Single Male Chaperone - Reimagined

It was witnessing the anal, and Heather's wide-eyed response to it, that really caused me to think we would be turning back though, at the moment of peak concern, we were saved.

"Dad! Oh, wait, I mean Will!"

We both turned to see Bethanny waving from just around the vegetation line, not too far away from where we were. Instinctively we turned and started walking toward her, immediately we noticed that she was, as were the others she was with, nude.

"Hey, ladies."

We had just gotten up to where they were sitting on the beach. Bethanny had stood up to greet us while her friends stayed on their towels and, when she spoke, my daughter didn't even acknowledge me.

"Oh, my God, Heather! I love your suit!"

I saw a smile quickly spread across Heather's face and my worries about her cancelling our day together melted away. Thank goodness for flattery.

Bethy and Heather immediately got into some very animated conversation about the swimsuit and a few different things happened:

First, Heather pulled off the wrap she was wearing to display the bikini bottoms, a tiny, matching black g-string that looked similar to the one that I had seen Bethy pack just before our trip. True enough, she almost immediately pulled hers out of a bag and onto herself and, when modeled next to one another, they were nearly identical.

Second, as the conversation progressed and the minimal coverage of the suit was discussed, all of the teens in the group lamented the visibility of razor burn around the bikini line and how the suit seemed to irritate the skin. To my surprise, the topic was apparently close to the heart for all the girls and, before I knew it, each of them were spread eagle on the sand as Heather demonstrated proper skin care and shaving techniques for each of them.

Finally, after one of the girls (basically the only one who had no razor burn) mentioned her propensity to do her own self-bikini waxes, Heather offered to leave behind her own waxing supplies that she had brought on the trip with me and the girls could use it to clean themselves up for the rest of their vacation.

"Besides," she whispered to me as the girls chattered about the new opportunities afforded to them, "having to return the stuff will force you to come see me once we return home."

I couldn't deny that I liked her thought process.

When the conversation finally started to die down and the girls began to pick up on my hints that I wanted to leave so I could spend some time alone with Heather, we grabbed our few belongings and headed a bit further down the beach, far enough for some privacy.

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"Will?"

I could hear a bit of hesitation in Heather's voice as we began settling ourselves into a little area on the beach.

"Yeah? What's up?"

"Can I ask if you planned on us having sex out here? Like, that is why you offered to bring me out here?"

"No. No plan on sex," I replied truthfully. "But very much a plan to just spend some time with you."

"I know that I am flirty and touchy and I know that I am the one who has been kissing you. I want to add that it wasn't just a casual thing for me either, I legitimately feel like there is a connection between us. It's just that I can't have sex with you. Not because we just got to know each other or anything is too quick, just that I have things I need to take care of first."

My hands had already been on the waistband of my shorts and I had been preparing to get naked but her commentary stopped me short.

"Heather," I replied, "it really is no issue. I expected nothing other than to spend a day on the beach with a wonderful woman. No sex? No problem. No nude? No problem. I have no problem walking back to the resort and we can stay fully covered in the pool area."

"Well," she said with a smile, "let's not go too far."

She stepped into me and wrapped her arms around my neck, her small body pressed up against mine, and pulled me down for a prolonged kiss. And, wouldn't you know it, Will Jr. decided to wake up.

Damn it.

Thankfully it wasn't like I just shot from 6 to midnight. Afterall, I am a middle-aged man. But I definitely felt a twinge.

Heather stepped away from me and turned around, dropping her sunglasses on her towel and grabbing the sunscreen.

"So," she said, her back still to me, "do we just do a count-down or something? 1-2-3-naked?"

The look of shock on her face when she turned around to find me, standing nude in front of her after dropping my shorts to my ankles, was priceless, and watching her drop the sunscreen and seeing her eyes dart around, not sure of where to focus, made me laugh out loud.

"I win," I responded, "and you're overdressed."

She didn't pull off her suit immediately and instead stepped back to where she was, her arms around my neck, a happy, innocent look in her eyes.

"You're a heck of a guy, Will."

