Trip length: 13 minutes. Trip distance: 3.8 miles.
Fare: $11.36 Year: 2015.
Song of the trip: “Roxanne” by The Police
It's a sleepy Friday night but a fare earlier in the night had brought me up to Stanford University and I haven't been able to get away from the area since. The Stanford kids are generally decent enough riders, but sometimes things can get a little dicey.
What I'm trying to do right now, though, is figure out what the hell is going on.
About an hour ago, I brought the car to a stop in front of one of the dorms, and the phone said I was waiting for someone named Kyle. But a Kyle was not forthcoming. Instead, a brunette girl sauntered out, carrying a bag with her. Lovely, no denying, dressed in a rather slinky black dress, the classic little black dress that every girl keeps in her closet to make an impression, or so I'm told. No one's ever used a little black dress on me before. I can't tell if that means I'm too easy to manipulate, not worth the effort or just not found anyone who wanted to impress me that much. Maybe a combination of all three.
“Kyle?” I ask, when she opens the door.
“He sent a car for me,” she says. “I'm your fare.”
She had a remarkable figure, and a sense of confidence that I'm sure any man would find attractive. And for just an instant when she gets into the car, she turns that megawatt smile my direction, and at that moment, I truly understand why beautiful women make men do stupid things. Her hair was a shoulder-length bob, and her makeup was impeccable. It was the kind of look that seemed intent on capturing the attention of every set of eyes in the room when she entered it. She almost looked like she was going to a formal dinner of some kind. Gussied up like Christmas morning, and set to make a solid first impression.
The beauty didn't want to provide her name, much less engage in conversation, so I simply let the music fill the silence. Some people don't like to talk, and I don't mind. To each their own mood. She spent much of the time typing into her cellphone, messaging to one or more people, although she would look up every so often, just to get her bearings.
We drove about twenty minutes to the western edge of Palo Alto, to this ritzy hotel that I felt too cheap to even be in the parking lot of, called the Rosewood Sandhill Road. The girl starts to get out of the car and then pauses and reaches into the little clutch she's been keeping on top of her bag, pops it open, pulls out a five and holds it out to me. “I know what it's like,” she says, and hits me with that spotlight smile again. And then she's out of the car and disappearing into the night.
Half an hour later, I was doing the same thing again, but with a different girl. The name on the account said George. This time it was a redhead, who had sort of a librarian look to her, that fiery mane up in a bun, with a pencil through it, and a dress that was retro in ways that got my attention when she approached. It was alluring while showing so very little, but I'll be honest, the dress had competition for my eyes. I have a weakness for gingers, and it was clear from the dusting of freckles on her face that the shade was probably natural. She wore glasses, but I have to confess I wondered if they were purely just glass lenses that she didn't need. Most college girls these days seem to wear contacts rather than glasses. It almost felt like an accouterment to complete the image.
The cut of the top of the dress was low, daring, but not so overt as to command a room. And instead of only getting the smile when she closed the door to acknowledge my presence, she was smiling the entire time. Not the blinding show of teeth and power that the brunette had had, but this intriguing, mysterious smile, coy and friendly while still not giving anything away. It was impressive, and it sort of put me at ease. I sort of wanted to put Van Halen's “Hot For Teacher” on the stereo. Is that wrong of me?
She had a bag with her, too, one that she asked if she could put in the trunk. I hopped out to pop the trunk, but she smiled at me and bent over to put the bag in herself, although she seemed to delight in giving me an eyeful of her ass when she did. When she closed the trunk, I realized I'd been caught staring, but she only flashed me a saucy little wink.
This girl was a little more chatty than the previous one, asking all about me, where I was from, what had brought me to the Bay, how long I'd been here, was I married, etc. It was a laser-like focus, but instead of making me uneasy, it actually calmed me down. In fact, she was chatty in a way unbeknownst to me before then. She was super intent on me, in a way I wasn't accustomed to. Most people when they get into an Uber, either they're looking for you to tell them a story, to hear what weird things you might have endured, to get you to tell them all about it for their own amusement, or they're looking for an excuse to talk about themselves, waiting for you to hit on that particular word that will let them unload. This, this wasn't that. Wasn't either of those. In fact, if I didn't know better, I'd almost think this girl was hitting on me. But I do know better.
Still, she was asking questions, not because she was passing the time, but because she actually seemed genuinely interested in me. She didn't want to talk; she wanted to listen, and if I wasn't talking, I wasn't holding up my end of the bargain. When my answer started to peter off, she'd ask something else, no judgment, not upset that my words had run out of steam, that I couldn't find something more to say. Just a sign for her to find a new topic to engage me in. And it wasn't a distraction technique, or if it was, it was a damn fine one. I felt like she was... invested in me.
