Single Male Chaperone - Reimagined

"Did I do something wrong?"

"Let's just take a moment to really enjoy this, we're in no rush."

I had her lay back on the bed and put my face between her legs, coaxing her open with my mouth. Like when I kissed her neck, I was greeted with a sighing moan that was much more obviously natural, and much more appreciated from me.

"There will be times for fast and furious," I said in between long, drawn out strokes of my tongue, "but, as a general rule of thumb, starting off slow is usually better. No matter how much your brain wants things, your body needs to get up to speed."

I took my time, coaxing her natural wetness out of her to the point that it dribbled down to her asshole. When that happened, I expanded my real estate and included that as well. When the time was right, I spun around into a 69.

"Now, you try."

Her second try was much more pleasurable. We were more in tune and she had cut out the theatrics. I took a moment and enjoyed it.

"Listen for audible and verbal cues from your partner and, above all else, let your partner know what you want."

I was practically whispering the words and I questioned just how much coaching I should do but it seemed like a reasonable comment when I said it.

"I want you to fuck me."

The severity of her comment had taken me back. I guess she didn't need or want to be coached. Tiffany wasted no time, she scrambled away from me, pushed me on my back and climbed over me, guiding me into her with a long, single, easy stroke. She was obviously past the point of me taking charge, she knew what she wanted. The foreplay had done its task, she was very wet and she found her rhythm quickly. Like Shannon, I was now along for the ride.

Tiffany climaxed quickly and, to even my own surprise, I again did not. She spastically flipped off of me and lay collapsed, a spread mass of flesh and limbs, next to me. She had managed to flip herself around and her knees were at the approximate height of my head, with her legs spread wide in her post-climactic state, I lay witness to her pussy and anus still experiencing "after shock" contractions from her orgasm, the erotic nature of the sight only causing my still-hard cock to twitch in the humid air.

"Holy shit," she breathed heavily. "I've never orgasmed during sex before. I had no idea what it was like."

"I guess you liked it."

My blue-balls aside, I had a smile on my face. It was fantastic to be responsible for a woman's pleasure.

"Oh, my God, yes! I feel tired and energized all at the same time."

She rolled over onto my leg and side, her arm naturally finding its way across my dick.

"You're still hard? My boyfriend always went immediately limp afterwards."

"Not today, I guess."

I decided to keep any additional commentary to myself. Afterall, we were on day one of a 10-day vacation, there was plenty of time left for my pleasure.

We lay silently for a bit, Tiffany still coming down from her climax, my erection dissipating away before she got up and headed to the bathroom.

"We should probably go," she commented. "The girls will be wondering where I am."

"Agreed. I think I have a chair being saved by the pool."

"Was that any good for you?"

I could tell she was looking for validation.

"Tiffany, that was fantastic. I couldn't think of anything better."

It was a tiny white lie, one that I did not feel at all bad about telling, and she beamed at my approval.

"Are we supposed to keep this a secret?"

"Well, that's up to you," I replied honestly. "I am not one to kiss and tell so it isn't like anyone is going to be getting details from me. But how you handle it is your business. I just may caution you regarding the unfair standards that women are still held to regarding casual sex."

"Thanks, Mr. Patton," she said as she stepped into me for a hug. I had been re-tying my wrap around my waist and she literally wrapped her arms around my arms, trapping me like an over-loved pet cat.

"Will would be preferred, Tiffany. We're both adults."

"Thanks, Will."

We left the room at the same time though I was quickly left behind when Tiffany, in her excitement, jogged off in front of me, desperate to meet up with her friends. Her cute little ass taunted me as I watched her leave and I let out a small groan of frustration.

"Patience, Will," I said to myself out loud. "Patience."

--------------------------------

I got down to the pool and, after a bit of searching, found Kate and an empty chair.

"Did you get lost?"

"Sorry for the delay," I responded, "just helping out a kid in need of a confidence boost."

"That's good of you," she responded without the slightest hint of sarcasm. "These girls are going to meet their share of assholes over the next few years of college. It's nice to let them know there are good guys out there."

"I wouldn't go too far with your praise, but I do appreciate the compliment."

I informed Kate that I was going to hop into the pool quickly and, after she declined my offer to join me, I dove in alone. After two morning sex sessions the reality was that I just needed to rinse off.

