Serendipity

"I understand," told her. "You decide to share your biggest fantasy with a near stranger and then he springs this on you. I get it."

"I'm not always the most tactful person," she continued by saying. "So I hope you'll forgive me if this blunt but I'm just gonna ask. Would you even consider going out with me sometime as Callie? I mean, do you date women when you're her?"

We arrived at her floor and as the elevator came to a stop I said, "Well, I'll have to ask her, but I think there's a pretty good chance she'd say 'yes.'"

Kay laughed out loud and said, "Be serious. I took a big risk asking you so don't be mean."

"Sorry," I said. "I often use humor—good or bad—to deflect serious things. I certainly didn't mean to hurt your feelings."

Kay stopped the doors from opening and turned to me and said, "You're really adorable, Cal. Maybe that picture has tainted what I'm about to say and you can't really blame me if it has, right? It's just that you're the first guy I've even been willing to consider going out with you since I came out. And it may not mean much to you, but considering I'm a girl who sees herself as about 95% gay, that's pretty high praise, ponytail guy."

I knew she was being serious, but I just couldn't help myself when I said, "Yeah, that is high praise. But let's be honest here. I'm still not sure you're up to my high standards."

She let go of the button and the doors opened. Kay turned around and feigned punching me in the stomach. She stood in the doorway to keep the doors from closing and said, "I feel like I'm back in high school or something. My stomach has butterflies in it and I'm wondering if I'm going to get a goodnight kiss."

I smiled and said, "I think you're confusing me with my twin sister. She's probably the one you're wanting to kiss you goodnight."

When I said that, Kay closed her eyes and moaned softly. "Mmmm. You are so right. My God! I've never even considered...well, a girl like you...er, her but she's...no, you're so...gorgeous...and she's got all the right equipment and...this is just so...crazy. I can't believe we actually met and talked AND found this out about each other. You know, I don't believe in God or fate or that kind of thing, but this is serendipity at best, don't you think?"

I leaned over and kissed her on the cheek and said, "Most definitely."

The door started to close and I said, "Oh, wait. What's the protocol for this relationship? Should I call you or will you be calling Callie?"

Kay smiled and said, "You're a nut. An adorable nut but still a nut. Good night, Cal. I had a really nice time."

"Me, too," I said as the doors pulled shut.

We had an early breakfast together the next morning, but we didn't talk about the night before or dating. We were both focused on the race and I liked that she was someone who seemed really centered and self-confident without being cocky. I don't like arrogant men, and I can't stand loud women. The few lesbians I've met have tended to be like that and I found them to be a little too over the top for my liking. Kay, on the other hand, seemed to be pretty damned near perfect.

The race started at 10am and I finished in 2:39:03, a personal best for me. I finished 7th in my division and was more than satisfied with my performance. Kay also had a personal best coming in in 2:53:18. I was waiting for her at the finish line. She was absolutely exhausted and fell into my arms a few steps beyond the "Finish" banner. I congratulated her on her time and while trying to catch her breath she said, "I gotta tell you, ponytail guy, the thought of going on a date with Callie was the best motivation I've ever had. Anytime I started hurting, I'd thought of the beautiful girl in that picture kissing me goodnight and I was able to keep going."

We grabbed some Gatorade and Kay downed two cups immediately then sipped a third as she began recovering. Jason saw us as he came across the line about five minutes later and we waved him over to join us.

"Holy shit!" he said while panting heavily. "You gotta have at least five years on me and you kicked my ass. What was your time?" I told him and he just threw up his hands. "Kiss my ass!" he said jokingly. "How'd you do, Kay?" She let him know she beat him, too, and he said, "Shit! If I had a gun I'd shoot myself." Both of them laughed and hugged each other. "See you guys around, okay?" he said as he headed off.

The hotel was about a mile walk from the finish line so we slowly strolled back together. We barely said a word until we got to the lobby. I opened the door for Kay and she said, "That makes me wonder who should open the door for whom when Callie and I go out." Kay wasn't serious. She was just letting me know she was really looking forward to our date.

"Callie's only been on one date with a woman and that was her ex-wife who was with another man so it's kind of um...virgin territory for her, too. I'm sure she'll be fine no matter who goes inside first."

