Single Male Chaperone

I could feel my face turn beet red immediately but, verbally, I at least tried to play it cool.

"Well, you know what we talked about. This is an adult resort and sometimes adult things will happen. Sorry if I offended any of you."

"Offended? Hardly. You do you. Not bothering any of us."

I looked around and saw the other girls, 4 more total, all nodding along. A couple of them were suppressing smiles but none of them looked shocked in any way. Maybe they were more adult than I thought. Nonetheless, it seemed like a perfect time to get up and check out some more of the resort so I excused myself from the group and went to wander.

Incidentally, I ran into Brie walking in from the beach.

"Hey, Dad. I mean, Mark."

"Hey, kiddo. Watcha' up to?"

"Just gotta' go pee. You?"

"Just checking things out. Before you go though, can we talk?"

I told her about my conversation with Sara and my thoughts of it.

"Do you really think I have lost my identity? I was hoping I was giving you a good life."

"I have had a fantastic life! But I worry about you. Next year when I am off at college, what are you going to do with your time? You are such a fantastic guy, I want you to go have a life."

I sighed. We had the conversation before. She had been harping on me for a couple of years.

"Okay, I'll try. But, quickly, why did it sound like you talk about me not having sex?"

Brianna wrapped her arms around me in a hug.

"Well, it isn't like I talk about it. Just that I have mentioned that I think you need to. Get out there and show the world what I already know. What have you always told me? Go make the world a better place? That means doing stuff other than just being my dad. Go get laid. I want you to be happy."

Of course, it could have been a moment for us, a touching father/daughter hallmark with a sappy soundtrack playing in the background but real life is a little bit different and Brie pretty quickly let go of the hug.

"Sorry, I really gotta' pee," she giggled as she pranced off toward the resort, leaving me by myself.

I guess there was no better time to get "out there."

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Part 2:

I woke up the next morning after a relaxing first day. Nothing had happened the rest of the day that stood out from the multiple displays of toplessness, thongs and my daughter telling me to get laid. The resort was nice and offered a variety of amenities, none of which I tried. Instead, I hung out on the beach, hung out at the pool, ate and drank and generally did nothing. Afterwards, I even went to bed early. I felt fantastic.

Sara was still asleep in bed but as I heard from noise coming from the room next door, I hopped out of bed to take a look. Gina was in bed, Melanie was toweling off with her back to me, the shower was running.

"Good morning," I said, loudly enough to startle Melanie and who dropped her towel and spun around immediately.

"Oh, my, Mark. You scared me. Good morning to you too."

I saw her eyes dart to my crotch and, as I looked down myself, I realized that I was stark nude. A reminder to how I normally slept but forgetfull-ness to the mixed company I found myself in.

"Shit," I said as I threw my hands in front of my dick, "I'm sorry about that."

But, I didn't back away from the door. I just stood there and stared at her and she stared at me for what seemed like an eternity until she mercifully cut the tension with a joke.

Melanie had also made an awkward attempt to cover up but slowly put her arms down to her sides. "Ain't this great? All this empowerment and ownership of our sexuality?" Her tone was wry and sarcastic.

I chuckled and allowed myself to move my hands away from my crotch, tossing her a "go-ahead-and-look" glance. "Oh, yeah. Loving every minute of it. I had no idea just how empty of a soul I was before."

Then, a funny thing happened, life went on. We started having a conversation and, at least for me, it was as if the nudity wasn't even there. We talked about the resort. We talked about Sara and Gina. We talked about how we had both been given lectures about finding ourselves. We talked about how we thought that it was silly but maybe we both could stand to break out of shells a little bit.

"I just worry, you know," Melanie said to me.

"Worry about what?"

"Worry that maybe it is too late. Maybe I lost my chance to be something other than a mom."

"Aww, that's a bunch of crap."

The voice startled us. As we got caught up in conversation, we apparently both lost track of the time and the fact that the shower had stopped. Emily was standing in the doorway to the bathroom, herself nude except for a towel wrapped around her hair.

When I turned to her, I could see that Emily sized me up quickly, an ever so slight pause on my penis, but her main focus was her mom, who she rushed over to and wrapped in an embrace.

