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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 6: A Day on the Island
The next morning, I woke up and stretched. Bo had slept with Todd and as I walked down the hall, I saw him cuddled up on our master's chest. I smiled and went into the kitchen to get some breakfast started. As I was frying up the sausage to go with the eggs and toast I had prepared, Todd walked in.
"Something smells good."
"Hey, Sir!" I replied. "I was going to surprise you two with breakfast in bed."
Todd smiled and came over and hugged me from behind and kissed my neck.
"You still can. Bo hasn't quite woken up yet and I was just taking a bathroom break. Bring it back when you are done."
"Ok," I replied.
Todd wandered back and I finished cooking. I put everything on a large tray and slowly made my way into the bedroom. Todd was naked and sitting on top of the covers and Bo was just waking up and rubbing his chest. When Bo saw the food, he perked up and smiled.
"Well, this is a nice treat!"
"Nothing but the best for my Sir and Alpha," I replied.
Bo laughed as I put the tray on the bed and went back to grab them two cups of coffee. When I returned, Bo was munching on some toast, and Todd was bent over the plate eating some of the eggs.
"Well, how is it?" I asked as I handed them their cups.
"So good," Bo replied.
Todd grinned and motioned me over and kissed me.
"Very tasty, boy."
"Well, when you are done, give me a shout," I said. "I am going to go clean up the kitchen."
"Are you not going to eat?" Bo asked.
"I have a plate in the kitchen," I replied.
"Ok," Bo said with a smile.
I returned to wash the dishes and eat my food and when I was done, I heard someone walking on the floor and saw Bo appear around the corner with the tray of empty plates.
"I said I would come to get that," I replied.
"I know," Bo said. "But Sir asked me to bring it to you. He wants to fuck me this morning and then we can get going."
"Sounds like a plan, bubba," I replied. "I'll get a shower and start getting ready."
Bo kissed me and returned to the bedroom. When I had things cleaned up, I walked around and heard moaning coming from behind the closed bedroom door and I grinned as I headed down to the bathroom. After my shower, I was brushing my teeth when Bo came in walking funny and covered in sweat. I laughed and reached around and felt his butt and the cum that was dripping out of it.
"Someone got bred well."
"Ugh," Bo replied as he rubbed his ass. "He fucked me twice in a row. The man was horny today."
"Oh, don't act like you didn't like it," I replied.
Bo grinned and winked at me and then got into the shower. I headed into the living room to open the windows and let some fresh air in and I found Todd sitting at the kitchen table drinking another cup of coffee and reading something on his tablet. I walked over to him and rubbed his head and kissed it.
"Bo tells me you got your balls drained well this morning," I said as I opened the windows.
"He's got a good ass, that one," Todd replied with a smile. "But, for that matter, you do, too. I'll catch you tonight."
"I'll be ready, Sir," I replied.
"Are you two still driving down into the city?" Todd asked.
"Yeah, that is the plan," I said. "We wanted to do some touristy things and enjoy the day."
"Good deal," Todd replied. "If you don't mind, I would like you to take some things to Bill."
Bill was an old friend of Todd's. We had met him last year when we first visited Todd's vacation home. Bill was older and a little shorter than me. He was bald with blue eyes and a bright white beard and reminded me of an old sailor. He had a nice belly and a decent cock and balls, which I was able to drain during that visit.
"Sure, we can do that," I said.
"Good boy," Todd replied.
Once I had aired the place out, I sat down on the couch and pulled out my computer to catch up on some emails. Bo came in later in his cargo shorts and a bright pink shirt and sat next to me. I looked over at him and smiled. His shirt read 'boy for hire'.
"Advertising much?" I said.
Bo looked down at his shirt and laughed.
"A friend gave this to me."
"OK, well are you ready?" I asked.
"Yup," Bo replied. "I just need to put some shoes and socks on since we will be walking around."
"Cool," I said. "Well, let me go put clothes on and I'll be right back."
After getting dressed, we each kissed Todd and then he handed us the keys and I drove us down to Key West. The first stop we planned was Bill's so we could drop off the package that Todd had given us. Bill lived above a shop on Whitehead Street and when we got there, we parked and walked up the staircase, and knocked on his door. When it opened, Bill was in his underwear and he smiled.
"Boys! Good to see you again! Please, come in!"
We smiled and walked in and handed the package to him and he took it and placed it in the kitchen.
"I'm actually getting dressed to run some errands," he said. "Todd called and told me you were coming down. Are you going to be in the city long?"
"We are just going to do some sightseeing," I replied. "No big plans."
"Well, why don't you stop by about 3 pm, then," he said. "My sack has been riding heavy and needs some relief."
Bo smiled.
"We would be happy to help you with that."
"Good boys!" Bill replied. "You can leave your car here if you want and save paying for parking in town."
