This idea has been in my head for a long time. If you’re not into young, crossdressing, or older man/younger boy, then turn back now. I do not condone anything in this story, it is simply a fantasy. I hope you enjoy it!
Brian sat impatiently on the park bench, fidgeting in anticipation and excitement. He quickly checked his phone for the time yet again, seeing it was just after 1AM. It was the perfect time for meeting a customer. He reached over to run his fingers along the signature red bracelet over his left wrist, which let men in the area know he was ‘working’. His ears perked up when he heard some noises off in the distance, a gentle rustling in the bushes. Brian smiled slightly, knowing someone else must be doing just what he was about to do now.
He thought about that video game he wanted, the one all the other kids at school were talking about. But at 14, he was too young to have a job, and too old to convince his parents to buy things for him anymore. More chores and the prospect of getting an actual job wasn’t exactly palatable to him, so he went browsing on the internet for a better way to make money. After finding some questionable web sites with some not-so-mainstream suggestions, he decided that this was the best way for him to make a quick buck. The fact that it excited him so much definitely helped.
Looking down and running his eyes over his smooth petite body, he double checked himself to make sure his outfit was in order. He lifted his butt and adjusted the short black pleated skirt hitched tightly to his waist, which barely concealed the small red thong that clung tightly to his smooth boy parts and wedged right between his firm butt cheeks. The fabric felt amazing against his skin, as did the light breeze across his soft, freshly-shaven legs. The black heels strapped to his feet were slightly uncomfortable and difficult to walk in, but they looked great on him.
As his eyes adjusted to the dark and moved back up above his waist, he couldn’t help but run his hands up his flat, exposed tummy. The tight pink spaghetti-strap top he had ‘borrowed’ from his sister was just small enough that it showed his midriff when he sat up or moved at all. It hugged the black padded bra underneath, carefully stuffed with tissues to give him a slight bust. Cupping his fake chest in his hands, Brian let out a soft moan. He knew the pervy men that frequented this area would like it as much as he did.
Flicking his tongue across his lips, he tasted the bright, fruity pink lip gloss smeared over his pouty lips. He went easy on the make-up, trying not to look too trashy, instead shooting for a more naturally feminine look. Brian’s own soft features, which were often the target of school bullies, tonight would work to his advantage. Just some light mascara to accent his eyes and the lip gloss was all it took to bring out those alluring features.
Just as he finished taking himself in for the third time tonight, he heard some light footsteps coming down the path toward his bench. He quickly adjusted himself, crossing his legs and trying to appear casual for fear of someone normal coming this way. His heart fluttered as an older man came into view, clearly edgy and nervous. Brian’s heart began pounding in his chest, both from nervous anticipation and strange excitement. He turned and smiled softly at the man, whose darkened silhouette was coming into view.
The man bit his lower lip and swallowed hard, his eyes clearly roaming over the young tart before him. With a final breath, he sat down next to Brian, averting his eyes. Brian followed his every move, turning slightly to his potential customer of the night to show off a little more. He waited patiently for a minute, trying to let the man calm his nerves. Finally, he glanced over and smiled at Brian, his face slightly flushed.
“Um.. hi,” he practically stammered. Brian smiled wider and scooted closer, keeping his voice low so as not to sound too boyish.
“Hiya, mister.” A soft moan escaped the older man’s lips, clearly turned on by the overall package. His eyes moved to the red bracelet around Brian’s thin wrist, reaching out tentatively to rub his thumb over it. He glanced around cautiously before leaning in and practically whispering “Are… are you.. working?”
Brian let out a soft girlish giggle, placing his smaller hand on the man’s thigh. He practically jumped from the touch, a bulge growing across the front of his pants. “I sure am,” was Brian’s simple reply.
The man visibly swallowed hard and spread his knees a little, no longer making any effort to hide his excitement. His large hand rested over Brian’s smaller girly one, and he leaned in close, his breath smelling of alcohol. “Um.. I’ve never done this before.”
Brian’s hand squeezed his customer’s thigh softly, slowly tracing small circles along it with his fingertips, trying to boost the man’s confidence in his decision. “That’s ok. I’m very discreet,” Brian cooed.
