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Rocking her Yacht

‘Sir, may I take your jacket and bag?’, the very young looking teen in a white t-shirt too long to see her bottoms took the belongings she asked for and walked me into the yacht, the first that was private to just one person. Through the decked out minimalistic white entertainment room, we passed the dining room before climbing a spiral staircase, to the highest point of the boat covered in faux carpet grass.

She pointed in the direction of the girl who invited me, and quietly set my bag and jacket that looked so ever ‘cheap’ given that setting. Angela and I, began chatting on Whisper (app) a few weeks ago, in a topic of ‘self-contentment’ she couldn’t quite comprehend. A super rich, second generation of a multi-billionaire, had chartered a private jet to fly me from Singapore to the States where she lived.

Donning the fairest, visually-softest skin, that glowed in the setting sun, the messy shawl strewn over her body had me distracted by what was under it. I took the other day bed that was empty, and removed my top as she asked, to bask in however much sunlight there was. Taking off from where we stopped chatting on the app, we hit off and got back on track without much discomfort, although it was mostly me doing the talking.

The girl with no concept of poverty, difficulty, simplicity of life, had nothing but interest in how I lived. To think I could manage to get attention from someone like her, I was more fearful of the luxurious indulgence I might be falling into. As the moon revealed itself behind the clouds, the gaze in her eyes got more mesmerising, staring at me so much that it embarrassed me a little. Such privacy, comfort, tranquiilty, was impossible to achieve in my busy little country. Yet, for someone who was raised amongst these, her mind was much noisier than mine.

Besides the seriousness of what we spoke about, I found it extremely hard not to admire the beautiful contour figure of hers, especially at her waist that was unobstructed by the thin shawl. A simple, black-white bikini bottoms closely wrapped her fine ass, as if too toufu to touch.

‘Angela, dinner is ready’, the same voice whispered between us and she led us to the dining room, where a 6-course, Mediterranean-style dinner filled my tummy up well. Resuming our conversation in her bedroom, we laid even closer in comfort, with her trailing my (round) curves as my voice bedazzled her.

‘What would you do if a girl throws herself at you?’, the question came along with a cheeky smile, which I guessed was more of a teaser than having it actually happening. ‘I’d trust that she knows what she was doing, and would let her have her ways’, I replied the same way if anyone else asked, and she began untying the bikini top under the shawl she wore around her shoulders, still baring her tiny thongs with pride.

The huge difference in our lives, wouldn’t be just in terms of net worth. For someone of her status, a ‘don’t you have a boyfriend’ question, would certainly draw the line between ‘getting shot in the head’ (by him), or ‘too good to be true’. In a calm and smitten smile, she gave her answer, ‘On the contrary’.

She took my frightened-cold hand and slipped it through the cross-fold of the throw (a.k.a. shawl) to let me caress her wealth-filled cups. Playfully pinching her nipples, the innocent, highly-responsive body signals surely did surprise me. While I imagined playboys to have their ‘choice’ of biological ‘outlets’, it wouldn’t be too crazy for her to have a toy boy exclusive to herself – you know? With body checkups and probably a NDA or contract.

In little time, I found myself fingering her in a position where her ass was right by my shoulder, while she curiously inspected my dong. At no point, I felt her sharp, manicured nails. Instead, the gentlest, caring, mindful hand went around that unimaginable piece of sex-driven cock. ‘It’s beautiful’, a whisper floated like the sea breeze into my ears, confusing my ego and humility.

A moist, puffy surface then swiped across the tip, leaving much to my creativity to wonder what she was up to. The most satisfying moment came when her lips sealed around the head, and descended down that glorious piece of meat, filling my mind with nice, good sensations that shivered my whole self.

‘You’re good at it’, I groaned as another wave travelled along my thighs, to the toes that curled up. ‘Oh don’t give me that. It’s just my third time’, according to her history I didn’t probe too much into. Her sensual blowjob lasted for a good ten minutes, before I started turning numb to the predictable cycle of her deepthroat attempts.

Turning her around, coming face-to-face with such a gorgeous girl instantly melted my heart. For a change of location, we went back to the day bed, where the stars sparkled like winks. There, I went on top of her and inserted my urban manliness into her, going in as carefully as she played with me earlier.

At that moment, jazz music came on and we began making love to the tempo, taking all the time we could to enjoy the endless strokes of my shaft thorough brushing the insides of her vagina. Unhurried, we were caught in the right momentum, increasing our pace as the climax built up.

There was no other positions we attempted, since I didn’t want to put her into doggystyle, her being too perfect to be put on her fours.

‘Where do I end tonight?’, I blurted my concern out in the best relaxed tone I could, and she wrapped her legs around me tighter. ‘Inside me. I’m on birth control’, she hugged me closer after and we left the rest of the work to my hips, jutting faster, deeper, and quite mercilessly into that well-maintained little thing.

Battling against my quick breaths, I exclaimed a whisper too loud into her ears, ‘Here it comes!’. ‘Here you cum’, the correction came at the same time as I did, pumping my seeds deep into her love-entrance as I slowed down to a halt. We fell away from each other a minute later and remained on our backs, slanting our bodies to soothe the overworked genitalias.

Honestly, I haven’t fantasised that far to even do what we did, with all those firsts on a boat, in the middle of the sea. That night, we spent a long time in the entertainment room, talking about the possibility of ‘working’ for her, as a companion or sorts.

Some things were finalised, but most weren’t. That attendant on her boat that took my stuff earlier? She tended to us the whole night when we were awake, bathing us, serving us as if she had seen too many times her employer brought men on board.

At the end of the trip, that staff accompanied me back on the private jet home (back to Singapore) and confessed her crush on me. Well, the only thing I could confirm then, was that I will be with Angela in a few weeks’ time, at her own residence this time.

