Single Male Chaperone - Reimagined

"Hey, what's up?"

"Just looking for sunscreen. What's so stupid?"

"Oh, nothing," I responded, handing my daughter the bottle of SPF15.

"Your father claims that his penis can tell the difference between women."

Bethy had a confused look on her face as she spread the thick white lotion across her breasts and shoulders.

"As in," Kate continued, clarifying her earlier statement, "he thinks that he has some sort of super dick that can feel the difference from woman to woman."

"Well, I should hope so!"

A sense of pride for my daughter coming to my defense swelled through me.

"Bethy, honey," Kate repeated while slowly shaking her head, "you're young and you're sweet. But I think you are going to come away with some hard life lessons in the future."

Thankfully, Jenn and Shannon also both came to my defense.

"I don't know, Kate. I have to agree with Will on this one. I think that a guy would be able to tell the difference," Jenn added.

"Seriously, for me I think it is some nerve ending stuff that occurred during my deliveries. I think guys could tell just like women can."

Shannon had actually stood up and next to me when she spoke, both a verbal and physical defense.

Of course, we were all still laughing throughout the entire discourse as the exchange wasn't angry, rather silly.

Kate walked up to me, a smirk on her face. For the briefest of moments there was silence, like a scene in an old Western flick, everyone just waited to see what she would say.

"Okay," she said, wrapping a hand around my chubby cock, "prove it."

Bethanny's eyes nearly popped out of her head. "Holy shit," she laughed, "are you serious?"

Kate called our entire group around us and explained the situation.

"I am wondering if we can have some volunteers," she continued in her announcement. "It doesn't matter which side of the argument you are on or who you would be siding with to win, just that you want to help with the contest."

"Do you think you can do this?" Jenn had been stroking my cock, getting me hard and whispered her question so only I could hear.

"I mean, I think so," I responded truthfully. "I guess time will tell."

I was instructed to lie down on a couple of beach towels and was blindfolded with the wrap I had worn during our walk over. It was a little nerve wracking, to be honest, to be so exposed and not really have control of what was going on. In hindsight, when asked by the few people I have told this story to why I went along with the entire thing I can only offer a couple of weak explanations. First, I was still quite drunk. Second, the Viagra still hadn't worn off. Third, well, c'mon! I am a guy and I was being offered the opportunity for sex with any of a number of beautiful women.

"Rules are as follows," I heard Kate announce. "Will will lie still and refrain from as much movement as possible. He is not allowed to use his hands at all. Obviously factors such as smell or sound can impact his choice but it is suggested that the girls be as quiet as possible."

Though my erection never subsided under what I assumed was Jenn's soft touch, I admit I was a bit nervous.

"Our target will mount Will, cowgirl style and ride him for two minutes. After that, each of the seven volunteers will get 90 seconds each, hopefully in relatively quick succession, before Will makes his choice."

"Seven?!" I was shocked to hear the number.

"That was what it was narrowed down to in an attempt to keep it somewhat reasonable," Jenn whispered in my ear, "more actually wanted to be a part of it."

"Will, are you ready?"

It was like the starting blocks of an Olympic race.

"I guess," I replied. This trip was absolutely out of control.

ELEVEN, TWELVE, THIRTEEN, FOURTEEN, FIFTEEN and SIXTEEN:

I felt movement around me, my cock being released and, soon, the very obvious sensation of being straddled. I attempted to stay cool as I felt my dick being positioned but did find myself unconsciously holding my breath as its head pressed up against an obvious opening.

It wasn't altogether very wet, not surprising considering the circumstances, and it took a bit for my target to get herself not only fully impaled on me, but into any sort of rhythm of movement that I might be able to pick up some mental cues from my partner. Yet, as my brain spun, I couldn't think of a thing. Was Kate right after all?

I figured we had to be getting close to the two minute mark when I felt a couple of small hands press up to my chest. I had felt our bodies begin to adjust to one another, my partner had most certainly become wet and I heard a very soft shudder in her breathing. It felt sensational, but there was nothing in particular that was able to say to myself 'look for this' in the future.

"Okay," Kate announced. "Time's up."

