Everybody wants to fuck Cindy. She’s young, attractive and single. She always dresses tastefully and she’s on the fast track in the company, at least as far as I'm concerned. I’m her boss. My name is John, which you probably know by now if you’ve been following my stories. I’m the boss of eleven beautiful girls who work under me, at least in my dreams. Cindy is a special challenge, almost too nice to fuck, if you know what I mean. I’ve wanted her so badly ever since she started working for me that I’ve gotten into the habit of pulling up her pictures from the office holiday party on my computer when my wife isn’t at home (or even sometimes at night in the office, I’ll have to admit) and jerking away at my rod until I explode on her face on the computer screen. God, if I could only really cum on her face! The thought always makes me hard again in an instant and launches another slideshow of her pictures and another jerk-off of my knob.
There never has been much of an opening to slide through (sorry for the cheap pun) when it comes to plotting to fuck Cindy. Several men around our office building have made attempts to get something going with her but she always politely refuses any advance, stating that she is in a relationship and isn’t interested. She’ll always thank the men for their interest and tease that if she ever finds herself alone, she’ll dial them up in an instant. It leaves the guys with a faint hope that they really might have a chance someday. I can’t help but think that she gets off knowing that leaving a little opening for them (sorry again) that they are probably jacking off at home or in the bathrooms in the building, thinking about her tight fitting clothes, pretty face, wet lips covering those beautiful teeth, and those beautiful long legs!
Cindy's legs scream, “Bend me over and fuck me!” She wears snug fitting skirts most of the time that come down to the top of her knees or sometimes just a bit below. They’re never too tight but fit her just tight enough that when she walks around the office you feel like you’re watching her ass through the fabric. She wears her pretty dishwater blonde hair down most of the time but occasionally she’ll pin it up in a bun, don some high heels, and display the best “naughty secretary” look that anyone will ever see. And of course she knows that she can pull it off with ease and seems to make a point of walking around the office more on those days than others.
Everything about her is exquisite. She has beautiful skin, an infectious smile and a charming school girl type personality to go along with it all. Officially her personnel file says she is 26 but she comes off as much younger, almost like a girl about to get out of high school or a young college coed. I know from talking to the other girls in the office that she has never been married. So who is this “relationship” partner she has? I also know that she has a female roommate, Dawn, but the few times I’ve seen them together it doesn’t seem like there is anything going on between them. There isn’t a “dominate” looking one in the pair and in my warped male mind that’s the way I see the typical lesbian relationship, one butch like girl pounding away on the other. These two just look like a couple of innocent cheerleader types, like the ones that hang out together at bible study instead of the bars.
Recently I walked into the kitchen at the office as she was explaining a change that was coming up in her life to Susan, another lady in the office that I have been intimate with on occasion. I slowly poured myself a cup of coffee and began to fumble around with the sugar packets and the cream dispenser even though I drink my coffee black. As I mixed the awful concoction and slowly stirred the goo into a brown swirl, I caught what must have been the end of the conversation. I listened intently to Cindy as she explained, “Yeah, Dawn is moving out tomorrow for sure. She met a guy and they’re getting pretty serious and it was just getting a little awkward around the apartment. They were always sneaking back to the bedroom and I knew what they were doing, which was fine with me, but I guess it weirded them out to know I was within earshot and listening to them making love. God, they could sure go at it. There was no mistaking when they reached a climax together. I think the whole complex could hear it.”
She cracked a big smile toward Susan and then turned around to leave when she suddenly became aware that I had been behind them. She knew instantly that I had heard her confession of eavesdropping on her roommate making love and the embarrassment quickly took over. Her pretty cheeks reddened and she tried to stammer out an apology. “Oh, I’m sorry John. I didn’t know you were there. I, um, I shouldn’t have been going on about Dawn. Oh, this is so embarrassing.”
