My legs ached from the wishbone he had created, pushing them apart with his knees as though to see which side broke off from the body.
He pulled out of me with a grunt. His cum was leaking out of my pussy while the last few drops of it dripped slowly from the head of his cock onto my belly. We both stared at the tip, with its cream pooling and dripping; our minds were a million miles away or maybe just a few feet away. At one time, I would be licking those last drops with my educated tongue, washing the shiny residue from his rock solid shaft. Not lately, though.
"You bastard, I didn't cum; give me my fucking vibrator."
"I'm tired; go get it yourself."
"Eat me then, damn it."
He ignored me.
And they call this 'making love'?
My husband is a good man, a good husband, a good father. He supports me and the children, he does charitable work, he doesn't deduct a penny more than he actually contributes, I'm sure, totally sure that he doesn't cheat on me. They say that the wife is the last one to know, but believe me, I would know. I love him dearly; he's not fucking anyone else.
It's just that in the bedroom he is totally thoughtless and useless. That's why I fuck around at work, almost every day. I work as a stock research analyst for a medium size investment firm. I make an excellent salary which I dutifully bring home to Stephen and which is faithfully reported to Uncle Sam every April 15th. What my limp-dick husband doesn't know is that I make an equal amount, in cash, off the books, putting out on the job. I never cheated on him until recently, and it's all his fault.
I fuck for Michael, the big boss, as well as for three of the married Vice Presidents, Paul, Nate and Sid. In addition, the firm makes my snatch available, on a strictly confidential basis, to any client who brings in at least five million dollars for the firm to manage, and there are a number of these. Not all of them want to fuck me, but enough do to make it worthwhile for the firm to pay me the money. I phrase that incorrectly; they would all love to fuck me, of that I have no doubt, but many of them just don't have the nerve.
Stephen and I met in college, and it didn't take long for us to find out that in bed we were totally 'simpatico'. Whoever taught him how to fuck-I mean how to make love-had done a great job. He never came without making sure that I did so first, or together; we fucked morning, noon and night. He delighted in eating my pussy, cleaning up his sperm when he shot it into me, and I loved to swallow his cum when he delivered it into my mouth. We could have made porn films together, except that we didn't do wet shots for a camera; when Stephen shot his cum, it was always inside me, never on the outside to assure viewers that he actually had an orgasm. I even took Stephen up the ass once in a while, although when he wanted that, he had to give me a little advance notice, so that I could get a little drunk first.
We've been married about thirteen years; the girls are eight and ten, little angels. Stephen started a wholesale grocery business right after college and has done quite well for us. The problem started about two years ago, when his biggest customer teetered on the brink of bankruptcy. If he had gone under, he would have taken us with him; we would have lost everything, cars, house, boat, stocks, and country club membership. My salary would not have helped much. It was touch and go for too long, and during that period Stephen couldn't get it up too often; when he could, he had to cum quickly before he lost his erection.
I understood, and quietly purchased a vibrator so that Stephen wouldn't feel the pressure to make me cum. But until the financial crisis finally passed, my husband had changed in the bedroom. He no longer worried about getting me off and he soon stopped trying. If he hadn't remained such a good person otherwise, I would have just taken off.
One morning, about six months into the crisis, Stephen straddled my head and just shoved his cock into my mouth. Normally I love it, licking it up and down and playing with his nuts, waiting for what felt like a gallon of cum to shoot into my mouth, proud of the fact that I never lost a drop. But I was getting pissed off at his new sexual lack of caring, so I just lay there and let him fuck my mouth. I swallowed it all, still not losing a drop, but it was no fun. And worst of all, I had no time to use the vibrator before I had to leave for work.
At eleven thirty, I sat in my office, staring at financial statements on my computer screen but thinking about my suddenly lousy sex life, when I heard a voice.
Stephen? What the heck was he doing in my office at this hour? I focused on the numbers on the screen and said, "Fuck off, I'm busy."
My head snapped up. It was Michael, my boss, not Stephen. I turned beet red, said "I'm sorry, I thought you were someone else," and then I began to cry.