The destination? The same damn hotel as the previous fare. And this girl gave me a tenner when she left. “Maybe we'll have more time together later,” she said, before turning and heading in. And I swear to you, that smile seemed to genuine. “It's been fun.” I have to confess, I did wait long enough to watch her into the hotel, just so I could see that ass sashay out of sight. Hey, at least I'm honest, right?
Which brings us to here and now. Back on Stanford campus, in front of another dorm, waiting to pick up a Clarence. And at this point, I'm starting to see a bit of a pattern, so I'm not expecting someone named Clarence to walk out. I'm right, of course, but still no less surprised at who does come to the car.
The girl who walks out this time is tall, lean and blonde. The California special. She's got a big gym bag with her, so I have to hop out of the car again to pop the trunk and help her load it in. She's at least half a foot taller than I am, built like a volleyball player. I'll bet she's flexible as hell.
It dawns on me almost immediately that she reminds me of that stripper I was talking about way earlier. She's in a Stanford athletic outfit, like a track warmup suit, but the front of the jacket is unzipped down enough so that I can get a hint of that black lacy bra that she's showing off, to my surprise. Much like the librarian before her, she catches me sneaking a glance, and then gives me a reassuring smile that says she's not going to kick my ass, maybe that she even enjoys the attention. That riot of blonde curls is done up in a sporty ponytail, and after the bag's loaded into the trunk, she moves around the car and decides to get in the front with me, setting her little purse on the floor of my car.
People ask sometimes if they should get in the front or the back. Personally, I don't care all that much, but one of the suggestions I usually make to people is that if you've got a lovely lady in your party, sit her up front with the driver. It just makes our nights a little easier, and if you decide to be difficult, it makes us that less likely to spike your rating in retaliation.
If you're a drunk obnoxious dude, though, do us a favor and sit in the back. You're paying for transportation from point A to point B. Sometimes a driver will be fine talking with you, sometimes not. You can ask us to turn the music off, or set it to a station you like. You can ask us to take particular roads, or make additional stops. You can ask us to pull over so you can puke or take a leak. But you cannot, no matter how much you want to, you cannot make us talk to you if we don't want to.
Most of the time, I try and be at least cordial, if not jovial. I'm self-effacing, and always willing to point out how weird our jobs are. If I'm in a particularly good mood, when someone asks, “How's your night been?” I'll respond with “No nymphomaniac supermodel with low standards yet, but the night's still young.” That usually gets a laugh.
I'm almost afraid she'll ask me how the night's been. I'll give that joke as a reflex, and she might, might, say, “Well now you have...” And then what the fuck do I do?
Thankfully she doesn't ask how my night's been. Instead, she goes the other way.
“Enjoying the view?” she says as she stretches out a bit, like a cat in sunlight, a bemused smile on her lips. “If I didn't want you to look, I wouldn't be giving you the free show. I like it when men look at me.” She turns her head to look out the window, drawing in a long breath before slowly pushing it between her pursed lips, as she teases the front of that track suit open a little more. “I could tell you my name is Celeste, but it's Jenny. That's the one thing I don't like the most about all of this... the goddamn lies.”
I cock my head as we're starting to pull off Stanford's campus. “Alright, I'll bite. What the hell is going on at this hotel tonight, and why are you lying?”
Her left hand reaches over and brushes along my forearm, her fingertips just lazily dancing along the skin, like it was just the two of us in bed together. “You're sweet to ask. Lots of people in town. There's a conference nearby so a bunch of the businessmen are holed up there. And I'm lying because nobody wants the truth. Nobody cares about little old Jenny. They want the fantasy. They want Celeste, the athlete, the sport fuck. Bouncy, peppy, pure Californian. It'd kill them to know I'm from Indianapolis.”
I'm driving under the speed limit this time. She seems in no rush to get there, and I'm enjoying both the story and the attention. “I have a hard time imagining you with difficulty drawing men to you, no matter what your name is or where you're from. You're like a goddamn spotlight to moths. I imagine there's boys all across Stanford looking at you any time you set foot in public.”
She bristles with a laugh far wiser than her years, turning her gaze away from the window to bring those oceans of cerulean to focus on me with a hint of mischief. “Oh, silly boy. If I wanted a Stanford boy, I'd just go and pick a few up. No, a girl has to pay the bills one way or another, and the attention of older men is an easy way to draw a salary. By the look on your face and your earlier remark, I'd say I'm not the first girl you've ferried over to this hotel tonight?”
“You're the third in the last hour.”
