Single Male Chaperone

"Sorry... again," I groaned.

"Mark," Heather inquired as she seemingly disregarded the erection bobbing in her face and continued her work, "do you think it is strange that I seem to know quite a bit about your sex life? Or, as I have been informed, your lack of sex life?"

"You too? Jesus, was it Brie? I don't know what the hell has gotten into that girl."

"No, not Brie. Though it actually doesn't matter who I heard it from. The only thing that I can say is that it was from multiple sources that I wouldn't have expected to speaking about the same thing."

Her hands were warm and the simple touching motions she had on my cock, practical as they may be, meant that I wasn't going to lose my erection any time soon.

"What can I say? It's been a while and this trip has not exactly been easy on my hormones. But, it doesn't change the fact that I think that everyone is blowing things out of proportion. Yeah, I have been getting some unexpected erections. Considering the circumstances, I don't think it is completely unwarranted."

Heather, who had been working with clippers, continued about her job and began slathering my shaft with shaving cream, obviously looking to trim down any hairs that grew along it. I thought about the conversation we were having and, while she had a professional job to do, she had to know what she was doing would not help my situation.

"What about Tiffany?"

"What about her?"

"She wants to have sex with you."

"Heather, I can only hope you are kidding. She is a kid, I am an adult. She is friends with my daughter. There is zero chance I would have sex with her."

"Okay, fair point."

"I guess I blew my chance at sex on this vacation when I stood you up last night." I was probing with my comment and, honestly, it was a bit bolder than I normally would have been in a normal state of mind.

Heather first looked up and smiled, then stood up and wrapped me in a hug. "That's sweet of you. But I can't quite yet. There are things I need to take care of first. I hope we can keep getting to know one another though." It took everything in me not to sigh my disappointment out loud. She looked me in the eyes and smiled, and gave me a quick kiss. "I think we have a connection though and would love to see where this goes." I simply smiled and kissed her back. Friendship and connection were not going to relieve my swollen nuts. Though, that was not my biggest problem.

Heather had returned to her chair and finished everything up. She had a warm, damp towel and had just finished cleaning up my junk when we were both startled.

"Oh, uhm..."

Two of Brie's roommates were standing in the entrance way of their own room just staring at me, buck naked, and Heather, on a chair with my dick right in front of her face.

"The door was propped open..."

Shit.

Of course, I wanted to shoo them out but, in hindsight, I know that would have been a bad idea. Heather played it cool and just continued about her business as if it were the most normal thing in the world to walk in on.

"Oh, sorry about that. We just finished up with Brianna. If you are looking for her, I think she went with Tiffany to her room. If you don't remember me from yesterday, I'm Heather." The girls said their hello's but still stood in the entry awkwardly for a moment, eyes glued to my dick. Thankfully, the nervousness I was feeling had me rapidly shrinking. As Heather realized my shrinking state, she decided to continue acting as if everything was normal. "Ladies, you were at the beach yesterday, so you saw Mark previously. Can we get your honest opinion? Is this better?" An odd thing happened in that, with the direct engagement, the two seemed to relax and actually stepped further into the room, still staring at my groin but now with assigned purpose.

"Much neater."

"Yeah, much cleaner. So, yeah, better."

"See, Mark," Heather said as if she was concluding a long conversation, "always trust a professional. Why don't we get everything cleaned up and leave the girls to the room."

"Actually, we were just looking for Brie. We can go see her in Tiffany's room."

The two girls left the room and Heather and I could hear clear laughter in the outdoor hallway, something that made my face burn bright red with embarrassment.

"Easy there, Tiger," Heather said as she saw me get flushed. "Not a big deal. Nothing to get worked up about."

After everything was cleaned up we locked up the room and said our goodbyes. Heather was spending the rest of the day and evening off-resort with her crew of girls. I was left to my lonesome self.

-------

As I should have expected, news traveled fast.

"Tell me, Mark," Melanie asked me after I bumped into her at the beach and situated myself next to her, "why on earth did you wait until after we went to the nude beach to get yourself all trimmed and groomed."

"The opportunity presented itself a bit too late, I suppose. That is, it is only too late if you are saying we aren't going to go back to the nude beach."

