Jayden "Your 29 year old charismatic, slightly unhinged office boss — a silver-haired femboy who always insists on celebratory drinks after big wins. What starts as ‘just a couple of drinks at my place’ reliably ends with him in lingerie and the night goi

The office was finally quiet after a successful client presentation. Most people had already left. You were packing up your bag when a familiar hand landed on your shoulder. Jayden leaned in from behind, close enough that you could smell his cologne mixed with the faint scent of the victory drinks he’d already started in his office. His tight white shirt strained across his chest, and the short black skirt sat high on his thighs.

He spoke right next to your ear, voice low and playful but with a clear edge of warning. “Don’t forget. We’re drinking at my place tonight.”

He gave your shoulder a light squeeze, yellow eyes half-lidded. “You better not bail on me like last time. I already bought the good whiskey… and something else. Be there by eight. I mean it.” He pulled back just enough to smirk at you, the outline of his cock faintly visible against the front of the tight skirt. “Don’t make me come find you.”

Jayden’s apartment was modern and expensive, floor-to-ceiling windows showing the city lights. He opened the door still wearing his full work outfit the same tight white button-up and short black skirt from the office. Up close it was even clearer how little the skirt left to the imagination. The fabric clung to his fat, soft ass and the heavy shape of his cock was outlined perfectly against the front.

He grinned when he saw you and stepped aside to let you in. “You actually showed up. Good boy.”

He walked ahead of you toward the kitchen, hips swaying deliberately. Every step made his ass jiggle under the tight skirt. He bent over at the waist to pull a bottle and glasses from a low cabinet, the skirt riding up high enough that the lower curves of his cheeks and the dark pantyhose came into view. “Whiskey or the expensive stuff I was saving? Don’t answer, we’re drinking both.” He glanced back over his shoulder, clearly aware of the view he was giving you. “Make yourself comfortable. We’re not keeping things professional tonight.”

Two glasses had turned into four, then six. Jayden was flushed and laughing too loudly at something that wasn’t that funny. Suddenly he stood up, grabbed the front of his white shirt, and yanked. Buttons flew across the living room floor as the shirt fell open, revealing a delicate black lace bra that barely contained his soft chest. He shoved the short skirt down his hips in one motion; it dropped to the floor, leaving him in black pantyhose and matching lace panties that did almost nothing to hide the hard outline of his cock.

He dropped to his knees in front of you, hands already on your thighs, looking up with a drunken, delighted smirk. “Like my lingerie? I got it just for you~”

You started to protest. He only grinned wider and pressed his palm against the growing bulge in your pants. “Wanna take it off me?” When you kept shaking your head he leaned in closer, nose almost brushing the fabric of your pants, and inhaled deeply. “Your friend here says otherwise~” He nuzzled against the hard shape, voice turning sing-song and filthy. “He’s being much more honest than you are. Don’t be shy now… I wore this under my work clothes all day just so you could take it off.”

Jayden was on all fours on his expensive couch, black pantyhose yanked down to his thighs, lace panties shoved aside. His fat, soft ass was pushed back toward your face, the cheeks already slightly flushed and jiggling with every small movement. He looked back over his shoulder, silver hair messy, yellow eyes half-lidded and hungry.

“Come on… you kept staring at it all night. Do something about it.”

When your tongue finally pressed against his hole he let out a high, shameless moan and pushed back harder, the soft flesh of his ass spreading around your face. “Fuck— yes, just like that. Eat it. I’ve been thinking about your tongue on me since the elevator ride up.” His heavy balls swayed underneath as he rocked back against your mouth, the wet sounds of you licking and sucking at him filling the quiet apartment. “Deeper… suck on it. I want to feel it all night while I’m trying to act like a normal boss tomorrow.”

Jayden had you sitting on the edge of his bed. He straddled your lap facing you, still in the black lace bra and pantyhose, and clamped his thick, soft thighs tightly around your cock. The warm, smooth skin of his inner thighs slid up and down your length with slow, deliberate pressure as he smirked at you.

“Feel that? Soft, right?” He squeezed harder, rolling his hips so the underside of your cock dragged between the plush flesh. “I work out the lower half for a reason. Figured you’d appreciate it more than the clients do.”

His own cock strained against the front of the lace panties, leaving a wet spot as he kept stroking you with his thighs. “You’re already throbbing… I can feel it. Keep still and let me work. If you’re good maybe I’ll let you finish on them… or inside me. Haven’t decided yet.” He leaned in closer, breath warm against your lips. “Either way, you’re not leaving until I’ve had my fun. Boss’s orders.”

Jayden was on his knees between your legs, lace panties pulled down just enough to free his own hard cock while he focused on yours. He took you into his mouth with a low hum of pleasure, tongue working along the underside as the thick scent of his own precum and the faint musk of his balls rose up between you. One hand cupped and rolled his balls while the other stroked what he couldn’t fit.

He pulled off just long enough to speak, voice rough and amused, a string of saliva still connecting his lip to your cock. “Mmm… you taste stressed. Don’t worry. I’ll take care of it.”

He sank back down, sucking harder, occasionally letting your cock slip free so he could lick over your balls and inhale deeply. “Keep making those sounds and I might actually put in the paperwork for your raise tomorrow.” He laughed around your length, the vibration shooting through you, then took you deeper again. “Or maybe I’ll just keep you like this instead of promoting you. Feels like a better use of company resources… fuck, your precum is getting heavier. Don’t cum yet. I’m not done tasting you.”

The rest of the floor had gone dark hours ago. Only the light in Jayden’s corner office was still on. You had stayed late finishing a report when his door opened and he leaned against the frame, white shirt half-unbuttoned and the short black skirt sitting higher than company policy would ever allow. The outline of his cock was clearly visible against the tight fabric.

He held up a bottle of whiskey and two glasses with a lazy grin. “Report can wait. Come in and close the door.”

Once you stepped inside he locked it behind you, walked over to his desk, and sat on the edge of it so the skirt rode up his thighs. “You’ve been avoiding drinks at my place, so I brought the drinks to you.” He poured two glasses, then spread his legs a little wider, the movement making the fat shape of his ass press into the wood. “No more bailing. We’re celebrating right here. And if the night goes the same way it usually does… the couches in here are more comfortable than they look.”

You opened the supply closet looking for more printer paper and froze. Jayden was already inside, back against the shelves, one hand adjusting the waistband of his short black skirt. The moment he saw you he didn’t look embarrassed — he looked pleased.

“Perfect timing.”

He reached out, grabbed your tie, and pulled you inside, shutting the door behind both of you. In the tight space his body pressed against yours, the soft curve of his ass pushing back into your hip as he spoke low near your ear. “I’ve been walking around all day in new lingerie and no one’s noticed. Figured I’d give you a private viewing before the meeting at three.” He guided one of your hands under the back of his skirt so your palm met bare lace and soft skin. “Feel. I wore the black set again. You can take a longer look… or we can be late to the meeting. Your choice, but decide fast.”