Single Male Chaperone - Reimagined

After our few dates, circumstances where we had sex a couple of times, Christina had taken to sunning around my pool topless when she joined us on our rare combined free time. I was happy to let her do so, not only because of the wonderful visual it offered me, but also for the body-positive image that she relayed to the girls and, to this day, I am convinced it was her carefree confidence that transferred to our daughters, something I am eternally grateful for.

Her long, blond hair trailing in the warm sea wind behind her, Madison stepped into me and gave me a hug, wrapping me up in a tight embrace, only atypical in our dual nudity and my sandwiched erection in between our two sweaty bodies.

"Hey, there," I offered, planting a kiss on the top of her head. "What's going on?"

"I think that is more of a question for you," she replied with a smile. "In all the years I have been over to your house I don't think I have ever seen you walking around with a boner."

"It won't go down," I responded honestly and without shame. "I am not sure if it is this resort or what, but normally I can keep much better control of these things."

Madison giggled.

"Why don't you come with me," she responded, pulling on my arm. "It's just me, you can get yourself a bit more settled."

We walked up toward the vegetation and we both sat down on her towel. Looking around, there was nobody in sight.

"You're by yourself?"

"Yeah. I actually just got here. Some girls may join a bit later but they were sticking around for the pool games for now. I just had to get away from the music, it was starting to annoy me."

EIGHT:

"I hear yah," I responded. "Not my scene."

"Well, apparently this is your scene," she laughed as she again acknowledged my penis as she bumped her shoulder into my side.

"Yeah, sorry about that. It's like puberty all over again."

"What?! You used to walk around with boners during puberty?"

"Ha!" Her inquiry caught me by surprise. "No, not walk around with them. Or, who knows, maybe I did. I was just more referring to the fact that I would get them for no apparent reason. My body had a mind of its own."

"Aww, that makes me sad," she playfully pouted. "I thought it was for me."

"Well, that too." I returned a playful nudge to her side.

"I know what you mean though," she continued after a moment of silence. "Unfortunately it didn't stop with puberty but, ever since then, my body just sometimes has its own reactions."

"Like?"

"Uhm..."

She hesitated and looked up at me, her sweet, doe eyes obviously questioning her own thought process, determining her next move.

"Yeah?" I prodded her just a bit.

"Okay, fine. Like, I just get wet. Like, for no reason."

I smiled. "Oh, I don't know. It's not uncommon to be a bit wet."

Madison seemed offended by my response. Offended enough that she took my hand, pulled it into her lap, and dragged my fingers across her cleanly shaven vulva. The tip of my middle digit slid between her lips easily, she was, in fact, really wet.

"A bit wet?! I don't get a bit wet! I'm practically dripping! And, I am like, so horny. Like, so horny, all the time, and then my pussy starts tingling and getting wet for like no reason and it just kinda' drives me nuts."

I layed down on my side and faced her though didn't say a word. I decided to see just how serious she was about what I thought she was pushing for. And, as if scripted, she followed my lead.

"So, what do you do about it?" The innuendo in my comment was obvious.

"You know," she whispered, breaking eye contact, "my mom still talks about you." She surprised me when she reached down and grasped a hold of my dick and hesitated in her last statement. "She said you have an amazing penis."

There was no hesitation in her response when I leaned in to kiss her... and she very clearly kissed me back.

Though her hands never left my cock, sweat and sunscreen making the contact slick and smooth, I flipped myself around and pushed my face between her legs, my tongue leading the way to the wetness she lamented.

Her taste was surprisingly sweet and the entire experience of her on my mouth was legitimately pleasurable for me. Sincerely speaking, even without the warm, soft attention of her hands - and then her mouth - on my phallus, the sensations provided to me would have been plenty enough to keep me aroused. Her pussy was neatly packaged, a simple slit against her smooth, shaven skin and I learned the touch and taste of all of it. The minimal ridges between her inner and outer lips, the heat of her swollen clit, the taste of her inner walls.

I was surprised when she began to push my head away as I had not sensed she was anywhere close to an orgasm. Looking up, I saw a pleading in her face and, with no words spoken, I could tell she did not want to wait to have me in her.

