The low hum of the highway filled the camper van, Wanderlust, as Maggie cruised down the open road. The van, decorated with personal touches like tasseled curtains and a well-loved ukulele propped in the corner, was more than her home—it was her sanctuary. Here, Maggie was free from the chaos of people, especially men, whose company she’d long since tired of.
But that didn’t mean she didn’t know how to handle them.
She spotted a hitchhiker ahead, his long blonde hair catching the afternoon sunlight. From a distance, he looked almost delicate. That was the only reason she slowed down. But as she pulled to the shoulder and he turned to face her, she frowned. He wasn’t the woman she’d assumed but a man—a tall one, broad-shouldered, with a confident stance that grated against her nerves.
He approached the van, flashing a charming smile. “Thanks for stopping,” he said, his voice rich and warm.
Maggie tilted her head, sizing him up. “I thought you were someone else,” she said bluntly.
His smile faltered. “Someone else?”
“A woman.”
He let out a short laugh, running a hand through his hair. “I get that a lot. Look, I just need a ride. I’ll be no trouble, I promise.”
Maggie’s lips curved into a slight smirk. “You promise, huh? I don’t usually pick up men. Too much… male energy.”
“I get it,” he said, raising his hands in mock surrender. “If there’s anything I can do to make you feel more comfortable, just say the word.”
Her eyes flicked to the glove box. It wasn’t often she encountered a man on the road she felt like testing, but this one had potential. He carried himself like someone who was used to taking control—confident, even a little cocky. She liked that. Breaking confidence was always more satisfying.
“There is something,” she said, her tone casual as she opened the glove compartment and pulled out a shiny metal object.
He raised an eyebrow. “What’s that?”
“A cock cage,” she said, holding it up. “You put this on, I hold the key. It’s a symbol that, in my van, you follow my rules. And, it’ll knock down some of that male energy of yours. -negotiable. ”
He hesitated, eyeing the chastity device, then her. “Seriously?”
“Dead serious.” Her smirk widened. “If you can’t handle it, you’re welcome to keep walking.”
Something shifted in his expression. The charm faltered, replaced by curiosity, maybe even intrigue. “Alright,” he said finally, holding out his hand. “I’ll play along.”
Stepping around to the side of the van, away from the traffic and prying eyes, he unzipped his jeans and began fumbling with the device. He wasn’t quite sure how it went on. Unknown to him, Maggie watched him from the passenger-side mirror, amused by his clumsiness.
Eventually, he learned the metal ring had to be fitted around his dick and balls before the cage is locked in place. The first time he tried to attach the cage, he pinched his scrotum, causing him to grimace. Maggie smiled from her observation perch.
Caleb returned to the passenger door. Maggie sat back, crossing her arms and said, “Show me.” She knew perfectly well that he was wearing the cage, but she wanted to humiliate him by making him show her. Caleb complied and then handed her the key. “Now we’re clear. My van, my rules.”
He climbed in, touching the cage through his trousers. “You carry this around with you often?” he asked.
“Sometimes,” she said, keeping her eyes on the road. “It’s not my first rodeo.”
The truth was, it was far from her first. Maggie had built an entire side business around men like him—men who craved structure, control, or just the thrill of submission. On her OnlyFans page, she called herself The Keeper, offering to hold keys—both literal and metaphorical—for her subscribers. Some sent her chastity keys in the mail. Others paid handsomely for nothing more than her sharp words and unwavering dominance.
As the miles passed, Caleb’s initial bravado gave way to a quiet curiosity. He asked questions—nothing too invasive, but enough to show he was intrigued.
“So, do you do this a lot?” he asked.
Maggie chuckled. “More than you’d think.”
“And they’re… okay with it?”
“Oh, they love it,” she said, glancing at him. “Some men just need a reminder of their place. It’s… freeing for them.”
His expression shifted again, and for the first time, she thought she saw something vulnerable in his eyes.
“Why’d you really me ride with you?” he asked finally.
Maggie’s smirk softened into something subtler. “Maybe I was curious. Maybe I saw something in you worth testing.”
Caleb didn’t reply, but he didn’t argue either. By the time they reached the next town, the dynamic in the van was clear. Maggie had the upper hand, as always, and Caleb seemed strangely comfortable with that.
The engine of Wanderlust purred to a stop on the outskirts of a small town, the sun hanging low in the sky. Maggie leaned back in her seat, stretching her arms as Caleb glanced down at bulge in his pants.
