A Work Event Worth Attending

In tradition of trying to bring all the people at work closer together, my workplace management team has decided to host a "team building" event, which always felt more like an obligation than something worth attending. When the store manager (we'll call her Tara) announced that it was offsite at a go-karting track, I was actually interested for once. Something fun, having no real work related games, and a chance to see "her" outside of work. Who's "her"? Oh, just someone who've I've not been ever able to keep my eyes off since the day I started my job. For the sake of anonymity, let's call her Jenna.

Jenna was almost a porn star in looks. Medium height, slight curves, natural blonde hair, sexy melting smile, and big boobs. Oh god her boobs. She was someone who was obviously more than simply "well endowed", and she knew it. Her normal clothes gave her cleavage without trying, and when she did want to show off her chest, everyone's eye's fell victim to her plunging neckline. It was the main reason I wanted her.

So when the night came for the meet up, it was a record breaking heat wave with humidity to match. Unless you were straight out of the air conditioning, you would already be hot and sweating. So when I showed up, everyone was dressed to be comfortable, especially Jenna. And it seemed it was a night where she wanted the looks, and had no shame about it. A loose fitting white tank top with spaghetti straps with a black push up bra to make the stars of the show right up at center stage. A short micro skirt that was cut shorter so her pockets were hanging out the back, and her thong strings were hiked out like they were bikini bottoms, her ass hanging out just a bit, it seemed inviting all it's own. Long shaved smooth legs going into a pair of white high heel sandals that showed off her red sparkle nail polish.

At this point in time I was thinking I might need to go rub one out in the car just so my cock doesn't start pitching a tent and call much unwanted attention with everyone around, but I decided to quickly, and discreetly do some rearranging out of eye view so any unsightly bulges would be minimal, and possibly unseen. As I approached the crowd, the few coworkers I had on a more friendly level all came for a hug or a hand shake, and I took a seat to try and get my discreet peep show in.

After only a moment, our Tara called everyone into the safety briefing room for anyone who wanted to race. While I was more than content with just getting some discreet ogling, and time with my friends in, I was down for some racing. So about 2 dozen of us jump suited up, got a fitting helmet and went through the motions and lectures of how to drive, how to be safe and how to obey the rules of the racetrack.

We head to the track, some of us run to get as close to the front as possible to get a head start. All the engines cut out from the auto safety of the race announcer, and Tara walks to the front with a mega phone. She tells everyone who's racing, that there's a reward for first, second and third place. First place gets 2 weeks paid vacation, second place gets a $500 gift card, third place gets to have a manager of their choice do their work for 3 days as they get to supervise and kick back.

All of a sudden, all the engines start and there's a timer counting down. All the people who are racing start revving, all the people who are watching stand up and walk to the fence line to get a good view. After 29 laps, the first 3 are head and head. (Fake names for anonymity) Kent is first, Julia is second, Sarah is third. I'm a close fourth.

Coming around the final bend, Kent decides to try and drift, but spins out, knocking himself into the tire wall and causing Julia to swerve and hit the wall too trying to evade the rain of tires from Kent's accident. Sarah about to pull to first hits a chunk of rubber from one of the many busted up tires now scattering the track, and I decide to slow down and hug the outside and serve through the mess. Punching the gas, I take the finish, and first place. Jared and Ellen finish second and a distant third. As we're flagged into the filling station, and the last car parks, the engines cut and everyone hops out to meet up with the rest of the staff in the viewing area.

Tara turns on her mega phone, and congratulates the victors, and announces that while we won, the prizes are transferable, then proceeds to hand out tickets for redeeming said prizes. All of a sudden, Jared, Ellen and myself are swarmed and bombarded with offers. New shoes, tickets to shows, nice dinners with all expenses paid, the works. Jared caves and gives his away to Julia, and Ellen gives hers to Sarah, hoping to cash it in for owing her later. I keep mine and return to the chair from earlier to see if I can get a good look at Jenna who's probably sweating through her shirt showing off her glistening cleavage.

As an hour passes of jokes, laughs, pranks and just having fun, Tara announces we're all expected at a restaurant about 40 minutes away, giving out bus directions, driving directions, and recommending giving those who came by car, drives to those who didn't. I decide to offer a ride to a few, but no one is really interested in going as its hot, late and far away. So I say goodbye to my friends, thank Tara for the winning ticket and head to my car.

