Story Details

The bosses' boss

thatguyisalways on True Stories

Back in 1992 I started my first real job out of college working for a major technology company in the bay area. I was a grunt in the finance department dealing with partner marketing. I was just happy to be employed because the economy was not that great at the time. My manager's supervisor worked in my area and was high enough up to have a private office. For purposes of this story, I will call her Claire. Claire’s office was on a corner near my cube so I got to see her a lot. She was divorced and drop dead gorgeous. She was tall, 5’8”, with most of her height in her perfectly shaped legs. They only had to carry about 125 pounds also, and that weight was distributed to all the right places. Every time I saw her I checked her out. She dressed in very nice suits and expensive silk blouses with her skirts a bit higher than most women her age, but she had the legs for it and I loved looking at them, particularly with the classy high heels she preferred to wear. Wearing those heels also produced a motion to her walk that made her perfectly shaped ass move in a fashion that would give a priest a hard on! I was not alone in my admiring glances, every guy in the office noticed her, and often to the jealous disgust of the other women in the office. Claire was really quite beautiful and had a face reminiscent of Bo Derek, but with auburn hair and incredible green eyes. She also had really great tits that even at her age didn’t really need a bra for support. I would sometimes get half hard (didn’t take much at that age, lol) thinking of what I would like to do with her which kind of freaked me cause she was 43, just two years younger than my mom at that time, but she still looked incredible and not anything like my mom. I masturbated at least twice a week thinking of being with her in bed.

After I had been there a few weeks I started timing my trips to the break room to coincide with her trips and made small talk as we got coffee. She was really nice, but usually in a bit of a hurry. Over the next several weeks we got to know each other a little bit, and she seemed to like me, and would sometimes take a little more time for our conversations. She had a son a couple years younger than me in college and she would tell me about what he was doing and how school was going and stuff. I offered observations based on my own college experience, and she seemed to appreciate my interest and input.

One day while we were in the break room sitting at the high top chatting Claire got a page and answered it at the wall phone behind her next to the door. She turned her back and leaned up against the wall cocking her hip a little. It made her skirt kind of raise and move away from her legs on the back side of the skirt. I had an impulse to look up her skirt and took advantage of the opportunity by dropping some newspaper that had been on the table onto the floor under the table and when I got down to pick it up I looked under the table and bent over far enough to look up her skirt all the way to her gorgeous ass! She was wearing sheer pantyhose, and a thong! Her legs and ass were incredible. I stared longer than I should have and was starting to get hard by the time I stood back up. Claire’s call ended in another minute but before she left, she turned and looked at me with a rather strange expression. My heart stopped. Had she seen me out of the corner of her eye? About ten minutes later my line rang, and it was Claire. She asked me to come to her office. She was standing as I walked in and she turned telling me to come in and close the door.

After I closed the door she sat down and asked me if I knew why she had called me in. My heart was already racing, and I could feel my face getting flushed. I looked at the floor and just started blurting out my apology and rambled on about "you're just so pretty and sexy and I've fantasized about you and don't know what came over me but when you turned and leaned on the wall I just became obsessed with seeing the rest of your legs and took the chance and I am so – so - so sorry and it will never ....." Claire cut me off with a very breathy "WHAT?" I looked up to see she had stood up and had a wide eyed expression and open mouth and immediately realized she had no idea what I was talking about. She held up a file in her hand and said "I was asking about the - - - - - account and the co-op crediting error you made. The partner is very upset and called earlier. That was my boss that called while we were in the break room”. The silence that followed was deafening. I could feel and hear the blood rushing in my ears. I looked back at her. She still had that shocked look, but now her face was flushed too. She started stammering “You …. you ………… we'll …….. we’ll deal with this later". She turned, walked to the door and held it open for me. I heard the door close behind me as I walked back to my cube. I was in a daze and feeling panicked. I started thinking about where my next job would be and what people would say about me after I left and whether or not anyone would hire me if they found out what I had done. My ears were hot and ringing. About 30 minutes later my phone rang. It was Claire and she told me to come back to her office. I was shaking as I entered, and she pointed to a chair in front of her desk. As I sat, she closed the door, and locked it. I figured this was it and that I would be fired. I was hoping that the reason everyone would think I was fired would be because of the accounting screw up but I knew they would find out that the real reason was because I had been busted as a perv.

