Growing up in the midwest Alex was a good student, popular with both boys and girls. As a kid he was athletic, playing baseball, football and track. When he reached puberty he went through the usual growing pains that other kids went through, but his body never developed enough to continue playing competitive sports. When he stopped growing he was 5' 7" and thin with narrow shoulders and hips. In High School he ran the gamut of dating; taking a girls out just once, multiple dates with one girl, and even a 3-month period with the same girl, but never a long commitment.
In college he joined a Fraternity and dated many women. He was brilliant with computer languages and was recruited by many top software companies. Life couldn't have been going better for Alex.
He graduated from college and set himself up as a freelance consultant. This enabled him to work from home while companies periodically paid for his travel to various cities for meetings or for longer term projects. His sex life was great, he knew how to please a woman and due to his good looks, inner confidence and successful business acumen he had no trouble meeting them.
One night after a particularly enjoyable romp with a beautiful young woman he'd picked up, he found himself staring at the ceiling while she slept next to him. He couldn't remember her name, but that wasn't what concerned him. What was concerning him was why he was starting to wonder what it felt like to BE her. Did she enjoy sex as much as he did? Did she enjoy wearing sexy clothes? What about all the makeup and preparation women went through to "make themselves pretty"? What did it feel like to have sex with a man, not as another man, but as a woman? Alex had never been attracted to men, but he was starting to wonder what women liked about men.
He got out of bed trying to shake these strange thoughts. He was naked as he walked to the sliding glass door and out onto the balcony of his apartment. It was dark and windy, no moon tonight. He looked out at the lights of the city and thought again about the girl asleep on the bed behind him. The wind felt good on his naked body and he started to stroke his 8" shaft. She had worn a small black dress and pantyhose last night. He glanced back and saw the dress hanging on a chair. It felt so good to run a hand up and down the legs of a woman wearing hose. What did it feel like to wear them?
He quietly walked back inside. The girl was sleeping soundly. Alex picked up her dress and pantyhose off the chair and slowly walked into his study and locked the door. Without really thinking about it he sat down on the couch and started to put on the pantyhose. He tried to do it like he had seen women put them on, but he snagged a toe and put a run in one leg. Damn. He finally got them on, stood up and smoothed out the material, running his hands over his legs, ass and penis. Wow, he thought, this feels great! He looked at her dress, wondering if it would fit.
He lifted the dress, holding it up in front of him. He could smell her perfume on it and it made his cock strain against the pantyhose. Lifting it over his head like a T-shirt he put his arms through and let the dress slide down his body. It was a little tight, but it fit! He pulled the dress down over his hips and adjusted it on his body. It felt so sexy! He walked around the room feeling the dress sway and lightly brush his hose-covered ass. His cock was really getting hard now and he needed some release.
He carefully removed the dress and pantyhose and walked back into the bedroom. The girl was still sleeping. She had rolled over onto her stomach, the covers falling away from her body. She had apparently gotten up at some point and put her panties back on. She was a vision lying there. Alex carefully put the dress and hose back on the chair and crept into bed. He moved down to the girls ass and started to rub his face lightly over her panties, breathing in her scent as he did. She moaned. Using just his face and tongue he rubbed and licked all over her ass. In the back of his mind he wondered what it would be like to wear silky panties like these. He carefully rolled her over and proceeded to lick her shaved pussy through the panties. She was getting wet now and was only partially awake. He kept going, burying his face in her sucking on her large clit thoroughly enjoying the feel of her panties on his face. Finally he felt her hands on his head, pulling him into her as, writhing and moaning, she came again and again.
Alex moved up to his pillow and, once again, stared up at the ceiling. The girl rolled over and half-asleep, started playing with his cock as she snuggled against his chest. She started kissing his chest and moved lower and lower, Alex' smile growing wider the lower she went. As she took him into her mouth, Alex couldn't stop thinking how good the feeling of the pantyhose and dress had felt on his body. In only a few moments he was bucking and came in the girl's mouth. She sucked greedily, swallowing as much as she could. He glanced down and saw her wipe some of his cum off of her chin and lick it off her fingers. Her eyes were still closed as she moved back up and put her head on his chest. She was asleep almost immediately.