Single Male Chaperone - Reimagined

"Wait," I felt my face drain of color, "you saw us?"

Kate got off the bed and stood up in front of me.

"Yes, Will. For the second time in two days I witnessed you having sex with one of my friends."

Her comment made the blood rush back to my face, my ears immediately burning red. She smiled at my embarrassment.

"This trip wasn't just about the girls, Will. It's a good thing you are getting back out there."

"If I didn't know better I would have thought you were talking to my daughter about me," I responded, looking for my shorts as a distraction to my embarrassment.

"Bethy wants what all of us wants," Kate responded as she stepped up behind me, grabbing my hips while I was bent down to grab my swimsuit, "she wants you to be happy, she wants you to share yourself with the world."

I stood up and turned around, Kate didn't wait a heartbeat before wrapping her petite fingers around my cock. Though I was flaccid, it still felt nice.

"Are you going to share?"

There was minimal innuendo in a comment that direct.

"You want to have sex with me? Like, now?"

I felt weird about the situation. Afterall, Kate and I were friends, she was still married and I was friends with her husband as well.

"Want? Sure." She was giving me gentle squeezes and reintroducing a healthy blood flow back into my organ. "But, alas, it isn't meant to be. Though my husband and I offer each other a significant amount of flexibility in the boundaries of our relationship, penis in vagina isn't one of them."

'Gee', I thought to myself, 'ya' think?'

Kate had let go of me, leaving me a little bit fuller though still quite a ways from hard, and had walked into her room. I took a minute to put my shorts on before following her. In her room I found her fully nude, bending over her suitcase, her pussy and ass positively calling to me.

"To be honest, and even though I understand that you can't," I said, trying to focus on my own train of thought, "I don't know if I could. Not that I don't want to. Shit, Kate, you are incredibly sexy..."

I felt my voice just kinda' trail off.

She had turned around and was facing me, fiddling with what looked like a new bikini. I was surprised to see a tiny patch of neatly groomed pubic hair. With my eyes having a new focus and not knowing how to explain my thought process, I kind of froze.

"And?" She stood in front of me, the look on her face obvious that she was looking for me to finish my thoughts.

"Okay," I responded after a deep breath, summoning up the courage. "If I am being honest I am not sure I even could. Like, 'the-mind-is-willing-but-the-body-isn't' type thing, ya' know?."

"Aww, hell," Kate retorted. "That's it? You're getting tired? I could give you something to keep you going. You know, if you want to party."

"Wait," I responded, pausing in my confusion, "like, coke?"

"Ha! No, not coke," she laughed, "Viagra... or something else like it."

She had already gotten dressed and had taken my hand, pulling me to the door.

"Like, you brought some? Why?"

"Oh, Will. You are so sweet."

The conversation was left at that.

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There was no more sex that afternoon and, if I am being honest, I was glad for the rest. I was also glad to have had some wonderful bonding experiences with the moms and various girls of the group. We hung out by the pool and chatted while we snacked and drank. We talked about normal stuff: future plans, current relationship statuses, etc.. We cheered each other on during various poolside games and contests. We were excessively thorough in our application of sunscreen and tanning oils with each other. Though I was glad for the rest, it didn't change how nice the feeling of a soft, warm, petite hand up the inside of my loose shorts felt.

After dinner and after a moonlit walk along the beach with a handful of girls, I left them in the dance club before heading up to my room. Afterall, the next day was the nude beach and I wasn't a teenager anymore. If anything, I figured I needed some beauty sleep.

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I was disappointed not to see Heather after my run the next morning and was surprised to see more than a handful of girls already at the breakfast buffet, including Bethy, both Sophia's and Shannon's daughter, Kara.

Though it was a cool morning I was still pretty sweaty when we first bumped into each other and the girls chided me for how gross I was. Most of them, appropriate for the slightly cooler weather of the moment, were dressed pretty conservatively in t-shirts and shorts that one would normally see in a resort dining room but, true to the direction of the trip, it was very obvious that none of the girls were wearing bras or bikini tops or, based on a few very loose pairs of shorts, any sort of panty or bikini bottom either.