"I've been waiting for this for so long," she whispered through scatto breaths as I slid into her. "Ever since I saw you kiss my mom, I wanted to kiss you. I wanted this."

She was tight and, even with her extreme wetness, it took time for her to accept me fully, with slow, consistent strokes in and out, back and forth.

Her entire body was flushed beneath me and I held myself up over her in order to take in the sights; her tightly trimmed light brown pubic hair, the musculature of her abs, the swollen pink of her puffy nipples, the pleading need of her face.

I was happy when she requested we flip over, not because I had any problem with the position we were in, but because I was glad she was telling me what she wanted. I was surprised when she turned her back to me, reverse cowgirl, and guided me back into her, her peach of an ass grinding on my pubis, her little pink asshole, her slender back writhing with her movements.

Damn, the view was amazing.

I was happy when Madison began to whimper, not because I was ready to finish, but because I was glad that she was going to and was again delighted by the visuals, this time of her ass clenching and winking at me, the internal convulsions taking control.

I was less happy when she fell off of me.

"Oh, God," she moaned from her curled up position on the sand, "that was fantastic. I can't believe people told me to wait."

I couldn't believe my ears and I immediately propped myself up on my elbows to face her.

"Wait. What? Honey, you're a virgin?"

Madison got to her knees and crawled over to me, pushed me back into the sand, straddled me and laid down on my chest, her heart still racing.

"Was. Not anymore," she replied.

My mind was racing.

"But... but you seemed so... confident... so sure of yourself. I mean, how did you know that you wanted to do the position you finished in?"

"Honestly, I didn't. But it isn't like I don't watch porn and since I love the look of that position I figured I would give it a try."

"I gotta' say I'm impressed. I would have thought you had at least some experience."

Madison propped her chin on my chest so we could look at each other.

"Well, I do masturbate," she said without the slightest bit of embarrassment. "I have a vibrator and a dildo and a little device that you can put on your clit that makes it feel like someone is sucking on it. So, I know how to get myself off. It's just the first time with an actual guy, an actual penis."

"Glad I could help, I guess."

"I'm glad it was you."

We laid in the same position for a moment, a happy couple on the sand, before two things happened:

First, I felt my cock twitch. I had not gotten flaccid since I hadn't orgasmed and the soft, warm weight of Madison on me wasn't about to make it go down. Madison obviously felt the twitch and rolled to a sitting position next to me, taking me back into her hands, massaging me gently.

"You didn't finish, did you?" She had a little frown on her face.

"No, but that's okay," I responded truthfully. "I'm glad you did though."

Second, as if from some sort of divine timing, another girl from our group, Shelby, walked up to our little nest in the sand.

"Hey, Shel." Madison greeted her friend while still massaging my cock, as if it was the most normal thing in the world.

"Hey, Mads. Whatcha' got there?"

I didn't know Shelby that well. I knew that she and Bethy shared a few classes and obviously common friends but, besides that, I only had to go off of what was directly in front of me. She made sizing her up, at least physically, easy.

I made the guess, from my angle, that she was about 5'5" and 140lbs. She immediately began stripping off her swimsuit, a surprising one-piece with massive openings on each side and an extremely low cut in the back. She was thick all around but not heavy in any way, she had large breasts, a soft tummy and birthing hips like she was pulled from a renaissance painting. She had shoulder-length brown hair and a tiny brown landing strip extending up from her pussy.

"Just lost my v-card," Madison replied in a voice that barely registered any emotion. "But this guy didn't finish. I was thinking about going for round two. Care to join?"

Shelby looked at me and I smiled, it was the only reaction that I could think of.

"Sure," she responded to Madison's inquiry, "why the hell not?"

NINE:

The sex with Madison was much better than the sex with Shelby. But, in Shelby's defense, I did end up finishing.

Madison sat to the side while Shelby began to blow me. Now, don't get me wrong, while a mouth on your cock is a wonderful thing, it doesn't mean that some felatio is better than others. In Madison's case there was a bit too much sucking and not enough wetness, it was obvious that she didn't have much experience... or never had a partner to offer her feedback.

Though, in direct contrast with my own preached thoughts on communication, I decided not to immediately coach her, rather just change the position. I had her lay on her back with her head in Madison's lap while I spread her legs.

