Holiday Loving

Holiday Loving - Memoirs of a Woman of Pleasure Ch. 03

I visit a special club with Jeffrey

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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 3 of this series. It makes more sense to read chapters 1 and 2 first, but this is not essential.

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Stan and Gloria returned soon after lunch and both hugged me as I arose from sunbathing.

"Did you have a lovely dinner with Phil?" asked Gloria.

"Absolutely delightful," I replied and proceeded to tell them about the dinner, leaving out the panty episode. I also did not mention about him coming home with me, although I wondered if that had been my decision or whether I had been manipulated to make that offer.

"That's lovely," cooed Gloria, "And what time did he leave?"

"About 11am," I replied without thinking, then realizing that I had just confirmed that I'd spent the night with him here.

"Well you two must have had lots of fun together I guess."

"Yes, we sure did," I replied enthusiastically, mentally berating myself for having fallen so easily into Gloria's traps.

"Well, that's great. So will you be seeing him again do you think?"

How do I answer that, I wondered? Do I call her bluff and simply tell her I know what her game is and how much did he pay for me? No, I didn't have any real evidence; she'd just laugh at me.

"No, he said he doesn't have girlfriends but just plays the field, although he did tell me I was one of the best, but I guess he might say that to all of them."

"Oh, I'm sure he meant that. Such a pity you two won't be hooking up; he seemed like a nice guy and he's really loaded. Hopefully I might be able to find another lonely male friend and perhaps he'll want to hook up with you. Would you like to meet another man if I know of one?"

How to answer that, I wondered? I looked back over the evening, night and morning. Had I enjoyed it? Had I ever; it had been wonderful. Did I want to repeat it? Absolutely. Would it make me a whore if Gloria was pimping for me? I put that thought out of my mind.

"Yes, I enjoyed this one so I'd love to do it again," I replied.

Stan and Gloria left me to my sunbathing, going to their room to strip off no doubt and make love most probably, an assumption that was confirmed by the sounds from the room a short while later. My thoughts drifted back to my conversation with Gloria. So what if they're making money from me? I'm enjoying myself, I'm giving pleasure to somebody else as well as me, I'm made some money, where's the harm in that? Why shouldn't I do what I'm doing and why shouldn't Gloria and Stan do whatever it is to find men for me to do it with? Who's getting hurt? Nobody.

Life returned to normal and the memories of sex with Phil faded as I continued to enjoy loving experiences with Stan and Gloria. Taken overall, life was great; I was not expected to do a great deal, had plenty of free time, was taken care of and loved by two wonderful people. As Phil's memory faded, so too did my concerns and suspicions about Stan and Gloria's possible ulterior motives for allowing me to stay with them free of charge in an expensive holiday resort.

However, I did remain hypersensitive to some things. I noticed that when I went to the beach wearing my skimpy bikini, one or both of them always seemed to accompany me. I was also never alone when I was shopping or out of the resort. Was that just coincidence, I wondered? I resolved to try to find out how far they would go. However, before I could do that Gloria announced that they had decided to have a weekend away this coming weekend and also that a friend of theirs, Jeffrey, was here for a weekend so they'd offered him the use of the apartment. They concluded by saying they hoped I didn't mind but were sure that Jeff and I would get on well together.

For an instant I wondered what they would say if I told them that I was going away for the weekend also, but decided that, in view of my previous contemplation, why rock the boat? If indeed their story was true, then that was fine and if Jeff and I found we went further than simply chatting for the weekend, that was also fine. If, on the other hand, I asserted my independence, that could rock the boat enough to mean I could lose this very desirable lifestyle to which I had grown accustomed.

The Thursday before the weekend Gloria told me that Stan had a very sore back and had decided that sex was out of the question and, although he didn't want to say anything to me himself, he was concerned that I would hurt it if I slept in their bed. I agreed that I would sleep in my own bed Thursday and Friday nights in the hope this would help his back.

