Work Related Fringe Benefits
My name is John and I’m fortunate to have landed my dream job just a few months ago. I’m the only male in an office of eleven female co-workers. And equally as fortunate, I’m the boss. The ladies range in age from 18 to 45. I’m married and 55 years old so the ladies generally don’t see me as much of a threat from a sexual standpoint but I’m in very good shape for my age and have a well-built body riding on my 6 foot 2 inch frame, so I do get my share of attention around the office. Mostly though the ladies view me as sort of a buddy or even “father figure” type that they can confide in when they need to get something off their chests. I’m a good listener and I’m always willing to spend a little off-hours time with a damsel in distress. Our department provides administrative support services to a larger organization and for the most part we fly under the radar screen and don’t draw much attention. The work is not demanding and that provides us ample time for long lunch hours and the occasional happy hour get together in the afternoon.
All of the staff members are what I would describe as attractive, active, fun-seeking individuals and I enjoy the company of each and every one of them. Recently however, I have developed a much closer relationship with a few of the ladies who have sought me out for counsel on a more routine basis. Susan, a 36 year old divorced mother of twin teenage girls is a knock-out MILF if I ever saw one. She is just as attractive as her twin daughters, with nice tits and what I would call a perfect ass. It’s frankly hard to tell her and her gorgeous young daughters apart, especially after I’ve had a few drinks. Debbie, a 43 year old remarried empty nester whose husband travels during the week has a lot of free time on her hands and she doesn’t like to waste it! Debbie is movie star gorgeous and has the best boobs by far of the entire staff and always wears clothing that reveals just enough of her treasures to keep a strain on my zipper. Any man seeing Debbie’s tits for the first time instantly wants to find a way to slide his dick in between them, and I am no exception to that rule.
Debbie had sort of become the den mom to the group and most of the other ladies look to her for help with work and personal related issues from time to time. I took notice of this early on and quickly determined that my best chance to be part of the show was to solidify my relationship with Debbie in hopes that she might get me into the middle of the juicy stuff when it comes up. We are, after all, the closest in age and it is easiest for me to relate to her and where she is in life. I too am an empty nester and my wife spends a lot of time with a group of personal friends that she has developed over the years while I was grinding away on the job. Both Debbie and I have our weeknights essentially to ourselves. Shortly after I took the job I asked Debbie to join me for lunch under the guise that she could fill me in on the rest of the crew. I really just wanted to stare across the table at her beautiful tits for an hour, but if it would help to ease me into the office then that was a plus.
I asked her to pick her favorite place for lunch, hoping this would get us off on the right foot. She took me to a quiet restaurant where she had a regular table in an area near the back. I know what you’re thinking, here goes the typical “new boss fucks the best looking lady in the office right off the bat” story, in a dark secluded restaurant booth no less! I wish, my friend. No such luck with Debbie, but I readily understood her position as she explained her world to me over a very nice lunch and a bottle of wonderful red wine.
“I’m only recently remarried,” she explained. “I went through a nasty divorce and lost almost everything I had because I had been the guilty party in the relationship. You see, I had a blistering affair with my former boss, the man who you replaced just last month. He and I regularly met at this very spot and many times we ended up fucking each other’s brains out most of the afternoon. I am very easily sexually aroused and I love to feel a man’s cock in my pussy or a woman’s tongue on my clit. But I want to be true to my new husband and I want you to help me do that.”
I asked her why, if she liked sex so much, she couldn’t separate her love for her new husband from her sexual needs. Did she plan to never fuck another man or eat another woman’s pussy the rest of her life? “You’re a handsome man, John”, she started in. “In fact, you’re better looking than your predecessor. Hell, you’re better looking than my new husband! I’d like nothing better than for you to slide your fingers in my pussy under this table right now and for me to jack you off before we finish this wine. But if I go down that road I’ll never turn back. Can we just agree to be really close friends, at least for now?”
“At least for now”, was the important phrase I took away from that exchange. It gave me a glimmer of hope that I might one day slide my bulging cock into the tight space between those two beautiful tits. I was really disappointed but agreed to her request of course, as any gentleman would, especially a new boss. I bargained with her that she had to at least not bust my balls with the top brass when she caught me looking at her tits in the office. And I wanted in on all the scoop with the other girls and their personal exploits as well. She laughed and agreed to keep me informed of all the “hottest” issues as they came up. “I really want us to be good friends”, she pleaded, as she rested her hand on my thigh for a brief moment before we left. I wondered if she timed her move deliberately just to see the bulge in my pants when I arose from the table. She shook my hand in agreement with our new engagement terms. “I hope you can keep your part of the bargain”, she quipped as her eyes fixed on my crotch.
