The Last Time We Met

"Let me get this straight. Are you asking my permission to take Regina out on a date?"

"After all, you are sort of her big brother, aren't you? I have a feeling if you give your blessing, things will work out fine."

"What the hell... you two crazy kids go out and have a good time, but not too good a time. Get her home by midnight and remember: if you break her heart, you'll answer to me."

"Thank you, Roger. And don't worry: I won't break her heart. It's too precious to me."

I suddenly remembered an errand I had to run and left Don sitting there; or was it Donald I left sitting there? I no longer knew. I walked to my car as quickly as I could before the inevitable tears came. Were they tears of joy or sorrow? I honestly didn't know, but I knew my fate was now irrevocably tied to his.

When I got home, an email was waiting for Regina. After changing into panties and stockings, as was my custom when Regina had mail, I opened it.

My dearest Regina,

As you know, I spoke with Roger this morning. He (and you) now know how I feel about you. Next week is Valentine's Day. I would be honored for you to go out with me for a special celebration. It's a surprise, but I'm sure you'll love it.

I hope you can take the day off. Go to the hotel at noon. I'll text you the room number. When you're dressed, I'll join you and we'll slip down the stairs to my car for a trip to Mei's. When she's finished with you, I'll have to beat off the men. Then our special evening will begin.

To be honest, I don't know how it will end, but, as long as you are in my arms, nothing else matters.

Yours from the beginning,

Donald

My toes curled at the thought of a date and what would follow. My clit was fully excited and I rubbed it with one hand while I played with my nipples. A special celebration. What could that be? Dare I hope? Would Donald at last take my virginity? My pussy twitched at the thought.

Roger had refused to engage in anal sex throughout his explorations. As much as he was curious about how it would feel, he knew that only gay men penetrated each other anally. He had no problem with a cock in his mouth, as that made him submissive, not gay.

But I wasn't Roger; I was Regina. I was Donald's woman. And, as his woman, my body was his to use as he pleased. If he wanted to claim my pussy, it was his. More than that, I wanted him to be the one to take my virginity. What could be more special?

I was pinching my nipples, imagining him nibbling on them as he leaned over me making sweet love. I could feel his teeth on my nipples and his tongue on my breasts...

My breasts. I felt them again and called Mei, who was able to see me on the 13th. I wanted to look perfect for Donald, and she would know just what to do.

I replied to him:

Donald, dearest,

I've been awaiting this moment with mixed feelings. Being seen in public terrifies me. Being seen in public on your arm exhilarates me. I've trusted you with my body. Next week, I'll trust you with my heart.

Your Regina

I hit the Send button and wept for Roger. Whatever happened, his time with Don was drawing to an end. Once Regina and Donald consummated their relationship, I could never appear as Roger to him: I would be forced to admit that he and I were having sex and could no longer plausibly deny my attraction to men as men. As irrational as that sounded, it would be a step too far.

And if Donald and Regina were truly happy together, I was prepared to renounce Roger. It would make for some awkward moments with my coworkers, perhaps, but HR had a track record of making accommodations for gender issues. Some of my team members were already working from home full time.

The next few days went surprisingly normally. I was at peace with myself for the first time in years. Whatever happened, I knew I would survive. Regina wasn't a freak: she was a woman who was desired by a man. If this relationship didn't last, she would be hurt, but not devastated. If she was desirable to one man, there would be others who also found her lust-worthy. She had finally stepped out of the shadows.

As for me, I understood that I wasn't a freak, either. Don was the first true friend I had made. Not only that, he accepted who I was in all my complexity and relished it. I knew there were others out there who would also accept me.

And my family? We may have some difficult conversations, but I knew I could handle them. I finally accepted and respected who I was. I was no longer ashamed of Regina. More importantly, I was no longer ashamed of Roger.

February 13-14: Preparations

The weather here is capricious. I often tell people we have four seasons, often all on the same day. After a blustery first week of February, the weather gods chose to grace us with warmer weather. The week of the 14th was going to be sunny and mild, with temperatures in the 60s. It was, I hoped, an auspicious sign.

Monday, I worked a half day and let the team know I would be out the next day to take care of some personal business. Driving to Mei's, the butterflies started to reemerge. I was about to take a big step. What if I had misread the situation? Was I going to push Donald too hard?

