Holiday Loving

Holiday Loving - Memoirs of a Woman of Pleasure Ch. 04

Love under sail

Author's notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author's knowledge, bears no relationship to any factual occurrence.

3. This chapter 4 of this series. It makes more sense to read chapters 1 to 3 first, but this is not essential.

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"What gives you that idea?" asked Gloria.

"Well, both Phil and Jeff left me what I can only assume to be a tip. While they each professed to love me, neither made any commitment to future meetings. It just seems to be strange that you happen to know people who are unattached, are spending only a short time here, think I'm sexy, want to take me to dinner or a club, and who spend much of their time with me having sex with me. Are they paying you? Am I your prostitute and you're my pimps?"

Gloria and Stan looked at one another, then back at me. "What if that was the case?" asked Gloria.

"Then that would be fine. I'd just like to know and I'd like your end of the story. I'm quite happy going with these guys and so far they've both been great fucks, and I really enjoyed dinner with Phil and I think I enjoyed the club with Jeff," I stopped and rubbed my ass which still showed where I had been caned, "But if that is the case I think you owe it to me to tell me."

"Ok, I guess it's time to come clean with you. When you and Stan met on the beach we had been having marital problems, as sometimes occurs in marriages. I had been a real bitch to Stan and I know he was feeling horny because we hadn't had sex for ages. So when you were willing to move in with him, he was very happy and wasted no time in showing you how happy he was. He let me know so I knew what to expect when I arrived. Once I saw you and saw how well you and Stan were getting on together, I realized that there was a possibility that we could mend our differences if I allowed you to stay. So I did, and we did.

"I think it was Stan's idea that maybe if we found guys you would like to spend time with he wouldn't be so drained by your high sexual demands. So we searched on the web and found many sites where women offered their services for a fee. We discussed what we could do and eventually decided to set up a website for you. We already had some photos of you but we took others and added them to the site. We had the usual group of sleazeballs wanting to fuck you or marry you or whatever, but after a while we managed to weed these out and improve the site so that only gentlemen of class would apply. The first one we chose was Phil, as you know. That worked out well for everyone, so we then selected Jeffrey. He was a slightly greater risk, we thought, so we're very pleased how he worked out for you. I guess it's time now to ask you if you're willing to continue this system or do you want out?"

I thought about what Gloria had told me; I had enjoyed my time with both Phil and Jeff, I certainly would be happy to continue with others. Then a thought came to me.

"So how much did Phil and Jeff pay you? I'd really like to know how much my body's worth to these gentlemen of class."

"Phil paid us $4000 for his time with you, plus the $500 he gave you plus all costs of the dinner. Jeffrey paid $5000 for a longer time plus the $400 he gave you plus the costs associated with being a member of the club, which we didn't know about."

"And remember, added Stan, "It's not just your body they like, it's your whole self, your personality. You seem to make people feel good about themselves. When we make love I know that's true for me."

"So you got $9000 from my work for two clients and didn't even think I should get any of that?" I asked, feeling a little angry that they pocketed all the takings and I did all the work.

"Now hang on a minute," said Stan, "That's really unfair. You live here in this holiday resort on permanent holiday free of charge. We clothed you, we feed you, we care for you as though you were one of our family. It costs $2000 per week to stay in this resort and we have additional costs when we leave you here and have to spend time in other accommodation. It's not like we're coining it. It's also not like we're insisting that you're with a guy every weekend, only one a fortnight so far. We're barely breaking even from a financial perspective."

I calmed down a bit. Stan was correct; I did enjoy living on permanent holiday and spending time with different men, experiencing different forms of loving. Did I want things to change? No, I did not. So why was I being so aggressive?

"I'm sorry. I really have enjoyed you both as well as the Phil and Jeff interludes. Thinking about it, I'd love to continue just as we are. So far you've selected great guys; I can barely wait to see what sort of person you'll select for me next."

"Well, now that it's in the open we can ask you a few questions about your preferences," said Gloria. "For example, would you be willing to be the only female with a group of guys?"

I knew instinctively what that meant; I'd be fucked almost non-stop, one after the other, maybe two or more at once. I shuddered, not in fear, I noticed, but in excited anticipation.

