The following story is a true life adventure. I did not change the names of the people in this story since it took place so long ago. All characters were over the age of 18 at the time of the wedding.
As we all know, destination weddings can be a double edged sword. On the one hand the cost and hassle of traveling to a unique location for a destination wedding can be expensive, but on the other hand it can also offer some great opportunities for sexual adventure. I was about to embark on the most memorable wedding experience of my life. My name is Jimmy.
My friend Stan and his girlfriend Kathy decided to get married at an expensive resort in Cabo. He invited me to the wedding but also wanted me to keep an eye on his eighteen year old sister, his fifty year old mother and his sixty nine year old grandmother. Even though I had not met any of these women, I agreed to keep an eye on them. I had no idea what I was getting into.
The wedding couple decided to hold a get together cocktail party on the first night at a beautiful location on the beach. Stan introduced me to his eighteen year old sister Lilly who just recently graduated from high school. His mother Janice was a fifty year old recently divorced attorney. Stan's sixty nine year old grandmother named Cheryl was a very attractive marketing professional who was just recently widowed.
I commented to Stan on what an attractive family he had. The three women laughed and enjoyed the compliment. Stan had no idea what nasty thoughts were running through my mind for his younger sister, his mother and his grandmother this weekend.
I was twenty eight years old at the time and had been with a lot of women. I particularly enjoyed older, more mature ladies, but I still had a craving for teen pussy. This wedding offered me the opportunity to put three notches on my belt with women from one family.
My buddy Stan had no idea that I was going to violate every woman in his family except for his new bride. I couldn't guarantee that I wouldn't also try to defile her if given the chance. Years earlier I had seduced a bride on her wedding night, while she was still wearing her wedding gown. She wasn't my bride. The groom had sloppy seconds with his new bride on their wedding night after I had totally pillaged her pussy. That's how much I love pussy. I am shameless.
The pool area at the resort was magnificent. There were two large pools, a very nice hot tub, and multiple swim up bars. While the wedding party was preparing for the big event, I decided to go down and hang out at the pool and keep an eye on the female family members that Stan had asked me to chaperone. I fully intended to keep more than my eye on these three vulnerable generations of ladies. I had a secret for all of them.
Stan introduced me to one of his family friends at the pool. Wallace was an impressive black guy about my age who had been a friend of Stan's family for years. Wallace played basketball with Stan in college and was still in great shape. He got a lot of looks from the white ladies at the pool.
Wallace and I were sitting at one of the swim up pool bars when the three women arrived and joined us at the pool. All three ladies gave Wallace a very friendly hug when they arrived. I found that interesting.
The teenage girl Lilly, was wearing a very revealing bikini top holding her ample firm teen torpedo tits, and a thong bottom with her ass cheeks on total display. Fifty year old mom Janice was wearing a very sexy high waisted, two piece bright purple bathing suit. The grandmother Cheryl was wearing a very sexy one piece, cut very high on the legs. I was wearing my traditional surfer swimsuit, and my new black friend Wallace was wearing a black speedo showing off what appeared to be a very impressive package.
The ladies took notice of Wallace's large bulge, especially mom Janice and grandmother Cheryl. Lilly didn't care much for the speedo style but she couldn't take her eyes off his cock. I suspected that there was something going on between Wallace and these three women that I didn't yet know about. I would soon learn about the family secret.
All three women were very friendly while we were chatting with them at the pool bar. Janice and Cheryl seemed to always be touching Wallace. I noticed that Janice and Cheryl had their hands on Wallace's upper thighs, getting very close to his huge package.
At one point Lilly got up to go to the restroom and Wallace gave her exposed ass a hard slap leaving a distinct red hand print on her tender white ass. All the women laughed. It was a bit awkward for me, but I also found it very interesting and arousing.
Janice and Cheryl were also constantly touching my arms and thighs while we sat at the bar chatting and getting drunk. I had my eye on both of them. I was in the mood for some mature pussy. Wallace pulled me aside. He gave me some background on the family.
69 year old Cheryl was a widow. Apparently all three women inherited a lot of money when Cheryl's husband Chuck passed away. He was very wealthy, lived a swinger lifestyle with Cheryl but was also an adventurous sex addict.
He was beaten up by a jealous husband who found out that Chuck had been tying up and molesting his kinky wife twice a week for years with her full consent while he was out playing golf.
Apparently the husband came home early one day with a couple of his golf buddies after a bad round of golf. They walked in the house to find his wife bound and gagged on all fours with Chuck ass fucking her in the middle of the livingroom. The husband and his friends beat the hell out of Chuck and then gang fucked the wife for revenge at the husband's request. Chuck later died from his injuries.
He and Cheryl had also been into the swinging life style including bondage and role play. Cheryl's daughter Janice was also involved in the swinging lifestyle. Apparently being kinky runs in the family. We would later discover that young Lilly also had a kinky side.
Wallace then shared with me the family secret.
Wallace said he fucks both Janice and Cheryl on a regular basis. Both of them crave big black cock but neither one knew he was servicing the other. High drama for sure.
Stan would be pissed if he found out his trusted college buddy was banging not only his mom, but also his grandmother and potentially his younger sister.
Wallace was a shameless sexual beast who loved to let white women use his big black cock for their personal pleasure. He was a human dildo for multiple women. He considered himself to be a very generous man by sharing his big black cock with mature women so they could fuck themselves to orgasm. A true humanitarian for sure.
The only reason he had not yet tried to fuck Lilly was that she was underage. She was a high school cheerleader who had just graduated a few months earlier. Lilly was tall, blonde and loaded up top.
She had just turned 18 before the wedding trip and Wallace was going to use this wedding opportunity to take her eighteen year old virginity and fill her young, tight pussy with hard black cock. He was making the assumption that she was a virgin. He would later have his doubts.
