Son of a Sailor - Cover

Son of a Sailor

Copyright© 2023 by SmokinDriver

Chapter 6

Coming of Age Sex Story: Chapter 6 - 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 made the walk a few blocks over to the parade route and found a place in the front row. I had a couple blankets to sit on. It seemed like hours before the parade started and another hour for the high school band to make it to where we sat. We cheered for Kari and Barb pointed out Tina to me so I could cheer for her. When they heard their names, they looked and smiled but kept dancing with the rest of the group. I saw Kari say something and a couple other girls looked over and smiled. They were around the corner and out of sight five minutes later. We went back to the apartment to drop off the blankets, use the restroom to get rid of some coffee and to get another cup.

We went to meet them at the end of the parade route and they had their luggage stored under the bus. They got in and found their sweat suits and put those on before running over to give us hugs and introduce Tina. They had their luggage and we all went back to my place. The moms had a 6pm flight home and would be heading to the airport about 3pm. It was already noon so we went to the club for lunch and wished each other a Happy Thanksgiving.

The girls were antsy and excited to be away from the band, the chaperones, the moms and be free in the city. There were some hugs goodbye and the moms telling the girls to be good and make good decisions. I almost laughed out loud when Brenda told Tina, “Don’t do anything I wouldn’t do.”

The moms were soon in the cab and on their way to the airport. Kari was jumping up and down. She was hugging me and little screams of excitement. She said, “What do you want to do first?”

“I made some plans for you girls if you don’t mind hanging out with an old guy like me.”

“I’m going to pretend that you aren’t my cousin and just the date of both Tina and me the rest of the time we’re here. What do you have planned?”

“We just had a late lunch so I was thinking about going to a show tonight. I have a friend that has offered to take you to the best Black Friday sales in New York if you want to fight the crowds in the morning. After that you’ll just have to wait, see and be surprised.”

“You got us tickets to a show? You’re the best cousin.”

Tina laughed and said, “You are the best date,” before walking over and giving me a kiss.

Kari said, “I meant date too.”

Kari then got a little serious. “Do you think we could do some drinking while we’re here away from the parents? I’ve never been drunk before.”

“Kari, you know I love you but I want you to listen to me. You can drink, get drunk, smoke or get stoned. You’re your own person to make your own decisions. I’ll tell you that most people that get drunk and especially their first time end up puking, and passing out next to the toilet. They wake up with a headache and can’t eat or drink anything for a day or two. Is that how you want to remember your trip?”

“That doesn’t sound as fun or exciting as I had pictured it.”

“Drunk people are not fun but they do some crazy shit and may be fun to watch for a while. I tend to have a drink or two to get a nice buzz going then slow down and try to maintain that the rest of the night. I don’t get sick, don’t get headaches and can still function and have fun all night.”

Tina asked, “I hear that you are not too much older than us but out on your own. What do you do to have fun in the city?”

“I do different things. I work more than anything else. I have some girls I date and some I play with. I’m not looking for a girlfriend or wife so I’m pretty laid back. I’m not old enough to get into most clubs so I frequent a few private clubs or go over to a friend’s place.”

“What are we going to see tonight?”

Just get dressed and be ready to leave by 7:00. There will be a line of cabs trying to drop people off and then getting in and finding our seats for the 8pm show. I hope you enjoy it.”

When we pulled up in front of Radio City Music Hall both girls screamed. They were dancers that all would die to be on that stage. I had fun watching them move while the girls danced on stage. Afterwards they hooked arms and did a few high kicks as they left the theater. They were in a good mood. It was almost 11 by the time we found a cab and made it back to my apartment. We’d all been up early for the parade. They were soon in panties and t-shirts brushing their teeth and they gave me hugs and thanked me for the tickets. Both spent time pressing their breasts into my chest.

There was a banging on the door at 5am and I was in my boxers when I opened the door to Cathy. She asked, “Where are they?”

“Who?”

“The girls I’m taking shopping.”

“It’s only 5am.”

“I know, I’m running late. She opened the door and both girls were in the queen sized bed. Tina’s top was not covering her boobies but she looked peaceful as she slept. Cathy smiled and held the door for a minute and then closed it and I heard her yell, “Time to get up if you want to go shopping. You can take a nap this afternoon.”

Soon both girls scooted into the bathroom and closed the door as they took care of their morning business, showered and dressed. Cathy came over and gave me a kiss. “Next year you’re going to have a whole building full of girls that look like that. I’m only 26 and wish my body defied gravity like those two. I wish I had time for a quick fuck but you can owe me one.”

