The Last Time We Met

"Do you think I'm so shallow as to care about a bit of body hair or a tummy? They are beautiful because you are beautiful. The tragedy is that you don't know it, but I do.

"You are a very special lady, Regina and I want you to realize that and let yourself truly live. Do I want to turn you into my perfect woman? No, because, deep down, you already are. What I want to do is let you emerge in all your glory. I want you to look at yourself and say, 'My God, I am a beautiful woman.'

"But if you're going to continue to call me a liar, tell me know and we'll end this right now."

He choked up as he ended his words; I couldn't tell if he was starting to tear up because my eyes were already brimming. Of course he was lying: I was nothing like that. But in our previous meetings, he had never been less than open and honest. If he was playing a game here, it was a deep and devious one. But, why would he do that? And what if he's not?

At that moment, I realized he was telling the truth: here I was again, overanalyzing and tearing apart what he was telling me. I really was self-sabotaging, because I was afraid of making a mistake and being hurt. It wouldn't be the first time I had misread someone and scared them away with my intensity, my need for passion, for belonging.

But how many other opportunities had I missed because I was too clueless or frightened to catch the signals? Donald was not being ambiguous at all in his signals, if I believed him...if I believed him...

"I don't care what I said!" I shouted.

I stood up, grabbed his head, and crushed his lips to mine. He stiffened in shock, then returned my kiss, his arms wrapping around me and pulling me into him. His cock was pressing against my crotch and my clit was trying to tear a hole in my panties. It grew stiff enough to cause me pain, but I didn't care. We remained this way for who knows how long, until I pulled my lips away and surrendered my eyes to him.

"You're not a liar, Donald: I believe you. God help me, I believe you. Make me your woman. I want you to be proud of me. I want to be proud of myself, proud of being yours. Show me who I am."

"I'm already proud of you, Regina," he said, giving me a kiss on the forehead. Then, with a sparkle in his eye, "And do you know why?"

"Why, Sir?"

"Because," he said, pulling his shorts down and laying on the bed, "you know just what do when my pants are getting tight."

I licked my lips. "Indeed, I do, Sir. Thank you."

He knew just what I needed at that moment to calm me and settle me. It was one more reason I was in...one more reason I was happy to be his woman.

June: Boundaries

The next morning, Donald sent me the name and address of the woman who took care of his grooming. He also sent me links to several sites specializing in the deportment of ladies. They all had a 50s vibe, when women were elegant, sophisticated and knew how to be treated by a gentleman.

Donald was definitely a gentleman. Even when he was feeding me his cock, he let me set the pace and never set out to gag or choke me. In return, I made sure every time I took him in my mouth, it was to make love to his cock.

There was a single attachment to the email: a calendar file that set aside every other Thursday from 4:00 to 8:00. It simply said "Training." Once again, he showed his consideration and concern for my privacy. I was looking forward to the first official training session.

The following Friday, I met Donald in the lobby of the Arcadia, the local art house cinema, for "Solaris." I had just got off work and was in my usual business casual. He was wearing khakis and a golf shirt. I was relieved, but also slightly disappointed, that he wasn't wearing his cargo shorts. We shook hands and got in the concession line.

I ordered a small popcorn and water. He looked surprised, as did the concession attendant, who normally sold me a large popcorn/soft drink combo.

I smiled at them both. "I'm watching my girlish figure."

The attendant laughed. Donald did not.

The movie was excellent. Being in Russian with subtitles, we had to focus on the screen for its almost three hour running time. Afterwards, we discussed the distressing tendency for American studios to do bad remakes of good foreign films.

By the time we left the theater, it was dark. The lights in the plaza illuminated the fountain and the large cement steps that provided a place for people to gather and talk. Donald sat down and I joined him. He looked pensive and I could see he was serious.

"Roger, we need to come to an understanding about certain things if this whole arrangement is going to work." Another deep breath. "I told you earlier that I'm not gay."

"And I told you I'm not gay, either."

"Yes. And that brings us to Regina."

I watched him closely. He was staring at the ground, as if trying to remember a memorized speech. He had my attention: I needed to be very sure I heard and understood what he was saying, and not saying, and that meant keeping my mouth closed.

"I'm listening, Donald."

