Working for My Boss - Karla

by Tom Land

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Cheating, Slut Wife, DomSub, Oral Sex, Anal Sex, Masturbation, Petting, Pregnancy, .

Desc: Sex Story: Tom gets hired to a new job as an admin assistant but his sexy boss Karla has more than paperwork in mind for his daytime activities.

Chapter 1

I'd interviewed for the job as the administrative assistant for the director of the communications division. I did all the application process with the secretary and another woman who I'd be working with and on my second visit I finally met the person who would be my actual boss - Karla. I immediately thought she was very sexy although she was obviously a woman in her middle 40's from what I could tell. She was a very snappy dresser and I thought immediately that I'd enjoy working for her and hoped that this job would last for many years. I liked the professional looking outfit Karla was wearing that day, a business suit consisting of a very nice silk blouse, a wool skirt and a matching jacket. I tried to size up her figure but all I could tell from what I could see was that she was very trim and I thought her face was rather pretty and her hair looked wonderful. Her hair was cut just above her shoulders and stylishly highlighted. I couldn't really tell much about her breasts but there was a distinctive swelling underneath her blouse that told me she was probably a B or C-cup in that area. I was almost self-conscious as I sat there and realized that I was actually getting the stirrings of an erection as I mentally tried to undress my potential new boss.

The woman I'd be working with was pretty sexy too, a woman in her 30's who had a very nice set of large breasts and a pretty face and attractive hair. She had possibly a few pounds more than she needed on her figure, but she looked pretty hot as well.

Karla had a small interview with me and then I received a call the next day that I'd been hired. They asked when I could report to my new job and I gave my other employer a two week notice and then made my move.

I had only been in my new position about a day when Karla called me into her office. This time she'd was wearing a skirt and a blouse that buttoned up in front. She'd apparently been wearing a matching jacket with her outfit but it was lying folded neatly on a nearby chair. Karla waved me into a nearby chair beside the side of her desk where she was sitting and she began to ask me questions about myself and my experiences in other recent jobs I'd had. I wasn't sure, but as I sat there watching Karla, I felt like she was sizing me up and occasionally I could see that her eyes were wondering into my crotch area.

After a few minutes, Karla motioned for me to come over beside where she was sitting and look at some of the kinds of materials I'd be working to help her produce. I immediately picked up the faint but very distinctive aroma of Karla's perfume as I stood there next to her and I could also see that she'd left the top two buttons of her blouse unfastened and when she'd bend over to show me something, I got a very hot view down her blouse to the sexy demi-cup bra that was holding her tits. I loved what I was seeing. Karla had some very nice breasts and I only wished it was possible for me to get something more than a peek.

Karla and I finished our little conference and I headed outside her office to my own work space. Again, I had gotten a hardon from the sexiness of looking at her and smelling her sensual perfume. Actually, I returned to my desk for only a few minutes and then I went to the men's room where I stroked my horny cock until I blasted a big load of cum from imagining that I was fucking Karla. She was a married woman but I didn't care about that. She was fucking hot and the more I was around her the stronger my sexy fantasies about her became.

The third day I was in my new position, Karla came to her door and asked me to join her in her office. Unlike the other two times, she pushed the door shut behind me after I walked through it. I really didn't pay any attention to that but as soon as Karla walked over to the couch she had in a corner of her office, I suddenly began to think that I was about to learn even more about my new job's duties. Hmmmmmmm, "duties" I thought to myself and then Karla started talking to me.

"Tom, I didn't mention a very important part of your job here working for me the other day when I interviewed you. I've been watching you since we first met and I think there are some other things you can do for me on a regular basis," Karla said as she sat there with one shapely leg crossed over the other one. "You're a very attractive young man, Tom, and I'm a healthy woman who has certain needs and desires that I need to satisfy occasionally. I'd like for you to become an important part of my daily schedule in all that I need to do," Karla said as she let her fingers toy with the button on her blouse.

