A man gets some extra money and lives out a fantasy
Three generations of pussy
I made a suggestion that made my company millions of dollars and they gave me a $50,000 bonus. I spent hours and hours deciding what I was going to do with it. I finally invested $40,000 of it in my retirement account and decided to have fun with the rest. But how? My name is Bud. I am a 58 your old horny, divorced white male.
For years now I have had a fantasy that I decided to see if I could make come true while I am still man enough to enjoy it. The fantasy is to have sex with three women from three generations of the same family at the same time. I put an ad in the largest swingers on-line web site that said that I was looking to have sex with a woman, her daughter and her grand daughter at the same time. The grand daughter must be of legal age. I would invite them for an all expenses paid vacation trip to the Caribbean. I gave them information about myself. 58-year-old attractive white male, 6'1", 180 pounds and a 7 inch cock that was still good for several times a night. The ad ran for three months before I got a reply.
The reply was from Janet. She told me that she was 38 and her mother was 54 and her daughter was just about to turn 18. She said that they were from a large, loving and very incestuous family that enjoyed each other as well as others that they inviting to join them. The kids are introduced to family sex on their 12th birthday and everyone enjoyed everyone else as long as they were able to still do it. The oldest still active member of the family was Uncle John who is 79. She described themselves and sent nude photos of each. Her mother was Julie and her daughter was named Jane. They think that Jane's father may also be her grandfather but are not sure who the father is. Anyone who was going to marry into the family was brought into the family action before the wedding to make sure that there were no misunderstandings and that he or she fit in. She said that the trip sounded like a lot of fun and that they all thought that the sexual adventure sounded even better.
I corresponded with Janet three more times before I felt comfortable that this was honest and would work out. I told her that I wanted to start our trip on Jane's 18th birthday. Janet said that they had a big party planned for family and friends but had talked about it and would delay the party till after they got back from the trip. I was going to get to fuck Jane on her 18th birthday. Even though she was far from being a virgin it made me excited. My timeshare group has a resort on St. Johns Island. I went on line and was able to get a two-bedroom ocean front condo for three nights starting the day I wanted. I booked it. I booked the airline tickets for everyone. I was careful to book them in a way that if they were not used, the only way the cost would be refunded was to my credit card. I had heard to many stories of guys getting ripped off when they gave money to a woman who promised to come to him but kept the money and never showed up.
I kept in touch by both e-mail and phone for the next five weeks till the day of our trip. I boarded my flight and had an erection all the way there. I arrived at about 3pm, about three hours before the ladies were to arrive. I checked with their airline and confirmed that they had boarded their flight. That was a relief. I picked up the rent-a-car and went and checked into the condo. I was very pleased with it. It was very large and right on the beach with a great view of the sandy beach and palm trees. The master bedroom had a king sized bed and the other had a queen. The master bath had a large spa tub and a shower big enough for all of us at once. I headed back to the airport to pick up Janet, Julie and especially Jane. As they deplaned I was standing there with a sign in my hands with their names on it and a big grin on my face. They had seen my photo and came right to my sign and me. I dropped the sign and gave each of them a tight hug and a big kiss with tongue. Several people notice and had different reactions. We gathered their luggage and headed back to the resort. They were all even more attractive than I had expected from their deions and photos. They were all dressed in what I would call tennis outfits and they all made it a point to make sure that I saw that none of them were wearing panties and that they had all shaved their pussies like I had asked them to do. It was about 8pm and they had not been fed on the plane, just snacks, so we stopped at a nice seafood place on the way.
At 9:30 we got to the condo. It was already dark so they did not get a good look at the view but could see it a little and could hear the surf. I went back and got a cart to bring in their luggage. When I got back to the unit and closed the door behind me I found three naked women standing in front of me. A huge smile came to my face. The three of them came over to me and started to undress me. Shortly, we were all naked and they all kneeled in front of me and started to kiss, lick and suck my fully erect manhood. Everyone was pretty tired after traveling much of the day but they were ready to play. I told them that there would have plenty of time to do anything that we wanted to do, in bed and as tourists, but tonight I wanted to fuck Jane on her 18th birthday. I took Jane into the master bedroom and Judy and Janet followed us. Jane started sucking my cock. She was great at it and after just a few pushes I was balls deep in her mouth. Julie and Janet took turns eating her pussy till she had her first orgasm. Then they left together to the other bedroom. Still breathing hard, Jane climbed up on me and guided herself down onto my waiting shaft. She was so wet that she had no problem sitting all the way onto me the first push. She bounced up and down for several minutes and brought herself to a couple more small orgasms. She flooded us with her lubricating fluids. I stopped her and put her on her hands and knees and got behind her. I started pounding her cunt hard and fast. My balls slapped against her pussy lips. Soon she and I came at the same time. She spun around and caught the last blast from my cock in her mouth and then sucked my cock and balls clean of our cum till it started to go soft. Jane said that she would be right back. I assumed that she was going to the bathroom but she went down the hall to the other bedroom. A few minutes later when she returned I asked her where she had gone. She told me that she had gone to the other bedroom and rode her mother's and grandmother's faces sharing my cum with them. Then we then cuddled and went to sleep.