Looking around the crowded pool area I took in the sites available to me. I knew that the resort held a maximum of 800 guests and I knew that rooms were fully booked. I could see that the vast majority of the guests were a bit older, from their 40's to 60's and it wasn't unexpected. What was somewhat unexpected were the numbers of younger folk as, besides our group of 20, there had to have been at least 80 guests visible that were under 35... and that was by the pool alone. By their dress I could tell who the American's were and who the European's were. I saw a number of pairs of exposed breasts and men in tiny swimsuits. To be honest, there were really no surprises. The only real surprise was the staff, as most of the men were topless and most of the women were wearing only bikinis, many of which were thongs.

"I would think they would be concerned with over-exposure."

"Huh?"

My non-sequitur comment caught Kate by surprise as I returned to my chair.

"The staff. I mean, don't they get sunburned? It's a little different for tourists as we are out here for a limited period. They're out here all the time."

"I suppose," she responded sleepily, "I suspect their skin is just a bit more tolerant of the rays though."

I had always been attracted to Kate and had become decent friends with her over the years. Bethy and her daughter, Elle, had been in similar classes and extracurriculars for some time. She was a tiny ball of energy - maybe 5'1"; 105lbs - and she had to have been smoking hot in her youth. Age and motherhood and taken away some of that peak physical form but what was left over, the lean body of a woman who I knew still attended gym classes multiple times a week, was still pretty spectacular. Her breasts had gotten smaller over the years, something she lamented to me prior to the trip.

"Did I tell you?" Her question came as if she was reading my mind though she did not wait for a response. "I'm getting my tits done. My flappy pancakes will be a thing of the past."

"Flappy pancakes?"

Sure, her breasts were smaller, but they literally didn't even sag, let alone have that "pancake" look she was sarcastically referring to.

"In 5 weeks I will be 300cc larger in each breast. The goal is a full C-cup."

"Yeah? What made you finally take the plunge?" It was something that she had mentioned multiple times in the past though always said that she wasn't actually serious about.

"Mid-life crisis? Who knows. The time just felt right. Afterall, I'm not getting any younger, might as well try and look it while I can."

"You know that's bullshit, right? I'm not here to convince you either way but just know that you are extremely sexy just as you are."

"You're sweet, Will. You can let me know what you think after it's all done."

-----------------------

The action around the pool was hopping, typical of what I would expect from a Caribbean resort. There was pumping dance music, animated bartenders slinging drinks and frivolity, games and activities around waters edge. While the girls were not of drinking age in the US and not technically of 19-year-old drinking age where we were, it was well known that the resort was not carding its guests and it was agreed upon prior to the trip that the girls would be allowed to drink as long as two rules were abided by. First, drinking was to be kept on resort grounds unless the adult chaperones were nearby. Second, they would look out for each other regarding over consumption.

Bethanny had informed me that prior to the trip, Sarah, Kate and Jenn had gotten the group of girls together and talked to them about femininity, indepence and the power of women. While I was a little upset about not being included in the conversation (though I understood why) I couldn't have agreed more with the message. As I watched 4 of the girls from our group compete in a "skin-to-win" wet t-shirt contest, each getting raunchier than the other, I was doubtful the message took hold.

"Let them have their fun," Jenn said to me from across an apparently sleeping Kate. "You can only be young once."

She had obviously sensed my apprehension.

Jenn was the supermodel of the parents. 5'10" tall. Long, red hair. A toned-yet-curvy body with large, perky c-cup breasts, shapely legs and a flat stomach. She had long been an anomaly, a woman who seemingly had it all yet was still down to earth, friendly, approachable and kind. I couldn't think of a single person who didn't have a nice thing to say about her other than the occasional jealous remark on how she maintained her standards. Recently however, cracks in the wall had appeared as she and her husband completed their divorce over his alleged infidelity. She had taken some time away from the parental social scene but Kate convinced her that this trip, like it hopefully would be for our daughters, could be beneficial to her; a chance for her to reshape her narrative. Instead of a perfect trophy wife, that of a strong, independent woman.

"I get it," I responded. "Afterall, they are adults now in the eyes of the law. It's just strange to see."

