On the Road Adventure

Story Info
Trucker opens his eyes.
1.2k words
4.55
6.2k
12
Story does not have any tags

Part 1 of the 2 part series

Updated 02/17/2024
Created 02/12/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I figured I would try a story from the opposite view of how my stories usually go. This is out of my comfort zone, but be brutally honest, I like criticism, good or bad. It helps. Characters are over 18.

All My name's Bob. I'm a long haul trucker. Divorced, like a lot of us, it's hard to keep a home life when most of your time is on the road. It ended as amicably as possible, I guess. Fortunately, there were no kids (Or child support) to fight over. Since most of my time is spent on the road, in my rig (Freightliner Cascadia), my "residence" is a studio apartment, over a friend's garage. It ain't big, but suits my needs.

Anyway, I was coming back from Washington, running empty, and stopped in a truck stop for a meal, and a shower. The shower relaxed me and three cups of coffee (some of the best I'd tasted on months) with my meal had me high stepping to the john. I stepped up to the urinal, and pulled out my business, and let it fly. I was painting the back of that urinal with a stream that would make anyone proud, when I happen to notice, out of the corner of my eye, what I initially thought was a girl. Couldn't be, though, though, cause he/it, whatever was standing at a urinal, too. What really caught my attention was, he/it, whatever, was staring at my dick. Not just glancing, I mean a fixed stare.

Thinking I'd just embarrass him/it, I said, "ever seen anything like it, honey?" (I couldn't resist) Well, he/it looked like I'd hit him/it, with a brick, and turned deep red. I had to laugh out loud. It was obvious that he/it didn't MEAN to get caught looking. Well, being the asshole I'm known for, I added, "have yourself a feel of a real dick, instead of that little nub you got." I hadn't REALLY intended on doing anything, but I turned to him/it and waved my dick around, , pushing it up closer. He/it looked scared, and was stammering, apparently felt threatened, and took me seriously. I'll be damned! Those little hands reached out and wrapped around my business. They were shaking, but the reaction was instant, I got as stiff as I've ever remembered.

This seemed to amaze he/it, and started stroking me. Well, NOW, I'm the embarrassed one, looking around to make sure no one else is in here, and can see this fairy giving me a hand job. My little joke got out of hand (no pun intended) real quick, but, the little head has no conscience. After a few seconds, I grabbed he/it by the collar, and pulled him into a stall. It was only a few steps, but he/it never let go. I'm thinking, This sissy is either terrified of me, or wants my dick. Either way? Why the fuck not take advantage? I've been horny for three weeks now, and damned sure ready to bust a nut.

As soon as I latched the stall door, I pushed he/it to his knees. Eyes wide, as he figured the next step that was coming. He/it opened his mouth to whine, I said, "No, Baby, you started this, you're finishing it!" He looked defeated, but timidly leaned close. Holy shit!

I've never felt anything like this. He/it MUST have done this before. Imagine the finest pussy you've ever had, this beat it. It was like being fucked by an angel. So warm, so soft, but...more. My head was swimming. I tried to fight off cumming, to make it last longer, I swear I did, but That little head wanted, no, NEEDED to give this sissy it's reward. I latched onto his/it's head, and shot load after load. It couldn't have just been because I was horny. I'd gone longer bouts without, before. He/it was gagging sniffling, coughing, but also, swallowing everything that didn't spew out of he/it's mouth. THEN scraped what did off his/it's chin, and licked it.

I'm not sure WHICH of us was more surprised. Me, for feeling like I'd won the sexual lottery, or he/it, for realizing what he/it truly was. I pulled him/it to stand, as he/it wiped tears off his/it's cheek, still trying to clear his/it's throat. "What's your name? And what are you doing in a truck stop? This ain't a place for... people like...you." (Okay, yeah, I felt a little hypocritical, saying that, since I'd just face fucked him/it) I stood there, taking a better look. He/it couldn't have been more than 5'5", 120 lbs, soaking wet, with shoulder length brown hair, and a baby face. Sharp contrast to my 6'3", 240 lbs.

He/it looked up at me, with a look that truly puzzled me Instead of anger, or contempt, I saw... something, I don't know,...soft...grateful? It was weird. He/it finally answered. "I...didn't mean to stare at you, Sir, I really didn't. M-My name is Leslie, and... I... came here, trying to get a ride, out of here. My life... sucks, and I want to find... something else." With that, tears started again. Fuck, DON'T cry. I hate when people cry...

