Pleasure Island Ch. 04

"So, do you think I should do anything about my pussy hair? Is it too much, too long, or what?"

"That's a personal choice. My partner, Tina, has a very small, trimmed landing strip from an inch or so above her clit for about two inches upwards. that looks tidy and sexy, to my way of thinking, and is hygienic, but it really is just my opinion. I've noticed, though, that most of the women who we've seen while we've been here are trimmed quite severely, if not totally bald. I've also noticed a few guys that are totally bald as well, although I have no plans to go to that extreme."

"No, a bald cock doesn't look as good, but I think I am sporting far too much hair. After lunch, could you arrange for an appointment for me with someone who can remedy that please?"

"Certainly, shouldn't be a problem. Anything else you'd like while you're there? Maybe a massage, pedicure, manicure, beauty treatment? Of course, they also offer what are known as full-service treatments, but as a virgin, at least until tonight hopefully, you probably wouldn't want that."

Imogen chuckled. "You're right, maybe later in the week. However, anything else would be most luxurious, thanks."

We spent a while chatting about friends and family and other aspects of our lives as we finished the meal, then I escorted Imogen to the service wing, obtaining an appointment for her in a short time, which we spent wandering along the beach, searching for any unusual shells. I dropped her off in good time at the service wing and headed back to our room, where we had arranged to meet when she was finished. I set the alarm for an hour, then slept.

Once I awoke, I had a short time to make a coffee and sit on the deck before I saw Imogen walking up the path. She entered and, after I stood to greet her, without hesitation we embraced and kissed. I poured her a coffee and she shared her experience.

"It was heavenly," she began, "I really enjoyed it and feel so relaxed."

"So, what happened? What did you have done?"

"I started with a trim. Like it?"

She stepped back to give me a better view of her beautifully trimmed pussy. I crouched down and examined her slightly puffy labia hiding her clit and a neatly trimmed landing strip above. Just like Tina's, I thought. I grinned up at her and then, cupping an ass cheek in each hand, I pulled her closer and kissed her just above her clit and below the base of the landing strip.

"It looks gorgeous," I said, "Lovely and sexy. How's it feel?"

"It feels great, sexy as well and cooler than before. I can't wait till you explore it further tonight."

She sat down again and proceeded to tell me about the massage, which she said was very arousing.

"So arousing that I came as he was massaging my pussy. It was heavenly; far better than the ones I give myself."

That explained the puffy labia, I thought. She then showed me her finger and toe nails, and told me about the facial she'd received.

"Larry, the masseur, suggested I might like to return after you've made me a real woman and then he could give me the full treatment," she commented. "He sounded really enthusiastic, so I think I'll make an appointment for later in the week. You wouldn't mind, would you, darling?"

"Of course not, honey. That's what you're here for, to enjoy all the facilities as much and however you wish. And, yes, Larry would be very enthusiastic - he's got a great job spending lots of time fucking all the women visiting the island. Almost as good a job as mine," I added thoughtfully.

The afternoon passed quickly as we shared stories of our past experiences. Soon it was time to head to the dining area for pre-dinner drinks and socializing before eating supper. It had cooled off a little so I wore a loose-fitting toga-like garment, open in front and held closed with a tie, which I left unfastened. Imogen pulled on a similar garment of almost completely sheer fabric, leaving the front open so most of her breasts and all of her pussy were exposed. She chose a high table close to the bar where she knew we'd be passed by a lot of people, and she posed herself on a stool to best advantage, heels on the crossbars and thighs spread apart to fully expose her newly trimmed pussy, much to the delight of the guys walking past. After several cocktails, she was feeling no pain and was allowing more of herself to become exposed as the room warmed up.

We went in for supper and joined a table of couples, sitting opposite each other between diners of opposite gender. This allowed everyone to chat amiably while hands beneath the table could roam delightfully over their neighbors. It was a delicious and leisurely meal and, by the time we'd finished, everyone was well and truly sexually aroused and ready for action. We were invited to join the group in what promised to be an orgy, but we declined the invitation, telling them we had an important private appointment ourselves. I suggested to Imogen that we could dance for a while before returning to our apartment, and she accepted this invitation with pleasure.

The music was slow and sensuous, made for slow, close dancing, and we took full advantage of it. Our naked fronts were pressed together, my aroused cock sliding easily between Imogen's slippery pussy lips. Had she not been a virgin, I'm sure I could have entered her and danced coupled together. As it was, we could only tolerate this level of arousal for a short time before leaving the dance floor and heading back to our apartment.

