Arrangements

He glances at her across the car as they speed down the highway. The far off look in her eyes intrigues him, but he doesn't think it appropriate to ask his boss why she's flushed and staring out the window at the horizon. Their trip should only take a few hours; he wiggles a bit in his seat thinking about simply sitting beside her in silence for any given length of time. She's beautiful, but in an intimidating way. Her body is fit and he loves when she wears short sleeves because he can see her toned arms. And when she opts for a skirt at work, her calves make him imagine what it'd be like to have her legs wrapped around his head. Dammit, some days he has to stay seated at his desk for extended periods so his cock will calm down. Her long, dirty blonde curly hair always has this just-been-fucked look, but her confidence and professionalism allows her to simply look beautiful. And her breasts... God, her breasts. He tries to catch glimpses when she bends over her desk or conference table and just a peek of her cleavage gives him material for his morning shower jerk-off, thinking of his dick fucking her tits or shooting his cum all over her creamy white skin.

As the mile markers blur by, he startles when she finally speaks to him.

"Do you have a girlfriend?"

"No. ma'am, I'm between relationships, so to speak."

She nods and turns back toward the horizon, lightly dragging her finger across her pouty bottom lip. He'd imagined sucking her lip a few times. Again, she startles him from his naughty thoughts.

"Do you find ways to cum?"

What the fuck kind of question is that? "Ma'am?"

"Do you find ways to release, do you jerk off, fondle yourself, hire a hooker, have a fuck buddy?"

I'm floored. Never had I imagined I would have to answer questions like this from her.

"Yes, ma'am, I do some of those, but I'd never hire a hooker." Where is she going with this?

"I see. Forgive me the intrusion; I just wondered if a striking man like you was finding ways to release his stress."

Seriously?! Most people just ask what you do in your spare time...

"Ma'am, I..."

"Please, call me Michelle. This clearly isn't a professional conversation."

"...Okay, Michelle. I have many hobbies, sex isn't one of them, but I don't find myself without, if that's a better answer."

She smiles. "Yes, it's a better answer." She returns to her horizon, her fingers now lightly drawing lines on her neck.

As my mind recovers from the conversational blow, I allow my gaze to drift to her lip again, and then her neck, then to what may be under her silk blouse.

"I'm sorry to have been so forward, Austin, I just couldn't help but notice how your gaze lingers on me from time to time. I didn't know if I was walking around with lunch on my face a lot, or if your needs weren't being met."

"Needs?" I manage to mumble.

"Yes, needs. I would hate to think you're not able to fuck someone on a regular basis."

"Ma'am... er... Michelle... I am quite capable of finding someone for "need meeting" purposes."

This is possibly the most bizarre conversation to have with your boss.

"Well good, Austin. However, I'd like to see if I can improve the way your needs are met."

I'm dumbfounded. Did my boss just offer to play sexual matchmaker, or have I wandered off so far in my thoughts, I've entered in the twilight zone.

"I'm confused by your ... uh... proposal, Michelle."

"I'm sorry, I'm not very good at being vague. Austin, I'd like fuck you."

HO...LY...FUCK.

She continues, "See, I've been titillated by your stares. I'm not sure if you're aware, but when you look at me when you think I'm absorbed in something else, there's a hunger in your eyes, which frankly, makes me so wet I have to escape to my private bathroom and finger myself until I cum. The thing is, I enjoy a certain way of fucking. I like to be bold and have my way. What does that sound like to you?

"It sounds like you like to dominate," I squeak out.

"Precisely. I find deep satisfaction in controlling what my partner does. I don't mean it in a demeaning way. I like to think it's akin to ultimate fighting, but with toys and orgasms."

I've truly entered an alternate universe.

"Michelle, I'm flattered, but forgive me, I'm concerned for our professional relationship."

...like if I'll be fired for not fucking her or fucking her wrong, or fucking her too much.

"I understand. This would be a separate, personal thing. Two consenting adults, who just so happen to work in the same place. Yes, I'm your boss, but in this case, I'm just an attractive woman, seeking fun with an attractive man."

I flush, not sure how to answer.

"How about I provide a test, before you consider my offer? Something simple, and I'll leave you to your thoughts for the next few days to see if you're able to separate the juxtaposing relationships."

I glance her way. Her face is relaxed, as if we're trying to decide where to eat lunch.

