The Dearing Chronicles Pt. 01

Business trips always put me in a good mood. Not that I really liked being away from Rachel, but 'the intangibles' as I called them were worth it. It took some slight-of-hand to pack those 'intangibles' so that my lovely wife didn't catch on, but I had figured out a system, and for the past five years, it had worked like a charm.

One last adjustment of my skirt and I stepped into my heels. I thought I still looked like a MIAD or 'man in a dress,' but I felt wonderful. There was something relaxing about the women's clothes I had bought covertly at thrift shops and on line. The wig had been problematic, and I had settled for a cheap $35 one because it was easier to explain a small purchase from an online costume shop than a $500 purchase at high-end wig shop, so I made do.

So, there I was in my hotel room admiring myself and relishing the feeling of my stockings against my legs.

I didn't hear the door open.

"Well Carson, I love how your top brings out the purple in the flowers on your skirt, but that wig is absolutely atrocious." It was Rachel's voice.

"Rach, I can ex..." my voice dropped off because I knew it was a lie. How could I explain something I didn't understand myself? I could see the disappointment and the fear in her eyes even as she tried to hide it with her sense of humor.

"Why don't you put on something more comfortable. Those heels look like they hurt, and I think you and I need to talk." She dropped her suitcase and sat and watched as I changed. "The keynote cancelled, and they called me at the last minute. I thought I'd surprise you, but it looks like you beat me to the punch." The laugh that followed was forced and I knew I had hurt the woman I love, and badly.

By the time I packed away the 'intangibles' and once again looked like the man she married, I went to join her on the bed. "Um, no. You sit over there. I need some space to try and wrap my head around what I just walked in on. Would you care to try and explain 'this'?", she made a broad sweeping gesture with her hands. "Just how long has this been going on and why, Carson? How could you not tell me something like this?"

"I honestly don't know what to tell you Rach." I stumbled to find the words to tell her that it had always been this way.

"OK, Carson. Let's start with what you can explain and go from there." She was talking to me like we were in a planning meeting trying to decompose a complex issue in our software. "How long have you been doing this?"

"For as long as I can remember.", I started. "I can remember playing dress up with Sarah when I was four or five and I really liked it," Sarah was my older sister, "Something about it just felt right, and still does. My mom had to explain to me that most little boys didn't wear dresses and that I should keep it just between me and her and Sarah or the kids at school might start to tease me. In middle school and high school, I used to steal Sarah's panties to sleep in and sometimes her nightgowns."

"So, is it a sex thing? I mean do you do this to get off? Do you not like making love to me?" I could see the tears welling in Rachel's eyes.

"Oh, Rachel, No. God, no." I wanted to hug her so badly but knew she still needed her space. "I love you and making love to you more than anything. I mean in high school, I used to masturbate in the panties, but a stiff breeze would have done just as well. I really can't explain why; it just feels right. Does any of that make sense? If it does, please help me understand because I have never understood why I need to do this. Logically, it's silly. I mean the clothes don't really fit quite right and I know I look like a clown, but, It just 'feels' right. What else can I say?" I was rambling and hoped she heard the desperation in my voice.

After a long pause, Rachel softly asked the million-dollar question, "So, do you want to be a woman?" averting her eyes from mine and not wanting to hear the answer.

"No, I don't think so." I answered weakly. "I never really thought about it." I wasn't sure I believed the answer and was not convinced that Rachel did either.

We talked for hours. Rachel asked question after question and I did my best to explain. I had moved next to her on the bed and we were holding hands when we realized that it was two in the morning. Rachel had to give the keynote address at the conference opening session in eight hours and, like it or not, we had to get some sleep.

"Well, for what it's worth, you didn't really look all that bad. Some makeup might help, and oh, my god, that atrocious wig." She offered a weak smile. "Just one more question, Carson, why didn't you tell me before we got married?"

"Well, I guess I could have said something like, Rachel will you marry me? and by the way, I want to wear the dress at our wedding." She laughed. I squeezed her hands and continued, "I didn't understand it myself. I still don't. I just didn't know what to tell you. I had hidden it from people my whole life, I mean, my dad doesn't even know, and I'm pretty sure my mom and Sarah have forgotten or written it off as a passing faze that is long gone. I guess I figured it would be easier to hide it than to take a chance on losing you." I could feel the tears welling in my eyes.

