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    Sleeping My Way Through a Job Part One

    I started this new job a while back and when I walked into the small office I knew I wanted to work there. The office manager Connie, was a petite single asian woman very cute, very sexy, great ass. She always wore skirts, heels and pantyhose.

    Next there  was Celeste. She was the accountant. She was in her 50's but she was an avid tennis player so she was tan and tone. She also had a great ass and nice big tits.

    Next was Chrissy. She was in her early 20's. Very beautiful, and overall the sexiest girl in the office. She has curly blonde hair and an ass and tits that won't quit.

    Then there was Fiona, she sat right across from me. She is a tall  beautiful Chinese woman, never wore a bra to cover up her 34B's, one of the greatest asses I've ever seen. She had shoulder length chestnut brown hair. She made me the horniest.

    Sitting in the back was Malika. She is Indian with a petite body and huge tits that that jiggled nicely when she walked.

    Last but not least was Dawn. She is a petite strawberry blonde. Very thin, but judging by the way she talked, she was a nympho. I'd save her for last, not wanting to pass along an STD's I may get from her. (Just kidding she was a nice girl).

    Surprisingly, Chrissy was the easiest. I thought she would be harder to fuck becuase she was so pretty, but she fell first. It was my job to open up in the morning, and I was driving there when I saw Chrissy waiting for a bus. I pulled over and offered her a ride which she accepted. When we got to the parking lot, I shut the engine off and looked at her. She was showing a lot of cleavage that day and my cock got instantly hard. We had some time, so I asked her "wanna make out?". She said sure and we started going at it. I unzipped my pants to show her my 10" dick, which she immediately went down on. She managed to get all 10" of my cock down her slutty little throat. It didn't take long before I shot a load of cum in her wet little mouth. She swallowed every drop. Our company had another location out East, and I had to go there frequently, and I always found an excuse to take Chrissy with me. The other place was a warehouse that was mostly empty that has a nice office upstairs with a couch. I fucked her long and hard everytime we went there. I usuall just pulled up her skirt and pulled her panties to the side and fucked her doggie style, but we got bolder and bolder eventualy stripping naked and doing more vulnerable positions. More on that later.

    Next on the agenda was Celeste. Again, she was relatively easy. I think she was just lonely since her husband had died. She asked if I was interested in playing tennis with her, and I said yes. When we got out onto the court, I couldn't believe how good she was. I'm OK but Celeste was out of my league. She also looked really hot in her tennis skirt and pollo shirt. I could see her nipples through the thin material. Her outfit not withstanding, she beat me in straight sets. We went out on the patio of the clubhouse and had drinks and she started talking about her husband and how she missed him. She also told me she was 58 years old. I was about to order another round of martini's for us, when she stopped me and asked if I'd like to go back to her place for those drinks. I hesitated a moment, but said yes. We got to her apartment, and she fixed us a couple of drinks. She brought out 2 glasses of 12 year old scotch on the rocks. She sat on the couch next to me and apologized. I asked why she was apologizing and she said I usuall don't drink scotch but I needed something stronger for what she was about to do. Before I could even ask the question "What is that?" she leaned in and kissed me gently on my lips. I looked at her and said "No apologies needed." and we started kissing passionately. When she pulled off her pollo and skirt I couldn't believe what a great body she has, and not just for a 58 year old woman, but most girls in their 20's I know. She did things to me that afternoon that I never experienced before. At one point, she mounted my cock and I could acually feel her pussy gripping my cock like a closed fist. It was like fucking and getting a hand job all at once. When we were finally done, she pulled me out of her pussy and stroked my cock until I came all over her tits. She was totally amazing. That was the only time we ever fucked and we never talked about it again. I tried to engage her a few more times but she always shot the idea down. I guess she just needed a hot fuck.

