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.
