Five in One Night

When I walk into the bar there are only a handful of people inside. The bartender gives me a grin and a nod; guess that happens when you're a regular. The waitress comes over to take my order and I admire her uniform. This place is attached to a very nice hotel, so the waitress's uniform is a cross between professional and slutty. For some reason, that turns me on. Her blouse shows a lot of cleavage and her skirt is short so that combined with her high heels she's got legs that look like they go from the ground all the way up to the ceiling. She eyes my wedding ring and I smile at her. Yeah, I'm married.

After my second drink I notice a gentleman sitting at the bar. He's dressed in a suit, but as is typical for the end of the day, his tie is gone and the top button of his collar is open. He looks like he's getting ready for a GQ shoot or something. He glances over his shoulder and I catch him giving me the once over. Thinking nothing of it, I turn my attention back to the television. I'm nursing the tail end of my drink when he strolls over and sets a freshie on the table.

"I noticed you were just about done. I thought I'd beat the waitress to your refill," he says.

I mumble a thank you and stare at the drink. He's so good-looking he makes me uncomfortable. Polished. Suave.

"Mind if I sit?" he asks.

Not really in the mood for company, I look up at him hoping that my trademark "fuck you" glare will scare him off, but he just smiles at me and sits.

He introduces himself and tells me he's in town for a conference with some of his co-workers. I don't really pay much attention; in fact I don't even catch his name. He tries to make conversation but I tune him out until he asks, "What brings you in here tonight?"

"Argument with my wife," I snap. Maybe domestic ugliness will make him go away.

I'm wrong again, though. He just nods and smiles. "Tough night," he says, with sympathy. "Maybe you need somebody to talk to."

"Do I look like I really want to talk?" I ask, and now I'm getting pissed off. Mr. GQ needs to take his metrosexual ass back to his hotel room before I bust him right in his facial.

"No," he says. "But I thought you looked hot sitting here brooding, and I wanted to talk to you." He laughs then, a happy, carefree sound rolling from his lips before he wraps them around his glass to drink.

I'm dumfounded. I can't even imagine what my face looks like at that moment, but I bet it's pretty fucking entertaining. Mr GQ's eyes dance as he sips his drink and stares at me, waiting for some kind of response, and I get that he's ready for any response, from me knocking his teeth down his throat to me grabbing his dick right out in the open.

This guy is slick.

All I can manage are the words, "You thought I was hot, huh?"

"Still think you are," he says, a cocky grin on his face.

"Well I didn't come in here tonight to get picked up," I say, fighting a blush I can feel right under the edge of my collar.

He doesn't go away though. He sits at the table with me chatting up a storm. He seems to want to know all about me: where I'm from, what I do for a living, my hobbies. I have a strange thought that I'm being hit on, like some poor woman in a bar who can't fend for herself.

I finish telling him about my love of skiing when he asks the $100 question. "So what did you and your wife argue about?"

"Money, as usual. She lost her job a while ago and started her own business. It's been really slow getting started. I'm getting to the point where I would do just about anything for some extra cash to pay the bills and keep the peace."

"Is there anything you wouldn't do for money?" he asks, looking up at the ceiling.

"Rob a bank," I say immediately, "or anything else illegal."

"But you'd do anything else?" he asks.

"At this point? Yeah," I say, nodding, morose. I don't bother going into just how bad things are right now. I don't want to start crying in a bar.

He leans forward. "I have a proposition for you then. I'm here with three co-workers and friends. We'd pay you 500 bucks each if we could fuck your sweet ass."

I'm buzzed but not that buzzed! Mr. GQ's about thirty seconds away from me kicking his well-manicured butt. Then a thought flickers through my mind: two thousand dollars. I stare at him as all kinds of thoughts whiz through my head. My need for the money is first, of course, and how far I can spread $2000. But then other things intrude on my mental landscape.

Images of a much younger me dressed in women's clothing spring up before my eyes. I know it's just the alcohol, my mind, and Mr. GQ's suggestion playing tricks on me, but I can't help it. I get hard anyway. I remember those days. I remember my "special" friend, the one who did for free exactly what Mr. GQ is offering to pay me for, and I remember how good it felt. Though I never had a boyfriend and have never desired one, I know I have bisexual tendencies.

Labels suck.

I never did. I do have a few standards.