"Ahh, touche," she responded with a wink.

Melanie had really surprised me in her rapid change of demeanor on the trip. At first she seemed self conscious and nervous. Now, laying out in the sun, topless and with what I can only assume was a borrowed thong, it was as if she was born for this life. And, I can admit, with a healthy glow to her skin, she really did look great.

"I actually thought you went with the group. I guess I was mistaken."

"I don't know what you are talking about. Did they go back to the nude beach?"

"No, shopping in town."

I had heard Sara and Gina speaking on the way down about wanting to head into the little tourist town to go shopping at least one of the days. I had told them at that point it didn't particularly interest me so apparently that is why it wasn't mentioned. I was surprised to hear that Brianna hadn't told me.

"Everyone went?"

"No, not everyone. I am pretty sure a number of the girls are still here on the resort property. But, both Sara and Gina went and I think at least about 10 girls."

The timing could not have been better as Brie, Tiffany and 3 other girls strolled by on the beach in front of us, Tiffany being the first to spot us and wave, Brianna and the others following suit. All 5 were topless, Brie and Tiffany were in the tiny micro g-strings they had prepared themselves for and may as well have been nude.

"So, what are you up to then," I asked Melanie as the girls passed by.

"A little sun, a few drinks, making the least of my time," she responded with a coy smile.

"Mind if I join you?"

------

A few drinks went down quickly and easily and Melanie and I found ourselves getting more and more flirty as the alcohol broke down any sense of public decorum. It was good that we were pretty much alone on our section of the beach because at various points, our alcohol induced sense of impropriety found Melanie practicing her lap dancing skills in pretty raunchy form. When we both admitted that we really needed to pee we made our way to Melanie's room.

It was not a surprise when, stepping into her bedroom, where she was going to put back on her swimsuit bottom though instead stumbled onto her bed, she pulled me with her and "one-thing-lead-to-another."

The sex was a relief and, with the alcohol, I believe neither of us had any apprehensions as to the fact that it was our first time with one another or the first time in quite a while for either of us.

We rolled around and played, we kissed and we petted.

She gave me a blowjob, I licked her pussy until she quivered.

I sucked her nipples, she sucked my earlobes.

She asked me to put a finger in her ass as she was about to orgasm, I asked her to just give me a moment after I came.

We got sweaty and sticky and flopped on the bed when we were done, both of us breathing heavy but, at least for me, somehow not completely fulfilled.

After catching our breath each of us cleaned off in our respective showers and, after I was done well before she was, agreed to meet back at the same spot on the beach that we had previously.

"Hey," I said to her as she walked back, her bare breasts moving tantalizingly with each uneven step in the sand.

"Hey to you," she responded.

"That was fun."

"Yeah, it was."

There was what seemed to be an awkward silence in between us as she spread out a towel and again got herself situated. She asked me where the girls were.

"Not sure, to be honest. I haven't seen them here on the beach."

"Okay. Just curious."

The small talk was excruciating. It was obvious that there was something on both of our minds but neither of us could get it out. The alcohol had very much worn out.

"So, uhm..." I made an attempt to start a conversation but she mercifully cut me off.

"You obviously feel it too," she said.

"Not sure what you mean, but I feel something."

"Well, I guess I will just say it." Melanie sat up and faced me. "The sex was fun. But, if I am being honest, it felt like something was missing."

"It felt like a one-night stand, right?" I too sat up, thrilled that she had addressed the obvious 10,000 pound gorilla in the room.

"It was a physical relief but I just didn't feel like we had a connection beyond that."

"It was good though," I said, making sure she didn't think I wasn't satisfied.

"So good!"

"Just no lightning.

"

"Nope."

We both had silly smiles on our faces and started laughing.

"Does this make us sluts?" Melanie had an excited, wide eyed smile on her face. She was excited at the prospect of being naughty.

"Well, not to rain on the parade, but I think it would take a bit more than one session of sex with a friend to make us sluts."

"Damnit, well that is no fun. I thought for once in my life I could be a bad girl."

