Son of a Sailor - Cover

Son of a Sailor

Copyright© 2023 by SmokinDriver

Chapter 8

Coming of Age Sex Story: Chapter 8 - 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  

We finished eating and we went into the bedroom. I tied her wrists to the headboard. I was just about to claim her third and last hole when the phone rang. I answered and it was Jenn. “Hey where are you guys? Gina said that Casey wanted to be your fucktoy and you took off.”

“We’re at my place. We just finished breakfast or lunch.”

“What are you doing?”

“She’s tied to the bed and I was just about to fuck her. Do you want to come over?”

“Hell yes. I don’t know if you are telling the truth but after what we did last night, I think we need to talk and I would love to see what you’re really doing.”

After giving her my address I went back to the bedroom and said, “Jen is jealous and wants to come down and watch you get fucked. I hope you’re okay with that?”

“Green, Sir ... Big Green.”

“Do you just like the idea of being watched or is Jen part of the fantasy?”

“Both I think. Jen is gorgeous and so much nicer than Gina. You heard how she can act.”

“I don’t want to have to stop fucking you to answer the door so you’ll have to wait. I don’t know if she is in a cab right now, saving money by walking, had to shower and get dressed first or is stopping for lunch along the way. It shouldn’t be more than a couple hours for you to wait.”

“I wish my hands weren’t tied so I could do something while we wait.”

Her petite frame and small breasts made her look younger than she was. Her bush was trimmed close but not shaven. I almost gave in and climbed on but there was a knock at the door and I went to let Jen in. I was in my boxers and the door to my bedroom was closed. Jen closed the door behind her and gave me a hug.

She asked me point blank, “Are we done?”

“Your name is still on the list but like I told you on the couch, I’m not looking for a wife or girlfriend to settle down with. I thought I was clear. I didn’t mean to lead you on or hurt you.”

“I was just asking. I’m busy with work and have a second job. I’m not looking to make any commitments either. I just didn’t want to be pushed out by anyone.”

“I was giving Gina some lip back and asked her if she was just jealous of your screaming orgasms and maybe she wanted to be my fucktoy. She said that she wasn’t interested but Casey was very interested and was ready to walk out barefoot to follow me home.”

“Where is she now?”

I just pointed to the door and she walked over and opened it to see Casey tied to the bed completely naked. “I slept in for a couple hours and my slut roommate steals my man?”

“He doesn’t belong to you and I don’t own anything. He is just using me and doing a very good job of it.”

I walked past Jen and dropped my boxers as I climbed between her legs and slotted my cock. A couple thrusts later I was all the way in and fucking her with a steady pace. Jen was in a chair, watching and had her hand in her panties. Casey was saying, “Oh yes, yes, One last load and you will own all of me. All three holes, my ass, my mouth and now my cunt. Please, Sir. May I cum?”

It was a few seconds before I could answer but gave her permission. I think she wanted to show Jen that she could match her in loudness as she screamed out her orgasm. I was ready a few minutes later and when I told her, “I’m going to fill your cunt with my seed,” She asked for and got permission to cum at the same time as me.

I looked over to Jen and she was smiling. “That was hot and I can’t believe she let you fuck her ass. I don’t think I could do that.”

Casey smiled at her and said, “That is why you’re a slut but I’m a little fucktoy. I love it when Bull uses me. You just like to use his cock. You’re probably daydreaming about him fucking your well used cunt, while I’m wishing that I was untied so I could clean his cock with my tongue. When he does fuck you, I’ll want to clean him and lick all his cum from your pussy. I enjoy the orgasms but those are just gifts from my Sir, or icing on the cake.”

“I hope you aren’t expecting me to lick your pussy clean?”

“Only if he wants you to. I’m fine either way.”

Jen blushed at the answer and looked at me. “Is that a look of curiosity or hope? Casey has already admitted to me that she wouldn’t kick you out of her bed but I think she prefers my equipment to yours.”

“Would you want me to eat her pussy and clean up your mess?”

“Jen, I think that if I would have brought it up in the middle of our session last night, you wouldn’t have blinked an eye at the suggestion. But now, you just walked in to find your roommate stole me while you slept. I’m not sure if you’re happy that she took care of me, mad that I wasn’t holding you when you woke up or somewhere in between.”

“I thought Gina was joking but then she swore she was telling the truth. Then I thought you two were just playing a joke on Gina and just went to lunch or something. When I saw that everyone was telling the truth, I was mad, jealous and turned on when I watched you. I don’t even know your last name or what you do for a living. I don’t see any roommates so you either make money, come from money or they’re away for the weekend. With such little intimacy, we’re just fuck buddies I guess and I can’t get mad if you find another to play with. I guess I’m okay with it. I have kind of been seeing a guy on and off so I don’t have much ground to stand on. Last night was the best sex I’ve ever had and whoever says that size doesn’t matter is being kind to the disadvantaged.”

