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Damn That Brad

Category: Anal Sex
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Ever since he started working here, he had been nothing but arrogant, cocky and condescending. He looked harmless enough the first day he walked in here but the minute we began working together, I knew it was going to be a doomed relationship. Why did my bosses place his desk right next to mine? Probably because they didn’t want him next to theirs. The office we worked in was actually a loft studio, a big open space filled with groupings of desks and other office equipment. No walls to shut us off from one another. Which was unfortunate when there was such a man like Brad in the room.

God, I couldn’t stand him. This week, we had a meeting discussing our methodology of production for we all collaborate on the same projects, and synchronism is essential in our work methods. I specialized in website production, meaning I take the graphics, cut the them and insert them into html pages. Brad’s job was to organize the structure and hierarchy of information for websites, so I had to follow his lead, organizing my html pages to reflect the structures he created. Which makes it all the more aggravating, since he was so particular and anal about it. Everything had to be organically structured according to him but the maddening part was that he couldn’t be bothered to explain it properly, it was as if he expected us to read his mind and if we couldn’t, well, it was because we were just naturally inferior, not blessed with his brilliant genes.

One night, we were having a company get-together at Ella’s, a neighbourhood drinking hole. My bosses thought it would be a good idea every so once in a while to get out and drink together to foster closer relationships and to reward us, their employees, for being the hard workers that we were. I didn’t know if it was actually working but hey, free drinks were free drinks. The downside was that Brad was going to be there too. I divested much of my time and energy to ignoring him as much as possible at work, to avoid interacting with him directly in any way. Granted, he’s nice to look at, even though he was blond, pale and blue-eyed whereas I preferred tall dark men. But that was just about the only decent thing I could say about him.

The clock was quickly sneaking up on five p.m., the end of the office day. We were carpooling over to Ella’s. Brad was tagging along with me and Simon, the head graphic designer. Damn. I avoided eye contact with him when I offered a ride to the staff this morning over the coffee machine but he said he would accept my offer. Great, I will have to listen to his obnoxious banter in the car on the way to the bar. I glared at the clock, for it seemed to belligerently hurry to the end of the day as if to deliberately piss me off. Ordinarily, I was quite happy to see the workdays speed by but not today, not when it meant that I would have to actually socialize with this teutonic asshole.

Ah! The hour hand just arrived on the number five. Sullenly, I put away my work materials and cleaned up my desk. Turned off the Mac and grabbed my purse.

“So, ready?” asked Brad.

“Yes,” I lied.

Of course Brad wasn’t ready to leave yet. Simon and I sat on the couch that was by his desk and waited for him to finish, he patiently and I, not so much. I glared at Brad, mentally willing him to hurry up and meanwhile, resenting him for making us march to his tune. How did he do it? How was it that he could be so oblivious to the fact that the world actually does not revolve around him? As I mulled over this, I could feel my nostrils flaring and billowing invisible smoke. Brad looked up finally and saw us sitting there. “Well, are you ready yet?” he asked, getting a pissy look from me as I got up from the couch and began walking out of the office. I don’t care if he’s ready to go or not, I’m leaving and that’s all there is to it. Simon looked around uncertainly, not sure if he should follow me or wait for Brad. They are best friends and tend to stick together like Jekyll and Hyde. They followed me finally, meeting me in the parking lot where my car was. Simon and Brad haggled over who was going to get the front seat until I impatiently started up the car. They scrabbled to get in any which way when they realized that indeed I was not going to abide their squabbling.

I live in the same neighbhourhood as the bar and knew the fastest way to get there, bypassing the usual traffic jam. But Brad could not resist directing me on where to go for he wanted to get there as quickly as possible. Which I found insulting considering that I drive home to this neighbourhood every day and by now, knew the fastest way for I am not the most patient driver. But when he, sitting in the back seat, saw my face in the rear view mirror, he quieted down and within a matter of minutes we had arrived. I couldn’t resist giving him a smug look as I switched off the car ignition.

