Red Eye Flight
I boarded the aircraft with the two men that would be the pilots. I was looking forward to having the whole cabin to myself and getting some sleep. At the last minute we were informed by the company that we had a VIP onboard. This happens from time to time, employees of our company catch fights with us for their vacations, free flying. But they never called them VIP so I figured this person must be a high level employee or maybe one of the owners of the company. As we prepared for takeoff I went back to introduce myself. To my surprise it was an attractive older woman that I did not recognize. Her name was Abby, tall, skinny, flat chested, grayish blonde hair, and nice smile with warm brown eyes. I would guess her to be in her late fifties. She was very well educated and I could tell she was very wealthy. She asked me to sit with her and keep her company. After we got in the air I made both of us some drinks and we started talking. We hit it off almost immediately, we were laughing and having a great time. Our conversation started pretty tame but got pretty raunchy the more we talked. Then out of the blue she asked me about the mile high club and if I was part of that. I thought it best to play stupid and told her I did not know what that was and I was thinking that Abby would launch into some sex story, actually I was hoping. She explained to me what the mile high club and that she had always wanted to join in. Stupid me was still waiting for a story to start about her and her husband (she had a massive wedding ring on). Abby looked at me right in the eye with this very sexy look and asked "Are you game?" I was taken off guard as the last thing I would think that this woman would want would be sex. I stared at her, her smile and look in her eyes made my cock hard as steel. This woman wants to fuck me right here right now. I have never fucked an older married woman before, I have always went for the young hot single slutty girls, but I am always up for something new and it has been a few weeks since my last fuck. We embraced and started kissing passionately, our hands exploring each other. My hands made their way up under her skirt and around her panties to her super wet cunt. We both stood up and Abby pulled up her skirt and took off her panties and flipped up the armrest and laid across the four seats with her legs open. I took off my pants and knelt down and buried my face in her golden brown untrimmed snatch. It only took about two minutes for me to bring Abby to orgasim, and it was a big one. She bucked and screamed and locked her legs tightly around my head. She said it had been a while for her and she needed that. Now it was my turn and I moved up and plunged my cock deep inside her. Her pussy was not the tightest I had ever been in but it not the loosest either. She was a good fuck, she was meeting my thrust and I was really putting that old pussy threw its paces. After several minutes my balls were boiling and I buried my cock as deep as I could get into that pussy and blasted her womb with a massive load of cum. After laying limp inside her sweet pussy for several minutes I pulled out and sat in the seat with legs on me. Abby laid there enjoying the afterglow. I gently played with well fucked pussy smearing our cum around her bush. After about fifteen minutes my cock hardened and was ready for another round. So I moved in and fucked Abby again. We both came after three minutes of fucking. She had to go clean up. Came back and laid down across the seats very satisfied. She told me that had to be the best fuck she had ever had in her life. We fucked two more times on the plane. When we landed back in the states, she had to catch a commercial flight to her home city but it had about six hours to kill. So we got a hotel room near the airport and fucked like teens till her flight. That old lady surprised me with how much cock she could take. Several months passed since I fucked Abby. Then our company was having a summer BBQ party at the owners estate. During the party the owner was mingling with everyone. He came up to me, he and I knew each other, and introduced me to his wife, Abby. I was shocked to learn that it was my bosses wife that I fucked that night on the airplane. We both played it cool. I guess it kind of pissed me off that she knew the whole time who I was but she never told me who she was. A little later I ran into her inside the house, we were alone. She kind of giggled and laughed and tried to play it off when I quizzed her about what had a happened and why she had not told me that she was my bosses wife. I got even more mad and took her to bathroom. I pushed her against the vanity, she spread her legs as I pulled her skirt up. I pulled her panties to the side and unzipped my pants and pushed my cock into her. I grudged fucked her right there in her own house. She came hard and as she did I planted my cock so far up her and drained my balls. I was so deep in her that I was afraid my cum would shoot out of her nose. She again told me that was again one of the best fucks she ever had. I told her to fuck off. I wiped my cock off on the hand towel and walked out of the bathroom leaving her there with her pussy full of my cum. I left the party and figured I would get fired in the next week or two. I never got fired and I never saw Abby again. All I have to say is be careful who you fuck.