Single Male Chaperone - Reimagined

"Have you ever done this?"

Her question was obviously for me though her attention was on the room as she was pushing me backward into the chair, my erection pointing at the ceiling.

"Ha, who am I kidding," she continued, as if speaking to herself. "Of course you have. I should be the one letting you show me stuff."

I laughed, a reaction that surprised her though thankfully did not make her feel bad.

"First off," I responded, "never hesitate to take control with your partner to have them do things that make you feel good. Unless they are literally getting hurt in the process there would be no reason they shouldn't want to be a part of it."

She was sitting on my lap, face to face. I could feel the tickle of her pubic hair against the back side of my erection and its mini-stimulations made me throb. I so desperately wanted to be in her.

"Second," I continued, "I think you would be surprised at just how uneventful my sex life has been. I'm learning here too."

Rosie leaned in and kissed me, her small breasts pressing into my chest and the touch of her nubby, eraser-like nipples continued to excite me.

She was wrong in her assumption that I had ever experienced the position before and, even without entering her, I realized I already liked it as it left my hands completely free and at a perfect angle to explore.

Free to touch her breasts and nipples.

Free to trace the contours of her face and neck.

Free to enjoy the sensation of the soft skin of her sides.

Free to explore the firm curves of her lucious ass.

Reaching around, under her ass, past her butthole, right to her pussy, I could feel her wetness. The old saying that she was literally dripping wasn't hyperbole, she was literally that wet.

"Oh, my God," she moaned as my fingers dragged her own wetness across multiple erogenous areas, "please just fuck me."

I aim to please.

Rosie got on her tiptoes and allowed me enough space to slide into her and the immediate sensation was incredible. My mind was having difficulty processing just how wet she was. My mind was racing with the thoughts that, at a certain point, wet was just wet, right? How could it feel more of something it already was?

I thanked my wandering thoughts as I felt her pussy begin to clench around my cock. Christ, if she orgasmed this quickly no wonder she liked the position.

Rosie, unlike during oral, began to cry out loudly as she ground her clit into me with each even, progressive thrust on my groin. Heat radiated off of her entire body. While her skin had started sticky, it was now slick with our combined sweat.

"Fuuuuuccckkkk!"

Her eyes were closed, her hands were on my shoulders, her body had become rigid, no longer directing stimulation toward her clit, instead riding the waves of pleasure as the ripples of orgasmic contraction unconsciously forced her pussy to attempt to milk me of my seed.

Unfortunately, I wasn't ready to cum.

I had slid a bit uncomfortably down the chair and took the opportunity to get up and, with my arms in the nook of her knees, I took her with me.

Standing cow-girl? Add another position to my list of experiences.

I walked to the wall and pushed her up against it, thrusting into her for a few moments before realizing that the position was not that great for either of us and, upon that realization, took the opportunity to throw us down onto the bed. The action was met with an excitedly fiery look from Rosey that confirmed to me that she too was not ready to call it a night.

I crawled onto the bed after her, diving my face back into her steamy pink and licked her clean of all of her wetness, leaving a fresh canvas to work with.

After arranging a couple of pillows under her hip I pulled one of her legs up against my shoulder, spreading her widely open, and took the opportunity to plunge deeply back into her depths.

"Urrrrgggghhhh..." Rosie groaned as I bottomed out.

"Bad?"

"No," she moaned, unable to open her eyes. "Very, very good."

In that position, another first for me, it didn't take much for the sensations of an orgasm to come on and I continued with my deep, hard strokes until I could take it no more.

"I'm gonna' cum," I grunted.

Rosie, now finally drained of energy, said and did nothing other than let her body go limp and, after pulling out, I finished myself off with my own hand, launching raindrops of cum across her torso before I too collapsed on the bed.

After a moment of rest I looked at the clock.

12:43am.

Another day.

Though, over the course of 24 hours, 5 women. The least "normal" day I had ever experienced.

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I woke up in my own hotel bed somewhat early though surprisingly refreshed. Sarah was asleep in the bed next to me and, in the still-warm air of the room, she was sprawled fully nude across the sheets, the look of her body being the very definition of soft and warm. Personally, I was thankful that I had insisted on both Rosie and I showering before I left her room as there would have been no way I would have slept soundly otherwise.

