Masturbating for a Hooker

I was about 30 when this happened. Every word is true.

Around my 30th birthday, I decided to treat myself to an escort. A hooker. A prostitute. It had been about two years since my last serious girlfriend and I needed some energetic sex and fantasy without, frankly, spending all of the time dating building up to bedtime.

Fortunately, this was in the days when Craigslist was very reliable for connecting with independent hookers, depending on the location, of course. I connected with one woman, a gorgeous ginger named Danielle, with all natural D cups and some gloriously slutty pictures on her website. Heart in my throat, I called her and arranged a visit as easily as I would a doctor's appointment. We made a date for the airport Sheraton two weeks later, on the Monday after I would get back from a work trip.

I didn't cum for the next two weeks. I did beat off, to Danielle's photos, imagining all the dirty, nasty, sexy things we would be doing in the two hours I had with her. When I arrived at the hotel, Dani greeted me very professionally, but didn't kiss or hug me -- she just shook my hand. She excused herself to the bathroom to freshen up, and I took this as my cue to leave the money on the desk, which I did.

Dani reappeared in a very flattering business suit, with a skirt, her smart and sexy bobbed hair framing her elfin face. Quickly I understood what the ruse was. She began a pro forma discussion of travel and tourism in the area. This was the fig-leaf, I was paying her for a "consultation" and then if we were so turned on by each other's company, well, that was our choice. I sat back sipped from the cocktail I had poured, and grinned.

Dani wanted me to be sure that I didn't visit any places in the touristy parts of our city, where guys would be lured in by sexy women who would take all of their money. I giggled and let her continue her advice. And then I said ... why the hell not, unbuckled my pants and shot them to the floor around my ankles.

Danielle's eyes widened and she gave a startled smile as I started stroking my dick. It ain't bragging if you got it, and I have an eight inch cock, very large mushroom head. Danielle hurried up her silly schpiel and started to take off her jacket, then her blouse. I kept jacking off.

Once she was fully nude, Dani motioned me to the bed, but I stayed where I was. "No, let's just do this for a while," I said. Danielle was confused -- why would a guy pay $500 for a hooker only to sit there and jack off? But I was enjoying her giggling, flattered reaction to my masturbation. "I've been fantasizing about you for the past two weeks," I said. "I want you to see what I've been doing when I was looking at your pictures."

Dani slipped out of her panties, turned on her side, and faced me, staring at me through the professional-looking glasses she was still wearing. She traced her index finger up from the bottom of her pussy, over her lips, and then started rotating and strumming her pussy lips with her fingertips for me. "That is so hot,"she said, watching me stroke and pump my dick.

We talked dirty for a few moments. "You like this?" "Is your pussy wet?" "Look at me." "Watch me." "I'm going to cum." As soon as I said I was going to cum, Danielle got up off the bed and held out her hand to me, then walked me over to a full length mirror at the foot of the other bed in the room. Dani got down on her knees and smoothed her hair back with both hands, still looking up at me through her glasses. I took this as my cue to cum on her face, and I did, trying to keep it out of her hair.

Two weeks' worth of horny thirty-something sperm showered her face and neck. Thanks to the glasses, she was able to keep her eyes open throughout my sticky fusillade. Danielle cheered me on throughout the cumshot. "Cum on my face, cum all over me, shoot it all over me," she purred, and I readily obliged.

Weak-kneed, I retreated to the bed to get my stamina back as Danielle stood up smartly and strode into the bathroom to clean my cum off her face. She came back into the bedroom clean and smelling of fresh perfume, and we made cute talk. I still had another 90 minutes with her. When I got my erection back, we did so many other things together. But the masturbation that kicked it all off was the hottest part of my rendezvous with Danielle.