Reacquainting Oneself Ch. 07

Robert was the driver, so we let off Carol and Stu at their places first. The hug I received from Carol at her place set me at ease. She was her usual bundle of energy, promising to call me, and to arrange a girls' night out.

I was so caught up with emotion, that I forgot about my bag sitting by the entrance of her salon.

Then, as promised, we did grab a few items from my place. Even if I was currently dressed as a woman, it felt strange to reveal my secret drawer.

I could see the tent in Robert's pants when I pulled out the infamous dress from high school. How many times had he fantasized about me in this dress? It was further assurance that moving in with him was the right decision.

The work related items were not questioned. Robert helped bring my laptop, files, and various computer accessories to the car. He assured me that he had a space which could become my office area.

There was however more debate when I grabbed some of my 'work clothes'. I argued that I had video calls, and had to go into the office about once per week, and I couldn't be in women's clothes at work. He begrudgingly allowed me 2 dress shirts, 1 pair of dress pants, a suit, and a tie. He drew the line with underwear, insisting that no one would see them. Furthermore, he promised to buy me some blouses, slacks, and a proper women's suit.

It was all slightly overwhelming, but he had been right thus far. I had to trust him.

What I was not prepared for was Robert's home. I knew he was more successful than me, but I didn't realize he could already afford a house in the city. It was worlds away from my dingy 1-bedroom apartment.

However, it did feel somewhat empty. It was clear that he had only moved in recently. It needed a woman's touch, which I guess is where I now fit in.

That evening there was little for us to do. With the drive back, and bringing my items over, it had been a long day. Therefore, we quickly settled into the bedroom.

Somehow, this seemed more profound. Yes, we had slept together the past two nights. However, this was his home, his bed.

I stood nervously by the bedroom doorway for a moment.

He recognized my apprehension, and tried to calm my nerves. "We don't have to do anything tonight. I'm kind of tired as well, and have an early morning. So, we can just sleep."

Fatigue wasn't really my concern, but it did help to know there was no expectations.

He was undressing completely. And before I called him out for contradicting his last statement, he noted, "I always sleep in the nude."

I wasn't certain if I could just sleep with him next to me naked. Yet, then I looked at him, and that gorgeous body of his. How could I possibly refuse sleeping with him?

"I'm sure there's a nightie in the bag from Carol. We can pick up some more items this week for you to wear."

Oh yeah, I can't just wear my usual briefs. I nodded, not knowing what to say. At least I wouldn't be naked. I opened up the bag of clothes, that I now knew was always meant for me, and did indeed find a cute nightie.

I slipped it on, and was once again aroused by the silk brushing against my skin. This was going to take some getting used to. Equally exciting was the lustful gaze of approval I received from Robert.

Following his lead, I crawled under the covers. Then, with an instinct I didn't realize I had, I curled up to him as the little spoon. My ass gently pressed against his cock, which sent shivers down my body as the silk rubbed between us. It had a similar effect on Robert, as his cock hardened.

Apparently, he was content with this simple intimacy. He draped his arm around me, holding me close, and kissed my cheek.

"Goodnight sweetie."

I returned the cute endearment. "Good night dear."

To my surprise, we actually did sleep. I resisted the urge to rub my butt against him, and just relaxed in his embrace.

I was completely refreshed the next morning. Initially, it was somewhat disorienting to be in an unfamiliar room, wearing a silk nightie, and feeling a muscular body pressed against me. Yet, I soon realized this was now my place.

This was the start of a new adventure. I had never been in a relationship. I had never shared a bed with anyone. This was going to be a whole new life experience.

For the moment, I wanted to start a new tradition. Roberts cock, even soft, rubbed against my silk-covered ass. It would only be appropriate for me to show my appreciation.

I slipped down the bed, under the covers, being careful not to wake him. I couldn't really see, but I was drawn to his cock like a magnet. It was soft at first, but some gentle sucking soon fixed that.

As I did the previous morning, I started slowly bobbing my head, up and down, my lips wrapped around his hardening manhood.

When I felt his hand on the back of my head, I instantly intensified my sucking. I suppose the lack of play last night had heightened his arousal, because it wasn't long before I was swallowing his salty cum.