"We all wore the loosest clothing we brought," Bethanny told me as we stood in line for omelets together, "that way we hopefully won't have any marks on our skin once we get to the beach."

"Good thinking," I replied in as dry a tone as I could muster, "it would be so incredibly embarrassing otherwise."

"You," she responded flatly back, "are the worst. And, I mean that truthfully. As you seriously stink and you need to clean up before we leave."

"This?! These are my pheromones! Evolutionary biology. Drives women mad, makes them want to have my babies."

Bethanny smiled, rolled her eyes and walked back to her friends. This was a routine that we had been through many times over.

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After breakfast, after a shower, after having a toast of some bitter drink Kate insisted on before we really started the day, I tied on my loose wrap, even forgoing my tan-through shorts, and we set out for the beach.

Realistically, considering we had no idea if, as a group, we were going to enjoy the fully-nude aspect of the day, we brought way too much with us. Chairs, umbrellas, beach games, a bluetooth speaker, a backpack full of water and snacks and a second backpack full of liquor. I couldn't help but be impressed with how generous the resort was with everything they offered to loan us. While I had originally figured it was going to be an extremely old-school day of "towel on sand," it evolved to looking like it was going to be quite an adventure.

The walk was a kilometer though felt somehow longer and shorter than that at the same time. The initial 150 meters were tough with not much more than a 6" wide footpath through pretty heavy jungle brush. It seemed the resort took advantage of natural fencing and allowed the vegetation to grow thick and tall, a natural deterrent to whatever they wanted deterred. While walking it wouldn't have been that bad, and the distance was manageable, the only problem was trying to get all of the chairs and umbrellas through with no issue.

Suffice to say, we survived.

After the thick brush it opened up quite a bit. Not to say we were no longer in the jungle, just to say that it no longer felt the jungle was trying to devour us. The thick bushes made way for high trees and wide-leaf shrubbery that made for a very nice walking surface and, when we got to the beach... well, hell, it was worth any inconvenience of a walk.

It was a small cove, maybe 300 meters wide in an incredible crescent moon shape. Both sides were walled by a rocky cliff about 15 feet high yet, from the vegetation, we were able to simply walk out onto the pristine, white sand. It was an image from a postcard that legitimately took my breath away.

"How the hell hasn't this been developed?"

My question was to nobody in particular. Considering how close it was to our resort it just didn't make sense that the property wouldn't have been privatized as the infrastructure was already in place to get paying guests there.

"Supposedly it is bank owned," Shannon responded, putting her belongings down on the sand and starting the process of getting situated. "Financial trouble for 2 or 3 companies who have expressed interest in developing it. In the meantime our resort and a few locals are basically the only ones who use it."

The place was empty and the girls were as excited about its beauty as I was... though expressed their excitement in a very different way.

As if they were in their bedrooms at home, the fine white sand was soon an explosion of everything they had on them. Chairs, towels, umbrellas, games and clothing were dropped to the powdery tan grains beneath our feet and the only thing left on each of them were their phones... and, instantly, the amateur photoshoots started.

"We've already talked to them about the pictures and the internet, Will. The moms and I talked to them about it before we ever came and again yesterday. The reality is though, it's different than when we were young. We can guide them but also trust them to make their own decisions."

Jenn must have seen the look on my face when she spoke out without any sort of other prompt. She, unlike our daughters and the rest of the teenagers, was calmly arranging herself in the sand, preparing for the day.

"Get my back, will you?"

She handed me the sunscreen bottle and pulled the loose sundress she was wearing over her head, revealing nothing other than her smooth, sun-kissed skin.

I felt a stirring.

"I know," I said as I began rubbing the lotion onto her back. "I'm still having a parental moment though. Not even as much about the pitfalls and dangers, just more about them growing up."

The poses and pictures the girls were involved in were all innocent enough, other than their nudity, it was typical group stuff. Arms around each other, hand-in-hand walking, all the same stuff that you see on any sorority sister or "influencers" Instagram page.

"I can't stress enough that you did a fantastic job with Bethy, Will. I am sure she... and you... will be just fine."