Susan helped us both out of the jam. “Don’t worry Cindy. John enjoyed every bit of your story, didn’t you John? He’ll be jerking off in the bathroom as soon as we leave.” Susan could be brutal when it came to office situations and sexual matters. She and I have fucked a few times and even had a three-way of sorts with my direct assistant in the office, Debbie. I could only wonder what this innocent young lady would think about me after that comment. After all, I’m 55 years old, not exactly a spring chicken, and not exactly what a young budding woman like Cindy dreams about at night, although certainly from my end she had been in a few of my dreams. And Susan was right. I did want to go jerk off. The vision of Cindy outside her roommate’s door, listening intently to the lovers pounding away at each other while maybe, just maybe, she was sliding a couple of fingers in and out of her own pussy. Geez, I headed off to the bathroom as soon as they left!
Susan came to my office later in the day. I wanted to dress her down for putting me in such an awkward spot with Cindy but she started talking before I could form my words. “You should go talk to Cindy, John. She’s going through a tough time with her roommate moving out and I think I made her pretty uncomfortable today with my comments about you wanting to jerk off to her story. Maybe you can show her some of that fatherly-like compassion you’ve shown some of the other girls in the office.”
Susan was referring to her own imaginary daydreams that I was fucking everything with legs in our all girl office. While it would be nice, I’ll admit, I’d really had only the one experience with Susan and Debbie that I’ve written about previously, and of course a couple of unmentionably erotic twists with Susan’s twin daughters, Tiffany and Amber. That latter fact always made me uncomfortable because I could never be sure the two 18 year old cock pleaser’s had not told their mother about their escapades with their mom’s boss. I wasn’t too comfortable at this point with talking to Cindy after jerking off in the bathroom to her story telling, but I agreed to give it a try before the end of the day.
At 5:00 pm sharp I buzzed her on the phone. “Cindy, can you come by my office before you leave? I’d like to discuss something with you before you head home tonight.” She agreed to stop by but it was a full 45 minutes before she made it to my office. By then everyone had taken off for the day and it was starting to darken outside the windows of our high-rise office building. The city lights at night made the tension of the day lessen quickly. I offered her a drink which I was relieved she accepted. “I’m really sorry I was listening in on your private conversation today”, I said as I handed her the glass of red wine she had chosen from my executive bar. “It was very unprofessional of me”. The wine wet her pretty young lips and they glistened in the darkening evening light.
“Thanks John, but you don’t have to apologize. I shouldn’t have been discussing something so private in the office. I’m really embarrassed that you learned about me listening in on my roommate making love. Dawn and I have been roomies for years, since our college days playing soccer together. She’d kill me if she knew I did that”. My mind conjured up a few lustful thoughts of girls in a hot steamy locker room as she continued. “We’ve never been lovers or anything; although I’m sure everyone thought that we were. We’re really just great friends, soul mates almost. I’m really going to miss her. But it’s the right thing for her to move in with her boyfriend. I guess I’m secretly jealous a bit. No, I’m jealous a lot.”
Tonight was “naughty secretary” night for Cindy’s wardrobe. Her hair was up in a tight bun, a pair of black glasses accented her beautiful glowing coed looking face, and she wore a tight skirt that was made all the tighter when she crossed her legs as she sat in the chair in front of my desk. I freshened up her wine glass and sat down in the chair next to her, finally blurting out a question, “You must have a lot of men dangling on a string of your own Cindy, right? As beautiful as you are, why would you be jealous of Dawn?”
Her eyes brighten as she looked up at me, while she took a long sip of wine. A huge smile burst across her face, “You think I’m beautiful, John? You wouldn’t believe how seldom I hear something like that. Really, you think I’m beautiful?”
“Look Cindy, I’m old enough to be your father, but I’m still a man and I know a beautiful woman when I see one. Yes, Cindy, you’re strikingly beautiful.” I couldn’t exactly understand why I was taking the conversation this direction, but wine will do funny things to a man, especially when a 26 year old subordinate employee is sitting in a tight skirt in the chair next to you. I wanted to know more about her and I wanted to hear it now, while we both had our guard down. I continued to probe, “Don’t you realize the effect you have on men around the office? You could have a lover a day if you wanted to.”
