Work Related Fringe Benefits, Pt. 2

Last night was an incredible night and the start of what I hoped would be a string of beautiful encounters with Susan, her twin daughters, and not to be left out, my top girl at the office and lustful ringleader, Debbie. Even the waitress at the bar, Tammie, posed very interesting possibilities as she demonstrated a forwardness and sexual mindset that I felt must hold some sexual secrets somewhere deep inside. And as to the office staff, all women as I mentioned before, I had now had a real, dick pounding, exploding cum fest with two of them. With 11 beautiful employees, all working directly under me (at least I hoped), the variety of sexual experiences should be endless. And not to mention, each of these lovely ladies no doubt had interesting lovers and friends that might surface once things started rolling, as was evident last night when I was introduced to Tammie, the group’s favorite sexy waitress, and then Susan’s twin daughters, Tiffany and Amber.

Today started off a little slow at the office as might be expected for Debbie, Susan and me. The three of us had not left the office until very late last night after our awesome three-way. Actually, it was more like a two and a half way, as Debbie only fingered herself to an orgasm and allowed me to shoot my load on her face after I fucked Susan to an orgasm of her own. Because of her commitment to her new husband she has a set of self-imposed sex rules that forbid her from actually engaging in sex acts with others, male or female, but she loves to watch people get it on in front of her as this arouses her and enhances her own masturbation ritual. I’ll say that it does that for sure as her orgasm last night as Susan and I watched her cum at her own touch was magical to say the least. She could hardly keep herself upright in the chair she sat in to watch Susan and I have our own consensual fuck fest on the couch in my office. The drinks we had at the bar after work had provided the perfect mental lubrication to set the scene for a wild night of sexual experimentation after I had suggested we go back to my office for a nightcap.

Susan was the first to stop by my office, the “scene of the crime” just a few short hours before. “I really had a great time last night John. Well, I guess it was actually this morning wasn’t it?” She giggled cutely at the realization that it was after midnight before we split up to go home. She panned the room with her beautiful blue eyes as if she was looking for something lost. “Did I leave anything in your office last night, ‘er, I mean this morning? I think I’ve lost an earring. Nothing expensive but I wouldn’t want it to turn up on your couch during an important meeting.” She ran her hand along the crevices between the couch cushions and sure enough came out with her missing earring. “You might want to run a rag over the cushion here John. It looks like I might have gotten a little wet last night and left you a little reminder. Sorry about that”. There was nothing to apologize for in my mind but I thanked her for the tip and made a note to take care of the situation. Susan had indeed gushed a load of female cum and pussy juice as we fucked for the better part of an hour on the couch while Debbie masturbated in front of us. It would be hard not to leave some of that behind.

“Tiffany and Amber weren’t home last night when I got in”, Susan continued. “You didn’t hear from them last night did you? I was worried a bit that they might have gone partying with someone after we put them in the cab at the bar, but they finally stammered in about two hours later. They must have had a good time whatever they were doing as they both had huge grins on their faces when they walked by my bedroom.” Her twin 18 year old daughters are spitting image clones of their mom, in more ways than just looks. Besides sharing a beautiful full rack of very fuckable tits, gorgeous blue eyes, long blond hair and legs to die for, they are both sexual dynamos just like their mom. They’ve grown up watching their divorced mom fuck in every way imaginable in her bedroom at home. The girls had snuck into the office and secretly watched our love making three-way orgy last night, just as they have crept into their mom’s bedroom at home since they were about 13.

I pleaded ignorance to Susan’s query but I was concerned she might know that they girls had actually finished me off with a “stereo” blow job after Susan and Debbie went home. It was “stereo” in the sense that watching two identical twin blond bombshells lick and suck your dick until it explodes, especially when the three of you are half drunk at the time, you begin to think you are seeing double. Moments after I had shot my hot cum all over Debbie’s face, I escorted her and Susan to the elevator and while walking back to my office the girls came out of hiding from a cubicle in the darkened outer office. They wanted to show me their thanks for fucking their mother who had been without a sexual partner for months. At first we were just going to share a drink but the girls insisted on experiencing a “real man’s” dick, as they referred to it. I thought I might actually end up fucking these two hot 18 year old cunts, but they left me dripping in cum as they left for home as soon as my dreamy blow job came to a volcanic erupting end. Something told me that this would not be my last sexual encounter, and definitely not my most intense sexual encounter, with Tiffany and Amber. They intended to use me to take their sexual experience to a new level. Or was it me that was going to be taken to a new level by them?

