Jack Wilson had never been in this position before and never thought he would be. He was the bottom half of a wonderful 69 with his wife Diana. This was not so unusual for them. What made today different was the cock he felt moving in and out of his butt. Also the cock sliding in and out of Diana's pussy was new. The sentences "Lick my pussy while that cock fucks me", "Get him wet before he fucks me", Open your ass up to this cock" had been used for the first time.
How did Jack Wilson, a completely heterosexual man of 55 years find himself in this position you ask? Well, Jack wondered the same thing as his mind drifted back to earlier that evening.
That Saturday evening he was looking through his wife's panty drawer. No, it wasn't anything perverted. Diana usually kept her diamond jewelry in the same drawer and he needed to take a couple of photos of the earring and necklace set he had given her for their 30th anniversary. His jeweler was going to use the photos to create and matching bracelet for their 35th anniversary.
He found the diamond set and took several photos. As he returned them to the drawer he saw it. He had seen it before but didn't know it was in this drawer. He knew he shouldn't touch it, but he was drawn to it. He remembered what she had done to him last time he touched it, but he couldn't stop. He picked up the small book and noticed there was no lock. He knew he had promised but he opened it. He opened Diana's diary.
OK, you are thinking, her diary, what's the big deal. Well, it is a big deal to Diana. Diana has kept a diary since she learned to write. There is a locked hope chest in her sewing room with 43 years of diaries inside. Her entire life is chronicled day by day in the pages of countless diaries.
The curiosity of what was written on those pages has driven Jack crazy for 32 years. His curiosity had led to his downfall 20 years ago. Diana had caught him reading an old diary and had exploded. It was a solid week before she would even acknowledge his presence. That first acknowledgment consisted of her pouring a pitcher of sweet tea on his head when he asked for a refill during a family dinner.
Jack had swallowed his pride and begged for forgiveness. After three more days of begging Diana finally forgave him with conditions. He had to promise to never touch her diary again. He had to agree to vacation at the Outer Banks of North Carolina instead of Myrtle Beach that summer. Finally, he had to agree to let her shave off his pubic hair and wear a pair of her panties to work on Thursday. She picked Thursday because that was the day Jack met his friends for racquetball after work. To say the least, it was a very strange day. A day his friends still tease him about to this day. The aftermath was not much better as the hair grew back. Hair stubble does not feel good on testicles. It was an uncomfortable couple of weeks, to say the least. Jack has never asked Diana to shave her pubic hair.
So with the wisdom of twenty years thrown out the window, Jack opened the diary. He quickly noticed the theme of her last entry:
June 21st
I had them all at the same time today. It felt so nasty and wicked but it also felt so good. I can see how women can get addicted to multiple men.
The three cocks are so different but that is what makes them so perfect. Black Beauty fills my pussy and Slim Jim fills my ass. JC is wonderful to just hold and suck. I especially like sucking it after it has been in me.
I think it is time to bring Jack into this nasty fun. He is a nasty boy. I think he will go for it with a little persuasion.
What the hell did I just read Jack thought to himself. Jack and Diana had a great sex life. They had been adventurous in bed but had never included others, never even discussed bringing others into their bed. Now she is having gangbangs. Jack knew this didn't make any sense. He had to read more.
June 20th
Dixie brought me off three times today. God, I love the vibrations on my clit.
Dixie had me so excited I had to get Slim Jim to fuck my ass. I think Slim Jim has my ass almost ready for JC. Once I know I can handle JC I am going to give Jack the surprise of his life.
I wonder if Jack would let Slim Jim take his ass? That I would love to see.
Jack read the other days' entries. It seemed that Diana had been entertaining her lovers almost every day for the past three weeks. He thought back as to what had happened three weeks ago.
Heather had gone to college. That was it. The sexual activity had started two days after they had taken their youngest to college.
Jack and Diana had looked forward to being empty nesters. The three boys, Jack Jr., Sam, and Zack were all on their own. Heather was the last to leave. Jack and Diana had made many plans for this time together. They wanted to travel to Europe, the South Seas, Australia, and Hawaii. Due to the nature of Jack's job, they had never been on a trip longer than one week.
Jack had a great job but a stressful one, and he had planned on fixing that. His company was going through a merger and a reorganization. Jack had been chosen to lead the team working on the reorganization. It had meant very long hours for the past three months. His workweek had evolved into 12 hour days six days a week. What Diana didn't know was that Jack was reorganizing himself out of a job. The company had offered him a generous golden parachute package. He was just a couple of weeks away from retiring. He had already booked a three-week trip to Paris.
Diana knew how important this task was and had been very supportive. She had taken over many of his tasks at home. They had a two-acre yard that would take all day to mow and trim. Diana outsourced that job so Jack could work on Saturdays. Handymen came in and performed the other minor tasks that a large house needed to be done.
Jack realized this is where Diana started cheating. Of all the clichés, she was having sex with the hired help.
Jack organized what he knew so far.
JC was the first lover Diana had taken. Diana had never given any description of this man other than his cock. His cock was roughly the same size as Jack. She seemed to like sucking on him a lot.
Black Beauty was Diana's second lover. By her description, he was a well-endowed black man. She had enjoyed his girth but seemed to be having problems with his size.
Slim Jim was fairly new. His cock was long and slim. Slim Jim was the only lover whose meeting she had described in any detail. She looked for him in the mall and online. She had talked about how many cocks she had to try before getting just the right size. She took him as a lover specifically for anal sex. She had never let Jack have anal with her.
It was apparent to Jack that Diana had many more lovers than she had written about in her diary.
Dixie was the newest member of the Fuck Diana Group. There was no description of this man or his cock. Jack realized that Dixie had to be a woman.