My bosses were already there, and gone ahead with the ordering of beer pitchers. As soon as I sat down, I gratefully poured myself a glass, still seething from having to be in the same car as Brad. He sat down next to me, leaned back on his wooden chair, spread his legs out on the floor and lit up a cigarette. “Would you like one?” he asked, proferring a cigarette that was poking out of his pack of smokes. Since I had just ran out of mine, I grudgingly accepted. He pulled out his lighter and uncharacteristically lit my smoke as if he were Cary Grant. Hmph.

I downed my beer and as I reached for the pitcher, which was across the table, Brad leaned over and got it for me. He filled my glass and gave me a small smile. For all the resentment I harboured towards him, I still couldn’t deny his manners so I gave a perfunctory smile back by way of thanks. Now that I had some beer and a cigarette, I allowed myself to relax, also leaning back in my chair, not really paying attention to the dialogue at the table. I was content to look around the bar and people-watch. Study how people interact, how the women pose, how the men preen. How the waiters harry to and fro, trying hard to keep up with the demands of the thirsty clientele.

I felt a tap on my arm, it was Brad. “How are you doing?” Why are you talking to me? I thought to myself, as I turned to look at him. I just wanted to chill out and enjoy myself. The last thing I was interested in doing was paying attention to him.

“I’m all right, I’m all right,” I replied curtly, hoping to discourage him from speaking to me further but to no avail for he kept on talking. “Thank god it’s Friday, eh?” he said and I nodded briefly, still clinging to the hope that he will turn to someone else and bother them instead. But I could feel his eyes on me even though I was avoiding eye contact with him. “You don’t seem to like me much,” he observed. Gee, no kidding. I reluctantly turned to look at him and said “I have a hard time abiding you.”

His eyebrows went up in surprise, perhaps at my bluntness, or my honesty or both.


He opened the can of worms, for I kept on talking, telling him that I found him to be quite frankly obnoxious and that his sense of intellectual superiority was misplaced and uncalled for. He stared at me slackjawed while I ranted on and when I finally finished, he laughed and asked if I would like another cigarette.

His response caught me off-guard. For one thing, I didn’t expect him to take my ranting with such humour and unflappability. I had to give him kudos for that as much as I really didn’t want to. He was starting to strike me as being more human, more appealing, and irritatingly enough, more attractive.

I turned around to strike up a conversation with someone else for by now, friends of ours had joined the table and it was starting to become quite a beehive of tipsy conversations. As the night wore on, I drank more beer, all of which Brad poured, smoked more cigarettes, all of which Brad offered. By the time the end of the evening came around, I wasn’t feeling such animosity towards him anymore and even laughed at some of his stories, for he did tell them well with enviable wit and an excellent grasp of language.

As tipsy as I was getting, I didn’t lose my own grasp of the awareness that my feelings towards him were starting to change. But would admit that the alcohol certainly helped smooth out the roughness of my perspective of him, rendering him pleasantly smooth to talk to. At the same time, I was also aware of how strange and unexpected it was to see him in a different light. I began to pay more attention to him, observing his behaviour and expressions. I liked how he sat in his chair, laidback and calm. He exuded masculine sexuality that I could not deny existed. It was fascinating to see these new facets of him.

Before long, it was closing time and it was time to go. Everyone was slowly getting ready to leave, prolonging their farewells and making promises to get together on the weekend for predictably more drinking. I did the same and wandered out of the bar. Brad was leaving at the same time.

“You’re not going to drive home, are you?” he asked.

“Nah, nah,” I replied, “I live pretty close by, just gonna walk home.”

“Mind if I walk with you?”

“Suit yourself.”

We walked towards my place, mostly in silence when at one point, he abruptly stopped and pointed out his apartment which was quite close to mine, only two blocks away.

