The Wife Ch. 05

To Whomever the Hell this is,

A week passed before I was forced to return to the world. I hadn't stepped out of my apartment since I had stumbled in and crashed on the couch. When I finally woke up the following morning, I was in pain. My whole body locked up from the deep sleep I had put myself in, sore from the barefoot walk home. The pain reminding me of the night prior, his shirt smelling of his intoxicating cologne reminded me of his muscular embrace, bringing a pleasurable arousal to the pain.

The cum stained panties and bra were easy enough to clean. I had a brief thought of tossing them and the shirt, but something stopped me. There was a new feeling arising within. Not just the thought of how good the sex was, but of how amazing I had felt while wearing the lingerie. Feeling Professor Phillips fingers sliding the panties to the side and pushing inside me, the way the fabric felt on my chest. It was like I had slipped into a bath of silk and comfort.

The feeling I got whenever I held the garments filled me with a feeling I had been completely unprepared for and unable to recognize in the heat of the moment. They felt right. As if I should have been wearing them for some time. I wanted to repeat that experience. For the first few days I used that feeling to pass the time. IT was a hard feeling to ignore, so I spent hours online, perusing my newfound fascination. Surprising to me, there were quite a bit of resources for crossdressing. Online stores, forums, and advice columns.

On the other hand was the embarrassment. Professor Phillips had sent me one text since that night. It had taken me a lot of hours to build the courage to open it.

'Good morning, sexy. When you are up to it, I would love to see you. I hope you're doing well.'

The thought of seeing him again was appealing. His commanding and muscular presence making me quiver in excitement. I even have to admit that I couldn't help stealing smells from his shirt and masturbating to the memory of how he had taken me. His hands running over me as he shaved me. The thought sent shivers to my toes. However, the excitement couldn't overpower the shame I had felt from having to flee half naked from his home. As such, when the time came for me to go to his class, I couldn't go. Fast forward a week and I received another text.

'Mr. Evans. Your absence from class has gone on too long. Please see me in my office to discuss your options.'

The tone change sent a shiver down my spine, catching me off guard. I felt my face suddenly flush red as I reread the text again and again. How was I supposed to face him again? Yet I was intrigued. My mind should have been filling with my school work but all it filled with was the thought of Professor Phillips sitting at his desk, his shirt off and telling me to get on my knees. Shame mixed with excitement filled me.

I could just not go and face the music of having to start the whole semester over. The class was very important for my grades and I was getting very behind. Or I could swallow my pride and hope that it wasn't already too late. That he hadn't reported me to the school board or failed me already. Either way, he was now in complete control. In the end there was only one option.

Within an hour I found myself in front of the door to his office outside his classroom. I hesitated before knocking, the weight of the situation building in me. I took a steadying breath and knocked.

"Come in," Professor Phillips voice said.

Professor Phillips was sitting at his desk, dressed in his usual shirt and tie. He greeted me with a smile. Which surprisingly relieved some of the trepidation. He motioned towards a chair.

"Have a seat Mr. Evans," he said. He waited until I was seated to continue. "I'm pleased that you came in."

I didn't say anything but felt my face burn red, which had been consistently blushed since I left my apartment. His cologne was strong and fresh and while he appeared calm and collected he had his hands clenched firmly on the desk. His piercing emerald eyes never leaving mine. They held that same hunger he had had that night in his bathroom as if they were already undressing me. I held his gaze only barely, not wanting to appear nervous, even though I was sure it was written all over my face.

I couldn't help but imagine him naked, rock hard and ready for my eager mouth. I swallowed hard trying to ignore the sudden image, but being here now, it was all I wanted. The silence seemed to last too long but he seemed unfazed. Was he thinking the same things?

"Well, I guess I should start," Professor Phillips said. "I'm sorry about the other night. I realize it must've been a bit weird for you."

I didn't say anything. Weird wasn't even the half of it.

"I want you to know that I'm not going to dock you for missing the last week, and if you need to transfer to another class, I'd be more than happy to help make it happen; but it would be amiss of me not to mention that I enjoyed every moment and I would love to see you again."

