Charlene

This is part 6 of the Charlene series. It will make more sense if you read the prior chapters first. Thanks to those who have read, commented, and rated! There are explicit descriptions of sex acts in this chapter, all by fictional, adult characters.

There were moments when I considered concluding my adventure. At one point, I went so far as drafting most of a letter to Judith explaining my decision to resign from the secret section of her website. There were myriad reasons to do this, of course, and the more perplexing decision, especially in hindsight, is how I had rationalized continuing. With respect to the infidelity and its implications, there was a surprisingly effective process of psychological compartmentalization: in essence, it was just fantasy, and just as I had kept my imagined sexual fantasies private throughout my life, the physical realization of them was also walled off as a private part of my experience that did not impinge upon or carry implications for my relationship with Michael. As long as I was careful and he didn't know, it would not hurt him, and the short episodes with others would remain safely quarantined in the same space as all fantasies.

The more proximate trigger for possible resignation, perhaps surprisingly, was a concern that the hedonic value of the events would decline over time due to habituation. The crossing over from idea to realization in the first episode was the most intense feeling yet, one that took experience from the grey, inchoate hues of imagination to the vivid colors of multi-sensory experience, and that sent an absolute jolt of excitement through me. How many such jolts were humans allocated during our short lives? But since cresting that first event horizon, I found that I was gradually building tolerance to the mere act of sex itself and required increasing doses of the metaphorical drug to obtain similar highs. And hence, the excitement that followed from a series of firsts: first anal sex, first sex with a much younger man, first threesome, first performed cunnilingus, first facial, first rimming, first overnight. And now, keeping me going in spite of my better judgment, the yacht trip and its collection of other likely firsts. The thought of being the center of desire for three men at the same time--and the attendant challenge of sexually satisfying them--was pulling me toward what I started to frame as one last adventure.

It was a beautiful Friday morning when I began my drive south to Santa Barbara, reminiscent of the weather for my first appointment with Paul exactly four weeks ago. Once out of the city traffic, I always enjoyed the drive south, taking the 101 the entire way. I was listening to music, sipping coffee from the cup holder, and whatever misgivings I had had about continuing earlier in the week gave way now to a sense of surprisingly calm anticipation for the weekend events. In prior drives when I had to give various high stakes presentations for work, there was always some anxiety about performing well, but now I felt entirely confident in my ability to perform sexually and so could just look forward to enjoying the attention of the three men. My cycle was highly regular and I knew that I was very close to 14 days from my last period (beginning on the night of the threesome with Judith) and so should soon be ovulating, which was generally when I was most horny. Looking down at my bare legs sticking out of my shorts as I drove, I pictured them spread open and felt myself start to lubricate.

I had arranged an early check in at a hotel near the harbor and began preparations soon after my arrival at 1 PM. I trimmed my bikini area a little given my attire, then proceeded through my routine of enema, rinse, and then butt plugs. I rubbed my clitoris periodically during my stretching, picturing group sex on the boat, though in my fantasy the men were all fucking me raw. I had chosen a yellow bikini that I thought contrasted nicely with my dark hair and Asian skin tone, the bottom shaped in a way that supported my ass and made it look tight and firm. I used a high SPF skin cream with a nice bouquet in lieu of traditional sun block, and rubbed it all over my skin. A thin, white sundress completed my outfit, the yellow bikini mostly visible beneath it.

I brought a smaller overnight bag with supplies and then parked at the harbour parking lot. I walked past tourists, boaters, families walking along the water and felt that I fit in well enough. Someone held the gate to the boats open for me as they entered and I soon found the slip just before 3 PM, which was our appointed meeting time.

Kip scrambled quickly up some stairs from below deck and saw me standing next to the back of the boat (the stern, as I was soon to be reminded). He looked 50 or maybe a little younger, thin and fit, about 5 ft. 10, tanned skin, with a generally friendly face, wearing a blue T-shirt, cargo shorts, and a black baseball hat with sunglasses perched atop the brim.

"Charlene, hello, welcome aboard," taking my bag and then holding out his hand to help me step in.