“So,” he said, trying to sound casual, “I guess this is where you unlock me?”
Maggie smirked, resting her elbow on the door as she turned to face him. “You guess wrong, Caleb.”
His brow furrowed, and for the first time since she’d picked him up, he looked genuinely unsettled. “Wait—you’re serious?”
“Dead serious,” she said, her tone calm and measured. “That’s not how the game works.”
He shifted in his seat, clearly uncomfortable but unwilling to argue outright. “Okay, so how does the game work?”
Maggie’s lips curved into a sly smile. “I decide when you’re done wearing it. And, if you’re lucky, I might give you a way to earn the key.”
Caleb blinked, then let out a short, nervous laugh. “Earn it? Like… what, do chores for you or something?”
She tilted her head, her gaze sharp enough to make him squirm. “Something like that. But let’s make it interesting.”
“Interesting?” he repeated, his voice edging on disbelief.
She leaned forward, her tone dropping to something both playful and commanding. “You want out of that cage? You’ll have to be my girlfriend for the afternoon.”
He blinked. “Your what?”
“My girlfriend,” she repeated, savoring the way the word made him squirm. “That means you wear a dress, maybe some lipstick. You hold my hand when I feel like it, and you answer to ‘darling’ until I decide I’m done.”
Caleb’s mouth opened, then closed again. He looked at the ring, then at her, as though weighing his options. Finally, he sighed. “You’re serious about this?”
“Completely,” she said, her voice steady.
“And if I don’t?”
She shrugged. “You keep the cage on and be on your way.”
He groaned, running a hand through his hair. “You really don’t make this easy, do you?”
“Life’s not easy, sweetheart,” she said, her tone laced with amusement. “So, what’s it going to be?”
Caleb stared at her for a long moment before finally slumping back in his seat. “Fine. You win. I’ll do it.”
“That’s the spirit,” Maggie said, her grin widening.
Within twenty minutes, Caleb was standing awkwardly outside Wanderlust, wearing a floral sundress Maggie had pulled from her closet. It fit him surprisingly well, though he tugged at the hem as if trying to make it longer.
“Stop fussing,” she said, adjusting the wide-brimmed sunhat she’d placed on his head. “You’re a natural.”
He shot her a look but didn’t protest. “This is… humiliating.”
“It’s supposed to be dear,” she said, linking her arm through his. “Relax, Caleb. Own it. You’re my darling girlfriend now.”
As they walked through the quaint downtown, Maggie reveled in the sight of him trying to keep his composure. She bought ice cream and made him carry her purse. He flushed every time she called him “darling” loud enough for passersby to hear, but to his credit, he didn’t back out.
By the time they returned to the camper van, Caleb looked exhausted but oddly calmer.
Maggie leaned against the side of Wanderlust, watching Caleb fidget in the floral sundress as he handed back the wide-brimmed sunhat. The afternoon sun dipped below the horizon, bathing the small town in hues of gold and pink. She was enjoying herself more than she expected—a rare thing when it came to the company of men.
“You survived,” she said, smirking.
“Barely,” Caleb muttered, tugging self-consciously at the hem of the dress. “Can I have my clothes back now?”
“Eventually,” Maggie teased, tilting her head toward the van. “Why don’t you come inside first? I’ll pour us a drink.”
Caleb hesitated, the lingering tension of the day visible in his shoulders, but he nodded and followed her into the camper van. Inside, the space was cozy and eclectic, filled with warm lighting, colorful throw pillows, and a faint scent of lavender.
Maggie handed him a glass of whiskey and settled on the bench seat, motioning for him to sit beside her.
“To a successful date,” she said, raising her glass with a sly grin.
Caleb chuckled nervously, clinking his glass against hers. “Some date,” he muttered before taking a sip.
They sat in companionable silence for a while, the van swaying slightly in the evening breeze. Caleb was loosening up, the tension draining from his frame as he finished his drink. Maggie, however, was watching him with a glint of something playful—and dangerous—in her eyes.
“You know,” she said, setting her glass on the counter, “for someone who looked so uncomfortable earlier, you played the role of ‘darling girlfriend’ pretty well.”
Caleb gave a weak laugh, rubbing the back of his neck. “Yeah, well, you didn’t exactly give me much choice.”
Maggie leaned closer, her voice dropping to a purr. “No, I didn’t. And you know what? I kind of liked it.”