Kay laughed at the virginity reference and said, "She sounds like my kind of woman." We got to the elevator then she said, "And she definitely looks like my kind of woman."

I made a split decision to say what I was thinking and chimed in with, "Yeah, and you haven't even seen all of her yet."

Kay stepped inside then closed her eyes and said quietly, "Don't remind me. I'm already unable to think about anything else."

I pretended to be greatly offended and said, "I don't think Callie would appreciate being talked about that way. She's a very nice lady, you know."

We were at Kay's floor and as the doors opened she said, "That's okay. I have a way of dealing with nice ladies I think she'll like." As the doors closed she looked over her shoulder and added, "A lot. Call me soon, okay?"

I was too tired to get hard, but I knew I'd be spanking the monkey later that night dreaming about a first date with this smart, funny, and beautiful young Navy officer. Another first for Callie coming up!

I got a text from Kay the next morning. "When you ask your sister about going out with me can you ask her what she'd like to do? I hang out in gay bars a lot, but that doesn't seem like her thing. I don't even know what to wear for her. Okay, a sweater, for sure, but what else? In case you can't tell, I'm pretty nervous about this first date. I want to make a really good impression so anything you can tell me would be appreciated. Oh, btw, please don't tell her any of this. I don't want her to think I'm some kind of flake. Kay."

As Callie, I didn't go to gay bars and rarely ever went anywhere crossdressers hung out. Mainly, I wanted to seen as a unique individual not one of many people with the same thing in common. I preferred being seen as a beautiful, straight girl so I tend to spend my time at singles bars or lounges where young, single (or married) men congregated. The one time I did go to a gay hangout called Screaming Queens, I met Tim. Even so, that just wasn't my choice of venue for Callie.

After giving Kay's text some thought, I texted her back. "Callie said she'd love to go out with you so you can stop worrying about that, okay? She just wants you to take her somewhere nice. Doesn't have to be expensive. Just something quiet and comfortable. Oh,I showed her the pic I took of you and she loved it. She said if you want to wear something like that be very happy. Sound okay to you?" I ended it with the ubiquitous smiley face.

I got a reply moments later. "Oh, my. You see, I'm usually the girl in any relationship, but it sounds like I'm gonna have to take the lead in this one. Okay. No worries. I believe every challenge is just an opportunity to excel so I'll find someplace...nice...and I'll do my best to look pretty for her. Tell her I can't wait to meet her, okay? K."

"Callie says you won't have to try because she thinks you already are pretty." Smiley face.

The next evening I got another text from Kay. "Can we please talk? K."

Uh, oh. She must be having second thoughts. I should've known. "Sure. Anytime."

The phone rang almost as soon as I hit 'send.'

"That was fast," I said as I answered the phone.

"I wanted to call you because I didn't want to say this in a text," she said very seriously.

"Okay. What's on your mind?" I asked knowing what was coming.

"Can we get together and talk in person? Tonight maybe?"

"Are you breaking up with me before our first date?" I said in a tone of voice that belied my fear she was doing just that.

"What? Breaking up? Are you crazy? No! I just need to talk with you. I mean, with...you. With Cal before I go out with Callie who is you which is why I need to talk to you...Cal." I heard Kay make an 'argh' kind of noise.

"Everything okay?" I asked.

"Yes," she said. "No. Not really. I mean, maybe it is, but that's why I need to talk to you right now. So can you? Can we? Do you have time tonight?"

"Calm down, Lieutenant! I'll be right there. Just text me your address. I'm on my way. Oh, and Kay? Breath, okay? Just breath. I'll be there as soon as I can."

I lived in the suburbs on the west side of the city and Kay lived in a nice apartment in downtown DC. There was very little traffic and I got to her place in less than an hour. I walked up one flight of stairs to the second floor and rang the doorbell.

"Hi. Thank you for coming over. I'm sorry for sounding hysterical or psychotic or whatever. I'm normally so calm and so focused people think I'm stoic. This is really out of character for me. I just don't want to blow this—whatever 'this' may be."

Kay showed me to her sofa in what was a very nicely furnished place. "Please have a seat. Can I get you anything? A beer maybe?"

"Only if you're having one," I told her.

Kay returned with two Bud longnecks and we clicked bottles before taking a first sip.

"So whatcha got on? Your mind?"

"What?" Kay said with a puzzled look. "Oh, okay. I get it."

