Single Male Chaperone - Reimagined

It was as if Kate could sense where my head was at when she directed me to use my arms to hold up Elle. The process of balancing - and basically bouncing - Elle on my dick had a distracting effect on me mentally and I was happy to sense the feeling of an oncoming orgasm subside. Elle, now unencumbered from balancing herself, was able to use her newly freed hands to apply some personal attention to her own clit. The combination of the two things resulted in a beautiful crescendo.

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When we viewed the video some time later, back from vacation and over friendly drinks after a day around the pool, I was impressed by Kate's filming and cinematography. The finished product was able to capture the intensity of the moment perfectly: the defined lines of the underside of my cock, the swollen pink of Elle's pussy, the creamy residue of her wet along the length of my shaft, the precision of her fingertips as they worked her clit; and that intensity drove us both over the edge in real life.

It was Elle who started cumming first, her body glistening with sweat, her mascara smeared a bit on her cheeks, her pussy clenching with contractions, and the intensity of her climax initiated a sequence that I was powerless to stop.

Of course I told her that I was about to cum and figured that she had to have felt my cock harden for the last pushes into her, yet she did nothing to stop the process. As I thrust my hips up to meet her, my cock instinctively driving its seed as deeply into her as it could, there was neither a word from Kate, who was still focused on the screen of her phone, making sure to capture every last detail. When Elle finally cried out that she was done and I felt her body go limp, I lowered her back down onto me, back to chest, and did my best to catch my breath and regain my senses.

The video showed my cock staying stiffer than usual, the effects of the Viagra I had taken previously, still slowly dragging itself out of its warm cocoon, unleashing a slow drip of my milky white jizz. My mind, though not even thinking straight, was put at ease when Kate hopped on the bed next to me, an excited smile on her face, and went straight to kissing me.

"That was so hot," she whispered in between breaths, "I am so damn wet right now."

TWENTY ONE:

I took the opportunity to roll Elle off of me and onto the bed before returning to her, my fingers slipping between her legs and verifying the accuracy of her claim.

The woman did not lie.

We kissed for a bit, unable to embrace one another as our hands fumbled about between us, each of us pawing at the others sex. It was obvious we were hot for each other and I was thankful for the chemical enhancement of the pill as I hadn't lost my erection and was looking to take advantage of it. It wasn't like I specifically asked for consent from Kate, it was just the way things were progressing. Plus, it wasn't like she was resisting in any way either. Quite the opposite.

With the way things had been progressing I had figured we were going to go straight to the fucking though was pleasantly surprised when she got on top of me in a 69, planting her soaking pussy right on my mouth, her own lips around the head of my dick.

I was amazed by how hard my dick got and was astounded by how amazingly in sync we were. With each lap of my tongue across her clit she responded with a ring of her own around me. I could feel my head beating through my swollen, purple head and was thrilled when her thighs clamped around my ears and she shook through an orgasm, I just wanted to be inside of her.

With surprisingly little recovery time, Kate spun around and lay on top of me, our tongues once again wrestling, her tiny body sandwiching by cock against my own.

"Shit, Will," she moaned into my ear, "you have no idea how much I needed that and need you."

There was zero hesitation in her actions when she reached between us and guided me into her, my entire length slipping easily into her slick opening and each of us let out guttural sighs of relief at the fulfilling sensations it brought to us.

There was no resistance as I began to flex my hips and groin, drawing myself in and out of her at an even pace, her pussy walls clenching with each smooth stroke.

She made no attempt to stop me as she quickly climaxed, her body quivering practically uncontrollably, her walls desperately trying to milk me of my seed.

There was no commentary as she dismounted me and spun into a 69, taking me into her mouth and presenting herself back to my own.

I hadn't said a word when she quietly commented on how hard I still was and sat on my lap, her back to me, her body blocking my view of my dick, which I felt her hands moving up and down on, slick with her own saliva.

There was no uncertainty in her actions when she, without another word, raised her hips up and, once again directed my phallus into her, though this time into the extra-tight opening of her ass.

It was Kate's whimpers that really stirred Elle, who previously had been passively watching the action from beside us on the bed but now apparently wanted to get a closer look. I caught her wide eyed look when she saw her mother sliding her stretched sphincter up and down my length. Though, if upset, she certainly didn't convey the emotion as her only real reaction was to grab the phone her mother had been using to record our action and turn the tables on documentation for posterity.

By my own admission, I didn't have that much experience with anal and to that point had experienced it maybe a handful of times in my life. The reality was that, without a willing (and potentially enthusiastic) partner, it was less enjoyable for me than "normal" vaginal intercourse. Afterall, biologically speaking, there was a warm, wet, welcoming opening just centimeters away that actually wanted attention, why deviate?

Kate made me a believer in deviation in the right circumstance.

I can't say what it was that made the experience so fantastic. There were no pornographic verbal theatrics, there was no squirting or other visual cue, it just worked.

She had spun around and faced me though still sat almost upright across my waist. She was grinding her clit into me, working her hips back and forth, her tight abdominal muscles clearly defined with each movement. The only sounds coming from her were a deep, breathy moan interspersed by the occasional whimper though, with the only other real sound in the room being that of the shifting mattress below us and the soft click of the digital shutter, it was as clear as day.

Perfectly timed, she began to orgasm just as I felt mine come on. It has always been my experience that, with a second orgasm in a short period of time, though not necessarily as fulfilling as the first, I did find that my dick did swell just a bit more; a bit thicker, a bit harder, a bit more effort to blow. It did not go unnoticed.

