A Good Friend of the Family Pt. 02

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One lucky boss.
5.3k words
3.95
12.8k
17

Part 2 of the 3 part series

Updated 06/14/2023
Created 03/18/2023
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I guess you won't believe my story and I'm having some trouble believing it myself. I'm middle aged man. Keeping myself in good shape and taking care of a successful manufacturing business I inherited from my father. About a decade ago I hired this young guy Tim at the start of his career. Pretty soon it became clear to me that he was a manufacturing genius. He had lots of improvement ideas and as long as I gave him the resources he needed and my approval to make some changes he was making my business to boom.

On a personal level he was more hard to read but always very polite. Sometimes I had the feeling that he just might be the smartest person in any room he walks into but he never let it show. And he always talked very nicely about his wife whom he clearly adored. As time went by I got to meet Mrs. Tim on one fateful night. I had mentioned earlier at the work to Tim that I was going out to this one dancing place. He immediately went on how his wife loved to dance and how he should take her out to dance. So I was not completely surprised to see Tim and his wife at the same venue when the evening came.

However I was most surprised on what a catch Tim's wife was. All the curves in all the right places and this innocent but glorious face framed by light auburn hair. She was certainly dressed to kill as her dress was skin tight and showed plenty of cleavage. The backside of the dress even snugged a little between her butt cheeks making it extra hot. All though I was completely surprised by her looks I tried to play it cool and introduced myself officially as Mr. Brown, Tim's boss. But before I could help it I added "but you can call me Dick" and I saw her eyes tinkle.

My friend whom I came there with had to leave early and I was trying to wish Tim and his wife a good night and head to my home but Tim kept on insisting that I should stay for few drinks with them and enjoy the music.

Tim's wife Betty clearly liked dancing a lot. After dancing a few songs with Tim she headed to the toilet and Tim said to me that I should not just stay alone here but we should take turns dancing with Betty. I was tempted but tried to calm Tim down. After all I had no knowledge on whether or not Betty would even like to dance with me. They danced one more song and were having some conversation during it and when they returned Betty all most dragged me to the dance floor. I still wasn't sure and tried to ask Tim's approval for it but Betty didn't want to have any of it and off we went.

And it was smoking. Her body was on fire and I tried my best to follow. We melted down to the rhythm and danced in a very close proximity. I span her around and she pushed that perfect ass against my crotch. She even glanced at me and said 'ups' with her mouth but her playful eyes told me that it was no accident. Every now and then she went for Timmy as she called her husband and danced one song with him but never more. With me she danced like five or six in a row. Once there was a slow dance coming just when she was going to pick her husband from the table but turned around and just said that on a second thought it was not the time for a change yet. So basically I and Betty were having a dance night as Tim guarded our drinks and her purse.

For the slow ones we always went for the far most corner from our table. And she just glued herself to me. I was still trying to keep some part of it official after all she was my employees wife but she would have none of it. She was holding my arms tight and even pushing my hands lower to her hips. She turned around during a slow song and again swayed that booty against me firmly. Nothing could be helped and I became aroused right there and then and my cock became semi hard in my pants. She was grinding herself on it and even though I would never articulate it aloud this was a woman in heat. She turned around and pressed her front side against my semi erection and smiling gorgeously asked if "mister boss-man" was having a good time. I mean there was no way she wouldn't be feeling my cock all the time so she knew I was. I just leaned in and placed both on my hands on her ass and whispered to her that she's just amazing.

We danced like that many times more but finally it was time to call it a night. I was there with my car and offered to give them a ride home. Immediately Tim and Betty insisted that Tim would be driving us. I was not sure where this was going but agreed. Furthermore Betty insisted on us to sit in the back and let Timmy drive us. And what wouldn't I do to please a beautiful lady.

Betty was little tipsy from the drinks and she leaned into me in the car. We chitchatted and were just completely enjoying each others company. Betty made some remarks on how it was only suitable that Timmy was driving his boss around and we both laughed. And then her hand found it's way to my crotch and she started to massage my cock through my pants. I raised my eyebrows and was wondering if this was some cuckold fantasy of theirs. Quite soon I was as big as my trousers let me to be and there was a huge bulge reaching halfway down my thigh which Betty was constantly squeezing and stroking. And right then we arrived at their house.