"Sorry. Just me trying to deflect again. I'll be quiet and listen," I promised her.

"I hope not," she replied. "I need you to talk to me. I know you'll be honest so that's not the concern."

"What is the concern then?" I asked as I took a long pull from the bottle. I didn't drink beer very often but it tasted so good for the first few days after a marathon.

"You're an engineer and I majored in math at the Academy. That means we're both rational, logical people. That means we can separate fantasy from reality. So when we talked about my fantasy and you told me you knew someone who could be my fantasy, I temporarily lost the ability to think rationally. I was so caught up in the fantasy, reality didn't matter. Then I came down off of the endorphin-induced high and started having doubts."

"What kind of doubts?" I asked as I took another drink.

Kay took a long drink of her own beer and said, "The list of doubts I'm not having might be the one to start with because it's a lot shorter." She stared at me to gauge my reaction then said, "Sorry. That was my attempt at humor. Looks like we both have some work to do in that area." I smiled and let her know I was paying attention.

"I'm gonna try not to ramble. I'll try and stay focused. But something tells me I'll end up being all over the map anyway." She looked at me again and I didn't say anything.

"The fantasy is dating Callie. A pretty 'girl'"—Kay used air quotes to emphasize the word—"who has that special something I want so bad. But the reality is I'm dating you. A guy. A man with a dick."

"And that troubles you I take it?" I asked. I felt like I was a psychiatrist asking my patient questions.

"Well, yeah. I mean, I'm not really attracted to guys. I like women. Pretty women. Like Callie. But you're Callie. There is no real woman who is available 24/7 named Callie. She's a fantasy who can only appear now and then, right?"

I finally realized where she was going with this and said, "That's true. I spent a week in drag once on a cruise—including two days of flying—and by the third day I was tired of it. By the fourth, all I wanted to do was drink beer"—I took a big gulp—"and belch"—I ripped one off that startled Kay and made her laugh.

"Exactly!" she said excitedly knowing she was getting her point across. "So if I have a relationship with Callie—something I very much want—I'm also having a relationship with you."

"Something you very much don't want, I assume."

"That's what's really confusing," she said as she took another drink.

"How so?" I asked as I finished my beer.

"You want another one?"

"No, thanks. One's my limit. Sorry. Go ahead. How is that confusing to you?

"Let me me see if I can explain this. When I looked at your pictures, I felt sorry for the little boy growing up being teased mercilessly. When I saw the guy with the ripped body, I wasn't turned on in the least. Sorry, that's just how my brain works. I obviously LOVED the pic of you as Callie, but what's really hard for me to wrap my head around is that I find myself somehow attracted to you. Like this," she said as she used her hands to indicate she meant me as I currently looked.

"I think I should say thank you but I'll wait for the other shoe to drop when you give me the 'however' part that's sure to follow."

"No! That's just it. There isn't any 'but' coming. I really am attracted to you and I think it's because you're so thin and small and...."

"Feminine looking?" I said filling in the blank.

"Yes. That's exactly it! Does that bother you? You know, as a man?"

"Not at all," I said honestly. "You know how I used to look and I worked unbelievably hard to get strong then worked just as hard to get thin. It's very difficult for me to maintain this weight, but it's the only way I can fit into a size 8 dress."

Kay put her hands over her mouth as she laughed loudly. "You're a size whore!" she joked.

"Guilty as charged. I'd die if I had to wear a size 10," I told her. And while I wouldn't actually die, I would be very unhappy.

"All kidding aside, I have no idea whether this will be one-time thing or whether we might really like one another but if it is going to work, it has to work with me and you and me and Callie and it kind of scares me to think I might be falling for a girl who's a guy and I'm confused as hell."

"Would you like my opinion?" I asked sincerely.

"Oh, my God. I've been doing all the talking. I'm so sorry. Of course I want your opinion. That's why I asked you to come over."

"I think we take things one day at a time. Let's go slowly and see whether or not you really do like Callie or if you just like the fantasy of Callie. That means you and I have to take it slowly, too, to find out whether or not you and I actually like each other as friends. I can tell you you're the first woman I've really been attracted to since my divorce, and I'll also tell you I pretty much gave up on even trying to find another woman because of Callie. Even so, I'm never giving her up again and what I most like about you—other than you being cute as hell—is that you not only don't mind Callie, but you find her attractive. That is a 'must have' for me in any possible future relationship with any woman."