When I thought about this situation later, I wondered how true it actually was. Both Gloria and Stan knew that as a nympho, two days without sex would have me climbing the walls, let alone the prospect of Thursday to Sunday without sex. By preventing me from having sex with them for four days, they were making it almost certain that I would want sex with anything with two legs, meaning that Jeff would certainly strike it lucky. I had to admire their planning, if, indeed, my hypothesis was correct. After the two days alone in my own bed I was really horny, despite having masturbated several times each day.

Saturday morning arrived and Stan and Gloria departed an hour before Jeffrey arrived. I greeted him at the door and noticed he seemed to be a little overweight and flabby, and was certainly not going to attract women with his good looks. However, his Gucci case reeked of money, as did his bright yellow Lamborghini parked in the apartment carpark. As I invited him in I felt his eyes running up and down my body. This could have been in anticipation of potential pleasures or simply the natural glances I was used to receiving when I wore my bikini in public.

"So how do you know Stan and Gloria?" I asked once we were lounging on the deck in the morning sunlight with cocktails in our hands.

"Oh Gloria's my second cousin," he replied glibly, "I haven't seen her for years but wanted to visit them, so I'd booked this weekend a few months ago and was devastated when they told me they had to be away this weekend. However, I decided to come here anyway as I needed the break from my work as a stockbroker."

I assessed his story; on the surface it was plausible except for one slight slip: we hadn't been in this apartment a few months ago so he couldn't have booked a trip here then. Should I mention it or let it pass? I decided to mention it just for devilment to see how he'd reply.

"Yes, that's correct," he chuckled, "But their holiday here was planned about eight months ago and they invited me here at that time. I thought about it for a few weeks then accepted. Such a pity that they had this last minute appointment elsewhere."

I really couldn't push him harder on this and it was a plausible answer, so I decided to just let it lie. After all, he seemed good company; I wondered what he was like as a lover. I soon found out.

"I'd have thought a girl like you would have sunbathed nude in a place like this. I'll place a small wager that you're tanned under that bikini. I've got a hundred that's yours if you can show me that your body's tanned all over; hell, even better, you can have the hundred even if it's not so long as you show me."

A hundred bucks just to strip in front of him. That sounded like easy money to me.

"Ok, with one proviso; you have to strip naked also."

"Me?" he guffawed, "Now why would a cute girl like you want to see a flabby guy like me naked? However, fair's fair; you've got a deal, but only if I can strip you myself after I strip myself."

"Deal," I grinned.

Jeff stood and quickly removed his shirt, shorts and undershorts, showing much skin that had never seen the sun. However, it also showed a good-sized cock that was rapidly rising to the occasion. He approached me and wrapped his arms around me, fumbling with the clasp of my bikini top then removing it. He stood back a little, ogling my firm tanned naked breasts.

"Hmmm, I like them," he said approvingly, stepping forward again and slowly pulling the string bow of my bikini on each hip. Once they came loose I parted my legs allowing the skimpy fabric to fall to the deck, exposing my tanned pussy for his inspection. After a few seconds I spun around so he could see my tanned ass.

"You like?" I grinned at him over my shoulder.

"Very much," he replied, "May I touch please?"

"Of course, as much as you wish."

Jeff came close again and began rubbing his hands over my body, not as gently as Phil had, but certainly enough to start my body responding. He then held me in an embrace and kissed me. I could feel his cock between our bellies, pulsing with sexual readiness. A wave of horniness passed through me. I wanted him, no, needed him in me now. I wrapped my arms around his neck, pulled myself upwards, wrapped my legs around his waist and held on, my wet entrance right above his cock head.

Of course he got the idea. He placed his hands under my ass cheeks and moved me a little to position himself, then he lowered me, allowing my vagina to slowly engulf his cock, sliding all the way down until my clit pressed hard against his pubic bone. I held on tightly, feeling as though I was in heaven. I slowly moved my hips back and forth, stimulating myself on him. I could feel him pulsing deep inside me and could also feel my hard nipples pressing into his chest. It didn't take me long at all, horny as I was. In less than five minutes I was cumming, holding him tightly, moaning in his ear as I enjoyed my first orgasm with a man in two days. Part of me was amazed that it only took that short time to have me behaving like a wanton harlot and throwing myself at the nearest male around.

