The Escort Chronicles Ch. 01

I exhale deeply. There is only a minute or two until he'll be here and this suddenly becomes real. I'm propped against several pillows in a dimly lit hotel room. One hand is holding onto the corner of a pillow and the other is rubbing my thigh. I think back on the past several hours.

I got the call in the middle of the day from a girlfriend looking for someone to take care of her boyfriend while he was out of town. At first it sounded like a scam, but she was very particular about what they wanted, and she was very respectful about my rules.

Then I find out that he is setting me up with his credit card and someone to help me shop for lingerie. Even though I cater strictly to a certain demographic with deep pockets, this was totally new. It put me a little more at ease as to the validity of the situation, but it also brought some nerves that I haven't experienced before. I have enough experience that things don't typically surprise me, but there are always nerves with a new client. Still, I was surprised by the instructions to go purchase new lingerie.

I was to meet a personal shopper at a very high end clothing store, and she would assist me. However, neither of us were given any idea of what he wanted me wearing. That added some stress as well. Does he want sweet and sexy, slutty and naughty, or just classic and classy sex appeal? Well, he didn't give either of us any ideas, is it possible he doesn't care? Maybe just wants me to choose something I like? Why would he do that? Wait, why do I care?

I couldn't help but wonder if she assumed I was the girlfriend or that I was a hooker. If the latter, I'm impressed by her ability to treat me as very well respected client, which leads me to believe that he must be one...which I suppose fits the category of my typical client, so it makes sense.

I was asked to bring toys, and what I am open to in that regard. As a woman with a love of bondage, I was sure to let it be known that is always welcome, and when it comes to S&M, I'm open to pleasure, not pain. One thing she was very clear about it is that they want me in a blindfold the whole time. A huge piece of this for them is they want this to be totally anonymous. That works for me, I am an upstanding citizen with a career outside of the fact that I fuck very wealthy men for money.

It has been awhile since I got a new client. I have an extremely exclusive clientele and my price puts me out of most men's range. I am also very discreet due to my professional career outside my escort services.

For those who are able to afford me, however, they are fortunate to have a woman who absolutely loves to fuck and get fucked, is incredibly multi-orgasmic, both enjoys and excels at giving oral, and is borderline insatiable. (If the truth be told, even with my multi-orgasmic blessing and the fact that I can often make them cum multiple times too, they are usually done before I am.)

I am curious about the man that I will be servicing tonight. With such an exclusive clientele, most are regulars, and while great for the bank account, it can get a little uninspiring. I always enjoy sex, but it has been a long time since something blew my mind. And as the paid giver of pleasure, I am seldom in a situation that I get to just focus on enjoying and receiving. I also have the rules that are designed to protect me and establish boundaries, but they also can be a hinderance to feeling pure passion (not that it is typically part of this kind of transaction anyway, but sometimes I miss just having non-contractual GREAT sex.)

The Rules...I wonder how he will be with them. His girlfriend seemed very agreeable. It was cute, she even asked about kissing. I laughed and told her that Pretty Woman is only a movie. But I did tell her that I won't kiss him unless he kisses me. No fucking me without a condom. No cumming inside me or in my mouth. Anal is not a guarantee, I reserve the right to refuse it, but if I'm feeling it in the moment, it is a possibility. Still, it is easy for the girlfriend to agree, she probably wants these rules too, and she's not the one with a cock fucking me. He might have a different feeling on them.

I got a good look at myself in the mirror before I put the blindfold on. The lingerie he told me to pick out and paid for is sexy with a touch of slutty, black lace and strappy. The black leather collar that he left for me in the hotel room and requested that I wear really completes the outfit. I look hot as hell and I know it. I put on some deep red lipstick which will make my lips stand out when they're around his cock. It was almost a shame to put the black satin blindfold on, my hair and makeup look fantastic and I look beyond fuckable in this ensemble.

The door opens and I hear ice clinking in a glass. I wait until I hear the door close and then I say "John?" He greets me and I hear him put the glass down. I apologize for not having music playing like he requested. He says its okay and a couple moments later club music fills the room. Yeah, I can fuck to this.