    Dawn was a bit of a skank, but that was Okay because I liked skanks. Dawn might actually have been the easiest, she rang my bell one saturday morning with a 1/8th of coke wanting to party. She asked me if I knew any friends that would want to join us. I immediately thougt of my downstairs neigbor Cynthia. She was another one who would fuck your brains out for a few lines of coke and a joint. I have other stories about Cynthia, but that's for another time. Cindy is short but nicely proportined and pretty cute. She also gives the best blowjobs ever. She came up with a bag, Dawn looked her over and said "not exactly whay I had in mind...but Okay". As the girls started doing lines of coke I popped opened a beer and started to enjoy the show. As the girls started to get high, they started kissing and taking off their clothers.. Dawn looked over at me and invited me to take my cock out and start jerking off to them, which I gladly did. Dawn was eating Cindy out pretty good, and Cindy asked me to join them. I stripped out of my remaining clothes, and put my hard dick into Dawn's wet pussy. I was surprised that it was so tight. I saw Cindy shudder with an orgasm as Dawn licked her tight asshole. Cindy then asked Dawn, "Ever get DP's?". Dawn said that she hadn't. That's when Cindy pulled a strapon dildo out of her bag. Dawn said "I like where you're going with this". Cindy asked me if I wanted the ass or pussy. I said I was perfectly happy with her tight wet pussy. Cindy instructed Dawn to get get on all fours, where she proceeded to expertly lick Dawn's wet holes. Every once and a while during this Cindy would let me do a quick face fuck to her to keep me hard. At his point Cindy had her finger moving in and outof Dawn's ass, and they were both getting turned on. Cindy was a wet sloppy mess. She told me to sit on the couch and told Dawn to mount my cock. When I was fully inside of Dawn, Cindy entered he ass with her strapon which made Dawn scream with delicious leasure and pain. We proceeded to erotically torture this girl for what seemed like an eternity. When I was finally ready to cum, I pulled out of Dawn's soaked and gapping pussy and both girls got on their knees in front of me. I stroked my dick and It didn't take long before a spewed like what seemed like a gallon of cum on both girls faces. Cindy cleaned up my cock licking all of my cum and Dawn's pussy juice off of my cock. The girls then licked my cum off of each others faces. Dawn suprised me when Cindy stood up and put Cindy's bi strapon in her mouth. Dawn got dressed and wobbled out of my apartment. Since we were already naked and horny, me and Cindy went at it for a few more hours and then let me fuck her in the ass in the shower.

    The one that surprised me the most, was Connie. Connie was single and in her 30's. She was 5 feet tall and weighed 95lbs soaking wet. She spoke with a heavy Chinese accent. She wore glasses and was kind of nerdy. She has short black hair, and always dresses in business suits and slacks. And ALWAYS wears pantyhose. One time she was helping Chrissy with something, and I couldn't her but watch her tight little ass sway back and forth as she was bent over Chrissy's desk. Fioni caught me checking Connie's ass out and whispered to me, "get your mind out of the gutter". We had to go off site for a demonstration one time; she drove. After the demo was over we were driving back to the office, and I noticed that her skirt had rode pretty far up her thighs, and she looked good. I got erect pretty fast. She caught me staring at her legs and noticed the tent I had pitched on in my baggy pants. She didn't say anything or react in any way. As we got closer to the office, she turned to me and said "We are very early getting back. I wouldn't mind if we stopped at my house for a while. We have to make it fast though" I was surprised  but said "Okay, I'd like that". We got to her house and went inside. She asked me to take my clothes off and I did. She opened her blouse revealing her small but perky tits (I suspected that she had this planned out being that she wasn'r wearing a bra). she unzipped her skirt and let it slip to the floor, took off her shoes, and peeled her pantyhose off. she approached me and ran both of her hands up and down my muscular chest.She stood on her tippy toes and kissed my mouth, letting her tongue explore the inside of my mouth. She then kissed down my chest and my belly until she got to mt hard cock and shaved balls. She gently kiss and licked the head of my cock and then my shaft alll the while massaging my balls. She seemed reluctant to put my entire erection in her mouth, but I didn't care, It felt great. She grasped me by my dick, led me to her bedroom, laid on the bed and pulled me down on top of her. I slid my huge erection into her tight asian pussy. It took me a few minutes to get it all the way inside of her, but it finally got it all the way in. She moaned with pleasure every time i thrust my 10" into her. She was so tight that it only took me about 10 minutes to cum, and I accidently came insider of her. She said not to worry she's on the pill. With my cock still inside of her and slowly softening we made out until my cock finally slipped out of her, at which point we both gave out a gasp. We hook up everynow and then, but she still refuses to deepthroat me, but every now and then she lets me hit her in her super tight ass.

