Darren learns to trust those he loves

Waking up the next morning felt almost like waking up with a hangover. My thoughts were sluggish, a deep feeling of mental exhaustion weighed me down and made it difficult not to roll over as I heard Melissa’s alarm go off. As if it had been waiting for the alarm to go off, Missy’s phone rang out with a message as well. Rolling over, I turned my back to my wife as she turned off her alarm and picked up the phone we shared for Missy’s work.

“You’re going to want to read that.” The short sentence was the only warning I got before the phone sailed across the room and landed on the bed next to me. During the best of days I wasn’t a morning person, and today was not the best of days. Reaching around behind me, my hand lethargically searched for the phone as I heard Melissa close the bathroom door and the shower turn on. Unable to find it, I turned over and picked up the small plastic device. Opening it up, I read the message from Ben.

Ben - Need you on camera again today sorry to ask this of you but at least it’s friday

Falling back against the bed I closed my eyes in frustration. The weirdness of last night still seemed to sit in my mind as I thought over the day before. Thoughts that had felt so pure and perfectly formed from yesterday, now felt muddy and fake. It was like waking up after a day of using **** and trying to piece the last twenty four hours together. I could remember what had happened, but the things I had felt so sure of seemed more like distant memories than something that had just occurred.

The sound of the shower cutting off turned my thoughts towards Melissa as laid there. Looking over at the door, I thought of all the effort it had taken the day before to get ready. Knowing that I would need her help, as well as having the vague feeling that I had disappointed her last night, I stood up and wandered over to knock softly on the door.

Leaning against the doorframe, I spoke through the closed door. “Hey, I’m sorry about last night.” One of the first things I had learned about being married to a woman as strongly opinionated as my wife was that it was often just easier to apologize for whatever she thought I had done, than it was to figure it out and fix it. “I guess I was just off after the weird day.”

I could hear the muffled sounds of her getting ready pause as she heard the knock and then they resumed shortly after my apology. “Makes sense. I know it is a lot of stress on you Darren, but we can’t quit that job. We can’t afford it.” I nodded along on the other side of the door as if she could see me. “So what will you do today? I saw the message from Ben.”

I took a deep breath and spoke the words I never thought I would hear myself say. “Do you think you could help me look feminine today?” The sounds froze for a second after I **** the question out. Suddenly, the door opened and there stood Melissa in a pair of black lace panties and bra, her hair up in a towel.

“Sorry, what was that? Did you ask me to help you look feminine?” Her eyebrow was raised in a gesture of curiosity, although the rest of her body language almost vibrated from excitement. I let out another short sigh as I realized just how much she had been enjoying this. Unable to voice the question again, I simply nodded to answer her. “Well, alright then Missy, feminine you will be.”

The cheshire grin on her face sent both alarm bells and feelings of bliss through my body at the same time. It was obvious that my question had pleased her, and I could feel the happiness of pleasing her lance through me. Still, I saw the chance for her to go too far with this and take things too far. I had never had a good poker face, so when I opened my mouth up to try and make sure she didn’t take it too far, she beat me to the punch. “What’s the matter Missy, don’t you trust me?”

I froze as the question reverberated around in my still foggy mind. I loved my wife. That meant I trusted her didn’t it? I trusted those I loved. My teeth clicked together as my mouth closed. Her question had taken the wind out of any argument I could make. The look on her face showed that she knew it too. “Good. Now, why don’t you go shower and shave. We have a lot to get done.” Stepping past me, patted me on the ass and giggled. “Hurry up.”

And so it was for the second day that I found myself in the bathroom showering and shaving closely. In fact with the shaving involved, it ended up taking me even longer to get ready than it had taken Melissa. So I was unsurprised when I walked out of the bathroom with a towel around my waist to see her dressed up in a pair of casual leggings and a hoodie. What did surprise me was what I saw laid out on the bed.

The maxi length white long sleeve high necked sweater dress sat next to a pair of white cheeky panties and a white corset. I recognized the corset instantly. The steel boned foundation garment had been what Melissa had worn under her wedding dress. I still remembered the look of relief on her face when she had taken it off the night of our wedding. I swallowed and shook my head from side to side as I froze in place. “I can’t wear that.”

Melissa turned and raised an eyebrow. “Can’t or won’t? I ask you to trust me and this is literally the first thing you say? Good lord Darren get over yourself.” She walked up and stood in front of me, staring into my eyes. I could see from the expression on her face that she was displeased by me again. I winced and broke her gaze, unable to stand up under the scrutiny of it.

Reaching over, she lifted my chin up till our eyes met again. “I need you to trust me. I know that this is hard for my husband to do. But, what if it wasn’t my husband doing this? What if it was just Missy?” I tilted my head to the side and tried to understand what she was getting at.

Seeing my questioning look, she went on. “You talk all the time about the roleplaying games you play. How you're not the one making the decisions, the character is. How you settle into their personality after a few games and you can wear it like an outfit you take on and off. Like a cosplayer right?” I nodded along suddenly seeing where she was going with the idea.