He froze, his glass halfway to his lips. “Uh… what do you mean by that?”
She smiled, reaching out to trail a finger along the edge of his jaw. “I mean,” she said slowly, “I’m feeling a little… restless. And I think you could help me with that.”
Caleb’s eyes widened. “You’re… you’re serious?”
Maggie leaned back, her smirk widening. “Completely. But let’s be clear—I’m in charge here, just like always. You want to help me out, you play by my rules. Got it?”
He swallowed hard, his gaze flicking to the door, then back to her. “What… what are the rules?”
Her grin softened, but her eyes stayed sharp. “Relax, Caleb. It’s not complicated. You just do what I say.”
The van was quiet for a moment, the tension thick in the air. Then, slowly, Caleb nodded.
“Good,” Maggie said, leaning closer, her voice low and commanding. “Now, let’s see if you’re as good at following instructions as you are at wearing a dress.”
“Do you know how lesbians have sex, Caleb?” Caleb knew from the get-go that Maggie was a dike, but where was she going with this. He responded lamely, “ I suppose.” Maggie was intent to get Caleb to play along. “Give me examples of sex acts that lesbians perform.”
Caleb, stated the obvious in the form of a question, “They lick pussy?” “That’s right, Caleb, they perform cunnilingus.” Standing up, Maggie pulled down her panties, hiked up her skirt, leaned back in her chair, and spread her legs, and stated the obvious, “That’s what I want you to do.”
Caleb had licked a few pussies in his day, but it had always been his choice. This was fucking blackmail. But, what choice did he have. He started to move towards her when she stopped him, “I like my bitches to be naked when they go down on me.
In shock, Caleb recoiled at being spoken to in such a domineering way. His first instinct was to fight back, but he caught himself before digging a deeper hole. He just wanted to get past this. He pulled the dress off over his head. It was the only piece of clothing he was wearing. Embarrassed, his eyes turned downward, staring at the metal contraption that surrounded his junk.
Maggie didn’t let up, “Crawl over to me.” It was only a few feet, but he did ask she commanded. As his face approached her crotch, she smelled her ripe, hairy pussy. He always found hairy cunts to be repulsive, and this added to the disgust he felt towards himself for what he was about to do.
When Caleb got close enough, Maggie grabbed the back of his head and pulled his face towards her muff. She continued her emasculating verbal abuse, “Stick your tongue out, cunt.” Caleb began to lick, almost gaging as he performed cunnilingus. Maggie leaned back. She was clearly enjoying herself, not just the oral sex, but the head games she was playing.
After several minutes, Caleb sensed Maggie was near orgasm. Her labia were swollen, and her vagina was gapping. After a few more minutes of licking, Maggie’s legs began to shake, she threw her head back with a scream, and then she squirted all over Caleb’s face. He tried to withdraw, but Maggie held the back of head and pressed his face into her geyser.
Maggie must have held him there for at least two full minutes, until her body stopped shaking and she had milked everything she could out of the orgasm. Pushing Caleb away, she stood up. Caleb tried to stand too, but she pushed him back to the floor with her foot.
“Not bad pussy licking for a faggot”, she said. Caleb pressed his face to the floor and remained motionless and silent. He was afraid of what might come next. His fears realized, Maggie’s next question made it clear her ‘fun and games’ were not over. “Do you know what else lesbians do, Caleb?”
What could this bitch have in mind now. No doubt more humiliation. Not wanting to give her any ideas, he looked up from the floor and simply said, “I don’t know.” Maggie smiled and said, “They fuck.” Stepping to the back of the van, she returned a couple of minutes later having changed black tights and a black bra. She was also sporting a strap-on with a large black dildo.
His face was still planted on the floor, Caleb sensed Maggie was behind him. Although he had not looked up to see Maggie’s strap-on, it was apparent that he knew what was about to happen and he surrendered by assuming a doggie position. Maggie acknowledged his action, “You have a very pretty pussy, Caleb. Are you a virgin?” Caleb did not respond.
Maggie was not gentle. She was not going to peg him for her own pleasure and certainly not for his. She was going to stick her girl cock in Caleb for the soul purpose of completing his emasculation. Instead of loosening him up, she simply squirted some lube on his butthole and pressed her cock against it until it was forced into his rectum. She didn’t ease the shaft in, but once past the entrance, she buried the dildo in his rectum with a single thrust.