I remained silent for another moment, weighing his words. Not really what I expected him to lead with but it did help my nerves a little bit. When I finally spoke, my voice surprisingly was not as shaky as I felt.

"I have some questions," I said.

"I thought you might," Professor Phillips said. " I will do my best to answer as best as I can. What's your first question?"

"Are you married?" I asked before I could think of any other question. Professor Phillips didn't seem surprised.

"I am not," he replied calmly. "I was married years ago. The story is long and most of it unimportant for this. We weren't happy together and got divorced. She and I aren't super close aside from our daughter, Jessica. She is the one who interrupted us last week. I messed up and forgot a very important date for her."

"Does she know about me?" I asked, unsure how to phrase the exact question. He seemed to understand though. In my mind it was his quick reaction to hide me in the bathroom, he didn't want anyone knowing I was one of his students either.

"Does she know you are one of my students? No. I told her nothing about you, just that you were my date and I had mixed up my days."

His look was sincere, though I felt guilty still that I had been the reason Professor Phillips had missed whatever the important date was. He must have sensed my guilt as he assured me.

"Don't blame yourself. It really is on me."

"But it is though," I said, surprised at myself. "I may not be the sole reason but I do share some of the reason. I can't be the one who comes between someone else's family."

He nodded firmly. "I understand. You won't. I've already made things right with her and I will make sure it wont happen again."

I sensed he used the same apology with Jessica, but that didn't really concern me. Family drama was weird enough on my end, I really didn't want to end up entangled in Professor Phillips. Just his arms. They were bursting through his shirt making it very hard to envision anything other than them wrapped around me.

"Does you're daughter know I'm a man?" I asked. She had referred to him as 'she' when she had interrupted. What I really wanted to ask was more personal. Did he really want a woman? Was he out to his family?

"No." He responded. "I'm not scared of my sexuality if that's what you're worried about, but like I said, I really didn't tell her all that much about you."

His words lingered heavily, which surprised me more than my question. I was almost kind of bummed he hadn't. As if I was hoping he had sung praises of me while the other part of me was glad he hadn't done that with his daughter. It was a truly bizarre feeling for one night of sex.

"So, what now?" I asked. I genuinely didn't know where to go from there. "I've never been in a situation like this before."

"Like I said, that's up to you. I would love to see you again, but I understand that might be a bit awkward for you. Honestly, this is awkward for me too. I've never had sex with a student before."

His hands and jaw loosened a little. His sincerity didn't catch me off guard but I had half expected him to have done this before, with how attractive I suddenly found him, I had a hard time believing this was the first time a student or anyone had been in his bed.

"Never?" I asked. "It seemed so natural for you."

Professor Phillips laughed.

"No, you're the first."

I weighed my options for a moment. I didn't really want to transfer classes. It would mean a lot of catch up, and now that I was here, all the scenario's kept battling with my other thoughts. I couldn't stop thinking about sliding under the desk and unleashing his manhood, feeling his hands run through my hair as he guided my head on his dick; or riding him on his chair, my face close to his.

"I enjoyed the other night to, though, not the running out half naked part though." I finally said. "I haven't been able to stop thinking about it. I also don't want to transfer classes."

"You don't have to transfer, if that's what you want to do." Professor Phillips said. "Now I have a question. I really enjoyed that night, and since we were interrupted, I would like to try again. Maybe this time a little more grace?"

"I would like that," I said. I didn't really have to give it much thought. An actual date sounded like an appealing way to ease back into it. See how I felt.

"Perfect," he said, letting loose another smile. "I hope you don't mind, I did buy you something in hopes you said yes. Since you enjoyed the lingerie so much, I thought you might enjoy this as well, it pairs nicely and I think it would look good on you. Do you still have the lingerie?"

"Yes," I said.

He opened his desk drawer and withdrew a large whit box. I took it opening it with shaking hands to reveal a dress. The fabric felt soft and silky, flowing out of the box like a wave of water. Holding it up I could see a slight floral pattern around the hem of the dress running up the side to the bust. stopping just beneath the shoulder straps. The cups were somewhat small, looking like they would fit over the bra while not being competitive with it. I was stunned. I had thought it might have been more lingerie.

