Annie and I always had a special relationship. She gave me the scoop on all the girls that worked under me and let me know what was going on in the mind of each of them. What was their relationship status? What was their income situation? In essence, she fed me all of the important details I needed to find my way into their panties.
Annie was closer to my age, 42 in fact and well preserved for her age. She was married with a couple of kids (already out of the house) and stuck in a somewhat less than fulfilling relationship at home. Her husband didn’t make a lot of money and didn’t seem to want to either. Annie had been with the company for quite a while, much longer than I, and was doing pretty well for herself if you took into account her salary, benefits, and a sizable balance in her 401(k) account. She really didn’t need her husband’s meager income to get by and this gave her a sense of independence and freedom to be herself whenever she wanted to.
Annie often accompanied our department on our weekly happy hour excursions. The more I was around her the more I became attracted to her. She had long curly blond hair, actually sort of dishwater blond, wore a lot of sundresses and generally had that wholesome 60’s-like hippy aura about her. She ate a lot of wholesome foods and generally was a health nut, but her one downfall was that she enjoyed a glass of red wine whenever she could. I always made sure she didn’t pay for a drink when she went with us and I always made sure her glass was full.
My waitress friend Tammie, our regular server at our local watering hole and occasional lesbian lover of one of my girls, Susan, noticed I was making sure the wine kept a steady flow and I could tell she sensed that I was on the prowl. “Got a new target tonight, John?” she whispered in my ear as she refilled Annie’s glass for the third time. I had made sure that Annie joined us at this particular happy hour as I had sensed earlier in the day that I might have an opening. I had dropped by Annie’s office around 9:30 to get a little scoop on a new girl I had spotted on another floor earlier that day. She took me back to the file room where all of the employee records were kept and pulled on the drawer containing the new girl’s file.
“Here you go fuck head,” she blasted. “Don’t you ever get tired of fucking the help?” I could sense a bit of frustration in her tone as usually she just grinned at me with a seductive smile and then left me alone with the file so I could get the data I needed. “Don’t you ever consider that there are plenty of people closer to your own age with needs to be filled? Why are you always looking to fuck the young new hires? Damn John, you’re such an inconsiderate bastard. Why don’t you just go in the men’s room and jack off?”
Holy shit. What had I done, or not done, to piss this woman off? Annie turned quickly and started to walk out of the file room as I tried to assess her comments. A man’s mind doesn’t always work as fast as it should but my instincts did usually react quickly enough. I reached for her arm as she started to walk away, her flimsy little dress swirling around her lovely legs as she tried to make her getaway. “Whoa, girl. What the fuck was that all about? Something going on that I need to know about?”
“God John. Are you a totally dense fuck? Every week you come in here wanting information on some pretty young chic that you usually end up banging. I could only wish my sex life was that exciting. Do you know how much trouble I would be in if one of those girls found out that I had supplied you with intimate details about them for you to use to your advantage? I can’t afford to lose this job with the mess I have at home. And it isn’t exactly a thrill knowing you’re getting fucked all the time while I risk my job for you and end up with nothing but a dildo in my cunt at night. Why don’t you find me someone to play with and return the favor? You’re just a typical dickhead male. All of you are a bunch of fucking bastards!”
Annie lowered her face into her hands and started to sob slowly. My slow male brain now registered the issue. Things weren’t good at home. I knew that already but they must have taken an even sharper turn for the worse. Annie was a beautiful woman. I guess in current terms you would label her a “cougar”. At 42 her body was in fantastic shape. She had nice perky tits, very shapely legs, a tight ass, and she almost always had a smile on her face. There was nothing not to like about Annie, nothing at all. In fact, I had more than once ended up in the bathroom jacking off to the smell of her light perfume after one of our file room sessions.
“Hey, Annie, what’s wrong?” I asked as she tried to compose herself.
“Fuck you, John. Just fuck you!” She obviously wasn’t herself and I felt the need to pursue the discussion.
I took her in my arms and felt her head lay against my shoulder. I held her for a moment without saying anything more. I wasn’t sure I had the right words so I decided not to risk another comment. I felt her slim body and her nice tits against me as I held her. There really wasn’t much between that sundress and my cock. This was the first time we had shared anything remotely resembling an embrace and it felt good, even if the situation was not optimal. I pulled my face back so I could see hers and looked into her teary eyes. “Hey, I know I’m nothing but a dickhead but how would you like to join our group tonight for happy hour?”