“Everyone calls me Bull but my given name is Bjorn Fadden. I come from the land of the vikings and I buy, sell and rent things. Mostly real estate.”

“Where did you meet Cathy?”

“The school needed a place to house students for the next few years and I own a building nearby.”

Casey said, “I’m happy to stay tied up but at some point, I’m going to have to pee.”

As I untied her I said, “I’m ready for a nap but can postpone it if you want me for something.”

Casey scooted off to the restroom and Jen came to me and we laid down together with me on my back and her head on my shoulder. Casey came back and put her head on my other shoulder as I held them both and drifted off. I was beat and when I woke up and looked at the clock, it was just after 7pm. I was alone but could hear voices in the other room. I walked out in just my boxers and the two girls sat on the couch on each side of Sin. “Who let you in?”

Jen said, “She knocked and I didn’t want to wake you. We’ve just been talking about you and why you didn’t call her last night. It wasn’t much of a secret the way we were dressed when we answered the door.”

My shoulders shrugged. “What’s the verdict? Is everyone okay or do I need to lock my door and hide?”

“Let me in the room first, if you decide to lock yourself in,” said Casey.

Sin said, “We all know who you are and with my side of the story added in, I think we’re all comfortable.”

I asked, “Do you think it would be a good idea to take Casey to the 3rd basement at the club tonight to see how she does?”

It took her a second to think sex club and not yacht club but when she did, a wicked smile crossed her face. “We can ask her.”

“I don’t ask her, I tell her. I’m asking you. I’m sure Jen the voyeur wouldn’t mind watching. I should probably sign up now that I’m old enough. I still don’t have a driver’s license but plan to get one soon.”

Casey laughed, “You don’t have a driver’s license? Were you born and raised in the city?”

“No on a boat. But a car is not needed in either case. I want one and may use my place in Florida to establish residence for tax purposes.”

“It’s cold out and getting colder. Maybe we should all go check out your place in Florida.” Jen said.

“I share a tiny house with my parents. All of my other places are rented out or should be rented out. I have a new place or two here in the city. We should go take a look if you want to stop by on the way home.”

Sin said, “I’d like to see it in case you move without calling me, I’ll know where to track you down. If I don’t, these girls will take up all your time and all your cock.”

“Let’s drive up now and see the view at night. Then I’ll take everyone to dinner and then we can decide on the club.” I winked at Sin and she winked back.

The place was a construction zone with paint, flooring and trim carpentry tools and supplies spread around the place. They all wanted to go out on the roof when we arrived but I led them into my new place. They all loved the high ceilings and the view along with my own patio. Jen said, “When it’s time for the school to pay rent, I can just walk it over.” She rubbed her hand over my bulge.

“You can walk over the receipt and mail the check to the CPA. If you dropped off the check, I would leave it on the counter for two weeks until he called to ask about it and then I would take a couple days to drop it off.”

“It may take a while to review the receipt.”

Casey said, “You just want to see the view while he bends you over the couch, you slut.”

Sin said, “If you don’t, I’ll drop it off for you. I like the view from here and like to be bent over the couch.”

We walked out onto my private patio but didn’t stay. I didn’t want to mess up any of the work that was in progress. We walked out on the roof that would be open to the girls. Sin said, “If my college had a place like this, I would be out here sunning, studying and drinking every day and night if it wasn’t raining.”

“I had planned on some fake grass and plants along with chairs, tables and maybe a permanent structure to keep people dry. Maybe a gas grill and a sink.”

Casey said, “A hot tub would be nice.”

“Now that is a great idea. I may have to put some cameras up here for security purposes since most of the things you all keep mentioning can be done in little tiny bikinis or naked.”

“What a guy. Can’t miss any of the action.” Jen said, “What is going in on the ground floor?”

“I don’t know. I have a realtor working on it. I hope a restaurant bar or some kind of place to hang out. A coffee shop would do well. Maybe a small neighborhood grocery if the kids don’t all go on the school meal plan.”

They all threw out some other crazy suggestions like saunas, a beauty parlor and such but I didn’t really want to think about renting space or spending more money. Sin said, “I think Casey has earned a trip to the 3rd basement but being this far north in the city, there are other places that are closer but not as nice.”

“Have you been to them all and rated them?”

“Marina versus yacht club. Just a different level of clientele. Maybe a younger crowd with less disposable income. Not worse, just different.”