"Yes, is the short answer."

"Ok, we had an enquiry from a guy who wants a young nubile female to accompany himself and several of his mates on a yacht for a weekend. Does that sound like something you'd enjoy?"

My imagination ran wild. I saw myself on a yacht with several men using me as they saw fit, far away from any help if I needed it, finally imagining my sore and ravaged body being tossed over the side to feed the sharks. I shuddered again, this time to rid myself of such awful pictures. I then visualized me as the center of attention with four well-built, muscular sexy guys who treated me really kindly, made love to me carefully and extremely sexily, and with whom I enjoyed a peaceful, sexy weekend cruise. That was more like it. I reassured myself that Stan and Gloria had so far chosen well and that they would keep choosing well. After all, they relied upon my goodwill for their income. I made up my mind.

"Yes, that sounds great, just make sure you choose all the guys on the cruise well."

"Oh you can be sure of that. We even do police checks on them, but of course that only covers what the police know, it doesn't cover such things as membership of BDSM clubs, as we found out. Was that fun, by the way?"

"Fun was not a word I would use to describe being caned and I'm certain the woman who rode the wooden horse would not think that was fun. Remember, my disk was in that bowl so it could have been me. I'd say it was more challenging and certainly enlightening, and it was absolutely sexually hot. I was so horny when we arrived home, even despite my sore ass. Would I do it again? Absolutely."

"Ok, we may ask if potential clients are members of any sexually oriented club and maybe you'll be able to return sometime or visit other similar clubs."

"What are the chances of having Phil or Jeff again for a weekend?"

"Well, they'd have to request you again. We don't contact them again after their time with you, so maybe if they had a great time they'll contact us, maybe they'll play the field. There's a lot of women on offer as escorts, which is the more polite term for what you are, but rest assured that you seem to be one of the best we saw on the web. Anyway, I'll contact Neil and tell him that you've agreed to the cruise on the yacht with him and his mates. Ok with you?"

"Yes, absolutely. I'm pleased we cleared this up. It didn't feel right when I had suspicions but not really any proof of my role. Does that mean you'll discuss possible clients with me before I meet them now? So we won't have any non-existent second cousins."

"Yes, I'm sorry, maybe we should have been more open but we had no idea how you would react. Perhaps we should look at paying you, say ten percent of their payment? Plus your tips, of course. Would that help you to feel less used?"

"Yes please, that'd be great thanks."

The following Tuesday I met Neil. He was tall, over six foot, and well built. I looked him up and down, as he did me, and I imagined what size his cock must be if it was in proportion to his body. A shiver of excitement ran up my spine. He didn't stay long, just long enough for a drink and to get me wet between my legs at the thought of being in bed with him for a night.

After he left I quickly stripped off to my usual unclad self and coaxed Stan into my bed, where he proceeded to fill my vacant hole and my sexual needs. As I lay on my back with my ass at the edge of the bed and Stan pushing inside me, Gloria knelt over my head so I could lick and suck her pussy while she squeezed and twisted my nipples. I had two massive orgasms like that before I felt Stan fill me with his hot cum. I lay there imagining it was Neil 's cock and cum inside me.

The following weekend, Stan and Gloria were able to stay home in the resort as I was going sailing with the guys. This immediately cut costs, I realized, which was better for everyone concerned. Neil collected me in his shiny new BMW early Friday afternoon and we were soon at the docks where the 60 foot yacht was moored. I knew little about boats but it appeared to be all ship shape, as the term goes, on the outside and Neil escorted me down the steps into a living area, which looked very tidy and comfortable. He then led me through a narrow passage to my cabin, which he told me was the largest suite on board. It had a king size bed which felt very comfortable when I sat on it, and I tried to imagine what it would be like with five guys and me all piled onto the bed.

Over the next half hour the other four arrived and I was introduced to Bert, John, Hal and Trevor. Neil told me they were all experienced sailors and had been sailing together many times but had missed female company in the past so for this trip they'd decided to do something about that. They loaded the yacht with all the necessary food and drink then I heard the dull throb of the motor beneath my feet. Next I knew we were moving, the ropes being cast back onto the pier as we slowly moved into the channel and towards the harbor entrance.

