Single Male Chaperone - Reimagined

"This is my friend Hunter."

Of course I should have gotten up and shook his hand or at least offered some sort of more formal introduction but, in my predicament, I simply offered a greeting and a 'pleased to meet you' and left it at that. It was the same from Jenn.

"I'm glad we ran into you," Bethy continued, "we were looking to go back to the hidden beach tomorrow. Are you guys up for that? I figure I can talk to the resort beforehand and even plan a little bit better."

"Absolutely! It was so much fun last time, we'd love to."

Jenn responded before I even had time to compute what was going on but it didn't much matter as my mind had obviously been made up for me.

Bethanny and Jenn excitedly roughed out some basic plans. Hunter and I stood by. He seemed to be at least relaxing to the situation in front of him, no longer a deer in headlights. I couldn't believe that my erection hadn't subsided in the least; still impaling Jenn, still rigid and twitching at her slightest movement.

When the conversation was finally done and Bethanny and Hunter left us (unfortunately making their way further down the beach instead of back toward the resort) and they were clearly out of eyesight, Jenn collapsed back down onto my chest.

"Think we were caught red handed?"

She was giggling in my ear when she said it so it wasn't as if I really thought she was upset. It was just more ridiculousness of the trip.

"I actually think not," I responded. "I am pretty sure Bethanny would have said something and picked on us if she knew. On the other hand, maybe she was just trying to play it cool in front of her new friend."

"He was a good looking guy," she said, beginning to work her hips a bit, bringing some real movement back between us, "she could do a lot worse."

"As long as he is a good guy. That's all that matters to me."

"That's sweet," she whispered in my ear, her voice getting breathy, "that's the right attitude to have."

It was surprising to me how quickly she was coming to climax but it was more surprising to hear Bethanny's voice again.

"Hey, guys? I forgot something else."

She was standing in the exact right (or wrong) place and there was absolutely no chance she couldn't have seen the explicitness of our union. Jenn stopped her movement and buried her face into my neck. I craned my eyes up over her shoulder and attempted to address my daughter.

"Uhm. Yeah? What is it?"

Though I swear I did my absolute best, I can't be certain there wasn't a bit of annoyance in the sound of my voice. Realistically, in hindsight, I think it was more one of shame.

"Kate has been looking for you, Dad. She said that it is important she talks to you before dinner."

"Thanks, honey. I'll make sure I do that. See you later."

It was my last comment that drew a smile from her face. It was obvious I was telling her to take a hike and it was obvious that she interrupted us - and specifically approached us from the angle she did - for a reason: just a little bit of a power play on her part.

Well done.

I wish I could say that our climax was perfect afterwards but the reality was it just wasn't. After having been stopped twice, and after Jenn couldn't stop thinking about what could possibly be so important for Kate to speak to me (not because of Bethanny interrupting, rather just why Kate would have any topic of importance), we somewhat limped across the finish line. While I know I finished - it is tough to deny the existence of a milky-white load of ejaculate - I couldn't be for certain that Jenn did as well. Though as she lay next to me and expressed her contentedness in the trip... and the day... and the specific situation, I took it that it also really didn't matter. Afterall, life was good.

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It hadn't been 3 minutes after finishing lunch (we had returned to the resort after agreeing on a shared need for sustenance) that Jenn had left me to find some of the girls and I happened to run into Kate. She didn't say much but instead pulled me into a quiet alcove and pitched a proposition to me; a scenario that somehow felt wrong but also felt just too intriguing an opportunity to pass up.

It was obvious that, even considering everything that had already happened, my evening was going to be a bit wilder than I would have ever expected.

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The group dinner was fantastic, just like all of the other dinners had been thus far, with good food and good friends, and had been appropriately lubricated by some shots of tequila and fruity bar drinks. It had been hours since I had spoken to Kate earlier in the day and I found myself getting a bit nervous. I wasn't sure why. Afterall, after everything that had gone on so far on the trip, the plan for the night wasn't altogether that different: it was just going to be sex. That said, I think it was the fact that it was planned that rattled around in the back of my head. Everything up to that point had been just taking advantage of a situation that presented itself. Now there were... expectations.