He tells me I look amazing and asks if he can take a picture. I pause for a moment because I hadn't thought about that. It isn't a request I get often, but I'm also not usually blindfolded. But he's right, I do look amazing, so I allow it, telling him it needs to be just for him.

There is a pause and then I feel a hand start to slide up my thigh. "Is it okay if I touch you?" he asks me. I laugh softly at this. We both know he's paying me to be here to fuck him and he's politely asking if he can touch me. I reach out and make contact with his chest.

"You're going to be doing a lot more than touching me tonight. Yes, I would say its okay if you touch me. Is it okay if I touch you?" I start smoothing my hands over his shoulders as I feel his sliding all over me. He tells me it is, and I start unbuttoning his shirt. This act of feeling the buttons come undone and touching the skin beneath it while hands move over me has an incredibly erotic effect on me. I slip my hands into his shirt and feel the skin underneath as I explore, finding nice broad shoulders and a strong chest under my hands.

I have been blindfolded many times before, but never with a stranger paying me for sex. I'm getting turned on by the minute. His hand finally moves to my tits and I moan softly and arch into his hand. I told his girlfriend that I would only kiss him if he kissed me first, but I'm dying to feel his mouth on mine. I move my hands up to his hair and bring my face to his. I press my cheek to his and just the softest brush of my lips against his...I'm blindfolded, it could have been an accident.

I ask him what he wants, and he asks me the same. I remind him that this night is all about him, that I'm here to service him. He promises me that I'm going to be very well fucked by the time the night is over, and admits that he hasn't done this before.

I tell him that it has been a long time since I've been well fucked and remind him again that tonight is all about him and tell him that usually my clients want me to suck them and fuck me and that's about it. His response to that is to push my hair aside and start kissing and sucking on my throat. This is a sensation that drives me wild but also makes me jumpy. I start panting and in the same breath I tell him "there is one other rule that we didn't talk about. No marks."

He lifts his mouth to my ear and I feel his lips and breath against me as he says "there is probably going to be a big handprint on your ass." I remind him firmly no marks where anyone can see it. His response is to fasten his mouth on my throat again. At this point I don't care if he marks me, I can tell that I'm going to cum any moment.

I feel his hand cup my breast again and my head falls back and I moan out an orgasm. Turning my head, I press my forehead to his, lips just inches apart. I slip my hands around the back of his neck as he asks me if I just came. I laugh lightly and rub my cheek softly on his "I guess I should have warned you. I cum a lot."

His response is to pull the lace of my bra aside and start sucking on my nipple. My tits aren't generally super sensitive, but whatever he is doing with his mouth is fucking amazing. I start running my fingers through his hair, my back arching to get closer to that incredible mouth, and then another orgasm throws my head back.

I feel his hand cup and hold my pussy firmly, covering it fully with his hand, but there is no penetration or playing with my clit, just holding onto me. The simple contact is driving me wild. There is a patience to the way he is holding me, like he knows I am going to cum from this lack of movement, that this simple hold is going cause intense arousal and eventually orgasm.

He comments on how wet I am, and I pant my response. He has me incredibly turned on, not to mention that I have cum a couple times already. I try to grind against that hand, but his cupped hand doesn't move and his mouth continues to focus on my breasts.

This cupping of my pussy is a whole new sensation for me and he has me firmly in his grip. The lack of control I have in this situation combined with the pleasure and newness of the cupping puts me over the edge...I moan out the orgasm I think he was waiting for and my head drops to his shoulder.

He surprises me by taking my hand and fastening a wrap around it. I'm a sucker for bondage, but I don't know this guy. I gently remind him that the goal we agreed on is no pain, only pleasure. His response is to lock my wrists together, lifting them to the dog collar and fastening them there too.

Then to my shock and pleasure, I next feel his tongue on my clit. I didn't expect this from a man who is paying for sex. I slide my leg along the side of his body since I can't touch him. He doesn't stay down there long, but I definitely get a few more orgasms in before he stops. His tongue is incredible and not being able to have my hands on him or see him made the sensations so much more intense.

My pussy is soaking wet at this point and I am dying to fuck this man. I'm a pro, I am trying to play it cool, but he is making me want him. It is going to be hard to abide by my own rules. I want to feel him inside me, and I want him to pour cum into me. The fact that my hands are locked into place makes it even harder. I want to feel him.