I felt a small amount of weight press into my chest from the small hands and, as the participant dismounted me, I felt a tiny scratch of a fingernail as her hands left my chest.

I got nervous.

"Participant One."

It was the only thing that I heard before I was mounted again. While it was probably only about 30 seconds from my target leaving and "participant one" getting on me, my mind raced. Had I gotten too cocky? Would I be able to do it? After all, maybe it was the entire experience that defined one woman to the next. Not just her pussy, but her touch, her kiss, her smell. The sensation of her breasts on your chest or in your hands or mouth. The scent of her perfume or natural musk.

I felt two knees get to each side of my hips and a hand grasp my cock to guide it into place and, as soon as they had settled themselves onto me, I immediately knew. Fireworks went off in my brain and my confidence began to come back. Certainly there were differences in the new participants weight and touch but it was my dick that really called it out to me.

"Nope!"

"Damn it!"

A female voice that originated obviously from just in front of my face expressed their frustration in not being able to trick me and a chorus of giggles emanated from the bystanders around me. A smile came to my face as I heard Kate shush the audience and warn them as to giving me clues and the second participant straddled me.

Numbers 2 and 3 were also obvious and immediate non-factors and I called out my negative assessments almost as quickly as the first. Each was nice; warm, wet and smooth, but neither was the original.

When participant 4 straddled me I was suddenly filled with a sense of deja vu. It felt very familiar. Could this be the one? The participant was more wet from her initial mounting than the original target was but my mind justified it as just being turned on from the displays of sex I had been a part of offering.

We settled into a comfortable rhythm pretty quickly and it seemed altogether too soon that Kate called out that the 90 seconds were up and that participant 5 should mount me.

That was when I panicked.

The fifth pussy to accept my cock felt just like the 4th. Was it a trick? Was it actually the same person? What else could I use to try and decide? The touch of her skin? Her scent? I tried, discreetly, to take a deep breath in through my nose but all I could pick up were the smells of the beach and the sea.

Too soon after it started, time was called and I was almost immediately mounted again and, like numbers 1, 2 and 3, #6 was an immediate no though, as number 7 mounted me, my mind was still racing on numbers 4 and 5.

Number seven was familiar. Not that I thought that she was my original target, just that she was familiar. Though I could originally feel my face contorted into a "deep-in-thought" kind of pose, I literally felt the smile come across my face when the thought of that familiarity began to lead to the memories and experience of the last few days. My life had gotten crazy, I had experienced different things and different women and number seven was almost most definitely one of them.

"Time!"

I heard Kate call out though number seven did not stop her gyrations on top of me. Instead of dismounting, in fact, my partner increased her movements.

"Time!" Kate's voice rang out again and I heard a number of laughs from around me.

Number seven still did not abandon her perch and, whether it was me just getting into the action or whether it was a mutual disregard for the rules of the game, I felt my own hips begin to thrust into my willing participant.

It was when I broke protocol and allowed myself to use my hands to grasp the hips of my rider to steady my thrusts into her that I heard Bethanny's voice coming from the crowd.

"Holy shit," she said, a chuckle of disbelief in her voice, "that's my dad."

A number of voices began laughing and Kate's voice rang out again.

"Oh, for God's sake, I said time!"

Number seven had already taken to laying on my chest and a rush of cool air hit it when it somewhat abruptly was pulled from mine, our skin sticky between us. There were chuckles from the crowd and my imagination, aided by the sounds of movement around me, pictured her physically being pulled off of me, my wetness slick cock offering an audible slap against my stomach when it left its slippery home.

"Okay, Will," Kate said, trying to shush the crown in the meantime. "What's your choice?"

"I think I know," I said semi-truthfully. "But I am hoping to feel numbers 5 and 4 again."

There was a bit of a hum in the crowd before Kate agreed to my request.

"Okay, Will. First is number five."

I felt the familiar warmth wrap itself around me again and, almost immediately, a small set of hands press onto my chest. Was this my target? I so desperately wanted to grab onto her, to rip my eye covering off, to experience every aspect of this partner with more than just my cock but, before I knew it, without Kate even calling for it, she dismounted and left me alone on the towel.

