Single Male Chaperone - Reimagined

"All you need is love," Taylor purred, still not moving from her comfortable little perch across my body.

"I gotta' say I am surprised you know Beatles lyrics."

"What?"

"All you need is love... the Beatles."

"Really?"

I chuckled at the generational gap.

Taylor didn't move and, if I am being honest, I actually was enjoying the feeling of her on me. It had been a long time since I had been so close with a woman in a seemingly non-sexual scenario. Her skin was soft and warm, her legs were draped around me comfortably and I could feel her heart beating through her small, soft breasts pressed into my chest. I let out a long sigh and settled back into the sand, it too was soft and warm, enveloping my body in a comfortable hug.

Of course, that type of comfort... and the situation I found myself in, had certain effects on me. I couldn't just not think about the physical situation I was in. I couldn't just not think about the events and experiences that led up to this. However, instead of panicking, I let nature take its course.

FOUR, FIVE & SIX:

Taylor was the first to notice my erection, afterall, it was throbbing and bobbing against her hip. She had thankfully laid over me in a way that didn't restrict its movement so, when I got hard, it stood up tall and proud before flopping over onto my belly.

"Mr. Patton! Is that because of me?" She whispered to me excitedly.

"Taylor, Honey, please. Call me Will. I mean, considering the situation, considering you're an adult, I would really appreciate it."

I felt a hand wrap around my cock though I knew it wasn't Taylor. Looking up, I could see that Sarah had shifted over and was fondling me lazily.

"Guys are so lucky to have these," she announced to nobody in particular. "I could just sit and play with it all day."

"Based on what I saw on my walk down the beach, you aren't the only woman who thinks that exact same thing."

"Isn't this resort the best?" Sarah was practically giddy in her response. "No tan lines, free drinks and all the penis you can play with."

It didn't take long before Sarah's manual curiosity turned into an oral one and it wasn't much longer after that before the other girls joined in.

Leona was also in Bethanny's tight friend group though, unlike the others, I had never seen her breasts prior to that day. Whether due to embarrassment, nervousness or a simple desire to maintain some coverage, she had never gone topless at my house. In fact, when other girls were wearing smaller and smaller bikinis, she had actually gone in the opposite direction, moving to higher-waist two pieces all the way to some of the one-piece suits that were in style as well. Yet, on the beach, there she was, nude and seemingly as confident as one could be about their body.

I knew she was of mixed race as I had met both her parents and her creamy, mocha skin was a testament to her more "exotic" family tree. She was shorter, probably about 5'2", but was also fantastically proportioned, with measurements that probably sat around 38-24-36. Her large, full breasts were topped with fantastic, hershey-kiss nipples and, when she shifted her body and exposed herself to me, I saw she had fantastic butterfly-wing labia that were just begging to be sucked.

Of course, with a single guy and 4 women, there was the potential for awkwardness as there is only so much that I could do on my own. But, those that say the younger generations are lazy couldn't be more wrong. Where I was lacking, they took charge themselves.

Taylor had taken to sucking my cock when Brie positioned herself over me, knees to each side of my head, her pussy demanding attention from my tongue. It was obvious she was ready and I lapped at her natural wetness eagerly. With long, attentive strokes of my tongue across her clit she climaxed quickly and fell to the sand to the side of me, a heaving body, still contracting from her orgasm.

It had turned out that, while Brie was on my face, Leona had taken to sucking my cock while Taylor and Sarah played with each other to the side of me. I was thankful for two things: First, that I had never in my life climaxed from felatio and, based on what seemed like a lack of experience on the girls' part, I suspected I wouldn't that day. Second, the girls taking charge meant that each of them was never at a loss for attention. Where I could not administer stimulation, they took it upon themselves to do it; whether it was manual self love or same-sex attention, the scene was that of an orgy. While Leona sucked my cock and Brie recovered, Sarah was giving head to Taylor while I used a free hand on Sarah to work her clit.

We stayed in similar types of positions for some time, rotating between oral and manual stimulation around the group. When I began to feel numb I had the girls servicing me stop. When someone came we let them recover. Everyone seemed to be content.