"Hold up, ...Leslie. Don't cry. Are you hungry? I'll buy you a meal, and you can explain it. And, I'm the one who's sorry. I mistreated you...badly, I should never have done that, but... I did. I want to make up for it." I saw a little smile, as he nodded his head. I opened the stall door. He walked over and picked up a backpack, that I hadn't noticed before, that was next to the urinal he was using. We walked to the restaurant, and I had coffee while he ate like he hadn't eaten in days. He started telling me that his mom died, and since then, and even before, his step-dad treated him like crap. His school life wasn't much better. He was picked on, because of his size, and looks. He felt there had to be something better, if he could just find it.

He took a deep breath and added, that he was scared, at what I had made him do, but that he didn't hate it. He'd been secretly curious and even if I hadn't meant to, I'd helped him with that. " You REALLY never had done that before? But, you were so damn good. " He smiled when I said that, and thanked me.

"M-Maybe it was a first step in finding myself. It really felt... natural." He blushed, but gave a timid smile. Wheels started turning. I'm not gay, never thought about dudes before. BUT... a boy, who looks like a girl, and can suck like that? Maybe we can help each other out. If I could convince him to DRESS like a girl, then it could work. Because, Well, I um, don't want my buddies thinking I'm gay, right?

I leaned closer, whispering, "Leslie, since you don't have any clear plans, you wanna ride with me for a while? I... have an idea I'd like to run by you, but it might take a while. AND, maybe, if you want, we could do that OTHER thing... again." He blushed again, and beamed. I paid the bill, and we walked out to my rig. He looked around, didn't see anyone, and hugged me. You know what? It wasn't as weird as I thought, and I hugged back.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
AnonymousAnonymous2 months ago

I have been to the truck stop. I know the aggressive, denial, lust filled man that can be found there. This of course does not seem to be your character. But a taste of that reality can a long way.

EricaDoesNowEricaDoesNow2 months agoAuthor

I am glad most of you got what I was trying to do. Trust me, it wasn't easy, as I am definitely the submissive, and HAVE felt the "he/it" vibe from people before. I believe it is essential for my story, AND, if Literotica ever publishes the second chapter, (They tend to hold my stories out about a week before publishing), You'll see a progression. One of my favorite sayings is, "The only thing worse than being talked about? Is NOT being talked about." Good or bad, I got some conversation going! Go me! :)

nemanja1503nemanja15032 months ago

Nah don't worry Erica, I think most people understood that it is meant to show the trucker is not the most open minded, or even merely good, person. Though the he/it writing is awkward from a linguistic standpoint. He might be at first unsure if to refer to Leslie as a he or an it but he is unlikely to keep thinking like that all the time even inside his own head. He would go with either he or it for each particular instance, though he can mix it up, going with one or the other as he goes along.

Anyway interesting to see you write from the perspective of the man for once, so far the experiment is a success.

As an aside I hope you write a more romantic story one of these days. I'm kind of weird in that I like things to go hard in the bedroom, like really hard, but be lovey dovey the rest of the time. I also don't like cheating, sharing or group stuff in general very much. Basically I want my girl to be a one man slut ;) So having a story of yours where a young trans girl slowly awakens to her nature with a dominating but caring daddy would be juuust prefect. Think about it if the premise is appealing to you too. Who knows it might even be this story if the trucker learns to be less of an ass ;)

AnonymousAnonymous2 months ago

The he/it didn't bother me. I just assumed it was from the trucker's perspective since it's written in the first person. Anyways, I would love to see a continuation of the story!

AnonymousAnonymous2 months ago

That was a hot story, and I look forward to their future adventures together. And there is a but. And it is the he/it bit. I read your comment and I know where you are coming from, as I have looked at some people and thought those questions. But after the first confusion has left me, I pick one title in my head.

Please continue the story, I want them to be very happy with each other (and a lot of dirty and clean fucking .)

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
Monica Turns Me Out My domme ex girlfriend finishes what she started.in Transgender & Crossdressers
Keeping a Secret After a discovery, should he keep their secret or not?in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories