The Pickup

I'd been watching her for over an hour, saw multiple men approach, only to leave not long after, snubbed.

The outfit she wore said without words that she was there for some action. Her dress was too young for her, the skirt falling only a couple inches below her ass, the bodice revealing more cleavage than a lot of women could even dream of.

She didn't look exactly comfortable being there, as if bars weren't her usual hangouts. The first glass of wine led to another. When she ordered the third, and turned away a guy who obviously was trying to buy it for her, I thought I'd make a move. Worst that could happen is I'd be rebuffed like the others.

"Hi, honey. Whatcha drinking there?" Not real smooth, I know, but picking up women in bars isn't what I normally do.

"Red," she replied with a slight slur, lifting her glass to illustrate.

"I see," I told her, taking a seat beside her. "I gotta admit, I've been watching you a while now, and was thinking maybe you should get out of here before glass number three there's finished."

"Oh yeah?" she said, turning to me. The skirt on her little yellow dress was short enough, and her legs were spread just enough, I could see matching lace panties peeking out from between her thighs. "And what can you offer that these other guys haven't already volunteered for free?"

Her question stumped me. "Uh, nothing, I guess. I just thought maybe you should leave before glass number four and you do something you might regret."

"What makes you think I'd regret anything?"

I held both hands up in surrender. "Just guessing. I don't know you, and you might do this all the time. It just seems to me like you've turned down a lot of opportunities."

She took a draw from her glass. "Nope. Just waitin' for the right guy to come along."

She then slammed the last two thirds from her glass, set it down, then said, "You're the lucky winner. Let's go, stud."

With that, she grabbed my hand, picked up her little pocketbook and practically dragged me outside.

"Which one's yours?" she asked, scanning the parking lot.

Placing a hand on her hip, I guided her to my rental. Opening the passenger door for her, I received, "Such a gentleman." In getting in, I got an even better view of those panties I'd got a glimpse of before, and her breasts nearly fell out of the low-cut top of her dress.

I was nervous as I went around to get in, myself. That afternoon, I'd made a significant withdrawal from the bank, in preparation for what I was now setting in motion.

My hotel wasn't far, so the drive wasn't long, and it was passed in silence. She seemed self-conscious, walking through the lobby. The girl at the desk barely looked up when we walked in, but the young man who emerged from the "employees only" door as we passed on the way to the elevators gave her a hungry up-and-down, then me a thumbs-up once she'd gone by ahead.

I gave him a nod and a half smile, then hurried to catch up.

In the elevator, she mashed her ample chest into mine, one hand going to my swelling cock.

"This isn't costing extra, is it?" I asked with a slight quiver in my voice.

Her lower hand gave my cock a squeeze, drawing a moan out of me.

"Not at all, honey. Just wanted to see what I'll be working with."

"And?" I managed.

"Not bad," she admitted. "This doesn't have to be fun for me, but it's always nicer if it is."

About this time, the chime went off and the doors opened. She gave my now-hard cock one more squeeze, then dragged her hand slowly up its length as she turned and exited.

Feeling a big, burning spotlight on the erection in my trousers, I hurried down the hallway, fumbling my keycard out of my wallet and getting the door open as quickly as possible.

When the door had clicked shut behind us, she sauntered into the room and plopped herself on the edge of the bed.

Fishing a lipstick from her clutch, she applied a new, garish coat over what she'd worn.

Dropping the tube back into her purse, she said, "I'm Krystle, if you're a name guy, but you can call me anything you like, cause you're the one paying.

"Speaking of which, it'll be a flat $XXX for an hour, up front, just for having me sit here. Anything else'll be extra."

I began to sweat nervously as I pulled out my wallet and dropped a pile of Bens onto the nightstand beside her purse.

She watched the bills land, then turned back to me.

"Whattya want to do? You don't strike me as a talker. You'd be surprised how many guys just want to bitch about their wives, girlfriends or boyfriends. Easy money for me," she shrugged.

