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Office Affair

Category: Anal Sex
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About 10 years ago I worked as a programmer for a small company and this is a story of what happened one afternoon between me and a colleague.

I’d always had a crush on Karen since we first met over 4 years ago, I had asked her out a number of times when we first met, but she always refused my advances and eventually I gave up and we became good friends and subsequently work colleagues.

Karen was one of the lads, she gave as good as she got with insults and comments, nothing fazed or embarrassed her.

At the time Karen was 23 and had just had a child with her partner who she had been with since they were at school. I was also living with my girlfriend and had been going out with her for a number of years.

Karen and I were working alone in the office one afternoon. All the other staff were either on leave or were working out of the office that afternoon. I was working on coding problems with a new system we were trying to implement and after fixing a few problems I passed the updated code to Karen for her to test. A few minutes later the test was complete and the code had worked perfectly.

“Fuck me!” Karen said, “It worked.”

“Ok, whenever you are ready,” I laughed.

Karen looked at me with one of her mischievous looks and got up from her chair and lay down on the floor behind me in the missionary position.

“What are you doing?” I asked.

“Well you said ok so I adopted the position,” she smiled at me.

Wondering how far this would go, knowing that she was used to playing practical jokes, I got up and stood between her legs. Being the middle of summer and with no air conditioning the offices were always hot and stuffy, so we were allowed to wear casual clothing which this time of year consisted of shorts and T shirts. From my vantage point I could see right up her short legs, she was certainly showing me a fair bit of leg and it didn’t half look good.

“Come on then,” she smiled, “What you waiting for?”

I decided to call her bluff, thinking she would quickly get out of the way when I made a move. Getting down on my knees between her legs, I leaned over her and supported myself by putting my hands on the floor next to her head.

Surprisingly Karen never moved, but continued to smile at me. “Aren’t you going to get undressed?” she asked.

“Are you?” I replied, not believing she would.

“OK,” she said, and used a foot to remove one of her trainers.”Your turn.”

I reached back and also removed one of my trainers. Karen followed this by removing the other shoe, before I followed suit.

Karen was now barefoot, but I had an advantage as I was also wearing socks.

“Your turn,” I said, knowing that she would have to make the bold move of removing a piece of clothing.

Karen then reached for her blouse and started to unbutton it. My heart was pounding fast as her bra slowly came into view. I cast my mind back to those years that I had lusted after her for weeks on end. “I’ve always wanted to see those. They are just as I imagined they would be.”

“I know, and now’s your chance,” she said as she pulled the shirt apart to reveal herself. “Your turn,” she smiled back at me.

I sat back up on my heels and pulled the T-shirt over my head and dropped it on the floor beside us.

Karen reached up and ran her hands over my chest. I was not as muscular as I used to be. I used to be very active before I changed career and ended up behind a desk all day, but Karen appeared to approve of what she saw.

Karen then sat up and pulled the blouse off her shoulders and let her boobs fall forward emphasizing their large size. She reached for my hands and put them to her bra covered boobs.

“Fuck me, they feel fantastic,” I said while gently squeezing and massaging them. I grasped and tweaked her nipples that were now pushing through the front of the fabric.

“Someone is getting turned on,” I said.

“Hmm yes and I doubt I’m the only one.”

I reached back and removed one of my socks and placed it on the growing pile of clothes.

“Not fair,” she said in mock anger.

“Well I’ve only got these shorts on nothing else to remove,” I said.

Karen then reached behind her and unfastened her bra, slowly peeling it from her shoulders. Her large but surprisingly firm boobs came into view and I moved my hands back to them feeling them and the hard nipples poking into the palm of my hand.

Karen leaned back and lay on the carpet again while I reached back and removed my last sock and placed it on the pile.

“Now what do we do?” I asked.

Karen beckoned me with her finger to lean over her, so I did, hovering above her face. My hard cock was now tenting my shorts and was within inches of her pussy, just a few layers of fabric were between us.