I had just witnessed a whispered exchange between Leona and Sarah when Sarah began to laugh.

"I'm sure it's okay," she said to her friend. "Just ask him."

"Ask me what?" I responded between lazy tongue strokes around Brie's clit.

"If you'd have sex with me," Leona asked sheepishly. "Like, actual sex."

Sarah gave me the face of a loving parent, one who was requesting another adult go out of their way for their child. It seemed strange and sweet at the same time considering the situation.

"I'd love to."

It seemed the only appropriate response.

Leona laid on her back and I guided myself into her. She had already progressed through an estimated two orgasms and her pussy accepted me easily, hot and wet, devouring my cock. We developed a rhythm quickly and she offered vocal confirmation that she was enjoying herself though, without direct stimulation on her clit, I wondered if she would climax again. Sarah, seemingly sensing my thoughts, used her own hands to not only stimulate Leona's button, but also tweak her nipples at the same time.

Similar to my experiences of the morning, she finished quickly, releasing muffled moans into the crook of her own arm as the waves of pleasure washed over her body and, when she was done, I pulled out.

Brie was already on all fours, waiting for my penetration as Leona finished and, after a quick tongue bath on my cock from Taylor, I plunged into her with long, even strokes. While I added additional stimulation as I saw fit, in the form of gentle circles of my thumb around her winking asshole, it was most likely the similarly added clit and nipple stimulation from Sarah again that put Brie over the edge for the final time.

I had felt my initial stages of orgasm start to build with Brie when I laid down on my back and Taylor mounted me, her tiny pussy seemingly stretched to its limits accepting my cock. I was glad to be in the woman-on-top position, a favorite of mine in the past, as it seemed to offer the best combination of external and internal stimulation for the female. Surely enough, whether it was due to the fact that she had already gone through at least one... or the syncopated motions we found ourselves in, Taylor began to come to a crescendo. I could tell that, unlike my experiences so far that day, I too would finish and I made my intentions known as Taylor's cries of passion woke up any napping soul within 50 meters.

"I'm gonna' cum," I groaned, desperately holding back as long as possible as Taylor rode her final wave.

I was able to guide her onto the sand beside us when I felt my cock tighten to steel for its final climax and figured that I would just finish myself with my hand though was delightfully surprised when I felt the warm mouth of Sarah wrap around my cock, sucking down every last drop of cum I could produce, the pent up frustration of an entire morning of stimulation releasing into the back of her throat.

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Only Sarah was with me when I opened my eyes again. I had closed them as I caught my breath after orgasm though I had not figured that I would have fallen asleep.

"Hey," I said to her, getting myself into a sitting position.

"Oh, thank the Lord," she responded with a shocked look on her face. "We thought you were dead! The other girls just went for help!"

"What?! Why?!"

Sarah laughed.

"Nah, I'm just messing with you. You only had your eyes closed for about 5 minutes."

I rolled my eyes but smiled. While she had always been comfortable busting my balls in the past, our past couple of interactions gave a whole new definition to the term and I was happy she was still keeping her cool.

"That was something, huh?"

"Yeah, I think you could say that."

"So, you and Taylor?"

"Yeah, I saw you watching. What a dirty old man you are!"

"Yeah, yeah, yeah. Any backstory there or just caught up in the moment?"

"Well, we're both bi and have messed around a little in the past but nothing like that. It just seemed right. I was a little worried about what Brie and Leona would think but they didn't seem to care at all. Hell, Brie even let me play with her clit when you were in her."

"Speaking of which, where is everyone?" I had noticed that we were the only ones left at our location.

"Well, they said they were going to get some food. Honestly I think they just wanted to talk about what happened without you being around.

"Sounds appropriate on both accounts. Care to join me for a bite?"

"Nah, I think I will stay here. Thanks though."

Just like the stereotype of a 1950's wife, Sarah helped me with my wrap and saw me off with a kiss. She was quite a young woman.

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It was dinner time before I ran into Jenn and Kate again and they light-heartedly chastised me for leaving them earlier in the day.

"It's not you, it's me," I pleaded and, indeed, it was true. Afterall, upon returning from the beach I really hadn't seen anyone from our group.