He closed my office door and said, "What's the matter?" I just shook my head and continued to cry. He stared at me for a while, then said, "Wash your face and we'll go have lunch." I nodded, still crying, as he left my office, closing the door again.
Once I was ready, face re-powdered but eyes still red, we went to L'Auberge, the fancy place we took all the good clients. We sat at the company table and Michael just waited for me to speak. "Stephen's best customer is way behind in payments, and if he goes under, we go with him."
"Do you need some money?"
I looked at Michael with new eyes. Working for the firm for three years, I already knew how good looking he was, early forties, nice wife, two nice kids. Yet I had only known his as a tough businessman, had never seen the kindness in his face except when he was talking to a rich client. I shook my head slowly. "Not yet, hopefully never. We're optimistic that he'll make it."
"Do you need anything?
My mind flashed back to early morning, Stephen fucking my face without love, without even lust, just fucking. I began to giggle silently, but Michael could see my body shaking with the internal laughter. My thoughts had been drifting this way for weeks; I closed my eyes, then opened them again, hesitating.
"I can't remember my last orgasm."
A good negotiator knows never to show surprise, but Michael blinked twice, then resumed his straight face.
"Can whatever you're working on wait a couple of hours?"
"Let's go up to the company apartment."
I nodded again. The firm maintains an apartment near the office, for use in transit strikes, blizzards and for the occasional out of town client when the good hotels are filled. Michael held my arm as we walked, sort of like a policeman walking a perp, but not so hard. With each step, my resolve grew, Go fuck yourself, Stephen, it's my turn today. My pussy began to leak as I smelled Michael's aftershave.
Inside the apartment door, we turned to face each other. He held me by the shoulders but didn't bend to kiss me. I couldn't tell if that was because he was afraid to make the first move or because he thought of me as a whore, and guys don't kiss whores. I reached an arm around his neck to pull his face to mine; our lips met, tongues touching slightly but not invading. I broke the kiss and removed my jacket, tossing it on to a chair.
"Would you like some wine, Jamie?"
I had never cheated on Stephen before, but I wanted to keep a clear head. "No thanks."
"Good." He was smiling as his hands reached up to unbutton my blouse. I moved in close to resume the kiss, my hands starting to fumble with his belt. This big strong brute picked me up, one hand under my back, the other under my ass, and carried me into the bedroom, laying me on the still-made bed, the kiss unbroken.
I wanted to tell him how much I still love Stephen, my husband, that being in bed with Michael was just a diversion to obtain the screaming orgasms that I need, that Stephen is not giving me and has not since the financial problems began, that a vibrator will not satisfactorily substitute for, that nothing can replace the exquisite feeling of a pulsing cock stretching my vaginal walls, of fingers or tongue working my clit.
But Michael had his own agenda, and he wasn't interested in my psyche at the moment. And he was after all my boss, the majority owner of the company. Where was this going? Would I be fired, or would I instead become enslaved to him as his personal slut, dependant on his pleasure for my paycheck? With the business teetering, Stephen and I needed that check badly.
As I lay there, Michael continued to unbutton my blouse, his eyes drilling deeply into mine.
"How long has it been?"
"Your last orgasm."
"Not since the financial problems started. Stephen has a lot of trouble now getting an erection, and when he does, he doesn't have the staying power to get me off. He just cums as fast as he can; he's afraid to lose his hard-on."
Michael nodded, but I don't think he really cared. He lifted my back to ease off my blouse, then opened my skirt and lifted my ass to get that off me. Still fully dressed himself, except for his open belt, he ogled me in bra and panties, yet he made me feel that it was not an ogle of lechery but a drinking in of beauty, of even more beauty than I myself possessed. He was seducing me with his eyes and my panties were damp as a result. My bra closed in front, and he unsnapped it, the cups falling to the side to reveal full breasts and hard nipples.
He stood to undress himself, winding up with nothing on except his bulging jockey shorts, the lump in front announcing that he was glad to see me. Was he bigger, fatter than Stephen? I wanted to know, so my hand reached to caress him.