"This is not over, Carson. I do love you and we will figure this out, but you must be completely honest with me. Promise?"

I nodded yes, "I love you, too, Rach." and pulled her close.

"I know. Now let's get some sleep. Tomorrow is a big day for us. If I do well on the keynote, it could be really big for our company." She kissed me sweetly on the forehead and I knew she had not forgiven me. I just hoped that she could.

I awoke the next morning alone in the room. There as a note on her pillow, 'Dinner at 6??? See you then. Love Rach, XOXO.'

I knew where Rachel was, the same place she always went when she needed to think and to compose herself to face something big. Being asked to present the keynote at this conference was a huge opportunity. The 'surprise' she had walked in on last night had to be a distraction, a huge distraction. She was in the pool, swimming laps. On a normal day, I would have joined her. Today, I took the implied message of her note and resigned myself to a day of worrying about what was going to happen at dinner.

Dr. Rachel Baxter-Dearing is my best friend and I do love her. By far the most brilliant and the most beautiful person I know, we met in college. I had graduated in the top five percent of my high school class and that meant I could get into The University of Texas. I had also turned out to be a bit of a programming prodigy, and that meant I got to take some graduate Computer Science classes as part of my undergraduate degree program.

Rachel was a teaching assistant for Dr. Mitchell, my graduate level, 'Computer Security and Forensics' professor. I knew who she was but considered her so far out of my league, I didn't really pay her any attention. Besides, what would someone like her see in a gangly geek like me. I had been on the swim team in high school. Not good enough to move the next level, but I enjoyed it. Swimming helped me focus and destress, especially when I needed to deal with a particularly difficult problem.

It was the morning of the mid-term exam for Dr. Mitchell's Forensics class. I was ready but there was just too much information. I needed to let it all settle so I headed for the pool. I was about fifteen laps into my swim when I heard someone else entering the pool. It wasn't unusual and I kept my pace, focusing on my stroke and counting out the laps, down and back, on my way to the 66 I needed to complete my mile.

Twenty minutes later, I rested on my elbows at the end of the pool feeling that good tired that comes after a workout, the kind that seems to energize you. I pulled myself out of the pool just in time to see and almost imperceptible flip turn to my right. I watched mesmerized as her form moved through the water like it had been born there, the water moving past her sleek curves as if bowing to allow royalty to pass. For several long minutes, I just stared as her long arms pulled her from one end of the pool to the other and her powerful legs beat the water into submission.

I recognized her immediately when she pulled up on the side of the pool. She pulled her goggles off, "Hey, I know you. You're the guy in Forensics that asks all the questions, right?" Her smile was mesmerizing.

It was a simple question but for some reason my mouth couldn't form the word, 'Yes.'

"Hello." She threw her goggles at me, laughing.

"Um, yeah, I mean yes. I'm sorry. Just lost in thought there for a minute." I was pretty sure I sounded like a complete idiot.

"Well, with all the questions you ask, we probably should have met by now. I'm Rachel, Rachel Baxter." She pulled herself out of the pool. Her skin-tight suit revealed a perfect body, long and athletic with modest breasts and prominent nipples announcing themselves to the cool air around the pool.

"Carson, Carson Dearing." I offered my hand.

Rachel smiled as she shook my hand. "You know, Dr. Mitchell likes the questions you ask. You should stop by his office sometime. He is really a great guy and I know he'd love to go deeper on some of them than he can in class." She stood up and started to walk toward the dressing rooms.

"Thanks, I will." I got up and walked behind her trying not to stare at the perfection in front of me and failing miserably.

"By the way." She stopped suddenly and turned around. I almost ran into her. "My research partner and I could use a coder to help with our project. Stop by our office after the test this afternoon and I'll introduce you to Wilson. Maybe you can help us out. Can't promise and it certainly doesn't pay much, but it should buy you a couple of beers every now and then."

"Yeah, I'd like that." I smiled timidly.

"Great, and I hope you're ready. This test is a real bitch." She turned left into the women's locker room.