I came again as he spurted into me a short time later. These weren't mind-blowing orgasms like I'd experienced with Phil, but they were orgasms and they did provide temporary relief, even though each one pushed me to experience another soon afterwards. I knew I was addicted, hopelessly, helplessly and totally addicted to sex and orgasms; what was wrong with that, I asked myself? Can the need for something that is pleasurable and natural really be an addiction? I refused to answer, afraid of what I might find out about myself.

He lifted me off his now diminishing member and we kissed, then wiped ourselves dry on a towel.

"Did you enjoy that?" he asked.

"Oh yes, thank you darling, that was wonderful. You're just the best." No harm playing to his ego, I reasoned.

"Thank you; there's more where that came from."

I looked at his cock pointing to the floor, and wondered if there really was.

"How about some lunch?" I asked.

He agreed and we made lunch together, eating it naked on the deck.

"Would you like me to rub some sunscreen into your white bits?" I asked after lunch.

"Yes please, sweetheart."

I did, spending a great deal of time massaging it into his skin, paying particular attention to his cock and balls; I didn't really want the weekend to end due to a sunburnt cock. The afternoon progressed without further major sexual adventures, both of us chatting about inconsequential things as we lay in the sun, caressing each other from time to time. Towards evening he suggested we go out for dinner, saying that he knew of a great place to eat, then asked if I'd like to go to a night club that was his favorite place.

"Not many people know about this place," he told me, "It is a members and partners only club and I usually go there when I have a lovely sexy partner like you to take."

I wondered what sort of club this really was but didn't push it, figuring I'd been able to look after myself in all the situations I'd been in so could surely look after myself at this club. It turned out that I was mistaken.

Dinner was delicious; not the high class dining and dancing I'd experienced with Phil, but certainly more than passable. Jeff had insisted I wear the most sexy clothing in my wardrobe so I was without a bra, wearing a pale gray satin dress that hung around my neck, strips of fabric covering my breasts leaving their sides clearly visible and attaching to the waist of the skirt section, which was split from the hem below just below my knees up the front, rear and both sides up to my waist. Beneath this skirt I was only permitted to wear my tiny sequinned G string. Walking in this I felt almost naked and was both flattered and embarrassed by the stares I attracted in public.

After dinner we walked a short distance to a plain doorway where Jeff used a plastic swipe card to gain entry. I began to feel a little nervous, wondering what I had let myself in for, especially when we were met inside by a tall, well-built man wearing only a loin cloth. He greeted Jeff and was introduced to me as Toro. Jeff explained he was responsible for keeping any undesirable types out and joked that I was welcome as I didn't appear to be one of those.

We went into a large room where there were many people standing talking, with drinks in their hands. There were an approximately equal number of men and women, verifying Jeff's statement about partners, and Jeff went to two large glass bowls on a table in the center of the room and tossed a pink in one and a blue disk in the other. I asked what that was for and he told me that they had his membership number on them and would be used later in the evening. We were served drinks by a waitress who was naked except for a leather studded collar around her neck and a cord around her waist from which hung closely spaced and beaded cords that reached just below her crotch. They did little to cover her pussy or ass. Her only other adornments were nipple rings through each nipple and a clit hood ring that could be seen momentarily when the beaded strings parted as she walked. I looked around and noticed that there was waiter also serving drinks and also wearing a studded leather collar around his neck. He also wore a cord around his waist to which was attached a narrow leather strip that was obviously meant to cover his cock but which spent most of its time alongside it, exposing a massive, slightly hard member over a large ball sac. I wondered what he'd be like inside me.

We joined a group and chatted with several people for a while about life in general and a some political matters. It appeared that everyone in the group was well informed and quite astute; this seemed not to be a club for dummies. I wondered how I could join and decided I'd as Jeff later in the weekend.

After a while another man entered the room carrying a gong, which he struck three times with a mallet. Immediately everyone ceased talking and turned towards the door. After a few seconds a statuesque woman wearing a mask and dressed as a dominatrix, I thought based on what I had read, entered the room, ascended the two steps to a formal looking chair and sat down. She greeted everyone and then asked who was new here; who had never bee to the club before. Timidly I raised my hand, looking around to see that there were a few others who were also newbies.