She smiled and wiped a tiny tear from under her eye. “That would be nice”, she replied in a soft voice. “I’m sorry I went off on you John. Maybe we can talk about it tonight.” Then she did something that cluttered my mind the rest of the day. As we pulled apart from each other she gave me a kiss on the lips, not a peck mind you, but a very deliberate and passionate kiss on the lips. I left without obtaining the file that I had come for but I sensed that I might be leaving with something equally as valuable.
Back at the bar I was enjoying the wine at an equal pace with Annie. Some of the other ladies had joined us that night – Susan and Debbie, and my most recent conquest, Cindy. All of these ladies had proven to be voracious sexual partners and one would think that there would be a bit of cat fighting or jealousy among the group, but no such condition existed. In fact, the girls chatted amicably during the night, occasionally winking at me from time to time or giggling to each other about something. My mind could only dream about what stories they might have shared about their sessions with me. The only rationale I could come up with for this congenial atmosphere was my age and marital status – 55 and hitched. I guess none of them saw me as anything more than a detached roll in the hay. Ok by me, or at least it was tonight.
I sat next to Annie and made sure our bodies were in contact with one another. I wanted to put my hand on her thigh under the table but I hadn’t had enough wine and my courage was lacking. “So tell me what was on your mind today when I came by your office. That was an awkward scene in the file room.” I thought my comments were gentle enough to get her talking about her feelings but not too overly pushy to make her withdraw. She was ahead of me by maybe a drink or two and her courage was at a much higher level than mine.
“I want you to fuck me John, …tonight.” Wow. Her direct request registered immediately in my crotch but not so clearly in my mind. Her hand rested on my inner thigh, slightly contacting the head of my instant erection. “You’ve fucked everyone at this table except me. I don’t think that’s quite right. Do you John?” She paused for a second as her fingers moved further up my thigh and stopped on the head of my dick, no longer just touching it but resting fully around it, separated only by the thin material in my suit pants.
I was fairly certain the other girls had not heard this private offering by Annie. The bar was loud and abuzz with the sound of drinkers and partiers and the girls were nearly yelling at each other in conversation. Annie though had spoken these words directly into my ear from close range, punctuating her comments with a flick of her tongue into my ear. That action caused a twitch of my cock which registered against her fingers that were resting on its’ bulging head. How did she know this was a turn on for me? Had the other ladies schooled her in “Sex with John 101”? Again my mind raced and I looked at the girls for clues.
Susan and Debbie seemed oblivious to the situation and looked like they might be planning a rendezvous of their own for later on. They had a habit of sharing a girl on girl thing which I had been a partial player in once before. My eyes went next to Cindy, the youngest of the women at the table at 26 years old, and my most recent conquest. Cindy and I had made incredibly passionate love for hours on end one night last week while her roommate enjoyed a final night of sex with her boyfriend before moving out of the apartment the two girls shared. Her eyes were twinkling when they met mine and she tipped her wine glass toward me and winked her eye approvingly. Damn, she surely had leaked something to Annie about us. I suddenly felt a bit vulnerable for the first time since taking my new job.
Having a few twists with office mates wouldn’t normally be that big of a deal but I was getting around a bit. This was going to end one of two ways – really good or really bad. I now suspected I had a 26 year old female employee confessing our sexual experiences to the company HR director. And the HR director wanted to fuck me… tonight! I had better be good and I had better watch my manners. Whatever Annie wanted tonight, she would get. Nothing more. Nothing less.
Annie took a cell phone call and walked away from the table to find a spot away from the noise of the bar. I took the opportunity to slide over next to Cindy. “What the hell is going on Cindy?” I asked in a somewhat desperate tone. “Annie is coming on to me like nobody’s business and you’re over here winking at me. What do you know about this?”
“I think she wants you to fuck her John. Looks pretty obvious to me.” Cindy could barely hold back a giggle and it was clear she was in on this in some way. She’d also had too much wine but it made her all the more sexy as she leaned into me and hooked her free arm inside mine. “You don’t mind helping a girl out do you John?” Was she talking about Annie or herself? Damn, I must have had too much wine myself. I wasn’t thinking clearly but I was thinking double. I wondered for an instant what it would be like to have Annie’s lips sucking my cock while Cindy ate her pussy.