I could tell that last comment embarrassed her and she uttered a quick response. “I think you’ve had too much wine John. You’re starting to imagine things. I’ve never really felt like men were that interested in me. I’ve always thought their advances were just to try to get me to help them market their clients. They’re always asking me out to dinner with them to meet some new prospect. I think they think I can help them close the deal somehow.”
“Haven’t you heard that sex sells, Cindy? Sure you can help them land a prospect.”
“Look John, I wouldn’t sleep with some client just so one of our sleazy salesmen could get a commission. You’re not serious are you?” She seemed really appalled at my suggestion.
I tried to recover. “Look, I’m not suggesting anything of the sort Cindy. I’m just making a point that men like to go out with beautiful women. It loosens their pocket books. It makes them more vulnerable to saying yes. Get it? It’s like when you’re up for a raise or a promotion. How do you dress for the interview? Do you wear a plain outfit, or do you dress it up a bit? Get it now?”
Cindy sipped the last of her second glass of wine. “I guess I see your point John. I never really thought of it that way, but I’ve done that all my life when I really wanted to get somewhere with someone. I guess the sales guys are just trying to work the same angle. You know, I put my hair up before I came to your office because I’ve seen you looking at me when I wear it this way. I thought it might help me get what I want. I’ll have to admit that I’m guilty of doing the same thing.”
“So what are you trying to sell me?” I tried to roll the words out slowly but my adrenaline and a few other chemicals were taking over and I must have appeared anxious and eager. I’m on those daily pills that help me get an erection when I need it and I was afraid I might get one and not need it. What a cruel dilemma that would present. I waited for her response as I felt my cock starting to stiffen. I tried to sit in a non-revealing position but I saw her lower her gaze to my crotch when I shifted my position in the chair.
“I’d like another glass of wine, sir,” she said, adopting a subservient manner as an employee to a superior might do. “John, this is Dawn’s last night at the apartment. She and her boyfriend are packing up a few last boxes and will be out before morning, but she asked if they could have the place alone tonight for a few hours. I know she just wants to fuck him in the apartment one last time without me listening in. I really don’t have any place to go until around midnight. Could we just have some more wine and kill the time together? That’s all I’m asking for John.”
Well, I certainly didn’t want to disappoint a damsel in distress, the one in my office or the one in Cindy’s apartment. I poured us both another glass of wine and got a little bolder. “So when Dawn and her boyfriend would make love, what did you do while that was going on?”
“It’s really hard to not do something while that’s going on, if you know what I mean.” She had to be referring to masturbating, but I wanted to hear the details. I pursed my lips and made a questioning facial expression, raising my eyebrows in a silent gesture for her to continue her explanation. “You know what I mean John. Don’t make me say it out loud.” I still sat silently, increasing my inquisitive look and drinking longer on my wine. “Alright you pervert, I fingered myself to an orgasm while I listened at the door. There, does that make you happy?”
Yes, it did. It also made my dick happy and it got hard as a rock as soon as her words registered in my wine drenched mind. Cindy noticed my erection immediately. “You sick fuck”, she feigned a shocked response while grinning all the while. “You’re getting off on me talking about masturbating?” She took a long drink of her wine glass and sat it on my desk, standing and smoothing her skirt as she stood up. She slowly removed the clips that held her hair up and shook her head from side to side as it unfurled before me. I watched as she slowing walked over to the door. The calf muscles of her legs were taught and firm and her black high heels clicked a rhythmic tap in the quiet emptiness of the office. My eyes followed each step as she approached the door, then I followed her outstretched fingers as they wrapped around the door knob, holding and turning it gently as she pushed the door closed. She turned out the main light leaving only my desk lamp to light the room and then turning to face me, she leaned back against the door.