We walked slowly along the block and a half route back to the office. I had shared with her at lunch that my sex life was somewhat lacking since my wife and I led essentially separate lives, and I apologized for dominating what should have been an office discussion with mostly sexually explicit questions. “It’s totally ok, John”, she replied, letting me off the hook. “I actually enjoy talking with a man about his needs, and mine! I think I can help you find a little relief for your problem though”. I was all ears, or maybe I should say, all dick and balls. My cock was just starting to give me some relief from her lunchtime lap brush when it burst to attention as she began to talk about Susan. “This is the woman who could use your attention the most, and the one who is in the best position to reciprocate in return.” I listened as she went on. “Susan is not in a relationship right now and I don’t think she has been fucked in months! She has two beautiful twin daughters who tag along with her a lot when we go out who are trying to help mom get back on the horse”. Debbie giggled a bit and then said, “Maybe I should have said, back on the cock”. We both had a laugh but I knew exactly what she meant the first time.
I had spotted Susan at the introductory meeting with my new employees on the first day on the job. She is absolutely stunning. She always wears snug fitting dresses that show off her exquisite curves. I said earlier that she had “nice” tits. Really, they’re just right for her size and complete a “Barbie Doll” proportioned figure. I can’t sit in a meeting with Susan for more than a few minutes without having to excuse myself to the men’s room to release a load from my cock. The thought that I might actually be able to “release” that load into her beautiful warm cunt had all my attention. Debbie suggested she could set up a happy hour get together for Susan, Debbie and me to help break the ice. I readily agreed.
The clocked ticked off the afternoon hours at a snail’s pace. I sat at my desk shuffling papers for what seemed like forever waiting for the four o’clock happy hour to roll around. Susan had agreed to the outing with the stipulation that her daughters could come along. At the age of 18, both Tiffany and Amber were sexually active, according to Debbie’s deion of them, and I couldn’t wait to meet them for the first time. My hope was that they would have an effect on their mom and help move things along. Debbie said they both liked to drink, something you can do at 18 in the bars here if you are with a parent, and that when they got a few shots in them they usually took over the room. In fact, she warned me that if I wanted a chance with Susan that I needed to cool my jets when it came to the daughters. This didn’t seem like too big of a chore given our age difference. How much could they be interested in a 55 year old man? On the other hand, I could already sense that Susan and I had at least gotten off on the right foot. I always complimented her on her appearance, and her work of course, and she seemed to really like the attention.
We all left together for the bar and when we arrived, Tiffany and Amber greeted their mom with a big hug and a not so subtle kiss on the lips. Interesting I thought, but then they did the same with Debbie. I guess it was just the custom. I got a simple handshake and was kind of relieved at that. The girls definitely lived up to their advance billing, but more on that later. We all grabbed a table. I sat next to Susan and Debbie sat on my other side. The twins took the other side of the table and I had my first head on look at what appeared to be a mirror reflection of their mom. They both had the same long blond hair and perfectly sized tits. Holy shit, I thought. How could a man have a relationship with Susan, a stunningly beautiful 36 year old, sexually experienced woman, and not blow his wad every time he laid eyes on one of the daughters. Shit.
The young attractive waitress came over to take our drink order and grinned as she assessed the table. “Aren’t you the lucky one?” she asked bluntly, referring to the extreme talent around the table and only one male to go around. “What are you, a porn star or something?” I was a little embarrassed and didn’t quite know how to respond but before I could even try Debbie jumped in. “Cut him some slack Tammie. This is our new boss, John. He’s just taking us out to blow off a little steam. But he is a lucky stiff for sure!” They introduced me formally to Tammie who I later learned was their regular waitress which was another bonus in my book for sure. Tammie was probably mid to upper twenties with stripper looks and an attitude to go with it. “If he’s not “stiff” after sitting with this group he needs a medical check-up”, she blurted out as she left to put in our order at the bar. Well, this was certainly getting off to an “uplifting” start.
