Single Male Chaperone - Reimagined

AUTHOR'S NOTE: I received a bit of feedback from one of my stories (Single Male Chaperone) regarding my male protagonist not fully taking advantage of the sexual opportunities potentially afforded to him. While I try to write my stories with at least an inkling of reality, I also understand that for many people the purpose of reading these stories is to step out of reality. And, hey, different strokes for different folks. So, whether you classify this story as "exhibitionist" or "group sex" or "free use" or "just plain stupid," here is a similar base concept with very different results. It's quite a bit longer too as, well, there is quite a bit more activity and, let's be honest, I can't just quit my wordy writing style. I even thought about breaking it into a few parts but, meh... fuck it. So, sit back, grab a drink, loosen those pants and settle in for a bit of an adventure. Thanks for reading, comments welcome.

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I was helping my daughter finish packing when I realized our vacation was going to be a bit more wild than originally envisioned.

"What's this?"

"One of my swimsuits."

I held up the absolutely tiny black micro-thong.

"Looks more like an eyepatch," I said with a wry smile.

"Yeah?"

She paused a moment after her initial response but I knew an equally sarcastic response was about to be hurled my way.

"Not sure how you got that, I figure my brown-eye is still going to be pretty darn uncovered."

"Jesus. What's wrong with you?"

I wasn't actually offended. My comment was just a bit of exasperation as to how far she took her response.

"Oh, whatever. You're gonna' be surrounded by a ton of hot girls, all of legal age and all ready to have some fun. I think I am the least of your worries. My friends are already scheming to get you back in the game and, you know what, they're right to do it. It's been too long since mom died. You need to live a little, you have a lot to offer the opposite sex. Seize the day, seize the opportunity, dad. Carpe Diem."

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My name is Will Patton. Not the actor, but a decent looking 41-year-old widower and father of one. My daughter is Bethanny (Bethy), 18-years-old, recently graduated from high school, off to college in just a couple of months.

We were on our way to an adults-only, all-inclusive resort in the Caribbean with a group of her graduating classmates. 20 girls in all, 4 parent chaperones, I was the only male. I hadn't been involved too much in the planning but there were a few things that I did know:

First, objectively, Bethy's friends were in fact hot. There was no question about it. I understand the subjective nature of beauty and attractiveness but there are also certain standards that anyone can agree on. Even through varying body types, skin colors and personal styles, these girls met these standards.

Second, the resort was known as a "free-spirited" locale. No, it wasn't a swingers resort. No, it wasn't a nude resort based on municipal law. But, it was liberal enough that female topless bathing was widely accepted and practiced (not revolutionary) and, if you did a bit of off-site adventuring, it was a somewhat open secret that hotel guests would take advantage of the warm tropical climate to get some outdoor sex bucket list items checked off (slightly more revolutionary). Was it odd that a dad-and-daughter were going to this destination together? Probably... and most certainly by American standards.

It had been 12 years since my wife, Katie (Bethanny's mom) died. Since then it really had been just the two of us. Katie had gotten sick when our little girl was only 2 so it was single parent, single child, single life. Interestingly, Bethy and I were extremely close. I watched sadly as other male (and female) friends of mine became estranged from their children as they went through those difficult teen years but it just didn't happen with us. I am not saying I am some sort of super-parent, nor am I saying that Bethy is somehow "different" as a child. I am only saying that, thankfully, we got lucky. As far as the potentially sexually charged nature of the trip? Well, I trusted her as a person, as an adult and as a woman to make smart choices that were the best for her. It was time for her to be able to do just that.

Third, she was right. Since my wife's passing I had only been on a handful of dates. Nothing had ever stuck and, if I am being honest, I had been doing a disservice to those women in that I most certainly wasn't ready to be with anyone yet. Though, in the last couple of years I had started feeling ready to get back out into the dating pool. With how busy our schedules were I figured to just put things off until I was an empty-nester. Maybe she was right in that I should accelerate that timeline.

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"Tiff and Sarah are coming over in a few minutes," she told me as we closed up her suitcase, a monstrosity of an item that I was sure was going to cost me an overweight fee.

"What the hell is in here?"