“Would you like to hear what I heard behind the door, John? Her question was accompanied by a beckoning finger bending slowly out and back inward repeatedly, motioning me to come over to her. My pants were bulging noticeably now and I didn’t try to hide my arousal. When I arrived in front of her at the door her hand went immediately to my pants and she held my cock in her hand through the thin fabric. She slowly began to speak again in a soft whisper while she continued to gently stoke my hard on. “I could hear Dawn moaning quietly at first, John.” The way she personalized the details by adding my name to the statement made it obvious her intent was to arouse me.
“I could only imagine through the door that her boyfriend was stroking her pussy from the outside of her panties, like you’re going to do for me John.” She took my hand in hers and lowered it first to the bottom of her skirt. Together we lifted the skirt upward and she released my hand from hers, leaving it at the base of her panties, my fingers coming to rest on her soft mound. I gently rubbed on the outside of her panties and she moaned softly in partial role playing of the scene she had just described, and also partly in the growing reality of the moment.
“I heard her gasp as he moved his hand inside her wet panties, inserting his fingers slowly into her vagina, first one, and then two. At first entering her ever so lightly and then plunging deeper as her moans grew loader and her breathing grew faster.” Cindy stood quietly for a moment, her arms now wrapped around my neck in a gentle dance-like hug. I took the cue that I was to mimic her narration. I moved my hand from the base of her panties and slid it slowly into the lace fabric at the top. I eased my fingers inside and then downward toward the dictated destination of Cindy the narrator. That destination was wet, creamy wet, and moist. My fingers slipped easily inside her wet cunt, first one, and then two, just as the narrator described. As it was scripted, she started a slow moan. Not a copy of the moaning of Dawn, but clearly her own uttering, and her hips began a slow back and forth gyration in advance of the narrator’s coming description.
“I could hear her begin to buck forward as his fingers worked deeper into her. Then there was a wet, licking sound.” She began immediately to tongue fuck my ear as I continued my finger assault on her wet pussy. She nibbled and sucked and explored each ear in turn and then began to kiss my neck as she started to unbutton my shirt, although not issuing a new command. I listened intently for a new measure of pleasure to be described as I continued to perform as instructed. “She continued to stroke his cock from the outside of his pants and I could hear the fabric ruffle as it rubbed against him”. Cindy complied with her own narration, stroking my dick through my pants.
“I heard the sound of a zipper, then a belt being undone.” She followed her own narration again. My pants fell to the floor and against only a pair of thin boxers the head of my engorged cock poked out at full mast. Cindy looked up at me and met her eyes directly with mine. “My god, your cock is huge, I heard Dawn exclaim from behind the door”. She stroked me slowly and brought her lips up to meet mine. We embraced without narration, out tongues too engaged for anything to be spoken. Cindy was now jerking me off at a slightly faster pace and a drop of pre-cum oozed out of the head of my dick. She felt it on her fingers and added, “I heard Dawn say she wanted to lick the pre-cum off of his dick.” Something told me the narration might have strayed from the audibly observed event and could simply be a live description of whatever Cindy felt should come next. I hoped so.
She lowered to her knees in front of me and began to lick the tiny droplet of cum on the engorged bulb at the head of my cock. First her tongue moved slowly in circles and then with the command, “I heard her tell him she wanted to suck his cock,” Cindy plunged her mouth over the entire shaft and down to the base of my dick. She moved slowly back to the tip and then plunged the shaft fully into her throat again. She continued several strokes and at the conclusion of one outward thrust she raised her gaze to my eyes and uttered, “Then I heard him beg Dawn to lick his balls.” I felt this was an act I should follow and I replied in kind. “Cindy, please, will you lick my balls?”