"O-o-okay," I stutter. Smooth, Austin, real smooth. "What do you have in mind, Michelle?"

She uncouples her seatbelt and her hands are instantly in my lap.

It's embarrassing my cock has been hard for most of this conversation, but it works in my favor at this point because Michelle has unbuckled my belt, undone my trouser button and zipper, and has pulled my erection out to see daylight. Her speed and efficiency in releasing my cock is appreciated at this point, because I probably would have crashed the car had she taken her time.

She gasps, "Austin, I never imagined you'd have such a beautiful cock. No weird veins and bulges. Smooth tip with over and inch before the shaft. And I can tell it's larger than what I'm seeing now since I've only been able to draw it part way out of your pants."

Again, I flush with embarrassment, but also pride. I've never had a woman go into so much detail about my cock with, I dunno, admiration?

"Thanks?" I manage to utter. Yep, alternate universe.

She looks me in the eye, smiles out of one side of her pink mouth, then drops her head to my cock. Some part of me had anticipated she'd do this; if I hadn't been so perceptive, I may have just careened off the highway and killed us both.

Her lips are soft, and she has just enough saliva to allow them to slide around the tip, but not too much that it's dripping down my shaft. Her tongue draws lines from the bottom of my tip to the top as she adjusts her head to partially circle my cock. When she's not able to continue the lines, she uses the underside of her tongue. The sensation is mind altering. Unlike the top of her tongue, the underside is smooth with subtle ridges. The whole scenario is mind altering, really, but what red-blooded man would say, 'Ma'am, you should really stop sucking my dick.' Exactly.

Michelle abruptly sits up for a second, and starts to under her blouse.

"I'm sorry, I'm a little hot right now. Don't worry, I won't take it the whole way off, but if you'd like to fondle my breasts while I suck you off, feel free."

Now this is an offer I fully intend to take her up on at the moment. Her breasts are beautiful. They sit just high enough that you can tell they are real, but just low enough that most of her clothing shapes around the side curve. From my experience, I'd place her at a d-cup for sure, maybe double d.

She only unbuttons her blouse to the top of her skirt and slightly fans it open, allowing me to see her tits in her black lace bra. Her bra isn't really fancy, but the way the lace caresses her breasts and supports them makes me want to grab my cock and jerk off on her chest right then and there.

She leans over to take my cock in her mouth again and I allow her to settle before I reach around her back to touch her breast. Her skin is warm and feels almost like velvet. As her mouth starts working my tip again, I reach through the side of her bra and lightly touch her nipple. Michelle softly moans as her nipple puckers instantly, and the entire sequence almost sends me over the edge.

"Michelle..." I manage to whisper. "I'm going to cum very quickly from... from... all of this..." Am I a thirteen-year-old boy moving to second base for the first time? For crying out loud she's going to think I've never done this.

She abruptly stops and raises her head off my cock.

"Austin, if this is too much, just tell me and I'll stop. We can forget this happened."

Her voice has an edge to it I don't like. It's almost as if she's giving an ultimatum in a business deal.

"Michelle," I utter after I swallow to regain some composure. "This is amazing, but I'm on sensory overload right now, and I'm pretty sure I may crash the car. Not to mention two semi-trucks have passed us and seen your head in my lap. It's... um... yeah... I want to shoot my cum in the back of your throat right now... but I've never been one to cum quickly and not reciprocate my partner." Yep, I sound like teenager getting his first blow job.

She bobs slightly to kiss my cock before she lifts her head to meet my eyes.

"Austin, making a man cum is euphoric for me. I'm not interested in my orgasm right now. Like I said earlier, I like to be bold and have my way. What I'm doing right now is a basic example of that. Your hand felt good on my breast and I wanted to show my appreciation vocally. But if this is too much, then I will stop, and we can forget this. I don't want someone who is soft, so to speak, and can't keep up. I think you can, and it's probably in our best interest you cum quickly before we get pulled over. I want your cock in my mouth, your hand on tits, and in a brief period of time, I want to feel your cum slide down my throat."

I've never been one to get off from reading porn stories, but the way she just spoke to me was possibly the hottest thing I've ever heard described.

"Okay then," I say with a little more confidence. "Michelle, please carry on."

