White Wedding Whopper

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.

The idea of fucking three generations of women from one family peaked his sexual passion. In hockey terms, he was going for the family hat trick by fucking all three generations of women. He was my new hero. He told me if I played my cards right I might have the chance to join him with all three ladies. That's exactly what I had in mind.

He then advised me, "Just don't let any of them figure out you are fucking the others."

Both Janice and Cheryl found it exciting thinking that they were the only one secretly taking black cock. Wallace knew that both Janice and Cheryl were kinky sex addicts just like Cheryl's dead husband. They were both very submissive. They would let Wallace do just about anything he wanted to do with them including gangbangs with his black friends.

It was the perfect plan. Janice and Cheryl had their sexual fantasies fulfilled on a regular basis with no strings attached and Wallace got to fuck both mature white women anytime he wanted. He did however tell each of them to keep quiet about their relationship. They both kept their big black cock secret to themselves.

Wallace and I agreed to start our sexual wedding adventure with the grandmother Cheryl. He invited her to join him at the hot tub that night and let her know he was bringing a friend and she was expected to put out.

She said, "Great, I'm looking forward to it."

In reality, she was looking forward to getting fucked by his big black monster cock. It had been quite sometime since Cheryl had felt his thick, hard, raging cock in her mature pussy. She had to rely on her huge black dildo that she kept in her nightstand at home that she used almost every day. She had an intense desire for big black cock that needed to be satisfied. Wallace gave her that secret satisfaction. I too had a secret of my own that both Wallace and Cheryl would discover later that evening.

Cheryl showed up at the hot tub right on time wearing a sexy two piece swimsuit. She looked great considering she was sixty nine years old. She was a little drunk. She had a deep rich suntan with large tits to go with her short, blonde, professional hairstyle.

She was pleased to see me. Wallace gave her a deep kiss and slid the straps of her top bikini top off her shoulders and said,

"Cheryl, please show our new friend your magnificent tits."

She lowered her top and exposed her large mature breasts with huge nipples. Wallace and I each pinched one of her nipples then pulled and sucked them until they were rock hard. She threw her head back in ecstasy and put her hands on the back of our heads as if she was breast feeding two young infants.

Wallace got up and locked the door to the hot tub area. Before getting back in the hot tub he pulled off his speedo revealing a huge hanging black cock. His black balls hung as low as the head of his cock. Cheryl gave the head of his cock a nice grandmotherly kiss and laid his cock on her face while she sucked his swinging black balls. She then put her hand up my shorts. Her eyes widened and she blurted out,

"Oh my God." She was the first in her family to discover my secret. She had just met the Big White Whopper.

I was blessed with an enormous cock. It was a source of embarrassment for me growing up but that all changed when I got to high school. The girls found out about my huge cock from my buddies in gym class.

I became very popular not only with the students, but also with a couple mature faculty members including the girl's gymnastics coach. Being a former gymnast herself she was incredibly flexible. I had no idea that the female body could be contorted into so many positions. She could literally cross her ankles behind her head or do the splits while sitting on my face or my huge cock.

That is how I developed my lust for older mature women. My big white whopper became a destination cock for a lot of women. I also considered myself a big cock humanitarian just like Wallace.

I stood up and said, "Cheryl pull down my swimsuit." She eagerly pulled it down and my cock sprung out hitting her in the face. Wallace was stunned.

"He said, "Dude, that is the biggest white cock I have ever seen." He gave me a fist pump. I was a match for Wallace's big black cock and I wasn't even hard yet. I would let Cheryl take care of that.

Cheryl sat in the hot tub holding two massive cocks that were growing larger in her hands. She worked both our cocks by stroking them from our balls to the tip. Both of our cock heads were sticking above the surface of the water. She was getting drunk and more aroused by the second trying to decide what to do next with our two massive cocks and balls.

Wallace and I sat on the edge of the hot tub and let her indulge herself with the two biggest cocks and sets of balls she had ever seen. We let our balls dangle in the water as she went back and forth sucking on both of our massive cocks. Cheryl wanted cock and I was ready to impale her with some big white whopper.

I laid on my back in a lounge chair and watched Cheryl mount up and cautiously work the head of my cock into her waxed mature pussy. The expression on her face was both pain and pleasure. I put my hands behind my head and just let this sixty nine year old kinky swinger grandmother fuck herself to multiple orgasms on my big white whopper.

She fucked me hard while Wallace shoved his cock in her mouth. She was almost out of her mind with lust. Wallace blew his load in her mature mouth and then left her alone so she could focus on fucking herself to orgasm on my white whopper.

I made her do all the work and finally gave her a deep cream pie in her mature pussy. I had never fucked a woman her age before that weekend but she had opened my eyes. I was hooked on senior pussy.

I now had one notch on my belt. Mother and daughter were next to be impaled by the big white whopper. Tomorrow mom Janice would get the same double big cock treatment as grandmother Cheryl.

Cheryl was very affectionate towards both Wallace and myself at the pool the next day. She played it cool not letting anyone suspect that she had drained two massive cocks the night before. We now turned our attention to milf Janice. She didn't know it yet, but she was going to be pushed to the limit tonight with two big cocks double penetrating both of her mature holes.