She then moved her head up slightly and kissed me lightly on the lips. “Your turn,” she said.

I lowered myself down and our bodies touched, I crushed her boobs under my chest and my cock came into contact with her still short covered pussy. I could feel Karen moving her lower body around feeling the hard lump now pressing into her pussy, trying by instinct to get inside that warm hole.

I reached for her hands and held them both above her head then lowered my lips to hers and kissed her again and again, with longer and longer kisses.

We were now breathing hard through our noses as things were starting to get out of hand. Karen released herself from my grip and reached down between us and slipped her hand inside my shorts and grabbed my cock.

I moaned at her touch and slowly moved my cock through her hand, mimicking a fucking motion.

“Sit up now,” she whispered in my ear, “I want to see your cock”

I sat back up on my heels and she started to remove my shorts. “Are you sure about this?” I said.

“Yes, it will be our little secret, nobody must know.”

“Damn right, Kate would kill me and I’m sure Jason wouldn’t be too happy either.”

I stood up above her which allowed her to pull down my shorts, which she then dropped onto the pile of clothes beside us. Karen took hold of my cock which was a little over seven inches, not large, but I’ve never had any complaints, and started to stroke me.

“I’m going to suck this cock now,” she said with a smile.

“Yes Karen, do it, I want to feel it sliding in that warm mouth of yours”.

Karen sat up and licked up the pre-cum from the end of my cock that had been leaking for a while now. Slowly she took me into her mouth going deeper and deeper, until I touched the back of her mouth making her gag.

“Fuck yes, that feels good, keep doing that.”

Karen continued to take me as deep into her mouth as she could, before withdrawing and licking my cock all over. She certainly knew how to suck a cock, as this was one of the best blow jobs I had had for years.

“I’m going to come soon if you keep doing that,” I warned. So she slowly pulled away from me and lay down on the floor again.

Kneeling down between her legs again I grabbed her shorts and slowly worked them down and off her legs. Her pussy was almost shaven, with just a small patch of hair above her slit. I could see her lips were glistening with her juice. She was obviously as turned on as I was.

I moved down to her pussy and pulled the lips apart and ran a finger up and down her slit stroking her clit lightly. Moving my head down I closed in on her pussy and took a long hard lick of her pussy slit and clit. Karen grabbed the back of my head and pushed it into her pussy and ground herself into my face.

“Fuck that feels good. Eat my cunt, make me come with your tongue.”

“Your pussy tastes wonderful, I want you to come over my face.”

Karen continued to curse and moan at my actions on her wet pussy.

“Fuck I’m going to come, here it is. Yes,” she screamed pushing my head hard into her pussy.

I slowly moved up her body licking and sucking her boobs on the way past and ending up above her face looking down at her.

“Fuck me. Now!” she demanded. “But don’t come inside me, I’m not on any protection so just pull out before you come.”

“Ok.” I said, slightly apprehensive at the fact I was about to slide my cock into the girl I had had a crush on for the few years and also from the fact that she was fertile at the moment.

I slid my cock up and down the outside of her pussy while kissing her hard on the lips, “Stop teasing me and put it in,” she pleaded. I lifted myself higher and aimed for her hole and pushed in slowly feeling the head part her lips and make its way inside. I kept moving in a slow movement until I was fully buried within her. Once I hit bottom we both moaned.

“Fuck. That feels good.” I said. Karen didn’t reply, she had her eyes closed but was squeezing my cock with her pussy. I pulled back out and slowly inserted myself in her again, picking up speed until I had built up a good rhythm. Karen had wrapped her legs around my back allowing me to go deeper into her.

I could feel that I was about to come and told Karen, but she kept her legs around my back stopping me from pulling out. “I’m going to come.” I said louder and Karen reluctantly released me.

“Come in my mouth, I want to taste you,” she said.

I crawled up her body and held my cock above her face, she guided it to her mouth. “Fuck my mouth,” she said.

