The Tranny Trucker

A gust of freezing wind blasted across my face. I succumbed to worries of frostbite as I walked aimlessly along the side of the highway.

The wind of passing trucks nearly knocked me off my feet. This must have been dangerous. It's something I should have considered.

My parents separated about a year ago. It was a tough ordeal. I won't get too much into that. My mother moved to Ohio. We had a rocky relationship but I visited during holidays. This was one of those visits. Christmas is only days away and I'm stuck out here in the cold. I have to get back to Michigan.

That's easier said than done with no transportation nor money. Mom and I had a big fight. She kind of kicked me out and I kind of stormed out at the same time. Being brave like that wasn't so difficult with the sun out and the freezing temperatures kept at bay.

I didn't know how I'd get home. The cold was impairing my brain. I couldn't even feel my ears anymore. Another truck passed by, the wind resulting from it really did knock me down this time. I was small and skinny so it didn't take much.

Another truck's headlights were on me. I looked back. The massive big rig was slowing. They must have felt I was in some serious trouble. Well, I was, wasn't I? Wait, what if I couldn't trust the person who was stopping? I'd never met them so what if they wanted to rob me?

The truck pulled over to the shoulder. I waited on the ground in the grass as I heard the driver's side door open. I waited another moment and then stumbled to my feet as I caught my first glimpse of the driver.

The guy was dressed in a big winter coat. I couldn't get a look at him as he approached.

"Yeh alright over there?" The person called out.

It wasn't a man at all. The person had a woman's voice. It was kind of rough but seemed sympathetic to my situation as well.

"Ummm... yeah... kinda. I think I'm alright."

"Oh yeh sure don' look it. What ta hell yah think yer doing out here at this time? An' in this cold."

The woman walked closer and I got a better look at her. She was a little plump and quite large in general. Her face was round and she wasn't ugly. The first lady trucker I'd ever seen up close. She looked to be around forty or forty-five years old.

"I'm heading back home if I can get there. I didn't mean to make you stop..."

"Where's home, boy? An' what's yer name?"

"I'm Travis... and home is back in Michigan."

She seemed to look over her shoulder a moment, "Well now that's too long ta walk. I don't want yeh out here in this cold. Something bad could become of you. I can take yeh as far as teh border. How'd that sound?"

"I... I don't want to be any trouble..."

She interjected, "No trouble."

I thought for a minute. Things couldn't get much worse than they were now. I didn't know this strange woman but getting as far as the border would be nice. It would probably only be a day's drive and then I could call a cab in Michigan and pay them once I got home. My future looked much better with this woman's offer than without it. It was so damn cold.

"Come on now. It's dangerous out here with these cars passing like this."

I nodded a yes. The woman bridged the last few feet between us and shook my hand. Like the rest of her, they were very large for a woman. She had a few inches on me in height as well.

"My name's Daisy."

"Nice... nice to meet you, Daisy. Thank you for stopping." I shook her hand limply.

Daisy led the way back to her truck. My eyes wandered to her backside. I watched her big butt wobble back and forth in the thick pants while we walked. I was ashamed that an erection began to form in my pants.

Daisy opened the passenger's side door for me. The wheels on this truck were the biggest I'd ever seen. I practically had to climb just to make the first step up the side of the truck. Daisy pushed me with a firm hand up the rest of the way. She slammed the door behind me.

I got my first glance inside the vehicle. Directly behind the two seats was a bed. Off to the side was some rudimentary cooking equipment. Daisy must live here. I didn't understand how, having lived with all the amenities of a house my entire live.

Daisy walked around the back of the truck and came around the driver's side. She stepped up into the truck without any trouble.

"You look some kinda freezin'," Daisy turned up the heat in the truck, "How about I get yeh a blanket?"

Daisy slipped between the two seats, her side brushing into me, and grabbed a quilt off her bed. She slung it around my shoulders, smiling for the first time. I feigned a smile back, though I wasn't terribly excited about my situation.

Daisy plopped down in the driver's seat. She started the truck and threw it into gear. I noticed the many dials and other pieces of equipment in the dashboard. A radio hung nearby. I watched her flip a couple switches and then give the truck some gas.

I looked out the windshield and was amazed at how high we were. Everything else was small and insignificant. My only experience close to this was being on the second level of a train. This seemed somehow cooler. My perspective, going from walking along the highway, to traveling it in this massive piece of machinery, put a smile on my face.