So there I was trying to hide an erection given by my employees wife while he himself was thanking me for the fun evening and assuring me that we would do it again soon. They went for the house but Betty asked me to wait for a while. Soon she returned without Timmy and jumped on kissing me with full mouth. Then she went for the pants digging out my cock. "We don't have much time" she whispered and when my cock came out she almost laughed "big boss man oh my" and enveloped the head of my cock to that sweet mouth of hers.

I'm not complaining but there was no foreplay. She just bobbed her head up and down sucked harder than any woman I have ever met. Her other hand stroked the shaft and the other cupped my big balls. I took the liberty of exploring her body with my other hand. Fondled her boob and caressed her ass. Both felt just extraordinary good. She used lots of saliva and my cock head was in heaven. Obscene slurping noises were filling the car. I pushed my finger between her ass cheeks and moved the thong string aside and found her wet pussy from behind. It felt tight for just one finger. She gasped from the intruder but doubled her efforts on my aching cock.

She was moaning with mouth full of cock. I added another finger to her pussy. She winced but never missed a stroke. I was getting very close and told her so. She made no attempt to stop but stroked my shaft and balls in perfect unison with her head. The head of my cock was swelling to the max and since I felt it so clearly I bet Betty did so also. I knew I was over the edge and for few seconds the pre-cum just flowed in a continuous stream to her mouth and then it happened. I literally exploded in her mouth. Six seven maybe even nine or ten full jets of cum shot from my cock to her waiting mouth. Even the torrents of cum did not stop her but she still continued. She even tried to deep throat me but my cock was just too big. As my orgasm subdued she slowed the rhythm. I could imagine her swallowing since there was no way she would have been able to accommodate all that cum in her mouth.

She gave few last loving kisses to my still twitching cock and rose. There was some cum visible on the corner of her mouth. She smiled at me and said with teasing voice "thank you soo much mister-boss-man. I had a wonderful evening. I hope you did also" and then she kissed me on the cheek and left. What a woman.

Next day my mind was cleared. It was like I had been under her spell. It had been foolish from me to play with my employees wife. I could not manage the company without Tim. So it was fair to say I was worried. However Tim came along and was acting all cheerfully and actually inviting me over to a dinner at their home. He went on about how much his wife had enjoyed my company and made me little embarrassed. Again I was thinking that was all this some sort of kinky sex game for them. Tim didn't see the type. Betty on the other hand? Well maybe. At least plausible.

Tim was insisting on me to visit them and reassured me time after time that whatever made her wife happy would make him happy also. So I decided to go for it. After all I was also desperate to see Betty again. But then something came up and we had to cancel the dinner. Tim was needed on a business trip so I figured we have to postpone. However I got a sudden call from Tim where he was actually telling me to meet his wife without him. I was shocked. But on the other hand I was ecstatic since without Tim at their home I was quite certain how the evening would turn out.

I took some wine with me and was there at the agreed time. Her dress was just breathtaking. The moment I saw her I knew we would be making love that night but we started slow. I gave her a hug and kisses on the both cheeks and even one little tester one on the lips. She responded kissing me back and then smiling oh so happily. There was electricity in the air but we were not in a hurry. We wined and dined and shared stories. Got to know each other pretty well. After the dinner she put on some music and we sat in the living room sofa glued to each others. We started kissing and both of us were getting pretty heated up.

Then she remembered something and took her phone. She called her Timmy but when the call started actually sat her perfect behind to my lap on top of my hardening cock. She was swaying her hips in my lap all the time she was talking with him. I couldn't believe it when she asked Tim for his approval for me to spend the night and was even more surprised when she got it. After the phone call I decided to ask about what is going on with her and Tim? I mean did he know about us making out or about what had happened in the car?

She was perplexed and answered that honestly she did not know. She thought that Timmy must figure out something but they had not have any sort of discussion about this. But on the other hand she thought that Timmy had been pushing her towards me on the evening when we went dancing and even after that. So maybe he did get exited about the idea of his boss with his wife. But then she said that enough about Timmy lets focus on us and we went back to kissing. She straddled on my lap and I placed my hands on her round ass. I started to fondle and squeeze it firmly. And she was breathing heavy. All most making little audible moans between our kisses.