As I sat there watching Karla as she was talking to me, I couldn't decide if she was simply referring to another part of my job as her administrative assistant or if she had something far sexier on her mind. I could tell she was sort of nervous in broaching the subject -- well, either it was nervousness or sexual tension. Right then it wasn't apparent.

"Karla, I'll be willing to do whatever you ask me," I replied as I realized once again my cock had begun to thicken and grow hard inside my pants. It had gotten to where every time I was around Karla I ended up in the men's room for a lusty masturbation session to relieve the sexual arousal she made me feel. I didn't think anything would ever come of my hot fantasies about Karla even though I'd had several experiences of fucking co-workers and even fucking some of them at work. But, it's one thing to "get into" a co-worker and another to envision ever doing something sexy with your boss. Well, that's what I was thinking then...

Karla caught on my last words -- "do whatever you ask me" and she immediately responded: "You're willing to do whatever I ask, Tom?"

I nodded my head in acknowledgement and she undraped her leg, and started spreading them wide as she pulled her skirt up high on her thighs and said, "Then, I want you to start by coming over here in front of me and lick my pussy."

For only an instant, I thought I was hearing things, imagining things like I'd want them to be. But, then as I watched Karla move to pull her skirt up high enough to expose her horny pussy to me, I knew I was hearing exactly what she'd said -- Karla was telling me that she wanted me to eat her pussy and I couldn't get over there in front of her fast enough to suit me or her. As Karla scooted her skirt up, exposing her upper thighs to me I could see that she'd "lost" her panties somewhere along the line already. She didn't have any on and all I could see what a sexy naked and already aroused shaved pussy. Oh yeah, Karla had shaved her pussy that morning or the night before and there was no pussy hair on her at all. Her pussy was shaved baby smoooth and just ready to be licked, kissed, fingered and fucked. I was ready.

I knelt in front of Karla, taking just a moment to survey the hot naked flesh I was about to lose myself in. I moved closer, watching Karla settle back onto the couch to get comfortable while she let me at her pussy. I reached underneath her naked asscheeks, pulling her forward nearly to the edge of the seat so I could readily bury my face in her crotch. I grabbed hold of Karla's ass tight so I could control her and then let my tongue slide down the center of her already swollen and very wet pussy slit. Her clit was firm and I diddled it with my tongue and then buried my tongue in her pussy and started nibbling and licking her, listening as she started to moan and encourage me that I was really making it feel good for her.

"Ohhhhhhhhhhhhh fuck yeah, Tom, do me, ohhhhhhhhhhhhhh, yeah, do me, mmmmmmmmmmmmmmmm," Karla moaned as I went after her pussy as hotly as I could. I knew that she'd been sitting there just waiting for me to come into her office and I didn't figure it was going to take much to bring my boss off in her first orgasm from my mouth and fingers. I was exactly correct. I loved the taste and the smell of Karla's horny hot pussy. Her pussy tasted like that of a hot hormonal 16-year old and I loved how easily she began to moan and buck her horny orgasm-hungry pussy against my face. I wanted to strip her naked, eat her to orgasm and then mount her and fuck her soundly right then and there... but I know all things would come (and cum) in good time. For now, I concentrated on licking and eating Karla's horny cunt and the moans and sighs she was freely letting me hear just pushed me on in hot sexy enthusiasm. In only a few minutes, I had Karla bucking her pussy against my face like she wanted to fuck my face, and then she screamed that she was cumming and she pressed her pussy against my face as tightly as she could, and I was rewarded by a face full of her hot pussy cum streaming from inside her horny orgasming cunt.

I thought maybe Karla would be at my mercy at that point and I could have my way with her, but Karla was no young babe. She was obviously a woman of vast sexual experience and one hot strong orgasm only took the edge off her sexy needs of the moment. As soon as she'd come down from her climax, she lay there in her chair, wallowing in the sensual feeling of cumming from my oral attentions to her. Then, as she allowed her sexual ardor and horniness to take control again, Karla stood up from her place there on the couch, unfastening her skirt and sliding it down off of her legs onto the floor. Then she quickly unbuttoned her blouse, pulling it off and throwing it onto the floor beside her skirt, and then she took me by the hand and led me to a nearby chair. Leaning over, Karla quickly unfastened my pants and pulled them down off of me along with my boxers.