She spun around and wrapped her arms around me, her warm, soft skin pressing up against me. She placed a soft kiss on my lips and what had previously been managed and under control was now a 4 alarm fire, my cock was fully erect and throbbing.

"What the hell is going on?!"

Jenn stepped back and giggled, before grabbing the sunscreen from me and squirting a healthy dollop onto her hand.

"I guess it wants to make sure it is protected from harmful UV rays," she said, stroking me with the thick, gooey lotion.

"I need to sit down or go in the water or something," I said, pulling her hands from me. "For every ridiculous thing that has happened so far on this trip, I really don't think that walking around with a hard-on is how I want to spend the day. Nor, I am sure, would the girls want to have me around like this."

"Like what?"

As if the beach gods were looking to make my day miserable, Jenn's daughter Brielle stepped up from behind me and next to her mother, facing me directly. I covered myself up, of course, but having never known she was there to begin with it was after she had gotten a very clear look at my swollen cock pointing up toward the sun. Her eyes went wide.

"Mr. Patton, is having a bit of a moment, honey," Jenn said with a smile, pulling her daughter toward her and wiping a stray hair out of her face. "What's up?"

"Just looking to get the sunscreen."

Brielle's eyes could not stop moving, darting back and forth, anywhere and everywhere, but always re-focusing every half second on my crotch, desperate in their attempt to get my hands to move and reveal the incriminating evidence.

"Sure, let me do your back before you go," Jenn responded, seemingly without a care as to my predicament. "Just stand still."

I took the opportunity to commandeer Jenn's chair. It didn't get me out of the area, but at least the sitting position would hide me just a little bit. Of course with every movement my dick bobbed around, glistening in the sunlight from Jenn's oily application, and with every bob, another wide-eyed grin from Brielle, her line of sight never even attempting to break.

She was chip off the block of her mother and everything I figured Jenn probably was in her youth. Tall at approximately 5'8"; maybe 118lbs. She had small, pert breasts topped with bright pink, already puffy nipples, wide hips that framed a luscious bubbly ass, a neatly groomed naturally red landing strip, some of the most full, pouting lips I had ever seen and doe eyes straight out of a comic book. All of that topped with long, flowing, wavy red locks that always looked like she had just stepped out of a salon.

Her body reminded me of Rosie who was, at the time, dancing on the beach for a paparazzi of cell phones but, as Bethanny reminded me just the day prior, her red hair made a lot of difference.

I liked it.

A lot.

Of course the two of them, naked as the day they were born; phenomenally beautiful, long red hair... let's just say my erection did not die down.

It didn't die down then.

It barely died down as I got myself to relax and enjoy the sun.

It came roaring back to life when the girls started situating themselves around me, spreading out towels and chairs, situating themselves for maximum sun... and visual... exposure.

Why the hell was I so hard?

It was right around 1pm when Kate strolled over to me, a bottle of tequila in her hand, a straight look on her face. It had been hours since we had gotten to the beach and my cock was still out of my control. Thankfully it wasn't as if I had been hard for the entire time we were on the beach but it was popping up regularly, at the smallest amount of stimulation. I had barely gotten out of the chair the entire time we were there. While others swam and played, I sat.

"I'm sorry," she said, offering me a plastic cup that felt like it had about 3 shots of liquid in it. "It's my fault. I thought it would be a funny joke but now it seems like you are so embarrassed you can't even enjoy yourself."

"What are you talking about?"

"I ground up Viagra and put it in your drink this morning. That's probably why you said it tasted so bad. It's also probably why you haven't gotten out of the chair today."

I got embarrassed, and I got mad.

I got mad enough that I felt my ears burn. I felt the blood rush to my face and mercifully away from my dick. I was able to stand up and I was about to give Kate a piece of my mind when I stopped myself and forced myself to answer a question.

Why?

Why bother? Why bother making a scene? Why bother potentially ruining the rest of the trip?

I took a cup from her hand and downed the liquor, feeling the delightful burn the entire way down.

"I guess now I just need to get you back," I finally replied, a comment that appeared to be a relief to Kate.

She stood next to me and wrapped her arm around my waist and called all the girls around.