As I get to the parking lot, there's someone at my door, I figure it's parking authority, so I pull out my phone to take a check of the time, and then send a quick text and get ready for whatever the problem is. As I finish with my phone, put it back in my pocket and look back up, I see that it's Jenna, and she's waiting while killing time on her phone as well.

"Uh, Jenna? Need something from my car?" I ask.

"Yeah, sorry. I didn't know when you were leaving, but I saw you drive in and figured I wait a few minutes, maybe catch you as you left" she replies.

"Well, what's up?" I inquire.

"Could I either get a lift to the bus, or home if it's on your way? I called a cab, but they said they'd be at least 40 minutes before they get here, and I figured I'd call back if I couldn't get a ride from someone first. I'm happy to pay you for the ride, I just didn't want to wait almost an hour if I could get a rid now from someone." Jenna replies with full detail.

Without much hesitation, I respond and inquire with "Yeah, no problem at all. I'm in no rush to get home. Where do you live?"

"About a 3 minute drive from work." she responds.

Not actually caring where he house is, as I'd drive her to Paris from Hong Kong if she'd asked me with that revealing tank top on.

"Yeah, I can swing that. Don't worry about gas money though, the company alone will be nice. Long quiet drives at night tend to get me tired and I don't need to end up in a ditch. You're pretty much doing me a favor." fulfilling her request.

"Cool, thanks. I owe you one anyways." she humbly says to me, ending the conversation.

I open the doors, and we belt in, starting the car and pulling out of the parking lot. As we hit the road, after a brief moment of silence, she opens up.

"So, I was hoping you still had that prize ticket, are you willing to trade for anything?" she cuts right to the chase.

"Yeah, but only if it's something I want more." I respond with an open ended opportunity.

"Well, has anyone offered you anything close? My family is heading out for a 2 week for a vacation out of the country, and I really want to go with, and this way I have a good chance of coming along, it's worth a lot to me. Seriously, I'll pay you a weeks worth of wages if you trade it to me. Is that cool?" she pleas.

"Tell you what. I'm going to come straight open with you and hope it doesn't come back to bite me, I don't want judgment, I don't want you to read too much into it, I'm just going to be honest, and put my cards on the table with a request. Are you OK with that?" I offer, with hesitation and hope.

"... s-s-sure. Ask, as long as it's not illegal or something. Actually, even then, it depends. What did you want?" she says, openly seeing what the offer could be.

With more anxiety than any request I've ever made, I spill my guts, "I think you're crazy hot, and I really really want you. I'm sorry if that makes you feel uncomfortable, but I want to be straight. And, well.. if you're open to it, I want to have some fun with you to finally get some of the fantasies I've had under my belt, and see if it's everything I've hoped it could be."

About 10 seconds pass, but it feels like a life time.

"I'll do it. But only if you can get me the other 2 prizes too. Otherwise, that's a bit much. But I'm super flattered by your comments, and I'm not uncomfortable. It's nice to feel attractive."

Realizing this is my shot, I tell her I want to pull over a minute, and make some phone calls. I call Jared and Ellen on speakerphone so Jenna can hear, and say I'll pay them each $1,000 for their prizes, if they give them to me, no questions asked. They agree, with confusion, but happy agreement.

"Do we have a deal? I held up my end." I ask, hoping she'll keep her word.

"Yeah, we're on, but can we get off the road, and find someplace less open?" she proposes.

"Done, gimme a few minutes." I finish with.

I drive about 10 minutes, and find a building that is private property, closed for the day, and park behind from street view so no one will find us.

"OK, so what do you want? I'm not willing to do just anything, but I'll keep my end up and we'll see what you want to do." She opens up to negotiate.

"Well, I just love your boobs. I'm a huge boob guy, and I would love to do anything you let me to them. Suck them, squeeze them, fuck them, motorboat them, cum on them, really anything you'll let me. Frankly, I want to just fuck you. Doggy, cowgirl, missionary, whatever you're down with, I want to finally just fuck you. I'll be playing with your rack the whole time, I just love it, so just a heads up. I want a blowjob, till I cum, and I'd love it if you swallowed, it's just fuckin' hot. I'll return the favor, I've wondered for ages what your pussy tastes like. And lastly, I want to fuck you in the ass, I don't know if you're down with anal, but I've had a fetish for it, and I just figured I'd ask." I list all my requests, and wait.

