tagTransgender & CrossdressersTim, Callie, Dave and Beth

Tim, Callie, Dave and Beth


Some time ago, I wrote a story called The Agreement in which my first, former, and only wife came home one day and discovered I liked to wear her clothes. The long and the short of it was that she saw this as her opportunity to act on her own fantasies of being with other men by appealing to me to act on mine—which was...to be with a man—something I had never done. We went on our first and only double date which ended rather nicely for both of us but as it turns out, that was the beginning of the end for our marriage. It wasn't my crossdressing that ended it nor was the fact my ex-wife readily admitted I looked as good as she did when I was in drag. Both of us just came to the realization that we weren't enough for one another, and the marriage ended rather amicably.

I'd been an avid weight lifter from high school on and a pretty decent distance runner. I still run several times a week, but I've quit lifting entirely because muscles don't add to one's ability to pass in public. By the way, I've written some other stories which predate my crossdressing days you might enjoy. One is about my high school English teacher and another is about a lonely, neglected Mormon wife. I had affairs with both of them when I was a senior in high school and at the top of my lifting game and after getting my braces off. When I later realized how much I loved dressing up, the lifting had to go. When I first started getting into crossdressing, I still had some hard muscle tone as you may be be able to see in the standing blonde pic, but that's all gone now. I've also since had some work done on my nose and eyes. I kind of regret the nose job because while it looks just fine now, it was actually pretty cute and feminine before. Oh, well. As they say, that ship has sailed. I'm obviously a few years older and about 15 lbs lighter mostly due to muscle loss. (Big sigh on the age thing.) C'est la vie, no?

I've dated both men and women but I prefer dating men by far. Women are nice and we fit together perfectly, anatomically speaking. I just can't deal with all of the compromises women expect. I understand them and they make perfect sense. I just don't feel like putting up with all that so I tend to stick to dating men during my time as Callie.

I've had several private emailers ask me why I don't transition and go full time. The answer is simple: I like being a man and can't imagine that ever changing. Being a woman is a lot of very hard work. I agreed to go on a cruise with one of my boyfriends a few years back and spent the entire time as a woman. The first day was utterly thrilling! The hair, makeup, jewelry, pretty clothes, etc. Yummy! The second day was still pretty great. But by the third day, I was sick and tired of having to sit up straight, keep my legs crossed, smile at everyone all the time, and use my feminine voice. I couldn't wait to get home and change into some shorts and a t-shirt and slouch all the hell over my couch, drink beer, and belch out loud. No, I'm not kidding. Being a girl is fun, but only if it's part time and when I feel like it. So no transitioning for home boy who still works as an engineer at a Navy base. (And no, I am not on active duty as others have asked. I could never deal with those six-month deployments. God bless the folks who can but I'm not cut out for that.)

I also wrote about a great experience I had with a neighbor woman named Shada and her husband. That was simply awesome and the three of us got together one other time after that. But a couple of weeks ago, I had THE best, most fun experience to date. I'm still dating "Tim" so who knows what the future may hold. I'm not sure how to top this one because I'd never do something crazy dangerous like an impersonal orgy or a bukakke party. Okay, I might be willing to try three or four guys but only if I knew them all and trusted each one completely. That's not likely to happen, though, because meeting men who admire girls like me in my female persona is easy. Meeting guys I'm both attracted to and can trust is not. And all the fantasy stuff aside, trust is essential because no one wants an STD or to end up dead from an encounter with a handsome guy who's really a "fag-hating" sicko. So I pick and choose very, very carefully and I only agreed to do this because I trusted Tim completely.

Once we got um, better acquainted, he suggested meeting his best friend from college and his wife. As it turns out, his friend, Dave, was also fascinated by girls like me and his wife, Beth, was also extremely curious. I trusted Tim and he trusted them so I was willing to meet them for dinner. Dinner led to...well...read the story and find out, okay? I'll just say it was an absolutely amazing encounter I hope to repeat again—soon!