"I like to go slow and wet," I whispered. I hoped that my comments on what I was going to do to her would translate to what she did to others. That said, maybe her other partners enjoyed the way she gave head. "Let me know if you like it."

Her pussy, with big, puffy labia, was wonderfully musky, a smell I savored as I used my fingers to open her up. After offering a gentle kiss on her clit and a long, drawn-out lick up across her entire opening, Shelby responded.

"Holy shit," she gasped, trying to even her breath, "yes, I like it."

I admit, for whatever reason, the entire scenario seemed a bit transactional. Maybe because I had absolutely no emotional connection with my partner, maybe it was because I was basically handed over to her in a casual manner, though, while my head wasn't into the exchange, my body certainly was..

Shelby rolled through a first climax and I took the opportunity, while she was regaining her composure, to position myself between her legs. It was a somewhat silly scenario for me to hesitate a bit: me with my cock standing up tall and proud; Madison to the side, playing with herself; Shelby looking up to me in anticipation, but, that said, I did feel the need to ask.

"You're okay with this?"

"Sure," she responded.

My brain decided to process her less-than-convincing response as an enthusiastic "yes" and I took the opportunity to slide into her. The action took us both by surprise.

"Oh, God," she gasped, "you're so big."

Note: I'm not that big.

"Oh, God," I grunted, "you're so tight."

My misconceived preconceived notions were blown out of the water that day on the beach in that Shelby, a slightly bigger girl, had the tightest pussy I had ever (and would ever) felt.

There wasn't much doing after that initial penetration. Having already been with Madison, having already been so primed from my thoughts of Heather, having Shelby's tight pussy milking my cock from my first thrust, I felt my orgasm build quickly.

"Holy shit," I moaned after just a couple of minutes, "I'm so sorry, but I am gonna' cum."

Shelby didn't seem to be fazed by my declaration but it was Madison that took me by surprise.

"Pull out," she instructed, positioning herself on all fours, her face at my belly.

I did as I was told and she took me directly in her mouth, my dick still slick from Shelby's wetness, that layered upon Madison's own. She worked her mouth expertly, tactics picked up maybe from her apparent porn watching, maybe from an "everything but" type of relationship with a boy, maybe from a natural talent, and I groaned as she sucked down every last drop of me. It felt fantastic and, after I was done, I finally, immediately, mercifully, felt my erection go down.

We all laid on the sand for a moment, maybe 30 seconds, before Shelby popped up into a sitting position.

"Hey, Mads, you wanna' go get something to eat?"

Madison smiled and eyed me knowingly as she packed up her towel and the girls re-dressed in their suits. 'She's weird', she mouthed.

Yeah, 'no kidding', I mouthed back.

The girls left me, alone and bemused on the beach. It isn't to say that my carnal urges weren't satisfied. Just to say that this trip, and all the women around me, were more thought provoking than I had ever imagined.

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I made my way back to the resort after letting the girls get out of eyesight. I realized that Shelby was on the right track and I was pretty hungry and I got myself a bite to eat.

Though I had gone in alone, I found a number of the girls from our group eating in the main buffet dining area and joined them for lunch.

The conversation mostly revolved around me and how everyone was so happy I had agreed to accompany the group to the nude beach the next day. Based on the fact that each was only wearing a tiny bikini top (tops, no matter how small, were mandatory in enclosed eating areas) it seemed a bit funny to me that any of them would care about that little a difference in coverage but, even I could admit that it was nicer to be nude. Although I was only encumbered by my thin, tan-thru shorts and a t-shirt, I agreed that I wished I could have stripped down nude. The girls were neither shocked nor upset with my declaration, rather happy that I shared the same sentiment as them and were all in agreement that "next time" we should just book at a fully nude resort... a comment that I laughed at as none of the girls were paying their own way. But, hey, there's no problem with a dream.

When lunch was done, and though I was invited to join the girls back around the pool, I excused myself and bid them farewell until dinner. I had some other priorities.

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The reality was the priority was singular: I needed to shower.