Debbie wanted to talk the moment she arrived at work. I meet her as she was getting off the elevator that stops at our 17th floor penthouse office. I was about to go outside for a break but she grabbed my arm and quickly spun me around in the direction of my office. “I need to speak with you… in private, please?” she uttered softly, the last word being more of a hopeful question. I could sense some sort of vulnerability and since last night was a bit strange as sexual encounters go, I definitely wanted to be a good listener and hear all that Debbie wanted to say. She closed the door to my office behind her as I sat in my chair facing the room full of ladies outside my glass office. While we would enjoy audio privacy from the outside, there would be no hiding the visual aspects of our meeting the staff outside. As much as I might want to put my arm around her to console her if need be, or as much as I might hope to get lucky and feel Debbie’s mouth around my dick, it would not be possible in this venue. There was no need to jump to conclusions though, so I settled in and listened to her begin to explain her personal challenge.

“John, yesterday when you took me to lunch I briefly explained to you that I was divorced and recently remarried, all due to an affair with the man who used to sit in your chair. Then at the bar when Susan told you about my love affair with her as well, you got another side of the story. What you didn’t hear last night was that Susan and I have had encounters as well with her daughters, Tiffany and Amber.” I couldn’t tell Debbie that I had heard this directly from the twins as that would require divulging that I had been with them myself last night. Debbie continued, “John, I just want you to know that I meant what I said yesterday about wanting to be faithful to my new husband. It’s not so much a matter of love as it is that I am such a sexual woman, as you can tell from my past involvement that I’ve confided in you.

“Debbie, you don’t need to explain further,” I replied, trying to give her a break from a heavy conversation and also wanting to assure her that I wasn’t sitting in judgment in any way. “What you do in your sex life and your commitment to your husband is perfectly ok with me. It is not in any way a reflection on the fine work you do here, or your friendship with me.”

“You’re very kind, John, but I do need to explain further. Before last night I saw you as a very nice looking man who was also fun loving, gentle, and caring. What you did to give Susan and I a chance to be together in a sexual way that didn’t cause me to cross the line, was a wonderful thing for her, and for me. And I know you enjoyed fucking her too. As I sat in this chair and watched the two of you lunging at each other in such a passionate embrace on the couch it made me more aroused than I could have ever imagined. And when I was about to reach my orgasm, the way Susan pulled you out of her pussy before you came and then jacked you off, shooting your cum on my lips, well, it triggered something in me that was unexpected. I found myself wanting your dick inside me, at that very moment, and it was all I could do to leave with her and go home, without dropping to my knees and begging you to fuck me as well. John, I can’t work hear under this sort of pressure.”

I was floored to hear her confession, and cock swelled at the same time. Here was the voluptuous dark-haired beauty spilling her intimate sexual desires to me, and at the same time, resigning from her job, surely not? There must be a way to salvage the situation. Think John, and not with the head of your dick, for once. Use your real head. Last night I had not so much as touched Debbie, let alone had my dick inside her. Watching her put her own fingers inside her pussy and then watching my exploding cum shoot across her lips as Susan jacked my load off with her hand was all I could stand as well. I was the one who wanted to drop to my knees and beg Debbie to fuck me. “Debbie, I’m sure there is something that we can do to work this out. I don’t want to lose a valuable employee over something like this.”

Debbie quickly set the record straight. “Look John, I’m not quitting my job. And I’m not leaving my husband. I just want you to know how hard this is for me. I had no idea before last night that I could want someone as much as I wanted to be fucked by you, right then and there. And I wanted to go down on Susan like I used to when she and I shared our beautiful lesbian romance a few years back. I wanted it all again. And I wanted it all at once, you and Susan, fucking me together, me fucking you, me fucking Susan. It was just so intense. When I finally got home I had come back to earth and although I didn’t sleep much I was able to get past my desires. I hope we can all three be together again, soon. But I need your help to keep my promises. Please, John, tell me we can continue as we did last night and that you will help me stay strong.”

Well, that was certainly better than being handed a resignation from one of your sexiest, most beautiful employees, but I honestly didn’t know how I could have Susan hand jerk my dick into Debbie’s face and not want to end up with my dick embedded deep into Debbie’s cunt. Damn, what a ball buster. I assured Debbie that I would make it a matter of utmost importance and that I would be thrilled to participate with her and Susan in suitable love-making arrangements anytime in the future, although, I was sure I wasn’t being honest with myself about keeping my dick out of her pussy.

