Chapter 15: Charlotte and Key West

I secretly and silently cheered. We’d all just voted, unanimously, to participate in the swinger parties that Ross and many of the others we’d met at his yard party did. My porn-star sweetheart from next-door, Sarah, actually seemed enthused about going to the next adult party in about three weeks.

The group started talking. I saw Charlotte start to collect most of the dessert dishes, and head for the galley. I also collected the remaining four plus some cutlery, and followed her. I set them on the quartz countertop in the galley next to the others and started to put some of the leftovers away. She looked surprised, “Thank you. That was very nice of you, but you don’t have to lift a finger on this trip. My job is to make sure you are pampered and try to wait on you hand and foot.”

I smiled, “And given what you said earlier, it is my job to do my part in pampering YOU, and making YOU have the most orgasmic experiences that can be had as a welcome to our little group.” I held my arms open to her, and she took the three steps into them and then hugged me.

I kissed Charlotte, and she kissed me with her arms around my neck in a romantic maneuver. She slowly allowed her body to press against mine, and I held her that much tighter, even allowed her to feel the swelling urges that I had between my legs. She gave a delightful little hum into about our twentieth kiss and ground her hips into mine in a very sex-inspired gesture.

Charlotte said, “Jon has been open with me about your group of lovers. I know that I’m not that old, but I’ve had some boyfriends and ... I think an unusual affinity for things romantic and sexual. I have no one in my life right now; except for a tiny piece of Jon, I guess. I find that I’m emotionally needy about what you’ve got going on with each other, and that you can openly share every part of you without guilt, embarrassment, or recriminations as you all make love with each other – even together. I heard there was some incest, but I don’t care. I have my own bit of that same situation.”

I made a leap of assumption, “Troy? I noted that you have the same last name, plus he’s old enough to be your father.” I pointed in the general direction of the flying bridge where Troy had gone after his quick supper, supposedly to install a new weather radio.

“Yes, my father. We’ve been occasional lovers for a while. I’ve always had a daddy complex, and he had no willpower when I decided to seduce him. My mom died when I was very young, so I was always a surrogate wife in many ways. I just expanded my duties – only they weren’t onerous. I love him more than any other man, but I know that I need some ‘real’ boyfriends, too.”

I shrugged, “Fine with me. That older woman that you met at dinner, Dot; she’s my mother. We’ve only just started to redefine our relationship with a sexual component.”

Charlotte said, “And Greg and Sandy are brother and sister.” She laughed, “I guess I’ll feel right at home then.”

“What about Troy?”

She shook her head. “He knows what’s going to take place, even tonight. He knows that I want to be part of it, and he’s supportive but ... well, he’s not participating tonight. I think he needs to play captain to all of us, especially when we’re underway. He’ll keep us on track from the helm through the night until we’re anchored in Key West harbor – probably around two a.m. He’ll then catch some sleep and join us for breakfast unless there’s some nudity or sex going on then. He can be shy, and he’s got some funny notion that he has to avoid that with all of you when he’s in charge – as he is on this trip. To my knowledge, he’s never been in a group sex situation.”

“Tonight, do you want to be with Jon, then, or go off with Troy?”

Charlotte kissed me again, “I hadn’t made up my mind about which of you gentlemen I wanted to be with until you brought the dirty dishes in and kissed me. I want you. The way you act and talk turns me on.” She broke into a smile that lightened the load of the world, although part of it was embarassment.

I said, “Given that your arms are holding me close to your sweet body, I’d say that you have me already. That also makes me glad.” Our kisses got pretty hot after that.

I reminded Charlotte that the galley was still a mess with the leftovers and detritus from dinner. I patted her on the rear and said, “Come on. Many hands make light work.” I pitched in and helped with the dishes and clean-up. This was the first boat I’d ever been on that had a dishwasher and an extra-large refrigerator. Clean up and put away took twenty minutes, and that included some preparations for serving breakfast.

I was amazed at how smooth the ride on Jon’s toy was. Smaller boats rocked and rolled with the waves and swells, especially cruising along at twenty knots, but not his sixty-five-footer, at least in this sea state. We soared along through the waves, and except for the drone of the engine, it was hard to believe we were moving on a great circle path right towards Key West.

I led Charlotte back towards the living-dining area on the main deck. I went ahead of her, and held her hand. Predictably, there was a lot of sex going on as we tiptoed upon the scene. I heard the sharp intake of Charlotte’s breath as she took in what was going on. Her eyes opened to the size of saucers. She’d heard about our group sex love-ins, but to see it in reality was almost another thing to her. Every person was sexually involved with one or two other people, and everyone was already naked.

Jon had Dot slowly riding his hardness in the cowgirl position on the cushy sofa. Atop his mouth Sandy was slowly twerking her gash across his active tongue, working herself towards an orgasm. Her eyes were closed as she soaked up the pleasure, but Dot was also fondling her breasts and gently pinching her nipples as she rose and fell on his shaft.

