The Crush: An Affair in Three Parts

by Ben Boswell

  The “problem” got worse with Elena, our office manager. I can’t say I saw that coming. She was blond, tall, and busty, but married and closing on forty. Not really my type. Her chin was a bit squarish, sort of Jennifer Aniston-style, and her body a little soft, sort of what Kate Upton is going to look like in a few years. Now those are two beautiful women, but, well, to be honest, I’m a shallow douche in many ways, although I like to give myself credit for admitting it.

  Here’s the thing. Men are visual creatures… to a point, because, look, a hot, wet pussy is a hot, wet pussy. And you close your eyes, and the truth is, a lot of stuff that looks good doesn’t feel as good, and conversely some things that don’t catch your eye are… amazing.

  So I had that in mind when she started to get a little flirty with me. I had in mind also the fact that she was married, and as I’ve mentioned that’s a weird turn-on for me. With Cassidy, it was just a bonus. She was hot enough that I’d have happily fucked her even if she were single. But with Tina and Peggy already sucking me dry, I probably wouldn’t have gone for Elena if she hadn’t unwittingly appealed to my dissolute nature.

  Tina had just left my office after enthusiastically twerking on my prick, when Elena came in to see me.

  “Haven’t you ever heard that you shouldn’t shit where you eat?” she asked.

  “I don’t know what you’re talking about,” I replied blandly.

  “It’s not like you and your whores are particularly discreet, even if they weren’t going around bragging about it non-stop.”

  I shrugged. “We’re consenting adults.”

  She snorted. “They’re both young enough to be your daughters.”

  “Only if I’d fathered them when I was in my teens.”

  “I’m guessing that wasn’t out of the question.”

  I laughed. “We’ll be more careful.”

  “No you won’t,” she replied. “You like everyone knowing.”

  “Why would I?”

  Now she shrugged. “Probably because you’re an insecure narcissist.”

  That got my attention. I watched her closely. Definitely not a bad looking woman. A bit of that Mrs. Boyer vibe. My prick, still sticky from coming in Tina’s tight cunt, twitched.

  “I think you’re jealous.”

  She forced a laugh and I noticed her cheeks flush.

  “You really think you’re God’s gift, don’t you?”

  “I’m willing to let you find out.”

  “You’re so generous,” she snarked.

  She was trying to convey contempt, but she also wasn’t leaving.

  “You’re married,” I noted.

  “What’s that have to do with anything?”

  “It means you probably shouldn’t be so eager to fuck me.”

  “I’m not.” Softer. Less angry. Trying to convince herself.

  It would have been easy enough now to seduce her. First let her off the hook. Then come back around and woo her a bit. Help her convince herself that she wasn’t really cheating. Women are guilty creatures. But find a way to ease that guilt and they’re just as horny as men. But I wasn’t interested in a feel-good seduction. I was coming around to the idea of having her, but if I did, I wanted it to be dark and dirty.

  “Close the door,” I ordered firmly.

  She startled.

  “Do it!”

  She did and then looked at me, surprise at her actions written on her face.

  “I don’t know what you think –“

  “I think you want to suck my cock.”

  She looked shocked, but she didn’t run. Instead, she took a half-step toward me before she caught herself. But I knew I had her.

  I don’t claim to be able to read a woman’s mind. Not always at least. But a woman is like a lock, you just need to find the right key. Cassidy was just looking for a quick fuck to spite her hubby for ruining their wedding night. Peggy liked the idea of being my co-conspirator. Tina was just looking for a little fun. Elena wanted to be taken. What did Red want? I’d need to focus more on that later.

  “Get over here.”

  “You’re a pig,” she hissed.

  “And that’s why you want it.”

  “No.”

  “It would probably be better if I was a sweaty construction worker or a stranger in an alley, but this’ll have to do.”

  “I don’t know what you mean.”

  I laughed. “My dick still smells of Tina’s cunt. Come lick it clean.”

  Her knees buckled and she took a half-step forward.

  “I’m going to fuck you like your husband never has. Like a dirty whore.”