I frowned and thought over the suggestion she was making. Could I treat this just like a game of D&D? Could I really play the role of Missy? Honestly, I had already been doing that for months at this point. It wasn’t like I was completely removed from the office gossip or questions about weekends or hobbies. I had lied through my teeth about what Missy did in her spare time. I had even made Missy out to be a bit of an air headed ditz just to mess with Melissa. Her weekends were filled with shoe shopping online and watching reality TV. The more I thought about the character of Missy the more I realized that the corset was something she would wear.

Melissa’s eyes searched mine as we stood toe to toe in our bedroom. She seemed to like what she saw in them after a moment. I swallowed and nodded slowly, but there was a question I needed to ask her before I went forward with the idea. “I need to ask you something. Since yesterday, you have been all about this idea. I don’t get it. Where is this coming from? Does dressing me up like this please you somehow?”

I could see concern well up in her eyes at the question. She seemed to think it over briefly as she stepped back and looked down at the clothes on the bed. Turning back, I could see the flush of embarrassment color her cheeks as she took a breath. “It really does please me. I don’t know why hun. I think it is fun.” She paused to let that sink in before she spoke up again, this time her words came out softly and with more care behind them. “But if it bothers you that much, we can stop I guess. I just don’t know how we will pay bills.” Sitting down on the bed she looked at the ground and sighed sadly.

My mind suddenly began to find reasons that this wasn’t so bad. That perhaps it wasn’t such a big deal. Guys had dressed up as women for hundreds of years, for all kinds of different reasons. It seemed like doing it to not only keep my wife happy, but to keep food in our mouths was a worthy reason. Still, I balked at the thought. A real man would have been able to take care of his family. Here I was not just dressing up as a woman, but pretending to be my wife. Just so she could keep supporting us. I wanted to please Melissa and do as she asked, but the idea that I could only do that by wearing a dress just seemed so absolutely wrong.

Turning around, I walked back toward the bathroom. “I need to think.” I turned and stared into the mirror. The man that looked back at me looked scared, weak, and frazzled. Leaning down, I turned on the cold water and splashed my face repeatedly. Scrubbing my hands over it, I tried to think my way through the quagmire of competing emotions. My eyes glanced up as Melissa slipped into the bathroom and held her hand out towards me.

Reaching out, I held my open hand under hers and felt the pair of recharged earbuds drop into my open palm. Looking up into Melissa’s eyes, I saw the fear and determination that was combined there. I knew she was afraid of us not being able to pay bills, and that fear hurt me. Closing my eyes, I reached up and slipped the earbuds in wordlessly. With a tap the music began to play. It was different from the one the day before. There was a softness to it, a lilting melody that reminded me of the color pink and the feeling of silks sliding across your skin.

As the song seeped into my mind, I could feel Melissa’s hands grasp mine and slowly pull me back into the bedroom. I floated along with the melody and allowed her to direct me where she wanted me. As I stood next to the bed and felt her slip the towel from around my waist, I heard the words of the song begin. It was muscle memory at this point to follow along with them.

“I am comfortable.” At the moment I said it, I knew it was true. I was at home, in a safe space, with someone I loved and trusted. Fresh from a hot shower and a long night of sleep, my body felt wonderful. As I stood there, I felt Melissa moving my body. Each leg was directed into the leg holes of the white panties as she pulled the soft cotton underwear up. As the settled into place and I felt the wrap around my ass, I felt my member twitch at the smooth soft fabric. It seemed the memory of my reward from the night before was being tied to the feelings of the clothes I had on.

“I obey those I love.” Trust and obey are the same thing aren’t they? No one would choose to obey someone they didn’t trust. I was free to make decisions and I trusted Melissa completely. In my heart I knew that she was the reason we were able to live the life we lived now, it was her drive and successes that had gotten us this far. I simply needed to give up on my own mental bullshit and let her direct me. As I slowly began to rationalize the thought of obeying Melissa, I felt her wrap the white satin corset around my waist.

“I will dress to please those I love.” When I first met Melissa I had been the exact kind of nerd you saw lambasted in the media so often. Graphic T-shirts, sweat pants, and dingy shoes were my everyday wear. Slowly, as I somehow convinced her to spend more time with me, I allowed and encouraged her to help me dress so I stopped being quite the embarrassment to her that I thought I was. Over the years I had morphed from the nerd kid, to the tech adult. It was all thanks to her. With the last clasp of the corset done up, I could feel her slowly begin to pull the satin ribbon that laced the back and felt it begin to constrict my waist. There was a moment where I thought about calling it all off, but the next sentence came along and I forgot all about my reservations.

“I trust those I love.” It was easy to say this particular affirmation. You can’t obey someone you don’t trust, and you can’t trust someone you won’t obey. The logic simply fit together perfectly. I closed my eyes and mouthed the words silently to enforce the thought process. I trusted Melissa, I loved Melissa, I would obey Melissa.