Well, that was a lie. I saw people, I just didn't interact with anyone.

I saw most of our girls just lying around the pool, drinks in hand, working on their tans, only one or two topless. It was the most logical of places, of course. For as wild as things had gotten over the day (and days prior) I could admit that sitting around the pool would be the actual definition of normal.

Of course this was not to say that I didn't see members of our party getting a bit crazier. Afterall, there were the poolside games and activities, every last one of them sexual in nature. Besides the wet-t contest (realistically a hot-body contest) of the morning, there were also ring-toss games with strap-ons as targets, pop-the-balloon games between two mostly-naked-and-oiled bodies, all the typical stuff. With so much happening on just our first day, I was curious as to what the staff still had up their sleeves for the rest of our stay.

For the most part, I stayed away. Not only did I prefer the beach and saltwater to the pool and chlorine, but the constant thumping dance party music was not really my scene. Plus, most importantly, I had told Bethanny that I would give her space. Besides dinner - a meal we had agreed to pre-trip to try and eat together as a large group - I only saw her once more during the day and that was just in passing as I walked by her at the pool.

Whether due to travel, the drinks with dinner, the extended time in the sun or the multiple sessions of playtime that day, I fell asleep early that night, content with the day and looking forward to what the rest of the trip would bring.

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I woke up early in the night with a slight headache and the need to pee. I wasn't surprised by either as alcohol-on-top-of-dehydration had that effect on me. It was warm in the room and I realized I was still alone in it, the sounds of the resort still lively through the room walls. I responded to nature's call and, after downing a large bottle of water and tossing on a shirt and shorts, I decided to venture out into the night to see what everyone was still up to. Incidentally, my wandering didn't take me that far, only into the main open space of the resort, not yet to the source of the music and revelry.

"Bethanny, Rosie, hey."

The two young women were walking towards me.

"Hey, dad. Where have you been?"

"Asleep, actually. You?"

"At the disco."

Both girls were technically fully dressed in tops, bottoms and shoes but the string bikini tops, micro-skirts and flip-flops left little to the imagination. I supposed it would be on me to check out the vibe of the on-site dance-club.

"Are you two calling it an evening?"

"Only me," responded Rosie. "Bethy was just walking me back."

"Well, tell you what," I responded. "I don't like the idea of either of you walking alone at night so why don't all three of us drop Bethy back off at the club and then I can take Tara back to her room."

The girls agreed to my plan and it wasn't much more than a moment later that Bethy was back dancing with her friends and Tara and I were heading back to her room.

"Tired?"

"No," she responded. "Not at all, actually. Just have a bit on my mind and I was getting annoyed in there. Just wanted a quieter place to think."

We had already gotten to her room and she was using her key to open the traditional, non-electronic lock. Her mind seemed elsewhere.

"Uhm, do you want to talk... or maybe just vent? I can hang out with you if you want."

"You know what? Yeah. That would be good."

The tone of her response was that of pent-up frustration, not of emotional insecurity. My mind could not immediately process as to whether that was good or bad but I knew I was in for an earful.

Rosie Espinal. Birth name: Jimena Rosa Espinal. 18 years old. Shoulder length, straight black hair. 5'3" tall. Measurements of approximately 32-24-38 including perky, B cup breasts and one of the most bubbly of bubble-butts that I had ever seen. Fluent in Spanish and English and conversational in Mandarin Chinese. 4th overall academically in their graduating class and would be attending Duke in the fall on a pre-med track. Also of interest: Bethanny had confided in me that, upon turning 18, Rosie had started posting face-less nudes online and had, as of about 4 months prior, launched a subscription service which was apparently netting her almost $11,000 per month... and rising.

"It's my boyfriend. Well, ex-boyfriend."

We were in the hotel room and Rosie had thrown herself onto one of the beds. The room was trashed, with clothing and accessories thrown everywhere. I slid a pile of damp towels off of the bed opposite to her and sat down, my ears open.

"I got into an argument with my boyfriend before the trip because he didn't want me even coming here. He said that because we only have a few weeks left together we should be spending it together. But, considering this is a once-in-a-lifetime trip and we haven't been together that long, I told him that it was only 10 days and I was definitely not going to miss it."