“Oh wow, we’re neighbours,” I sarcastically commented to which he wryly grinned. We paused there on the sidewalk while he pulled out his smokes. He lit up a cigarette and gave it to me. As I took it from his hand, I noticed how warm his fingers were. I looked up at him and he was unwaveringly staring at me, or more my lips really. I am not vain at all, but I know I do have nice full lips for I’ve been told that many times. I also know that being the tall lean brunette I am, that many men find me attractive but I never thought he would for he certainly had never given that indication before. I stared back at him and could feel the flush of heat rising up in my neck, a sure sign of pure attraction. I wondered if he could see it, my skin turning pink from the heat. He must have for he imperceptibly moved in a little closer to me, close enough for me to feel the heat radiating from his body. I could also smell his cologne, which was tinged with a delicious musk.

I just couldn’t help it. I leaned over to smell his neck. He didn’t move at all, not even in surprise. He actually seemed to have predicted I would. Ah, there was the Brad I knew, that cockiness. In a way, it was reassuring to see him being familiar for it was actually starting to be disorienting to see him behave almost unrecognisably tonight.

The late night wind blew gently, causing me to shiver. He put his arm almost paternally around me, lending me the warmth of his skin. Our bodies were now pressed together, close enough for me to feel his arousal pressing against my lower tummy. Close enough for me to feel my own swelling up in reaction. I gave into the sensations of our mutual chemistry and began to kiss his neck, and move upwards to his ear that I nibbled gently and over to his mouth that I tasted with my own. I could feel his arms wrapping more tightly around me, as if he were trying to pull me right into himself. And I did the same with him. It was funny, he didn’t seem so muscular, but he certainly felt so. I could feel the muscles in his back ripple as he embraced me, and it weakened my knees, I had to roll my eyes at myself, for being so clichéd but I didn’t care. My neck was getting hotter and hotter the more we kissed for damnit, he could kiss.

After a while, we broke apart, to take a breath and to take in the realization that we were actually making out, us two. I was especially surprised for it was only hours ago that I was full out filled with disdain and dislike for him.

He took my hand and walked me up the front steps to his place. He opened the door and pulled me in. We began to make out like animals in the front hall, he grinded his hips against mine as we frantically kissed. We had no control whatsoever, we had submitted purely and entirely to our desires. We took off each other’s shirts, unbuckled each other’s jeans, let our hands roam where they wished, our tongues following. I was in awe of Brad’s body, the way it felt, the way it smelled, so delicious and erotic and even dizzying. All I wanted to do was inhale him. Absorb him, fill up my clitoris with his sexuality until I explode, releasing all the pent-up tension of having had worked with him in uncomfortable proximity for several months.

We stumbled clumsily over to his bed for our limbs were still entwined as if we daren’t let each other, as if it was impossible to disentangle ourselves from each other. He pushed me down on the bed so my face was pressed against the mattress. He pushed apart my legs and laid down between them so that he was lying down on top of me, his legs between mine. I could feel his cock, hard and thick, resting in between my buttocks while he kissed the back of my neck. I tried to roll over but he wouldn’t let me. He began to move downwards, following the line of my spine until his warm and wet tongue was at the top of the crack in my ass.

Then he paused.

What now? I wondered.

And what the hell? It hit me hard at that moment, the awareness that here I was, lying in the bed that belong to the bane of my existence, with no clothes on. Naked in front of Brad whose tongue was on the verge of trespassing into my very personal and private places.

The shock of it overwhelmed me in very strange manifestations. I was turned on by the fact that this asshole was manhandling me, was taking control of me and submitting me to his control. It was so profane that it was making me even more aroused.

Brad pulled up my hips until I was on my knees with my face still against the cool sheet on the mattress. I could feel his hands spreading apart the cheeks of my ass, which was enough to make me gasp, but then I could feel his tongue following the line between the buttocks until it found its way into the deep recesses of my vagina, which by then, was already oozing out wanton desire onto his clean crisp white sheets. Oh my god, I can’t believe this, I thought to myself while my hips moved backwards, wanting his tongue to enter even deeper.