"Last one, number four."

When my cock was again nestled into the comfortable, waiting warmth of an unknown woman for what was supposedly the last time, I had a sense of sadness. Not only for the fact that I did not know who I was sharing the moment with, but that I honestly did not know if my original target was number four or five. While I could potentially be commended that I was able to immediately dismiss over 70% of the pool, I still figured that I would have been able to tell more clearly. While I did my best to clear my mind, get rid of the negative thoughts that were only a reaction to the competition and instead focus on the beauty of the experience I was having in that moment, I was sad when I felt #4 begin to get off of me, knowing that it would only be a guess, and if I guessed wrong I would potentially be inflicting a tiny emotional scar on what was most likely an impressionable young woman.

But, then, a miracle happened.

As number four allowed my cock to slide out of her and used her hands to push off me, I felt the familiar scratch of a fingernail on my chest.

I let out a deep sigh of relief and laid back on the beach, allowing myself a moment to collect my thoughts.

"Okay, Will," I heard Kate say. "Now or never."

I stood up and pulled the scarf off from over my eyes, taking a moment to let them adjust to the light and allowing myself a chuckle at the sight of my cock, still hard, still pointing more up than down.

"Number 4," I announced.

I heard Jenn and Shannon start to offer an overacted cheer while Kate said nothing and instead offered a slow clap in response, an annoyed but playful look on her face. I looked around the group, all somewhat standing awkwardly, not necessarily knowing how to react to the display that was put on in front of them. Of course I also tried to figure out who the 7 mystery contestants were but, alas, I was unable. However, in my examination of the faces, both in passing and under a bit more scrutiny, I swear I did see a small look of interest in many of the girls. Whether they were intrigued by the contest or it was something else altogether, I most certainly did not see any disgust so signs of being upset. Not even close.

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I was hungry.

We all were.

We had been on the beach for a number of hours at that point and the snacks just weren't cutting it. Everyone was still having a fantastic time, nobody wanted to leave and we needed a solution.

Though we were informed it was going to take two sets of hands, Jenn had contacted the resort and they agreed to provide us two bags of packaged meals. Enough for all twenty of us, enough to keep us on the sand for a while. We would meet the hotel employees at the entrance to the pathway and they would provide us with everything we needed, not only the food, but also sides and garbage bags to clean up after ourselves.

"You should just go now," Jenn informed me to my surprise.

"I'm going to get the food?"

I really didn't mind doing it, honestly, I was just a little surprised to be volunteered.

"Sure. My Brie can go with you since they said we would need two sets of hands."

Brielle had been standing by, I think she was the one who actually suggested her mom contact the resort, and had already taken one of the large, flowing wraps and begun folding it around herself.

"C'mon, Will," she said with a smile, "it will be fun."

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We had been talking for a bit, general small-talk like future plans and how we were enjoying the resort, and were still in the lush, green, soft portion of the trails, when, seemingly out of nowhere, Brielle's wrap fell off. Literally, just fell off.

"Oooohh," she gasped, legitimately shocked as to the occurrence, and crumpled to the jungle floor, chasing after the thin cloth.

"Well," I chuckled, "that's not something you see every day."

There was nothing flirtatious about the scenario. It was obvious that it was an innocently occurring incident and also obvious that she was embarrassed to have happened. I mean, one doesn't normally watch a person's skin turn that bright red that quickly during a planned activity.

"I'm so sorry," she said, doing her best to open the cloth back up in order to get it wrapped back around herself.

"No need to be," I responded, offering to give her a hand, "I mean, afterall, we have just spent the entire morning with one another fully nude."

It was adorable to watch the lightbulb go off in her head and watch, just for a split second, as the look on her face went from embarrassment to acknowledgement of reality and then back to embarrassment, as if she should have already thought about that.

"Yeah," she laughed, "I should have thought about that."

With a determined look on her face, Brielle took the wrap and simply draped it over her arm, her act of defiance against unnecessary propriety.

She, like her mother, was really beautiful. And, as the chemicals in my body still hadn't worn off, I felt myself begin to grow aroused, just from the sight of her. Good lord, I loved red-heads.

