Office Fling

by Amy Brent

  “Would you ever want to do a three-way with me and Wynn? Is that something you’re open to? Being with two men at the same time?”

  She was quiet for a few seconds, then quietly said, “I don’t know. Maybe.”

  “Never done a three-way? No history of raging orgies in your past?”

  She put her chin on my chest so she could look me in the eye and shook her head. “No, I’ve always been a one fuck at a time kind of girl. I’ve never really thought about it. But you know my motto.”

  “I didn’t know you had a motto,” I said, brushing a strand of hair from her damp forehead.

  “Sure, I do.”

  “Well? What is it?” I asked.

  She leaned up to bite my bottom lip. “Never say never.”

  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.”

  CHAPTER FIVE: Wynn

  My flight into Midwestern Regional Airport landed on time at 9:15 Friday night after a quick connection in Denver. The little airport was relatively deserted at that time of night, so it didn’t take long for me to find the Hertz counter and pick up the 2017 Nissan Maxima the psych association had rented for me for the weekend. I tossed my bag in the trunk, rolled down the windows, cranked up the music, and nodded at the lot attendant who was dozing in the little gate house as I passed. As I pulled out of the airport and onto Interstate 45 south to Madison, I felt like I was going back in time.

  It had not been that long since I was a struggling professor of psychology at Midwestern University, one of the small regional universities dotted around the state. I had come to Midwestern just over four years ago when my old college roommate and best pal on the planet Holden called to say there was an opening in his department.

  At first, I was hesitant to leave the sunny days and sandy beaches of California, where I was working as an assistant psyche professor at a small community college while working on a motivational book called The Psychology of You.

  I know. The title was pretty fucking hokey, as was the whole concept behind the book, which was probably why I never got past writing the first chapter. Chapter One… uh…

  Honestly, I was inspired by another buddy of mine named Lane Curtis—Dr. Lane Curtis, to be exact—who had written several books on psychology and now made a fortune doing seminars and on speaking tours. Lane was a former college linebacker who was much smarter than he looked. Still, I figured if Lane could do it, so could I. Granted, I’ve since written a mega-bestseller, but at the time I was in way over my head.

  Then Holden called to tell me about the job at Midwestern and I realized that my affinity for surfing and fucking beach babes was only matched by my affinity for eating, and since I was barely making enough to keep my surfboard waxed and my belly full, the job at Midwestern could not have come at a better time.

  Two weeks later, I flew in for a round of interviews, ended up fucking the woman in charge of the hiring committee, and the rest was history. I started a week later, and spent the next three years sleeping in Holden’s spare room and fucking my way through the student body and much of the faculty, often with Holden on the other end of the same woman.

  I had not been in town three days when Holden and I resumed our little adventures in the land of group sex, which we had perfected back in college and grad school. We had been best buds since our freshman year at UCLA and had double-teamed our first girl that same year: a brunette undergrad named Beatrice Porter who had the biggest tits I’d ever seen in my life. I mean, honestly, the damn things were huge, with nipples as long as your thumb. Seriously. Like down to her waist huge. Like four handfuls huge. Like more than enough for two guys huge. It was amazing, what Beatrice could do with those giant tits, not to mention the rest of her body, which was proportionately small compared to her breasts.

  Our most memorable time with Beatrice, at least for me, was the night she ordered us to take turns fucking her cleavage while the other fucked her pussy. Hell, me and Holden were up for anything, so we took turns. Holden straddled her belly and she held her tits together with his cock sliding between them. He fucked her cleavage while she leaned her head forward to lick his cock each time it came through.

  At the same time, I had my cock buried as deep inside her as it would go, and I was jackhammering her like there was no tomorrow. She had her legs wrapped around my waist and kept nudging my ass with her heels as if she were riding a horse. We all three came at the same time and nearly broke her bed in the process.

  Then we caught our breath, smoked a joint, drank tequila shots, and did it all over again, this time we me fucking her tits and Holden between her legs. I gotta tell you, that Beatrice was something else. Last I had heard she was living in Des Moines with an accountant named Irv, raising three kids, all of whom I’m sure had been breast fed.

  I pushed thoughts of Beatrice Porter out of my head because I was getting a freakin’ boner just thinking about her. Hard not to think about those tits… simply amazing.