As I swallowed the pills that Kate had given me I was thankful for two things: first, the liquid courage of the alcohol; second, the easily consumed pharmaceutical "sure thing."

I had seen a number of our group heading for the dance club when I first made my way up to the room, fiddling with the key card that Kate had slipped me prior. It seemed strange that she insisted on going through the trouble and expense of getting another room, a suite nonetheless, just for the evening. My thought process, in it seemed that nobody in the group, considering what had happened so far, would be judgemental as to anything that we would be doing, may have been naive, but I didn't argue her desire to keep things as private as possible.

When I stepped into the room I was surprised by the size of it. Instead of the standard hotel room layout where we would walk into a small hallway, bathroom on one side and bedroom at the end, I walked into a relatively large foyer that led into a large living and dining area with a fully glass back wall. Though it was dark out, it was obvious the room looked directly out over the ocean

"Hello?"

Kate came out from around a corner. She was fully nude and her hair was wet.

"Hey!"

I was surprised as to how upbeat she was.

She walked to me and started pulling my shirt up from my waist and over my head, quickly removing it from my body before dropping it casually to the floor and taking on the rest of my clothing. I was nude in no time.

"Hop in the shower and get cleaned up," she instructed, "I'll talk to you again when you get out."

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I wasn't surprised that the water was already running and I wasn't surprised to find Elle standing under it. She wasn't surprised when I stepped into the large, glass stall with her.

"Hey, Will."

There was a tiny amount of hesitation in her voice.

"Hey. How are you doing?"

She stepped out from under the water and somewhat into me, a move I completely misread on purpose when she reached around my body and to the wall behind me, activating another shower lever I hadn't even noticed and getting a second stream of water started. She hadn't responded verbally yet, instead just offered me a look that only a teenager can offer to the clueless adults of their lives. I smiled back, acknowledging my thanks for her turning on the shower.

"Good," she finally responded. "A little nervous, I guess. How about you?"

"Good," I offered in return. "Also a little nervous."

"Really?"

Her response was somewhat incredulous and somewhat relieved at the same time, affirmation of her own feelings.

"Sure," I continued. "If I am being honest, I get a bit nervous just about every time, let alone something like this."

Elle stepped deliberately away from her side of the shower and over to me, inquisitively taking my dick into her tiny hands.

Physically, it was obvious that Elle got her build from her fathers side of the family. Though she and her mother shared some physical traits in their lean athletic-ness, there were enough differences to even question maternity. But, while I had already expressed a long-standing attraction to her mother, to say she was different was not to imply that she was unattractive - a notion that couldn't have been further from the truth - simply different... and very sexy in her own way.

She was a petite young woman at 5'3". Though her body was thin and obviously athletic, it was also blessed with a plump, youthful ass and larger, surprisingly pert and firm breasts that stood out like cones from her body, each topped with puffy pink areola, each areola topped with nubby large nipples, each nipple pierced horizontally with a gold bar adorned with tiny rhinestones on each side. The jewelry was enough of a curiosity that I instinctively brought my right hand up to her breast, rubbing her nipple under my thumb.

Elle shuddered.

"Bad?"

"No," she responded, not at all. "I was just never prepared for how sensitive the piercings made my nipples."

She stepped back away from me, leaving my cock standing parallel to the shower floor, and took her breasts into her own hands, looking down and inspecting their be-jeweled caps.

"I got them done about 8 weeks ago. I wanted something special for the trip. What do you think?"

I over-acted a moment of academic inspection and thoughtful ponderance before delivering a truthful verdict.

"To be honest, pierced nipples have never really been my thing. But, if there ever were breasts - or nipples, specifically - that called for them, they would be yours, and the simple jewelry you chose really looks great."

My response did not gain my hoped-for response in that she didn't step back into my arms, but I did get a smile of appreciation and a request to objectify her further.

"And what about this?"

She used her hands to frame a relatively large geometric flower pattern tattoo on her hip.

"The plan is that this is going to be the start of an entire side piece. Basically, from here to here."

