Chapter 16: Troy

We prowled around more of Key West on Sunday morning after breakfast on the boat, but the town was about as dead as could be. At breakfast, Troy had suggested a noon departure. We left Key West harbor at twelve-thirty and started heading back north.

At least on Sunday, Charlotte dressed really sexy at my request. She wore that little short tennis skirt and no panties, and again dug out her crop top. She did not have a droop problem with her breasts, so the bra-less look went over well. She loved walking around the city and feeling so naughty. I kept feeling some of her hidden skin much to her delight and occasional embarrassment when I had a hand on her tight bare ass.

Back on the ship, Charlotte served lunch for all of us about one o’clock as we motored north. I chuckled and reminded her that we got in bed twelve hours earlier. Of course, we spent about an hour making love. At least she laughed and I got an eye roll.

I’d cued in Sarah about Charlotte’s curiosity about her previous career in pornography. I suggested she fill her in on the ancillary jobs that went with it. Thus, after lunch, Sarah volunteered to help Charlotte clean up the galley and prepare for our shipboard dinner. The rest of us prowled around the yacht, read, and napped out on the foredeck in the nude as we cruised along at about twenty knots.

I went and talked to Troy about the cruise, yacht, and then we shifted to his possibly moving to Sarasota. I also sized up the man and his personality. Physically, he stood about six feet, was kind of stocky, clean shaven with sun bleached brown hair. He was perhaps a dozen years older than me.

After some small talk, I said, “I hope you weren’t upset that Charlotte spent time with us. I think she’s a real sweetheart and fits in well with us. I hope she starts to hang with us. You, too, for that matter.”

Troy glanced at me and smiled, “It made her happy, and that makes me happy. Plus, she told me that she did want to start to be with all of you more often – you especially, Doug. She’s got an immense crush on you. I haven’t seen her like that with anybody else, I might add.”

I stated, “She told me that you two were an event. My mother and I are sometimes, too, so don’t be upset that I know. We don’t mention those kinds of things outside the group.”

“Thank you. You probably know how I feel – guilty-as-all-fuck sometimes. I’m over twice her age, so I want her to be with others and have great experiences. I’ve always urged her to go out and have her own social life – and sex life. She’ll need to partner with someone else eventually to have a more normal life.”

“I invite you to hang out and participate with our group, too. I assume that you know what went on the past two nights.”

Troy chuckled and glanced at the yacht’s immense instrument panel, “I couldn’t resist; I peeked. The boat has a security system.” He pointed to one of the blank displays on the instrument panel as we cruised along through the light chop. He touched a few buttons, and suddenly on the screen displayed the sedate scene of what was going on in the boat’s living room just then.

Troy touched a few more, and suddenly the screen split and filled with the video of all of us the night before, fucking and swapping around, from two different angles. He commented, “I can zoom, too. The system saves everything to the cloud by way of our satellite link. I think it stays up there for about sixty days before it’s overwritten. Jon had it put in as a security move but it also works for peeping toms like me. There are hidden cameras all over the boat both inside and out.”

“Why didn’t you join us? You know you would have been welcomed. My future sister-in-law Lindsay loves older men.”

“I don’t feel it’s the thing to do while I’m captain of the vessel. I also didn’t want to cramp Charlotte’s style. I thought she might feel some need to coddle me in some way, even if I was with somebody else.”

“Were you jealous?” I posed.

“Honestly, yes, a little. I was more aroused than anything. The two of you are really something. You made her very happy with the great sex and cunnilingus. You sure like giving oral sex to your partner. My God, you made her pass out from pleasure. I know it’s strange coming from her father, but thank you.” He blushed.

“All that taken into account then, why don’t you join us once we’re on land. We’ll all be going to Sarah’s and my condominium. Bring some gear and stay over.”

“And you’ll repeat last night or the night before?” Troy asked. He actually sounded hopeful.

“Possibly. That decision usually rests with the women, but given what I know, I’d say that a repeat of our small orgy would be highly likely, especially while Lindsay is around. Please come. We have plenty of guest rooms, and there’s no requirement that you have to be in the group setting to enjoy the pleasures of the evening with somebody else. You and your partner can be as public or private as you want.”

“You don’t mind somebody as old as I am?” he worried suddenly.

“Heck, no. You’re not much older than Jon. I’m the youngest man in the group, and Jim, my father, is the oldest. He’s got at least ten years on you. My mother is his age. Age is not an issue with us. Dot, my mom, would really get off being with you with your rugged good looks and supportive personality.”

“I’ve got to close up the boat and refuel, and do the logs once we’re moored.”

I chuckled, “No excuses. Some of that can wait until tomorrow, I’m sure.” I grabbed a pen and piece of paper and made sure Troy had directions to our condo and phone numbers. He was already conversant with Uber and Lyft.

