The Wife Ch. 06

To Whomever the Hell This Is,

Go figure, I love shopping. That's what I discovered over the following months. It wasn't just the thrill of buying, which holds a weight all of it's own. It was the image I got of myself every outfit I tried on, or every outfit I imagined buying. The thought of the feel of the new shoes, on sale. The feeling of coming home and trying them on or the feeling of buying a new piece of jewelry, one compounding the other. Each new dress, skirt, blouse, shirt, etc. was like slipping further into myself. Never would I have imagined fake leather skirts would be what brought me happiness, but they did in bounds.

There were drawbacks. I discovered I was horrible at makeup, never able to match the same level of quality that James had been able to do that first night. He was always encouraging me to practice and I always did, sometimes at the cost of homework or other social activities, but I couldn't recapture that beauty. The frustration only compounded as each day that passed, I found myself spending less time on anything else aside from the pursuit of that person I saw in Jame's bathroom mirror.

I became more aware of every masculine feature, every time I had to shave my legs was great, but my chest drew more and more of my gaze. Since the first pair of underwear that James had given me, I had gotten more, but I felt frustrated that they weren't real. That they were something I had to slip on and off like a shoe. Even more frustrating, is the shame that came with it. I still carried the idea that the dresses and skirts were for behind closed doors. Not something for the outside world. It all still felt taboo.

However, when I wore those dresses, I knew there had never been a time where I felt more alive. More me. That version of me was clawing it's way out and whenever I tried stopping it, I was met with such a pain in my soul. As if I had drunk a most horrible poison and it was slowly dissolving me away. The inside version of me always won. Yet, I still lived that life in secret, never stepping outside the walls of the safety of my apartment.

James had been a great support. I had been over quite a few times after, always ending with me covered in his cum, some dripping from every orifice. My ass more and more sore each time. Each time I went over he had a new present for me. A necklace or a ring or a new pair of shoes. Each time I was all too happy to model them for him as he fucked every last drop of energy from me.

There were others too. I had found myself frequenting the dating sites more frequently and more boldly, some of them I would model the same way for, but more than half the time, they weren't as satisfying. Some only paying attention to themselves leaving as soon as they had cum, which was never very long. Others were kind but flaky and all but sensual. The most unsatisfying of which had been an encounter with a gas station manager who smelt of weeks old cheese and looked like the sun hid from his very presence. Had barely gathered the courage to go through with it and apply a condom before he was done. I had just rolled the condom on, giving it two quick strokes to make sure it was a good fit and he was screaming and filled it up. Though I was surprised he could cum so much.

My frustration was growing. I was wanting more, to chase the feeling I had unlocked and now it felt like it was getting away. Even with James and the occasional chance with Tom, who had only had a layover flight once in that time. By the time we met up, we only had time for a quick blowjob in the airport bathroom, which was hot but then he had to fly away. Not even getting the chance to tell him about the rest. I had decided to dress 'normally.' I was needing something more than crappy hookups and quickie's in the airport bathroom. I wanted to do something exciting outside of just going to James' home.

That was when I had the idea. It was a simple idea, one that didn't require any prompting or thought. To others it might be normal but to me, it was like stepping into a minefield without a map. This idea was the one that would shame all the ones before it, though I could hardly recognize that as I began my work.

I started with my best attempt to apply makeup, which took several hours and many YouTube tutorials to get right, but for once it seemed to work in my favor. Maybe it was because I was so caught up in planning that I didn't have time to focus on the small things, though I was still pretty proud of myself. Then I had to choose the right outfit, and I knew just the one. It was a newer one, I hadn't tried yet, a short skirt that barely covered my ass matched with the classic white blouse over my new padded bra, that put me up a cup size so they were more pronounced. My own dick twitched with excitement, another problem I had come to be annoyed with.