"You've never cheated on Stephen before, have you?"
The bastard knew, but I hated to give him the satisfaction. Still, I nodded. I didn't know why I felt such anger at the man who, clearly, I had invited to fuck me.
"I'll try not to make you sorry." What a con man!
I released his hidden cock and removed my own panties; moist pink labia awaited him, surrounded by true blonde hair. He dropped his short to reveal his love muscle; it was really no different than my husband's. As it approached me, I closed my eyes.
Since the day I first interviewed her, I have wanted to fuck this delicious piece of ass. The trouble is, someone once reminded me that you don't shit where you eat. I've never had any trouble getting laid, even with a wedding ring on my hand, but it's always a struggle to make money, so I decided to leave this one alone.
It wasn't that she was drop dead gorgeous, which she was, but that she exuded such a virginal sexuality, which may sound like an oxymoron but it fits. I've always been a tit man, and when her tits led the way through the door for the interview, my cock jumped. They weren't watermelons, but, probably 34B or 34C; they were perfect for her body.
It was an important job, requiring a series of interviews. Since it would require some travel, we insisted on also meeting her husband, to be sure that he was comfortable with the irregular schedule that trips to corporations she would be analyzing would cause. Stephen's a heck of a nice guy, obviously devoted to Jamie, busy enough with his own successful business to survive a few temporary absences. As I sat across the desk from him, I wondered if he could read my mind, if he knew that I wanted to fuck his wife.
He was astute enough and she was good looking enough that he probably knew that every man she met wanted to fuck her.
That was obvious after one of the final interviews, with me and my three vice presidents, who are actually minority partners. They were all cool, no ogling or drooling, but once she left, it sounded like a high school locker room, each one of them, each one of us announcing which of her holes we would want to cum into first. The vote was three to one in favor of her mouth; my own choice was her cunt. The conversation degenerated into talk of gang bangs and such.
As I stood over her, staring at the wet stain on the front of her panties, my mind flashed back to that interview, then back even farther to the first interview, the day I realized that it was a bad business move to fuck an employee. I wasn't worried about a shakedown, because I didn't give a damn if my wife knew; she herself was boffing pool boys, meter readers and anyone else with meat between his legs. Damn lucky thing that I had a good tight pre-nup so the cunt couldn't wipe me out. I was somewhat concerned about a claim of sexual harassment; I didn't have a tape of Jamie just about offering herself up to me, and I knew that some State commission would believe the woman if she complained. But really I was more worried about our relationship becoming so tense that she would quit, and that would have been a shame, for she was a damn good analyst.
But when you're standing over an almost naked incredibly luscious piece of ass, with you bare cock hanging out, all those thoughts are subsumed into the foremost thought of where your waiting load of cum is going to be deposited. And I had long since voted that it be into her cunt.
Only she didn't make that easy. I knew I had to get her off quickly, that's why we were here, and I began to rub her pussy from outside the panties. Rather than just laying there to enjoy it, she reached her head up and took my cock into her mouth. Shit! I knew I could hold out long enough for her to cum first, still a blow job was not the way I wanted to cum. But it felt so good having her warm lips wrapped around me, her tongue circling the purple crown atop my cock, her hand tickling my balls. Shit, that mouth, those hands, she's liable to make me blow my wad before I get her off.
I slid my hand under the waistband of her panties and pulled out of her mouth. My finger slid easily into her soaking love tunnel.
"Jamie, you're the one who hasn't had an orgasm in a long time. If you don't stop what you're doing, I'm going to explode and then I'll be no use to you."
Son of a bitch, the sight of that beautiful cock had me so hot that I forgot we were here to get me off first. If he hadn't stopped me, I would have sucked every little drop of his cum down my throat and I would have had to give myself a hand job.
What's the worst possible sexual insult? When you masturbate and your hand falls asleep!