Then she rose up and dropped the dress. Under the dress there was even more breathtaking lingerie and her body was perfect. We undressed me as well and when I was fully naked she looked me from head to tows and back and was clearly impressed what she saw. I may be all most ten years older than her husband but I have kept myself in shape. Having a huge cock also helps. We kissed standing up and my erect cock was pressing her stomach. Then I shifted adjusting my cock towards her pussy and she took it between her things. I dry humped her and could feel her pussy lubricating my cock.

She pushed me back to the sofa and and closed on to my member by kneeling down to the floor in front of me. "This time there's no hurry baby" she whispered as if to herself and closed her lips around my cock head. It was just awesome. Here she was. A perfect sex doll kneeling for my cock in her most seductive lingerie. I enjoyed the visual image of her greatly. I watched as her small mouth tightened around my cock as she tried to fit more and more of it in. She was deliberately slow and used a lots of saliva. Her warm and wet mouth massaged every vein and ridge of my big penis. I was leaking in her mouth and she was savoring it gently. But I was not close by any means. I have always found it easy to postpone my orgasm even thought I was highly exited by her efforts.

For some time she used her hands on my balls and shaft. Then both hands and mouth on it. And then she gently let her hands wander on my muscular thighs as her head continued the slow up and down movement. I decided even to hold her head and pushed my pelvis up to fuck her mouth a little but she did not mind at all. Actually it made her moan around my rigid cock. Then her mouth parted my cock only to dive in to my balls. She suckled them with great care and used her hand to stroke my cock simultaneously. I was impressed.

Finally she gave some more attention to my cock head with her lips staring me in my eyes while doing it. My god I felt like I was in love. Still a minute or so taking it deep and then ending with little kisses all over my cock. I guess it's safe to say she was really worshiping my cock like no woman has ever done before her. Then she asked if I would like to take her to the bedroom and I eagerly agreed. We both rose up and she literally walked me by my cock to upstairs. Her hand felt super good on my cock.

I laid her down to the bed and she spread herself for me. I kissed her and my hard member was searching its target. I kind of rubbed my penis against her opening and suckled her neck and breasts. She asked in a small voice that I would be gentle with her since my cock was biggest by far she had ever taken. I obliged and proceeded softly. She closed her eyes and was breathing heavily as I penetrated her tight pussy inch by inch. We intertwined with each other tightly and she was whispering to my ear how she had never felt anything like this and how I should make her my woman. I sawed in and out of her and her moans were getting harder. Her pussy was like the sweetest velvet around my cock.

Needles to say we fucked the whole night. In the middle of the night we dosed off some but quite soon either her or I was twirling in our sleep and the sex began again. In the morning I had to call to work that I would take the day off and I fucked with her several times more. We did it once in their shower and then finally when I was almost leaving from their front door the farewell kiss turned too hot and I decided to bend her against their kitchen desk so that she didn't have any room to retreat away from my thrusts. I had a firm grip from her neck and other from her hips as I pummeled away. And she was having an orgasm after orgasm screaming.

After that I was just crazy about her. We had some hot texting and were both trying to figure out how and when to meet the next time. Betty somehow made Tim to let us go dancing but especially the couple of first times we went just straight to my place for an adulterous sex sessions. And no matter how much I had sex with her it never seemed enough. I would have liked to spend a longer time with her and she was feeling the same.

And finally I decided on this plan where I would suggest Tim that they could borrow my vacation home at the Caribbean even though I knew quite well that Tim would not be able to go in the middle of our busiest season. The plan worked almost by itself. When Tim was too busy to go Betty told me that she didn't even have to suggest it to Timmy but he took the initiative and promised to ask me to go with her. How sweet was that. Once again I was thinking that he just can not be this naive and he must know I and Betty are lovers. But I did not care. I was just thrilled I was going to get away with Betty.