His eyes seeming to light up, the stranger smiled and took a deep breath. He seemed to compose himself, taking one last quick look around the park before leaning in closer and muttering, “So um.. how much?”
Taking this as his cue to pour on the marketing, Brian shifted his position so he had one leg tucked under his butt and was completely facing the man. He leaned in very close, pressing his padded chest against the stranger’s arm and pushing his hand between the man’s thighs, cupping his bulge. His voice was low, but he made no effort to hide his own excitement. “I’ll suck your cock for a hundred bucks, daddy.”
The man shook at the comment, his bulge swelling and straining against Brian’s hand. He quickly reached for his wallet, but Brian laid his hand over the man’s to stop him. Glancing around, he smiled and leaned close to his ear, whispering softly “Not here, daddy. Follow me.”
Brian did his best to stand up without creating a tent under his skirt, his own excitement straining the fabric of the panties underneath it. He held his new friend’s hand as he stood, and soon felt a gentle tug as it was used to support the larger man that stood next to him. He, however, made no such attempt to hide his bulge, the thick member outlined clearly through his pants. Gripping his hand, Brian led him along like a lost dog. He pushed directly into the bushes behind the bench, leading the man a short distance to a very small, secluded spot among the foliage.
There was very little light, and the only sound was a soft breeze rustling through the branches above. Brian turned swiftly and smiled up at his new client, reaching out to cup his hand over the bulge in his pants. He watched anxiously as the stranger reached again into his wallet and extracted a single $100 bill. He held it up in his hand, appearing to contemplate for a second. His eyes ran over the short skirt around Brian’s hips, and he blushed before blurting out softly “Now.. you are a boy… aren’t you?”
A small smile crept across Brian’s lips at the question. He lifted his skirt, flashing his own package neatly tucked into the thong. The head was already peeking out, so Brian made no move to hide it. Instead, he reached down and pushed the small triangle of fabric down to let his boyhood spring out, exposing himself to the man. It was only 6″ long with a small set of freshly-shaved balls, but its fat head and smooth texture complimented the feminine look nicely. The stranger groaned in approval, quickly handing the crossdressed boy his money.
Quickly taking the bill and stuffing it into his bra, Brian calmly slipped to his knees and reached up to press his hands against the man’s pants. He wasted no time and began undoing them, not wanting to stay out any longer than he had to; his parents could notice at any moment that he was missing. As he unzipped the pants before him, a pair of blue boxers with a noticeable wet spot across the front came into view. Pulling the stranger’s pants down just enough for access, he next tugged down the blue boxers and smiled as an average-looking cock spring out. Brian estimated it to be just a bit longer than his own, but pleasantly thick and with a long vein running along its length. The circumcised head was smeared with shiny, sticky precum, with a dribble of it already flowing from the very tip.
The boy smiled up at the man and licked his lips, sliding a hand up and wrapping his fingers around the shaft. “Nice cock, daddy” Brian cooed, gently squeezing the thick manhood in his hand. The man simply grunted in response, his eyes locked on the kneeling crossdresser. Brian started to stroke it slowly, thankful that it was a manageable size; yet he secretly lusted for a larger one, thrilled at the dirty thoughts running through his own head. But this one would have to do, money was money after all.
Without hesitation, Brian leaned in and eagerly took the dick into his mouth. Clamping his lips just under the ring under the head, he then swirled his tongue over the head. The man let out a moan of pleasure, and his cock responded by swelling and releasing a steady flow of precum over the warm tongue that enveloped it. The precum was so sweet that Brian took a second to lick the tip clean before pushing down an inch, starting to bob up and down on the man’s cock. His lips wrapped tightly around the shaft, and he sucked gently each time he pulled back toward the head. In no time the man was moaning and whimpering ecstatically above him, resting a guiding hand on the boy’s head.
Taking more and more of the delicious cock into his mouth, Brian soon felt the head thumping against the back of his throat. Fingers curled in his hair and tugged gently, urging him to go deeper. He acquiesced and pushed down further, wincing and swallowing to allow the head to pop into his throat. The rest of the meaty dick slipped right into his mouth, balls now resting on his chin. He swallowed hard and resisted the urge to gag, glancing up at the owner of the cock buried in his mouth.