"My friends call me Don. And that's what you are, I hope: my friend. It was nice to find someone who can talk film intelligently. I'm a bit of a nerd; so are you. And we nerds have to stick together.

"But Regina is something else altogether. Look, I know it sounds weird for me to talk about her as if she's a separate person, but, when we're together, she is. She's not Roger, she's Regina, a sexy, vibrant woman, who draws me in a way I don't fully understand. It's not just about the sex; she has a vulnerability and a passion that are an intoxicating mix."

I had to agree with him. When Regina appeared, I was a different person. I had tried to analyze it, but gave up, afraid of what I might find if I dug too deep. For the moment, I was content to go with the flow. I was surprised, but pleased, that Donald was having the same struggle.

"I don't know where this is all going, Roger, but I really need to keep you and Regina separate, or I'm going to wind up on the mother of all guilt trips. I'm sorry to put this on you: I know it's really messed up, but I'm really messed up right now."

"Hey, Don, we're all messed up. Normal is dull, and this is definitely not normal. But I like you. It's great to have someone I can talk old movies with, even if you do have terrible taste in coffee. And I know Regina is crazy about you. If it takes a bit of a split personality to keep this going, I'm willing to give it a shot."

"Thanks, Roger. I appreciate it."

"One question for you: in the theater, you didn't seem happy about my girlish figure joke. Is this why?"

"Yes, and I'm sorry I was a jerk about it. It was a reminder of the biological realities of our situation, and it jarred me."

"In that case, Don, I won't mention her when we're together. I'll be your macho, good old boy buddy and pal. And I guess I won't be calling you 'Sir.""

Don looked up and laughed. I grinned back.

"'Don' will be fine."

"10-4, good buddy."

"And, Roger, thanks. This means more than you know."

"The vice is definitely versa. I'm looking forward to our next movie outing. Are you going to be Siskel or Ebert?"

Another laugh. "You're the one wearing glasses, so you're Ebert."

On the way home, I mulled over the conversation. A normal person would be running away from this as quickly as possible. Fortunately, I had never been accused of being normal. Besides, he was right: as long as Regina was the one gazing adoringly at Don, er, Donald, I was still safe as a bi man. After all, it was only gay guys who loved men, and I wasn't the one longing for him: it was Regina.

And so started the strangest relationship in which I had been involved. It was, I suppose, a triangle of sorts, with two sides and three angles.

Every other Thursday, Regina met Donald at the hotel. We had developed a routine. He would text me the room number. I would go in, dress in the outfit of the day and shut Roger away in the dresser, along with his drab clothes.

I was now fully Regina and texted him I was ready for him. When he arrived, I would greet him with a brief kiss on the lips, followed by a blow job to take the edge off his lust and my hunger.

This was followed by my ongoing lessons in becoming his lady. I was learning to walk in progressively taller heels, until I could handle a five inch heel without stumbling. Other times, I wore kitten heel slide ons and learned how good it felt to pull the shoe along with my foot and hear the satisfying slap of the insole on my foot. Best of all was the way my heel would rise off the shoe when I was on my knees feeding on his cock.

My wardrobe was growing. He must have had a walk in closet at his house to keep all the dresses, blouses and skirts he was buying, not to mention the shoes and lingerie. Ah, the lingerie! I loved the way it caressed my skin. Even more, I loved the lascivious looks Donald gave me when I modeled the latest bit of nightwear for him. I had finally learned to strut and pirouette in my kitten heels.

At his request, I had created my own email account, to which he regularly sent words of encouragement and links to sites that would improve my femininity. I learned how to walk properly, like a lady and not a streetwalker. I kept my head tall and proud and eyes focused straight ahead.

On occasion, Donald would escort me, fully clothed, to the nearby stairwell to practice walking up and down stairs. I loved the sound of my chunky heels echoing in the stairwell. He insisted that I not wear stilettos, as the risk of breaking an ankle wasn't worth it. That was the kind of considerate man he was. And when I would stumble, and he grabbed my and held me close for balance, my heart grew warm.

We would finish the lesson with a passionate kiss, followed by a farewell feeding. I looked forward to those, as he was generally naked and on the bed, allowing me to explore and worship his magnificent body in detail. Though he apologized for his physique, I adored every bit of him, from his dad bod to his age lines. He had given me his body, just as I had given him mine, and I was enamored with it. Soon, my hands and mouth knew as much about his body as they did his cock, and gave me nearly as much pleasure.