Nothing was said, instead they just held each other for a tender moment, eyes closed, appreciating one another. It wasn't until a few moments later that Melanie opened her eyes, found me standing directly in her line of sight, and chuckled.

"I think it is going to take me a bit to get used to all of this nudity."

Emily released her mom from a hug and swung around to where I found myself with two nude women staring right at me.

"I kinda' like it," Emily chimed in. "Certainly beats having to wear a bra."

Not that, in my male mind, Emily needed much of one. She was a little taller than her mother, probably about an inch, but quite a bit more lean, a testament to not having borne children. She had nice legs, curvy hips a relatively flat stomach and a torso topped with small, maybe b-cup breasts that were topped with small, red-ish nipples and almost invisible areola. Like so many her age, her pubic hair was fully shaved with just a bit of dark stubble. She was a lovely young lady, with a pretty face and just-past-shoulder light brown hair.

"Did you spend the night in here?" I was confused as to why Emily was even in the room.

"No, got up to work out with my mom but figured not to wake the girls in my room so I took a shower here."

"Obviously no problem waking up me," said Gina somewhat grogilly.

The movement and voice surprised both Melanie and Emily and each went into immediate damage control apology mode.

"Oh, it's fine," Gina responded as she got out of bed and wandered to the bathroom, she too fully nude, "I need to work out too. Next time wake me up beforehand."

The splash of an early morning pee against porcelain rang out into the air and Melanie and I both offered a raised eyebrow and a smile. This most certainly was a different experience than either of us were used to.

-----

Day 2 found all except two of the girls wearing significantly smaller swimsuits with 3, including my Brie, going in full g-string thong (though not the one I had seen her pack, this one had a larger covering in the front).

The pool was hopping by noon, with games and drinking in full swing and while I could tell a few of the girls were still a little shy about getting involved, others were front and center on the pool deck enjoying the fun and attention. I assumed the vast majority of the activities would be prescribed in nature, the kind of stuff that bored, drunk suburbanites do while "being crazy" on vacation: bikini/hot body contests, balloon popping between members of the opposite sex, etcetera. I had my reservations if these types of activities legitimately offered anything in the way of the female empowerment that Sara had spoke of, but can admit that the girls did seem to be having fun as I watched them try and catch foam rings on a waist mounted apparatus that was obviously meant to mimic a strap-on or male erection.

All of that said, it wasn't particularly my type of scene so I made my way to the beach with a towel, book and a drink to catch some sun and relax. Besides, my justification for not being a party-pooper was that I had promised the girls that I would give them a wide berth.

I figure I had been locked into reading for about 45 minutes when a voice startled me.

"Is this seat taken?"

I looked up to find a woman standing practically over me.

"What was that?"

"This chair, is it taken?"

I had to focus my bearings to realize that she was referring to the chair directly next to me.

"Uhm, no. It is not, you can feel free to take it."

"I'll actually just stay here if you don't mind."

She began to spread out a towel and arrange herself on the chair under my curious gaze. I admit I had expected her to have dragged the chair somewhere else, instead she kept the chair exactly where it was, not more than 4 inches away from my own. Her gear was typical, towel, sunglasses, sunscreen, book, all pretty much the same as my own. Her final act before settling in was stripping off a patterned, opaque mu-mu of a sundress to reveal an athletic, curvy body clad in a small string, cheeky bikini. I immediately doubted if I would be able to concentrate on my book again.

"Avoiding the action at the pool?"

"Yeah," I responded. "I don't want to burn myself out too early. Plus, I am here with my daughter and her friends and don't want to hover."

"You're with the girls?!" Her face lit up. "That's fantastic! I just saw them at the pool. Looked like they were having a blast."

I explained to her the empowerment concept that Sara had preached to me and my reservations in cock-ring-toss being an empowering act but I was hushed immediately.

"They are young and having fun. That type of thing is actually perfect for their age. What are they, early 20's?"

"18, actually. Every single one of them."

"God, to be 18 again."

"Well, life is about experiences. I hope this trip is a good one for all of them."