He pulled his tongue out and followed the line back upwards until he found the other hole. No, he wouldn’t, would he?

He did! His tongue pushed in and pushed in and pushed in until it managed to wriggle inside the opening of my tight asshole, creating sensations of pleasure that I had never known. In fact, those feelings almost transported me into a different reality as if I were no longer inside a human body, as if I were made of nothing but pure 100% orgasmic pleasure. Time no longer had meaning, I would not have been able to tell you then if it was day or night, I would not have even been able to remember my own name, I was so far gone into another realm where disbelief and arousal mutually fed each other.

Then I felt him pull out. I groaned with some disappointment for I didn’t want it to end but within seconds, I felt something bigger and harder and stiffer push against my asshole. Oh! Brad’s cock! I braced myself, knowing it would initially hurt. I relaxed my anal muscles as much as I could as I pushed my hips backwards, slowly and gently. Brad let me take control at this point, he patiently waited while I eased myself over his cock. Once he was fully inside me, the thickness of his cock rubbing against the walls of my anus, rapture once again emerged, compelling me to move back and forth with quicker rhythm until I could hear him moan. He held onto my buttocks, rubbing them as I fucked his cock with my asshole.

The whole time we were fucking, the same thought circulated through my head “I can’t believe I am having anal sex with Brad.” The shock value of this only added to the incredible delight of having a hard-on in my ass. I have never really enjoyed vaginal sex, always wanting the guy to hurry up and get it over with within ten minutes. But anal sex? I could go on all night.

For a long while, we fucked in near silence, letting out gluttonous sounds of exquisite satisfaction, the shaft of his cock rubbed me like I was a genie in a bottle, I was raised to higher and higher levels until indeed the genie came out in form of vaginal and anal orgasms, so strong that they pushed out Brad’s cock. When I came back down to reality, I collapsed on the mattress and Brad fell down next to me, his blond head, closely cropped, resting on my shoulder. We laid this way for a while, catching our breath.

“Jesus H. Christ!” mumbled Brad. “I’ve hadn’t come like that in ages!”

I smiled and chuckled quietly, staring up at the ceiling, watching the lights from the streets flicker upon it.

Brad placed his hand on my leg, stroking it gently, letting his fingers trail slowly from near my knee upwards to my sopping wet cunt. He found my clitoris, still swollen from the orgasm and began to circle it slowly with his fingers, before he moved them downwards to the opening of my vagina, letting his fingers go in and out, covering them with my wetness. Brad rolled over onto his side and gazed at me while his fingers continued to play. He was watching my reaction, letting it be his guide, each time I sharply inhale or slowly sigh, he knew he found the right spot, the right stroke and kept going.

Then Brad began to slide down on the mattress, kissing me on the way, from my shoulder, around the curves of my breasts and then down towards my clit waited in anticipation. I closed my eyes and opened my legs to let him in. He kept moving down the mattress until he was kneeling on the floor at the bottom of the bed, his head directly between my legs. I propped myself up on my elbows to get a better look of his face, of his tongue licking my clit and fucking me. Brad looked at me the whole time his tongue fucked me, which was so scintillating and almost an invasion of my personal space which made no sense for we had gone as far as we could to invade each other’s personal space.

Ah, but not quite. Brad’s space didn’t quite get invaded just yet.

Realizing this, a wicked grin spread across my face, and Brad noticed. He wrinkled his eyebrows questioning, wondering why I was smiling that way.

“Come here.”

Brad got up off the floor and laid back down besides me.

“Roll over.”

“Hmm?” I rolled him over until his back was facing me. I began to nibble the back of his neck while my fingers gently tugged on his nipples. I pressed my body against his back, letting him feel my breasts. I stroked his back, I stroked along his hips and gave him a gentle spank. Brad smiled languorously and unsuspectingly. This time it was I who slid down on the mattress, for I had something in mind.

