The Business Traveler

It had been two weeks since my girlfriend broke up with me and I was still down in the dumps. Nothing was helping me cheer up, not alcohol, food, video games, it was rough. When I finally mustered up enough energy to masturbate, it triggered something inside of me, the urge to dress up returned.

I had stifled and suppressed my thoughts about crossdressing and presenting female while I was dating her but suddenly I felt free to explore my feminine desires. I took two large bags filled with clothes and shoes out of the depths of my closet and laid everything out on the floor. I had quite the range of possible outfits but to start I just grabbed a thong and a pair of black tights, opened up my makeup bag and got to work.

It wasn't long before I had a face full of makeup and seeing myself in the mirror was like running into an old friend you hadn't seen or spoken to in a few years. It was a warm familiarity that I didn't realize I had so desperately needed. I threw on a wig and some fake nails, stepped into a cute black dress with little white polka dots and found my tallest heels. I slipped on the shoes, I left my depressed state and became someone else entirely. I wasn't Daniel Alexander anymore, I was Talia Jane.

As I was admiring myself in the mirror and taking an extensive amount of selfies, I decided I might as well put them to good use and created a Grindr profile. Within minutes, my inbox was filled with men ready to meet Talia. I chatted with a few of them, silly pickup lines mixed with some dirty flirting but one man stuck out above the rest. A business traveler staying at one of the nicest hotels in town. He was my age, well built and just a little bit of stubble and his dick pic wasn't so bad either.

As if life was on fast forward, the next thing I knew I was stepping out of my car at the hotel's valet and handing over my keys. I checked my app again and his message said "Room 528, knock three times so I know it's you." My heart was pounding in the elevator and I was overcome with a rush of excitement and nervousness then "ding!" and the doors opened. Room 528 was at the end of the hall and around the corner. I took my time, soaking in the anticipation and enjoying how I felt in my outfit before it inevitably came off.

The number was staring home right in the face. 528. Knock, knock, knock. The peephole went from light to dark, the door slowly opened and there he was. I nearly melted, he looked even better than his photos and was standing before me in only a tight pair of black boxer briefs, taller than me, even in my heels.

"You must be Talia Jane," he said. "You can call me Jay." I nodded as he gestured to invite me inside. His room was spotless, as if housekeeping had just left. "I wanted to make it feel a little more inviting, how did I do?"

"Just fine," I squeaked out. "I mean, it looks great!" I smiled sheepishly.

He smiled and put his hands on my waist, "My goodness you're beautiful" he said, pulling me closer. All I could do was blush and throw my arms over his shoulders and around his neck. He leaned in for a kiss and I froze but as his lips touched mine, it was as if emotional fireworks went off inside of my body. When the excitement dwindled, I became instantly relaxed and melted into his arms.

Still softly making out, we made our way to the bed. He sat down, looked down at his growing bulge then up at me and coyly raised one eyebrow. I quickly dropped to my knees then slowly and seductively pulled his underwear down until a hard eight-inch cock popped out. My eyes got wide and I bit my lip then without even thinking about it, went right for it. I started with my tongue at the bottom of the shaft, licking all the way up to the tip as he moaned softly and leaned back on the bed.

I sucked on his tip and licked up the leaky precum then took as much of him into my mouth as I could. My tongue swirled all over him, slurping up everything, feeling him throbbing while he moaned. I tasted more precum and was about to give him another round of sucking when he sat up and whispered into my ear, "your mouth is amazing but it's your ass I want."

He pulled away and I just silently nodded. He unzipped my dress and slowly pulled down my tights. "Leave the shoes on for me?" I nodded again and stepped out of the dress and tights but slipped the shoes right back on. My hard cock was clearly showing through my lace thong then before I knew it, he was touching me there, gently rubbing as if to invite her out from hiding.

He slid my thong off, grabbed my cock and pulled me closer to make out again and stroke me softly. "Are you ready?" he whispered. I nodded again. He let go of me and lay back on the bed, stroking himself while he covered his cock in lube.

"I want you to ride me so I can watch you experience this." I felt those fireworks again and crawled over him onto the bed. Straddling his torso, I grabbed his cock and teased my hole just a little before slowly taking all of him in. Inch by inch I felt overwhelmed with pleasure, my hands balancing on his chest as I lowered myself down, down, down, moaning sounds I didn't know I could make until I felt my ass touch his thighs. I felt like I was at the top of a roller coaster, that sense of anticipation right before you're about to drop.

I started riding him, slowly at first to get the feel of it but once he put his hands on my hips, I lost all care for being careful. I'd spend countless hours riding my dildo at home but none of that prepared me for the real thing. It was intense euphoria, something I had desperately been missing in my relationship with my ex. But she was the last thing on my mind at that moment. I was letting Talia shine and she was as bright as the midday sun.

The harder I went, the more the intense pleasure overwhelmed me. I started to notice precum leaking out, transferring itself onto Jay's stomach every time my cock flopped down onto him. He noticed too and would scrape it up and feed it to me, enhancing the experience even more. Suddenly he gripped me tight, his eyes got wide and he shouted "oh fuuuuu" and before he could get to the "-ck" I felt him shoot hot cum inside me. He pumped inside me as I bounced and the second he grabbed my hard cock that sent me over the edge as I came all over his chest. He scraped some up and fed it to me again and I shivered.

After cleaning up, he gave me a t-shirt and extra pair of pajama pants to wear as we sat in his bed and shared a room service burger and fries.

We had sex again before going to sleep, this time doggy style and I almost came the second he got inside.

I woke up the next morning to him sucking me off which was unexpected but very welcome. He let me keep the t-shirt and we exchanged numbers, promising we'd connect if we were in the same city again. A week later I had a flight booked to see him and he insisted I spend the entire trip as Talia.