“Yeah, I’d love that.” I pushed my cock into her warm mouth until I hit that back of her mouth again, making her gag.

“Here it comes baby, yes, I’m coming in your mouth. Swallow it all for me!”

Karen moaned keeping a tight grip with her mouth on my cock and greedily swallowed it all without spilling any, sucking out the remaining sperm before releasing me.

I lifted up and sat back on the chair catching my breath. Karen got up and straddled me, squashing her tits into my face and rubbing her pussy over my now shrinking cock.

She leaned down and we kissed lightly, I could taste my sperm on her lips, but I didn’t care. “That was fun,” she said, “but I want you to eat me out again.”

She cleared some papers from her desk and lay down with her pussy and arse hanging over the edge of the desk. I moved over to her and placed two fingers into her sloppy wet pussy.

“You like that?” I asked knowing the reply.

“Yes, finger me, eat me. Make me come all over your hands and face.”

I went to work on her pussy again using fingers and my mouth, our combined juices were running out of her pussy and down over her asshole. I decided to test the anal water and rubbed her crinkled hole with my thumb. “Oh yes,” she said, “I love anal as well.”

I smiled to myself and pushed my lubricated thumb into her tight ass right to the first knuckle. “Ahh!” Karen moaned, “that’s good.”

Karen passed me a tube of hand cream from her desk, “Here, use this.”

I opened the tube and inserted the thin nozzle into her ass and squeezed a quantity inside.

“Oh, that’s cold,” she giggled.

“Sorry, I’ll warm it up now.”

Using a finger I spread the cream around the inside and outside of her ass. Karen was squirming around on the desk, her hands were alternating between my head, her breasts, hair and mouth.

“Fuck, you’re making me come again!” I felt her pussy and ass clamp down on my fingers and she screamed as her orgasm took over her.

My cock in the meantime had come back to life and was now rock hard again so I stood up between her legs and rubbed it over her pussy and clit as she came down from her orgasm. Karen looked into my eyes and guided my cock to her pussy.

“Fuck me again, this time do it hard. I like a good hard fucking and I know you’ll make me come again.”

She used her legs to pull me towards herself spearing her pussy on my cock again. She dropped her legs to floor but I grabbed them and lifted her feet over my shoulders and started to pound into her pussy hard.

“Oh yes, that’s it. Fuck me hard. Make me come. Your cock is so long, I can feel it hitting deep inside me.”

After a while I took a breather and slowed my movements, pulling my cock out of her pussy and rubbing it over her clit.

Karen reached down and held my cock in her hand and guided to her ass.

“Fuck me in the ass. Nice and slowly. I want to feel you deep inside.”

“Oh yes, I want to fuck your ass so bad. I’m going to fuck you so deep you’ll beg me to stop.”

I lifted her legs higher raising her ass off the desk, I lightly pushed at her ass and her tight ring quickly gave way as Karen relaxed her muscles. The head slipped inside easily, she was obviously used to taking a cock up her ass.

“Ahh,” I moaned feeling my cock head squeeze past her tight inner muscles. “That feels fucking fantastic.”

“Oh yes, your cock feels wonderful in my ass honey. Now fuck me as deep as you can.”

I pushed at her ass feeling my cock slide in all the way, then starting a slow fucking motion in her ass, I slowly started to build up speed and was soon thrusting into her for all I was worth.

“Yes, fuck me hard and fast. Oh you’re so deep inside my ass!” Karen worked on her pussy and clit with her fingers while I pounded into her ass.

With no sign of my orgasm, we changed positions. Karen leaned forward over a chair and pulled open her ass cheeks as an invitation for me to fuck her ass again.

I stood behind her and pushed in all the way in one slow forceful movement. “Oh yes, fuck that’s deeper than before. Fuck, I’ll not shit for a week after this,” she laughed.

I continued to fuck her ass as she inserted as many of her fingers as she could into her pussy. Soon she had all five fingers in her pussy and was trying hard but failing to get the whole of her hand inside. I could feel the familiar tingling in my balls and knew I was about to explode.