I got into my room and immediately stripped down and hopped into the shower, the door barely closed behind me before the water was running. I laughed at myself for thinking that the water should have gotten hotter faster because it was warm out and waited those slow, 30 seconds before being able to drench myself in the satisfying fresh water. Don't get me wrong, I love the beach and pools are pretty great too... but clean, fresh tap water and a bar of soap is what makes me feel the most refreshed. My life was a regular freakin' Zest commercial.

My shower was complete and I was drying off when I first realized I wasn't alone and, though nobody was in my immediate room I did find the shower running in Kate and Jenn's attached bath.

"Will's here," I offered into the steaming room, doing my best not to panic the occupant.

"Oh, hey," Jenn responded back before pulling the shower curtain and offering me a smile. "What are you doing back in the room?"

"Looking to rinse off, get out of the sun for a bit. Hell, I'm on vacation, maybe I'll take a nap."

"You need some lotion, honey," she said, her eyes darting up and down my otherwise nude body, only a towel hanging over my shoulders. "You're a bit red."

I stepped into the bathroom and took a look at myself in the mirror, I didn't notice what she was talking about.

"Tell you what," Jenn continued. "I'll help you when I am done if you return the favor."

"Lotion buddies? Again?!"

I responded with cheesy, overacted, overly-enthusiastic excitement. Jenn rolled her eyes and pulled the curtain shut though, a moment later, yanked it open wide and spit a mouthful of water all over me, resulting in my own eye roll and her own squealing laughter. She appeared so excited about her offense that I couldn't help but smile.

TEN:

When we were both dry and we began the task of applying the lotion, I can't say that it surprised me that it rather quickly turned from "functional application" to "erotic massage." Afterall, when Jenn first suggested we move to her bed and straddled herself over my waist while applying lotion to my chest... easily the most readily accessible area for anyone to apply on their own... it was obvious she had more in mind. I was surprised at how nervous she seemed to be and, considering how quickly I had broken out of my celibate ways, how nervous I was as well. No matter the cause for either of us, things progressed and we shared what I can personally say was some of the most tender lovemaking I had experienced in a long, long time.

Each of us were soft and gentle with the other. Soft in our kissing, gentle in our touch. We whispered to each other about what we liked in the others actions; I told her that the sensation of her dragging her breasts, specifically her hard nipples, across my chest was an excrutiatingly pleasurable torture; she whispered to me about how much she loved my little nibbling kisses on her neck.

When I finally entered her; after petting, after me going down on her, after exploring just about every inch of one another's bodies with our fingers and mouths, neither of us lasted long. I finished inside of her at her request and continued my even tempo thrusts post-orgasm in order to guide her across the proverbial finish line as well and, when she too had climaxed, she collapsed on my chest, each of us breathing hard, our skin no longer shower clean.

"Did Kate tell you about me?"

The question pierced the air after what seemed like many minutes of still silence.

"What do you mean?"

"That there is no way I can be in a relationship right now?"

"Uhmmmm..."

I was taken a bit back.

Jenn rolled over onto her side and propped herself up on her elbow, an honest to goodness tear rolled down her cheek.

"That was the most wonderful sex I have had in I don't know how long, maybe ever. Will, if you had asked me to marry you about 5 minutes ago I probably would have said yes. I felt like we were so in tune with one another it was practically like we were sharing a brain."

I wiped the tear from her eye and smiled.

"But I cannot be in a relationship. I need to figure things out for myself, you know?"

"Believe me, I do," I responded.

"But," she said, getting herself up into a sitting position and sniffling herself back into a state of composure, "I also hope that is not the last time we get to do that. Because it was, honestly, fantastic."

I pulled her down onto me. We hugged a bit, we kissed, we tickled each other.

We both knew that we would be just fine.

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We decided a nap wasn't in order for that day and, after seeing Jenn out the door, I stepped back into my room to grab my shorts and possibly follow up on a couple of emails.

I audibly gasped when I found Kate sitting on my bed, mindlessly scrolling through her phone.

"You two done?"

"Uhm," I started to stammer my response, "uh... uhm..."

"Calm down, Will," she replied in a somewhat maternal manner, "you have nothing to worry about."

"How long have you been in here?"

"A little while. It seemed like the right thing to do to give you two your privacy. How on earth neither of you noticed me coming into that room is beyond me."