Single Male Chaperone - Reimagined

I hopped off and grabbed all of the pillows in the room, setting up a little cushion-y platform on the bed and instructed Kara to lay on it, upper body only, while I sat at the the base of the pillows and wrapped her legs around me; her entire young, smooth torso, her fully shaved vulva, all accessible to me. Nothing was said as I gently started caressing her body; her chest, her breasts, her neck, her sides, her hips, her pussy, her clit. It was fantastic to watch the tension in her body change, first just melting away, and then start to build... though in a different way... as her body began to react to my touch.

She was worried when I first unwrapped her legs from around my waist and pulled the pillows out from under her, laying her flat on the bed and spreading her legs, garishly exposing her sex to any advance I felt like making. She didn't say anything at first when I situated myself, on my belly, my face between her thighs, able to take in the scent of her excitement, of her actually being ready to be touched.

"Oo..Ooooo...oooooooohhh..."

It took her a second to catch her breath when I first dragged my tongue across the entire length of her opening and I took the same second to savor her flavor and how the entire experience of her being in the room had changed so drastically from questionably negative to extremely positive.

It was a pleasure for me to feel the soft contours of her lips and labia in my mouth, the smooth skin of her thighs on my cheeks and shoulders, the hot button of her clit on my tongue.

When the waves of orgasm began to wash over her body, Kara began to whimper and her body became tense. I took the opportunity to weave my hands into hers and I swear she practically broke my fingers when her body clamped down after its final climax.

"Holy shit," she said, trying to catch her breath as she wriggled herself away from my oral attention. "Holy shit, holy shit, holy shit."

Her chest was heaving and her nipples were puffy, seemingly trying to absorb their piercings, and her sex was red and tender, her labia puffy and swollen to match her nipples.

Though I hadn't been touched and though I was tired from a long day, I felt myself throb under the weight of my own body and found my dick pointing at the ceiling when I got to my knees.

What ever should I do?

I grabbed a couple of the pillows and shoved them under Kara's butt, raising her hips into the air and aligning her with my groin. I grasped my cock and dragged my engorged member across her entire length, making it slick with her wetness.

"Oh, my God."

Kara was wide-eyed, her focus directly on my phallus, an excitedly worried look on her face.

"Do you not want me to?"

"No. I do! I do want you to!"

I positioned my swollen head at her entrance and pushed in, little resistance being offered, and progressed, slowly back-and-forth, until I was enveloped to my base.

"Oh. My. God!"

She was a bit louder when she said it and I was somewhat worried that Kara would wake Kate and Jenn and I shushed her a bit.

"Shhhhhhh," I whispered, "just breathe."

I began slowly working my cock in-and-out of her at the same time as using a lubricated thumb to apply even attention to her nubby clit, each bit of attention not going unnoticed.

Kara moaned.

I watched her nipples go from soft to hard as the feelings within her built toward crescendo and Kara, somewhat instinctively, not only started pulling on her nipple piercings but also wrapped her legs around my waist, locking her ankles behind me.

I somewhat regretted not having her on top of me and I longed to have the feeling of her soft breasts drag across my chest with each of her movements though the fret was short lived as I felt the stir of climax within me.

Kara continued to moan when I first whispered.

"Kara..."

She ignored me.

"Kara, honey, I'm going to cum."

Though I had stopped much of the movement of my own hips, she replaced their absence, working herself vertically, never releasing the lock of her ankles behind my back.

"Kara..."

I couldn't take it anymore.

As my cock surged in stiffness and I felt my balls tighten, three things happened concurrently:

First, I came. Surprisingly hard. I have no idea what quantity of cum actually released from my body but the spasms of my penis - in their warm, moist cocoon - were most definitely real.

Second, a deluge of wet, a clear, warm liquid, flooded the topside of my dick as I continued to piston in and out of her and then sprayed across my lower abs, dripping down between us, down my thighs and onto the bed.

Third, Kara let out a final, long, breathy cry of passion.

"Jeeeeeeesussssssss Chriiiiiiiiissssssssst!"

