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Sam, Her Boss and Her Cuckold

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herboy63

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Sam, Her Boss and Her Cuckold

I was distracted. My eyes gazing at her long brown hair, her smoky hazel-green eyes, the cute button nose and those lovely, luscious lips that I knew so well. Even the dark blue, tailored business suit couldn't hide the swell of her perfect 36-D breasts that I so loved to squeeze tightly in my large hands while rubbing my thumbs firmly over her erect pencil eraser nipples. Her girlish voice had a soft but assertive tone that belied her sharp, aggressive legal mind that made her an excellent negotiator. The poor twit listening to her from across the conference room table had no idea who he was dealing with as she laid out the facts and the strength of our position and the reas on why his claim had no merit. I glanced at him and noticed he was trying not to stare at her cleavage as he shifted uncomfortably in the big leather conference room chair and tapped his fingers nervously on the stack of papers in front of him. I'd worked with idiots like him my whole career and knew that after the foot-stomping and bluster he would eventually cave-in and either leave with his tail between his legs or wish that he had later when we turned up the heat and buried him one way or another. That's why I was shocked and snapped out of my distraction when I heard Sam, my brilliant attorney and lover, say, "Therefore, we are making a one-time, take it or leave it offer of $25,000 that expires at the end of today."

We had never discussed making a settlement offer with this over-blown asshole and even though it was less than half of what he was claiming she knew that any offer should have been approved by me in advance. He looked as surprised as me and after a bit of babbling he quickly agreed to the offer and said his attorney would call her before the end of the day. She must have felt my steely gaze upon her as she made a furtive, nervous glance toward me at the end of the long conference room table. I never said a word and just sat silently in my large leather chair at the end of the table as I watched her shake the idiot's hand and show him to the glass door at the other end of the wood and glass conference room. As she started to leave the room with him, I said sharply while still sitting in my chair, "Sam."

She stopped in her tracks and turned partially toward me and turned her eyes shyly in my direction. I stared at her for a moment before saying, "We'll discuss this further over the weekend."

She rubbed her lips together nervously and licked them before answering softly, "Yessir," and walked quietly out the door to return to her office down the hall.

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As I absentmindedly stirred the noodles on the stove, I started to wonder if I made a mistake in settling the case on Friday. It had been two days and Trevor did say he wanted to "discuss this over the weekend" but he still hadn't called or contacted me since the meeting in the conference room. I knew the settlement was the right thing to do. We would have spent more time fighting over the claim than it would have been worth and, even with the settlement, we still made good money on the project. I also knew that Trevor didn't necessarily like to settle things easily and fairly. He liked to win. I could have explained why my solution was the best approach and might have convinced him to do it my way ..... but at the last moment I decided what I really wanted was to "discuss this further over the weekend." Now, I was wondering if I went too far. Was he so mad at me for not getting his permission first that he was done with me? I could accept getting fired. My reputation as a lawyer was good enough to get me a job almost anywhere in the city. But, of course, that's not what I was afraid of. What if he didn't want ME anymore? What if he no longer wanted to call me into his office "just to gaze at your beauty"? No longer wanted my head laying in his lap as he stroked my hair? No longer wanted me kneeling at his feet with my arms wrapped around his legs? No longer wanted to bend me over and fuck me senseless with that glorious cock? I couldn't bear the thought of never hearing his sexy, deep voice saying, "come to me girl" and staring into those piercing gray eyes as he held me by my hair and then crushed my lips against his while squeezing my ass and holding me tightly against his muscular body.

So much has happened in the past six months – the past year really. I turned 30 shortly after the birth of our second s on and I was feeling old and wasn't feeling sexy anymore. I needed a change. For the first time in our five year marriage, I wasn't feeling as happy and in love with my husband as before. Dan, my husband and soulmate, is the love of my life. He is funny, smart, good-looking, a great dad and we can talk about anything for hours. However, I think the bad sex was finally catching up with us and causing friction in our otherwise happy marriage.

I knew of his "shortcomings" before we got married but somehow I convinced myself that all of the other wonderful things between us would make up for the lackluster bedroom performance. Dan was so eager to please me and he spent many hours with his face between my legs. We experimented with vibrators and an assortment of adult toys and I got more massages and foreplay than most women could ever dream about. But, with his teenie weenie, six-strokes-and-squirt performances, it was becoming evident that I desperately needed a good fucking. At first, I was just frustrated and we would have disappointing sex less and less frequently. Eventually, I knew it was time to talk before my frustration caused things to really get bad between us. We agreed that we needed to do something to put a spark in our sex life and started to share fantasies.

