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Anal sex with my boss

by SexStoriesClub on Jan 1, 2017 Anal Sexstories 18233 Views

I guess I'd had the hots for my boss Ray for a very long time, but I knew he was married, and so I'd never done anything about it. I also had a policy of at least TRYING to keep work and sex separate, although in the past I had a co-worked I was fuck-buddies with, before I met and married my husband Steven. Now Steven and I do have an open relationship, having met over the internet, on a swingers and adult sex site ourselves, but still, most of our encounters with others, we share together.

Somehow, I just couldn't see myself explaining that to my boss, or even seeing him in bed with another man, much less my own husband! And so my fantasies about Ray my boss, stayed just that, fantasies!

One day I was in the bookkeeping room doing some filing. It is also the room with all our office copy machines, and as I filed people would come and go, using the copiers. At one point, I was on the other side of some file cabinets, and in walked Ray and another male co-worker, and they were talking.

Neither man knew I was there, and I kept it that way, as the topic they were discussing was sex, and their wives! The one guy said something about how his wife hardly ever gave him oral sex any more, and Ray just chuckled and told him that HIS wife hadn't done that for him in well over a year now! The topic then shifted to anal sex, with both men agreeing that neither of their wives would even consider it, much less do it! It then got quiet for a minute, and then came a confession from Ray, that really surprised the hell out of me!

Ray was telling the other guy that his marriage was probably over anyway, as he and his wife even slept in separate bedrooms now, and had been for over eight months! Our surprised co-worked asked him if that meant that he hadn't had sex for eight months now, and Ray responded, telling him it was more like closer to a year since he'd last had sex! A YEAR! I personally couldn't even imagine going without sex for a month or two, but a YEAR! It was right after that the two men left, and I was again alone in the room. Waiting a minute or two, I went straight to my office and got my purse, and then went straight to the lady's room. The purpose of my visit was to pull out a maxi-pad and shove it into my panties, because they were absolutely, and positively soaking wet from my pussy!

I was so turned on, that I had trouble concentrating the rest of the day that day, and Ray popping into my office with questions certainly didn't help either. By the time I got home that night, I was so horny, that the kids thought I was nuts making them go to be almost an hour early, just so I could hurry up and get naked in bed with Steven. (of course they didn't know that part!) Once in bed, Steven immediately knew something was up, and so as we lay there, me stroking his hard cock, and him fingering my wet pussy, I told him the whole story! We were both getting really worked up, but Steven's two word response, really through me off guard. "Fuck Him" was all he said, and so I had to ask him why he was bring so cruel about another man's situation?

Steven laughed, and told me that he really meant I should fuck him, and that I had his permission. Now since we'd first married, he'd known I had a "thing" for Ray, but this suggestion, even took me by surprise! I asked him to explain, and Steven even went so far as outlining a plan, where I would accidentally be working late the same night I knew Ray would, and that I simply use my female charms, and seduce him! I asked him if he was serious, and he quickly pointed out how hard the cock I was holding right then was, and then he rolled on top of me as I spread my legs open, penetrated me, and started fucking me! Before he stopped talking though, and really started slamming his hard cock in and out of my VERY WET PUSSY, he added one last thing, and that was that "after" I had to come right home and tell him every single, juicy detail!

God, I love my husband!

I didn't want to just chance springing things on Ray though, and facing possible rejection, and so I took things one step at a time. Additional flirting, and giving him quick glimpses of my 40DD tits. Sometimes clothing a little too suggestive for the office, but not enough to get me into any trouble. Then there were the lunches, and accidentally brushing against him as we walked, and other lots of other little things women do, to hopefully show they have an "interest " in a man. I felt it was all working too, as he was a lot more attentive than ever, and he was also in and out of my office, a hell of a lot more, than ever before. No one ever walked into another persons office with knocking first, but more and more Ray was doing that to me, and often catching me bent over, "filing", and getting a rather nice shot of my panty-clad ass!