  Panic, shock, excitement written on her face. A wordless question: How do you know?

  “That’s your fantasy, isn’t it?”

  “No,” she replied, though she nodded her head instead of shaking it as she did.

  “You’re running out of time.” This is just a pity fuck.

  She got my meaning. “Fuck you,” she snarled. But she was walking toward me.

  I spun my chair to face her and spread my legs. “On your knees.”

  She hesitated again, but I knew she wouldn’t be able to resist. She was flushed, licking her lips unconsciously. I unzipped my pants. She stared open-mouthed and gasped satisfyingly as I pulled out my prick.

  “Don’t,” she groaned.

  “Do a good job with it, and I’ll consider fucking you.”

  “I don’t know why….”

  “Because you know I’ll do things to you that no one else will.”

  She swallowed loudly.

  “But you need to earn it first,” I added.

  She nodded but still hesitated.

  “On your knees, Whore,” I growled.

  It’s a thrill to say shit like that, even if you’re pretty sure it’s welcome. I’ve never been one of those dudes who feels the need to humiliate women to get even for some transgression or insult, imagined or real. But, on the other hand, there is something undeniably sexy about fucking a woman after you’ve degraded her. I can’t explain it. But, fuck, do I have to? Why else is porn so full of come shots to the face and rough anal? And it’s not just a male fantasy. Chicks dig it too. At least some do. Elena, I suspected, would.

  Her knees buckled and she didn’t catch herself. I reached out and snaked my hand into her thick, blond hair. I grabbed a handful and yanked her forward. She groaned, but her mouth opened just the same. I pressed her head into my lap, forcing my prick deep into her mouth. Is there anything sexier than the sound of a woman gagging on your cock? I didn’t throat fuck her. Not yet. Just forced her head up and down deep enough to trigger that gag reflex before letting her back up.

  I let her up to catch her breath, spittle dripping down her chin, her eyes red-rimmed, yet flashing with excitement.

  “You like tasting Tina’s cunt.”

  She recoiled slightly, but she wasn’t going anywhere. At this point she was committed. And anyway, even though she probably didn’t fully realize it herself, it was what she wanted.

  “You haven’t earned anything yet,” I added.

  I pushed her head back into my lap and she began slobbering again all over my cock. I leaned back in my leather desk chair and guided her up and down.

  “Show me your tits.”

  She rocked back on her heels, a string of saliva joining her lips to my prick. She twirled one of the buttons on her blouse flirtatiously.

  “Forget the show, Elena, just whip them out.”

  She hesitated a second. I reached out and grabbed her expensive, sheer, silk blouse.

  “Or do you want me to do it?”

  I tightened my grip.

  “No, don’t,” she whined.

  I nodded. Then obey.

  Her fingers flew now, unbuttoning her blouse and yanking it open. She had an impressive rack. A creamy expanse of meaty tit. I reached out and yanked her bra up so that they spilled out. She cupped her breasts and pressed them upward, offering them to me. I could tell she wa
s proud of her chest. Her tits were sexy. Very full and topped with dark red, erect nipples, silver dollar areolas, puffy with excitement. But I wasn’t going to give her the satisfaction.

  “Nice cow udders,” I snapped.

  She flinched as if stung.

  I laughed and grabbed a long nipple between each thumb and forefinger and gave a firm pinch. She whined in pain.

  “What’s the matter, Slut, having second thoughts?”

  “You’re an asshole.”

  I smirked. “Now there’s a thought.”

  She seemed puzzled for a moment, but then it dawned on her. “Oh no, no way.”

  “What’s the matter, Whore? I’m sure you’ve taken it up the ass more than a few times in your life.”

  She shook her head.

  I nodded mine. “Get up on the desk.”

  She was still shaking her head as she stood. She backed up and leaned back against the desk. I grabbed her legs and lifted them up, levering her ass up onto the surface, and bunching up her skirt. Without asking permission, I reached between her thighs and tore off her panties. She gasped.