The next morning about 10am I woke with the sun coming in the window when I felt the bed move. I opened my eyes to find all three nude women in bed with me. They each gave me a good morning kiss and then told me to go over and sit in the chair and they would give me a little show. First I went to the bathroom to empty the nights worth of piss. Julie followed me in and stepped into the shower and kneeled down telling me to relieve myself on her. I aimed my piss filled cock at her and let fly. The yellow stream flew into her hair and on her face and ran down her body. She showered off and went back to the bedroom. I went to the chair. Julie reached into a bag that they had with them and pulled out three dildos. They all were on the bed forming a daisy chain sucking each other and fucking each other with the dildos. They didn't stop till they each had had an orgasm. They invited me back into the bed with them. They gathered around my cock and shared it. Taking turns deep throating my manhood till I came. Lastly they deeply kissed each other sharing my cum back and forth.
I ordered breakfast for the four of us from room service. Before long a young black man came to the door with our food. When I opened the door and he wheeled the food in he found three very attractive white women standing nude in front of him. His first look was that of shock but that was quickly replaced by a big shit-eating grin. Jane said to the others that he was cute. I tipped him $10, he put the dishes on the dining table and he left with a big bulge in his pants. Janet commented on the size of the bulge in his pants and asked if it would be ok to ask him to join us one time. Sounded like fun to me. I had noticed his name on his white server’s jacket so I called and asked them to have him bring up some more butter for our toast. I was surprised at how fast he got back to our room with the butter in his hand. The girls were still standing there nude and made kissing motions to him as he came in. I asked him what time he got off work and he said 7pm. I asked him if he would like to come back to the room then. "You bet I would" was his answer and I told him that we would see him then and he left, almost skipping down the hall.
We found out that there was a nude beach a ways down the shore and got a taxi to it, right after lunch at 2pm. We frolicked in the water and watched the others on the beach. There were black, white, young, old, fat and skinny bodies to look at. Many looked at us as I strolled down the beach with three attractive naked women pressed tight up to me. In chest deep water I fucked each of them. We got back around 6pm and cleaned the sand out of our ass cracks.
Promptly at 7pm there was a knock at the door. When I opened it, there stood Juan, the room service boy. He was about 5'6' and slim but muscular. He looked to be about 20. His skin was almost as black as charcoal. He was wearing loose fitting shorts that came just above his knees and a colorful print tropical shirt. He stepped inside and quietly, in heavily accented English, said. "My sister also works here at the resort, as a maid. I told her about you and she asked me to see if you would like her to join in with us. If you say no, we will understand." I replied, "The more the merrier. Go get her." He stepped out into the hall and waived. The cutest little black girl you could dream of hurried up to the door. She was about 5'2" with short curly hair. She was almost skinny but had good sized, well formed melons. Her skin was the same dark black as her brother's. She still had her maids uniform on but she had bought it a size or two small so it fit tight and really showed off her fantastic figure. "This is my sister Tanya. She is 16."
I told Tanya to go over to Janet, Julie and Jane. When they came together, the three started to feel Tanya's breasts and kiss her. She returned the kisses. Then they started to undress her. I took Juan to the side and took a minute and told him what I had in mind. He smiled and nodded. We got out of our clothes about the same time as all of the ladies did. Juan stood there in his glory. We have all heard the stereotype of blacks having the biggest cocks and I know that it is not always true but Juan could have been the one that got that idea started. He stood there limp but as big as I am when fully hard. And I'm no lightweight. He was very big around and I knew he was going to do some hole stretching in the next little while. I told Jane and Tanya to go 69 with Tanya on top and for Janet and Julie to do the same with Janet on top. It did not take long for them to get into it. Juan and I stood there and watched while stroking our cocks. As they came to full attention I could see that Juan was easily over 10". I reached for the KY that I had brought. I squirted some from the tube onto Juan's hand and some onto mine. We rubbed some onto our cocks but put most of it on the girls ass holes. We worked our middle fingers into their asses and then followed with two fingers. I nodded to Juan and we moved in and lined our cocks up to the girls ass holes. I pushed into Tanya fully, with ease, but Juan had more trouble working his huge member up Janet's shit hole. Janet screamed into Julie's pussy, partly in pain and partly in pleasure. Soon he was fully in her and we pounded their rumps while they ate each other. I loved the contrast as my white cock pumped into Tahya's black ass and Juan's black cock pounded Janet's snow white one. About every tenth pump or so we would pull our cocks out and Jane and Julie would take us into their mouths for several pumps and then it was back into the asses where they had come from. We continued our fucking, switching from ass to mouth and back again. I was the first to come. The first couple of spurts went into Tanya's ass. Then I pulled out and shot the last couple into Jane's open mouth. About two minutes later Juan did the same thing with Julie and Janet. The girls turned around and shared their prizes among all four of them. Juan and Tanya got dressed and he stood by the door with his hand held out a little just like when he delivered the food. I got the idea and got out a $50 and gave it to him and they left. That night the four of us shared the same bed. In the middle of the night I woke and felt that my cock was hard and pressed against someone’s ass. I spread her ass and slipped my shaft into her cunt and slowly fucked till I came. I did not even know who it was that I fucked. Then I went back to sleep.
The next couple of days went much the same with some touristing but even more fucking and sucking. When it was time to leave Janet gave me their address and invited me to come any time and get to know more of their family. She said that they would be very happy to get to know me. Very happy! I arrived home happy that I had another day to rest up before going back to work. The trip had cost me a total of almost $4,000.00 but I considered it money well spent.