While I always enjoyed cumming and receiving oral, I never liked the fact that despite it wasn't the biggest, it certainly had the tendency to ruin a few outfits. I would get excited and 'boing!' meet the mayor. Luckily this was an issue easily solved. After the umpteenth time of this I had taken to the internet. Many people suggested cock cages, which would prevent the erection and looked painful. Plus, I didn't want to remove an area of pleasure for me. Although for some I would swear that suggesting that point of view was like spitting in their face. Once again though, there was another solution: a gaff.

There were many options for these that I had bought. One for every flavor of simulation and stimulation but general idea is that they offered a place for me to to tuck my penis securely until it was needed. Which was usually only when someone was going down on me and that was usually James. I slipped the gaff on and tucked myself in, applying panties over that. The overall feel was a little bulky but not too much as to throw me off. I pulled a pair of stockings over that for my legs, which were smooth but the feel of the nylon was too good to pass up. Now for the hair.

It had actually been my idea to grow out my hair, which had started slow at first. The first few months it just was short boyish hair, but with some pointers from James and the internet, I soon had smooth shoulder length hair. Which with it came the issues usually associated with long hair. More clogged drains, hour long brushings, and waking up with a wad of it in my mouth were just a few but the end was worth it. Seeing myself with long hair filled me with a joy I still struggle to comprehend. Like seeing your friend after years apart, or coming home to your dog after a long day. I loved every inch of it.

Although it had given me quite a scare the first time I brushed it out. I'd combed out knots before and they weren't fun then, it seemed to be ten times worse with a brush. My scalp still remembered the pain of a thousand hairs simultaneously being pulled and although I had eventually gotten through it, I still thought I was going to be bald when I saw how much of my hair was caught in the brush. It was quite a relief when I didn't go bald and my hair continued growing healthy and fully.

Styling it turned out to be pretty fun too, once I had gotten used to all the different kinds of product to use. From mousse to holding spray, I spent much of my free time learning how to apply them and style my hair in various ways. Oddly enough though, my favorite was usually a high ponytail or a bun. Something about them seemed right for me, but I did enjoy adding volume and making a new kind of bob each day. Today though, I decided to go with an updo, braiding my hair upwards onto my head.

Once I was satisfied with the hair, I took a small gold pendant necklace and hung it on my neck. The pendant was no bigger than nail and held the shape of a lily, my favorite necklace, despite it's simplicity. I took a step back in the mirror. Admiring my handiwork. Not a trace of my old features, I was a totally different person and I love it. I grabbed some high heels that were a little too pointy to walk in but I would definitely need and put them in a sort of purse, instead applying a pair of sneakers. I called it that because for all intents and purposes, it was a purse, yet I always hesitated to call it that, it was more of a book bag to me. One day, maybe I would own one. Right now, I had blown all of my broke college money on outfits and makeup.

Then came the hard part. Leaving the apartment. I had found myself in this position a few times. Trying to build the courage to step out the door and walk in the real world as this new version of me. I always chickened out though and peeled off whatever I had put on to watch TV and do homework.

'Not this time,' I told myself and reached forward. I swung the door open to the empty hallway that hosted my apartment. Not a soul insight. I felt a pleasurable shiver of pride ripple through me as I put the first leg out, and then the other, until finally, I was standing in the hall, ready to go but frozen in fear. I had taken the next step and before I knew it, I pushed forward and was moving toward the street where the Uber I had ordered was waiting for me.

"Evans?" The driver asked as I got in the back seat being careful not to let my skirt ride to far up. I simply nodded. Luckily the driver shrugged and started to drive. To him, I was just some woman who didn't want to talk. Nothing he hadn't seen before. To me, it was a relief. Even though my voice wasn't deep, it was still distinctly male. There were some classes that could help with pitch and what not but I hadn't had time to look at taking any.

The drive wasn't very long until I had found myself at my destination. The Literary Arts building. Where James's office was. This would be the first time I had visited him at his office since that one fateful night months ago. Since then I had only seen him in class or his bed. Truth be told, I wasn't sure he would be very receptive to this idea of mine, but I found myself horny and needing his special touch to release it. Plus I'd already put in all this effort into getting ready. No turning back now.

