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This story is the sequel to my first book, "Southern Chastity". I encourage you to read it to get the backstory on Matt, Bo, and Todd. https://www.amazon.com/L-D-Cub/e/B092JRPVJ6/
Todd's Boys
Part 24: A Caribbean Surprise
The next morning, I opened my eyes and groaned. I had not slept well for some reason and I rubbed my face and sat up. Bo had his head on Todd's chest in the bed next to me and was lightly snoring. Todd was rubbing his back and reading his tablet. He looked over at me and smiled.
"You had a restless night."
"I feel like it," I replied.
"Anything wrong?" Todd asked.
"Eh, maybe I just could not get comfortable," I said.
"Well, you can sleep with me tonight," Todd replied.
I smiled and stretched and got up and opened the door and walked out onto the balcony. We were in port and I could see the city of Nassau below. There was a nice breeze off the water and I closed my eyes and took a deep breath as I stood there. I felt hands move around my waist and when I opened my eyes I saw Bo putting his head on my shoulder and kissing me.
"Morning, babe."
"Good morning," I replied.
I felt Bo's nub rub against my crack. He had his morning wood and he pushed it between my cheeks. I moved forward and turned around and looked at him. He was grinning at me.
"You know you are not supposed to use that thing," I said.
"I know. I know." Bo said as he leaned in and kissed me. "Your ass is just so inviting."
I laughed.
Todd walked outside behind Bo and grabbed his waist and pulled him back into him.
"Looks like it will be a nice day today!"
"Yeah," I replied. "And this one's pole is trying to find a home."
Todd looked down and saw Bo's hard nub and laughed. He reached down and grabbed it and Bo groaned.
"Do I need to put ice on this, Bo?" Todd asked.
"No, Sir," Bo replied. "I can manage."
Todd released his grip and hugged Bo and kissed him.
"Be a good boy for me today and don't touch it. You aren't cumming today."
Bo pouted and looked down and I raised his head with my hand and smiled at him.
"Come on, let's get you in the shower. Once we are cleaned up we can grab lunch and head into the city and explore."
"Ok," Bo replied as I kissed him and we all turned to go inside.
The ship was slated to be in port only until the early afternoon, so once we were dressed and grabbed a quick breakfast, we headed out and down the gangway to the dock below. It was a nice sunny day and we first headed to Rawson Square and took some pictures before browsing some of the markets that were nearby. I was not very good at haggling, so I let Todd handle anything we saw that was interesting and wanted to try to purchase. We each got some small souvenirs before we boarded a vehicle that took us on a tour of the island.
The excursion was nice. The weather was pleasant and we saw several local landmarks and even drove over to Paradise Island and explored the Atlantis casino. We grabbed some lunch there and Todd played some poker and slots before we got back in the car and drove back over to the ship again. Todd wanted to take a nap when we got back on board, so Bo and I grabbed our trunks and we went and got in the pool for a while. Bo even tried the boogie board at one point, though he was not balanced right and fell a few times at first.
After we dried off, we grabbed some drinks and met a few of the bears on board, and had a good time whiling away the afternoon while the ship left for sea again. We were scheduled to be sailing all day on Tuesday before arriving at St. Thomas on Wednesday. Bo told me that he had booked a spa day for us the following day, in addition to a nice dinner, so I was looking forward to that.
By the late afternoon, Todd appeared again with some cubs in tow. He apparently found them in the hall after his nap and managed to pound a load into both of them before coming down to meet us, so he was sedated. Bo, on the other hand, was horny and made it known. As he drank, he got more handsy with me and his nub was poking out of his pants noticeably. Even the cubs around Todd took note.
"That looks like a kickstand in your pants!" a ginger-haired cub replied as he sat down.
Todd laughed as he took a seat and a dark-haired cub sat next to him.
"Eh, it has a mind of its own now," Bo replied. "Sir hasn't let me cum in several days."
"I seem to recall that you once went six months without an orgasm," Todd replied as he took a drink and sat back.
