Pleasure Island Ch. 04

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Imogen and Keith


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. All characters in this story are over the age of 18.


I greeted Imogen as she disembarked from the helicopter; she greeted me with a handshake as I introduced myself. I carried her main bag, while she carried her handbag, and escorted her to the apartment we’d be sharing. Once inside, she looked around the luxurious rooms while I arranged hot drinks.

“What’s your favorite hot drink?” I asked her.

“Earl Grey tea, please, black with a slice of lemon, no sugar.”

I knew we didn’t have that in the apartment.

“Ok, I’ll need to get that from the main kitchen. Make yourself comfortable and I’ll be back in a few minutes.”

I returned to find her seated on the deck, in the shade, admiring the view of the ocean. I made her tea and my coffee and joined her on the deck.

“Thank you,” she said, smiling up at me as I placed her tea on the table beside her. “It’s certainly a beautiful view; lovely place.

“Yes, it is. I’ve been here for a few weeks now and really enjoy the freedom, the activities that are available and just being here with lovely people.”

“Mmmm, yes, I can see you would enjoy that. So, what have you planned for me this week?”

“That depends entirely on what you want to do. I can be with you all the time or you can go off by yourself if you wish. There’s a list of activities in the information folder, which I’ll get for you soon, so you can choose what you want to do. It’s a clothing optional resort so you can wear whatever you like or nothing at all. The pool is very popular, especially to cool off on hot afternoons. Did you have anything that you really wanted to do this week?”

She turned her head and looked directly at me for a few seconds, then looked away. I also looked directly at her, noticing that she was a beautiful woman, slim, moderately tall, beautifully proportioned breasts beneath quite conservative clothing. I had the feeling that she was holding something in, that she had something to tell me which she felt was embarrassing. I held her gaze for a few seconds, then she looked downwards and I saw a slight flush come to her face. When she spoke it was hesitant, unlike her earlier conversation.

“I have a confession, I guess you’d call it. I didn’t make this booking; the women I work with made it for me. They decided that this was something I really needed, like, really, really, REALLY needed. Oh, I feel all embarrassed even talking about it, but I know I have to go through with it. They thought that, as I was the only one in the office like this, I really needed to come here so that I could join in with their conversations instead of being left out.”

She paused, far too long simply to take a breath or think. I felt the need to ask a question.

“So, when they’re together, what do they talk about that feel that you can’t join in?”

“Oh, the usual womanly stuff, you know, well, I guess that actually you don’t. Boyfriends, dates, what they did on their dates, Ok, sex. That’s mainly what this group talk about and I can’t join in. Here’s the confession; drum roll; I can’t join in because I’m a virgin. There, it’s out. You’re stuck with a virgin for a week.”

She bent forward, cupping her head in her hands and her body shook as she burst into tears. I sat still, not knowing what to do. Should I attempt to comfort her, or sit quietly until this passed, or what? I moved around the table and crouched beside her chair, placing my arm around her shoulders. She turned towards me, rested her head on my shoulder, an arm around my neck and continued to sob. After a few minutes she recovered a little and murmured “I’m sorry,” as her breathing became less ragged and her body calmed. A few more minutes and she pulled away, sitting back in her chair.

“I’m really sorry, Jeff. You don’t deserve to have a broken woman for the next few days. Sorry.”

She rummaged in her handbag and I produced a box of tissue from inside. She took two and wiped her face, then sat back and gave a hint of a smile. I had sat back in my chair and she seemed to be waiting for me to say something. Instead, I sipped my coffee, and she also sipped her tea, which seemed to lubricate her throat, because she began talking softly and unemotionally.

“My parents were very strict with me as I was growing up, telling me a little about sex but mainly not to do it until I was married. I put all my time and effort into study, went to college, worked hard, excelled, passed everything, and eventually left with a PhD. I was headhunted for the job I have in a research eryaman genç escort bayanlar laboratory, where I’ve been working now for two years. I had one boyfriend about 18 months ago but he told me I was cold and unemotional and ditched me after a couple of months. I really loved him, but I just couldn’t seem to show him love and I wouldn’t let him touch me, well, not sexily, if you know what I mean. So here I am, a 27-year-old virgin crying my eyes out in a beautiful holiday resort to a wonderful young man who only has my best interests at heart, or so it seems.”