Her body contorted a bit as she repositioned her hands and moved to block out the area of her side from the middle of her rib cage to just above her knee. Truthfully, I hated the idea. Of course I knew that tattoos and other body mods were popular with a large demographic, I just wasn't one of them. The only consolation to the proposal was that I could clearly see the work she already had done was top notch, truly art from an obviously talented artist.

"What do I think? Well, I think you better save your money. Work like that can't possibly come cheap."

"Ha! Now you sound like my mom."

Her response ignored that I really didn't comment on the subjective nature of my opinion of inked skin... and I was perfectly fine with that.

"Hey, you two. Get out of the shower! You're gonna' be all pruned. The point was just to rinse off!"

Kate was standing in the doorway to the bathroom, still nude, and apparently a bit annoyed with our delay. I turned off the water from my showerhead and offered a smirking roll of the eyes before opening the door and stepping out on the dry, soft shower mat.

"Yes, boss," I responded to Kate. Her only reaction was to turn and leave.

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After drying I stepped into the bedroom of the hotel suite and could see that Kate was getting antsy to get started.

"Okay," she announced. "I figured to just start and end on the bed. That is, unless you have other thoughts or plans. I am not sure if you want to utilize the other rooms or anything. It was the only hotel room available so that is why I got it."

Her lack of confidence in how to handle the situation betrayed her normal steady, controlled manner.

"Bed's fine," I responded. "I figure you'll just tell me what to do. Like I said, you're the boss."

Kate pulled the covers back on the bed and bit and fluffed the pillows when Elle spoke up behind me.

"No, I'm the boss. She's the hired help."

Elle threw herself on the bed and faced me, a mischievous look in her eye. Her dyed blonde hair was wet and somewhat stringy from the shower and it was obvious that in just the couple of minutes we had been apart she had applied eye-liner, mascara and lipstick. She was propped on her elbows and her legs were splayed wide, her fully shaved - or possibly even waxed - vulva on graphic display. Her delicate lips had naturally parted, leaving a luscious pink gash to admire. She looked like a rockstar and I admit I was surprisingly drawn to her.

"Hired, ha," Kate scoffed. "As if she is paying me."

My erection hadn't gone down but my heartrate had gone up and I wished there was a shot or two of liquor I could have taken to calm my rising nerves. For the first time, I was no longer intrigued by the situation, I was legitimately nervous.

"So, Will," Elle said after a mildly awkward pause and silence, "you ready?"

Nervous or not, here went nothing.

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TWENTY:

I feigned as much confidence as I could and knelt to the side of the bed, pulling Elle to the edge, draping her legs over my shoulders. I placed a direct kiss on her naturally exposed clit and got a bit of a gasp from her. Under normal circumstances - meaning in a situation that did not find me with a presumptively single-time lover whose mother was hovering just over us, smart phone in hand, hi-definition video and pictures documenting the event in front of her, all while nude herself - I would have spent a significant amount more time on foreplay and preparation. But these were not normal circumstances.

She didn't have much of a taste or aroma right from the get go as the shower had left her squeaky clean though, Elle, to her credit, did not seem to care in the least that we had an audience and quickly got primed - her nectar sweet and tangy - her guidance as to what she wanted me to do refreshingly bold.

"More on my clit."

"Pinch my nipples."

"Squeeze my ass."

It was very obvious that she was her mothers daughter.

Of course I had known what the situation would be. It was what Kate had proposed and prepped me for earlier in the day: Elle wanted to be a bit naughty and apparently their relationship was close enough that Kate felt comfortable being the official documentarian. I can't say that it wasn't strange at first to feel the mattress shift around with her steps as she moved to get different angles... or when she literally put her hands on my face to have me "open up to the camera" and allow a more direct view of my tongue working its way between her daughters slick, lower lips. But what was most strange was how quickly the involvement or distraction of her faded into the background. The reality was, I was really into what Elle and I had going on.

She had rolled through an orgasm and had expressed interest in getting some pictures of my cock in her mouth (Author's note: those were her words, she insisted it wasn't a real blowjob) and had me lay on my back. The position, literally in the middle of the bed, flat on my back with nothing under my head, was neither uncomfortable nor enjoyable. What I wanted was to watch her soft lips wrap around my head and shaft. What I was hoping for was a ring of her freshly applied lipstick to be left as a reminder on the base of my cock. Instead I stared right at the ceiling.