Her jaw just drops, a mixture of overwhelmed, being caught off guard, and just plain speechless from such specifics. She composes herself and says with a bit of a crack of hesitation "Yeah, I can do all that. But if anything. ANYTHING. Starts to hurt, or he do more than what you listed, we're stopping. End of story. That's it. You have 1 chance. Is there anything else, this is your only chance, and I want all 3 tickets"

"Can I take a video, or some pictures? I want to remember this, and some parts of you for the future." I add to the list.

"Only if I'm comfortable with what you want to record, and make sure no one ever can see them. No internet bullshit, nothing. Agreed?" she firmly enforces.

"Agreed" I happily reply.

I stick my hand out to shake, she returns the gesture.

"OK, how do you want to start?" she asks a bit shyly.

"Tell you what, let me just play this out on my own, I'll tell you if you need to do anything, and I'll make sure I don't change anything from what I asked. And you just speak up obviously if we have to stop, or you just need something. That way I can enjoy myself, and maybe you might enjoy a few things to. Just, no judgment or any bullshit that kills the fun, that sound cool?"

"Yeah, lets get this over with," she says, undoing her seat belt and starting to sit up.

"Get out of the car first, by the trunk, it's warm out and we have more room," I start instructing.

"K." She follows with.

We both get out of the car, head to the trunk, and I put my phone on the side of the trunk, and set the camera on, getting her in full view. She stands, back against the trunk door, and waits for me.

"Ready?" I ask, hungry to start.

"Whenever you are." She responds, about to keep up her end.

I go right to take her shirt off, as she lifts her arms, letting me drop it on the trunk, showing off her spectacular rack. I pause for a moment and just enjoy the view. Pushed up and popping out from the bra. Then I reach behind her to unclasp her bra, and slowly pull it off her her shoulders to let her sweet soft perky tits be revealed, and all of a sudden, I feel like it's Christmas, my birthday and I won the lottery all at once. They they were, staring right at me. Unobstructed, free hanging, and just waiting for me to enjoy. I was in such awe of this moment that I've fantasized about that I was standing there stunned and staring, not a care in the world.

She suddenly says "Are you going to do anything? Or just stare?"

I snap out of it, realize I've probably been stuck in a daydream stare for at least a minute, and lean my face in between her breathtaking, warm, perfect boobs and use my hands to press and squeeze them around my face, soaking in the moment, reveling in my opportunity to do just about everything I've always wanted to do.

I pull my face out, and start sucking on her nipples, alternating back and forth every few moments. Taking time to give them the proper squeezing and soft bouncing I so often wanted to give them when I saw her at work. I continue sucking, tonguing her nipples, as they get wetter and erect from the foreplay, I can feel my own cock already damn near splitting my pants apart. I've barely started and I already am ready to pop.

"Fucking hell Jenna, I'm going to cum, I can't believe I'm to close already. I want you to swallow my cum. I don't want it to go to waste. Get on your knees."

Jenna takes to her knees as I unzip and pull down my pants and underwear, my cock has already been throbbing and pulsing, trying not to blast a load in my shorts before I can use it properly.

"Suck it out Jenna, I don't want to miss a drop." I say about to flood her cheeks.

She barely puts her lips on it before I can feel my balls spewing cum out like I'm putting out a house fire and I can actually see it almost getting out of her lips and she starts swallowing, trying to keep up. I close my eyes for a moment and realize what just happened. And I already am back to being at full mast.

"Get back up here, I want more." I order, watching her swallow my last shot of cum as she gets off her knees.

"Close your eyes, lean back," I command, ready to take another adventure into those perfect boobs.

I hold them by the sides, and stick my face back into them, and shake my head, motor boating. Feeling them bounce, shake and squish around my cheeks. As I slow down, I hear a faint moan from her, which gets my attention.

"Did that hurt?" I ask, making sure I didn't blow my chance to continue.

"No, sorry. I.. I.. I actually started to enjoy it." she says meekly.

My mind just focuses on what she admitted to. She's getting off on my rocking my world with her breasts. I can barely handle it. This is too perfect, I feel like I'm ready to cum again.

"Holy shit, I'm ready again. I've got more for you. Get on you knees again."