That, to me, was the number on indicator that he was possibly primed and ready, as I mostly wore thong panties anyway, which really meant that sometimes he was even seeing my bare ass. I never scolded him, and he never said anything about me NOT scolding him! I now felt the time was right, and so all I had to do was wait. I wanted to wait for a night he would be working late, and then I would be working a little overtime, myself! A little after five, when I knew Ray really was staying, I called Steven and let him know I was working late on a special project that night, and that was all that was said by either of us. After all, we both already KNEW the real reason I was going to be "working late"!

It was almost two hours later though, before the entire office was deserted. Ray had no idea I was still there, as our individual offices are on opposite ends of the floor we worked on, but I knew he was still there, having check, and seen his light on, and even heard his voice, as he was on the phone. As soon as I was really sure everyone else was gone, I locked my office door, stood and took off my blouse and bra. I then put my blouse back on and started to pull my panties off too, but then thought better of it.

Most men I know love to strip a woman's panties off during foreplay, and I also knew Ray had seen my thong and ass before, and I knew it had excited him, and so, I decided to keep them on, at least for now!

Leaving my office I walked over to his, and started to knock, when I realized he was again on the phone. It didn't sound like a happy conversation either, and I quickly figured out, he was talking to his wife. I honestly hoped this wasn't going to put a damper on what might happen, but at the same time, I thought that just maybe it would be the final push he needed, to make this happen! I heard him slam the phone down, and then I waited. I waited a good five minutes, wanting to give him a chance to calm down a bit, and then I knocked. I'm sure he wasn't surprised someone would be knocking on his door at that hour, because a lot of us often worked late or came in very early. We were all on salary on my floor, and so no one really cared how much "overtime" any of us worked.

I heard him say to come in and so I did. Ray is a VP, and so he has one of those large, executive type offices, complete with the big oak desk and executive chair, his one private bathroom, and a huge soft couch, and a couple of big plush chairs. As soon as I stepped in, I saw him perk up right away, and he said my name (Shannon) and asked what I was still doing here. As I'd stepping in and the office door had shut, I locked it, trying to be a sneaky as possible, and hoping he hadn't noticed! Apparently he hadn't since he started talking right away. Ray was sitting on his big couch, a bottle of scotch on the little table next to one end, and a glass that was less than half full, indicating he'd already had at least part of one drink. He seemed pleased to see me, and invited me right in, patting the couch, and indicating for me to sit.

I asked him how things were going, and for a split second there was a frown. He told me things were just so-so, but now that I was here, they were much better. I scooted a little closer to him and nudged him with my elbow, and then scolded him for not at least offering me a drink. He started to get up, and I stopped him, telling him I knew were the glasses were and I was perfectly capable of getting one for myself. I then put my hand on his thigh, as if to push myself up, making sure my fingers at least should have been right were the head of his cock would be under his pants, and then I got up and strolled over to the little cabinet across the room. I was sure he was watching my ass as I walked and I had worn a skirt that day that was maybe a little to tight, but not THAT tight.

As I turned to walk back, I swear I saw his hand quickly move away from his crotch. I was also glad then that I had taken off my bra. Not only could Ray SEE my tits giggle under my blouse, but my nipples were so hard by then, that a bra would have only irritated them, and not stimulated them! This time, when I got back to the couch, I sat down right beside him, thigh touching thigh, and he damn sure didn't move, and he damn sure didn't seem to mind. He poured me a drink, and then we toasted to something silly about our jobs and the company, and then as I sipped about a third of mine down, Ray drained his glass! Setting his glass down, he half turned to me, and then managed to get my name out once again, Shannon, and I turned into him, and we kissed!

I wish I could tell you I had to work at it, that I had to SEDUCE HIM, but that just wouldn't be the truth. This was a man who was both lonely and hungry. A man who, if he wasn't lying, hadn't had sex in over a year! (AND NO, masturbation DOES NOT count!)

