Single Male Chaperone

"Oooooooooohhh," she moaned, her relief obvious in her voice and via my touch, "you know what you are doing, don't you?"

"My kid is an athlete and I can't afford to have a professional do this whenever she is sore. It is amazing how much you can pick up online and with a bit of practice. I just hope I can help."

"Oooooh, God. Just keep doing that." I smiled to myself as I really hadn't touched much on her other than her shoulders and she was making it sound like she was about to climax.

I settled into a system and I worked methodically around her body: shoulders and arms, back, calves and hamstrings, butt. The entire back side of her glistened from the oil in the candlelight as I worked each ass cheek, going much more thoroughly (and erotically) than I ever would on my daughter but for an enticing adult female who seemed very much in need of the relief. I was bold in the movement of my hands, firmly rubbing the inside of her thighs and allowing the sides of my fingers to brush up against her professionally groomed pussy, which absolutely radiated with heat.

After some time I requested she flip over onto her back and she did as she was told wordlessly, not only responding to my direct request but also spreading her legs open a bit, to me an obvious response to enjoying my touch.

Again, I worked down her body, professionally when I needed to, erotically when I thought appropriate. Her arms became jello in my touch, her nipples the exact opposite. Similar to her back, I started at the extremes and worked my way into the middle. Hands and feet, arms and calves, breasts and thighs, hips and pubis. There was only one final, obvious spot I had not offered direct attention and I was gratified to find her labia absolutely engorged and a small amount of milky white liquid dripping from between her brown lips. The only question I had for myself was: should I be so bold?

"Sara," I whispered.

"Yes." She responded in a statement, not a question. She was not inquiring as to what I wanted. She was responding to what she wanted. It couldn't have been more clear.

I sat in between her legs and wrapped her lower legs loosely around my back. The sight that was presented to me was like an erotic dream and everything about her at that moment screamed sex. Her hair was strewn about as if in a shampoo commercial. Her breasts, flushed and full from arousal, protruded higher from her chest than natural breasts should and the folds of her sex begged for attention.

I continued with both hands at first, stroking her inner thighs and just barely grazing her lips. With each carres, my attention became more focused, more centered, zeroing in on her clitoris and the relief attending to it could provide. Saras body also began to respond rhythmically to my movements and in the buildup to her climax her breath became faster and more shallow, her legs wrapped tighter around me, nipples tightened and her hands grasped the sheets as though she was hanging on for her safety.

When she finally came over the edge and I assessed the situation I was presented with two obvious truths. First, Sara had needed that orgasm and she was physically spent. Her breasts were no longer high and proud, her muscles no longer tense, she was loose and yet still catching her breath all while in a practically unconscious state. Second, I was left with an extremely painful erection.

I slowly unwrapped her legs from around me and got a warm washcloth from the bathroom that I used to clean her up. She did not resist as I shifted and moved her body, using gentle strokes to wipe up the wetness covering the most intimate areas of her body. When done, I simply lay a sheet over her and blew out the candles, knowing that the best I could offer her at that point was some peace and quiet in her state of pseudo post coital bliss.

------

I hadn't realized how late it was when I left the room and made my way out to the beach for a walk, finding Heather leaving the bar with her group.

Shit. Heather.

"I am so sorry," I rushed over to explain. From the look on her face I could tell she was hurt but at least seemed to be willing to give me the benefit of the doubt. "I had a friend in need. Someone who asked me to be there for them and I just didn't feel comfortable leaving. I am sorry I was unable to let you know ahead of time."

Thankfully, her features softened.

"I believe you. And it isn't to say I didn't have a nice evening," she responded.

"I need to go for a walk, care to join me?"

"I was actually going to go to bed."

"I understand. I guess I kinda' blew my chance."

"Oh, don't be silly. You were helping a friend. Besides, who is out on one strike?" I smiled and there was a moment of silence before she continued. "Tell you what, wait by the pool and I am going to get my sister back to our room. I will meet you out here in a few minutes."

We spent the late evening hours enjoying the company. We never did have the drink and, if I am being honest, I never did get the satisfaction of the physical contact I hoped we would have had if we had continued our evening onto the dancefloor like I had imagined it. But, it was obvious that Heather and I had an attraction for one another and, even beyond that, a legitimate bond. I looked forward to seeing where it could go.