I lifted my legs and my ass presented to his view. He glanced down there and I briefly wondered if he planned to start in my back door, but he spread my legs, still upraised, and put his mouth on my wet pussy lips. He had the tongue of an expert, just what I needed then. His lips sucked in all my flowing juices, his tongue twirled around my clit, he buried his nose inside me and licked my taint. He had long curly hair and I grabbed it, pulling his face into me as tightly as possible. Eat me, Michael, eat me, eat me.
Usually, when I cum, I don't make a lot of noise; rather, I moan a lot, and sob, without tears. That's what I did this time, also, but in my head I was screaming at the ecstasy his tongue was giving me, as my ass humped up off the bed to push my cunt into Michael's face. My tits bounced undisturbed as his hands were busy gripping my ass. I pounded him with the sides of my fists on the top of his head, yet his tongue continued to work my clit, never pausing for a breath. Oh, Stephen, on your best day you've never eaten me so well. My thighs clamped around Michael's face as I rolled to the side, still sobbing.
I barely had the strength to speak. "Now are you ready for the blowjob of your life, Michael?"
He didn't answer, nor had I expected one. He rolled me again onto my back and walked on his knees to straddle my face, presenting his cock for examination and pleasure. I held it up, studied the veins underneath, the wrinkled sac. I pulled his balls into my mouth, gumming them, slobbering saliva all over them. I kissed my way along the bottom of his cock, ran my tongue around the ridge behind his crown, tried to force the tip of my tongue into his little piss slit. He sat back on his heels, reaching behind him to squeeze my tits, to flick my nipples. Moisture poured from my pussy lips.
Then I swallowed him straight on, sucking away, my hands playing with his balls, one finger creeping toward his asshole. Would he like an examination there? He is after all my boss. On the other hand, right now, he's my slave, begging my body to make him cum, and I can do whatever I want. So I shoved the finger in, and he didn't flinch. But the contact with his prostate brought him over the top; he grunted and his cock spit rope after rope into me. I never lose a drop, but when he slowed down, I pushed him over and kissed him, sharing his creamy gift with its donor.
His tongue probed my mouth; obviously the taste of his own cum was nothing new to Michael. The kiss lasted longer than necessary to transfer the sticky white love juice as our hands caressed each other. Finally he pulled away, lay back puffing.
"You have some fantastic mouth, Jamie."
"Let me know when that cock is hard enough for a fantastic pussy, Michael."
He sucked my nipples while we waited, his fingers buried inside me. I tried to make small talk, but he wasn't up to it. I would remember that.
It was an hour before he rolled on top of me, his cock sliding in easily to a wet welcome. He moved in and out slowly, in marked contrast to my recent Stephen, and my hips rose to meet his every downstroke, my vaginal walls contracting as he pulled out and then spreading eagerly as he plunged into me again and again. My legs went around him, my heels butting up against his ass to pull him into me. Our lips were locked together, and his hand made sure that my clit was continuously massaged. Faster, faster, faster, Michael. He heard my unspoken words and sped his thrusts until I moaned my orgasm.
"I'm there, Jamie." I felt the contractions in his cock as his next load spewed into my cunt; my squeeze on his balls didn't delay things either. His cum swirled in my pussy, leaking out on the backstroke to drip down my ass cheeks. He rolled off me again, and I bent my head up to reach and clean off his dripping cock. Then I lay flat again.
"Lick me clean, Michael." He did so, obviously savoring his own cum as his tongue washed me, then using that tongue to lick me to a continuing orgasm. This time I had to pull his head off my pussy.
"You're a very considerate lover, Michael."
"That's because you're so sexy, Jamie. I think I could make more money putting your ass on the street than I can selling your research."
"I'm very fussy who gets into my pants, boss."
I was exhausted. I had hoped to fuck all three holes that afternoon, and I was still planning to try for the Trifecta, but I wasn't going to object if she didn't want me in her ass that day; I knew we weren't finished.
But I lay there thinking about her last remark, and mine. I share most everything with my three junior partners, including a love for cunt. At least once a month, we do an out of town trip to visit some good client, or some company we're researching, but the basic reason for the trip is to rent two whores for the four of us and fuck every minute we're not working. I don't know what their wives know, but I'm sure they're not sluts like my own wife.