"I'd" spent the better part of a month by then, taking our work-related friendship, and using every trick in my rather large book of womanly tricks to let him KNOW I wanted him, to let him know I wanted his hard cock! NO matter what anyone says, "I" know that once the pheromones are flowing and the hormones going, there isn't a man OR woman on this planet, that DOESN'T know when the time is right, when I want him and when he wants ME! We were both kissing with a pent up passion that can only happen the first time a man and woman are together sexually! Almost immediately his hand was inside my blouse, and he was cupping my big tit. His fingers sought my hard nipple out, and right then he sighed, telling me how big and hard my nipples are! Like, "I" didn't already know that!

"My" hand sought out his hard cock, squeezing it though his pants, and then it was me saying the dumb thing, as I told him how big and hard his cock felt, as if HE didn't already know that himself!

From that point, it was all happening so fast! Ray's shirt, my blouse, and then me undoing his pants. Suddenly Ray seemed to freeze, and then a single word, "Door?", I used my hot breath in his ear, and I told him I already locked it, and then, clothes were again flying! I wanted to be somewhat in charge, because there really was a certain way I wanted things to go, but at the same time, I did let him have his way for a while. Ray attacked my tits! I knew his wife was much smaller breasted than me, and I guess he'd probably looked at my tits, maybe even fantasized about them for so long, and so for a while at least I let him suck them.

At this point, HE still had his boxer shorts on, and so after letting him play with and suck on my tits for a while, I sort of pushed him back, and then before he could say anything, I slid off the couch, and got down, kneeling between his legs! I slid his shorts down, and his beautiful hard cock, sprang into view! He had a very nice cock too! Just guessing, I figured he was an inch or so longer than Steven, and since HIS (Steven's is exactly six inches long, that meant Ray was around seven, maybe seven and a half. He was the same thickness as Steven though, and I had ALWAYS been satisfied with how "thick" Steven's cock was! Ray also had big balls as well, and one of my own private, secret little turn-on's has always been men with large balls!

As soon as I leaned over and ran my tongue around the head of his beautiful hard cock, Ray groaned. He groaned and his hips came off the couch. Normally, I would have started licking his hard shaft next, but with him, with this situation, I immediately opened my mouth, and immediately sucked his cock in!

"Oh God Shannon!"

"You have NO idea how good that feels, and you have NO idea how long it's been for me!"

OK, well I may not have had a real idea how good it did feel to him, but I DID have an idea how long it had been. I'd heard that for myself, even though HE didn't know I'd heard it! Looking up at him, I let his hard cock slip from my mouth, for just a second, but I still held it firmly in my hand.


"TELL ME ... to suck it for you, oh God baby, tell me to do it, tell me, it turns me on SO MUCH!"

His eyes were glazed over, his look, one of passion, and one of, well, I can only describe it as one of pure lust!

“SUCK IT FOR ME SHANNON, Oh Yeah, suck my hard cock!"

I was doing just that, my mouth sliding up and down his thick shaft. As I said before, normally I would have taken a lot lore time, done a lot more licking and then licked and sucked his balls as well, but that night, I knew hw long it had been for him, and so I just sucked! Just as I'd figured too, it didn't take long. His hips were gyrating and he was moaning loudly. His hands were on my head, and his fingers tangled in my hair. As I sucked up and then back down, he would thrust his hips up, attempting to fuck his hard cock into my mouth. Only a moment or two longer, and then his voice;

"Oh God Shannon, you're gonna make me cum!"

He was being a gentleman, warning me, but all that made me do was suck harder, and my head bob up and down over him even faster, and then he groaned loudly, and I felt his cock jerking in my mouth. He had quite a large load, but he tasted wonderful, and so I did my thing, and I sucked and swallowed, sucked and swallowed, until his balls were drained, at least for the time being! When I sat back up beside him he kissed me. I was still holding his cock and it was still very hard, not surprising for a man under his circumstances. He again attacked my big tits, and this time I let him, and then as he pushed me back, I lay back on the couch, and lifted one leg, hanging it over the top of the couch, and spreading myself open even wider for him.

