I knew that Amy’s kid wasn’t mine, I’d known I was infertile since high school, but I also didn’t really care. I wasn’t the kind of guy who got super jealous about what his wife was doing, and I also didn’t have what you might call “fatherly instincts.” I was more than happy to let some dumb high school kid squirt his cum inside her as long as it made her happy. And, if I ever wanted to divorce her, I had a built in excuse. What was more important to me was that I was able to keep getting off when I wanted. Amy being pregnant meant she wasn’t really interested in sex, and terrified of hurting the baby when she was, so I began to look elsewhere to get my rocks off. I’d called up ex-girlfriends and fucked them in hotel rooms, picked up girls at bars for a night of no-feelings sex, and even called up super high tier escorts when I felt like really getting freaky. But I’d never thought of sleeping with any of the girls at my office where I was a vice-president, even though there are so many who are young, dumb, and sexy as hell.

That was before Cassie became my secretary. Cassie was about 22 years old, give or take one. She wasn’t really my type, I had always liked busty blondes with serious edges, but Cassie was skinny with defined hips and tits that were on the small side of B-cup. She was gorgeous though, dark haired, olive-skinned, and freckly, with a constant cheeriness and bubbly nature. I hardly noticed her for the first few months, but when summer hit she began to show off more and more skin in sundresses and tank tops. She rarely wore a bra. We began to flirt more and more, and she became almost overt in her come-ons to me. She would say double entendres and flick her eyes down at my crotch, talk about her sex life in explicit and inviting detail, and make shows of flirtatious sex appeal solely for my benefit.

I felt that she thought she couldn’t act on any of her urges because I was married. She had bought gifts for my wife, made dinner plans etc. So I needed to show her it was okay, and that I wanted to have her as much as she wanted me to give it to her.

One day I was walking back to my office after a business lunch. Cassie was at her desk and Eve Draper was talking to her in a manner I felt was rather rude. I could over hear the tail of the conversation as I approached.

“…this is just lazy formatting, Cassie, and it slows down the entire office when other people have to constantly correct for your mistakes.”

“I’m very sorry Ms. Draper. I’ll make sure it doesn’t happen again.”

“What seems to be the problem?” I said as I approached. Cassie’s eyes showed a visible relief that I was swooping in to save her, while Eve just looked annoyed, perhaps sensing that I would take Cassie’s side.

“Nothing, Roger, just making sure Cassie knows what is expected of her at this office.” Cassie rolled her eyes while Eve was looking at me.

“Well let me teach Cassie. She’s my secretary.”

“Whatever. As long as things are done to acceptable standards.” Eve turned and walked away briskly. That woman was built like the figure head of a ship., or Jessica Rabbit. Almost impossibly curvy with long red hair, as much I disliked her I loved to watch her ass swing in her skirt as she walked away.

“Sorry about that, Roger.”

“Oh don’t be, Eve can be, between you and me, a total bitch sometimes.” Cassie was wearing a free flowing, yellow sundress with a vaguely African print. Perfect weather for a hot, early summer day. Towering over her, I could look right down the front without drawing too much attention. Her tits were small and perky, her nipples stiff in the air conditioned office.

“Don’t worry,” Cassie’s smile was innocent and heartwarming. “She doesn’t really bother me. If you had a problem I’d be much more upset.”

“Well I think you’re doing fine. Keep it up.” I tore my eyes away from Cassie’s breasts to go into my office. Between Cassie’s nippples and Eve’s ass I was already sporting half a boner. I leaned back in my chair and unzipped my fly to jack off. With my eyes closed I could imagine Cassie, naked and laughing as she bounced on my dick, or Eve’s milky breasts and glasses covered in my semen. After a few strokes I opened my eyes and sighed. This was getting me nowhere. I knew Cassie was craving my cock, why hadn’t I seized the opportunity? I didn’t want to possibly drag myself and the office into some kind of sexual harassment scenario, I reminded myself. But my libido needed to be released, and the best way to do it was just outside my door. I zipped up, rubbed my forehead, and turned on my intercom.

“Cassie, come in here for a minute,” I said.

“You got it boss,” came the reply. She came waltzing in to my office, practically floating with her effervescence. I adopted a stern demeanor. “What do you need?”

“We need to talk about your relationship to me.”

“…oh.”

“Cassie I know you’re attracted to me. You’ve made that clear enough. In truth, you’re a beautiful girl, and I would be lying if I said I wasn’t attracted to you, too.”

“I see.” She looked crestfallen, and I began taking a few steps toward her.