Without saying anything, I laid a few more Franklins on her pile, unbuckled my belt, dropped my pants and boxers, then grabbed her head and forced my hard-on down her throat until she started to gag.

Gagging women not being my thing, I backed off a little, but kept fucking. After a while, I let go of her and let her drive.

The pace slowed, but the enthusiasm didn't. She seemed to know just what I liked, and even got a hand in caressing my balls.

Before long, I was pumping my first load into her mouth. When she started pulling away, I grabbed her head again, threw another Ben on the pile, and held her there till she swallowed.

I held her in place until I was sure she'd swallowed it all, then finally let her go.

She sat panting for a little bit before speaking. "Been saving up for Krystle, I see. That's good. I like my boys to get their money's worth.

"Got any more in there, or was that your whole wad? Maybe your girl doesn't like using her mouth on your big, fat cock, is that it?"

I didn't feel like answering. It seemed like she was speaking plenty for both of us.

Kicking off my shoes, I ditched my pants and underwear, then got the rest of my clothes off.

Krystle gave a whistle. "Nice, " was surprisingly all she said.

When I reached under her skirt and pulled her little panties off, she knew what I was looking for.

Taking her hand, I helped her off the bed and guided her to the window and out onto the balcony. From here, there was an incredible view of the city. The only view I was interested was the one that'd been hidden beneath the patch of yellow lace on the floor inside.

Giving her a guiding push between the shoulder blades, I let her lean on the railing and watch the view.

She wasn't too talkative right then, because she was preparing for what came next. Without much preamble, I found the yielding spot and shoved forward.

Krystle gave out with a grunt, but said nothing as I slid into her cunt with surprising ease.

"Now that's what I'm talkin' 'bout," she managed after a little bit. "And bareback, no less.

"That'll be extra," she added as an aside.

Still not feeling real talkative, I pushed the hem of her dress higher, exposing her entire ass, then grabbed her hips and started to pump.

Oh yeah, she had a great pussy. I don't think I could identify a bad one. I'd cum once already, so I was going to last a while.

I didn't bother being quiet. Hell, I didn't know anybody here, what did I care? And Krystle seemed of the same degree of "who gives a fuck?" because she moaned, groaned, grunted and screamed as I pounded her as hard as I could manage. That we were doing this in semi-public was a dangerous turn-on, too.

Then, just like with the blowjob, it had to come to an end. My orgasm tore through me like I'd never cum before in my life. I shoved forward and filled Krystle's cunt with another flood of my jizz while letting the world know what she'd done to me.

Once my orgasm was over, I stayed buried in her until I felt my cock start to soften. When I pulled out, a glob of white spilled from her hole and onto the balcony's concrete floor. I then turned and headed back inside.

Krystle came back in to join me a minute or so later. As she came in, I was enlarging her stack of C's...

"Hour's almost up," she told me. "If you're done, I'll go now." She started reaching for the panties on the floor.

"Wait." I grabbed her arm, then made sure she watched me lay the remainder of my cash on the "Krystle pile."

"One more time," I said, my voice as flat as I could get it. My heart began to pound as I rasped, "Back door."

Krystle looked at me, then at the stack of bills next to her pocketbook, then back at me.

She didn't sound quite so confident when she asked, "Got any lube, honey? Cause I don't do dry."

I reached into the nightstand drawer under the pile of money and placed a small bottle of lubricant in her hand.

Krystle looked at the bottle a moment, then pulled her dress over her head and flung it over the desk chair. She laid back on the bed, her ass right on the edge, throwing her legs up and back. She then squirted some lube in her hand and rubbed it on and into her tightest hole. That done, she handed the bottle back to me.

"Your turn, honey. I'm not doing this unless we're both slicked up."

Pouring a good amount into my palm, I rubbed it all over my cock, hard for the third time. I was damn proud of myself.

This hole didn't give as readily as her pussy had, not surprising. Still, I kept a steady pressure until the head popped in. Her hiss of surprise told me she didn't do this much.

