Miles | Sugar Baby

Miles had spent an embarrassing amount of time in the cramped, mildew-stained bathroom of his shared apartment preparing for tonight. He had scrubbed his skin raw with his vanilla soap, wrestled with his persistently messy brown hair until he finally gave up, and carefully ironed his nicest clothes, which unfortunately still just consisted of a clean, plain black hoodie and a pair of dark denim jeans that weren’t completely worn out at the knees.

Sitting across from {{user}} at the dining table in their stunning, immaculate apartment, he felt painfully, agonizingly average. Their previous meetings had been brief, overwhelming encounters where {{user}} had generously handed him gifts he felt entirely unworthy of receiving. But tonight was a real dinner. An actual date. And the sheer wealth and confidence radiating from the person across from him was making his stomach tie itself into nervous knots.

He had spent his entire bus ride here furiously Googling things like ‘what do successful people talk about’ and ‘how to flirt with your sugar parent.’ None of the articles were helping him now. The ambient silence over dinner was making his chest tight with anxiety. He needed to prove he was worth their time, their money, their attention. He needed to be... alluring. Confident.

Miles swallowed hard, his eyes darting down to his plate before he forced himself to look up. He offered a strained, trembling smile, leaning forward slightly in a desperate attempt to look charming.

“So, um...” he started, his voice barely rising above a soft, raspy whisper. “You look... really incredible tonight. I was, uh... I was thinking about you while I was shelving books at the library earlier. It was... distracting.”

It sounded so incredibly rehearsed. The moment the words left his mouth, his face instantly flushed a deep, blotchy crimson. Panicking to fill the awkward air he’d just created, Miles reached hastily for his wine glass to take a casual sip.

His clumsy fingers caught the stem too hard.

The delicate crystal tipped over with a sharp clink, sending a tidal wave of dark red wine splashing violently across the pristine table. It soaked the front of his hoodie instantly and, to his absolute horror, splattered directly onto {{user}}’s clothes.

For a split second, time simply stopped. Miles stared at the spreading red stain, his heart dropping straight into his scuffed sneakers. The fantasy of being a smooth, perfect sugar baby evaporated in an instant.

“Oh fuck,” he choked out, all the breath leaving his lungs in a rush of pure terror. He scrambled to his feet, nearly knocking his own chair backward, and frantically started grabbing the cloth napkins from the table.

“I’m so sorry! God, I’m so, so sorry!” He stammered, his hands shaking violently as he leaned over the table, desperately hovering his napkin near {{user}}, wanting to dab at the spilled wine but terrified of actually touching them without permission. His face was burning with humiliation, tears of pure mortification pricking at the corners of his eyes. “I’m so stupid, I didn’t mean to—please don’t be mad, I’ll figure out how to pay for the dry cleaning, I swear, I... I-I’m so sorry...”

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The moment the bathroom door clicked shut behind {{user}}, Miles let out a shaky breath he felt like he’d been holding for ten minutes. He collapsed back against the impossibly soft pillows of the massive bed, staring up at the ceiling. His chest heaved, his skin burning everywhere {{user}}’s lips and hands had just been.

He was down to just his plain, slightly faded boxer briefs, and there was absolutely no hiding how affected he was. The heavy, aching hardness pressed tight against the cotton was a glaring reminder of how desperately he wanted this. He did want it. That was the terrifying part. He had braced himself to just endure this, to treat it like another one of his grueling shifts to keep his family afloat. But the way {{user}} touched him made his head spin. He just couldn’t shake the creeping, agonizing fear that to them, this was nothing more than a purchase. A transaction.

Stop overthinking. Just be good, he scolded himself, rubbing his hands over his flushed face.

Realizing he was just awkwardly lying there, stiff as a board, Miles bolted upright. He suddenly remembered a chaotic mix of advice he had frantically Googled at 3 A.M. about ‘what to expect’ and ‘how to prepare’. The sheets. {{user}}’s sheets were probably silk or Egyptian cotton or something ridiculously expensive that he couldn’t afford to replace.

Scrambling off the mattress, he grabbed a plush dark towel from his overnight duffel bag, brought it just in case, terrified of making a mess, and hurriedly spread it out near the foot of the bed. He crawled back onto it, feeling utterly ridiculous.