"Would you like a drink to cool off?" I asked.

"Who needs to cool off, lover. Fuck me now, make me a non-virgin. Deflower me, pop my cherry and all those things that men do when they fuck a woman who's a virgin."

She threw herself onto the bed, lying on her back, then pulled her legs back and apart, exposing her pink, glistening, open entrance.

"Fuck me, darling."

Tempted as I was with this invitation, I wanted her first time to be enjoyable rather than painful. Instead of lying on her, I lay beside her, my hard cock reaching towards the ceiling.

"I suggest that you should be in charge this time. That means that you'll be able to regulate the pain by the pressure you apply. So, straddle me and gently lower yourself onto my cock as hard or as gently as you wish."

Imogen rolled away from me and off the bed, removed her gown, then crawled back onto the bed at my feet, moving up my body as she kissed her way to my cock. She surprised me by taking about half my cock into her mouth, then continued her way up until her knees were outside of my thighs. Then she lowered her pussy onto me, sandwiching my cock between us as she nuzzled my neck then kissed my lips.

"You want to put your big hard cock into my poor little tight cunt, darling?" she asked playfully.

"Oh, yes, darling, I want to push it so far in that the head comes out your mouth," I replied with a grin.

"Ooooowwwww, that sounds like fun."

She moved upwards a short way until the head of my cock slipped between her labia, then she relaxed, moving her hips to position her entrance at the end of my cock, then wriggled slightly backwards, forcing the head into her virgin cunt about an inch. It felt wonderful having my cock head lodged inside her and I was sorely tempted to simply thrust hard and get it over with, but I lay still, waiting for her to engulf me in her own good time. She kissed me some more, then lifted up slightly before pushing downwards again. I slid inside her a little more, then felt the barrier which I knew needed to be broken. She'd told me she'd used tampons, so I expected that the barrier would be partly opened at least, so it shouldn't be too painful or difficult.

"You ready to push through my barrier?" she asked, "You want to push your cock right up inside me and pop my cherry?"

"Yes, darling, I want to fuck you hard, make you a woman. But you'll need to do this at your speed, so just push back and down when you're ready."

"It'll hurt, won't it," she said, a statement, not a question.

"Probably, but you'll find the pain will be minimal compared with the pleasure it will bring."

I hoped this was true in her case, having heard of cases where the pain of first entry was incredibly severe and some where the hymen had to be surgically broken. I hoped this would not happen tonight.

Without warning, she pushed backwards and downwards hard. My cock was hard enough that it didn't bend and I actually met her thrust and pushed against her as I felt the pressure build then the membrane release and with a rush I penetrated her further than I intended for a first entry. She tensed, then relaxed against me, her teeth biting my shoulder as she dealt with the pain, which seemed to go quickly as she released her teeth from my shoulder and turned her head sideways, breathing rapidly. I could feel her cunt grasping and releasing my cock until she lifted her head and shoulders off me and looked into my eyes.

"Is that it?" she asked.

"That's the worst part. You're no longer a virgin. Now the fun part can start."

"Oh, goody," she replied, like a small girl being offered a treat.

Instead of withdrawing, as I expected, she pushed herself further down, sliding my cock into areas hitherto unexplored. I was surprised how far in I could reach. I was quite well endowed, around eight inches when fully erect, like now, and she took most of that before I finally felt the end. Even then, she wriggled her hips in an attempt to take more. She looked into my eyes again.

"Are you fully inside?" she asked.

"Almost, incredibly deep for a first time. How's it feel?"

"Ohhhh, it's heavenly. The pain's nearly gone and it feels wonderful having you deep inside me. Now that initial entry has been achieved, gawd, it sounds like a space mission," she laughed, "Now you're inside me, honey, can we roll over so you can fuck me good?"

I held her close to me and we rolled over together, leaving me on top. She parted her legs further, bending them and spreading wide apart as she pulled her knees towards her shoulders with her hands, and pushed her hips upwards, wanting more. I withdrew slightly, then began fucking her, each thrust expelling air from her lungs in a grunt. She moved her hands under my ass cheeks, pulling upwards to encourage me to plow her deeper. Slowly I lengthened my strokes, moving out further, plunging in deeper until she'd taken everything I had. I felt her engorged clit against the root of my cock as I ended each stroke and could see that she was becoming more and more aroused. I covered her breasts with my hands and squeezed her nipples rhythmical with each thrust. She began rolling her head from side to side, moaning with pleasure, her hips pushing upwards to meet each thrust. Then she became even more vocal and animated.