Cindy let the cat out of the bag as she began her explanation. “Last week when I came to your office at the end of the day and we had that great night of lovemaking… remember that night John?”
I wasn’t stupid and I sure wasn’t forgetful. I must have fucked Cindy five times that night, coming on her, and in her and also unloading in her pretty mouth once or twice. She was incredible to say the least, everything you would expect from a 26 year old sexually active woman.
“Well, Annie came by to see you that night. Apparently you had asked for a file from her on some new girl in accounting. She saw everything we did that night and called me to her office today. We talked for almost an hour about it. Funny though, she wasn’t interested in whether you did something inappropriate or violated any policies. She just wanted to know how I was able to get you to fuck me.” I found myself needing more wine and I belted down the rest of my glass as she went on. “I just told her that I came on to you and didn’t give you any choice. I thought it would be better to say that than to say it was mutual. I didn’t want to get you into any trouble.”
Things were starting to make a bit of sense, I guess. I really need to get some curtains for my office. Having an all glass office has a few disadvantages sometimes. Annie returned to her seat and said the call was from her husband. He wasn’t going to be home from his hunting trip until tomorrow. How convenient I thought, for Annie at least. Was she making this up or was good fortune smiling upon me? She settled in beside me and once again her hand found my crotch. With a light massage she had my cock pressing against my pants again. The physical excitement was overshadowed however by my growing sense of possible repercussions from my sexual exploits.
“Did you tell him?” Annie grinned over at Cindy as she launched the question. A childish nod was all that came back from Cindy as she kept her lips intentionally planted on her drink. “Great,” Annie fired back in response. “I hope you don’t feel awkward John, but I had to talk to Cindy today about what I saw the other night from outside your office. Wow, it really looked like you two were having fun. I got so hot crouching outside behind the cubicles that I had to finger myself over and over. I think I came as many times as Cindy did.”
I was either a dead man, destined to end up broke and homeless, or something extraordinary was going to take place next. Annie continued, “You know John, business is business and I’ve got to do my job. Both of you could be dismissed if I turn in the correct report as required by the company policies”, she looked over at Cindy when she uttered this last warning and the two girls winked at each other and clinked their wine glasses together in a mock toast. Cindy didn’t seem disturbed about the possibility of getting into trouble at work. Then she broke into a wide grin and as I turned to look at Annie she was doing the same. Any fear of true consequences melted away at that point. I let my mind wander into the possibilities for the night.
By now Susan and Debbie had disappeared and I was alone with Annie and Cindy. Cindy slid her chair over and I found myself surrounded between the two hot and obviously horny ladies. There were hands in my crotch from both sides now and they seemed to be headed for the same object. Annie spoke up, “I want the two of you to come back with me to the office so we can get something straight between us. I need to finish my report on this incident tomorrow.” Another grin appeared on her face as she looked over to Cindy. “Yes ma’am,” Cindy replied obediently.
They were now engaged in their own form of foreplay from what I could tell. I sensed as well that something sexual may have already transpired between the two. Any doubts about that faded when Annie leaned across me and met Cindy’s lips right in front of my face. If the wine wasn’t playing tricks with my eyesight I also witnessed the two girl’s tongues entwined. Sure enough, Cindy was being more the aggressor and sucked Annie’s tongue into her mouth, giving it sort of a blow job motion as it went in and out until it finally, slowly was released. Holy fucking shit!
My cock was now ready to explode under the table and I hoped the girls might unzip my pants and finish me off right there! Both had continued to stroke me from the outside of my pants as they had engaged in their hot tongue sex in front of me. But alas, no such explosion was going to take place for me at the bar as both of the girls settled back in their chairs and removed their hands from my crotch. Annie broke the silence. “Shall we make our way back to the office John so we can put the finishing touches on my report?"
