannon stated, and Peter merely nodded.

Just thinking about what he’d been offered got Shannon hard, so he slipped the condom on, lubed it up and then went over to prepare Peter. Shannon worked the lube along Peter’s crack, before using one and then two fingers to work it inside. Once he felt he’d done sufficient preparation, he looked at Peter and spoke.

“Are you still sure about this?” Shannon asked.

“Yes, what you did even felt good,” Peter confessed, “so go ahead.”

Without needing more encouragement, Shannon moved into position. “Just push out a little…”

“I know,” Peter replied, cutting him off. “Andrew told me the same thing when he used the dildo on me.”

Hearing this, Shannon pushed his dick against the resilient ring and entered. Peter let out a little grunt when this happened, so Shannon froze.

“Are you okay?” he asked, concerned.

“I’m fine,” Peter confirmed. “Just a bit of a shock. It feels bigger than it looked.”

Both boys chuckled after that was said and it seems that Shannon took the comment as a compliment about his size. He basked in the good feelings momentarily, before he started to slide slowly forward. Once he was completely inside, he stopped and gave Peter time to adjust.

“Let me know when you’re ready for me to continue,” Shannon informed him.

“Go ahead,” Peter replied. “I’m fine. I just feel full.”

Shannon now began gliding in and out of Peter’s love channel, as he slowly made love. He even bent down to kiss Peter, as Peter had done to him. Peter didn’t object and responded in kind, and both boys seemed to be enjoying this new connection (pardon the pun.)

After several minutes of this action, Shannon began to speed up, until he eventually arched his back, drove his penis as far forward as it would go and released several bursts of his warm boy cream into the condom’s reservoir.

Once he finally recovered and withdrew, Shannon looked down at Peter, to see how he was doing. Peter was merely lying there, with his eyes closed, but there seemed to be a slight smile etched on his lips.

“Are you okay?” Shannon asked.

“Yes, quite,” Peter replied. “You made something inside me tingle and that felt quite alright.”

“I’ll bet it was your prostate,” Shannon suggested. “Some boys are more sensitive there and I guess you might be one of them. So you didn’t have a problem with it.”

“No problem,” Peter confirmed. “I’m not sure I’ll ever do this again after I leave here, but it wasn’t bad at all. In fact, it actually felt good.”

Seeing Peter was okay with what they’d done, he merely leaned over, kissed him again and they both cleaned up. After that, they went to sleep in the same bed. They didn’t cuddle, but they did sleep fairly close to each other.

I was also happy to hear that Andrew had gotten in on the action too. His recent problems concerning his delayed puberty had created other problems for him and made me worry about him. Sometimes he even refused to do things with the others, but that might possibly have just been to prove to himself he was still a baby. It might have also been due to the fact that seeing the others naked bothered him because he wasn’t as developed as they were. Regardless of his reasoning, tonight he ended that drought and got together with Graham. I heard things went very well.

Even though Graham is sixteen and Andrew is only thirteen, they were still close and had been for quite some time. In fact, Graham had been Andrew’s first sexual partner. Graham and Andrew were also both uncut, which gave them another bond, and they’d always enjoyed each other’s company. It also didn’t bother Graham that Andrew hadn’t reached puberty yet and still had a boy-sized penis. Since Andrew realized this, it helped him feel more comfortable when they were together. So, tonight the pair shared Andrew’s room, while Sammy went to Cole’s room for the evening.

Once Graham and Andrew were alone, they just sat and talked for a while.

“You know, I was hurt when you got close to Cody, instead of me,” Andrew told Graham. This caused Graham’s mouth to fall open, because he hadn’t suspected it. He didn’t realize Andrew felt that strongly about him.

“Really? I didn’t mean to hurt you. I really didn’t,” Graham apologized. “I’m very sorry about that.”

“Thanks and I know better now,” Andrew explained, “but then I thought it was because you didn’t think I was old enough for you. I thought it was because I had such a little dick and no hair or anything.”

“That’s ridiculous. It was just that Cody and I got close, and well… when he got sick I just had to be with him all the time,” Graham explained. “There was nothing wrong with you, but I did love Cody and thought I could help him deal with what he was going through.”

“It’s okay. I understand now,” Andrew replied. “I don’t feel bad any more.”

