Office Fling: A Single Dad Baby Romance

by Amy Brent

  “Fuck me hard, Wynn,” she said, smiling at me in the mirror. Her big tits swung beneath her. “Fuck me really hard.”

  “Yes, ma’am,” I said again. I took a step closer as the head of my cock pressed to her hole, then easily slid inside her. I dug my fingers into her hips and watched her in the mirror as my cock impaled her an inch at a time. Her eyes were closed. Her mouth was open. I could hear her exhale with every inch invading her from behind. When I felt the tip of my cock hit her innermost wall, I slowly pulled out until the head appeared, then slid back in again.

  “Oh… fuck…” she moaned, eyes closed, head hanging. “You are… so… fucking… huge… my pussy… stretching… oh… fuck... yes… yes…”

  God, she was tight. Tight as any twenty-year old I’d ever fucked, and I’d fucked a lot of them. Her pussy suctioned around my cock, gripping it tight. I could feel her cunt muscles squeezing my shaft as it slid in and out, in and out. It didn’t take long before I could feel the orgasm building deep inside my balls like a volcano about to blow.

  “Faster… Wynn… faster... fuck me… faster…”

  I dug my fingers into her sides and started slamming it to her, ramming her wet pussy with my hard cock as fast and hard as I could without hurting either of us. Her big tits swung like pendulums from her chest. She opened her eyes to look at me in the mirror. Her mouth was open, her tongue draped across her bottom lip like a panting dog.

  “Fuck… Jean… I’m going… to… fuck…cum…”

  “Cum with me… baby…” she moaned, pushing her ass back toward me until my cock rammed against her cervix. “Cum in me… cum… harder… fuck… yes… yes… yes…”

  For the life of me, I had no idea how the other twenty people at the party didn’t hear us going at it like wild animals. I totally forgot that I was in Professor Milton’s upstairs guest bathroom fucking his hot wife. And Jean didn’t seem to care. She was practically wailing as she came all over my cock, squirting, drenching me, milking me with her magic pussy.

  When it was over, I fell against her and reached around to get a handful of her big tits. She wiggled her ass against me and smiled in the mirror.

  “What were you thinking?” I asked playfully as I nipped at her shoulder. That’s when she said the words that changed my life forever. She smiled at me in the mirror again and gave her ass a little wiggle.

  “I wasn’t thinking,” she said. “My pussy was.”

  I blinked at her for a moment as a tiny spark of an idea went off in my brain. “Your pussy was thinking?”

  She pushed herself up and leaned back against me. My hands cradled her tits. I rested my chin on her shoulder to stare at her. She said, “You know how men think with their cocks?”

  I gave her a nod. “Yes.”

  “Well, women think with their pussies. And my pussy thought it would be a great idea to meet your big cock.” She turned to face me and reached down to take my damp, softening cock in her hand. She rubbed the head of my cock against her clit and sighed. “So, Professor Wynn Driver’s cock, nice to meet you.”

  “Likewise,” I said as she moved to sit on the toilet to clean herself off.

  As I pulled up my pants and stuffed my cock back into my boxers, her words stuck in my brain.

  What’s your pussy thinking?

  What’s Your Vagina Thinking?

  A year later it would be a question I’d be asking the world.

  And the world—or at least many of those in the world with pussies—would be more than happy to answer.

  CHAPTER THREE: Judith “Jude” Allen

  “I can’t believe you’re reading this book,” Izzy said after plopping down on the sofa next to me and picking up my dog-eared copy of What’s Your Vagina Thinking? from the coffee table. I had been sitting peacefully on the couch in our little off-campus apartment working on the dissertation for my Master’s psychology class when she blew into the room like a hurricane and started giving me crap.

  Izzy—Isabelle Miranda Parks, to be exact—was a beautiful black girl from Atlanta who was mastering in clinical psychology at Midwestern. She was tops in her class and had a brilliant mind for psychology, though her boisterous personality and foul mouth would probably belie that fact to anyone who didn’t know her.