As per my phone it was 6:45am, slightly earlier than I would normally wake up at home and most certainly earlier than I would have ever expected anyone on vacation to get up. So, I slid on a pair of athletic shorts, grabbed my sneakers and headed out for a run.

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She was coming out of the water as I made my way back to the resort. I had noticed someone swimming about 30 meters off the shore previously but hadn't put much more thought into it other than a little bit of jealousy. While a strong pool swimmer, I admit I was a bit nervous as to attempting open water swimming on my own.

I was still about 400 meters down the beach so it wasn't like I was able to get an extremely clear look but I was intrigued by what I saw: Full, racer style swimsuit with open-water goggles; long, red hair when she removed her cap; large, full breasts and hourglass figure when she removed her suit.

She disrobed, dried off, put on a robe and made her way back to the resort surprisingly fast; quick enough that even by the time I got to where I thought I would catch up with her there was nobody in sight, just a few random hotel employees wandering around and getting ready for the day.

I showered, had eaten breakfast by myself and was heading down to the beach by myself, book in hand, before I saw even the first glimmer of life from our group, a few sleepy girls heading toward breakfast. After offering and receiving a friendly wave, I set up shop in a resort lounge chair under a palapa.

I lost track of time though figured it must have been about 90 minutes when she approached me. I had noticed the other chairs filling up though had not realized that the one next to me, the second of the organized pair under the palapa, was literally the only seat left on the beach.

"Excuse me. Is this seat taken?"

I looked up to see a Jackie O. type figure: large hat, large glasses and large draping swimsuit cover-up.

"No, not at all," I responded truthfully. I hadn't made any specific plans with anyone, no need to let the chair go to waste.

I had expected that she would have pulled the chair away for some privacy but was surprised when she immediately started dropping her items and getting herself situated.

"Can I give you a hand with anything?"

"Nope, all set. Just working to get as comfortable as you look."

I laughed and attempted to get back to my book, an attempt at privacy for my new companion but was just unable to focus.

"Will!"

I turned to the voices and saw Kate and Sarah with a couple of the girls and waved to them.

"We're going for a walk for a while. Care to join us?"

I waved them off and turned to find my new beach mate who, having already taken off her sun coverup to expose a string bikini, was in the process of taking off her large hat... which in turn let down her long red hair.

I felt a smile on my face.

"Well, if I can break the ice even though you probably figured it out," I said with my hand outstretched, "I'm Will."

"Heather."

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After confirming that we had in fact seen one another on the beach that morning, we fell quickly into conversation and were fascinated to find just how much we had in common.

To start, we were both acting as chaperones on our trips. Hers was more of an honorary designation as she was traveling with her sister's bachelorette party and, at 9 years older than even the closest other attendee... and the groups focus on getting practically black out drunk each night... she felt like a "mother hen."

"I figure to just stay out of their way for the most part," Heather explained. "I'm not going to ruin their trip nor let them ruin mine. Besides, it's day 4 for us and all of them are in such rough shape already they can barely get out of bed. Bunch of lightweights if you ask me."

We were both into running and swimming; me moreso running, her moreso swimming. And immediately agreed to share a workout or two during our aligned days at the resort.

We were both single, though her relationship status was based on a more-traditional divorce as opposed to the death of her spouse. There was a bit of hesitation in her voice when she spoke of her relationship status though, as we had just met, I didn't press the issue.

We both owned our own businesses; myself with consulting, she with a small boutique "gallery" (as she called it).

"Do you like my swimsuit?" Heather inquired with an accompanied arm gesture across her body..

"Yeah, it's great. To be honest most of the suits I see these days tend to look the same, that one is somehow unique."

Her suit was pretty nice. In addition to being a shade of green that I just hadn't seen before, it actually consisted of a significant amount of sheer mesh. While all of her "private bits" were covered by opaque fabric, the majority of the suit itself was completely see-through, a fantastic combination of give-and-take to the interested viewer.

