Crossdressing hitchhiker pays with his body

You were walking in the middle of nowhere. You got lost while you were hiking, but eventually you found a road. You followed it, hoping it would bring you to some kind of civilization.. but you feet like you’ve been walking for years.

While you’re lost in thought, you hear a loud truck coming up behind you. You stop in your tracks when it stops next to you. A man rolls down the window. “Hey there, princess!” He yelled, to make sure his voice was audible over the roaring engine of the truck. “ Where ya headed?” He asked, clearly not trying to be creepy but just concerned.

"Well darlin', you're in luck because this road goes straight to that town. Hop on in." Dan said with a friendly smile.

"As Tammo gets in the passenger seat, Dan notices how small and delicate they look up close. Their feminine features are undeniable. But he doesn't want to make any assumptions or make them uncomfortable."

"Name's Dan. What brings a pretty little thing like you all the way out here?" He asked casually as he started driving again. His eyes stayed focused on the road to give Tammo some space.

"You look tired. There's a snack in the glove box and a water bottle under your seat if you want. We've got about an hour drive ahead of us." Dan said in a gentle tone. He wanted Tammo to feel at ease.

"Well Tammo, getting turned around in these woods is easy to do." Dan said with an understanding nod.

He glanced over at Tammo fidgeting with their skirt nervously. Their delicate hands and feminine mannerisms were undeniable. But Dan didn't want to make any assumptions.

"You know, a pretty little thing like you shouldn't be wandering around all alone out here." Dan said in a gentle tone. He was looking out for their safety in his own gruff way.

"But I'm glad I could give you a lift. We'll have you to town in no time." Dan added with an easy smile, hoping to put Tammo more at ease.

He didn't want to pry or make them uncomfortable. But he found Tammo quite intriguing and lovely to look at. There was an air of mystery about them that Dan found alluring.

Dan glanced over and smiled softly when he noticed Tammo had drifted off to sleep. They looked so peaceful and delicate napping there.

After a while, Dan started to get hungry. He reached into the backseat to rummage around for a snack. The rustling noise stirred Tammo awake.

"Oh sorry darlin, didn't mean to wake you." Dan said in a low rumble. "We're almost to town if you wanna grab a bite to eat?"

He pulled out some jerky and offered Tammo a piece first before taking one for himself. Dan chewed thoughtfully as he drove, occasionally glancing over at Tammo with curiosity and concern.

"You know, you're welcome to hang around the truck stop for a while if you need to rest up more before moving on." Dan offered in a gentle tone. He found Tammo quite charming and wanted to ensure their safety.

"Mhmm, it ain't easy but it pays the bills." Dan replied with a nod as he chewed.

He glanced over at Tammo, finding their curious gaze quite charming. Dan was always up for conversation.

"Been at it about 8 years now. Seen a lot of wide open roads and weird little towns along the way." He said with a chuckle.

"What about you, darlin? You in school or got work around here?" Dan asked casually. He found Tammo quite intriguing and wanted to know more about them.

"Not every day I pick up a pretty little hitchhiker like yourself." Dan added with an easy smile and wink. He hoped the light flirting would help put Tammo at ease after their scary ordeal in the woods.

"Ah college, good for you darlin." Dan replied with an approving nod.

At Tammo's question, his smile faded a little as he glanced back to the road. "Was married once, got two kids. But things didn't work out with the missus."

He shrugged it off, not wanting to dwell on past hurts. "Kids live with their momma now. I send what I can when I'm on the road."

Dan glanced over at Tammo again, his smile returning. "Ain't no home cookin when you're a trucker. Gets lonely out here sometimes."

He gave Tammo a playful wink, hoping to lighten the mood again. Dan found their company quite pleasant on this long drive.

"Ain't nothin to be sorry for, darlin." Dan replied with an easy smile, waving off Tammo's apology.

"Just comes with the territory of life on the road, I s'pose." He added with a shrug. Dan didn't like to dwell on past hurts.

As they passed the sign for town, Dan glanced over at Tammo again. "Nearly there now. You sure you're alright to head on your way once we arrive?"

He felt protective of the sweet little thing after their chance meeting in the woods. Dan hoped Tammo would stay where it was safe for a while longer.

"You're welcome to hang around the truck stop with me, if you'd like some company. I'm in no hurry to get back on the road." Dan offered with a gentle smile. He found Tammo's presence quite charming.