"You don' mind me askin' how yeh ended up on teh side of ta road? Yeh didn' really answer earlier."

I looked across at Daisy, whose eyes were still on the road before answering. "I got thrown out. I couldn't think of any other option but walking with no money. I'm very grateful to you for stopping like you did."

"Options? No, there never are many. Prob'bly happens more often than yeh think."

There was a lull in the conversation. The truck cab was warm now. I was a little restless, straining against the seat belt. Daisy must have noticed it.

"Yeh sure yer alright? You look a little flush. Prob'bly some rest would do yeh good."

"I think I'm okay."

"At least take a drink, kiddo," Daisy picked her thermos up from the cup dispenser and offered it to me, "Here."

I shook my head no.

"Don' be afraid of germs now. Go 'head and take a drink." She offered me the thermos again.

I tentatively took it from her hand. I unscrewed the top and gingerly took a sip. It tasted like warm mint chocolate. I took another sip and put it back down.

"I imagine we'll be beddin' down in an hour or two."

"Umm... what do you do for that?"

"We'll park at a rest stop and close up for teh night. I got teh bed back there. Nothing special, you know."

I turned my head and looked over the bed again. It looked barely big enough to fit Daisy. I started to wonder why she would live like this.

"Do you like... doing this?"

She glanced over at me, "Driving, yeh mean?"

"Yeah."

"Mmhmm. I won't be on teh road too long this time. Just carryin' some electrical supplies back there. Ta money's good."

"That sounds good."

I suddenly felt like we were sharing a very intimate conversation. I was wearing the quilt she slept with. She slept just behind us and spent most of her time living in this truck I assumed. This was her living space. Despite myself, I felt myself attracted to the big woman. She had a southern charm and the girls my age never had curves like Daisy did.

"Teh only bad thing I can say about it is it does get lonely sometimes. Being out there, 'specially on the holidays."

Her words brought me back from my thoughts. I found my eyes drawn back to her, hers were on the road.

"I bet it would be. Do you ever have family to spend them with?"

"No, no I don't," She said with a hint of sadness, "That's teh way it is."

Before I knew what was happening, my arm had traveled across the gap between us. It rested on Daisy's shoulder. I gently squeezed there. It must be this heightened feeling of intimacy.

"I don't have any family to spend holidays with either as you can see."

Daisy returned my shoulder squeeze with a pat on my knee, nodding her head while concentrating on the road. Even though it was gone within the span of a couple seconds, I could still feel her hand on my knee. The hair on the back of my neck was standing up. It might just be the mind of a teenager, but everything seemed to have an sexual element to it. We weren't even a foot from her bed. I mean this was her bedroom!

We talked longer, learning the basics about one another. She was independently contracting for a company currently. She lived in Cedar Rapids, Iowa and was born in the country down south somewhere. I was too sheepish to ask what state the place she described was in.

She was concerned that I might be sick after my time out in the cold. Daisy seemed very interested in the fight I was having with family. We also talked about what would have happened if Daisy hadn't been there to pick me up.

She said this wasn't the place for a boy like me. I was lucky she had been there because I wouldn't have made it otherwise. Daisy said there were a lot of people out there looking to exploit someone like me and it sounded like she knew what she was talking about.

"Yeh really better get to sleep, boy." She finally moved to end the conversation.

I yawned, "Maybe you're right. I can try." I turned over in the seat and closed my eyes.

"Silly. Go on and sleep in teh bed. That's what they're for, yeh know."

My eyes flared open, "Oh no. I couldn't. Where will you sleep?"

"We'll both make out alright. Now don't you worry about me. Do it." Daisy raised her eyebrow up at me and smiled, "Or I can pick yeh up by yer pants and put you back there myself."

I could see this wasn't an argument I was going to win. I didn't want to either. The prospect of sleeping on a bed instead of the passenger seat was appealing. Besides, I think she really meant it about picking me up and putting me in bed herself.

I let out a little laugh and headed behind the seats. I pulled the mound of covers up and slid underneath them, relishing the warmth. I hadn't realized how tired I was until I laid down. My eyelids starting drooping almost immediately.

"Daisy?"

"Mmmhm?"

"Thank you for helping me."

"Goodnight now, boy... Travis." She told me soothingly.

