It was past 10.00 am when I dragged my carcass out of bed. I stared at the bottle of Macallan sitting on the hotel dresser, and the events of last night crystallized in my mind. Holy shit, I thought, I have a business meeting and supper with the husband of the women I fucked last night in that bar. This could louse up all the effort I put in getting this deal for the last six months.
I showered, shaved and went down for breakfast. My meeting was set for 1 pm, and I spent two hours reviewing my notes and presentation. With much trepidation, I arrived at Vanguard's offices to meet with Bill, husband to the woman I had come to think of as Dizzy Izzy.
I stepped out of the elevator into an atrium, which was a veritable jungle of tropical plants. The receptionist looked up, and I gave her my name and that I was here to see Mr. Jessup.
She murmured my name into her headset and told me he would be with me shortly and to take a seat.
I settled into an armchair where I was partly hidden by a giant philodendron and waited. I realized that my palms were sweaty, and I had the jitters. After what seemed to me to be an eternity, Bill stepped out of his office and walked towards me. He stuck out his hand, which I grasped as I stood up.
"Roger, it's nice to meet you at last," he said.
"Likewise, Bill," I stuttered inelegantly.
"Come into my office. I've studied your proposal, and I have some questions which I would like to clear up."
He led the way into his office, sat behind his desk, and motioned me to an armchair across the desk.
"Roger, this is not your first time in NY?"
"No, Bill, I'm in the city at least once a month."
"Did you fly in this morning?"
"No, I came in yesterday."
During this exchange, he had been looking at me quizzically. Shit, I thought, the shoe is about to drop.
"Guess you enjoyed the deluge last night. That was something else. My wife and I had to take refuge in a bar in the Village to escape the downpour. Speaking of the Village, do you ever go to the Village in Montreal?"
"Uhh… Not really."
"I go when I'm up there. I like the atmosphere."
It hit me like a ton of bricks, Why, that son of a bitch is gay or bisexual. What the hell is he doing with a woman like Izzy? Montreal's Village is the gay area of town.
As if he was reading my mind, he glanced at Izzy's picture in a frame on the credenza behind him. He said, "My wife, Izzy is looking forward to hosting you at our home tonight for supper."
"That should be delightful," I responded. I wonder if you will be as delighted that I've already fucked her.
The conversation then moved on to business matters for the next four hours. During the whole time in the back of my mind was the thought of how I could beg out of the dinner invitation without jeopardizing the deal we were ironing out.
All the transaction details were finally ironed out, and we got up and shook hands on the deal. "We'll let the legal beagles iron out the details. Now let's get out of here. I need a stiff drink. Izzy should be expecting us soon."
We grabbed a cab and headed downtown. The drive was pure agony for me. I had visions of all that I had accomplished over the past year going down the drain if Bill discovered what had happened last night and withdrew his financing offer. I was sweating bullets.
I remembered his offer from last night when he told me to call his wife whenever I was in town; however, I was no longer an anonymous stranger. How would he react if he found out?
The cab finally arrived at our destination, an elegant art deco building. We got out and went through a pair of magnificent brass doors into a gleaming marble lobby.
Bill stopped in front of the elevators and turned towards me. "Roger, I want to give you a word of warning before you meet Izzy. She is a wonderful person; however, she has some
idiosyncrasies which I hope will not shock you."
Idiosyncrasies! My god, she's a fucking sex maniac. Emphasis on the word 'fucking.'
"Bill, all women have idiosyncrasies. That's what makes them lovable. Mind you, men have their own idiosyncrasies."
"Yes, I guess we do," he said with a smirk.
We entered the elevator and proceeded to the penthouse floor. We stepped out of the elevator directly into the foyer of an elegant apartment.
Izzy came to greet us, and her jaw dropped when she saw me. She threw me a questioning look as if to ask whether Bill was aware of what had taken place last night. I gave a slight shake of my head to indicate that he didn't.
"Izzy, I'd like to introduce you to Roger, one of my new business associates. Roger, this is Izzy, my wife."