As I stepped in, a younger, shorter man walked toward me from the starboard side (boat lingo all the way down). He was trim but with well-defined muscles in a tight-fitting shirt, and had thin, light brown hair and especially masculine facial features that made him look a bit menacing. He had a look that was entirely dissimilar to that of any man that I had ever dated or even been friends with, reminding me of an aggressive captain of a college wrestling team or perhaps a character actor playing an inmate in a movie. An image of him riding me hard in doggystyle popped into my mind, triggering some genuine nervousness.

"This is Johnny," as Kip set my bag on the steps. Johnny had a firm, strong grip to his handshake, which only reinforced all of my first impressions of him.

Kip took me below to start a quick tour of the boat. There was a pretty nice sitting area with a curved sofa, a galley kitchen on the front right side of the room, and two sleeping berths with wooden doors tucked under the deck of the stern at the rear of the room. A stairway at the front center of the room led to an upper sun deck and the helm with its steering wheel, and a stairway from there led back down to the main deck surrounding the boat.

As we stood on the upper deck looking over the harbor, Kip said that Tom should be along shortly and then we would head out after a quick safety briefing.

"Tom lost his wife a couple of years ago and he had a rough go of it for awhile there, and so I really wanted him to have a nice trip this weekend. I wouldn't bring it up to him, but just to let you know."

"Sure, I understand."

When we went back below, Tom was already there. He was taller than the other two men, probably a little over 6 feet, and older and more heavy-set, somewhere in his 60s I would say, with reddish hair, and speckled reddish skin, a large head, and a protruding abdomen. Like Kip, though, he looked friendly. I strode over and offered my hand with a warm hello.

"Charlene, this is Tom."

Kip stood in front of the sofa on which the rest of us sat for his boat orientation and safety briefing. There were the stern, port, starboard definitions, locations of flotation devices, and a longer segment on procedures in the event of 'man overboard.' The briefing had a friendly tone but was so devoid of any sexual undercurrents that it felt implausible that I had actually been hired to provide sexual services for them. For a moment, it seemed instead that I was just going for a run-of-the-mill boat ride.

Kip did betray a subtly sly smile when, upon finishing, he asked me whether I would like to go over any rules for the group.

I decided to ham this up a little. I stood up, Kip taking my place on the sofa, and said that I would shift into my work attire and so pulled the sun dress off and stood in front of them in only my yellow bikini. This triggered some smiles but also some hungry looks as they scanned over my body, the partial stripping having immediately injected a sexual tone to the gathering.

"Thanks for inviting me, Kip. Sailors make me excited since I have always liked seamen." (Tom laughed at this; Johnny just seemed to take me in with a predatory stare, and I found myself directing my gaze away from him.)

"OK, so, my main safety rules are the use of condoms in the stern portholes (pointing to my groin area), and lube in this one (pointing to my rear)." This triggered a laugh from all of them; maybe I had missed my calling. "No tongue when kissing. Other than that, not many rules or limits. Um, let's see, speaking of semen, feel free to... (gesturing to my face and then pointing to my open mouth). Seriously, I really do like sex and want to show all of you a good time, so you shouldn't hesitate to ask for whatever you like. I'm also open to group activities if you are comfortable with that; it has always been a fantasy of mine."

Kip standing, "Thanks, Charlene. If you guys can prep for launch, I have a little business to address with Charlene."

Kip had me log on to an app for the bank account that Judith set up to show me the latest wire transfer. We had received $5,000 in advance of the trip, I now saw a pending transfer for $10,000 that Kip had just sent, and the final $5,000 would be sent after I completed the job. All good. Given the amounts, I had earlier started doing some research for possible donations to charities.

I put the sun dress back on for the motoring out of the harbour and stood at the rail of the bow with Tom as we passed the wharf, then some buoys with sea lions on them, and finally began to move out into more open water. The water was blue and glistening in the sun, and the ship started to bob up and down more as we encountered a more serious swell. I had rolled the dice by passing on Dramamine given that I had not gotten seasick on prior boat trips and did not want to be drowsy for the sexual activities.