He can tell I'm thinking about his offer and he grins at me. Another thought... He and his buddies are from out of town so I won't ever see them again. Nobody would ever know what I did to score those two grand.

"I don't suck dick," I say.

"That's fine," he says, and winks. "I'll give you half right now. You come up to room 314 and you get the other half when we're done." He puts an envelope on the table and leaves.

I stare at it until I can't stand it any longer, then grab it and head to my car. Once inside I open the envelope and there it is: one thousand dollars. I count it several times. The idea of simply fleeing with Mr. GQ's money does cross my mind. Knowing that another grand is available is what keeps me from doing it. I struggle and wrestle with my scruples for another five minutes before I toss the envelope in the glove compartment, get out of the car, lock it and head up to room 314.

I knock on the door and Mr. GQ opens the door. I still don't remember his name. The room is huge and his three friends are sitting on the couch watching TV. They all turn to look at me as I'm introduced.

One of them says, very clearly, "Great choice, Paul!"

So Mr. GQ's name is Paul... I vaguely remember that. Paul pats me on the back and leads me to the next room. He offers me a chair.

"How's this going to work?" I ask as I sit.

He points to the envelope on the table next to me. I can see the cash in it. I look back at Paul as he sits across from me.

"All we want to do is fuck your ass, with you on your knees and on your back. We'll all use condoms and when we're done, that's it. Take your money and go. If you're having second thoughts just return the first envelope I gave you and we'll forget we ever met."

My eyes dart around the room; I point to the bathroom.

"Help yourself," he says. "Use anything you want."

I close the door behind me. My heart is pounding and I can't catch my breath. I grab the edge of the sink and stare into the mirror thinking that I should give him his money back and get the hell out of here. Decision made to forget this whole fucked up, insane idea, I turn to go and see a pile of shimmering cloth on the floor.

How's that saying go? If it had been a snake it would've bit me? I reached down and picked the soft, smooth material up, thinking some waitress or guest must've left a pair of pantyhose behind, but it isn't pantyhose. I can actually feel my pupils blow out in direct proportion to my dick hardening as I realize I'm staring at a bodysuit, obviously made for men who need to feel... smooth and pretty. I never had the cash for anything like this when I went through my little cross-dressing stint.

Nylon and spandex, the suit covers the full body but for the genitals, of course. I don't know what possesses me to pick it up and put it on, but I do, slowly and carefully so that I don't snag it. Watching myself in the mirror only keys me up even more because it's a perfect fit. The material is amazingly soft and smooth. Unable to resist, I rub myself which gives me a straining hard-on. I'm still having trouble breathing and my eyes are way too wide. I turn and walk back to the bedroom.

Paul is sitting in his robe and his eyes widen as he sees me walk out in this bodysuit. I can see his cock get hard under his robe immediately, and it kind of makes me feel proud. Mr. GQ really does think I'm hot; his body can't lie.

He walks over to me, takes my hand and leads me to the bed. Yeah, these guys have totally done this before, because the headboard on the huge bed that Paul takes me to is a large mirror. Paul puts his hand on my shoulder and bends me over so that my chest is on a pillow and my feet are on the floor. He begins to rub his hands over my body. The feel of the silky smooth bodysuit against my skin makes me tremble. It's been years since I did anything like this, and even though I'm being paid, even though I'm technically a whore, I resolve that I'm not going to be humiliated by these guys. I'm just performing a service. That's all. Just a... necessary service.

Right.

The mirror is torture. I can't decide if I want to watch what Paul's doing or if I want to close my eyes and get lost in the rub up and the fuck I know is coming. He has no such dilemma. His attention is squarely on me as his fingertips trace my hips, back, and the divot of my ass. I watch as he drops his robe, and the muscular, ripped body underneath surprises me. As he moves up he spreads my feet a little wider and places his hands on my hips. His legs bump and touch the inside of mine as his cock rubs under my balls, a sensation that drives me wild. I grab two fistfuls of the heavy bedspread and force air into my lungs.

I'm trapped in the mirror as he slips the condom over the head of his cock and rolls it down to the base. He picks up a tube of KY and squirts what looks like way too much lube into his palm, but I remember how this goes. There can never be too much lube, not really. The slick gel is cold on my ass, but it warms quickly. At first my ass resists as the head of his cock pushes against me. I can't help it; it's instinctual. But Paul's a pro, and leans forward, stroking my cock with a rippling grip that makes me relax and rock back into it. As soon as I do, he's in, rubbing my ass to relax me more as he slides his cock to the root. I can't tear my eyes away from the mirror, and watch as a stranger fucks my ass. He slams deep, pushing me against the bed. His hands roam all over me while that fucking cock just feels better and better sliding in and out of my ass.