"Yes, well, that was then and this is now, Sir," Bo replied with a grin.
I laughed.
"That training went out the window quickly."
"How long are you going to make him wait?" the dark-haired cub asked.
"For a while," Todd replied. "I want to see just how strong his will is. He will get a reward if he waits and obeys."
"I'm almost glad I am in my cage," I replied. "That is too much temptation."
Bo laughed.
"Especially when that bare ass of yours is moving around the room."
I leaned over and kissed him and he winked at me.
The cubs joined us for dinner and then Todd followed us out to the pool again and then a relaxing soak in the hot tub after. Todd reached over and played with Bo's nub on several occasions and teased him. Bo groaned whenever he was stimulated, but he did keep his hands off and I was impressed at his self-control.
In the evening, we hung out with Jonathan again and played some cards before getting ready for bed. I pulled out the bed in the couch for Bo and then crawled into bed with Todd, who wrapped his arms around me and snuggled with me as Bo brushed his teeth and then laid down.
"When is your spa time?" Todd asked Bo.
"We have to be there at 10 am," Bo replied. "I have a deep tissue massage booked for us both, but we can use the thermal spa at our leisure. I figured we could do the massage and then use the sauna and steam room to relax after and then grab lunch."
"That sounds lovely," I replied.
"I booked us all dinner at the steak restaurant in the evening," Bo said.
"Wined and dined!" I replied. "You are too good to me, Bo."
Bo grinned and blew me a kiss.
"Get some sleep babe."
Todd squeezed me and then I pulled the covers over us and we drifted off.
The next morning, I woke up to Todd's cock poking me in my butt. I turned and he smiled at me from over my shoulder and I felt his lubed fingers as they pushed inside me. I groaned as I opened up and he playfully bit my ear. He rubbed his dick over my ass and I felt his precum cover my hole before he pushed forward.
"Oh fuck," I groaned as I felt him slide inside.
"That's my boy," Todd whispered in my ear. "Take me into you."
I closed my eyes and held on to his arms that were wrapped around me as I felt his dick fill me. His balls met my ass and he wrapped his legs around me and kissed my neck. As he slowly pulled out and pushed back in, he squeezed me tight and I moaned.
"How does that feel, boy?" Todd asked me.
"So good, Sir," I replied. "Your cock feels so good."
"That's my good boy," Todd replied as he turned and put me under him.
I gripped the pillow and pushed my face into it as he put his arms on either side of me and thrusted inside. My cage was pushed into the bed and I felt my nub swell and start to leak. I breathed in deeply as I felt him rub over my prostate and energy shot through my body. Todd put his arms under mine and brought his body close. I felt his groin on my ass and his large, heavy balls lying over my caged ones. I felt loved and dominated at once. He licked my neck and nibbled on it and then lifted himself off and fucked me harder.
I moaned loudly as I felt him push deep inside and as he picked up the pace, he groaned. When he climaxed, he growled loudly and collapsed on me and I felt the pulsing of his shaft as it sat right over my prostate. His deep breaths resonated through me and I felt the warmth of his flushed skin. When he rolled off me, his cock slid out and cum ran over my butt cheek.
I closed my eyes and moaned. I felt empty without him inside me and my nub was aching. It was then I noticed a tongue running up the crack of my ass and I opened my eyes and turned and saw Bo behind me cleaning up Todd's cum. He smiled at me as he ate me out and I turned and moaned some more. When he was done, he crawled next to me and kissed me.
"That was fucking hot," Bo said.
I looked down and he had his nub in his hand. It was swelled and dripping and his balls seemed even fuller and heavier than yesterday. I reached down and grabbed his arm and pulled it up to me and he whimpered. I kissed his hand and then wrapped my arms around him and he put his head on my chest.
"I know you are horny, babe. You can power through it."
Bo groaned again and embraced me and Todd leaned over and rubbed Bo's shoulders.
"Talk to me, Bo. What are you feeling?"
