The Crossdressing Couple

A day in the life of Rachel

Rachel Powell worked at a tech company. She was a lower tier manager, she was the bottom of the managerial totem pole but was just below the middle. Her days weren't always happy. It's not that she didn't enjoy life, she did. She just wished that she could be more relaxed at work sometimes. She seemed to always be the one called on to fix problems, and she'd get them done! She was reliable, dependable, and would do the job that needs to be done. That was part of the reason she was where she was in the company so young, the other part was that she was damn good at her actual responsibilities. Most of her compatriots were ten to fifteen years older than her, and that proved she was good at her job. She knew that rumors floated around about how she got her position so young. She hated that they existed but decided that those rumors wouldn't bother her. She kept her appearance up, she was the good-looking, get-it-done manager. She just wished she could let her secret out sometimes, just wanted to not care about appearances. Her secret was simple: she liked to dress like a boy.

That part of her started when she was fourteen. Her mother pressured her to be a stay-at-home mom like she was. Rachel loved her mom, but she was overbearing at times, having her learn to cook so she could take care of her husband and children, learning the proper way to fold a fitted sheet -who cares anyway? - and basically being the traditional 50s housewife. That just wasn't for her. For as long as she could remember she wanted to ride bikes, play in the mud, and get in rowdy trouble like her brothers. That wasn't a problem till she turned thirteen.

"Now that you're a teenager it's time to put those rough things away," her had said.

She was a young woman now and it was time to learn her responsibilities. She got in a lot of trouble for sneaking out to keep playing with her brothers and their friends. Her dad defended her, and bailed her out a lot. She would be forever grateful to him for that. But at fourteen Rachel decided that it was time to appease her mother and she put her brothers hand-me-downs away and put on the dresses that her mom wanted her to wear. On the outside she was the prom and proper young woman her mother wanted, but she still wanted to dress like a boy and have fun. Whenever she had a chance she would sneak into her brothers room and wear his basketball shorts or jeans and wear a baggy shirt. She never brought herself to borrowing their boxers because there are lines that shouldn't be crossed, underwear was one of those lines.

Throughout the years she would find ways to be boyish without her mother finding out: wearing basketball shorts to family theme parks, social events like Halloween costume contests (she won once as Al Capone when she was sixteen), or going on hikes.

Eventually she moved out to a college dorm and was able to be more tomboyish but all the FaceTimes with mom meant that she had to wear makeup all the time because she didn't know when mom would call. I suppose that would be her biggest flaw, she was a people pleaser and wanted her mom to be happy.

Her mom encouraged her to go to a church Christmas party on campus, Rachel didn't really want to but had nothing else going on that night and figured she would go. She dressed quickly, putting on an old polka dot dress that she had gotten for her eighteenth birthday, and only wearing some mascara and foundation. At the party she saw a guy looking at her. He was wearing a sharp suit with a neat grey and orange tie. ZZ Top had it right, "every girl crazy 'bout a sharp dressed man." He had dark disheveled hair, intentionally messy. His hazel eyes sparkled behind thick black "nerd" glasses, and he seemed all to at ease for someone at a church party. He walked up to her and shyly asked for her number, and almost forgot to ask for her name. It seemed strange that someone who apparently exuded confidence was so shy, for that reason she gave him her number and had him text her so she had his.

He hadn't texted her yet and it had been a few weeks; granted it was the holidays, but still. She texted him and invited him to her friends for a New Years movie night. He said yes. Rachel was excited and for once was grateful for the things her mom forced her to learn. She made sure she dressed cute, but not slutty. She wore a cute red dress and made sure to put some lipstick on to encourage him to make a move. At the end of the night, she decided to make the move after it was clear he wouldn't. Later he told her that was his first kiss. She felt kinda bad for taking that control away from him, but it made her feel a bit more masculine and she enjoyed that.

Eventually he proposed, though he was taking so long she almost asked him, and they had a wonderful, small wedding. She wore a simple white dress that wasn't too girly and had a great time. It's been five years and she tried to be, as her mother had taught her, a good wife. That included looking beautiful for her husband. Thankfully, Ben not only was ok with her working, he encouraged it; and she enjoyed that she made more money than him. She was the bread-winner and that made her feel a bit more like the tomboy she was, even if that tomboy had to wear dresses.

She decided she needed some boy time and pulled out her phone.

I won't be home for a while, got stuck at the office. This wasn't an unbelievable lie, she got stuck here a lot, sometimes not getting home till one or two in the morning.

No problem, babe! I'll go get some dinner with the guys. Just get some dinner on your way home.

Ok. She replied. He'll probably get a ride with Jacob, his work buddy, to whatever restaurant they went to.

She finished her last hour of work excitedly and went down to her clean Toyota. Normally, her husband had dinner ready for her when she got home, but today she was so excited she was fine skipping a meal.

When she pulled up to their cottage she saw Ben's car out front, she was right about him riding with Tanner. She grabbed an extra bag out of the trunk and headed inside. She noticed the kitchen light was on, He must've done dishes and forgot the light. She checked the kitchen, bedroom, and bathrooms to confirm she was alone before returning to the bedroom.

She saw a small box on the bed with a bralette and a couple pairs of panties in it. "When will he learn that frilly isn't my style?" She asked herself. Ben constantly got her little gifts like this for birthdays and whatnot. She would wear them to humor him of course, but she preferred the lingerie she got herself, it wasn't nearly as feminine.

She dropped the bralette back into the box and began taking her skirt-suit off. She pulled some ace bandages and a pair of boxer shorts out of her extra bag. She carefully replaced her suit in the closet then slid the doors over to reveal her husbands side. She selected his grey suit and placed it on the bed. She also grabbed his white button-up and a tie.

She put the boxers on first, enjoying the freedom of them. They were so much better than the form fitting panties she wore on a daily basis. She then began wrapping her chest, this was something she started doing after she got married. If she didn't bind her breasts she ended up looking like she just got out of bed wearing Ben's clothes. She pulled the bandage tight and checked the mirror, satisfied there were minimal bumps on her chest she grabbed the shirt.

She remembered borrowing her brothers white shirt the first time she snuck around to dress up and struggled because the buttons were on the wrong side, now it was almost second nature.

She pulled the pants up, liking the loose cut that hid her body. She tightened up the belt after tucking the shirt in. She tied the tie, walking through the steps in her mind, then shrugged the jacket on.

She was once again astounded by how well she fit into his clothes. Granted, if it wasn't for her breasts they would be the same size since he was only a couple centimeters taller than her.

There was only a couple things left to do. She tossed her clothes into the laundry hamper, noticing it was empty. Ben was so thoughtful. She reached the bathroom and gently wiped her make up off, placed her earrings in a small box on the counter and combed her hair back, placing it in a low ponytail. She'd love to get a pixie cut that could be styled like a man, but she was worried about Ben not liking it. She'll bring that up tomorrow at dinner. For now she slipped a pair of his socks on, and went back to her bag.

Inside the bag was a tiny box. Inside it was a small black mustache. She had purchased it on a business trip and was surprised with it. It felt and looked real, and the adhesive wasn't painful when she went to take it off. She gently pressed it under her nose. Appreciating the idea of facial hair. She didn't like it on Ben, but she didn't mind having it herself.

"Rachel?" Her husband asked.

She turned and stopped cold. Standing before her in the doorway was her husband. In her dress.

"Ben?" She asked.