As if he read my mind, he grabs me by the bonds and pulls me up onto my knees. He slips behind me and plays with my tits and lowers a hand to rub my clit. "I want you to suck me" he breathes against my ear. I turn around and he unfastens my bonds but leaves the braces on my wrists. I drop my head and take his cock in my mouth. I give great head and I know it. With how bad I want this man, I want to make sure that he gets a taste of what I am capable of, so I don't ease him in.

As I expected, he starts to lose control right away. "Oh my God, you're going to make me cum already." I pull my mouth away just long enough to tease him that he isn't allowed to cum in my mouth before I practically swallow his whole cock again. He lets me suck him for a moment longer before pulling me away.

I stand up on my knees and press my body against his, sliding his cock between my legs so it is rubbing against my wet pussy. I brush my cheek against his and he starts stroking his cock, sliding it against my wetness. "You made me cum a little" he says and rubs some cum onto my nipple. I'm dying to suck it off his finger and lick it off my tit, but I don't want to open that door. I was clear that he can't cum inside me or in my mouth.

He lays me back on the bed and gets on top of me, rubbing his wet cock head against my clit, sliding it up and down my pussy lips. I orgasm quickly, and wiggle so that the tip slides into me. "You can't fuck me without a condom" I pant, even as my hips move to take him a touch deeper. He slips just the tip of his cock in and out of me, continuing to give attention to my throbbing clit and teasing my opening with the tip. I want to feel the ridge of the head of his cock, the soft pop when it penetrates me.

I slide my hand down and start stroking him, pressing the head against my pussy so it is soaking with my cum. Who am I kidding, we both know he is dripping into me, and since he came a little already, more has probably made its way inside me.

I want to feel his whole cock. I love the teasing of a cock head playing with me, it is one of my favorite things. But this man needs to fuck me. His foreplay is amazing and it is killing me. He tells me that he wants to feel my pussy. This is exactly what I want to hear, but I have to hold to the rules. Still...it is what I want... "Everything is available for a price" I tell him.

He pauses at that, leaving his cock pressed against me, and buckles my hands against the dog collar again. I'm at his mercy and I know it. Then suddenly, he thrusts all the way inside me. I moan instinctively. This is what I want. This is what I'm dying for, but it breaks all the rules we agreed to.

"You shouldn't be doing that" I barely get the words out and he is thrusting into me again. For a brief moment, my brain thinks not of The Rules, but the agreement that I made with the girlfriend about them. HIS girlfriend. I've broken not only my own rules, but the strangest bond I have ever had with another woman...I couldn't help it, I NEEDED this.

All thought slips from my mind when he thrusts hard with that cock that I was craving, and I cum all over it, feeling my wetness soak him. No condom, just this amazing hard cock that I have been trying not to beg for. I can't help but thrust my hips to meet his and wrap a leg around him.

I keep saying things about breaking the rules and shouldn't be doing this, but I'm definitely not making him stop...and having a leg wrapped around his waist is sending a different message. I want my hands on him, but they are still tied up so I touch as best I can his chest, face, and hair. I can suddenly feel his cock start to throb, and I tense lightly and start to pull away.

"My cock is throbbing, I'm trying so hard not to cum" he tells me. I remind him again that even though everything is available for a price, he isn't supposed to cum inside me. "I want to cum in you" he tells me, but I refuse. Then he moans and pulls out. "I'm cumming on your pussy!"

I relax and lay back. I can handle that, again, I know he was dripping into me, so spilling onto my pussy lips is fine. He lays down next to me and I turn my head towards his. I still want to feel his lips, but I promised that I wouldn't kiss him first.

Suddenly there is a warm vibrating sensation on my tits. Soft pain, not enough to complain about, but just to draw awareness to the spot. "Nipple clamps" he tells me, "I've never done this before either." I admit that I never have either.

Before I have time to give it much thought, I feel his fingers sliding over my cum-covered pussy lips and clit. Then thrusts his wet fingers inside me. "What are you doing?" I ask teasingly.

"You know exactly what I'm doing. I've already spilled some cum inside you, and you rubbed my cock against your pussy when it was covered in my cum. I want to fill this sweet pussy so bad. I'm putting my cum inside you, where I want it to be."