"Girls," she addressed them loudly and clearly.

The initial pain of her explaining to the twenty 18-year-olds that she had drugged me and that I would likely be sporting a raging erection from time-to-time that day on the beach was significant. I felt the girl's eyes burn into me, burn into my dick. I couldn't even look at my daughter, ashamed of the humiliation I had brought on her. But, as the tequila kicked in, as my nerves began to go down, as the soft tickle of Kate's small fingers moved their way up and down my side, the pain went away. The pain went away and my erection came back.

It didn't just pop straight up from six to midnight, but it obviously started getting a bit chubby. Afterall, the circumstances were stacked against me. The warmth of the sun, the combined tequila and lack of food, the sight of a pack of hot, nude, nubile women, all smiling and focusing on me.

It was Sarah who took things over the edge, the girl who started my entire personal transformation. She stepped out of the group and up to me and casually took hold of my budding boner and brought it to life, with soft, long strokes from her soft, small hands.

When she was done, when my dick was sticking straight up, its swollen head pointing to the sky like a light-needy mushroom, the faces and eyes of the group all glued to me... and it, Sarah opened her mouth and spoke a comment that apparently was for the entire group.

"Meh, it's all good."

She gave me a kiss on the cheek, a final squeeze of my cock, and the day, at least for me, finally began.

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A few things happened after that point:

First, my dick became the singular focus of beach-wide attention. Instead of letting it go down, everyone wanted to keep it up. Hands were constantly on me, massaging me, squeezing me, stroking me. Thankfully, most of it was gentle enough that my skin did not get raw.

Second, booze started flowing. While I had only been aware of one backpack of liquor, it appeared that we had more as everyone started doing shots... a lot of shots... and inhibitions started dropping.

Third, phones and cameras came back out and the pictures started getting a bit more... risque.

It had been probably 90 minutes of increasingly brazen poses when I found myself taking a picture of three girls, Bethanny being one of them, on the beach. They were each on all fours, presenting themselves for the camera, pussies and assholes on garish display, each doing their best to look sultrily into the lense.

"Are you sure," I asked hesitantly, lining up the shot, "I mean, this is pretty graphic."

"Dad! It's fine, just do it! I mean, what about you?!"

I took the shot and handed the camera back. The booze had kicked in for everyone and inhibitions were at an absolute low and my daughter had a point. After all, how else could I justify the pictures of Brie and Rosie, each individual poses, but each with my cock in their mouths?

I figured things would calm down from there, I couldn't have been more wrong.

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I had gotten a minute to sit with the other parents, desperate to take a breath, desperate to let my cock get a rest from the attention. Everyone was drunk, everyone was seemingly pretty horny, the topic of conversation was focused solely on sex.

The women were talking about their favorite positions and sex acts and one of them, I honestly don't remember who, mentioned that, while it could have been based on her limited pool of participants, she really didn't think too much difference between one penis to the next, they all felt pretty much the same to her. At the time, though I wasn't really part of the immediate conversation, I scoffed at the notion. Afterall, it seemed a ridiculous concept that there would be minimal difference from one phallus to the next.

Kate, in a drunken challenge to my scoff, chirped back at me.

"Oh, no commentary from anyone that has a penis. Every woman knows that it doesn't matter what a guy sticks his dick into, as long as he gets off."

I couldn't believe what I was hearing.

"Are you seriously trying to argue that men not only couldn't care less, but also can't tell what we are putting our dicks into?"

"Well, no," she replied, "I know you could tell the difference between say a cactus and a bowl of jello..."

She pulled her knees up to her chest and pulled her legs wide open, gesturing to her neatly groomed kitty.

"But, if we are talking about pussy? Well, no way!"

The concept was ridiculous.

"Then why bother with foreplay? Why bother with kegels? Why bother with anything other than in - out - done?"

"Because that stuff is for our benefit! Typical guy... always thinking everything is about them."

Kate was laughing away, though was apparently also taken in by her own sexy line of discourse and was lazily dragging a finger up and down in between her opened petals.

"I really don't have much to say," I responded. "It's just so stupid."

"What's stupid?"

Bethanny stepped up next to me.