There were a few people in the hall, most not paying me much attention, but some turning their heads. I imagined they were checking me out, wondering who the hot new thing was on campus. Though the reality was more likely to be a vague interest, the idea of eyes on me walking through the hall to James's office filled me with a fresh confidence and I fastened my pace.

When I reached his door, I paused, pulling out the heels and quickly switching them out with the sneakers. The look was complete. I re secured my bag and gave a brief knock before entering the well lit room. His blinds were open to the campus below, but being on the third floor offered more than enough privacy. James glanced up as I entered.

"Yes?" He asked. "Can I help you miss?"

"I certainly hope so, professor," I said slyly. "I think I need help with my grades."

James eyes lit up with recognition.

"Max?!" He said incredulously. "Damn. You look sexy."

I giggled, surprising myself a little at the noise, and felt my face burn. Hidden behind the blush. It wasn't like he didn't compliment me often but it was always nice to hear.

"I'm sorry," James said, standing from his desk. "It's true though, that a new blouse?"

"Special delivery, just for you, Daddy," I said, giving him a little twirl. I had become so used to him that I knew he'd like it but the nerves lessened as he examined me.

"Come here," he said, motioning for me to come closer.

He pulled me in for a kiss holding me close against his muscular frame. Even with the heels I had to lift myself a little to pull completely into his embrace. His warmth causing me to melt into him and his smell of sawdust and eucalyptus deodorant filling my nose. I always liked that smell, mixing with the sweet smell of my perfume. He broke the kiss and sank into his chair leaving me to take a seat on the edge of his desk, next to his keyboard.

"What really brings you down, sexy?" he asked. "I thought we were going to see each other tomorrow? Not that I'm complaining, I'll never pass an opportunity to see that scrumptious ass of yours."

"No, I really need help with my grades," I purred, leaning forward and running my hand up his leg to his crotch. I was pleased to discover he was hard as his slacks would allow. "I've been really struggling, Professor, and I think I need some extra tutoring to make it through."

"I see," James nodded, giving an understanding smile. "Well, I'm sure I could help. Give you some tips and pointers."

I slid off the desk and straddled him in the chair, pushing my body and crotch into his, feeling his muscles and penis stiffen as I rubbed against him.

"I'll do anything to pass," I said. "I'll take whatever tip you give me."

"Hmm," James said lowly. "Get on your knees and prove it then."

I didn't hesitate, obeying him immediately sliding off his lap and undoing his pants, as it had become routine. As soon as it was free, his cock sprang up to meet me. I gave it a quick kiss on the tip before running my tongue from the base to the top, its delicious taste overwhelming my senses. I played with it using my tongue for a while, teasing it and enjoying its flavor before I traveled down and with one hand stroking his massive cock, I took both his balls inside my mouth.

James groaned with pleasure as I felt them tense in my mouth as I sucked on them. They were thick and heavy and I could tell he hadn't had any release today. A pity, I thought to myself, a majestic sight like these need attention. I let them pop out before sucking them back in, letting my tongue break the suction every now and then to run it over the bottom of his balls, each run causing James to tense and groan with pleasure. This wasn't the main prize though, and I let the tenderized balls fall running my tongue back up the shaft before looking up.

"Does that feel good Daddy?" I asked.

"Oh god, yes!" he responded. "Don't stop now slut, suck my dick."

I smiled at the command and took him in with one big gulp, running expertly down to the base of the shaft on the first bob. The head lightly hitting the back of my throat, which welcomed the familiar feeling. I moaned with pleasure feeling my own penis getting excited but still tucked and secured against my leg in the gaff. I had just started getting traction when I felt James place a hand on the back of my head pushing me down, causing me to gag slightly and pushing me backwards. I struggled to catch myself at the sudden motion. I was aware that I was under the desk and James's hand was holding me in place.

"Don't make a sound," James said sharply, his tone low and commanding. That's when the most heart dropping sound I'd ever heard occurred. The office door swung open abruptly and a familiar voice filled the room.

"Professor Phillips," it said, curtly. "I thought you were going to meet me a half hour ago for your evaluation."

