Chapter 22 Business Turns to Pleasure

My position at work was such that I didn’t really interact much with clients. I ran the back operations, while more public-facing “engineers” (usually under the project managers) handled the clients. But, from time-to-time, I had to meet clients when a technical issue needed to be explained. It was in a situation like this that I met Jake and Ashley Samuelson, a rich philanthropist couple building a new music hall.

She was absolutely stunning, in just the way that my ex-Wife was. We met for lunch at a fancy restaurant to discuss acoustic issues my engineers had run into with the architectural plan for the project. As soon as I sat down, they seemed titillated and captivated by me. As I explained the issues, they both seemed to hang on my every word. He was a bit older, maybe in his fifties. A thin prim and very stylish, maybe even foppish man. He wore a tight gray pin-striped suit, with large silk colorful, mostly purple, ascot.

I don’t know what it was about him, but something told me that he would be a good Cuckold candidate. Her manner and tone suggested that she was in control, and he was submissive to her. It was certainly not my job to recruit; and it seemed hare-brained for me to look at a woman like Mrs. Samuelson and think she would make a great slut for my fiancé, but that was my first inclination.

I tried to lay on the charm as much as I could. I brought up my fiancé, and spoke intimately with Ashley about him. I asked casually how they’d met, how long they were together. He would join in from time to time, but seemed to content to just stare at me with a bemused look on his face.

I finished explaining the engineering problem and the upshot was there would have to be a redesign of the backstage area of their new project. I reassured them that it would not add to their building costs and that I had already discussed it with the architects. There would be a brief delay while the architects worked out the redesign, but I soothed their rich egos and made them feel smart with their suggested solutions.

Then–I was way more forward than my old male self could have been; I asked them to dinner at our place the following Friday. They couldn’t have accepted more quickly. They would be delighted to come and to meet my fiancé. As soon as I got out of the lunch, I texted Daddy to call me as soon as he could. He called me when I had gotten back to the office.

“Hi Daddy, how is your day going?”

“Hi Sissy, what’s going on?”

“Well, I just had a very interesting lunch with a client. And, I think you are going to like this. Are you by a computer?”

“Yes, what is it?”

“Google Ashley Samuelson.”

“Ok?”

“She is my client. What do you think? Isn’t she Hot?”

“Yes, sissy, she is very Hot.”

“I think her husband is a potential cuck. I invited them for dinner the next week. What do you think?”

“Interesting! We’ll have to talk later; I have a patient. We’ll talk at home.” He sounded distant and distracted. I chocked it up to being busy.

When I got home, he had done more research than I had. He was even more sure than I was of my premise. He had looked up their net worth; the causes they supported and bios of both. He was heir to a lesser railroad fortune. This was his second marriage, his first Wife divorced him for an indiscretion that was never really explained but there were whispers it may have had to do with another man rather than a woman.

This second Wife was not a trophy, though she might look like it. She had been running most of Jake’s companies and foundations as the CFO of the organization before they were married three years before. He was nominally the CEO, but everyone knew she had all the real power.

Daddy had already secured Vera to make the dinner and plan the menu. He was beaming at me as soon as I came in the door. “Michelle, I am really proud of you for taking the initiative on this and for being so straightforward about it. I know it’s not every fiancée that finds new sluts for her future husband.”

“Thank you, Daddy. It’s the least I can do after… you know who. I can’t be jealous and keep you under lock and key even as my master.”

“That’s very good, sissy. You know, I have lived my whole life just on the very edge of New York high society. They’re all a bunch of hypocrites, but this would be a really big coup for our little network. I am going to give you a big treat for this, Sissy.”

He seemed very happy about this whole thing, but with him, I had learned to take “big treat” with large scoops of salt. These days it could be a real treat… or some scheme he hatched to humiliate me further. “Yes, Daddy, what is it?”

“Well, it’s been weeks since we watched an episode of our favorite reality TV show, The X-Wife Files.”

“See?! I knew I would be sorry.”

“Let’s order in and get comfy in the media room.”

“Sure, you feel like Thai?”

After ordering the food, I showered–cleaning inside too–and got comfortable and came into the media room with just a silk robe and some boy-shorts. I knew he would want ready access to me as we watched my ex-Wife confess to some heinous acts against me. I took these episodes in stride now, I thought. When I came in the room he was working on his tablet. Dinner had come and he had set it up on TV trays. He looked at me with a look of genuine Love and affection. I smiled at him.

