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Introduction:

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Walking along the road on a cold winter night in Wisconsin, cars passed by honking their horns. Shivering cold, I didn’t know how much longer I could go. I didn’t know where I was going, didn’t really have a place to go. I just knew I couldn’t stay there any longer. I had no money, no phone, just the clothes on my back. My hands and feet were beginning to feel numb as I trekked through the snow while it continues to fall.

Cars continue to pass by until finally a large semi-truck with an even larger trailer pulls off to the side. Feeling skeptical, I was more than scared. What if this guy was some kind of rapist or something? As the trucker opened the door and jumped out I noticed he was rather tall. I hesitated as he walked up to me. “What are ya doing out this late on a cold night like this?”

It’s a woman! The sound of her voice was sweet like honey. Finally, she got close enough for me to make out her features. She was definitely taller than me, that’s for sure. Her face was hidden underneath a ball cap. She was covered in a large winter jacket, which hid all of her upper body. She wore jeans that barely were able to stretch over her thick muscular legs. A large pair of warm boots covered her feet. “Nothing,” was all I could say.

“Where ya heading? Maybe I could give ya a lift?”

Hesitating, I don’t know this woman, but I relent. “I don’t know..” She didn’t seem like she was dangerous or anything.

“Oh.. I see… Who ya running from?”

I swallow a big gulp. “I.. I just need to get out of here.”

“Well I’m heading south, you’re welcome to join me.”

“Are you sure? I don’t want to intrude.”

“Oh don’t worry about it. Now come on, it’s dangerous out here. You could easily get hit by one of these cars as dark as it is.”

I followed her back to the truck. My eyes couldn’t help but drop to her thick sculpted ass that barely fit in those jeans. She opened the passenger side door and I start to climb in. She placed her hand on my rear and gives me a shove helping me up, slamming the door behind me.

I finally got a good look at her face once she got in. Wow… She wasn’t what I expected. She was gorgeous. She had dark chocolate skin. Even though she had a strong jaw, her face was one of those faces that gave you butterflies. She had the most luscious lips I’d ever seen. Her sleek black hair was done up in a ponytail that came out of the backside of her ball cap.

She glanced over at me and gave me a smile. “The name’s Edna by the way, mind giving me yours?”

“Alex.”

“Well Alex, it’s nice to meet ya. Now let’s get moving.”

With that, she shifted into gear and we were off. We rode in silence giving me a chance to look around. There wasn’t much. She had a giant thermos sitting between the seats next to the stick shift. She had a monitor with GPS and a radio below it in the center of her dashboard. Her phone was mounted above it. It wasn’t until I looked back that I saw a bed, a mini-fridge, a microwave and a few cupboards. Holy shit, it’s pretty nice in here. Like a mini motorhome. A really small, tightly compacted motorhome with barely enough room to move.

“So Alex, ya never answered my question.”

I look up at her trying to remember what she asked.

“Who ya running from?”

I guess it’s not going to hurt to tell her. I doubt she’s going to judge.

“Home…”

“How come? Can’t be that bad.”

I finally give in, what harm could come from telling a stranger about my life?

“My mom… she has some problems. Mostly drugs, alcohol and her taste in men. She brings home guys that like to beat her. I could only take it for so long. I finally made her choose between the things that are destroying her.”

“I see…”

After a long awkward silence, she finally spoke up. “I can’t really blame ya for that. What about your dad?”

“Don’t know, never met him.”

“Oh… No other family?”

I shook my head no.

“What was the plan? Just gonna keep walking until ya freeze to death?”

“I didn’t really have a plan, to be honest, I just couldn’t take it anymore.”

“I get that... I really do. But you need to think this through. I don’t blame ya for leaving and I’m certainly not telling ya to go back. I’m just saying it’s dangerous out here.” She gave me a long gaze before looking back at the road. “You’re lucky I found you when I did. I know a few other truckers who would love to take advantage of a kid like you, especially Big Joe.”

“I appreciate it, I really do.”

“I don’t mind at all. I could use the company. Being a trucker can get awfully lonely. How old are you anyway?”

“I just turned 18 a few months back.”