"My hormones are raging, Sir. I touched myself several times while I was watching you have sex with Matt. But I stopped and sat on my hands every time I noticed."
"Do you need to be locked up to stop yourself from being tempted?" Todd asked.
"No, Sir," Bo said. "I want to prove to myself I have the power to abstain."
"It's not easy," Todd replied. "I won't fault you if you need me to cage you."
"I'll be ok, Sir," Bo replied. "Can I at least get a prostate milking today?"
"Not today, Bo," Todd said. "No cumming and no milking. I want to test you."
Bo groaned loudly and grabbed onto my waist. I kissed his head in response.
"Remember our training, Bo. Subs put their emphasis on the needs of others. Use the energy inside you to serve Sir and please him. You can do it. I believe in you."
Bo looked up at me and kissed me.
"I love you."
"I love you too, baby," I replied. "Come on, let's get cleaned up. I am hungry and we have a day in the spa after!"
Bo's expression changed and he smiled.
"Yes!"
Bo got up out of the bed and went into the bathroom and I sat up and rubbed Todd's legs. I looked at him and smiled.
"I know it is not my place, but he is trying, Sir. That is a lot of temptation being unlocked and I don't know how much he can take."
"We will see," Todd replied. "I am not trying to be cruel, but I want to see just how disciplined he can be. You and I both know he has struggled in this area. If he can make it through today, I will reward him tomorrow. I promise."
"Ok, Sir," I replied.
"Just keep an eye on him and be with him," Todd said. "With your support, I think he will be fine. Just watch out. There are a lot of hot bears around."
I laughed.
"That is for sure. Cubs too, apparently."
Todd blushed and tossed a pillow at me.
After we were cleaned up, Bo and I went out for breakfast. Todd had made plans to hang out with some friends he had on board in addition to Jonathan and he told us he would meet up with us at dinner. Bo and I headed down to the spa area and they gave us some robes to change into and then brought us into a private room for the two of us where they began to rub us down with oils and then worked out the knots in our back and arms.
It was a lovely time. It included aromatherapy and the smell of the room helped me relax as I was being worked over. When the masseuse was done, we moved over to a warm chair that relaxed us as soothing music played. I looked over at Bo and he had a smile on his face.
"How are you feeling now?"
"I have never been so relaxed in my life," Bo replied.
"Good," I said as I turned and closed my eyes.
After a rest in the warm chairs, we went into the sauna to sweat out some and then finished up in a cool room with some water flavored with cucumbers. Bo leaned on me and rubbed my chest and kissed my shoulder.
"Was it worth it?"
I put my arm around him and hugged him.
"Absolutely, babe."
After we were done, we headed up to the room and when we entered, there was a lunch waiting for us inside.
"What is this?" I asked.
"I ordered it for us so we could relax in the room," Bo said. "Let's take it out on the balcony and we can enjoy the water."
After our lunch, Bo and I sat outside and enjoyed the sun. I looked over at him and he had his arms behind his head and his eyes closed. His nub was still at full staff below him and I chuckled as I closed my eyes and leaned back to nap. When I opened my eyes again, Bo was leaning over the railing and looking at the water below.
"Anything down there?" I asked.
"Some fish were near the surface earlier," Bo replied as he turned to face me. "Did you have a nice nap?"
"I did!" I replied as I stuck my hands out and sat up.
Bo came over to me and sat next to me and I wrapped my arms around him. He leaned on my shoulder and I rubbed his head.
"Thanks for all this pampering," I said. "This has been a wonderful day."
"Anything for you, babe," Bo replied.
Todd walked in a few minutes later and we turned and smiled as we saw him. He was covered in sweat and had that glow about him that we usually saw after he had vigorous sex.
"So, who did you fuck?" I asked.
Todd laughed.
"Jonathan and I had a three-way with another hot sub. I came twice."
"Very nice!" I replied.
"How was your day at the spa?" Todd asked as he walked outside.