I knew exactly what she meant and I also knew that, even though it was still weird coming from by daughter, Brie was right. I did need to get out there, to see women, to not just be a dad. Especially to a single child that would be moving out of the house in meer months.

With the weight off of our backs that it was okay to have just had sex for no other reason than having fun with a friend, Melanie and I enjoyed the rest of the afternoon. Plus, even without additional alcohol, the endorphins from the sex had each of us relaxed and at ease.

-----

Stopping over to see us, I really focused on the fact that, other than the tiny patches of lycra that covered their newly waxed kitties, Brie and Tiffany were a picture of physical opposites. Brie was tall and lean; Tiffany was short and thick. Brie had high-chested, perky breasts; Tiffany had large, full breasts that swayed and bounced with each uneven step she took in the sand. Brie had blonde, straight hair and an almond shaped face; Tiffany had dark, curly hair and a round, heart-shaped face. Brie had pale, almost Nordic skin that was gently sun-kissed; Tiffany had olive skin that had soaked up the rays easily and she, after only a couple of days, had a dark, even tan. Yet there they were, a picture of opposites, standing in front of Melanie and I in only an eyepatch worth of clothing and both (yes, even my daughter) were incredibly sexy in a very adult way. It was something specifically about the two of them. The other three were attractive girls but that was it, they were girls. Though all 18, only the two of them seemed like women. I felt bad about the thought, especially considering the conversation I had with Heather just hours before. I told her that Tiffany was a child to me and all of a sudden... bam! Woman. Tiffany had one other difference between my daughter in the way she was wearing her suit. Whether accidental or not, the patch of fabric was pulled low enough to leave the top of her remaining groomed pubic hair very clearly exposed. While I had never told anyone this before, that had been a fetish of mine for many years. I felt myself staring. Tiffany was very seriously turning me on.

One of the girls informed us that they were heading in to get ready before dinner and Melanie decided that we may as well go with them. Getting back to our rooms, we found Sara and Gina trying on some apparently new dresses they had purchased and were planning on wearing to dinner.

"Did you have sex in our room?" Gina's question was direct and to the point. Melanie turned bright red, I laughed and looked at her. She didn't seem to know what to say. She had a look of terror in her face, not knowing what to do. I realized afterwards that my reaction actually gave us a few different options as far as how the question was handled but Melanie, cool under pressure when the girls walked in on her grooming my dick, instead just froze up. She stood there like a deer in headlights, face still flushed, staring directly at Gina. "Well, I guess that answers that," Gina responded to the non-response. "That's cool. I just wanted to make sure it wasn't some random hotel employees fucking on your bed. You can tell me all about it later."

Melanie hurried herself into the bathroom and, once there, spun around and mouthed the words "what the fuck" to me in wide-eyed amusement. I also hopped into my shower and in the middle of showering the curtain was yanked open and Gina, dressed beautifully in her new dress, said to me "I heard you got your balls trimmed, just wanted to see them."

What the fuck, indeed.

------

Part 5:

On Day 5 everyone felt like seasoned resort pro's. It was determined that nobody needed to go topless anymore as it was no longer a bucket list item or a feeling of rebellion. I did notice that throughout the day, girls were changing their swimsuits more often and I swear one of them had 4 different suits on at different points. And, while it was previously stated the girls didn't need to go topless, it didn't mean that there were any fewer breasts exposed. In fact, every single one of the girls went topless at least at some point during the day. "Better for tanning," it was explained to me.

It also seemed to be the day that the girls determined that having the parents around was not only not-so-bad, but could be fun too. All four of us were invited to hang out at the pool and, in general, had a very good time with the next generation. Of course, with all of the sexual innuendo games going on poolside and our groups excitement with participating in them, there was certainly more than one cock-eyed glance exchanged between the other parents and I but, as promised, we continued to allow them to experience the resort and have fun.