Another long awkward silence took over. Even though the cab was nice and warm I couldn’t help but shiver. I was still freezing cold from the walk. She turns the radio on.

‘More panic in southern California as the missing person’s count rises. 29 people reported missing so far. Some of them children, most of them are teens. We're going to quickly go over the names of our 29 missing people. If you have any information about these individuals that will help locate them please call 1-213-334-3431 to report any vital information. The names are in no particular order. Zachary Easley, Justin Walters, Eliza…’ Edna flicks the switch and turns the radio off.

“It’s always such doom and gloom on the radio these days. There’s a blanket back there, go ahead and take it, you must be freezing.”

“I don’t want to be a bother.”

“Kid I’m not going to have ya catching a cold, now go on. By the way, if you’re thirsty I got a thermos full of hot coffee, feel free to have a drink.”

I crawled back and grabbed the blanket off of her bed and wrapped myself in it as I climbed back in the passenger seat. Then I took a big swig of her coffee. It was just black coffee, kind of bitter, but it was hot.

“Thanks... For everything.”

“Just glad to help. So do you have any other family or friends you can stay with?”

“No…”

“Really?” She looked at me with a puzzled expression.

“I’m not the most social person. I’ve always just stayed in my room on my computer.”

“That surprises me, I would have thought a cute boy like you would have lots of friends.”

“I wish… I was always picked on and bullied…”

“I see… I was bullied in school too.”

“Really?!”

“Yeah! All the time! I’ll let you in on a little secret... I’m transgender.”

“Oh... “ OH! Wow, I didn’t expect that! And yet, I’m not all that phased by it. “Was it tough growing up as a transgender?”

“Like you wouldn’t believe! A black trans woman, you can bet I got a lot of crap!”

“Where you ever able to get them to stop?”

“Short answer… No. But I learned to accept it and I also learned how to defend myself and accept who I am.”

“It seems like you turned out alright.”

“Why thank you!”

An awkward silence took over, as we continued trucking through the snow.

“So… do you enjoy all of this?” I ask, breaking the silence.

“Trucking?”

“Yeah.”

“Well besides for the loneliness, it’s not bad. Pays good.”

“Doesn’t it get boring?”

“Ha, well it’s definitely not the most exciting job.”

“What do you do to keep yourself sane?”

“Well, besides masturbate a lot? I don’t mind listening to the radio. Although I much prefer having someone to talk to.”

I look away, feeling myself blush.

“You?”

“I usually just read or play video games.”

“What do you like to read?”

“Mostly sci-fi/fantasy.”

As the conversation continued the small talk gradually deepened. Eventually, Edna started to open up more. I happily listened to some of her tales on the road. She had some crazy stories.

“You wouldn’t believe how many times I’ve had to fight off some lunatic with road rage. People sure are crazy. One time this fucker in a minivan pulled out in front of me and gave me the bird. I rode his ass all the way to the next stop.”

“What an asshole.”

“Right!?”

She continued to tell more stories as we made our way. Things were getting worse out, snow started to come down hard.

“You look tired, how about you go lay down. I’m probably going to pull off here soon. Getting pretty bad out.”

“I can’t sleep there, that’s your bed. Where are you going to sleep?”

“There’s enough room for the both of us. Don’t worry.”

“Are you sure?” The thought of sharing a bed with Edna for some reason excited me.

“Yeah go right on in and make yourself comfy. I’ll join ya once I find a place to park this thing.”

“Okay.. Once again thank you so much for all you’ve done. If there is anything I can do to repay ya, just let me know. I don’t have much… Well, I really don’t have anything, but I’ll do whatever I can to help you out.”

“You mean that?”

“Yeah absolutely!”

“I’m sure we can come to some sort of arrangement, now get some rest.” With that being said I climbed into the back and collapsed on her bed, quickly drifting off to sleep.

Chapter

I woke up the next morning wrapped in Edna’s arms. I could feel the rise and fall of her chest as her breast are hard pressed against my back. Her hand tightly clasped around my abdomen, gently rubbing up and down against the shirt that covered my stomach. And her large cock pressed tightly against my ass, the only thing between that massive python and my butt is just a few layers of clothes. I don’t know what to do… I’m somewhat terrified, but at the same time really aroused. I pressed my butt back, rubbing it up and down her shaft. I leaned over to look at her, realizing she was awake with a rather large smile. “Morning sunshine. Sleep well?”

