Son of a Sailor - Cover

Son of a Sailor

Copyright© 2023 by SmokinDriver

Chapter 10

Coming of Age Sex Story: Chapter 10 - This is a story about a young man that come from a family that made their living on the sea for generations. How does he take what he was born to do and make the most of it. Coming of age, rags to riches. 30 chapters. I hope you enjoy it.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Fa/Fa   Consensual   Rags To Riches   Light Bond   Anal Sex   Masturbation   Oral Sex   Size  

It was nearing the end of the day when I walked out of my front door and looked out onto the roof patio and saw Gary talking to Jay. I went over to say hello and they were both happy to see me. Jay had put in his two week notice, two weeks ago and was now full time at the restaurant. I sat down and they started to tell me about the place.

They had decided on the name, “Hemingway’s,” which gave us a lot of flexibility in what we serve and the atmosphere. Jay had a good menu idea but Gary challenged him on a few things. Jay added some lower cost dishes and dropped some that had very hard to get ingredients just because we didn’t want to have to change the menu when the prices took big swings. They seemed to be working well together and Gary mentioned a general manager for the front of the house and a good bartender that he knew and had offered jobs to. The bartender was going to start mixing some signature drinks for the place.

It all sounded great and was making me hungry so we went down to look at the space which was in full construction mode with materials spread out for all the tradesmen to work. Gary showed me the bar area and where the riser would be for the music or extra tables. I was blown away by the bar that was already installed as well as the windows. We all went to dinner afterwards and I got stuck with the tab but kept the receipt for the CPA.

Cathy stopped by the next day to talk about the building. We walked through and the painters and finish guys were getting it move in ready. Cathy said, “As soon as it’s ready we’re going to move the girls. I don’t think they’ll mind too much since this place is nicer. We’ve had to keep the bad areas covered in the attic space above the ceiling tiles. As soon as they’re moved, we can open it up and start removing the asbestos. The faster we can start and finish one building we can start on the next. Of course the risk is low being contained in the attic space so we’re doing full remodels and upgrading the spaces. we’re supplying boxes and movers to get the stuff from the dorms to this place.”

“It sucks that they have to move mid-semester but I’m sure you’ll make it as painless as possible.”

“We’re planning an open house next weekend with food and drinks on the roof. The girls will get their rooms assigned and be able to see them when they stop by. The following Friday, Saturday and Sunday the movers will be free to get the stuff moved. I don’t think it will be too bad. They don’t need to clean after they leave since the place will be gutted.”

Soon my place would have three hundred and sixty new residents. It would be a change but I had no idea how big of a change it would be with me on the top floor by myself. I spent the next few days unpacking and buying things I needed for my new place. Darren called to see if I wanted to go out and do more research. The things that I’d discovered and suggested were mostly already known and in place per Gary’s experience but there were a few small things that I mentioned that he said he would do some tests on and see how things worked out.

Would it be better to give away free salty snacks at the bar and sell more drinks or charge a small fee for some chips and salsa or other salty snacks? Other things like that or selling two for one drinks against selling doubles for the price of a single? Only one glass to wash, one time to mix the drink and they couldn’t share with a friend. I decided to go out with Darren and do more research on Saturday.

Friday afternoon and evening, the girls started to show up around noon or when they got out of class. They seemed to like the newer and bigger spaces. The sun was shining down as they walked out onto the roof to get some food and drink. The view was nice but they also could all picture themselves studying out on the rooftop. There were a lot of smiles and many asked if they could move themselves and move in today. They were told that there was still work being done and for insurance purposes they would have to wait.

Cathy and Jen were there and it was good to see them both. Jen and Cathy both came by about 7pm after the open house was over and we had a few drinks and they both commented on the space. Cathy had to go and get ready for her hostess gig but Jen stayed and asked if she could call Casey to come over for a drink. I wasn’t going to turn that down.

Jen and I were on the couch talking when she showed up. She jumped into my arms when I opened the door. “I’ve missed you, Sir. I’ve missed you a lot.”

“I’ve missed you, Little One. Have you been a good girl?”

“Probably not. Did you want to spank me?”

“There’s more than one way to punish. Have you sucked anyone else’ cock, let anyone fuck your pussy or ass since I’ve last used you?”

She looked at the ground. “Yes, Sir. You make me horny just thinking about you even when you’re not around. I have been fucked and I’ve sucked but you are the only person to ever fuck my ass. I did play with Jennifer a few times and she used some toys on me and I did with her.”

“Thanks for telling me. Get naked and go sit on the chair over by the couch.”

Smiling, she said, “Yes, Sir,” and did as she was told.