She patted her hand on my thigh and complimented me. "That is a wonderful mindset to take." We sat in silence for a while before she opened conversation again. "So, don't get me wrong, I love the fact that you are here, but how is it that your daughter's mother did not get chosen as her chaperone?"

"I am a widower, actually. She passed quite a few years back."

"Oh, I am so sorry. This is why my friends tell me to keep my mouth closed."

"No, it's okay. Brie was young. It was a long time ago."

"Brie was the mom?"

"No, sorry. Brianna is my daughter. Since it has always been just the two of us, we were thankfully able to avoid the drama and instead have always just been really close. She actually asked me to come along."

"Well, that is just fantastic."

"How about you? Here with a boyfriend or group?" I knew the resort catered to couples and groups of singles, not singles by themselves.

"No boyfriend or other significant other. Like you, I am also babysitting. In my case, I am the old matron watching over my little sisters bachelorette party."

"Fun."

"Yeah, hopefully. We'll see. Right now they are all so hungover just from the flight here that only one is even out of bed. And I get the feeling that I was only invited because I am family, not because anyone actually wants me here. Nonetheless, they are the rookies that can't hold their booze and I am going to get some color."

I chuckled my response. "I'm Mark by the way."

"Heather."

We spent time talking and sunning. It was surprising how much we had in common, including that she lived only about 40 minutes away from me. She was divorced, but with no kids. She owned a boutique shop and salon that specialised in swimwear and lingerie. She also rarely traveled but, more so than poolside hedonism, she was looking forward to relaxing and getting some color.

"Considering my line of business, it is pathetic that the only tan I get these days is the spray-on kind."

When the time came, we went to get some lunch together at one of the resort restaurants and ran into the group of moms. Though the women were cordial enough in their interaction, I swear I felt a bit of animosity directed my way from Gina, like I was somehow cheating on her just by having lunch with another woman. Nonetheless, the conversation remained enjoyable at lunch and when we decided to go back to the beach together afterwards, we ran into a group of the girls, not including Brie, who were planning on the same thing. I was pleasantly surprised when they all acknowledged me and graciously met Heather. I was not at all upset or disappointed when they informed me that they would be heading a bit further down the beach and away from us.

It wasn't that long before Brie, who had apparently already been on the beach, wandered over to us to say hello and meet my new friend. Out of the corner of my eye I think I literally saw Heather's mouth drop when my daughter sauntered over wearing nothing other than the tiny g-string I helped her pack before the trip. It could be said that, objectively speaking, my daughter is a fantastically attractive young woman. She is 5'9" tall, lean and curvy, a perfect shape for the sport of volleyball she loves. She has long, dirty-blonde hair, an attractive face and, I know this because I help her shop for clothing (including bras) measurements that come out to 35C-22-34. So, if I can admit it, her wandering over is about the same as a mens-mag centerfold walking directly into the scene.

"Hey, Brie."

"Hey, Dad. My friends said that you were hanging out with someone and I thought I would say hello."

"Brie, this is Heather. Heather, my daughter Brianna."

The two shook hands and made some very general small talk before Brie asked to pull me aside for a moment of private conversation.

"Hey, a couple of things," she began, peeking over my shoulder at Heather. "First, way to go! She is really pretty, a red-head too; right up your alley! You took my conversation to heart I see."

"Brie," I tried to interrupt to clarify that there was nothing going on between Heather and I though she was having none of it and just continued on.

"Second. A few of us were talking to the staff and they told us there is a fully nude beach within walking distance and we want to go. But, they said that unless we want to get harassed by the locals trying to sell stuff on the beach we should have a guy with us. So, the other girls suggested that you come with us."

"Your friends want to go to a nude beach with me?"

"More like my friends and I want to go to a nude beach and need you to go with us."

"Do I need to be nude?"

"It would probably be awkward if you weren't."

"I'm gonna' have to think about this."

Brie said her farewell and I slank back to my chair with Heather.

"That is your daughter? Oh, my God, Mark! She is gorgeous!"

"She just told me that she and her friends want me to go to a nude beach with them."

"Well, she was already practically nude. And, hell, if I had her body I would show it off as well."