I strained to get the bag off the bed.

"It can't be swimsuits based on the size of the one that I just saw."

"Oh, don't worry about it. You know that girls pack a lot. I just want to be prepared."

Bethy had just finished stripping down and was wrapping a huge loose scarf around herself that she used as a beach and swimsuit coverup. Though, that day there was no swimsuit.

I can't say I was 100% surprised. Our house was pretty secluded and our pool had been the spot for a number of years that Bethy and her friends would have fun or lay out and get sun. In the early years it had been one-pieces. It then progressed to bikinis. From there the suits got smaller and more revealing. I had always felt that each of the styles had been age appropriate and, with all the girls' legal status recently changing with their 18th birthdays, one could potentially say that was still the case as, with the excuse of the oncoming trip, the girls had taken to sunning topless.

"No bottoms?"

"Last chance to get rid of tan lines," she responded nonchalantly. "What's the point of heading to paradise and starting it off looking ridiculous?"

I heard voices coming from the back of the house and she quickly left to be with her friends.

I peeked out of the bedroom window and saw Tiffany and Sarah, two of a solid group of about 10 girls that Bethy normally hung out with, coming into the pool area.

Ah, to be young again.

The thought drifted around an otherwise empty mind as I watched the girls greet each other and then begin stripping down. My cue to exit I suppose, no need to be a creeper.

I lugged the suitcase down into the kitchen and mused as to what was in it as it had to have weighed at least 80 lbs. Seeing that the girls were in the water I peeked my head out the back door.

"Hey, ladies! Any of you want lunch? I'm making sandwiches."

A chorus of responses volleyed my way.

"Oh, yes please!"

"I will! Thank you, Mr. Patton."

"Me too!"

I slid the door shut and got down to figuring out a menu, a task that took significantly less time than I had hoped for as, based on my own pre-trip planning, we had no food in the house.

I called in an order with a local deli that delivered and went back upstairs to do my own packing. But, what to pack?

I was practically embarrassed to pull the package out of my closet, a simple envelope that I had received in the mail a couple of weeks prior. In it was my new swimsuit, a tan-through option I had purchased online. Maybe I could go without tanlines too.

I stripped down nude but, before putting it on, I admit I checked myself out in the mirror. I had always been lean and stayed in shape with running, swimming and some very basic weight training. I enjoyed the running and swimming though I loathed the weights. That said, at 5'11" and 185lbs, I felt I was doing okay. Of course, being a guy, I also had a bit of a fascination with my own dick: was it the right size, the right shape? Did women find it attractive? I got myself to half-chub, enough to get a bit of girth in it, but otherwise still hanging, and continued to pose in the mirror.

"Not bad for an old guy," I said to myself, out loud.

"Aww, you're not old."

The voice startled me and I spun around to find Sarah standing in the doorway of my room, as naked as the day she was born, just a shimmer of oil on her skin and a smile on her face. She was one of the curvier of the group of girls Bethy was close with, characteristics that I had watched develop over the years and that were now on full display in front of me. She was about 5'4" tall, light brown hair and had a full, oval shaped face. Her breasts were large and sun-kissed, no doubt at least a d-cup and were topped with round, sun-soft and tanned areola and nipples. The rest of her body was a perfect hourglass and her shapely legs directed a viewer's eyes to her fully shaved pubis, her protruding labia clearly visible.

"Sarah! Shit, you scared me."

"Sorry. I came up to get some towels. Is that okay?"

"Yes, of course, you know where they are."

Sarah had spent enough time at my house over the years to practically qualify as a dependent on my taxes.

"Yeah, all the ones in front are gone and I can't reach the ones in back. Can you help me?"

My mind went to the task and I walked with her into the hallway to grab the towels. Though I almost immediately regretted bringing it up as the words left my mouth, I couldn't help but comment on her attire.

"So, no tan lines for you either?"

"Your daughter is very convincing," she replied. "I'm not a hundred percent sure I will go nude once we are down there but it seemed reasonable enough while we are just out by the pool here. I mean, it's only you."

Her comment got a chuckle out of me in my response.

"Ha. Only me."

She sighed and gave me a playful hit on the arm, then hugged me in mock apology, pressing her sun-warmed breasts into my skin.