Tom and I went back down below to get some drinks as we continued chatting about his work and a few prior boat trips that he had taken with Kip. He made some gin and tonics as Kip steered the boat in the helm above us. Tom seemed like a gentle man and I was very much enjoying our conversation. I had stripped back down to the bikini, though Tom warned that the middle of the channel often got windy and overcast due to the marine layer, so he went to get me a windbreaker jacket for when I went back up top.

Johnny came below from one of the upper decks and quickly put his arms around me from behind as Tom was retrieving the jacket for me. I felt like I was building a rapport with Tom and wanted to continue that process, but realized that I didn't necessarily have much choice in the matter given the general free-use agreement for the weekend. I wasn't very comfortable with Johnny touching me--it triggered some unwanted-contact type of reaction from the civilian world--but I did my job and just said, "Hey, you."

"Let's see what we've got here," as Johnny unhooked my bikini top, dropped it to the floor, and started to squeeze my tits hard. His strong grip had his fingers pressing firmly into my breasts with some occasional flicking of my nipples with the tips of his fingers. He kissed my neck and the whole operation had me arching forward a little, my head turned to present my neck.

Tom walked back in with the jacket while I was in that pose, and we made eye contact. He gingerly leaned forward to put the jacket on a table near me, nodding at it silently, then almost seemed to tiptoe away as though to give us our privacy. I felt like we had been on a date when returning from the restroom he found a stranger crushing my naked tits from behind, but then simply left the scene.

Johnny moved us over to the sofa and then knelt in front of me, quickly removing the bikini bottom. He pried my legs open and began licking my pussy. I had a general aversion to him touching me, though he really wasn't doing anything different from what any other client might have also done.

Kip came down the stairs as Johnny continued to eat me out. "Getting started, I see."

"She tastes great."

Kip grabbed a few things and returned topside. I figured that Johnny would pull his cock out and fuck me on the sofa, but he left it in his pants. After a few more minutes of licking, he said it was just foreplay and that he planned to fuck me on the sun deck after we reached the other side of the channel. Good to know, I thought.

Johnny grabbed a beer and went back to the deck using the stairs up to the stern. I put the windbreaker on--otherwise remaining naked--and walked up the stairs that led to the helm. It had in fact become blustery and foggy with minimal visibility, the boat pitching a bit more in the choppy water. The previously glistening water in the perfect sunshine had taken on a much less cheerful tone, choppy and darker and colder, and I found that it matched a concomitant darkening of my mood.

"This will clear up once we make it through this part of the channel," Kip steering the boat, monitoring some instruments. "All reports are clear and sunny near the islands."

Kip looked down and saw my bare ass peeking out beneath the jacket. "You really have a beautiful body, Charlene."

"Oh, thank you, Kip." I gave him a kiss on the cheek. It may have been the contrast with Johnny, but I was looking forward to having sex with him.

Tom was standing at the railing of the bow looking out over the choppy water. I went below and put on jeans, old sneakers, and a Stanford sweatshirt, with the jacket over it.

"Thanks for the jacket," patting him on the arm.

"Oh, sure. You got to know Johnny a little."

"I was disappointed that he interrupted us; I was enjoying our chat."

We each hung on to the railing, the boat at times bouncing up over a wave and then crashing back down with a splash, the pitching and lurching starting to assume a regular rhythm as I would see the approaching waves and then anticipate the vestibular feeling of the rise and fall and small pitches left and right, the motion taking on an almost sensual quality.

Tom looked pensive as he looked out over the water, then became a little poetic.

"Life has times when the water gets really rough and you just have to hang on to the railing for a while."

OK, a little too overt with the metaphor; a poet he wasn't, but I accepted the feeling as genuine and leaned against him, my head on his right shoulder. I was aware of the image that this must have presented to Kip who I assumed was looking down at us from the helm as he steered the ship. I hadn't considered the psychological effect of a job with multiple clients and multiple spaces in which at any moment activities with one man might be seen or overheard by the others.

Tom and I went back below to finish our drinks from earlier. While sitting on the sofa next to him, I took his hand in mine (his covered in some combination of freckles and age spots or maybe just freckles that looked like age spots) and leaned against him. Then I moved my face up and kissed him, rubbing lips but with Tom respecting the no-tongue rule.

"That's nice, thanks, Charlene."