"I am Mistress Angelique," said the woman, "I am very pleased to welcome newcomers and trust that you will have an enjoyable and stimulating evening. In case you don't know, this club specialized in mild BDSM. If you haven't experienced this, you're in for a treat tonight because we have first up Mistress Tracy and Erica to give a demonstration of caning. Erica has been caught having sex with one of Mistress Tracy's slaves without permission and must be punished, as, of course, must the male slave, but that is for later. In case you're wondering, everyone here is able to use a safe word if they wish to prevent what is happening to them from continuing. Use of the safeword means that you will no longer be able to attend meetings here in any capacity unless you pay a forfeit of 100 cane strokes. For those who are new, 100 cane strokes is a horrific punishment and has only been administered on two occasions to my knowledge. So I give you Mistress Tracy and Erica."

A spotlight came on and I watched as presumably Mistress Tracy, dressed as a dominatrix, led a female by a short lead from her neck collar onto a small stage to the left of Angelique's chair. Two other males, presumably slaves by their collars, brought a bolster on short legs onto the stage and Erica was bent over the bolster. Mistress Tracy fastened her wrists and ankles to rings in the floor using short Velcro straps, ensuring her ass was facing the audience. This meant that Erica's legs were splayed widely apart while her ass was raised and tightened ready to be caned.

"Are you ready, slave Erica," asked Mistress Tracy.

"Yes, Mistress," replied Erica.

"And do you confess to unauthorized sexual union with slave Richard?"

"Yes, Mistress."

"And do you agree to pay the price of such an act by receiving 25 strokes of the cane?"

"Yes, Mistress," replied Erica, choking off a sob at the end.

"Let the punishment commence," ordered Mistress Angelique.

Mistress Tracy was handed a black fiberglass cane and took up her position. She swished the cane in the air a few times, then applied the first stroke to Erica's naked ass cheeks. Erica screamed. Immediately a white line showed the path of the stroke and this line quickly turned red as the blood rushed back to try to alleviate the damage caused by the impact. After about five seconds Tracy applied the second stroke just above the first. Erica remained silent for this stroke. There continued a series of strokes, each one striking Erica's ass in a new place. Tracy seemed to know how to handle the cane and applied a series of parallel strokes until she had reached 20, as counted by the slave who had provided the cane. She then changed her position and struck across the stripes, causing the cane to strike already damaged skin, tearing it in places and causing a small amount of blood to trickle down the back of Erica's thighs. After that it was soon over and Erica was released, then paraded amongst the attendees, who were able to stroke her ass and feel the ridges and indentations left by the hard cane.

"I'd hate to be caned like that," I whispered to Jeff, "Although watching it made me very hot and sexy."

"We'll have some great sex tonight then," whispered Jeff, a grin on his face.

"Thank you, Mistress Tracy and Erica," said Angelique as Erica was escorted out the back. "Now it's time to witness the punishment of slave Richard. Please bring him on."

This time a female slave brought a man onto the stage, leading him by a short lead attached to his collar. He was naked and stood facing the crowd, his cock seeming to be partly aroused.

"So, you think you can have sex with a slave whenever you want to, do you?" asked Mistress Angelique.

"No, Mistress."

"Well, I certainly hope that you'll learn your lesson tonight. Your punishment for this offence could be permanent, even costing you your cock and or your balls. You are aware that you could be castrated or completely nullified for this offence, aren't you?"

"Yes, Mistress."

"So you can thank Mistress Tracy for her leniency this time. She has asked that you be sentenced to have your cock and balls whipped with 25 strokes of a flogger. Tie slave Richard to the bolster."

Two female slaves tied him to the bolster so that his legs were parted, his ass against the bolster and his cock, now at least semi-hard, and balls were visible to everyone. Mistress Tracy was handed a flogger and swung it in the air a few times then brought it down hard on the end of the bolster, making a satisfying thump.