Single Male Chaperone

Part 1:

Basically, you have to believe in wild, ridiculous, "well-it-could-happen" types of scenarios to believe this story.

That said, it did happen.

The setup:

At 41, I was the sole male chaperone for a girls trip to Cancun.

20, 18-year-old girls.

3, moms. 2 of which divorced and single. 1 of which had been flirting with me for years even though she was the only remaining one married.

And me.

41 years old. 6' tall. 185lbs. Decent looking to the population in general.

I'm Mark Simons, my daughter is Brianna (Brie). I am the young dad to a wonderful girl who has great friends. And even though those friends used to be little girls and, though the time went in the blink of an eye for an adult, those girls were now women... and women are very different than girls.

We had booked a middle-of-the-road, adults-only establishment, a condition the moms actually insisted on. If we were going to be going on vacation with the girls they wanted to enjoy the fact that we were no longer parents to little kids. The girls couldn't care less anyhow. "We're not kids anymore," they all opined. Though, as a parent it can sometimes be hard to get over that idea.

The resort, like so much of Mexico, was a fantastic value for our American dollar. I am told that the reviews said the grounds were clean, the staff was friendly, the food and drinks were plentiful and all-included. We let the girls do the overall planning with the moms getting the final approval. Of course I could have been more involved in the planning but the pics I was shown looked fantastic and I trusted my daughters judgement.

All the parents had made deals with the girls that they were allowed to drink while on vacation (18 is the legal drinking age though even that is loosely enforced) yet had to stay on the resort grounds if doing so. The girls, again, couldn't care less. For many of them it was their first time out of the States, first time in the Caribbean, first time vacationing as an "adult."

The room situation, on the basis of cost, was 4 girls to a room (5 rooms) and 2 parents to a room (2 rooms).

"We could squeeze into one room as well," Gina (the mom who always flirted with me) said with a coy smile. "It might go over better since we are making the girls share."

Thankfully, I still had my head about me and knew where she was heading with her line of conversation. "Well, the beauty of being an adult and the one paying is that I get to make rules that aren't necessarily fair but to my benefit. I think we would all be much better off in our own beds. One extra room won't kill the budget."

Thankfully, the other moms agreed with me.

It wasn't to say that Gina wasn't attractive. Quite the opposite actually, she was a beauty. Each of the moms was quite good looking. My concern was that she was married and, since my wife died, I admit I hadn't done much in the way of dating.

"You've gotta' get out there again," my daughter would tell me, almost pleading with me to go out on some dates.

Honestly, she was right. Though, while I am not sure there was ever one specific reason why, I just didn't.

-----

I had an inkling the trip was going to be a bit wilder than I had originally planned when I helped Brianna get packed.

"What's this?" I asked as I held up a tiny lycra g-string.

"One of my suits."

"Pretty small."

"Yeah. A few of us ordered them and figured to give them a try. We figure the less tanlines, the better."

"Does it have a top?"

"Not that one," she answered matter-of-a-factly. "But I am bringing a total of 3, two of them have tops, and the girls all agreed to trade suits so we can have a lot of options for sharing and mixing-and-matching."

"You all wear the same size?"

"Well, obviously, no. But suits are stretchy and there are enough options between all of us that we probably won't go a day wearing the same thing."

"Or, apparently much it all," I said sarcastically. "I guess we will need to pick up more sunscreen."

Brie grabbed the scrap of cloth out of my hand and stuck her tongue out at me in a joking mock. We had a great relationship.

It wasn't as if I didn't know she didn't wear thongs and other skimpy underwear already. Heck, I did the household laundry. I also knew the resort policy was "toplessness is not sanctioned though widely tolerated/accepted." It's just that one of the problems with raising your child in a body positive manner is that sometimes they actually listen to what you say.

------

The travel down was typical. The girls were all squealing with anticipation while the parents tried to keep their volume down for the benefit of the rest of the plane. When we walked into the big, beautiful entry of the resort I almost started squealing with delight myself. It was more fantastic than I had pictured it and perfect for someone who hadn't been on an adult vacation... ever. While the resort was relatively empty (we got in quite early and were told that it would fill up over the course of the day with other travelers) I could already sense the energy that it held within its walls.