“But relationships between superiors and subordinates are explicitly banned at this company. And you’re
also 15 years younger than me.” I was standing very close to her now. She wouldn’t meet my gaze.

“So what I’m saying is…” I lifted her chin up with my fingers to look her in the eyes. When I did she inhaled sharply, and her eyelids fluttered. “No one can know.” She threw her arms around my shoulders and, standing on tiptoes, kissed my deeply. Her body was hard and warm. Her nipples pressed into my chest. I put my hands on her boney, wide hips and for a few moments we played with each other’s tongues before separating to breathe.

“Roger, you’re married. You can’t do this.”

“Cassie, my wife doesn’t know a lot about who I sleep with, and she’s hardly innocent herself. This is what you’ve been waiting for, enjoy it.” We kissed deeply again, and I cupped her toned buttocks with my large hands. She pushed me away and bit her lip.

“I want to taste your cum.” I walked back to my chair and sat down. I gestured in a broad “come and get it” manner. She smiled and walked behind my desk, kneeling before me. My cock was seven inches, but she wrangled it out of my pants and began to stroke it into a full, hard erection. I was already feeling the waves of pleasure her small, nimble hands were giving me, and the thought of her soft, wet mouth was driving me crazy with anticipation. She licked, exaggeratedly, my tip, before sinking the rest of my rod past her lips. I felt her gullet part for me and my cock enter her throat until my balls were on her chin. She beamed up at me and began to give what was, easily, one of the top five blow jobs of my life. I was about to fill her stomach with cum when there was a knock on the door.

“Roger, it’s Jim, I need approval on this change to the campaign.”

“Shit.” I said quietly. Cassie was holding my dick in her hand now, neck twisted to look at the door. “No time, hide under the table.” Cassie nodded and obeyed. I quickly tried to pull myself together. “Come in!”

“Cassie seems to have stepped out.”

“Yeah she had to run an errand. You need me to sign something?” Jim began a thorough, long-winded explanation of what it was he was changing, the reasons for the change, the chosen course of action, and the myriad other options and why they were discounted. Cassie sat patiently under the desk for the first two minutes, but rounding the third began to twiddle by knob between her fingers. Eager to finish what it started earlier, my penis swelled up in her hands. She began with just fondling, but soon progressed to outright stroking, then licking, then, as Jim was on page five of his 10 page report, sucked my cock entirely into her mouth. I managed to hold out for half a minute before I decided I needed to act.

“I think I’m ready to sign it.”

“Are you sure? I haven’t even covered third-party demographic differentials and their bearing on potential consumer drop off.”

“Yes I’m sure,” I practically hissed. Cassie had one hand rubbing my balls now, and was furiously swallowing the last half inch of my cock in an effort to get me off. I signed whatever Jim put in front of me and quickly talked him out of the room. The second the door closed I slid my chair back to look at her. Her eyes smiled at me above a mouth full of cock.

“You fuckin’ bitch,” I tried to say playfully, but my last syllable became a drawn out moan as I released my load into her hungry belly. My hands clamped down on the back of her neck and my dick plunged to the hilt in Cassie’s esophagus. Her eyes quickly flashed to shock, then she relaxed and let my cum flow through her into her stomach. I shuddered as I fired my last shots down her gullet. It was only then that I realized that Cassie had done a terrific job of taking my eight inch cock down her throat. My cock’s length had stymied many blow-jobs, but Cassie took the whole thing in her mouth. Easily the best secretary I’d ever had.

My balls drained, I leaned back in my chair, letting Cassie clean up my base and her chin, onto which some drips of cum had leaked. She finished her last swallows and hopped onto the desk. Her ankles flew up to rest on the armrests of my chair.

“Now you do me,” she said, grinning. Eagerly I obliged, shoving my bald head under her dress and devouring the neatly trimmed pussy I found there. When she came her thighs grabbed my head like a vice until I thought it would explode. She didn’t scream or moan, but only because of the office beyond the door did she restrain herself to petite sighs and delicate grunts. After that we had to at least pretend to work for the rest of the day. Before she went home I convinced her to jack me off on my couch, and I draped her tits in my silky cum. I, unfortunately, had to stay late and make up for the work I hadn’t done while I was fucking her, so it was going to be a late night for me.