To make sure things were better now; Graham gave Andrew a huge hug and kissed him aggressively. This brought a rather large smile to Andrew’s face, as they moved apart, and now he realized he might have overreacted before.

After that, Andrew went on to explain how he felt about not being as physically developed as everyone else. In response, Graham felt it important that he assuage Andrew’s concerns, not just by telling him, but also by showing him. He began by pushing Andrew back and slowly undressing him, as he took charge of the situation. Andrew wasn’t sure what to expect, but soon Graham had him lying naked on the bed. Graham began to lovingly stroke his body and tell him how wonderful it was. Andrew thought he was just being nice, but quickly acknowledged that Graham was having as much fun at this as he was, so he just leaned back and enjoyed what his partner was doing.

Graham bent lower now and began to kiss and lick all the various parts of Andrew’s body, but took special care when he reached his genitals. It didn’t take long before Andrew’s little boy mast was standing tall and proud. He didn’t seem to care it was so small just then, because his pleasure was intense. Graham continued to run his tongue all around it, pulled the foreskin back and forth, and sent Andrew squirming around on the bed. Andrew’s slender hips were bouncing up and down off the mattress, as Graham took his penis between his lips and began to let it slide in and out of his mouth. Andrew was in overdrive now, seeking the pleasure that only sexual release could give him. Soon his body began to tremble, as his dry orgasm overwhelmed him.

Once he recovered, he thanked Graham for what he had done and let him know he wanted to return the favor, but not in the same way. “Graham, I want you to stick yours inside me tonight,” he announced, which caused a little panic to register on Graham’s face.

“Are you sure?” he asked, concerned it wasn’t time yet.

“Yes, I’m not a baby any more,” he assured him. “Dad said so.”

“But you’ve never done it,” Graham pointed out.

“I know,” Andrew conceded, “but I’ve been practicing with the dildos you guys gave me for my birthday.” Graham still looked concerned, but replied.

“Okay, but let me go get some things then, to make sure you’re ready.” Andrew thought that Graham was merely going to get a condom and some lube, but instead he ran downstairs to make sure this was okay with me. He knew I was protective of Andrew, so he wouldn’t do this without my expressed approval. After knocking on my door and getting my attention, he told me what bothered him.

“Dad, Andrew wants to try anal tonight and he wants me to do it to him.” I thought this over for a few seconds and realized a refusal would probably send Andrew into another bout of depression over his lagging level of physical maturity. I had a decision to make, and quickly, so I looked at Graham and discussed it with him.

“Look, this will have to be your choice, but let me tell you what I’d do, if I were in your shoes,” I offered, to assuage his concerns. “I’m not sure Andrew would take rejection well, so why don’t you grab some of the dildos out of the bathroom, the smaller ones and up to one you think is about the same size as you. If he can handle those all right, then I guess it would be okay. If not, maybe he’ll change his mind and take you off the hook.”

“Are you sure this is okay with you?” Graham persisted, still looking concerned.

“It’s not me who has to be okay with this,” I told him, “but you and Andrew, and he seems more than willing, from what you’ve said.”

“Okay, I’ll try that then,” Graham agreed.

“Are you okay with this,” I asked him, in an effort to be certain he wasn’t having any doubts about his role in the matter.

“Oh, I’m fine with it. I’ve wanted to do this with Andrew for ages,” he confessed, “but I thought he wasn’t ready for it yet. I’m still not sure, because he is pretty small.”

“Yes, but using the dildos should determine if he can handle it,” I told him. “If you’re okay with it and he takes the dildos all right, then I don’t see any reason he can’t have what he wants, as long as you don’t object.”

“No, I don’t,” Graham assured me.

“Okay, then,” I agreed. “By the way, where does he think you are right now?”

“I told him I needed to go get a few things,” Graham admitted.

“Then go get them and get back to the room,” I warned him, “before he comes looking for you. I don’t think he’d appreciate finding you here talking to me about this.”

Graham nodded, took off and returned to Andrew’s room, but not before picking up the needed items along the way. Andrew did ask him what took him so long, so Graham made up some excuse about one of the others having one of the dildos he wanted, so he had to go around, from room to room, until he located the items. Satisfied with that response, Andrew waited as Graham got him ready.