After several rounds we all were getting a little loose. The twins were dominating as Debbie had warned me they would. All night every stay dog in the room wandered over to the table wanting to buy them a drink. Their standard brush off line was, “We’re with John tonight, boys. Isn’t that right John?” and they would look over at me and wink while rolling their fingers seductively around the rim of their drink glass. I would always have to affirm their statement and after a few times Susan admonished them saying, “Girls, you’re going to have to stop that. You’re embarrassing John. Remember, John is my boss.” She then excused herself to freshen up and I tried to assure the girls while she was away that it was no big deal. Tiffany chimed in asking, “You wouldn’t mind being with us tonight would you John?” Amber echoed the question, “Yeah, you wouldn’t mind would you John?” Debbie rescued me again and told them to mind their manners. “I warned you about the twins, John”. I just smiled and tried to tuck the bulge in my pants away.
When Susan returned she insisted on sending the girls home in a cab. After a brief protest they agreed and when the cab arrived I escorted them out to the street. They each apologized saying they didn’t mean to come on the wrong way but they echoed that they really just wish their mom would loosen up and have some fun. I was a little embarrassed when they said she needed a good “fucking” and asked me if I could help her in that department. I just laughed at their brashness and put them in the cab. Tiffany and Amber were no doubt well in command of their own sexuality and both together were quite a handful, a handful that any breathing male would give his nuts to bang. But, what the hell was I thinking? I ran back inside to Susan and Debbie.
The lights had been lowered in the bar as it was after dark outside and the atmosphere took on a cozier feel. As I found my way back to the table I noticed Debbie had slid over next to Susan and she seemed to be kissing her gently on the neck. Was I dreaming or drinking too much? Had I not heard Debbie say just today at lunch that she wanted to remain faithful to her new husband? I stopped just out of sight and observed for a minute. Sure enough, Debbie was placing small nibble-like kisses along the base of Susan’s neck and at the same time Debbie had her own hand between her legs, fingering slowly away on herself. I needed an explanation as I sat down to their surprise.
Debbie immediately opened up, “It’s not what you think John. I am trying to remain faithful to my husband, but I have to get off somehow when he is traveling. I needed something that would help arouse me and Susan agreed to let me touch her with my lips while I masturbated. That’s all it was.”
Susan jumped in immediately, “Debbie, you might as well tell John the truth. We have been involved sexually for a number of years John, but agreed to put it on hold when Debbie went through her divorce and then remarried. That’s why she coaxed me out to the bar with you tonight. I haven’t had sex, of any kind, man or woman, since we put our relationship on hold. Debbie has her own needs and I am willing to take the affection she offers me, however little it may be. We sometimes engage in this minor touching while we each masturbate ourselves to orgasm. This must seem disgusting to you I know.”
“Ladies, why don’t we go back to my office? I’ll pour us all some more drinks and we can work something out.” I was actually feeling pretty lucky, even if I was only going to get a female masturbation show. We walked the short block back to the office and took the elevator up to the 17th floor where my office overlooked the downtown skyline. My office is all glass so I can keep an eye on my beautiful hot staff as they walk around the office all day. Just as it allows me to look out it allows others to look in. We could only hope the janitorial crew had already made their rounds. With a few more drinks consumed the girls were once again feeling the need to touch. I sat Debbie down in a chair facing Susan and I as we took a seat on the couch. I began to kiss Susan on the neck just as Debbie had been doing in the bar. She moaned softly and her hips thrust slightly upward as her sexual rhythm seemed to come back to life from its exile. I kissed her slowly but continuously as I also eased my hand under her tight fitting dress until I found her wet panties. I wanted to go slow, very slow, to let the flood gates ease open instead of bursting like a breached dam. Susan had been without a man’s touch for a long time and she was eagerly lunging at my every move.
I looked over at Debbie in the chair and she had pulled her skirt off and sat clothed in a half buttoned white blouse and white lace panties. I knew her goal was to explode in a crescendo without engaging another person in the act. I wanted the visual of Susan and me building to an explosion to be her lubricant. As I watched Debbie ease first one finger, then two, into her tight, wet pussy, I knew she was well along the way.
Susan could now see my hardened cock bulging through my dress pants. She reached for my belt, quickly undoing it and dropping my pants to the floor. I ripped my shorts off and before I could sit back down on the couch Susan had my cock in her mouth. She lapped at my rock hard pulsing dick with an obvious experienced touch that was coming back to her. Her lips slowly went back and forth over the big purple head that was almost ready to explode and then suddenly the full length of the shaft disappeared as she took me in her mouth, deep-throating my entire manhood. She gently cupped my balls with her hand and slowly massaged them with the skill of someone who had done this a few times before. I almost came at that point, not being ready for such a lovely sensation. My eyes gazed at Susan’s beautiful tits and I rubbed each nipple lightly then gave them the full attention of my wet tongue. Her hip thrusts grew stronger as I began to slowly finger her clit.