“You look lovely, Sissy; you’re so fucking sexy.” He kissed me tenderly and romantically, then said, “Come let’s eat.”

“Yes? thank you, Daddy.” We ate quietly with some small talk. I explained the acoustical problem Ashley and Jake had to meet with me about. He talked about rehabbing a professional ball player. It was like we were already an old married couple.

When we finished dinner, he was ready to pounce with the video. I knew he must have some plan afoot, but had to just wait for it to happen. He fiddled some more with the tablet and turned the TV monitor on.

“Remember the phone call you got from the ‘fertility clinic.'” He made scare quotes with his fingers. “It turned out to be a co-worker. Ever wonder who or why they did it?”

Sure, I had. I knew most of the people she worked with at least casually. They were mostly guys, so I supposed it could have been any of them. I imagined the why was: she was fucking them.

Her entire office was about a dozen people. Three of them were women: two junior engineers and the administrative assistant. There were eight suspects, including her boss who was probably not the culprit. He was diminutive wimpy guy, she would (I realize now) never go for. I was pretty sure that two of those guys were gay, which was, I guess, not completely dispositive. I thought of the larger guys in the office.

There was Marcel, who was very large, but a really sloppy guy–kind blubbery–which wasn’t quite her style, and George, who was my prime suspect. He was big handsome square-jawed black man. The only thing is that he was the one guy with whom I had the most interaction, and I thought I would have recognized his voice on the phone. That left Terrence, who was not very large, but maybe he was bigger down below. Anyway, I was about to find out…

In a moment, her face came into focus on the screen; there she was again ready to humiliate me like an unfaithful haunting specter plaguing me from beyond. She was wearing a blouse I recognized. It was a thin frilly see-thru lacey thing, which she would normally wear with a camisole, but was wearing it braless, her big tits almost bursting out of the delicate material. Her big tasty nipples poked through the lacey fabric.

“So, you’ve done some rather deceitful and nasty things to your poor Cuckold husband.” Daddy’s disembodied voice was asking.

“Wow! I suppose he is a Cuckold; I had never thought about it quite that way. Yes, I have done some terrible things to him. I am sometimes ashamed of those things, but he kind of deserves it though; he’s such a dupe. It’s almost like he calls out to be tricked and humiliated. He doesn’t even notice is the thing.”

“So, what do you think is the most deceitful and hurtful thing you have ever done to him?”

“You mean besides fuck his best friend for years and try to get pregnant by him? Yeah, it’s probably part of that. I only ever wanted to have Joe’s baby. But when that turned out to be impossible, I had to make sure I didn’t get inadvertently get pregnant by Mitchell. I’m sorry I just didn’t want to have his tiny-dicked baby.”

This was painful confirmation of what I had thought the last time this subject came up. She had always only planned to get pregnant by Joe. It wasn’t an afterthought; this really hurt, again. Although I was already fairly sure this was true, having her corroborate it hurt even more.

She went on, “as soon as I knew it couldn’t be Joe, I got right back on the pill. But I couldn’t just drop it just like that with Mitchell, after I had made such a big deal about trying to get pregnant. So, I had to make it his fault. I made an ‘appointment with a fertility clinic,’ and when I got home, I handed him an official looking jar for his sperm sample and told him that they needed to see if it was him because it didn’t seem to be me.

“I waited a few days and had this guy at work call him from the ‘clinic’ to tell him he had such a low sperm count there was no point in trying.”

“Who did you get to do it?”

“That’s a funny story; I was planning have this guy George to do it. I had fucked him a few times in the supply closet, so I was sure he would do it. But I thought he wouldn’t be convincing enough. So, I asked this other guy Terrence, but he wouldn’t do it. I wanted to do it early in the morning when Mitchell was on his way to work so that he would be alone unfocused and didn’t have too long to think about it before facing his workers.

“I went in extra early that morning, wondering who I could get to do it. When I got to work, the office cleaner was emptying my trash bin. He was a Pakistani man, who, it turns out, had trained to be a doctor there, but had never practiced and was still working on getting his American medical license. He had just told me that story some weeks before, while staring down at my tits.

