My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise!
I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, short, and very insecure, especially about my looks and attractiveness to the opposite sex. Girls have never been attracted to me (and I've always really wanted them to be, always sought approval from girls, which may have been part of the problem, since, as I know a lot better now, girls generally want to be the ones getting approval from guys and they view a guy caring too much about what they think as sort of wussy.
Ever since I was little, I have had thoughts about what it would be like to be a girl. I guess because I liked girls so much-the way they talk, walk, dress, act, everything-I became fascinated, almost obsessed, with femininity. I started crossdressing a little at home when my parents weren't around or, if they were home and I had the "urge", I locked myself in the bathroom to do it. I also started sneaking some of my father's Penthouse and Playboy magazines to look at. That part seems normal, right? Wrong-because the prettier one of the girls inside was, the more I wished I could be like her, be her, instead of being with her.
The part of the magazines I really enjoyed, though, were the "Forum/Letters" sections, where people wrote in to tell stories of encounters or fantasies they wanted to share. Again, I always imagined that I was the girl in the story, and I was especially taken with any story where the girl was shy and reluctant as sexual things were being done to her, which seemed to be the way it was in a good number of the stories. I found out eventually that a girl being this way, trying to remain a "good girl" while a male overpowered her and had his way with her, was called "submissiveness"...this was often painted as a fetish, or something kinky, but I figured out over time that even the most straightforward sexual situations, where there was no "scene" or 'kink" or such but that a girl was just being "taken" by a guy in whatever setting, featured this element.
I realized that most girls, deep down, in those secret places that they only share with their girlfriends and their diaries, were submissive, and both liked and sort of needed to be dominated by boys.
This began to explain somewhat my inability to make girls see me as anything other than gross or invisible. Girls wanted a boy who was confident, aggressive, a "bad boy". I was the furthest thing from this ideal, and this was confirmed repeatedly over the years. Sometimes girls who I was friends with ("just" friends, of course) would try to help me when I whined about my luck with other girls, and the advice was always the same-girls love confidence in a guy, you have to be confident, you can't be insecure. Well, sure, it's easy for the confident guys to be confident-they're, like, tall and cute and athletic and uncomplicated. I had no reason to be confident; confidence on my part would have looked even more ridiculous than my wimpy demeanor did-what girl is going to be swept off her little heels by a short, fat guy who everybody in school knows backs down from fights with other guys? Exactly.
I also now had a good understanding of why I identified so strongly with the girls in those naughty stories. How could I identify with the guys? I had nothing of what they had-I wasn't tall, strong or confident, I never took control of a situation, and girls never looked at me as someone they could be submissive to. God, what could I do? I was so into girls and their girlishness, and I found that whole dominant male/submissive female "dance" so intoxicatingly sexy, but there was no way I could ever occupy the male role in such a scenario, despite the fact that I was born male. So I did the only "reasonable" thing-I internalized the other side.
I began to inhabit the girl role, in my mind, in my dreams, my fantasies. I even learned to masturbate in a way that physically emulated the way a girl touches herself and couldn't get myself off in the "normal" way for years!
I had a few relationships with girls but things would get weird when my story, which I would try to repress, emerged. As much as some of these girls tried to deal with my gender issues, eventually they would need someone more masculine to satisfy them and things would end. I always thought that if, somehow, I ever met a girl who I could tell, for certain, was truly attracted to me (especially if she was someone I was really hot for as well), my need to be girlie would fade and I would realize my "normal", true maleness.
Well, back in 2001, it happened. I met JoAnnie, a brilliant, creative, deeply wonderful girl who also happened to be an incredibly gorgeous, feminine Latina (my #1 "type"). She was 21, she's 5'4", 122 lbs., with shoulder-length, dark brown hair, big brown eyes, pouty, pink lips, large, round breasts, and long, lean-but-not-skinny) legs. We hit if off great and within weeks we were hot and heavy, and it was clear, from things she said and the general way she interacted with me physically, that she found me attractive and perfectly normal in terms of sexuality. However, there would soon be trouble in paradise.
You see, when JoAnnie and I met, I was at perhaps the happiest, most stable point in my life. I was away from the dysfunctional environment I'd grown up in, had a nice place in a nice town, a good job, and I was exercising and eating particularly healthfully, which had resulted in a weight loss that put me at an almost-OK size (these days I'm heavier than I've been in ages). So I was confident and carefree at that time, certainly contributing factors to how attractive she found me. Right around 9/11, however, things started to crumble. Much of my life to that point had been filled with abuse, hardship, and depression; now, it was heading back down that road-I lost several jobs, eventually lost my apartment and had to live in near-squalor, was unemployed and nearly homeless for months, and began eating poorly and gaining weight as well as getting sick a great deal. Relations between JoAnnie and me, needless to say, grew strained, and it became obvious that she was no longer terribly "into" me sexually.