As it turned out, the adult rooms were actually adjoining and the moms (Gina, Melanie and Sara) immediately declared that the door between should never be shut over the course of the 10 days we would be vacationing.

10 days.

I hadn't had 10 days off in a row since before we had Brie. Sure, we had gone on vacations, mostly with her sets of grandparents, but nothing more than 6 nights. This was 9 full nights in paradise and I was looking forward to every moment of it.

The moments started immediately when the moms each changed into their bikinis and insisted on doing 2 rounds of shots to "get the party started."

The moms:

Gina - Mother of Brittany and a 5-year-old son I did not know. 47 years old. Married. Extremely good looking. 5'3" tall. Probably about 110-115lbs. Rock hard abs and an overall athletic, not very curvy, build. 365-day-a-year golden spray tan and blonde highlighted light brown hair that was very obviously professionally done. Measurements came in at an estimated 28-24-30. She informed me as she pulled on her bikini top, with not a care in the world that on day 1 she was topless in front of me, that she was getting implants in 6 weeks so she would "no longer be shaped like a boy" and was only disappointed that she hadn't planned them sooner to be able to "show them off to me."

Melanie - Mother of Emily. 42 years old and the closest in age to me. Most typical "mom" of the group. Had 3 kids and Emily was the oldest. Youngest was 8 and she informed us prior to the trip that she had a bit of trouble losing the final bit of pregnancy weight. 5'5" tall. 135-140lbs. It was obvious she was a looker in her younger years but had somewhat fallen into the tedium of middle age, marriage and parenthood and was a bit more plain in her appearance. Measurements estimated at 34-26-38. Melanie did not change in front of me, but did make a quick appearance in her run-of-the-mill bikini when summoned and looked pretty darn good to my eye. Yes, it was obvious her breasts were a bit smaller and "looser" than they once were and she carried a bit of a baby paunch, but her face was kind and warm and inviting and she had a full set of lips that were fantastically sexy. Melanie had finalized her divorce not 6 weeks prior and informed us that she was "ready to have some real fun after all the bullshit" she had been through.

Sara - Mother of Priya. Sara was a medium-skin-toned Indian woman whose name was not particularly befitting of how exotic she was. 45 years old, 5'7" tall, voluptuous. Always has called me "Honey" or "Sweety" when we saw each other. Sara changed into a tiny, string, thong bikini that brazenly flaunted the curves of her body. Measurements estimated at 44-38-42 of pure sex. Her breasts were large and full and barely covered by the tiny triangles of her top, her hips were wide and, though she was heavy, her skin was smooth and without a hint of cellulite. Her bikini bottom was so small it gave evidence to a professional wax job and her skin glistened even in the artificial light of the room. I had never seen Sara not done up in full makeup and dressed to the nines and her gold, sequined bikini and accenting wedge sandals continued the image she had crafted for herself. Which was, in essence, she was hot and she was worth it. Sara, was my roommate for the next 10 days and I worried myself with how I was not going to offend her with what were most likely going to be constant erections.

------

After shots we went down to the pool and found that the girls were already there and already enthusiastically drinking their first round of drinks at the poolside bar. Each girl was fully covered in a relatively modest bikini ("cheeky" bottoms and string tops at most daring) and I figured that each of them, including my daughter, were waiting to absorb the overall vibe of the resort before doing anything a bit more daring. While the moms and I had agreed to give the girls their space for the majority of the trip, it did seem appropriate to at least have a first drink with them.

Drinks in hand, we toasted to our vacation and threw back our drinks. Being the only male, having just chugged my drink and never one to be have particularly showy in front of my daughter and her friends previously, I got the loudest reception.

"Mister Simons!"

"Whooooo!"

"Part-aaayyyy!"

It was pretty shrill and loud and it was then that I realized I had to lay out some new suggested ground rules. Thankfully, they were well received.

Nobody was to call me Mr. Simons anymore. Each of the girls were 18 and we were on vacation. Instructions were made to call me Mark. Gina, Melanie and Sara all followed suit with insisting on first name greetings.