Annie’s words, I hoped, were code for let’s go back to your office and fuck each other’s brains out. We made our way out of the bar and completed the short walk back to the office. As we walked past the concierge and the security guards I gave the guys a “thumbs up” sign and they grinned back at me and just shook their heads. I could tell by the smiles on their faces they knew what was coming next. The girls didn’t wait for the elevator ride to the 17th floor to come to a stop. Cindy pinned Annie into the corner of the elevator and planted a hot kiss on her lips as Annie opened her mouth to accept Cindy’s invading tongue. I just stroked my dick through my pants as the two gorgeous ladies went at each other.
When the elevator doors opened we wasted no time getting into my office and Annie immediately knocked everything off the top of my desk and climbed up on it, hiking her dress up to her panties and spreading her legs to demonstrate a willingness to be conquered. It was such a turn on to see the more mature Annie allowing herself to be dominated by the younger, more aggressive Cindy. And Cindy was up to the task. She reached her hands under Annie’s behind and slowly eased her panties off, tossing them over to me for safe keeping. I sat down in my high back executive chair and put the panties in my mouth after taking a good long sniff of the tiny crotch area.
From my vantage point I had an up close and personal view of the pending lesbian session about to unfold. Annie had up until now had been more the passive recipient of Cindy’s more aggressive demeanor. But now she began to assert an authoritative role which in the workplace was hers by seniority anyway. Maybe getting back to the office had some sort of affect on her confidence. “Get your lips down there girl and lick my pussy,” she ordered to Cindy. Cindy willing followed orders and once again issued a polite “Yes ma’am.” I was getting rock hard at this girl on girl thing and thought for a second that I might undo the zipper in my pants and give my bulging rod a few yanks. I didn’t get the chance to act on my own.
“Pull your pants off John. I want to see that big cock of yours,” Annie issued the order and I readily complied. Her hand reached for my stiff cock as it sprung upward into the semi-darkness of the room. She jacked me slowly for a few strokes then released me so she could raise her dress over her head and off onto the floor. She reached around her back and unclasped her bra and tossed it aside as well. Her breasts were ample but not large and were accented by nice eraser sized nipples that were immediately erect upon exposure.
Cindy had stopped her assault on Annie’s now dripping wet cunt and began to remove her clothes as well. I stood silently and watched as she first unbuttoned her white blouse and tossed it aside. Annie once again had a firm grip on my cock and slowly jacked me off while we both watched Cindy do a teasingly slow undress. With her hands around her back to undo her bra, Cindy’s tits projected forward through the fabric. Her boobs were larger than Annie’s and the areola around her nipples was a bit larger with slightly smaller nipples in the center. With her top exposed she unsnapped her skirt and tossed it to the floor, then kicked off her high heels and slid her panties off. Both women were now butt fucking naked on my desk. What more could a man ask for?
As luck would have it I wouldn’t have to ask for anything tonight. It was all going to be dictated by Annie, the master of our fates this evening. Annie lay back on the desk and slid to the end allowing her head to dangle over the edge. She pulled me around the desk by my cock and in one motion inserted my hot rod into her mouth. From this upside down insertion I could see the bulge of my cock pressing against her throat as I plunged it in and out of her mouth, fucking her mouth like it was a warm, wet pussy. Raising my gaze upward away from the slurping pounding my dick was giving Annie’s throat, my eyes feasted on her hard nipples that my fingers had found and started to caress. Beyond that I could see a small tuft of slightly darkish blonde hair above her pussy which had Cindy’s face buried in it. There were slurping sounds going on from both ends of Annie’s lightly tanned body.
As my dick continued to fuck Annie’s mouth she reached toward Cindy’s head and grabbed at her hair in an effort to pull her tighter against her arching mound, forcing her lips onto her clit. She moaned as Cindy lapped and tugged at her erect little love trigger and squirmed slightly as Cindy lightly nibbled at her clit. I could see Cindy reaching down to stroke her own clit while she eagerly ate Annie’s pussy. Both girls where getting hotter by the minute and I was not far behind. When Annie pulled my cock out of her mouth and lowered her face to suck on my balls, I reached a point of no return and I felt the cum began to rush forward in preparation for what was going to be a giant launch across Annie’s tits and stomach.
