Serendipity

I couldn't believe I was openly discussing my dressing habits and now my sexuality with Sarah like it was baseball box scores. "I've thought about that a lot since he and I, um." I took a deep breath. "He's gorgeous. Falling asleep next to him was nice. The rest was well...." I blushed. We both laughed.

This was so easy. Talking to Sarah was like walking in flats, simple, natural. A conversation with my ex had been more like six-inch stilettos. It was a skill I had mastered, but only after great effort, a lot of failure, and significant personal risk.

I didn't have any trouble at all filling in the few missing details, finally answering one or two very intimate details about Victor and his prowess.

"How many times?" Sarah and I were laughing and giggling when we got back to Sarah's table. "Charlie, this is my cousin Mikala, sometimes Mike. Mikala, meet Charlie."

"Nice to meet you." Mikala offered me her hand.

I was stunned. I thought I looked good. Mikala looked like she had just stepped off the cover of Vogue. If I concentrated and looked closely, I could almost tell. Her hands were a little big, and her voice had that Lauren Bacall huskiness that a lot of guys, including me, found so sexy.

"Shit," was all I could think to say.

"I'll take that as a compliment. Not bad, yourself." Damn, her smile was better than Sarah's.

We sat and talked. I told her where to find size twelve Jimmy Choo's and she gave me a hint or two on my makeup. Sarah just watched and tried not to laugh. It was so liberating to talk to someone like me. We shared horror stories and victories. I had found a sister.

"There you are." That familiar baritone resonated from behind me, his hands finding my shoulders.

"Damn, you must really like my ass." I laughed. "You always seemed to sneak up behind me."

"Hard to argue with the truth." Victor chuckled.

"This is Mikala, Sarah's cousin." I smiled at Victor. "It's amazing how much she and I have in common."

Mikala stood up and shook Victor's hand. From the look on her face, she was going to eat him alive right there.

The wheels spun, the tumblers turned, pieces slowly moved in my mind until it finally clicked. I smiled at Sarah, nodding at Victor. She just smiled. This was Sarah's plan all along, setting Mikala up with Victor. That and finding out about me.

The two of us had become irrelevant as Victor and Mikala stared at each other. I could have been jealous, but Victor and I had mutually decided on the friend zone, with an occasional side trip to benefits-ville. I had my answer about Sarah, too. It was all working out, just like someone had planned it this way. Who knew? Maybe someone did. I'd put my money on Sarah.

"Would you like to dance?" I offered Sarah my hand, and we disappeared onto the dance floor. The music was more of an eighty's retro, but dancing is dancing, and Sarah had moves. It differed from what I was used to. She was shorter than me and, well, didn't have a cock for me to grind into. There were no muscular arms to melt into, but under my dress, I had those things for her, and we took full advantage.

On the slower songs, we melted into each other's arms and swayed with the music. It was so easy to lose myself in her hazel eyes, sometimes green, sometimes blue, sometimes both. I leaned down and kissed her.

"Took you long enough." She laughed, wrapped her arms around my neck, and kissed me back.

Victor and Mikala disappeared. "They have to come up for air, eventually." I joked with Sarah as we left the gala. Of all things, I won the Kate Spade purse and the dog sculpture. Sarah agreed to go out to dinner with me, but only if I wore the dress that went with the purse.

"How ok are you with me dressing up like this anyway, really?"

"As long as you're not cutting off any pieces, you can wrap it any anything you want." She pulled me into another kiss. "Now, since I'm pretty sure I'm your ride, why don't we go say hi to Roscoe and you can prove to me you're worth it?"

Versace and Jimmy Choo look like anything else scattered across the bedroom floor. Sarah insisted I keep my garter and stockings on and loved playing with my fake boobs, but not near as much as I enjoyed playing with her real ones. It had been too long, and I didn't have the stamina I used to, but Sarah covered for me. Evidently, she enjoyed giving blow jobs more than I did.

While she sucked me dry, I did my best to make her scream, licking and teasing her clit while my fingers explored the soft inner wall of her pussy.

"You are so sexy like this." Sarah traced the satin and lace of my garters, spreading her fingers and caressing the nylon of my stockings. "You ex was crazy to let you go."

"I'm not complaining." I smiled as she slid her nylon covered legs against mine.

"And this," her hand found my cock again. "So delicious."

I had already cum twice, but she got me hard again anyway, climbing on top of me and sliding me inside her, riding me hard until I exploded a third time. We finally collapsed, exhausted.