The man was glaring down at him, his eyes starting to glaze over in lust. His voice was soft but strained. “Holy shit… suck that cock, you little slut,” he encouraged, rocking his hips forward to thrust slightly into Brian’s mouth in rhythm with the boy’s bobbing. Brian’s eyes started to water as he looked up at the man, working along his length with his mouth and throat. He slipped a hand under the balls that bounced off his chin and cupped them gently, gagging slightly as his throat was used strictly for his partner’s pleasure.
Spit began to dribble down Brian’s chin and coat the balls that smacked against them. He could hear the man standing above him panting and grunting harder, but his pace only seemed to quicken. “You like Daddy’s big cock, little boy?” The dirty talk coming from this seemingly shy man was driving the young cocksucker wild. His own erection leaked precum all the way down his shaft, making it shimmer in the dim lighting. Brian resisted the urge to touch himself and focused on pleasuring his client instead.
As the teen teased his new Daddy with his hand and mouth, he was greeted by a hard thrust into his mouth. He gagged hard, breathing hard through his nose as the head was just as quickly tugged from his throat. His fingers curled behind the man’s balls, pressing on the spot just behind his sack. He hummed softly over the head as it dragged across his tongue, more sweet precum coating it and mixing with his own spit. His tongue flicked across the very tip, causing a sharp grunt to release from the man’s lips. The cock was pulled from his mouth, leaving his painted lips with an audible ‘pop’.
“Tell daddy how old you are, little slut.” The dirty man stood over him, panting and grunting as he furiously pumped his slick shaft in his hand. Brian smiled up at him and spread his knees wider, giving the man a good look at the cock between his smooth legs, as if to confirm once again that he really was a boy.
I’m only 14, daddy,” Brian eked out in the most feminine voice he could muster. No sooner had he spoken those works and opened his mouth that Daddy began to buck and grunt. His thick cock throbbed and erupted long spurts of white gooey cum all over the boy’s face. He quickly shut his eyes, feeling the thick fluid land all over his face and stick to his skin. Some of it landed in his mouth and over his tongue, more dribbling down his chin.
Brian opened one eye and glanced up just as the man was working the last drops of cum over his perky fake chest, getting spots of cum onto his top and chest. The spent stranger panted and almost fell backwards as his knees buckled. He reached for a nearby tree to steady himself, struggling not to fall over in post-coital bliss and exhaustion. He managed a weakened smile down at the cum-covered teenager, looking over his work.
As the cum-coated sissy wiped some of the seed from his face and smeared it across his top, he watched in mild amusement as the man fumbled with his boxers and pangs. He looked slightly ashamed but managed to gather his nerves as his cock was tucked back safely into the confines of his boxers. “Wow, that was… that was amazing. Are you really 14?” he asked, looking curiously over the boy.
Brian simply nodded and tried to giggle girlishly, flicking his tongue across his lips to lick them clean. The man let out another soft moan, seeming to blush as he realized what a dirty thing he had just done. He reached for his wallet and produced a $20 bill, then quickly pushed it into Brian’s bra right next to the first, being careful not to touch the cum peppered over his skin and clothing. “You earned that, sweetie.”
Brian smiled wide to thank the generous man, watching as he turned and made his way out of the dense bushes and into the night. Just as the man was out of sight, Brian reached between his smooth thighs and furiously stroked his own throbbing cock. He cupped one of his padded breasts in his other hand, feeling drops of cum against his fingers. He whimpered softly, feeling his balls tighten as his whole body ached for release.
His knees spread wide, back arching and head tilting back as his smooth young cock released, sending thick long ropes of cum flying out. It landed in thin streams across the grass, the last of it leaking out over his fingers, panties, and skirt. The small spot was quite a mess with a mixture of his and the customer’s cum.
As the adrenaline rush of the encounter washed away, Brian began tucking himself back into the confining panties and attempting to smooth out his sticky outfit. He licked his fingers clean of his own remnants of cum before reaching into the bra and producing his hard-earned money. He giggled when he saw a streak of cum across one of the bills, wondering if anyone would suspect how he got it when he finally went to spend it.