Single Male Chaperone - Reimagined

"Holy shit," I exclaimed, wide eyed at the sighe. "Where did that come from?"

"Everyone talked about it before the trip. I'm not quite sure why they thought it was a good idea to bring their toys into a shared-room but hey, who am I to judge? Then when girls started chickening out about bringing stuff Bethy offered to collect everything from everyone and just bring them all herself. The arrangement is that anyone can use anything, just wash it when you are done."

"Well, that answers the question of why her bag was so heavy," I said dryly and with a roll of my eyes.

Sophia giggled but her attention was squarely on the cornucopia of options on the bed in front of her.

"Which ones are yours?"

"Are you kidding? None of them. Remember what I said about no privacy?

Well, if nothing else, it seemed like the right thing to do to at least take advantage of the opportunity.

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I had Sophia lie on the bed and I grabbed a bottle of massage oil that I found in the pile. I took my time on her entire body: her hands, her feet, her calves, her neck, her breasts, the insides of her thighs...

When I could tell that she was totally relaxed I had her lay back and instructed her to spread her legs wide and, using a liberal amount of lube and just the tip of my finger, began working tiny, clockwise circles around her clit. It was the direct access to her "most" erogenous zone that I wanted to stimulate, to build up that feeling inside her, that... pressure.

For quite some time I teased her, bringing her right to the edge and back again, never over the brink. Sophia's body was at odds with itself. Physically, she was so primed we put a towel under her to soak up the stream of wetness. Mentally, she was a bit tortured, so desperately in need of relief that she was a bit manic.

Of course I didn't actually know if what I was doing was going to work, edging her like that. I had no idea if the concept was going to work in reality, especially considering the inexperience she had confessed to me, but it wasn't going to stop me from trying.

It wasn't just her clit, it was her nipples, her ass, her g-spot. It was with my fingers, with toys, with my tongue. Each time, right to the edge. Each time, easing up just before getting there.

It had to have been at least 30 minutes later when the moment of truth was upon us and the question as to whether or not the experience was worth it was about to be answered. There were 3 devices in use: nipple clamps, an external clitoral and an internal "j" vibrator that was pressed up against her g-spot. Sophia, for her part, was no longer relaxed. I had instructed her to hold her legs back but she was having trouble doing so, the contractions emanating through her core were so powerful.

"Holy shit," she moaned, her face red from holding her breath, "it feels so good."

I pulled the internal vibrator out and eased two fingers into her, cupping them and stroking the fleshy nerve endings inside her. Sophia, for her part, groaned and let go of her legs, whether it be that she was unable to hold them anymore, or because she needed to focus some attention on her nipples, which she immediately did. Me, well, with the clit vibrator still applying direct stimulation and Sophia working on her nipples, I decided to slip a third finger into her.

Big mistake.

It's a good thing that Sophia had a soft body as her legs clamped down on me so hard I thought she was going to break my hand.

"Bad?"

I could only whisper my question as I was so taken back by the force of pressure.

"Don't stop," she moaned back, pinching her nipples so hard it looked like they would pop.

Her moaning was guttural and it was probably a solid 45 seconds of max climax before her body began to go limp and I was able to pull my hand free. As to whether or not she was a squirter, I could not confirm, but my hand was soaking wet.

"I had no idea I could feel that," she said when she calmed herself down a couple of minutes later. "What did you do to me?"

I chuckled at her innocence and explained exactly what I had done and why I had done it. I talked about understanding what made each one of us feel good sexually and being okay with figuring it out. I told her I didn't do anything groundbreaking, rather just focused on tried-and-true methods that were suggested to work for other women.

"But, hey, maybe you will find that there is other stuff that could be even better for you."

When I made my comment, it was a bit of a throwaway, an indicator that one was never potentially done with their sexual journey. It was as if I was her acting therapist and mentor. How she took the comment was a bit more literally.

"You mean there's more? Show me!"