I hope you enjoy reading about it as much as I enjoyed living it. Lastly, I've had other emails (I get a LOT of them) who say I spend too much time "bragging" about how I look en femme. I'm not bragging. I just write about my experiences and that includes what people tell me. I won't apologize for writing what others say about me. I obviously can't recall every comment word for word, but I do my level best to report them as closely as I remember them. If it sounds like I'm tooting my own horn, that's something you'd have to take up with those who are so very generous with their kinds words.

As you might suspect, I've changed everyone else's name except my own which, of course, isn't my own—except when I'm being Callie.


Callie Lynn Coe

I met Tim at a drag show called Screaming Queens earlier this year. I rarely attend events or go places designed for the transgendered but I'd heard this show was really good so I decided to go see for myself.

One of the performers saw me in the audience and made such a fuss over me that I ended up going on stage with her after she kept egging me on. I tried to say "no" several times but she was having none of it. By that point, every person in the room was staring at me and egging me on get up on go on stage. For the most part, she was very gracious but like most drag queens, she was also one foul-mouthed, caustic bitch! She went on and on about me and how I bet I thought I was "all that" and she shredded me for my hair and my nails and my fake boobs and...well, pretty much everything to include things no lady should talk about. Well, at least not in public!

After a lot of laughs—mostly at my expense, I went back to my table where I'd been sitting with a couple of other girls who sadly, couldn't pass in public. A few minutes later, the girls on stage took a break and that's when I noticed THE most gorgeous man smiling at me. I'm not shy about flirting, but this guy took my breath away. I remember thinking he looked like a cross between Tom Brady and Matt Bomer from the TV show White Collar. (Tim looks a LOT like Matt. Yum!)

Only this guy wasn't gay. Okay, let's put it this way. He'd never been with anyone but a woman in his entire life, but he'd developed an enduring fantasy about meeting a girl like me which finally drove him to act on it. For a couple of years, he indulged his fantasy by watching on-line porn and makeover/transition videos but eventually, that wasn't enough. A website called TV Bunni was his favorite but even that wasn't sufficient when he ultimately realized he wanted to experience the real thing.

He finally decided to take the first steps to try and meet either a transsexual woman or a very passable crossdresser. He told me he'd been to several clubs looking but had only found two other "girls" he found reasonably attractive. He introduced himself and chatted them up only to learn that both of them were absolutely straight—which is the case with most crossdressers, btw. He was beginning to think he'd gone on an impossible mission and then...he found me.

He's told me several times how lucky he felt, but I'm actually the lucky one. He is so very—delicious looking!! (I was flattered when he had to ask me whether or not I was TS. In fact, he said that had I not been up on stage and shown my silicon breast forms he wouldn't have know I wasn't a GG—genetic girl.)

Now that the stage (pun intended) is set, this is how our most excellent adventure began.

"So thank you all and especially thank you, Miss Callie Coe for being such a good sport—bitch!" Roars of laughter. "Okay, ladies—and admirers—how about a nice round of applause for the bitch—I mean—the belle of the ball?" Once the applause died down, she announced, "We'll be right back folks after a short break. My girdle is KILLING me!"

"Callie? That guy over there has been staring at you since you sat back down," the girl next to me said. She'd introduced herself to me as Kristina and we'd made small talk off and on for the last hour or so.

I turned over and saw him looking at me. I thought for a moment I was dreaming or watching a New England Patriots game on TIVO. This guy was so hot I could feel fire spreading from my rosy cheeks to the man-gina between my legs. His smile made my legs weak and I was hoping against hope he wasn't gay in the traditional sense and that he was indeed smiling at me. I decided to smile back and to my great delight he stood up and walked over to my table.

"Oh, my God! He's coming over here!" Kristina said.

"I hope so," I told her without taking my gaze off of this absolute hunk of a man.

My heart was pounding furiously in my chest as he stood next to me and said, "Hi. I'm Tim. Nice performance up there."

I smiled and thanked him. He asked if I'd mind if he sat down and I told him, "Not at all. I'd like that. My name's Callie."

"So I heard," he teased. He took a seat next to me and said, "Nice to meet you, Callie. If this sounds cliche I'm sorry, but you are an incredibly beautiful woman."

"Cliche or not, I'll take it. Thank you!" I said sincerely. "That's so sweet of you."

