Single Male Chaperone - Reimagined

Though we seemed to sync into a rhythm quickly, things between us changed as soon as I was inside her. Instead of the passionate, vocal partner I had started with, Lilly went quiet and basically laid still. She had her eyes closed and her body was limp and, if I hadn't known better, I could have been having sex with an extremely realistic sex doll. Physically, she was there, mentally and emotionally, I was on my own.

"Lilly?"

"Yeah?"

She opened her eyes but otherwise didn't move.

"Are you okay?"

"Yeah, I'm okay."

She lay still for a moment, eyes still closed, me hovering over her, my dick still in her, before opening her eyes and propping herself up onto her elbows.

"Why do you ask?"

"Well," I responded, "it's just that you stopped moving. You really don't seem to be into it."

"No, I'm okay."

She had a blank look on her face. She didn't seem upset, she didn't seem happy, she just kinda' seemed there. Something just wasn't right.

I pulled out and sat on the sand to the side of her. Taking my lead, she sat up next to me, shoulder-to-shoulder. We sat in silence, just staring out into the ocean, before I decided to break the tension by putting my hand on her knee. She turned her head to me. Though there were no tears in her eyes, there was obvious anguish.

"So, I like the kissing. I like the touching. I loved the oral. I love the togetherness."

Silence.

"But?"

I prodded her a bit to continue.

"But I really don't like the sex part."

"With me or at all?"

"At all."

"Does it hurt?"

"No. It doesn't hurt. There have been times when I can admit it actually feels kinda' nice. It's just the concept of it."

"The concept of sex?"

"The concept of a penis. Inside me. It's awful. Like, to just see one is kinda' like 'okay, it's there and it's fine, just stay away from me.' But to then have it in me, well I can't take my mind off of it and how unappealing it is."

"And it's not just with me, it's been with other guys too?"

"Well, other guy, singular. My last boyfriend. Yes."

"And you were attracted to him?"

"Yeah, sure."

Not exactly convincing.

"Lilly, are you saying that you aren't attracted to guys?"

"Uhm, I don't know. Like, I like you and I like how nice you are and that is attractive. And it was the same thing with my last boyfriend."

"Look," I continued, "I am not looking to overly simplify things or anything, but are you a lesbian?"

"Oh, my God, no! Definitely not! Like, why would you say that?"

I could see she was triggered.

"Whoa, whoa, hang on. I'm not trying to label you or tell you that you are something you aren't. I'm just trying to see if we can figure out what is going on?"

"Well, I am definitely not a lesbian. Okay? Like, I am totally straight. And, besides, guys are totally into me so I obviously can't be gay."

Her attempt at logic made no sense and she was about as convincing as a puppy caught making a mess.

"Well," I continued, again patting her on her leg, "I think it best if we just leave things as is. Sex is best when it includes two willing and interested participants. It's just not going to work if you are saying you don't like it."

"Okay."

Her response was practically a whimper.

We stayed where we were for a while, just continuing to watch the water, not saying much of anything to each other. It was obvious that the day, based on actual time or experience, was coming to an end, though it didn't seem right to just pack up and leave. Afterall, what kind of message would that send? If we're not having sex then you aren't worth my time?

As the sun started to go down and we realized that it was probably time to get back to dinner, Lilly again spoke.

"Will?"

"Yeah?"

"Do you think girls would like me the same way that guys do?"

She was obviously tormented inside. I wanted to give advice but I was also just so out of my league. This was a trained therapist type scenario and I was just about as far from one as you could be.

"It's been my experience that guys can be a bit more superficial than women when it comes to expressing their attraction so, excuse me for being so blunt, with beauty and a body like yours, it will still probably be guys that are doing the hitting on you."

She had a smile on her face but I could also see that there was worry in her eyes.

"But," I continued, "it's also been my experience that women can very often be much better partners in a relationship and..."

I put my hands on her shoulders and made sure she was looking at me when I said it.

"... and that's what you are looking for: a relationship. Not just some person who is lusting after you or some person you are lusting after but someone who you can share an actual bond with."

She was looking at me and just kind of staring, waiting for me to respond to what she actually asked.