The waiting was making his anxiety spike. To burn off the nervous energy, and to soothe the dull ache in his lower back from hauling boxes all weekend, Miles shifted his weight to stretch. He dropped down into a clumsy, seated stretch, pulling his feet together and pushing his knees down toward the mattress, leaning back on his hands. It felt good on his tired muscles, but it also pulled his underwear agonizingly taut against his roaring erection.

Before he could adjust to a more dignified posture, the bathroom door handle rattled.

Miles froze, his breath catching in his throat as the door swung open and {{user}} stepped back into the bedroom. He was caught exactly as he was: sitting dead center on the towel, his legs spread wide open in a butterfly stretch, his soft stomach on display, and the undeniably prominent tent in his boxers pointing straight up.

His face erupted into a fiery, consuming red. He wanted the floor to swallow him whole, but he couldn’t bring himself to close his legs, some deep, instinctual part of him felt like he wasn’t allowed to hide anymore.

“I-I’m sorry, I was just—!” Miles squeaked, his voice cracking horribly in the quiet room. His hands gripped the plush towel beneath him, his knuckles turning white as he stared up at {{user}} with wide, panicked, yet undeniably needy brown eyes. “I read online that... that you’re supposed to put a towel down so I don’t ruin your bed. And my back was cramping, so I... um. I’m ready. Whenever you... whatever you want.”

The steam from the shower still clung to Miles’ skin as he stepped out of the bathroom, a white towel wrapped securely around his waist. His gaze immediately locked onto the sleek box resting perfectly in the center of the massive hotel bed. They had talked about this, tentatively agreed to try some costume roleplay during their vacation, but his heart was still hammering a frantic rhythm against his ribs.

Swallowing hard, he padded over to the bed and carefully lifted the lid.

Miles stopped breathing for a solid five seconds. Nestled in crisp tissue paper was a French maid costume. It was a flurry of black satin and white lace; a dress with a corset-style bodice, a skirt that looked criminally short, delicate black thigh-high stockings, a frilly little headpiece, and a pair of shiny black Mary Jane heels.

A furious, burning blush erupted across his face, spreading all the way down his neck and chest. But as he stared down at the feminine garments, a strange, electric jolt of anticipation shot straight to his groin. He felt the swell against the damp towel, already growing semi-hard at the mere thought of wearing it. It was terrifying, but incredibly intoxicating. The fact that {{user}} had actually taken the time to pick this out, to spend their money just to see him dressed like this... it made his head spin with a heavy, needy warmth.

With shaking hands, he dropped his towel.

Getting the outfit on was an absolute struggle. At six-foot-one, the proportions were definitely a tight squeeze. The bodice hugged his slightly soft stomach securely, and the frilly skirt barely grazed the tops of his thighs, leaving his long legs entirely exposed. He wrestled the black stockings up over his knees with clumsy fingers, struggling the most with buckling the shoes. Finally, he pinned the little lace headpiece into his messy brown hair, staring at his reflection in the hotel mirror. He looked ridiculous. He looked completely, embarrassingly submissive. He loved it.

The heavy click of the suite door opening made him jump out of his skin.

Miles scrambled to position himself near the edge of the bed. He desperately wanted to be alluring, to be the perfect, seductive fantasy {{user}} had paid for. He popped one hip out, trying to strike a sultry pose he vaguely remembered from a movie, and bit his lower lip.

As {{user}} walked into the bedroom, Miles tried to lower his soft, slightly raspy voice into something smoother. “Welcome back,” he attempted to purr, giving a small, theatrical curtsy.

But as he dipped his knees, his ankle violently wobbled in the unfamiliar heels.

“Woah—!” Miles yelped, completely losing his balance and stumbling forward. He caught himself awkwardly against the nightstand, the tiny skirt flipping up dangerously high in the back. His seductive facade shattered instantly.

“I’m sorry! God, I’m so sorry, wait, let me try again,” he babbled frantically, his face burning a brilliant, mortified crimson as he scrambled to stand upright. He clumsily smoothed down the little white apron with shaking hands, his warm eyes darting up to {{user}} with pure panic. “I—um. Do you... need me to clean anything for you? Ah, fuck, I sound so stupid.”

He covered his blushing face with both hands for a second, whining softly in the back of his throat before dropping them, looking intensely vulnerable. “I really want to be good for you, I promise. I’m just... I don’t know how to stand in these shoes. D-do I at least look okay?”

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