The club had some dance music blaring and Tim didn't feel like talking over it so he leaned toward me and said, "It's really loud in here and I'd like the opportunity to talk with you if you wouldn't mind. It's a whole lot quieter in the lobby." He nodded in that direction and I was more than ready to spend some time alone with him.

I turned to Kristina and said, "I had a lovely time chatting with you, Kristina. You take care, okay?"

"Same to you, Callie," she said in a distinctively masculine voice. Then she leaned closer and said, "Be careful, okay?"

"Definitely and thank you, hon!"

Tim stood up and pulled back my chair. I was impressed. Looks and manners. Wow!

He offered me his arm which I took as he escorted me out of the noisy showroom and into the lobby. "Would you like something to drink, Callie? Some wine possibly?"

"That would be lovely as long as you're having a glass, too," I told him.

He caught a server's attention and ordered two glasses of Zinfandel. There were several tables and a few benches in the lobby and Tim suggested we have a seat where we could talk more privately. Again, he pulled back my chair to seat me and I thanked him. As he took his seat our drinks arrived and he offered a toast: "To the possibility of a new friendship?" I repeated the phrase, touched my glass to his, and we each took a small sip.

"I'm rarely at a loss for words," he began. "But I have to tell you this is completely new territory for me. In fact, I'm not really sure how to even say this. It's just that, well...I'm pretty sure you're the kind of girl I've been wanting to meet for the longest time so..."

I smiled and pretended I wasn't sure what he meant. I said, "What kind of girl are you trying to meet, Tim?" I raised my head slightly as though I was anxiously anticipating his reply—which I actually was, by the way.

"Well, this is where my inexperience in this area is a real handicap because I'm not sure how to put this but here goes." He looked uncomfortable and I sensed that was something he was used to when it came to meeting women. He looked down, took another drink of wine, then said, "I'm a totally straight guy." He stopped, looked at me, then seemed even more flustered.

"Go on. You're totally straight and..." I tipped my ever so slightly to one side to again indicate I was paying very close attention to every word.

"Well, at least I think I am. Or at least I always have been. It's just that for the last couple of years or so I've had this...this...interest in meeting a girl who's well..."

I interrupted him by saying, "Like me?"

"I beg your pardon?" he said. He looked confused.

"You've been wanting to meet a 'girl' like...me. In other words, you're confused about your sexuality because although I look like a girl, you're interested in meeting one who has um...something...special...that other girls don't have. Am I correct?" I teased.

Tim smiled that killer smile and said, "That's exactly what I meant to say but didn't know how to say it. So thank you for putting it so well. I've only shared this new um...interest of mine...with my best friend from college and he warned me that most girls like...well, like you...are completely straight. Straight as in they only date women. So before I stick my foot any deeper into my already wide-open mouth, I guess I should ask whether or not you...you know...date..."

Again I finished his sentence. "Guys like you?"

Tim laughed and looked relieved as he said, "Okay. Yes. Guys like me."

I took another sip then smiled at him. "That depends."

He looked crestfallen as he said, "On?"

"Well, it depends on whether or not this is purely hypothetical or whether you're actually asking me out on a real date."

He looked relieved as he smiled and said, "I would love to go out with you sometime, Callie." He got very serious and then asked, "Would you do me the honor of having dinner with me one evening very soon?"

"Yes. I would love to, Tim. So in your case, yes, I do date guys like you." I smiled broadly then asked him for his cell phone so I could enter my contact information. I have a "burner" phone I use only for whatever guy I happen to be dating. When the relationship ends, the phone gets tossed for privacy reasons.

He looked at the info I'd provided and thanked me. "Callie? I just wanted to say again that you are incredibly attractive."

"Thank you. That's very kind of you to say. It takes a lot of work to get Callie ready for a night on the town."

"Well, she certainly does a fantastic job. I've dated some really attractive women before, but you're as pretty as any of them. You're...gorgeous." He hesitated then quickly added, "And that's not a line. It's the God's honest truth. You are really beautiful."

