Something New: Night Ride

I didn't go back to the adult store for another couple of weeks. I knew I'd loved it, but I wanted some time to process what all of this really meant. I knew that I was a cocksucking anal slut, but there was more to life than gloryholes and backrooms. Did I want to be a woman? Was I gay? I didn't think I was gay; I still enjoyed the idea of fucking a woman, and spent one weekend jacking off to straight porn just to prove it to myself, but I couldn't deny that it paled in comparison to what I'd experienced as Sheila. When I finally went back to the adult store, I probably sucked a half dozen cocks at least, but no one decided to join me on my side of the wall; I went home feeling satisfied with several loads of cum in my belly, but still unfulfilled. I knew that my first experience had been a fluke, and if I wanted more I was going to have to try something different.

Still, while I explored options, Sheila became a regular at the gloryhole, and I honed my oral skills as well as my dressing and makeup. My wardrobe grew to include stuff that was genuinely slutty, unlike the generally conservative stuff my ex-wife had rejected, and I reveled in every aspect of it. My social life outside of my gloryhole nights improved as well, and it was obvious that my buddies saw that I was happier than I'd ever been, though in typical dude fashion, no one ever asked why.

Then it happened. One night of restless browsing, I came across an app called TrapFinder, and it was exactly what I'd been looking for. It was a hookup app like the half-dozen others out there, but this one hooked horny men up with crossdressers and trans women. I spent some time browsing before creating a profile, but I knew I'd found what I was looking for. The next time I went to the gloryhole, I brought my phone and snapped some super slutty pictures and even recorded a short video clip of me gagging on a monster cock, and uploaded them with the caption, "This could be you, and so much more..."

It didn't take long before my inbox was filling up with thirsty men looking for a slutty crossdresser for some no-strings-attached sucking and fucking. I could afford to be picky, so I perused the messages, eliminated anyone who didn't have a pic or info in their profiles, and soon had a rendezvous planned out. The next weekend, I took a long, hot shower, shaved every inch of my body below my eyebrows and spent a couple hours on my makeup and outfit.

Sheila had evolved since my college boy. Instead of being a blonde, I chosen a wavy auburn wig, and wore contacts to bring out the blue in my eyes. My makeup game was better than my ex-wife's had ever been. I selected a pair of thigh-high stockings with garters and an pair of panties that had been designed to tuck my dick and expose my ass. I topped it off with a strappy bra and my newest breastforms before slipping into a slinky black form-fitting number and a pair of fuck-me heels. I was so excited and nervous that I almost forgot my keys, but shortly I was on the road to the club where we'd agreed to meet.

I walked in to the club and looked around. It didn't take long for me to spot him, sitting at a table; he'd sent a picture once we'd set up the meet, and maybe it was just the lighting, but he looked even better in person. He'd caught sight of me as soon as I'd walked in the door, so I made a point of walking slowly toward him, letting my hips sway and my eyes lock with his as I approached.

"RideMyCok74?" I asked in my best sultry tone as I reached him. He didn't answer, just nodded as his eyes devoured me. I'd never felt so feminine or wanted, and I was loving it. "Don't mind if I do," I teased, then sat down at the table.

"You want a drink?" he asked. I nodded.

"Something fruity and strong," I added. He flagged down a waitress and ordered for me, and shortly I was sipping on some sort of tropical concoction that definitely had a bunch of rum in it. I didn't need the liquid courage, but I drank it down anyway, then slid closer and leaned in to kiss him. He didn't pull away, and I found myself for the first time since the bartender locked in a kiss with another man. It lasted a moment before I pulled away teasingly.

"You want to get out of here?" he asked in a husky tone. I didn't answer aloud, but dropped my hand down to stroke at the cock that was pressing against his slacks, and felt it jump in response. He arose quickly, dropped a couple bills on the table, and took my hand. Once again I felt eyes on me, knowing what was going on, and felt a thrill pass through me. This was really happening.

We made idle, suggestive chit-chat once we were in the car, but as soon as the lights of the busy club district faded behind us, I hesitated no longer. I reached over and slipped my hand down the front of his pants, feeling for the prize that lay within. He groaned when I found it, and I wrapped my hand around his shaft, pleased at the size. He wasn't a small man by any means, but not so big as to be scary, either. I stroked it gently a few times, then leaned over to unbutton and unzip his pants, letting it finally rise into the dim, flickering light from the passing streetlights.

"Wait," he said. "I have a bed and everything." I smiled at him for a moment before leaning down further and taking the head of his cock into my eager mouth. Despite the awkward angle, I was a veteran cocksucker by this point, with dozens of blowjobs behind me. The confidence with which I sucked his dick must have been appreciated, because he groaned and I felt the car swerve a little bit. Finally I felt him pull the car off the road and lean back, giving me better access to that beautiful tool, and I sucked and licked it like I was made for this.

I felt the end approaching as his body tensed and his breathing quickened. He tried feebly to get me to pull back, but when I felt his hips start to buck, I sucked even harder and was rewarded for my efforts by a hot shot splashing the roof of my mouth. I bobbed up and down a few more times, milking the last of it out before pulling back with a mouthful of cum. I showed it to him and then swallowed it with a grin.