Claire turned, and with arms crossed, she said "now show me what you do when you fantasize about me". At first I just stared at her and thought I had heard her wrong. She then softly said in a somewhat mocking tone “Come on now, I want to see what you do when you have your little fantasies”. I started to laugh nervously and say something dismissive but she cut me off and hissed quietly "Show me or I will have HR show you the door!" I must have looked terror struck, because just then her demeanor softened, and she said, "I’m sorry, here, let me help you". She then slowly pulled down that side zipper some women's skirts have (why do they put zippers there anyway?). She held the skirt with one hand as she lowered it, and stepped out one leg at a time. Her white lace thong was sheer enough for me to see her mound and her little tuft of pubic hair. My cock was now getting hard fast. She cocked her hips to one side and placing her hands on them and swaying slowly back and forth, while softly saying “Go on now, this is what you wanted to see, so now you show me what I want to see." I nodded, stood up, slowly started to undo my slacks. "That’s it, don't stop" she whispered. I completely undid them, and let them drop to the floor. I then slowly pulled down my boxers, releasing my already hard cock to spring up and twitch to each throb. My heart was pounding so hard I thought I could hear it. Clair continued to nod as I proceeded to grasp my erection and masturbate. "That’s it, don't stop" she whispered again as she walked over to her credenza to pull some tissues. I could see her entire gorgeous ass as she did, and my cock just throbbed!

What was happening was more than a little scary; I mean this was my boss’s boss for crying out loud! It was downright bizarre, but also exciting. Soon I was jacking really good and it was really turning me on the way she just stared at me while I masturbated. I knew I wouldn't last long. She came closer as she handed me the tissues she had taken from the credenza but never took her eyes off my cock as she did. She backed up and leaned on the credenza behind the desk, still staring at my cock as I jacked it, and as she did she unbuttoned her blouse and pulled it open to reveal her tits (36C) held in a sheer bra that barely showed her nipples. She undid the front clasp, and her breasts fell out. Her nipples were totally erect! She asked in a whisper “There, do you like that too?” I nodded as I stared in disbelief! It was obvious that I was becoming more aroused, and then while staring at my engorged cock she reached up to the desk and moved some papers off the corner and softly but excitedly said “When you cum don’t cum in the tissue, cum on my desk there". She stepped back to the credenza, leaned back on it and watched while rubbing one hand over her breasts, first one, then the other, and lightly rubbing her thighs and crotch with the other hand. In just a few minutes that familiar feeling was filling my groin, and I whispered, “I’m going to cum!” Claire whispered “Yes, cum for me, cum on my desk for me!” Hearing the woman of my many weeks of fantasy telling me to cum for her was more than I could take and immediately I started cumming. My first spurt flew clear over her desk, I then bent over a little and jacked the rest onto her desk. My white cum on her dark wood desk looked incredible, and I don’t think I have ever jacked more cum out in one ejaculation than that day in her office.

I looked up at her as I was finishing cumming. She was now seated on the credenza, slightly leaning back, legs spread, squeezing a tit and pinching one of her nipples with one hand and furiously rubbing her mound with her other hand! She was staring intently down at her legs, and then I noticed; my first huge spurt of cum had landed on her leg high on her thigh. It was starting to run down the inside of her thigh in a long wet string of cum and sperm. The sight made my cock twitch hard. Suddenly Claire reached up to the top of her pantyhose, and quickly slid her hand inside, and then down inside her panties where she started rubbing her clit quickly. She was so wet that her rubbing made those “wet cunt” sounds of a woman really turned on. She alternated between looking at my cock and then back at the sperm on her leg, all while masturbating intently. Very soon her breathing started becoming heavier. She was talking quietly saying “yes yes yes yes yes yes” as if in a trance. She looked up and made eye contact with me as she continued rubbing her clit and pinching her nipples with that look a woman gets when she is on the edge of an orgasm. Suddenly Claire spread her legs a little further, jerked forward a little, stiffened, and while rubbing with increased ferocity, threw her head back with open mouth and quietly gasped several times while softly jerking in orgasmic spasms with a guttural sound of “unh …. unh …. unh” coming out of her mouth as her spasms gripped her. She was cumming, intensely and I was transfixed by the beauty of her in orgasm and this totally improbable yet incredible sight. She was in her own world at that moment, and it was as if I wasn’t even there.