"Thanks!" I replied.
We waved to Bill and left and headed over to Duvall street and then down towards the heart of the town.
"What do you want to do first?" I asked.
"Well, it is still early," Bo replied. "The Hemmingway house is just down the way here. Why don't we do that and then we can get some drinks."
"Sounds like a plan to me!" I replied as I reached down and held his hand.
The house sat behind a stone wall. When we came around and entered to buy our tickets, we saw several cats wandering around and the two-story house sitting before us. It looked like a relaxing place to stay and when we entered, we walked around and admired some of the memorabilia around.
"The Old Man and the Sea" was a book I had to read when I was in grade school and I had been fascinated by Ernest's life and his travels. I had heard he was a well-known visitor to the bars in Key West. Some of the pictures of Hemmingway in later life looked a lot like Bill. A fact that Bo pointed out too.
When we came upstairs, we saw another cat at the landing and noticed it had six toes. Bo thought it was adorable and petted it and it ended up following us around after. We next took a guided tour that took about thirty minutes and when we were done, we headed back out onto the street and wandered around in some of the shops.
We passed by the frozen daiquiri place right as they opened and Bo wanted to stop in for a drink. We sat on the side of the outdoor space to relax and people-watch while we enjoyed it.
"You should have seen this place last New Year's," Bo said. "It was insane."
"I forgot you came down here with Sir for that," I replied. "Did they do anything special?"
Bo laughed.
"They lower a drag queen in a giant high-heeled shoe at midnight."
"Now that must have been interesting!" I said with a grin.
"We stayed with a friend of Todd's that had a room on one of the side streets," Bo said. "We only drove down to party on the street and ring in the new year, but there were so many people. I even felt claustrophobic."
"Oh, wow!" I said. "So, no sex fun?"
"Well, I didn't say that," Bo replied with a smile. "After the shoe dropped at midnight, I got taken back to the room and loaded up for the new year."
I chuckled.
"So, a good time overall, then."
"Yeah," Bo replied. "Todd got too drunk and passed out on the sofa and I slept on the floor next to him till the next morning and then we drove back to the house."
"Well, I am glad we are getting a chance to see it when it is not so crazy," I replied. "The weather is nice too."
"Yeah," Bo said as he reached out and held my hand. "And the company is good too."
I smiled and kissed him and when we finished our drinks, we continued walking towards Mallory Square. We stopped off at a restaurant and had some Cuban sandwiches, which were out of this world, and then walked out onto the square where we had been the last time we both were in town together.
A cruise ship was making its way into port and we watched as they came in and docked. I was amazed at how big the thing was and Bo laughed.
"Just wait till you see the cruise ship we take next year. It would dwarf this one."
"It's simply amazing that these things can float as massive as they are," I replied.
Bo and I walked around and did some more window shopping before stopping at a saloon for some beers and to relax. After we had a few and were feeling good, we noticed it was getting close to 3 pm, so we made our way back to Bill's house. It was a good thing we left when we did, too, because the cruise ship passengers filled the area as we walked down the street.
Once we got back to Bill's, we walked up the staircase and knocked on the door and when the door opened, we saw him standing naked in front of us.
"Right on time," he said. "I like boys that are punctual. Come on in and strip down. You can place your clothes on the couch here."
We walked in and undressed and did as he said and then followed him back into his bedroom. The lights were off, but the windows were open and there was a breeze coming in that made it feel nice. Bill got on the bed on his back and told us to stand near the wall. He reached over and grabbed a small box on his nightstand and then proceeded to light up a joint and smoke it while he looked at us.
"I have to say, Todd got himself two handsome subs. I hope you two are treating him well."
"Yes, Sir!" we replied.
We watched as Bill smoked and blew clouds into the air. The smell of the weed was pungent, but the open windows helped to air out the room. I never liked marijuana myself, but I didn't mind those that did partake. When Bill finished, he put the box back on the table and rubbed his balls.
"I think I will take you first," Bill said as he pointed to Bo. "Come over here on your belly and get me hard."
Bo smiled and walked over and got on the bed between Bill's outstretched legs. He moved up till his head was over the man's soft cock and he cradled Bill's balls as he sucked on the man's cock. Bill put his arms on either side of his pillows and leaned back on the headboard and closed his eyes. I heard him moan as Bo worked on him and as Bill's cock hardened, my nub swelled too.
Bo has this cute way his ass wiggles when he is in the zone and pleasuring a man. I saw him start to shake as he deep-throated Bill and I smiled. Bo was flexing and curling his feet and Bill brought one of his hands down and rubbed the top of Bo's head.
"Such a good boy," Bill replied as he looked down at him. "Ok, time to switch with your fellow sub."