"Yes, honey, oooohhhh, yes, like that, harder, harder, yes, fuck me hard, oooohhhh, honey, yes, yes, Yes, YESSSS, OOOHHHH, I'M CUMMMMINGGGGG!!"

I made a final hard thrust into her and held still, feeling her body trembling and writhing beneath me as her cunt pulsed around my cock. Her orgasm seemed to last forever, until finally she relaxed, opened her eyes and grinned widely at me.

"Oh, darling, that was wonderful. Thank you soooo much. My first orgasm on a cock. Beautiful. Incredibly wonderful. Thank you, honey."

She pulled my head down and kissed me, hard, lovingly, tongue twistingly. Once we broke the kiss, she again grinned up at me.

"More," she said, "Please give me more. I want you to cum in me, honey, fill me up with your cum."

In the service industry, they say the customer is always right. I certainly wasn't about to debate that. I began moving back and forth, slowly at first, then faster, deeper, pulling almost completely out, then thrusting back in, hard, my pubic bone pressing against her slit, the end of my cock just touching the end of her cunt. Again and again I thrust, feeling myself drawing closer to my orgasm until suddenly she stopped.

"What's wrong? Does it hurt?"

"No, nothing like that. I wanna be on top this time."

Once again we rolled over and she sat on me, knees wide apart, most of her weight resting on her pussy and her clit as it pressed hard on my pubic bone. She began tentatively moving back and forth, sliding her clit over me, her eyes closed, a smile on her face that told me she was very much enjoying the sensations. I rested my hands on her hips, then began moving her back and forth further, feeling the head of my cock moving inside her, sliding over her cervix. She reached for my hands and pressed them to her breasts, so I began kneading her tits, pulling and squeezing her nipples. She moaned in pleasure, then her movements became faster, harder, she began lifting off me and thumping back down. I felt my orgasm approaching and began thrusting upwards, higher, harder, in time with her movements, then I couldn't hold on any long.

"I'm cumming," I cried as the first jet of sperm spurted against the end of her cunt.

"Yes, yes, fill me up, oooohhhh, Yesss, YESSSS, I'M CUMMINGGGGG!!"

After our moments of ecstasy, she lay forward on me, her cunt still pulsing around my cock, our rapid breaths mingling as we gradually recovered.

We made love twice more during the night, once when we both awoke, once with the sun streaming through the windows. Both times were wonderful, blissful ecstasy. I had a sudden thought.

"As you were a virgin, what have you done about contraception?" I asked.

"All taken care of," she replied, "Dob't worry, you won't be a daddy from me. I went on the pill a few months ago; the women in the office said I probably needed to because of what they'd planned."

"Good idea," I replied with relief.

We enjoyed a late breakfast, I ordered a linen change from housekeeping to replace the stained sheets, and we spent the morning lazing on the beach, swimming, talking, much like honeymooners, which to some extent we were, but only on a temporary basis. Late in the morning, Tina and, I presumed, Keith walked by and came over to us. We stood up as they approached.

"Ok if we join you?" asked Tina.

"No probs," Imogen replied before I could answer, "Are you Tina?"

"Yes, and this is Keith."

"Oh, hi Keith and Tina, I'm Imogen."

"Hi, Imogen and Jeff," replied Keith, "You're a lucky man to have Tina," he added with a grin as they removed the towels they had over their shoulders, spread them on the sand and sat on them as we sat down also, Tina beside me, Keith beside Imogen.

"Well, that means they both must be lucky, because Jeff's just divine," said Imogen.

We chatted for a while about the resort, the weather and other inconsequential things to break the ice, and then, almost inevitably, the talk turned to sex. Keith and Tina described their erotic encounters since Keith arrived, and Imogen described ours, going into detail about losing her virginity the previous night. I noticed that Keith's cock had hardened considerably as she described in detail how I popped her cherry, as had mine, and Tina was idly stroking my thigh as she listened intently.

"So, now you're no longer a virgin, does that mean you're available?" asked Keith.

"Oh, I could be, for the right guy, in the right place and at the right time," replied Imogen teasingly. "It might cost you a dinner though."