With my arms around her back I pulled at the string of her bikini top, undoing the tie and allowing it to fall to her sides, the tiny triangles of fabric just barely covering her nipples.

"Oops."

"Well, aren't you presumptuous," Heather said with a grin as she pulled the cups of her bikini away from her breasts and over her head, "maybe my plan the entire time was just to get you out here to see you naked."

"Uhm... oops again?"

She pulled the tiny g-string off of herself and stood in front of me, in all her glory for just a moment, fantastically easy on my eyes.

"You, my dear," I said with a satisfied exhale and shake of the head, "are stunning."

Heather spun back around to grab the sunscreen and handed it to me.

"Stop getting fresh, mister. And don't miss any spots."

I was conservative in my application, not in that I didn't cover her back properly, but in that my application was not quite as sexual as it had been with Kate poolside. With the conversation that we had just had, I liked where things were going and figured there was no reason to push things into an uncomfortable area. And, besides, especially when I was done and she had turned around, the visuals were enough for me.

I could see that Heather had implants, something that I had somewhat figured the very first time I saw her in a bikini but now, with a faint scar at the bottom of each areola, could pretty much confirm. Though augmented, they still had a fantastic natural shape and hang to them that made them look like a genetically blessed 20-year-old as opposed to an obviously unnatural bolted-on look.

"I got them done 2 years ago," Heather said, sensing my gaze.

"What," I responded with an overacted pretend look of shock on my face, "was I staring?"

"Once I started getting back into shape with running and swimming the reality was that much of the weight I lost was in my boobs. So, 8-K later I am able to fill out a bikini top again."

"Well, you look great and I apologize for the drool. As I told you when we first met, I rarely get out."

We finished our applications and laid down in the sun, soaking up the rays and enjoying the positive energy of just being in one another's company. In fact, that was how we spent most of the day, just normal beach stuff: swimming, talking, answering the quiz questions in Heather's magazine about how to know if you are a fantastic lover.

"You may not believe me but I am not normally this comfortable with being nude in front of other people," Heather said to me at one point.

I was coming out of the water and she was still laying on her back, in the sun, with her knees bent and her legs spread wide, her pussy pulled open just enough to show a bit of pink, her small patch of red pubic hair practically glowing in the sun.

"No?" I responded.

She giggled when I shook the wetness out of my hair, spraying her with a light mist of cool seawater.

"Nope. Not at all."

"Well, on behalf of myself and all of humanity, the world is a better place when naked Heather is in it."

She rolled over onto me, her breasts pressed into my ribs, and rested her cheek on my chest.

"I really wish I could."

"Could what?"

"Jump your bones. Everything about this is just so sexy. I really want to but just know it isn't the right thing to do."

"No worries," I replied with a kiss on her forehead. "Good things happen at the right time. It'll happen if it's meant to be."

"You're a good guy, Will Patton."

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My alone time with Heather came to an end even sooner than expected when Bethy and one of the girls she was with, Lilly, wandered down to our section of the beach. Heather had noticed them before I did and almost scared me when I saw her eyes go wide and her jaw drop at whatever was coming up from behind my back.

"Holy shit," she exclaimed in a soft voice.

I spun around to catch the sight.

"We got ditched," Bethanny said while they were still 20 feet away from us, "would it be okay for us to join you?"

"Absolutely," Heather responded before I even had a chance to react, "make yourselves comfortable."

They strode unevenly in the sand toward us, their breasts jiggling with each step, their skin glistening in the sun. I had known Lilly for years. She was not one of my daughters closest friends but she was certainly close enough that she had been around the house many times. I had seen her fully nude for the first time the day before but, as she walked over to us, she honestly seemed to have a glow of holiness around her. At 5'7" tall, 130lbs, measurements of 39F-24-36, with wavy brown hair and a full, silky bush, only a single thought came to mind:

Marilyn.

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A Note to the Reader: I was probably 12 years old when my older brother (who received it from a friend, who, in turn, had swiped it from his uncle's stash) presented me with my first look at a Playboy magazine. Back then, when the internet wasn't a thing and the JCPenney catalog was enough to make my breath go short, to see a woman, fully on display and solely for the viewers pleasure, was a revelation.