How do I share Jamie without causing her to quit? My mind raced. I knew I had an hour of small talk while my balls regenerated cum, and there would be enough quiet moments for me to figure something out. I was still grasping at straws when my cock finally got hard again. I kissed her softly, went down on her for a short time, then said, "Roll over, baby, I'd like to try your back door."
"That's nice, Michael, but I can't do that without a couple of drinks in me, and I can't very well go home tonight smelling like I've been drinking. Maybe sometime we can do an out of town trip together."
Bingo! I had my opening.
"Jamie, I do an out of town trip every month with my three partners. Do you think maybe..." I let the sentence trail off deliberately.
"You really do want to put me on the street, don't you?" She said it with a smile.
"As long as Stephen is not taking care of you properly, how about just the four of us and once in a while a very big client?"
She looked at me without a word. I'd better sweeten the pot.
"We could really make it worth your while."
Still nothing. "How about double your salary?"
Now I could see her mind at work, and the silence didn't scare me anymore.
"I can't justify a raise like that at home; it'll have to be cash off the books. And I need enough time to do good research. Someday it'll be time for me to move on and I want a quality portfolio to show my next employer."
It didn't take me long to think it through. "The cash is no problem. We can limit the stuff in the apartment to three part days a week, plus the out of town travel. The occasional big client we can handle on a case by case situation."
"And if your partners don't make me cum, they're off the list."
"I'll tell them."
Jamie seems in a good mood tonight. I guess she had a good day at the office. It sure feels good to have her warm naked ass butting up against my lap. I wish to hell this fucking cock of mine could get hard quicker, could stay hard while I took care of her.
That fucking bastard of a customer scares the shit out of me; if he goes belly up, we're in serious trouble. We'll lose everything. At least she knows why I'm having so much trouble taking care of her body, she knows I'm not out catting around or fucking some bimbo in the warehouse.
Get hard, you damn little prick. I thought about the V pill or one of the others, but they say that if there's no desire, the pills won't do a thing. But I do feel the desire, only worrying about the business fucks up everything.
I love this woman so much, I just wish I could make her happy in bed the way I did before all this financial shit started. Maybe if I just filed for bankruptcy, we'd be broke but I wouldn't have all the worries that go with owing money. Then we could live on her income while I look for a job, and I could fuck her the right way, I could make her cum like the maniac she used to be.
I love the feel of these tits, these perky nipples sticking up to meet my fingers. Ah, she's pushing her ass back into my lap; that means she's awake. And wet! It's only this fucking dick of mine that's not awake. Maybe if I rub my meat up and down the crack of her ass, it'll get a little blood in there. Ooh, the way she squirms when my fingers are inside her snatch. C'mon, boy, get hard, damn you. Shit, if I ever get my hands on that customer who owes me all the money, I'll kill him. He says he's trying to refinance; yeah, right.
Oh, boy, is that a hard-on I feel? It's a little stiff, not as much as it should be but a lot more than it was. Put your hand behind you, Jamie, give it a rub; maybe that'll do the trick. Yes, yes, your hand and mine together can do it. Ah, yes, roll this way, baby. Spread those beautiful legs. I love the way you kiss, your tongue polishing my teeth. That's it, baby, it goes right in to your cunt.
Plunge, plunge, plunge, fuck, fuck, fuck, oh shit, it's gone. Shit, shit, shit.
"I'm sorry, baby, I just can't help it. This fucking cock has become my enemy."
"That's all right, Stephen. Please let me have my vibrator."
Damn. This morning, I had refused to get it for her and we both went to work pissed off at each other. I'd better get it for her this time.
"Here you are, dear. I'm sorry about this morning."
"That's all right. Thank you, dear; now why don't you go watch a movie in the den while I get myself off?"
