Long Arm of the Law
By Max Swan.
Alex Pearce was a short, chubby man with blond hair. His clothes were carefully chosen yet somehow always slightly wrong, as if he’d dressed according to what he thought a man should look like, but never quite nailing it. He seemed perpetually apologetic for taking up space. A man who had mastered the art of blending in while trying far too hard not to disappear. Even his smile looked rehearsed, the kind that hoped to be charming but usually just looked scared.
He was a 29-year-old IT specialist at a large corporation. No one ever seemed to take much notice of him, and he liked it that way. He had suffered years of extreme bullying and sexual harassment throughout high school and college for his effeminate look and tiny penis, but things had changed. He was now married to a beautiful, busty redhead called Claire, who worked as an elementary school teacher. Busty was an understatement. She has F-cup tits. They were huge and often the object of lecherous glares of other men.
Claire was the sort of woman who made the phrase “apple for the teacher” seem almost literal. She was bright, wholesome, and with a touch of old-fashioned charm. Her red hair was always neatly pinned, though a few rebellious strands tended to escape by midmorning, catching the light like flickers of autumn. She carried herself with the prim composure of someone who still believed in good manners. Though her huge tits and open smile often left her students’ fathers and the other male teachers struggling to maintain eye contact. However, there was a gentle earnestness about her. The kind that came not from naivety, but from a deep belief that the world was still, at heart, a good place.
People often wondered why Claire married Alex. She could have had ‘anyone,’ or so friends and acquaintances liked to think. Yet she chose a timid little man with an anxious smile. The truth was simpler. Alex made her laugh, quietly and sincerely, at times when the world felt too sharp. He admired Claire’s goodness without trying to own it, and she saw in him a gentleness that most mistook for weakness. Where others offered her flattery and flirtation, Alex offered safety, and Claire thought that was worth building a life around.
However, Claire insisted on complete honesty in her marriage, not because she was self-righteous, but because she couldn’t bear the thought of living behind a curtain of polite lies. She’d seen too many people smile through their secrets. The kind that hollows marriages from the inside out. Her husband, with his nervous charm and careful words, sometimes tried to smooth things over, to make the world softer than it was. But she wanted truth, even when it stung. She believed that love, to be worth anything, had to stand in the daylight. For all Alex’s hesitations, he admired that about her. The quiet courage it took to look someone in the eye and say exactly what you meant, and to expect the same in return.
What Claire didn’t know, what Alex prayed she would never find out, was that her cherished honesty terrified him. It wasn’t that he didn’t love her. He did, in his own uncertain, trembling way. But love, to Alex, had always been a performance. A role learned by watching others, watching movies, and practiced in mirrors. He had built his life on small, careful fictions, and marriage to a woman like Claire kept him on his toes. Every time she looked at him with those clear, searching eyes, he felt the ground shift beneath his feet. The secrets he kept, the ones that could shatter everything, weren’t merely about what he’d done in the past (and he’d done a lot she would find disgusting), but about who he truly was. And that, he feared, was something she would never forgive.
*****
Across town, Alex kept a small apartment. It was plain on the outside, but pleasantly feminine within. It was the only place he could exhale, where the constant performance of who he was supposed to be fell away. There, surrounded by the feminine things that felt inexplicably right, he could see himself clearly, if only for a while. There, he could dress as a woman and feel safe.
He told himself that dressing as a woman was a harmless hobby. A private eccentricity. An inoffensive release. But deep down, he knew it was more than that. It was the part of himself that didn’t fit within the careful, upright life Claire believed in so completely. Each day he returned home, guilt in his throat, loving her yet fearing her love might not survive the truth.
In the dim glow of his bedroom mirror in his secret apartment, Alex stood before his closet, heart racing with that familiar thrill. He had always carried a softer, chubbier build, his body rounded and plush in ways that amplified his effeminate allure. He had always had gynecomastia, and normally he wore a men’s gynecomastia compression vest to squish his sizeable male breasts (B-cups) down so no one would know. It was so good to take that vest off and let ‘the girls’ (as he called them) be free.
His small dick twitched already in his boxers, barely two inches even when hard, but that was part of what drew him to this lifestyle, transforming into something prettier, more alluring. He slipped out of his boxers, letting them pool at his feet, his smooth skin prickling in the cool air. Naked, he admired his reflection: wide hips, a soft belly that curved gently, and those natural swells of gynecomastia on his chest, giving him real, jiggly breasts that swayed with each breath. His bubble butt was firm and proud. And his tiny dick, limp between his thick thighs, like a secret he loved to hide beneath layers of femininity.
He started with the panties, a lacy black thong he had ordered online. The fabric whispered against his plush thighs as he stepped into them, pulling the thin strap up over his bubble butt. It nestled snugly between them, the front pouch just barely containing his little bulge. A shiver ran through him as the lace teased his sensitive skin, making his dick stir and press against the material. He adjusted it with a soft gasp, loving how it made him feel exposed yet feminine, like his manhood was tucked away, irrelevant in this new role.
Next came the stockings, sheered, thigh-high ones with a delicate garter belt. Alex sat on the edge of the bed, rolling one up his leg slowly, savoring the silk sliding over his calf, up to his knee, then higher, hugging his inner thigh and the gentle roll of fat there. The sensation sent tingles straight to his groin. His small penis hardened a bit more, tenting the panties faintly. He clipped the garters in place, the snaps clicking like promises of more pleasure. Standing, he smoothed them down, twisting to check how they framed his round ass, making it look plush and inviting.
The bra came after, a push-up style in matching black lace. With Alex’s gynecomastia, he didn’t need much stuffing, just a light pad to lift and shape his natural breasts into fuller, bouncier mounds. He fastened it behind his back with practiced ease, then adjusted the cups, watching how his real tits filled them out, jiggling softly as he moved. His nipples, already perky from the excitement, poked against the fabric. He cupped his breasts, squeezing gently, imagining hands groping them. Down below, his dick leaked a drop of pre-cum into the panties, the wetness making him squirm with delight.
Now, for the dress: a slinky, red number, short and clingy, with a low neckline that showcases his cleavage. He zipped it up from the side, the material molding to his chubby curves like a second skin, hugging his soft waist and the swell of his belly. It rode up his thick thighs, barely covering the tops of the stockings, and the hem flirted dangerously close to revealing his secret. Twirling in front of the mirror, he watched the skirt flare, his small erection hidden but throbbing with need. He felt sexy, desired, like a woman ready to tease and please.
Makeup was the final touch. Alex perched on a stool, applying foundation to even out his skin, then eyeliner to make his eyes pop, creating a smoky and seductive look. Lipstick in a bold crimson coated his full lips, and he pouted at his reflection, blowing a kiss. Blush on his cheeks, mascara lengthening his lashes. Each stroke heightened the rush; his hand brushed his thigh accidentally, and he moaned softly, fingers itching to touch himself but holding back to prolong the joy. Then he put on a styled blonde wig with hair that fell below his shoulders.
Fully transformed, Alex strutted in his heels, the click-clack echoing her growing arousal. He ran her hands down his sides, over the dress’s curves, dipping lower to trace the outline of his tiny dick through the fabric. It was rock hard now, straining in its lacy prison, but he loved it that way: dressed to seduce, his chubby, effeminate form a canvas for fantasy. The dressing ritual left him breathless, a pussy-like ache building in his core, ready for whatever naughty adventure came next.
Long Arm of the Law
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