A mix of anticipation and uncertainty flooded my senses. He thought I could look good in this?! I wasn't even sure it would fit but all that was overtaken by my desire to try. Professor Phillips must have sensed my uncertainty, he eyed me pointedly as I held the dress in my lap.

"Remember what I said about my tastes, it will good on you. I got a good sense of your size last time."

His confidence showing more and more. Reasserted by our new understanding of each other. I hadn't thought that so soon I would be wearing a dress. I knew right then I would though. Suddenly it was clear to me that he had me and he knew it. Knew it from the moment he had sent me the text to come in. He bought the dress knowing that even if I transferred classes, I was going to agree to the date, agree to the dress.

He had known it when he decided to set up the meet last week, when he discovered I was a student. His intense emerald eyes didn't just burn with hunger, they saw something else. This knowledge bolstered me. His confidence stripped all of my hesitation. He knew who he was and what he wanted. I was beginning to understand just a little piece of who I was, and he seemed determined to discover that person with me.

"Do you want to try it on?"

"I do."

"Good. Be ready for me at 8 then.

Getting ready wasn't the hard part as it turned out. Shaving the hair proved easy enough, since I had been doing it every morning since. The dress complimented my figure very nicely actually. Given the dress was such a feminine piece of clothing, I had been surprised to find that my worry wasn't if it would fit, more so it was if I would look to masculine in it. After putting it on over the lingerie however, I saw that it actually brought out some of my softer features. I was taken back most by how I looked with the padded bra.

Seeing the simulated breasts awoke a sensation that felt familiar, but buried. A certain longing that hadn't shown itself in so long, it greeted me as an old friend, waiting for the right moment. It was definitely weird seeing myself with breasts, freshly shaved. If my hair was a bit longer, I would've certainly not been able to recognize any masculine features that moments before, were so pronounced. I would've confused myself for a woman.

The worst part was waiting for eight. Once I was ready and dressed, time seemed to slow down. Dragging each second as it had every time prior to me taking such a step. I wasn't sure how to pass the time, so I perused more forums I had been accustomed to frequenting now. Seeing other testimonials made me wish I had a piece of jewelry or something else. Which only added to this new envy sensation. Maybe I could try some later, now that the initial discomfort of the situation was replaced by excitement.

When eight finally arrived, I was already a bubbling mixture of horny, nervousness and anticipation. Professor Phillips was right on time, knocking on my door with spry fervor. I opened the door, unsure of how to hold myself, but trying to pose in a sexy manner. He smiled, visually pleased with what he saw.

"I told you it would look good on you," he said lowly, his voice saturated with desire. "You look absolutely stunning!"

I felt my cheeks burn red as I thanked him. A feeling I was getting incredibly used to and addicted to the butterflies that accompanied it. He motioned towards his car and I followed him out. The drive followed a similar theme, as he explained to me his plans, he ran his hands up and down my legs.

"Hmmm," he said, squeezing my upper thighs firmly. "So soft. You did well."

"Thank you," I said.

"Don't forget about our terms," he said.

"Thank you, Daddy," I corrected myself.

"Very good," he grinned. "Although, I was thinking, I'd like you to call me by my name too. Give it a good mix. Plus, I kinda want to hear what you sound like screaming my name."

"Oh, ok, James" I said with slight hesitation. It felt better using an actual name. The added implication of the way the night would end only made me more horny than I already was and made the name usage feel more taboo and sexy. I found myself wondering what he had planned. Was another unknown boundary about to be pushed? What else could the night hold?

No matter, in that moment, I wanted to do anything he wanted. Time to process the roller coaster of emotions flowing through me would come later. Right then I was intoxicated by him. Swept away by his charm, his assuredness, his demeanor. How he looked at me and saw something I seemingly couldn't find. Like he was devouring every inch of me in his head. Like I was the first beautiful thing he had ever seen. The desire in his voice every time he spoke. A totally different light than I had ever seen him in before.