I found out that Dan actually got excited when I talked about my old lovers and even more so when I teased him about having the smallest cock of any man I'd ever been with. After drin king one night, I shared a sex story from my college days where my boyfriend would tease me and get me right to the edge but not allow me to orgasm, sometimes for days, and I admitted it was really exciting to have someone that kept me horny by controlling my orgasms. Dan was hard as a rock after hearing the story and said how exciting it must have been to be denied like that. When I asked him if he would like somebody to do that to him, if he would like for me to do that for him, he very eagerly agreed and we started practicing orgasm denial and chastity that very night. Keeping Dan denied was fine by me since I didn't get much out of fucking him anyway and teasing him was kind of fun but momma needed some satisfaction. That is when we started to talk about cuckolding and things got more interesting. We found a dating app where we could seek an occasional hook-up for me with some random guy and agreed this could add an exciting spark to our less-than exciting sex life. We arranged a few one-night stands where I would meet someone at a hotel bar and if I liked them then we would go up to my room (that Dan paid for!) and have a wild night of sex. Some dates were pretty good and some were great. If I'm being honest, then I'd have to also admit they were all better than the sex I'd been having for the past five years.

Shortly after we started our cuckold dates, I also decided to change jobs. The demands of working in a law firm were competing with the demands of being a mo ther of two and budding hotwife. So, I sought a less demanding corporate position where my hours were more predictable and I could be home in the evening. That led me to getting the job working for Trevor and nothing has been the same since.

I almost burned myself when the phone rang, causing me to drop the spoon into the pasta sauce, and I made a big mess on the stovetop. I was flustered and trying to quickly wipe up the splash of sauce while going for the phone. "Do you want me to answer it, honey?" my loving husband, Dan, asked from the kitchen table where he was feeding our two year-old boy while entertaining our four year-old s on at the same time.

"No, I've got it," I said quickly. We both knew who was calling by the melodic strum of harp strings that was the ring tone on my cell phone. Trevor had picked it out himself. He said, "An angelic summons to my beautiful angel." He's so sweet sometimes.

As I danced across the kitchen wiping my hands on a towel and grabbing my phone from the countertop, I saw my husband watching me with curious, expecting eyes. He knew about Trevor. He had even met him a few times.

I picked up the phone and answered in my most cheery voice, "Hello?"

"Did I call at a bad time?" Trevor's deep, sexy voice purred through the phone line.

"No, I'm just making all of us lunch."

"Well, Dan is going to need to finish making lunch for him and the kids because you have somewhere to go. Don't change your clothes, don't put on makeup, just grab your car keys and get to the office right now. You will go to the conference room, strip naked and stand in the corner until I get there. Do you understand?"

I felt my knees tremble and my head swooned for just a moment as my mouth went dry and in a whisper I stammered in a mixture of relief and excitement, "Yessir." Then he hung up and the line went dead.

I looked at Dan who was watching me the whole time I was on the phone and he had a puzzled, concerned look on his face. "Everything alright honey?" he asked.

"Yeah sweetie, I just need to go to work. I think the pasta and sauce is finished so can you take care of lunch? I need to hurry over there." I really wanted to run upstairs and change out of my yoga pants and at least put on some panties and a bra but he said to leave right now without changing, so no makeup, tight yoga pants, and a loose t-shirt would have to do. I slipped on some sandals, grabbed my car keys and purse and headed out the door.
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herboy63

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Posts: 407
#2
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Those familiar feelings of concern, worry, angst, curiosity, and lust were coursing through my body as I cleaned up the lunch dishes and got the kids ready for a nap. Whenever Sam's boss called, I knew she would drop everything to take the call and she always answered in that flirty playful way that made it obvious he was more than just her boss. It had been almost a year since she took the job at his company and he seduced her within the first month of working there. We had just started exploring cuckolding so when she told me about her hot new boss I got swept up in the excitement that they might get together sexually. Little did I know how things would evolve.

I could remember the conversation while we lay in bed one night – well, I was laying in bed and she was sitting on my face with knees on either side of my head while her hips glided rhythmically over my lips while I licked her pussy hungrily. She was pinching her nipples between her fingers and thumb as she asked me, "would it excite you if I started having an affair with my boss?" I couldn't really speak with her sex covering my mouth so I just grunted a "mmm hmm" in response. "You know I really enjoyed fucking those guys we found through the hook-up website but that was just sex. I want to have a real relationship so the sex will be even hotter." Her eyes were closed and she was incredibly wet as she kept grinding on my face and thinking about her new boss. "What if he got possessive and wanted me to only have sex with him? Would you like that Danny boy?" I didn't know how to answer that one as she reached back behind her and jiggled the cage that was trapping my cock and balls. "Would you like knowing some other man owned your wife's pussy? Maybe he could even keep the leys to your little cage," she laughed. We had just bought the chastity device as our experimenting with chastity was becoming a more frequent part of our sex life. I couldn't remember the last time we actually had penetrative sex.