I made the suggestion that the girls make an effort to meet and mingle with other guests in the resort. I gave the reminder that we were at an adult resort and "adults" did not tend to roam in packs of 20 girls. Good things could come from opening their eyes and learning about other peoples lives and experiences.

Hand-in-hand with 2, do not go off with strangers alone and ever be outnumbered in a group.

We eat dinner as a group each evening.

That was it. Of course, I had already talked to Brie about knowing her limits when it came to alcohol. While we had never lived in a dry household and she was allowed to have a drink periodically, the unlimited access to alcohol and bartenders that had no qualms on overserving was something that gave me pause when it came to how to guarantee the trip was a success. At a certain point, however, they have to make their own decisions. At least I would be generally around if there was any fallout.

------

I excused myself from the group and set up camp in a poolside chair that seemed destined to get a lot of sun over the course of the day. Eyes closed, I felt like I was about to doze off when my siesta was interrupted by a familiar voice.

"Mark, honey, do you have sunscreen on? I don't think you are going to want to ruin 10 days by getting fried on the first morning."

Sara and Priya were standing over me. Sara's gold sequins sparkled in the sun and reflected onto my body like a disco ball. Priya's bikini, though a crocheted style, was not much larger than her mother's, but more appropriately sized on her thinner, teenage body.

"You're right. I should run up the room and grab some."

"No worries, we'll take care of you. Stand up. Priya, you get his back."

I stood and each of the girls took dollops of sunscreen onto their hands and started rubbing it into my skin. Priya's job was pretty utilitarian, Sara was a bit more wandering with her hands as they slipped slightly under the waistband of my shorts.

"Why do you wear these massive things?" Sara asked as she was down in a squat position, her hands well up under the legs of my shorts and dangerously close to my inflating manhood.

"Why do I wear a swimsuit?"

"No, why do you wear this swimsuit? It's huge and probably leaves your butt looking as white as a dead fish."

I chuckled at her comment.

"I guess I just haven't thought about it too much," I responded honestly.

"Well, you need to start thinking about it. Everyone should pay attention to their appearance and do their best to look their best."

The ladies were done slathering me up and Sara cut Priya loose to go back with her friends.

"Thank you," I said as I went to sit back down.

"Oh, honey," Sara replied as she grabbed my hand and pulled me back up. "That wasn't free, you need to do me now."

Sara handed me the bottle of sunscreen and turned her back to me.

"I decided to give you a break this first time though and already did my front."

I put some lotion on my hands while she got a lounge chair situated, the adjustments causing movements and jiggling in her body that drew attention to just how little of it was covered and when she lay down on her stomach her large breasts, even though partially spread to the side of her body, levitated her torso above the chair.

"Make sure you get all of me, Sweety. Brown people burn too."

I took my time covering every square inch of skin that I saw and Sara invited application in areas that I had not necessarily seen previously as she spread her legs a bit and instructed me in no uncertain terms that her inner thighs still needed to be treated. I also took some time to open conversation as to how the decision was made to come specifically to this resort in Mexico.

She paused and sat up, inviting me to sit at the end of her chair, basically between her legs, and insisted on holding my hands for the duration of her explanation.

"I grew up in a wonderful household. We were wealthy and my parents spoiled me with gifts and displays of status and my mother always encouraged me to push for whatever it was that I dreamed. Did you know that I was a doctor? Well, am a doctor, was working."

"No, I did not."

"Oncology. I worked in a research practice that was part of the University. It was a wonderful 5 years."

Sara paused for a moment and smiled at me. She really was quite pretty. I was curious as to what she would look like not "done up." I could only assume that she was still very attractive and her body certainly wouldn't be any less appealing. I noticed that her bikini had shifted and a large portion of one of her areola was uncovered.

Focus, damnit!

