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.