"It was nice!" I replied. "Bo got us lunch in the room after and we have been relaxing out here ever since."
Todd rubbed Bo's shoulders and leaned down to kiss him. He then sat in the chair next to us and sighed.
"I could use a nap myself!"
I chuckled.
"What time do we need to be ready for dinner, baby?"
"Our reservation is at 6 pm," Bo replied. "I know that is a little early, but that is when I was able to get us a table."
"That is fine," Todd replied. "Give me an hour to rest and I will get up and get ready."
"Come on, Bo," I said as I moved to get up. "Let's go spoon on the bed."
"Watch that nub!" Todd replied as Bo walked by.
"I will, Sir," Bo said with a groan.
Dinner that evening was very nice. We all dressed up and had a lovely meal that included steak and all the trimmings. Todd even ordered us a nice bottle of wine to go with the meal. When we finished, we ran into the two cubs that Todd had met earlier as they were walking around. The ginger-haired one was named Sam and the dark-haired one was named Paul. They were a couple and were from Chicago. Todd suggested they join us as we were going to have some ice cream for dessert and they agreed. As we sat down to enjoy our desserts, Todd looked over at the cubs.
"What do you two have planned for the evening?"
"Nothing much at the moment," Sam replied. "Figured we would see what trouble we could get up to."
"Why don't you follow us back to the room," Todd said. "I'd love to play around some more."
"Sure!" Paul replied. "I'd like that!"
"Me too!" Sam said.
When we got back to the room, I stripped down and hung my clothes up and Bo was not far behind me. Sam was fascinated by my cage and was playing with it when Bo snuck by me to sit on the couch. Paul sat next to him and noticed Bo's nub already starting to harden and he reached over and rubbed it.
"Oh, fuck!" Bo replied as a spurt of precum shot out.
"Damn!" Paul replied. "I barely touched you!"
Todd was still in the bathroom and I turned and looked at the two of them on the couch.
"Bo is not allowed to be touched, Paul."
"I'm sorry!" Paul replied.
Bo was groaning as Todd came into the room.
"What is going on?"
"Nothing, Sir," I replied. "Bo had a little reaction to Paul. He touched him before we told him he couldn't."
Todd looked over and saw the glistening of the fluids coming out of Bo's hard nub and he smiled.
"Are you sure you can handle yourself out of your cage, Bo?"
"Yes, Sir," Bo replied.
"Are you willing to put that to the test?" Todd asked.
"How so, Sir?" Bo asked.
"Can you promise not to touch yourself no matter what happens?" Todd asked.
"Yes, Sir," Bo replied.
Todd had this evil grin appear on his face. I had not seen him look like that before. He bent down to whisper to Sam and they had a quick conversation before Todd looked over at Paul.
"Strip down and get on your hands and knees on the bed, Paul. I want that ass."
"Yes, Sir!" Paul replied as he moved to the bed.
Sam walked over and took his clothes off and then sat next to Bo. He rubbed Bo's leg and Bo looked over at him.
"Bo. I have given Sam permission to do whatever he wants to your body as long as he does not touch your nub. You cannot touch it either," Todd said as he dropped his pants and moved over to Paul.
"Yes, Sir!" Bo said as he turned to Sam.
Sam rubbed Bo's legs seductively and moved his face over Bo's chest. He stuck out his tongue and licked up Bo's side and then put his face under Bo's pit and rubbed his beard under it. As he did so, he let his hands roam over Bo's body and Bo shuttered. His nub engorged and pulsed and I saw fluids dripping down over his full balls.
"Oh, fuck!" Bo groaned.
Todd had his face in Paul's ass and was licking the boy's crack. When he heard Bo, he pulled out and looked over and smiled. He then glanced down at me.
"Matt, go over and give Bo a foot massage. Make it a sensual one. I want him to really feel it through his body as Sam does his best to pleasure him."
"Yes, Sir!" I replied.