"Thanks for the warning." I had to physically fight the urge to follow her, turning right instead. I had met a goddess and lived.

I breezed through my Advanced Data Structures mid-term and grabbed a quick lunch before heading into Dr. Mitchell's classroom. Rachel was already there handing out exams. Seeing her helped me relax a bit. "Good luck," she smiled and winked at me as she handed me the papers.

"Thanks. I heard this one was a real bitch." We both laughed, "I'll see you in your office after. I think I'd be interested in what you mentioned."

The test was just what she had promised and took everything I had to complete. I was exhausted when I handed Rachel my paper. I knew I had done everything I could and was somewhat gratified, and a little worried, to see the room still half full of people frantically writing.

"Looks like I'm going to be a bit longer," Rachel motioned to the students still working on the exam. "Most of them will drop this week." She said with a sad smile, "Go on and introduce yourself to Wilson. He knows you're coming."

"Thanks for the chance Rach..., um Miss Baxter."

"'Rach', I can go with that, and you're going to have to earn that chance. See you in a bit." The way she raised my test paper before she dropped it on the pile suggested it may have been an audition of sorts.

Wilson Dalton looked more like he belonged on a beach with a surf board than he did in a computer lab. He was a few inches taller than me at 6'2" with long blonde hair. He sported ratty jeans, flip flops and a Tommy Bahama shirt with a huge parrot on it. "Hey, there. You must be Carson. Rachel told me about you. Come on in and sit down. Can I get you a beer?" His Texas drawl was the perfect contradiction to his appearance.

"Um, yeah. A beer would be nice. Thanks." I took the Lone Star from him and twisted the cap, making sure to check inside for the puzzle. The beer was just what the doctor ordered after the brain-dump I had just been through. We talked for a while about what classes I was taking and what I liked and didn't about each one, not going too deep into anything, more like he was trying to figure out what I was doing here. "So just what did Rachel tell you about me", I finally asked?

Wilson looked at me, trying half-heartedly to look menacing, "Well, she said you asked really great questions and your code was fantastic." He paused a minute looking past me toward the door, "She also said she thought you were kinda hot, if you know what I mean."

"Wilson, you shit. Stop picking on him." Rachel's voice drifted over my shoulder and I almost dropped my beer. "You got one more of those, I think we're going to need them to grade these. She plopped a stack of papers on the desk in front of Wilson.

I could feel the electricity between the two of them. It wasn't sexual at all. They were just tight, a team, and had built a connection over the past two years of working together on a joint thesis on the practicality and limitations of using Artificial Intelligence to deal with global concerns in Computer Security.

We sat down and Wilson and Rachel started explaining what they needed somebody, possibly me, to do. They needed to build a POC, or proof of concept, for an application that proved their theory on the effectiveness of AI to the computer and internet security world. I caught a lot of the concepts and the bottom line was they could do the high-level design and complex logic. They just didn't have the bandwidth to fill in the supporting functions and methods.

The phone rang and Rachel answered it immediately. "Yeah, Mike, I think about what you expected. Probably half, maybe a little less." We're talking to him right now. Sure, I'll let you know."

Wilson had fished through the pile of exams pulling out one I immediately recognized as mine, and while Rachel talked to who I assumed was Dr. Mitchell, began skipping around from question to question, mumbling to himself, making notes on the test and occasionally smiling and then frowning. When Rachel hung up, he wrote something on a post-it note, and handed it to Rachel, who repeated the process with much the same results.

"So, you want to know how you did?" Rachel handed me the test.

I opened the test to see a cluttered mess of circles and underlines and exclamation points. Words and phrases like 'more here' and 'good stuff' and an occasional 'NOPE!!' or 'Ouch' punctuated their brutal review. "So, what does all this mean?" I looked back and forth from Rachel to Wilson.

"Well," Wilson started, "assuming my esteemed colleague agrees with me, it means we want you to work with us."

Rachel nodded, handing me the yellow post-it. The average of the two numbers on the paper was a 91. I had an 'A' on the test and a new part time job.

The next eighteen months were crazy. I was carrying a full load and working effectively full-time helping Rachel and Wilson with their project. It was stressful and fast-paced and amazing. I was loving every minute of it. We rented a three-bedroom house together and were almost inseparable. Rachell and I swam together every morning and I could feel something different beginning to grow in the way I felt about her.