Once through the entrance the guys busied themselves with fitting sails to the mast and front wire rope, which I was told was the forestay, then they turned into the wind, hoisted the sails and when they were happy with how the yacht was moving, they stopped the motor. It was wonderful in the relative silence to simply glide though the small waves, the mid-afternoon sun still warm and the breeze blowing gently.

"Well," said Neil, "It's probably time to start behaving as we will for the weekend. I propose that on deck we wear a bare minimum of clothing, brief shorts for the guys, bikini for Mandy. Below decks we can be naked, but there is too much other boat traffic to be naked on deck all the time. If it gets too cold, then people can wrap themselves in a coat or blanket."

"Hear, hear," agreed the others and everyone looked at me. I wasn't sure whether they wanted me to agree also or whether they wanted me to strip off first. I figured that if I stripped off I was also tacitly agreeing so began removing my top.

"No. please let me do that," offered John, stepping awkwardly towards me across the sloping deck of what they called the cockpit, aptly named with five randy guys sitting around the edge. John continued where I stopped, removing my top then kneeling down to unfasten my stretch pants and pull those down around my ankles, leaving me standing in front of five guys who I barely knew, in bra and brief panties. What a buzz! John leaned forwards and kissed my pussy through my panties, amid cheers from the others.

"Right, so I want to see you guys in just your undershorts now," I told them, "Let's see what you've got for me this weekend."

It took a very short time before they were stripped and I enjoyed looking at the guys' crotches, noticing the pronounced bulges in the front of their shorts.

"I'm going inside to get into my bikini. Anyone who wants to can come and watch and I'll watch them get into their swim shorts."

"I'll stay on deck and steer for a while, there could be some other boats around," said Neil, "You guys head below with Mandy but don't have too much fun."

I went through into my cabin, leaving the others in the lounge area or going to their smaller cabins. Once I found my bikini I returned to the lounge area and the others arrived with their shorts.

"Ok, who wants to strip me?" I asked.

They all volunteered, so I chose Bert, who seemed to be a little shyer than the others. He unclipped my bra and removed it hesitantly, then stood back to admire my breasts while I cupped them with my hands.

"Well, come on, kiss my nipples," I encouraged him.

He blushed, but stepped towards me and gave each nipple a kiss. Then I asked Trevor to remove my panties, which he did, repeating John's action of kissing my pussy as I stood in front of the four guys stark naked. I grinned at them, turned around so my back was facing them, bent to touch my toes then spread my legs, giving them a good look at my ass and my slippery love trench. I felt one of them run his finger through my trench, then I stood and turned back to face them.

"Ok, Bert, your turn. Please dress me in my bikini."

I handed him the two small pieces of material and he looked at them then at me, possibly trying to work out what went where. Men, I thought, hopeless creatures. I turned the bra up the right way and placed his hands at the shoulder straps so he just had to slip it up my arms, which he did. I reached behind and fastened the clasp, pulling it off my breasts a little so they were more exposed. The bottoms were even more of a problem for him as the two ties on my hips were unfastened. Eventually I took it from him, fitted it between my thighs and he tied the bow on each hip while I held the fabric.

"Thanks, honey," I said once he was finished, and I gave him a kiss for his efforts. "I hope you guys won't have so much trouble taking them off as Bert had putting them on," I said jokingly. "Now, I want to see what you guys have."

I watched as they stripped off their undershorts and put their swim shorts on, making sure that I gave each cock a few strokes, cupped each set of balls and finally kissed each cock head before they were at least partly covered. Their cocks had hardened in the process so each waistband had a cock head protruding out the top. I thought I knew how I could solve that problem, but later.

Neil eyed up my brief bikini as we returned to the cockpit, taking one hand off the wheel to caress my breasts and feel my crotch, which by now was quite damp. Hal took over the steering while Neil changed into his swim shorts, but once he was back on deck I pulled them down in front and massaged both his cock and his balls, noticing that both were in proportion with his body size. Once I released them and pulled the front up again he also had his cock head protruding well above the waistband.

