Single Male Chaperone - Reimagined

I stepped into her and gave her a hug... with an unexpected reaction from Sarah.

"Ewwwww," she whined as she pushed me away, "that feels so gross."

I felt my face go pale. After what we just did she thought a hug was gross?

"Your pubes are so scratchy. You seriously need to do something about them."

Being so close, I reached into my vanity and grabbed a pair of clippers I kept and handed them to Sarah.

"Okay, expert, make me presentable."

Sarah sat back down on the toilet and pulled me in front of her, my dick dangling directly in front of her face. With clippers in one hand and my dick in the other, moving it up and down and left and right, she inspected with a focused eye while I just stood and mused at the absurdity of the scene. Though, while I was not particularly focused on anything, I was surprised by the voice at the door.

"Uhm, okay. So, like, what's going on here?"

Tiffany was standing in the doorway to the bathroom, also fully nude, with a curious but amused look on her face.

"Where the hell are the towels?" Bethanny was yelling in the background.

"In here," Tiffany responded. "Your dad's bathroom!"

Sarah never let go of my dick.

Bethy appeared in the doorway, her hair dripping wet and a slight shimmer of wet on her body.

"WTF, Sar! You were supposed to be bringing towels down!"

"I got distracted," my stylist responded as if the scene were the most normal in the world. "I actually hold you responsible for this, Bethy. As the only person to live with him and see him nude on a regular basis, it is your responsibility to remind him of proper grooming habits."

"Right. Because grooming is what kept you up here so long." Her response came in a manner that made it obvious they had heard us previously.

"Maybe not, but it's what keeps me here now, so suck it up. Anyhow, both of you come here, let me know your thoughts."

The two other girls crowded into my small master bath and joined their friend in inspecting me.

"Thin out the top and shape it," Tiffany responded as if it were the most objective situation one could come across.

"No comment," Bethy said flatly. "I am sure you two can make the right decision."

Sarah flipped the clippers on and made a motion to begin her work when I stopped her.

"Whoa. Hold up. Is this some sort of elaborate prank that you three put together just to make me look like an idiot?"

Sarah's response was less than convincing.

"Live a little, dude."

And with that, she just started clipping.

"Towels are on the dresser," I told Bethy and Tiff with a sigh. "And the food should be here soon. I forgot we had nothing in the house so I ordered from the deli. It's already paid for but you might want to cover up before opening the door or you'll give the delivery person a heart attack."

"Thanks, Dad," Bethy replied and leaned in to give me a kiss on the cheek before pulling Tiffany out of the room. Who, I may add, seemed to want to stick around for a free show.

I was not surprised when I heard laughter in the hallway. I had nobody to blame but myself.

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Later in the evening when the girls had gone home and I had finally finished packing, I went into Bethanny's room.

"Hey."

"Hey, Dad."

She was lounging on her bed in her most typical sleep wear, a huge old, worn t-shirt and a super-loose pair of flannel pajama shorts.

"I just wanted to check in. See if you are doing okay. If there are any issues with everything that went down today."

"No, it's cool."

"You're sure?"

"Yeah, really, I'm sure. I want you to be happy and I want other people to know what a great guy you are. It's not like I think you and Sarah are getting married or anything. I think I would have a problem with that. But my friends and I, and hopefully you too, are just looking to have some fun, have some new experiences. You know?"

I felt my head nodding along as she spoke. She had become such a mature young woman.

"Can I be honest with you?"

"Of course," Bethanny replied.

"I never thought it would feel so right. Not specifically with Sarah but just in general. I didn't think I would like having sex again. There have only been a couple of instances since Mom died and each one of those was transactional at best. Something about today was different. I felt alive. If I am being honest, I want more."

"Well then go for it! We only have one life to live."

"And you're okay with that?"

"I seriously don't think that you are going to completely reverse your personality to the point that I would somehow feel crazily offended or abandoned. And what about you?"

"What about me?" I honestly didn't know where she was going with her question.

"How do you feel about me? You know I'm not a virgin, right?"

Of course I knew. My daughter and I were close. We told each other things. This current revelation was not anything groundbreaking for us. As a single parent, I was the one who talked to her about sex and pleasure and respect.