“Uhhhh yeah, actually I did.” Her hand crept under my shirt, this time rubbing the bare skin of my stomach. The touch of her hand on my skin sent tingles through me.

“I’ve been thinking… I could use a boy like you around. I haven’t had decent company in only God knows how long. Or a good fuck,” Her hand slid down my pants, causing me to fidget. “I’ve got an offer for ya.”

Her hand wrapped around my already hard shaft. “WH.. what kind of offer?” I stuttered.

“You can stay with me however long ya like, you’ll have a nice warm bed to sleep in, free meals and what not. I’ll treat ya real good…” Her hand started to stroke my cock.

“That’s awfully nice of you…” I had the feeling she wasn’t doing this out of the kindness of her heart. She wanted something in return.

“Of course, you’re going to have to do something in return…” I knew it. I started to quiver, her hand felt so good. What does she want with me?

“I don’t have any money…”

“Oh darlin, it’s not your money I want…” I felt something press up against my butt. “It’s your ass I want.”

“What!?!” Woah, She rammed her steely hard cock against my rear. I reached back and brushed my hand up against a massive cock straining the fabric of her underwear. Her cock is at least 9 inches.

I look up at her completely horrified. “I’ve never had sex before…” I whimper, I’m completely terrified at the thought of losing my virginity something as large as her cock. I don’t know if my ass can handle it.

“I figured as much. I’ll be gentle.” She whispers in my ear as her hand squeezes my cock causing me to gasp.

“Relax! I’m don’t want to hurt ya. Although I’m not gonna lie, it’s going to hurt just a little, but once I break that ass in, it’ll feel wonderful,” She gyrated her hips, rubbing that constrained cock up against my ass. “Trust me, I want you to enjoy this just as much as I’m going to.”

“I don’t know if I can do this. Your cock's too big! It will tear me apart!” I argue.

“Hmm, baby I’ll make sure your ass will be nice and ready. And you can get my cock slick with spit,” she whispered in my ear. “This will be your way of repaying me for my generous hospitality.”

“What choice do I have?” I ask.

“You always have a choice. If you don’t want to do it, I completely understand. I’ll drop you off wherever you want.”

I roll on my back and look into those dark brown eyes of hers. “Really!?”

She nods. I don’t know why, but I trust her. There is something about her… I want to stay with her.

I’m absolutely terrified of that giant cock of hers, though. But… The thought of belonging to her, having her protect me… It doesn’t sound all that bad. Having a place to sleep and free meals. She is beautiful. “Please… just go easy on me. I’ve never done this before.”

A giant smile crosses her face. Her hand slips out from under my shirt and grasps the back of my head pulling me into a kiss. Her tongue slips past my lips and wrestles with my own tongue. I’ve never been kissed like this before. Well… I’ve never really been kissed before. I feel her other hand grab the button of my pants, undoing them. She breaks away from the kiss and leans up, unzips my pants and yanks them off. There is a tent in my boxers and an even bigger smile appears on Edna’s face. “Looks like you want this just as bad as I do.”

She pulls off her shirt revealing a large pair of breast, her areolas are huge. She’s got a rock hard set of abs too. She then takes off her panties, her monster cock springs free.

“You’re gonna want to come over here and get my cock nice and wet, trust me... “ she reaches her hand down and starts to stroke that python. “It’ll hurt a lot less if it’s coated in spit.”

I crawl over to the end of the bed where she eagerly waits. Just looking at that massive log makes me shiver. I look up into those dark brown eyes as she urges her hips forward, bringing her cock a little closer to my face. It’s only a few inches away. A musky scent hits my nostrils. “Go on, give it a taste.”

Reaching out, I can’t even wrap my fingers around the girth of her pole. I close my eyes as I stick out my tongue and lean forward. Pressing the tip of her cock against my wet tongue, it doesn’t taste half bad. It’s sorta spongey. “That’s it!” she moans.

I open my eyes as I bring my tongue down her shaft. Holy shit, it can practically cover my face. “Good job! Now put it in your mouth!” she says.

