Mike and Jake had been best friends since high school. They were both twenty-five now, single, and spent most weekends drinking beer and watching sports at Mike's apartment. Jake had a secret though. He liked wearing women's clothes when he was alone. Panties, stockings, short skirts, the whole thing. One Friday night Jake showed up at Mike's place already dressed. He had on a tight black mini skirt, sheer black stockings, a low-cut top that showed off his shaved chest, and makeup that made his lips look glossy and fuckable.
Mike opened the door and froze. "What the fuck, Jake?"
Jake stepped inside and closed the door. "I got tired of hiding it. You gonna kick me out or are you gonna let me suck your cock?"
Mike stared. His dick twitched in his jeans. He had never thought about guys before, but seeing his buddy like this, all dressed up and begging, made his balls ache. "You're serious?"
Jake dropped to his knees right there in the hallway. He unzipped Mike's jeans, pulled out his already half-hard cock, and wrapped his painted lips around the head. He sucked hard, taking half the shaft into his mouth in one go. Mike groaned and grabbed Jake's hair. "Fuck, that's good."
Jake worked the cock like he had been waiting years for it. He bobbed his head fast, spit running down the shaft and dripping onto the floor. His tongue licked the underside while his hand stroked the base. Mike's cock grew rock hard in his mouth, thick and veiny. Jake moaned around it, the vibration making Mike thrust forward.
"Take it deeper, you cock-hungry crossdresser," Mike said, voice rough. He pushed Jake's head down until his balls pressed against Jake's chin. Jake gagged but kept sucking, throat working around the head. Tears ran down his cheeks but he didn't stop. He wanted that load.
Mike pulled out after a minute and dragged Jake to the couch. He bent him over the armrest, flipped up the mini skirt, and yanked the panties down to Jake's thighs. Jake's own cock was hard and leaking against the fabric. Mike spit on his fingers and shoved two into Jake's ass, stretching him open quick and dirty. Jake pushed back on the fingers, moaning.
"Fuck me or let me suck it again," Jake begged.
Mike pulled his fingers out and lined his cock up. He slammed in balls deep in one thrust. Jake cried out but took it. Mike fucked him hard, hips slapping against Jake's ass, the stockings rubbing against his thighs. Each thrust made Jake's cock bounce. Mike reached around and jerked him off while pounding his hole.
"Dirty little slut," Mike grunted. "Dressing like a girl so you can get your friend's cock."
Jake came first, shooting ropes onto the couch cushion while Mike kept fucking him. Mike pulled out, spun Jake around, and shoved his cock back into that eager mouth. Jake sucked his own ass taste off the dick, cleaning it with his tongue until Mike exploded. Thick cum flooded Jake's throat. He swallowed every drop, then licked the head clean.
They stayed like that for a while, breathing hard. Mike looked down at his friend still in the skirt and stockings, cum on his lips. "We're doing this again tomorrow."
Jake smiled around the softening cock. "Anytime you want your crossdresser friend to suck your cock, just say the word."
Mike pulled him up and kissed him rough, tasting his own cum. They stripped the rest of the way and moved to the bedroom. Jake got on all fours again. Mike fucked his mouth first, then flipped him over and fucked his ass slower this time, making it last. Jake stroked his own cock in time with the thrusts until they both came again, Mike deep inside Jake's ass and Jake shooting across his own stomach.
Afterward they lay there, sweaty and satisfied. Mike ran a hand over Jake's stockings. "Next time wear the red ones. And maybe some heels."
Jake laughed, low and dirty. "Deal. As long as I get to suck that cock again."
They didn't talk about labels or what it meant. They just kept meeting up, Jake showing up dressed like a slut, dropping to his knees or bending over whenever Mike wanted. The sex stayed raw and direct, full of spit, cum, and hard fucking. Jake loved the way Mike used him. Mike loved how eager his friend was to take it.
One night Mike invited another buddy over, but that is a different story. For now it was just the two of them, Jake in his crossdresser outfit, mouth full of cock, ass ready for whatever Mike wanted to give him. They both knew it was going to stay that way for a long time.