I had to admit it was a relief to know that she was no longer frustrated with our disappointing sex life. The pressure was off of me after she agreed to try dating and having sex with other guys. I was never the jealous type and all I ever wanted was for her to be happy. I knew she was out of my league when we met and could never understand how I was so lucky to have such a beautiful, fascinating woman fall in love with me. My insecurities about sex were always in the back of my mind but we were perfect together in so many ways. I tried to make sure she was happy and satisfied in every way but it was becoming evident that something was wrong and she wasn't happy. Thank god we were open and honest with each other and could talk about our feelings. Although I still wonder if we let the genie out of the bottle with our honesty.

At first, I didn't even know our sex life was all that bad. I always made sure I brought her off with my very talented tongue before we had sex. Unfortunately, I would usually only last a minute or so and then apologize when I could tell she was disappointed I was already done. I assured her I'd rather give her oral than have sex anyway and she'd nod her head and say, "I know honey and you do that so well." So, it wasn't a big surprise when she told me one night that even if I could last longer it wouldn't matter because my penis was really too small to bring her to orgasm. Then, she told me about her boyfriend in college and how good of a lover he was and the sex games they would play together. I didn't want to dwell on the "your little weenie is too small to make me orgasm anyway" thing so I asked her to tell me more about their college sex games. She thought for a moment and got a twinkle in her eye and told me how he liked to tease her to the verge of orgasm over and over and then would just stop and say "Let's go get a pizza" or something like that and refuse to let her orgasm. She said she hated it at first but then orgasm denial became a big part of their play. She never knew when he was going to fuck her to orgasm or stop and make her wait. As a result, she was always horny and could orgasm at the drop of a hat. I was enthralled at her story and when she asked if I wanted her to do that with me I jumped at the chance to give her total control over our sex life.

We quit having conventional sex after that since we both knew that she couldn't have an orgasm with my penis in her but the sexual tension picked up considerably as she took more control and became somewhat more dominant overall. She loved to openly tease and torment me and wouldn't hesitate to demand I orally please her while denying me any sexual release. I was in heaven!

At first, I was surprised when she suggested we look for men to have sex with her on a dating app but it was the obvious evolution and solution for her newfound control over both of our sex lives. I had quit working and was a full-time stay-at-home dad due to the long hours she was working at the law firm, so I would screen potential candidates for her during the day and then we would review them together at night when she got home. She found several men that piqued her interest and then, acting as her own personal concierge, I set them up on a date with dinner and a hotel room if she decided she liked them. I loved being part of the planning and would spend the night barely slee ping while wondering how her night was going with this new stranger. She would return the next morning smiling and relaxed but acting as if she was just returning from a workout at the gym. I would be eager to hear all the details but she would tease me by saying, "You'll just have to wait until we go to bed tonight and maybe I'll let you out of the cage to wank while I tell you."

Shortly after she started dating the men on the dating app, she decided to change jobs and that is when everything changed.

I still think she took the job at Trevor's company because of her immediate attraction to the tall, masculine businessman. She says he seduced her but I doubt he had to do much seducing to convince her that she wanted to get to know him better. After work dri nks turned into working dinners and then business trips together within a month of her working there. She was always honest with me when I asked about what they were doing but she wasn't as open and eager to tease me about it as she was after the dates with the guys from the dating app. This was obviously something more serious and I could tell she was still processing the relationship in her own head.

The night she sat on my face teasing me about having an affair with her boss was apparently the night she got her first kiss from him. They had gone out for dri nks after work and he kissed her goodnight before sending her home in a taxi. It was an intense night and she would have gladly done more than kiss him – and he knew it – but he sent her on her way saying, "You are lovely and I want to know so much more about you but now it's time for you to go home to your family. We will do this again soon." Within a week she was on her knees in his office and gave him a blowjob at his desk. He didn't fuck her for the first time until a month later when they went on a business trip together. He did everything on his own time and in his own way.

After six months, their relationship has become very intense and very intimate. My cuckold angst and concern isn't focused so much on losing my wife to him, although that is always somewhere in the back of my mind, but instead it is on the changes I see in her – both physically and emotionally. On the one hand, she is obviously having the sexual time of her life. She is excited, satisfied, and downright giddy all the time. Her horniness overflows to me so that I am getting the chance to suck on her fabulous breasts and lick her pussy more than ever in our time together. However, I am also seeing more and more marks on her body from their rough sex and, while her dominance in our relationship hasn't changed, she is clearly becoming more submissive in her relationship with him. He demands it and she most willingly gives it!