I could feel his breath on my pussy, and then he said something about how he just wanted to look, for just a minute. I told him to take his time and the he told me I might think he was silly, but mine, was the fist completely shaven pussy he'd ever seen close up in his whole life! I would have laughed had it not been so sad, and I spread my legs open even wider, and told him to look all he wanted. I felt and heard him breath in, and I knew he was smelling my pussy. I looked over and saw his hard cock twitch, and it turned me on to know my "smell" was turning him on too! His tongue came out and slid between my pussy lips, and I moaned softly and told him to lick me, and told him how good it felt!

Ray ended up being very good a licking pussy, especially for a man who had not had much practice in a long, long time! I knew he could make me cum that way, but by then I wanted to fuck, I wanted to BE fucked, and in the worst way. Looking down at him between my legs, I sort of tugged at his shoulders, and he immediately got my intention. Moving up my body, he was now on top of me, and I could feel his hard cock poking, probing at my pussy. I reached down between us, and held him, held his hard cock in my hand, and I guided it between my wet pussy lips and up against my wet fuck-hole! The head of his hard cock felt huge, and it was just beginning to press into me. I groaned and looking right into his eyes, I begged him to fuck me! He thrust forward, and the head of his cock penetrated me!

"Oh God YES Ray!"

"Fuck me!"

"I need you to fuck me now!"

He thrust forward hard, and his balls smashed into my ass. He was all the way inside of me, and without hesitating he withdrew, and then thrust into me again! It was immediately wild, and it was animalistic. As he thrust down into me, I lunged my hips back up at him. His balls were smacking off my ass, and we were fucking like two teenagers in heat! I was actually surprised, and majorly caught off guard, as my first orgasm blasted through me! It had been a while since I'd climaxed this easily, this soon after starting to fuck, and it was wonderful! My orgasm caught Ray off guard too, as well as the intensity of it, and he even slowed down for a moment, to ask me if I was OK! My hands slapped down hard on his ass, and I told him in no uncertain terms NOT to stop now!

Our "fuck" may not have lasted long, maybe fifteen minutes all together, but it was so fucking intense! After my first orgasm I could quickly feel another building. I knew he was getting close too, as the power, the intensity of his thrusting only increased. His balls was just smacking off my asshole, and then in one huge and powerful thrust, he suddenly buried his cock as deep inside of me as he could get it, and then he held himself there! As soon as I felt the first jerk of his hard cock so deep inside me, and then felt the first blast of his hot cum shooting into me, I lifted both of us off the couch, and just ground my pussy into his crotch. My tits were smashed into his chest, and I was grinding so hard against him as he came inside me, and then I blasted off myself, into an even more intense orgasm, than my first!

We were both breathing hard, our bodies all hot and sweaty. I held him, as he lay on top of me, his body covering mine. Neither of us spoke, and then we kissed, tenderly, but still with passion! His cock grew soft and slipped out of me, and eventually he got up, and got us both a towel. We sort of half sat, and half lay together for a long while, whispering softly, and talking about nothing. Little by little, I let my hand wonder, until once again, I was toying with his now soft cock. He began to grow hard again, even though it took a little while, and as his cock stiffened in my hand, he whispered to me, telling me I was in satiable! I thought to myself, if he thought I was insatiable now, then he ought to see me in bed with TWO MEN, and TWO HARD COCKS!

Eventually I slid back off the couch, and then once again had his cock in my mouth, bringing him back to full erection! When he was fully hard again I let his cock go, and slid back up by him, and then, probably almost gave him a heart attack, as I told him point blank I wanted him to fuck me in my ass! The look on his face, his expression, was just priceless, as he asked me if I was serious, and if THAT, was what I really wanted. I assured him that I DID want just that, or I wouldn't have asked. He then got the oddest expression on his face and he told me he really, really wanted to, but only if I would let him do one thing first. I quickly asked him what, and he told me he wanted to lick my ass, and I sighed, and told him I would love for him to do just that!