So that's it; my contribution to my wife's sexual happiness consists of getting her vibrator for her, then going into another room to jerk off. Yeah, that's not a problem. Shit, the only time I can't cum is when my wife is in bed with me. Maybe I should just file for bankruptcy; then it'll be all over. We won't have a pot to piss in, but we won't have creditors calling us all day and night.
Can you believe it, me thinking only about bankruptcy as my cum shoots out into my hand. Shit!
Well, at least he got the vibrator for me tonight; there's hope for him yet. I do love him, but if I have to use Michael to get off, so be it. Michael, who knows how to use his cock; I wonder how good he'd be in bed if he had the financial problems that Stephen and I do. And the money won't hurt either.
So began my experiences with Larry, Curly and Moe, the three stooges who passed for vice-presidents of Michael's company. They acted like drooling little kids at the thought of fucking me. Paul went first, the following Monday.
Getting out to the apartment was easy. All of the analysts were in and out of the office without pattern; I answered my own phone so I had no secretary to snoop on me. Even my dictation went to a pool steno, whoever was free at the time. Of course, all the analysts filed time sheets, but guess who reviewed them: Paul, vice-president for finance. Paul as an executive came and went as he pleased.
I had arranged to meet him there first thing, without even going to the office, so I could get it over with and still put in a day's work. They had given me a key to the apartment, so when I got there I changed into one of the robes hanging in the closet, nothing underneath, and put up a pot of coffee. Paul brought the donuts. When he came in, he hugged me and took off his jacket. I noticed that he hadn't kissed me, and I didn't give a damn. I wanted orgasms, not love, not even affection.
I bent over him to pour the coffee, noticing without surprise how his eyes fixed on the tits hanging out the front of the robe. He reached for one of them and began to suck; his hand went in low, thumb into my cunt without ceremony, the other four fingers splayed on my ass. His middle digit went to the crack in my ass, working its way toward my asshole.
"No asshole except out of town, Paul." He nodded, backed off with that finger, then stood up to remove the rest of his clothing. The coffee remained to get cold as his cock pointed the way into the bedroom. Just as Michael indicated in his first chapter, Paul's vote was for my mouth, and he pushed me onto my back. My mouth opened to accept the dick he presented; then he proceeded to simply fuck my face, not caring when he hit the back of my throat. You'll notice that the bastard never said a word. No kisses, no talk, you are one cold son of a bitch, Paul.
He didn't even warn me before his first shot of sperm hit the back of my mouth, followed by the rest of his load. I like to swallow, and his didn't taste bad at all. I licked him clean and he finally spoke.
"Thank you, Jamie." He began to dress and I stopped him.
"Hey, Paul, the deal is that you have to make me cum too."
"Oh, yeah, I forgot." Was that the way they treated whores? But I'll say this for him, once I reminded him, he did a great job of eating me, tongue flying like a madman, lips sucking my clit, until I moaned an orgasm into his mouth.
He left; I stayed and ate two donuts.
You would think that three times a week meant every other day, but these guys were so horny for new meat that the first time around would be one right after the other. I guess that made sense. So the next day I entertained Nate. Again, we met first thing in the morning; it's easy to convince a married man to do a matinee. Nate's contribution was a couple of Danish.
Despite what he had said in the locker room discussion after my interview, as least the way Michael described it, Nate didn't go straight for a blowjob. First he finished the coffee I had made, complimenting me on the taste. We went into the bedroom, where he undressed. As he got to the point where his shorts had to come off, he turned sideways, whether deliberately or by accident I couldn't tell, to show me his cock in profile. It was plenty big, but nothing I couldn't handle.
He helped me off with my robe before laying me onto the bed. We kissed like long-time lovers, hands playing with each other, mouths on each other's nipples. I've found that a lot of guys like that. He rolled on top of me, pushed my legs apart with his knee and was inside me without difficulty. He had me wet without the need to eat my pussy, and he was hard just be being with me. My vaginal walls spread to comfort him and he stroked away, our lips together. In order to make sure that I could cum first, his fingers were between us, playing with my clit to add to the rubbing from his cock.
