High Rise Ch 01

I answer an ad on Craigslist for a casual encounter with an older executive in his office downtown. It's my first time doing this, but I've been divorced for three years and threw myself completely into work once the marriage failed. I have been celibate the whole time and have recently realized that while my career successes are nothing to regret, I have entirely left myself wanting. A lot. My ex was very prudish in bed, so it's been a very long time since I've been fucked really well. I'm so horny I can't even stand myself and masturbating just isn't enough anymore. I want a big, hard cock inside me, and this man has said he will satisfy all my needs. His office is only a few blocks from mine, and we agree to meet on our lunch break.

I'm nervous as I take the elevator up to his 23rd floor office. I'm already wet, but it all feels so risky and I'm a little scared too. This is not a familiar feeling for me. I am known as a tough executive and I hold a position of great power in my company, the first woman to hold this position. So I am a little off as I find his office and step into the reception area. His secretary is away at lunch and the office is completely quiet. Then I see him come out of his office. He's wearing a gray suit and a red tie. He's in his 50s and is very fit and tan with hair going almost all gray. He smiles and comes and kisses me on the cheek, welcoming me into his office. He locks the door behind him.

I'm glad you made it, he says.

I almost didn't, I say.

Are you worried?

Yes. I've never done this before.

Are you wet?

Yes.

It's a very nice combination of feelings, he says, scared and wet.

Behind him is a wall of windows looking out on another high rise across the street. There is a partial view of the Sound and I see a ferry heading out.

Would you like to see the view? he asks.

I nod and he beckons me over to the windows. His desk is only a couple feet away from the windows. As I get close to him, he puts a hand around my hip gently but possessively and pulls me closer to the window. He moves me in front of him, so that I am pressed back against his chest. He wraps his arms around me as we look out the window.

Then slowly he starts moving his hands up to my breasts. He massages them gently then slides his hands down my belly to my crotch. I have a pencil skirt on, so he can only cup my mound and can't get any further. He reaches down for the hem of the skirt and pulls it up around my hips and finds that I don't have any panties on. I had taken them off at work in the bathroom in anticipation.

Nice, he says. His slides a hand between my thighs and moves slowly up to my pussy. He grabs it firmly and squeezes, his fingers pressing slightly into my wet hole. Nice, he says again. Then his hands move quickly up to my blouse and he starts unbuttoning it. I can feel a hard-on growing against my ass. I push back against it. When my blouse is completely unbuttoned, he slips his left hand down the top of my bra and grabs my right tit. He squeezes it hard and then takes the nipple between his thumb and forefinger and pinches it.

Oh! His right hand slides back down to my pussy and he begins slipping two fingers up and down my slit. I'm so wet I'm practically dripping and he spreads my wetness all around my pussy and up onto my clit. He starts massaging my clit real slow while he starts nibbling on my ear. Before I know it, he's got my bra unclipped and off with the blouse.

I'm standing there in front of a wall of windows in my high heels with my skirt up around my hips and breasts hanging out for all to see. I am ready to cum, but suddenly self-conscious. I look at the building across the street to see if anyone is there.

That's when I see you in your office, at your desk, just staring at me. I don't know what to do. The man behind me has me completely in his hands. I want to cover up but I also want to cum. I see the look on your face as you watch me. You are shocked, but you are not turning away. In fact, you are watching with much interest.

The man behind me sees you too. He starts grabbing my other breast and massaging it as he picks up the pace on rubbing my clit. I moan. Oh, god. I decide to go with it. I decide it's even hotter to have another man watching me get masturbated. I moan again and lean back into the man. I feel his hard-on getting harder.

I'm going to cum, I pant.

No, not yet, the man behind me says. He stops rubbing my clit.

No! I need to cum! I say. Please don't stop.

Not yet.

I see you stand up from your desk and walk over to your window. You obviously want a better view. I see you unzip your pants just as I hear the man behind me unzip his.

Bend over the desk, the man says in a deep, tight voice. Bend over. Now.

I bend over the desk, bracing my hands in front of me and sticking my pussy up towards the man. God I want his cock so bad. I see you have your pants and boxers down around your ankles and your big dick is out and being firmly grasped by your hand. Your shirt is parted around your dick and you are staring at me intently. You start pumping your dick, back and forth, slow.

I want you to watch him the whole time, the man behind me says. He reaches his hand around so he is fingering my clit again. Are you ready for this? he asks.

Yes!

He takes the head of his dick and starts circling it around my wet hole while he still rubs my clit. Are you ready for this?

Yes! Fuck me!

I see you pumping faster now. The man behind me takes his finger away from clit, grabs my hips and slams his hard cock all the way in me. I scream out. Fuck! He starts pumping fast and hard, god he is so fast and hard. I'm screaming and screaming. Fuck! Yes, fuck me! God I'm so wet and it feels so fucking good.

I feel my orgasm starting to build again. I start moaning and moaning now. I feel it starting in my cunt and then moving up into my uterus. I feel the contracting starting and I moan long and low.

Keep your eyes open! the man behinds me barks. Open your mouth and stick your tongue out. He wants to imagine you are sucking his cock right now.

I look at you. You are pumping yourself so hard now. You have your other hand bracing yourself against the window, and your dick is pointed straight at me.

Keep your tongue out, the man barks again. He reaches his right hand up and grabs my breast, hard. Oh! He then pulls my nipple out and pinches it, hard. OOOH! I grimace in pain. It hurts, but it feels so fucking good. He is slamming so hard into me now I can't keep up with him. My hands keep sliding forward on the desk, and I have to keep pulling them back to keep myself up. He has lost control of his rhythm and he's slamming and slamming into me. I love that he has lost control. I see you are out of control too, and you open your mouth and scream out but I can't hear you. I see your cum shoot out and hit the window in front of you. I see it dripping down the window.

That puts me over the edge and I start cumming too, I am moaning so loud and long. Onnnh. Onnnh. I feel the orgasm wave throughout my body. Ooooonnnnh. Oooonnnh. Everything starts contracting and I'm moaning and moaning. The man behind me loses all control then and I feel his dick twitching inside me as he shoots his load. He is crying out now and he is cumming so hard, pumping all he has into me. He collapses against me, but I'm still cumming. I push back against him, still contracting around his dick. Ooooonh. Ooooonh. You are still watching me, still holding your dick in your hand. I'm suddenly sorry you had to shoot your cum at the window. I wish I could have had your cock in my mouth when you came.

I smile as my orgasm starts to diminish. The man behind me is panting. I keep smiling because he is just a man. He was in control before, but now, he is just another man who will always lose control over a wet pussy and a woman moaning out her orgasm. I smile at you. I think this is the beginning of a very enjoyable time in my life.