I fell off to sleep. My dreams were dark. Literally. I seemed to be stranded in the pitch dark of night. Suddenly I felt a great weight. It pushed me down into the ground and I couldn't move. The weight brought with it warmth. Heavier and heavier it felt and warmer and warmer it got. I woke up with a bit of a start.

"I didn' mean to wake yeh." Daisy whispered.

My eyes slowly adjusted to the darkness. I took a quick account of the surrounding area, realizing pretty quickly that I was pinned against the back of the cab with Daisy partially on top of me. Her bulky breasts laid on my neck and chest. Her right leg was crossed over mine.

Any normal person waking up to this would naturally be frightened. I wasn't. In a strange way, nothing felt more natural in the world. I was still very groggy though.

"I parked. We're locked in for teh night. It was mighty tough. There's a blizzard out there."

"Oh."

Another extremely natural thing happened. My cock started to grow. The warmth of her body seemed to melt into mine and being in such close proximity to her tits didn't hurt either.

"I'm glad I found yah tonight. Curled up in a ball outside. I didn' know what to make of yah." She chuckled. Her leg seemed to stroke up the length of mine, closer to my crotch and the erection I was sporting.

Daisy kissed my forehead, letting her lips linger there. It might have been an innocent kiss, but we just met earlier tonight, even though it felt like we knew each other better than that, and my teenage hormones never perceived any contact from a girl as innocent.

"Sleep now." She told me, pulling my head deeper into her chest.

I listened but sometime later I woke up again. It felt like a while later. I wasn't sure why I was awake. I was quite warm under the blankets and under Daisy. Her breath seemed steady. She must have been asleep as well.

I was inundated with our current closeness. To say I was inexperienced in sexual things would be charitable. I'd never had this opportunity with a woman before. Daisy probably didn't even see what we were doing through a sexual lens but I sure as hell did.

My hand was shaking. I didn't know what I was doing. I watched my hand, almost in disbelief, as it hovered over Daisy's body and then fell to her lower back. I felt her body rise and fall in rhythm. Feeling somewhat safer in the situation after a minute, my hand slid lower.

I passed over the seam of her shirt and hit the top of her pants. Going lower, my hand ever so gently cupped her butt. A smile must have washed over my face at that point. I cupped it again, feeling the big thing through her thick pants with my fingers.

My erection was painfully hard. Daisy's knee dug into the material of my pants and put my cock in an uncomfortable position. I tried, never taking my hand off my backside, to delicately readjust and give myself more room.

I gently pulled the side of my pants, trying to pull it out from Daisy's knee without waking her. The strategy of tugging a few millimeters at a time was working well. I was almost free and excitedly gave it one last tug. Then it happened.

The bed creaked. In an instant, Daisy's hand grabbed my wrist. Yes, the wrist whose hand had been resting on her ass.

"What're yeh doin'?!" Daisy growled. Her grip on my wrist tightened.

While struggling to free myself from her grip I answered, "I... I was just sleeping. Please let me go."

"I didn' know I picked up a little liar. Tell the truth," She sneered, "Or yer gonna get it."

"I'm sorry. So--so--sorry." My eyes started to well up.

"Thought you'd wait 'til I fell asleep and then cop a feel, huh?"

"I wasn't thinking. I promise."

"Do yah have any idea how old I am? Yer just a damn kid."

"I'm nearly twenty years old."

"An' you think yer a man. Enough of a man to be feelin' on me." Daisy face started to soften, along with her grip on my wrist.

"I'll go if you want me to go. I'm sorry I abused your trust." I told her with sincerity.

"Oh," Daisy seemed almost hurt and let a minute pass, "Men finish what they start. Is that who you are or not?"

"What... what are you saying?"

"You let your intentions be known. Now are yeh going to follow through?"

I gulped, "Well, yes."

Daisy smiled. I was relieved that I wasn't in trouble. I didn't want to go from her warm bed to the freezing streets. And now, now it seemed like she was coming on to me. My boner, which had shrunk when she grabbed my wrist, came back in force.

Daisy licked her lips, "A good, strong man pleases his lover first. Are you up to that task? If yer really the man yah say you are."

I nodded my head and opened my mouth to speak. Daisy beat me to it, pressing her lips against mine. We kissed. Her tongue splitting my lips apart and entering my mouth. She pushed and prodded against my tongue, hungrily smacking her lips on mine. She wrapped her arms around my back and I did the same around her broad back. Daisy pulled me closer until her chest ground into mine.