  Izzy had been my roommate and best friend since freshman year. Now, four years later, we were both in grad school at Midwestern and were just a few semesters away from starting our professional lives.

  Izzy as a clinical psychologist and me, well, I wasn’t sure what I would do with my life yet. I would graduate with a Master’s in Psychology, but I was now thinking about getting my Doctorate, so I could practice as a psychiatrist.

  Honestly, like so many people do, I got into psychology to address my own mental health issues, to figure out my own warped shit, primarily because I thought I was a nymphomaniac with an older man complex.

  Now, with the help of my lover, Professor Holden Moss, I had figured out that I wasn’t really a nympho, just a horny bitch who liked to fuck older guys. Just coming to that revelation cleared the way for me to devote my time to helping others do the same.

  “Why aren’t there any pictures of actual pussies in this book?” Izzy asked, clicking her tongue as she flipped through the book written by Holden’s best pal, Dr. Wynn Driver. “Girl, there ain’t a single pussy in this book, thinking or otherwise. That title is false advertising!”

  “The title is a metaphor,” I said, doing my best to sound serious despite the smile that was itching at my lips. “It’s about the female anatomy’s effect on the brain.”

  “Like a man thinking with his dick,” she said, shaking her head as she scanned the chapters.

  “Yes, pretty much.”

  “What the fuck ever,” she said, rolling her eyes. “Still, if the title says it’s about a thinking pussy, I wanna see pictures of thinking pussies!”

  “Maybe your pussy thinks too much,” I said, giving her a sideways grin.

  “Girl, the problem with my pussy is Earl don’t give it time to breathe, much less think!” She cackled at herself and slapped the book on her thighs. Izzy had been dating Earl Winston, the extremely cocky and arrogant captain of the Midwestern University Buccaneers, for nearly three years. Earl had offered to fix me up with his football buddies, but I had always declined. I was never into jocks that much, and now that I was involved with Professor Holden Moss, Earl had stopped trying.

  It wasn’t that I averse to screwing a hunky football player every now and then, but I preferred sex with educated men. Okay, the truth was, I loved the idea of being The Teacher’s Pet—and no I did not consider that to be a psychology issue I had to deal with.

  I loved being dominated, commanded, directed, coddled, being taken care of. And I loved giving as good as I got. I had always been attracted to smart men… brilliant men… teachers… professors... doctors… scientists… sorry, no lawyers (a girl has to have her standards). For some reason, the thought of sleeping with a lawyer just made my skin crawl.

  Izzy turned the book over and grunted at the photo of the author on the back. “Mmmm mmm mmm… Now there’s a man I could do some damage to. Wynn Driver… wonder if he likes hot chocolate?”

  “I’m sure he does,” I said with a smile. “From what Holden tells me, Wynn Driver loves women of all shapes, sizes, colors, ethnicities…”

  She held up the book so I could see the photo of Wynn and tapped a long fingernail to the book. “Wait a sec, this is your man’s best friend? The one you told me about? Rich dude, lives on the beach in California? Used to teach psychology here at Midwestern?”

  “Yes, that is the Wynn Driver that Holden is always talking about,” I said with a nod. “They’ve been best friends since their freshman year at college. I think Wynn was sleeping on Holden’s couch when he landed that book deal and got stinking rich.”

  “I think I saw him on Ellen,” Izzy said, narrowing her eyes at the handsome face in the tiny photo. “So, this is the man who will fu
ck anything with a pulse,” she said, pressing two fingers to her wrist. “Well… lookee here… I just happen to have a pulse… And a thinking vagina…”

  “I never said that he would fuck anything with a pulse.” Izzy was wearing a pair of black lace panties and a tee-shirt with no bra. It was her usual attire when we were home alone. I glanced at her long legs stretched out in front of her, feet on the coffee table, ankles crossed, and poked her with an elbow. “But I’m pretty sure he’d be all up in your hot chocolate bidness.”