"Brie isn't my concern. I've always raised her to be confident in herself and that nudity is natural. The problem is that not everyone shares my same views. How will the girls parents or significant others feel about the responsible chaperone getting nude in front of the 'kids' of the trip?"

"I don't know. They are all here, right? People had to know what that came with. Besides, this could be a perfect opportunity to spread the actual confidence and empowerment message you were telling me about earlier. Something other than faux sex games on the pool deck."

"I suppose."

"What would the other moms think?"

"Two of them will be in and encouraging in a heartbeat. The last I don't necessarily know."

"Well, while my two cents is that you go for it. You can offer a positive experience to these girls and show them first hand a much more European experience as opposed to a bunch of hooting frat guys."

She had a point. It still seemed a little weird. 3 days ago I had a comfortable, positive relationship with my daughter. Now I appeared to be expected to automatically have the exact same relationship with 19 other girls and 3 moms. I think I needed to speak to Melanie. Her thoughts would get me my answer.

------

"I am all for it." Melanie was laying out at the pool, drink in hand, bikini top nowhere to be seen. "Not only do I think it would be fun for the girls, I think it will be fun for the adults too." Emily had already told her about the proposal to go. It seemed that Melanie, after the brief hesitation and moment of self doubt, was fully vested her idea of having fun and getting past the bullshit of her divorce.

"And you think it is okay for me to be there? No repercussions for my exposure once we get back home?"

"First, the girls are done with high school so the gossip mill will drop exponentially. Second, they are all adults. Third, everyone already knows you are a good guy. Seriously, Mark. Have a drink. Whip out your cock. Live a little."

It was a happy surprise to get Melanie's endorsement though a little shocked to hear the way she did it and I admitted I did need a drink. Two days into the trip and I had only the first shot in the pool to show for it. While I had never been a person to equate alcohol with fun, I could admit that a drink will help loosen most people up and, with the nude beach proposal, I needed exactly that.

A familiar face was at the bar.

"Hey, stranger," Heather said and greeted me with a kiss on the cheek. "Did you figure out a plan?"

"I haven't talked to Brie yet but it looks good to go. Now I think I need a drink."

Heather called the bartender over and ordered me a double shot and then a fruity, frozen drink to chase it down with. In addition she introduced me to the group she was with.

"I told them your dilemma," she explained to me. "They not only think it isn't a problem, they also think that they want to go too. Can we join you or can you at least let us know how to get there?"

There were 8 total women in her group, meaning that in addition to mine, it would be 31 women and me, assuming everyone went. But, as the alcohol quickly hit me, I threw caution to the wind and let them know I would give them the details.

-----

Part 3:

It was the next day that we decided to go as the general consensus of the group was "why wait?" The previous night had been enjoyable. Dinner again as a group and then dancing at the nightclub into the night. I saw that everyone was drinking more than I had previously noticed but there were still no concerns with anyone overdoing things and getting into regrettable situations.

Once the morning came, I was surprised to find that I was the one who slept in longest but was not surprised to find that the moms had abandoned any pretense of modesty and had already taken to walking around in the nude as they got ready for the day at the beach. What was a secondary surprise was the group of girls that crowded into our two rooms, ready for the walk to the beach and seemingly giddy about the prospect of going full-nude out on the sand. Did they care that I was still laying in the bed they were practically bouncing on? Apparently not.

In the end, only 12 of the girls decided to go and, because 8 seemed to be too high of a number to leave at the resort alone, Gina decided to stay behind with them. With Heathers full group tagging along we had a total of 23 and, as expected, I was the only guy. It was admittedly a bit nerve wracking but Brie assured me that it was just fine. The walk over was slightly technical in that we did have to go off resort and through was basically amounted to wildlife paths and over a series of rocks and small cliffs but, when we got there we determined that the hotel staff was right, it was a fantastic beach.

There were probably about 15 other people already on the beach when we got there, mostly men and, presumably, mostly gay couples. That said, the beach was large enough to easily hold a couple hundred without anyone crowding on one another so we found a spot for our large group not too far away from everyone else but not to bother the other patrons either. Putting our minimal amount of gear down, we got down to business: sunscreen.