Serendipity

*Note to readers: I recently wrote about a cruise I went on in the Fall of 2012with my former boyfriend, Tim. I wrote it in response to the many private emails I got asking me why I don't live full-time as a woman. The short answer is: I don't want to because I enjoy being a man. I only want to be Callie a few hours at a time.

Tim and I broke up shortly after the New Year because he, like me, seems unable to be satisfied with any one person for very long. While he was gorgeous and a genuinely nice guy, I got bored with him and just couldn't put any more energy into the relationship.

I stayed single for almost about ten months—a record for me since I got my braces off in high school. And then, purely by chance, I ran into someone at a marathon I was running in mid-September of 2013.

I've only dated a handful of women since I stopped lifting and starting crossdressing again. I like women. If a cute girl hits on me and wants to hook up, I definitely won't say no. I honestly believed no really attractive female would be comfortable living with a guy who loves to crossdress and dates men. And by dating, I of course mean....

So for the most part, I stick to dating guys when I'm Callie. However, this very special person I met has been my girlfriend and lover for just over two years. When I told her I enjoy writing erotic stories, she encouraged me to write "Cruisin' for a Bruising" and when I mentioned writing about us, she was very supportive. So thank you, honey. This is our story and I love you very much!

*****

"Name?"

"Cal Petersen."

The official scanned the registration and handed me #8. "Wow. A top-ten qualifier. Here you go, Mr. Petersen. Good luck."

I thanked him and took my bib with the number eight on it and turned to go back upstairs when I saw her. She was in another line waiting her turn. I excused myself as I cut through two other lines to get over to her then moved alongside and said, "Well, this is a pleasant surprise!"

She turned to look at me and it took her a second to make the connection. "Oh, my God! I know your face, but I'm drawing a blank on the name. Can you help me out?"

"It's Cal. Petersen."

"Yeah, right! The flight engineer guy on base. The guy with the ponytail. You really helped us during that two-week sea trial. I recognized you as soon as I saw you, but that's been, what, maybe a year ago now?"

"Just over," I told her. "And I have to admit I can't remember your name either, Lieutenant." I remembered her rank and her face but that was about it.

"Randall. Kay Randall," she said.

"Is that like Bond, James Bond?" I kidded.

She laughed and then I remembered that smile. She was really very pretty. I'd only ever seen her in uniform and remembered thinking she was cute, but seeing her in shorts and a tee-shirt with no make up told me she was downright good looking.

I have a thing for short hair on the right girl, and she most definitely had the face for it. She had that kind of pixie cut I really like. Not spiked. I hate spiked. What I really like is when it's both short and smooth. The most beautiful woman I could think of with that kind of cut was Halle Berry who also sometimes wears the dreaded spiky kind of pixie I despise. Hers was most definitely not spiked or gelled. It was very short, soft, and smooth and sexy as hell.

Not only was her face incredibly attractive, she had a thin, runner's build and I've always liked thin. Not emaciated—thin. I tried not to stare, but I managed to get a good look at her boobs and I guessed she was probably about a full B. (My suspicions were confirmed later on.)

"I could tell you, but then I'd have to kill you," she said, thus showing me she could both give as well as take. Any career military person, officer or enlisted, has to be good and getting and giving sarcasm as the military thrives on it.

"Number 8," she said admiringly as she looked at the bib in my hand. "What's your qualifying time?"

"I could tell you but...well, you know."

She laughed and said, "Ha! Cute and funny. That's a winning combination in my book."

I stood and talked with her as she inched her way toward the registration table and as we were chatting another guy I recognized made his way through the lines and told her, "I'm all set." He was holding #316.

I said, "Oh, sorry. I didn't realize you guys were together." I didn't show my number but I did raise the bib slightly as I said, "I saw Kay in line after I picked up my number and was just saying 'hey.' I'll leave you two alone.

Both of them smiled as Kay said, "No. It isn't like that. Jared and I are both Naval Academy grads and old friends. Nothing more. Besides, he isn't my type."

I looked at him and wondered what her type was. He was tall, athletic, good looking, and had a great smile. He was obviously intelligent. I knew he was good natured and easy going from having kinda, sorta worked with him during the sea trials. That comment peaked my curiosity but I didn't ask and she didn't tell.