Part 4:

After getting in late the previous evening and never having had gotten any release from a day and evening full of erections, I can't say that I was very well rested the next morning when I woke up. Heather and I had decided to go back to our respective rooms when we heard my group coming back in from the club. We actually ran into Brie and the other girls, all flushed from dancing and glistening from sweat, in the stairwell to our rooms and they confirmed that they had had a wonderful time dancing with one another. Every one assured us that they needed a shower before bed and Heather and I smiled at the girlish laughter that arose when they playfully argued about who would get the shower first or if they would just end up sharing. Before parting, Heather even surprised me with a kiss. All of these things, combined with the lack of sleep, meant that the massive boner I woke up with would not be tamed by mere un-sexy thoughts. In fact every time I tried to think of something unappealing all I ended up doing was getting sexy imagery in my head that made things worse.

Drudging my way into the bathroom that morning and desperately needing to pee, I was greeted by Sara who was also nude and in the middle of what I assumed was a lengthy makeup process.

"Good morning," she greeted me in a somewhat relaxed, sultry voice.

"Good morning," I responded in the only croaking baritone I could manage.

"Before we even get our day started I want to thank you for last night," she said. "Your hands were magic and you gave me exactly what I needed."

"My pleasure," I grunted grogily. "Happy to help a friend."

"Taking a shower?"

"No, just need to pee."

"Pee? Oh, honey, I don't think you are going to be peeing any time soon with that thing." She was looking directly at my cocks reflection in the mirror. "Do you want a minute alone?"

"No. Thank you. I think I maybe just need to walk it off."

I slugged my way out of the bathroom and into the main room, only to confront Melanie and Emily prepping themselves in the mirror. Emily immediately turned when sensing the motion and her eyes practically popped out of her head when they directed their attention to my bobbing member.

"Oh, my God," she exclaimed in a gasp while trying to stifle a laugh.

Annoyed with the lack of privacy, I turned into the other room.

"Mark, wait," called out Melanie, but I wasn't listening.

I stepped into the room where approximately 8 girls were strewn about. All were dressed (or at least more covered than I was, no matter how small their swimwear) and seemingly waiting for Gina. There were a couple of gasps and a couple of phones that had previously been the object of attention popped up in a desperate attempt to take a picture but Gina actually saved me. Grabbing a used towel off the back of a chair, she simply wrapped it around my waist and walked me into the bathroom, hushing the clamor of the girls behind her.

"Good morning, Mark. Nice of you to join us today. I didn't realize the stage show started so early today."

"I need to pee," was the only thing I got out of my mouth. I wasn't embarrassed, I wasn't ashamed, I was annoyed.

"Go here, take your time." Gina backed out of the room and left me alone, closing the door behind me.

The cold shower started as painful but, as my only defining characteristic subsided I was able to warm up the water and finally get myself clean, though no more satisfied than I had previously been. It became obvious to me that everyone had left the two rooms and I was able to get dressed before Brie came to my room, letting herself in with what I only assume was Sara's key.

"Dad. What is going on here? Again?" She was still speaking in the same whispered tone that she had when we were in public previously.

"I know, I know. It's honestly just getting worse."

"Dad, you need to get some release, you know?"

"Excuse me?"

"C'mon! You know what I am talking about. You said it is getting worse and it is only going to continue to get worse until you take care of it."

"Take care of it?"

"Yeah! Dad, you have to cum!"

What. The. Fuck.

"What the hell do you know about this?!" I had always had an open verbal relationship with my daughter but this caught me off guard. I immediately regretted my tone and saw a hint of hurt in her face.

Thankfully, she remained calm.

"Dad, I get it. You're frustrated. But this trip is supposed to be about fun and relaxation. You are never going to be able to relax unless you get rid of that pent up... stuff. Trust me on this, okay? I'm not a little kid. I know about things too."

I, of course, knew she was right, it just wasn't the thing you wanted to hear from your kid when you are already in a bad mood.

"I'm sorry, you're right," said with a sigh. "The last couple of days have been something else. Certainly not what I am accustomed to."