I licked my lips, and smiled at him.

He had a satisfied grin. "That was fantastic sweetie. I hope this can be our morning routine."

I scooted forward and kissed him. "You bet."

* * *

A number of domestic routines were established that day, and in the days that followed. I had always cooked for myself, and readily assumed that duty. And since I was home during the day with a flexible schedule, it was natural for me to clean-up, and do the laundry.

The area set aside for my office was a welcome relief from my cramped apartment. And since Robert had never used this room, I was able to organize it to my liking.

Typically I would start the morning off by making breakfast for us. That is, after the customary blowjob. Then, after Robert left for work, and we kissed at the doorway, I would check my messages, and address any work tasks. This usually only kept me occupied for a few hours. After which, I would generally have a light lunch.

Fortunately, I have always been a healthy eater, which now helped with my figure.

In the afternoons, I was generally free to mix my time between work and domestic chores. Unless there was some pressing work assignment, I could even do some decorating, and experiment with my new wardrobe.

Before preparing dinner, I was increasingly finding sexy or cute outfits to wear. I was taking pride and attention to my style of dress in a way I never did with men's clothing.

True to his word, Robert did buy me some new clothes. Well, to be more precise, he gave me money for clothes.

This was nerve racking at first. Fortunately, on my first shopping excursion, Carol joined me. She delighted in dragging me from shop to shop, trying out outfits. The initial dread I felt, worrying about being ridiculed as the sissy, dissipated as this never happened. Either my fellow shoppers and clerks didn't realize I was a man, or they didn't care. Either way, I relaxed, and started to enjoy the experience.

I was beginning to understand why women enjoyed clothes shopping. It was no longer a chore. It was an adventure, discovering the wide assortment of colours, styles, and fabrics. It was fun.

Over time, I even found my own style. It could best be described as the 'fifties housewife' look. Carol didn't understand why I chose this style. It was quite different from her brash outfits, but she had to admit that it worked for me.

I remember her asking, "Won't he expect you to be the good, obedient housewife, always eager to serve him."

I winked. "I am."

She laughed. "In that case, it's perfect."

These excursions highlighted the change in my life. For years, my days and nights blended together in a monotonous routine, with no one to care. Now, I looked forward to the evenings.

In anticipation of his arrival, there was a flurry of activity. I checked my outfit to ensure I was wearing something sexy. I refused to wear pants, or even women's slacks, after 5pm. My hair and makeup also had to be done properly.

Typically, I had to complete some preparation in the kitchen, and I would do any cleaning touch-ups that were necessary. The home and I were made ready for his arrival.

I greeted Robert at the door, like a puppy eager to welcome her master. "Hello dear."

He kissed me. "Hi sweetie."

I could tell what kind of day he had with the kiss. A perfunctory kiss meant it was a tiring or tedious day. A passionate kiss indicated a good day, and he was looking forward to seeing me.

With his jacket and shoes removed, he led me to the living room, where he would sit in his sofa chair.

I dropped to my knees without prompting, and unzipped his fly. Whatever the day he had, I was going to make him feel good now. I gently pulled out my object of worship, and wrapped my lips around it.

The night was young, so I always sucked him off until there was a healthy load of cum down my throat.

So, with his balls drained, along with any stress from the day, he would go change into something more casual. And by the time he was back downstairs, dinner was ready on the table.

It's said that one should enjoy life's simple pleasures. I certainly did. Curling up to him on the sofa, and making love to him each evening.

My ass had now been stretched enough to accommodate his cock with only a quick dab of lube. I had even begun to squirt, experiencing my own sissy-gasm, when his thick cock stimulated my prostate.

This embarrassed me at first. Yet, I received some assurance from Robert. "Don't worry sweetie, I think it's cute. I don't want you touching yourself, and I'm certainly not touching that little thing. So, this is how you cum now."

Initially, I was put off by his dismissal of 'my little thing'. Yet, he was right. And truth be told, jerking off had only ever fed my self-loathing. I don't believe I had ever experienced a true orgasm until now.

If possible, I became even more eager to have his massive cock deep inside me.