"Tom, I want to return the pleasure you've just given me by sucking that

hot big cock you've got sticking up from your groin. But you work for me, Tom, and right now I want one thing -- to have you sit in this chair and let me sit down on your cock and fuck us both to a hot orgasm." Without saying more, Karla pushed me towards the chair, and as soon as I'd situated myself, she walked over to me, slid herself over onto my lap as she grasped the thick long hard shaft of my aroused cock in her hand, and began lowering her wet swollen pussy straight down onto the big full head of my cock. The instant her pussy lips touched my cockhead, I reached up, grabbed her by the waist and pulled her down onto my hot meat, impaling her on my cock as she felt it filling and spreading her horny pussy. "Ahhhhhhhhhhhhhhhh, yeah, fuck me, baby," Karla moaned as she slid straight down, taking all of my hard thick cock inside her pussy.

Chapter 2

"Tom, I want to return the pleasure you've just given me by sucking that hot big cock you've got sticking up from your groin. But you work for me, Tom, and right now I want one thing -- to have you sit in this chair and let me sit down on your cock and fuck us both to a hot orgasm." Without saying more, Karla pushed me towards the chair, and as soon as I'd situated myself, she walked over to me, slid herself over onto my lap as she grasped the thick long hard shaft of my aroused cock in her hand, and began lowering her wet swollen pussy straight down onto the big full head of my cock. The instant her pussy lips touched my cockhead, I reached up, grabbed her by the waist and pulled her down onto my hot meat, impaling her on my cock as she felt it filling and spreading her horny pussy. "Ahhhhhhhhhhhhhhhh, yeah, fuck me, baby," Karla moaned as she slid straight down, taking all of my hard thick cock inside her pussy.

I couldn't believe how my "work day" was turning out. Yeah, I'd jacked off more than once imagining Karla fucking me, but to actually be sitting in a chair in her office, feeling the hot wetness of Karla's hot aroused pussy engulfing my hard long cock was far more than I'd have ever believed possible. I don't know if you've ever had the experience of actually fucking your boss -- whether a man or a woman -- but there's something very erotic and extremely arousing about knowing that you've got your cock buried inside the woman you work for -- and she's loving every single moment of it.

Karla was very much in control of our fuck together -- and I think that's just the way she liked it. But, she didn't know that I loved having a woman sitting on my lap, riding up and down on my fuckpole and bringing me to a hot sexy powerful orgasm just as much as she was delighting having my big horny dick filling every single inch of her wanton hot pussy. Hehe, I'd just let her think she was in total control and not spoil one second of it for her by telling her that I was loving it just as much as I could tell she was.

With Karla in my lap, my cock already buried in her wet pussy and her starting to slide smoothly up and down on the full hard length of my dick, I reached up, grabbed each of her breasts in my hands and I began flicking my tongue over first one erect nipple and then the other one. Karla's titties were very aroused, her nipples were perky, and when they were both hardened into small visible signs of her arousal, I started rubbing my thumbs over the hot little peaks, driving her to higher and hotter states of lusty desire. At the same time that I was paying attention to her naked breasts, Karla was literally fucking herself on my cock. And I was benefiting from the hot tight clasp of her pussy around my erect cock the entire time. I could tell that Karla was a very sexy, and very sensual woman. She obviously loved being naked and having sex. She obviously loved to fuck and be fucked. And she obviously had no problem experiencing orgasms. Within five minutes after she'd moved onto my lap, impaled herself on my jutting cock, and began riding me up and down, she was breathing hard, panting breathlessly and then she began begging ME to fuck her harder, deeper and faster. Well, when she said that, I grabbed her tightly around the waist, and I instantly took control of our hot fuck. Karla could tell that she'd let me take over and she threw herself into the final stages of her arousal to the point of orgasm. She was flinging her head around wildly and that just made me hotter and more determined to fuck her until she passed out.