"Seems incredibly reasonable to me," I responded.

"So, anyhow, I just got a random... and I am sure it wasn't actually random... butt dial of that asshole clearly having sex with some rando."

"Seems much less reasonable."

"Exactly! Like seriously... what the fuck?! I'm gone for a week-and-a-half and it's cause to go bang some other chick?! Why are guys such jerks?"

Rosie had gotten off the bed and had started slowly undressing, seemingly unconsciously, like muscle memory at the end of a long day. She paced about the room after having undone the back tie of her bikini top, the cups dangling haphazardly across her chest, her small breasts eliciting a small jiggle with each step.

"And before you say 'not all guys are jerks,'" she continued, "yeah, I know that. But a lot of them my age are. They're just just insecure, you know? And they wonder why we are always lusting after older men."

The bikini top was gone, thrown somewhere into the unknown void of the room floor and she had begun unzipping the side of the tiny skirt she was wearing, the lycra string waistband of her underwear now clearly visible.

"I'm not sure if you are looking for a two-person conversation here or if you are just looking to blow off some steam," I responded. "I can do either."

Her skirt dropped to the floor and she stood for a moment in her panties, a tiny mesh number that rivaled the size of the g-string I had originally helped Bethanny pack. Did all teenage girls own these?

"I don't even know."

She shimmied the panties off of her hips and plopped herself on the bed, propped up and facing toward me, her legs naturally open, her pussy fully on display. She had a perfectly groomed triangle of pubic hair hovering just north of what appeared to be an otherwise fully waxed vulva. She stared at me with a look of upset frustration.

"Is it hot in here?" My question was legitimate and I made a mental note to contact maintenance regarding how to use the air conditioning.

I went to the mini-fridge and grabbed a couple of bottles of water, opening them both and handing one to Rosie, arranging myself on the side of the bed next to her. I put my hand on her leg, a gesture of solidarity in the moment. Her eyes never left mine as she took a drink of water. The tension in the room was practically paralyzing before she let out one final whisper of conversation.

"And the worst part about it is this resort has me so horny I am about to burst."

SEVEN:

I placed both bottles of water on the bedside table and then took my hand and gently placed it on the side of her face.

"It still needs to be said," I commented in a low voice, "that not all guys are jerks."

Rosie smiled and grabbed at the bottom of my shirt, pulling it over my head before responding.

"Good, prove it."

I grabbed her hips and slid her down the bed a bit until she was flat on her back, a position more meant for my own comfort as I settled myself down onto my stomach, my face between her legs.

Her smell was strong, though in no way bad. Just nature's pheromonal fight to create the ultimate aphrodisiac. Upon inspection with my tongue she was sweet and salty, an unsurprising combination considering the aforementioned horniness and dance club sweat. I deployed the same methodology I had found so successful in the past, first using little lashes of my tongue to coax her lips open and then long, regulated strokes of it against her clit. She began to moan just moments into the experience and it brought a smile to my face that her intonation was somehow clearly latina. When her thighs pressed hard against my ears and the heels of her hands pushed against my forehead, I knew it was my time to stop.

Rosie was taking a moment to recover on the bed beside me and I spent the time lazily playing with her nipples and applying soft kisses to her neck and ears.

"Jerks don't do that," she said with a smile, turning her face to direct some of my kisses to her lips.

"Go down on you?"

"Yeah, my boyfriend never did. Not once. Always just wanted to get blowjobs or fuck."

"Wow. That does sound like a jerk. His loss too. You're a fantastic woman."

Rosie beamed a happy smile and started becoming a bit more animated, hopping up and off the bed and pulling at my shorts.

"Can you sit," she asked me just as my cock sprang out into the warm room air, "I mean, would you mind?"

"Like, in a chair?"

There was a chair in the room, of course covered by random towels, underwear and other clothing.

"Yeah, in a chair."

She was pulling me by the hand, not aggressively, but certainly forcefully enough that I knew there was no point in trying to resist... not that I had a reason to try and resist.

I got off the bed and she released my hand, only to grab onto my cock, firmly but comfortably, her tiny soft hands immediately instilling it with new life.