"Anyhow, then I got married. I was surprised when my parents even suggested the arranged marriage. Especially my mother, she always struck me as such a feminist. Though, as it turned out, she was a feminist only for single women and she was very much a traditionalist when it came to me and marriage and the rest of my adult life. Anyhow, as I had had such a wonderful life till that point I decided to meet my future husband and hear out the plan. Honestly, it didn't sound so bad, I would still live a very upscale lifestyle but just would not work anymore. But, as soon as the ceremony was over things started to change. My ex was never physically abusive but he was very controlling. I had to be his trophy wife and that was it. I had to dress a certain way, I had to play a very specific part. Now, please don't get me wrong. I very much enjoy dressing up and looking nice. There would be no way that I would go through the effort if I didn't. What I refused to get on board with was that it was my duty to do these things as I was his wife, his possession. Once I realized that he could not care less about me as a person the marriage started to dissolve. Also, he would not allow Priya the same life my parents gave to me. He wanted her groomed to be a wife, not a self-reliant woman. And then, a few years ago, when I found out he was also maintaining a secret lifestyle that involved a completely second family, I decided to cut our losses. I got us out, with a major settlement of course, and started over. Priya still sees him, but I have made it very clear to him that I am the main directional force in her life if he wants to maintain a relationship with his daughter."

Without a care in the world, Sara let go of my hands and reached behind her back to undo and remove her bikini top. Her heavy breasts dropped a bit but otherwise remained full, proudly showing off two perfectly round, tan areola that absolutely absorbed the soft nipple they held. She shifted down in her chair, laying out in the sun, her large breasts shifting to her sides though still large enough to project forward. She opened her legs more and spread them to each side of me, her tiny bottoms quite obviously barely covering her pussy lips.

Jesus Christ! Did she want me to cum right then and there?

"Which brings us to this trip. A couple of years back I overheard Priya and a smaller group of girls here whispering about school and crushes and dreams, etcetera. It was silly school-girl chatter but it became obvious to me that the girls in the group were all incredibly naive when it came to what I consider to be a life fulfilled. Since that point I have made it my mission, and after talking to Gina, her mission too, to make our girls the most intelligent, informed, sensual, confident and empowered women they can be. There were a group of about 15 that we have been mentoring. Then with Mel's divorce it became obvious that she could use some work herself. And then you."

I had found myself rubbing her thighs, not with sunscreen, just rubbing. I believe that was her aim all along with the position of her legs, but it still nonetheless happened absentmindedly on my part. Her comment took me by surprise.

"Me?"

"Yes, you, Mark."

Sara sat back up, her breasts slowly swinging in front of her.

"Do you know how wonderful a job you have done parenting Brie? That daughter of yours is fantastic in every way. She already has all of the attributes that I was talking about before. She is smart, she is beautiful, she is confident."

"But?"

"But, in conversation with her it seems obvious that somewhere along the way you lost your way as a man and instead just became a dad. Your little girl is going to be out of the house in a few months and then what? Those things we want for our daughters? Those are universal. You too need to know that you are not just a dad, you are a fantastic man with value to the world. And, if I may be so bold, I think you could probably benefit from some time with a lady."

I admit I was a little embarrassed by her comment. How did she know about my sex life... or lack of sex life?

"So, is this what this is all about? This little display?" I gestured my hand over her body to bring attention to her nudity. "Are you trying to get me to sleep with you?"

Sara smiled.

"Oh, Sweety. This? This isn't for you, this is for me. I dress and undress the way I see fit and do it for me. If I want to sleep with you, don't worry, I'll just ask. If you decide you like me too then I think we can have a good time. In the meantime, I am just going to relax and enjoy life."

I got back into my chair and laid out for some tanning of my own. Thankfully, the combination of the sun, the drinks and that I was frankly too tired to really start to overthink her commentary meant I fell into a relaxing nap.

-----

I woke up and found that Sara was gone but I was actually surrounded by a few of the girls from our group. None of them had taken her lead in removing their tops but I did see that a couple of them had changed to more risque bikini combos with one sporting a full-on g-string bottom.

"Hey, welcome back." It was Tiffany, one of Brianna's closest friends in the group. "How are you feeling?"

"Relaxed. Seriously, seriously relaxed."

"Really? I am not sure you look very relaxed." Brianna had actually mentioned in the past that Tiffany had a bit of a crush on me but I never really thought about it until I looked and saw that she was staring directly at my crotch... and the crotch of my suit was very clearly highlighting an obvious erection that was straining against the leg of my shorts.