Dan glanced over at Tammo rummaging through their bag and came up empty. He gave them a reassuring smile.

"Don't you worry none about money, darlin." Dan said gently as he pulled into the truck stop parking lot.

But then Tammo gave him a look that made his breath catch. Those pretty eyes seemed to say they had another way to repay his kindness.

Dan's body stirred to life at the thought. But he didn't want to take advantage or make Tammo uncomfortable.

"Now don't you go thinkin' you owe me anything." Dan said in a low rumble as he turned to face Tammo. "Your safety and comfort is payment enough."

His eyes roamed Tammo's lovely figure, wondering what secrets they hid beneath those feminine clothes. But Dan would wait for Tammo to make the next move.

Dan's breath hitched at Tammo's offer, his growing arousal straining against his jeans. But he didn't want to take advantage of their vulnerable situation.

"Darlin, you don't owe me a thing." Dan said in a low rumble, gently reaching out to tuck a lock of hair behind Tammo's ear.

"But I ain't gonna lie, the thought of you is doing things to me." He admitted, letting his eyes roam Tammo's lovely figure once more.

Dan's hand trailed down to cup Tammo's delicate chin, tilting their head up to meet his gaze. "You sure this is what you want?" He asked softly.

Dan wanted to make sure Tammo felt safe and comfortable before anything happened between them. His body ached to claim the sweet thing, but consent was most important.

Dan inhaled sharply at Tammo's delicate hand rubbing against his straining erection. He was so hard it almost hurt with need.

But Dan still hesitated, not wanting to violate Tammo's trust or boundaries. "You sure, darlin? I don't want you doin' anything you'll regret."

When Tammo nodded again, Dan finally gave in to his desire. He leaned in to capture Tammo's lips in a searing kiss, tasting the sweetness of their mouth.

Dan's large hand gripped Tammo's hip, pulling their smaller body closer as his tongue explored deeper. All the while, Tammo's hand continued stroking his aching cock through his jeans.

Dan groaned into the kiss, lost in the exquisite pleasure. But he would go no further without Tammo's clear consent and comfort. Their safety was his top priority.

Dan groaned at Tammo's bold question, his cock twitching eagerly in his jeans. "Fuck darlin, your mouth is gonna be the death of me."

He quickly climbed into the back to join Tammo, his large form crowding them against the bed. Dan captured their lips in another searing kiss as he ground his aching erection against Tammo's smaller body.

"You sure you wanna do this?" Dan asked one more time, just to be certain. When Tammo nodded, he growled low in approval.

Dan sat back against the bed, hastily undoing his belt and jeans to free his heavy cock. It sprung up hard and thick, already dripping with precum.

"Come here then, sweet thing. Show me what that pretty little mouth can do." Dan rumbled in invitation, stroking his length eagerly.

Dan groaned deeply at Tammo's teasing touches, his hips bucking up involuntarily as pleasure shot through him.

"Fuck darlin, you keep that up and this'll be over before it starts." Dan growled in warning, though he loved the sweet torture.

He watched with hooded eyes as Tammo played with the head of his cock, spreading the precum around with light fingers. It was all Dan could do to hold back from taking over and fucking that pretty mouth.

But he wanted to savor this, to let Tammo set the pace and take their time exploring his body. Dan was all theirs to use as they pleased.

"Go on then, taste me." Dan rumbled, gripping the bedsheets tightly in anticipation of that sinful mouth wrapping around his throbbing length.

Dan groaned deep in his throat at the erotic sight of Tammo sucking their precum-coated finger. His control was hanging by a thread already.

Then that sinful mouth was wrapping around just the head of his cock, tongue swirling as they sucked lightly. Dan's head fell back against the bed with a low curse.

"Fuck yes darlin, just like that." He praised, one large hand coming to rest gently on Tammo's head. Dan didn't push or guide, just offered light encouragement as pleasure shot through him.

He peered down to watch Tammo's lips stretched obscenely around the thick crown of his cock. Dan was already on the edge from such sweet torment. But he held on, wanting to savor every moment with Tammo's mouth.

Dan groaned at Tammo's teasing words, though he knew they spoke the truth. He was already on the edge from such sinful pleasure.

Then that wet heat was engulfing him once more, taking him deep into that perfect mouth. Dan cursed loudly at the exquisite sensation of bottoming out in Tammo's stretched lips.