To be honest, everything at home felt good. I was in love for the first time. I was in a beautiful home. I had friends, such as Carol, that I had never had before. And most of all, I had the freedom and support to explore this new me.

The only thing that weighed on my mind was the outside world. I worried about what could happen if my boss found out. Although, frankly, I don't know why I was so concerned. It was a shit job, and Robert could easily support me, if only I let him.

However, there was some security in holding onto some modicum of independence.

Likewise, my trips outside terrified me. Shopping, or just hanging out with Carol, while dressed as a woman remained nerve racking. And even more daunting were evenings out with Robert. I took pride in not only being feminine, but a sexy girlfriend that he deserved.

I had trouble believing those who said I was beautiful. After years of being the lonely outcast that no one looked at twice for so many years, it was hard to believe I warranted this attention.

For my work day, I continued to wear shirts and pants. My wardrobe was limited by the few items Robert had allowed me to keep from my apartment, and I dared not defy him by buying more men's clothing. So, with time, I began to experiment. An assortment of women's dress shirts and slacks became my preferred daytime outfits.

By themselves, I thought I was able to pull it off without anyone noticing, particularly through video calls. Yet, I had started wearing a padded bra, my nails were painted, my hair style was distinctly feminine even pulled back, and I occasionally forgot I was wearing earrings.

My direct manager, Amanda, never said anything. If anything, she seemed a bit nicer, but I figured that was just me being less anxious about my job.

I figured the jig was up one morning, in my third week living with Robert. I had been pulled into an early morning video call with Amanda to troubleshoot the new program we had just deployed. And as luck would have it, Robert was running late that morning.

I was at the computer, camera on, when Robert popped into my office area, shirtless. Normally, something I appreciated.

"Diane, do you know where my blue shirt is? And the silver tie?"

I was flustered for a moment. "Oh, uh, yeah." My gaze shifting between Amanda on the screen, and Robert with his muscular upper body on full display. Did she hear him call me Diane?

"Two secs." I hastily muted the audio, and I think the video.

Turning to Robert, still flustered.

"Sorry honey. I didn't realize you were on a call." He hastily apologized, still pressed for time.

"'I did the laundry yesterday. So, it should be hanging up in the closet. If not, it's in the laundry room."

He nodded, somewhat surprised that clean clothes would magically appear in his closet. And just like that, he was off.

No morning kiss for me this day, but that was due to me.

I returned my attention to the computer. Now a little disoriented. What did my boss see or hear? What were we discussing?

Amanda was grinning. "That was hot."

"Oh yeah, that's my roommate, Robert." My extremely hot roommate.

"Uh huh." She clearly didn't believe me. Yet, she had no interest in putting me on the defensive.

We got back to work, and I forgot about the incident. Although, I couldn't resist teasing Robert later.

"My boss thought you were hot, not wearing a shirt this morning."

He laughed, puffing out his chest with mock bravado. "What's not to like?" He brushed my cheek, faking concern. "Is Diane getting jealous?"

I shook my head. "No!"

Even I knew that I had over reacted to his teasing. The lady doth protest too much methinks.

Fortunately, he let it go.

Over a week later, I was in the office. I had managed to minimize my trips to the office, but it was only a routine work day. Only now, I begrudgingly donned my old dress shirt and pants. I also had to take care to remove my nail polish, brush my hair back, and ensure I wasn't wearing any jewelry.

I thought I had escaped without any notice. A reasonable assumption. After all, I had been largely ignored for years.

Yet, just as I was about to head home, Amanda called me into a meeting room. That, in itself, was not all that unusual. However, I was somewhat alarmed to see the lady from HR, Susan, Samantha, Stacy... it was something with an S.

Whatever her name was, she was present when people were fired.

Amanda was smiling, so that was reassuring. "Have a seat Dan. I just wanted to touch base, and review a corporate policy with you. Sylvia can confirm any details, and answer any questions you may have."

In my experience, a 'review' of corporate policy only happens when something was violated. Never a good sign.

"Uh sure." I feigned nonchalance, and took a seat.

"I know you went through all this during orientation, and we have periodic updates. But I know it's been a few years for you. We wanted to remind you that we are an equal opportunity employer. And given some recent changes I have observed, we wanted to reach out to you."