It was everything I remembered, only better. I woke up with Sarah nestled in my arms, my breasts firmly mashed into her back, and my burgeoning erection poking her amazing little butt. We had entangled our nylon clad legs in the most delicious knot.

"Hey, girl." Sarah turned to me, rolling on her back as she pried her eyes open. "This is nice."

I leaned down to kiss her, running my hand up her side to her naked breasts, fondling them as she opened her legs invitingly.

I lasted longer than I did last night and then, with Sarah's urging, licked and sucked her to another orgasm while I cleaned up the mess I had made. She returned the favor by giving me another blow job, this time shoving some of her fingers in my ass and pressing on my prostate as I came.

"You really enjoyed being with Victor, back here I mean?" Sarah nestled under my arm, her fingers still massaging my ass.

"Yeah, I guess I did. It was a unique experience. Why?"

"I was just thinking that if you really liked it, well, I have some toys I could bring over." She shoved her fingers all the way inside me. The moan I let out answered her question better than I ever could.

I was so fucked, probably literally. Hopefully, literally. I just smiled and pulled Sarah into my arms, spooning in behind her and relishing everything about her.

We met Victor and Mikala for lunch. I recognized the look on Victor's face, and the one on Mikala's, too. They had enjoyed as good a night as Sarah and I had.

The next few months fell like dominoes. I met Sarah's mom and got her approval to date her only daughter, making the mistake of sitting on Belle and Lady's sofa. I might never get the dog hair out of those slacks. Sarah moved in with me, bringing her toys. Chloe and Roscoe figured out how to share the backyard and Chloe finally seeded the frisbee was Roscoe's.

Victor and Mikala were inseparable. It helped that Mikala was Mikala all the time. She had breast implants but wasn't interested in getting anything cut off. Yeah, she was perfect for Victor. I even caught her a few times carrying Lord Biscuit around in her purse. It was so adorable, the way she snuck table scraps to him while she thought no one noticed.

"You could get smallish ones, you know. And maybe talk to your work about wearing your comfortable clothes to work." Sarah lay next to me, her hand playing with my fake boob. We had been out dancing with Victor and Mikala, and that meant I had to get dressed.

"Sarah, what are you saying?" What she was saying was obvious. It was just something I never thought I'd ever hear.

"Maybe you're more like Mikala than you want to admit. I just want you to know I'm ok with that." She smiled and kissed me hard.

I rolled her onto her back and took her hard. Most of me agreed with her. The part that still had doubts wanted to prove he was still there. Sarah closed her eyes and moaned loudly, her hands still squeezing and fondling my fake breasts. It would be nice if they were real.

We collapsed next to each other. Oddly though, it was Victor that was on my mind. How would he feel if I showed up one day with breasts that didn't live in a box most of the time? How would he feel when he found out I was dressing like a girl at work? Would he think I had lied to him? Could I have really stayed with him?

Sarah delicately extracted herself from my embrace, scurrying across the room to the bathroom. I needed to follow her, but you know, ladies first. Well, genetic ladies. Based on what she had just said to me, I felt that clarification was important. Watching her body as it bounced across the room, and then openly ogling it as she returned, I decided what Victor thought didn't matter quite so much. He and I had decided a long time ago to just be friends, after all. If Sarah wanted to have this talk, then she and I would have this talk.

I took my turn in the bathroom, smiling when I came out. Sarah was lying on the bed, grinning broadly, her largest strap on standing proudly between her legs; the one with the double penetration vibrator that would make her scream louder than I would. She dangled a bottle of lube from her dainty fingers. I did my sexist walk across the room to the bed, climbing in next to her, opening myself to her intentions and my desires.

Yesh, Victor could just deal with it. Sarah slipped inside me and made me feel things Victor never could. There is just something about being able to fondle the breasts of the person fucking you. Doing it while their long blonde locks fall and frame their face as the throes of passion fill you both, well, that trumps everything else. It also helps if you love that person more than life itself.

Of course, I talked to my therapist about what Sarah had suggested. Her professional opinion was that modest breasts would probably help me normalize the way I always felt about myself. "It might be a really good thing for you." She smiled, and we spent the rest of the session talking about me and Sarah, and what I really wanted from the relationship. Was I ready for a commitment like that?

My answer was one word: "Absolutely."