"So, to answer your question," I concluded, "yes, I think that girls will like you the same way that guys do. Just don't feel like you need to rush anything. You're the prize. Wait for the right person and don't have any preconceived notions of who that person is supposed to be."

I can't say that I was totally surprised when I saw the tear stream down her cheek or when she stepped into me and squeezed me in a tight hug, our bodies fully pressed against one another, I will say that I was surprised when she stepped back and chuckled a response.

"See? And now I want you to fuck me."

I laughed, pulled her in close for a hug and placed a kiss on her forehead.

"And you have no idea what an amazing offer that is," I responded. "But I think we already figured out that we aren't right for each other. Remember, wait for the right person."

Truth be told, just being around her had me, contrary to what I thought my body was capable of, somewhat riled up - she was just that hot - but I also knew that right was right and taking advantage of her vulnerability was most certainly not.

Lilly smiled and squeezed me one more time before we grabbed everything and headed back. Who knew, maybe our paths would meet again in the future.

We split up as we got to the resort, Lilly seeing some of her friends that she wanted to meet up with, me heading back to my room to get cleaned up before dinner.

But, sometimes, things don't work out as originally planned.

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"Will! Can you come in here?"

It was Emily, one of the girls that had been in Bethy's group on the beach earlier in the day, was peeking outside of one of the resort bedrooms, coincidentally next door to Bethy's room. The look on her face was not that of worry, rather of excitement.

"It's so awesome you just happened to be walking by," she said as she opened the door to let me into the room, "we could use your help."

With the door closed behind me I took a second for my eyes to adjust to the change in the light and found myself standing in the front hallway leading into the room. Emily was next to me. Bethy and two other girls, Hope and Jamie, were standing in the bathroom to my right.

All were fully nude.

"Oh, hey, D-...Will!"

Bethy had caught me out of the corner of her eye.

"Dwill?"

"Do I really need to call you Will? I mean, it's just weird. Can't I keep calling you Dad?"

I chuckled.

"Yeah. That's fine."

Bethy and Hope were checking themselves out in the mirror, Jamie was seemingly just standing there. I, standing in the hallway with Emily, was still not clued into why I was pulled into the room.

"Oh! Wait!"

Bethy, who had seemingly forgotten in the last 15 milliseconds that I was even there, perked up again and grabbed Emily and pulled her into the bathroom with her, facing both of them towards me.

"Check it out!"

Bethy already had but Emily immediately followed in pushing her hips out to me, presenting very shiny, very red and very smooth pubis'. They had obviously waxed.

"Smooth as can be! Heather's stuff is amazing! Barely hurt at all!"

I still didn't know what to say and just stood there, awkwardly.

"That's what we've been doing," she continued, "giving each other bikini waxes. I can't believe I have never done this before. It is so much better than shaving. And! Check this out!"

She spun a shocked Emily around, who appeared to just be going along for the ride, and bent her over, spreading her butt cheeks apart. Bethy was just super giddy.

"No hair, anywhere! No stragglers. No stubble. Perfectly smooth and clean."

Bethy pulled Emily back upright and spun her around. Bethy was grinning like an idiot. Emily just looked harried and confused. In the background, Jamie was wide-eyed. Throughout the entire experience, I just stood there.

It was a heartbeat and a half later that Bethy seemed to snap to the moment.

"Wait," she said, a newly confused look on her face, "what are you doing here?"

"I was hoping someone could explain that to me," I responded.

"I thought he could help," Emily responded, directing her comment to Bethanny. "With Sophia."

Bethanny's face lit up.

"Oh, my God, yeah! That's a great idea!"

Bethy stepped out of the bathroom and grabbed me by the wrist, pulling me toward the bedroom area. When we got around the corner, both Sophia's and another girl, Annie, were in the room. Annie and one of the Sophia's (I didn't know their last names) were wearing bikinis, the other Sophia was on the bed, fully nude and seemingly waiting for something.

"So, Sophia is the last one to want to get a wax but she is so ticklish!"

"And?"

I still didn't know why I was there.

"And," she continued, "maybe you could do it. Guys hands are bigger and rough-er and less tickle-y."

Bethanny pulled my hand and, after spreading Sophia's legs open, placed it on her inner thigh. Sophia shivered an almost imperceptible amount but otherwise layed still.

"It works!"