"Oh, my God," Kate wailed, catching Elle a bit off guard, her eyes going wide once again, a huge smile brimming across her face.

"Don't stop! Don't stop! Don't stop!"

Truth be told, I wasn't doing much as she was driving the action. But if her calls were just to the heavens, that she didn't want the sensations and pleasure to stop, then I was in full agreement.

Her ass was so tight.

Like, SO tight.

It squeezed my cock and made it feel like it would legitimately split open.

Thankfully, the pop came in a different form.

I unloaded deep into her at what seemed to be the peak of her own climax, a point in which she did break through vocally and let out a legitimate battle cry. Elle was practically buried in the action, the video later showing the high-definition detail of each of our loins pulsing through our orgasms: in unison, in conflict, in any way that our bodies needed them to in order to process what they were going through.

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When we finally came down from our dual high all three of us collapsed on the bed, me in the middle, Kate and Elle in each arm. I wish I could have gotten a picture of that, the little bit of calm in an otherwise chaotic scene. The bed was a mess, the girls' hair equally so, the area around it strewn with pillows and covers and towels and anything else that could have gotten in the way. As I write this, in hindsight, that mess couldn't have possibly foretold the shit-show lay in front of us: the next day, the rest of the trip, the rest of my life.

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It is going to seem anti-climactic to breeze through the next day's events like I now will but the reality was that words will just never do them justice. It started with 28 of us (our 23 and Hunter's 5) traipsing into the jungle, gear, food and an overwhelming amount of booze on hand. Camp was set up, clothing was discarded, fun was had.

By noon I had witnessed a few of the girls performing a blow-job competition on a couple of the guys as well as Kate and Shannon messing around with each other.

By 2pm I had already cum during a threesome with both Sophia's, a delightful sexcapade that at least found us alone at one end of the beach but also included the enlightenment that I had put my dick into every girl on the trip: the few that I had not known about were a part of the sex contest earlier in the week.

By 4pm the beach was the scene of a full-blown orgy: Guys and girls, girls and girls, older and younger, oral and anal, there was nothing that I didn't see. I can't deny it wasn't strange to look up from my spot on the sand, being ridden by one of the girls on the trip, to see my Bethanny riding Hunter, not more than fifteen feet away from me. While I can't remember who it was my dick was in at the time, I suspect the other visual was one that I wouldn't forget... whether I wanted to remember or not.

By 6pm a few of us were sobering up and starting to survey the damage: passed-out bodies and exposed flesh, puddles of puke, missing clothing, trash everywhere.

By 9pm we were back at the resort, those of us who were able taking those who were not back in shifts with promises to help with bathing and bedding once the cleanup was complete.

By 1am I was finally finishing up myself. Shannon was already passed out in the bed next to me, Kate in the room adjoined. Jenn and I were the last remaining survivors after seeing all the girls... and guys... back into their rooms in at least a manageable state. There had been some tears, there had been some sickness, the question of how many memories would make it out would yet to be seen. For our part, I was surprised when she asked me to lay with her, figuring that she too would have wanted some space and the ability to sleep things off on her own. But it was undeniably nice to fall asleep with her, cuddled into my chest, her warm, soft skin draped over me, the fresh, clean scent of the shower a welcome replacement to that of grime and booze.

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The few days left in the trip were, by all accounts, tame as compared to what we had experienced in the days prior. It was brought to my attention afterwards that I was not the only one "sowing their oats" in the tropical paradise and the number of stories that were told in lore in the weeks and months to come did not seem to have an end.

It wasn't to say that there was no sex moving forward, just not to the same degree as that final trip to the hidden cove. There were a couple of hookups, a few vacation rendezvous', the things that we had originally figured would be the extremes, not the "child's play." For instance, I myself spent an extremely enjoyable evening with Rosie and Emily (one of the sex challenge participants) and had the honor of a third hookup with Jenn.

But, when the trip came to an end, it all did.

Well, I can't necessarily say that either.

A few things in my life changed when we got back home and experienced the evolution of what would be my new normal.

First, for the rest of the summer and for a few years to come, my pool was the place to be and nobody ever wore a suit. Every hot, sunny day I was treated to a Playboy grotto-esque display of flesh and fun as the various original women from the trip practiced their love of life "au naturale." No, there weren't any orgies. No, there weren't any poolside sexual displays. It was much more in line with a classical definition of nudism: everyday life, though in the buff.

Second, Heather and I became an item. It turns out that the "thing that she needed to take care of" and the reason she wouldn't hook up while on the trip was because of a possible reunion with her ex-husband. The reality was, after their breakup, they were individually lonely and considered getting back together just to be with someone and she wanted to at least give it a proper chance. But, in attempting the reconciliation, they realized they broke up for a reason and parted on amicable terms as opposed to ending up hating each other.

That said, we come to our third change in my life: a significantly more busy sex life... at least more busy compared to my life prior to the trip. While my direct relationship with Heather consumed the vast percentages of my experiences we can also add that she turned out to be a bit of an adventurous soul. Not only did she not fault me after learning of the experiences of the trip, but even invited a bit of that adventure into our own bedroom.

As for the rest of the group? Well, each has gone in their different directions over time though some fun reunions have occurred here and there. In fact, a few of us are in the process of setting up another trip down to the resort.

But that will have to be another story for another day.