A Weekend Away Opens Many Doors Pt. 01

I knew I was responsible for the divorce. Not because of anything I said or did but mainly because I hid my feelings for so long. She was OK with going to bed early, reading a book or watching a Hallmark movie. I wanted to go to nude beaches, do over night fishing trips, hang out by the pool naked, fuck in the hot tub.

Since I was 13, I had worked whenever I wasn't in school. I never figured out dating. It was basically going from one relationship to another, with long dry spells in between.

I would have been very happy continuing to have sex with her but I wanted her to open her mind and herself to experiences she could never wrap her head around.

When we won the lottery with a sizeable 8 figure cash prize and with our children now out of the house, all the old excuses for our differences went away but the differences remained. I did not argue or fight the splitting of our assets so I was overly generous in my initial offer and didn't push back when she asked for more. Whether it was out of spite or because her lawyer felt it was his job, I didn't care. I no longer wanted things, I wanted experiences.

The divorce had been finalized for about 6 months and I got a text from my cousin Natalie.

Natalie had been my wing man through the process. She had gotten divorced about 10 years before me, she left the house to her ex as that had been the source of many of their problems. They shared custody of their two sons, Danny (18) and Scott (20).

After her divorce she took a low level job with a large company and worked her way into management. Not C suite but she was well regarded and given opportunities to grow which she seized with both hands. She juggled this with always being present for her two sons as they grew up and taking care of herself as well.

About 5'-4" light brown hair that went blonder in the summer, she had always been pretty but in her mid 40s, with the confidence and the financial resources that came with all her success she was hot. Even when she dressed down to go a soccer game, the store or the gym, she was always well put together. When she dressed up, it was stunning. Sexy dresses, high heels, her long hang framing her face. She turned heads but none of that ever went to her own head.

She'd never had close friends growing up but once her sons were born, the moms of their friends were her friends.

But as my wing man, we'd get together for drinks, go to the beach, go to concerts, always with a mixed groups of men and women, some in relationships, some not. She reintroduced me to the single life as my own 'friend group' had become the husbands of my ex-wife's friends so I was starting from scratch.

One of her friends (Helena) worked for an airline and as a perk, she often got last minute tickets very cheap. They'd gone to London, France, Madrid, Miami, LA, etc. Always at the last minute and as a result, it was usually a motley crew on the trips based on who was available.

The reason for her call was she was to ask if I had any plans for the weekend. Helena had secured 6 tickets, they were going to Cancun. So far it was Natalie, Helena, Maria and me if I was interested. She was making more calls about the other two tickets.

I answered, only half joking, that if it included those three gorgeous women, there was nothing I couldn't cancel.

I asked where we were staying and they replied that they hadn't booked the hotel. I offered to take care of that. Natalie said that's great, just let us know what we owe. I replied that I was taking care of in gratitude for all the support and friendship she and her friends had provided. While she pushed back, I insisted and said don't bring money. I won't accept it.

We agreed to meet at the airport Friday morning. Over the course of the week, there were several group texts back and forth and it was still undecided who the 5th and 6th would be. Being graduation party season everyone had obligations they couldn't get out of.

On Thursday, Natalie texted that they were out of ideas, she wondered if we minded that Danny and Scott, her sons joined us. I reminded her that the resort I'd booked was an adult only all-inclusive. She answered that Danny, the youngest was 18 and it's not like we were going to Hedonism.

Everyone agreed that it would be fine and we were set.

Friday morning we met at the airport lounge and waited on our flight. The flight was uneventful and given the early hour, we all nodded off until we landed in Cancun. After checking into the resort, everyone was very grateful for me taking care of the accommodations to which I replied that it was the least I could do after they'd all welcomed me in to their circle.

The rooms were 2 adjoining suites each with their own private pool. The boys stayed in my room, the 3 ladies in the other.

We agreed that everyone would freshen up at their own pace and we'd meet by the swim up bar at the main pool.

The boys and I were ready in about 10 minutes. Only needing to grab our swim trunks, sunscreen and we headed out.