We all laughed, knowing that all meals were included. "Well, at least that wasn't a 'No'," replied Keith grinning, "Is this the right place and time and will lunch afterwards suffice?"

Imogen looked at him closely to try to assess if he was joking. He slowly stroked her thigh, moving his hand upwards until his fingers were stroking her pussy lips, which I noticed were glistening with her juices. She was obviously aroused by the talk and actions. In return, she reached towards his cock and began slowly stroking it, producing a bubble of precum.

"Looks very much like it could just be the right time and place. Do you mind an audience?" she asked.

"Not at all," he replied, turning towards her and beginning to caress and kiss her. She lay down on her towel and welcomed his attention, reciprocating by caressing and cupping his balls as she stroked his ass cheeks with her other hand.

I turned towards Tina and opened my arms to her. She came to me, kissing and embracing me as I also lay on the towel. It took only a few seconds before she was straddling me, her pussy seeking my engorged cock. Once she was perfectly positioned, she slid downwards and I entered her fully. We then lay together and watched Keith enter Imogen and begin fucking her deeply as he kneaded her breasts and she pulled him deeper inside her with her hands beneath his ass cheeks. I felt Tina's cunt muscles clenching and releasing my cock, stimulating me even without any body movements. I wondered if I could cum just from that and lay still to see what would happen. Imogen began making soft grunts with each of Keith's thrusts as he squeezed her nipples and fucked into her as hard as he could.

It was incredibly arousing lying beside Imogen as she climbed the slope of arousal, impaled by Keith's cock in her cunt, the cunt I had only opened for the first time last light. My arousal was made much greater by Tina beginning to move up and down on me, causing my cock to slide almost completely out of her, before thrusting her hips downwards, engulfing me completely in her warm, wet tunnel. At the end of each thrust, when she was fully impaled, she would wriggle her hips a few times to rub her clit against my pubic bone, before repeating the process time and time again. I wondered how much of this I could take before I filled her with my cum.

Beside me, Imogen was showing clear signs of her approaching orgasm, writhing beneath Keith's body as he increased his speed and power, intent now on providing Imogen with a dose of his sperm. I knew enough about Imogen to know that she came easily and strongly, so was not surprised when she suddenly let out a shriek, wrapped her legs around Keith, rolled her head from side to side as her body shuddered with her release. Keith was apparently caught just short of his orgasm and was unable to complete due to being locked in the vice-like grip of Imogen's legs.

Watching this beside me must have also pushed Tina over the edge because she tensed up, her body shook for a few seconds, then she seemed to relax and lie on me, breathing hard. Keith gave up trying to continue fucking Imogen and lay gently above her, supported on his elbows, watching her recover from her climax.

A few minutes later, Imogen and Tina had fully recovered. "Bet I can get Keith to orgasm before you get Jeff to cum," said Imogen with a grin.

"Right, you're on," said Tina, "Loser has to ride a Sybian for 15 minutes."

"Ooohhh, a Sybian, I've only read about those. That would be fun. What does the winner get?"

"Winner gets to ride it for a quarter of an hour," chuckled Tina.

Imogen laughed, then began using her hands on Keith's ass to push him back and forth. As I began moving Tina again, intent of bringing her to a second climax before filling her, she sat up to ride me in a position she knew would bring me to orgasm quickly. I felt her cunt slide down my cock, fully encasing it with slippery sensations that quickly brought me back to where I'd been a short time before. I used my hands on her hips to slide her back and forth as she used her legs to push herself up and down, the combined effect being to stimulate us both towards what I expected to be a rapid mutual orgasm. However, when I glanced sideways, I was not so sure Tina would win.

Keith was fucking into Imogen hard and fast, each thrust ending with hip movements to stimulate her clit, while his hands were massaging her tits and squeezing her nipples hard. Imogen was panting hard and giving all the signs that she was about to cum again. The sight of this couple fucking together beside me probably distracted me from my main task and when I refocused, Tina had her eyes closed and was trying to hold off her orgasm until I reached mine. I increased my speed, trying my best to cum, when I heard grunts beside me followed by Imogen's scream as they both came hard together. That was enough to cause Tina to cum and her clasping cunt muscles did the rest. I spurted several hard spurts of cum into the end of her love tunnel, then she collapsed onto me, lying on my chest, breathing hard.