I put out my hand to shake Izzy's hand, but instead, she bypassed my hand and gave me a hug. It was Bill's turn to look at us wide-eyed and slack-jawed. "You two know each other?"
"Bill, you don't recall much about last night, do you?" Izzy asked.
"No, things are pretty foggy after we got to that bar."
"Do you remember that I went to the washroom with a guy we had just met at the bar?"
"Vaguely. I remember standing at the door of the washroom until he came out. I think I even gave him my business card with your cellphone number on the back and telling him to give you a call, but for the life of me, I have no recollection of what he looked like."
I pulled out the business card from my pocket and handed it to him.
"I'll be a son of a bitch. What are the odds of that happening?" he asked.
"Bill, I don't know what the odds are, and I hope that this does not jeopardize our agreement. I've been on pins and needles all day about this. I wanted to tell you earlier but did not want to spoil my chances to involve you and your company with my plans."
"Roger, all I can say is that you are considerate not to have brought it up. Don't worry about it as I never know with this ditzy blonde what I will discover after the fact. Well, you are now part of the family, so to speak. Let's go and have a well-deserved drink before supper, and I'll explain Izzy and my rather odd relationship."
He ushered me into an elegant living room, and I was shown to a plush leather sofa while Bill seated himself in an armchair across from me. A few moments later, a woman in a maid costume bearing a tray with an ice bucket and glasses entered the room. At the same time, Izzy came in with another tray bearing assorted appetizers.
Izzy placed the tray on a coffee table and came to sit next to me. Meanwhile, the maid asked what I would like to drink. "If you have Scotch, that would be great," I said.
"Do you prefer a blend or single malt, Sir?" she asked.
"A single malt if you have."
"Would Dalwhinnie Directors' Cut be acceptable, Sir?"
"I've never had it, but a friend recommended it to me, so I'd love to try it. No ice, please and water on the side."
The maid served the drinks, a Scotch for Bill and a white wine for Izzy and left. Izzy forked a smoked oyster from the appetizer plate and fed it to me while saying, "Here you go, you might need these later," with a giggle.
Bill interjected, "Izzy, behave while I bring Roger into the picture."
She pouted at him and cuddled up to me. I could feel her breast rubbing against me. She was obviously not wearing a bra. I felt my cock start to wake up at the contact and the thought of what might be in store for me tonight.
"Roger, as you may have guessed, Izzy and I have a very different relationship. Izzy has an insatiable appetite for sex. While I am bisexual with a distinct preference for men. I think that you twigged on that when I mentioned that I frequent the Gay Village in Montreal."
"Yes, Bill, that was something that hit me when you mentioned it back at the office. Just to clear the air, I am not bisexual at all."
"Well, life is rarely perfect, but you don't have to worry about me. Now in my position, I cannot allow people around me to even come close to guessing my penchant for men. That's where Izzy comes in. She and I met at a vernissage many years ago when she came on to me. She and I got together, and I found her witty and charming.
"We got together that night. In my particular way, I was able to satisfy her needs. I fell in love with her and wanted her in my life, so we came to an arrangement. I needed her as arm candy, and she needed me as a protector. Based on that, we got married.
"Now, I let Izzy entertain other men sexually. In most cases I approve only as long as I am present, while Izzy permits me my idiosyncrasies."
"You mean that if Izzy decides to bed me tonight, you would be present?"
"That would depend on what Izzy decides. She has an innate sense of self-protection. I would certainly enjoy it as I love to see her pleasured by a well-built male, but it is not an absolute requirement.
Let's go and have supper and see how things progress as I believe Izzy has plans in mind for you. We are eating on the patio."
I turned to look at Izzy, and she gave me a sweet smile and reached over and grabbed my cock through my pants. "Let's see what comes up, Roger," Izzy said with a wicked smile.
"I'll tell you what's just come up," I said with a groan as I developed to a full-fledged erection.