Everyone was now totally naked, having paused only briefly in the action to shed the last remnants of the threads covering our torsos and the girls big, beautiful tits. Debbie was moaning in a deep guttural tone yet her eyes remained fixed on the action with Susan as I was now plowing my cock deep into her eager pussy. With a violent shudder and a tight clasp of my ass Susan exploded on my dick and balls as I continued to pound her revived cunt which was now oozing pussy juice and contracting in pulsating rhythms on my cock. I could tell she was almost spent as this re-emergent night had been more than she expected. I had a feeling she would want more and more after tonight. I eased myself out of her and nursed my unspent load, slowly jacking off the shaft of my cock to keep it at the edge of eruption, yet stopping momentarily as Debbie drew closer to a climax.
Susan lowered her lips to Debbie’s neck and placed delicate little kisses at the base. I moved the head of my cock to within just a fraction of an inch from Debbie’s mouth, knowing her own exiling rules would not let her suck it, but I certainly could provide her with a blast of hot cum as she came. The instant my hard dick neared her mouth she lurched violently in the chair, her fingering becoming faster and more frantic. Susan closed her lips around Debbie’s neck almost as a teenager would apply a hickey as a sort of act of dominance and Debbie began to explode. Susan grabbed my dick and jerked me off in the direction of Debbie’s face, splashing my load directly on her lips and then she gently licked every drop off of her former lover’s face and chest in a manner that violated none of Debbie’s rules, finally turning her mouth to my still throbbing member and sucking in the last drops of cum as we all collapsed in a heap.
“Well”, I asked with a satisfied grin on my face, “did that work for everyone?” They both smiled and nodded their agreement. I poured the ladies one last strong drink for the road as we all got dressed and then I buzzed the building concierge to call them a cab home. He would come to expect this call from me many times over the next few years as my office became a popular late night exhibition room. I gave Debbie a light peck on the cheek which I thought might be within the rules but I gave Susan a deep passionate kiss and she pressed her hand firmly against my crotch as we embraced. I walked them both to the elevator and we bid each other good night. I couldn’t wait to see how this would play out in the future and how long Debbie could resist either Susan’s pretty cunt or my eager to please cock.
I went back to my office to gather my things as I prepared to head over to my condo on the other side of the street for some much needed rest before returning to the office in the morning. I thought I sensed a presence in the outer office at one of the cubicles but couldn’t really see very well in the dark. As I walked across the room to my office I realized with only the lights on in my office and the rest of the floor dark, it really was a fish bowl sort of theater for anyone who might want to sneak around and watch the show. I thought out loud, “Might need to get some curtains…”
Suddenly a stereo of voices replied, “Don’t do that!” I turned to find Susan’s twin daughters, Tiffany and Amber, coming across the floor and before I could even get an astonished word out they both had their arms around me in what turned out to be a “thank you” embrace for my breakthrough night with their beautiful mother Susan. “We’ve not seen mom experience so much pleasure in months,” they uttered.
“When did you ever see your mom experience pleasure?” I asked, wondering just how much spying these two 18 year olds had done in their careers. “And how did you get in here in the first place?” The second question was easy. Susan had given the girls a pass key to the building in case they ever needed a safe place to go at night. Great, that meant these little sex starved vixens could bust in on me anytime they wanted to.
“Really”, Tiffany said, “getting past the guards is easy even without a pass key.” As her words trailed off they turned to each other and slipped their tongues together in a passionate embrace. “Do you know any guard who wouldn’t let us in after seeing that?” Amber asked.
Hell, she had a point. I wasn’t about to throw them out.
“And what about spying on your mom? How long has this been going on?” I was curious just how liberated and experienced these two magnificent bodied creatures were.
“We used to sneak into mom’s bedroom starting when we were about 13,” Tiffany offered. “Mom and Dad got divorced shortly after that and that’s when the best sex really started. There’s probably not much that can be done sexually that we haven’t seen firsthand. Mom is a very experienced woman. You’ll find that out if you’re lucky.”
“Yeah, that was a pretty decent show you put on tonight by the way,” Amber added.
