My Two Dads (Dress Up) Sex stories – Y2-Stories

Eleven-year-old Jimmy goes to a party dressed as a teenage girl.

Alan and Peter were a successful gay, black, married couple. They had been together for over a decade and had adopted their son, Jimmy, from an East European orphanage 10 years ago. Jimmy was now a handsome 11-year-old blonde boy on the verge of puberty. Secretly, his adoptive fathers had been training him to be a little cock slut since he was young. Today was a special day; they were dressing Jimmy up as a teenage girl to attend a party at their friend’s house. The purpose of this party was to expose Jimmy to teenage boys and hopefully provide him with the opportunity to suck some cock.

Jimmy was an expert cock sucker, having practiced on both his fathers’ and various others over the years. He was eager to put his skills to the test with real teenage boys at the party. He knew that if he played his cards right, he could not only make his fathers proud but also have the time of his life. As he looked at himself in the mirror, admiring his feminine appearance, he couldn’t help but feel a surge of excitement and anticipation.

Alan and Peter were pleased with the way their son looked. They knew that with his blonde hair, big blue eyes, and petite frame, he would be able to pass for a 14-year-old girl with ease. They had carefully chosen his outfit, which consisted of a form-fitting but padded dress, that gave the allusion of girlish curves, a pair of high heels that made him appear taller than he really was, and a delicate necklace that added a touch of femininity. They also made sure to style his hair in soft waves that framed his face.

Once they were satisfied with his appearance, they drove Jimmy to the party. As they arrived, they could see that the other guests were already gathered outside, enjoying the warm summer evening. Peter nudged Alan and pointed discreetly to a group of teenage boys who were standing near the pool. “Look, there they are. Jimmy, remember, just play it cool and wait for the right moment.”

Jimmy nodded eagerly, his heart racing with anticipation. He slowly made his way over to the group of boys, careful not to draw too much attention to himself. As he approached, he could feel the heat in his cheeks and the nervousness in his stomach. He cleared his throat and smiled shyly, “Hi, I’m… um… Alice. You guys all look like you’re having fun. Mind if I join you?”

One of the older boys, around 16 or 17, glanced over at Jimmy and smirked. “Sure, Alice. Have a seat. What brings you to the party?” Jimmy sat down on the edge of the pool, his legs dangling in the water. He tried to act natural, but he could feel the other boys’ eyes on him, assessing him.

“Oh, you know,” he said, shrugging casually. “My parents are friends with the host. They thought it’d be fun for me to come and hang out. I’m just looking to have fun, really.” The older boy leaned in closer, his voice dropping to a lower register. “Well, if you’re looking for someone to show you a good time, I’m your guy.”

Jimmy looked up at him with wide, innocent eyes, batting his false eyelashes coquettishly. “Really? You’d do that for me?” The older boy grinned, clearly enjoying the attention. He placed a hand on Jimmy’s knee and gave it a squeeze. “Sure, Alice. Just tell me what you want to do.”

Jimmy swallowed hard, his heart pounding in anticipation. He glanced around nervously, making sure that no one was watching too closely. Then, he leaned in close to the older boy’s ear and whispered, “Can we go somewhere private?” The older boy smirked, his hand moving higher up Jimmy’s thigh. “Follow me,” he said, leading Jimmy away from the group of boys, towards a small wooden summer house, in a secluded spot beneath a large tree.

Once inside the summer house, the older boy closed the door behind them and pushed Jimmy against the wall. He kissed him roughly, thrusting his tongue into his mouth as his hand moved up under his dress, cupping his bare ass. Jimmy moaned into the kiss, arching his back as the older boy’s fingers dug into Jimmy’s ass cheeks.

The older boy broke the kiss, panting heavily. “God, you’re so hot, Alice. You want my cock, don’t you?” Jimmy nodded eagerly, his eyes glassy with desire. The older boy reached down and unbuckled his belt, letting his pants fall to the ground in a pool at his feet, revealing his hard, throbbing teenage erection.

“Oh fuck, yeah,” Jimmy breathed, reaching out to grab the older boy’s cock. The boy groaned and pushed him down onto his knees.

