From Booth to Hotel

I had to drive across the country for my job and after a few hours on the road, all I could think about was getting to Kansas City, Mo so I could get a hotel room and check out the local establishments. Long drives tend to give me a lot of time to think and I eventually get horny after a long day of enduring the vibrations of the road.

In the past, I've had my share of rest area romps, but driving in broad daylight allowed me to stay focused on getting to KC. I arrived and set myself up in a hotel to relax.

Later that afternoon, I went out to check out the adult bookstores that were in the area. I put on my stockings, carried my heels and went out in drag. I didn't really care because I wasn't from the area. If I got pulled over, big deal. I found a small place north of where I was staying and it looked pretty promising. If I was told not to come in dressed the way I was, I'm sure I could find another place.

When I went in, no one was at the counter, but I could hear someone talking behind an office door and videos playing in the back of the store. I sauntered to the back where the video booths were. Typically, one would find guys standing around, but there was no one standing in the hall; they were in the booths.

I picked a booth and plugged a bill in to flip through the channels. As I flipped through channels, someone lightly tapped on my door. My heels clicking on the floor, I walked over to the door to see if I was going to be escorted out. I opened the door waiting for the worst when I saw that it was a rather young looking guy that barely looked old enough to be in this establishment.

"Can I join you?" he smiled. He barely looked 18 and he wanted to share the booth with me.

"Sure. Come in." I said with a seductive smile.

"They have larger booths on the other side and I reserved one." he said shyly.. "They're a bit larger and much more comfortable than the benches and chairs in these booths."

I thought the booth I was in was rather large, but evidently I was wrong. I joined him in another booth that was a little larger, but it had a nice large, cushioned vinyl platform attached to the wall. It was cleaner than the other booths also. It didn't have the smell of dried cum and sweat.

To be certain, I asked him his age. He was slim and handsome but oh so young looking.

"I'm 20." he said. I looked at him sternly in disbelief. "Ok... I'm 18. But I can still come in here."

I wasn't arguing. I just wanted to make sure I wasn't going to be busted.

The video was already playing... Two guys were spit-roasting a MILF with gusto. She turned out to be a squirter. 'Fine choice of entertainment', I thought.

"My name is Tyler." he said. "I'm Dinata... and I like to crossdress". I remarked... Awkward to say the least. It's rare that names are exchanged. I took this moment to ask him what kind of pleasure he was looking for. Judging by his bulge, he definitely had to empty his balls or he would eventually strain those poor testicles to the point of blue balls.

"Well, I like to jerk off and I think it would be fun to have my cock sucked." He stammered. I thought to myself 'Was this his first time?'... Couldn't be.

"Well... Show me what you got." I said as I licked my lips like a hungry slut. As he dropped his pants, I noticed that he didn't have much pubic hair, which was nice for me. However he did have an impressive size member dangling in front of him. I was on him like a rabid she-wolf, throating his impressive cock like I was sucking to save my life. For an 18-year old, and being well-endowed, he should be out fucking his neighbor's daughter, but he's here getting his cock sucked by a crossdresser with no inhibitions.

As I was sucking the hell out of him, he tensed up, then hot sperm flooded my mouth and throat, surprising me and causing me to choke on his sweet choad. He tasted so good, and fortunately he had great stamina because I was wanting more.

Surprisingly, he stayed as hard as rock. I stroked him until every drop of cum was spent. I asked him if he would like to come back to my hotel room to have a few drinks and then see where we can go from there... He graciously accepted the invite and as he pulled up his pants, he said he would follow me in his car. As he walked by the clerk that happened to be at the counter this time, they made small talk and then he was out the door.

On my way out, I stopped at the bathroom and freshened up and as I walked by the counter, the clerk looked at me, smiled and winked at me. "I'll be back for more." I said sweetly as I walked out.

Tyler followed me in his car as we made it back to the hotel. Once in my hotel room, I excused myself to 'change into something more comfortable', as they say. I returned about 20 minutes later with fresh makeup and sporting a strappy little number with garters for my stockings and it accentuated what little breasts I had. I really didn't have any tits, but it made it look as though I had something. I had my heels on which made me slightly taller than Tyler, but he was loving what was in front of him. Me!

As the sun was setting outside, I made us drinks and we made small talk about what led us down the road we were currently on. It all came down to hormones and getting it when the opportunity presented itself. With the mood just right, I took my place on my knees in front of my shy but well-endowed friend and began to tug at his cock once again.

"Does your mother know that you hang out with sluts like me?" I asked teasingly as I freed his cock.

"She thinks I'm watching a game at a friend's house." He remarked... She never wants me to drive if I've been drinking so I usually spend the night on his couch."

