CHAPTER FIVE: Holden
The biggest question was not whether Wynn would want to have sex with Jude. That, was a given. No, the biggest question was one only I could answer and that was: was I willing to share Jude with Wynn? And would Jude even be open to the idea?
I believed Jude would be open to the idea, given our past conversations and her free-wheeling sexuality and noncommittal attitude toward sex. I had always been totally open and honest with her when it came to my own sexuality.
I was as heterosexual as a man could be, but I enjoyed sharing women with my best friend, Wynn. We had double-tapped more women than I could remember, usually one of our older students or a faculty member or some woman we’d met at a restaurant or a bar somewhere.
I had no problem getting naked or fucking in front of Wynn and vice versa. We were there to give pleasure to the woman and get pleasure for ourselves. Period. And we enjoyed doing it together. Some people might have thought that we were weird and maybe a little gay, but that’s just the kind of friendship we had. We liked to bang the same girl. In our highly-trained, psychologically-enlightened minds, there was absolutely nothing wrong with that.
So, again, was I willing to share Jude with Wynn if that’s what both of them wanted? Wynn and I had not shared every woman in our lives because some women did not like the idea of having sex with two men at once. They think it was slutty, immoral, beyond their imagination, simply something they would never do. So, if I told Wynn that Jude was not a good fit for our little three-way play, he’d totally understand and not question me again.
On the other hand, how presumptuous of me would it be to deny Jude the incredible pleasure a guy like Wynn could offer a woman like her? Not sharing Jude would have been a totally selfish act on my part. I would have been thinking only of myself, not of her, and that would not be fair.
Besides, neither Jude nor I had branded ourselves monogamous. We were not a couple. We were not exclusive. We had no dibs on each other. To the contrary, we were both free to have sex with other people if that’s what we wanted. It wasn’t like we had that much extra time to fuck other people. Jude and I had been spending every waking minute together, which left neither us much time to explore sex with other people.
I was sitting in my classroom pondering that very point on Thursday afternoon when my phone buzzed on the desk. I looked at the screen at the smiling face of Wynn Driver calling from California.
“Sup man?” Wynn said with a big grin on his face. “You still at work?”
“Just finishing up,” I said, looking around the dark classroom. It was a stark comparison to the blue sky and ocean waves behind Wynn’s head. “You at your beach house?”
“I am,” Wynn said, glancing around as the ocean breeze blew his surfer boy hair in his eyes. “Wish you were here, my man. Another gorgeous day on the beach. Bitches in bikinis everywhere!”
“So, did you call to make me jealous that I’m here and you’re there, or was there a purpose to the call?” I asked, cocking one eyebrow.
“There is always a purpose to my calls,” he said. “I wanted to clarify something before I land there tomorrow night.”
“Clarify away,” I said.
“I assume that while not busy at the conference, we will be back to our old hard-partying ways while I’m there.”
“You assume correctly,” I said. “You think I’d let you come to town and not get your pipes cleaned?”
The he asked the question I’d been considering. “Sooo… does that mean that Jude is going to be partying with us?”
I had told Wynn all about Jude and had even sent him a few naked pics I’d snapped with her permission while she was sucking my cock. She had her pink lips suctioned to the crimson head of my cock and was taunting the camera with her bright blue eyes. I knew Wynn would want to meet her. After seeing the pics I’d sent, there was no way he couldn’t.
“I’ve broached the subject with Jude,” I said honestly.
“And?”
“And she is intrigued to say the least,” I said.
“Does she know about our little tag team act?”
I chuckled at the reference. There were many times when we had high-fived each other like wrestlers while changing ends of the woman we were fucking. I said, “I may have mentioned a few things to her about our act, yes.”
“And did she seem open to playing along?”
“Let’s just say that she did not shut me down,” I said. “In fact, now that I think about it, some of the hottest sex we’ve had was after I told her a story about you and me fucking the same girl.”
“Bam!” Wynn said with a big grin. “You got her on the line, my brother. All I gotta do is reel her in.”
“Maybe,” I said, nodding. “Just be aware that Jude is not like any woman I’ve ever been with before. Probably not like any woman you’ve been with.”
That piqued his interest. He gave me a thoughtful look through the video. “How so?”
“She is hypersexual, and considered herself a nymphomaniac with a teacher complex until I helped her see that she was just a healthy young woman who likes to fuck.”
“My favorite kind of healthy young woman,” Wynn said with a big toothy grin.
I smiled at him. “She is open, honest, and in your face. She is also fiercely independent and if you piss her off, well, just don’t piss her off.”
“Gotcha,” Wynn said, mocking a serious face. “I will not piss her off. And I’d never do anything that she didn’t to do. You know me, man, I’m a pussycat in the bedroom.”
“You’re a pussy hound,” I said, chuckling. “So, we’ll just play it by ear then. If Jude isn’t up for a little three-way action we can find someone who is, no problem. Maybe we can line up Marsha Clarkson and a couple of her bisexual friends who are not ardent man haters. Maybe we go to the RC and work ourselves into a little orgy. I know half the women on the association board would be willing to play.”
“I can always booty-call Jean Milton,” Wynn said, referring to the wife of Jefferson Milton, the head of the psyche department and my current boss. Jean was a hot forty-something piece of ass that Wynn screwed the entire time he was a professor at Midwestern. It was only by sheer luck that her husband never caught them fucking in every room of his house, sometimes while he was in another room entertaining guests.
“I’m not that big on tapping Jean Milton,” I said. “She’s hot, but I don’t think she would be up for a threesome. And I’m not sure I want the headache of fucking Jefferson Milton’s wife. Unlike you, my independently wealthy friend, I need this job.”
“Fine, I’ll fuck Jean by myself while I’m there,” Wynn said with a shrug. “You don’t know what you’re missing. Jean is a hot, hot fuck.”
“I’m sure she is,” I said. “I just don’t need the heat.”
“Then we’ll find another lucky girl to go three-way with us if Jude is not interested in playing along.”
“Sounds like a plan,” I said with a firm nod. I glanced at my watch. It was nearly five o’clock. Jude was waiting on me to have dinner. “Okay, I’m going to have to run. What time’s your flight?”
“Fuck, I don’t remember the exact time,” Wynn said. “It’s an afternoon flight out of Los Angeles, arriving late Friday night there. I’ll email you the itinerary when I’m back at my computer.”
“Okay, I can pick you up, no problem.”
“Fuck that,” he said, shaking his head. “You guys rented me a car, so I can drive myself from the airport. You just concentrate on lining me up some nice ass for the weekend.”
“That, I can do,” I said with a smile. “Okay, partner, see you soon.”
“Later,” Wynn said, holding up a thumb. “And don’t forget to talk to Jude.”
“I will,” I said with a sigh. “I definitely will.”