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Our next 45 minutes or so were testing out everything I could think of when it came to stimulating a woman; more of what we had already been doing... but with none of the edging. We lost count of the number of orgasms she had (though it was probably close to 10) but minimally figured out that the most powerful orgasm she suffered through was when we once again used the clit vibrator and I massaged her g-spot but, as opposed to getting direct access, it was a sort of secondary stimulation from two fingers in her asshole, all while she was on all fours.

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When we were finally done, when I had cleaned up all of the toys we had used and Sophia's heart rate, breathing and muscular coordination had gone back to normal, she announced that she was going to shower and, much to my surprise, asked me to join her.

Under the warm, cleansing water, and with absolutely no prompting, Sophia took the lead, not only soaping me up and washing me, but also posing an inferred question in a statement.

"You didn't have sex with me."

"Some might disagree," I responded. "We did what most would consider to be very sexual things."

"Yeah, but you know... we didn't actually do it."

Her soapy hands were stroking the length of my penis and getting me hard.

"No, we didn't."

"But I thought you were trying to have sex with all the girls on the trip."

Her comment took me a moment to respond to. The worst nightmare I could possibly have was being presented to me. Basically, I was seen as a predator. And, why not, I mean, I did go down on her without her consent, why should she believe me?

"Sophia," my voice was one of embarrassment, "I'm not trying to have sex with anyone. Sure, there have been circumstances that I have been with some of the girls a bit more intimately, but every one of those experiences was mutual, if not even them being the aggressor."

"Except me?"

"If you believe me, yes. Except you. I am not necessarily sure what came over me."

"I'm glad you did," she responded. "I said it before and I'll say it again now, I wouldn't have had the guts to do anything myself."

"So you're good?"

She smiled.

"Yeah, I'm good. For now."

Lordy, what ever could that mean?

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I felt like we parted ways on good terms, afterall, Sophia couldn't seem to keep her hands off of me for the remainder of the time we were together, constantly pulling me in for hugs, constantly kissing me and constantly playing with my dick. In the end it was messaging on her own phone that was the distraction that concluded our time together as the other girls were wondering where she was and telling her she needed to join them. We finished the afternoon with her promise to me that our time together was not done.

When I got back to my room I started running some mental calculations as to the last few days regarding Sophia's comments about my having sex with every girl on the trip. I decided that, penis in vagina or not, I should and would count the time I had spent with her as "having sex." So, from my time with Sarah at my house before leaving up to Lilly on the beach that day, whether I had climaxed or not, she was right in that my dick had been in a lot of different women.

I was still unsure about who took part in the beach challenge other than Brielle and Shannon but each of them I had been with "formally" in addition to the short period of time on the sand. I made an assumption that Kate would have insisted on having "fresh" participants (other than Shannon... who probably insisted on participating on her own) which meant, girls and moms, I very well could have been with 19 different people over the last 5 days.

19. Multiples more than I had been with in the many years combined before and almost our entire group.

But, if I was that close, who was left? There were the girls in the room for waxing: Jamie, Sophia (2), Emily, Annie and Hope, only a couple of which I knew very well. Plus there was Elle, Kate's daughter, and finally there was Kate herself, but she had already indicated that she wouldn't be "putting 'P' in 'V." And that was okay. The trip wasn't about me.

It all got me thinking though, why not? I realized that I had been deluding myself over the last couple of days in that my motives were somehow altruistic. 'I'm doing this for their benefit,' I kept telling myself. But why? Was there some reason that I couldn't or shouldn't be interested in pursuing these interactions? Sure, things were completely different than how I had ever lived my life previously, but was there anything particularly wrong with wanting to be with these women (and all of them were, in fact, women)? But I also had thoughts of Heather in my head; how desperately I wanted to be with her, how much I wanted to see what type of relationship developed.

I chuckled to myself. Of course my mind was going to be doing some gymnastics as the ethical nature of my actions or this trip in general, that wasn't surprising, it was just who I was. I was only surprised in myself that, as I plopped back down on the bed, a singular thought process and overall feeling was coursing through me.

I was really freakin' horny.