Talking Charlotte into coming home with us took no effort at all. She really wanted to continue to be with us – with me. I also thought that she might want to try making love in some setting other than on the boat, especially in her narrow berth. I promised her a king-size bed with satin sheets and she swooned.

After mooring and clearing the boat, all the landlubbers congregated at Sarah’s. Thirty minutes later Troy called and said he had just left the marina in an Uber. I’d expected him, so went downstairs to meet him, opening the outer door to the building just as he got out of the hire car. We shook hands and I took him up into the building, showing him the routine to get in from outside.

As we got on the elevator, I politely warned him, “When I came down to get you, there was some nudity and couples playing together. I just thought you should know. You met Lindsay on our voyage. She kind of has her eye on you, and she’s a lot of fun. I encourage you to just jump right in with both feet.”

Troy laughed nervously, “No foreplay?”

I chuckled, ‘That’s between you and Lindsay. Just ask. She’ll tell you her preferences. From experience, she can go either way.”

Troy said nervously, “Charlotte told me that two of the women are porn stars. Who is that?”

I grinned, “Sarah and ... Lindsay. Let me assure you that you are NOT competing with the men that you see with them in their videos. The two of them are sisters and got into the business independently of each other. Their opinion of the men they worked with is pretty low. If you’re expecting a high bar set by one of them, it won’t be from their work in the adult entertainment industry.”

Troy just nodded firmly to indicate that he’d taken in that fact. I could see that he was nervous but intrigued.

As we came into Sarah’s living room, Greg and Dot were already naked and coupled together in a cowgirl on one part of the sofa. Next to them Jon was getting a blowjob from Rachel. They both looked over and waved in welcome to Troy. Charlotte was naked next to them and she’d obviously been making out with Jon and probably feeding one of her young breasts to his mouth. She did not look embarrassed being seen naked by her father. She even gave us a little wave.

Sarah and my father were in the kitchen – naked. She was atop one of the tall bar stools that put her pussy at just the right height for him to bury his cock in her. She had one leg resting on the counter and the other on his shoulder. They ignored our peeking into the room.

Sandy came over to me along with Lindsay. They were both deliciously naked, and Troy started to salivate. I reminded Troy of the names, and he smiled warmly but nervously at the two of them.

Lindsay said to Troy, “I’ve got two glasses of white wine out on the patio balcony overlooking the city and one has your name on it. Why don’t we go and get acquainted ... and let me get you to relax a little after all the work you did to bring us home. Just ignore all of this stuff going on ... for the time being.” I put my arm around Sandy as Lindsay gently took Troy’s hand and led him across the room to the large walk-out door to the balcony. I noted that she left the door open, so that our sounds of passion would filter out onto the outdoor deck.

Sandy asked after they were gone, “Will he be okay? He looked kind of numb.”

I chuckled, “He is numb. He also knows that he’s with a porn star. Lindsay will talk him off the ledge. Don’t worry.”

“I like him. I was tempted to swap with her, but I figured he’d want to start with her. She told me about her ‘thing’ for older men.”

“Not sure about that, but we’ll see the outcome a little later. You do know there’s a sofa out on the balcony. There are really no lights except for the indirect light that shines up from the street, and we’re high enough that no one can see, so they could get right into it out there, even fuck with her holding onto the railing. Sarah and I like to be out there when we fuck sometimes. It feels like you’re being an exhibitionist to the entire city, except you know that after dark no one can see you.”

Sandy said, “Charlotte wants to join us. Should I get her?”

We looked over and Charlotte and Rachel had changed placed. Rachel was standing on the sofa and squatting slightly so she could lower her pussy to Jon’s upturned mouth. Charlotte knelt in front of him and was doing her rendition of a world-class blow job.

I said to Sandy, “Leave them be. She’ll find her way over when she’s ready.”

I spread out one of Sarah’s yoga maps and a towel on the cushy rug in the room, and then went down on Sandy. She tasted wonderful, as usual. We played for a while and then coupled together. I got four orgasms from the younger woman, and then she begged for a respite.

About that time, Charlotte, slid onto the floor beside us and delivered kisses to both of us. She tasted like Rachel. She then withdrew slightly and looked at each of us to see whether she had overstepped some line by interrupting. I smiled and pulled her in for another kiss, and that one became serious and lasted. When we were through, Sandy did the same, and I could see that the two of them got into it. I felt that Charlotte was starting to appreciate her sapphic side as well as how to respond to the arousal we all felt.

Our foreplay after those tentative deep kisses with Charlotte seemed limited to about two minutes worth of romance and smoothing, and then she was impaled on my shaft as I lay back and she rode me ‘girl-on-top’. Sandy had directed the coupling; I think mainly because she wanted to get her mouth on the two of us simultaneously.

Sometime later, after we’d all had some orgasms and were cuddling, we heard a moan from the open doors to the patio. Since it was a male tone, I assumed that Lindsay had finally gotten Troy to relax and enjoy his orgasm.