I just kept pushing, and her asshole kept reluctantly letting me in. It took longer, but after a while, my cock was buried in this woman's ass.

The sensation was indescribable. I have no intention of ever giving up pussy, but I could sure get used to this.

"Bet your girl doesn't do this for you, does she?" Krystle gasped, her concentration apparently on keeping her ass from clamping down and intensifying whatever it was she was feeling.

"Rub yourself," I ordered. I figured it might distract her from what was happening in her butt just enough. Not that it was necessarily part of her job to be comfortable, but at the moment, I was paying the bill, so she reached to her shaven cunt and began masturbating.

As Krystle worked her clit, I took it as my cue to start fucking.

Oh, yes, this was beyond nice. A totally different feel from vaginal, but I could see where a guy could get hooked on it. And in this position, I had a perfect view of her pussy while she worked it hard. The added visual stimulation -- both her masturbation as well as the fact she had a truly superb set of tits -- made a third orgasm a distinct possibility.

I fucked this woman's asshole hard. It only took a minute or so until it had loosened up enough that I could fuck it like it was a pussy.

It was surprising how quickly that sensation of impending orgasm came over me, especially given the two enormous climaxes I'd already had. Nevertheless, I knew I was going to be able to cum again, and it would be a lot sooner than I expected.

"Cum, Krystle," I told her when she seemed to be getting close, "but don't stop rubbing yourself." I was enjoying watching her work her pussy. It was going to aid me in Cum Number Three, so there was no way I wanted her to stop.

About fifteen seconds later, she came. It was her first orgasm since we'd begun. Of course, her job was to get me off. Her pleasure was immaterial. I liked seeing it, though. Few things sexier than a woman cumming.

And I felt it in my cock. Each vaginal contraction affected her anal muscles, so her asshole gripped and released me several times as she came.

As ordered, she continued rubbing herself, and I could tell it wouldn't be long after that...

Indeed, about a minute later, my third hit. I unleashed another load into Krystle's amazing ass while I yelled and moaned, letting her -- and anybody in earshot - just what this woman had done for/to me.

This time, when I pulled out, I headed for the bathroom. I got myself cleaned up then went back out to where Krystle sat, counting Hundreds.

With a satisfied grin, she tucked the cash in her pocketbook, then stood and went into the bathroom, herself. The feel of the room was that our transaction was over.

Out of the bathroom, Krystle took her little dress and let it cascade down her body.

There was a palpable awkwardness in the air. I felt like I should say something, but the only thing appropriate, considering, was, "Thank you."

Krystle held up her purse. "Thank you. I hope it was what you were looking for, honey."

Without waiting for an answer, she opened the door and was gone.

I stood there a while, still nude, going over what had just happened. I felt a surge in my cock that indicated another erection was possible, but I'd already cum more times in such a time frame than I had since I was a horny teen.

Taking a bottle of water out of the fridge, I went back out to the balcony.

Avoiding the blob of cum still on the floor out there, I leaned on the rail and looked out over the city.

While I contemplated, I heard the door open and close. A few seconds later, I felt hands on my hips and a body press against me.

"You didn't call me any names," said the voice of "Krystle."

I turned to see the woman I'd just fucked -and paid - standing there, still in her yellow dress, still showing more than a woman her age probably should.

"And you left your panties in the middle of the floor." My cock was again at attention, but by now, there was an ache at the base that I was probably going to feel for a day or so.

She reached between our bodies and acknowledged my fourth(!) erection of the evening with the caress of a finger.

"Those are for you. You can do what you want with them."

I smiled and kissed her. There was a faint aroma of semen around her. "You really like that anal stuff, don't you?" she said with a grin.

"With you, I like it all," I told her with utter honesty.

"Next time, it'll be your ass," she insisted, wrapping her hands around my cock now. "We're going to be doing a little 'domme and slave' thing."

"I can hardly wait."

With that, I put a hand on her ass and we headed inside to get some sleep...