This weekend is a good example of the changes where Friday night she got home from work and it was evident that she was pretty worked up over something. When I asked how her day went, she said something about Trevor being mad at her but she surprisingly seemed pleased about it - so much so, that she had me put the kids to bed early so we could go to bed ourselves. I was even thinking that I might be finally getting to have penetrative sex with her! After a nice long bubble bath she put on something sexy and told me I could relax and take off the chastity cage for the night. Once I was totally naked and laying next to her sexily scented body in bed, she took the large dildo from the beside nightstand, closed her eyes and told me to slowly massage and suck her breasts while she pleasured herself with the dildo. She must have already been pretty wet because the thick 8 inches of latex seemed to slip right into her tight pussy.

She never said a word as she pleasured herself but she was getting closer to orgasm quickly. She gasped, "Dan, suck on my clitty and make me cum," while the dildo made sucking and slurping sounds as it plunged in and out of her dripping sex. She pushed the phallus all the way into her as I found her rock hard clit with my lips and began to desperately suck and lick the tiny nub as the base of the dildo pressed against my chin. She almost immediately began to convulse and scream out her orgasm as it rocked her entire body. She moaned loudly and shouted for me to stop licking her pussy as it was becoming too sensitive. As she withdrew the large cock-shaped tool from her velvety lips, it made a popping sound from the suction that it made with her copious amounts of lubrication dripping from the shaft.

After she caught her breath, she smiled at me and wrapped her hand around my erect penis and squeezed the shaft. Her one hand pretty much covered the entire shaft so she didn't need to move her hand much to squeeze the head and shaft in one short stroke. She had a sultry look on her face and said, "Do you want to suffer for me Danny? Do you want to be my good boy?" She moved her hand slowly and I could feel the cum welling up in my balls. I was still on my knees next to her as she lay on her back on our marital bed.

"Yes," I answered in a gasp. "Anything sweetheart."

"You could put it in me if you want. It won't do anything for me. You will be the only one that gets any pleasure from it. But you can if you want." She paused and stared at me with her sexy, teasing eyes. Then, she licked her lips and continued, "Or, you can thank me and pull your little thing until you cum on my tits and then lick every drop off." She smiled as she saw the desperate look in my eyes and waited. "Well?"

I leaned down and kissed her passionately on the mouth. I loved this woman so much. When I finally ended the kiss I nibbled her earlobe and put my lips next to her ear and whispered, "Thank you Sam. Thank you. Thank you." Then I returned to my knees at her side and saw she was beaming at me as I replaced her hand with my own. I pumped furiously while aiming my manhood at her perfect breasts and squirted almost immediately. I almost fell over on top of her as the wave of pleasure swept over me. When I was done and the flow from the tip had stopped to a trickle down the side of the boob closest to me, I laid down next to her and began licking up every drop. As I moved over top of her to get the drips on her nipples and other breast she wrapped both of her hands around my head and crushed my face into her sticky, wet bosom. She held me tightly like that for what seemed to be forever and I was in heaven. She finally released me and we fell into a deep, blissful sl eep.

The next day, Sam was like a different person as she paced nervously around the house all day and when I suggested we go out to dinner she insisted that she just wanted to stay home and read but she fidgeted until she finally went to bed around midnight. Then, when she woke up today she seemed even more distracted but in a melancholy way that didn't change until that phone call from Trevor at lunchtime. She almost jumped out of her skin she was so happy to get that call. However, whatever he said to her in that short call seemed to totally change the mood and there was no doubt she was both excited and nervous when she left. What in the world were the two of them up to?
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BumNote

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#3
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What a brilliantly written piece! I'm loving it and can't wait for further developments 😊
herboy63

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I sat in my office and watched her pull into the parking lot in her sleek little Audi. Now that Dan was staying home with the kids, she usually left the Toyota SUV with the car seats for him to drive and she drove the turbo-charged Audi TTS. This car fit her well – fast, exciting and sexy. I was glad to see that she obeyed me and arrived at the office quickly. As she came into the lobby and waited for the elevator, I switched the security screen on my computer and could see she was wearing tight-fitting yoga pants that left little to the imagination, a t-shirt that clearly showed her nipples were already hard, a pair of strappy sandals and a small handbag. At least she was following directions today.

I had parked my car up the street so she wouldn't know I was already in the office. I had this office building built several years ago and had high-definition security cameras installed throughout so I could monitor all of the cameras on my computer at will. She was fidgeting in the elevator but never even looked at the camera so I didn't think she had any idea I was watching her. My office door was always closed and locked after hours so she wouldn't be able to see me if she decided to check my office. Besides, I told her to go straight to the conference and strip and wait in the corner for me so coming to my office would just be one more thing to add to the list.