"Oh, don't start. You know I didn't mean it that way. I just mean that I am comfortable around the girls and I am comfortable around you as well."

"Well, I'll take that as a compliment."

"You should. And, take this as a complement as well: you are definitely not an old guy and you are definitely looking good."

I felt a smile drift across my face. Inappropriate situation or not, it felt good to get the compliment and a bit of affirmation.

"Hey, can I get your opinion on something? I might as well take advantage of an extra pair of eyes while I have them."

"Sure, what's up?"

"A new swimsuit I bought. Yay or Nay?"

We went back into my room and Sarah sat on my bed while I pulled on the thin, kinda' mesh-y suit.

"Okay, here you go. What do you think?"

I didn't quite know how to stand, so I moved into a couple of "I-think-this-is-how-models-move" types of poses. Sarah, for her part, had a legitimately studious look on her face.

"Come here."

Her comment was accompanied by a hand motion for me to join her by the bed. The gesture also caused me to really notice her nudity due to the most subtle jiggle of her breasts. Of course I looked. Of course she caught me looking. Thankfully, her response was just to continue playing it cool.

She watched my every step as I took the few paces toward her and stopped about a foot in front of her. A distance that was, apparently, a bit too much. Sarah hooked her fingers into the waistband of the shorts and pulled me closer, my knees now practically touching the bed, her face just inches from my belly.

"What is the material?" She had her hand up the leg of one side of the tight shorts and her fingers were pulling and stretching the fabric.

"Some sort of light mesh, I guess," I responded. "The website claims that is how the sun gets through."

"I've heard of these," she replied somewhat absentmindedly, "I've just never seen one. Do me a favor, walk around the room."

I took a few paces and walked around the room as naturally as I could before stepping back in front of her.

"Okay, initial thoughts." Sarah laid back onto her elbows, her large breasts jiggling with her movements, her pose that of a model. "First, while I can't see it through the material, your dick bounces around pretty obviously. Also, while I can't see your dick, I can see your pubes so you are really going to have to trim them up."

She sat back up and ran her hand up my shorts, her small hand immediately grasping my cock.

"Uhh..."

She caught me a bit off guard.

"Oh, sorry. I just want to see what it will look like when you aren't limp."

She was so matter-of-fact in her words and actions. She was 18-years-old but had the confidence of someone twice her age. It was strange, but it was also extremely appealing.

It didn't take much for her to get me a bit chubby again and when it happened, almost clinically, she released me and had me walk around the room again.

"Yeah, not the greatest look."

I looked down and saw that it was quite obvious the way my shorts bounced around with my movement, the material was just so light it did nothing to minimize, only emphasize.

"Suggestions?"

Sarah smiled.

"You're kidding, right?"

She got off the bed, took my hand, and walked me across the room, through the hallway and into Bethy's room, straight to the window.

"What do you think I am going to suggest?"

We peered down into the pool area and were greeted with the site of two fully nude bodies reclined in the sun.

"Why are you worrying about a swimsuit?"

"One," I responded, "I did think about that and, while I don't have any particular hangup about being nude, I don't want to make anyone uncomfortable. After all, I am still one of the odd-balls out when it comes to age and I'll be the only guy. Plus, it isn't like I can just drop my shorts any time I feel like it. I have no idea how much off-site adventuring we will be doing. Second, did you just say that you weren't sure if you were going to go fully nude at all? Being a little hypocritical maybe?"

"Fine. If the situation allows it, I'll go nude and you will too. Deal?"

It was certainly not a conversation I ever envisioned having with one of my daughter's friends and I didn't respond, instead just gave her a hug and a paternal kiss on the forehead. We walked back into my bedroom and she again plopped herself down on my bed.

"Okay, your turn, opinion time. What do you think about pubic hair?"

"You already told me I need to trim."

"Not you, me."

Sarah scooted herself back on the bed far enough that she was able to bring her feet onto the mattress as well and, when she did, she spread her legs out wide in garish exposure.

"You don't have any," I said flatly. It was something I already knew.