We spent the next half hour chatting, getting to know each other a little, enjoying the slightly cooler air at sea and, towards the end, sipping on cold beers that Bert had rescued from below decks. Apparently we were heading towards an island, which Neil pointed out in the distance, and we'd moor in the lee of that for the night, he said. Tomorrow he had plans that we'd go ashore and explore the island a little, then return to the yacht and sail to another island for Saturday night. To me it all sounded like a great adventure and I simply sat and absorbed the environment; the sea whooshing past, the yacht rolling and pitching slightly, the seabirds flying overhead, occasionally squawking as if asking to be fed, and five sexy guys all sitting with me. The sexual tension was so strong it could be cut with a knife and I was interested to simply observe to see what would happen next.

What happened next was that Neil asked Trevor to replace him at the wheel, pointing out where we were heading, then he came and sat beside me, running his hand up my thigh, gently stroking me with one hand while he placed my hand on his cock.

"He really would like to pay you a visit," he said into my ear, but not so softly that the others couldn't hear, "Would you like me to show you some of the interesting things he can do in your cabin?"

I nodded and he stood and led me below to my cabin. Once inside he closed the door and we embraced. I ran my hands over his naked back, feeling his muscles, his smooth skin, his whole sexy being. I felt his cock moving against my stomach as he also caressed my back before unclasping my bra. I eased away, allowing him to remove it completely, which he did, then we pressed together again and I felt his hairy chest against my nipples. He ran his hands over my ass cheeks, firstly outside the cloth then inside it, before reaching a hand onto each hip and undoing the bows. Again I moved away slightly so the fabric could fall away in front, but I guessed if I wanted to go much further it was now my turn.

I reached down and hooked my thumbs into his waistband, then pushed downwards. His shorts moved down a little and I felt his cock head rubbing my stomach, leaving a trail of precum. I could reach no further so I disentangled myself from his arms and knelt on the floor, urgently pulling his shorts down to the floor and holding them as he stepped out. I then looked at his cock, pointing straight at my face, and I began kissing the head, licking it, tasting his precum, swirling it around then I opened my mouth and slowly took his rigid member inside. I gagged slightly as it reached the back of my throat but overcame that and swallowed it, feeling it travelling down my throat. I couldn't breathe so I quickly moved back, took several gasps of air then moved down his cock once again, this time holding my breath until my lips touched his pubic hairs. I cupped his balls and gave them a gentle squeeze, then I removed my mouth once more and stood up.

"You like that?"

"I love that," he replied, "But I think I'll love your pussy more."

He lifted me while I was still upright and moved me the few feet to the end of the bed before lying me down on my back, my ass cheeks right on the edge. He then stood back and gazed at me for a few seconds, his cock twitching, a smile on his face.

"Lift your legs up," he said. I did. "Now spread them apart; hold your knees with your hands."

I did that, spreading them widely apart, thrusting my pussy forward so he could see it easily in the dim light of the cabin.

"Beautiful," he muttered reverently, "Just beautiful."

Neil reached down and stroked my gaping pussy, feeling my trimmed hairs, running his fingers through my trench, feeling my wetness as my pussy ached to be filled with his cock, so large, so long, so close.

"Please fuck me, honey," I whispered, loud enough so he could hear, not so loud as to break the spell.

He took a step towards me and leant forwards, his hands reaching for my breasts, which he cupped, his fingers and thumbs squeezing my nipples as he bent his head forward to kiss my lips. It was a very sexy, tongue entwining kiss and as it continued I felt the head of his cock sliding slowly back and forth in my trench. Then it was at my entrance, opening me, pushing inside me, feeling his smooth skin of hid hard cock against the wet walls of my vagina, deeper, deeper, still one single thrust until finally he hit the end. He stopped, holding himself inside as he continued the kiss. I let go of my knees and wrapped my legs around him, pulling him forwards, wanting more of him, wanting him to thrust deeper inside me, to lengthen me, probe my depths completely, hurt me. When had I become such a masochist that I always wanted to be hurt when making love, I wondered, fleetingly.