Pleasure Island Ch. 01

Once we arrived at the island, we were met by the Administration Manager, Betsy, who guided us to our accommodation, where we dropped off our small backpacks, having been told that everything we needed, including clothing, would be provided. After that, Betsy took us on a comprehensive tour of the island, introducing us to many people, most of whose names I immediately forgot. I expressed my concern about this and Betsy laughed.

"Of course, you'll forget their names," replied Betsy, "That's why they have them embroidered on their clothing. At the end of our tour, we'll do the paperwork then I'll take you to get your clothing supply, which will have your names on it. Why else do you think they measured you when you applied?"

Sure enough, once we'd visited the whole complex, including the admin area where we completed some paperwork, Betsy took us to the stores section and pulled out two plastic-wrapped packages, handing one to each of us. "You can change into these now so you're official," she instructed.

We both looked for some changing rooms, which caused Betsy to chuckle. "Just here is fine. Neither of you has anything I won't have seen before. Nudity is perfectly fine anywhere on the island. Once guests have been here for a few hours they usually adopt nudity as their new uniform. You are also welcome to adopt the nudist fashion if you wish, but while you're on duty in public you are requested to wear the lanyard with your name on it included in your kit. Anyway, open them up and have a look."

We opened the plastic wrapping and found zipped bags each of which contained many items of clothing. We spread this out on two tables apparently provided for just this purpose. Most of the items were self-explanatory; shorts, light trousers, which Betsy explained were useful in avoiding insect bites in the evening, some canvas shoes and sandals and some shirts with our names on them. Other garments were more interesting, including very brief lycra shorts for us both, and a tiny bra top for Tina, as well as the lanyards with our names on plastic name plates.

"The guests like to see what they're getting," explained Betsy, "So these are multi-purpose garments that can be worn on their own or as underwear or swimwear. Try them on and see how they fit."

I looked at her, then at Tina, thought 'What the heck', and pulled off my shorts and underpants. Just the thought of how I'd look in these tiny briefs, plus the presence of Betsy watching us change, had me at least semi-hard. I turned away from her.

"Spoilsport," she chuckled, "I hope you're not always that shy."

I took that as a challenge and turned back to her, my cock even harder than before, pulsing in time with my heartbeat.

"That's better," she replied, "May I have a hold?"

I nodded, and she gently held my cock as it continued to pulse and harden. "I can see that I could have some fun with this toy," she said, "Sometime soon, I hope."

I felt my face reddening and saw Tina grinning out of the corner of my eye. Then I relaxed, accepting the new normal, moving towards Betsy before embracing her and pulling her closer to me. "So do I," I whispered into her ear, before releasing her and reaching for the shorts.

I pulled them on, feeling their tightness, noticing that my name was embroidered on the front and also that my upright cock poked above the elastic waistband. I would have to wait a while before I could reposition myself comfortably inside them. I looked at Tina and saw she was also pulling on her lycra bikini shorts. They were a G-string design, a thin strip of fabric sliding between her ass cheeks, the front triangle, with 'Tina' embroidered on it, just large enough to cover her pussy lips and the lowered front waistband sitting just above her the top of her clit. She looked incredibly sexy, even more sexy than when she was naked.

Tina looked at Betsy nervously. "Do I wear anything over this?" she asked.

"If you wish. It's not necessary and after a while you possibly won't want to, but you can now if you like. You've got the top to put on also."

I checked my clothing pile and found a pair of shorts, then pulled them on over my briefs, at last hiding my cock from Betsy's hungry eyes. I also found a shirt, with my name on it, and pulled it on, noticing that it fitted me like a second skin, clinging to my skin and showing off my not inconsiderable six-pack. I watched Tina as she removed her top and pulled on the very brief bra-like top, also named, consisting of two small triangles over her nipples and not much else.

"There are several bras to choose from," Betsy told her, "That's the briefest, but there are others including one you might like to try now."

