My First Time Getting It in Heels

I went out to the gay club on a Saturday night for some dancing. I don't go out very often dressed en femme and this was a rare night out for dancing in heels.

I wore 12cm, silver high heels, back-seamed stockings, garter belt, lacy thong, and matching bra. I also wore a black, snakeskin mini-skirt, and black satin blouse. Pair this with an auburn, mini-bob style wig and I looked like a sultry no-nonsense seductress.

Cut to an hour later and I'm at the bar sipping strong, cheap drinks.

I hit the crowded dance floor in my heels and let the beat move my body. In a matter of minutes I could feel a pair of strong and manly hands holding my hips and sliding up and down as I danced. It felt good. I didn't turn around. I kept my back to him and let him work his hands on my hips, legs, and eventually grope my ass while he brought the rest of his body up against me, breathing on my nape.

The music ended and I left the dance floor. I sensed he wasn't too far behind, so I went toward the door. Outside, I nervously took a breath of fresh air and he stepped out. A dark, tall, man in a tailored suit. I can't remember but, I think he said something like, "Come with me to my car for a foot massage an a tongue up your ass." and I was like, "Sure..."

His luxury sedan was parked in a dark corner of the club parking lot. He opened the door for me, I stepped inside and without much notice, off the heels went and he started sucking on my toes. I didn't know how good it felt until he really worked his tongue along my stockinged feet and massaged my legs. He lowered the seat back and with his deep voice, he told me to lay on my stomach.

I turned around, ass up, and I felt his big hands hike up my skirt and pull my panties to the side. His hot breath warmed my ass as he exhaled, then inhaled the perfumed aroma of my asshole. "You smell like sweet candy," he said and circled my anus with his pointed tongue. Ooh, this tickled and I giggled a little, then he penetrated me with his tongue. At first it was just shallow dips of his tongue, then it got deeper. His tongue rubbed my anus as he rhythmically pushed his way in and out of my ass. Eventually, I relaxed and he slipped his tongue deeper. I was in heaven, moaning and breathing heavy and that's when he sat up, unzipped his trousers, and let a generous amount of spit drop down onto my asshole.

I could feel his mushroom tipped cock rub on my anus, circling around and dipping in, just a little. Just to tease. I couldn't believe how easy it was for him to just dip his cock-head into my ass, and just like that he wrapped his arm around my torso and he pushed his cock in past the tip.

I felt the mushroom head pop in past my anal ring then gently pull back. I could really feel myself opening up and with my ass getting wetter, I could feel his cock pushing deeper with each thrust.

Did I mention how turned on I was at this point?

"Mmm, your ass is so soft," he whispered and pushed all the way in, to the hilt! "Unh!" I let out a whimper and he slowly pulled out, then quickly thrust all the way back in. His cock must have been at least 8-inches. I didn't get a good look. I only had the sensation of it sliding all the way through my rectum. "Oh, you feel so good!" I exclaimed. I must have been dripping. He hinted to me that he could fuck me deeper if I rolled over on my back.

With that, he withdrew from me and I rolled over and before I could catch my breath, he was in my hole again. He was right, this time it was like being split open! My ass was impaled on his cock and that's when the real fucking started.

He slid a hand up my blouse and tweezed a nipple while gripping both of my wrists above my head with the other. Thrusting his cock in and out. He breathed into my neck giving me kisses and tracing his lips up to my ear. His cock was deep up my ass while me pushed the weight of his pelvis up against mine and ground up against my cock. We started working into a rhythm as I pulled up my legs from his waist to his shoulders where he kept my feet on each side of his head.

His pubic bone rubbed my taint, balls, and cock. His pubic hair was tickled my skin. I couldn't catch my breath but I began to beg for him to fuck me harder. His cock pistoned in and out of me in a come-hither motion, perfectly rubbing my prostate with his head while simultaneously filling my ass.

"Please, fuck me harder!" I begged.

"You like this cock?"

"Yes! yes!"

"You want me to cum?"

"Yes, oh yes, cum in my ass!" I whispered. "Pump my ass with your cum!"

"I'm getting real close. I'm going to cum in that asshole!"

"Yes, please! Please, pump that hot cum in me!"

His rhythm sped up and I could feel him shudder. He grunted, his torso tightened up and I could feel his cock get really stiff; rock hard, then it pulsed and that's when he did it. I felt his cock throb as his cum poured into my ass. It was hot and the inside of my ass became wet and squishy. His cum coated all over the insides of my ass. It tingled and worked it's way around inside of me. This was all too much for me, the hot cum, his grinding, and his pubes tickling me. I came. I came real hard and squirted in my mouth, chin, and my neck. I let out of squeal, while his hand held my wrists.

He slowed to a stop and held his cock in me.

We laid for a moment to catch our breaths and he pulled out and got dressed. A couple moments later, I stepped out the car and cum dripped down my leg.

We went back into the club and went our separate ways back to the dance floor. I could feel the rest of his cum run down my legs as I danced and it felt wonderful.