  “Well, my hot chocolate bidness might just have to let him come all up in here if he ever comes to town.”

  “He’s coming into town later tonight,” I said. I could hear the anticipation in my voice. If Wynn was half the man Holden proclaimed him to be, it might prove to be quite an interesting weekend.

  “That man right there is coming here? What for? Why would anyone escape this shitty little town and come back?”

  “He’s speaking at the psyche conference this weekend. He’s staying at Holden’s for a few days.” I nodded at the book. “That’s why I’m reading that book, to get an idea of who he is and what he’s all about.”

  “Well, my vagina is thinking that maybe he can check your vagina’s pulse while he’s here,” Izzy said. “Or check your internal temperature with his big, thick thermometer cock.”

  “How do you know he has a big, thick thermometer cock?” I giggled at the concept of Wynn Driver taking my internal temperature with his cock, which Holden swore was nearly a foot long. The thought made the juices between my legs start to flow.

  “Look at those eyes,” Izzy said, holding up the book. “Man looks at you like that, it means he has a big cock to back that shit up.”

  “You’re nuts.”

  “Hey, you said him and Holden were gangbangers.”

  “I said they had done three-ways before. I never called them gangbangers.”

  “You say three-way, I say gangbang,” she said, her dark eyes dancing with delight. “I’ve never been gangbanged myself. Wonder what it would be like. Having two cocks going at you at once. How does that even work? One in your mouth and one in your pussy, like book ends? Or one in your pussy and one in your ass… Lordy… talk about a tight fit…”

  “You’re asking the wrong person,” I said with a sigh, even though I had wondered—and dreamt of—the same thing myself several times since learning that Wynn was coming to visit.

  “Am I asking the wrong person, really?”

  I narrowed my eyes at her. “What does that mean?”

  She shrugged one shoulder and flipped more pages. She wasn’t reading. She was just avoiding looking at me. “Well, it’s just that, you know, out of everyone I know you are the most… shall we say… experimental and open when it comes to sex?”

  “So?”

  “So, if the opportunity to do the nasty with your boyfriend and his best friend came up, would you say yes, or would you say no?”

  “Holden is not my boyfriend.”

  “You’re avoiding the question.” She turned sideways on the sofa and tucked her long legs beneath her. She poked me in the arm with a stiff finger. “Come on, Jude, fess up. If Holden Moss and Wynn Driver wanted to do double duty on that cute, tight ass of yours, would you say yes, or would you say no?”

  “I’d say that was none of your business,” I said with a smile.

  She gave me a “point proven” smile in return. “See. I thought so. Whoo, girl, I see some gangbangin’ in your future. Just don’t let them two big cocks stretch you out at once. That pussy might never be the same.”

  “Whatever,” I said, forcing a smile. Izzy was right. It was true that Holden and Wynn had double-teamed lots of girls. Holden had told me stories about their adventures that got me so worked up I literally raped him on the spot. And I’d be lying if I said the thought of having sex with both of them at once had not entered my mind on more than one occasion. I loved having mad sex with Holden, but we were two consenting adults who were not caught up in petty jealousy or commitment. We fucked each other like breeder rabbits, but that didn’t mean we couldn’t fuck others, as well.

  “You’re awful,” I said, trying to tug the book from her hands. She pulled the book away and clutched it between her mounding breasts. “And you’re also full of shit.”

  “How am I full of shit?” I asked.

  “What’s your vagina really thinking, Jude?” she asked with a sly grin. “Lord knows the poor thing has been working overtime since you took up with Professor Holden Moss. Is there room in there for this Dr. Wynn Driver dude?” She leaned over and lowered her voice. “One big cock in your pussy and another in your ass? Mmmm mmm good…”

  I rolled my eyes at her. “Jeez, Izzy, stop!”