Wallace invited Janice to the hot tub that night and also told her he was bringing a big friend. She said,

"Oh, a big friend, well that sounds like fun." She laughed not knowing what was lurking in my pants waiting to assault her mature pussy. Both Wallace and I also laughed, knowing full well what was hanging between my legs ready to be unleashed on unsuspecting Janice. She was about to experience some pain, but also some pleasure. He could hardly wait to see how his fuck toy Janice was going to handle my oversized cock.

Janice showed up at the hot tub with a bottle of wine and three glasses. She was wearing a black bikini and mid high heel shoes looking totally ready to fuck. She was glad to see me. Wallace gave her a deep kiss just as he did with Cheryl last night. He reached behind her and pulled the strings to her bikini top letting it fall into the water.

Her big tits did not move. They were high and firm and real. Her nipples were rock hard. Wallace and I both locked on to a nipple and starting sucking. Janice was in heaven. She stood up and told us to take her bikini bottom off. We both pulled the strings on her bikini bottom and it dropped into the water revealing a nice shaved mature pussy.

She had the type of pussy that is upfront with easy access to her clit even while she was standing up. We both took turns licking her clit. Wallace then stood up and once again locked the door to the hot tub area. Janice was about to receive some cock.

Same as the night before, Wallace stood up and removed his speedo. Janice kissed his black cock head and gave it a little suck. She obviously was very familiar with Wallace's cock and loved it. She now wanted to see her next big surprise. Janice said,

"Okay big boy, let me see if Wallace was telling the truth." I stood up and said,

"Janice, bring your face closer, and slowly pull down my swimsuit."

She did as she was told. The base of my cock was starting to appear in front of her. She kept pulling my swim suit down expecting the head to pop out at anytime. It didn't.

After about six inches she started saying, "Oh my God, this can't be real." Wallace said, "Oh it's real baby, keep going."

She kept pulling down my swimsuit but it was still all cock shaft. No cock head yet. She couldn't believe her eyes and started to laugh. After nine inches and still no cock head she was starting to panic a little thinking what my cock might do to her delicate mature pussy.

After twelve inches my cock finally sprung out slapping her in the chin. She recoiled putting her hands over her mouth saying, "Holy shit." Wallace had earlier told me that Janice was submissive and likes it rough. He instructed her, "Janice, suck his big white cock." Once again she did as she was told.

She knew what she was doing. She was familiar with super sized cocks having sucked Wallace for many years. She lifted my cock and went right for my swinging balls. She let go of my cock and let it lay on her face while still sucking my balls. She was about to experience twelve inches of white whopper cock up inside her mature pussy. I was not going to be gentle with her. She had good reason to be nervous.

I laid on he same lounge chair where I had fucked her sixty nine year old mother the night before. I told her to mount me. She was reluctant. Wallace was growing impatient with her. Wallace put his hands under her arms, lifted her up and set her down on my hard, twelve inch whopper, facing me cowgirl style. She started to resist. To my surprise, Wallace slapped her across the face and told her,

"Take all of his cock you fucking milf. I have another cock just as big that I am going to put up your ass. Do you understand bitch?" She nodded her head yes saying, "Oh god."

Once again I just laid on my back with my hands behind my head and let this lovely mature woman fuck herself to orgasm on my big white destination cock.

Wallace positioned himself behind her and pushed her forward on my chest. I bear hugged her with my cock still in her pussy. Her mature asshole was now totally vulnerable for Wallace's assault. He spit on her mature asshole and worked in the head of his cock into her pink, delicate anal starfish.

She yelled out, "Yes, fuck me, fuck me."

Wallace replied, "You got it wrong bitch, you fuck us, fuck us. We provide the cock, you provide the motion. Move your fucking white ass and fuck us."

He gave her a hard slap on her white mature ass. It left a red handprint just as it had on Lilly's ass at the pool. He slapped her other ass cheek to even it out. Once again she did what she was told.

She worked us hard. She was bouncing, pumping and grinding her pussy and ass against our cocks sweating as if she was in a steam room. She was making so much noise Wallace had to shove her bikini bottoms in her mouth to shut her up.

She was now getting tired and worn out but we were relentless. We wanted to make her work and sweat and make sure both her mature holes would remember us for the rest of the weekend. We kept her going for another five minutes watching her sweat and moan while still pounding both her holes for our own selfish pleasure.

Wallace and I both decided to unload in her ass and pussy at the same time. We grunted like animals as we dumped our loads deep in her holes lifting her off the lounge chair with the power of our thrusts.

We had her stand up over me straddling the lounge chair and spread her legs so we could watch our loads drip out of her ass and pussy. Both of our massive loads dripped onto my stomach. We then made Janice lick up both loads off my belly and swallow. Janice was submissive for sure.

We had both conquered grandmother and mom. Now it was time to introduce young Lilly to the world of big black and big white cock. However, that new world would have to wait until after the wedding.

The wedding was perfect. It was a very nice ceremony on the beach. The wedding party looked great especially the bridesmaids. I would also eventually end up sharing my big cock secret with a couple of the bridesmaids before the weekend was over. However, now our focus was on Lilly.

The reception was a blast. Lilly was wearing a short tight skirt and high heels. She looked like she was dressed for high school prom. She was starting to get a little drunk and I noticed she was paying a lot of attention to Wallace. I wasn't the only one who noticed. So did her mother and grandmother.