My orgasms are quiet but unmistakable, and when he heard my moans he sped up, jack- hammering into me, announcing with a loud grunt when his first string of cum was about to shoot into my waiting cunt. He never stopped moving until his balls were empty, in the meantime drawing his creamy offering out of me on each backstroke.
I bent to suck his cock dry, but kept going once that was done. He gently lifted my head off him. "Thank you, Jamie, but I'm only good for once a day; don't strain your back."
What a nice man, so much gentler and more considerate than Paul.
Sid was on the schedule for Wednesday, but begged off until Thursday. I examined myself in the mirror to be sure that I hadn't lost my looks; the idea of being turned down was foreign to me. His gift was crullers; if these guys didn't stop with the sweets, I would become too heavy to interest them. Once we were both down to bare skin, his problem became obvious. Only with him it was physical, not mental.
"I've had this prostate operation and it's almost impossible for me to get it up. I don't mind eating you all day long, but it may take your mouth and hands that long to get me stiff. I can only cum with a lot of work. I hope you don't mind."
"Oh, Sidney, you dear, as long as you're willing to take care of me, I'll work on you all day and night if it'll make you feel good.
Damned if he wasn't right. We went straight to a sixty-nine, eating each other with pleasure. He had me cumming in a few minutes, and then every ten or fifteen minutes after that until I was so sensitive that I had to push his face away. Meanwhile, it took me the better part of an exhausting two hours to get a little spurt out of him; it was so much work that the little spurt felt like a huge victory.
Also very gentle, not a prick like Paul.
Janie, In Chicago
We got into the swing of things, working and fucking. Stephen was still having trouble with his erections and I was now getting all the orgasms I needed, without my vibrator. The three times a week became four, as Michael took charge of the rotation, but the mostly quickies didn't waste too much of my time. After a few weeks, the opportunity arose for an out of town party. I was going to Chicago to meet with the financial people of a company I was researching, Michael decided that it was a good time to visit an old biddy client, and the other three just made up some lies for their wives.
Michael is one of those executives who's afraid of too many key people flying together, so we went on three different planes, although that's not a real problem flying into O'Hare. There are so many flights into there that often they're not crowded. Michael and I flew together. It was an experience I've never had before; he and I changed seats to a vacant section, then he finger fucked me while I jerked him off. No one passed us except the occasional user of the rear lavatory, and no one noticed. Well, maybe one flight attendant did notice, because she seemed to give us a funny smile, but they must see everything over the course of a career. I've never washed my handkerchief that Michael used to cum into; it was still sticky when I put it into my purse and I felt like such a slut. What a wonderful feeling.
I knew that one or more of the guys would be in my asshole that night, so at dinner I had a couple of drinks. Each of them had fucked me several times back home, so they were rather blasé at dinner; we looked like an ordinary business group. Michael, ever the boss, said, "Do you want to choose the order, Jamie?"
I felt the liquor. "How about all four of you together?"
He hesitated. "We've never been naked in front of each other, the four of us."
"I've never done four guys before, and I do have to get some work done in the morning. If you go one at a time, I'll never get any sleep." Actually, before that, my personal record had been one guy at a time, never even two. Well, one guy and another woman, but that doesn't count. "Let's go to the bar for a nightcap."
By the time we got to my room, I was pretty wasted, but still I knew where I was and why I was there. I thought a little bit about the possibility of Sid being embarrassed, but decided that it was his problem, not mine. I ran into the bathroom to give myself a quick whore's bath, then rejoined the men. The clothing became a blur, as each of them undressed me partially; the pile on the floor looked like a charity warehouse. I knew I'd be able to identify my own, but all those white shirts, gray suits and black shoes looked alike to me. Then the four of them carried me to the bed as I held on to the two nearest cocks.
Looking up, I could see that they were all queasy about being naked in front of each other. Most guys have been naked that way in locker rooms after athletics, but rarely if ever with four hard and pulsing cocks as the center of attraction.