God, I missed this. I forgot what this felt like.

His pace quickens, though, and I know what that means. I'm actually glad he has friends, because Paul and his lousy five-minute fuck are not enough to get me off. I want to cum, too, damn it. He grabs my hips and slams me hard for a few strokes, filling the condom. When he finishes he leans his chest against my back and whispers to stay where I am.

As Paul leaves the room, I think to myself, well gee, where does he think I'm going to go? I'm in this now. Does he think I'm going to take my candy and run?

A few minutes later the next ass banger walks into the room and eyes me. He pats my ass and grabs my shoulder to stand me up. Taking my hand, he whirls me around like we're on "Dancing With The Stars," only we don't end facing the judges and smiling. I end up flat on my back on the bed, a pillow under my hips with Fred Astaire by the bed. Where does Paul find these guys?

Fred's grinning like a lunatic as he drops his robe and rolls on a condom. I never particularly enjoyed this position before; it's too intimate and difficult for some tops to move well. Fred's light on his feet, though. My ankles are over his shoulders quicker than I can say "A Chorus Line," and I'm treated to the view of the ceiling mirror. My hungry ass devours his cock, and after being with Paul, Fred slides hilt deep in one stroke. Wrapping his hands around my thighs, he works his cock in and out of my ass, watching as he plows me.

I'm hard and it feels great, but his angle isn't right to do much for me. Within minutes I can feel his cock swell and his grip tighten on my thighs as he cums. When he is finished he doesn't say a word, just grabs his robe and leaves. I lay there waiting for the next guy. I can't believe I'm doing this. What's crazier is that I'm enjoying it.

I'm so out of it that I don't even notice the next guy until he's standing between my legs. He puts out his hands. I place mine in his and he pulls me up. This guy is a lot bigger than Paul and his dancer friend. He drops his robe and I automatically look down. Yup, ripped. I can't tell by looking if his cock is bigger than theirs or not; for all I know he could be a grower and what I'm seeing isn't what I'll actually be getting. Pressing our chests together, he reaches around and massages my ass. The strength of his hands is amazing.

He puts me in the center of the bed on my hands and knees. I use the mirror and watch to make sure he puts a condom on. He does, squeezing the lube down his dick like he's putting toothpaste on a toothbrush. When he plunges into me, he spreads me wider then I've ever been before, and I can't hold back the moan that whistles free. I get maybe a ten count to adjust, then without warning he squeezes my hips and starts to pound me mercilessly. I can't help but grunt and groan with every thrust.

I'm moaning like a sick cat and he must be irritated, because he stops. With his cock buried up my ass, he produces a ball gag from out of nowhere (actually, it's under one of the pillows, but in my condition, he might as well be Harry fucking Houdini). Once it's in place, he meets my eyes in the mirror and puts his finger to his lips. I get long, slow strokes to warm my ass back up, and then he pounds me for all he's worth, the gag muffling my agony. Hours later, or so it seems, he finishes. He reaches down and squeezes my balls as he pulls his cock from my gasping, abused ass.

As he leaves I lay there thinking about the story of the three bears. I know, crazy, right? But that part where Goldilocks keeps trying everything and it's just not quite right – too hot, too cold, too hard, too soft, too high, too low. Then Goldilocks finds one of everything that's just exactly right and she gets the best meal, seat, and nap of her life. I always figured the next part of that story was where Baby Bear came home and fucked the shit out of her, because if all his junk fit her so well, his cock was probably a perfect fit right up her sweet cunt. But the reason I'm thinking about the three bears is because I'm feeling a lot like Goldilocks. Not that Paul and his friends are a bunch of bears, not at all, but because I'm really waiting for one of them to walk in and just fit with me exactly right. Then I remember that I'm just tonight's paid whore, and nobody cares about how they fit with me.

Yeah, well, Goldilocks had it rough, too.

The next guy walks in, shuts the door, and drops his robe. All thoughts of fairy tales go out my left ear when I see the monster cock he's sporting. Holy donkey dicks, Batman!