"Changes?"

"Yes Dan." She could see that I was nervous. "It's not a bad thing. We just want to assure you that you will be supported. Our company supports the LGBT community, as do I personally."

It took me a moment to register what she was saying.

"We will be there for you. If you are transitioning, or simply coming out, we have support systems in place for you."

Wow! This was a lot to take in. "Transition? What do you mean?"

Amanda paused for a moment, looked to Sylvia, and then back to me. "Forgive me, I don't want to make any false assumptions. However, the man you are living with is clearly more than a roommate."

I blushed, debating whether to dispute her assumption.

"And the rest is minor things I've recognized. If you had one of the guys as a manager, they may not have noticed. Yet, I've noticed a touch of blush on your cheeks. And your hair style, particularly with its length, is certainly not masculine."

She was thinking of other examples. "And then there's your nails, long and trimmed. And sometimes, although you try to hide them, I can see they're painted."

There was clearly other things she was struggling to remember, but she had made her point.

Sylvia appeared concerned, perhaps worried that Amanda had invaded my privacy. Yet, she said nothing.

My clever ruse was not so clever. I still considered disputing her claim. I was at a loss for words.

She sensed my trepidation. "As I said, this is not a bad thing. We want you to feel welcome here in the office. We respect your right to self-identify, and assure you that you will be protected from discrimination."

'Would you like me to dress more feminine?" There didn't seem to be any point in contradicting her statement.

She paused, looking to Sylvia. She appeared conflicted between her personal thoughts, and that of her managerial role. "It is not our place to tell you how you should dress. We only want you to know that you can dress as a woman." She hastened to add, "If you want to."

Recognizing I was putting her in an awkward position, I asked the question again. I really wanted to know what women thought of me. "Yes, but would YOU like me to dress more feminine?"

She once again looked at Sylvia. Sylvia nodded, knowing the unspoken question.

"Well, with the caveat that what you think is most important, and speaking as a friend, not your manager..."

She wasn't really a friend. A good boss, but never anything more. Yet, I needed her to be personal.

"... I do think femininity suits you."

Holy crap! Did every woman think I looked better feminized?

I looked at Sylvia. "And you?" Don't know why I asked, since I didn't really know her. However, she was another woman.

She appeared awkward. She shuffled through her papers, and handed me one, 'Dress Code'. "Dresses and skirts are permitted, but must not be too short. And since this is an office position, there are no limits regarding jewelry or hair length. "

She was hiding behind bureaucratic-speech.

"... I do think you would look nice with your hair out, and with some colour."

In other words, feminine. It was increasingly evident why I never had any success with the ladies. They considered me one of them.

I looked to Amanda. "And all this because you saw my roommate shirtless for about a minute?"

My statement could have been argumentative, but was more curiosity. My lack of contradiction implied agreement. I hadn't forgotten her reaction to seeing Robert.

She had to think about this. "I guess I always regarded you as somewhat effeminate. And as I said, I sensed certain changes, but I couldn't quite place what they were. Then I saw you with him, a real man, and it all came together."

She turned to Sylvia. "Seriously, you should see this guy. Gorgeous. I'm even a little jealous."

It was hard to argue with that.

She returned to me, and the question at hand. "Suffice to say, it's clear who is the man, and who's the woman in your relationship. Or to use the phrasing of gay relationships, who is the top, and who is the bottom."

I was a little stunned that she actually said it. Even Sylvia seemed concerned that she had over-stepped the boundaries of appropriate office communication.

I debated challenging the assumption that Robert and I were a couple. If it was a competition of masculinity, there was no contest. Yet, why should I be ashamed of my relationship with a man that women regarded as a hunk?

"The bottom?" I was almost teasing with my tone. For some reason, it surprised me that she knew the lingo.

"Why wouldn't you be? Truly, I'm happy for you. It must feel amazing.. " She looked to Sylvia, and stopped what she was going to say. She wanted the full gossip details, but her manager status prevented her.

'It does indeed,' I thought. My body still had the sensual ache from last night, and I was constantly yearning for more.