At the airplane the flight attendant asked us what sort of trip we are having and I choked on my champagne as she joyfully informed her that we were newlyweds and this was our honeymoon. She congratulated us and even winked an eye on me and told me I was the luckiest man alive.

And that was true. We were having sex like bunnies. One night was particularly great as she asked me to enjoy the sunset at my balcony gave me a beer to my hand and then gave me one of her legendary blowjobs. But the interesting part came after I had filled her mouth once she refused to stop until I came a second time. I think it must have taken like almost half an hour but she didn't seem to mind. She just happily pleasured my cock with every way a man can imagine. It was hard to understand how she was so god damn good at it even though she had told me that she hardly ever gave oral to her Timmy. Her guess was that my cock was just so inspirational to her that she wanted nothing more than to give pleasure to me and my royal penis.

Another very hot encounter was on another night as we first walked to some secluded beach and after some petting I took her doggy style by the sea shore. It started romantically she turning her head over her shoulder to kiss me as I was making some slow but steady fucking circulations with my hips. In a while she encouraged me to give it to her hard and when I did she started to role play that I was too big for her pussy. "Please mister-boss-man your ruining my pussy with your godly cock. Please go slower. Its too big please."

She was so convincing I had to stop but she immediately looked back at me and asked whats wrong. "Why are you not giving it to me harder" and smiled devilishly. So I did. I slapped her ass. And I pulled her hair. She was whining. I even stuck my thumb in her asshole and that got her really wild. But she continued the role play. Please mister. Don't put your finger there its too nasty. Oh you bad bad man defiling young and innocent housewife you should be ashamed of yourself. She even tried to run away from me on her fours but I followed her with lust and kept poking my cock into her from behind. "Oh poor me. Being manhandled by such a brute of a man. My pussy will never recover." and then she changed tactics. "O.k. I let you do it but please cum fast. My pussy can not take it anymore. You are too much of a stud for this small filly. Please cum mister-boss-man into your pussy. Please do it." And I did. I moved my hands to her shoulder for the leverage and rose to my feet into this stand up doggy. I was pile-driving it to her from behind. She made her rump as round as possible and arched her back. And I filled her pussy to the brim.

This was not the only time we went to my vacation home together. But the next time we just could not avoid getting Tim there with us. Again it was just unbelievable how Betty could make him to assist us on our infidelity. Right on the first night I was prepared to going to sleep alone when Tim knocked my bedroom door and explained how his wife did not like the bed on the guestroom and if it wouldn't be too inconvenient for me they would like her to sleep in my bed. I shit you not this was what he asked and there was no hint in his manners that he would have some cuckolding fetish which would cause this strange request. I of course agreed and so Betty came to me. We made some sweet love and I was actually little worried if Tim might hear us but mostly I was just very focused on Betty.

In the morning I went to the shower and thought that Betty has already gone to breakfast with her husband but she sneaked up on me from behind and reached her hands around me to my cock. "Oh mister boss-man needs some help washing this huge cock". And then she soaped it and fell into her knees and waved it in front of her nose. "I can't believe you put this thing inside of me. It's too big. You are an evil man breaking me every night with this huge meat". And then she sucked it like there was no tomorrow. She grabbed my hands and placed them on her head. Looked up between her slurps and told me to help her deep throat it. It was just impossible to anyone deep throat my huge cock but I did not mind her trying. She looked like some sexy chipmunk trying to eat up corn cone or something. I knew she liked to play and was pulling her face to my crotch with quite a force when I felt my cock head somehow miraculously penetrate her throat.

Her eyes bulged out but her hands gripped my ass tight and she encouraged me deeper. After the initial break through in her throat the rest slide in with surprising ease. Couple of times she had to have break for some air but every time she invited me back in. In the end her nose was touching my pubic hair and I just let go. I came deep in her throat and it was just pure pleasure. With her usual post mouth cum routine she made sure she sucked every last drop of my semen in her tummy. Then she slapped her face with my cock and smiled at me "You dirty old man you fucked my poor throat. I love you and you only think about new obscene ways for me to satisfy your hung bull cock." Then she gave one final loving kiss to it and left the shower. How come I was so lucky to meet such a sex genius. I don't know but I sure was not complaining.

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