I lick my way back up her cock and open up my mouth as wide as I can. Placing the head of her cock at the entrance of my mouth, it can barely fit inside. She urges her hips forward, pushing the tip of her cock completely inside. My mouth is utterly filled with her tip. Her hands grab a handful of my hair as she pulls my head in, further forcing more of her cock in my mouth. The tip is at the entrance of my throat. I place a hand on her hip and I try to push back, but her iron grip pulls my head in as she thrust that big dick down my throat. I can’t breathe! It’s completely blocking my windpipe. The sad part is barely half of it will fit in my mouth. I struggle and try to push myself free. She relents and pulls back allowing me to catch a lungful of air. But the reprieve is cut short as she slams that fat log back down my throat.

I gag and squirm as tears roll down my eyes. Finally, she lets go of my hair and I pull back as her cock pops out of my mouth leaving a trail of spit. “That was amazing! Fuck!” she moans. “Now let me get a piece of that ass!”

She forces me down on my stomach and I look back at her flooded with fear. “You promised you would be gentle!”

“Relax! I’m going to keep my word, I promise. It’s just been too long since I’ve had a nice piece of ass like yours.” She says as she pulls my boxers down revealing my bare butt.

“Oh my god, it’s gotta be the best ass I’ve ever seen.” She then pulls my ass cheeks apart and buries her face in between them. I can feel her tongue lick up and down my crack until it makes its way to my butthole.

SMACK! “AHhhhhh!” I yell as she gives my ass a good slap and a squeeze.

“This is too good to be true,” She mumbles as her tongue tries to penetrate my asshole, which oddly feels kind of good. I feel it push pass my rectum, it’s the weirdest pleasure I’ve ever felt.

I let out a moan as she starts to tongue fuck my anus. She gives my ass another slap, causing a grunt to escape my lips. Her tongue retreats from my asshole, but something else takes its place. She works her finger in my ass, pushing it down to the knuckle. “Uhhhhh fuck!” I groan.

“Do you like that?” She asks. Honestly, I don’t know how I feel about it. It’s oddly stimulating.

She pulls her finger out and then forces two fingers down my ass. “Oh fuck!” I grunt in surprise. This time it’s a little painful. She starts to fuck me with her fingers eliciting all sorts of gasps and grunts to escape my mouth. Finally, she pulls out her fingers.

She then climbs on top of me and straddles my thighs. I lean up to look back at her, but she places a hand on my back forcing me back down. “Relax, the tenser you are the more it’s going to hurt. Take a deep breath.”

I do as she tells me to and inhales a lungful of air. As I do, I feel her cock rub up and down my asscrack. She spits on my asshole as her cock finally lands on its destination, my little rosebud. She rubs the spit around my butthole with the tip of her cock. “Remember just breathe.”

I take another deep breath, but as I inhale she presses her massive cock against my asshole. “OOHHH FUCK!” I yell out. It hurts so bad! Her cock feels like it’s tearing me apart. I could feel the head of her dick finally break through my rectum. She held her dick there for a few moments, allowing me to finally catch my breath as my ass tries to adjust to the massive intruder.

She doesn’t hold it there long. Slowly she starts to force that fucking log further in my ass. “AHHHHHHH!” I scream out. “It’s too big!! Please no more!”

“Baby, this is the worse part! It’ll get better, trust me!” She says as she continues to push that anaconda further in. “God I can barely get halfway inside of you! You’re just so fucking tight!”

At this point, I’m panting for air as sweat starts to drip from my forehead. She holds that beast inside of me and leans her weight on top of me. I can feel those large breasts against my back. “Just relax, the pain will lessen, I promise. It’ll start to feel good,” she whispers in my ear.

I can feel the heat of her breathe against the back of my neck. She then slowly starts to pull her hips back, bringing that tree trunk out to the tip. Without warning, she urges it back in. I gasp as my ass is completely filled up with her cock. “Ahhhhh fuck!”

Again she brings her hips back, this time she forces it back in a little harder, pushing the air out of my lungs. She reaches out with both of her hands and grabs my wrists, bringing them out in front of me. Once again she pulls out to the tip of her cock and this time slams it back it. I cry out in pain. “That’s it, baby, let it all out.”