"Ohhhhhhhhhhhh, yeah, Karla, fucking take every last inch of this big horny cock, lady, take it, Karla, oh yeah, fucking ride my dick like you've never ridden one before, babe," and just seconds after that as I pounded her womanly body up and down on my hot dick, Karla started screaming and moaning that she was "going to fucking cum" -- and she did. I continued to slide her up and down as she climaxed and then without pulling my cock out of her, I stood up, holding my dick still tightly inside her pussy, moved around where I could lay her back in the chair. Still situated firmly inside her horny cunt, I began bucking my hard muscular ass in and out of Karla's legs, watching as my super pussy-soaked thick cock slid in and out of the hidden spaces deep inside my boss's pussy. She was loving it -- and I was too. I pounded her like this for another 10 minutes and then I thrust my cock inside her as far as it would go -- and I stopped moving totally, letting my nuts cut loose and my cumload blew deep into the hot darkness of her horny womb.

Breathing hard, feeling slightly dizzy and loving the hot satisfied feeling of having my cock fucked until I blasted my jizz inside my boss Karla's pussy, I stood there with my dick deep inside her as I reached up, caressing and playing with her breasts as I wondered what was next.

Chapter 3

After my first sex session with my boss, Karla, I really didn't know exactly what to expect after that. After all, when you interview for an admin assistant job and you suddenly find out that your new female boss has really hired you cause she think you'll give her a good fuck and pussy eating, then you find yourself wondering what the ground rules really are. What will you be doing every day when you go to work??

A few mornings after my last fuck with Karla, I started to not bother wearing any underwear -- at least any briefs -- since I figured I'd "lose them" when I got to work anyway. But I didn't go that far on that occasion. I went ahead and dressed like it would be any other normal workday behind my desk. I was wrong.

Part of the reason this particular day was different from normal was because of a decision I made in regards to my "in the office" relationship with Karla. So far, Karla had been "in the driver's seat" in this budding sexual relationship. Or whatever you'd call it. I'll be honest and admit that I wasn't sure what my job longevity would be with Karla because of what my job really entailed. I wasn't exactly used to be a woman's gigolo and the idea of finding myself in a one-way dom/sub setup didn't appeal to me. But, that's sort of what things had been starting out -- Karla, of course, had called the shots. While I'd only fantasized about getting in her panties and fucking her, Karla had those intentions in mind for real and had brought me fully into her own desires and plans. Now, I decided to see how far I could "push the envelope" in molding the "office environment" to my own tastes -- and I might be flirting with the end of my employment for Karla if I chose incorrectly.

When I got to work that morning, I quickly plowed into the normal administrative routines that one would have thought would be my job. I spoke to Karla when she came into the office and I loved what she was wearing that day. She had on a very nice looking skirt and sweater with a nice gold necklace and earrings that made her look rather formal and dressed up. Karla always looked very professional, almost to the point of it appearing somewhat pretentious but she was an attractive woman and it didn't take much for her to look nice and very business-like. I certainly couldn't help noticing how nicely her breasts filled out her sweater and I caught myself wondering what type of bra she had on underneath it that was showing off her sexy tits so nicely.

About midmorning, Karla went sashaying out of the office for some departmental meeting, and I sat there at my desk just waiting for her return so I could spring my own personal "fuck plan" into action. My cock stayed nearly half hard the whole time Karla was gone, and than about 90 minutes later, she returned and lingered for a moment at my desk, looking me over and giving me what I interpreted to be a definite "I'm interested -- but don't have time to fuck you right now" look on her face. But that was my signal to put my own plan into action.

I let Karla walk back into her office and she pushed the door slightly shut behind her. I wasted no time at all pushing the door ajar and walking in, pushing it closed behind me as well.