"I know. I also know that some of the girls were teasing you yesterday at the beach, trying to literally get a rise out of you. I actually said something to them and they said they won't taunt you any more. Unless you want them to. I mean, I bet a few of them would sleep with you if given the chance. This morning really just confirmed that."

"What?"

"Dad, you need to get laid!"

"Brie, we have an extremely open relationship. I am glad we do and I am glad we have always been so up front to each other about everything. But, I think this may be crossing the line."

"You might be right." Brianna turned away and started walking to the door before turning around and addressing me with one last statement. "I'm going down to breakfast. You should join me. I'm sorry if I made you uncomfortable. You might be right with what you said. Then again, I might be right too." She opened the door and left.

------

I didn't join my daughter for breakfast. I instead went to the fitness center to try and work off some of the pent up "stuff" that Brianna had been talking about. Yes, I realize that you cannot "work off" full balls but I am a firm believer that you can work off the tension and emotions that were otherwise causing my issues. It went well too, a bunch of miles on the treadmill, a bunch of heavy things lifted. I can't say that I felt great, but at least my body was distracted.

I ran into Heather as I left the gym. She surprised me when, even though I was completely gross, she greeted me with a quick hug and another kiss.

"Busy day today. How about you, what are you up to?"

"Not sure, honestly. May just head back to the beach," I responded.

"Oh, yeah, speaking of which, I saw Brie at breakfast and we agreed to do her bikini wax today. How about I groom you up too?"

"You're on vacation. I don't want you to have to work."

"It's no problem, I am glad to help. She gave me her room number, why don't you meet me there in about 30, okay? It will be easier to keep everything in one room."

While I didn't relish the circumstances, I did want to spend as much time as possible with Heather so I rushed back to my room and showered for the second time before heading over to meet her.

The security latch held the door open once I got there so I just walked in and was greeted by Brianna in the short hallway entrance to the room. She was checking herself out in the mirror, completely nude, pre-wax.

"I should at least leave something, right?" She was speaking directly to me though still probing her pubic growth in the mirror.

"Wrong guy to ask, honey. Wrong relationship, wrong generation."

I caught the reflection of her sticking out her tongue at me in the mirror as I walked around the corner to greet Heather.

"So, where are we doing th..."

I cut myself off in mid sentence when I caught a visual I wasn't expecting; Tiffany, on the bed, fully nude, spread eagle and legs pulled back with her hands, a very nervous smile on her face, a single teer dripping down the side of her eye, one side of her spread vulva bright red... but completely hairless.

"Okay," Heather said to her, "You know what it feels like now. Not so bad, right? Do you want to finish it up?"

"Yes, let's do this," was her reply in a quivering laugh.

"Mark," Heather instructed me, "hold her hand. Give her something to squeeze."

Tiffany, who had been pulling back her legs like she was giving birth let go with one of her hands and reached out to grab mine. It was obvious that she needed some emotional support so I did as I was told and also, at Heather's instruction, grabbed the leg she let go off and pulled it back.

"Okay, this one is going to hurt like the last one but we'll make it quick."

Heather applied the warm wax, a cloth strip and yanked. Tiffany squeezed my hand tight but nothing so much that I legitimately thought she was in real pain.

"Great job," Heather said in a calming, professional manner. "Time for your butt. For this it will probably be best if you get on all fours."

Tiffany did as she was instructed and Heather, comfortable with drafting me as her assistant, explained that it would be my job to hold her young subjects ass-cheeks apart as to give her the maximum workable area. Of course I looked at the subject while I was doing so and was greeted by a browned patch of skin that wanted to wink at me.

The wax went on, the wax went off. Tiffany gave a sigh of relief when told the waxing is done.

"One last thing though," Heather informed her. "Sorry kiddo, you might think this is the worst out of all of it." While Tiffany repositioned herself onto her back, she called me over to her little work station and gave me my instructions. I was a bit shocked, a bit nervous but Heather assured me it would be for the best and suggested I do it as quickly as possible.

"Tiffany," I explained, "Heather wants me too put this on you." I held up a bottle of post wax balm.

