Andy’s Anal Adventures: Jill


Jill couldn’t climax. That was too bad for her, definitely, but I never let it bother me all that much. I mean, I tried. Hard. I’d go down on her until she nearly hyperventilated, but it just didn’t happen. I think it was her breathing. I’d eat her and she’d gasp in short, panting bursts that never quite let her crest.

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 almanbahis 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.

Like a good girl, Jill grabbed my joint and coaxed a final stream into her waiting mouth, latched her lips around the crown so she could suck out some more and then jerked vigorously until I was totally dry. Oh my god. I leaned back on my knees, my drained sack swimming in a cum puddle collected between her firm tits. Her upper torso plastered, she licked leftovers off her lips, looked down and giggled.

“Oh my god I’m sorry,” I said, wiping the jizz away from above her eye.

“It’s OK,” she answered almanbahis yeni giriş as I reached above her to turn off the cam. “I’ve never seen so much cum in my life.”

“Yeah, me neither,” I sighed, spent. She took a shower and I took her out to dinner. Hey, when you explode on a girl’s face dinner seems like the least you can do, right?

But when dinner was over, she was naked and on her knees within moments of our return, ready for round two. She sucked the remnants of our first fuck off my stick and lashed my circumcised head with the tip of her pointed little tongue.

I positioned her in another 69, this time with her ass inches from the camera. While she inhaled my thickness I slurped at her box, occasionally making brief forays all the way up her swollen slit – still puffy, pink and battered from our earlier tryst – until I rimmed her puckered anus. Once wet, it winked for the cam.

I briefly forced a finger inside the vulnerable hole, her insides gripping at my knuckle. When I removed it, I dug my hands into the soft flesh of her cheeks, holding her open so the cam got a great look at her separated pussy folds, tiny clit and, most importantly, slightly spread rectum. Her tiny browneye wasn’t so tiny now; the small black circle gaped slightly for the camera. That slight gape would soon be a yawning cavern.

We got up so I could rearrange the camera and she stayed in doggy style, her ass still pointing at the lens. She reached a hand between her legs and worked vigorously, fingers disappearing within her own welcoming body. I didn’t notice until later when I watched the tape, but she wasn’t just pleasuring her pussy. No, she was digging the middle digit deep into her ass and rooting it around it an attempt to prepare for my invasion.

I lay down and she sat her groin over my hardness. Facing the cam, her blond curls framed her glowing, impish face. “Where do you want it?” she playfully asked, stroking my cock gently against the skin between her holes.

“Where can I put it?” I replied, knowing the answer.

“Anyplace you want.” God I loved hearing that.

“Put it in your pussy,” I said. “Let’s start there.”

She slipped it in and rose to her haunches, riding me in reverse cowgirl while I guided her hips up and down. Reverse cowgirl. Sometime back, that had been her idea, too; I’d sure never done it. I had never even heard the term before. I stared at her tasty ass and slightly agape pucker as she rose and fell, her cheeks slapping my pelvis on every stroke. Moaning each time my spear separated her walls, she kept the bouncing up for awhile – the woman’s horse riding had left her with strong quad muscles – before I turned her around.

Her small jugs stopped jiggling for the camera and she stood briefly to stretch her long, lean legs, knowing another tight muscle was about to get stretched.

“Where can I put it now?” I asked.

“In my ass,” she answered. “Put it in my ass.”

Upon turning, she immediately directed my dick to her back door. For as often as I’d done her there, entry was never easy, and as she tried to slip the wide tip into her rectum, my cock instead slid back into her pussy. She drove down my girth in one swoop and realized I missed my intended target.

“I knew that was too easy,” she said, giggling. “I was wondering why it didn’t hurt!”

I paused for a second as I returned my cock to nether region. “Oh,” I asked, not sure what I wanted to hear in reply. “It doesn’t hurt too much, does it?”

“It hurts,” she answered, impatiently wiggling her ass and prodding my prick with her hole. “But I want you to do it.”

Like I wasn’t hot enough for her already. As I’ve been saying, she was a turn on. Her back hole engulfed my crown as I spread her cheeks. Stuck for a moment, she took a deep breath and forced almanbahis giriş her bottom down. The first couple of inches plowed inside her tender, velvety ass, and she shut her eyes tight and bit her lip.

With her right knee on the bed and her left in the air, she half kneeled, half crouched over me. I raised my legs behind her and she slowly moved her bud off my cock before sinking down again. After a minute while she adjusted to the intrusion, Jill began bouncing on about two-thirds of my thick stalk, her cheeks slapping against my thighs. God it was good, feeling her snug passage parting for my forbidden penetration.

I straightened my legs and she lowered her raised knee, her ass sliding slightly further down my dick. Her fingers left imprints on my shoulders as her tightest space stretched wide. Hot and humid, her hole held a vise grip as it pulsated around my pole. Nearly completely sheathed inside her warmth, I pulled my length out of her gulping ass until just the head remained.

“Ready?” I whispered in her ear. “Are you ready to really get it?”

“Yes,” she squeaked, the word catching in her throat. She knew what was coming: My rod ramming roughly into her pliable star. She tightened her grip. “I’m ready.”

I shoved my girth through her defenses as she yelped, her cry changing to a long moan when my pelvic bone slapped her pussy. Removing all but the tip, I did it again, this time burying my bone even deeper within her reticent recesses, widening her soft walls.

“God, oh god,” she whimpered. She knew there was no point in asking me to be gentle, but I held my throbbing meat still for a moment, content to luxuriate in her heat. The narrow channel hugged my thickness and her chest expanded as she finally drew a breath.

I withdrew slowly, her defenses returning as my invader retreated. But only for a moment. Driving back into her, I established a nice rhythm, her hole yielding more readily. She continued to screw her eyes shut and bite her lip, but that didn’t prevent small cries from escaping her cute mouth.

I drilled into the tiny treasure for a bit before pulling out and pushing back into her soaking pussy. I held Jill’s adorable cheeks apart, her dilated, abused rear hole opening for the camera. I knew nothing about gaping beforehand, but I’ve definitely had a soft spot for it ever since. There’s something about a woman’s stretched ass that’s so beautifully nasty.

After several deep strokes in the place more than a dozen pricks had plied, I returned to the space that knew only my meat. The sides scraped my girth and she gasped, adjusting to the feeling of fullness traditional penetration just can’t provide. I quickly picked up the pace, pulling her ass all the way down my dick.

The change in my breathing signaled the oncoming of another enormous cum. “Yes,” she choked, driving her hips hard onto my pelvis until my balls brushed those half moons. “Come on, come on!”

The feeling surged through my groin, tingling nerve endings as semen charged up my rod. My grunts gone desperate, the release exploded simultaneously with Jill grinding my fully engulfed member deep into her guts. Another spurt coated her tube before I urged her ass just off my tip so I could stroke a couple feeble streaks onto a cheek.

Totally sated, I giggled ecstatically as she collapsed on top of me. “How was that?” she teased with a chuckle.

“Oh my god, that was so good,” I breathed, barely able to utter the words. “You’re amazing. Fucking amazing.” She sighed happily, hugging my neck.

It’s been a few years now since I had Jill’s amazing ass. I haven’t had one since, either; my recent partners haven’t been into it. That’s depressing, but I’m fortunate to have the moment memorialized on tape. Occasionally I’ll break it out, reliving how blazing that woman was.

The final shot shows Jill resting over me, cum glistening on her spread ass flesh. As we nuzzle, her misshapen rectum refuses to close. Instead, a steady stream of seed seeps from the once tight, virgin territory and drips onto my softening cock. Damn.

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