We ended up in a cab that took us north a few blocks to a brownstone on the corner. We went into the entryway then had to knock and wait. A guy answered and looked at the three pretty girls and me. He asked, “Is anyone a member?”

Sin said, “No we’re members downtown. We just wanted a day pass.”

“Which one? We have some reciprocating agreements in place.”

“Sherry’s fun house on 28th”

“I hear that’s a nice place. We don’t have anything in place with them. Fifty for the guy and twenty for the ladies.”

Reaching for my wallet, I said, “A hundred for the group?”

“Sure. Next time you talk to Sherry see if she is interested in talking about it.”

“We will. There’s no basement here. Everything is upstairs. The first floor is vanilla and then it goes up from there.”

When we stepped inside to a sitting area and bar Cassie asked, “What did all that mean?”

Smiling at her, I said, “It means that you will visit the top floor before we go home tonight. You don’t have to do anything you don’t want to do. Just say, ‘No.’ You don’t even have to get undressed. If you do want to do something, take Sin or me with you so that you don’t say or do something that puts you in a bad spot. I would like to start with a drink. Is that alright?”

We each had a drink then went up the stairs where the changing and shower rooms were. We all stripped to our underwear but Jen left her bra on. Sin said, “You never know when things are going to heat up. I can afford to lose a pair of panties and normally carry an extra pair if I know that I’m coming to a club but my bras are expensive so I leave them in the locker. I’m not telling you what to do but just letting you know my thought process.”

Jen nodded but left the bra on. Casey rubbed her small chest and said, “I almost never wear one anyways.”

We walked around and watched some and then went upstairs to the roleplay or themed rooms. There was a group that was up on the top floor. One guy had some ropes and was tying up a girl. He was talking like he’d done it many times before and was an expert. The patterns were symmetrical but nothing fancy.

Casey asked, “What are they doing?” To me. I just shrugged and looked at Sin.

She said, “It’s rope play. It can be used for binding someone or suspending someone.”

Casey said, “That would be cool. Can you suspend me and fuck your hanging little fucktoy, Sir?”

The guy was taking a while and I didn’t see the benefit of all the crisscrossing. I’ve made plenty of harnesses for hoisting myself up a mast to fix a stuck line. I picked up a line or what the landlubbers call a rope and wrapped it around her waist between her legs and then pulled it tight and I could hoist her up. I stopped long enough to make some hoops for her arms and shoulders and now I could suspend her and let her fly around the room like Peter Pan. We hadn’t taken off her panties so I grabbed them and yanked as the fabric shredded into my hands. There was a pulley above and I used a ladder to thread the line through and pulled it taught.

Casey’s feet came off the ground and I cinched off the line. I pushed her away from me like she was on a swing and she came back to me. I pushed her again and dropped my boxers. By now, most of the people in the small group were watching me do the ropes and a few gasped at the sight of my cock.

As she came back to me she spread her legs and soon she was swinging on my cock and calling out her pleasure. Sin was smiling and Jen was wishing her bra wasn’t in the way as she tried to play with her nipples. I had both hands free and was pushing and pulling the small girl, up and down the length of my cock. Casey had her arms crossed around the rope and was pinching and pulling her own nipples.

Ten minutes later, she said, “Please Sir, May I cum?” I gave her permission as she came hard. I went to the rope where it was tied off and as she hung in her bindings, I lowered her until she found a place on her knees. She took my cock in her mouth to clean me and I started to fuck her face. I was close so when tears started to form, I didn’t worry too much. When I pulled out of her mouth, she looked like a goldfish with her lips looking like a big “O,” trying to get my cock back. I didn’t say a word but sprayed my cum on her face and tits as she had another orgasm.

She stayed in her place with a huge smile on her face. I was trying to catch my breath when Jen knelt in front of her and started to kiss and make out with her. LIcking her face and taking the cum back to her lips. I thought it was hot so I didn’t try to stop her. When she dipped her head to Casey’s nipples I was hard again. They ended with a long hug and French kiss.

Jen got up and I undid the ropes that had bound Casey. One of the women in the group came over as the man was still tying up the same girl. She said, “Will you do me next?” I felt like the guy that threw the kid high in the air at the pool and a line of kids wanted to be next. I took the rope and did the same harness in about thirty seconds and soon had the line up and through the pulley. I looked around for the guy that was going to play with her but she wanted that from me as well. I was hard and she was an average looking lady in her early thirties with brown hair, brown eyes and a pleasant C cup looking breast. Her ass was nowhere as tight as Casey, Jen or Sin but I was just there to have fun. As I pushed her to check the hold on the rope and give her the feeling of flying I said, “I can’t guarantee that Jen will come and lick you clean. Do you have someone else here that will want to do that for you?”

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