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After a run and short swim the next morning, I was sitting for a solo breakfast, well before most of our group was even up, when Bethanny joined me. We exchanged normal pleasantries while she began to wake herself up and it seemed like we were enjoying normal, father-daughter conversation until, I have no idea why, I decided to open my big mouth.

"So, I saw your big bag of toys. No wonder your luggage was so heavy."

As a note to the reader, I can't stress how open the conversation between Bethanny and I - or even Bethanny and her friends and I - would be back in our normal lives. As previously stated, I knew - and was fine with - the fact that she wasn't a virgin. While I didn't believe her to be some sort of wanton deviant, I wasn't bothered by the conversations that she and her friends had about their relationships and was often included in the conversation to add color from the male perspective.

"Ah, yes," she responded. "Well, not all of us have a harem of options just waiting at their beck and call. What's the count up to now? Huh?"

I felt my ears burn red. Progressive as I may think I am, I could sometimes forget my daughter was herself a flesh-and-blood woman.

"Get over your embarrassment, old man," she said, sensing my awkward pain, "it would be hypocritical of me to have a problem with something I encouraged you to do to begin with. So, let me reiterate that everything - and everyone - you are doing is just fine. And for me, the sun may be beginning to shine my way."

Bethanny told me that she and a number of the girls had started befriending a small group of single guys. They had met them at the dance club a couple of nights prior and had been hanging with them at various times since.

"There's only 5 of them, so not exactly enough to go around. But they are nice and they are fun and they are, so far, the exact opposite of what I would have expected from a group of single guys at a resort like this. They aren't pushy or 'frat-y' at all, just nice guys. They're a couple of years older, but not enough to make it weird. I guess one of their parents is rich and paid for everyone to come."

She was obviously pleased with her turn to good fortune and the potential opportunity to experience a vacation romance. That said, it still felt strange for me to encourage her to go out and get laid.

After breakfast we wished each other the best for the day and I headed out onto the sand, alone for the day.

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It was late morning and I was blissfully alone.

Or, at least I had been blissfully alone.

I had spent my morning tanning and reading. Finally, actually getting into my book that, so far during the trip, I had just really been unable to do. I had set myself up way down the beach, away from the resort, away from the amorous adventure seekers, away from everything. My book was a typical mystery adventure, engaging and exciting, and I was legitimately enjoying my time, the exact image of how I pictured my time spent before we left.

This was not to say that I ever really was upset by company, especially when it was specific company. That being the ever enticing Jenn, strolling her way down the beach directly toward me, wearing nothing but a tiny black g-string.

"Hey!"

Though we had caught each other's eyes when she was about 50 meters away and each of us had yet to wipe the smile off of our faces, it was still obvious that she had not expected to have found me where I was when she exclaimed her greeting.

"Hey, you," I responded, not the least bit upset in knowing that I would not be doing any more reading that day. "Aren't you the vision coming down the beach!"

"You like my suit?"

She twirled around on the sand and showed off just how microscopic it was.

"I do. I swear I had no idea how popular suits like that apparently are. I have seen a number of girls wearing them and even my Bethy packed one for the trip."

"This is Bethy's," Jenn responded with a giggle.

"Well, that explains it."

I certainly knew the propensity of the girls to swap and wear each other's swimsuits, it didn't seem completely unreasonable for Jenn to get in on it as well.

I had brought two towels, one to lay on and one for a pillow and got up to spread the extra out on the sand for my new guest. It was obvious she hadn't originally intended to stay out here as she literally had nothing with her. She responded with thanks and pulled off the miniscule lycra before laying herself down next to me.

"Avoiding everyone today?"

"And yet here I am with you."

She had a brief look of panic on her face, a moment of terror in realizing she hadn't asked if she could join me, not even thinking about the fact that I put the towel out for her.

"Don't worry," I added with a chuckle, "I'm glad to have your company."

I couldn't get over how incredibly beautiful she was and marveled at how, even if I tried, I couldn't find anything wrong with her physically. Jenn, seemingly sensing my awe struck stare, stretched out in the sun like a playmate in front of the lense, only increasing her appeal.