Caleb cried out. It wasn’t a manly cry, but more of a squeal. The sound made Maggie laugh openly as she began fucking him. In a combination of pain and humiliation, Caleb’s eyes began to water and he made a grunt with each thrust that sounded like he was sobbing. What followed was a good twenty minutes of Maggie pounding Caleb’s ass, punctuated by verbal insults. “It looks like you have a lot of experience taking it like a girl, Caleb. Are you going to come for me?
At one point Maggie withdrew the dildo to admire her handywork. “Look at that gapping pussy. I should go get a bigger cock.”, then she stabbed him again and went back to work rearranging his innards.
Finally, Maggie grew weary of the game she was playing. She stood up. Caleb could hear her unbuckle the harness and let the strap-on fall to the floor with a thud. After Maggie retreated to the rear of the camper to clean herself up, Caleb tried to regain his composure.
Maggie returned fully dressed. Marcus stood by the kitchenette staring at the floor, his bare shoulders slumped, his chest rising and falling with shallow breaths. Maggie pushed past him, opened the small fridge, and took out a bottle of beer. Twisting off the cap, she pushed past Caleb again and made the way to the built-in bench.
Maggie sat down, and adopted a posture that was casual but commanding. She cradled the bottle of beer in her hand, her thumb lazily brushing the neck of the bottle as she tipped it back for a slow, deliberate sip. The bottle clinked softly as she set it down on the tiny table, her gaze fixed on Caleb like a predator savoring the final moments before her prey fled.
“Well,” she said, her voice carrying the weight of the day’s triumphs, “I didn’t think you’d make it this far. You surprised me.”
Caleb didn’t respond. He was a far cry from the man who had entered her camper that morning, full of bravado and defiance. The self-assured confidence, the sarcasm, the masculinity he had worn like armor—it was all gone now, stripped away task by humiliating task.
The day had been a slow unraveling. She had broken him down methodically, starting with indignity of making him wear a cock cage and later a dress and lipstick. Forced into the public after his appearance feminized was the moment his defiance finally broke.
Now, standing before her at the end of the day, he felt hollow, his pride reduced to rubble. His voice trembling. “I’ve done everything you asked. Please… let me go.”
Maggie tilted her head, her smirk deepening as she leaned back, taking another slow sip of her beer. The amber liquid sloshed lightly in the bottle as she set it down again. For a moment, she seemed to savor his plea, letting the silence stretch. Then, she reached into her pocket and pulled out the small brass key, holding it between her fingers like a trophy.
“You’ve earned it,” she said finally, tossing the key onto the counter.
Caleb lunged for it, his hands fumbling as he unlocked the cock cage. The cold metal fell floor. He rubbed at the red mark it had left, his breathing shaky, his body trembling with relief.
But as he straightened, his reflection caught his eye in the small mirror above the sink. The smeared lipstick stared back at him, a cruel echo of her power over him. His eyes, swollen and bloodshot, brimmed with fresh tears at the sight. His face was abraded from rubbing on the floor when Maggie had humped him doggie-style. Slowly, he raised a hand and scrubbed at his face, smearing the red further before finally wiping it away.
“I want my clothes,” he said quietly, his voice barely more than a whisper.
Camille raised an eyebrow, the corner of her mouth curling into a grin. She stood and walked to the small wardrobe at the back of the van. When she turned, she held the flowery sundress he had worn earlier, the fabric dangling from her fingers like a taunt.
“Here you go,” she said, her voice dripping with mockery. “This is yours now. It suits you.”
Marcus shook his head weakly. “No… my real clothes,” he croaked.
She laughed softly, a sound low and rich with condescension. “Oh, sweetheart,” she said, shaking her head. “Your old clothes are mine now. You’ve outgrown them.”
The weight of her words crushed what little resistance he had left. Trembling, he reached out and took the dress, his hands closing over the fabric in defeat.
As he turned toward the door, clutching the garment, her voice followed him, calm and teasing. “You make a better woman than I thought you would, Caleb. Maybe it’s time you embrace it.”
He stepped out into the cool night, the camper door clicking shut behind him. The gravel crunched under his bare feet as he stood there, the dress clutched tightly to his chest. The stars above seemed distant and uncaring, indifferent to the man he had been and the person she had shaped him into.
With a deep, shuddering breath, he took his first steps into the night, the fabric fluttering softly in the breeze, as if mocking the man he used to be.