Then I felt it. The hard bulge pressing into my side. I immediately stopped kissing Daisy, my arms around her back going limp. She responded by kissing me harder, her hands mauling my back and backside.

It was a cock! Daisy was a... a he! I mean she was a woman but she had a cock! The concept wasn't completely foreign to me. I've spent hundreds of hours beating off to various shemale porn and hentai porn. I never thought I'd be this close to one. And I hadn't even known! These revelations invaded my mind while Daisy's tongue invaded my mouth.

I weakly kissed back, rationalizing that kissing this woman wasn't very different in the end than jerking off to shemale porn.

Daisy, presumably satisfied that I was 'game' tore her lips off mine and kissed my face over and over again. "Is my man ready to please? I know yah feel what I feel. My girl down there needs some attention."

"Hmm.." I kissed Daisy's full lips again, "What kind of attention does she require?"

"She's very jealous 'cause she wants to be kissed too. Cuddled like we are. She's jealous of my tongue when it slips into yer sweet mouth."

"Well then... I can do that for her."

I seemed to have a new confidence, my body slipping down Daisy's. Daisy undid her pants and spread her legs. I looked at the pole tenting out of her pants and then rubbed my cheek along it.

Daisy lifted her butt up and slid her pants down her waist. I picked up the slack, pulling them down the rest of the way. Her cock was left in only a pair of cotton panties. I could see just how large it was. Much larger than mine and I didn't seem to mind.

I attached my lips to her hardness, still through her panties. Daisy let a moan escape her lips at first touch. I could feel just how hard it was. My fingers looped into each end of her panties and peeled them down her thighs. Daisy's cock bobbed out into the open.

Daisy smiled down proudly as her thick tube came into view. Dark blue veins ran up the length of her shaft. The whole thing was capped off by a large purple head, presently leaking a creamy liquid.

Daisy saw my eyes travel up the length and focus in on that big impressive head, "Yeh can start there. Teh cherry on top." She chuckled.

I dragged my tongue over the tip of Daisy's cock. Her hand ran through my hair and pressed my head lower. I panicked, opening my mouth wide to accept the big head.

"Suck on it real hard and yah might just get yer present at teh end."

I tried adjusting to having Daisy's cock head in my mouth. It was difficult at first, but I did adjust. Her cock seemed to have a mind of its own, twitching in my mouth and leaking precum. I flicked my tongue across the tip and swallowed the precum that had accumulated there.

The taste was tangy and kind of rich. It didn't seem to have just one flavor. I took another lick, holding the tip tighter between my lips. Daisy seemed overjoyed at these developments. She responded by lightly jabbed her butt upward. That sent another inch of her cock into my mouth. I struggled to stop from choking, getting over my shyness and starting to suck on the inches of cock between my lips.

"Yer gettin' the hang of it, boy. Just make me feel good. Mmm.. just so good."

Out of the corner of my eye, I could see Daisy's big balls. They laid out on the ball, all red and tender looking. My hand crept up the bed and I gently squeezed them in between in my fingers. I pulled them, rubbing my palm on the big things. Daisy seemed to like that.

Meanwhile, my head started bobbing up and down on her shaft. I managed to fit another couple inches into my mouth. I worked my tongue the way I thought would feel good on myself, running it over the underside of her cock head and teasing the shaft with it.

The texture and warmth of Daisy's dick felt good in my mouth. I liked it. That thought sent me a little out of control and I took too much into my mouth. I gagged, then tried to slip my mouth off Daisy's cock. Daisy was there, though. She held my head firmly as just the tip was left in my mouth.

"It's first-time jitters. Don' go leavin' now. Just when it's feelin' so good."

Daisy took over more control of the situation. She directed my mouth on her cock and wiggled her hips to manage how much of her dick was getting sucked. I concentrated on making the inches that were in my mouth feel as good as possible.

"An' get them warm hands back on my balls."

I obeyed Daisy, teasing her balls with my fingers again. She lifted her butt up and slid those extra inches of cock meat into my mouth. I shut my mouth hard, partly to bring her the most pleasure and partly to ensure she wouldn't stuff another inch in my mouth, which was already so full with her massive hard-on.