As expected, she got off the elevator and headed toward the conference room but stopped for just a moment outside her office before changing her mind and continuing to the conference room. I was almost disappointed that she didn't give me one more thing to discuss with her. I switched the camera view to the conference room and watched as she entered the room. She looked around for a moment and walked over to a window to look at the view. There was a lake and the road into the office park came around the lake. I suspected she was looking to see if I was on the road yet. Our commute to the office was about the same distance so she knew I would probably be coming soon. As she looked out the window and I watched her on my computer screen, I saw her hand go to the front of her t-shirt and she brushed her fingertips lightly over her nipples. She slid her other hand under her t-shirt and it looked like she might be squeezing her nipple between her fingers while she did the same to the other nipple with her fingers on the outside of her t-shirt. I was enthralled watching this incredible woman pleasure herself on my screen. Obviously, we would be discussing this later but I was a happy voyeur knowing she was getting hot as she waited for my arrival.

She stopped almost as quickly as she started and stripped all of her clothing off. She folded her clothes and put them in a neat little pile on the far end of the conference room table where I usually sat. Then, she walked around the room a few times while glancing out the window every few seconds. She even sat in my chair and spun around in a circle before sitting on the edge of the table right in front of the chair and slid her middle finger sexily up the slit of her pussy and licked it clean. I could easily imagine sitting there and watching her do that in front of me because we had done things similar in my office on many occasions. Then, she seemed to resign herself to the task at hand and walked to the corner that was nearest the row of windows and stood there, naked, leaning against the wall and watching out the window.

I waited for a full five minutes watching her lean against the wall but she stayed in the corner the whole time while looking out the window the best she could. I finally turned off the computer and opened the door to my office quietly as I walked stealthily down the hall to the conference room. She must have heard something because when I entered the room she was standing upright with her nose in the corner, feet together and both hands holding the back of her head like a criminal under arrest waiting for instructions. She didn't say a word or turn her head as I entered the room and I didn't say anything to her at first. I just walked to the far end of the room and sat in my chair where she had just gave her little show. I think I could still smell her musky scent.

"So, girl," I started. She began to turn toward me and I snapped, "I didn't say you could take your nose out of that corner." She quickly returned her nose to the corner and her hands to her head as she seemed to stand even more rigidly than before.

I loved staring at her naked body. I never tired of her beautiful curvy body and lovely-scented, long brown hair. Her ass had a perfect curve that ended in a crease at the top of her leg that just made you want to grab both cheeks and squeeze them tightly as you pulled her to you or to run your hand smoothly over those mounds as you spread them and ... I digress.

I waited a moment before continuing, "It seems we need to re-establish some ground rules around here and make sure there is no confusion over how things work or who is in charge. I'm hoping that after today there will no longer be any confusion or a need for a repeat reminder." Then, I got up and walked to a wall near her where we kept a table with the water service and a bar underneath. The table was about four feet long, on wheels that could be locked and with a 1" thick black marble top. I lifted the serving tray with the water pitcher and glasses off the table and put them out of the way on the conference table. Then I rolled the table to an open area and locked the wheels.

"Come lie face down over the table Sam," I commanded. She turned to see the black marble tabletop and didn't hesitate to walk over to where I stood. The tabletop was even with her hips and she bent at the waist and lay facedown onto the black marble. She immediately gasped as her rock-hard nipples and flat stomach made contact with the cold marble. I placed my hand on her back and pressed down, smashing her tits onto the stone top saying, "Don't you dare move or take your hands off the table." I knew the cold marble must be incredibly uncomfortable on her naked skin but she grasped the table tightly and did as I said and did not move.

Her head lay on the black marble tabletop and she was facing the window as I walked over and removed the rod that adjusted the blinds over the windows. It was the perfect length and would make an excellent cane. I smiled at her as I removed the rod and swished it in the air a few times so there was no doubt what it would be used for. Her eyes were wide open now and I couldn't tell if it was fear or lust but she was totally focused on what I was doing now. I walked behind her and lay the rod across both of her butt cheeks to measure the distance and let her feel the tormentor and to allow her to anticipate what was going to happen.

This wasn't the first time she had been in a similar position but this was the first time she had ever felt a cane. Soon after we started having sex with each other, I had playfully slapped her on the ass when she visited my office one day and she just giggled and turned her ass back toward me and bent over slightly. "You're such a tease," she said over her shoulder. I told her to be careful what she wished for or she might find out what a spanking really felt like and gave her a hard swat and sent her on her way. Later that afternoon when we went back to my house for a quick fuck before she went home for the evening, she told me, "I was so fucking horny all day after you slapped my ass." I told her to lay over my knees and I'd be happy to warm her up as foreplay. I was kind of surprised that after every smack of my hand she raised her hips up to let me know she wanted more and would moan to let me know that she wasn't done. After a dozen smacks or so, I was super turned on and told her to get on her knees and thank me for the spanking by sucking my cock and proceeded to fuck her like a madman. That seemed to let the genie out of the bottle and the woman's desire for kink and sex was insatiable. Our favorite sex position became doggystyle because I could smack her ass while fucking her and sometimes she would cum from the spanking before she came from my cock. I also began to introduce nipple clamps and other toys to our games as she clearly loved each new level of sensation. One day, I gave her a butt plug and made her wear it the entire day at work. It was exciting for both of us as she sat uncomfortably in a meeting in this very conference room and negotiated a deal with one of our customers. She was a true professional and nobody but me could tell she was anything but the soft-spoken but aggressive corporate attorney that we all knew so well. I couldn't wait to fuck her later and ask her how she liked her new toy.