The cloth wrapped around my waist bobbed almost immediately... and though she most definitely saw, Brielle was not at all phased by it.

"That was pretty crazy out there," she said, her eyes never leaving the thinly veiled outline of my swelling dick. "The sex on the beach. The contest."

"Yeah," I responded, admitting truthfully, "can't say I have ever done anything like that before."

"Me neither," she responded, taking a micro-step toward me, closing an already small gap.

With the way I had tied my wrap it most certainly would not be just falling off my body but based on the weight of the fabric and the wide open seam down the front of my leg, it wasn't as if an erection would be restrained by anything either.

"May I?"

I hadn't released more than a grunt of approval before the nearly sheer wrap was pulled to the side and her fingers were wrapped around me and, even though I had technically just had (somewhat incomplete) sex with 7 different women on the beach, the simplicity of the touch of her hands sent a shockwave down my spine, even causing my dick to twitch a little in her palms.

Her eyes went wide and a huge smile spread across her face.

"That was so cool," she said, the focus of her attention never shifting.

What started as literally just holding my dick soon turned into a very basic hand job and what started as a slight swelling turned into a hard and proud erection.

"Can I..." She paused in her inquiry, "taste it?"

I slipped my hand in between her legs and dragged a finger along her groomed opening.

"Can I taste you?"

Cautious excitement filled her huge, round eyes when she looked up at me and my first reaction was to lift her up, off the ground and into me, her arms and legs instinctively wrapping themselves around me, our lips and tongues biologically drawn together like magnets.

We made out for a while, still in that standing position, each of our tongues jockeying for position. I could feel her heart beating through her soft breasts pressed into my chest. I could feel my erection straining against the bottom of her ass. I could feel her soft pubic hair tickle my belly.

When it was obvious that she was holding her own weight, I used my hands to explore her body; the tiny bumps of her spine down her back, the firm handfuls of her ass cheeks, the roasting heat of vulva.

I still wanted to taste her.

I lowered us down to the ground and, when her back finally met the soft leaves covering the jungle floor, she released her arms and legs from me, throwing them open as wide as they could be, an open invitation for me to take her body as I pleased. With no hesitation, I spun myself in a 69 position over her and got myself a taste of her waiting sex.

I took my time savoring the whole of her, with all of my senses enjoying the experience: Her musky scent, the slight saltiness of her taste, her whimpers of delight as my tongue worked its way around her swollen clit, the incredibly soft touch of the skin on her inner thighs as they pressed against my face, the sight of her winking asshole as she quickly rolled into an orgasm.

Though I admit I had positioned us in a 69 for her to return the favor of oral sex, I was so taken by her obvious enjoyment of the cuniligus that the thought of my own neglect was just a fleeting thought and, when she had recovered just enough from her orgasmic high to beg me to enter her, I was glad for the lack of build up on my own part as, to be blunt, the sensation of her pussy enveloping and gripping my cock was fantastic.

We stayed in our initial position, missionary, for some time before Brielle asked if we could switch. I had no problem with her riding me, cowgirl style, as it was not only a position I preferred but one that I knew provided more direct contact for an attention hungry clit.

We kissed for a bit, her body on top of mine, our skin sticky between us. Unlike what had happened on the beach, it was truly a mutual, sensual experience that, sticky skin and all, I was enjoying every moment of.

Of course, enjoying a sexual experience induces Mother Nature's intended consequences.

Brielle had sat herself up and positioned herself over my groin, reaching around herself to guide me into her. For my own part, I had settled into a little naturally formed indentation in the ground. It was not deep enough to affect our position in any way, rather just allowed for a bit of stability on the jungle ground. The sensation of it actually reminded me of my body being cradled by the sand of the beach earlier that morning.

She accepted me easily, our foreplay and initial penetration having done their job, and, as she settled herself down on me, my length fully consumed, I had a feeling of nostalgia... or deja vu... something was very familiar.

It took little effort for us to settle into an appropriate cadence and my senses were again rewarded for a job well done, most notably the contracted squeezing of my cock by her spasming vaginal walls. She was cumming and I was going to as well.