If you could lose your virginity all over again, would you be smarter about it?

That was the question I posed to myself as a sensible, wise 26-year-old woman. I’d enjoyed years of likeable partners and gratifying experiences. These were much different from my first clumsy, desperate forays into sex, but that’s true of everybody, isn’t it?

I found myself longing for a “perfect” de-virginalizing experience. But since I couldn’t travel back in time for a redo of the actual loss of my virginity, I needed to figure out something else.

The answer was obvious. My body was equipped with several entrances conducive to sexual activity. I’d had my pussy pounded plenty of times, and more than a few cocks had plugged my mouth, much to my delight. But… I’d never done that other thing.

My anal cherry was intact. No guy had ever done me up the ass. It just wasn’t a sexual deed I’d ever really considered, although I had lots of anecdotal evidence that it was a worthwhile experience.

“When Zack gets behind me,” my best friend, Nanette, said to me about her boyfriend, “and my lubed-up hole is waiting for his cock to ream it… Erin, it’s just delicious! And then there’s the first penetration, my asshole widening to let him in. I nearly go out of my mind. It’s so good!”

Nanette was definitely an advocate. But the idea scared me a little. I kind of liked that, though. It simulated those early virginal fears I’d had. Sex had once seemed so mysterious, so exotic. It wasn’t like I had grown bored with it (hardly!), but I did miss that sense of newness, like I was about to explore unknown territory.

As it happened, my ass was totally unexplored. All I needed was to find the right guy to plant his flag in it, so to speak. I was ready.

None of the men I’d been dating lately seemed like the ideal candidate. I realized with a thrill just how picky I could be about this. I didn’t have to settle for anything and could take as much time as I wanted to find the right man.

Problem was, now that I’d seriously considered anal sex for the first time in my life, I was growing obsessed with the notion. I resisted the temptation to perform any experiments on myself. I had a modest dildo collection, but it was better, I thought, to feel that first ingress from an actual live cock.

I trawled through my social circles, considering and rejecting men who had even vaguely interested me. I wasn’t certain what I was looking for, what trait would tell me this was the guy I wanted to take my ass-cherry. It would be something instinctive, I eventually decided.

A week passed while I squirmed with anticipation and growing need. Then I happened on Elliot. He was a pitcher on a local baseball team sponsored by the company Nanette worked for. His body was long and lean, with arms corded with muscles. He was incredibly limber. When he went into a windup to throw a pitch, every part of him was in coordinated motion. He moved fluidly, with perfect control.

Somehow that clinched it. Such precision, such poise. Would those skills on the baseball diamond translate into sexual performance? On the surface that seemed a ridiculous assumption, but my instincts were telling me otherwise.

The team was meeting up at a club later. Nanette invited me along. I wore     a little black number with matching  high heels.

“Expecting some fun?” she asked.

“Can you introduce me to Elliot?”

She grinned, always happy to help. “Hell yes.”

The place was busy but not too noisy. Nanette’s coworkers were mingling with the members of the team. I didn’t see Elliot anywhere and felt a crushing disappointment, until Nanette tapped me on the shoulder.

“Elliot, this is Erin. Erin, Elliot.” Then she promptly disappeared.

I felt an immediate crackle between us. Elliot was desperately handsome up close. He got me a drink, and we retreated to a quiet corner. I asked him about that day’s game, trying to sound like I knew something about baseball. He explained his pitching technique and other details about the sport, though his eyes kept going distractedly to my tits and legs.

“Very slowly, he let me sink just the slightest bit onto his straight-up shaft.”

When he started telling me about a pitch called a “backdoor slider,” I took it as a sign from the love gods. I moved closer to him and purred, “I’d rather you showed me your backdoor slider.”

We slipped out to the parking lot without anyone noticing. My body tingled and trembled. My pussy was wet, but I had something else in mind. The erotic tension of the past week had come to a boiling point. I would get my ass fucked that night.

When Elliot asked if we should go to his place or mine, I grabbed him and shoved him into the back of my car, in a dim part of the lot. It occurred to me that I’d originally lost my more conventional virginity in a car’s backseat. This time was different, though. I knew myself and knew what I was doing. I was in control.

Except I really wasn’t in control — but in the best possible way. I dove on Elliot, mashing my mouth down on top of his, flattening my breasts against his hard chest. He stabbed his tongue into my mouth, his hands closing over me. He slid those hands down my back and groped my perky ass through the black dress. I jammed my thigh between his legs and rubbed his bulge. He moaned.