"Yeah, I've been shaving for years. I have been thinking about changing things up though. It seems that most of the girls my age are either fully shaved like me or basically going full feminist and not shaving at all."

"My preference is somewhere in between."

There was a pause in the conversation where she did not respond to my statement. I stood there in front of her, she just stared into my eyes, a small smile on her face. The sight of her body was appealing and I felt myself getting hard. I had a hot, 18-year-old posing for me in graphic detail in a manner that seemed like an invitation.

Carpe Diem.

ONE:

Sarah got wide eyed as I made my obvious move toward her, scooting herself backwards on the bed.

"I'm on the pill," she informed me with absolutely no prompting.

"Good," I responded, "because you're going to need it."

There was nothing particularly romantic about what happened afterwards but, for the first time in a long time, I was thoroughly invigorated, thoroughly aroused.

I went down on her for a bit, sampling the sweet nectar that quickly formed after just the slightest stimulation from my tongue. I made long, smooth, sweeping motions across her clit, the folds of her lips and the tight ring of her asshole, all to the sounds of increasing louder "oohh's" and "aahh's."

After she climaxed, I spun her around into a doggy-position and mounted her, entering with long, smooth strokes as her body began to adjust to my penetration. Once it became evident that she and I were physically in tune, I pulled out and laid down onto the bed, having her mount me cowgirl style, her large breasts high and proud on her chest, a visual stimulus that only made me hotter and harder.

"Oh, God!"

Sarah had begun moaning as we got into a rhythm and, as I could sense her begin to climax again, her voice got loud enough to the point that I was sure Bethy and Tiffany could hear us by the pool. Did I shush her? No. Something about it just felt so right, as if it were supposed to happen, as if it wasn't an illicit affair or something taboo. The reality was, as both legally consenting adults, it wasn't.

Sarah had already been lying chest-to-chest on me for a bit, slowly building through a third orgasm, her body quivering with waves of pleasure, when I felt my cock swell inside of her. That last instant, when I should have potentially thrown her off of me, the pill not being 100% effective after all, was when a moment of clarity hit and I realized my life had just changed. I pumped her full of cum in what seemed like a never ending orgasm, holding her tight to me the entire time, both of us breathing hard into the nooks of the other's neck. When it finally was over, when we could take no more, our bodies went silent; Sarah a lump of flesh, immovable on top of me, both of us just trying to catch our breath in a post-orgasmic fog.

"Bethy said that you have been hesitant to get back out there," Sarah finally said to me as she came to, rolling off of me and onto the bed. "While I can't say I have a ton of experience, that was pretty much the most intense sex I have ever had. It certainly didn't seem like you had any hesitation."

"I suppose in this day and age I should have been asking specifically for consent," I replied, "and I hope we didn't do anything that made you feel less than special."

I rolled onto my side and gave her a kiss, my hand somewhat instinctually moving to caress one of her large, soft breasts.

"To be honest, I am not sure what came over me but can only say that it felt so right. It has been a really long time since I have been with a woman. Though, as we were together, I realized that Bethy was right, I do need to get back out into the world. I really appreciate you being here for me."

Sarah laughed.

"Are you getting sappy? After what we just did?" She put two fingers inside her pussy, withdrawing them to display them to me, dripping in my cum. "Mr. Patton, you have been so good to us for so long, we just want to see you happy... and fulfilled."

"Mr. Patton? Are you kidding me? In your words, 'after what we just did?' My name is Will. Don't call me Mr. Patton again or I'll have to spank you."

"Oooo," she whined playfully, "is that a promise?"

I kissed her again before she started to slide off the bed.

"I gotta' get cleaned up," she said, waddling into the bathroom, a hand pressed tightly in between her crotch. "I think you might have set a jizz record or something and I am dripping all over the place."

I gave her a minute before following in, looking to clean myself up a bit as well, and found Sarah giving herself a final wipe. As I stepped through the door, she smiled.

"Are all girls these days as confident as you are?"

She laughed.

"Definitely not, but most of the group of girls that are going on this trip are. We all agree that people get too hung up about stuff."

"I agree with you in theory. It's just rare to see it in practice."

"Well, here I am," she replied, getting up off the toilet and putting her arms in the air, "in all my glory!"