"Yeah, I heard," she responded with a smile. I obviously hadn't thought about the fact that we were standing right in front of her but it was also my way of talking through the process. "Are you okay with this?"

"Yeah, it's fine."

I asked Heather if she had a rag or something to use but she instructed me that it would be too abrasive on the extremely sensitive skin. "Just use your hands," she instructed, "and be gentle."

Tiffany pulled her legs back and, one more time, brazenly exposed herself to me. For my part, I loaded some of the balm on the palm of my hand and fingers and gave myself a little internal pep talk to psych myself up for the situation. When my hand touched her skin her reaction was not that from a porn. She did not moan, she did not "ooh" or "aah." She screamed.

"Holy shit, that burns!"

Tiffany clamped her legs together so hard and so fast that she literally yanked my hand down and pulled me forward.

"Tiff, honey, you need to let him continue. The burning will go away quickly," Heather immediately called over.

After a second of contemplation and catching her breath, Tiffany opened her legs back up (though tentatively not as wide) and I finished covering the entire area with the balm, my fingers weaving in between the folds of her lips and across the pucker of her asshole, leaving the entire region a glossy shine. I could tell she was having conflicted feelings as to the gentle contact. One one hand the skin was still tender, on the other hand, I watched her eyes go wide as my hand crazed across her exposed clit.

"Okay, Mark, now gently blow on it."

Oh, for God's sake.

I bent down and gently blew cool air across the entire region. This time the response was a bit more positive. The balm had a pleasant smell and I could admit that being so close was doing a bit for me in the way of arousal. Concerned as to what state I would be in I was relieved when, after a moment, Heather had me stop and moved me to the side while she held up a mirror for Tiffany to be able to thoroughly see her newly groomed pussy.

"Was it worth it?"

"Yes! Oh, my God, it is so clean and smooth," Tiffany exclaimed. "Hurt like a bitch but worth it. Thank you so much!"

Tiffany popped up and wrapped Heather in a hug.

"Glad you like it. Tell your friends! My shop and studio aren't too far away from where you live."

Brie went through her process and, whether it was the forewarning she had gotten from her friend or she was just tougher, seemed to handle it pretty well. Heather did not have me rub any balm on my daughter, Tiffany did that while the girls giggled and laughed and, after they were done, they went back to Tiffany's room to "air out a bit more." Both girls were left with two finger wide landing strips right at the tops of their pussies, clean and neat and a reminder that they were women, not bald like little girls.

------

Once they were gone, Heather had me strip down and prepare for my grooming.

"I actually set you up for that, sorry if it made you uncomfortable."

"Set me up for what?"

"Putting the balm and blowing on Tiffany. I would normally do that myself in the salon. The reality is that she and Brie thought that it would be funny and I decided to go along. Call it my own mid-life crisis; trying to be "cool" instead of the adult in the room."

"You're serious, she and Brie wanted me to have my hand on her crotch?"

"You have to know she likes you. Tiffany that is."

"Yeah, Brie has mentioned that over the years. Can't say I know why. I am just an average dad."

"Oh, don't sell yourself short. And, don't discount a girls crush. It means a lot to them while it is happening."

Unlike the wax jobs, where the superfluous hair was all caught up in the sticky wax, since Heather was going to be using clippers on me, she had me just standing on a towel to hopefully catch everything.

"So, what do you want here," she asked me as she gazed inquisitively at my junk.

"What do I want? I think you are forgetting why I am here. You and Brie were the ones to insist on this." I was practically laughing at the situation as this was so far out of my lane of normal life.

"I see your point. Well, as long as you are good with it, I will clean you up to quote-unquote-ideal from a woman's point of view, okay?"

"Hey, you're the pro."

Heather got a chair in order to get her face down to a lower level with a more direct viewpoint and, after a moment of additional inspection, started clipping. When I had agreed to this I was not oblivious to the fact that, in order to groom me, Heather was going to be handling my penis. I got it and I knew that I could be an adult about it. What I had not thought about were the other factors that would possibly affect me: I was tired, I had blue balls and I had just been rubbing the most intimate part of an attractive, younger woman. Plus, the buzzing of the clippers themselves seemed to be at a frequency that turned me on. In short, I again got hard.