The Crossdressing Couple

A day in the life of Ben

Benjamin Powell works a warehouse job as a forklift driver. He spends long days loading and unloading trucks. He likes his job, though he wishes it wasn't as much work at times. It was physical enough to keep him relatively skinny, with only a small amount of belly fat rolling over his shorts. He kept his long brown hair neatly trimmed, most days he tries to make it look like Obi-Wan Kenobi's hair. Unlike Kenobi, however, he kept his face clean shaven. He wears bright green gloves as a way to protect his hands from the rough work he does on a daily bases. He enjoys organizing and keeping things arranged in their proper place. He has a secret pastime, he likes to dress as a girl.

It all began when Ben was twelve. He was playing in his pool with his friend from up the street, MT. The boys were messing around in the pool, as boys do. Ben's youngest brother was having a bad day and the two boys decided to attempt to cheer him up. Ben and MT snuck into Ben's younger sisters room. Ben pulled a dress from the closet. He still remembers what it looked like: the bodice was a maroon velvet that tightly hugged the body, the skirt was white with gold sparkles around the trim, a white ribbon tied around the waist. Ben slipped it over his head and let it fall into place over his swim trunks. It was a tight fit, but luckily his sister was tall for her age and Ben was quite slim at the time - he didn't bulk up until puberty started when he turned fourteen. The joke was enough to cheer his brother up and he shed the dress, making sure to replace the dress on its hanger in the closet before returning to the pool.

That first dress was a special moment for Ben, he realized that he enjoyed wearing it, it was comfortable and he liked how he felt wearing it. He began crossdressing in secret whenever he could. He was never caught growing up, but had a couple close calls. The closest of which was when he was fifteen, he had pulled his sisters one-piece bathing suit out of the dryer to sneak a swim while everyone was gone. His dad came home just before he left his room. Ben quickly threw some clothes on and was forced to spend the rest of the day with the swimsuit on under his clothes, praying his sister didn't want to swim that day.

He also choose to be things on Halloween that let him wear dress-like costumes: the grim reaper or a Greek God. He went as a girl when he was seventeen, it was the first time he wore panties and a bra, his girlfriend went as a baby and thought that it was funny to be mother and daughter.

He never knew if his sister ever suspected her wore her clothes on occasion, he knew his ex-girlfriend thought it was a funny one-off joke, and he also knew that his wife didn't know anything about his girly hobby.

Ben had met Rachel in college at a Christmas party at their church, about a week prior to Christmas itself. He immediately found her attractive, but he wouldn't say he fell in love with her immediately. He remembered that she looked stunning in a white polka dot dress. She was slight but tall with soft brown almond eyes and long, flowing black hair. Ben was too nervous to ask her out but did ask for her number. A couple weeks later she asked him to join her for a New Years party, the rest was history. He thought about telling her about his crossdressing while they were dating but feared she'd leave him. Now, it was just too late and he was forced to keep this secret from her. He hates that.

There were a few things she did know, of course. Ben was on Swim team in high school and used it as an excuse to keep his legs and armpits shaved. He continued it after high school, truthfully admitting that he liked the feeling and did not like hair on his legs. Rachel liked that he stayed smooth for her, and encouraged him to stay shaven below the waist. The real reason Ben wore gloves at work was to keep his hands soft, the protection was an added bonus. He pretended he kept his hands soft for Rachel but it was to feel more feminine. Ben also did more feminine things around the house; he did all of the cooking and most of the cleaning. Rachel joked that he was her housewife at times, he would reply that she was his Mr. Fixit and she would laugh. Ben also shared deodorant with Rachel, it was Old Spice Alpine. He liked it because it smelled nicer than most mens deodorant and she wore it because women's deodorant caused her to breakout in a rash.

Ben's workday finally ended and he parked his forklift, he double checked that it was charging before he left. He looked at his phone and saw a text from Rachel.

I won't be home for a while, got stuck at the office.

No problem, babe! I'll go get some dinner with the guys. Just get some dinner on your way home. This was a small lie, Ben had no intention of getting dinner with his coworkers. He didn't get many opportunities to crossdress lately and was going to use this time wisely.

Ok. Came Rachel's simple reply.

Ben hopped into his beat up little Nissan and quickly sped home. They lived in a small little cottage. It had two bedrooms, one and a half bathrooms, and was perfect for the two of them. He pulled a small box out of his trunk and stepped in the house moving to the bedroom.

Ben opened his wife's side of the closet and pulled out her polka dot dress, the one she wore when they first met. One reason his attention was drawn to her that night was because he was jealous of that dress. She wore it often because she knew he liked seeing her in it. Mostly he wished he could wear it, but couldn't deny she was hot in it!

He gently laid the dress and the box on their bed. Inside the box were two bras and three pairs of panties. One bra was grey with white straps and little flowers printed on the cups, the other was a bralette that was teal and frilly. Two pairs of panties were boy shorts with lace trim, one was orange and the other a bright blue; the other pair were some hipsters that were a vibrant red, also with a lace trim and a little ribbon on the front.

He undressed and put the grey bra on then slid the red hipsters up his legs. He paused to look at himself in the mirror. He has lost a significant amount of weight since the last time he looked at himself in panties and he looked good. Hot even! If he said so himself. He grabbed a red headband of his wife's and stepped into the bathroom. He brushed his hair and placed the headband on. Then he opened her top drawer, grabbing the makeup bag.

If he crossdressed rarely, he wore make up even more rarely. But it had been a long, long time and when Rachel was stuck at the office she was there for a while, sometimes returning late into the night. Ben had watched Rachel do makeup several times to learn how. He started with the foundation and blended it lightly into his skin. He then did some light eyeshadow and mascara, he didn't want to use a lot of her stuff in case she noticed. He finished with red lipstick, slowly and carefully painting his lips. He liked the feeling and wondered what it would feel like to be kissed wearing it. He slid his finger over his lips and smiled, he did good. He looked pretty!

He returned to the bedroom and stepped into his wife's dress. He slid it over his hips, placed his arms into the sleeves and slowly zipped it shut. He twirled once, loving the feel of the air around his legs and the swish of the dress.

He spent an hour dressed like that, feeling wonderful while crossdressed. He decided to really play housewife by emptying and loading the dishwasher, doing some laundry, and finally vacuuming. He was engrossed in the feeling. He returned the vacuum to its proper place and then heard the key in the door!

He rushed down the hall, skirt flaring, as he dove into the second bedroom - Rachel's home office. He slid behind the desk. Why did I run in here? He thought stupidly. He hadn't been this close to getting caught in a long time. He pulled his legs close to his chest and sat, waiting for discovery.