I’d had a few drinks while filling out reports, and it was around 8:30 when I stepped out of my office for a break. I noticed a light at the far side of the floor and the clicking of high heels. I thought I might investigate, and depending on the source of those high heels, get rid of the semen that had been building in me since I kissed Cassie goodbye. I poked my head into the copy room, where I could here the printer chugging away. Standing with her hair down and her blouse a button lower than it had been earlier was Eve. Eve had been irritating to me since I’d first started working here, and her being rude to Cassie earlier today only made me angry. Still, her cleavage heaved in her shirt, and her ass had never looked fuller or juicier.

When she stood at the copier I crept into the room and sidled up behind her. With my two big hands I grabbed her supple cheeks and pushed her hips against the copier. She jumped, then sighed.

“Roger, I always thought you were better than this.”

“Eve, you don’t have much say in this matter.” She gasped as I moved to grope her tits through her blouse. They were as soft and big as I’d always imagined. Eve was becoming flustered.

“Honestly Roger, while I admit I’ve always found you attractive in an abstract kind of way. I don’t have the time right now!”

“Jesus, Eve! You don’t get it. I’m filling your cunt with jizz tonight and there’s nothing you can do about it,” I punctuated this by ripping open the buttons on her shirt. I heard them skitter across the floor. Eve finally got it, gasping sharply.

“Oh God…” Eve’s bra was lacy and sheer, and I could just about feel her nipples through the fabric. Meanwhile, my erection was pressing stiffly into Eve’s ass. As she protested, I forced pushed her down against the copier glass while I took my cock out with the other hand. Swiftly I pulled her skirt up and her frilly panties down. I pushed my erection against her softness, rubbing it in her juices. I returned my hands to her breasts and ripped open her bra this time, letting her massive tits to flop out. I grabbed the fleshy expanses and squeezed until Eve yelped. I pushed her back down to the glass to insert my cock. I also decided to make some copies of Eve’s tits, just for personal use. 100 should do.

I guided my tip into her pink cunt and thrust forcefully until my manhood hit cervix. Even then I pushed a little harder than normal, prompting another yelp of pain. Eve was audibly weeping. I twisted and pinched her tits with reckless abandon. Glancing to the side, I noticed my copies were coming out nicely.

Slowly, the tenor of Eve’s cries changed. She wasn’t being very loud any more. Her sobs sounded more like… moans of pleasure?

“Oh Roger! I’m such a slut. Rape me!” It looked like my suspicions were being confirmed. Eve had always had a cock-craving whore locked deep inside her, and I guess some forced sex was the way she could finally let it out. I was of two minds about this. On one hand, my power play to finally but the bitch in her place wasn’t quite panning out as I expected. On the other, I didn’t really have to worry about consequences if she ended up being into it. I might even be able to turn this into a multiple time thing.

“Fucking whore!” I yelled. I slapped her pale ass with my right hand as hard as I could. Eve screamed and her ass quivered where my red hand print remained.

“Again, daddy! I want your cock!” Well this had just taken a Freudian twist I wasn’t quite expecting, but in for a penny, in for a pound, I guess. I slapped her more and called her names. She only seemed to enjoy it more the filthier I got.

“You fucking bitch slut! Daddy’s going to fuck you until you cry.” I was running out of ideas, so it was fortunate Eve chose that moment to cum.

“DADDDEEEEEEE,” she wailed. Eve finally got into it, grabbing the copier with both hands and thrusting herself back and forth on my dick. She continued to scream about her father, and I started to come back around to the weirdness of this fuck. “Don’t stick your dick in crazy” was the old saying, but crazy has the nicest pair of titties I’ve ever felt, and I’ll admit this roleplaying was starting to work it’s way into my mind.
There was a familiar pressure at the base of my cock, and I figured there was no point in trying to hold out the orgasm any longer.

“’Bout to blow it,” I grunted.

“Oh God, please fill me!”

“Uh! Here it comes!” I grabbed Eve’s swinging tits with everything I had and completely exploded in her. Releasing right against her cervix, her uterus filled with my seed and more flowed out of her cunt and onto her thighs. When I was spent, which was relatively quickly, given that I had already came twice today, I pulled out. Eve flipped around and slumped down against the copier, silent. Her boobs were bruised and red. Her makeup was stained. She was practically catatonic. I’d almost feel bad for her if I hadn’t there to witness that mind-erasing orgasm. My copies were excellent. Eve’s tits filled the entire page, and her nipples were well defined, and bright pink. I looked down at the woman in front of me. Yeah. They were that great. She had easily the nicest rack I’d ever seen, even though I had beat them half to hell. Not just the size but the shape was perfect, full, and surprisingly perky for what I estimated had to be DDD-cups. Just looking at them was starting to get me hard again. I towered over her.