It wasn’t five minutes later that the two girls shot out of the bathroom and were ready to go. After I closed the door behind them, I went back to bed but had to rub one off before I could sleep. They were back about 2pm with bags of stuff and big smiles on their faces. “Cathy knew all the best places to find the deals and knockoffs to save tons of money. I’m exhausted. I think Tina and I are going to take a nap.”

I got two hugs and then the door closed and they were out. I read a book and relaxed while they slept. They woke up four hours later and we went to a real New York City pizza place to get a slice or two. They liked the authentic feel and both decided that shopping was exercise so they could eat whatever they wanted.

We were back at the apartment around 8 and Tina asked, “I thought we were doing some other surprise thing today.”

“Did you bring any nice clothes for going out?”

Kari said, “We both bought some dresses today. Cathy almost always wears dresses and she said that she could tell the difference in the way people treat her.”

“Go and get dressed. The nicer you look, the nicer a place I’ll take you tonight.”

There was a squeal as they went and took over my bathroom again.

It was just before 10pm when we got in the cab up to 110th Street in Harlem. Tina said, “At home my curfew is 10:30 and here we’re just getting ready to go out.”

The cab ride took a little time and the girls looked out the window at the city all lit up at night. We got out and I led them down a side stairwell. When we were at the door I said, “Don’t order anything to drink or you can get the owner in trouble. I like the owner so just enjoy the night.”

They both nodded as we walked in. Cathy was there with her big smile and gave both girls hugs after looking them up and down with approval. She came into my arms and I held her and thanked her for helping the girls shopping and finding them such pretty dresses for tonight. I saw Tina look at me with wide eyes as she watched me hand Cathy $60 for the cover charge.

We sat on a couch near the stage and Cathy brough us all drinks in tall glasses. The girls each had a coke with some rum snuck in and mine was a Jack and Ginger. I tasted mine and nodded my thanks to Cathy. I looked over at the owner and she just smiled. She knew she would get a big tip from me at the end of the night but that was usually the case. The girls weren’t big fans of Jazz but they were huge fans about being in a speakeasy in Harlem at 3am with a couple drinks in them and slightly buzzed.

The goodbyes were shared as I settled our bill and Cathy told the girls to have fun while they were in the city and they were always welcome back. The ride home was a nice chat about the people, the club and the music. We were back at my place at a quarter to four and we were all beat. I was down to my boxers and brushing my teeth when both girls came in wearing panties and a t-shirt to brush their teeth. I got more hugs and rubs and looks at my boxers.

Tina said, “Bull, Kari snores. Do you mind if I sleep in your room tonight?”

My first look was to Kari. I saw her nod her head that it was okay with her. I said, “I didn’t think someone as pretty as you could make such noises.” That made her smile as she kissed my cheek and trotted off to the other room. Tina was nervous as she climbed into bed and I laid down beside her. She rolled onto her side towards me and said, “Thank you so much for everything. This has been the best trip I’ve ever taken. I saw the price on the tickets and then you paid for both of us last night and dinner and Thanksgiving. I don’t have a lot of money but I don’t want to put you out just because we showed up.”

Leaning into her I kissed her forehead. “You don’t have to worry about me, little one. I do well enough to afford a few dinners, drinks and shows.”

“I’m not sure if I’m ready to have sex but I’m dying to have you hold me all night. You can touch me anywhere but I’m not ready for sex yet. Is that okay?”

“Anything you want, Little One.”

She took off her top and dropped it on the floor by the bed and scooted back into me so I was spooning her. She took my hand and put it on her breast. I kissed her neck a few times as she purred and then rubbed her nipples until I fell asleep. It was afternoon the next day when we woke up and Tina had my cock out of the hole in my boxers and was stroking it. I saw Kari in the doorway and they were looking back and forth at each other. Kari looked over and saw that I was awake and smiled good morning.

“Do you want me to fix some breakfast or lunch or do you just want to let the girl play with her new toy?”

“I’m here for you girls. We can do what makes you happy.”

“I would love to watch Tina try to get your cock in that tiny little snatch of hers.”

“How do you know it’s tiny?”

Kari blushed, “Don’t you worry about that.”

Tina stood up on the bed and took off her panties so she was naked. She straddled me as I rolled onto my back and she lowered her pussy to the head of my cock. Her pussy parted like the red sea to allow the tip to enter her and then she pressed down to get the whole head inside of her. She took a couple breaths and sank down another inch or so before dropping to her knees and leaning forward. I took both of her breasts in my hands and gently rubbed them. I said, “Cathy said your breasts were beautiful. She wishes hers looked as good.”