“Oh, god. Shit! Fuck! I’m gonna cum,” I warned the girls almost out of embarrassment more than any desire to direct the landing of the big glob of cum that would follow. Just before I came I placed both of my hands on either side of Annie’s head and held her up as her mouth engulfed one of my balls. My dick was pointed at an upward angle that looked surely like I would launch directly at Cindy who had raised her face out of Annie’s snatch when the ejaculation alarm was sounded. It was almost too late to change the outcome when Cindy crawled on top of Annie and lowered her mouth onto my cock. The wet cunt juices from Annie’s pussy covered the purple engorged head of my cock and I released a violent thrust of cum into Cindy’s pretty little mouth. I bucked and strained until the last possible drop of cum had filled her mouth and then withdrew my cock at the same moment that Annie let go of my ball sack she had been mouthing so tenderly.
I held Annie’s head for a moment before she moved herself forward and rested her head again on the desk. She was now directly under Cindy who had come to straddle her while taking in my full load. The two girl’s faces were just inches apart. Cindy began to lower her mouth until it was just above Annie’s and as she parted her lips slightly the mixture of cum and cunt juice began to dribble out. Annie opened her mouth in time to accept the white milky gift. Cindy continued toward her and in a moment the girls were engaged in a tongue dance with my cum providing the lubrication. They French kissed each other and slowly swallowed the fluids until it had all disappeared.
They were still enjoying this female embrace when I made my way onto the desk and pulled myself up behind Cindy’s rounded smooth ass cheeks. I had not even had time to remove my pants and shoes before now, or my shirt for that matter. I quickly disposed of them all and was on equal footing with the girls finally. The feeling of being butt naked, on top of my own desk in the evening light, staring right into the tiny asshole of Cindy who was kissing Annie was all I needed to get another erection. I let my cock come to rest in between the butt cheeks of Cindy who writhed and gyrated slowly which only made my erection harder.
“Oh no you don’t, John” Annie cried out. “You’re fucking me first. You’ll get your chance with Cindy later. “Cindy, turn around girl,” Annie commanded. Cindy was a dutiful servant and reversed her position to face me and eased her cunt down toward Annie’s face. Annie seemed more interested in licking the pussy juices from Cindy than she did in how and when I fucked her. I didn’t want to be pushy so I just dropped my cock onto her pubic mound and let it lay their while I began a passionate kiss with Cindy. I could taste the mixture of cum and pussy juice still in her mouth. We tongue kissed for a minute and then Cindy reached down to my cock and began to stroke it and in a moment she had positioned the head at the entrance to Annie’s moistened pussy.
“Put his cock inside me, Cindy. Ram it in deep,” Annie ordered to Cindy. Cindy pulled at my rod and with a slow pulsing shove began to bury it deeper and deeper into Annie’s arching pussy. As she jacked on the shaft and pushed me inside I grew harder and harder both from the touch of her lovely small fingers pulling on the shaft and the wet inside of Annie’s pussy as it finally enveloped the full length of my shaft. Cindy moved her hand to Annie’s clit and provided an extra measure of stimulation as my cock began to assault the inner reaches of Annie’s love hole. Occasionally on an inward thrust I came in contact with Cindy’s fingers and experienced an added pleasure of my own.
With one hand on Annie’s clit and the other alternately teasing her nipples, Cindy was taking good care of her older friend. And Annie was bringing Cindy’s pussy to a wet and warm climax of her own. Cindy began a series of slow jerky convulsions and closed her eyes as she enjoyed one climax after another. Her love juice was soaking Annie’s face and rolling onto my desk. When Cindy couldn’t take the physical overload any longer she rested herself on her hands and sat motionless, doggy style, lifting her cunt away from Annie’s face as if to signal, “I can’t take any more!”
Cindy lowered her head toward Annie’s pussy and gave my cock an occasional lick as it was pounding faster and harder inside Annie’s swelling pussy. In a tumultuous eruption I began again to summon a large load of jiz that would fill Annie’s hole to the brim. At that same moment Annie cried out, “Oh, my god. I’m cumming John. Fuck me! Fuck me, John. Awhhhh. Fuuuucccccckkkk!” She let out a scream at the end of her sexual rant that lasted the duration of her orgasm until she finally collapsed on the desk. I pulled my cock out of her pussy slowly and came to a stop just as the head reached the outer lips of her reddened hole. Cindy’s face was still hovering over Annie’s pussy and she seemed ready and eager to consume the product of our mutual orgasm.
