Brian watched patiently as his roommate got ready to walk out the door, heading off to work once more. It was the middle of the week and Diane had worked 10 hours overtime already and she was in no mood to go back. Her heels clanked on the floor as she hurried out the door and off to grind.
He wasn’t glad that she was so stressed about work, but he was glad she wasn’t spending so much time with him. Their relationship was pure friendship and neither of them had ever thought of making it more than that, which is why Brian never sought to make her something that was more than a friend. Truth be told, the only reason he asked her to be his roommate was because of his addiction to female clothing.
Ever since his teens, Brian had had a horrible addiction to wearing female clothes while he masturbated. The soft silks and satins of bras and panties against his skin made his cock grow long and hard every time he put them on. He just loved wearing the lingerie and he knew that Diane had the clothes that he wanted—even needed—to wear while he jacked off.
As soon as Diane left the apartment, Brian turned the television off and went to her room. The feel of her red satin bra around his chest made his cock twitch, stretching the fabric of her black laced thong. His nipples were tickling in pleasure as his strong hands whipped up and down his shaft.
Brian’s toes curled in Diane’s red pumps, a small glob of lube sliding down his wrist. His eyes were squeezed shut as he felt the string of her thong digging in his ass, Diane’s nylons caressing every sensitive spot in his legs.
His concentration was broken as his ears focused on the door of Diane’s room being swung against the wall, a tired looking Diane frozen in the doorway. Her black hair lazily draped around the curve of her full breasts as her brown eyes stared at her room mate in shock.
Not once in her life had she ever thought of Brian as a cross dresser, nor any of her other male friends had ever brought up the idea, and the sight of him clad in her underclothes made her heart jump in her throat. The bra and thong did not match, nor fit the contour of his masculine physique. The material was obviously stretching against his flat ribcage, straining by the thread to stay on his body. To say the least, the clothes looked completely deranged on him, but she couldn’t ignore the stiffening of her nipples.
“I came home because they said they didn’t need me,” Diane whispered after a pregnant pause. The tingle in her pussy made her stumble over her words, the soft pulse of her clit pushing against her dampening panties.
The thought of emptying his load completely left his mind as waves of shock rolled down his body. In a flash, Diane had covered his body with hers, her lips searching for an accepting touch. Her hands fluttered around his neck and torso, confused on where to settle themselves as their owner furiously attacked her room mate. Small groans met Brian’s silence, the grunts coated with thick aggravation. Brian came out of his stupor and mashed his lips against hers, feeling her acceptance and encouragement of him wearing her garments as he stroked his thick cock.
Just as she had suddenly pounced upon her prey, Diane pulled back and told him to continue his self-love as she watched. Her smooth legs separated gracefully as the wet, dark spot of her panties became visible from her creamy thighs, her polished fingers pressing the material into her excited flesh.
The erotic folds of her damp gusset aroused Brian to heightened want, his engorged cock throbbing to burst in his pumping fist. Diane moaned at the sight of her room mate pleasuring himself, her dripping hole begging for her pounding fingers. With one hand, she rubbed her proud clit, sticking out from beneath its hood, while the other hand slowly plunged into her velvety, pink depths. Lust filled the air as the two busied themselves, their eyes never leaving their companion’s working fingers.
“I want to see you come,” whimpered Diane in a moan, her fist quickly burying itself in her gash. Her throbbing cunt was so close - so close to that edge! – and all she needed to tip her over the cliff was to see his hot, creamy cum shooting out of his purple mushroom-capped cock.
Brian’s fingers milked and squeezed at his cock, feeling his load working to freedom. He felt that familiar twinges of release as thin ropes shot from his head into his nimble hand. Dripping cum coated his hand as Diane pushed her fist, thumb and all, wrist-deep in her gaping cunt, coating it with her own brand of nectar. Waves of pleasure washed over her limp body as her mind’s fog evaporated from thin air with a ring from her work phone.
Hurried words melted into another as Brian sat in a daze, watching his room mate gather her things to get back to work: a girl had gone home with exhaustion and the company was in need of another employee. He was left to sit in his cooling pool of cum as Diane rushed out the door and left him alone once more.