Abeam of them, Jim was fucking Lindsay in the missionary position on the other facing sofa. They were kissing a lot, too. Next to them, Greg had just sunk his cock deep into Rachel’s wet twat in the spoon position as they reclined on the plus carpeting. Sarah was next to them leaning against the sofa, masturbating as she watched.

More than just the impact of what was going on, the sounds of the ongoing sex also filled the room: moans, panting, squishy sounds, the slap of body against body, and more than a few words of dirty talk inspiring more sexual interaction.

I whispered to Charlotte, “Shall we join them or do you want something more private? Don’t be afraid to ask for what you want. We all try to be very accommodating of each other. Also, just to be sure you know, you never have to do something you don’t want to do. It’s not an emergency that we do anything together. We can go somewhere and just talk.”

She replied in a hushed tone with her eyes locked on Rachel being fucked, “No ... here is good, but I’ll probably blush for a week. I’ve never had sex in the presence of another person. This is already making me so wet and horny, I can’t wait to be part of all this.”

I helped Charlotte divest herself of her clothing right where we stood at the top of the hatchway up from the galley. We watched the others, and I took my time and kissed all over each section of newly expose skin. We did stop so that our lips could meet often, however. Somehow, my own clothes seemed to fall away at about the same rate as Charlotte’s. She was all eyes watching one couple or threesome and then another.

The most comfortable space near the others appeared to be on the other end of the plush oriental carpet from Greg, Rachel, and Sarah. As we adopted that acreage, I extended more of my kisses to Charlotte’s breasts, and then to the entire landscape between her legs. As my tongue made the first swipe from her taint past her clitoris, Charlotte’s whole body spasmed. While the reaction was orgasm like, I think it was more surprise than not. I found her looking down her body at me with a very adoring expression.

“Oooooh, Doug. More.”

I really got into the cunnilingus with my newest lover. She was exceptionally tasty plus I had been getting more ‘dining in’ experiences and a growing know-how for how to really bring pleasure to a woman. A lot of that expertise had been developed based on instructions from the porn star that lived next door to me. Whatever I was doing seemed to Charlotte’s liking. I did ask her for suggestiosn, but she just shsook her head indicating that I was doing fine. Her first serious orgasm came five minutes later. I thought for a minute that I’d killed her. I think she might have lost consciousness. If she didn’t, the fog of the sex had overtaken her.

I didn’t let her physical state deter me from giving her more pleasure. When I felt her stir and moan slightly, I hugged and kissed her a lot, and then went back to work with mouth and fingers in her nether region. I’d located her G-spot and took advantage of that tidbit of knowledge as I ramped her up again over another five minutes to another orgasm, with similar results. I repeated all that again over the next ten minutes.

Charlotte finally pleaded with me, “Please ... as much as I am loving this ... and you ... come and fuck me or else I’ll be useless the rest of the week to you or anybody. Make love to me.”

I got her halfway there over a few minutes, and then raised myself between her widespread legs. She had a beautiful pussy, with swollen labia from my work and pretty little nooks and crannies that were wet with my efforts and her excitement.

I lay my hard cock atop her mons and slid around in the moisture there. Charlotte sat up slightly and took hold of my shaft, running her hand up and down, and then she ran the head along her sodden pinkness over and over again. The stimulation for me was awesome. I caught at the opening to her interior, and then gently pushed into her body. Our eyes were locked together, and as I reached full depth. If ever there were loving communications, those were the moments. We then had the most passionate kiss ever. Only a few minutes later, Charlotte came again. This time I rolled us to our sides and remained in her body.

Charlotte said in a nearly incoherent voice, “I didn’t think girls had orgasms from intercourse.”

I said quietly, “I guess we blew that myth out of the water. I confess to having taken graduate courses in how to make things like that happen.”

“Really?”

I didn’t respond, but I did snort with a bit of a laugh. Charlotte was gullible, but she was also deep in a sex fog by then.

Charlotte had a wide berth adjacent to one of the heads on the lower level. It wasn’t too private, but it was comfortable. After kissing the other women in my life goodnight, Charlottee and I went to her bed and made love again, and then slept together without separating. She thought my cock remaining embedded in her body was a great thing. I loved soaking in her warm and wet vagina.

I got up early when Charlotte did and we showered separately since the enclosure was small, and then we dressed. She was ‘on-duty’ in the galley and started to prepare for making breakfast.

I went topside and looked around at where we were. We were about a hundred yards from several open slips for smaller boats, but we were definitely in Key West. Already, there was a buzz of activity in the marina we were in as some of the fishermen headed out to try their luck. We were the second largest boat at the marina as far as I could tell. The other large boat made ours look dinky, too; it was probably 120-feet long.