My heart sank into my stomach. The voice, I recognized, belonged to Dean Williams. A woman who the student's on campus avoided whenever possible. If you weren't doing well in class, she would know and you'd be in her office faster than you could say, "oops." Detention wasn't really a thing in college but she found her way into that as well for anyone who wasn't keeping up, she'd give you a 'detention' to catch up. And you hoped you'd never want to have an emergency with her around.

'School waits for no man, woman or child,' She would say.

"Absolutely, Dean Williams," James said, trying to hold his composure, his dick still rock hard in my throat. "Give me ten minutes and I will meet you at your office."

I tried as hard as I could not to make a sound, frozen in fear of being caught in such a position, but the air was beginning to run out and tiny gags were starting to escape. I needed air. I thought maybe I could just pull up a little but James hand shoved me back down. This didn't help as I felt him twitch hard as his dick hit the back of my throat again. It turned him on and as I kept trying, I was getting less air and more horny.

In the back of my mind I knew it was a bad idea. I could've just relaxed my throat, sat incredibly still, but with his cock reacting to each push and my own desire growing; I did my best to be silent and continued bobbing my head. James tried to resist at first but gave in as I felt his body tense with pleasure. I could tell he was holding back an orgasm. I could only imagine what his face was showing. The fear of being caught only fueled me to keep going, only a tiny voice in the back of my head was telling me to stop.

"No," Dean Williams said intently, a way that usually made her sound as if she was angry. Maybe she was, didn't matter, because from the few encounters I had with her she always seemed to be. "I need to have these done for the academic board and HR is already up my ass for pushing yours back already."

James shifted. He was close, and he was trying to hide it. This should've been the next sign for me to stop but I kept going. A small gag slipped from my throat as I stepped up the pace, still I didn't stop. The driver seat had been given up to the overwhelming desire to feel his cum sliding down my throat.

"What was that noise?" Dean Williams voice asked.

"What noise?" James responded, but his voice betrayed him. He wanted to scream it to the world. It was written all over his body as I gave a final push as deep as I could and felt his cock give one final throb and release into the back of my throat. It was a lot. Way more than he usually came which caught me by surprise and caused me to sputter, some of his cum landing on his slacks as he finally let my head go, the rest either in my mouth or the last jet hitting the side of my cheek as I fell back.

I didn't have time to collect myself, while I was still reeling from the excitement as James was suddenly wheeled back and I found myself face to face with Dean Williams. Her expensive tan dress suit wrinkled as she bent down to where I knelt under the desk. I would've thought I would see anger in her dark brown eyes, but her face was even more stoic than usual. The expression similar to the first time I had met with James in the coffee shop, as if she was hiding her true emotions. I looked over and caught a glimpse of James's face. While he too hid his emotions among, there was something more. He seemed tense, his jaw clenched as he fumbled his still half hard cock back into his pants.

"Stand up," Dean Williams addressed me, holding out her hand to help me up. I took it begrudgingly. James stood as well, standing straighter than I had ever seen.

"What the fuck is going on here?" Dean Williams asked in a commanding tone. I hesitated and James said nothing, both of us apparently unsure of how to answer. She looked between both of us and I couldn't help but get the feeling like I'd just been caught with my hand in the cookie jar. Dean Williams shook her head and furrowed her brow.

"Follow me both of you," she said, taking a handkerchief from her suit jacket and handed it to me. "And clean yourself up."

I quickly wiped the cum from my cheek as she led us away, down and out past classrooms and other professor's offices. When we exited the building and began making our way to the administration building was when the knot that had been building in my stomach really took hold, the adrenaline of the under the desk blowjob wearing off. I had to fight the urge to run.

'Just run.' My nerves wanted to be gone and how easy it would be. James could just claim I was some date he had brought back. Maybe the consequence wouldn't be so bad then. Plus, it had appeared to me that Dean Williams hadn't recognized me. So, she had no idea I was a student and had no way of finding out who I really was, unless she got me into the administration building. There she would get me to talk, find out who I really was and fire James.