Graham began by lubing up his finger and putting extra lube around Andrew rectum, so he could spread it inside his anal cavity. Andrew took his finger easily, so Graham moved on to two fingers, and again Andrew had no problem accepting them. Now, Graham took the smallest dildo, lubed it up, and slowly inserted it into Andrew’s love canal.

“I’ve done this to myself,” Andrew announced, answering Graham’s unasked question about why this seemed to be going so smoothly. “I’ve used all the ones you have now, trying to get ready for doing this with you.”

Graham smiled at the thought his little friend must have been planning this moment for quite some time. It also made Graham want to please him even more. After pushing the dildo in and pulling it out several times, he switched to the next larger one, but soon he moved on to the one that was approximately the same size as him, the final step before the real thing. Seeing Andrew had little difficulty in taking this, Graham decided it was all he could do to prepare him for what he actually wanted. He looked at Andrew, to see if he was still intent on losing his virginity, and could read the eagerness on his young partner’s face. Hurriedly, he got undressed.

“Okay, let’s do this then,” Graham suggested. “I’ll lay back on the bed and you can squat over me and lower yourself onto my dick, so you can take it as slowly as you want or even stop, if it hurts.”

Andrew grinned and pushed Graham backward, since he didn’t want to give him time to back out. Immediately, he began to suck on Graham’s dick, to make sure it was fully hard. When Graham pulled him off, for fear he’d shoot just from the oral stimulation, he put on a condom and added some lube, ready to do the deed.

Once this was accomplished, Andrew quickly positioned himself above Graham’s waist and began to lower himself downward. Eagerly, he guided Graham’s penis toward his opening and then sat down on it faster than Graham thought he should. Seeing Andrew didn’t seem to have any trouble doing this, Graham suspected Andrew had been using even larger dildos for practice, for now the boy was sitting on his pubic region.

“Are you okay?” Graham asked, concerned.

Graham was still worried Andrew had done too much too quickly, but Andrew merely nodded and grinned. To him, this was just another verification he was no longer a baby. Forcefully, he began to bounce up and down on Graham’s cock.

The tight, warm fit soon sent Graham reeling, as he enjoyed the lustful pleasure this action sent through his body. Andrew seemed to be enjoying it just as much, even if it was probably more a psychological thrill he got from doing what he considered an adult activity, rather than from the physical pleasure he might be receiving from this coupling.

The quick pace Andrew was using, in combination with his tight opening, soon had Graham moaning and reaching his climax. Even though he wished it would have lasted a bit longer and he tried to prolong his orgasm as long as he could, there was only so much he could do or how much he could take. Soon, Andrew brought him to the point of no return and Graham arched his back, grabbed Andrew by the hips and held him steady, as he slammed his penis into him one final time.

At this point, his juices exploded out of his dick and filled the tip of the condom with his semen. It also made Graham see stars. Realizing what happened, Andrew was totally ecstatic, thinking he was now one step closer to being a man. With Graham’s penis still inside him, he leaned forward and began kissing his partner, before he stopped and thanked him for what they had just done.

“Thank you for doing this with me, Graham,” he gushed. “Did I do it okay?” He obviously needed a little reassurance that he performed satisfactorily.

“Oh, yes,” Graham gasped out. “You did super.”

This made Andrew beam even more and he wiggled on Graham’s cock, trying to bring it back to life. Even though that wasn’t going to happen soon, he wanted to keep it inside of him for as long as he could and Graham wasn’t about to complain. However, the physiology wasn’t cooperating, and Graham’s penis continued to wilt, until it plopped out of Andrew’s anus.

Since this signified his first time was officially over, Andrew snuggled up beside Graham, after Graham disposed of the condom and cleaned up a bit. Andrew hugged and kissed Graham, in appreciation for what they had just done, and then he let his body meld into the older boy’s torso. Before they fell asleep, Andrew had one more surprise.

“Can we do this again, tomorrow night?” Andrew asked.

Slightly surprised by this request, Graham quickly found his tongue and spoke. “Hey, if that’s what you want, I won’t say no. I really enjoyed it.”

Pleased with the response, especially the part about Graham enjoying it, Andrew’s wrapped his arm and leg over Graham’s body and they both fell asleep. Truly, this was the Christmas present Andrew wanted, and maybe now we could get past all the nonsense about his still being a little boy.