The familiarity of the resort and the girls settling into being allowed to act as adults also gave rise to our first regrettable scenario of the entire trip. The good news is that all of our foggy moments could have ended up much, much worse. The bad news is that they happened. In this case, Jamie, one of the girls I didn't know very well, got drunk at the pool and started hitting on a guy. After making out and giving all the wrong/right signs, the guy suggested that they "take the party elsewhere" and she agreed. In his defense, I didn't feel like he was predatorial when I was alerted to the situation and stopped them in the hallway, he was just allowing things to progress as she seemed to be pushing them. However, after getting her cleaned up (why I was the parent chosen for the task I don't know) and closer to right-minded, she thanked me, embarrassingly admitting that she went overboard. I lost the evening on the bed of a darkened hotel room with a nude teenager curled up on me, desperate to sleep off the inebriation that had caused the problems to begin with. It wasn't too bad though, I hadn't really napped since the first day and, as I was determined to slide into my geriatric years as quickly as possible, I ended up passing out myself on the bed with her.

I woke up a couple of hours after Jamie and I had fallen asleep and was sweating. It wasn't so much that I was still wearing shorts and a t-shirt, it was that she was still draped over my side and the combination body heat was practically unbearable. Figuring that she was able to handle herself, I started trying to ease out from under her in order to go back to my room. When doing so, however, I woke her up enough that she grabbed me tight and begged me not to leave. As there was nobody else in the room I felt bad enough to agree to it. Nonetheless, I took off my shirt and shorts, leaving on a pair of thin cotton boxers to "cover me up."

Good enough. Or, at least so I thought.

------

Part 6:

I woke up on day 6 with not one, but two nude, teenage bodies draped over me. One was obviously Jaime, the other, unfortunately, was Tiffany. To make matters worse, my dick had popped out of my boxers and I was sporting extreme morning wood. That's what I got for being the good guy, I guess.

For the second time in less than 24 hours I tried my best to wriggle out from under the soft, teenage flesh and for the second time I got reprimanded and whined at to stay where I was. This time I stood my ground and said that it was time to leave. As I got out of bed I realized 2 things: First, I needed to find my clothes. Second, I really had to pee. With the second item instantly obvious that it was the far more pressing of the two, I shuffled my way into the bathroom to relieve myself.

I found myself standing there, door not completely closed as I didn't want the latching sound to wake anyone else, trying to figure out how to make my boner go down. While this was certainly not the first time I had woken up with a night time erection, it was the first time that I just couldn't will it away. In fact, it felt like every time I even thought about anything... anything at all, my dick just bobbed a little higher and a little stiffer than previously. I was contemplating this, my hands back on the vanity, my boxers around my knees, my hips thrust forward, my cock pointing to the ceiling, when the door swung open and a sleepy Tiffany walked in and immediately sat on the toilet to relieve herself. I stood frozen as she appeared not to notice me at first, peeing like I felt I had to, her face in her hands. When done, she wiped and stood up, practically bumping into me.

"Hey," she said with a very groggy voice, "I thought you left."

"About to," I responded, "I just have to pee first."

"Oh, did I cut the line?"

It seemed obvious to me that she was completely out of it, as if she did not remember at all where she was or who I was.

"No," I said to her as she stood in front of me, rubbing her breasts as if she had just taken a bra off after a long day, "you're good. I just had some things on my mind."

"Probably can't pee with that thing either, huh?"

"What's that?" I knew what she was talking about, of course. I was just playing dumb because it seemed like the best thing to do at the time. I hoped her sleepiness would trump logic.

"This." Tiffany wrapped her hand around my dick and just held onto it.. "You have a hard-on. I bet you can't pee with it."

"Nope, it is tough," I responded, afraid to move.

"Well, good luck with that." Tiffany let go of my erection but did not immediately leave, instead she wrapped her arms around the back of my neck and pulled herself in for a hug, her warm body pressed up against mine, my cock sandwiched in between us. She held there for a moment, her face nuzzled into my chest, before she got up on her tip-toes, gave me a kiss on the lips and let go.

"Okay, bye," she said in the same sleepy voice as before, walking out the door, just dragging her finger tip up the length of my penis as she stepped away.

Holy shit, I had to get out of there.

I yanked my boxers up and tucked my dick into the waistband. I found my shirt but not my shorts in the room and snuck out out of the room, a foolhardy plan that found me needing to go to the front desk in just my boxers and explain that I needed a new key to my room. Thankfully, other than a knowing smile, the key was produced without further hassle.