I thought about putting my hand over her mouth. I thought about going and closing the door between the two rooms. My body let me do neither. I collapsed to the side of Kara, panting and exhausted, ready to sleep and recharge.

But, there was good news and bad news.

The good news was that my eyes caught the bright-red digital display on the in-room clock and it was still just before midnight. I must have fallen asleep almost immediately after Shannon left and Kara must have snuck in soon after that. Jenn and Kate most likely weren't even back from the dance-club yet and therefore we would not have bothered them. There was still plenty of time to rest before meeting with Heather in the morning.

The bad news was that the bed felt awful. As our climax had found us right in the middle of the mattress, the light bedspread and sheets had an unavoidable wet-spot in them that made getting comfortable completely impossible.

While I would have loved to have joined in on what Kara was doing, attempting to fall asleep in the fetal position, curled up in one tiny corner of the bed, I knew that it would not conclude with the restful rejuvenation that I knew I so desperately needed. So, to make a long story short and, in the right order, I... got Kara up and had her hop into the shower; stripped the bed and contacted the front desk about a new set of bedding (which I would have to pick up on my own considering the hour); cleaned myself off in the shower with Kara, an experience that found more playing with one another's soapy bodies that attempting straight-forward, functional bathing; brought Kara back to her room and the soiled bedding down to the front desk for replacement; back to the room, bed made and under the sheets by 12:30.

On any other night the action and excitement of the evening would have had me wired and awake for hours to come. On that night I fell blissfully asleep almost immediately, a full pallet of experiences looking to be revisited in my dreams.

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I was surprised when I woke up with my body's natural clock - just before the alarm I set for myself to meet up with Heather - though I was not particularly surprised to find Shannon asleep in her bed, knowing it was one thing to hook up with a stranger for some feel-good sex and something else entirely to also spend the entire night in their bed.

I had just hopped out of a quick shower, an action taken with the sole focus of making my hair combable, and was brushing my teeth when Kate stepped into my bathroom door.

"Good morning, Will."

"Hey," I responded through a mouthful of toothpaste.

"Workout?"

I grunted an affirmative confirmation.

"No morning wood?"

I turned my face down to address my flaccid penis. Though I had been up long enough and active enough that any sort of natural chubbiness would already have been gone, based on the events of the prior day, I was sure it could also just use some rest. I turned to Kate and shrugged my shoulders in response.

"Well," she added before stepping away, "remember that I can get you more Viagra if you want it. It doesn't even have to involve me unknowingly drugging you."

Okay, I thought to myself, mental note taken.

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The prospect of not having to even think about containing my erections for some time was a welcome thought. The last thing that I wanted was to spend the day fighting my dick while with Heather. And I knew, upon seeing her that morning on the beach, as fit and fantastic as ever, that it could have been a problem.

We had setup plans the night before where, in addition to heading to the fully nude portion of the beach that day, we would also workout together in the morning and, running along the beach after already having gone for a 1200m open water swim, I found myself in a happy place. After all, what could be better than doing the things you love with someone you are attracted to? Plus, Stacy kicked my ass on the swim, and the prospect of having a legitimate training partner in that same attractive person was a turn-on like no other.

"How are you doing?" Running was my stronger discipline and, while she was certainly keeping up, I could see that Heather was pushing.

"Don't you dare slow down," she replied in between steps. "I'm doing just fine."

We were getting to the end of our pre-agreed upon 5k and my watch told me we only had about 400m to go, Heather insisted on pushing it and sprinting to the finish.

"Holy shit," she gasped, her chest heaving for air after we stopped. "Thank you!"

"You know," I replied, myself also sucking wind, "I used to always question the people who took their workouts seriously when on vacation. In hindsight, they were right. I just never had anyone to do it with."

Heather slowly walked over, first looking for a high five and then for a hug.

"You're hired," she said, jokingly. "That was the best run I have had in months. I normally train by myself. You can't possibly be so cruel as to let me go back to that."

Maybe Bethy was right, maybe this could be a long-term thing.