We tore at each other’s clothes. Our hot breath quickly fogged the windows, giving us some privacy should anybody wander past. I wasn’t worried about getting caught, though — I was a big girl, all grown up, and nobody could tell me I couldn’t take a cock up my ass if I wanted to!

Elliot’s shirt was off, his pants undone, and my dress was shucked halfway off when he suddenly stopped with his hand on my heaving tit and his cock throbbing in my fist. Quite apologetically he said, “I don’t have a condom with me. I don’t want to risk getting you pregnant.”

I grinned. “Don’t worry, stud. My pussy isn’t in play tonight.”

He looked baffled but didn’t pause again as we got out of the rest of our clothes. His meat stayed fiercely hard. I reached into my purse, squirted lube from a tiny tube onto two fingers, and then turned to let him see me oiling up my butthole. That contact alone sent wild shivers over my naked flesh. Elliot gaped.

When I daubed the remainder of the lube on his swollen cockhead, he understood what was going to happen. I gave him a last hardy kiss, then faced away, squatting over his cock. He cupped the undersides of my butt and lowered me gently toward his waiting tip.

Everything went in slow motion for me. My senses were heightened. The scent of my pussy was strong, as was the aroma of Elliot’s masculine sweat. I felt the nap of the floor mats under my bare feet. I was hunched forward to keep my head from bumping the roof and felt the flex of every individual tendon in my body.

My backdoor pucker felt like a glowing jewel. At the first brush of Elliot’s cockhead against my untapped entrance, a ripple of nervous pleasure went through me. I was 26, a fully realized sexual being, and I was about to pass through a completely virginal experience. It was amazing.

Ever so gently, Elliot’s rounded crown slid between the halves of my ass and settled flush against my hole. He was still cradling my backside, supporting most of my weight. Very slowly, he let me sink just the slightest bit onto his straight-up shaft.

I won’t lie. That first hint of penetration scared me some. However, I felt my cinching ring start to open, just as Nanette had described it. A sense of extreme vulnerability overtook me. Elliot’s cockhead gradually slipped inside, and I gasped. It felt huge.

But he held me there as I drew steady breaths. Soon I was aware of a simmering pleasure. It seemed to travel a different route than the sexual joy that came from vaginal penetration — and I liked it.

I pressed down and took in another inch of him. My channel expanded with his girth. I could feel how he was still throbbing urgently. But he must have been very practiced at this. He let me decide the speed, taking my cues. Pleasure rose hotter in me.

Finally, my ass cheeks pressed against his crotch. I had impaled myself completely on him. I savored the moment, recording every atom of the experience, each minute sensation.

Elliot said, “It’s so fucking beautiful! My cock is all the way inside your ass!”

That touched off something completely wild inside me. It was a reminder that this wasn’t some museum display. Sex was supposed to have an unruly element to it. Without warning, I lifted myself and dropped back onto his straining staff. It was like a bolt of fire tearing up through me, but a fire of excitement, of runaway desire and bliss.

The mechanics were odd but not totally unfamiliar. I was using a slightly off-kilter set of muscles to raise and plunge myself onto him. I gripped the headrests of the front seats and rode his cock faster, more recklessly.

Elliot’s fingers sank into the flesh of my ass, and he started fucking upward into me. I was past any feelings of vulnerability or fear, and I loved every thrust he gave me. He was saying, “So good, fucking this sweet ass!”

I totally agreed. Dark pleasure radiated out over me. I relished the freshness of it as my body writhed. I impaled myself again and again on that lovely cock. He jammed up inside me with every downstroke I made; we moved with perfect coordination. I took him into my deepest passage, where dormant pleasures had awoken.

Some part of me had wondered if I could actually come from anal sex, even though Nanette assured me she got off on ass play with Zack all the time. But the vast erupting rapture that took hold of me told me I didn’t have to worry. Orgasmic euphoria hit me with a wallop. Strange joys coursed through me, finding their way by unused pathways. I cried out, savoring the bliss.

At the same instant, Elliot shot his load. I felt the exquisite sting of his spunk deep inside me. My pussy overflowed in sympathy, but this occasion belonged to my ass. My lucky, de-virginalized ass.

Eventually, we uncoupled and sat side by side on the backseat. Elliot looked happily dazed. I kissed him gently, to thank him for being so skillful.

“I’ve never had anal with a woman before,” he confessed. “I hope it was okay.” I hid my surprise and assured him it was.

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