All five of the girls crowded around the bed, giddy with enthusiasm.

Teenage girls are weird.

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

The process was straightforward, first we used clippers to trim her hair down to a shorter length, then we covered her entire vulva and butt crack with powder and then we got down to the actual waxing.

By "we," I mean "me."

If I am being honest, I learned a lot that day and, while I was at first annoyed to be thrust into the position of administering the brazilian, the technical aspect of it was somewhat interesting. All of the girls were chiming in with details whenever they thought necessary which was, apparently, a lot.

"More powder!"

"Against the grain!"

"Just pull her lips to get the skin tight!"

"No, not on her asshole! Around it!"

I was just about finished with the last section of her front when one of the girls' phones buzzed with a notification and she was informed that there was some sort of contest going on down on the beach that would be of interest to them. I can't say that I wasn't annoyed when all of the girls (except the Sophia on the bed) pulled on swimsuits or coverups exited the room though, when I witnessed her never moving an inch, it also didn't seem like Sophia cared about the situation we found ourselves in, just the two of us.

With the clamour of the girls around us suddenly gone, the most uncomfortable part of the experience for me was not that we found ourselves in such an intimate and compromising scene, rather how quiet the room got. Sophia hadn't been saying much the entire time, with her arms covering her eyes and her legs spread wide, she prepped herself with deep breaths each time the wax went on and I told her I was about to pull the cloth strip, and she acknowledged the violent depilation with not much more than a whimper and another deep breath or two.

The majority of her vulva had a bright red flush to the skin that stood out in contrast to the deep tan of the rest of her body. As things began to wind down and the lack of distraction became more of a reality, I found myself being taken in by the sights and situation in front of me.

A damsel in distress.

Her large, soft breasts that heaved and jiggled with each movement and breath.

The smooth skin of her voluptuous body.

Meaty, defined labia, just begging to be sucked.

I finished with the last strip of wax on the inside of her thigh and told her it was time to turn over. We had already been informed that the best way to address the backside was to have her get on all fours, ass in the air.

Sophia sat up and I watched as she went wide-eyed, staring directly at my crotch and, when I followed her line of sight, I saw my beach wrap tenting comically in front of me. I had never even noticed myself get hard as the thin wrap basically offered no resistance.

"Oh, crap," I said. "Do you want to hold up a minute? This should go down a bit."

She smiled.

"I'm fine with it as long as you are. If it's okay, I'd prefer to just finish as my skin kinda' burns."

"Geez, yeah. I didn't even think about that. You're okay to keep going?"

"Yeah, I think so. The other girls said that the oil you put on afterwards is amazing so we might as well get to that point."

She flipped herself over and presented herself to me, her large, wide bottom pointed straight at my face, and she instinctively reached back and spread her cheeks, stretching herself wide open and offering a site that nearly took my breath away. If we were both looking for my erection to subside this just wasn't going to do it.

The reality of my explanation of all of these events is drawn out as, truthfully, we did our best, front and back, to make the entire waxing experience as quick as possible in order to make any associated pain as minimal as possible. Nonetheless, when the final waxing strip was pulled it wasn't just her red skin that called for relief, Sophia did as well.

"The coconut butter, please!."

I grabbed the mason jar on the counter as she collapsed to the bed and got an extremely liberal amount of the thick white cream on my hands, immediately spreading it, gently, across every affected region.

"Oh, God... yessssssssss..."

"Good?"

"Better than good. They weren't kidding."

I quickly covered all affected areas and stepped away to clean up the supplies. Sophia was having none of it.

"No. Please, keep rubbing. Just gently, lightly."

I got a bit more coconut butter on my hands and began massaging her affected regions, all around her vulva, in and out of her ass-crack. The greasiness of it was terribly slippery and I felt myself taken in by the feeling of her newly waxed skin under my fingers, slick and smooth, it was like playing with warmth.

And, of course, my hands started to drift. As opposed to being completely clinical in my application, I soon found myself drifting: across her clit, across her puckered butthole, her labia weaving their way through my fingers. There was something playful about it but, at the same time, my cock was rock hard and it was most definitely terribly erotic.

"Can you do me a favor," she whispered, seemingly taken in by the moment, "can you blow on my skin a bit? Just some cool breaths?"