I slowly exited the head of my cock from Annie’s pussy and a second or two later a small stream of cum began to ooze out of her slit. Cindy was on top of it instantly and began to lap up each stream as it flowed out of Annie’s cunt. When she had sucked her dry she covered the end of my shaft with her lips and gave my rod a bath in my own cum and Annie’s love juice. Then she rose up to my face, ran her finger around her lips before inserting it into her mouth, followed by a large swallowing motion. She grinned at me, displaying her beautiful white teeth, her mouth still sporting a drop or two of love juices. As she moved toward me and planted a deep kiss on my lips I didn’t hesitate to accept the offering.
The girls had both achieved more than one orgasm by now, as had I, and I felt this was surely the end of the evening for us all. Annie, however, did not see it that way. “I told you that you would get your chance to fuck Cindy tonight, didn’t I John?,” she offered. There may have been a shocked look on my face but Cindy seemed genuinely pleased at the prospect. “On the carpet girl, doggy style,” she ordered to Cindy. “Yes ma’am,” came the usual obedient reply and Cindy assumed the doggy style position on my plush soft carpet. I got on my knees and directed my cock at her tight young pussy.
“Not so fast buster. You’re going to have to bury that thing in her ass. Her pussy is mine!” I’m not sure who was more surprised, me or Cindy, but I readily replied with the usual reply of the evening. “Yes ma’am,” I uttered and redirected my aim. “Yes ma’am,” was also the reply from Cindy although it didn’t seem quite as enthusiastic as mine. Annie grabbed a pillow from the couch and positioned it on the floor between Cindy’s legs and lowered herself onto it so she was in perfect position to suck on Cindy’s pussy while I plummeted her asshole. Annie licked up and down the lower regions of Cindy’s pussy and also slipped her tongue over her tiny asshole a few times to provide some lubrication.
Cindy’s ass was pointing almost straight into the air as she had lowered herself to a more comfortable position on her elbows. As Annie began to lick and suck on Cindy’s pussy, I got up off my knees and bent my legs slightly to take direct aim at the object of my desire. The head of my cock touched her tiny pink asshole and she pulled back slightly at the touch. Then as if accepting her fate she pushed back against my cock and the head slipped half way inside her before sliding back out again. The almost natural repeating of this process allowed the head of my swollen cock to finally stretch and then breach her opening before plunging inside her hot canal.
“God, your fucking cock is huge,” Cindy cried out as she continued to slowly allow me to inch deeper inside her. “Are you gonna put that thing all the way in?” Before she could finish her desperate question I felt my balls slap against her pussy where they were met by Annie’s exploring lips. The tightness of her ass and the fact that I was doing anal with this young chic meant that I was not going to last long. Her grunts and groans as well as the licking of my balls by Annie each time I plunged into Cindy’s ass was all I could take. Annie was fingering herself to a climax while she sucked on Cindy’s wet pussy and about the time that Annie shook from a thundering orgasm I felt Cindy begin to cum on Annie’s face.
I had reached the end as well. My cock convulsed one final time and I felt my load begin to crash into Cindy’s lovely ass. I pulled the tip out and let it rest on the tiny pink target and just let the jiz that was pulsating out of my cock splash onto her asshole. It began its’ decent downward and Annie began to lap it up as it reached Cindy’s pulsing pussy. When our collective motion had subsided I collapsed on the floor and the girls fell onto the floor on either side of me. Cindy began stroking my balls and Annie had a gently grip on my cock. It was the action of completion as it was slow and gentle and beginning to end. Their hands stopped and came to rest on my stomach as we all lay there spent.
“So what are you going to put in your report tomorrow, Annie?” I asked as our heart rates and our breathing began to return to normal. The girls both raised up on one elbow and looked at each other and smiled.
“I’m not sure. I think we need to have another meeting next week before I conclude my findings. Don’t you Cindy?”
“Yes, ma’am,” came back the reply. Cindy remained obedient to her superior. “I’m sure I can help straighten John out if given the chance.” A big grin broke across her face and she playfully reached down to grab my spent cock.
“And how about you, John? Are you good with that?” Annie posed the question to me as if I actually had a say in the matter and moved her hand to cup my balls.
With Cindy’s hand stroking my cock and Annie cupping my balls in hers, I uttered the only response appropriate at the time as I laid my head back on the carpet and closed my eyes.