"Well, you're with me now. You're more than welcome to stay over in my suite, provided you're not some crazed psychopath, then I would have to ask you to leave." We both laughed and I got down to business, chumming on his mushroom head again.

He had one of the most beautiful cocks I had ever seen on any guy. It was straight, meaty and erect. The lack of hair made giving him head much more enjoyable. I edged him a few times until he nearly came, but then I held firm, pulled his nut-sack and teased him a little. I looked into his eyes as he moaned softly. I swirled my tongue around the head, and then went down on him and came back up, occasionally rubbing my teeth across from the base to the tip of his glans, teasing him mercilessly.

"I would really like to fuck you in the ass..." He said through his heavy breathing.

"Have you ever done that before?" I asked.

"No... But I would really like to. I've been watching movies and I read things, so I can be gentle." He said with a shy smile. By now I was leaking pre-cum on my stocking tops and they were getting soaked.

Getting some lube from the bedroom, I showed him how to lube me up properly using a 'lube launcher'. A device that looked like an oversized hypodermic filled with lubricant. I had already douched early and cleaned myself out, so there was plenty of room to accommodate him and lots of lube.

I was feeling loose with the sexy background music and heady after a few drinks, so I laid on a blanket in front of him and rubbed light oil over my body while he slowly stroked himself. He was like a young man experiencing his first erotic encounter at a strip club as he looked intently at me as I rubbed my body to a glistening sheen. I turned away from him and arched my back as I reached between my legs and rubbed my ass like a wet pussy. I gyrated my hips slowly and that was all the coaxing he needed.

He positioned himself behind me and I felt his swollen head at the entrance to my sphincter. I teased him by pushing back and then moving forward as if I was a virgin being penetrated and unsure if I wanted to give it up... The heat emanating from his cock was so intense that once the head was positioned just right, I lunged back onto him with one push, taking his cock up to the hilt. We both moaned in unison as I gyrated my hips once again to show him that I could milk him dry if I desired. But this time, I needed him to take control. Be the stud, making me his fuck hole for his cock.

He leaned forward and wrapped his arms around my waist as he started to hump me like a dog getting a piece of ass. I was in heaven feeling his chest on my back as we moved together to become one with his cock deep inside of me. He started to pick up speed, but his cock rubbing my prostate was something I had somewhat experienced before but not this good.

"Slow down a little, hon. Don't cum so soon. It feels so good. having you fill my ass up with your cock." I moaned to him.

"Your ass is so tight, I want to ride you all night." he panted in my ear. "I have never felt anything like this."

My miniscule penis was oozing long strands of precum and it broke off with each thrust when his ball slapped my balls. At this pace, we were both going to cum sooner rather than later.

After several minutes of teasing each other, I looked at him seductively over my shoulders. "Let me roll over" I panted... He pulled out and I quickly rolled over onto my back and placed both of my stocking covered legs over his shoulders and pointed my heels toward the heavens and asked him to "fuck me and make me a proper whore." Without delay, he pushed his purple headed cock back into my ass and proceeded to fuck me, lfting my ass up as he plowed into me again and again.

He laid into me as the head massaged my prostate again and I began shaking as I felt an orgasm cumming on from the pure act of being a fuck-puppet. My moans turned to cries as I beckoned him to pound me more and more. Cum was pouring from my cock like pussy juice from a spasming snatch. "Fill me up baby. Blow your load into my pussy." Picking my hips up he convulsed and I'm certain I felt his first shot fill my bowels with pearly lava. "God damn! Fuck me, Ty! Cum in my snatch!" I wailed as we both climaxed simultaneously.

With an animal-like groan he blasted rope after rope of hot, steamy jizm into my bowels while practically standing and holding me by my hips. As Tyler gently laid me back down he pulled his cock from my ass-pussy and finished stroking it onto me.

"That was intense.:" he remarked as he stroked his semi-rigid man-cock. I was nearly exhausted from the experience, but I knew that I would recover after a while, but a good nap would sound good right now.

"Shower or hot tub?" I asked...

"Huh?"

"Would you like to join me in the shower or the hot tub?

"Why not both?" Tyler responded. "Good! We'll have both..."

I stayed another day in KC because Tyler and I could not find the motivation to leave the hotel room. We spent the days and evenings in every position we could muster and it seemed like gallons of sperm had been coaxed from his testicles. I spent hours sucking his cock, riding his cock and jerking him off whenever I was in the right position.

By the time I did leave, I'm sure I was walking a little differently and had a few new wrinkles around my lips. Ty was one of the best fucks I ever had from a younger man. It's been several years since we communicated. I'm sure that by now, he's making some young lady happy. He made me feel like a real harlot and I will have these memories for the rest of my life. Wherever you are Ty, I miss you and your cock!