"Oh, that's marvelous, can I have it for dessert?"
"Izzy, behave, or I'll have Roger spank you."
"Roger, would you really spank me?"
"Izzy, right now, I'm just trying to figure how to get to the dinner table without tripping over my hardon."
We finally got to the patio. The view was magnificent. I could see the river gleaming in the distance while the city's lights formed a dazzling panorama to my left. Izzy seated me where I would get the best view on Bill's left while she sat across from me.
The maid came out and served us sizzling plates of Chateaubriand with Duchess potatoes and parsley'd butter, mushrooms and chateaubriand sauce. We were offered a red wine, which I declined. We dug in like trenchermen. I realized that I was starved, having not eaten since breakfast.
Bill and I discussed Montreal and the possibility of him and Izzy coming up during the Jazz Festival. I told him that I would be delighted to host the two of them for the duration of their trip. Izzy smiled at me and I felt her bare foot reach across the table and caress my leg. It rose inexorably higher till it was pressing against my cock. She smiled at me and asked if I was enjoying the meal.
"Izzy, this is delicious."
"Yes, but are you enjoying the added feature?"
Bill lifted the tablecloth and peered under it. "Izzy, you are incorrigible," he snickered.
"No peeking, Bill. If you are a good boy, you will see Roger's cock soon enough. Now I think it is time for Roger and me to have dessert. Alone! Once Roger is comfortable, I might invite you to join us."
With that, Izzy stood and took my hand and led the way to the bedroom.
"Izzy, I'm not sure I'm comfortable with this," I said.
"Why not? You had no qualms last night, knowing then full well that I was married. What's changed?"
"Well, Bill is now my business partner, for one. I also feel uncomfortable with having him here seeing me naked and fucking his wife, not to mention drooling over my cock."
"Roger, first, let me assure you that Bill will never get close to your cock without your explicit permission. You have to realize that Bill wants you to enjoy me. He derives extreme pleasure when other men enjoy my body. Bill is psychologically unable to fuck me. He does pleasure me in other ways, as if you give us a chance, you will see how."
She slowly and sensually removed the white dress she was wearing and stood there in all her glory. She was completely nude and posed proudly in front of me. Her body was breathtaking with her breasts proudly thrust forward, capped by two tempting pink and erect nipples begging to be sucked. Her totally bare mons with its succulent pussy lips already gleaming with moisture begged for attention.
Any misgivings I might have had vanished. Truly a stiff prick has no conscience.
She came to me, knelt at my feet and unbuckled my trousers while I removed my shirt and then proceeded to kick the shoes off my feet. She lowered my boxers and removed my socks. As my cock sprang out at full attention, her eyes gleamed.
"Roger, that cock is just magnificent. Last night I knew it was big. However, I did not realize just how big," she said, grasping it in her warm hand.
She brought her tongue to bear and licked it from the base to the tip, scooping up the precum that was already leaking from the tip. "Delicious," she uttered before lowering her mouth to engulf me right to the base.
Soon I could feel my cock throbbing in her mouth. She was moaning each time she swallowed me deep in her throat. Her hand gripped my cock at the base, and she started sucking the glans like a lollipop and stroking me till I shot string after string of cum into her mouth. She swallowed greedily and with apparent enjoyment until she had drained me of every drop.
She finally pulled away with a long string of cum still connecting my cock to her mouth. Smiling at me, she stood up and pulled me to the bed, where she had me sit at the edge. "Roger, I'm a bad girl. I need a spanking."
"A spanking?" I asked, astonished.
"Yes, a stern hand spanking to redden my lily-white ass."
With that, she draped her body face down across my lap. I stared down at her nicely rounded ass, thinking, What next? She indeed was the most exciting woman I had ever known. "Are you sure?" I asked.
"Yes. Warm it up for later."
I caressed those beautiful cheeks as she moaned with pleasure. I brought my hand back and swatted her across her cheek, amazed at how her resilient ass bounced back after being spanked.
"Harder," she pleaded.