When we adjourned to the bed for me to worship his naked body, I still remained clothed. I sucked and licked on every inch of him, from his toes to the tip of his nose, but one area remained forbidden: if I approached his rosebud, he would gently push me away. I knew better than to push the issue, for Roger had figured it out long ago.

Once our passion was consummated in my mouth, Donald would get dressed, give me a kiss on the forehead and depart, leaving me glowing and, strangely, not frustrated at not ejaculating. I may not have been having a traditional male orgasm, but my whole body was ablaze and I glowed. I would lie on the bed smiling, remembering each moment spent with my Donald.

When the afterglow passed, I would take Roger out of the dresser and return to him, leaving Regina behind, her clothes neatly folded on the bed. I would return home, open some transexual porn and get the release denied Regina by watching virile men giving Natalie or Ella the pussy pounding she wanted so much.

February: Invitations

I had tried male bonding in the past, but the traditional macho exchanges and activities were a complete turn off. When I tried to veer the conversation away from sports, boobs or the latest superhero schlock, to more interesting and important topics, I found the conversation dwindling to whatever the current talking points were. They found me tedious and I found them boring. My work relationships were superficial at best.

My non-work relationships were non-existent, except with my family. They were far-flung, but we kept in touch and had regular visits. My sister' children loved me, and I treasured those times together. I was the oldest and my siblings still looked up to me. I could never let them know the desires lurking inside me, lest I lose them. I couldn't let any of that slip.

Don was different. He shared many of my cultural tastes, though we agreed I wouldn't talk about freestyle jazz if he wouldn't talk about alt-country. His biggest fault was not getting that Deep Space Nine was the greatest of the Star Treks: he was a hopeless conformist to the traditional wisdom of TNG. Oh well, no one's perfect.

Our movie night had become a regular event every other Friday. We usually caught the double feature at the Arcadia. The next day, we'd meet at a local coffee shop for java and conversation. It took several months, but I finally persuaded him to try some real coffee at my favorite spot. They specialized in single sourced, sustainably grown coffee. Once a year, the owners traveled to Central America to select the beans personally. While it was more expensive, it was wonderful coffee, with actual flavor instead of the bitterness of burnt beans.

Don was impressed. "Wow, this tastes great!"

"It's amazing what the real thing tastes like, especially when it's brewed with care. They roast the beans themselves to get just the right flavor."

"And it shows," Don agreed, "I guess you're right: I can almost taste the love that goes into the brew. I'm sure it was hard to find just the right coffee farm and even harder to roast them just right for the perfect cup of coffee. It's definitely a labor of love for them."

"You're waxing poetic this morning," I bantered.

He looked up. "Sorry, I was just thinking about..."

"Thinking about what?"

"Ummm, thinking about those delicious looking pastries in the case. Want me to bring you one?"

"No, thanks. I'm..."

"...watching your girlish figure, I know," he laughed.

I watched him walk to the front and admired how, at his age, he still had tight buttocks...I closed my eyes and took a breath. No, Roger, you're not allowed to think that. Lusting after Don's body was Regina's job, not mine.

He came back with a chocolate torte. He took a bite and smiled orgasmically at me.

"Mmmmmm, Roger, you don't know what you're missing. It's amazing."

My stomach growled, but the scales hadn't lied this morning. I was down almost ten pounds over the past two months; I wanted Regina to have the best body possible.

"That's mean, Don."

"You should try a bite. Here."

He held out his fork and I leaned in to taste it. It was, indeed, delicious and I licked the fork clean of the ganache. I closed my eyes and licked my lips.

"Oh, wow, you're right. That's delightful!"

I opened my eyes and saw him giving me a funny look. Suddenly, I felt the profound discomfort of two bros realizing they've just engaged in unmanly behavior. He looked down at his torte and I blushed.

"Speaking of delightful," he said, changing the unspoken subject, "have you been enjoying Mei's talents?"

"Have I ever! I've been seeing her the past six months. Thanks for recommending her. Now I see why women love their pedicures. They're heavenly!"

"Yep. They're very relaxing. Has she given you the hot stone leg massage?"