"I do, and I trust you to make the right decisions for you. And, I may add, the same rules apply in the future that have always held in the past: if you find yourself in trouble I will always be there for you, no questions asked."

"Well, I hope you know you raised me well enough that I figure to never have to take advantage of that... but, thanks."

I leaned in to give her a kiss on the forehead, we had an early morning with a lot of travel in front of us. Leaving the room, she stopped me.

"Oh, by the way, how did she do with your grooming?"

The thought of the situation made me chuckle.

"Okay, I guess. I'm no expert."

"Let's see."

I dropped the front of my shorts to show her my newly groomed pubes. While it may seem strange, the reality is that we had an extremely lax attitude when it came to bodies and nudity in our household. She had seen me naked plenty of times and I the same with her. Heck, the entire time we were talking I could see her fully exposed vulva through the open leg of her shorts.

"Not bad," she commented. "Maybe that girl has a future as an aesthetician."

"And maybe now I won't embarrass all of you on the beach! It's a winning situation for everyone! Good night, kiddo. Love you."

"Love you too."

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Besides having 20, 18-year-old girls practically squealing on the entire plane-ride down, the travel itself to the resort was pretty uneventful, though it did give me a chance to get to know my roommate for the 10 days we were traveling.

Shannon was 45 years old, the mother of Kara, and had been divorced for about 7 years. We had actually known each other for 4-5 years, mostly through the girls, but had also found ourselves in conversation at a couple of summer parties and whatnot. She was a lovely woman physically, 5'5" tall, probably about 145lbs, larger breasts and a curvy butt. We had always gotten along well and, while I can easily acknowledge the trials and tribulations that occur in any marriage behind closed doors, I couldn't for the life of me figure out why her husband left her. Especially for someone who he was divorced from within 2 years. Kara was her only child who, as confided in me via Bethanny, was known to be a bit of a wild-child outside of school. Indeed, Shannon had said that she questioned even coming on this trip as the environment was not exactly one of chaste celibacy. Though, after Kara's father agreed to pay for the trip behind Shannon's back, she decided to at least come along to be a voice of reason in circumstances that Kara might be getting out of line. That said, Shannon herself said that she was personally excited about the resort and was optimistic as to the availability of single men as she wanted to "dust the cobwebs out of her va-jay-jay for a few days."

As the parent chaperones, we had agreed that the girls would be bunking 4 per room while we each would only be 2 per room. Unfair? Possibly. Did we care? Absolutely not.

It was only late morning when we got to the resort. Checking in was straightforward and, as Shannon and I finished getting everything settled with our bags, I had a bit of a pause.

"How does all of this work? Should I stay in the bathroom while I change?"

I was in the bathroom speaking directly and hypothetically at the same time. Had I just been in the same vicinity of my roommate, I would have seen that she just didn't have the same apprehension that I did. Though, walking back into the main space I was greeted to a welcome site.

"What were you saying?"

Shannon was fully nude and checking herself out in the mirror. I could see that, for the slightest microsecond, she too had a bit of panic, as if she had already forgotten that she was sharing the room with anyone, let alone a male.

"Oh, nothing," I responded, "you already answered my question." I took her lead and began pulling off my clothing.

While obvious she was past her physical prime, I took the opportunity while stripping down to check out Shannon as she checked out herself. Her breasts were indeed large, bigger than I thought even, and hung naturally on her chest. Her tummy was soft and sensual, her ass was a little flatter than previously expected and she sported a significant patch of pubic hair which, though obviously groomed, was certainly larger than I had seen on a woman in a while. Whether it was the circumstance of simply seeing an attractive woman nude for the first time or something specific about her, I liked what I saw and surprisingly started becoming aroused.

Of course I had noticed her eyes checking me out in the mirror. They were darting about my body the same way that mine were darting about hers. She went a bit wide eyed and tried to repress a grin when my erection began to form, a situation I decided to tackle head on.

"Beautiful things cause certain reactions. Though I'm sure the nudity will be normalized soon enough, in the meantime... well, you know." I smiled back and folded my clothes into a neat file, something I would do in my own life but felt particularly inclined to keep up in the shared space.