  She wasn’t shaved or even really trimmed. Luckily she had a blond muff, and I’ve always had a thing for that. Also, she was so revved up that her wet, swollen cunt was on prominent display. I shoved two fingers inside her, and twisted them from side to side. She groaned sensuously and her juices coated my digits.

  “Beg for it,” I commanded.

  “Fuck me,” she gasped.

  “Where?”

  “My pussy.”

  “You have to earn that,” I taunted. “So, where do you want it?”

  She looked up at me. Her eyes filled with both hatred and lust. It was a potent combo.

  “My ass,” she groaned.

  “Say it together.”

  She resisted, but my fingers squishing into her pussy broke her resolve. She finally spit it out, “Fuck my ass.”

  I withdrew my finger from her snatch and trailed it down to her anus. I could feel her sphincter quivering, which matched the anxious look in her eyes.

  “Beg,” I ordered.

  She closed her eyes and grunted in frustration.

  “Do it, or I’ll never fuck you.”

  She didn’t last long. She fixed me with a murderous gaze. “Please fuck my ass, Stud. Please!”

  I chuckled and pressed my finger into her tight, hot rectum making her hiss and buck on the desk. I sawed my digit into her bottom. She was tense, but after a few minutes she’d relaxed enough that I knew I could get my cock up inside of her. She hadn’t taken it up the ass recently, but I was pretty sure I wouldn’t be her first. I edged up closer, until my cockhead was just about at her anus, and then with a quick movement, I withdrew my finger and replaced it with my prick. It was just the head, but even still it made her gasp.

  “I can’t. I can’t,” she whimpered.

  But she didn’t try to squirm away or even stop me with her hands. I pressed down on her thighs and went in deeper. Another hiss. The tight ring of her ass spasming wildly, at once trying to expel my invading cock but at the same time feeling so good that I wanted nothing more than to thrust in deeper. Which I did. Her eyes rolled back in her head.

  “Tell me you love it.”

  Staring at me with red-rimmed eyes and through clenched teeth, she hissed, “I love it. I love your dick in my ass.”

  Deeper still.

  “I love it. Fuck my ass. Fuck it.”

  I almost came right then. The fact that I’d broken her was even hotter than the sensation of her tight hole.

  I pulled out slowly and peered down at my prick. Nothing untoward, so I cupped the back of her neck and yanked her upright.

  “Suck it, and I’ll fuck you,” I offered.

  I could see her mind spinning, and I could imagine her thoughts. In for a penny, in for a pound.

  “You’re disgusting,” she snarled as she slid off the desk and down onto her knees.

  She gripped my cock firmly and sucked it deep into her wet mouth. I let her service me for a couple of minutes, before lifting her back to her feet. Roughly, I spun her around and bent her over my desk. I gave her soft ass a firm spank and then without any more games, shoved my prick balls deep into her eager cunt.

  I fucked her hard, like a whore, and she loved it. Her whole body shuddering in pleasure. And when she came, she slammed her palms down on the desk exuberantly. When it was time for me to come, I pulled out and shot it all over her ass, dripping it down between her cheeks so it coated her battered anus.

  I pulled up my pants. I was up to three office sluts, which was a lot even for me, and I hadn’t even nailed the one I really wanted to get my hands on. I know, I know. Boo-fucking-hoo.

  CHAPTER FIVE

  The next couple of weeks were a blur. We were all crunching on Red’s big proposal. And I was fucking Peggy, Tina, and Elena whenever I could fit them in, but with a tight schedule and three women to satisfy, it became a bit of scheduling challenge.

  I could often get Peggy and Tina together, but Elena wasn’t down with that. I could have probably given her an ultimatum, and she might have given in, but she wouldn’t be into it, and even I have lines I won’t cross. The upshot, though, was that there was a lot of tension, and Tina and Elena particularly squabbled with each other.

  It all came to a head one day when the three of us were in the office kitchen together, and the two of them got into it. I had to separate them after Tina started taunting Elena.

  If I remember correctly, Tina said something like, “how does my ass taste?” I’m not sure if she was channeling Shaq or if she meant it literally. In any case, Elena responded by heaving a metal napkin dispenser at her head. She missed, and I broke them up, but needless to say it quickly became office gossip.