She rummaged through the pile of clothes and pulled out an item which she held up for Tina's approval. Tina grinned, then slipped off the brief bra and pulled on the new on, helped by Betsy. It had fuller cups which had complete elasticized circles around the base of each breast, but it also had a hole at the apex of each cup. Once it was in place, Betsy then showed Tina how to coax the base of her breasts through the elastic loops so her breasts looked far larger and firmer than usual, then pulled her nipples through the holes. I found it interesting also to see how the pressure of the elastic caused her nipples to engorge, filling the holes through which her nipples were poking. The sight of her like that, G-string panties and protruding nipples, did absolutely nothing to help with my problem of fitting into my briefs.

"Who on earth designed this?" asked Tina.

"One of our guests started this by simply cutting holes in a normal bra so the nipples could peek through. We thought it a good idea and this is the result."

"Feels incredibly sexy, but maybe not now, perhaps when I'm a little more used to showing off my sexy bits."

Tina removed that bra and donned the first very brief one, apparently feeling happier with covered nipples even though the sides of her breasts were bare. She turned to Betsy for approval.

"You both look fine as you are," commented Betsy, "So repack your spare clothing into the bags and I'll escort you to your rooms. It's time for lunch as well; you must be hungry after a big morning."

Tina packed her clothes into the bag, while I did the same with mine, then followed Betsy to our room, dropped off our clothing, then accompanied her to the dining room, where we met a few other uniform-clad staff. With our names on our clothing, introductions were unnecessary and we quickly found everyone to be friendly and chatty, probably because those were traits for which staff were selected.

Looking at how the other staff were dressed, I realized that Betsy had been right in what she said, that basically anything goes. Several women wore bras like Tina's, some wore no bra, one wore bra and no panties of any type. Guys were much the same, several wearing only their swim wear shorts. The food was delicious, as we'd expected, and we ate a full meal while chatting with other staff members. I soon realized that much of the conversation was an informal assessment of other staff for possible future liaisons, which I found myself looking forward to as I had quite a prolonged conversation with a gorgeous young blonde woman whose tiny bra said her name was Sue.

"You can call me Sexy Sue, if you want," she told me when she saw me reading her name, "The sexy part isn't for everyone though," she chuckled.

She also was a student and was unattached, but hopeful, as she said with a grin. She questioned me about my relationship with Tina and appeared to be quite pleased that we allowed others into our partnership.

"So, you'd be up for a threesome?" she asked.

"Yeah, sure, so long as Tina doesn't get dragged away by some other guy. Maybe you'll latch onto another guy and we could have a different threesome, or maybe a foursome," I suggested.

"Sounds promising. I like being single; no commitments, eh. That's why I like guys who are already in an open relationship; less chance of them becoming possessive."

I noticed that Tina was also involved in deep conversation with another couple, the male half of which was sending definite signs of interest in more than just a chat. I noticed his hand rested on her thigh; this was shaping up to be a very interesting holiday job already.

Tina and I lay in bed together, discussing the day's activities as we each caressed the other. The afternoon had been spent checking out the guest rooms, meeting other staff, learning protocols and expectations, and being assigned to guests, who were due to start arriving tomorrow. Once that was completed, it was time for supper, then we came to bed. In some respects, I was slightly saddened by the lack of approaches by Betsy or Sue to spend the night with them, but maybe my imagination was running riot and teasing was more prevalent than actually living out those suggestions. At least I can relieve some of my sexual tension inside Tina, I thought as my cock hardened still more under her gentle touching. I was about to pull her over onto me when I heard a tap on the door, followed by a voice softly calling.

"Are you still awake in there?"

"Yes," I replied.

"Can we come in?" the voice asked.

I wondered who the we were that wanted to come in and looked questioningly at Tina, then saw her nod. "Yes, come in," I replied.

I awoke the following morning and glanced at the time; still early. I went over in my mind what had happened yesterday, then reviewed last evening and quickly looked to where I could hear soft breathing. I wasn't dreaming; I had spent the night with Sue. My mind went back to the soft tap on the bedroom door, then to Sue and a guy named Troy who she brought into our room. They had climbed into bed with us and for a while there was lots of cuddling, caressing and kissing until Sue had fallen off the bed and had decided that the bed was too small for four, so she grabbed my hand and led me out the door to her room across the hallway.

