I Met My Crush

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows?

Anyways, my regular readers know that I enjoy writing about the transgender experience from different perspectives. I try not to misstate the reality of being transgender too much.

This story is inspired by an older story I read.

~~

The phrase "He didn't know I was trans" is often used by transgender women as a humble brag when they're talking about being hit on by a guy who thought that they were a cis gendered woman. I'm not one of those women. I've been taking estrogen long enough for it to have feminized my features some, but no man can credibly say I tricked him into thinking I was a natural born woman. Even if they thought I might be a cis woman my voice would give me away. While I do speak softly it has some bass to it because I still have my nuts.

~

My catering company was working a party being held in a suite at the local NFL team's empty stadium. I was on the concourse looking at some of the memorabilia on display when a guy who looked as though he was lost walked past me. He was so consumed with trying to figure out where the party was being held I don't think he saw me. I'm a big sports fan, so I recognized him. He's someone in the local sport's media who I just happened to have a crush on.

"You look lost," I said using my softest voice, but it was still deep.

He looked at me and stared at my perfectly applied make-up and cute pixie haircut for a long moment. While I look reasonably feminine I am nearly six feet tall and I have that voice, so I'm sure he'd clocked me before he said, "You'd think I'd know my way around this place, I cover games here all the time."

I tilted my head to the side and wrinkled my forehead as a show of sympathy before saying, " I'm gonna go out on a limb and guess that you're looking for the Sportswriter's Social that's going on in suite 69A."

"Yes I am," he replied. "When I come to the stadium I go straight up to the press box. I can't find how to get up to the club level over here."

"Go around to portal 69 and take the escalator up. Even you can find it from there," I said, teasing him as I smirked.

"69 huh," he stated and grinned mischievously, which caused his dimples to show; making my heart skip a beat.

~~

When he saw me at the party a short time later he stretched his eyes wide for an instant. My first instinct was to check for a wardrobe malfunction, then I realized that I'd taken off the sheff's jacket I was wearing when he saw me on the airish concourse. He was now seeing me in the spaghetti strap black dress I wear to the events my company caters. It showed my toned arms and shoulders to their best advantage. It was loose fitting, but the material it was made from draped my body and accentuated my b-cup breasts and modest curves.

Based on the way he was licking his lips while looking at me it was pretty obvious that he liked what he saw. I caught him looking at me several times as I walked the suite making sure that my staff's service was on point. After making him wait several minutes I stepped up to him and said, "I see you found us."

"Yes, thanks to you," he stated with a slight nod of his head while lifting his glass as if to toast me.

"It was my pleasure," I responded, intentionally sounding sensual and hopefully signaling my interest with my eyes.

"Excuse me for staring....., but you..., I didn't expect you to look like this," he said while looking me up and down.

"Y thank you, I think," I responded and grinned.

"I meant it as a compliment," he stated, smiling with one side of his mouth. "I figured you were flat chested with no shape," he admitted honestly.

"Ah yes. Like a drag queen or a cross dresser," I said with an amused look on my face.

"Yeah," he replied and took a sip of his drink. "Would I be asking for trouble by telling you that I think you'd be an attractive woman?"

"You wouldn't be offending me," I replied while tilting my darned head to the side again. God I'm so easy. "That's the idea, to look like the woman I truly am," I stated

"Oh, so you consider yourself to be a woman?"he responded with a thoughtful expression.

"I do," I replied. Sensing that this was a good time to give him some space to think, I excused myself to go check on my staff.

~

After staying out of sight for about 15 minutes I walked through the suite again, and as I'd hoped he was still stealing glances at me. I casually made my way over to him, stopping for brief exchanges with a couple of other men who'd been trying to chat me up. I abruptly excused myself; asking the older gentleman I was talking to at the time to hold that thought when I saw my crush go to the bar alone.

"Is everything to your satisfaction?" I asked after making a graceful beeline to him.

"Perfect," he replied. Based on the way he said it and the look on his face I was pretty sure he wasn't talking about the event.

"Awesome. Let me know if there's anything... I can do for you," I said, putting emphasis on the word anything.

"Anything?" he repeated, now staring into my eyes without blinking.