"I gotta tell you that even when the fantasy high went away, the butterflies I feel every time I think about Callie didn't go away. What surprised me the most was when I got them thinking about you," Kay said sheepishly. Kay was looking right at me until she finished her sentence. She looked down and away as if she feared me saying I didn't feel the same way.

I reached my hand out and waited for her to notice. She saw it then looked up at me before reaching out to take my hand. "Come over here," I said. She let me help pull her toward me. "I like you, Kay. I'm attracted to you physically for sure but more importantly, I'm attracted to you mentally and intellectually. Smart women turn me on. Smart, pretty women really turn me on." Kay smiled. "But meeting a smart, pretty woman who loves and accepts Callie is more than a fantasy. It's well...I'm not sure. It's...too good to be true? Like you, I don't believe in God so I don't pray. Therefore, this can't be an answer to prayer. But it is, as you said, serendipitous for sure. I feel very fortunate to have met you and I'd like to give this...to give us...a chance. So if you feel the same way then...."

Kay leaned over and closed her eyes as she kissed me on the lips for the first time. "I do feel the same way. And I just had those butterflies again."

"Me, too," I told her as I kissed her back.

I knew we'd end up in bed if I didn't force myself to stop and somehow I managed to pull back shortly after Kay offered me her soft, warm tongue. "Oh, my God," I said with real desire in my voice. "Listen, if we don't stop right now, we definitely won't be taking this slow."

Kay heaved a sigh and said, "I know. I was thinking the same thing but I just wanted to be with you so bad."

"Me, too," I confessed. "But you need to meet Callie and see if you hit it off with her first. Well, me. No. Me as her. Sheesh. This really is confusing, isn't it? But you know what? I have a very good feeling about this so we owe it to ourselves to wait and see, don't you think?"

"Reluctantly, I have to agree with you," she said. As she slowly took her arms down from around my neck she said, "But I have to warn you. If I like Callie as much as I like you, then there won't be any stopping my freight train of pent-up emotions."

"Forewarned is fair warned," I told her with a smile.

"So have you decided where you're taking her/me/Callie yet?" I asked.

"I have," she proudly announced. "But it's a surprise. Just let her know it's going to be something very nice and very special. Ask her to be ready this Friday at 7 o'clock for me, okay?"

"I will," I said. "And I'm sure she'll love it. She really likes it when her date takes the initiative and makes plans for her. And you can order her food and drinks too, if that's something you're comfortable with. Well, if you're taking her to dinner, that is."

"That's a safe bet. I want to show off my beautiful date in public. That doesn't mean I'll embarrass her with any public displays of affection, though. Just in case she might be concerned about that."

"Callie is very open minded so while she might not want someone to paw all over her, I'm sure she wouldn't mind having her hand held or maybe even being kissed a time or two."

"Good to know. Thanks for the intel, ponytail guy," she said with a very bright, very happy smile.

Kay walked me to the door and said, "Thank you for coming over tonight. I really needed to talk to you. It means a lot that you dropped everything and did this for me."

"For us," I said as I put my hands on her shoulders. "There are essentially three people in this potential relationship, Kay. I'm in and I'm pretty sure Callie will be, too."

"I'm in, too—with you at least. I'm also pretty sure I'm gonna like Callie just as much. So, well...goodnight then, Cal," she said with a hopeful look on her face.

I wasn't about to leave without kissing her goodbye so I leaned over and gave her a short but nice kiss before leaving as I told her goodnight.

I was glad Kay was fairly tall for a woman. I was only 5' 8" which is a real help with passing in public but with heels I'd tower over Kay who was 5' 7" herself. As I left I was thinking about how that might look until I remembered she wasn't butch meaning there was a good chance she might also wear a sexy pair of heels on our first date. I felt myself growing hard as I got in the car and started the engine.

*****

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The weather was turning cool and I was thrilled about shopping for new sweaters. I hadn't been to my favorite stores much the last few months and I ran into several girls who didn't know me at a couple of them. They were very helpful and friendly even when I told them I was shopping for myself. I didn't go in drag because I hated messing up my hair and trying not to get makeup on my clothes when taking them on and off.