"If there is any time or place to let loose, this is it."

"I know. Again, just not normal for me. Not judging, just trying to adapt."

"Hey, has anyone put sunscreen on your back yet? You'll burn quickly down here. If you can return the favor I can certainly help."

Besides a friendly smile, Jenn was wearing an appropriately fitting black string bikini bottom. I told her that I might as well do her back first and she flipped over onto her stomach on her chair, revealing a cheeky, scrunch style back to her suit that only seemed to accentuate her fantastic ass. The woman had hit the genetic lottery.

Though I had moved myself in between their two chairs, I hadn't even started on Jenn when Kate's voice squeaked out over the noise of the pool deck.

"Me too, please!"

"Actually, do her first," Jenn said, returning back to a sitting position. "She really needs the sunscreen and I really need to go pee."

I switched chairs and watched as she slipped her feet into light sandals and scampered away.

"She likes you, you know."

"What's that?"

Kate was staring right at me, a mischievous little grin on her face.

"Jenn," she continued, "she likes you and thinks you are quite the guy. You being here is the biggest reason I was able to get her to come on the trip."

"Really? I wouldn't have thought she was ready to be with anyone yet."

Kate laughed at my expense.

"Hold onto your horses there, buddy. She isn't looking for a proposal. She needs a boyfriend like she needs a second ass."

"So what are you getting at then?"

"That's for you to figure out. Now, do my back."

I did as I was told, taking my time working sunscreen across her shoulders, back, sides and down her legs. She had fantastically smooth skin and, had my mind not been wandering about how much my life had changed in literally the last couple of days, I may have found myself physically aroused. As it was, when I patted her on the butt to indicate I was finished, my mind was in a bit of a daydream.

"Hey, you missed a spot."

"I did?"

Kate pushed her butt up into the air, her cheeks naturally spreading with her movement, the tight thong of her swimsuit pressed tightly against her pussy beneath it. I chuckled at the sight.

"You know," I said as I put a small squirt of sunscreen on my hand, "you're now the second person who has indicated this is a normal tanning position. I guess I haven't kept up with poolside trends over the last few years."

I took my time working the sunscreen around the insides of her upper thighs and between her ass cheeks. I worked my fingers under the edges of the fabric and through the folds of her labia, I felt every delicate ridge of the pucker of her asshole. I found my mind wandering again, not away from the subject in front of me, but rather more into the details of the sights and sensations afforded to me. What did she taste like? What would it feel to be in her?

"Don't get us kicked out of here," Kate said, dropping herself abruptly back down onto the lounge chair. "Much more of that and I think the cops might be called."

She flipped herself over and spread herself out a bit in the sun. She had already been topless and, though warm from the sun, her nipples were hard and standing at attention. I could see a bit of jitter in her movement and I was satisfied to know I was not the only one affected by the actions.

"This won't help either."

Kate slipped her hand up my shorts and grabbed my erection, which had formed without my even noticing it, and threw me a mischievous grin.

"What won't help?"

Jenn stepped up behind me, the scene blocked by my torso.

"Will's dick is hard," Kate replied.

"Whaaaaaaaaat?!"

Jenn gasped in amusement and hopped around to my side to get a look.

I had figured the embarrassment of their picking on me would have made it go down pretty quickly but Kate never let go of me. In fact, she not only didn't let go, she kept me stiff with gentle, kneading squeezes.

"Will! That's generally frowned upon," Jenn chastised me playfully as she settled back into her chair.

I gently released Kate's hand from my erection and switched my spot over to the side of Jenn's chair.

"I know, I know," I responded. "Look, it's just been a long time since I have had this much visual stimulation. Just give me a bit of time. I am sure I will adapt."

"No need," Kate chimed in, "all good in my book."

"Same here," replied Jenn, a smile across her face.

"Thank you for the embarrassment, ladies. Now, before I go drown myself in the pool, why don't I take care of your back, Jenn?"

She laid down in the chair on her belly and undid the strings of her biking, offering an easy, open canvas to work with. I took the same approach as I had on Kate, taking my time on Jenn's shoulders, back and legs. As I worked my way up to her feet and approached her butt, Jenn asked me if there was any way that I could avoid getting sunscreen on her bikini bottoms.