Once there, she made it very obvious what her intentions were for me, and within a very short time she was riding my hard cock to several orgasms, the screams of which she muffled mostly against my shoulder. After her third orgasm, I remembered her rolling off me and lying on her back, her legs held wide apart. "Fuck me, honey, hard. Cum in me. Fill my cunt with your hot jism."

Being an obedient partner, I wasted no time in following her orders, lying between her legs as my hard cock pounded her pussy. She had another orgasm quickly, then I spurted my cum deep inside her. After that, I only remember rolling off her so she could breathe more easily, then the next thing was waking up a few moments ago. I became aware of an urgent need so carefully climbed out of bed to relieve my bladder. I returned, then turned towards her and she stirred.

"'Morning, lover," I said softly, watching her eyes flutter open.

"Mmmm, so you weren't a dream," she murmured, a sleepy smile on her face, "Did we fuck?"

"Yeah, I seem to remember something like that happening."

She rolled towards me and lay partly on top of me. "Well, just in case we didn't, I guess we'd better make sure."

She wriggled on me until she straddled me as I felt my cock hardening between us.

"Of, fuck," she said, "I need to pee."

She climbed out of bed and ran the few steps to the bathroom, where I heard her seemingly endless stream in the bowl. She returned to bed, walking slowly across the room, putting on a show for me and her thighs partly covered then uncovered her pussy lips with each step. I felt my cock harden still more, then she climbed onto me, straddling me, her legs wide apart as she slowly slid her wet slit over my hard cock and began sliding gently along its length. She lowered her lips to mine and we kissed, long, lovingly, languorously, her hips continuing the stimulation until, without breaking our kiss, she positioned her now gaping entrance over the head of my cock and slowly engulfed it, sliding down on the shaft until she was seated as deeply as possible, her clit resting against my pubic bone.

I wrapped my arms around her, holding her tight as I felt the delightful feeling of her talented cunt relaxing and contracting around me. I slid my hands down onto her hip bones and began moving her back and forth, slowly at first, gradually increasing the movement until she was sliding almost off my rod, before plunging downwards, once again engulfing me completely.

"I think you like that," she murmured in my ear.

"You think right. You obviously like it too."

"Absolutely, it's my favoritest thing in the whole world, I think." She paused for a few seconds. "Well, almost," she said with a grin.

"What's your favoritest?" I asked, using her own word.

"Ooohh, maybe you'll find out sometime," she said teasingly, "If you're really good, I might let you experience it with me sometime soon. Enough, already, fuck me, make me cum, fill me up with your hot sperm."

She sat more upright and I was able to move her back and forth, stimulating us both as her clit rubbed along the underside of my cock with each thrust. It only took a few minutes before she was moaning in pleasure as I felt her enlarge internally and the head of my cock rubbed over her cervix from front to back. That movement stimulated me and seemed to stimulate her as she leant further back so I could squeeze her nipples hard, driving her to a shuddering orgasm and pushing me to mine also.

"YESSSSSSS!!" she hissed as her body tensed and shuddered and my cum filled the end of her welcoming cunt.

We both relaxed after a short time, panting as we lay together, recovering from our exertions. I reached out and checked my watch, 8.15. Breakfast was 8.30.

"Come on," I said, rousing her, "We gotta shower and head to breakfast. Can't be late on the first day."

We showered together, partly for the sensations, partly for speed, then she dressed as I ran naked across the hallway to my room, meeting Troy just opening the door, heading to his room to dress. We greeted each other briefly, knowing that we'd probably have time to share later and aware of the need to hurry. I kissed Tina good morning briefly, pulled on shirt and shorts, then Tina and I headed to the dining room, hearing Sue and Troy leaving their room a few seconds later.