"It came from my gallery. You should come check out the stuff I have for guys," she added with a wink.

The similarities continued in that we were in the same age demographic and I was surprised to find she was 38 years old as I would have guessed about 10 years younger than that based on her physical appearance.

And, finally (and potentially most importantly) we lived about 20 minutes away from one another back at home. Maybe that shop visit wouldn't be so unreasonable after all.

"Oh, my God," she squealed in delight at the revelation, "I'm in that area all the time! I can't believe we have never met before."

I confessed my rather hermetic lifestyle and tendency to revolve my life around my Bethanny though explained how she was encouraging me to get "back out there."

"She's probably right, you know," Heather said as she started adjusting herself next to me. "Obviously we don't know each other that well but you seem like a pretty good guy."

I felt myself blush and a shitty grin go across my face.

"Oh, boy," she chided upon my reaction, "another guy letting a compliment go to his head."

Heather had gotten up out of her chair to stretch and straighten her towel. Her standing and movement gave me a bit of time to size her up a bit more and continue my evaluation from the morning. She was on the small side, probably 5'1" and about 125lbs. There was no illusion to her hourglass figure that morning as I estimated her measurements to be around 34-22-32 consisting of full, large breasts; a narrow waist and flat-but-soft stomach; sensual hips and ass. The back of her bikini bottoms revealed a wide-band thong that only accentuated her round, peachy ass.

In a sea of beautiful and scantily clad women, this woman was leading the pack.

The conversation had been going for some time when I noticed some of our group, out of the corner of my eye, coming our way, Bethy was leading the pack.

"Hey, Dad!"

"Hey, there. What's going on?"

There were 3 other girls with her, Taylor and two additional girls, both named Sophia, that I didn't know quite as well. All of the girls were topless, all of them were wearing just slightly smaller than "normal" bikini bottoms.

The Sophia's, coincidentally, were two of the largest, curviest girls of the group. Some may even use the acronym BBW to describe them. It was interesting that they had the same name as they were so similarly in look and build: long, dark hair; oval shaped faces; thick all around; soft tummies; large breasts and areola; waists that narrowed from their busts and flared to their hips; pierced navels. Each had an absolutely lovely, renaissance-type beauty in their face and, for all of their additional weight, neither had even the smallest visual indication of cellulite.

To be honest, they were sexy as hell.

"Hey, Dad, I was wondering if I could talk to you for a minute, is that okay?"

I could sense that she meant for the conversation to be private.

"Absolutely. But, hey, before we step away. Ladies," I meant for my comments to be directed at all of them, "this is my friend, Heather."

I got up from my chair and explained how close she lived to all of us and asked for Taylor and the Sophia's to keep her company while I spoke to Bethanny.

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"Dad! Oh, my God! She is so hot!" Bethanny was barely able to suppress her excitement when she started talking and I was worried that we were not far enough away that Heather would still be able to hear us. "And a red-head too! Right up your alley. I'm glad you're taking to heart my comments on you getting back out there."

"Ha. Well, thanks," I responded. "But I don't think it's like that with her. Besides, I think I have my hands full with the girls on this trip."

"Yeah, I heard about you on the beach yesterday and I get it. But all of that is just for fun. Who knows, since she lives so close, maybe Heather could be a long-term thing."

I knew it was strange that, not only did my daughter know about...but also didn't seem to care at all about... me having sex with her friends. But, I was thankful about being able to talk to her so openly about things and for her to be so encouraging as I explored this new stage of my life.

"I suppose. You know it's all pretty new though, I don't want to rush anything."

"Sheesh, c'mon dad. Try to loosen up."

She playfully hit me on the arm.

"Doesn't it seem strange that I am the one having to encourage you to do these things? Besides, as far as my friends are concerned, the boys at school are mostly immature children. It's great that everyone can get some feel-good practice in."

"Well, glad to be of service, I guess," I responded through a chuckle.

"Anyhow, the reason that I am here is that we were talking to some of the hotel staff and they were telling us about a really great beach a short walk away. They said that it is really secluded and has a cool vibe to it. It would be totally nude but they did suggest that we have a guy with us as sometimes the locals go there and, for whatever reason, they would leave us alone as long as there is at least one male there."