"Oh, yes...it feels wonderful."

Mei was the manicurist Don had recommended. She was actually much more; she ran a one woman spa from a converted house on one of the main drags. Her clientele was strictly word of mouth. From what I could tell, she had dozens of women, and several men, who used her services: everything from mani/pedis to waxing, eyebrows, massage and makeovers. She was a petite Chinese woman of that indeterminate age between 40 and 60. Mei had the smoothest skin I had ever seen and strong hands she put to good use with chair massages. Her services weren't cheap, but they were definitely worth it.

"Uh, Roger?" Don asked shyly. That wasn't like him at all. I looked at him quizzically.

"What is it, Don? Is something wrong?"

"No, nothing's wrong." He took a deep breath. "I need to ask you something. I know I said we wouldn't talk about Regina, but there's something I need to know, something I need to hear from you."

"What is it, Don?"

"It's been almost a year since she met me. What does Regina think about me? What does she really think about me?"

"You mean apart from the mind-blowing sex you have?"

"Yes...I mean, apart from the fun we have, does she like me?"

I saw fear in his eyes...no, it wasn't fear, but something else...was that hope?

I wondered why he didn't ask Regina, but I didn't want to hear the answer to that question.

"Don, I think Regina is wild about you. She's never felt better about herself and never felt so wanted in her life. She thinks you're a fantastic lover, but more than that, a wonderful gentleman and a great friend.

"So tell me: what do you think about Regina?"

"I've never met anyone like her. She's passionate, caring, sensual, bright, beautiful and has great taste in mov...in clothing. What more could a man ask?"

"What are you trying to say, Don?"

It was cute watching the supremely confident Don stammering like a lovestruck teen. At the same time, my own heart was pounding in my chest.

"Do you...do you think she'd go out on a date with me?"

I almost laughed out loud. After almost a year of passionate sex, he wanted to have a date? After hitting a career number of home runs, he wanted to go back to bunt singles?

And then it hit me: he wanted her to go out with him. He wanted Regina to appear in public, on his arm, showing the world she was his woman. That was what the months of training had been about.

But what of Regina? In spite of all her exercises, she knew who she really was. No amount of fashion could hide her face, her bulk. In the hotel room, she could see herself through Donald's eyes. In the glare of the real world, harsher gazes would be fixed on her.

"Don, do you think she's ready to go out? I know how she feels about you. She'd go through Hell for you. And, if you asked her, she would say, 'Yes, Sir. I would love to.'

"But what happens when people start staring at her, when they point to the freak in a dress? I don't think she could handle that rejection."

His eyes blazed, not with anger, but with passion.

"Roger, do you think I'd put her in a position where that could happen? She means the world to me. I would never do anything to hurt her, you know that. And I would never do anything to hurt you, either.

"She doesn't see herself the way I do. She has a beauty that radiates from the inside out. Anyone seeing her will see that. I've seen her walk and carry herself. I'll put her up against any woman out there. She's more a lady than most of them will ever be. I want her to see that she belongs anywhere she wants to be."

"I suspect where she wants to be is in your arms. Of course, she'll do whatever you ask, even if it destroys her."

"Do I mean that much to her?"

"Do you even have to ask that question?"

"I want her to be all she can be, Roger, you know that. I've already spoken to Mei. She'll give her a complete makeover, and we've got an outfit in mind that will be perfect for her."

"You told Mei about Regina?"

"Only that she's someone very special to me who needs to have her inner beauty brought to the surface. Mei has many talents, Roger, and I count her as a dear friend. There's a lot about her you don't know. One day, I'll tell you about her."

The moment I had dreaded and hoped for had arrived. Regina had become my ideal, the perfect expression of my inner feminine. Roger was smitten with her and I was smitten with him...no, Regina was smitten with him. I couldn't be smitten with him: I'm not gay; I don't love men. But Regina...Regina was different. Was she in love with him? That would mean stepping into the abyss, going all the way for him. Could she take that risk?

And what would that mean for me? If he and Regina started going out, what place would there be for Roger? I knew how he felt about Regina: he would want to spend every opportunity he could with her, not with me. Would I lose the one true friend I have so Regina could have her one true love? It may not happen, but was I willing to take that chance?