“His name was Ayaan Baqri; I knew he could pull it off. His English was perfect, but with an appropriate foreign accent. I had to convince him to do it, but had little time. I knew Mitchell would be at work soon and it would be too late for my plan. I didn’t want him to get the call with anyone nearby, who might ask questions. I explained to Aayan what he had to do. I opened my blouse and showed him my tits, while sinking to my knees in front of him. He nodded his head and agreed to it immediately. I gave him Mitchell’s cell number and he dialed it from his cell.

“As he was introducing himself to Mitchell as my fertility doctor, I was undoing his pants and pulling out his sizeable cock. It wasn’t big like yours or even Joe’s, but it was nice nonetheless. It gave me a special thrill to be sucking this man’s cock–practically a stranger–as he gave my husband the terrible “news” that his tiny useless penis was never going to produce children.

“I had his cock all the way down my throat and my hand furiously rubbing my cunt. I almost came, when I heard him tell Mitchell with finality, in his posh Indo-British accent, that there was no point because his sperm count was sooo low he would never sire children.”

This really hurt me again, and finding out who, was not really at all rewarding. I wondered where this would go tonight and was a bit frightened. There was always a point to the choice of topic on The X-Wife Files show, and I couldn’t figure it out, and that scared me.

“It was 8:30 in the morning, my office is really laid back for engineers, people would start to float in at 9, but the whole office wouldn’t fill up until a half hour after that. When Aayan was finished destroying poor Mitchell’s future paternity plans. I settled into sucking his cock in seriously. I was happy with his performance and so Horny from what we had done, I wondered if I could fuck him before anyone got there.

‘You want to fuck my Pussy, Aayan? You want to cum inside me?’

‘Yes, please, Miss! I would Love that.’ He said in his posh accent.

“I got up and locked the door; took off my panties. Leading Aayan by his cock behind me, I folded myself onto my desk. ‘You’ll have to fuck me fast and hard; we don’t have much time.’

“He lifted my skirt and started fucking me just like I said, hard and fast. I couldn’t believe how wet I was, he slid in so easily. There was something about what I had done to Mitchell that was turning me on, just the way it turned me on to feed him other guys’ cum from my Pussy. I was coming pretty soon after he started fucking, and he just fucked me straight through. I heard myself moaning pretty loudly, when the door, I was sure I had locked, swung open.

“I looked behind me and it was George and Terrence coming through the door. They had both come in on time for once and heard what was happening, got the master key from the boss’s (Dan) office and broke in on me in flagrante delicto. I was so busted. I didn’t know how I would get out of it. Aayan’s dick shriveled up inside me and he stepped away gingerly.

“George was the first to speak. ‘Look, Lori. I don’t care what you do, but if you want to keep this quiet, you are going to repay us in kind. What do you say Terrence? Don’t worry, Aayan, you could finish later. We’ll come to an understanding, yes?’

‘What is it you want, George?’ I was pretty much fucked either way (literally); but I wasn’t that worried. All he would want would be to fuck me, which I was already doing, and would have fucked Terrence to get him to help with the low sperm count project, so no biggie.

“I pulled down my skirt and Aayan pulled up his pants, and we talked about how I was going to keep them quiet. I suggested we could just have “lunch” at our apartment. Mitchell wouldn’t be home until after five. George didn’t like that–there wouldn’t be enough time for what he had in mind. They wanted to have a more protracted time with me to make the blackmailing worthwhile, maybe a long weekend.

“It was Terrence who came up with the plan. He suggested that Mitchell would be devastated by the news he had just gotten and might want a distraction. Terrence already had plans to go on a ski strip with one of his pals (who would have to be included). Convince Mitchell to go on the trip as way to forget the bad news, and sneak out to spend time with the whole troupe.

“The whole thing made sense and we all agreed to put the plan in effect. I knew that Mitchell was into skiing and was always dissing on Texas for the lack of it. It would be pretty easy to convince him after the terrible ‘news.’ He would be happy to be getting away and doing something he enjoyed.

“I was so excited about the prospect of the trip and a bit frustrated from being stopped mid-fuck, that I was Horny the whole rest of the morning. By the afternoon, when Mitchell called to share the ‘bad news,’ I was in the employee bathroom with George’s fat black cock grinding into my Pussy.