The May 1974 issue was, coincidentally, the introductory centerfold of Marilyn Lange, a young woman whose breasts were as big as her saucer-like eyes, whose smile was as intoxicating as her hourglass figure, whose raw magnetic appeal subsequently landed her a follow-up photo spread as the Playmate of the Year in 1975... and whose image was burned firmly into my brain. It had been years since I had even looked up those original pictures on the internet and yet, here she was, walking toward me, carbon copied and resurrected before me in a young woman named Lilly.

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"What have you two been up to?"

Heather immediately started into conversation with Bethanny who, as opposed to sticking close by her friend, was setting herself up in between Heather and I, spreading out her towel on the sand.

"Nothing much. I actually think that was why the others left. We were just fine with laying out and tanning. They were getting bored and decided to go back to the pool."

Lilly had stood my somewhat awkwardly for a moment, watching Bethanny get settled, realizing that there was not enough room for both of them.

"Sorry for my daughter being so rude," I said to her with a smile and roll of the eyes, "can I slide down a bit? Give you enough room to sit here?"

I think it was the roll of the eyes that put her a bit more at ease and Lilly graciously rejected my offer and set herself up next to me, on the opposite side of Heather and Bethy.

We were quiet, both of us apparently content to weather the circumstances we found ourselves in silence, just laying out and soaking up some sun.

Heather and Bethanny, on the other hand, were talking up a storm... to the point that it got annoying.

"Well," I said after some time, "I think I am going to hop into the water."

I intentionally didn't invite anyone as I was looking for a bit of quiet but I was also not upset when Lilly, who to that point had not said more than a few words, indicated she would join me and, after I offered a hand to help her up, we walked side-by-side to the warm tropical water.

"I had to get out of there," I said in a low enough voice. "No offense to you, Bethanny or Heather, but I really can't take much girl-talk."

"I'm the same way," she responded. "I love your daughter and the other girls on the trip but sometimes I just can't take the girly-ness."

We swam and floated for a little bit, stopping every once in a while to make small talk and check to see if Heather and Bethy were still gabbing. Each time they were. It was obvious she was getting to be a bit more comfortable around me. I think it was because I was making a concerted effort not to stare at her, not to marvel at her body and beauty and instead just let her relax. Though, when we did finally say something other than trivial chit-chat, she caught me off guard.

"Can I ask you something?"

"Sure, what's up?"

I had been attempting to float, something that my body did not naturally do very well, and took the opportunity to dunk myself before popping up. Lilly, for seemingly the first time, was staring directly at me.

"Do you think I am attractive?"

I felt my face contort as there was absolutely no question as to whether she was attractive or not. Objectively, she was.

"Well, yeah, of course I do. You are a very beautiful young woman."

"And would you have sex with me?"

My jaw fell open and I stammered a response.

"I... uhhh... I... uhm... I... I don't know. May I ask why you are even asking?"

"Well," she responded in a matter-of-a-fact tone, "it's just that I know you have already had sex with a number of the girls on the trip and ever since Bethy and I met up with you and even since we have been in the water, you basically haven't been looking at me. Almost like you are intentionally trying not to."

"To be honest," I responded with a little grimace, "I kinda' have been."

"Why?"

"The same reason I try not to stare at anyone. It makes a lot of people uncomfortable."

"I guess I can see that."

She was bobbing up and down and her large breasts flowed with the motion of the water.

"So, would you have sex with me?"

"I wouldn't not have sex with you. If that makes sense."

She didn't respond and instead just continued to stare at me.

"Look," I continued, "I feel like any sex: in a relationship, casual, or friends-with-benefits types of scenarios, requires an appropriate mood for it to be successful. But another question that has to be asked is this: do you want to have sex with me?"

"Well, I think I like sex though admit I haven't had much. My boyfriend broke up with me and said I wasn't very good at it and my mom wants me to just see a bunch of different people and have different experiences. She says that I shouldn't be trying to settle down at such a young age. And you have always been a really nice guy and obviously there wouldn't be anything long term between us so, yeah, I guess I do want to have sex with you."