I proceeded to give her a succession of stiff slaps across the rump when I realized that my lap was being drenched with juice. I spread her thighs and ran my fingers through her pussy. My fingers were soaked with her juices. I spread her ass cheeks and gazed at her pink crinkled starfish; it seemed to pout at me.
I ran a finger back and forth over her pucker, and she writhed on my lap like an eel, while moaning. I took my moistened finger and started to probe that tempting orifice, seemingly much to her delight. With my other hand, I curved my fingers into her pussy and using both hands, I frigged both her holes to the sound of her appreciative moans.
"Don't stop, Roger. Please don't stop, make me cum," she wailed.
I was soon rewarded by her copious flood of juices as the orgasm erupted in her. I flipped her on her back on the bed, spread her long legs and worked my way up her thigh with licks and kisses as she panted.
"Dessert time," I said as I inexorably rose towards her gleaming pussy.
Oh, goody," she smiled at me.
Her aroma was intoxicating. A mixture of her muskiness and the delicate perfume she was wearing assailed my senses.
As good as she smelled, she tasted even better. My tongue parted her pussy lips and delved into her warm muskiness. I lapped and licked the intoxicating nectar, which flowed profusely from her. She arched her back, and I was able to run my tongue down to her exposed pucker, making her shriek in delight.
Her clit caught my eye, and I brought my tongue up to lick around it while I inserted fingers into both her holes. When I started to suck on that delectable nub, her whole body arched as she yelled, "Oh, Roger, don't stop. I'm going to cum again."
Cum she did, explosively, and she squirted her orgasm all over my chin and face.
As she lay there panting, I made my way up her body, making a pause to nibble and suck on her nipples before taking her into my arms. She looked at me and giggled, "I've made your face a mess." Using her tongue, she cleaned every drop and smear of her emission off my face. We ended up in a deep and passionate kiss with our tongues wrestling enthusiastically.
She reached down and stroked my cock till it regained its proud length. "Roger, I want you to fuck me now. May I, however, have your permission to have Bill come in and watch? You would be doing him a huge favor if you did allow that. He will sit in the armchair and just watch."
I wrestled with my conscience for a few seconds before grudgingly agreeing. I figured that his willingness to share this beautiful creature with me was somewhat out of my orbit. It was still an incredibly generous act. He was certainly entitled to get his jollies; after all, who was I to judge?
He came into the room when Izzy called out to him, which indicated that he must have been nearby if not just outside the door. Izzy pointed to a chair, and he meekly sat in it and started to shed his clothes. I did not pay much attention as she pushed me on my back and straddled my thighs.
She immediately started sliding her pussy back and forth on my cock, lubricating it with her copious juices. Once she was satisfied that I had reached a satisfactory state of firmness, she rose up, grabbed me and descended on my shaft, burying it to the hilt in her hot clinging pussy. It was amazing how tight she felt. She either did daily Kegel exercises or was an exceptional woman; whichever it was, I was not complaining.
She rose up and down on my shaft, milking it from base to tip while I reached up and toyed with her tits and nipples. I could feel myself bottom out against her cervix each time. Her face was aglow with lust and pleasure as she rode me relentlessly. The ride kept getting more frenzied as she filled the air with her moans of pleasure.
Inevitably I felt my balls tighten. I pulled her forward and reached behind her and thrust a finger up her ass. The moment I penetrated her back hole, she let out an ungodly shriek, and I felt her tighten up even more. We came at the same time. Her discharge flooded my pelvis, and it felt as if I had expelled a gallon of cum into her.
I remained flat on my back, panting while Izzy motioned Bill to come over. She lay on her back, and Bill took a position between her thighs where he eagerly and with relish lapped up my cum oozing from her pussy. I stared in amazement at the sight as he licked her pussy while she had a series of minor orgasms.
When he finished, Izzy stood up and took my hand and led me to the bathroom. After adjusting the shower temperature, she stepped in and dragged me in after her. "Roger, would you like to fuck my ass?" she asked.