That is, until my view was blocked.

It couldn't have been more transparent when Kate straddled my face. She had whispered to me that she needed to position herself for another shot just before swinging her thighs to the sides of my ears. Any doubt of her true intentions were alleviated when she settled her extremely hot, very wet pussy directly onto my mouth. If the stereotype of older women not getting as wet as their younger counterparts was based on any element of fact it was obvious that she had been left out of the survey.

Or, maybe Shannon was right in that Kate was just getting herself so worked up and primed it was an inevitable conclusion. No matter the situation, I was appreciative and took advantage of it... at least temporarily. Her flavor had a bit less tang to it than her daughter and, if I could be so bold as to portray myself as some sort of vaginal-solemelier, it was as if I could taste her age. It was a bit muskier, a bit fuller, a bit more mature, a combination of traits that equaled a single adjective: fantastic.

It wasn't long before Elle had declared that she was done with felatio and requested that I get on my knees. Though I recognized my role as a prop it didn't mean I couldn't enjoy myself and as Kate began to lift her leg over my head I brought my hands to her hips and pulled her back toward me, offering a parting gift of stimulation to her clit, her dripping pink, her asshole. I was pleased when I felt her body tense up for a moment as I ringed my tongue around her puckered anus as I had wanted to catch her slightly off guard and clue her in to the fact that I would be interested in pushing the limits of what she felt comfortable with in her "open relationship." The personal revelation was surprising to me as I never thought of myself as someone who would get involved in a complicated situation like that but, when in Rome... afterall, she did just sit on my face.

Elle already had her ass in the air and was waiting for me to mount her when I finally got up from my back. Kate had a smile on her face and, as I went to line myself up for penetration, she snuggled into me a bit, caressing my cock with one hand while deeply kissing me.

"You taste like me," she whispered in my ear after our mouths had released from one another. "Don't forget to turn your hips out for the camera," was her final comment before kissing me one last time and tending to her other responsibilities.

My staff swelled like iron in her soft but firm grip as I watched her lick her two fingers of her opposite hand and use them to spread her daughter's slick lower lips apart and prep her for my phallus. The taboo of the scene was not lost on me and it only made me hotter and harder. I could barely contain myself.

I was a bit overly enthusiastic when I first pushed myself into Elle. I didn't ease in, I wasn't slow or gentle, I instead basically rammed myself in to the hilt, an action that elicited an audible gasp and whose momentum caused Elle to fall flat to the bed, taking me with her.

"Sorry," I whispered into her ear, "you are just so fucking hot."

As she had gotten back to documenting the moment, Kate only encouraged me.

"Yes! My God, that was great! Will, keep at it. Honey, the look on your face was priceless."

Of course, while I knew the photos were supposedly the reason for the evening, I also wasn't looking to hurt her.

As gently as possible I pulled each of us back into our intended position and began slowly working my way in and out of her gripping pussy. I temporarily ignored Kate's previously whispered direction to open up for the camera and instead focused on Elle.

I caressed her breasts and tweaked her nipple rings.

I gently rubbed her nubby, swollen clit.

I pressed a thumb against her asshole and tickled its sensitive nerves.

I pulled her hair and gripped her hips and brought her to a state of no longer being afraid of an intense fucking but instead to cries of wanting me to do it harder and faster.

Until Kate made us stop and demanded a final position.

I got back on my back and Elle straddled me, not on her knees, but rather on her feet, reverse cowgirl, leaned back with her hands on my chest, her legs spread wide, the most garishly exposed for the camera lens she could be. I could tell she couldn't quite get her balance in guiding me back into her though I was shocked yet again when I felt a mouth wrap around me. Craning my head as much as I could I was able to see the back of Kate's head bobbing up and down a bit before popping up and winking at me, a devilish look in her eyes before she turned away and focused her attention on guiding me back into her daughter's waiting cunt. It was all too much and I knew I wasn't going to last.