“Mmm,” she says, lifting her hand from my arm. “All different too, I'd imagine?”
“Well, the edges of the pictures were different, but the subject was all the same.”
“Astounding beauty, but all to very different tastes. I suppose they all appeal to me, though.” I pause for a second, and then it dawns on me. “Wait, you're all working girls?”
She laughs a little bit, and rests her hand on my thigh, just above the knee. I don't tense up, but I do stiffen some, there's no hiding that if she moves her hand much. I can't tell if I'm hoping she moves that hand higher or lower. “We prefer to call it 'girls with arrangements.' Stanford certainly isn't cheap, so why should I be? I have tuition, rent, food, fashion... all of that takes a great deal of money. So, every month, I spend a few nights here, a weekend there, with some gentleman with too much money and not enough company.”
“Can I ask... how is that?”
She squeezes my thigh, just enough to get a further rise out of me. “Awww. Are you worried about me? You're adorable. I can take care of myself. Whores are clever. And most of us have someone who's screening clients for us, doing a lot of the work to make sure that we aren't going to walk into a room we can't walk out of.”
“And the money's good?”
She lolled her head to one side with a sleepy smile, then back, as if she didn't want to take her eyes off of me. “The money's fucking phenomenal. And it's nice to put on a false face and help someone who's lonely.”
“Are they mostly married?”
“Some of them,” she says, giving my thigh another squeeze, just in case I'd forgotten where her hand was. As if. “Not all of them. Some of them I don't even know. I have five regulars. Within any six weeks or so, I've usually seen each of them at least once. Some of them a lot more. The one I'm seeing tonight, Josh, he's an actor, so I see him a bit more than the others.”
I arch an eyebrow a little bit. “The name on the account says 'Clarence.'”
“Oh bless your heart,” she giggles. “Clarence is his assistant's name, who handles all the transportation and bookings. Josh is certainly my most inventive client.” She glances over and suddenly that hand squeezes a bit more firmly on my thigh. “You don't mind me talking about this, do you?”
“Not at all,” I say, although that hand is more than a little distracting, so I'm keeping the speed well under what I normally do. She hasn't complained yet. “What do you mean by inventive?”
She purses her lips in amusement, then pops them a little. “Well. My agent told me before the first time with him that I should expect anything, and if there was anything I didn't want to do, I should get that out of the way upfront, but I said that's silly. As long as he's not out to break me, I can handle anything he throws at me.” She pauses a second before deciding to continue. “He fucked me in the ass within the first ten minutes of me arriving to his hotel on the first time. Bent over the counter in the kitchen area. My feet weren't even always on the ground. Oh, it was so lovely.” She curled her fingertips just a little bit on my thigh, and I had to work very hard not to let my breath shiver. “But the next time, we had a lovely dinner and then relaxed on a couch for almost two hours before we fucked like a couple of teenagers in love, all romantic and sweet.” The tension of her hand on my thigh relaxes a bit, but her thumb starts drawing lazy circles on my flesh. “He's had me bring a partner a few times, which is always fun, and lightens the load a little. And one time, as a celebration for landing a big part, he actually had four of us, which I think overwhelmed him a bit, but what guy wouldn't love three girls blowing him while a fourth one whispers all sorts of dirty things into his ear? Expensive night for him, but he seemed to enjoy himself, and he said he didn't want to make a habit out of it, because he couldn't spend as much time just talking with me. That was sweet of him. It meant a lot to me. I like just sitting on the couch and talking with him.”
“Do you do a lot of that? The girl before you had an uncanny way of making me feel like she wanted to know all about me and that she was genuinely fascinated by me. She didn't want to hear Uber stories or know about how the night had been – she seemed delighted in taking the opportunity to get to know me for me. I can't even remember the last time that happened.”
“Oh, that's a lot of it,” she says, and her hand lifts up from my thigh, as she reaches to draw the zipper of the track top back up just a little bit, but her hand returns right back to my leg after that, graceful long fingers resting on the denim. “It's as much about emotional connection as it is the sex. Don't get me wrong. The sex is important, and if you can't figure out what the client likes, they won't come back to you. But the emotional investment is just as important, and it builds the trust you need to find out what sexual desires they have they won't bring up at the onset. They're clients, but they're friends, too. Partners. They call it 'the girlfriend experience,' but it's just about having that link. They don't have to hide who they are from us. They can cry, they can laugh, they can be silly. They can be less aggressive, or more. They can be softer, rougher. They can ask for specific kinks they think would frighten someone else away, and we tell them it's okay, which I think is the thing they want the most. To know that they won't be judged, for who they are and what they like. When Josh told me he wanted to fuck me looking like a sporty coed, I didn't tell him that he was twisted, that he should be ashamed of himself. I just asked, 'which sport?'” She laughs, her other hand toying with her ponytail a bit. “If the idea intrigues you, I could offer you an introductory rate. No offense, but you look like you're in such desperate need of a good fuck that I might even throw you one for free, just to see the look on your face when you popped.” That smile is sly, almost like the Cheshire cat, as if she's sizing up a meal. It makes thinking a lot more complicated. “You're not a bad looking guy, but the tension in you is visible from orbit. How long's it been?”
