Teens: The First Sting of Shame…

Mike was eighteen when he first bared himself to Sarah, a shy brunette from his college. They’d snuck into her bedroom, the air thick with nervous anticipation. As he dropped his pants, his tiny willy, barely two inches erect, sprang free. Sarah’s eyes widened, and a giggle escaped her lips. “Is that… it?” she stammered, her voice trembling with surprise. Mike’s cheeks burned as he tried to kiss her, but the moment her fingers brushed his minuscule shaft, he shuddered and came, a hot spurt landing on her thigh. Sarah recoiled, her disappointment clear. “I thought it’d be… more,” she muttered, pulling her skirt down and leaving him alone, his little willy still twitching in shame. That night, Mike swore he’d never let anyone see him again.

*****

Twenties: A Mix of Hope and Hurt…

By his mid-twenties, Mike couldn’t avoid his desires forever. He met Lisa, a confident blonde with a knowing smile, at a bar. In her apartment, she peeled off his clothes, revealing his tiny willy. “Oh,” she said softly, no malice in her tone. She wrapped her fingers around it- her hand dwarfing his length- and began to stroke. Seconds later, Mike groaned, his cum dribbling onto her wrist. Lisa didn’t laugh; instead, she kissed him. “Size isn’t everything,” she whispered, “and we can work on the timing.” They tried nights of slow teasing, her guiding his trembling hands to her breasts, but Mike’s insecurities gnawed at him. He’d finish before he even entered her, his tiny willy betraying him. Eventually, Lisa drifted away, leaving him frustrated but slightly less ashamed.

In his late twenties, Emily stormed into his life: bold, brassy, and unfiltered. The first time they fucked, she straddled him, her wet pussy hovering over his tiny erection. “Holy shit, it’s so small!” she laughed, grinding against it. Mike’s heart sank, but before he could retreat, she grabbed his head and pushed it between her thighs. “Use your tongue, little man,” she teased, her voice dripping with mockery and lust. He licked her eagerly, her moans drowning out his embarrassment as she came hard on his face. Later, she rode his tiny dick, giggling as he exploded in seconds. “Quick, but cute,” she smirked. At last, Mike was in a relationship that endured. Over the ensuing months, Emily helped him hone his oral skills and also introduced him to the use of sex toys to keep her satisfied.

*****

Thirties: Cruelty and Resilience…

Mike’s thirties brought a rollercoaster of reactions. Some women humoured him; others gave him a chance, but Rachel was a hurricane of cruelty. In her dimly lit bedroom, she stripped him down and just openly laughed at his tiny penis. “That’s the smallest willy I’ve ever seen!” she howled, snapping a photo before he could stop her. She jerked him off with two fingers, mocking his whimpers as he came in under a minute. “Pathetic,” she sneered, later spreading the tale to her friends. Mike heard the whispers at a party, “Rachel says he’s got a baby willy,” and retreated, his self-loathing reaching a peak. He stopped dating, his tiny willy a curse he couldn’t escape.

*****

Forties: A Turn Toward Acceptance…

By his forties, Mike’s scars had softened. He met Karen, a gentle woman with warm eyes, who saw beyond his body. The first time they made love, she cradled his cute little willy tenderly. “I love you for you,” she murmured as he entered her, his thrusts short and frantic. He came fast, as always, but Karen pulled him close, her fingers tracing his back. “It’s perfect,” she said, guiding his hand to her clit until she shuddered beneath him. With Karen, sex became less about his willy and more about their bond. His confidence grew, and he stopped hiding stopped apologising for his quick, pulsing orgasms and instead cultivated another relationship that lasted beyond the initial embarrassment of that first sexual encounter.

*****

Fifties: Embracing the Little Beast…

At fifty, Mike had a revelation: his tiny willy wasn’t a flaw; it was him. He met Susan, a sultry forty-something with a wicked grin, at a wine tasting. In her bed, she marvelled at his small willy, not with pity but delight. “Look at this little gem,” she purred, sucking it into her mouth. Mike lasted mere seconds, his cum coating her tongue, but Susan laughed–a rich, joyful sound. “Fast and fierce — I love it,” she said, climbing on top of him. She rode his softening willy, then used his fingers and tongue, teaching him to revel in every shudder, every release. Together, they fucked with abandon, his quick orgasms a spark that fuelled their fire. Mike finally loved his little willy: its size, its speed, its raw, honest pleasure, and he’s still with Susan to this day.

The End.

*AI has edited this story to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.