“Take it, Alice,” he growled, guiding Jimmy’s head towards his erection. Jimmy eagerly opened his mouth, taking the boy’s cock deep into his mouth as he began to suck. He moaned around the thick shaft, feeling the heat of it against the back of his throat. The older boy’s hands tangled in his hair, urging him on as he fucked Jimmy’s face, thrusting in and out of his mouth.

Jimmy sucked and licked and nibbled, relishing the taste of the older boy’s precum and the feel of his cock sliding over his tongue. He knew that his daddies’ cocks were bigger, but he found himself enjoying the smaller size as it allowed him to take more of it into his mouth. He could feel the older boy’s hips begin to buck faster, and he knew that he was close.

Finally, with a hoarse cry, the older boy came, shooting his hot, salty cum deep into Jimmy’s mouth. Jimmy kept sucking, swallowing as much as he could as the boy’s cock twitched in his mouth. When he was finally spent, the boy tried to pull his cock from Jimmy’s lips, but Jimmy stopped him. He held the older boy’s hips tight, and sucked desperately on the his sensitive rubbery shaft, savoring the taste of him. He could feel the boy’s hands trembling in his hair, and knew that he was just as aroused as Jimmy was.

“Fuck, Alice,” the older boy groaned, his hips starting to move again. “You’re killing me.” Jimmy smiled around the older boy’s cock, his own heart racing. He deepthroated the older boy again, taking him even deeper this time, making a wet, sloppy sound as he sucked. The older boy’s hips bucked wildly, and he let out a hoarse cry, his body tensing as he came again, this time shooting another thick rope of cum down Jimmy’s throat.

Jimmy swallowed every drop, his mouth and throat aching from the intensity of it. As he sucked the older boy’s cock clean, he looked up at him, their eyes meeting in the dim light of the summer house. The older boy’s breathing was ragged, his chest heaving as he tried to regain control.

“That was…amazing,” Jimmy gasped, his voice still shaky from the experience. “Now fuck off, and send in whichever of your friends you like the most.” The older boy smiled down at him in shock, his eyes twinkling with mischief. “You’re such a naughty girl, Alice,” he whispered, running a hand through Jimmy’s long blonde hair. “But okay, if you insist.”

Jimmy gave the boy one last lingering kiss before pushing him away gently. “Go on,” he said, pushing the boy out of the summer house and back into the party. “Find me someone else to play with.”

As the older boy wandered off, Jimmy took a moment to compose himself. He smoothed down his dress and adjusted his little cock.

Soon, another figure appeared at the door of the summer house. This time, it was a tall, lanky boy with dirty blond hair and bright blue eyes. He hesitated in the doorway, his gaze darting between Jimmy and the rest of the party.

“Um, hi,” he stammered. “I’m…I’m Eric. I heard you wanted to see me?”

Jimmy smiled, nodding eagerly. “Oh yes, Eric, come in,” he said, patting the space next to him on the bench. “I’ve been waiting for you.”

As the older boy sat down beside him, Jimmy leaned in, pressing their shoulders together. He took the boy’s hand in his, lacing their fingers together. “You’ve heard about me from your friend, haven’t you?” he asked, a teasing glint in his eye. “He told you I’m a real slut, didn’t he?”

Eric nodded, his cock already beginning to harden at the thought of what was about to happen. “Yeah,” he managed to choke out. “He said you’re…you’re really naughty.”

Jimmy smiled, leaning forward to press a wet kiss to the Eric’s mouth. “That’s right,” he whispered, his hand finding its way to the bulge in Eric’s pants. “I’m the naughtiest girl you’ll ever meet.”

He reached down and grabbed Eric’s cock, giving it a firm tug. The older boy let out a gasp, his hips jerking forward. Jimmy smiled around his new friend’s cock, taking it in his mouth and beginning to suck. He bobbed his head, moving faster and faster as Eric’s hips began to buck against his face. His free hand reached up, cupping the boy’s heavy balls, massaging them gently .

“Fuck, Alice,” Eric groaned. “You’re so good.” Jimmy smiled, taking more of him into his mouth, the head of his cock pressing against the back of his throat. Jimmy deepthroated Eric, gagging himself, making a wet, sloppy sound as he sucked. His hands moved expertly, teasing his balls and tickling his perineum.