Charlotte brought me a cup of coffee and kissed me in a very romantic way. I kissed back in kind. She ran her hand down my face and stared lovingly into my eyes. She whispered, “Thank you for last night. You have my heart.” I explained that the feeling was mutual.

The other signs of life on the boat didn’t appear until about eight a.m. Sarah appeared wearing her short robe and nothing else. We shared a morning kiss. She said, “Yummy. I just love the way you kiss me. I hope you had fun last night. I almost joined you, but the bed you were in could barely hold the two of you, yet again a third.”

“Who’d you sleep with?”

“Jim and Lindsay in the rear stateroom. King-size bed. The two of us gave him a night he’ll never forget until we all fell asleep. I don’t think he knew that he could cum so many times.” She giggled. I thought about how glad I was that my father got a great threesome with the woman that would eventually be his daughter-in-law – plus her sister.

The others, including Troy, appeared, also in robes or shorts of some kind. We ate the waffles and pancakes that Charlotte had prepared. There was barely any interaction between Troy and Charlotte, only acknowledgement and a wink that I caught between them. I figured they’d have more to say to each other later.

Jon was going to play tour guide for our group and had a list of ‘must see’ places to go, starting with the Hemmingway House. He’d been on the island only once before. For us to get around, he’d rented six mopeds. Each could take two adult passengers, so there was some doubling up on the bikes as we started playing tourist. Charlotte didn’t go with us as she had ‘duties’ onboard. Jon started us on some of the unusual architecture and history of the area.

We had lunch at the famous Hogs Breath along with a couple of hundred other tourists. Our flotilla of mopeds then descended on the huge buoy marking the southernmost point in the continental United States. We took about a thousand pictures, and got another tourist to take several of all of us. With all the mopeds, we were like a wimpy man’s motorcycle gang.

After prowling around all the busy streets, most with tacky tourist-inspired gift shops on them, we were riding around and saw a tattoo shop on Duval Street. Sarah was behind me on the moped. She pointed at the shop and said, “Okay, stud, it’s time to upgrade your image.” She already had eight small tats on her body.

The shop had an opening, but I didn’t want to spend the rest of the day or into the evening doing this. Because of my interest in flying, I got a simple tattoo of a compass tattoo on my upper left arm, along with an airplane silhouette headed north out of the compass for the top of my shoulder. After some elaborate prep and cleaning of my arm to ensure no infection, the actually tat took about ninety minutes. I’d gotten some slight coloring to it, so it wasn’t all just tattoo blue or black.

Sarah and Rachel said it made me look that much sexier. I’d always wanted one, and now that itch was satisfied, although the guy in the shop laughed and said, “Well, that’s your first tat!” The implication was that I’d be getting more in the future.

While I was in the chair getting my tattoo, Rachel lay a few feet away on a massage table getting a rose entwined with a heart tatted on her left breast. She was bare from the waist up, and the young man doing her tat looked exceptionally happy to have her bared breasts to fondle as he did his work. She encouraged him, too. I noticed her nipple was harder than steel for her entire session.

Rachel finished about the same time that I did. We got briefed on the care and feeding of our new tattoos, given some ointment to use on them for five days, and then were on our way. Sarah and Sandy announced that they were horny and wanted some sex, so we headed back to the marina and yacht.

The Zodiac from Jon’s boat was tied up with a couple of others from other yachts. Jon got the first load of passengers aboard, and drove us out to the yacht. He went back for the rest of our contingent. The marina’s tender was busy with other passengers from the larger boat.

By the time the last of our tourists reached the boat, I was balls deep in Sarah, and there were some other sexual things going on in the main living room between Rachel, Lindsay, and Jim. I was open about making love with Sarah and she obviously loved the exhibitionism.

The new arrivals quickly joined us. My mother, Dot, quickly stripped and got Greg naked, and then deep throated his cock. Had I ever known that my mother had that unique skill? He was no trivial matter, too.

Jon chuckled and then had Sandy spread eagled on what had been our dinner table. For him, that was just the right height for eating and then for standing and fucking as she got pulled to the edge.

Past the various couples and threesomes, I saw that Charlotte had come up the steps from the galley. She was wearing a very short little sexy skirt, no panties, and a crop top. She was barefoot, and she was watching the lurid scene and rubbing her pussy with one hand as the other stimulated her nipples under her top. I motioned for her to come into the room and join Sarah and me, or any of the group.

Charlotte transited the room to Sarah and me. Sarah smiled and said, “Lose the clothes.” She was naked in ten seconds, and then mounted my fiancée’s mouth and started a slow twerking motion as Sarah’s tongue, lips, and face went to work on her new horny friend. Charlotte was quickly adopting our wanton way of life. She obviously loved the cunnilingus from my fiancée.