“So how much did you girls see tonight?”
“We were already here when the three of you came in,” Tiffany said. “When you put us in the cab we had a feeling things were about to heat up so we just came here. We could tell by the way mom and Debbie where looking at each other. And the fact that they had you as a third element I think it finally broke through the frustrating log jam that they were in, thanks to Debbie’s stupid rules. You know, they really do care for each other.”
What they said actually made sense. At least it did now. As a man, I was too slow to figure out the angle that Debbie was playing by introducing me to Susan. Hopefully the result will make it worth exploring further for the both of them, and me. “Well, you young ladies are quite knowledgeable from what I can see,” I allowed, “but I think it’s time we all call it a night.”
“No, please John,” Amber pleaded, “let us have a quick drink and we promise we’ll head home. Promise. We’ve been here a long time and our happy hour buzz is melting away!”
I agreed on the one drink even though I thought it was not the best of ideas. I guess I was no stronger in their presence than the security guards downstairs. Men. We’re all weak!
“Besides,” Tiffany added as she knocked back the drink I had handed her, “there is one area where we really don’t have as much knowledge as you might think.”
“And what is that, Tiffany?”
The two of them drew closer to me and each placed a hand on my crotch. I felt a quick twitch at the touch of these two eighteen year old blonds, whose mother I had just fucked for the first time earlier tonight. Now here they were both standing in front of me, breasts heaving up and down, mouths slightly open, tongues wetting their lips, and a revelation about to be revealed to me.
Tiffany spoke for both of them. “We’ve done each other in every way possible. We’ve been fucked by young boys and we’ve blown young boys. We’ve even been with mom and Debbie and experienced the taste of real women. But we’ve never done or been done by a “real” man. We saw your cock tonight John when you took care of mom and Debbie. It’s nothing like the little boy dicks we’ve been with. We’d like to experience a real dick, John. Please?”
I shouldn’t have had that extra drink. I wanted to say no, no, in no uncertain terms, no. But something in my spinning head wanted this experience just as much as they did. After all, how often does a 55 year old man get to bed down two beautiful 18 year old tight pussies? Never! Well, almost never. But tonight could be my time. I gathered my wits as best I could and offered a small compromise.
“Look girls, I’m not so sure this is a good idea. First, I feel kind of weird that I just fucked your mother tonight and now you are asking me to fuck you. It doesn’t seem right, and yet I would love to fuck you both the rest of the night, believe me.” I took a small pause to accept the refilled drink glass being offered me by Amber while I watched Tiffany begin to undo her tiny schoolgirl blouse and skirt. I tried to refocus my thoughts. “Here’s my proposal, girls.” Amber was now removing her blouse and skirt as well. The both stood before me removing their bras and panties and Tiffany then reached for the zipper in my pants and slowly pulled it down as Amber helped my throbbing cock escape into the open air.
“What is your proposal, John?” Amber asked as she began to circle the tip of my cock with her tongue. Tiffany was stroking my balls while Amber licked me and jacked me off slowly. Somehow I had the feeling they knew what they were doing and how to do it very well. I was going to offer a compromise that we just go with a simple hand job tonight to give the young girls their first experience with a real man-sized cock, and then we could work up to other experiences at another date. Hell, the office staff would be coming in pretty soon if we didn’t get this over with. But I was already out of control of the situation, just as I was out of control with Susan and Debbie’s plans earlier tonight. Women. They really know how to fuck a guy around.
Tiffany had my cock in her mouth by now and was working up and down on it with a slow stroking motion that was surely going to make me blast off in her pretty little mouth. Had these girls ever tasted cum? Swallowed cum? Hell, it was too late to care now. I felt a rumble from deep inside my balls up through my cock and I knew I could not hold back. Tiffany pulled off of me enough for Amber to position her mouth to receive some of the hot gushing liquid as well. Both girls jerked on my shaft and each one had a hand on my balls. I filled their mouths with a giant blast of cum and they licked me dry, each one sucking gently until my spasms subsided.
“So John,” I heard one of them say as they gathered their clothes and slowly walked away (I was too drunk and spent now to know anything), “we really would like to hear about that proposal sometime. Maybe the next time you fuck our mom. We’ll be watching you know. Don’t worry John, we know the way out. Thanks for the drinks, John.”
I guess I wasn’t going to be fucking any 18 year old tight pussy after all. At least not tonight.