I arch into his hand and moan at his words. I want it, he knows I want it. This was supposed to be a transaction, but I want to fuck this man. I want to feel everything I would with a lover. I want his bare cock inside me, I want him spilling his cum into me, and I want his mouth on mine.

I hear a click and then my hands are suddenly free. I immediately slide them up to those broad shoulders again. He is fully nude now, and my hands explore his chest, shoulders and back, before stroking the stubble on his face.

I ask him to remove the nipple clamps, as one is starting to hurt. They are off me almost instantly, and he asks if I'm okay. I nod and gently pull his head toward my chest. "You could make them feel better..." Then I feel his mouth around the sensitive nipple. He is gentle and sucks lightly and works his tongue around the tip. I sigh and arch my back towards his mouth. He asks me again if I'm okay, and when I murmur "Yes" he lays down and pulls me on top of him.

"I want you to ride me." I remind him that he needs to put a condom on. (At this point I'm playing semantics, there is no point, but that's the rule.) He tells me he has one on, and so I slide onto his cock. I can feel the difference, and it is disappointing. I want to feel him again.

But then without warning he starts fucking me from underneath. Oh my God. I'm feeling his cock thrust up into me, and my tits are bouncing at the motion. I cum hard and loudly. My hands drop to the bed above his shoulders to balance myself so I can ride him back. But it becomes clear very quickly that he is in control of this situation, and this is for my pleasure and to make me cum...a lot...and it is definitely working.

This is a whole new experience for me. Typically when I'm on top, I take over and fuck my clients. He is completely in control right now, thrusting up into my pussy with force. I'm sitting on his cock, but he is definitely fucking me, not the other way around. The orgasms are hitting me with rapid intensity.

I want to fuck him back, but the combination of his firm grip on control of the situation and the intensity and frequency of my orgasms, I'm being taken for a ride, and now there is nothing I can do except moan, scream, pant and enjoy.

Finally, I pause for a breath after another orgasm, and I feel his hands move to my wrists and start guiding them behind me. I'm still sitting on his cock and I realize his intention, so I lean forward to make it easier for him. There is a click, and I'm bound again.

I lean backwards, shifting so that my tits are clearly on display, my chest pressed forward as my arms are pulled back. I keep leaning until my clit is exposed, and immediately his thumb is rubbing it. I start slowly sliding up and down on his cock while he plays with me. This is a balancing act and it gives me a touch of fear that I'm going to fall and hurt one or both of us. But I imagine that he is getting a hell of a show, and I'm pretty fucking flexible, so I arch further backwards and start riding him a little faster.

I want to pleasure him. I'm here to be his fuck toy and for him to use me however he sees fit, but with how this night has gone, I want him to want me. I want this to be something that he wants again, and I sure as hell know that I want him to fuck me again.

He figures out that I am not going to cum like this, and pulls me upright. I tell him that his girlfriend said he likes it when she rides him and ask if he wants me to. We have a momentary power struggle as he is holding my legs and rocking me back and forth against his cock, while I'm trying to get onto my feet so I can ride him hard. I win, and start bouncing up and down on his cock.

He moans that this always makes him cum. Hearing those words and thinking about him filling me pushes me over the edge and I cum again. I'm struggling with my arms bound behind me to keep this motion, and he realizes it quickly. "I want you bent over." The words come out of nowhere, but I slide off his cock and sit on my knees on the bed until I feel my wrists part. Then I drop to my hands.

I know how assuming this position can look hot as hell, so I arch my back deeply, lifting my ass into the air, spreading my legs, and then toss my hair and look back over my shoulder. Moments later, even with the blindfold on, I see a flash and I ask if he's taking pictures. "you're so fucking hot, I had to." I smile and lower my chest to the bed to make my pussy more accessible (and better access to my G-spot).

Without warning there as a sharp slap on my ass and I flinch slightly. Two fingers rub lightly into my pussy and a thumb starts to rub my asshole. I can't stop my body from responding...my legs spread a little wider to take his fingers deeper, and my ass presses back against his thumb. He laughs and starts to slap his cock against my pussy. His other hand lifts me up and wraps around me to fondle my breast.