     Fiona was the biggest surprise. I had to go out East again and Fi asked me If she could take her instead of Chrissy. I ran it past the boss lady and she said fine. Chrissy flashed me a disapproving look as we went out the door. Fi was 45 at the time, and drove a super cool Z28. Every now and then everyone in the office would go bowling on a Friday night, and those were the nights for flirting with Fi. She mostly brushed off my playful advances but every now and then I would make her blush and smile.On this particular day she was wearing her typical out fit, a pair of tight jeans that showed off her great ass and her leather and wood high heel mules, which of course made her fine ass even finer. The only thing I was disappointed in was she wore a dark purple botton down blouse instead of her standard t shirt. When we got out East we went upstairs and started doing our paper work. I looked over and I noticed she was tearing up, and her mascara was running a little. I asked her what's wrong and she started to explain that she was having problems with her husband, that she thinks he's fooling around on her. I put one hand over hers and said "why would he do that? You're beautiful." She blushed and said "thank you". She went on and said she "thinks that if he could, her husband would have 2 wives...one for cooking and one for sex. Unfortunately I'd be the one for cooking." I said "why would he say that? You're funny and pretty and have a great body". She thought that maybe she was "looser" you know...down here and motioned toward her crotch area. "I said "well that sucks for him...he must have a small pecker". She laughed and said "I'm going to the bathroom to fix my face. I'll be right back and I said "Take your time." When she came back she looked much better but I did a double take when I notice that she had unbuttoned her blouse more than it had been before. She stood over me as I was seated at the desk and motioned for me to stand up. When I stood up, she said "I'm going to do this before I lose my nerve", and put her arms around my neck and kissed me passionately. When we seperated, She had a big smile on her face and said she had noticed me hitting on her pretty hard and that the feeling is mutual. I put my hands on her slim waist and pulled her close to me and started kissing her again. She is a grrat kisser. As we started breathing heavy she stopped and said that she has a few things before we proceed with this. She said "I know you're fucking Connie, and Chrissy...that's gotta stop". I nodded in agreement. "I also know you're going to want to do it now. First I'm not comfortable fucking here." I said "that's OK we can finsh up early and go to a motel, and if you're worried about being to loose check this out..." He unzipped his pants and pulled out his huge cock. She said "Oh MY Godd!! That's huge" With that she said "I can't....I'm on my period". I led her over to the couch and guided my cock into her waiting mouth. She worked it like a hooker in the red light district....she was fantastic, even better than Cindy. When I came she swallowed every drop of my cum. She collapsed in my arms and said "I can't wait to get fucked by you" and I said "how long?" She held up 2 well manicured fingers and mouthed "2 days". Then said out loud "yeah I was pissed. It came early this month and I've hadf this planned out all week, but you didn't have to come her until today. My plans were to fuck you like you've never been fucked before." I replied "Well something to look forward to". "I do have some weird rules about where we do it though...I don't want to rule out your apartment, but I really don't want to be seen going in and out of there being that there's a deli on the ground floor., but there will be special occasions. Also, my house is out of the question. I won't fuck in my bed. We can meet for lunch, and fool around in our cars, go on special assignments, which we do anyway, and finish as fast as we can and get a motel room. Or you can find someone to let us use their place. Or you can buy a nice van with a bed in it." I thought for a second and said " Yeah and I can get a sticker on it that says "If this Van's a Rockin' Dont Come a Knockin'" She laughed and we made out for a few more minutes aen packed up our stuff and headed back to the office.