We eventually arrived at his house pulling me from my own head. The house seemed more familiar now that it was my second time back there and we followed the same path back to the master bedroom and the bathroom beside it. There were items on the bed but I didn't have time to see what they were as he guided me in front of the mirror. Displayed in front of me on the bathroom counter was an assortment of makeup. Not just the basics either, but tools I'd only ever seen but had no idea what they actually did. From blush to lipstick to hair products to perfumes, it was as if a cosmetologist had set up shop before abandoning her work.

"What is this?" I asked in surprise.

"This is for you," James said. "Well, I mean to say, it's mine but tonight, we're going to use it on you."

"I don't understand," I frowned. "You're going to apply makeup to me?"

"Of course," James replied. "It's going to make you look beautiful."

I was a mix of fear and excitement. A combo I was starting to get used to feeling. Some deep part of me was screaming 'YES!' while another was like "Whoa, don't you think you should slow down?' Each had it's own weight to it's own voice. The first voice was slightly louder and so I let James begin his work. He started by cleaning my face and walked me through the whole process.

"You always start by cleaning the face first," James said. "It'll help create a smoother application and help prevent any acne breakouts."

"Acne...?" I asked hesitantly. Last thing I needed was a breakout, I'd already done that through high school. It wasn't an experience I wanted to repeat.

"Don't worry, sexy," James soothed. "It's just a precaution."

Something told me otherwise, but I didn't press the issue.

"How do you know how to do all this stuff," I asked.

"I've helped my daughter with her makeup in the past," James responded, not moving his eyes from his work. "When she was young that's all she wanted to do was play with her mother's make up. Sometimes the only way I could spend time with her was if we were doing make up tutorials."

I was caught off guard by how sweet and normal the answer was. I was actually shaming myself for assuming the reasoning would be sexual. I wanted to push for more detail but paused as James moved on to what he said was a primer. It would help smooth my pores and help my makeup stay fresh. He ran the brush over my face firmly, spreading it evenly across.

I didn't say much more as it became difficult to speak as he applied layer after layer of makeup, moving from foundation to blush. Despite the fact that my cheeks had been in a constant state of red since he had picked me up, but I didn't argue. When he got to the eyeliner, he was very accurate and gentle.

"Don't want to miss now," he said.

Finally he picked out a lipstick and had me puff my lips so he could get a good coat. When all was said and done, I didn't recognize the person I saw in the mirror. Of course in the back of my mind, I knew it was me, but this was a stranger to me. Instead of an average looking young man, there was an elegant woman. While she was strange and new, there was at the same time, a familiarity to her that was different from the knowledge that despite what I was seeing, that was me. The feeling reminded me of seeing someone for the first time after not having seen each other for months.

I couldn't help but let out a small gasp. James smiled, his eyes betraying his delight at my own, and at the figure before him. A wave of emotions flooded through me once again, washing over me with silent cries of excitement and joy. A joy that filled me with a warmth akin to wrapping myself in a blanket fresh from the dryer.

"I told you it would make you look beautiful," James said for the second time that night.

"I...Don't know what to say," I said, unable to stop staring.

"Don't say anything," James replied, grabbing my hand. "but let me show you how beautiful you are."

He guided me from the bathroom back to the bedroom where I finally saw the assortment of toys he had prepared. An assortment of dildos, vibrators, and butt plugs. He sat me on the side without and pressed his face into mine. His hot breath heavy and minty as he kissed me deeply. The lipstick seemed to enhance the quality of the kiss. My head felt light, different from this kiss than the last and each kiss after, only increasing in intensity. His tongue found mine and danced. His hands roamed my legs and lower back, feeling every inch, starving for my skin. I couldn't help but do the same, running my hands along his back, pulling him in as close as I could.

Eternity seemed to last in that kiss, his chest rising into mine, brushing the bra and sending tingles through my heart. Until suddenly, James broke the kiss. I half expected lipstick to have transferred over to his lips but there was hardly any, leaving only my imagination as to what mine looked like. He placed a hand on my shoulder and gently laid me onto the bed, repositioning me to how he wanted, moving limbs this way and that.