Sarah and I found some smaller forms, and I started wearing them even in guy mode. Nobody seemed to notice. My work answered the questions I had when they sent a companywide email stating simple that a QA lead named Ben was to be referred to as Harper in the future. The email reiterated company policies regarding harassment for race, gender, and gender expression.

They even required everyone to watch a collection of videos on the subject. There would be zero tolerance for any unprofessional treatment of Harper or others like her.

Naturally, I told Sarah all about it. We met with a surgeon the next week. Since I didn't want to go huge, she used a fat transfer process that not only gave me nice full B cup breasts, but a slightly smaller waist. Bonus.

I talked to HR, and then my manager before I started showing up at work in a skirt wearing makeup. Greg just laughed. "Dude, a bunch of us hang as Zed. We've seen you. Just don't wear that skimpy red dress or those leather pants to work, and I think we'll be fine."

It's a unique feeling when the cleavage your bustier pushes up is actually yours. They move differently. They feel different, and not having to worry about them falling off as you jump and spin and rub your ass into a massive black man on the dance floor is liberating.

Victor wasn't upset at all. In fact, he laughed when I told him it was Sarah's idea. "So, you go all girl for some blonde chick and not for me. It's that way, huh?"

"Well, she lets me fuck her, and I don't see you going there." I folded into his arms and kissed him as the song ended. Mikala and Sarah joined us. Watching the two of them dance had been fucking hot.

"So, listen, we need a favor." Mikala looked at me and Sarah when we got back to the table.

"Anything." Sarah answered for both us.

"Victor and me, we're going to a place called Punta Mita. It's a resort in Mexico. We're getting married." The squeals and screams and celebrating delayed the actual asking of the favor until after the third tequila shot. "I, um, I need a maid of honor." She looked at Sarah. "And a bridesmaid." She looked at me.

So many things came together overlooking the ocean as Victor and Mikala exchanged their vows. Sarah's mom was there and knew who I was. My mom came, too, and even my dad. Maybe he was finally ready to accept this part of me. Or maybe he just wanted a week at a five-star Four Seasons resort with a world-class golf course right on the Pacific Ocean. The only point of contention for the entire week was whether I got to hit from the ladies' tee box. My dad and I shared a golf cart and, for the first time in my life, really talked about what dressing like a girl did for me. Cathartic would be an understatement.

"You better marry that girl," was the only admonition he gave me.

"Yes sir, and dad, thank you."

I could see him watching me, shaking his head, as I pulled my driver out of my bag on eighteen. My coral skort dancing above my long legs, my bare midriff exposed below the floral crop top. I intentionally bent at my waist as I teed up my ball and hit my best drive of the day. I knew he didn't really understand what I had told him. It was still foreign to him, but he accepted me as I was, and that was all that mattered.

The look on Roscoe's face was priceless when we picked him and Chloe up from the kennel. We went straight to the park and played frisbee until he gave out. Choe got in on the game, too.

Burgers at that little place just down the street; I couldn't help but smile at the gorgeous woman sitting across from me. I had thought about doing this on the beach, but that was Victor and Mikala's moment. This right here was more like Sarah and me. Tired, sweaty, with our dogs. This was our world, the world I wanted.

"My dad said I have to marry you." I smiled and slid the small box across the table.

"He did, did he?" She smiled and opened it, taking out the simple diamond solitaire and slipping it on her finger. "My mom and your mom say you should wear a dress, too."

And I did. Roscoe was my best man, and Chloe Sarah's maid of honor. Victor and Mikala were their human proxies. We got married in the park under a massive oak tree not too far from where Sarah had set up her table for the dog run.

My dress was ivory and Sarah's white. She had more lace than me and mine was a little shorter, but that was just who I was. Sarah even wore her grandmother's veil, one of those vintage ones that came down just to the tip of her adorable nose. It was just enough that I had to move it out of the way to kiss her when the pastor said we could kiss our brides.

We all convened at that little burger place after the ceremony. Sarah slid a small box across the table to me. Inside was a simple solitaire. Perfect. Just like our wedding bands, it matched hers. I slipped it on my finger. Everything was perfect.

My dress being ivory, her wearing the veil; they were subtle reminders of the dynamic of our relationship. Regardless of the clothes, the remnants of my manhood would always be there, and her femininity would never be in doubt. The matching rings told everyone we were equals in every way. It was just as fate had destined it to be.

Sometimes, despite all our fears and trepidations, the universe just puts everything exactly where it's supposed to be in our life. Some call it luck, or chance. I like the word serendipity.

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