Tina just moaned and pushed down further onto my cock. Kari was still in the doorway with her hand in her panties rubbing her slit. She pulled her top off and played with her nipples with her other hand. Tina would take a break to give her body a chance to adjust then do two or three strokes up and down as the head of my cock pressed into her cervix. When she paused the next time, I leaned up and kissed her and she pressed her nipples into my chest. “You are not my first but you are the biggest and the best.”

After that she started a slow rhythm and sped up just a bit as she tilted her hips. She was soon cumming on my cock and calling out her orgasm. Kari watched as my pussy soaked cock slid out of that tight little pussy. Her hand frantically moving in her panties and her getting her own cum. I signaled her to come closer and she climbed into the bed on the bed on the opposite side as Tina and I held them both as we cuddled for a half hour. They both got up and took a shower together as I waited for them to finish. When I emerged from the shower, they were in Jeans and t-shirts.

There was a silence and then Tina said, “That was so much better than getting drunk.”

We all laughed and Kari said seriously, “You know those two drinks got me a little buzzed and I felt good. I maybe could have done one more but falling down and slurring your words like that one girl didn’t look like fun at all.”

Tina agreed and came over to sit on my lap and give me a hug. “Thank you. That was amazing. I was like Kari and didn’t think it would fit but I had to give it a try and I’m glad I did. I think I’ll be leading the push to get the band and dance team back here next year.”

“I’ll be 18 next year so I will have to be careful about who I’m in bed with. I could get in trouble.”

Her eyes got big. “I never thought of that. I won’t tell anyone if you don’t. We may have to pull Kari into bed with us so she will keep our secret. But right now, all I can think about is food.”

We were just getting around to eating breakfast at 4pm. “I think we need to hurry up. The show tonight starts at 6:30. I don’t want to be late.”

“What are we going to see tonight?”

“Just make sure you wear your panties in case you do those high kicks in public again. I think you gave one grandpa a heart attack.”

“Do we have time to eat?”

“Get dressed and we’ll go to the club then the show.”

They both wore different dresses and we went over to the club for dinner before the show. I ordered a bottle of wine and we had a glass or two with dinner. They both looked very pretty and their smiles shone. When we pulled up in front of the theater. The marquee said, “Alice in Wonderland.” Both girls squealed again. If they weren’t so happy when they made the noise, I might have told them to stop.

The show started earlier because of the number of kids that attended and so all the shows on Broadway didn’t start at the same time. The girls who wanted to be all big and grown up at the club last night and in bed this morning were now little girls in their own wonderland. We stopped for a snack on the way home but we were all tired. They were flying out the next day after lunch. Kari told me that it was her turn to sleep in my bed but I just held her. She kissed me a few times and put my hand on her naked breasts. She was facing away from me and she said, “Tina said that you just holding her and rubbing her breasts made her feel like much more of a woman than having sex with the boys in our class. It was like she didn’t have to spread her legs to feel wanted or desired. She felt in control but pleasing as a person as well. Bull, thanks for everything but thank you for being trustworthy as a couple little girls try to figure out what being a woman is all about.”

Kari was naked and laying on top of me when I woke up. My hard cock was being used to rub her slit and clit as she slid back and forth along the shaft with it pinned to my stomach. She saw my eyes open and said, “I’m almost there. Please let me finish.” I reached up and played with her nipples.

“You’re beautiful Kari. A gorgeous young woman. I don’t know how the guys walk around school without tripping over their dicks.”

She came as I said that but then laughed and pounded my chest jokingly. She rolled off and pulled on her panties. “Because their cocks are nowhere near as long as yours so tripping over them is never a concern.”

She was laying with her head on my chest when there was a light knock and a panty clad Tina walked in. “Hey you two. Are you going to put on a show for me?”

Kari replied, “No but if you want us to watch you get off we can cheer you on.”

“My monthlies just started. It’s good timing since we head home in a few hours.”

“I’m sorry,” was Kari’s reply.

“I’m not. It should have started a couple of days ago but the stress of the parade and all. I know I’m not pregnant so that is all good.”

Kari called her a slut as she threw a pillow at her. I made us all waffles and we ate in just our underwear. The girls liked to be topless around me. They liked the looks they got and felt safe at the same time. I said, “I’m moving out of this place soon and into my own condo. I’ll be sharing the building with 360 girls.”

“You’ll be 18 next month so stay away from the girls.”

“I meant college aged girls. I bought my place and then Columbia University found out they needed to renovate a dorm so they needed a place for all the girls being put out.”

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