The rest of the day passed without much fanfare, although Susan did invite me to her house for dinner that evening and I accepted. She said the twins had cheerleader practice and that she would be home from picking them up about 6 o’clock. We agreed on 6:30 and I told her I would bring a bottle of wine to go with the meal. It seemed like a very normal invitation but I was a little nervous having just had sex the night before with Susan and then being blown blissfully by her two daughters afterward. The evening could be a little awkward if the girls chose to make it that way.

When I arrived at the door Susan greeted me with a deep, warm kiss and a playful hand on my crotch just as she had left me with the night before at my office. This must be her trademark greeting I thought to myself. Sort of an enhanced kiss you might say. I didn’t put up any argument of course. The twins were sitting on the couch, still in their cheerleader practice uniforms, watching TV. “Hi girls”, I said, hoping for a non-eventful reply. “Hi, John,” they came back in unison. So far, so good.

“John, I hate to do this but I promised a girlfriend I would come by for a minute and help her with a financial matter. She’s applying for student loans for her son to go to college and having a little trouble with the forms. The deadline for submission is tonight and she’s desperate. I promise I won’t be more than a half hour. Besides, the girls really like your company and I’m sure they can keep you entertained. Dinner is in the oven and won’t be ready for an hour anyway. Do you mind?” Susan seemed to have this all under control in her mind, but I was less comfortable due to last night’s encounter with the twins in my office. I agreed to her pleading of course and gave her a kiss as she walked out to her car. I turned to the twins and held up the bottle of wine I’d brought. “What should we do with this?” was probably the wrong question to ask.

Tiffany and Amber, although identical twins, could be distinguished from one another by a subtle difference in attire. Tiffany had her fingernails done in red polish, Amber usually preferred clear. I had only learned this last night when the girls had gone to the bathroom at the office while we were having drinks. When Tiffany came back alone first, I asked which twin she was and that’s when she gave up their little secret ID code. Of course, if they ever wanted to cover for one another, this would be an imperceptible swap that would be easy to accomplish. It worked for me, at least as far as I cared. I handed the bottle of wine to the outstretched red polished fingernails of Tiffany, I assumed, and sat down on the couch next to Amber.

Tiffany took the bottle into the kitchen and soon emerged with three empty glasses in one hand and the open bottle in the other. She handed Amber and I a glass and began to speak as she poured a glass of wine for each of us. “Now John, Amber and I know you are here to fuck mom tonight.” Wow, what a way to start a conversation. I thought I was there for dinner but the thought of fucking Susan did occur to me once or twice during the afternoon. “That’s right,” Amber stepped in, “and you know we are totally supportive of you having sex with our mom. In fact, we want to watch you John as you pump that beautiful large cock of yours into her pussy. Mom is such a turn on to watch when she’s getting fucked and last night at your office was the first time we’ve been able to watch in a long time.”

This news was both exciting and troubling at the same time. Sharing your sexual relationship with a beautiful woman like Susan, even if through voyeurism, was a strange thing to me made even stranger by the fact that the voyeurs were her two twin cock-tease teenage daughters. Tiffany picked up the conversation, “John, it’s important that mom’s experience tonight be a good one, so we want to get you ready for the action. We know a man doesn’t last very long the first time he shoots his rocks off, so Amber and I are going to get that out of the way for you so you’ll be able to last when mom pulls your dick into her tonight.”

“Look girls, I told you last night that as much as I would love to fuck you both, I don’t feel comfortable with this situation. I can’t be fucking your mother and fucking both her daughters at the same time.” I felt a tone of desperation in my own voice as I listened to what I was saying. I really wanted to fuck Tiffany and Amber. What healthy 55 year old male wouldn’t? Yet at the same time, I wasn’t being totally honest about being uncomfortable fucking all three of them. While it might be strange to bed them all down, together or alone, I would fuck them all at the drop of a hat. “Besides girls, you heard you mother say she would be back in a half an hour. We don’t have time for this tonight”.

“John, you need to understand something,” Amber said in an authoritative voice. “You’re never going to fuck either one of us. Not as long as you’re fucking mom. We’d never fuck one of our mom’s boyfriends. That is, not unless she asked us to! And as to having time for this, mom is at our friend Jeremy’s house, working with his mom on the computer. We told him to make sure things took a little longer tonight. He’s a good friend, if you know what I mean.”