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After a long cool-down walk we were somewhat disappointed to see that the resort beach and pool had already started to fill up with guests, making it difficult for our original plan of just changing on the beach before breakfast. But, that said and truth be told, both of us indicated a desire to shower and agreed to meet back for breakfast in an hour; plenty of time to get clean and all of our beach stuff together.

Back in my room, Shannon was just waking up, still laying in bed but playing on her phone.

"Hey there."

"Hey," she responded. "I don't think you understand the concept of a vacation."

I laughed at her comment.

"Yeah. There may be some truth to that. So, whatcha up to?"

"Looking for some porn. I was about to masturbate."

Her comment stopped me in my tracks and I stood still, awkwardly for a moment before even figuring out what I could possibly say.

"Uhmmmmm... sorry to interrupt?"

Shannon laughed.

"Sorry, Will. Didn't mean to put you on the spot like that. I'm just in a bit of a bad mood. My so-called date last night kinda' sucked so I was hoping for a little endorphin boost. I was going to use my ol' trusty fingers unless, maybe, you want to help."

I was sweaty and disgusting and honestly and surprisingly, not interested.

"Shannon," I could hear the uncomfortable-ness in my own voice, "I'm gonna' have to pass. I'm sorry. If I'm being honest, I don't even think I could get myself up to the task."

"I offered him Viagra!"

Kate's unmistakable voice rang out from the other room, startling me. Stepping over to the room dividing door, I found her sitting on her bed, fully nude, an annoyed look on her face.

"Uhm, hey, Kate. Whatcha' doin'?"

"Well, I was doing the same thing that Shannon was going to be doing but since you two can't keep your mouths shut I lost my concentration."

"Sorry about that, I guess."

I had no idea she was even in the room.

"Oh, forget it," Kate responded before hopping up, throwing a sundress on over herself and heading out the door. She didn't look in the mirror, she didn't put on a swimsuit, she didn't grab a towel, she just left.

"What was that all about?"

"Frustrated," Shannon replied. "Frustrated with the resort. Frustrated with everyone around her having sex, even if it was terrible sex like mine last night. Frustrated a bit with her marriage."

"Oh," I responded, intrigued. "How so?"

"I think that you know that she and Mike (her husband) basically have an open marriage, right?"

"Well, I hadn't known but a comment she made to me inferred that was the case. What about it?"

"Well, basically two things..."

Shannon had put her phone down but had absentmindedly started stroking her pussy, staring directly at me while doing it.

"First," she continued, "she and her husband have been at each other lately about how he has been doing more extracurriculars than she has. So, basically, she'd not getting laid. Second, she's gotten herself in a tizzy with all the flirting she has been doing with you plus the spectacle on the beach yesterday. She's pretty wound up."

Her middle finger was making little rings around her very exposed clit.

"To be quite honest, we all are."

What's a guy supposed to do?

I pulled off my shirt and got on the bed, nestling my face between her legs. Before I refocused my gaze elsewhere, I saw an excited smile spread across Shannon's face as she grabbed a pillow and got her head comfortable. I laughed to myself in my head. It was obvious she baited me into this. She lured me in with no problem whatsoever. Kudos to her.

Similar to our session of full intercourse, it didn't take long for her to climax though I decided to torture her a bit, revenge for her playing me, and refused to stop attacking her clit even when it was obvious she was done.

"Stop! Will! Please! I can't take any more!"

Her body was working in conflict with itself. Sure, she was using her hands to try and push my head away from her, but her soft thighs were also pressed so hard on my ears that I basically couldn't move anyway.

Thankfully for her, I am no monster.

After giving just a couple more excruciating licks, I abandoned my assault and waited for Shannon's body to relax. When it did, and I was finally able to get a look at her, I laughed, out loud, at the scene: her hair was a mess; her legs were garishly spread; her labia were swollen and red; it was obvious she still was trying to catch her breath.

"I hate you," she croaked in a broken voice.

"Love you too, honey," I responded.

I stood to the side of the bed and bent over her, turning her face towards mine and placed a soft kiss on her lips. She could only respond with a smile.

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"Did you realize that she left these for you?"