We got marked our territory with 6 chairs and headed into the pool. The 3 of us got rum punch and enjoyed the pool and relaxed. I noted that most of the crowd was my age or a little younger, in their 30's and 40's.

I asked the Danny, "So who's a MILF?" When he replied with Mother I'd Like to Fuck, I said "I'm 51, not 101!"

I said "I mean do you see any here?" I reminded him to keep his eyes open, "There's probably a few cougars here that would love to teach a couple studs like you a thing or two."

I told them to enjoy their youth while they're young. "Don't turn down any new experience, as long as no one is getting hurt, enjoy it and learn from it."

With that new found knowledge, I noticed both of them spending more time scouting the older, apparently single women instead of girls their own ages.

About 30 minutes later, I saw our three girls headed to the pool. Trying to tease the boys, I said "Wow! Check out these 3 smoke shows!" (Corny, I know but I was going for maximum effect).

They both snapped their heads around and saw their mom Natalie who I've already described and then Helena and Maria entering the pool. All 3 women had Mediterranean backgrounds and their rich tans and smooth skin underlined the fact that they enjoyed wearing little when out in the sun but were smart enough to take care of their skin while doing it.

There was no doubt all three women had lived a life that included giving birth but they were so confident in the skimpy bikinis that the small roll here and extra wrinkle there didn't detract from the whole package.

They waded over to the three of us and asked what we're drinking, Natalie admonished her two boys, saying "Don't over do it. None of your friends are here. You don't need to compete for who can get the sloppiest." Both boys rolled their eyes and when they looked at me, I did they same but in an exaggerated fashion that got a laugh from everyone.

I ordered drinks for the 3 girls and another round for the 3 guys.

We spent the afternoon enjoying the sun and the free drinks, occasionally dunking in the pool to cool off.

Now remember that these two women had essentially raised these boys as much as Natalie had. Carpools to soccer practices, birthday parties, school events, etc.

But away from home, with a powerful cocktail of pool drinks, the sun and exposed skin around us, Helena and Maria began to relentlessly tease the boys.

They wanted to know about who had been cheating on who, rumors they'd heard as moms about goings on at parties. The questions came rapid fire. The poor boys couldn't think of any acceptable answer fast enough before another question came on it's heels.

Natalie and I sat on our chairs, having worked in related fields, she was catching me up on few things at work when we heard Helena absolutely roar "I KNEW IT!" Helena and Maria couldn't control themselves laughing. Poor Danny looked like he was hoping the pool would open up underneath him and suck him into an abyss. Scott was grinning into the drink his was sipping. Helena and Maria excused themselves to go to the bathroom, leaning against one another as they walked because they we're still giggling.

When Danny and Scott came over to us, I asked what was that about. Danny mumbled "Nothing." Scott said into his drink,"Oh, it was definitely something."

Natalie and I looked at the two of them and she got motherly and said, "So what was it? Nothing or something?"

Scott started to speak, when Danny told him to shut his mouth but Scott went on.

Evidently, during the Inquisition that Helena and Maria just put Danny through, the question about a certain weekend came up. It had been at Helena' house when she was away. Her son had invited a couple friends over to use the pool. They brought their girlfriends and drank and ate and swam.

When they went inside, they split up, Danny and his girlfriend had stayed in the living room and were making out on the couch. One thing led to another and the two ended naked on the couch. It was a first time for both of them. After their clumsy romp, they got up and got dressed but noticed the combination resulting from their love making had stained the couch.

They scurried about trying to find a way to clean up their mess. But while is was faint, it was definitely still there. As a last resort, they flipped the cushion hoping no one would notice. Evidently Helena had noticed right away and grilled her son over it but whether it was outright cluelessness or covering for Danny, he insisted he didn't know what happened.

At this point, Helena and Maria were back from the bathroom and sneaked up behind Danny and Scott and dunked them both.

They both jumped up and turned on the ladies, pulling them under. Natalie and I laughed at their horseplay. I said "The adults are getting another drink, feel free to join us when you're done".

Natalie and I swam back to the bar and I could see a wrinkle in her forehead. I asked her "What's up?"

