The short synopsis of this story to date is included below, but reading the previous chapters may help. Also, in this chapter, I explore something that was recommended by a reviewer.
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This is the continuing story of a cuckquean, my wife, Ann. She had been reading cuckold stories on line and decided that she was a cuckquean, a kind of female cuckold. This was based on how enthralled and excited she became by imagining me having sex with other women. I was shocked, but she pursued it. She didn't show any tendencies toward the humiliation or denial part, but loved knowing I was having sex with other women. Apparently, this started with some voyeuristic tendencies about watching someone she was involved with have sex with another woman when she was in college and now she got off on thinking I was having sex with other women. I didn't understand it, but she pursued it and I started doing so.
In the last chapter, I welcomed Mary back to work, but she got an offer from a senior VP, so I was going to have to find another admin assistant. Then my wife, Ann, invited the voluptuous Anita over to make a movie. She wanted another movie of me fucking someone. But it turned out rather tame in her mind, so then we went over to Anita's house where we learned that Bob had a fantasy of seeing her fucked by another guy. He really got into and pushed her and then let Ann jerk him off all over his wife's tits while I fucked her and filled her with cum. It turned out that he was really pushing her to be slutty. It was a great night.
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For a couple of days, I came home to find Ann busy with the kids and we'd work on getting them through sports, homework, etc. Once they were in bed, Ann was a firecracker. She loved hearing me retell our time with Anita and Bob. When I got to the part where Bob called Anita a slut and pushed her limits while she was fucking me, Ann would cum every time.
Soon, however, we were back to barely keeping up with the kids and having any energy left by the time they were down. We got to one point where we hadn't had sex or fun in about a week. Finally, one Friday, Ann told me that her parents were coming over to pick up the kids on Saturday morning and keep them until Sunday afternoon.
That night, Ann got busy after getting ready for bed. She seemed especially turned on and when I asked her what was going on, she said she arranged for some fun tomorrow. I couldn't argue with either her being horny or having fun with others, so we had a very vigorous evening. She seemed particularly pleased with the way I teased her pussy and clit with my tongue, making her wait for a while before I let her cum.
On Saturday, we got the kids up and ready for a day with the grandparents. They were jumping for joy. Their grandparents bought them whatever they wanted, took them wherever they wanted to go, and let them do whatever they wanted. Well, maybe it wasn't that bad, but it was close!
The kids were gone by 10am and Ann and I relaxed and picked up a few things. At noon, the doorbell rang. Ann told me to stay put since it was a surprise. So I waited. Ann came back and said I had to wait a little longer after the first delivery. Delivery? What the hell did that mean?
About 15 minutes later the doorbell rang again. This time, Ann led a young woman that I hadn't seen in a while into the kitchen.
"Jessica! How good to see you again." The young redhead was wearing a tight white sleeveless top and tight jean shorts.
"Hey, John." Jessica grinned and came over to give me a hug. I pulled her in and gave her a hug with my right hand squarely on her left butt cheek. She chuckled and looked over at my wife. "I can't tell you how surprised I was when your wife told me that that was a setup the last time I was here babysitting."
"Yeah, but your reaction was interesting."
"Ha, ha. I was pretty scared at first. You guys had me thinking I was in real trouble."
"Well, you weren't. It was just a practical joke."
"Well, Ann tells me you guys are going to make it up to me today."
Now it was my turn to grin at the two of them. "I certainly hope so."
Ann turned to Jessica. "So are you ready?"
I turned to Ann. "Ready for what?"
Ann grinned. "Well, you need to go upstairs and make sure you are nice and clean, right Jessica?"
"Yep."
I narrowed my eyes at the two of them. "What's going on here?"
Ann giggled. "Okay, I'll tell you. You and Jessica have been hired to do another modeling gig for Kathy's line of erotic clothing."
I looked back and forth between the two of them. "Where?"
Ann pointed left toward the living room. "Right here. Kathy arranged to bring three of her favorite female customers here." Ann looked at her watch. "They should be here in about 15 minutes."
Jessica held her hand out. "Come on, John. Let's go upstairs and get ready."
I looked down. "I'm not ready?"
Jessica shook her head. "Ann told me to make sure to make sure you were trimmed close. She wants to show off your equipment."
I looked over at Ann and she smiled and shrugged, so I took Jessica's hand and she led me for the stairs.
"Hey!" Ann yelled at us and we both turned. "Don't play! You need to be ready for modeling."
Jessica grinned. "I know. I'll take it easy on him."
I shook my head. "Gee, thanks."
We went upstairs. I went to the bedroom and started stripping. Jessica just watched. I finished undressing and stood in front of her naked.
Jessica grinned. "You have a nice cock, John, but let's shorten the hair around your cock and balls."
My cock responded with a little twitch and started filling with blood at the frankness of Jessica's remarks. I grinned.
Jessica shook her head and looked at my cock. "Those things really do have a mind of their own, don't they?" I just shrugged. Jessica reached out and grabbed my cock. "This way, please."
Jessica led me into the bathroom where my wife had put out my electric trimmers. Jessica picked them up and dialed in the setting she wanted. "Step into here." Jessica pointed to the shower. "Then we can just wash the hair down the drain."
I stepped into the shower and Jessica toed off her shoes and stepped in, too. She reached down and lifted up my balls. "Put your foot up on the side." I did and Jessica went to work trimming around my balls. She continued to hold my cock and it hardened. Jessica then released my cock and moved my balls around as she trimmed. She got most of it from my balls and my legs leading to my balls, which was already pretty short, but needed to be trimmed a little closer. She then grabbed my cock and moved it around as she took care of what was around the base of my cock. It was barely showing, but she trimmed it much closer.
When she was done, Jessica moved everything around to check her job and cleaned up a couple of spaces. "There." She smiled up at me. "Much better."
Jessica pulled down the showerhead and turned the water on. Once it was warm, she rinsed me off from the waist down and put it back. She then got a towel and dried my ass and junk. "Now, step out onto the mat." I did and she dried off my legs and feet. Jessica turned and grabbed the lotion that was on the sink, she squirted some into her hands and massaged it into everywhere she shaved. My cock got hard again. Jessica grinned and gave my cock a light slap. "Not now. Let's get ready for the show. The clothes we're showing today are in the guest bedroom. Kathy should have put them in there already."