Although she was submissive with me, she was anything but with her husband. She was very open about their loving relationship and the fact that it had been challenged by their failing sex life until she started taking lovers. She said her feelings for me was helping her understand him better and to see what she needed to do to fix the intimate part of their sex life. Apparently, her solution was lots of teasing and orgasm denial mixed with a healthy dose of subtle and not so subtle sexual humi liation for the poor guy. That was fine with me because it only seemed to make her even hornier with me. One night, she even invited him to come along on one of our dates. They got a babysitter and she told him, "You can be our chauffeur tonight."

We went out to dinner and then to a jazz club for dr inks while Dan drove the two of us around town in my Mercedes S-Class. I wasn't used to sitting in the backseat but had to admit it was really nice having a driver while relaxing in the plush leather seats with a beautiful woman at my side. Especially when she leaned over and unzipped my pants to fish out my cock and gave me a blow job on the way to the club. I guess the wine at dinner and having her husband as our driver was making her feel especially amorous. I noticed Dan watching in the mirror and scolded him to keep his eyes on the road and to be careful not to wreck my car. Sam giggled and put even more effort into what she was doing. When I noticed that we were almost at the club, I told Dan to pull over to the curb so she could finish since there was no way my erection was going back in my pants at this point. She slid her velvety lips up and down the length of my shaft as she held the base of my cock with one hand and deep throated the head of my cock until I finally exploded into the back of her throat. She made sure that she captured and swallowed every drop so that nothing would stain the front of my dry-cleaned pants. When she sat back up and gathered herself once again, I said, "Okay Dan, you can drop us off at the club in the next block. We'll be out at the curb at 10 sharp so please be sure to be waiting when we come out."

I had smacked her ass later that night in the hotel suite after Dan dropped us off so he could go home to relieve the babysitter. He would be back in the morning in his SUV with the car seats and kids in the backseat to retrieve his bride. In the meantime, she was bent over a couch similar to how she was laying on this marble table and I spanked her as a few times to heat her up the way she liked and then had enjoyed a very satisfying fuck. However, it was not going to be like that today. No, this was something different. We had some business to attend to here.

I placed the cane along the length of her spine and let one end nestle between the luscious mounds of her ass. I wanted her to think about that rod and how it was going to feel when it whistled through the air and left a welt across those beautiful cheeks. Without saying anything, I gathered her long brown hair into a ponytail that I held in my left fist and then began to smack her ass with my open right hand. I alternated from cheek to cheek in a steady rhythm and wasn't surprised when she seemed to push her ass to meet each smack. She seemed to be enjoying this but that was not going to last much longer. This wasn't going to be our usual "smack and tickle". I stopped spanking her with my hand and grabbed the rod by the end between her asscheeks and pulled it so that the entire length slid between her upturned, reddening mounds. I stood directly behind her and admired the beautiful sight. She was gripping the table so tight that her fingers were white and I was sure that the cold marble must be setting every nerve ending in her nipples, tits and stomach into overdrive. I could only see the side of her face but she looked almost blissful. I was determined to change that and to make sure she understood why we were here. As I moved to her side with her head facing the other direction on the table, I said, "You know why we are here, don't you?"

She answered in her soft voice, "Because you are angry that I settled the claim."

I swung the cane through the air a few times so she could hear it whistling just above her and then placed it across both of her round mounds before raising it and snapping it forward to place a bright red welt across both asscheeks. She yelped loudly and gasped a few times at the intensity of the stroke but she settled herself quickly.

"No, I'm not angry at you for settling the case. I'm angry that you didn't tell me you were going to settle the case before making that decision on your own." I then applied two more rapid-fire strokes with the cane. She almost came up from the marble table but somehow her iron grip held and she was able to lay back down with her bountiful breasts smashed back down and highlighted so lovely against the black marble. Her head was still facing the other direction but I could tell her breathing was different now. She was panting just a bit as she processed the intense sensations.

I waited a moment and tapped the cane lightly on her red, welted cheeks, "Ready?"