"We're gonna get together for dinner tonight. You wanna join us?" she asked.

"Nah. No thanks. Third wheel and all that. I appreciate the offer, but I'll be okay but."

Jared chimed in and said, "I meant to tell you I can't make it tonight, Randall. I ran into Douglas and he wants me to meet his new fiancee. So problem solved, right?"

"No kidding? James Douglas is taking the plunge? Wow. Seems like everyone from our class is getting hitched. Jesus. I hope that's not contagious." She turned to me and said, "Lucky you, right? Seems like you and I can grab dinner together without the real third wheel over here being around after all," Kay said as she used her thumb to point at her fellow Navy officer. That confirmed what she'd said. There was indeed no romantic interest between them.

"Well, okay. Sure. I'd like that. What time and where?" I asked her.

"Is the hotel restaurant okay with you?" she asked.

"Fine by me," I told her.

"How about 7 o'clock? I'll meet you down here in the lobby if that sounds all right?"

"See you then," I told her. "Nice seeing you again, Jared," I said as I excused myself.

I'd been running six or seven days a week for nearly five years but hadn't run a marathon until a year before that. I ran a respectable 3:25:37 my first time out, and I'd whittled my time down to just under 2:45 since then. Kay was also a strong runner and could finish the 26-mile race in under three hours herself. Neither of us were anywhere close to world-class distance runners who could run the race in just over two hours, but we both really enjoyed running.

After a lazy afternoon, I took a shower and got ready for dinner. While I love to really get dressed up as Callie, I'm not into clothes as a guy. I wore a pair of jeans and button-down shirt which, for me, is really getting fancy.

I was sitting in the lobby waiting for Kay when I heard her say, "Hey! Ponytail guy!"

I put down the paper I was reading and looked up. "Wow. You look great," I told her honestly.

Anyone who's read my stories knows I have a thing (a huge thing) for women's sweaters. I'm insanely obsessed with them and as Callie I wear very little else. As Cal, I love seeing a cute girl in one and Kay looked amazing in the long-sleeved, pale green, rib-knit sweater and jeans she was wearing. Being a crossdresser, I pay attention to every little detail when I see a cute girl, and I noticed Kay was wearing a pair of small, gold earrings and a gold necklace as well as the perfect amount of makeup.

"Ah, a jeans guy, eh?" she teased as I stood up to meet her. I was thrilled when she offered me a polite hug which I accepted.

"Uh, sweater guy actually," I told her without offering any additional details.

"Oh, really? I've heard of sweater girls but never met a sweater guy before," she said continuing to be playful.

"Shall we?" I said as I led her into the dining room.

We made small talk about the sea trial—especially her former boss whom we all called Commander Napoleon. He was a flaming asshole that nobody liked, but everyone seemed to respect. As long as he got the job done, the Navy was happy to reward with promotions and command. "Flamers" was one more reason I could never have spent a career in the military. I don't do well with taking orders especially from hard asses. I'll do anything I'm asked, but if someone tires to order me to do something, we're gonna have words right then and there.

After gleaning some personal information, I kind of summed it up by saying, "So you're 27, a Naval Academy graduate, a supply officer, cute as hell and single. I couldn't help but overhear your comment to Jared about that guy named Douglas taking the plunge and the way you seemed to almost fear getting married. Care to talk about that or am I in need of being told to mind my own business?"

Kay took a sip of the one beer she always drank the night before a race and said, "No. It's not personal. Okay, what I mean is, it is personal because it involves me, but it's not a big secret with my friends."

"Secret? You have secrets, Lieutenant?" I said with feigned incredulity.

"Not any more," she said. "At least not since the repeal of 'don't ask, don't tell.'" She waited to see if my facial expression changed then said, "I'm gay. And although gay marriage is now legal, I really don't have any interest in marrying anyone and especially not any time soon. So when I see my former, fellow midshipmen all taking the plunge, it kind of scares me." She paused then asked, "How about you?"

"Long story," I told her. "But I'll be kind and give you the nickel version."

I briefly shared growing up overweight and having horribly bad teeth which made me invisible on my best days and the butt of endless jokes on my worst.

"Oh, my God. I'm so sorry to hear that. You have a great smile and you're really cute—for a guy," she told me.