She drops to her knees, like she's happy to get more. She opens her mouth wide, and waits for a second. I realize she wants it. She's excited to swallow. My toes go numb. I smack my dick onto her tongue and she nods forward, not just to get my cum, but ready to take it right into her throat. I can feel her cheeks tighten around my now engorged rock hard shaft and she starts to suck. She's working for it. I unleash another load, after load down her throat. Her eyes close, I hear her take a deep breath as I can feel her swallow, and swallow, and swallow. She keeps pace with every drop.

As I finish, she pushes further down, as if looking for more to satisfy her. I oblige her. I push forward with my cock to meet her enthusiasm. Next thing I know her lips are down to my stomach, her bottom lips reach my balls. She has my whole member not just in her mouth, by down the throat. Every single part of it. She starts to moan again as I can feel her tongue starting to massage my shaft. She doesn't pull off, she doesn't let go. She holds my whole cock in her throat for at least 30 seconds. Just savoring it. I almost panic, not knowing I keep living my fantasy, or enjoying the moment. I reach for my phone, and take a picture.

She hears the shutter, opens her eyes, and smiles. She doesn't care. She's gone from my coworker, to my fuck toy. This isn't about what I want anymore, she wants it too. I'm pretty sure the deal is over, and she wants a hard fucking. Well I'll be damned if I'll say no to that.

I pull my cock out, she gasps, grabbing for it.

"Please, more. I need it. Please." she begs, cum and spit dripping from her chin and lips. It looks so fucking hot and dirty, I'm almost willing to just be content with this, but I have other plans.

"Later, we have more to do. Stand up." I request, with intent.

She stands up, wiping the cum and spit from her chin, and licking it off her hand. What a cum slut. I can't keep my eyes off her. This is worth 10 times what I had to give up. I reach for her pants, and pull them down slowly, only to realize her thong is literally so soaked it's making her pants wet. Her pussy is literally dripping she's so wet. I realize this is something she wants almost more than me. Her body is begging for it. She's drunk on cock, and she's desperate for more. I pull her thong off and pocket it, possible souvenir for later.

I grab her shoulders, and turn her around. "Face down on the car" I tell her, pushing her over. Her ass sticks out, her pussy dripping on the parking lot, she's ready for anything I want to do to her. I don't bother teasing, or taking my time, I just ram my cock home. Every inch into her melting pussy. My stomach is pressing against her ass, my balls are pressing against her pussy lips. She bites her lips, and tries to start grinding on me. I pull back, and start into her, as hard as I can, by the third time, she screams for a brief moment, her head tilts back and she starts to cum.

I can feel her pussy tighten on my cock so hard I can't move in and out of her anymore. So I just keep swaying and gyrating my hips to keep some motion and sensation, but I can already I feel her gush on me, it's coming out like a fucking flood. I grab onto her rack and squeeze just to hold on tight. Her back arches, her teeth and lips clench as she fucking moans like a beast under her breath and her legs buckle. Her orgasms are so intense, she can't hold herself up. I let her ride it out for a few moments until she gets her composure.

"I'm sorry, that's never happened. I can't believe I needed that so bad. I almost passed out. Fuck. That was amazing. I want more if you do." she says to me, ready to take me further.

"You don't even need to ask, ready when you are." I try to play cool, but thinking I just want to get back inside her.

She reaches behind her with a free hand, and guides my dick back inside her now fully lubed up pussy. Ready for another ramming. I start pushing in and out, still feeling the moistness of her recent orgasm making its way out, but using it to my advantage to quicken the pace as I get harder. I take a bit of a risk, and slap her gently on her ass cheek, seeing if she's accepting. She doesn't seem to notice, so I take another slap, harder, leaving a bit of a small mark. She yelps a bit, and her pace quickens. She says nothing and does nothing to stop me. I slap her hard now, leaving a hand print.

"Oh fuck yes, slap that ass. I've been a bad bitch, hit me again!" she yells, clearly getting aroused.

I alternate hands, and alternate cheeks, making her a mix of red and pink on each cheek. Each slap increasing her pace and making her hips push harder into me. Finally I do a double pass and hit both cheeks with 1 big slap as she screams and she loses her balance. She rights herself and puts a hand on her ass where I hit, and squeezes it as it bounces. She's clearly along for the ride, and doesn't care what happens next. So I grab her hair, gently at first and start to tug back. Tilting her neck back, I can see her start to arch her back to let her head go back further.