I crawled over and touched Bo's foot and he stuck it out. I placed it in my lap and rubbed his soles as I watched Sam move around and sit in his lap. His cock was on top of Bo's nub and he leaned down and made out with Bo. Bo's feet flexed in my hands and his body shuttered.
I heard grunting to my left and I turned and saw that Todd was fucking Paul. Paul was on his hands and knees and his head was bouncing as Todd pounded him from behind. I turned back and watched as Sam continued to make out with Bo. Sam's hands were all over Bo's body. As they moved over Bo's skin, I heard him groan and his body continued to quiver.
Sam moved up and down. The movement must have registered on Bo's nub because he cried out.
"Oh god, you are touching me!"
"No, my hands are up here on your chest, Bo," Sam replied. "Todd didn't say I couldn't rub you with my body."
"Oh fuck!" Bo replied.
"Remember he told you that you could not cum," Sam said.
"Oh fuck!" Bo replied again.
Bo's feet were flexing in my hands. I don't think he even noticed I was massaging them. Sam was doing his best to stimulate his entire body and my nub was swelled just watching him. I felt bad for Bo because I knew he had to be in overdrive with the stimulation. I had no idea how he was going to control the natural impulse to cum from all of it.
The sound of sex going on beside us filled the room. The pounding of Paul's butt was mixed with the grunting of Todd. The smell of sex and sweat was building, too. Bo was writhing under Sam as the boy continued to move over him and grind his cock into Bo. This went on for several minutes until I heard Todd growl and he blew his load into Paul. I looked over and he was leaning over the boy as he unloaded. Paul cried out and Bo groaned loudly.
"I feel that nub of yours leaking all over me, boy!" Sam replied as he continued to move in Bo's lap.
"Oh fuck!" Bo moaned louder.
Todd looked over after he caught his breath and he sat back and pulled out of Paul. As he held his cock in his hand, he smiled.
"How's he doing?"
"He could blow any moment," Sam replied.
Bo's foot slammed into my hand and he screamed. He pushed Sam off him and startled me. I moved back and Sam turned to the side. Bo stood up and was shaking. His nub was bouncing and I saw precum flowing out of it. He looked over at Todd and hurriedly walked over and knelt in front of him and bowed his head.
"Please, Sir, no more. I am not allowed to cum and I can't take any more of the teasing from Sam. I want to be good and I want to honor my promise to you."
Todd grinned and walked over and put his hand on Bo's head. Bo looked up at him and Todd bent down.
"I wanted to see just how far you would let that go. I told Sam to stop anytime you told him to. All you had to do was say something. I am very proud of you, boy. You didn't let that thing control you."
Todd reached out and put his arms around Bo and kissed him.
"Go sit in the corner and wait."
"Yes, Sir," Bo replied as he moved over to the door.
"Sam, you did a good job," Todd said. "That was a good test. Now, how about you fuck a load into Matt as a reward."
"Hell yeah!" Sam replied as he looked at me.
As Sam bent me over the couch and fucked me, Paul turned around and cleaned Todd's cock off, and then they spooned for a while as they watched me. Bo knelt in the corner and did not say a word. He didn't touch his nub and he was expressionless the entire time. Once my ass was loaded, Sam collapsed on the couch. Todd then got up and walked over to Bo. While they had a conversation, I invited Sam and Paul out to the balcony to cool down.
"Is he going to be ok?" Sam asked. "I was just teasing him. He looked like he freaked out."
"Bo has had a hard time in the household," I replied. "He began in permanent chastity like me but was given more privileges over time. He has impulse control issues but has been working on it. I think Todd may have pushed him too far."
"Well, I am impressed," Paul said. "I know I could not have kept my hands off my cock. Of course, Sam is hot as fuck, too. I wouldn't have married him otherwise."
Sam laughed and kissed Paul and I grinned.
Todd walked out and joined us after several more minutes and Bo was behind him. He had a smile on his face and his entire demeanor was different. He walked over to me and hugged me.
"You look better," I said.