“Longer than I'd like,” I admit, sighing a little bit.
“Sure, but what's that mean?”
“Six years, give or take?”
She giggles a bit and slides her hand a bit more up my thigh and squeezes compassionately. “I'm sorry, I'm so sorry, I didn't mean to laugh. That was mean of me. That just means you haven't been fucked in the entire time I've been having sex, and that seems criminal. How do you even stand it? If I go a week without being properly fucked, I'm fidgety and grumpy until I am.”
I can see the hotel just in the distance, and I'm still not sure how that makes me feel at this point. “You get to be an accomplished masturbator, and you try not to focus on the void at the center of your heart too long,” I chuckle, hoping the laugh will let her know I'm not upset. She seems exceptional at picking up subtle cues. “What can I say? I'm picky. I don't want to have anyone in my past I regretted fucking.”
“Mmmph,” she mumbles, curling her fingers once more. “If it were any other client, I'd tell you to drive over in the back side of the parking lot and I'd blow you before I went in, but Josh likes to kiss, and he'd notice that,” she says wistfully. As I'm turning into the parking lot, her hand reaches up and presses against my cock, just for a moment, but enough for her to get a feel for it, and for me to shiver slightly, unable to contain it any more. “Not a small weapon you're packing there, either. Thick. Impressive. I'll bet you've stretched a few girls wide in your time. Such a shame.” Her hand pulls away and reaches down to grab her purse, which she pops open and takes out a card and a pen, writing on the back of it before she hands it to me. “Here. This is my website, and it has the contact info for my booker on it.” The front of the card is simple, embossed with her stage name I guess you would call it, 'Celeste Williams.' On the back, she's scrawled a shortened URL. “If you decide you're interested, I'll give you a first night, the whole night, whatever you want, for $500. You'll have to cover the hotel room, of course, but that's a 75% discount on my normal rate, and I promise you, I'm so worth it. Of course, that's a one time thing. You decide you want to move to the regular, it's the full two grand a night.”
“I'm not sure I can afford even the one discounted night,” I laugh, my voice a little unsteady, like a nervous teenager again, “but I'll certainly think about it.”
She laughs again, soft, like the crackle of Midwestern thunder off in the distance. “What's the harm in having one night of fun, hm? To fuck a coed who will make you cum so many times, you'll be bowlegged for days, who'll purr like a kitten and run her fingers along your chest when you're falling asleep, and sucking your dick when you wake up in the morning? I aim to please in ways you probably haven't even imagined yet. I like to think of myself as the Ferrari of escorts – sleek, fast, dangerous and oh so thrilling.”
I bring the car to a stop in front of the hotel, shifting it into park. “I have a feeling you're addictive, too.”
“Oh honey,” she says, leaning in to let her lips brush against my ear, her breath warm and utterly cutting to the heart of my libido. “I know that I am. But better to play once than to always wonder.” She pulls back, then kisses my cheek, and pulls away, her hand giving my thigh one final squeeze before she gets out of the car. “Don't get up. You can just pop the trunk and I'll handle it myself,” she giggles. “If that persists more than four hours, email my agent, and maybe I'll give the freebie one last consideration. I hate to leave a sweetheart in need. Ciao!” She winks as she closes the door, and I push the little switch down to pop the latch to my trunk from the car.
She moves around to the back of the car and grabs that big gym bag, then slowly brings the trunk down, not slamming it, but giving it enough pressure that it's clearly latched. The perfect touch in all things. Then she brings her fingers to her lips, kisses them and blows it to me before waving as she bounds into the hotel with a relentless energy.
I'm not so proud that I won't admit that I went offline for fifteen minutes so I could drive somewhere secluded and beat off before I went back to work. There was no way I was going to be able to focus with a hardon like that, and the scent of her lingered in the car, that inviting rush of sandalwood and jasmine, with just a hint of cardamon. It made it impossible to think about anything or anyone else while I jerked off.
I made sure that card she'd given me was secured inside my car, as I had something to think about. Might well never use it, but the offer was certainly tempting, like the lady herself.