She paused, then looked up at me, tears still glistening in her eyes. I felt an amazing love for this woman, so far destined to be alone, unloved, trapped by programs from her childhood implanted by her parents. How many others were like this, I wondered? I remained silent, knowing that there was more to come.

“So, a few weeks ago all the lab techs in the lab I run put on a luncheon for me and presented me with a voucher for a week at Pleasure Island. I did some research and found out what this place is all about, learning what types of pleasure seem to be their specialty, and frankly, I’m terrified.”

She looked back into my eyes. seeming to search for reassurance. I reached out my hand towards her and she clasped it tightly with her hand, almost like a drowning person gripping onto their only hope of salvation.

“It’ll be Ok, honey, I promise you; it’ll be just fine. We’ll have a wonderful week and you’ll be able to return to your work mates a different, refreshed and far less uptight and remote person.”

As I said this, I hoped against hope that my intuitive assessment of her situation in her workplace was accurate. Her reply reassured me.

“Thank you, darling,” she replied, astonishing even herself by the use of an endearment it seemed, because she paused, then rolled the word off her tongue again. “Darling; I don’t think I’ve ever used that word before. Thank you. Please teach me to be less uptight; please free me from the tyranny of my virginity. Can you do that for me, darling?”

I assured her that I could and we sat for a while in comfortable silence, watching the endless ocean, sipping our drinks. Once they were finished, I turned to her again.

“To accomplish what you need to do this week, I’m going to have to take the lead while you follow. I promise that we won’t do anything you really don’t want to do, and I hope that what you do want to do and will allow yourself to do will permit you to achieve your goals and change whatever beliefs need to be changed. Is that Ok, sweetheart?”

“Sweetheart,” she rolled the word off her tongue, “I don’t think I’ve ever been called that. Yes, sweetheart, that’s wonderful. Thank you.”

“Right. So, for a start, we can both get into something cooler. How far are you prepared to go?”

She grinned at me, a first, showing that she did still have a sense of adventure for the unknown.

“Take me inside and remove what you wish,” she said with a grin and a bravado which I hoped was more than skin deep.

I picked up the cups and we returned to the kitchen, where I deposited the dishes, then I held out my hand, which she took in hers, and I led her to the bedroom.

“Is this the only bed?” she asked.

“Yes, darling, it is.”

She blushed as she turned towards me and took my other hand in hers. “Then I guess we’ll be sleeping together,” she said, “That’ll be a first for me. I think I’m looking forward to that.”

“I know I am,” I replied, hoping I wasn’t being too forward. “Now, about these clothes. Do you want to remove them or will I?”

“Please strip me, darling,” she replied, the tremor in her voice belying her apparent confidence.

Although she gave no outside indication of the importance of these words, I knew that for her to make this simple request was undoubtedly life-changing and showed a commitment to change that was very encouraging. I started by removing her shoes, followed by her top, revealing her full breasts trapped in a brief bra, which I allowed to remain for the time being. I then knelt and unfastened her skirt, easing it over her hips and down her bare legs until she could step out of it. She was now wearing matching, lacy bra and panties.

“Your turn now, honey,” I told her, “Strip me to the same level please, sweetheart.”

She did, removing my shirt and shorts so I was standing in underpants only, the front pushed outwards by my partly aroused cock. I saw her watching the bulge.

“Have you ever seen a man’s penis?”

“No, never, only pictures.”

“Well, you’re in for a big reveal soon then. I’ll remove your bra and panties, then you can remove my undershorts. Ok with you?”

“Please do that, honey.” She grinned, probably due to her unconscious use of the endearment.

I removed her bra, exposing a beautiful pair of firm breasts with pale brown nipples, then again knelt and slid her panties down to her ankles, exposing her unshaven bush with her glistening labia peeking through. She was quite obviously ankara escort bayan aroused. I looked up into her eyes.

“Ok so far?”

She nodded.

“Your turn, darling, finish the job.”

She knelt in front of me and eased my undershorts downwards, over my engorged cock, which sprang outwards hitting her forehead once it was released.