No. This was what I had to do. I knew Donald would love it. But, even if he didn't, Regina would: it was always in the back of her mind. And, having finally brought her out of the closet, I wasn't going to push her back in. I had come too far emotionally. No more roller coaster.

Tuesday, I slept in, as the room wouldn't be available until noon and I was hoping not to be sleeping again until early Wednesday morning. After showering and scrubbing down with Regina's favorite body soap, I shaved, dressed in khakis and a brown polo shirt, had a light breakfast and got ready to leave for the hotel.

The butterflies were back in full force, but I expected that. I took one last giddy look in the mirror.

"Happy Valentine's Day! Looking good, Roger...and wait until Donald gets a look at Regina. We are going to blow his mind!"

While I was still five minutes out, my phone dinged. '415' It appeared Donald was as anxious as I was.

I stepped into the room. A bud vase with a single red rose was on the dresser, with a card propped on it. Next to it was my wig and a white lace bra. Next to them was a pair of white sandals with a 1" heel, with a pair of black leggings draped over them. Hanging in the closet space was a white sweater dress, with full length sleeves and a loose turtleneck top. On the closet knob was a small white handbag with a thin shoulder strap.

The card was addressed to Regina. I quickly stripped out of Roger's clothes and put them in a dresser drawer, out of sight. The first step was to reduce my engorged clit. I thought briefly about masturbating (it wouldn't have taken long, given how wet it already was), but this was Valentine's Day and I was saving that part of me for Donald. I took care of it the old fashioned way, with a cup of cold water.

Once it was under control, I pulled on the leggings. They were smooth and dark enough to show off my legs without showing any details. They had a high control top, which made my tuck that much easier. Donald was so thoughtful about the smallest detail: I smiled, thinking about him.

Next came the bra. It fit me well, just tight enough to hold in my flesh and almost fill the cups. The bra was lacy and felt good against my nipples. I took a couple of steps and confirmed the fabric rubbed against them in just the right way. Once again, my tuck was going to be challenged. I smiled: Donald was going to be surprised when he saw just how well it fit.

I almost put on the dress, but decided to complete the Regina look first. On went the wig and I shook it out. I had worn it enough that I felt undressed, not to mention unladylike, without it. Finally, the dress. It was form fitting without being clingy and gave me a decent shape. It extended to an inch above my knees. I sat down, slipped on the sandals and walked to the full length mirror.

I couldn't believe the woman who looked back at me. Regina was ready for an evening out on the town. She was casually dressy and fashionable. Did she always have that big smile on her face? I hadn't known Donald had such good taste in clothing. And how did he get the fit just right? He was a man of many talents, to be sure.

I opened the card and read it:

Regina,

I hope the clothes are satisfactory and that you enjoy wearing them as much as I'm going to enjoy seeing you wear them. I'll pick you up at 1:30.

Donald

I looked at my watch: 1:17. The purse had a small packet of tissue in it. I added my license and keys to it and set it down next to the rose. The shoes felt light and airy as I walked around the room to break them in. I wiggled my toes and made a note to ask Mei to add some polish. I spread out my arms and twirled around with my head up and eyes closed. I enjoyed being a girl!

A knock on the door.

"Who is it?" I asked in my husky alto.

"Your date."

I opened the door and gaped at the Adonis who stood before me. Donald was wearing a blue sport jacket, dress shirt with open collar and dark blue trousers, with black dress shoes. His perfectly aged face was aglow with the laugh lines from his smile.

"Are you going to ask me in?"

"Oh...I'm sorry, Sir...I was just...I mean...please come in."

He walked in and gave me a hug that melted me.

"I think we're past the 'Sir' stage, Regina. My sweethearts call me 'Donald.""

"Then I'd better not hear anyone calling you that except me."

He laughed. "You won't."

Then he stepped back and whistled.

"I think Mei did too good a job with the clothes. The men are going to be all over you."

"Mei picked out the clothes?"

Donald looked embarrassed. "I told you she was a friend of mine. She also has a much better fashion sense than I do. I asked her to help me with the styles."

"But how did she know my sizes so well?"

"Besides me giving them to her, she's quite observant and she's seen you several times."

"Wait. You mean she knows about..."