I would occasionally disappear for the weekend, telling them I was just overwhelmed and needed a break. They didn't ask for more explanation than that and I wasn't sure I could offer one anyway. I wasn't sure how they would handle me telling them I just needed to go play dress-up.

Rachel helped me keep up with my last few classes as we worked long hours balancing that and completing the project. When we got stuck, it was her who would get us back on track, "OK, let's go back a few steps. Let's start with what we can explain and go from there." She would say. It worked every time.

I aced my finals and graduated with honors. The presentation of our application had been met with incredible enthusiasm. Rachel and Wilson became Dr. Baxter and Dr. Dalton. Dr. Mitchell had introduced us to a friend from the law school who specialized in corporate law, and Baxter Dalton Security had been born. Due to the MBA Rachel had managed to squeeze in on the side somewhere, she was the CEO and Wilson was the President and CTO. I was the Director of Product Development. Not bad for a first job right out of college. The resulting celebration had been epic by any standards.

Rachel and I had tied for the honors of 'Last man Standing' and sat on the floor of our living room, leaning against the couch, watching Wilson sleep on the floor and joking about how he wasn't going to be able to move if we didn't roll him over.

"Thank you for letting me be a part of all this, Rach." I placed my hand on hers.

"I'm glad you decided to join us." She turned her hand over and slid her fingers into mine.

Our eyes met and we kissed, softly at first and then more and more passionately. Without a word, Rachel got up and led me to her room. I knew what she was offering and knew that I wanted it more than anything I had ever wanted in my life.

Rachel undid my belt and pulled my pants down as I unbuttoned her blouse and unhooked her bra. Realizing the inefficiency of our plan, we switched targets and I pulled my shirt off as she removed her jeans. We climbed onto the bed, removing my boxers and her panties at the same time.

Rachel pushed me onto my back and climbed on top of me, kissing me hard as I pulled her body close to mine. My hands eagerly explored as much of her as I could find, her back and sides and her perfect ass as we writhed in the excitement of the moment, our lips locked together, our tongues dancing an intricate dance of passion in our mouths.

Rachel broke free from my embrace rising into a sitting position atop me, gently settling her crotch onto the base of my cock so that it looked as if it might be hers. She rocked back and forth slowly as I reveled in the wonderous beauty of her body. She smiled at me, running her hands across my chest. My hands found her breasts and began to massage their perfect symmetry, catching her erect nipples between my fingers, pinching them gently as she began to rub against my throbbing erection harder and harder. Letting out a soft moan, Rachel lifted herself and, using her hand, guided my cock to her pussy, slowly taking me inside her until there was no more to take.

"Oh, my god, Rachel." I moaned.

"Fuck me, Carson, she whispered. "I want you to fuck me, hard."

I pulled her close as we rolled over. Climbing on top of her, I pushed my prick back into her wetness and began thrusting, harder and faster, harder and faster. "Ooh, that's it. Yes Carson, fuck me, fuck me hard. Make me cum." Her breathing got faster and faster. Matching my rhythm, Rachel began to roll her pelvis into mine, grinding her clit into the base of my cock.

"Oh, yeah baby, I'm going to fuck you until you scream." I whispered into her ear, biting her lobe and licking her neck with my tongue.

"Yes, yes, god, yes, fuck me, Carson..." her body arched and froze and then began to tremble as she exploded in a wave of orgasmic energy. "Oh, Carson, that was amazing." It was more of a whimper than a scream, but the look on her face told me I had accomplished what I wanted.

"Rach, we're not done yet," I grinned at her as I continued thrusting into her.

"You mean you haven't..." her expression was half disbelief and half ecstasy. I shook my head and smiled as I pulled my cock from her dripping pussy, turned over and took her from behind.

My hands on her hips, I thrust my prick deep into her throbbing wetness, riding the aftershocks of her first orgasm until we exploded together. This time, I got the scream.

We collapsed in a sweat-covered, exhausted, heap, kissed passionately for a few minutes and then softly and tenderly before we crawled under the covers and fell asleep in each other's arms.