A few minutes after that, I saw Rachel head outside through the open doors. Lindsay came inside a few minutes later with a smile. She spotted the three of us and came right over. She lay down beside us. She teased, “I think you may want to do a clean-up job on my hot little fuck box. I seem to be full of your father’s baby batter. Interested?” There’d been no indication that Charlotte did that type of thing, what Sarah called being a ‘cum slut’. I worried that we were grossing her out.

Charlotte nodded somewhat enthusiastically, and Lindsay spread her legs and then pulled her pussy lips apart. Charlotte seemed to figure out what to do without further instruction. Fuck. My brain turned to mush again.

I awoke on Monday morning with Charlotte and Sarah cuddled up to me in bed. I woke the two of them. I knew that Sarah wanted to be at work early, and wasn’t sure about Charlotte. Turns out she also wanted to clean-up from our sex the night before and connect with Jon to walk from our condo over to the building their offices were in. She’d brought the clothes she’d needed for her office from the boat the night before. The three of us showered together in our large enclosure. Great fun to start a new week, yet we all made it to work on time.

While at work, I got a text from Sarah; ‘Have to go to Virginia (near D.C.) next week for five days. Back-to-back tax and new IRS rules seminars that impact Jaycor.’ I chuckled and wondered how that would go for her, especially if she got recognized as Candy Sweet by some of the other seminar attendees. I’d tease her later.

While at work, I made up a little booklet of ten ticket-like coupons, each labeled ‘HALL PASS’ in large letters. The other words on it stated, “This ticket entitles the bearer to one extraordinary sexual session with the men or women of your choosing. There is no limit on location, frequency of sexual couplings, or other related items, other than they occur within a twenty-four (24) hour period.” I scribbled my signature on each coupon.

The hall-pass coupon booklet held ten tickets printed on cover stock and looked very official. I’d give them to Sarah so that she could REALLY enjoy her trip to Virginia. I figured that I’d get more information from her that evening at home. I tucked my present into the portfolio that I carried my iPad in when I went home, and went back to work.

Sarah and I arrived home at the same time. We took the elevator up together talking about dinner plans and recalling how hot the weekend had been for us and how great the trip to Key West had been. She did verify that Lindsay had flown back to Miami, but didn’t know about any of the others or their plans for the evening.

We hadn’t had some alone time for almost a week, so we took advantage of the time and were happily ‘together’. We went out for drinks and dinner, had some rich conversation, including the discussion of one of my mother’s primary statements we should talk about prior to marriage: ‘What childhood experiences influence your behaviors and attitudes that you have today? Is that good or bad?’

I talked about my having been a scout and the training to ‘be prepared’ and ‘be helpful, and the other scout traits that were emphasized.’ My dad had even been the troop leader for a couple of years. I’d learned to be helpful. I guess the other thing was my interest in all things electronic and technical, as well as aviation. My mother had been the one that inculcated in me the attitude of inclusion and broad-minded thinking, along with critical thinking. I’d been taught to challenge the status quo and think of ‘a hundred’ other ways to address whatever that was. She’d also tried to make me a social creature, teaching me to dance and how go on a date.

I also told Sarah, “Now, I find that I’m fucking my father’s wife and he loves to watch, and I have new and better relationships with both of them, plus he’s been fucking my fiancée.” We shared a laugh.

Sarah went right to growing up without a father figure, and the deteriorating relationship with her mother. She thought that the lack of a father made her want to please men more to earn their favor, and that had partly led to her career in pornography and doing escort work. The lack of closeness to her mother had left her and her sister on their own to develop their feminine sides while growing up fast.

Sarah said, “Since we were pretty poor, my mother was constantly concerned about money and how we had to save it for a rainy day. I guess that influenced my need to accumulate wealth and be sure I could make it for a long while if my income streams dried up.”

“So, did you come up with a figure that you had to exceed to be a success?” I asked.

“Yes. I did a lot of planning and research, so the number was pretty specific – just under four million dollars. My research was mostly looking at other people and finding out what they made to have a very nice lifestyle. On the interest and earnings on that amount of money, I could live in a comfortable lifestyle and never really have to work. I hit that number with my savings and investments, and then quit the sex industry to try something new. I’m still surprised that I did it.”

I was shocked. I knew that Sarah had a nest egg, but I had no idea it was that large. I struggled to contain my surprise.

“What about your relationships?” I asked as my mind raced.

“Well, I evaluated the various men and women that I’d worked with, and almost all of them came up short as lifetime partners. I had a normative idea of what a boyfriend or husband should be like, starting with being my best friend – and seeing that I wanted the same with that person for the rest of time. They also had to have a sense of humor and not take themselves too seriously. Part of leaving L.A. and Vegas and the sex stuff, was also to see whether I could find a new circle of friends, including at least one man that I wanted to spend the rest of my life with. That’s you, babe.” She smiled.