Trans Man Takes Coworker's Load

"You really think it's gonna get better tonight?" Will asked as he stared out the third floor window at the downtown street below. He and the new intern, Steven, had both stayed late at the office to work on their stories for the coming issue of their magazine and a mixture of snow and ice was rapidly coating the streets.

"I'm looking at the weather report right now," Steven insisted. "They say there's a warm front coming in as we speak that's gonna bring rain and melt this all out."

"Yeah?" Will replied. He glanced at his watch. It was 6:45pm but felt much later in the winter darkness. His article was now polished and ready for the boss's review, and he didn't have the energy to get started on his next assignment. After fifteen years in the profession, he actually found himself able to relax over the weekend between articles. His mind started to wander and he remembered that he needed to pick up his testosterone prescription tomorrow. But the pharmacy hadn't filled--

Steven was saying something about his car. Will didn't care much about cars, but he tuned in in case he might be expected to respond. "... so, I can give you a ride home if you don't want to be out in the slush," Steven offered.

With his perfectly pressed name brand slacks and wrinkle free shirts, Steven was just the kind of intern that the magazine always hired: trust fund kids just out of college with career goals unrelated to paying off nonexistent student loans. No doubt he expected to become chief editor here, probably wanted to make history by becoming the youngest to ever hold the post. He'd inherit his family's huge house in the suburbs and be a barely present breadwinner just like his own dad. Will's imagination was getting carried away. He realized he hadn't responded.

"Thanks, but no need," Will demurred. He should really just leave now before he lost his patience and started rolling his eyes at Steven. Maybe he'd be able to avoid the hills where it was most icy. He was surprised that a brash kid like Steven wasn't already testing his driving skills out there.

When Will turned away from the window, he was surprised to see Steven taking a seat at the table just a couple of feet away from him. In the empty and quiet office, there was plenty of space for them to spread out as they chatted.

"You know, Gina was telling me about the investigation that you broke open when you worked at The Post," Steven said. "It sounds pretty badass."

"Ah, my first cover story," Will said with a nod.

Before he could elaborate, Steven continued, "It's a shame we haven't gotten closer yet. There's a lot more I'd like to learn about you."

Will tilted his head slightly. Steven's choice of words was a bit odd. He wanted to learn about Will, not from him? Will's sense of confusion heightened when he saw the smirk on Steven's face. "Like what?" he pressed.

Steven sat up straighter in his chair and swept nonexistent crumbs off the thigh of his navy blue pants. He ignored Will's question. "Personally, I'm pretty good at keeping secrets. What about you?"

"Discretion is a key part of this profession," Will replied curtly as his stomach started to churn with uneasiness. What did Steven want from him?

A smile cracked open Steven's lips, and he leaned forward to put a hand on Will's hip. "Then, you'll consider letting me do something I've been wanting to do since I first laid eyes on you." Steven delivered the question with the tone of a statement. He started to rub up and down Will's hip.

Will stared at Steven, holding his breath. Never had he assumed that the young man might be anything other than straight. He had never looked at Steven in this light, but now that the opportunity had arisen-- no, he shouldn't. Steven wasn't part of his team, but still, if word ever got out... And then there was the fact that Steven probably didn't realize he was trans. That was the final straw. Will had to put his foot down.

"Look, Steven. I'm flattered, but whatever you're looking for from me-- I don't think I can provide it. There are plenty of other--"

Steven stood abruptly and cut him off. "You think I don't know what I want? I wasn't born yesterday." He reached between Will's thighs and cupped his crotch, then leaned forward and whispered in Will's ear. "I want to pound your man pussy until you can't take it any more."

The feeling of Steven's hot breath on his neck made Will shudder. The directness of the young man's words caused his t-cock to stiffen. He ground his crotch against the pressure of Steven's hand, already wanting more. It would just be this one time, he told himself. He reached for the cord and hastily closed the blinds.

Simultaneously, Steven was already unzipping Will's pants, showing no sign of timidness. He pulled everything down around Will's ankles. Now exposed to the air, Will realized he had already gotten shockingly wet. He leaned his back against the wall as Steven kneeled.

It was clear by the way Steven parted his folds with two fingers that he knew what he was doing. He chanced a glance up at Will, meeting his eyes, before touching the tip of his tongue to Will's t-cock. Will rubbed his hands through Steven's perfectly parted brown hair, taking pride in making a mess of it, in experiencing the raw instinctual side of the well-mannered rich boy.

Steven circled his tongue around Will's t-cock, drawing even more blood to the area. Will rocked himself forward and groaned. He wasn't prepared for how good it would feel when Steven swallowed him, and he lost his balance as his eyes cinched shut. "Oh, fuck," he cried out, feeling the young man's lips slide up and down his length. "Shit, you're good at this." It wasn't as if Will was new to receiving blowjobs, but he nevertheless felt himself getting close to orgasm. He pressed himself back against the wall and pushed Steven's head away.