    It took a while for an opportunity to presnt itself to Fi and myself that we could start our affair. We spent a week mouthing dirty stuff to each other, rubbing her ass on my hard cock when do one was around, or flashing me her tits. We wound up getting into Fi's Z28, driving to a park, and fucking each other's brains out (thank God for tinted windows). There was an akward weekend when the boss lady sent us to and Chrissy to Las Vegas for a trade show to help out on sales. Fi and I were in the hotel hot tub one night, when Chrissy joined us. She looked great in her bikini by the way. Anyway, she asked us bluntly if we were having an affair. Fi looked at her and said "Yes, and I would like to keep it quiet". Chrissy was obviously pissed of at what she viewed as Fi stealing me away from her. She had no idea I was fucking Connie at the same time I was fucking her. Chrissy laid out her terms in no uncertain way. She insisted on having sex with me once a week or she would blab about the affair. She then said, "you two don't mind if I take my top off do you?" I acted like I was bothered me but really, Chrissy had a great rack and I was instantly hard. I spent the whole weekend sneaking around, first fucking Fi, then fucking Christine. I was going to suggest a threesome to relieve the stress, but I knew Fi would never go for that, and then on th last day, I walked into Fi's room and what did I see? Christine in between Fi's legs licking her to an orgasm. What could I do? I whipped out my cock, and offered it to Fi, which she readily took into her mouth. I went to fuck Christine but she denied me and said "She's mine now. You have to wait your turn." and made me finish myself off looking at her tits. Somehow, Christine had made us submissive slaves.

    Things went on like that for a couple of months, and there were many nights when Fi and I laid belly to belly wondering how we were going to kill Christine. And then one day, I had to go out East, and Christine decided it was "her turn". When Fi and I went went to the east warehouse, we got our work done, and then fucked hard. With Christine, it was all about her depraved sexual desires. She started screaming when I fucked her yelling, more....harder, deeper, and there was no doubt that the ladies downstairs could here her screams. So long story short, I was fucking Christine one time in the upstairs office, when we were interupted by the boss lady, and I'm not going to descibe her looks. I'll leave that to your immagination. Maybe she was a good looking milf, maybe she was a sexy granny, maybe she was a nepo Diva accostomed to getting her own way, maybe she was weird looking old lady who hadn't had dick since the Nixon administration. Christine and I were both buck naked and Christine pussy juice was all over my cock. The Boss Lady says "Well well well, I heard the rumors but I didn't think it was true. Between you horrendous reports and the ladies telling me stories, I figured it was time I investigated it myself...and what do I find? I little young hussy fulfilling her own sexual desires, and a man who is so weak, he can't tell the young hussy to go fuck herself. Cheistine starts to utter "...but maam" when Boss Lady shoots back "but maam nothing get dressed and get into the Mercedes. I'll deal with you later." As for you, You will satify me the way a woman in my position needs to be satisfied". With that, this woman fucked me 3 ways to Friday and then some more. She screamed louder than Christine ever did, but I'm sure the ladies downstairs didn't report that. When I was spent and she was finished with me, she turned around, while she was getting dressed and told me I'm Fired. Come around the office again and you'll regret it.

    Well in the end, that little episode cost me almost everything. My job, Christine was too afraid to hook up with me, Fi, was pissed from the get go and never spoke to me again. I did run into Malika one weekend at a wedding, turns out she is a lesbian. Oh well at least I couldn't fuck that up (full disclosure, I did wind up hooking up with Malika and her lover after the wedding, but they Ross Gellered me...oh well). Celeste did meet me outside on the day I needed to sign my exit papers, and gave me a great kiss and said that she wouls miss being around me. 

    Last but not least, I still continued to see Connie (Truth be told I never really STOPPED seeing her). She got me another job in the city, and we wound up being like boyfriend/girlfriend. I introduced her to my parents, and I'm currently living with her. I've never been happier.

     

     
      Posted on : Jun 7, 2026
     

     
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