  I figured that would be the final stake in my hopes of nailing Ann. A serious girl like Red would definitely stay away from me now. But then it turned out she didn’t. She was looking at the calendar like I was. With just a couple of weeks left in the office, I think she was beginning to think, “now or never.” I was thinking the same, and luckily with the bid coming down the wire, I had plenty of excuses to spend time with her.

  Is there a secret to seducing women? Well, yes and no. I mean there is a technique, but it is so simple as to belie the label “secret.” Anyway, here it is. Listen to them. Figure out what they want, what they really want, and give it to them. The trick, such as it is, is that many women don’t know what they want, or if they do they’re often too embarrassed to admit it.

  Peggy wanted to be my partner. She probably was a bit of a closet lesbian, and she got to experience the excitement of picking up a new girl viscerally through me. Tina was just looking for a good time. She’d have run for the hill had I even once hinted that I was falling for her. Luckily, I wasn’t. Elena had self-esteem issues, and it turned her on to be degraded. Those are all shorthand versions, of course, but they get the gist of things.

  I finally got Red’s number one day when we were chatting in her office. It was a little thing. A small, unguarded moment. We were talking about the bid, at least ostensibly so. We’d just finished drafting the narrative.

  “Okay, so now let’s send it down to finance to crunch the bond issues,” I suggested.

  “Oh no. I’m not letting this thing out of my sight. I’ve already given them the parameters. They’ll send us proposals and we’ll vet.”

  “Um, Red, that’s not our job. This is a team. You have to trust your people.”

  She shook her head. “I do trust them. But it’s my responsibility.” I could tell she what she was thinking as well – It’s always my responsibility.

  I don’t know why, but in that moment, I got it. She wasn’t a hardass because she was a bitch. And it wasn’t that she was obsessively driven. She didn’t think she had a choice. At some point, someone had placed the burden of their happiness in her hands. Her father? Her mother? Her husband? All of them?

  And all she wanted w
as someone else to take control.

  “Look, you’ve been working like a dog. I’ll take care of it, okay? You go home, spend some time with your husband. I’ll get the bond issue nailed down.”

  She held out her hand to stop me, and I took her palm in mine. She seemed surprised, but she didn’t pull away.

  “It’s your project, but it’s my job to help. Let me help.”

  She nodded. I held onto her hand and looked into her beautiful eyes. I had the sense that if I pushed it, I might be able to nail her right then and there. It would have been fiery and glorious, but I knew she’d immediately regret it. I didn’t want that. She was a prize, and if I was going to have her, I was going to really enjoy every bit of her.

  I smiled and released her hand. Then taking the draft deal book, I left her office.

  ***

  I didn’t have to woo her much after that. I made sure we had plenty of opportunities to be together, but I never made an overt pass at her. I could tell she felt embarrassed about her feelings for me, and I didn’t want to give her to opportunity to vent her guilt on me. Instead, I wanted her to internalize it and rationalize it away.

  The last couple of days on the proposal were the hardest. An endless series of last-minute fires that we had to put out, side-by-side, working long, late hours. It was a crucible that could easily spawn an office romance, even if there hadn’t been a pre-existing connection.

  I have to admit, it was hard to resist. There were any number of times when I was sure she’d melt into my arms at the drop of a hat. But I was determined to make her come to me.

  Now, that said, part of what gave me the necessary patience was my other women. Most mornings I would start off the day by throat-fucking Elena. She’d come back around lunch to get bent over my desk and screwed while I told her what a pig she was. I mostly saw Tina and Peggy together, the two of them seeming to discover that they liked girls more than they realized. But I have to admit, Red was beginning to fill up my imagination.

  Even when I was coming on Elena’s tongue, I was wondering if Red would do the same for me. As I slid my dick into Tina’s tight little pussy from behind, I imagined how good Red’s would feel. And when Peggy bounced up and down on me, big tits bouncing, I mauled her breasts thinking about how much I’d like to do the same to Annie.