  I turned off the highway and soon found myself driving along the main drag that snaked through the center of campus. It was a Friday night, but there wasn’t much going on at Midwestern. It was early fall and a lot of the kids had gone home for the fall break. I pointed my nose toward the window and took a deep breath. I always enjoyed Midwestern in the fall; the changing leaves… the cooler temperatures… the coeds with thick sweaters and no bras… fucking in front of a roaring fire…

  Holden’s house was on the north side of campus, in a community of well-kept older homes where most faculty members lived. I arrived at his house around ten and parked on the street. The street was dark and quiet. Holden always said folks on his street went to bed at sundown. Apparently, he was right. The place was quiet as a tomb.

  In the driveway sat Holden’s old Jeep Cherokee and a late model Hyundai with a student parking sticker on the back bumper. Jude’s car, I expected. I switched off my rental and stared at the house for a moment. There were lights still on, along with the porchlight. I was sure Holden and Jude were inside. I licked my lips, wondering if I was going to catch them in the act. And if so, might they be open to a third player for their little games?

  Holden had suggested that Jude was open to the idea of a three-way, but you never knew how someone was going to react once things became real.

  A lot of women cringed outwardly at the thought of having sex with multiple men at once, even if the thought was exciting on the inside.

  I think most men would take part in a three-way if they weren’t horrified at the prospect of accidentally touching another guy’s cock with their own, or terrified of their wives finding out that they were unfaithful. I always found it funny that fear was what kept most men faithful. Fear of their wives and fear that they might immediately turn gay if their junk touched anther guy’s. Hell, my cock had crossed Holden’s numerous times during our sexcapades, but we were two of the most ardent heterosexuals around.

  My psyche training told me that such resistance to group sex was more often than not borne from the values, morals, and opinions of society that were instilled in humans from birth, even though humans were not necessarily meant to be monogamous animals, at least not from a genetically-wired point of view.

  The fact is only three to five percent of the roughly five-thousand species of mammals on planet earth ever form life-long, monogamous relationships, and that includes we humans, beavers, wolves, and some species of bats. That’s it. The other ninety-five percent of mammals have a hey-day fucking whatever they want to fuck without worrying about getting in the dog house when they come home. Male gorillas are not fearful of their wives. Lucky them.

  Then there is what is called social monogamy, which is the term that refers to creatures that pair up to mate and raise their offspring, but still have flings no the side. They are not sexually monogamous, but socially so. It would be like your dad and mom were married and raising kids, but your dad was still banging his secretary on the side or your mom was banging your uncle Ralph. They were socially monogamous, but not sexually so.

  Confusing? You bet, especially if you’re a guy like me and the call of the wild occasionally makes your balls tingle. Those who study the psychology of evolution (serious stuff compared to me studying the psychology
of pussy) suggest that we men are more likely to fuck around than women, partially due to that little snag in our DNA that urges us to spread our seeds like dandelions spores in the wind.

  Males are genetically predisposed to finding females who would make “good breeders” and planting their seeds to keep the species alive. That’s why men are often most-attracted to women with wide hips and big asses and big titties. A woman like that is, at least in our cave man minds, a good candidate to keep barefoot and pregnant. She is good breeding stock. It is our genetic duty to keep the species going, yet society tells us that’s not the acceptable thing to do.

  I know, sounds like I’m making excuses for men to fuck around. Maybe a little, but the fact is that males are not genetically predisposed toward monogamy. Think about the bible; if Adam and his sons had been monogamous (and not attracted to their own sisters), and if all those other dudes like King David and Gideon had been monogamous, there would probably be a lot fewer humans on the planet right now. Then again, maybe that wouldn’t be such a bad thing.

  Would I ever commit to a monogamous relationship? Me, the guy who has never been faithful to one woman ever? The guy who breaks out in hives at the thought of commitment? The guy who cannot fathom the prospect of being with—and having sex with—only one woman for the rest of my life?

  I never say never, but at this point in my life I can’t imagine committing to just one woman. Even if I met a woman and fell deeply in love I think there would always be that little cave man sitting on my shoulder yelling at me every time a beautiful woman walked by.