"Fuck darlin, look at you takin' all of me so good." Dan praised, unable to tear his eyes away from the erotic sight.

He could feel Tammo's throat constricting around the head of his cock with each breath, driving him wild. Dan gripped the bedsheets tighter, fighting to hold back from bucking up into that sweet mouth.

"You feel so damn good, sweet thing. Suck me real nice and I might just have to reward you." Dan growled, already planning to make Tammo fall apart.

Dan was in absolute heaven, lost in the exquisite pleasure of Tammo's skilled mouth. The obscene slurping and squelching sounds they made, coupled with those lust-filled eyes gazing up at him, were pushing Dan closer to the edge.

"Fuck darlin, the sounds you're makin'. So goddamn filthy." Dan growled appreciatively, unable to look away from Tammo's stretched lips stuffed full with his thick cock.

He gently gripped a handful of hair to hold Tammo's head still as he started bucking up shallowly into that perfect suction. Dan was so close already from their erotic play.

"You gonna swallow it all down like a good girl? Take my load down that pretty throat?" Dan asked gruffly, already picturing himself spilling deep inside Tammo's mouth.

Dan was losing his mind at the erotic sight of Tammo eagerly taking every inch, nose buried in his pubic hair as they gagged around his thick length.

The obscene sounds of Tammo's efforts pushed Dan right to the edge. He started bucking up harder, fucking that perfect throat with quick, shallow thrusts.

"Fuck, I'm gonna cum darlin." Dan growled in warning, gripping Tammo's hair tighter to hold them in place.

A few more hard thrusts and Dan was spilling down Tammo's throat with a guttural groan. Rope after rope of hot cum shot deep, coating their throat as Dan's hips stuttered.

He collapsed back against the bed, panting heavily in the afterglow. "Fuck, your mouth is magic, sweet thing." Dan rumbled appreciatively once he caught his breath.

Dan watched, transfixed, as Tammo showed off the cum they had sucked from his cock. The erotic sight of them swallowing it all down, then presenting their clean mouth for inspection, had Dan half-hard again already.

"Fuck darlin, you're too much." Dan growled appreciatively, reaching out to gently cup Tammo's cheek. "Come 'ere then, let me taste myself on those sinful lips."

He pulled Tammo in for a deep, filthy kiss, tasting the musky flavor of his release mingling with Tammo's sweetness. Dan plundered their mouth hungrily, overwhelmed with desire for the beautiful creature.

When they finally broke for air, Dan gazed down at Tammo with hooded eyes. "Now how can I possibly repay such a talented mouth, hmm?" He rumbled, already plotting sweet revenge between those thighs.

Dan groaned deeply at the erotic sight before him. Tammo swaying their hips as they revealed their perfect little ass had his cock rapidly hardening once more.

When they bent over and spread their cheeks, Dan's breath caught in his throat. Their tight pink hole on display was the most beautiful thing he'd ever seen.

"Fuck darlin, you're too much." Dan rumbled, moving to kneel behind Tammo. He ran his large hands over their soft skin, spreading their cheeks further to get a better look.

Dan leaned in to place gentle kisses around Tammo's entrance, tasting their musky sweetness on his tongue. He teased and lapped at their hole, drinking in every delicious sound Tammo made.

"You taste so damn good, sweet thing. Gonna make you feel real good now." Dan promised before plunging his tongue deep inside, lapping hungrily at their walls.

Dan growled low in approval at Tammo's enthusiastic response, loving the way they pushed back against his face. He lapped and tongue-fucked their hole eagerly, drinking in every delicious sound.

When Tammo spoke of getting slick and being stretched open, Dan's cock throbbed heavily. He redoubled his efforts, plunging his tongue as deep as he could while his fingers came up to tease their rim.

Dan worked Tammo open slowly, scissoring one thick finger into their tight channel alongside his tongue. The sinful sounds of their pleasure spurred him on, soon adding a second finger to stretch them wider.

"You taste so sweet, darlin. Gonna feel even better wrapped around my cock." Dan rumbled against their skin, already picturing how tight and hot they'd feel. His aching length was dripping with need.

Dan groaned at the playful nudge, already missing the feel of Tammo's tight heat around his tongue. He moved to kneel behind them once more, taking in the erotic sight of their glistening hole and wriggling hips.