She nods her head with a smirk and again, drops to my cock. This time, however, she takes as much in her mouth as my position will allow, and tightens her lips all the way around my shaft. Her tongue flattens to one side of my shaft before she pulls back slightly and swirls it all the way around my shaft while maintaining the pressure with her lips. After one full circle, I feel her start to suck my dick like a popsicle.

I reach around again to her breast, but this time, I'm not gentle about exploring her skin. I want to match her forcefulness. I want to be as rough as this incredibly awkward position will allow. Shit, I want to pull the car over and bury my cock in her wet pussy, but I know I'm not going to make it that far with what her mouth is doing. I jam my hand into the side of her bra, cup her breast and pinch her nipple between my forefinger and thumb before I start to roll her nipple while kneading her breast.

Her jaw goes slack for a moment as she groans in appreciation. She takes a breath and locks her mouth to my cock again. Her hands are now pulling my trousers apart so her mouth can slide further down to the base of my shaft. I slightly smirk. She has no idea she's only taken half my cock in her mouth and I can feel my tip touching the back of her throat.

As she starts to bob up and down, I notice a semi is keeping pace with us, and the pervert is looking down into the car, watching Michelle suck my dick. I smile a knowing smile at the guy and he gives me a thumbs up. While I've never been one to like to share, this entire event has pushed some boundary in my mind and I give the guy the what's up head nod. It's incredibly erotic to have this stranger watching my dick get sucked my Michelle, and I wonder if this is my indoctrination into Michelle's dominate world.

Michelle senses my momentary distraction and lifts her head. Her viewpoint allows her to also see the truck driver, and she smiles at him, then reaches to her breasts to drop her bra and expose her skin to him. He blows his horn and she drops her head to my pulsating cock just as I start to shoot hot cum in her mouth. The first shot fills her mouth before she slides down and starts taking my cum in her throat. I grasp her firm ass and grip the steering wheel for dear life as I shoot more cum into her mouth. I suppose I'm average in my cum production, but it feels like ten minutes pass as I shoot more and more creamy liquid into her, and she dutifully swallows each shot. The contraction of her mouth and throat when she swallows must be what's intensifying and extending my orgasm. Her mouth has become slippery with cum and the contraction and release of her mouth between swallows feels like I'm driving in and out of a tight pussy.

Thank God for cruise control.

My cum shots start to reduce, and Michelle relaxes her mouth to accommodate the sensitive end of my orgasm. She starts to gently lick my shaft and tip using a feather touch with her tongue, cleaning my cock as I slightly jerk from the sensitivity.

As my cock starts to soften, Michelle sits up, puts her breasts back in her bra and buttons her blouse. I realize we've only driven about twenty miles, but are nearing our exit. Returning to the present reality is surreal. Michelle reaches over and delicately adjusts my dick so she can do up my trousers and belt.

"Are you okay, Austin?"

"Yes..." I breathe out in reply. Holy fuck, I need a cigarette and a nap.

"Well, good," she replies.

In an (even more) unexpected move, she reaches up her skirt and pulls her panties off.

Well, now I know she wears thigh high stockings.

"These are for you," she says as she hands me her panties.

I can smell her feminine scent as I take her panties and shove them in my pocket. I can also feel a distinct wet spot, one I know full well I contributed to. If my cock had any energy left, it would be at full mast again from this simply gesture.

Michelle adjusts her clothing, clicks her seat belt on and reaches for her phone to check emails.

"Oh Austin," she starts and I register her voice as business like, meaning we've moved on already.

I clear my throat to match her tone.

"Yes, Ma'am?"

"I know I said I'd give you a few days to think about our arrangement, but given how responsive you were to, well, everything, to include our nasty little voyeur, I'm moving up your deadline to tonight at 9 p.m. I know it only leaves you about 6 hours to decide, but I have confidence you'll be able to analyze the facts of the event and reach my desired conclusion."

I feel as if she just presented me with a contract, but for what I have no clue. And dammit all, she's right. I would sign away every drop of cum to her mouth right now if I could, but I definitely need to sit and think. Delaying a decision would only drag out the process, and I've never been one to be incredibly impulsive or take too much time to decide.

"Ma'am, that's seem fair enough. How would you like me to report my answer to you?" If she wants to make this business like, I'll play her game.

Michelle looks at me with steely eyes, and I wonder if I've overstepped a boundary I didn't even know existed.

"Meet me in the hotel bar at 9 p.m. sharp."

To be continued...