Once a month, I get dressed up and go for a drink, merely to see if I still pass as a woman.

But every so often, when the mood strikes, I also look for some action. When that happens, I go all out. I’ll wear my highest heels and my shortest dress, and I always make sure that I wear a matching bra-and-panty set, because even if the guys I pick up don’t notice those little details, I feel more pretty and confident wearing lovely lingerie.

Last month, I decided I needed to get laid. Or, rather, that Emily — my female alter ego — needed to get laid. So, on a Saturday night, after I’d showered and shaved and primped for hours, I donned a slinky red dress and a pair of four-inch platform sandals, put some condoms in my clutch, and headed out to my favorite lounge.

It was early when I arrived, so the place wasn’t packed yet, but all the tables were taken, leaving me to grab a seat at the bar. That spot made it easier for me to meet the men who came in anyway, so I didn’t mind being “stuck” there.

I ordered a martini and scoped out the crowd. There wasn’t anyone there who caught my eye just yet, so I settled in and started chatting up the bartender whenever he wasn’t busy with other customers. He was cute and very flirty, and I felt relaxed around him, probably because I didn’t ever think of bartenders as appropriate targets. After all, if things go wrong with the bartender, you have to leave and can’t go back to that bar again without worrying about having an awkward run-in. So I avoid hitting on them — most of the time. But this guy, he was really pouring it on thick. He was definitely flirting, and he brought me a complimentary appetizer and drink after I’d bought only two cocktails. And the more he chatted with me, the less attention I paid to the obviously attractive and single guys congregating around the bar, even though I could tell that a few of them were checking me out.

I’d spent a few hours keeping my barstool warm when the hot bartender — whose name, I’d learned, was Geoff — told me he was about to end his shift. Then, before I could settle my bill, he asked if I’d want to grab a drink with him after he’d clocked out. “I live around the corner, and I could make you one of the new cocktails I’m testing,” he offered. I readily agreed.

When we got to his place, I let him mix me a drink, and then I followed him out onto the small balcony off his kitchen. After I’d had a few sips, he took the glass from my hand and set it on a nearby table. Then he cupped my face in his hands, leaned in and kissed me.

I felt my cock twitch as his tongue slipped between my lips, and by the time he finally broke away to catch his breath, my dick was positively rock-hard. After we had a moment to get some air, Geoff pulled me to him again, and this time, as our bodies pressed together, I felt his hard cock bump against mine through our clothing. I nearly swooned.

He groaned loudly as he crushed his pelvis against me, and he didn’t seem surprised to feel an extra bulge between us. In fact, he seemed quite pleased. After a minute or two of grinding together, he even reached down between our bodies and groped at the hard-on that was barely hidden by my dress. He rubbed my dick through the fabric, then reached under my dress to caress my erection through my panties, which were sporting a wet spot where my pre-come had soaked through the material.

Our lips stayed locked as we groped each other, and then Geoff pulled me back inside to lead me to his bed. As we crossed the apartment, our hands tugged at each other’s clothes, unzipping and unbuttoning, and we stopped for a second in the living room to kick off our shoes.

Inside the bedroom, I pulled his shirt up over his head and he tugged my tight dress down my body. Then he dropped his pants, and we maneuvered onto the mattress, both in only our underwear. He climbed on top of me and kissed me as he writhed against me. Our cocks bumped as our hands traveled all over each other’s exposed flesh. I ultimately grabbed his ass while his hands moved upward until his fingers tangled in my wig.

I pushed a knee up between his legs and wrapped my free leg around his hip, pushing myself as close to him as I could. I felt his cock twitch as we continued to rock against each other. My own dick seemed to get harder — if that was even possible.

Geoff was seriously worked up. He pulled me tight against him before rolling us over so that I was on top. Then he worked his hands into my panties and yanked them down, getting them as far as my knees before I took over and stripped them the rest of the way off. After tossing my undies aside, I knelt next to him and tugged his boxer-briefs down his legs, freeing his erection.

When I lay back on top of him, our bare cocks brushed against each other for the first time. I bit my lip to try to stave off what felt like an imminent orgasm. I couldn’t come prematurely — not that night, not with him. Geoff was the hottest guy I’d ever picked up, and I was already thinking that if things went well, maybe we could hook up on the regular.

“He cupped my face in his hands, leaned in and kissed me.”

As I stroked my dick back and forth along Geoff’s, he thrust upward, seeking more contact. In no time, he seemed to become as desperate as I felt and flipped us over once more, so I was on my back.

Reaching into his nightstand, Geoff snagged a condom and some lube. After dipping between my cheeks to slicken up my hole, he rolled the condom onto his shaft. In one quick motion, he pushed my legs up so my knees nearly touched my shoulders, and then worked his dick into my ass.

His cock was the perfect size, not too long or too fat, and he slid into me easily, filling me and making me moan. He was relentless, pushing in deeper and deeper, until I was absolutely stuffed with cock. As if savoring my snug passage, he stayed still for a moment, buried balls-deep inside me. 

Shifting my weight, I wrapped my legs around him, digging my heels into his back. I wanted him to pound me, and I thrust myself against him in desperation. He got the message and started to rock his hips. Geoff leaned forward and pumped into me with determined strokes. With each movement, his stomach rubbed against my cock, ramping up my arousal. I was going crazy. I needed to come more than I’d ever needed anything else.

I clenched my asshole, tightening my grip on his throbbing dick. Geoff increased his pace, loving the friction provided by the sudden constriction. The short, soft hair that covered his stomach tormented my cock, and I bucked frantically, wanting more of everything.

Geoff abandoned all propriety. He fucked me roughly, thrusting as fast and hard as he possibly could. The sound of our bodies slapping together filled the room, joined by the chorus of our heavy breathing. I was lost in the moment until I finally felt my cock jerk. I was about to come; there was no denying it.

I announced my imminent climax, and Geoff urged me to shoot, promising me he was on the verge himself. I sprayed my cream all over his stomach, and it smeared between our bodies as he continued to stroke in and out of my clutching back hole. He kept going for another dozen or so thrusts before he finally let loose himself. I felt his dick throb between my cheeks as he surrendered to his pleasure.

When he was empty, we collapsed on the bed together and spent a couple minutes catching our breath.

After we’d cleaned up and exchanged numbers, I called a cab and headed home. But I know I’ll see Geoff again soon. In fact, I was thinking of giving him a call tonight…