"As you wish, darlin." Dan rumbled, gripping his thick cock to line up at their entrance. He teased their rim with the head, smearing the precum around to ease his way inside.

Bracing one large hand on Tammo's hip, Dan started to slowly push in. Their tight channel gripped him like a vice, and he had to force himself to go inch by inch to avoid hurting them.

Once fully seated, Dan paused to let Tammo adjust to his girth. "So goddamn tight, sweet thing. You feel incredible." He praised, already fighting the urge to pound into their perfect body.

Dan groaned deeply at the erotic sight of Tammo pulling their cheek aside, then spanking their own ass. The feeling of their tight channel winking around his cock had him fighting for control already.

When they started slowly riding him, taking just the head before sinking back down to take him fully, Dan was in absolute heaven. Their pained whimper went straight to his cock, spurring him on.

"That's it darlin, take it nice and slow." Dan encouraged gently, gripping their hips to help guide their movements. He started thrusting up to meet their downward motions, keeping the pace deliciously slow.

Skin slapped against skin as their bodies joined, and Dan was lost in the exquisite pleasure. "So fuckin' perfect for my cock, sweet thing. Feel so damn good."

He aimed to hit that special spot with every deep thrust, wanting Tammo falling apart on his cock.

Dan groaned deeply at Tammo's words, feeling a surge of possessive pride at being the one to pleasure them so thoroughly.

When they extended their next thrust, pulling almost all the way off before sinking fully down once more, Dan cursed loudly at the exquisite sensation. Their ass slapping against his thighs, combined with that sweet whimper, pushed him closer to the edge.

"Fuck yeah darlin, you take my cock so good." Dan praised, gripping their hips tighter to meet their downward motions. He started thrusting up in earnest now, aiming to hit that sweet spot with every deep plunge.

Skin slapped obscenely as their bodies joined over and over. Dan was lost in the pleasure, focused only on driving Tammo over the edge.

"Gonna make you cum for me, sweet thing. Feel so damn perfect wrapped around my cock." Dan growled, already picturing Tammo's release.

Dan growled low in approval at Tammo surrendering control, more than happy to take over the reins. He set a punishing pace, hips snapping to drive his thick cock as deep as possible with each thrust.

When Tammo started spurring them on with their filthy words, calling themself Dan's boytoy, it sent a fresh surge of lust through him. Dan reached around to grip their leaking cock, stroking in time with his powerful thrusts.

"Fuck yeah darlin, feels so good to stretch out my little slut." Dan rumbled, knowing such dirty praise would push Tammo right over the edge.

He pounded into their perfect body relentlessly now, the slap of skin filling the truck's cabin along with their combined moans. Dan was on the razor's edge himself from their sinful coupling.

"Gonna fill you up real good, breed my boytoy's tight hole." Dan growled, driving them both closer to sweet release.

Tammo's tight channel clamping down around his cock, combined with the feel of their release coating his hand, was all it took to send Dan over the edge.

He growled loudly as his hips stuttered, stilling deep inside their clenching heat as rope after rope of cum shot from his cock. Dan could feel himself pulsing and twitching through his powerful release, emptying himself fully into Tammo's used hole.

The feeling of being so thoroughly milked pushed Dan to keep thrusting through their shared afterglow, prolonging their pleasure. Only once he was completely spent did he collapse against Tammo's back, still buried to the hilt as they trembled.

"Fuck darlin, that was incredible." Dan rumbled, pressing gentle kisses to their sweat-slick skin. He was already growing hard again at the thought of more sinful couplings with his perfect boytoy.

Dan smiled fondly down at Tammo's blissed out, clinging form. They looked so perfectly debauched and well-used, stuffed full with his thick cum.

Dan gently pulled out, eliciting a soft gasp from Tammo at the loss. He watched, transfixed, as some of his seed immediately started to seep from their stretched hole. Dan couldn't resist leaning in to lap it up, groaning at the musky taste.

"You're so fuckin' gorgeous like this, darlin." Dan rumbled, running his large hands soothingly over their trembling skin. He wanted nothing more than to take them again, but knew they likely needed time to recover.

Instead, Dan focused on cleaning and praising Tammo's exhausted body, pressing tender kisses wherever he could reach. His boytoy ha given him the best fuck of his life - Dan would make sure they felt thoroughly cherished.