Karla was still standing beside her nice large wooden desk, looking over some papers she'd brought back from her meeting. With her back half turned away from me, I wasn't sure if she'd seen me or heard me enter. I didn't care; I walked over and reached up underneath her armpits, closing a hand over each of her full rounded breasts. I could tell my sudden grabbing of her body like that sort of startled her, but then I squeezed each breast firmly in my hands and I could almost instantly feel her mleting back into my body standing behind her. Karla was responding as I'd hoped she would. I don't think anyone likes rejection when you're making a sexual advance to your sex partner and I don't either. I loved that Karla seemed open to my touch, and my sexual advance even though she'd seemed preoccupied.

After I stood there, pressing the hard lump of my horny cock against Karla's tight skirt-covered behind, I leaned forward, kissing up her neck and ensuring she could feel how much I wanted her body. Then, I released her breasts, allowing my hands to move down to the bottom of Karla's sweater, then sliding them up underneath it and taking a breast in each hand again. "I don't know what you've got in mind right now, Karla," I said as I firmly held her breasts and her body close to mine, "but I'm really horny to fuck you and I want you right now," I continued and then I pulled my hands from her top, took her papers and laid them on the nearby desk as I pushed the papers and other items on the top of Karla's desk off onto the floor to make a clear space. I'd never fucked anyone on the top of their office desk but Karla and I were about to "make a first" as far as I was concerned.

"Oh, Tom, so you're horny to fuck, huh?" Karla asked as she tried to act like she was only slightly interested. I thought she was kidding but I wasn't so I kept pressing ahead with my plan.

With the desk cleared, I sort of watched for Karla's reactions but at the same time, I reached behind her waist, unfastened the snap to her skirt and began pulling it down to her ankles. Underneath her skirt she had one a short slip which I also pulled straight down her shapely legs, and I'd also noticed that she'd been wearing pantyhose that morning. I started to rip a hole in her hose and fuck her through that but decided to wait on being quite that aggressive sexually. I leaned Karla back against the desk as I pulled her pantyhose off, and that left only her sweater with her bra under it and a sexy pair of bikini panties. I started to pull Karla's panties off too but then decided to tease her and get her totally horny to fuck me by caressing her and licking her pussy through them. Kneeling down in front of Karla, I caressed and licked her pussy through the thin material of her panties and quickly I saw a spot of pussy wetness develop there. Then, as Karla began to moan and fell fully into my foreplay with her, she shrugged out of her panties and she boosted herself up onto her desk and placed her feet squarely on the edge where I could get to her pussy but where she was lying there securely and wouldn't fall off.

I decided for the moment to deal with Karla just half undressed, leaving her with the bra and sweater still on her upper body. I hope that gave her a more adventurous and risque feeling than if I went ahead and stripped her totally naked. I'd prefer having her that way so I could enjoy her hot breasts but in due time.

I quickly dropped my pants and the briefs I had on, stroking my cock hotly and ensuring Karla could see how hard and thick my cock was. I could hardly wait to bury all of my hard cock inside her. I leaned forward, smelling the hot muskiness of Karla's wet pussy and I licked my tongue up and down her horny cunt. "Mmmmmmmmmmmmmm, fuck, Karla, you taste to good, lady," I said in a deep voice as I reached underneath her firm round asscheeks and pulled her hot cunt up tightly against my face. She began to squirm and moan under my oral attentions to her hot pussy and it took only about 5 minutes of licking before Karla shot into an orgasm and started cumming on my face. I licked her clean and then, pulling Karla forward on the desk until only her asscheeks were keeping her up there, I moved between her spread legs, dipped the head of my cock in her pussy juices, and then pushed forward strongly, watching the entire head of my cock and then several inches of my horny rod disappear inside her womanly body.

"Ohhhhhhhhhhhhh, yeah, Tommmmmmmmmmmmmmmmmmmmm, fuck me, baby," Karla moaned as she felt my cock spreading her tight pussy tunnel and filling her horny cunt. I knew I had Karla in my control at that point, and I grabbed tightly underneath her ass, holding each cheek firmly as I started pounding solidly and strongly in and out of her clasping hot cunt.