"Mmm, my pleasure."

I started rubbing his crotch through his pants while continuing to softly kiss him.

"That feels really good. I can feel the Cialis kicking in."

"May I?" pointing to his pants. I liked that Tom had been respectful by not spontaneously groping me when he felt an urge the way Johnny had, and I wanted to reward him for it by being the one who initiated sex. I also just generally wanted to make him feel good.

He had a thick, uncircumcised penis that was partially erect as I pulled it out. It was my first encounter with an intact foreskin. I started rubbing him with my right hand, the foreskin moving up and down smoothly, Tom pitching his head back and moaning softly from my touch. He was hardening up nicely and was about average in length, which would make him pretty manageable for my mouth.

I pulled off my sweatshirt, revealing my bare tits, then slid down onto my knees in front of him. I pulled the foreskin down and then began sucking mostly the head, before starting to push my head down further, taking most of his length into my mouth. He started moaning pretty intently and I responded to this with little humming sounds as I slurped and sucked on him.

Tom suggested that we move into one of the sleeping rooms for some privacy, and I was happy to have an arrangement that avoided Johnny walking in on us. I grabbed some condoms on the way in. It was a pretty tight space and we had to crouch down a little when taking off the rest of our clothes. I laid on my back on the mattress and Tom rolled on a condom and then started to press into my open vagina. I felt him fill me but his round and protruding stomach pressed against my lower torso and completely blocked my view of our genitals. The combination of the low ceiling and Tom's girth produced a slightly claustrophobic feeling, but I tried to focus on both the sensation in my vagina and Tom's pleasure, making eye contact with him and caressing his body softly with my hands.

Tom started pumping faster, breathing hard, and I began emitting a series of voluntary moans as I continued to make close eye contact.

"Ohh, that feels really good," though my statement was a bit of an exaggeration. I wanted to do something more kinky and memorable for him than just missionary sex and so purred, "You can cum in my mouth if you don't want to finish in the condom."

That statement may have had an overstimulating effect on him as he seemed to catch at his breath, pumped faster, then grimaced and appeared to be straining, before letting out a contented 'Ahhh' as he ejaculated into the condom.

"Got a little excited there; it's been awhile."

"All good, I really liked it," caressing him with my hands as I still lay supine and pinned under his body weight.

Tom went to the head (more ship lingo) to clean up a bit. I put my bikini back on and sipped some water on the sofa. I could see that the sun had come back out and I assumed that we had made it through the overcast portion of the channel. The sex with Tom had been short and mostly gentle, which was good for my endurance but left me feeling like I should do more exciting things for him. I scrolled through my phone while resting up for the next round of sex, seeing that Judith had texted to confirm the wire transfer.

Walking up to the main deck, I found Kip and Johnny sipping beers on chairs at the front of the boat, the weather now warm and bright and the contours of Santa Cruz island coming into view straight ahead of us.

"Oh, wow, that is beautiful," placing my hand on Kip's shoulder, Johnny looking at my body from the other chair. There was still some breeze and a swell, the boat occasionally bouncing over the oncoming waves.

"Should be a nice day from now on," Kip placing his hand on mine. "I know a small harbor where we can anchor and spend the night."

Johnny put down his beer and moved toward me. "Now that the sun is out, I thought we could go up to the top deck and have some fun." He put his hand into my bikini bottom and started to paw at my ass.

"Sure, let's have some fun."

Johnny asked if that was OK with Kip, and Kip said that he had to monitor this part of the channel for tanker ships and that we should go ahead and enjoy ourselves.

As we walked up the stairs, I was a little nervous about Johnny's aggressiveness, but that itself was producing some sexual tension that was increasing my arousal. I knew that I had agreed to do whatever he wanted and the submissiveness inherent in that produced both trepidation and excitement.

Once at the top deck, I immediately stripped off my bikini. The view from higher up was gorgeous in the sunlight, blue sky above us, the glistening ocean stretching out endlessly in multiple directions, and the sun feeling warm all over my naked body. Johnny quickly threw off his clothes, also, revealing his muscular body and a smallish but already very hard cock that had a pronounced upward curvature to it. He laid a towel in front of himself.