"Yes, anything," I replied as I tilted my head to the side as I usually do when I'm giving the signal to a man that he can get it.

He was obviously quite perceptive and as interested as I hoped he was. "And you're a woman," he said with a questioning tone in his voice.

"Mmm hmm, but you know what kind of woman I am though, right?" I replied

As fate would have it, at that moment someone tapped on a glass with a spoon into the hot mic to get everyone's attention. The program at the heart of the Sportswriter's get-together was about to start.

"Meet me in the parking garage on level A, in 10 minutes," he said in a tone of voice that told me he meant business.

I smiled, then said okay and walked away.

~~

He was waiting for me near the elevator when I stepped off of it into the parking deck about five minutes late. "I was beginning to think you weren't going to show up," he said.

"I had to put one of my staff in charge before I left," I explained.

"I understand," he replied, then touched the small of my back and said, "That's me right over there." Indicating a big late model SUV. We got inside and he drove to a spot about 50 yards from any other vehicle. Then we sat there for a minute or so just looking around the mostly empty parking garage.

"It's been a long time since I did anything like this," he said sounding nervous.

I chose not to share my sexual history, opting instead to reach with my left hand and find his stiff cock while I was still looking around the garage. I squeezed it a few times, then I felt him undo his belt and pants before unzipping his fly. A second later I felt him lift his butt off the seat and slide his pants and underwear down far enough to free his cock and balls.

I kept my eyes peeled for anyone walking in our direction as I wrapped my fingers around his dick, then ran my hand along it. "Average length, but good girth," I said in my head, then wedged my hand between his legs and took hold of both of his balls. I played with them and his dick for a minute or two and he started to moan. I glanced at him for a second and saw that his eyes were closed, but his mouth was open.

I loved the effect I was having on him and the more I could tell that he liked what I was doing the more I got into it. If there's anything I can do well it's Jack a dick. I did quick short pumps on its head, then mixed in long strokes of the shaft before combining the two until I felt precum.

I still hadn't seen anybody coming or going in the garage, so I suggested that he recline his seat. After taking one last good look around I leaned over and put my mouth on the head of his dick. I licked and sucked on it some before sinking down on it until my lips were around the base. After holding all of him in my mouth for a moment I started bobbing up and down on it while my tongue simultaneously licked the shaft.

I licked and sucked and slurped on his dick until his precum really started to flow, then I pulled off of it.

"Why'd you stop?" he asked between heavy breaths.

I usually finish men off with my mouth or hand when I hook-up like this, but like I said I had a bit of a crush on him. "I want you to fuck me," I said while looking at his eyes in the dim light inside the truck. He looked at me intensely for a second before looking around the garage as best as he could from his prone position. I took that as consent, then climbed over the console and straddled him. We stared at each other for a moment, then I leaned in to see if he'd let me kiss him after sucking his dick. He didn't flinch, so I shoved a yard of tongue down his throat.

He grabbed my soft ass and kneaded the fleshy globes as we kissed. After enjoying both sensations for a moment I broke the kiss and straightened up so I could reach underneath my butt and grab his dick. I then rose up on my knees and guided the head of his dick to my opening. After using my index finger to push my bikini briefs to the side I lowered my hole onto his dick.

It's well used and I've had some big ones up there so it's easily entered, but I'd put lube in there anyway before coming down to the garage. I knew he was worked up so I slowly lifted myself up before lowering myself down on his dick again.

"God damn girl, you have a good one," he said sounding like he was out of breath. We quickly got into a rhythm of me lowering myself as he thrust upwards. Unfortunately for me that didn't last long and all too soon he tightened his grip on my hips and slammed his dick into me. At that point I just stayed still and let him put it to me however he needed to so he could get his nut.

After I felt the last bit of his cum ooz out of his dick and into my bowels I pulled off of him slowly then quickly pulled my briefs over my asshole. I did my best to avoid making a mess before getting out on the drivers side. Then I stood there for a moment with a little satisfied look on my face while watching him recover. When he finally looked at me I smiled and said, "It was really nice to meet you." Then I excused myself and headed back to the suite after stopping in the bathroom to unload his load.

I'd had fun, but I hadn't had enough. I hoped the older gentleman was adventurous.