“What are you? 38DDD?”

“E,” came the murmured reply. Shit, if I didn’t just feel them I’d guess they were fake. I knew what I had to do. I started stroking my rod to a full erection. Since I’d just cummed, beating off felt like pounding meat, and I was seriously considering rescheduling this cumshot when Eve opened her mouth and placed it on my member. The poor girl could only take the first four inches in her state, but I handled the base on my own. On the edge for the fourth time today, I pulled out and let Eve gently lick me.

“Daddy’s gonna cum on those big tits, baby girl.”

“Just not on my glasses,” she said. Eve continued licking until I pushed her gently back against the copier. Taking aim at where her crossed arms pushed her luscious mounds together I fired, and sticky jizz landed from her chin to her wrists, hitting everything in between. Eyes closed, Eve took a drop from her hand and licked it. She smiled.

“Roger it tastes so goooood.”

“I bet it does, baby.” I fished my phone out of my pants and snapped a picture. Never know when I’ll need fapping material. After that, I called it a night.

When I got into work the next morning I only had one thing on my mind: finally giving it to Cassie hard in her cunt. We had an executive meeting at 10:30. So I walked directly into the boardroom to start my day. I wanted to defile that sweet minx right on the hardwood. After 20 minutes I called Cassie on my cell into the boardroom. She waltzed in quickly, a vision in a white dress. After closing the door, Cassie lept into my open arms and kissed me deeply.

“I’m not wearing panties,” she said in a whisper.

“Well then let’s get this dress off.” I pulled the thin fabric over her head and beheld the skinny girl naked before me. As usual, Cassie didn’t wear a bra. I usually like a little more curve to my women, but Cassie’s smiling face more than made up for it. I couldn’t wait to cover it in cum. Cassie hopped up on the table and wrapped her arms around my neck. I took out my fully erect phallus and guided it in as I kissed her. After a few seconds a problem quickly presented itself. Cassie’s cunt was just too shallow to fully take all eight inches of me. Last night Eve was deep and enveloping, but Cassie had quite a different build. Cassie was sure enjoying herself, but after a few minutes I was just bored, and felt myself soften.

Cassie had just finished cumming from the girth and length of my cock that I thought now was a good time to try her, full of gratitude as she might be.

“Keep going, I think I might cum again,” she said.

“Cass baby this just isn’t working for me.” I decided to keep fucking her while I made my case. Couldn’t hurt. “You’re too short, I’m not going to cum.”

“Uhuh.”

“I need to put it in your ass.” Cassie opened her eyes at me but kept bouncing on my dick. I’d never noticed how piercing blue her eyes were.

“Honey why didn’t you say so? I’d love to have that giant cock up my ass.” I sighed with relief. If this was going to be a sticking point I didn’t know what I’d do. Cassie lowered her back against the table and exposed her pert asshole to my cock. I dipped my fingers in her juice and rubbed them on the small hole and on my dick. Grabbing Cassie’s ankles and placing them on my shoulders, I slipped my head into her ass, and soon followed with the rest of me when her colon opened to me.

“Mmmm. It’s so big I can almost feel it in my belly.

“Feeling okay?”

“I’ve done this before, babe, pick it up.” Gladly I obliged. In truth her ass was tight and wonderful. With every thrust my balls slapped against her ass, and my entire shaft was buried in her. Cassie had her arms spread out above her head, feeling the wood and running her fingers through her splayed hair. I could see that her clit was engorged and absentmindedly rubbed it with my thumb. Cassie moaned maybe a little louder than I would have liked, and shuddered at the force of her orgasm. My cock, deep within her, felt the contractions of her muscles all the way from her abs to her sphincter, and the sudden sensation got me to suddenly cum.

I shot my seed into Cassie’s colon as she writhed, and kept pumping wave after wave into her bowels. I had never had anal sex this good before, but then the only woman I’d ever tried it with was Amy, and she generally couldn’t take it deeper than six inches. When her intestines were filled with all the jizm I could muster I quickly pulled out. We had to move fast to avoid suspicion from the executives, and I was still naked. Cassie threw her dress on and, winking, left the room. I was just getting my tie adjusted and sitting down when the rest of the board started filtering in. Eve, turtleneck clad sat across from me. I made eye contact with her but she blushed and looked away fixing her hair. She definitely was hungry for my cock after last night. As the meeting started I wondered why it had took me so long to fuck girls at the office. Better late than never, I suppose.