I cocked my head again and Tim said sincerely, "No. Really. I'm not just saying that. You look sensational." He paused for a moment then said, "Again, I'm totally new to this so I have no idea what's appropriate to say so if I say the wrong thing, please forgive me. It's just that I've been looking for a few months and I haven't seen anyone...and I mean not anyone...who looks like you." He hesitated for another moment then said, "Well, that's not completely true. I did meet two different TG girls who were attractive but neither was in your league. And neither of them um...dated guys like...me."

I thanked him again for the compliments then said, "I'm not new to this but I am very, very careful about whom I date. Let me just say that all I expect early on is complete honesty and to be treated exactly like any other woman. To address your um...fantasy concerns...yes, I do indeed have the something...extra...I believe you're looking for, but let me say this up front right here and now. That body part is completely off limits to all men." Then I paused for effect before saying, "Assuming of course we have dinner, we still like one another, and we get past a goodnight kiss. I keep that restriction in place so I can feel like a woman when I'm out as Callie. I like to try and do that twice a week but more often than not it's one night a week but... Anyway, a part of that—for me at least—is feeling like a woman in every way possible. So touching that part of the anatomy would make me feel like I'm a man with a man and for whatever reason, my brain isn't wired that way. Does that make sense?" I plowed ahead and added, "I'm not homophobic by any means. It's just that my male persona has zero interest in men and for whatever reason, that has to be a limit that is completely respected when I'm out as Callie who most definitely does have an interest in...some...men."

Tim seemed completely understanding and told me, "That does make sense. I mean, I've never thought about that but hearing you say it, it makes perfect sense. I have to tell you I'm really grateful for your honesty and I will be completely honest with you, too." I could see a look of...distress, maybe?...on his handsome face.

"What's wrong, Tim? Please feel free to ask me or tell me anything. I'm a big girl. I can ...take it." I emphasized the words "take it" and I saw Tim close his eyes.

"No, nothing's wrong. It's just that...you're so amazing. I feel like I'm in junior high school asking my first crush out on a date. I don't want to say or do anything to mess this up. I feel like I'm in the middle of the best dream ever and that I'm going to wake up and realize you weren't actually real."

"I'm very real," I assured him. "And for the record, I'm enjoying the view from over here very much myself."

Tim smiled again before saying, "Listen, I know a great place in the District if you'd like to have dinner with me this weekend," he said.

"I'd love to!" I assured him. "How formal is it?"

"It's not formal in the sense of black tie or anything. I'm suggesting it because it's a really nice, very upscale place and I definitely want to make a good impression on you. And even though I don't think anyone would ever guess you're a...special kind of woman...I don't want to go to my normal places where people know me. It's just that..."

I cut in and said, "I get it. That makes perfect sense. Friends want to be introduced and they ask a lot of questions and at this point you don't need to be doing a lot of explaining. So no worries, okay? In fact, I might think you're somewhat reckless if you didn't have those kinds of concerns. So no offense taken. I was mainly interested in knowing how formal it is so I can dress accordingly."

"Well, you look great dressed just like that. I mean, it's a really soft, feminine look and it...it really suits you."

It was the middle of summer in Northern Virginia so it was still very warm and humid. I was wearing a dark yellow, sleeveless, rib-knit top with a skirt that matched the color of my top and that had a thin black belt. That allowed me to wear a pair of open-toed, black sandals with three-inch heels and suntan colored stockings. In terms of jewelry, I chose gold earrings (I've had pierced ears for several years) and a matching necklace along with a gold watch and one gold ring I wear on my right ring finger. A cardigan sweater which I carried and a black purse completed my ensemble.

"I love everything feminine, Tim, but I adore sweaters and knit tops more than anything. I always have and over the years, that's never changed. Not sweaters in the sense of the heavy, bulky, baggy, grandmother type sweaters one stereotypically thinks of but rather the form-fitting, very dressy kind. Is that okay with you?" I inquired.

"Yes. Very okay. You'd be beautiful in anything you wore so as long as you're comfortable, I'm very happy with whatever you choose."

"Wow! Good looking, well-mannered, and not controlling! I think I like you, Tim," I said playfully.

"I'm very sure I like you, Callie." He paused and then looked down at his very expensive watch before saying, "I'm sorry but it's after midnight and I have to get up very early tomorrow as I have a deposition at 8am."

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