Again to Will's surprise, Steven resisted. "Let me make you cum, dammit," Steven insisted with a dirty smile. "I promise it won't be the last time tonight," he added right before getting back to work. He rubbed the tip of Will's t-cock with his tongue as his lips sucked, creating a powerful mixture of sensations. Will found himself grasping for the back of Steven's head so he could thrust himself farther inside the young man. With his eyes closed, he imagined his t-cock growing so large that it could press up against the roof of Steven's mouth, even press into his throat. He wanted Steven to choke on him. The thought was getting him was getting so, so hard. His entire body was a knot of tension.

"Don't stop," Will moaned as Steven's tongue and lips worked their magic. "Oh, fuck, I'm cumming," he whined. In the moment of his orgasm, he regained awareness of the fact that his t-dick was inside of the intern's mouth, that they were fucking in the middle of the office, that this was behavior was very wrong. These facts only made him cum harder. He held himself inside Steven as he imagined his t-cock spurting cum down the back of Steven's throat with each pulse. His pussy dripped its wetness onto the insides of his thighs. Steven enthusiastically sucked everything out of him.

When Will was finally done cumming, he loosened his grip on Steven's head. Steven leaned back, breathing heavily and licking his lips. "Goddamn," he muttered. When Steven stood, Will saw his cock was tenting his pants.

"Turn around," Steven instructed.

As Will did so, he heard Steven unzipping himself. His pants dropped to the floor. Between Will's slimy thighs, Steven slid his rock hard member. He rubbed himself along Will's slit, letting the heads of their cocks grind against each other. Steven had proved himself to be a skilled lover already, but he wasn't a patient one. He used one hand to coax Will's feet a little farther apart. Then, with the other, he guided his tip into Will's entrance.

Sensing Steven's girth, Will reminded himself to breathe and relax. Even with all the lube provided by his orgasm, his man pussy was still a tight fit for the young man. But the pressure against his walls felt amazing. He wanted Steven to stay inside him forever. Steven grabbed Will's hips with both of his hands for better leverage, rocking himself forward and back to gradually delve deeper inside.

"That's it," Steven purred. "I knew it would feel so good to be inside you. I could tell you have an incredible man pussy just by the way you walk around the office." He stopped talking as he focused on the rhythm of his thrusts.

Will gripped the nearby window frame as he felt himself being stretched out. The only sounds were of the two men's breathing and of Will's sloppy wet hole being thrust into again and again. Hearing the suction of his insides turned him on even more, and he reached down to stroke his throbbing t-cock.

Steven slapped Will's ass with a firm hand. "I love that you're touching yourself," he said. "I'm going to make you cum even harder than before."

Will didn't doubt this. He could already feel the heat building in his lower belly again, as if he hadn't just had a release five minutes earlier. He pictured the virile young man creaming a huge load inside his pussy. Oh, god, how hadn't he noticed Steven's sexiness before this night? He was grateful the intern was so forward. Will couldn't imagine missing out on this amazing cock, this firm and steady stroke that pleased his man pussy so perfectly.

"Give me everything," Will cried out. "Don't hold back."

"I won't," Steven promised, his fingers digging into Will's hips as he pulled the older man back over his cock. "I'm going to give you every... last... drop." Steven was gasping for air now as he muscled his strongest thrust yet. On the next one, he started to cum.

As soon as Will felt Steven's hot load hit his cervix, he couldn't hold back anymore. This time, his orgasm came from deep inside his belly as the walls of his man pussy contracted to grip Steven's cock, milking out every bit of seed the young man had to give. His legs shook underneath him and his sinuses suddenly cleared. His mouth was open and he was making sounds, but he couldn't really hear himself anymore. Not until, a few moments later, he started returning to the real world.

Steven huffed, holding himself inside Will. "Take my cum. Yes, take it you slut. Take it and like it," he muttered almost to himself. As the last drops of seed exited his cock, he started thrusting slowly again, enjoying the sensation of his cum mingling with all of Will's juices.

When Steven finally pulled out, he spun Will around and kissed him hard on the mouth. Since Steven was a couple of inches taller, Will had to tilt his head upward. Steven reached down and rubbed a finger over his softening cock, then brought it up to Will's mouth. "Open up," he said, thrusting his finger inside Will's lips and making him taste what they had created together. "Remember how we taste. That's it."

Then, reaching for his pants, Steven walked away toward the restroom to clean up, leaving Will alone and sore with cum running down his legs. It wasn't a night he would soon forget. He started to reconsider Steven's offer to drive him home.