“I’m going to come soon baby.”

“Oh fuck yes, I want you to come inside me ass. Would you like that?”

“Fuck yes.”

“Shoot it as deep inside me as you can. I want to feel your come in my ass.”

“Oh fuck, I’m coming. Yes, here it comes.”

“Yes, fuck… fuck … fuck. Shoot it inside me. Fuck you’re making me come again!”

Karens ass clamped down on my cock as I held myself as deep inside her as I could. We were both breathing hard and slowly my cock started to deflate, so I pulled out and lay down on the floor to rest and catch my breath.

Karen got up from the chair and lay next to me. “Fuck me that was intense. I’ve never had anything that deep inside me before. It was wonderful thank you.”

“No, thank you, I’ve always wanted to do this but gave up on the idea many years ago. What made you lie on the floor in the first place?”

“I’m not sure,” she replied “I guess I’ve always wondered what it would be like to have someone else. As Jason is the only person I have fucked. I’ve been thinking about it for weeks and when we got the opportunity of being alone today I thought what the hell and waited for the right moment.”

I leaned over and kissed her lightly on the cheek. “Well I’m just glad that you choose me to experiment on,” I laughed. “I’d better go and clean up.” I got up and headed for the washroom to clean my cock.

When I returned Karen was lying on the desk again, playing with her pussy, this time though her head was leaning back over the desk. She had her eyes closed while she fingered her pussy, so I walked over to her head and lay my cock on her cheek. She never opened her eyes but opened her mouth and took my soft cock into her mouth again.

“Oh yes baby, suck my cock, nice and slowly. It’s tender after banging your ass before.”

She slurped and licked me while she continued to play with her pussy. “Do you think you can fuck me in my pussy again?”

“Well you’ll have to try and get me hard first, as I’m not sure if I’ll be able to go again. I’m not as young as I used to be you know.”

Karen smiled and continued to work on me taking all of my flaccid cock into her mouth. I leaned over her and massaged her boobs while I slid my cock in and out of her mouth. Amazingly I started to get hard, but not as hard or big as I was before. Karen got up from the desk and pushed me down onto a chair and stood in front of me facing away, she bent forward showing me her ass and pussy.

I could see my come leaking out of her ass and her pussy juices were running down the inside of her legs. She reached between her legs and pushed a couple of fingers into her pussy showing me how wet she was. With her other hand she played with the cum leaking out of her ass, pushing in a finger or two bringing out more of my cum.

I stroked my cock at the sight before me and soon I was close to full strength again. Karen noticed this while looking between her legs and turned around and sank her mouth down my cock until I touched the back of her mouth, she bobbed up and down taking me all the way into her mouth.

She then pulled off me and lay back on the desk with her head leaning over the edge and opened her mouth wide.

“Come and fuck my mouth, then you can have my pussy again”. I moved over to her and slid my cock into her mouth, I was now at full strength again and touched the back of her mouth with a couple of inches still to go. Karen reached round behind me and pulled me closer to her forcing my cock deeper into her mouth and throat until my balls were touching her nose and her lips were forced into my pubes. I could feel her throat tight around my cockhead as I pushed in as far as I could.

“Fuck that feels good, let me fuck your throat now”.

Karen removed her hands and I held onto the sides of her head and withdrew my cock before slowly pushing it back inside again, feeling the head squeeze deep inside her. I pulled out again and allowed her to breathe. I continued to slowly fuck her mouth and throat occasionally taking a break to allow her to catch her breath.

Karen, tapped me on the leg and I withdrew from her mouth. “Sit on the chair and let me fuck you now.”

I moved over to the chair and sat down holding my dripping cock upright, ready for her to impale herself on me again. Karen walked over to me and positioned her pussy above my cock. She leaned forward and kissed me, her tongue made its way into my mouth as her pussy came into contact with my cock.