Suddenly, Jimmy felt a presence at his shoulder. He glanced up to see the first boy he’d been with. He was grinning down at him, his expression a mix of mischief and desire. He couldn’t help but smile back, feeling incredibly wanted and desired.

The older boy pushed Jimmy roughly onto all fours, his legs spread wide, and yanked up his dress, exposing his plump, round ass, winking open pucker, and smooth hairless preteen dick and balls.

“Oh yeah, I forgot to mention that,” Jimmy said, pulling his mouth off Eric’s cock. “I’m not a slutty girl, I’m a slutty little boy, but either way, I love to be fucked.”

The boy and Eric exchanged a look, shrugged in unison and carried on.

He felt the first boy press the head of his cock against his asshole, and then he pushed roughly inside. Jimmy cried out in pleasure, his body tensing as the older boy began to thrust into him. He reached back, grabbing Eric’s cock, taking it back into his mouth.

“Fuck,” Eric groaned, his hips beginning to move in time with the boy fucking Jimmy’s rear. “You’re unbelievable, Alice.” He gripped Jimmy’s hair, his other hand he casually slapped Jimmy’s face.

Jimmy moaned, feeling incredibly desired and wanted. “Yeah,” he panted, “I’m a very naughty little girl. Take what you want.” He reached back, grabbing the first boy’s ass, urging him deeper inside.

The second boy, Eric, leaned over, watching as his friend fucked Jimmy from behind. He could feel his own cock twitching in anticipation. Without warning, Eric grabbed Jimmy’s head and roughly face fucked him.

Jimmy gagged and coughed, feeling the older boy’s cock sliding in and out of his mouth. He couldn’t believe how wanted he felt, how much pleasure he was experiencing. The boys’ movements were in perfect sync, their hips in rhythm as they spit roast the preteen boy, using Jimmy’s body for their pleasure.

The second boy began to thrust harder, his grip on Jimmy’s hair tightening, while the first boy held him steady, fucking him roughly in hus well used rear hole. Eric’s hips bucked wildly, his cock throbbing as he felt himself about to cum. He yanked Jimmy’s head up, slamming his cock into the boy’s throat as he came, filling his mouth with thick, salty cum.

Jimmy gagged and choked, swallowing as much as he could as Eric held his head still, his cock twitching as he milked the last of his seed into the boy’s throat. He finally released him, watching with a satisfied grin as Jimmy gasped for air.

The first boy, still hard from fucking him, pulled his cock out and roughly wiped it on Jimmy’s ass, smearing his cum across the boy’s pale skin. Then he leaned in, positioning his fist next to Jimmy’s gaping hole. With a rough thrust, he slammed his fist into the boy, his knuckles digging into the tender flesh as he felt it stretch and give way. Jimmy cried out, arching his back as the older boy’s fist began a brutal pump inside him.

“Fuck yeah,” the boy growled, his voice rough with lust. “You’re such a little fucking whore.” He slammed his fist in and out again, harder this time, driving his knuckles deeper inside Jimmy. The boy’s body jerked with each impact, his ass clenching around the invading fist.

Eric, watching from the sidelines, couldn’t help but smile. “Look at that, Alice,” he said, his voice dripping with sarcasm. “Look how much you’re enjoying your punishment.” He grabbed Jimmy’s hair, tugging his head back roughly, and forced his own cock back into the boy’s mouth.

Jimmy gagged and choked, tears streaming down his face as he felt Eric’s thick cock fill his mouth once again. He was barely able to breathe, let alone form words as the older boy began to roughly fuck his throat. The other boy continued to pump his fist in and out of Jimmy’s ass, the pain mixing with the pleasure as he felt himself begin to approach climax.

Finally, with a loud cry, Jimmy’s body convulsed and he dry-cummed, his bald little cock twitching, but releasing no cum.

The boy who’d been fisting him let out a snort of laughter. “That will teach you to trick people ,” he sneered, pulling his fist out. Jimmy let out a whimper as his hole wink lazily and tried to close up, the feeling of sore pleasure almost overwhelming.