“I feel sexy.” With the corset fully pulled in, I was once again experiencing the same constricted feeling from the waist cincher the day before. It wasn’t uncomfortable, just restricting. Again, Melissa took a few handfuls of her stockings and stuffed the cups of the corset. I looked down and saw the soft nylon as it was jammed inside the cups and felt it rub against my nipples. There was something about those bumps on my chest that sent a tingle through my mind. I could feel it rubbing up against a strange thought from my run the night before, but I couldn’t quite pin down the exact sentiment. It was like forgetting a word you knew the meaning of. I kept trying to figure it out.

My mental struggles to remember the exact memory from the evening before distracted me from the spot in the song that was blank. My subconscious picked up on it and in that exact instant I spoke the words from the night before. “Feminity is Sexy.” It felt like a lightbulb went off in my mind. That was the thought I had been trying to remember from the night before. The words fit into the space, but didn’t quite feel right. They were true, of course, but not the perfect fit for the way the music seemed to draw me in.

With the corset and panties on, it was time for the dress. As I felt Melissa guide my hands up and through the garment, I continued to repeat the words in sequence. It was a struggle to fit into the tight gown. The soft sweater material felt good against my upper body, but as my hair legs brushed against it, I could feel them catch on the weave. I didn’t hate the sensation, but a part of my mind told me that it was completely wrong to have happen. As the dress settled onto me, I rubbed my hands around my smooth chest and upper arms and felt the material of the soft dress press against my skin. A stray thought of wondering how it would feel with smooth legs distracted me long enough to miss a space in my mantra.

Looking up, I saw that Melissa was motioning me over to her vanity to sit down for the red wig and another round of makeup. I took a deep breath and waited for the song to start the mantra over before I moved over to the chair and sat down. With the earbuds in, I didn’t get to hear the same running commentary as Melissa expertly applied my makeup step by step. Today’s makeup look was a soft professional look that still hinted at the girly girl that I had made Missy out to be. It was difficult to keep up the affirmations while having my wife put my lipstick on, but I managed to keep from faltering even as I tried to find the right words to fight the missing space.

With my makeup done, Melissa ushered me out of the chair and pushed me towards the door to my office. Following her unsaid commands, I slowly made my way there. Sitting down, I looked at Missy’s phone in my hand and saw the message again. Realizing neither of us had responded to it, I quickly messaged him back.

Missy - I’ll be ready.

The phone buzzed just moments after I hit send and I could see another message from Ben pop up.

Ben - Done already? Prove it

Prove it? He wanted me to prove that I would be ready for this? I didn’t understand how yesterday hadn’t been proof enough that I was serious about this. I grumbled and leaned back into the chair, the corset once again forcing me into perfect posture. The words of the song slipped through my mind as I spoke them aloud.

“I am comfortable.” I was home safe. Melissa was nearby. I knew that I was safe from any real harm.

“I obey those I love.” Usually saying a line would lessen my inner struggles, instead this one seemed to amplify them. Who was Ben to order me to prove that I was doing this? Sure, I worked for him. Sure, he was the one person who was making it so that I could be employed. Even if it was as Missy and not as myself. Sure, he had stuck his neck out for me just the day before with the company. But I didn’t love him. I couldn’t love a man I barely knew, could I?

“I dress to please those I love.” The words interrupted a thought process that I wasn’t sure I wanted to finish. Yet this affirmation didn’t help the situation either. I thought back to the eyes of the delivery man, even to Ben’s look when I had first turned my camera on. I didn’t love either of those men, I didn’t think. Certainly not the delivery man. Still there was something about the way they looked at me that mirrored the look I had seen in Melissa’s eyes as she had come to give me my reward the night before.

“I trust those I love.” I trusted Melissa. She trusted Ben. Did that mean I should trust Ben? Did that mean Melissa loved Ben? If I trusted Ben did that mean I needed to obey him? The thoughts swirled through my mind as I opened up the phone and turned on the selfie camera. I saw myself on the screen and was again astounded by how much like Melissa I looked. There were subtle differences, my jaw a bit broader, my nose a different shape. No one would ever mistake us for twins, but sister’s? Certainly.

“I feel sexy.” Sitting there in my wife’s clothes, holding up a camera and looking back at myself it was hard not to feel sexy. I loved this dress on my wife, the way it hugged her curves and hinted at the sexiness below. Knowing that under it was a corset, one of the sexiest things a woman could wear only made it even more alluring. It took me a moment to realize that I was getting turned on by my own image. I thought about what it would look like if Melissa really did have a sister. About how the pair of them standing side by side in this dress would look.

The blank space in the track appeared again as I realized something. “Dressing feminine feels sexy.” The words clicked into place. My finger snapped the picture as I sat there smiling at the camera right after uttering the words. Hitting send before I could stop myself, I tossed Missy's phone to the side and turned on my computer for another day of work.