Bo sat up and crawled off the bed and we swapped places. As I laid down and took Bill's cock into my mouth, I could taste beads of precum that were starting to form. I pulled him deep into me and felt him near the back of my throat. As my nose hit his bush, I could smell his scent and it was nice. I found myself wiggling my ass in response and Bill smiled at me and played with his nipples.
"You two definitely know how to pleasure a man," Bill replied.
I grabbed the base of Bill's cock and sucked on it and moved side to side and ran my tongue over his shaft. I then moved and stuck my nose under his balls to get more of his musk and proceed to suck on each of his balls in turn. When I returned to his cock, I saw that precum had flowed down and was glistening in the light from the window and I licked it slowly and tasted the nectar.
"Fuck, boy," Bill said. "I'm ready to fuck."
"Who do you want?" I asked.
"You sucked me off the last time you were here," Bill said. "How about I fuck the other one."
"That is fine!" I replied with a smile.
I backed off the bed and stood beside Bo and Bill grabbed the lube from the side table.
"Where do you want me, Sir?" Bo asked.
"Well, I am not as young and spry as I used to be," Bill said as he stroked his cock. "How about you ride me but put your back to me."
"Yes, Sir," Bo replied.
Bo walked over and Bill handed him the lube and he put some on his finger and pushed it into his ass. He then climbed on the bed and faced me and put his legs on either side of Bill and reached back and guided the man's cock into him. As he sat back, I saw Bo close his eyes and grit his teeth. Bill had his hands on Bo's waist and smiled as he saw his cock disappear.
"Damn this ass is nice!" Bill said.
Bo looked over at me and smiled and I winked at him. I watched as he adjusted his legs and then lifted and sat back down on the hard cock behind him. Bill held on to him as Bo fucked himself. Bo began to moan and I saw fluids start to appear under his cage.
"How does that dick feel?" Bill asked.
"So good, Sir," Bo replied. "You are so deep in me."
"That's a good boy," Bill replied as he put his hands behind his head and closed his eyes.
Bo locked his eyes on me and I saw the pleasure in them as he felt the cock slide in and out. His nub was dribbling all over his balls and it flowed onto the bed below. As he moaned, he bit his bottom lip and my nub got so strained in its cage I had to reach down and adjust it. Bo smiled when he saw me and he blew me a kiss and then looked down and moved up and down faster.
The bed shook as Bo pushed himself down to bring Bill deeper into him. Bill began to pant and he reached over and rubbed Bo's back. Bo leaned towards him and arched his back and I saw Bill's legs start to shake. He moved his hands to Bo's waist as he moaned louder.
"Fuck. Fuck. Oh, fuck!" Bill shouted.
His legs straightened and I saw his feet curl as he orgasmed. Bo sat down and moved side to side as the cock drained in him. Bill tossed his head back and to the side as he groaned.
"That's a boy! Milk my load out!"
Bo reached under and rubbed Bill's balls as they finished pumping and as he stood up, I saw a glob of cum drop from his ass and land on Bill's groin. Bo moved to the side and I walked over and got on the bed and took Bill's cock into my mouth to clean it and then moved down to swallow the cum that had escaped.
"Damn, Todd did say you both were little piggies," Bill said as he caught his breath.
Bo watched from the side and fingered his ass and tasted Bill's load. When I was done cleaning the man, we both moved back over to the wall and Bill fondled himself and smiled.
"Thanks for that, boys. I feel much better."
"Glad we could help, Sir!" I replied.
"Yes, we would love to help next time we are in town," Bo added.
"I'll remember that," Bill said. "Ok, you can go. I am going to smoke another joint and take a nap."
"Thank you, Sir!" I replied.
Bill smiled and waved at us and Bo and I turned to go back into the living room and dress.
"My ass is so flooded," Bo said.
"Come over here and bend over the couch," I said.
Bo smiled and bent over and I stuck my tongue in his ass and tasted as cum ran out. Bill had put a massive load in him and I swallowed some of it as I cleaned Bo's hole. When I pulled back and determined I got most of it, I rubbed his butt and Bo sat up and smiled.
"Thank you!"
"God, we ARE pigs aren't we?" I said with a grin.
Bo chuckled and grabbed his clothes and we both got dressed and walked down to the car to head back to the house. When we pulled back in the driveway, the sun was just setting and we found Todd out on the back porch drinking some whiskey.
"Well, did you two have fun?"
"We did, Sir," I replied. "It was a nice day and we got to do a lot of walking around the city."
"I haven't done that in years," Todd said as he took a sip of his drink. "Bill texted me to tell me you serviced him well. Thank you for that."
"Of course!" Bo replied.
"Well, let's grab some dinner, and then I owe Matt a load in his ass."
I smiled and wiggled my butt like Bo often did and Bo laughed and kissed me.