Claire came for what seemed like forever, but I know it was only because it seemed to me that time had stopped for a moment. As she came down, the occasional spasm would take her momentarily, and she would twitch and softly gasp. She leaned back to the wall, and clasped one hand over her chest as she breathed deep to catch her breath. Clair finally removed her hand from her panties and used that arm to steady herself on the credenza using only the heel of her palm making sure none of her moisture on her fingers rubbed on the credenza. It looked sexy as hell. She raised her other hand from her breast and lightly touched her forehead, veiling her eyes as she slowly shook her head and smiled a smirking smile while softly saying “Oh my, oh my, I don’t know what to say” she said as she shifted her spread legs to bring them back together. With that, we both became very self conscience and slightly embarrassed. Our embarrassment became obvious as we both started to giggle softly. I also became very aware of the aroma of wet pussy and sperm in the room. My breathing was nearly back to normal, but I was still shaking. She smiled and whispered “put yourself together”. I did, but as I finished wiping my cock and reached to wipe my sperm off her desk, she quickly whispered “No hon, leave that!” I don’t know what turned me on more; the idea that she was going to wipe up my sperm, or that she had called me “Hon”, lol! I was ready to leave and she finally stood. Unsteadily at first, but as I started towards her she held her hand up and shook her head “no”, and said, “I’m OK, just give me a sec.” In a moment she looked at me and smiled that little smirky smile that is on the edge of laughing again, and she nodded as she walked toward the door, motioning for me to do the same. She held a finger to her lips to indicate that I should be quiet. As she turned back to the door I saw her put that finger in her mouth and lick it. My cock twitched knowing that she was licking her own pussy juice at that moment. I watched as she listened at the door for a moment, my cum still running down her leg, then she turned to me and nodded to go. She stood behind the door as I opened it and walked out. I closed the door behind me, and I heard her lock it.

My head was spinning the rest of the day, and I couldn’t concentrate on anything. Finally around 5:30 or so as I was getting my stuff together to leave for the day, Claire walked by my cube, poked her head around the corner, smiled, winked, and said “see you tomorrow big boy”. I couldn’t even respond before she was gone, but my cock did. I was getting hard just thinking about what she meant by that wink.

The next day was Thursday, and everything actually seemed very normal. Claire was much friendlier with me however and smiled broadly whenever we saw each other that day. By Friday I was finally settling down with what had happened, and was long over my fear of losing my job. That morning around 10:00, my phone rang. It was Claire, and she asked me to come to her office and bring a particular file with me. I did as she asked, and as I entered her office, she motioned for me to close the door. “Lock it” she softly said after I closed it. I did, and my heart started racing again immediately. Claire motioned for me to sit down, and then she just looked right at me and asked “So what do you think about what happened the other day?” Not sure what she was looking for I hesitated. She sensed I was very nervous still and spoke up before I could. Claire said “Look, you are not in trouble with me or anyone else, and my question is purely a personal inquiry for my own gratification, and I will share my thoughts with you also, OK?” I said, “Sure, OK”. And proceeded to tell her that what had happened on Wednesday was without doubt the most erotic and sexy thing I had ever experienced. Claire smiled and nodded as she sat back in her chair and looked past me as if she was imagining something. Finally while still smiling she looked back at me and quietly said “You know sometimes I think I am a little crazy, but not because of what I do, but because I don’t care enough about possible consequences to stop.” She laughed softly as she stood up and walked around her desk. When she got to me she extended her hand to help me from my chair. I thought our talk was over, but she pulled me to her, wrapped her arms around my neck and shoulders, and planted a kiss on me like I was her long lost lover. I pulled her close, and we made out like Freshmen under the bleachers for five minutes. Our tongues were probing and our hands were all over each other. She moaned appreciatively as I felt her breasts and buttocks through her blouse and skirt. She pulled my face back momentarily and looking me in the eye and in a breathy voice said “Do with me what you want, right here, right now!” I didn’t hesitate, and led her to the desk, turning her towards it, and pushing on her back to indicate I wanted her to bend over. She did and as she did I pulled up at her skirt. She shimmied her hips to help, and as it cleared her perfect ass she stepped to spread her legs, and lay chest down, arms to sides on the desk and breathed “yeeeessssssss”. She was wearing thigh high stockings, and absolutely nothing else. I thought I would cum right then. I had my pants and shorts down in a second, and bent down to position my cock, and as I did, Claire rotated her hips forward to make her cunt more accessible. My cock head split her wet lips, and in one slow thrust met by her push back, my cock went balls deep in her. Claire whispered “OHhhhhhh fuuuuck me”. I had jacked off many times since Wednesday so I knew I could last a bit, and I did. We fucked like that for ten minutes or more before she reached under herself to rub her clit. Claire asked “How is that view baby?” I said “Sexy as hell”. Then Claire asked something that made me want to cum right then. She asked “Does it look a little slutty too? Do you like me looking a little slutty?” I responded, “Oh yah Claire, you do look a little slutty, beautiful, but slutty too.” Claire whispered “yes, yes, fuck your slut baby, fuck your slut, ummmmmmm.”. In just a couple more minutes she was bucking back into me hard, and cumming. I could hold it no longer and grabbed her by the hips hard and pulled her onto my cock hard as I came and pumped my sperm into her sopping wet cunt. Spent, we both sat down on the floor in front of her desk to catch our breath, hold hands and softly kiss.