He smirks at me and says, "I hope your ass is good and ready because I am going to fuck you till you scream like a little girl."

This can't be good. It's a little late for second thoughts, though.

He wraps his hand around his cock and oh yeah, it's huge. I watch it bounce as he walks toward me. When he gets to the bed he turns me over onto my back and straddles my chest, that monster cock staring me in the face. I know I said I didn't suck dick, but if it weren't for the gag in my mouth I would've tried. That fucking thing is beautiful, long, smooth, as big around as my wrist, and covered with pulsing veins nearly as thick as my fingers. When he starts rubbing it all over my gagged face, I get so excited and so hard my balls ache.

The smell of sex fills my nose and I imagine how salty his slick precum will taste. I'm drooling almost uncontrollably around the fucking gag and want it gone but he's sitting on my chest. Fucker. He laughs.

"Pretty boy," he says. "Too bad I can't fuck that pretty mouth, but Paul says no. Paul says just this luscious ass, and we always do. What. Paul. Says." He slaps my face with his dick on his last words, punctuating them, then climbs off me.

Grabbing a condom, he tries to stretch it over his monster dick and promptly breaks it. Motherfucker. He gets another one and tries again, managing to get the second condom on, though it looks painful it's stretched so tightly. I expect him to get on with the fucking, but no, he grabs another condom. He lubes the one he's wearing, then carefully rolls the third condom down. When he sees me staring at him, he gives me a shit-eating grin.

"Sorry, Pretty Boy," he says. "I'll fuck that sweet ass in just a minute. I always break these damn things. Best if I just start with them doubled up."

I roll my eyes and he chuckles. "Watch that 'tude, Pretty Boy. I'll have to fuck it out of ya."

Once he's happy with the condoms he moves between my legs. He grabs two pillows and elevates my hips, then spends some time with the lube. I lift my own legs over his shoulders and try to mentally prepare for the coming invasion. I'm totally not prepared for him to lean down, take my treasure trail in his teeth, and tug forcefully at the hair. I gasp, inhaling hugely, and as I exhale he presses in.

A dull pain fills my ass but it doesn't hurt; it feels wonderful. The head of his cock throbs with the beat of his heart, a crazy feeling that turns me on and keeps me hard. He takes his time inching his way into me, and I think I've got him until he grins at me.

"That's half," he says.

My eyes roll again, and this time it's not attitude, this time it's desperation. Without further ado, he slams his cock deep. His balls slap against me hard and as the pain shoots up my legs and into my back I let out a muted squeal. Gripping my shoulders, he lays over me and fucks me like I've never been fucked before. The pleasure and pain of this huge cock slicing in and out of me is unreal.

His stamina is amazing. He rocks into me and the little dancing lights start. My balls are so tight that I'm desperate to cum, but I can't quite get there, and the big fucker won't move to let me stroke off. Every time I try to touch myself he slaps my hand away or grabs my wrist and slams it down to mattress, fucking me harder and deeper. He bones me for a full half-hour, working the best spots until my vision is glitter and my balls are blue from the need to get off.

When his orgasm hits, I feel his cock swell and shoot as it fills the condom, and true to his prediction, I scream like a little girl. He finishes fucking my ass, pulls out, and leaves. I lay there in a half-orgasmic state, my ass worked over, my balls desperate to release.

Paul comes back in with Fred the dancer and unbuckles the gag.

"Hey man, how ya doing?" Paul asks.

"I'm okay," I say, "but it's be really fucking nice to get off."

"You think you're up for one more round? We'll see what we can do about your delicate condition."

I laugh despite myself. "Sure."

Paul slips on a condom, lubes up, and starts to fuck my ass. Fred's just sitting on the bed watching. I don't really care. The feeling of Paul's cock sliding in and out of my ass feels so good at this point that he could've put me on YouTube and I wouldn't have cared. After a few minutes Fred crawls over and takes my rock hard cock into his hot, wet mouth. The rush of that feeling makes me clamp down on Paul and he has to stop. I relax after a few seconds of working it, Paul and his friend get their mojo going sucking my cock and fucking my ass.

After so much sex and now the simultaneous stimulation of my cock, balls, and ass, the orgasm is incredible. It builds from the base of my spine and spreads like a brushfire, slow at first, hesitant, and then blazing away burning everything in its path. The release is such a relief that I feel pounds lighter, which makes sense. I did just get one hell of a workout.