She paused and after an audible exhale said, "Yessir." I applied another stroke and she yelped while squeezing herself tightly to the table and bringing her feet almost all the way to her ass and kicking her feet back and forth rapidly in the air.

I waited until she put her feet back on the ground and said, "One more for good measure." I was shocked when she pushed onto her tiptoes and with an arc in her back she defiantly raised her hips very subtly so her ass was pushed prominently in the air waiting for the final stroke. I could only shake my head at the spunk in this woman! I applied the final cane stroke right at the top of her thighs where the leg meets the ass and her knees buckled in just a bit and she put her forehead to the tabletop as she gasped out a loud, "Oh God!"

I told her to get up and to lay on her back on the conference room table as I pulled the belt through the loops of my pants.
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herboy63

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My ass was on fire, like a hundred bees were stinging me all at once. I could now strike "caning" off my To-Do list. At first, I thought I'd made a mistake riling Trevor up and that I might not be able to handle the intensity of the caning. The first few strokes were like lightning shooting through my body but now that it was over I could feel my head floating on a hazy cloud of subspace from the adrenaline rush elicited from the experience. I was happy to be getting off the ice-cold marble tabletop. My nipples felt like ice picks etching into the cold stone but the chill I felt from the marble was quickly replaced by the fire in my backside. My heart leapt when I heard him tell me to lay on the conference room table because the fire wasn't just in my asscheeks – my pussy was also overheating. I couldn't wait to feel his cock buried in my wet pussy and his fingers pinching my hard, sensitive nipples.

As I moved off of the marble and toward the large mahogany wood table, I noticed he was removing his leather belt from his pants and thought, "Oh crap, he is going to whip me with that belt," but remembered he told me to lay on my back. I did what he said and sat on the edge of the table before laying back and hoping he was going to grab my legs and put them over his shoulders.

Instead, he said, "Move back a bit and spread your legs with your feet on the table." I did as he asked and then saw what he had in mind as he wrapped the belt around his hand and left about a foot hanging down as he pulled up a chair and sat at the table between my legs with my pussy facing him as a very inviting target.
"So, why did you do it my love? Why did you settle with that overblown asshole?" he asked before snapping his wrist and bringing the very tip of the belt sharply across my pussylips. I yelped from the contact and noticed that the belt made more of a "splat" sound due to the amount of moisture dripping from my pussy.

"I knew it was the quickest and most cost-effective way to resolve the matter and I knew you probably wouldn't want to settle even though it was the right thing to do," I said truthfully – well .... almost truthfully anyway.

He snapped the belt two more times in quick succession that hit right on my engorged clit. I involun tarily snapped my knees together and yelled, "Fuck!" before slowly spreading my legs again as the pain and heat radiated up from my pussy to my brain.

"I don't disagree with you and think that makes a lot of sense," he said in an almost amused voice as he watched me from his vantage point between my spread legs, "We both know you can be a very persuasive woman so why didn't you just come to me and explain that so we could come to agreement that your way was the best approach?" He was waiting for my answer as I was anticipating the next assault on my pussy.

In my most sultry voice and with a sexy smile I answered softly, "My dear, I thought that is what we were doing right now."

Nothing happened for a moment as he absorbed what I had said and then he laughed and said, "You little vixen!" and then he snapped the belt one final time before dropping it on the table next to me and removing his clothes. It soon became apparent to both of us that my approach was indeed the best solution as I received a glorious fuck for the next half hour.
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herboy63

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"Yes Dan, he did take my ass too," Sam answered me as she lay on her stomach on our bed. I was massaging lotion into her asscheeks over the welts that were placed there during her trip to the office this afternoon. Trevor sent her home without letting her cleanup after their "meeting at the office". He made her get dressed with instructions not to cleanup in any way until after the kids had gone to bed and I got a chance to rub some lotion onto her sore butt. Then, she was to give me a blowjob with her butt plug in place and she wasn't to remove it until after I came in her mouth. She also wasn't allowed any orgasms this week until after he got back from a business trip.

When she returned home from the office wearing the same yoga pants and t-shirt it was evident from her "just-been-fucked" hair and the dreamy look in her eyes that they had been busy during the office meeting. Sam was always very open about what she did with Trevor and would answer any questions I had about what they did or how she was feeling. After verifying that she was fine ("better than fine"), she told me that we could talk more after the kids went to bed. Dinner, baths and bedtime stories came early that night!

She told me to get the lotion as she stripped down and laid facedown on the bed. At first, I was shocked when I saw the welts that striped her ass from the cane but it was obvious that she wasn't upset at all. She seemed proud of them. I also couldn't deny that I was rock hard after seeing her red ass and the dried semen on her upper thighs and on her butt. I was standing at the foot of the bed and she was stretched out facedown in front of me with her legs partly open. As I peered at the beautiful sight in front of me, it seemed that her pussy was still a bit stretched from his large cock and when I massaged her beautifully round and firm ass I noticed that it appeared her pussy may not have been the only thing stretched today. She seemed to almost purr as I ran my fingers lightly over the welts.

