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.