"To be honest," she responded, trying to work the smirk off her face, "it caught me off guard at first. It's been a really long time since anyone had that reaction around me. While maybe I should tell you that I am offended, that as a woman I am not interested in being seen as a sexual object, well, I admit that, right here, right now, it feels kinda' good."

She had left the mirror and was moving things around in her suitcase and, even from behind, I could watch her large breasts sway from the movement.

TWO:

I stepped up behind her and put my hands on her hips. First just waiting to see what her reaction was and then taking the opportunity to get a sense of her body by moving my hands up and down her sides.

"Mmmmm," she purred, "that feels nice."

I reached around and cupped her breasts, taking in the sizable weight of each and doing what I could with my fingers to elicit a response from her nipples. Meanwhile, I positioned my erection in between her legs, the top of it nestled between her the cheeks of her ass.

"Are you always this forward?"

"Not really," I responded honestly. "Though it has been suggested to me that I need to open up out of my shell a bit more."

"I'd say you're doing a good job at that," she responded as she turned around and pushed me toward the bed.

On my back, Shannon straddled me and we began kissing frantically, a pace she dictated. It was obvious that my advances were welcome.

"Do you know that it has been 18 months since I last had sex?" We had stopped kissing long enough for her to reach down and guide my erection into her. She was surprisingly wet.

"Can't say I did," I responded.

It wasn't long before I realized that I really wasn't doing anything physically other than kinda' "being there." Shannon was the person directing and conducting any movement and, quite honestly, it wasn't that bad. She was thoughtful enough to put a pillow behind my head. She was vocal enough to tell me what she wanted me to do (if and when she was actually looking for me to do something) and very quickly climaxed on her own. Though, in the end, while it was not a lot of effort, when she finally slid off of my still very-hard cock, having already finished her own climax, it was more than a bit unfulfilling.

"Oh, yes," she sighed while laying on the bed next to me, her large breasts heaving on her chest, "I needed that. Thanks, Will."

"You're welcome, I guess."

Was I allowed to bring up the fact that I did not finish? I mean, afterall, women may not finish on a semi-regular basis but guys... well, that is kinda' what sex is all about, right?

I took a mental note to attend some sensitivity training and gave myself a minute as Shannon got up and went to the bathroom.

"Well, I guess the rumors are true, you will catch people having sex at this place."

I immediately knew the voice was Kate, a second chaperone parent. Mom to Elle, roommate for the week to Jenn. Looking up, I saw both Kate and Jenn standing in the doorway in between the adjoining rooms. Had we opened that?

"Sorry about that, ladies. Not looking to offend anyone," I responded as I got off the bed. My dick was still perpendicular to my body.

"Not offended in the least," Jenn responded. "I'm just glad somebody else broke the ice. Maybe you can be the guinea pig for outdoor action too?"

From the sound of her voice I would have thought that she was joking, but, from the look on her face, seemingly sincere, it was possible she was propositioning me. I kept a mental reservation for that later.

"What are you two up to?" I decided to change the line of questioning as I grabbed my swimsuit from my luggage.

"Heading to the pool." Jenn was actually the one who responded.

Good lord, she was hot.

"Fantastic, I'll join you."

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I never actually made it to the pool.

At least not immediately, not when we said we were going to go down. A couple of things happened.

First, I was a little apprehensive about the tan-through shorts and also felt ridiculous wearing them under another pair of shorts so Jenn lent me an extra beach wrap that she had. It was a huge, lightweight scarf of sorts that I simply wrapped around my waist and I really liked the way that it looked and felt. If I'm being honest, I immediately thought about how much better it would have been without any shorts underneath it at all.

Second, as we left the room, we ran into Tiffany.

"Mr. Patton, hey! I'm glad I ran into you. Wondering if you could help me with something."

"Do you want me to save you a chair?" Kate was obviously not planning on waiting around for whatever Tiff needed me for.

"That would be great, thanks. I don't know what she needs but suspect it won't take that long."

"Give her all the time she needs."