Breakfast was a buffet of cereals as well as cooked meals. We greeted a few people, grateful for everyone being named, then Tina found a table for two and we shared what happened during the night, which were similar to those I'd experienced with Sue. At 9am, Betsy stood up and began addressing us, hoping we'd all slept well and were becoming acquainted with other guest service staff, welcoming us all to Pleasure Island, explaining the routine for the first day, which was when the first guests arrived in time for lunch, explaining that we were rostered in pairs, a male and female in each pair, to support guests in such a way that all guests could have at least one person of each gender available at all times. This, of course, meant shift work with good cover from 8am to midnight, and fewer staff available from midnight to 8am.

"However, that is just the formal arrangement for management. You and your clients will be able to organize your own schedules and you'll probably find everything works out very enjoyably. It usually has in the past," she added.

We were all issued with information booklets which, Betsy assured us, would probably have all the information we'd require. She then issued everyone with details of who their assigned guests would be, emphasizing that we would possibly be working with more than our main clients and informing us that, as there was no standard duration for the guests to visit, allocation to service personnel could seem irregular and chaotic. She finally re-emphasized the standards of service that were expected of us and explained that we never had to do anything that we were not comfortable doing. She elaborated a little on this, explaining that some guests had strange fetishes which they liked to practise and that we had the right to refuse to participate if we wished.

"Rest assured there will probably be other service personnel who will be very willing to cater to their needs if requested. I encourage you to take note of their requirements and to notify me of anything which you are unwilling to provide so that I can suggest willing participants, based on the questionnaire you all completed at your interview." She paused for a few seconds, looking around the room. "Of course, you are all aware that sleeping with your guests at their request is common, almost expected, and if anyone has any strong objection to this, please see me urgently after this meeting."

I suddenly realized the purpose of the questionnaire we'd both completed, asking about a wide range of sexually deviant fetishes and behaviors. I now knew its purpose and struggled to remember how I had answered. For an instant I remembered Sue's hint about what she liked most and I resolved that I would find out by the end of the summer.

Betsy then took us on a more detailed tour of the whole resort, explaining a few relevant rules for such places as the pool, the gymnasium and the dungeon. She emphasized again that clothes-wise, anything went from fully naked to fully clad, and that behavior-wise, the main rules related to safety, consent and consideration for others.

"We're all adults here; remember that. Many people come here because they can act out their fantasies, which may not be acceptable elsewhere. There are no children, except for the ones you create, and there have been a few of those, I must say, so leave your judgement behind. Unless something is dangerous, is adversely affecting others or is clearly being done without the consent of the other person, then it is acceptable. In relation to consent, on occasion you may find guests acting out a scene where one person is acting as though they do not consent to what is happening. A few years ago, we had a couple who acted out several rape scenes, but they were very realistic, enough for staff to forcibly restrain a guest, much to the dismay of both that guest and the person with whom he was acting. Since then, we have a word so that if you attend such a scene and the parties use that word, you know they are acting. The word is 'marshmallow'. If you feel the need to intervene, approach the people and ask if there's a problem. If the person that you feel may be in danger or may be being forced to do something replies with 'marshmallow' then you know you can safely leave the scene to play out. This is particularly relevant to bdsm activities in the dungeon. Any questions?"

There were a few, which she answered, telling us that yes, we were permitted to use all the facilities in our time off, but mentioning also that guests had priority.

"Your scheduled times and program for the first week are in your folder. Meals for you are at staggered times so there are always people available, but it is quite usual for you to ignore those and dine with your guests. Meals are available constantly, if required, even in the wee small hours of the morning. The only other thing I need to say is have fun, but I'm sure you will and probably are already."

I checked with Tina and saw that we were both together, at least for the first guest couple, Colin and Beth. They were due to arrive in a few hours so we had some time to read the documentation we'd been given and peruse the brief bios of our guests. Sue and Troy joined us after a short time and we discussed the whole situation with them. Like us, they were quite excited with the opportunities afforded by the work and also the play aspects of this job.

"Awesome that there's a dungeon," enthused Sue, "I've always wanted to experience some bdsm. I do hope that our couple are into that sort of stuff."