When she mentioned the impossibility of a long term relationship I felt a grin spread across my face, afterall, it was true. The only thing I couldn't believe was that her boyfriend said she wasn't good at sex. Afterall, I was a teenager once and there was very little that I could put my dick into that wouldn't make me happy. I couldn't imagine the experience with someone as hot as Lilly could be "bad."

I was about to respond when we heard chatter and splashing coming from the waters edge. Heather and Bethanny were joining us. For better or worse, saved by the bell.

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With Heather's time at the resort so limited I was disappointed that we were unable to spend it together and alone though the additions of Lilly and Bethanny turned out to be better than originally expected.

First, it was extremely pleasant to see just how well Heather and Bethy got along with each other. Not that there were thoughts in my head of having a replacement mother for my daughter or anything like that but, as it had historically just been the two of us, a third had the potential to ruin the dynamic.

Second, whether it had to do with her getting the thoughts out of her head or not, Lilly really seemed to open up out of her shell and was a lot of fun to be around.

As a group we spent right up until the last minute that Heather had to go get ready for dinner out on the beach, laughing and enjoying the company. The only surprise of the day was, when the time came for her to leave, Heather suggested that Bethanny come with her to grab the waxing supplies, seeing no need to have Lilly and I cut our time short on the beach. Our goodbye, which included a prolonged embrace and kiss, also included a rather graphic depiction of arousal whispered into my ear in addition to an unexpected hand wrapped around my cock, all in the presence of our two teenage companions, both of whom eyed each other mischievously, very aware of what was going on.

It was only when half of our foursome was out of sight that Lilly turned to me and asked if I wanted help re-applying sunscreen.

EIGHTEEN:

The sunscreen was never picked off the sand but it didn't stop us from immediately having our hands all over one another. It was surprising to me at how aggressive Lilly was, probably unreasonably so considering how aggressive she was in her solicitation of sex to begin with. Nonetheless, we attacked each other animalistically, hands and tongues moving about with little thought or hesitation, a sort of sexual reflex in which every sense acted like an addict in need of a fix and every part of her body offered a hit for multiple senses.

Her body was surreal, too much to be appreciated at any given moment. I could have spent hours exploring any one part of her: her heavy breasts; her toned calves and thighs; the salty nook of her neck; her smooth inner thighs, the bumps and ridges of each tanned areola and nipple; the wispy strands of pubic hair; her fantastic lips and smile; the folds and musk of her sex; the pucker of her asshole.

We rolled in the sand for a while, bodies and tongues wrestling before moving into a 69, allowing me to savor her sweet, salty flavor, and, after she rolled through an orgasm, Lilly flipped herself onto the towel next to us, eyes closed, body like jello, her brain trying to process what she just felt.

"Did you do that to the other girls?"

"Do what? Oral?"

"Yeah. That was intense."

"Every experience is unique," I responded. "And that is why I try not to talk about or compare one experience to another."

"I get it," she said. "Don't kiss and tell?"

She summoned some energy and popped up from the ground and straddled me, laying down flat on my chest.

"Well, let me kiss..."

She kissed me.

"And tell you this," she continued. "You need to do that to everyone because that was fantastic."

I flipped us over, her back to the towel we had been on, her hair somehow flopping out to look like a shampoo commercial.

"Glad you liked it. You do some good work with your mouth yourself."

She squeezed her hands in between our bodies and grasped my dick, still very much hard though appreciative of the soft strokes her petite hands offered it.

"Time for the main event?"

"I'm ready if you are," I responded.

She took control, directing my dick to her opening, sliding its head up and down her opening, making me slick with her wetness, priming each of us for penetration.

"Fuck me," she whispered in my ear.

'Jesus Christ', I thought to myself, 'where do these girls come from?'

I slid in with a single, long, slow stroke; her wet pussy accepting me with little resistance. There was something familiar about the sensation and I asked her if she was one of the participants on the beach. She denied that it was her and I chalked the confusion up to the fact that the experiences, to a certain extent, were starting to blur together.