“Oooohhh,” she said, moving her head back a little before taking my shorts down to the floor, where I stepped out of them. Tentatively she reached out for my cock, then stopped.

“May I touch him?” she asked.

“Certainly, any time you like. May I also touch your most private assets also?”

“Oh yes, honey, please do.”

We stood before each other, each stroking and gently handling the other’s genitals, until, after a few minutes, she looked into my eyes.

“Let’s have a swim together,” she suggested.

“Great idea. What do you want to wear?

“Well, I guess I’m perfectly dressed for swimming just as I am.”

We grabbed towels, then headed outside to walk the short distance to the pool. I noticed that Imogen was quite nervous whenever other people were around, holding her towel in a strategic location when she considered it necessary, but she didn’t wrap it around herself so I considered that was progress. Once at the pool, we dumped our towels and dived in, swimming a length, then sitting on the ledges around the edge with water up to our shoulders.

“How you going?” I asked.

“It feels wonderful. I’ve never skinny dipped before and it feels so free, the water moving over my skin feels amazingly sensuous and sexy.”

“It’s great; once you’ve swum naked you never want to go back to constricting swimsuits,” I agreed. “So, what sexual experiences have you had to date? For example, have you used toys, masturbated, experienced orgasms or are you truly a complete virgin?”

I noticed her face blush a little; she still was not confident discussing sexual matters and I didn’t blame her at all with her previous upbringing. It was still early days.

“Well, I have fingered my clit to orgasm a couple of times, and I have used tampons so I know they go in Ok, but I have never used toys or anything like that.” She paused and grinned at me. “Which is not to say that I wouldn’t be willing to try those in the next few days. I found orgasms to be exciting and releasing, but certainly not overwhelming, at least, not the ones I gave myself.”

She stopped talking and looked around as a group of several mixed couples walked casually naked alongside the pool.

“They come in all shapes and sizes,” Imogen said softly.

“What do?” I asked.

She looked at me as though I should have known what she was talking about.

“Penises, of course,” she replied quietly.

I let out a bellow of laughter, much to her surprise.

“Yes, of course they do, just as breasts and pussies do as well.”

She reached down to my cock and took it gently in her hand. It was smaller than earlier, the cold water affecting it, but I felt it immediately begin to engorge as she gently played with it.

“I guess he’s been in lots of pussies, eh,” she said, more an observation than a question.

“Yes, quite a few. My partner, Tina, and I have a wonderfully open relationship in which we can have sexual encounters with others safe in the knowledge that it’s only fun sex, not an intimate relationship.”

She thought this over for a while, then continued. “So, she’s home while you’re here having sex with whoever you like?”

I laughed. “No, she’s here also. For the past few weeks we’ve shared couples here but this week I’m with you and she’s with a single guy, the one you flew here with.”

“Oh, Keith. So, she’s his service person, so I guess he’ll be having sex with her.”

“Oh, yes, I can assure you that she’ll be fucking his ass off, that’s for real.”

“Fucking his ass off; that sounds like an interesting expression. So, are you going to be fucking my ass off too then?” she asked with a grin.

“Hopefully, although I’m more a pussy man than an ass man, so if it’s all the same to you . . . “

“Yes, I think I want you fucking my pussy not my ass,” she replied coloring slightly, “I don’t think fucking, I kinda like that word, I don’t think fucking my ass is a good idea. It was meant for different purposes.”

“I agree, though many would not. I far prefer pussy, or cunt if you like, to ass.”

“Cunt. That sounds delightfully earthy. So, you want to fuck my cunt with your penis?”

“Absolutely I do, but you can use cock or prick instead of penis. So, you can talk about me fucking your cunt with my cock which seems far more expressive that saying we’ll have sex by me putting my penis in your vagina, don’t you think?”

“Yes, definitely. I can see that my education has been lacking. Maybe I should have spent less time with books and more with guys.”

“Well, you can always catch up later, like this week. Want a cuddle?”

“Mmmm, yes, sounds good. I kinda feel a bit sexy, I think. What did you etimesgut escort have in mind?”

I took her hand and we moved a few steps to some circular underwater seats, spaced a few feet apart, and sat on one of them, the water coming to my armpits.

