Of course, it could’ve just been me. But my ego and I hope not, and she told me early on that she had never orgasmed, not even by herself – and that’s just fucking harsh (I think of the hell I’d go through if the same were true for me…).
So that sucked. Bless her soul, though, she never, ever let the fact that she couldn’t cum interfere with helping me get mine. And damn could she do that. It was about the best sex I ever had. It was odd, in a way; she was meek and mousy (though certainly cute), shy and self-conscious (though she knew she was cute).
She read Cosmo’s sex advice, studied how to please a man and could really conjure up some tricks with her talented tongue. She would fall to her knees, pull my prick from my pants and, after swallowing the whole thing for a while (she was the only woman I’ve ever had who would deep throat me), rub my thickness all over her face. Staring up at me with her grey eyes, she’d roll my tool over her full lips, pert little nose and rosy cheeks. Hot.
And she was up for about anything, too. I’d tell her to come to my place wearing no underwear, no problem. I’d ask her to shave her hairy blond box, presto – she’d show up shorn. I’d come in her mouth, she’d gulp it down – then jerk my still rigid rod on her tongue to make sure she got it all. I fingered her wet pussy in the work place, she agreed to do my best friend if he ever visited and she’d go as many times as I could get it up. Insatiable, agreeable and loving, that was Jill. But anyway, you get the idea, she was a dream. I had a permanent hard-on just thinking about the hardcore hellcat hidden behind her innocent, little girl good looks.
Maybe the best thing she did was ass fuck. Not at first, mind you. When I first suggested anal, she didn’t like the idea. “Have you ever tried it before?” I asked.
“Yes, and it hurt,” she answered, lying. The 22-year-old admitted later she was an ass-fucking first-timer. She put her little hand around my shaft, her thumb and forefinger unable to touch. “You’ve got a fencepost here, and it’s not going in back there.”
I’m persistent, though. Always have been when it comes to women. Lazy in most other endeavors, I guess that’s where my energy went in my younger days. But back to how accommodating she was. Or, more specifically, back to how accommodating her butt was. I began fingering her ass about every time I’d go down on her, and it got to the point where her little brown bud would blossom as soon as I’d pressure it, my spit and her copious cunt juice providing plenty of lube.
With my mouth gently locked in at the top of her pussy – my lips separating the hood of her clit and my tongue lightly dancing over her sensitive nub – the middle finger of one hand would wiggle its way up her ass while two fingers from the other curled inside her vagina, pressing behind her clit. That was as close to climaxing as she ever came, her piercing grunts gaining in volume and frequency until they nearly ran together like one long, loud plea for release. But she wouldn’t breathe and she wouldn’t cum. The lack of oxygen choked off her exclamations, relegating her to a series of panting gasps that would slowly lead to another near orgasm.
Anyway, it was during one of these times – my finger sawing back and forth through her tiny star – that she gave in to my persuasion and promised that my prick could pierce her last virgin place. Like I said, persistence.
If I get inspired, perhaps sometime I’ll relay the story of her anal deflowering. She was a natural, of course. The woman’s lithe body was built to fuck, and though she wasn’t the brightest brain around she was definitely Mensa-level in the bedroom. Even that first time she took it like a champ, holding her shapely pale cheeks apart as I pounded her poor little hole. So yeah, taking her final cherry was fun. For now, though, I’m thinking of another great thing she let me do. Screw her on film. Tape, actually. And one night, I taped us having anal.
She came over right after work wearing nylons (but no panties, natch), a short skirt and crisp white shirt. Sitting on my bed in front of the camera, she worked her hose beneath her knees, slowly unbuttoned her blouse and separated her slender thighs. Shoving one hand inside her shirt, fingers fondled braless b-cups while the other hand wandered to the space between her legs.
I zoomed in on her juicy pussy while she got herself wet and then entered the frame, my dick aimed right at her head. It wasn’t subtle, but she was OK with that, unzipping my khakis and taking my meat deep. I stood on my bed (which in those days was just a futon), turned her ass to the camera and pulled the skirt over her butt as her face flew up and down my dick. Leaning over her back, I spread her cheeks wide, exposing her pussy and anus to the lens.
She knew what I wanted to see and promptly put a finger in her gash. I wet a digit and played with her asshole, gently circling the sphincter until it loosened slightly. From there we performed several positions for the cam, including a hot 69 that featured her taking me to the root. Her eyes watered but she never wavered, she just played with my balls and kept bobbing to my base.
We finished in missionary, her head hanging off the bed and her pretty face staring almost upside down at the camera. I folded her in half so her knees nearly touched her ears, grabbed her wrists and held them above her head for more leverage. Thank god she was flexible. My prick rocked repeatedly into her squelching pussy, her thighs crushed against her tits as her ankles tapped my head.
Her cunt lips clung to my cock as I drove in and out, making sure the cam caught each slam. Her typical moans – rhythmic, high-pitched grunts, really – grew and I kissed her hard, mostly to muffle her cries because I worried they’d worry the neighbors.
A lifetime of riding horses had taken its toll on her twat; it wasn’t exactly tight, unfortunately. But her outer lips held on just right and she was so hot inside that wet cave that I knew I’d blow soon.
“Can I cum on you?” I whispered.
“Cum all over me,” she panted. “Do you want to cum on my face?”
Um, yes! Power fucking her now, I was verging on an enormous orgasm. When it overtook me I jerked out of her red pink, my stick already squirting. I lost two strong streams before I crawled to just below her tits and began jerking; and that’s when I really started spurting.
A deluge of cum cascaded all over poor Jill. Her neck, nose, lips, cheeks and even hair served as a landing zone. I’ve never shot so much in my life. It was like my one and only Peter North moment. A big glob splattered her right eyelid, streaking across her brow. Drops even flew over her head, falling just short of the camera.