"Thanks—I think," I replied. I went on to tell her how I started lifting weights, lost the baby fat, put on a ton of muscle and got the braces off.

"That must have been a huge change for you," she said. I could tell she was a good listener and that she genuinely cared. That was important to me because after the way I'd been treated for so many years I learned a lot of empathy for people. Not just sympathy but the ability to actually feel for them. I hated when people teased someone for the way they way they looked and even after my 'transformation' I never put anyone down for something physical over which they had no control or for being overweight.

I shared with her how I went from being invisible to being hit on by pretty much every cute girl in school but that I was still too shy to deal with all the new attention. Besides, I'd had a crush on my English teacher for two years and I had this fantasy of being with her. I wrote about her in one of my papers and that led to me having an affair with her for several months. I also told her about another brief affair with a lonely, married Mormon woman followed by my enlistment in the Marine Corps to escape my little hometown. I explained how during my last year on active duty, I'd met my former wife in South Carolina who became the woman of my dreams through her willingness to do and wear and be anything and everything I'd ever wanted.

"Wow. So how did something that great come to an end?" she asked. Quickly she added, "If you don't mind me asking something so personal."

"Not at all," I told her. "As this all unfolded, she slowly began learning she was a very, very submissive woman." I watched as Kay raised her eyebrows in genuine interest. "It got to the point where I dreaded going to bed with her because I had to be her dom. She needed to be tied up, handcuffed, chained, hooded, spanked, and many other things that just didn't do it for me. For a long time I felt obligated to play along because she did everything I'd ever dreamed of and it only seemed fair I do the same for her. But at some point, it got to be so burdensome, I lost interest."

"So what happened after that?" she said. I could see this was a topic she really liked discussing as much as I did.

"Well, that's where it gets really personal and I'm not sure I'm ready to talk about that yet. Let's just say it led to us going out with other people and my wife wanting someone very strong and very dominating in her life, and that was no longer me."

"It's hard to imagine you were ever fat or unattractive, but it's just as hard imagining you as a guy who lifts. That's quite a swing back and forth."

I pulled out my wallet and showed her a picture of me and my former wife at the beach. "Holy shit!" she said. "You really were freakin' ripped." She kept looking at me then my pic then back at me. "Wow. That's unbelievable."

Then I showed her a pic I carried of me in the tenth grade just before I got my braces put on. "I don't even know what to say. I feel like I just met three completely different people."

She handed me my wallet back and I said, "Well, there's actually a fourth me, but that's the personal part."

She finished her beer and said, "Okay, you can NOT leave me hanging like this. You were overweight and unattractive, then ripped and gorgeous, and now you're rail thin and still very good looking. Who or what is this fourth you?"

"Oh, no. Sorry. Not gonna share that with you. If we knew one another better and if I felt I could trust you then maybe. Even then, it would be a 'maybe' at best."

"Okay, how about if I share something personal with you?" she said.

"No guarantees even then but I am a good listener and I don't talk out of school," I let her know.

"I said I was gay but I'm actually bi. Well, kind of."

"Kind of?" I asked looking for clarification.

"Yeah. I mean, it's been really confusing. I only dated guys until my third year at the Academy although I was pretty much always attracted to other girls. I really enjoyed sex with guys, but I couldn't shake this overwhelming need to be with another woman. That's when I met this other Mid name Allison who was from a small town in Missouri. She knew she was gay all her life. We started spending all of our free time together and she was as gay as they come but hid it perfectly from everyone. Oh, and she was very butch. And for the record, it really is true that most lesbians are pretty butch and Allison was definitely all that."

"You don't look very butch to me. Do you hide that because of the Navy?" I asked her.

"No. Not at all. This is the real me. I'm what people stereotypically call a 'lipstick lesbian.' I like being a pretty, feminine woman. I just like...women." She quickly added, "Sorry. That must have sounded pretentious claiming I'm pretty. I just meant I like to feel pretty. Anyway, I stopped dating guys after that and have only dated women since. Yet sometimes I still miss having sex with a man if that makes any sense."

"That makes perfect sense and nothing you said was pretentious," I assured her. "You are pretty. In fact, you're a very attractive woman."