“Now, you can face me and sit on my lap,” I invited, guiding her with my arms.

She straddled my thighs and sat down just above my knees. I could just touch my fingers together with my arms around her.

“Come a bit closer, honey, it’ll feel much better.”

I helped her slide towards me, feeling her hardened nipples touch my chest as her pussy just nudged my erect cock. I didn’t want that in her yet, that would come tonight, hopefully, so I pulled her forward a little more so my cock was between our bodies. She reached between us and felt where the tip was against her belly.

“You mean, when you’re fucking my cunt your cock will go this far into me?” she asked.

“Yes, that’s about right. Why?”

“Nothing. Just wondering and surprised how I can take that. The body is amazing to be able to stretch that far.”

“Yes,” I replied as I gently pulled her against me, “Bodies are amazing things.”

After a few minutes we kissed, lips to necks to begin with, then lips to lips, soon changing to tongue to tongue. I was amazed how quickly she was discovering the joys of sexual pleasure, catching up in minutes on the years of missing out. We stayed in the pool for a while, just holding each other, allowing her to become accustomed to the feeling of my body against hers, my cock against her belly, her nipples against my chest, until I felt my shoulders starting to burn from the sun.

“I think we’re starting to burn in the sun, and we certainly don’t want that on our first day. Besides, it must be time for lunch. You feeling hungry?” I asked.

“Actually, yes, I am, and I feel a bit of burning as well. So, what now?”

I stood up, allowing her to slide down my thighs and stand in the water, then took her hand and together we walked up the steps at the end of the pool. I noticed several people watching us and wondered how she felt about that, but if she felt anything, she didn’t show it. We collected our towels and she unselfconsciously slowly dried herself. I watched her spend considerable time drying her pussy hair while turning to ensure that those still in the pool would have a good view. I noticed they were all watching, some overtly, some trying to hide their interest, but there was no doubt in my mind that she was playing to her audience. She seemed to be a born exhibitionist, probably beneficial when staying in a place where nudity and observing nudity were both quite acceptable. Once she was dry to her satisfaction, she threw her towel carelessly over her shoulder, took my hand and we walked back to our apartment.

“How do you want lunch?” I asked. “I could collect it for you and we could eat here, or we could collect it from the dining room and eat under the shade on the grass, or we could eat a more formal lunch seated in the dining room. Your choice.”

“Can we stay naked while we eat?” she asked.

“Yes, if you wish, although it is accepted practice to sit on a towel if using communal seating.”

“I like the idea of lunch on the grass in the shade, and I want you to wait on me. Actually, when I was younger, I often had dreams of being waited on by a handsome prince and for some unknown reason both he and I were naked. Seems like my dreams are coming true.” She stood up and held out her hand. “Let’s go.”

We walked to the dining room, selected our food and drinks, then carried our trays to a shaded spot that she chose. I was interested to see that she chose a place close to a walkway in easy view of passing people. It seemed that she was an innate exhibitionist or voyeur, or maybe both. I asked her about this and she blushed and appeared a little embarrassed before she replied.

“All this public nudity is very new to me. I sort of expected to be embarrassed by it because society out there has strict rules about what and where you can expose yourself, which leads inevitably to a shyness, at least in most people. However, I’ve always felt like I wanted to show off my body to others, but I’ve been constrained by mores and expectations, not to mention laws. Whenever I go to the beach, I enjoy wearing a tiny bikini, which on occasions has been unkindly commented on by some people as well as attracting its share of attention, especially from guys. However, today I’ve found that I really enjoy being naked and showing my body off, as well as watching others show themselves off, so I guess I’m right into voyeurism and exhibitionism. How about you?”

I’d never really thought about it before. Tina and I were often naked around each other; it’s just how life was. And I certainly enjoyed the views here as well as feeling perfectly natural naked.

“Yeah, I guess I’m much the same. Never really thought about it. I do think that in normal society the rules and expectations create an artificial goal for people to see others naked or partly naked, and it is the prohibition of this that creates many of the problems, as well as many of the business opportunities for strip clubs and the like. As far as I’m concerned, nudity with respect is very healthy. Helps you increase your vitamin D as well, which is good for you.”

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