I wrapped my arms around her hips and guided her down in one long slow stroke until I was fully embedded in her pussy again. I felt the head of my cock mash into the back of her pussy causing Karen to moan in my mouth. She then started to quickly fuck me, repeatedly slamming herself down on me.

After a minute or so she got up and turned around. “Time for my ass again,” holding my cock she lined it up with her asshole and sat down on me, forcing it back inside her tight ass.

We both moaned as she sat down on me, taking me all the way back inside her. She then slid up and down my legs repeatedly taking me deep inside her.

Soon her legs were getting tired, fucking on a chair takes a lot of stamina and we were both getting tired now. Karen stood up and moved back to the desk and leaned over it spreading her legs wide and looking back at me over her shoulder.

“It’s your time to do some work again, fuck my ass nice and deep.”

I stood behind her and slid my cock back into her ass and started to pound her hard and fast.

After a few minutes Karen pushed me away, “I’m getting sore there now, put it in my pussy please.”

“It’s just been up your ass though, should I go and wash it first.”

“No, I want a good fucking now, just put it in. God I need it in me.”

I moved lower and aimed at pussy and pushed in, this position allowed me to get deeper into her. Karen was now constantly screaming as I fucked her hard and fast, my cock was really smashing into the back of her pussy now causing Karen to scream loudly with each heavy impact.

I could feel the tingling in my balls signalling the end was coming soon, so I pulled out and sat on the chair. “No, don’t stop, I’m about to come,” she said

“I have to, I’m about to shoot again.”

Karen got up from the desk and sat on my lap stuffing my cock back inside her pussy again and started to ride me hard. “I need to come,” she said. “Make me come with your cock.”

I lifted myself up as high as I could so Karen could get me as deep as she could inside her.

“I’m going to come soon,” I warned.

“Ok,” she said, but she continued to ride me, seeking out her orgasm.

“I’m going to come,” I warned her again.

Karen moaned loudly but continued to bounce on me.

“Karen,” I shouted making sure she heard me, “I’m going to come now.”

“Yes, come inside me. Let me feel it. I want to feel you shoot deep inside me,” she said, as she continued to bounce on me. I was now extremely turned on, knowing she was unprotected. Had she actually asked me to come inside her pussy?

“Nearly there,” I said again just to make sure she knew what was about to happen.

“Oh God, Yes, do it. Shoot it inside me. I want to feel you shoot in me. Oh God you might make me pregnant. Yes do it, come inside me now.” I could feel her pussy clamp down tight on me signalling her orgasm had arrived.

“I’m coming, here it is,” I shouted.

Karen screamed out her orgasm and held me as deep as she could inside her. I held onto her tight and started to come inside her fertile pussy, grunting loudly with each powerful spurt.

“Yes, do it, fill me up,” she screamed. “I can feel you shooting deep inside me. Yes do it. Oh God what am I doing. I’m coming over your cock and you’re coming inside me!” I held onto her tight and shot my last load deep inside her as she eventually came down from her orgasm.

She looked down at me and smiled. “That was the most intense orgasm I’ve ever had. I’m not sure what came over me, it must have been the heat of the moment. I just hope I don’t catch.” she laughed.

“Well it was fantastic, now I’m completely drained,” I said feeling my cock shrivel up and drop out of her pussy. We went to the washroom and cleaned ourselves up.

The next day Karen pulled me to one side and thanked me for the session the previous day. She was so turned on when she got home, that they had spent most of the evening in bed and she had convinced Jason that they should try for another baby. Jason had filled her up twice that night, so the chances of her catching yesterday were extremely high.

Sure enough a month or so later it was confirmed that she was pregnant, though whose child it was may never be known. A few weeks later we repeated our sex session, this time at her house while Jason was away on business for a few days. Though it didn’t quite match up to our first session we still enjoyed it and I managed to deposit two large loads in her pussy and one deep inside her ass.

Our affair continued for many years, we didn’t get many opportunities to meet up, but when we did we made sure we enjoyed it.

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