  “Who knows,” she said, head bobbing, eyebrows arched. “Maybe they have a third buddy who could shove his cock in your mouth while they’re going at you from the other end. What would you call that? A four way? A quadruple fuck? What?”

  “Izzy! You’re awful. Stop it!”

  “You stop it,” she said, holding out the book with Wynn’s picture showing. “Hell, if you won’t fuck them both maybe I will.”

  I snorted a laugh and snatched the book from her hands. “Oh yeah, and then Earl will kill both of them.”

  “Might be worth it,” she said, smacking her lips. “Two big cocks at once. My, my, my what a lovely way to go!”

  Yes indeed, I thought as I stared at the photo of Wynn Driver, with the image of Holden Moss clearly in my mind.

  What a way to go.

  CHAPTER FOUR: Professor Holden Moss

  I’d been sleeping with (I suppose that is the politically-correct term these days) Jude Allen for a few weeks when I found out for sure that my best friend in the world, Wynn Driver, was coming back to town. Actually, I was the one largely responsible for bringing him back to Midwestern. The real surprise was that he was willing to take time out of his Hollywood lifestyle to come back and visit those poor souls he left behind at Midwestern.

  Our local Midwestern Psychology Association, which consisted mostly of psyche department academics, psychotherapists, psychiatrists, psychoanalysts, mental health professionals, and the like, was having its annual meeting, and who better to address the theme of this year’s gathering—Psychology & Sexuality in The Modern Age— than my old pal Wynn, who had literally written a bestselling book on that very topic.

  It did not take much convincing from me for the association board, which was made up mostly of women who had had sex with Wynn when he was a professor of psychology at Midwestern, and women who missed their chance but still wanted to fuck his brains out, to unanimously vote to have Wynn as the keynote speaker on Sunday night. There would be a dinner on Saturday night in his honor, followed by a book signing, and a cocktail party slash meet-and-greet. I found it funny that a group that had frowned upon Wynn’s teachings for years now saw him as their golden child celebrity. I guess getting on the cover of Psychology Today Magazine didn’t hurt. And I knew that there would be a number of female association members lining up to go home with him on Saturday night.

  Wynn would call it “like shootin’ fish in a barrel”.

  I called it just another night in the charmed life of Dr. Wynn Driver.

  Wynn was due in Friday on a late flight, would be crashing at my place for the weekend, and probably expecting to get laid several times while he was in town.

  Given the amount of talking I’d done to him on Facetime about the hot new grad student that was sharing my bed, I knew that Wynn’s curiosity had been peaked. Especially when I told him I’d mentioned our threesome adventures to Jude and she seemed interested in perhaps learning more.

  And to Wynn that meant he would expect a little taste for himself while he was in town, Jude willing.

  Jude was a twenty-two-year, old grad student majoring in psychology, and one of the most amazing young women I had ever met at Midwestern University. She was not only drop-dead-gorgeous, with long blonde ha
ir, bright blue eyes, tall, voluptuous, big tits, round hips, big ass, and best of all, she had an insatiable appetite for sex that nearly matched my own. She was also smart, witty, charming, driven, dedicated, and had a biting sense of humor and a fierce independence I rarely saw in young women her age.

  Of course, Midwestern University had a policy that discouraged—but did not strictly prohibit—its professors from fraternizing (again, the politically-correct term) with students. But Jude was old enough to make her own decisions and she was the one who seduced me in my classroom at the start of the summer term, so how could I possibly say no when she sat in the front row and flashed her pussy and then casually invited me to “fuck her brains out” after class? She said she was a nymphomaniac with a Teacher’s Pet fetish, and I was lucky enough to be the teacher she had chosen to bestow her favors upon. It would have been down right rude of me to say no. Right?

  It wasn’t as if the thought of having a threesome with Wynn and Jude had not been brought up in conversation, at least not directly. Jude and I had been together for a couple of weeks when the topic turned to crazy things we’d done, this after having spent the past hour fucking in the hot tub next to the pool at Jude’s apartment complex.