Couple this with the fact that, quite frankly, she's model-beautiful and lived in New York City and was hit on daily by a variety of men who were any combination of good-looking, fit, tall, interesting, artistic, spiritual, and financially secure (not to mention the ever-popular "not making her miserable with their problems and insecurities"), and, well, what's a girl to do, you know? I guess JoAnnie could only resist so much before she was overwhelmed by how fun all the attention was, and she started to give in, to date and flirt with other guys. I was never sure how far she went, but it seemed from her demeanor with me that she was just having a bit of fun, not really getting too intense with any of these guys.
At this point I suppose you could say I reached a sort of crossroads. I still had an opportunity to assert myself and my manhood and make an all-out, unflinching bid to reclaim my girlfriend. But I found instead that the more I thought about what she might be doing while she was out on dates (she didn't tell me but I knew when she didn't call on a given night, because we always talked at night), the more turned on I would get. Not that I didn't feel jealous, because I certainly did, but it was a jealousy that existed in tandem with a feeling that there was nothing I could do, nothing that she could do, that it was only right that a sexy girl should be out playing with cute boys...and I obviously wasn't the cutest boy she could be playing with. I realized that, despite all the years of being resentful toward girls for choosing other more stereotypically macho guys over me and marginalizing me sexually, that, if I were a girl, I would do the exact same thing, especially if I were a girl in the 99 th percentile of attractiveness (i.e. JoAnnie).
So I started tentatively coaxing the details of her dates out of her, like how she dressed, how he treated her, whether he was a good kisser (if he kissed her) and, most crucially, whether he was aggressive with her. I don't know exactly why, but I guess it turned me on to hear about someone else making her feel the way I couldn't. [A note here: I could have broken up with her, yes, but I love her and wanted to try to make things work somehow. She said she did too but for now-which has "now" been at least 3 years-she was going to be dating other men.] JoAnnie was a bit taken aback at first, but for some reason she came around and soon was describing exactly what she did on these dates to me, sometimes over the phone, sometimes in bed with me. She wouldn't let me fuck her anymore, nor would she even think about going down on me, but she did let me go down on her, which is the one thing I do better than most guys-surprise, surprise-and she would play with my nipples (which makes me feel very feminine) as I jerked off as she basically let me know that I couldn't really make her feel the way these other guys did, and that she and her girlfriends had all been giggling and girl-talking for some time about what a sissy I was-because she told them-and encouraging her to go out with more macho guys.
Which brings us up to the present. We have been trying to stay together spiritually, but JoAnnie has continued to flirt and play and, well, it's gotten a bit more intense. In the last few weeks, her girlfriends Karina, Melissa and Kathy have been calling and coming over quite a bit, and whenever I see them talking to JoAnnie, they're whispering in urgent breathless bursts. I hadn't been able to catch what they were talking about for awhile-it was schoolgirlishly secretive-but I could detect the unmistakably gushing tone of girl-talk, and it didn't strike me as totally innocent. Then this past Friday, the girls called to tell JoAnnie that they were coming over and apparently asked her if I could give them a ride to the mall. I agreed and in about a half-hour we were on our way. The whole ride over they were giggling and squealing (JoAnnie included) like a hyper cheerleading squad; about what, I couldn't tell at the time because they took care to keep me from hearing. When we got to the mall, the four of them made a beeline for all the stores which carried the cutest, flirtiest clothes in the mall-Forever 21, bebe, Charlotte Russe, Delia's, and, of course, Victoria's Secret. I tagged along like a good boyfriend, trying to take in as much of them shopping (and checking out boys shamelessly) as possible but not wanting to look like a perv (or, worse, more interested in their girlie exploits than a "real man" ought to be). I noticed that JoAnnie was the only one among the girls who was actually trying on outfits, something I found curious.
After about two or three hours of this, the girls looked to be as "finished" as four girls with no particular purpose in mind can look. At least, I thought they had no purpose. Little did I know, but I was about to find out. They emerged from their last attraction, Victoria's Secret (I found this a bit odd as JoAnnie doesn't wear fancy underthings that often), muttering something unintelligible, save for the phrase "finishing touches", which I heard clearly.
Then I heard Karina insist, "Now you have to go out with him-otherwise the outfit is going to go to waste!"
That got my attention but I was still slow on the uptake, stubbornly assuming that "him" referred to me. Before I had much time to turn it over in my head, though, I got another eye-opener. Of a sudden, my girlfriend and her friends were being approached by a guy. A very good-looking guy. A very tall, well-built, confident-looking guy. A very...different-than-me-looking guy. His name was David, and he was 6' 2", about 200 pounds, with a physique that fell somewhere between that of a basketball forward and a football quarterback. He strode cockily up to the gaggle of young ladies, barely offering me a sidelong glance.
Obviously feigning surprise, Karina gushed, "Hi, David!!! What a coincidence, we were just talking about you-well, JoAnnie was doing most of the talking, actually."
All the girls giggled when she spoke, and JoAnnie began to blush a delicate shade of pink.
"What's up, Eni?" he inquired, calling her by the more little-girlish nickname that her friends and family used. "Doing a little-or a lot-of shopping?"