She starts to pump that dick inside of me. I grunt with every thrust. I feel each and every vein as her cock sinks deeper down into my ass. The pain is still there, but I also start to feel a tinge of pleasure. I feel her lips against the back of my neck as she starts to get into a rhythm, pumping in and out of me. A moan escapes my lips.

“Now you’re starting to like it! I can tell.”

The pleasure is quickly starting to mount with every thrust. I moan and groan as her cock milks my prostate. “Ooooh, fuuuck!”

My cock is harder than steel as it rubs up against the sheets. “That’s it, baby, moan for me.”

She pushes her hips forward, lodging that fat cock down my ass. “Uuuuuuhhhh!” I moan.

“Tell me how much you love my big fat dick inside you?” She groans as she continues to hump my rear.

“OOOoooooh fuuuck! I ...I Love ...uuuuh I love your fat dick inside me!” I gasp as she picks up the past, thrusting and pumping that monster cock into me at an increasingly faster rate. “Oh fuck!”

“That's a good boy!” she moans into my ear. “Now take that dick.”

She really unleashes hell on my ass, fucking me like an animal at this point. “Oh Fuck baby, your ass feels so fucking good!”

My own cock starts to pulse as I unload a big rope of cum all over the sheets. “Uuuuuuuhhhhhhh fuuuuuckkkk!” I gasp.

“Tell me you want to be mine, tell me you’re ready to be my butt slut.” She moans into my ear, slamming that massive member into me.

“Yes, I’m yours! Oh, fuck me! My ass is yours!” I shout as I can feel that dick start to grow harder.

“Oh fuck! I’m gonna cum!” She shouts. She pulls back one last time before sinking that fat cock as deep as it’ll go. I feel a hot liquid fill my insides as her cock starts to pulse spewing out a load of cum. She paints the inside of me with her seed as she collapses on top of me. “Oh fuck! That was the best fuck I’ve ever had!” she pants as she kisses my neck. We’re both covered in sweat. Her hands let go of my wrists and just lay there on top of mine. She slowly gyrates her hips back in forth as she dumps the last bit of cum inside me.

Her cock slowly goes soft. I’m exhausted and desperately trying to catch my breath. She plants a few more kisses on the back of my neck as she interlocks her fingers with mine. “I want you to stay with me! I promise I’ll take good care of you!” she whispers in my ear. “Just please don’t leave.”

I lean back and turn my head towards her. Our eyes connect as she looks down at me. “I’ve never experienced anything like that!” I say to her. Even though it was so painful at first, the pleasure overtook all my senses.

She leans in and plants those luscious lips against mine. We kiss so deeply, a spark shoots through me. She breaks off the kiss and finally pulls her flaccid cock out of my ass. “Come on, what do ya say we go get something to eat for breakfast?”

“I’m starving!” I say. I haven’t had anything to eat in a really long time.

“I figured as much, good thing I parked outside a roadside diner, best one for miles.” she smiles at me. “You’ll love the food here.”

We both get dressed and jump out of her truck. As soon as I get out, the cold air sends a shiver down my spine. There are several other trucks parked alongside hers. Snow has completely covered the ground. For November, we sure have a lot of snow. We head into the diner and take a seat in one of the empty booths.

I wince a little as my bottom hits the cushion. My ass is a little sore from the constant pounding of her big black cock. A petite waitress stops on over and asks if we want some coffee. Edna nods and I figure I might as well have a cup too. She fills up our cups and tells us to let her know when we’re ready to order.

I start browsing through the menu. The biggest burliest man I’ve ever seen walks over to us. “Edna, see you got yourself a nice boy to keep ya warm…” He says. “When you're done with him, feel free to pass him my way. I would love to sink my cock in a sissy boy like that.”

“Not a chance Joe. This one’s mine,” she replies. I let out a sigh of relief. It doesn’t surprise me that this is Big Joe. I should've guessed just by the size of him. He’s at least 6’5’’ or taller. His gut is hanging out from his shirt and his pants barely stay on. On top of that, he smells kind of funny. Like he hasn’t showered in days. I shudder at the thought of what could have happened he picked me up instead of Edna.