"Damn, that's the hottest blowjob I've ever had," he said after he'd caught his breath. "But I really wanted to fuck you."

"Oh, so do I, baby," I crooned. "I think you'll find that you've got more in you still." That was something I'd learned, too; sometimes you could get them to stay at the gloryhole, and with a little work, you'd get a round two. Round two inevitably lasted longer, but especially now, that's exactly what I wanted. I gently played with his softening cock, stroking, teasing and he leaned back with a sigh and let me do it. "I don't want to wait to make it to your bed, though," I whispered; his dick jerked in my hand as he realized what I wanted. He chuckled softly and I felt it begin to rise again.

"You want to do this here?" he asked. "In the car?"

"No babe," I demurred. "It looks pretty quiet out there," I said, glancing around. "I bet you could rail me on the hood of your car, and no one would complain." That definitely got a response, and I suddenly found myself stroking a swollen cock, ready and willing.

"You're a dirty slut, aren't you?" he said with a laugh. I nodded brightly and squeezed his cock before releasing it and reaching for the door handle to let myself out. He followed quickly, looking around nervously before meeting me around the front of the car, and wrapping his arms around me to pull me in for a fierce kiss. I leaned into him, and his hands explored, down my back, groping my ass, lifting my short dress to expose my slutty lingerie. I moaned softly, and he pushed away, reaching down and pulling the dress up with one smooth motion. I squeaked in surprise as the dress came off, exposing me fully. I checked my wig briefly, but didn't have time for more before hands, rough with urgency, turned me around and pushed me down on the hood of his car. I braced myself, but instead of a rough push, he left me there a moment. I'd never felt so vulnerable as he walked around to the car, but I remained, waiting, willing. He rummaged a moment, then returned, and I felt something cold and slippery on my butt before his fingers came up and massaged it over my exposed asshole. He'd brought lube; maybe he wasn't so eager to get to a bed as he'd seemed, either.

He played with my ass a little bit, teasing at my hole with his thick fingers before finally slipping one in, drawing another moan from me. He finger-fucked my asshole for a moment, before finally withdrawing his hand, and replacing it with something much meatier. I let out a long slow breath as he slowly pushed into my tightly puckered ass. I wasn't as nervous this time as the last, since I knew what was coming, and it was easier to relax and concentrate on the feeling of his big cock sliding into me. Finally he was completely inside me, and I felt that glorious fullness that I'd only felt once before. He withdrew just as slowly, bringing that delicious pulling sensation that set my eyes rolling back in my head and pulled new moans from me. Then in again, picking up a slow and steady rhythm until I wanted to scream at him to just fuck me.

"Please," I whispered desperately. "Harder, please!" I splayed my fingers out on the hood of the car as he obliged my request, shoving his cock hard and deep in my ass, making me gasp and shudder. His rhythm increased to a steady pounding that rocked the car almost as much as it rocked me. I leaned back with each thrust, meeting him as he pushed hard into me, grunting with effort each time. I couldn't help my own moans which grew louder as the sensations in my asshole intensified. "Ooh, fuck," I said, "Fuck, fuck me!" The already steady pace quickened, but I could tell that he was still good for a while longer. I wasn't sure I was, though; my cock, tucked back in my panties, was oozing steadily, and I could feel that pressure building as I had only once before.

"I'm gonna cum," I moaned. It had an electrifying effect on my lover, and he managed to find even more, shoving me down hard on the hood of the car and ramming my ass so hard that the whole car creaked. "Oh fuck, I'm cumming!" I shouted, "I'm cumming!" As the words left my mouth, so did streamers of jizz from my tucked cock, dripping onto the hood of the car. I lost myself for several seconds as the waves of pleasure swept through my body, leaving me tingling as I came back to full consciousness.

The cock in my ass continued to pound in and out unabated, already beginning to ratchet the tension back up as each thrust sent more ripples of sensation through me. It felt like he was steady to go for a good time yet, and I felt grateful that the earlier blowjob had prolonged this experience. Just when I thought it was possible that I'd get another orgasm, I felt the tempo shift, taking on the frantic spasms of an approaching orgasm. My lover was gasping and moaning, his hands rough on my hips as he neared completion.

"Cum for me," I moaned between gasping breaths. "Cum deep inside me!" As if my words were a commandment, he thrust a few more times before slamming his cock deep into my asshole, and I felt him twitch and shudder as he emptied his balls into me again. He slid in and out a few more times, and I could feel the slickness of his cum-slathered cock in my deliciously abused ass before he finally withdrew. Though it was only the second time, I knew already that this would be my least favorite part, the feeling of emptiness that comes after a good hard fucking. Still, better to have had and lost than to never have had at all, as the saying goes.

He took me back to his place, but we were both too spent for any other escapades that night. We kissed and cuddled for a bit before falling asleep, me my head on his chest, and him with a handful of ass.

We saw each other a few times after that, but it soon became clear that he was interested in something long term. The idea might once have been completely laughable to me, but that wasn't the reason I cut him loose; I was only just beginning this journey of exploration, and I wasn't quite ready to consider settling back down. Sheila had a lot more cocks in her future.