"Well, thank you," she said almost demurely. "I guess the real problem for me is I want the best of both worlds." She looked at me to see if I was going to ask a question, but I just listened. "I can't plead being drunk after just one beer, so I'm not sure why I'm telling you this when I barely know you, but you strike me as someone who isn't judgmental and as someone who really gets this stuff. So here goes. In my ideal fantasy, I would meet a very pretty girl but that girl would have...well...she'd have a dick to please me with."

I felt something surge through me like a bolt of electricity. I didn't say anything but I felt my heart start beating faster.

"I know. It sounds crazy to me too, when I say it out loud. Too weird for you?" she asked with raised eyebrows.

"No. Not even a little bit weird. We all like what we like, right? I have this thing for sweaters and even just admitting that to a girl used to embarrass the hell out me of because I thought she'd think I was either weird or controlling."

"Sweaters? Wow, you're really are out there on the fringe, ponytail guy." She smiled then said, "Sounds pretty tame to me," she said. "What other um...things...do you like?"

"I could tell you, but then I'd have to...."

She put her hands and said, "Okay. I get it. That's crossing the line. I won't ask anything else. I promise."

"But I will," I said. I reached back and grabbed my wallet again. "I'm just curious. I have a sister some guys say is pretty good looking. She's a fraternal twin so she's obviously my age. I'm just curious to know what you think." I opened the wallet and showed her a picture of me as Callie and said, "Would you go out with someone like her by any chance?"

She reached for the wallet again, but this time she had that look in her eye that said, "I can't believe you're trying to set me up with your sister. You've gotta be kidding." She looked down and I saw her her eyes open wide. "Oh, my God. She's beautiful." She held the picture up so she could compare Callie to me and said, "Oh, yeah. I see the resemblance. You're definitely twins. You're cute but she's the looker in the family."

She handed the wallet back and said, "Yeah, I'd definitely go out with her. She's pretty and feminine and pardon me for saying this about your sister, but she's sexy as hell. If she lives around her I wouldn't mind you introducing me. If she's also gay, that is. Oh, and single, of course. I guess I should have asked."

"She's definitely single and she's also bi-sexual," I told her. I paused then said, "Can I tell you a secret about her?"

Kay laughed and said, "Sheesh! You and your secrets. Okay. I'll bite. What's the big mystery?"

"Um...well...my sister has the um...extra body part you mentioned you're looking for in a girlfriend."

Kay was a smart girl, but she was temporarily mystified. "I'm lost. How can your sister have a...." She looked at me then said, "No. Oh, holy shit!" Kay was clearly blown away. "Are you serious? Is that picture really...you?"

I nodded just once. "It is. So now you know my secret," I said wondering if I'd made a tactical mistake by telling her. I realized it wasn't really a big deal, but this just wasn't something I went around advertising. The last thing I wanted to deal with was a bunch of jokes and ribbing at work. You know, panties on my locker, someone handing me lipstick instead of Chapstick or asking me if I remembered to douche.

"You're absolutely freakin' gorgeous," she said still trying to process everything. "I mean, she's gorgeous. Well no, wait a minute. Since that IS you, then...Jesus. This is just so confusing to someone who considers herself so avant guard on this kind of stuff. I would have never guessed."

I laughed and said, "Honestly? I would have never guessed you're gay, either, but that just goes to show you really can't judge a book by its cover."

"Yeah. I agree. I tend to hang out at lesbian bars and because I'm so femme, I tend to be pretty popular with a lot of the dykes. But I want to find a lipstick kind of girl like myself to be with, you know?"

"Dykes? Oh, okay. I guess that's like a black guy using the 'N' word. He can but we can't."

"Bingo," she said. "Although being called a dyke doesn't bother me in the least. Like Popeye said, 'I yam what I yam', right?" Both of us laughed.

We talked for another half hour or so about my um...hobby...and how it led to my wife and I double dating once when I was dressed as Callie and the way it contributed to our eventual divorce. I was also completely honest about my affairs and hook ups with various men over the years as a kind of full disclosure thing.

After dinner, I walked Kay to the elevator and we both got in. On the way up, we were all alone when she said, "I don't mean to be weird a or anything, but I was just wondering. I know you said you...I mean...Callie...only dates guys, but I gotta tell you I can't stop thinking about her...sorry...you...as her. My head is really spinning here, you know?"