To make a long story shorter, we become regular lovers within the week and I started sleeping at her apartment 3 nights a week. We fucked like minks for a little more than 10 months before she left and took a job at one of our competitors across town. The last two weeks we worked together we fucked once in her office every day and at her apartment every night, usually twice a night. She loved being bent over and fucked from behind. Those last two weeks she wore thigh highs and nothing else underneath, and I bent her over her desk and filled her to the brim every day those two weeks. We remained occasional lovers for the best part of the next three months, but then we both moved on, and eventually for both of us to more appropriate love interests. I had heard that she remained single till her son graduated, and then she married a VP at the firm she worked at that time. I married my first wife a couple years later, but that only lasted two years. Wife number one ended up being a total whack job. I stayed single then until just four years ago. Wife number two is a doll, and I am lucky to have her.

I still think Claire was the hottest and best lover I have ever had in my life, even 17 years later. We saw each other at a charity event last Christmas. My wife and I were at the table adjacent to her and her husbands. After the speeches and dinner, our tables thinned out and they joined us for after dinner drinks. My wife and one of her friends were still talking, and Claire’s husband was engaged in conversation with another friend, so we had a chance to talk and I found that she is happy, a grandmother twice over, and enjoying her life. She is one of those amazing women that are sexy at any age, and I took the opportunity to comment that even at age 59 she was still drop dead gorgeous, and that even at that moment she was causing me to “stir” thinking of what I would like to do with her right then. She laughed softly, smiled and blushed a little. Quite frankly, the way she looked that night if I were a guy on the prowl I would have gone after her before most women there, including my wife, even though my wife is 27 years younger! That’s not to say my wife isn’t good looking, she is, but rather to say that my former lover is that beautiful and sexy. Her shape and body looked nearly as good as the last time I had seen her, and then it was almost “perfect 10” material.

After a while the band started playing some slow music and we had a couple of dances together. While dancing she smiled as she told me she also still often thinks of the times we had together. I shared with her that there isn’t a week that goes by that at least once while inside my wife I don’t fantasize that it is her pussy that I am inside of, and also at least once a week I still masturbate fantasizing about her.. She smiled and in a wide eyed somewhat mocking fashion softly said “Oh really”. To prove my point I pulled her closer and pressed into her hip with the erection she had given me with our conversation. She smiled and flushed a little, whispering now with excitement “OHHhhh my!” Her eyes darted from the dark and crowded dance floor to the darkened room for witnesses before pressing back, reaching down and gently caressing my erection, and then kissing me on the cheek as she whispered in my ear, “Thank you for always making me feel young and beautiful. I do still and often remember the time we shared, and yes, I do so while pleasuring myself”. I groaned softly as she gave me one last squeeze and as she did I gently caressed a breast. I heard her sigh as I did, and it made me want her even more. If we had been there without our spouses, I know we would have found a secluded place to have each other.

We exchanged phone numbers that night, have talked on a few occasions, had coffee twice, and even flirtingly hinted of reliving some of our past some future stolen afternoon together. But we have never followed through or made solid plans. Perhaps that is best in that we are both happily married, and maybe the memories are better than anything we could attempt to relive. But still, I fantasize.


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