"I can't believe I didn't want to come on this trip originally. To think that if it wasn't for Kate basically dragging me I wouldn't have gotten to experience any of this."

"It would have been my loss," I responded. "It has been nice getting to know you."

She rolled onto her side, facing me, her breast pushed into my arm, and put her hand on my dick.

"It's been nice getting to know you as well."

Not being too concerned about my dick, I pulled her on top of me and we began kissing - making out, really - working ourselves into a feverish frenzy pretty quickly. I could feel that I was hard - my erection sandwiched between our skin - and I could feel she was wet from my wandering hands, so I can't say I wasn't a little bit surprised when she got off of me and shimmied herself down my body, planting herself between my legs, her face directly at my cock. She had a twinkle in her eye.

"You don't have to," I said. I almost regretted the words coming out of my mouth as soon as I said them. Of course she already knew she didn't have to, what was I doing rushing things?

"I know," she responded, focusing her attention on my engorged manhood, "I want to. I never did the other day and I regretted it afterwards. Besides, I'm single now, I need the practice."

Spoiler alert: she didn't need the practice.

Jenn worked magic with her tongue and mouth and it was a wonder that I didn't blow my load down her throat after just a couple of minutes. I couldn't tell you particularly what was different in what she did as compared to every other woman that I had ever been with but, whatever it was, it was spectacular.

And, what resulted, was a totally sexist scene straight from the misogynist handbook: a scenic, tropical beach, a beautiful nude woman, her head bobbing across my groin and me, head perched up and taking it all in, most likely with a stupid grin across my face. As a few lost or adventurous souls walked by it took me back to the first day when I too strolled down the beach and witnessed the sexual displays provided. Being that we were so far down and away from the resort, it was obvious that, of the 8-10 people that strolled across in front of us, most were either accepting of or numb to the visuals presented to them. Having already passed (based on my own personal experience in days prior) multiple sexual acts potentially more graphic, the sight of a blowjob was practically rated PG.

It had been some time and I felt my loins begin to tighten and I informed Jenn what was going on.

"Oh, no you don't," she responded, immediately stopping her actions and letting the build-up to climax subside. "We're gonna' finish together."

I rolled over on top of her and we kissed and petted one another some more, enjoying the time we had with each other. My only surprise was her rejection of my offer to go down on her.

"No. I want you in me."

I live a tough life.

Jenn had me roll back over onto my back and straddled me, wasting no time in guiding me into her but then just settling down onto my chest so we could continue kissing. Even with no movement at our groins it was terribly pleasurable.

Across my body I could feel the weight and softness of her skin and curves.

On my dick I could feel the gentle pulse of her heartbeat through her warm, wet, inner walls.

With my hands I was able to explore the contours of her sides... her back... her ass.

We were talking and giggling the entire time, whispering to each other like teenagers hiding out from their parents. But, unlike the hyper-sensitive states of teenagers, scared to be caught, we were oblivious to our surroundings, our sole focus being on one another.

Big mistake.

"Hey guys."

Bethanny was walking toward us, hand-in-hand with a young man I hadn't seen before, both of them nude, both of them holding swimsuits in their hands. My daughter had a cheerful look on her face, the same as if she just happened to have come upon friends when alone in a strange place. The guy she was with had a look of abject terror.

I was not sure, based on the angle that they were approaching us, if they could actually see that I was fully penetrating Jenn. I was not sure if my dick was slick and wet. I was not sure if her asshole was presented and winking in the sun. I was only sure that it was easily the most uncomfortable situation I had ever found myself in and, while I expected to immediately lose my erection, the pulsing warmth enveloping it would not allow that to happen.

"Hey there!"

Jenn popped up from my chest but did not leave her straddled position across my waist. I saw Bethy's friend's eyes go wide at the sight of her, taken in the way that every other man inevitably was. I propped myself up on my elbows a bit but otherwise stayed down on the sand. The position was awkward. Not physically, rather visually, as my eyes were immediately positioned to stare directly at their crotches, forcing me to crane my neck to look at their faces.