"Yeah," Kate chirped, "take them off."

It obviously wasn't going to happen and I also had the feeling that Jenn was not quite yet ready for the type of application I had done on Kate.

"Don't worry," I whispered, "I am sure I can figure something out."

She responded with a mouthed thanks and I did just as I promised.

-----------------------------

When both women were done and Jenn had covered my back, I let them know that I was going to take a walk on the beach, an activity I legitimately enjoyed doing. As neither indicated any interest in joining me, I set off on my own.

With my waist wrapped in the large scarf, I slipped off my shorts and made my way down the sandy shoreline, getting a lay of the land and people watching the other pedestrians and sun-lounging guests. While I knew that the resort was relatively secluded, I was surprised at how quickly the crowd thinned out away from the 12-15 palapa canopies that sat in an organized bunch in front of the resort complex. That said, though the crowd split up, it wasn't as if there was nobody around. In contrast, there were quite a few people, just in much smaller groups.

It wasn't 15 feet past the sign indicating the resort boundaries that I saw my first public sexual act, an older man lazily stroking his own penis while equally nonchalantly fingering the vulva of his female companion.

Walking further, while most inhabitants were lounging quietly and normally, I saw more than a handful of additional activities in the form of blow-jobs, semi-concealed intercourse and LOTS of casual, lazy hand-jobs. What I had not seen was anyone I knew.

"Hey!" The voice cut out into the air that was otherwise filled only with the sounds of water and sea-birds. "We had a deal!"

The direction of the voice directed my eyes to the sight of Sarah, fully nude and walking toward me from the vegetation line up away from the shore.

"Hey!" I found myself surprised at how happy I was to see her.

She closed the gap quickly and wasted no time in pulling apart the loosely tied knot I had made to hold up my wrap.

"You agreed that you would be nude," she chastised, winding the scarf up into a loose ball around her hand.

"Actually, I didn't. You just assumed. But, that said, I was just by the pool. I didn't strip down because I just wanted to make sure I wasn't out of place. I'm still figuring out the unofficial rules of this place."

Sarah laughed. "Well, I can tell you that, 'unofficially,' it seems to be anything goes as soon as you pass the resort boundaries. When I just came back from getting us a round of drinks I saw one couple going at it doggy-style."

I laughed and rolled my eyes. "Yeah, I just saw some as well. How the hell did this resort get picked again?"

"Oh, stop," she responded. "There's nothing wrong with it and you know it."

"What have you been up to?"

"Just hanging with some girls, having a drink. Why don't you join us?"

She took my hand and pulled me along behind her.

When we got to her base camp I was greeted with an overly-enthusiastic round of hello's and the sight of about 25 large disposable plastic cups... all empty.

"A drink?" I questioned Sarah with a cocked eye and paternal tone.

"Oops," she giggled in response as she pulled me down to the ground with her, "maybe it was two."

There were 3 additional girls with Sarah: Brie, Taylor and Leona; all of them nude.

Brie was one of Bethy's normal 10-friend main group. She was muscularly built, a soccer and basketball player at school, but still carried some smoothing baby-fat on her frame. I had seen her topless already, around the pool at my house, though I was not opposed to taking in the sight of her full, c-cup breasts any time she wanted to have them out. I was surprised by the surprisingly full patch of pubic hair she sported though, unlike Sarah's previous suggestion that girls her age were just letting it grow, it was neatly groomed into a large, triangular patch.

I didn't know Taylor as well but, either due to a natural extroverted nature or an alcoholic-ly enhanced lack of inhibitions, she welcomed me, literally with open arms.

"Mr. Patton! O-M-G! I am so happy to see you! Give me a hug!"

She didn't wait for me to respond, rather just threw herself on top of me, her small frame draped fully over my body, pinning me to the sand.

"She's been doing that with everyone since we got here," Leona said. "It's been our social experiment: what will the reaction be to a hug from a random, nude stranger."

"And the results?" I was lying on my back, Taylor nuzzled into my neck like a toddler.

"Pretty good, actually," Leona responded casually. "Other than the one couple that propositioned her to a threesome, everyone else just happily accepted with a smile. I guess being invited for some girl-girl-boy action isn't really shunning her either."