"Izzy, you have the prettiest of asses, and I certainly would be privileged if you wanted me to do so."
"As you may have noticed, I am multi-orgasmic. I can also come by being sodomized."
"Really?"
"Absolutely. I also told you that Bill was able to bring me to a climax in many ways. In fact, he can orgasm by being buggered. And no, I am not going to ask you to bugger him. I am going to do that while you do me. I noticed your look of disdain when he ate me up after you fucked me.
"Don't judge him. He is not you, and in his way, he is coping with his devils the best way he can. I've been with him for many years and still have not figured him out. However, he is good to me, and we love each other. I'd love to be with a man like you; unfortunately, I'm not."
"Izzy, I don't pretend to understand your relationship. I know you stir every ounce of horniness in me. I will be eternally grateful for the opportunity you both have given me. I will try to respect Bill and try not to fall in love with you," I said.
At those words, Izzy wrapped her arms around me and kissed me passionately.
"Roger, you have my permission to fall in love with me. It is something I would treasure and would reciprocate. I need love, Roger, I need it even more than I need to be fucked. Now enough talk and let's soap each other, and then you can enjoy my ass."
After showering and drying off, we returned to the bedroom. Bill was lying there waiting for us. Izzy rummaged in her nightstand and brought out a big black strap-on that she attached to her pelvis. I noticed that part of it entered her pussy.
"Okay, Bill, get in position," she said as she liberally lubed the dildo.
Bill smiled and got on all fours as Izzy positioned herself behind him. She spread his ass cheeks and applied some lube to his asshole before bringing the dildo's tip to bear on his anus. She gently thrust forward, and I saw the thick dildo slide into him. She leaned forward and spread her thighs, motioning me to get behind her.
Her position was perfect, and I eagerly got into position. I reached under her to find her pussy was already leaking juices. I coated my fingers and used them to prepare her ass for my cock. I gently pushed my cock towards her pucker, and she groaned as the tip penetrated her. I stopped to allow her to adjust, but she would have none of that and thrust her hips back. I slid past all obstacles until I was firmly up her backside. If I had thought her pussy was tight, her ass was even tighter.
I realized that the dildo in her pussy was compounding the tightness as I could feel it rub against my cock through the thin membranes with each thrust I took. Every time I thrust forward, it caused her to thrust even harder into Bill.
Our combined sounds of enjoyment again filled the room. Her ass was warm and welcoming, and I could feel her milking my member. It was an exquisite feeling, and I soon forgot the ludicrous position we were in. After having cum as often as I had tonight, I was in for the long haul. Eventually, my balls tightened, and I could feel myself beginning to pulse in her depths.
When my climax came, I almost passed out from the sensation as I filled her with my cum. It was oozing out of her and around my cock and balls. I slowly withdrew and collapsed on my side. I saw that Izzy, besides buggering her husband, had reached around him and was milking his cock with her hand.
He was literally leaking cum like a faucet as Izzy, in turn, climaxed again. She finally withdrew, and the three of us lay exhausted on the bed.
Bill turned to me and said, "Thank you, friend Roger. That was quite a ride."
We eventually got up, and Izzy and I showered again while I think Bill showered in another bathroom.
Izzy handed me a bathrobe, and we went to the living room. Bill had prepared some drinks for us, and we sat around, me with a glazed look on my face.
Izzy cuddled up to me with a satisfied look on her face. "Roger," she said," you're going to spend the night with us. I will not take no for an answer."
After what had taken place, I would have been a cad to refuse. We ended up in bed with Izzy lying between Bill and me.
I woke up to an empty bed, and the smell of coffee lured me to the kitchen. Izzy, wearing a thin translucent negligee, came to me and kissed me. "Roger, were you serious about the invitation to receive us in Montreal?"
"Absolutely."
"Great," said Bill. "I will look forward to that, and it will allow me to go to the gay Village knowing you will look after Izzy. Now get dressed, and I’ll drive you to the airport."