She answered "Nothing". Recalling our earlier conversation with the boys, I said "So is it nothing or something ".

Recognizing the recall with a slight grin, she said "I'm just hoping it wasn't a mistake bringing Danny and Scott".

I said, "Why? They're fine, they look like they're having fun."

She replied "It's not them, I'm worried about. When Helena and Maria and I go on these trips, we usually meet up with guys and have a lot fun".

The way she stressed the word 'fun' and raised her eyebrow above her sunglasses, I think I understood exactly what type of fun she referred too.

Stepping in front of her, I said, "Look, I don't want to cramp your style. After dinner, you three go your way, I'll come up with something to pull the boys another way and it will be fine."

She thanked me for the offer but declined and said "No, that's silly. We all came together, I'm sure I can get those two to their keep panties on for three days."

Danny, Scott, Helena and Maria came up to us exhausted from their play. I got them a round and we talked about our plan for the evening.

As we were talking, a couple of girls walked by with tiny little bikinis. To Danny, our conversation was non existent as his eyes followed their path along the pool's edge. Helena, not wanting to let him off the hook from the earlier teasing, said " Danny, if you manage to hook up with one them, please don't stain the upholstery again."

With a confidence that was non existent just 30 minutes ago, Danny replied "If I get with one of them, I'll tear that pussy up just like I did on your couch and won't care about the stains."

Natalie gasped "Danny!"

The rest of us laughed hysterically, as much at Natalie's reaction as we were Danny's bravado, but Danny fixed his gaze on Helena and didn't let go. Now it was her turn to feel embarrassed under the heat of his stare.

Feeling he'd won the point, Danny joined our laughter while Helena focused on the drink in her hand.

We decided on what restaurant we were going to that night as we walked back to our rooms. The boys and I were ready in about 30 minutes and texted the girls that we'd meet them in the lobby.

The three of us watched the world go by for another 40 minutes when I looked over Scott's shoulder and saw the three women. Playing it back in my head as i write this, it's in slow motion.

Natalie was wearing a tunic dress that hung off her breasts and gave no hint of the smooth tummy and nicely shaped hips and ass underneath. The eyes got a treat though as they scanned below the hem of her dress, catching her thighs a few inches above the knees and down her legs.

Everyone got changed in to their suits and we met at the pool outside the girl's room. We all got in and just soaked for a little while. It was quiet, suddenly no one seemed very talkative and we just let the water ease the effects from the alcohol we'd consumed over the last 12 hours.

We climbed out of the pool and toweled off. Helena went inside and came back out with a joint. She took my lighter off the table and lit it up.

Natalie, dropping back into mom mode and feeling like she needed to say something in front of her sons said " Helena, really? Where did you get that?"

Helena released the smoke from her lungs and replied "I got if from your guy Natalie."

Danny and Scott raised their eyebrows at their Mom. Helena passed the joint to Maria, who passed it the boys, it came around to me and I passed it to Natalie.

She hesitated a moment and finally said, "Fuck it, Mom's on vacation too!" She filled her lungs and the passed it back around.

Danny said he was going back in the pool, Scott, Helena and Maria followed. Natalie said she was done with the pool and was going in for another drink. I got up as well and said I'd refresh everyone else's too.

For the first time today, Natalie's face was fully relaxed. I smiled and asked her if she was feeling better now.

She grinned and said "Yes. I am. They're not babies anymore, they don't need me fussing over them anymore and I needed this weekend away bad, so yes. I'm feeling much better and thank you."

"For what?" I asked.

"For booking this place. For keeping not making feel like I was on my own when I was being nutty today. It's your getaway too."

With that she kissed me on the lips, chastely , certainly no tongue but it was warm and on my mind as I followed her back out to the pool.

Now I don't know if it was the alcohol, the weed, too much sunscreen, being surrounded by these beautiful women all day or the simple fact that I needed to get laid but it felt like that kiss lingered longer than is customary between family.

We stepped out onto the patio. The other four were still in the pool but had congregated at the far end.