“I looked at my phone. When I saw his name, I was going to let it go to voicemail, but then I thought how delicious it would be to hear his blubbering about the terrible news, while George buried his fat cock in the Pussy that was not going to produce children for him.

“‘Hi, honey, it’s Mitch, sniff, sniff.’ Just then George slammed into me making me grunt.

“‘Ooph, Urhgh, hey hon… umph… wassup? I’m kinda of busy.’ I reached back with my Free hand tried to hold George still inside of me, but he started gyrating, and I could feel his cock squirming inside me, driving me crazy.

“‘I had some terrible news today, hon, are you sitting down?’

‘Yeah, on a big fat cock, you fuckin’ loser,’ I thought.

“But I said, ‘oh no! what is it honey?’ He told me his sad news, and I did feel a pang of guilt, as he cried pathetically and apologized to me repeatedly for his inadequacy. But George had other ideas; he started fucking me harder, and I fell into rhythm with him instead of stopping him. I couldn’t help it, but a moan escaped my mouth, and then I tried to turn it into sobbing.

“Sniveling and pretend sobbing, I was actually coming, when I said, ‘Sniff, I’m… erhm… so… ooof… sorry, honey, but I can’t talk right now; it’ll be alright, don’t worry. We’ll talk about it at home.’ I hung up before I gave the game away by moaning through the end of my Orgasm. As George got close, I was already plotting that evening’s entertainment.

“‘Come deep inside my, George, I am going to feed it to my husband.’ He came what felt like quarts of cum inside me. I cleaned off his cock with my mouth and he left. I then shoved a tampon in to preserve my hubby’s treat.

“I got home before Mitchell, as was customary, I showered and put on some nice lingerie for him. As soon as I heard him opening door, I pulled out the tampon and laid on our bed. ‘I’m in here, honey,’ I shouted when he made his way in. I posed for him on the bed with my knees together to keep the cum inside. I knew he could not resist especially after the terrible news.

“‘Come here, baby, let me make it all better,’ I cooed. He looked forlorn and depressed. He came over and leaned down and kissed me. I kissed him back hard and deep. He is actually a really good kisser that’s one of his best traits. ‘C’mon honey, I want you so bad. What do they know? We can still try anyway.’

“He couldn’t have moved faster. He ripped off his clothes and jumped on top of me. He was about to go down on me, so I stopped him instead and rubbed his little dickie, while I kissed him. ‘I want you inside me right away.’ I whispered in his ear, and I could feel his tiny prick stiffen. I could feel the cum slithering out of my cunt as he went in, so I said, ‘Oh, I’m so wet for you honey, fuck me.’ I knew this would drive him wild, I never cursed around him. I had always kept up the appearance of being an innocent Jesus girl.

“Maybe it was how slippery I was from the cum or the terrible news, but it actually took him like ten minutes of–what for him must have felt like–hard fucking to come. He was so hard that I actually felt him inside me maybe for the first time.

“As soon as he was done, I pushed his head down to my Pussy to collect his reward. He lapped at my Pussy with abandon and I was coming almost right away. The idea of him licking up George’s huge load and thinking it was his was just too much.

“I treated him as sweetly and delicately as I could that whole evening. I even let him stick his teeny peenie back inside when he had recovered and let him eat his tiny milky come, with I’m sure some of George’s seed still seeping out of me.

“Later that night I brought up the idea of the ski trip to take his mind off the terrible news. Two weeks later we were in Vermont. We were staying at fancy ‘ski chalet’ really just a cabin on the grounds of a larger ski resort. The boys had two rooms in the main hotel a five-minute walk from the cabin, which was fairly isolated and private.

“Even though I was being supposedly blackmailed, I was really looking forward to meeting the guys, plus there was the mystery guest, I didn’t even know. Mitchell and I checked in about 3 pm, but between dealing with ski gear and unpacking we weren’t all settled in the cabin until about four thirty. I took a quick Shower and got ready for the evening.

“The boys and I had decided that it would be less suspicious to ‘run into’ each other early rather than it happening inadvertently. Mitchell didn’t know Aayan and Terrence’s friend, so we left them out. When I was ready, I suggested to Mitchell that we should go down to the hotel bar and have a drink before dinner, and by 6, we are at the hotel bar drinks in hand.