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Deep Sea Drilling

Gladys: ‘Why are you sitting here alone? Thinking of swimming ah?’

The company chalet had came to an end after all the food was finished, majority of the staff headed home while a handful not on duty the next day stayed for the night. Among those who remained, there were three girls and two guys, which my other male counter part had too much to drink and fell asleep before the rest.

Me: ‘No la. Just enjoying the night sky. Lie down and close your eyes for a while. Then you’ll be able to see more stars.’

On the concrete jetty, the two of us laid quietly still, admiring the sight that most of our city lights had hidden. Gladys was the newest staff that joined us, working part time while studying in a private uni. Physically wise, she was the tiniest lady amongst us, but fashionably dressed outside work.

For that evening by the sea, she joined me in a bare back spaghetti blouse, bikini knots exposed around her neck and above the waistline of her shorts.

Gladys: ‘You want to go into the water?’
Me: ‘It’s dangerous eh. But I can save you if anything happens.’

She got up before I did and stripped her top and shorts off, ducking under the rope blocking the steps. I hurriedly threw my shirt away to follow her down in case she missed her step. In pitch darkness, we joined hands as our bodies dipped into the chilly waters, current pushing us around the pillars under the jetty.

Gladys: ‘Don’t let go of me ah.’

Within seconds of the pounding waves, she was hugging me on my back as I waded out into the open. Feet unable to touch the sand beneath, I executed the biggest strokes to get us to the side of the boardwalk, till I could stand firmly on the sand.

Me: ‘Ok ok. We are safe now.’

After she got off my back, she still could not reach the sand. Very cooly, she kept her grip on my arms as she floated closer to my chest. One arm wrapping over my shoulder, I could feel her other hand running down my waist.

Me: ‘Eh eh.. where is your hand going?’
Gladys: ‘Sorry la. Just trying not to die.’

Her fingers wriggled into my shorts that had a very elastic waistband, going around to my groin where my dick was shrivelled in coldness. She gently peeled the foreskin back and the erection came imminently into her grasp. I placed one hand on her back to hold her against my chest and ran the other across her thigh. Going straight for her pussy that only had a little triangle for shield.

Once I slipped my finger between her clit, hot breaths started blowing down my neck in contrast to the cold water. One thing leading to next, she had both her legs around my hips leaving a big gap to let our hands fit through her groin and my belly, still working hard stroking my manhood to keep herself warm.

As I dug my way into her pussy, moans drifted into my ears, increasing my speed till she was shivering in ecstacy. Minutes later, she let go of my cock and readied herself closer to me, guiding my arm around her back to hold her tight.

Gladys: ‘Let’s do it here. Shall we?’
Me: ‘No one will ever know right?’

I held her waist as she relaxed her arms and slid downwards, sheathing my sword into the warmest spot in the ocean. The tightness drew the largest breath of air I had and the fear of falling into the waters caused involuntary contractions over my dick.

Me: ‘You’ll float up and I’ll pull you down.’

A firm nod confirmed her enthusiasm and we did as I suggested, making our own waves as our genitals connected, driving deeply into her love hole. As our speed was greatly limited to the resistance in the water, we only managed to get close to climax but not able to satisfy our needs.

Like a jellyfish, we bobbed up and down to the steps and remained at the bottom, lifting half of our bodies into the open air. I did hope that the barnacles did not die when I sat on them, bouncing the petite Gladys on top till she was moaning in orgasms.

Rocking wildly on my lap, I was more distracted by the queerness of seaside sex than the waves of pleasure, drifting non-menacingly through my body.

Me: ‘Hey hey. Let’s change to doggie. There is a small platform for us to stand on here.’

She got up and we stood knees deep at the wider lowest step, bending over for me to ram her rear. My cock slipped into her easily and began ramming the foam out of the sea, garnering gasps as I went deeper than the (sea)cow girl style earlier.

Gladys (whispering): ‘You’re so deep inside me!’

My hands never let go of her waist as I repeatedly dragged her backwards, deep-sea drilling her pussy till she came another time. I continued fucking her as long as I could and it lasted for a good five minutes, against the freezing waters and the limits of my body. By the time I went all out, her elbows were shaking badly but moans never stopped exciting my senses.

Me: ‘Gladys.. I’m going to cum.’

A pat on the side of my hips slowed me down to a stop and she turned around to sit on the steps. Signalling for me to sit between her legs, I finally rested my tired calves and let her hug me from behind. Both her hands went around my two eggs, one sausage combo and jerked them rhythmically, caressing each of them like a dutiful mother hen.

Me: ‘Coming.. coming.. ‘

Her small palm wrapped around my dick head as hot cum sprayed out of the pee hole, filling her hands as she tried to catch all of it. While the last few twitches emptied my balls, she rubbed both her hands together on the tip and spread the warmth around, which I could not help but begged for her to stop teasing me.

Seeing her cum covered hands, we couldn’t be more happy to have each other in this specially romantic night. She washed her hands in the water and I wore my pants back, before returning to our clothes to head back to the chalet.

Our fingers magically interlocked for the walk back to our accommodations to which we could not find any of our friends inside.

Gladys: ‘Hey, Yi sent me a message.’
Yi (Whatsapp): ‘I can’t find your guys anywhere and we won’t be staying for the night. The key is in the corner of the BBQ, charcoal level.’

We found the key and went for a shower straight, in our birthday suits and of course, together. Since the both of us were not working the next day, there’s no need to describe how we spent the night together. Not especially when we have a fully air-conditioned bedroom to ourselves.

Somehow, the lack of condoms brought our night ‘activity’ to a whole new level, testing the ‘pull out’ method and holding a ‘cum tasting’ session in our comfy nakedness.