I was late reacting to my stage cue as she already had one in her mouth and the other in her hand. She was clearly describing her own goals now and I hoped they followed everything Dawn and her lover had done and maybe more. She gently licked and sucked my balls one at a time, taking them deep into her mouth and pulling gently away from me each time she engulfed one until I felt a slight strain on my sac, then she would release the pressure only to repeat the process on the other one. To my complete and utter surprise and indescribable enjoyment, while this oral ball message went on she slid her middle finger under my ball sac and along the sensitive skin beyond until it found and entered my asshole, slowly plunging in and out with the expertise of an experienced young woman. I just about shot a load on her hair but I held it back for all I was worth, hoping to deposit a hot load of cum inside her somewhere.
“I heard Dawn pull his dropped pants and boxers off his legs and remove his shoes and socks and it sounded like he pulled off his unbuttoned shirt at the same time.” I hadn’t waited for Cindy to narrate that part as I had my shirt off before she got me undressed. I stood in the dimly lit room now fully naked, my cock swollen and reaching for the ceiling as Cindy rose from her knees and grabbed my dick again in her small hand. “I could hear Dawn begin to unbutton her blouse and her boyfriend was clearly fumbling with her skirt from the sounds coming from the room”, she explained. I began doing my own fumbling on Cindy’s skirt but my eyes were fixed on her as she first unbuttoned her blouse and then reached behind her back to unclasp her bra. As I completed the skirt dismantling it dropped to her ankles quickly followed by her soaked panties. She kicked both garments and her high heels off, almost simultaneously. We were both fully disrobed and it felt tingly awkward for a second.
The tingly awkward part may have been caused by her nipples pressing against my chest when she leaned into me and planted a tongue searching kiss on my lips. My fingers returned to her pussy and I gently rubbed on her clit, trying not to get too far ahead of the story. Hearing Cindy vocalize each move along the way made for a wild, almost perverted ritual of lovemaking that I had never experienced before and it almost seemed like it made it easier for her as she could pretend she was just replaying a fantasy of Dawn’s lovemaking session. I slowed my stroking motion as she began again.
“I heard Dawn say, I want you to fuck me from behind.” I couldn’t believe my luck as Cindy turned her back to me and bent slightly over, bracing herself against the door. I would have to thank Dawn the next time I saw her. I eased up closer to her tiny beautiful ass. Her hand reached under and between her legs and grasped my cock, guiding me to the wet entrance to her vagina. She pulled the tip of my cock just inside then waited for me to do the rest.
I started a slow pushing motion into this tight schoolgirl sized pussy that just didn’t seem big enough for my grown up cock. “I can take it all John”, she said. Did I hear that right? Was that Cindy or part of the narration? Wait, she said John, right? Fuck. The realization registered in my brain before I could put any controls in place and I plunged the full length of my rod inside her cunt before I could restrain myself. She gasped and bucked toward the wall to release a bit of the pressure I must have caused. “Oh, fuck. My God that’s deep. Shit. Holy fucking shit!” She uttered a long rage of expletives in reaction to the deep gashing that had just occurred. She moved one hand back around to my hips and pushed me back slightly but kept me just inside her. “Okay, big boy, let’s try this a different way. You stand still and let me do the work.”
I complied and she began a slow back and forth fucking of my cock with her pussy, using the door as her brace, pushing back and then releasing forward, taking only what she wanted initially but finally plunging me again to the bottom of her cunt. “See, I told you I could handle it all,” she proudly proclaimed while turning her pretty face back toward me and tossing her hair to the side as she did. I continued to stand strong and steady, making sure I was anchored for each thrust she mounted on my cock, each deep and joyous thrust. After assuring that she was taking it all in without pain I bent slightly over so my hands could reach under her and I cupped each of her breasts in my hands. Cindy has nice tits, not overly sized but ample for her frame and with nipples like erasers that often make an appearance through her bra in the office. I slowly fingered each one and they hardened to my touch. I began to wonder how long I could keep this up without coming.