"What's wrong with nude here by the resort?"

"Yeah, I know. We thought of that. It just seemed kinda' cool. Like an adventure, ya' know? We've been taking a poll and literally all the girls want to go. Would you be cool with it?"

The thoughts bounced around in my head for maybe 3 seconds. Normal decision making points such as if it would be appropriate for me to be nude; if all the girls would actually be okay with my nudity; what about the other moms; all standard stuff. But, in the end, 3 seconds came and went in about 3 milliseconds.

Carpe Diem.

"Sure," I responded. "Why not?!"

Bethanny pranced off with her friends, giddy and excited. I settled myself back into my seat.

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"I think it's great," Heather said when I told her about the conversation. "Afterall, you yourself were saying that the goal of this trip was not just a vacation but for an empowering feeling for the girls. Most women... heck, most men for that matter... get hung up on their bodies, even when around friends."

Heather had gotten up and was gathering up her belongings to meet the rest of her group.

"So, c'mon, break out of that shell of yours. Besides, those girls are hot! And, if the conversation I had with them is any indicator, you might even get lucky out on the sand too. They are ready to party!"

I practically spit out the sip of my drink at her comment and felt my face flush with embarrassment.

"I'm here for another 3 days and will be back out here on the beach for as much of them as possible," she said with a mischievous grin. "I won't see you tomorrow obviously but maybe you'll meet me again the day after? You can tell me all about it then."

I sat there, basically dumbfounded. Heather, needing to leave but obviously wanting to put further stamp of approval on her own suggestion, leaned in and kissed me. It wasn't a little peck on the cheek, rather a direct kiss on my lips. And, like that, she was gone. Just the sexy sway of her ass, some racing thoughts in my mind and a bit of swelling in my shorts were all that were left. I needed to work things out in my head, I needed to get rid of the chubby, I needed to go for a walk.

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Inevitably, the conclusion of the walk was not the one I expected. I just couldn't get the thought of Heather out of my mind.

With each right foot step I saw the image of her amazing body in my head.

With each left foot step I sensed her lips pressed against mine.

With either foot I felt the bounce of the thin mesh fabric of my shorts against my blossoming erection.

Instead of the walk working in my favor to regain my composure, it did the exact opposite.

By the time I reached the edge of the resort property I had a full-blown erection that made my shorts stand out comically in front of me. Solution? Take them off.

Of course in a normal world, walking around the beach with a raging boner would have been a faux pas of monumental proportions, a cause for shame, possibly even arrest for indecency. I had hoped that the lack of covering, and therefore physical stimulation against my swollen phallus, would aid my cause in reducing my arousal but the warmth of the sun and visual stimulation afforded to me allowed nothing of the sort. Within 20 yards of leaving the property I locked eyes with an extremely attractive woman who, though in the process of riding her partner cowgirl style, still made very clear eye movement toward my crotch and offered in return a smile and increased volume in her love making.

Though, normally, I would have been mortified, considering my predicament, I was thrilled when the single voice called out over the monotonous sounds of the sea.

"Mr. Patton! Will!"

I turned to find Madison, an extremely close friend of Bethanny's, and our next door neighbor, walking toward me.

Madison was a girl that I had most certainly seen topless before but this, like most of the girls, was the first time I was seeing her fully in the nude. She was shaped similarly to her mother, with smaller, perky, b-cup breasts; wide hips; shapely thighs and calves; and muscular arms that totally screamed what I already knew about her: Madison was a competitive gymnast.

Madison and her mother, Christina, moved in next door to me back when the girls were 10. Christina, like me, had lost her spouse and was doing her best to "start new" with her daughter. For Bethanny, Christina was the closest thing she had to a mother. For Madison, I was the closest thing she had as a dad. In fact, the closest thing I ever had to a relationship after the death of my wife was in seeing Christina for a few dates. She was a lovely woman physically and personally, traits she passed on to her daughter and ones that anyone would love and a significant other, but each of us agreed that the fit just wasn't right. Instead we have spent the years as very good friends, both of us remaining single.