"I am better," Bo replied. "I proved I can be trusted."
I squeezed him and kissed him.
"I knew you could do it."
Sam and Paul hung out with us for a while longer and when they left, Bo crawled into bed with Todd and they spooned till Bo was asleep. The next morning, we awoke and found we were pulling into St. Thomas. Bo seemed like a completely different person. He was no longer acting horny all the time and was bounding around the room as he got dressed.
"What has gotten into you today?"
Bo smiled and walked over to me and kissed me.
"You'll find out."
I rolled my eyes as he ran back over to brush his teeth and I looked at Todd.
"What the hell drug is he on?"
Todd laughed out loud.
"Bo and I had a conversation last night. I let him know some thoughts I had and we discussed some other things. I will tell you about it later."
"Well, whatever it was, it sure has him wired!" I replied.
Todd had this look like he wanted to say something else, but he stopped and just grinned. When Bo was done in the bathroom, I got cleaned up and when I walked out, I saw that both Bo and Todd were dressed in the same Hawaiian shirt and khaki shorts.
"What's up with the matching clothes?" I asked.
"I've got the same thing for you to wear!" Bo replied. "It will be our island garb as we explore today."
"Ok you are freaking me out," I said. "Are you sure you are ok?"
Bo laughed and came over and kissed my cheek.
"Get dressed, silly."
Once I put on the outfit Bo gave me, we headed out to look around. Todd had booked us a skyride to Paradise Point that overlooked the island from a spot at the top of a mountain. While we were there, we did some more souvenir shopping and had lunch at a cafe. Bo held my hand nearly the entire time and Todd walked behind us. Bo's energy level was off the charts and I was sure he had done some drugs or something. Todd assured me he was ok with a chuckle and I put it down to enthusiasm for making it through his trial by fire.
After we took the tram back down, we hopped in a taxi that took us around to a nearby beach. It was a lovely area. The water was a beautiful shade of turquoise and the palm trees were swaying in the breeze. We took our shoes and socks off and walked around on the beach and Bo leaned on me as we enjoyed the weather.
"I wish we had brought our trunks," I said. "This would be a great place to swim!"
Todd came behind us and wrapped his arms around both of us and looked down at me.
"Matt, I think it is time I told you more about my conversation with Bo."
I turned to look at Todd and he smiled.
"Bo loves you deeply, but for any serious relationship to work, it has to be built on trust. Bo has shown that he has given in to temptation in the past and I told him that he needed to work on this if he was going to make his relationship with me work but with you, too. He proved to me last night that he has that capability, so I told him it was about time that he took another step with you."
Todd turned me and I looked over to see Bo was on one knee and had a small box in his hand. I gasped and put my hands to my face as he opened it and I saw a ring inside.
"Babe, I've known you were the one for me from the first moment I saw you," Bo said as he looked into my eyes. "I came so close to dropping out of Sir John's program just to be with you. You helped me continue and grow. You were there for me when I lost my father and you supported me when I stumbled. I wouldn't be the person I am today without you. So, I guess I have only one thing left to say. Will you marry me?"
I cried and Todd held me as I shook.
"Of course, I will, baby."
Bo took the ring out and placed it on my hand and then stood up and I embraced him. I squeezed him so tight I thought I might make him pop and he sobbed.
"Well, now I know you weren't on something today, at least," I said with a chuckle.
Bo laughed and then looked at me.
"Nah. Just love struck."
We made out passionately and then Todd put his arms around us both and squeezed.
"I think Bo earned his reward. You two get the bed tonight. I am going to stay with Jonathan. Feel free to pull as much out of those full balls of his as you can, Matt."
I laughed as I hugged Bo.
"Oh, and don't forget to drain Matt too, Bo!" Todd said.
Bo giggled and kissed me again and we all embraced on the beach for a while. When we finally broke, I wiped my eyes and Todd rubbed my back.
"Time to get back to the boat!"
"Yes, Sir!" we both replied.