Jen was just watching the interaction between us and was enjoying the banter. It was like a switch was thrown and Casey became a different person. I leaned over and kissed Jen and gave her a wink. Then we started to make out. As we slowly got undressed, I told Casey to masturbate and her fingers went to work. Jen was eventually on top of me and riding my cock.

Casey said, “Please Sir, may I cum?”

It was good to see that she remembered her place and role. I didn’t reply but had Jen turn around so she was looking right at Casey. She put her feet up on my knees and my cock stretched her open giving Casey a perfect view. I was rolling her nipples between my fingers as she raised and lowered herself onto my shaft. I could see that Casey was breathing hard and struggling not to cum. I said, “When Jen cums, you may join her and cum together.”

Casey sucked in her breath seeing that Jen wasn’t quite as close as she was. Jen smiled and then said, “I could just stop now.”

“No, please don’t stop.”

“I could use someone to do my laundry?”

“I’ll do yours with mine for a month.”

“Maybe you could clean my room?”

“Yes, please hurry.”

Jen started to move faster and used her own hand to rub her clit. It wasn’t two minutes later that Jen came hard and Casey screamed out her own orgasm. I shot off as I was like Casey and just waiting on Jen. Casey sat across from us, leg splayed and her head back with her eyes closed as she recovered. I said, “Little one, I don’t want my spend all over the couch. Come clean up our mess.”

She was soon over in front of Jen and her tongue was busy. When she was done cleaning the deposit from Jen, she started on me. When I was hard I moved Jen beside me and moved Casey to where she’d just been. It was fun to watch her struggle to settle down onto my cock. Jen decided to sit in the chair across from us and watch. We all enjoyed that round and then while Jen went into the shower. I fucked the fucktoy’s tight ass. We then showered together and got another round of drinks for all of us. We talked about the changes at the University apartments, the restaurant and what was going on in their lives. Casey said that she was thinking about changing jobs and had applied to be a stewardess. I invited them to call any time and to the grand opening of the bar in a few weeks.

Saturday I was up early and after my workout, I went for a run. I called my parents and was lucky to find them at home. It was good to catch up with them. I invited them up and Dad said he would try to schedule a job to get to New York but they had regular clients and regular routes that they were known for and got paid well for that knowledge.

That night I met Darren early like normal but it was a Saturday and the normal after work crowd wasn’t working. There were more people there than usual when we showed up and it didn’t get really busy until later in the evening. We had a good time catching up and I invited him to Hemmingway’s for the grand opening. I wasn’t on the prowl for company after the night before but did a good job as a wingman and sent Darren on his way with a cute Asian woman.

Sunday I was just going to chill, clean up around the house and relax which is what I was doing until my phone rang around 3pm. It was Amy and Mark Bellamy in town to start the research of the city timeshare idea. They were staying at a hotel near Time Square. We met at the building and did just a general talk through of my idea. Luxury condos in a timeshare. They could be offered as hotel suites when not reserved by owners. It wasn’t traditional mountains and beaches but the idea along with a hotel made it more interesting. Mark liked the idea and wanted to do another walk through and talk through the concept and idea the following morning.

Calls were made to Gary and Frederick and we all met for coffee before heading over to the construction site. Wearing hard hats, we made our way to the 4th floor. I said, “There are three floors of public access retail below us. I own the floor directly below us as well as this one and the one above us. I own others throughout the building but 20-29 were set aside for me to put in a hotel and besides the two floors below the penthouse, I have another block of ten floors 80-89 that I thought would be good for suites for the hotel or for a timeshare. I can build them out as condos, sell them and walk away with the cash but that seems too easy. This floor and the two above us I was thinking of as the lobby of the hotel with a restaurant, gym, spa and some meeting rooms but nothing huge. The ceilings are only fifteen feet tall.”

There was a lot of nodding and looking around but no response so I continued, “We can make some of the amenities open to the building residents if it makes sense. The timeshare owners will also have access to the rooftop patio. I don’t know if a bar will be up there or just space for the occupants. Any comments?”

Three people started to talk at once. I turned to Gary and he said, “Hotel space in New York is always a premium. I don’t know if people would be interested in ownership on a weekly basis.”

Frederick said, “I’ve lived here a long time. I don’t know much about condo rentals but I do know the Yankees, Knicks and Rangers all have teams coming in to play them and would like privacy and luxury if possible. They may buy you out or other companies that have high profile people in town for TV or News programs shot here. It could be marketed differently than other properties.”

Mark added, “I like the different levels. We can use discounted hotel rooms to get people in for sales presentations to prospective buyers. We can use the condos as high end upgrades at the hotel. I like that they’re in blocks. We can use the concierge from the hotel to set up tours of the city for the owners of timeshares.”