"She knows about you and Roger. And before you ask, she's suspected for some time something was going on with us. Something about a twinkle in your eye whenever she mentioned me to you?"

I blushed deeply. "And she doesn't mind that I'm..."

"She doesn't mind who you are. She's a lot more interesting than you may think. I hope you and she are going to become good friends. Speaking of which, we need to go."

He held the door open. "After you, milady."

"Thank you, milord."

We walked hand in hand to the stairwell and descended to ground level. By now, I was accustomed to taking stairs in heels, so the descent was easy.

At the ground floor, he walked me to his car and opened my door. I slid in and pulled the dress up behind me so my tush was in direct contact with his leather seat. I wriggled appreciatively and saw him stare and smile as he got in the car. He leaned over and gave me a soft kiss on the lips before starting the engine.

"Hello, beautiful."

"Hi, handsome."

"Are you excited about our date?"

I had never realized what a magic word that was until he said it. Damn! I was acting like a moonstruck teenager. What was I going to do next? Giggle? What was going on inside me? And why was I feeling so happy?

"I'm very excited about it, but I'm still a little nervous about being seen by other people dressed like this."

"You look nice, Regina, like a lady, not a trollop. No one's to notice anything except that I'm a lucky man."

He squeezed my knee and started idly running his hand over my leggings, slipping under my dress and moving slowly up my thigh. I took it out and slapped it playfully.

"Naughty boy. I'm not that kind of girl. Besides, I don't want you to get in an accident. I don't have a spare pair of panties. Actually, I'm not wearing any panties...gosh, I guess I am that kind of girl. As you were, then."

After kissing his palm, I returned his hand to my thigh, leaned back and closed my eyes, enjoying his caresses and trying to ignore the growing pressure in my leggings. I realized I had omitted an important piece of feminine attire and hoped Mei would be able to supply it.

Mei greeted us at the door. Donald made introductions, as I stood blushing.

"Mei, this is Regina. She's a very special friend of mine and I want you to give her the works. I have some errands to run. I'll be back around 5:00. Will that be enough time for you to work your magic?"

"That will be plenty of time, Mr. Donald. You won't recognize her."

When he left, she gave me a kiss on the cheek.

"Men! They know what they want, but we know what they need, don't we, Miss Regina?"

"Um, Mei, you do know you've seen me before, right? You don't have to play games."

"Games, Miss Regina? You do look a bit like another client of mine, Mr. Roger. He's a very nice gentleman, so I know you're a very nice lady. I've met a lot of people over the years, many like you. People are people, Miss Regina. I help them show who they really are. I see you are a beautiful woman who has never had a chance to be who she is. I'm going to change that. But, come on...the water is hot."

The water felt good on my feet and calmed the butterflies. I closed my eyes and enjoyed Mei's expert attention to my feet and nails. Her continued ministrations had made my feet extra soft, especially the soles. They were definitely ready for sandal season and I couldn't wait for summer to come so I could show them off.

Roger had rarely spoken to Mei when he had his pedicures. Perhaps he had nothing to talk to her about, but I did.

"Donald told me you picked out my clothes. I love them! Thank you."

"They bring out your femininity. I trust Mr. Donald likes them."

Remembering the iron rod in his pants when he hugged me, I smiled. "Oh, I'm pretty sure he likes them." Wei laughed knowingly and I joined in.

"I have just the shade of nail polish for you. Your fingers and toes are going to be as pretty as the rest of you."

"I've always wanted to have painted nails, but..."

"...but you were afraid what people would say about you."

"Yes. Mei, you said you've helped men like me before."

"No, Miss Regina, I said I've helped people like you before. Some men just like to look like women for sexual gratification. Some men really want to be women. What about you? Do you want to become Miss Regina, or do you want to stay Mr. Roger?"

"At this point, Mei, I really don't know. I love being Regina. I feel so alive, so...right."

"And your coworkers like Regina too?"

"Oh, no. I would never be Regina around them. I couldn't let them see me like this."

"But you feel so alive? So right?"

"It's hard to explain. They would just laugh at me. And my family would probably stop talking to me. I don't know if Donald told you, but this is the first time I'm going out in public as Regina. That's why he asked you to give me a makeover. I don't know what I'd do if people started pointing at me and laughing."