"I can tell," I said shyly as I slid my lotion-covered thumb very gently back and forth across her plundered orifice. "Did it hurt?" I asked with genuine concern and curiosity.

"Of course it did at first but then it just felt very full and ... wonderful eventually," she replied softly. "Why? Are you thinking you'd like to try that one day?" she inquired while turning slightly toward me.

I shook my head "No" and she laughed as she put her face back on the bed and enjoyed the gentle massage I was giving her backside. Then, I asked her, "What did he do to cause these welts on your butt?"

"He caned me," she answered matter-of-factly.

"That must have really hurt," I answered. Then, I rubbed my fingers gently over each welt to soothe the ache I imagined must be coming from them. "Do you think he'll do it again?"

She giggled and said, "I've always wanted to try it and it definitely lived up to it's scary reputation but I do hope he'll try it again sometime. It was really intense. I think he might have really been mad at me but once he realized I did it on purpose so he would do exactly what he was doing to me, then he gave me the best makeup sex ever." She wiggled her butt to emphasize how much she had enjoyed the sex with him.

I was getting hornier by the minute as my brain was swirling with thoughts of what she had done that day and what we were still going to be doing tonight. She must have sensed my growing excitement and said, "Let's get this over with. I'm exhausted and need to get some sle ep." She indicated that the butt plug and lube was in the bedside drawer on her side of the bed and I retrieved them with shaky hands. I couldn't believe that I was going to put this in her ass.

I squirted lube onto her puckered little rosebud and squirted more onto the firm, jelly-like plug. She lay face down and raised her hips to give me easy access to her most private area. I imagined this was exactly how she looked when Trevor did this to her and wondered if that is what she was fantasizing about as I did it. Although it seemed to be a rather large plug to me, it went into her asshole much easier than I expected and she only made a brief "Ohhh!" as the widest part of the plug popped past her sphincter muscle. I assumed that his earlier invasion of all her holes had loosened her up and made this much easier. I could only imagine the noise she made when he had taken her in the office.

Once plugged, she rolled onto her side and patted the bed next to her to indicate that I should lay down and get the reward that I was due next. I swallowed hard as I lay down on my back and my erection pointed up at the ceiling like a ch ild raising his hand in class saying, "Call on me! Call on me!" She slid her hand down and cupped my balls and massaged them gently while nuzzling my ear with her hot lips.

"How long has it been Danny boy? I can't even remember the last time your little wee-wee was in my mouth. Are you excited?" She was teasing me and I was loving every minute of it. She moved her hand off of my balls and started playing with my nipple instead. She slid down and sucked the other nipple and bit it lightly as she twisted the other one between her fingers.

For some reason, a question popped in my head and before I could stop myself I asked, "Why did Trevor tell you to give me a blowjob?"

She stopped biting my nipple long enough to say, "I guess he was feeling sorry for you."
"Why? Because I'm a cuckold?"

She laughed and said, "No. That doesn't bother him a bit. He knows cuckolding probably saved our marriage and that we both love our relationship like this." She kissed my nipple and chest again as she started to scoot lower down my body.

"Then, why was he feeling sorry? Because I couldn't give you oral sex this week while he's away and you aren't allowed orgasms?" I asked between gasps as she rubbed my penis and got closer with her lips.

"No, I think it was when I asked him when he was finally going to cut you off and no longer allow you to put your little thing in me, anywhere, anymore." She smiled with a sexy, taunting look as she let this revelation sink in. "He told me he didn't think I let you do that anyway and I told him that I felt sorry for you sometime and would probably let you unless I wasn't allowed to because he owned those things." She stroked my shaft while looking at my face. "He laughed and told me to give you a blowjob tonight but he did tell me that my birthday was coming up so we'll see."

Then, she moved her head and lips toward my throbbing erection and I only hoped that I wouldn't blow before she got her lips all the way around the head.
randyadrian

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Very nice! Thanks!
BumNote

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#8
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Better with every line! I love the three different perspectives and the story developments 🥰
herboy63

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#9
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BumNote and randyadrian I am glad you liked it! We'll see what inspires my next story. We're getting older and don't live the lifestyle anymore so I usually weave in some tidbits from back in the day and combine it with something that happens more recently and get a new storyline from it. Until next time!
macca121

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#10
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Excellent work. Thank you. M
randyadrian

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Posts: 1981
#11 
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Really good writing!
Rating: 6, 2 votes.
Cuckold Stories CuckoldPlace.com / Cuckold Stories /
Sam, Her Boss and Her Cuckold
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