Cindy was applying a personal touch to her clitoris for her own pleasure and occasionally she would reach beyond and stroke my balls, dipping her head and shoulders down and back so her hand could reach the full distance. While in that position she jacked the shaft of my cock a few times, getting a good dose on her hand of the juice from her pussy that had covered my cock, then she’d move her fingers back to her clit and raise her shoulders and head back up tossing her hair again onto her back. It was a ritual and a site that repeated itself for several minutes and I wanted it to never end. I held onto my load hoping for a big finish inside her, but please, just not now. She was plunging my cock deep inside her with each push back from the door and as her motions quickened even further I could tell she was about to come. “Oh, John, fuck me, John, give it to me. Oh fuck!” She cried out and with a deep lunge into her cunt I forced her into a violent shaking convulsion. I stood in place while my dick remained insider her, barely moving in and out as her breathing slowly returned to an almost normal rate.
As our motion came to a stop I pulled my pussy soaked dick out of her cunt and rested it between the cheeks of her ass. As it lay there it coated her bottom, including her tiny pink asshole, with her own pussy juices. I wondered if she would let me come on her ass. Exactly how experienced and liberated was this young lady? She started a slow rocking motion and her butt cheeks provided sort of a lubricated fuck channel for my knob and I realized I was going to lose my load on her if this continued, whether she was into it or not. Cindy began the narrative of Dawn’s love session again. “I heard Dawn say, I want you to fuck me in my ass!” Surely I didn’t hear this but if I did, she didn’t mention the name John this time so I knew we were back in fantasy land. This was no time to make a move. I would have to let this play out on Cindy’s orders. “Well, John, are you going to play along or are we done?” she asked.
That was certainly my cue and I didn’t hesitate further. I took the hard tip of my cock and pushed slightly on the little pink entrance to her ass. She reached behind with her hands and parted her cheeks, exposing her waiting hole and making the target obvious. With a few slow pushes the head of my cock disappeared into her ass. I noted a slight grimace on her face that quickly turned to a look of pleasure. I pushed an inch or so more and then I felt her rocking back on me and just that quickly I was in up to my balls and we were rocking furiously. I think Cindy knew I didn’t have much left to go and she began to buck harder and reached underneath to nurse the cum from my balls. “Tell me when you get close, John. I want you to cum in my mouth.”
That was the end of me. I bucked as hard as I could without exploding and then pushed with both hands on her butt cheeks, pulling out my cock. She wheeled immediately around and sunk to her knees in front of me. Her hand grasped my rod and jerked on it continuously for maybe five or ten seconds. I grabbed the back of her head with my hand and pushed her mouth onto my dick. She kept her lips slightly open so I could watch my load fill her up. As the first burst came from the purple engorged head, the milky white cum covered her tongue and each additional eruption added to the load until it forced her to swallow and take in the rest. She downed the remainder of my eruption and then licked me slowly, sucking the remaining drops from the end of my spent cock.
I slumped back against the door as Cindy walked over and picked up our wine glasses from the desk. We finished what was left and she poured us each a new glass. We drank together as she cuddled with me, facing me and pinning me to the door, pressing against my wet cock. We stood there silently for a few minutes, grinning occasionally at each other and sipping our wine. “So what did you hear from Dawn behind the door after that?” I queried, breaking the very comfortable silence we were enjoying.
Cindy paused silently, as if gathering her thoughts. I knew from her earlier admission that in the real scene she had been outside the door and had just finished masturbating. A slight smile grew on her face and I imagined she was remembering that exquisite moment when she erupted from her own manipulation as she listened to Dawn having an orgasm and slurping her boyfriend’s cum. But I was wrong, very wrong.
“Well John, as soon as I recovered from coming I pulled my fingers out of my pussy and I pressed my ear back to the door. Then I heard Dawn say to her boyfriend, I want you to fuck me all night!”
Cindy’s pretty young face looked up at mine and smiled as she downed some more wine. Her hand was already around my cock. It was going to be a wonderful night!