"Mmmmmmmmmmmm, you're such a horny fuck, Karla," I moaned as I nearly lost myself in the hot rush of "doing Karla" there in her office, right smack in the center of her desk. I found myself wishing we'd leave pussy and cum juices on her desk, but that was just the naughtiness in my sexual side coming out.

As I held Karla firmly there on the edge, I started thrusting my full hard thick dick in and out of her hot pussy. She seemed to grow wetter and tighter in her cunt while I was fucking her, and I loved the feel of this horny woman's hot pussy wrapped around my hole cock. I loved the sound of my cum-filled nuts smacking hotly against her tight ass and then after 20 minutes, Karla began to orgasm. I reached up, grabbing both her sexy round tits through her sweater, diddling the hard rock-like nipples underneath my fingers as she climaxed and as I pumped my dick in and out more strongly, I also began pumping my hot thick white jizz inside Karla's pussy.

"Mmmmmmmmmmmmm, man, a day at work with you, Karla, is better than a day off anytime," I moaned as I felt my balls empty their spunk inside her.

Chapter 4

I'd just fucked Karla to the first orgasm of the day, and it had felt so good as I'd continued driving my thick horny cock in and out of her tight wet pussy until I blew my first cumload deep inside her. But I wasn't nearly finished with Karla for that day. I'd only stripped Karla naked from the waist down when I'd first come into her office and put my arms around her. I'd left her clothed from the waist up in the sexy revealing sweater and bra she'd had on when I'd first seen her that morning.

Now that I'd fucked Karla to our first mutual orgasms, I pulled my cock out and walked over to where her head was lying on her work desk. I decided I'd move on to Stage Two of my Plan for Karla and our ongoing sexual relationship. I reached down, placing my right hand over the rounded mound of her left breast underneath her sweater. I could smell the hot musky aroma of her aroused pussy and the juices of the fuck we'd just enjoyed together.

"Mmmmmmmm, Karla, you've got such nice tits, baby," I said in my sexiest voice as I prepared to bring Karla on into our second fuck of the morning. I knew she was hot and horny enough for another round and I sure was. I just wanted to stoke her female sexual fires and get her pussy burning totally for another hot session of "cock stuffing".

"I know they're nice, Tom, and I know how hot they make you, baby. Wait'll you pull this sweater off and see what I put on just for you this morning when I dressed," Karla said as she lifted the bottom of her sweater to help me in getting it off of her upper body. I peeled Karla's sweater up off her body and when I could see the bra she had on, my cock instantly began growing very thick and hard again, even harder than for our first fuck. Karla had on one of the sexiest, skimpiest black lace bras I've ever laid eyes on. The cups barely contained her nicely shaped breasts and I could see the dark aureolae and nipples of her tits inside the thin translucent bra material. Man, what a hot bra, and Karla had just told me she'd worn it to seduce me. I loved it.

Pulling the sweater on off of Karla's body, I reached down between the twin mounds of her breasts, unfastened the front snap holding the bra closed, and then peeled first the left cup off her tit and then the right one. My mouth closed over her right nipple, tongueing and suckling it to erect hardness and then my right hand ventured down between her thighs again to warm her up for Fuck #2.

"Take this horny cock of mine, Karla, and suck me until I'm ready to fuck you a second time," I said to Karla in a voice that made it clear I was very serious. She'd said something on an earlier day about sucking my cock and now I intended to give her that opportunity.

Karla turned her head to the right, reached out and took the shaft of my semi-hard cock in her hand and leaned over where she could wrap her lips and hot wet mouth around the head of my dick. It felt so hot and sexy when my boss, Karla, took the tip of my dick in her mouth. That was something I'd sure jerked off thinking about and now it was happening for real. "Ohhhhhhhhhhhhh, man, that feels good," I moaned as she not only started sucking and taking more and more of my cock inside her hot mouth but she was stroking my cockshaft up and down, making me harder and very horny to mount and fuck her again. Karla also began caressing and rubbing on my nuts, which always brought me to higher arousal in no time at all.

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