It shouldn't have been too hard for them to figure out how I would take four at once, but they weren't thinking so they lay me on my back. I rolled over onto my hands and knees and started giving orders. "Nate, you slide under me and I'll ride you. You'd better not cum until I do. Paul, Sid, you two get on opposite sides of my mouth. Michael, come around back; you know what to do."
Nate got under me and I squatted down over his hard cock; his hands played with my tits as my sopping pussy enveloped his fuck stick. But I wasn't going to ride him until all four were in place. Michael came up behind me, rubbing along the crack of my ass before putting his first finger into it. Suddenly I realized why he was such a good businessman; he had prepared for the trip with a tube of KY and his fingers were well lubricated. The others waited patiently as he spread my asshole with a second and then a third finger before he finally greased himself up, and me some more. I gasped as he slid that educated cock into my back door, fraction by fraction until I felt his nuts resting against my cheeks.
When I nodded, Paul shoved his into my face, sort of like he was pissed off or jealous of Michael being in my ass. Sid held back until I winked at him, a signal, if he understood it, that I would cooperate if he had to fake an orgasm. I needed at least one hand to balance myself, so I pressed it into Nate's chest.
My hips rose and fell on Nate's cock as Michael began to stroke in and out. I could feel the two cocks rubbing each other through the membrane separating my cunt and ass. Meanwhile, I began to suck two cocks at once, keeping my tongue between them so that Paul would not notice that Sid's was still soft. I used my free hand to diddle their balls, but mostly for dear sweet Sid, because he needed the help.
I pushed my ass back toward Michael, and the angle kept Nate's blood filled cock rubbing against my clit. This crazy coupling-fiving?-was so unreal that it didn't take long for me to start moaning around the two cocks in my mouth. That was Nate's signal to start humping up into me, followed quickly by spurting cum flooding my cunt and dripping back out onto his balls.
Paul, who never had any interest in delaying his own orgasm, grabbed the back of my head and soon followed Nate, unloading a good shot, which I let ooze out of my lips. His cum dripped onto Nate's face and chest, but I didn't care at the moment. His meat slipped out of my mouth, leaving me inpaled only by Sid and Michael.
Michael was pounding away in my ass, in his usual unhurried style, so I decided to concentrate on getting Sid off, or at least hiding his problem. I sucked him loudly, for so long that it was uncomfortable. Then I looked up at him, winked and squeezed his balls. He took the hint and groaned, and I sped up my sucking to receive a make-believe load of cum, which I dutifully swallowed, licking my lips in mock satisfaction.
"That was some load, Sid." He smiled proudly, conspiratorially. Fuck Paul if he was hurt that I didn't compliment him. Now all I had left was Michael. As he pronged me, he reached his hand around my hip to caress my clit, ever so gently but letting me know that he would make me cum before he himself did so. I pushed my ass back at his driving cock, his legs hitting me with an audible thump on each stroke. It didn't take long anymore; with a gasp and a moan, my juices flowed down my leg and Michael poured his own cream into me, his cock remaining in place so that his cum stayed in my ass, long enough to be absorbed through the tissue of my bowels. My goodness, that man really knows how to fuck a girl's ass, even better than my pussy.
"OK, boys, bed time; I've got a lot of real work to do tomorrow."
It was Paul, who else, who ruined my reverie. "Jamie, you promised to let me fuck your ass when we got out of town."
Well, I hadn't, not really, but he could argue that I had, sort of. If I refused, there could be trouble in the office, maybe with the job, and certainly with this trip.
"If you can get it up again, baby, I can take it."
Unfortunately, the bastard was able to get it up, although the job he did on me was shit compared to the care Michael had taken to please me. Paul wouldn't even have used fresh KY if I hadn't insisted, his hands around me on my tits were clumsy, and I didn't get to cum again. Still, his partners seemed to enjoy the show. Fuck them all!
My husband's been dead for about three years. We had thirty-seven good years; we lived well and he left me well off. Michael and his firm have been handling our money for about ten years, doing an exceptional job in good and bad markets. I've always had the feeling that his firm really cares about me as a person, not just as a client.