My brain clicked and I reminded myself I was there for a functional purpose: To provide a bikini wax and to help in her recovery from it. So, I leaned in and applied gentle, light blowing to her skin.

Big mistake.

The smell of the coconut.

Sophia's squirming and moaning from my touch and breath.

The visual of her voluptuous body and glistening sex just inches in front of my face.

NINETEEN:

I didn't even think about the repercussions of it when I first dove in, dragging my tongue across her now swollen clit. After all, it was just there, begging me for attention.

I didn't stop when Sophia's head bolted off the mattress with a look of shock on her face that I caught out of the edge of my vision.

"Uhm. Mr. Patton? What are you do-... Ooooooohhhh... Will? Mmmmmm..."

I didn't slow down and instead solidified my position, kneeling on the floor and locking my face between her thighs, my arms wrapped around her legs, my hands finding their way to her large, soft breasts, her nipples now the focus of their curiosity.

"Will! Ooooooh! Oh, God!"

I thought nothing of the fact that I had basically chastised Kara for having her way with me less than 18 hours prior and I continued my oral onslaught. Soon, the taste of coconut was mixed with that of her natural sweetness, an intoxicating combination that made me only want more, not less.

Sophia's thighs pressed firmly against my head as she built steadily through an orgasm and her moans grew louder as I felt her body tense around me.

"Oh, God! Oh, God!"

Sophia began to shake under me.

"Jesus Christ!"

The reaction some of the women were having to my cunnilingus was really beginning to inflate my ego.

I felt her body begin to go limp but almost immediately stiffen up again as she attempted to push me away.

"No more," she whined, breathily. "No more, please."

I mercifully detached my mouth and audited the scene. Sophia was a mess, obviously drained; her eyes closed and her chest heaving, her swollen, red pussy still twitching with the tiniest of aftershocks, a tiny hint of milky white liquid dripping down across her asshole.

"You okay?"

She didn't respond to me. Not verbally, not visually. She instead just laid there, her hair a mess, her tanned body practically lifeless and, for the first time, I didn't quite know what to do with myself. I realized I was just standing there, fully nude, my dick still rock hard and pointing to the sky. My beach wrap had been pulled off of me by my own movements and lay in a pile on the floor along with the mess of girls' items strewn about the room. I thought about grabbing my belongings but couldn't muster the courage (or callousness) to do it. So, I stayed.

I got on the bed with Sophia and brushed the hair out of her face. For the first time after what happened, she acknowledged me.

"How did you do that?"

She looked at me with glassy eyes, a weak smile on her face.

"You okay?"

"I don't know. I was not expecting that. Any of that."

"I hope I didn't upset you."

"Only in that I have never had that before."

"Oral?"

"An orgasm."

"Really? Not during sex? Not with masturbation?"

"Definitely not during sex."

"Masturbation?"

"I really never do. I have 3 younger sisters and I share my room with one of them. I basically have no privacy."

We sat in silence for a moment,

"Is that what your worry was? Privacy?"

"No. It was that my friend's dad's tongue was in my vagina," she responded with an incredulous tone.

I felt my face drain white and then flush red. My ears were burning with embarrassment, the only good thing coming out of the situation was the rush of blood was diverted away from my dick and I felt my erection begin to go down. Sophia sensed my obvious discomfort and, after letting me sit in agony for a moment or two, did her best to calm me down. First, with statement:

"But, before you go and kill yourself or something, it was amazing and I'm glad you did because there is no way I would have ever made the advance myself. I didn't know my body could feel like that."

Second, by grabbing my dick and stroking it back to life.

"You know," she continued, "some of the girls have mentioned that you are pretty good with this."

Her comment began to settle my unease just a bit but it was her statement in the run up to it that really got me thinking.

"It's too bad we don't have any toys or something. It seems to me that if you have never had an orgasm until today that our time could be much better spent."

With a funny look on her face, Sophia got off the bed and, after composing herself just a bit (fingers combed through her hair and commenting that her knees were still a bit wobbly) walked into the adjoining hotel room and came back with a massive drawstring bag. No words were said as she took the bag and unloaded its contents onto the bed, a massive collection of lube, vibrators, dildos, butt plugs and other sex toys.