It was like a scene from a porno movie as neither of us was shy about anything now! I got on my knees on the couch and stuck my ass right up into the air. Ray got behind me, and immediately started licking my ass, and asshole! It was FANTASTIC! He was like a kid in a candy store, and I felt so open, so hot, so turned on, and so nasty! His tongue slid from the top of my ass crack, down across my asshole, and down to my pussy and then back up again. Eventually, he concentrated on just my asshole itself, and everything he was doing went wonderful! After several long minutes, he suddenly stopped and asked me in the most serious way if I had any lubricant. It wasn't like I wasn't an old pro at doing this sort of thing, and so, I simply told him my pussy juice would do, and he could START with his cock there, and then move to my ass!

Right away he was upright, and then I felt the head of his cock poking into my pussy again, and then once again he was inside of me! As he held my hips and started fucking me from behind, I began to think he was getting just a little to "into" fucking my pussy, and this time, I wanted his hot cum somewhere else! Looking back over my shoulder at him, I told him directly that his cock had to be slick enough by now, and that I wanted, no I NEEDED his hard cock in my ass, and that's when he seemed to snap back to reality, and he pulled his cock back out of me! I now felt the head, as it pressed against my asshole. He seemed to hesitate, almost like he was unsure, and so "I" pushed back, and suddenly the head of his hard cock, penetrated my tight ass!

His cock was a little larger than Steven's but Steven and I have anal sex often enough, that even Ray's increased size didn't hurt me. As he eased himself inside of me, inside my ass, I felt his fingers digging into my butt cheeks, and I continued pushing back into him as well. His pubic hairs were against me, and then I could feel his crotch pushing into me, and his hard cock was buried as deep inside my ass as he could get it! I heard him, almost gasping for air, and then his voice, so sweet, so gentle, as he suddenly spoke!'Oh My God Shannon, I never knew!"

"So Hot!"

"So Tight!"

"I just never knew!"

"Oh My God Baby, you ass feels so fucking good!"

I looked back at him. I wanted this to be for him, a fantasy moment he would never forget in his whole life, and so I looked back at him and the spoke to him!

"Oh Yeah Baby, and your cock feels so good in my ass, and I absolutely love a hard cock fucking me ass, so fuck me, fuck me now and cum in my ass whenever YOU are ready!"

His hands were on me, and his hard cock inside of me, and once again, he began to fuck me, only this time, DEEP, inside my ass! There had only been a couple of other times I've ever climaxed, JUST from being fucked up my ass. Once with a guy a long time again, and one time with Steven. It was incredible that NOW, as Ray fucked my ass, I was getting so close, and then I KNEW, I was going to climax! Once again, another rather intense orgasm, that surprised even me! I could feel my ass contracting around his cock. I could hear him grunting hand feel him thrusting into me. Suddenly he was clutching my hips hard, and then even more suddenly he thrust his hard cock up into me, impaling me onto his thick hard shaft, and then he held me tight, my ass pressed into his crotch, as his cock jerked violently inside of me, and he filled my ass with cum!

His body jerked hard against me, once, twice, three and then four times, and with each spasm, his cock jerked hard inside of my ass, and his cum blasted out into me! At the beginning of this night I had worried! I had worried about whether or not he would even want me, and now, well NOW, he'd cum in all three of my holes! His last orgasm, i my ass, had been the most intense by far, and now I knew, we were through, at least for this evening!

Ray almost begged me to let him keep his cock in my ass for a while longer, and I told him to take as long as he wanted. Over the next few minutes, he must have used the words, "fantastic", "wonderful" and "incredible" at least a dozen times each, and I accepted his compliments, and returned them, all the while thinking to myself, what an absolute FOOL his wife must be!

As Ray's cock grew soft and slowly slipped out of my ass, I knew several things! This wouldn't be the last time, and who knew what was to CUM, after this night?

Article source: https://sexstoriesclub.com/anal/4-Anal-sex-with-my-boss.html

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