This revelation had multiple implications as well. I wouldn’t be secretly fucking either of the twins while fucking Susan at the same time, but if I read between the lines, it was possible, maybe even likely, that Susan might allow or even encourage a sexual encounter between me and her daughters. Maybe she would suggest her daughters participate as willing partners while Susan and I fucked each other? Or would Susan want me to pleasure her two beautiful daughters while she watched? Or,… Hell, the possibilities were endless where this could go, or not go. As usual my mind was way ahead of reality. I turned my focus back to the situation at hand. “So girls, I find myself once again at your mercy. Just what exactly are we doing tonight?”

Tiffany and Amber grinned at each other without giving me a verbal answer. I was beginning to feel that the actions about to take place would be the only thing to provide an answer to my question. Amber grabbed the remote control from the table at the end of the couch and clicked toward the TV. The screen flickered as it changed from the local news station to a video. Instantly my mind absorbed the image of two young women stroking the shaft of a rather large cock on the screen. Talk about staging the scene, they must have had this set up knowing what direction the night would go. The girls were now on their second glass of wine. I continued to sip my wine as I sat motionless between these two dolls, still dressed in their cheerleader workout clothes. If the code system hadn’t been tampered with, it was Amber whose hand reached for my zipper and began to pull it downward, judging from the perfectly applied clear nail polish on her lovely teenage fingers.

The two women on the screen sat on either side of the male, sort of a mirror image of our reality. I noticed the man had no clothes on of any kind yet the two women were fully clothed. Were we going to act out the entire scene to the full letter of the law? Although the idea felt strange to me, there was something arousing about the idea of surrendering yourself, totally naked and exposed, to two fully clothed females. I began to hope that Tiffany and Amber would follow through but I couldn’t bring myself to suggest the outcome. While they both seemed to have plenty of sexual experience behind them, the idea presented on the screen seemed something more perverted than a pair of 18 year old girls would comprehend.

When the zipper reached the end of its track, my cock instantly stood at erection and made its way out of the opening in my pants. Tiffany provided the next visual image as I watched her red polished fingernails gently and very slowly make their way up and then back down my shaft. She closed her fingers around my rock hard cock and slowly stroked it while leaning her head against my shoulder. I moved my hand over to her beautifully tanned thigh that was exposed from under her little cheerleader skirt and started to stroke it lightly. To my surprise, Amber reached over and removed my hand from Tiffany’s leg. Was this a good sign or a bad one? The wine had me a little confused but I knew my only option was to go along.

I had come from work in my normal full business suit and now found myself slightly uncomfortable as the girls began to work their magic on my cock. Tiffany began to undo my tie in a seductive sort of “stripper-like” ritual. She was straddling my crotch while Amber continued to apply a light stroke to my erection and occasionally reached down to fondle my balls with her hand. With the tie now gone Tiffany unbuttoned my shirt and then rose to a standing position in front of me and pulled me upward until I rose off the couch. She helped me out of my suit coat, then my shirt, then immediately unbuckled my belt. With the zipper already undone, I was more than halfway to duplicating the video on the TV as my pants fell straight to the floor. Amber then moved down to the floor and removed my shoes and socks and slid my pants the rest of the way off. I now stood naked in front of them except for my shorts. And that didn’t last long. Tiffany removed the last vestige of clothing that I could claim. As she dropped the shorts down my legs she stood at my side and jacked me off slowly with her hand. Amber, kneeling on her knees in front of me, removed my shorts from around my feet and I finally stood entirely naked in the room.

As Tiffany continued to stroke my cock she leaned in closer to me and inserted her tongue in my ear sending a shiver straight to my cock and through my balls. She worked her tongue in and out of my ear, providing what I suppose is the closest sensation to a girl getting fucked in her cunt that a man can feel. It was totally erotic and I thought for an instant I would blow my wad. I looked down at Amber who by now was licking and sucking on my balls, her small hands fingering and cupping them as she worked them with her mouth. I was ever mindful of the clear nail polish as I watched her hand on my balls and equally mindful of the red nail polished fingers working my dick at the same time. Did they share this distinguishing fact with me as a mind game? If so, it was working very, very well.

A small amount of pre-cum had oozed its’ way out of the end of my cock and glistened a bit in the light of the chandelier above us. Tiffany took her index finger and smoothed the pre-cum over the head of my cock, making it slippery and ready for action. At that moment I thought I might have a slight chance to break though the barrier that the girls had laid down earlier about fucking them as I noticed each of them had begun to rub their cunts with their free hand, all the while making sure my cock was fully attended to. In fact, Tiffany was so far along, having shoved her fingers in her pussy by pushing aside the delicate fabric of her panties that she fell back on the couch and starting to finger fuck herself rapidly, leaving me on my own with Amber. Maybe this was my opportunity.