I let my tongue follow the contours of his muscled back, and kept moving down. I let my tongue reside in that little dip at the top of his fabulously rotund butt and waited to see how he would like it. He seemed to like it indeed for his butt moved a little closer to my face.

I was getting very excited at this point because I knew that I was taking him on the ride of his life. This time, I was going to tongue-fuck him.

I moved down even more, and found the opening of his anus with my tongue, which I let flicker teasingly, pretending that I was on my way to his testicles. I would move away and then come back a little more insistently. I licked my index finger and lightly pressed it against his anus. Brad kept very still, perhaps he was wondering what I was actually going to do.

Well, he was going to find out soon enough.

I let my tongue and index finger take turns tickling his anus, while my other hand reached in between his legs to reach for his cock which was as hard as hard can get. I rolled him over onto his back and began to suck him off for a while, but I only let the head of his cock push in between my lips that he had been staring so hard at on the sidewalk. Meanwhile, my index finger would match the rhythm of my mouth. Each time his cock went into my mouth, my finger would push a little further into his anus. I made sure to dribble a little of my saliva onto his asshole so my finger could slide in easily.

Then I backed off.

He looked up at me to see what was going on.

“Put your hands on the back of your knees, ” I said.

Brad’s mouth fell open and his eyes widened. When he saw I wasn’t joking, he did what I told him to do. He put his hands on the back of his knees and pulled them close to his chest. Now I had full access to his balls and ass. I licked straight from his assole all the way up to the tip of his cock like it was a melting Popsicle on a hot summer day. I could hear Brad whimper. I buried my face into his reddish blond pubic hairs, inhaling his raw sexual scent before I moved back towards his anus. I looked at Brad, sticking out my tongue. I demonstrated to him exactly what I intended to do by flicking my tongue slowly and he rolled his eyes back in building anticipation.

I licked my finger again and inserted it very slowly into his anus. Just the tip of it, then I pulled it out and replaced it with the tip of my tongue. I went back and forth like this for a while, until his asshole was stretched enough to let me put my tongue all the way in. That is when I began to seriously fuck him in the ass. I pushed in and out with my tongue as far as it could go, as quickly as I could while Brad helped by rocking his hips. He was moaning louder and louder until he began to yell out “Oh my fucking Go-o-o-o-o-o-o-d!” It was obvious he was going to come at any point so I pulled out my tongue, replaced it with my finger and moved upwards to inhale his cock deep into my throat. I tightened my lips around his cock to massage it as I sucked him off, making sure my finger that was buried into his anus was matching the intensity and pattern of the blowjob.

Brad was so turned on that he was almost crying, he was saying that it felt so good, in fact too good that he didn’t think he would be able to come.

“Yes, you can,” I reassured him before I sucked his cock back into my mouth again.

I could feel his cock beginning to ripple and there it was, the burning salty taste of his cum spurting into my mouth, the muscles of his anus reverberating against my invasive finger. When he was done, I pulled out my finger gently and gave a little lick to the head of his dick before I pulled myself up to lie down beside him.

“No one had ever done that to me before,” he gasped, trying to catch his breath.

I laughed and got up to get dressed. He didn’t ask me to stay nor did I want him to. I bent over to grab my panties and jeans, as I did so, he rather naughtily darted his tongue into my cunt for I was bending over in front of him as he sat on the edge of the bed. “Do that again,” I said and he did. He kept going while I rubbed my clit until I came. I was so turned on from fucking him in the ass with my tongue that I was already on the verge of coming.

He lit up a cigarette after I finished getting dressed and offered me a drag. I sat down next to him on the edge of his bed and shared the smoke. We didn’t say anything at all.

He put out the smoke and I walked out the door.

The following Monday, he was at work before I was. I walked past his desk to get to mine. I didn’t look at him and he didn’t look at me.

It was as if nothing had happened. And it stayed that way.

Until Christmas eve, that is.

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