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I followed Tiffany back to her room. I had been surprised to see that she had been wearing what would most likely be described as a "normal" bikini considering the fact that not only we were at a resort that practically encouraged toplessness, but that she had been tanning in just a thong (or fully nude) at my house for some time.

"You probably think I am overdressed," she replied with a sigh as she plopped herself down on her bed. The room was empty of other girls but their presence, in the form of a tornado of clothing, underwear and towels strewn about the space, was obvious. Tiffany, unlike Sarah, was not particularly curvy. She had smaller, A-to-B cup breasts and little hamburger buns of ass cheeks, but what she was lacking in voluptuousness she made up elsewhere. Tiffany was, in my opinion, one of the most naturally attractive girls I had ever seen. She had long, toned legs, a flat stomach, and the most beautiful long dark wavy hair that my own daughter constantly whined about not having.

"I was a little surprised, I guess. But, hey, whatever you are comfortable with."

"I want to wear something more daring but admit I am just a bit more hesitant about it than I thought I would be. I know that you and Sarah made a deal to be nude on this trip and I think I might want to join that group, I just need a final impartial okay to do so."

Tiffany stood up, took off her swimsuit and stood in front of me in a less-than-confident stance.

"Honestly speaking, do I have a nice body?"

She had stood in front of me nude after my session with Sarah without a care in the world. I was surprised to see her so nervous.

"Honestly speaking, yes." My response was flat and straightforward.

"My tits aren't too small? My ass isn't too little? My hips aren't too narrow?"

"Tiff, honey, you're one of Bethy's more recent friends so it isn't like I have known you for that long, but I can say your insecurities are misplaced. You are absolutely lovely."

"My tits?"

I stepped toward her and cupped a hand over her small breast.

"A perfect handful," I replied as I let myself gently stroke her hardening nipple. "Besides, it's said that breasts of your size are often so much more sensitive."

"I can attest to the truth in that," she replied, her breath just a bit shallow, "it can be bothersome on my runs sometimes if I let my mind drift. What about my ass?"

"What about it? It crowns probably the finest legs I have ever seen. It fits your body perfectly." I reached my other hand around and gently massaged a cheek. The resulting hunched position allowed for perfect access for me to place a kiss on her neck.

Tiffany let out a deep exhale and took a small step back.

"Jesus, you can be convincing. Just let me finish, okay?"

"Fine," I replied in a sarcastic whine.

"Lastly, what about my hair? Dark pubes can be problematic, is everything trimmed okay?"

Though her skin was tanned, I could see, if I focused, the visual shadow of dark pubic hair on both sides of a well manicured landing strip.

"I think you are getting a bit too in the weeds here. You are a beautiful woman, just leave it at that."

"Uhgg, you're no help. Fine, just tell me if I got everything."

Tiffany got on all fours on the bed and pushed her ass up into the air, her small cheeks spreading naturally, her little tan asshole staring at me.

"Umm, are you planning on tanning in this position?" I chuckled as I leaned in to inspect.

THREE:

She smelled of coconut suntan oil and I felt myself grow aroused. I consciously massaged her ass cheeks, gaping open her tiny pink pussy with each pass. My cock was rock hard and the wrap that Jenn had given me hung comically off of it. Indeed, my tan-thru shorts did nothing to conceal an erection. I leaned in and kissed her puckered little asshole, an action that drew a gasp from Tiffany, who plopped down on the bed before swinging around to me.

"How do you know I am into this?" Her question was coupled with a smile.

"I don't," I responded truthfully, my hand cupping her young face. "And, if you aren't, that's fine. I have been encouraged to take a different approach to life though. I have to admit I am being a bit more forward than I probably should."

"Well, I am into it. Girls love a guy who takes charge."

Tiffany pulled my waist scarf open and, with barely a moment's hesitation, took my cock into her mouth. She was eager and aggressive and it was obvious that she had learned her technique from watching bad porn. She made loud slurping and moaning noises as if she was auditioning for a role.

I thought about her comment, about taking charge, and I knew it wasn't just women. Guys too could very much enjoy when a woman took charge or made it clear exactly what she wanted. In this case, I knew I was going to have to continue being the teacher.

"Hey, hey, slow up," I whispered loudly as I gently pulled her face off my erection.