Frederick said, “I love it. Is there a theme or company logo that we can use in the design work?”

Everyone looked at Amy and she said, “Not yet. We have a shell of a building here and are just about to break ground in Fort Lauderdale. We have the room layouts and other features in the blue prints but nothing as far as interior design or marketing.”

Gary said, “I understand clubs, restaurants and hotels but don’t have any knowledge of timeshares beyond what I’ve read in trade magazines. When I think of New York, there are some times that are busier than others. Major conventions, the Macy’s parade, I don’t know if it’s a first come first serve or how that works. If it were a hotel, I would worry about selling out.”

Mark commented, “The same is true for beaches and ski resorts. They actually buy specific units and weeks. Depending on the size, location and view of the room the price could be different. If there’s a time of the year, that could affect prices as well. If you want the park view 3 bedroom unit the week of the parade, it will be much more than the studio overlooking the dumpster the third week in february.”

Amy added, “They can trade weeks or condos but they’re only guaranteed the one week and condo they bought. We do it on a points system. The week you buy is worth so many points. This makes trades work out more fairly.”

There wasn’t much more to do on site but Frederick and the others wanted to see the views from the higher floors of the hotel rooms and the high rooms of the timeshare. The roof was the last stop and not all the walls were up so we had to stay back but the view was spectacular.

The meetings lasted all day but they were not to nail down details but to decide on a game plan. The building was dried in and the windows were in place so we could start building out our spaces at any time. Mark suggested doing one floor completely in the condos for the timeshare so from when they stepped off the elevator to the last detail would be complete. When it was 80% sold, we could start on the next floor.”

Frederick was taking notes like crazy as his mind raced and his personality flared. He was talking with his hands and throwing out ideas to the entire team. He also asked if he could design the condos in Florida. I told him that He could make a presentation but we had others closer to the project.

Gary was a good sounding board. He wasn’t negative at all but was a voice of reason asking about prices and the dreaded question, “Why?” to give value to the ideas. He made people fight for what they wanted and have valid reasons for things.

Amy and Mark flew back to Florida. Frederick started to work on a lot of designs and Gary went back to work running the club and building out Hemingways. Friday came around and it was like someone kicked an ant hill with over three hundred girls trying to get moved in. They all wanted out of the old small spaces of the dorm and into the new spacious apartments. I tried to stay out of the way but the elevator stopping at the roof level to let girls on and off was a never ending thing.

That afternoon, I was going down to look at how Hemingways was coming along. I stepped out of my door and six girls waiting for the elevator looked at me wide eyed. At six foot three inches tall, blonde hair, blue eyes and in good shape I get my fair share of stares but walking out of a room in a women’s dorm had them surprised. One asked, “What’s in there?”

“That’s where I live.”

“I thought the school rented the entire building?”

“If you include this level there are eleven floors. The school has two through ten. I have eleven and the first floor is retail. The basement has your laundry rooms and the rest is to be determined.”

“So you live here and you have the entire place to yourself. Do you need a study partner?”

Now she was flirting and two could play at that game. “I don’t know if you’re in any of my classes. What would we study?”

“We should get together and review each other’s stuff, you know...”

“Maybe, stop by sometime and we can see what subjects pop up.”

Another load of girls got off the elevator and I rode down to the ground floor while others got off along the way. When I got off in the lobby, there was a person sitting behind the always empty desk. Cathy was in the lobby as well and introduced me to the doorman or door person. There was security in the building and I was given a card to show that I belonged. I was introduced to the female security guard Lilliane, she wouldn’t always be on duty but it had been explained that I lived in the building. I put the card in my wallet and said, “Goodbye,” before heading down to the corner and the restaurant.

When I walked in, I was surprised at how fast things were coming together. We were two weeks away from the grand opening. There was still plenty to be done but the bones of the structure were in place and you could see what it was going to look like. The appliances were in the kitchen with fryers, salamanders for broiling, a gas grill for grilling and both a flat top and burners to finish out the cooking stations. There were drawers and cabinets underneath that were all refrigerated to keep the ingredients cold until they were ready to be used. There was another area not too far from the cook line for prepping food. There was also an area at the end of the cook line for cold foods such as salads to be assembled.

The place looked clean but not spotless. Again, I could see what it was going to look like. The dishwashing area was set up with sprayers and a place for racks of dishes to be pushed through. A single wash could handle two racks of dishes. There were no plates, glasses, flatware or pans anywhere but it still looked good. A walk in fridge and then a walk in freezer for food storage as well as a pantry for not refrigerated items. There was a break room and an office that was large enough for a few desks.

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