Five Twenties

The most erotic thing about the time I spend with my weekly lover, X, is not his thick cock sliding between my lips; nor is it when his rosy, lubricated head finds my hole and pushes seven inches in; it's not even the moaning pleasure I get as he slides in and out of me for ten, even fifteen minutes or more; nor is it when, usually silently, X shoots his week's load deep inside my ass. No, the most erotic thing about my time with X is when, after he's orgasmed and pulled out of me, he returns to the bed folding over a quintet of $20 bills, which he then, with a smile, tucks inside the pink garter ringing my right thigh.

Still in my receiving position, on my elbows and knees, and with my balls hanging beneath their ringed weight, I quietly thank him.

"You're worth it," he says, giving my pale ass a pat. "Now why don't you get a cloth and clean me off so my bitchy wife doesn't suspect anything."

It's not what you think. I'm not a prostitute. Or, if you choose to view me that way, I'm a prostitute with—up until recent weeks—only one client: X and X alone.

At any rate, it wasn't always this way. Less than nine months ago I was an executive with a prominent munitions firm making over eighty thousand dollars a year. But then came the Christmas Day bombing that destroyed not only my company's factories but much of our city, and sank the local economy into deep recession. I've been unemployed ever since then and, for the most part, have been living off government assistance (it's about to run out) and my life savings (ditto).

The tradition of the five twenties started shortly after, with the New Year. X, a military man of some prominence, had always played the role of the Dom to my gurly sub. But on this first visit of the New Year, while portions of our city still burned, he behaved somewhat differently, more gently. He eschewed the riding crop, for instance. And after he fucked me, and as I was down on my stockinged knees wiping the lubricant off his beautiful cock with a warm washcloth, he said: "I have something for you."

Another ball-stretching ring, I wondered. Another frilly pair of panties?

Instead he returned from the pants of his uniform, neatly draped over a bedroom chair, with a wad of bills he folded, and folded again, and then tucked inside the lace top of my thigh-high.

"What's this?" I asked, warm cummy washcloth still in hand.

"Hopefully this will help," he replied. Then he gave my shaved ass a pat and went about pulling on his uniform.

After seeing him to the door (Me: "Watch for drones." X: "I eat enemy drones for breakfast.") I investigated the wad of cash in my stocking. To my amazement I discovered five $20 bills. I was ecstatic. I confess I got an instant hard on (something that normally doesn't happen when I'm in gurly mode). I'd just been paid for sex! I shot my load all over the floor!

I sent X an email thanking him profusely. He didn't reply. Then, a week later, on his next visit, and reprising his riding crop, he whipped the sides of my stockinged thighs as well as my pantied ass upon arrival.

"Don't EVER mention the money-for-sex thing again publicly!" he said.

"It was a private email!" I cried, dancing to his crop.

"There's no such thing. Don't be an asshole."

Still, after he finished fucking me that day, he once again tucked five twenties inside my stockings, and gave my ass a pat.

"Sorry about the whipping," he said, as he began putting on his uniform.

"I deserved it." (I'd actually rather enjoyed it.)

"These are parlous times," he said, using a rather antiquated term. "We have to be careful."

"Yessir."

He laughed. "And how come that little thing doesn't get hard till I stick money in your stocking?"

I had no answer. But I did go out and buy, shortly after that, a pink elastic garter. Where he sticks the five twenties every week. It has become our little tradition. I'm hurting financially. He has plenty of money. Not only his officer's salary but due to the fact that his frigid (according to him) wife is heiress to a major cosmetics company. Which, since the start of the war, has been converted to making synthetic plasma and such. Life-blood not lipstick, as the slogan goes...

At any rate, my gay lover is rich as a motherfucker. From his perspective I guess $100 a week is a small price to pay for a discreet, willing mouth and hole. Especially one that doesn't require him to wear a condom ("I'm healthy as a horse," he's assured me a dozen times. "If I wanted to wear a rubber I'd fuck my wife. The bitch!")

And so it has gone for months and months. Until, a few weeks ago when, his hands gripping my slender hips, his cock deep inside me, he asked: "You ever had two guys?"

After another pleasure-moan I said, haltingly: "No. No sir."

"Would you like to?"

"I...guess so." X was really banging me hard at this moment. Speech was difficult.

"Cause I got a friend...he just got transferred here. Same...rank as me. Sort of. God this is good! He...anyway we have the same...tastes so to speak. He likes...trannies too. Trannies, CD's like you...she-males...But that was in fucking Thailand. Anyway...I could bring him next time if you...It would, like, double your income. So to speak. I just came. Fuck. Get a cloth...," he concluded, pulling out of my ass.

"Yessir."

The next week X arrived with his friend Y. Both were highly decorated. Y was much larger, however. I don't mean just in stature but in cock and ball size. Y was a monster! For some reason the two men, perhaps out of embarrassment, insisted on being in the bedroom with me one at a time. Y went first. This was unfortunate. Y was so big it hurt being penetrated. He didn't take this into consideration, however, and fucked me hard, and deep, right from the get-go. It was five minutes before the pain gave way and the pleasure of being fucked kicked in. He came with a shout which, I have to admit, was kind of refreshing, and fulfilling, compared to X's usual orgasmic silence.

Y was so big he left me dilated (I could feel the ambient air flowing up my asshole). It made X's entry easier, but less pleasurable for both of us.

"Jesus," he complained. "I can hardly feel you."

"You should've gone first," I told my long-time lover.

"I will. Next time. Fucker!" slapping my roomy ass.

After several frustrating minutes X pulled out and did something he'd never done before. He jacked off on my crack, on my gaping asshole. When he finally came (with a shout!) some of it went in my hole while the rest ran down my weighted balls and dripped to the sheet. It was actually kind of fun. In the past he'd always cum deep inside me. This was my first chance to see his copious cum in all its thick, white glory.

"Jesus," he said afterwards, looking down at the dripping mess. "Fuck."

Indeed!

X paid me, per usual, in the bedroom. While Y, downstairs in the livingroom while his fellow officer took his turn, paid me at the front door.

"Like this?" he asked of X, stuffing bills inside my garter.

"Whatever."

"I prefer gurls with tits," Y said, exiting my house. Asshole. At that moment I wished an enemy drone would strike him dead. You want tits? Pay for the implants! X, meanwhile, gave my pantied ass (I'd tucked a panty-liner in to absorb the oozing cum) a reassuring pat.

"Believe me," X said. "He enjoyed himself."

"Hope so."

"Next week? The two of us?"

"Yessir."

"I'll go first."

"Good."

X gave my ass a parting squeeze before ducking out under a threatening sky.

"Be safe," I said. Then I turned to counting my gartered bounty.

Ten twenties. That was enough to nearly pay my mortgage. I was ecstatic. X was wonderful and Y, well, Y was an asshole. Maybe. Still, it paid the bills. A couple more army officers and I'd be on top again.

Well, bottom.