Amber had totally immersed herself in caring for my balls and didn’t notice at first that Tiffany had collapsed on the couch, leaving my dick unattended. When her eyes caught the visual of Tiffany stroking her fingers in and out of her pussy it caused Amber to take charge of the situation. She pushed me down on the couch and continued to kneel in front of me between my legs. Her hands now began to slowly stroke by cock and alternate back and forth to my balls, my cock, my balls, my cock. This was getting me ever close to an eruption that I had no control of.

“Don’t you want to help her out?” Amber asked as she nodded her head over toward the scene going on next to me on the couch. Was this an invitation to fuck Tiffany? Had my luck changed? I started to raise my hips off of the couch and mount the waiting pussy being fingered feverishly just inches from me. “Not so fast mother-fucker”, she said in a stern tone as she applied a heavier pressure to my ball sac that instantly had my ass cheeks back on the couch. I was in fact their “mother-fucker” but I didn’t appreciate the reference. I was in no condition to protest however, at the moment. Amber guided my hand to Tiffany’s crotch and forcibly inserted two of my large, long fingers in her already sopping wet cunt. I did the best I could to continue the progress of Tiffany’s masturbation while concentrating on my own need to cum.

I laid my head back against the couch and began my eventual surrender to the inevitable climax that Amber was now totally and masterfully in control of. I closed my eyes and continued to finger fuck Tiffany who by now had her head against the couch next to mine and had begun to slide her tongue in and out of my ear as she had done before, almost as if in appreciation of my fingers now taking over the job of fucking her young pussy. I didn’t think I could feel more close to ejaculation without exploding than I did at that moment but I determined to hold my load back as long as I could. Tiffany added her now free hand to the base of my cock and was stroking it as Amber continued to lick gently on my balls. Tiffany used her other hand to cover mine as I continued to attend to her masturbation. She forcibly pounded my fingers into her pussy and I could tell she also did not have long to go before a violent eruption would overtake her young cunt.
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Tiffany began to shudder uncontrollably and to my delight began to utter, “Fuck me, John. Fuck me with your fingers, John. Do it, John. Fuck me.” And then silence, and a hard squeeze on my hand as she forced my fingers deeper and deeper into her pussy and then held them in at the deepest point as she arched her back and pelvis forward as she came uncontrollably. It was such a beautiful spectacle that it took my mind off of Amber for a brief moment and I had not felt the sensation of her lips as they moved to cover the tip of my cock, but I sure felt it now. With the skill of an experienced woman she slowly mouthed the engorged end of my swollen organ and alternately moved up and down the shaft with her tongue. Her fingers kept a steady but soft grip on my balls as she kneaded them gently. Tiffany had slowly revived from her shuddering, erupting orgasm at my hand and now moved her mouth over to offer assistance to Amber.

I began to rock up and down with my hips and I had to work hard to control my urge to ram my cock down Amber’s throat. She was taking all of it in that she could voluntarily and I knew I was going to explode in her mouth in a matter of seconds. Tiffany was face to face with Amber and I could tell she wanted to share the load of cum that was about to erupt. I couldn’t hold this explosion much longer. Amber, who had been in control of my destiny for the entire evening, made one final move to end it all. As she engulfed the head of my cock in a tight grip in her mouth, she moved her hand in between my legs and began to slowly circle my asshole with her middle finger. When she gently inserted the tip of her tiny teenaged finger into my ass I erupted instantly in a violent explosion of cum! Her head rocked back at my thrust and her mouth released my cock and cum began to shoot into the air. Tiffany quickly covered my dick with her mouth and I rode her tongue the rest of the way to full submission, feeling Amber’s finger still pushing gently into my ass.

When I collapsed against the couch the two girls stood and looked down at my spent cock, which continued to pulsate and ooze a little cum. Tiffany retrieved a bottle of pills from the end table and tossed them on the couch next to me. “Here, John, it looks like we may have overdone it a bit tonight. You may need these when you fuck mom. She deserves to be taken good care of you know.” We’re headed over to Jeremy’s house for a good fucking of our own. We’ll call Jeremy on the way and let him know the coast is clear for mom to head home. Well, don’t just lay there John. You’d better get dressed! Remember, we’ll be back to watch.”

I didn’t know how I was going to perform for Susan after that. I grabbed the bottle of pills and starting reading the label…

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