“Fine, I’ll remember that..” He mumbles as he heads for the exit.

“That’s Big Joe?” I ask.

“Yep! See, things could have been really bad if I hadn’t picked you up,” she says.

“No kidding, I can’t believe anyone would stay a night in his truck,” I say.

“No one does so willingly,” she adds. “Do you know what you want to eat?”

“Not really, what are you getting?” I ask her.

“Pigs in a blanket! It’s the best breakfast ever! They take a sausage, wrap it in a pancake and drown in gravy.”

“Wow, that sounds good to me!”

Edna waves the waitress over here and orders us both Pigs in a Blanket. It doesn’t take long before she brings out our meals and we dig in.

“Oh wow, that was absolutely delicious!” I say as I pat my stomach. I’m completely stuffed, although, not, in the same way, I was earlier.

“What do you say we get in a round 2 in before we hit the road?” Edna asks with a big smirk. The waitress leaves the bill as she grabs our empty plates.

“My ass is still sore from earlier…” I sigh.

“Sorry about that, I couldn’t hold back after I had that tight ass of yours wrapped around my cock,” she says. I look around to see if anyone is listening to our conversation, but no one seems to be paying us any attention. “Maybe just a BJ then?”

I let out a little laugh. “Is this how things are going to be from now on?” I ask.

“I hope so, I like you Alex. If you decide to stay with me, I’ll try to take it easy on that ass of yours,” she says. “But I understand if you don’t want to stay.”

I look into those dark brown eyes. “Edna, I’ve never felt so good in my entire life. I mean, it hurt like hell at first, but it felt great at the end. Besides… I did say that I was yours. Didn’t I?”

A big smile appeared on that beautiful face of hers. She reached down and grabbed my hand. “I never thought I would get a handsome young guy like you who wants to be in my bed.”

“I never thought I would enjoy getting my ass filled by a big black cock.” She let out a giggle and then she got up left some cash on the table as she gets up and puts her jacket back on.

She looks back at me as she makes her way to the door, “You coming, baby?”

I nodded as I got up and followed her out to the big rig. Once we got inside she grabbed me, dragged me to the bed and pulled me into a deep and passionate kiss. I started to unbuckle her pants. As soon as I got them undone, I pulled them down along with her undies freeing that massive python once again. I pushed her on her back and took that monster cock in my mouth. I suck the tip as if it were a popsicle. Then I pop it out of my mouth and give it a few kisses. I lick up and down the 9-inch monster before plunging it back in my mouth. I try to go as deep as possible.

“Oh fuck, you’re getting good at this!” she moans. I pull out and stroke it as I look up into those gorgeous brown eyes. She grabs the back of my head and pulls me into another passionate kiss. Our tongues duel as I continue to stock that fat cock of hers. I pull back from the kiss and go back down on her dick. Shoving it as far as I can down my throat. “Oh fuck! That’s it, baby. Just like that!”

I start to bob up and down on her cock, every now and then pulling it out and planting a few kisses on the tip. I suck it back in between my lips and slurp it back down my throat once more. Her hand brushes through my hair. “Baby I’m going to cum real soon!”

I can feel her dick tense up and I know it’s about to erupt. I brace myself as I slowly suck it, bobbing back up and down that fat black cock. “OOoooh Fuck!” she screams as her cock starts to pulse spewing out a large load of cum. It instantly fills up my mouth. I try to swallow it all, but there is too much of it. Some of it escapes my lips and drips down her beautiful shaft. The salty, musky taste overtakes my senses. Just as I finish swallowing that delicious cum, another load erupts into my mouth. This time I manage to swallow all of it. Her hand grips my hair holding my head in place as yet again she unleashes more of that sticky white liquid in my mouth. I slurp it down as she finally releases my head. Some cum leaks out as I pull free of her cock. I make sure to clean up her sticky cum covered cock with my tongue. I look up at her as I make quick work of it. Her hand brushes against my cheek and she pulls me up for another long kiss.

“That was amazing! You sure learn quickly,” She gasps. “I think it’s time we get going, I still have to drop off my other load.”

“Sounds good to me!” I reply. With that, we get dressed and hit the road.

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