"He cares about you, Miss Regina."

"Yes, I know he does, and I care about him. He's kind and caring and bright. He makes me feel special inside. And we have such fun discussions about movies..."

My voice trailed off. I never had discussions with him about movies. That was Roger... No; I wasn't going to go there today, of all days.

"Miss Regina?"

"Sorry, Mei, I must have zoned out. I guess I'm nervous about tonight. I've never been in public with him before and I don't want to embarrass him."

"You won't, Miss Regina. Why do you think I picked a dress with a turtleneck top? You were worried about that, weren't you?"

She was a mind reader. One of the dead giveaways of a crossdresser is the Adam's apple. The biggest fear I had of appearing in public was knowing that I would have to swallow, and that would show everyone I was a man in drag. My dress had a loose top that hid my throat from all but the most curious. Donald was right: she was well worth knowing.

"You're right, of course. Thank you, Mei. You don't know how much that means to me." Was the room suddenly getting dusty?

"It's my pleasure, Miss Regina. I love spending other men's money on clothes." We both laughed, two women lightly mocking the foibles of men.

"But wait one moment, Miss Regina. I forgot something."

She returned with a bowl of melted wax and a wooden spatula. She pulled up my leggings.

"You have hair showing on your legs and feet. That won't do. I'm going to take it off just above where the leggings end. You can still wear shorts around your friends and family. No one will notice."

"Thank you, Wei. I hadn't thought of that. It's a good idea. How long does it...ouch!"

"Not long, Miss Regina. It does sting for a little bit, but you'll like the results."

She was right. After finishing her work, she rubbed a soothing lotion into my legs and feet, then wedged a foam separator between my toes. She had chosen a dark red polish that made my toes pop out. If I was with a woman with feet like mine, I would be sucking those toes in an instant. I wondered if Donald would do that and blushed at the thought. My clit's response to the image reminded me what I needed.

"Uh, Mei, before you start on my face, could I ask a favor?"

"Of course, Miss Regina. What do you need?"

"Well, I sort of forgot my panty liner. Do you, maybe, have one I can borrow?"

"Of course, Miss Regina. But you don't have to return it."

"No, I didn't mean that. Of course, I wouldn't return it, I just meant..."

"Stop, Miss Regina," Mei was laughing, "You're so sweet and so innocent. We girls take care of each other."

Sweet and innocent, indeed. She had obviously not seen me curling Donald's toes. And just wait until tonight. He was going to be cramping up when I got through with him. It would take him a week to replenish his precious bodily fluids...

She went to a room in the back and returned with a panty liner. I thanked her and retreated to the bathroom. Pulling down my leggings, I saw they were in danger of being soaked. I cleaned off what I could and squeezed my clit to get rid of any residual liquid. I licked off my fingers, readjusted the tuck and taped the liner in place.

When I returned, she took me to another room, which was set up as a makeup studio. I sat in the chair; she took off my glasses and examined my face closely.

"Here's what I see, Miss Regina. You are not a young hussy. You're a mature woman with a lovely face that carries its age well. You have no real wrinkles, except on your forehead, and I can minimize those. Your eyebrows are a bit too thick and not shaped. I think for your eyes, something simple. You're a lady, and ladies do not overdo their makeup. I'm going to apply just enough to let your inner woman out. The eyebrow changes will be noticeable for a while. Is that a problem?"

"I'm in your hands, Mei. Do with me as you will."

She spent the next hour on my face, tweezing and shaping my eyebrows, putting who knows how many powders and liquids and magic potions on my face. Finally, she was satisfied. She turned me around to the makeup mirror.

"Miss Regina, what's wrong? Why are you crying?"

"I never knew that's who I was. You've made me beautiful. I really am Regina."

And so she had. At first, I didn't recognize this vision, with her darkened, arched brows highlighting smoky eyes. My chin somehow looked narrower and my whole face glowed. My lips were a dusky red that blended into my face and were modestly sexy. I looked carefully for telltale signs of powder or caked makeup, but found none. Looking deeper, I saw she hadn't changed me: I was still Regina, but with no trace of Roger.

"Of course, you're Regina. I'm glad you like it. Now, stop crying or you'll ruin it, and I don't have time to start again."