Natalie and I sat in a pair of lounge chairs and passed a cigar back and forth. We talked about playing a round of golf this weekend as she had recently taken it up but had never played on a really nice course like the one we had access to at the resort.

When I stopped talking and was staring at the pool, she turned her head to see what had caught my attention. Helena was making out with Danny while Maria did the same with Scott. The women had their arms draped over the young men's shoulders and their bodies pressed together while the guy's hands ran down the women's backs.

We watched as first Maria, then Helena each dropped a hand down below the water line and the movement of their arms made it evident they were stroking the guy's cocks.

Danny's hands came up Helena's back and untied the strings to her bikini. She backed off his smooth chest just long enough to let the top fall to the water. She picked it up with her left hand and threw it onto the pool deck, never stopping what she was doing with her right hand.

Maria took off her own top and backed away long enough for Scott to get a good look at her tits as she added her top to Helena's on the deck. And then leaned back in to continue kissing.

I watched Natalie's face, getting ready to catch her if she she lost her cool and went after her sons, her friends or both. Feeling my gaze, she turned her head towards me but I couldn't tell what was going on in her head, so I asked "Want me to tell the to cool it so you don't have to be the bad guy again?"

She shook her head no and turned back to watch the four in the pool. As she watched, she turned her body on sideways to face the pool.

Seeing a space for myself behind her in the chair and remembering the kiss earlier I got up and moved to the lounge Natalie was laying in.

She turned her head to me, smiled and then went back to watching the action in the pool. As I laid next to her she reached behind herself, found my arm and them pulled my arm across her body, settling with her hand over mine on her smooth belly. Then she adjusted herself so that her back was pressed against my chest, her ass pressed against the front of my trunks.

I heard Natalie mutter something to herself and I asked her to repeat it, she said "I can't believe they're doing it." I asked "Doing what?"

She turned her slightly to me, still watching the foursome in the pool and told me the story,

Natalie started, "When we were in Miami last summer, two brothers around Danny and Scott's ages started hitting on us at the beach. We flirted with them, had some laughs. Said we're old enough to be their moms, they replied that that's what made the three of us even hotter."

"That night, we were at a club, Helena saw some guy that's evidently a big deal soccer player in Italy where she's from. She went up to him at his VIP table and started speaking in Italian and before we knew it, we were hanging out with him."

She continued "After the club started to wind down, the soccer player said he and his friends were going to a strip club where one of the girls we'd been partying with worked and did we want to come along."

Natalie reminded me "Of course, when we're on these trips, we never let the party end, so we got to the club with his entourage and headed for the VIP section."

"Just as we got seated, Helena pointed to the two guys we'd seen at the beach earlier that day. She asked her new friend, the soccer player, if she could invite them to sit in our section, to which he agreed. She made a beeline for them and came back with the two of them on either arm."

"The dancer's came through the VIP section and were a lot of fun to hang out with. They asked the two guys we'd brought over if they wanted private dances, to which they declined."

Getting a little more comfortable lying beside me, Natalie continued with the story, "I had always wanted to see this so I grabbed my wallet, pulled out a pile of cash and said to one of the girls, "I'll pay for them, but pointing to Helena and Maria, I told her that we wanted to watch."

The dancer got a big grin and asked "Are you their mom?" When Natalie said no, the dancer said "Too bad, that would be hot!"

They got to the section where the private dancers did their thing. The ladies sat together with the two guys across from them. The dancers worked themselves, it was obvious the guys were enjoying the attention"

Natalie, Helena and Maria turned into a bunch of rowdy construction workers, shouting cat calls at the dancers and the guys. Taking turns bringing more cash over to feed the energy in the room.

Helena leaned over to Natalie and said "I'm sorry for saying this but those two guys look just like Danny and Scott and I think it's making me even hotter" Pointing at one of the dancers, Natalie said that one looks just like Maria's and it's driving me crazy"

Maria said "Natalie, what are you talking about? I have a daughter, not a son"

Natalie stood up, looked at Maria and replied with a smile "I know." Natalie stepped across the room and interrupted the dancer that looked like Maria's daughter and took her hand and sat between the two guys.