I was already soaping up in the shower when I heard Shannon's voice from the other side of the curtain.

"What's that?"

I peeked my head around and found Shannon still fully nude, with 4 small, white pills in the palm of her outstretched hand.

"What are those?"

"Generic Viagra," Shannon responded. "Kate had left them on your nightstand before you ever even got the room."

"What a gal," I responded with a chuckle.

"You want to use them?"

She had a mischievous twinkle in her eye.

"Shannon," I replied, "I'd love to. And hope to. But for now, I really gotta get going."

She didn't seem to mind. At least that was the way I interpreted her leaving the bathroom for a moment but then coming back in and joining me in the shower.

We hugged.

We washed each other.

We kissed a bit.

I think she just wanted to know she was wanted.

It didn't change the fact that I had plans with Heather and I had to leave. But, if I can be so bold, I think I left on good terms. Yes, of course it had something to do with the time we spent in the shower and my honest declaration that she was incredibly sexy. But, if I am being truthful, I think it also had to do with the fact that, by the time I had left, Shannon had gotten me - without Viagra - quite hard.

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I was basically exactly on time, one hour past the time we had originally parted, when I met Heather at the buffet for a late breakfast. She informed me she had only been waiting for a few minutes and greeted me with a kiss, something that had become somewhat standard in our interactions. She looked fantastic, wearing a very small, black, black string bikini top and a flowy, tropical wrap around her waist.

"My last day," she said to me as we meandered through the selections of food.

"What? I thought you were here today and tomorrow. Did I remember something wrong?"

"No, you remember correctly, I thought the exact same thing. We were supposed to be flying out in the early afternoon. The plan had been to have one last relaxing morning on the beach before going home. But, our flight got changed and now we set to take off around 9am. Which means no relaxing morning anymore. Plus, my group had already planned a big dinner for my sister today so my evening is spoken for as well."

"Well that sucks," I replied sympathetically. Truth be told, I wasn't as sad for her as I was for me. I wanted to spend more time with her. A couple of days wasn't enough.

"I guess that just means we will have to make the most of the time we do have," she replied with a wink.

I couldn't have agreed more.

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We took our time at breakfast and it was the very late morning hours before we finally started making our way down the beach. Immediately we knew that the walk was going to be long as it was obvious that everyone from the resort was out in the sun. The pool area was hopping, the beach area was packed, everyone was enjoying the rays.

We saw quite a few people we knew on the walk, all, consistent with what we had seen so far at the resort, in various states of dress. I introduced Heather to a number of the girls from our group, most of whom were topless. She introduced me to her sister and a number of the women from her group, most of whom were not.

Neither of us thought twice about the walk to find a spot on the beach off of resort property when we first got to the marked boundary. Afterall, why would we? Heather had never been off of the resort property and I was so focused on my enjoyable time with her I never even thought about anything out of the norm that might cause her worry. But, as true as it was the first time I ventured down the beach just days before, it wasn't long before we got our first taste of concern.

"Will," Heather whispered loudly, elbowing me in the ribs. "Is that woman giving the guy a blow job?"

Indeed, when I turned my head, I was presented with the view of what looked exactly like a woman giving a guy a blow job. In all honesty, I didn't actually see a penis in her mouth, but the position of their bodies and the movements of her head painted a very clear image of truth.

"Crap," I responded.

It was a literal Homer Simpson 'D'oh!' moment.

"I forgot to tell you."

Our walk along the beach continued though at a vastly reduced pace and I could see Heather's eyes darting back and forth between me and the offending felator. I explained to her that it was an innocent mistake and that there was legitimately no ulterior motive on my part in not telling her. I went through how, off property, people were not bound by the resort rules and, because there was nothing other than undeveloped vegetation for quite a while, people had taken "fully nude" a step further.

"Holy shit," was her only response.

Of course, most of the people we saw were just fully nude and minding their own business, the same as it would have been on just about any other beach. Tanning... though with less coverage. But it was those that did take the further steps - the hand jobs, the oral, the woman-on-top-of-her-partner-with-a-dick-up-her-ass - that really caused some concern.