Monday, March 30, 2015

Jenna Talackova, and the importance of transitioning when young

I greatly admire Jenna Talackova, the beautiful, sexy, and courageous M2F transgender model, beauty contestant, reality television star, and actress. 

I sometimes wish I would have had the foresight and knowledge to transition and become physically female when I was young – when the results can be so lovely and perfectly feminine.  In my opinion, late-life gender transitions are generally undesirable, because decades of male hormones cause too much damage to successfully overcome.  Plus, if you truly are transsexual, you would naturally want to transition as early as possible in your life. The fact that I’m middle aged and I’ve never transitioned is evidence that I’m a transvestite, not a transsexual. But I suppose people could debate such matters endlessly...

Everyone has different circumstances in their lives that may either limit or encourage the actions they take, as well as different standards of what they may find acceptable in their own appearance. But I know that I would not find gender transition results acceptable for myself at my current age. I could no longer be the young sexy woman I would want to be, no matter how much surgery I got or how many hormones I took! My only hope of becoming the beautiful woman I fantasize about being will have to wait until my next life. (I hope reincarnation is real!)

In any case, please enjoy and learn from pretty Jenna…

Jessica Sayyida is the author of My Transvestite Addictions—The Story of One Individual’s Odyssey Through Crossdressing, Alcohol, Escorts, Strippers, Sex, and Money
(ISBN: 978-1-62646-325-7), published under the name of Jack/Jacquelina A. Shelia, by

Saturday, March 28, 2015

New therapist: trying to figure it all out (chapter 9 of my book, My Transvestite Addictions)

On Wednesday, June 8, 2011, I saw Dr. Mary Newhart for the first time. I went dressed as Jack. I immediately liked her much more than my previous two therapists. First of all, she was young and pretty, with long brunette hair, a nice dress, and high heels. She looked like my kind of woman—that is, the kind of attractive, feminine woman that Jacquelina wanted to be. Furthermore, she seemed to actually listen to what I told her. Over a four-hour session, she asked me many probing questions that made me think—about my childhood, my parents, my relationships, my sexuality, my feelings, my thoughts, my impulses, and, of course, my crossdressing. She took notes while I talked to her. She seemed genuinely interested, like she really wanted to help me.

Although Dr. Newhart’s questions made me think hard about my crossdressing and gender identity, I think—because of my recent feelings of unease with Jacquelina’s sexual and drinking behaviors—I went in there with a preconceived notion that I needed to stop or at least limit Jacquelina. Like, OK, I’ve spent a year experimenting with being a woman, and now enough is enough… I had fun, I learned things (including various insights into what it means to be a woman), and now I needed to be satisfied with being Jack. My Jack-Jacquelina duality ultimately causes more stress for me than it relieves—and more stress than it is worth. I can be only one person. So I have got to be Jack and Jack only in this life in this world…

At least, that’s the line that I was telling both myself and Mary. And that’s the mentality I had when I walked out of her office that day. I might have temporarily deceived myself with those ideas, but I don’t think that Mary ever believed them. She knew that it was not that simple or easy.

I would see Mary a few more times over the next few months—as both Jacquelina and Jack—until I decided that she probably couldn’t help me as much as I had hoped. In retrospect, perhaps I never gave her much of a chance to help me clarify my issues. But she did definitely get my mind to seriously thinking more about those issues. In particular, she got me to do some serious thinking about how boredom or stress combined with my impulses and alcohol use lead me to do things I later regret, and about how I might want to try to find additional social avenues to occupy my mind and time. She pointed me in a constructive direction to confront my addictions. I felt—and still feel—that Mary was at least more helpful than my previous therapists. Although I only saw her a few times, we’ve been in frequent contact via e-mail, and she has continued to offer me advice and helpful comments that way.

As unrealistic notions about forever getting rid of Jacquelina danced around in my confused head, I contacted some of my friends and acquaintances over e-mail about my positive feelings in finding a new therapist. People tried to let me know that they cared, and they also shared their thoughts…

From Helen, my former boss at a publishing company:

Hi Jack,
I was so glad to hear that you found a therapist that you can relate to. It sounds like you made astounding strides in your four-hour session… Working with someone to find the authentic you is the most important thing. And, in my experience, finding that authenticity just feels “right.” I’m not sure there is a way to quantify that feeling.
The main thing is that you feel good about yourself, who you are, and what you are doing, how you are being. It might take some time, but the effort is worth it…
The main thing is to take good care of yourself.

From Adriana, the editor and friend who had visited me at home and gone to dinner with me as Jacquelina:

Hey Jack,
Thanks for sharing all of that with me…. I’m no psychologist, but “controlling impulses” to dress and act as a woman seems strange to me. If you want to be Jack—not Jacquelina—I think everyone you know will be just as supportive as they have been with Jacquelina. I know I support you 100%. I just don’t know if it’s healthy to repress those feelings if you keep having them. But, from what you’re saying, maybe it’s not healthy to live them out either. In any case, I think continuing to see Dr. Newhart and becoming more social will really help, as I’m sure some days will be better than others. Anyway, those are my thoughts, even though you didn’t even ask for my opinion.

From my longtime friend Cathy:

You sound much more grounded and clear-headed. After four hours of digging around in your psyche, weren’t you exhausted? I think... no I’m sure, I would have broke down crying.
      Escape to the woods with pen and paper. Write a book! Become an artist and hang out with folks who wear black and use the word juxtapose in every sentence :-)
Focusing on Jack could be fun. Who knows who the new/real you could be in there? I’ll focus on Cathy while you’re focusing on Jack and perhaps we both will discover new things.

Even from Kara, a beautiful fashion model whom I had “friended” over Facebook:

Let me start by saying, I am very proud of you. It takes a big person to recognize what really is at the root that causes us to do and think like we do. It takes an even bigger person to want to deal with it and not mask it. I feel very honored that you shared your news with me. Always know that it really doesn’t matter what is on the outside. It’s what’s on the inside that matters. You are a very talented person and from the sounds of it, you have a huge heart. Fantasy is fun, but not forever... Believe me. LOL. I am happy to hear that you found your right path. Keep on it!! Don’t let the outside negativity bring you down. I am always here if you need a friend to talk to or just listen.
Thanks for Sharing.

And from Natalie, Kara’s colleague and my best model friend:
Hi Jack,
You sound happy…
Hopefully you will find some peace with it all.
I only wish you happiness and love.
Please keep in touch.
Much Love my friend,
Natalie XOXOX

Wow! It felt especially good to have such famous “friends” who seemed to care. But eventually I had to get back to struggling with my complex, confusing, contradictory life in the real world—all by myself.

The many words of support from these well-meaning folks came after I e-mailed them messages like the following:

I believe that Jacquelina started out as a healthy self-expression, but evolved into a type of unhealthy addiction that became all consuming. I feel I am free of her now... I think partly because I reached the one-year milestone of expressing her on May 25, and I actually think I did everything as her that I ever fantasized doing... so there’s nothing else I want to do as her anyway. And now I don’t feel compelled to be her anymore... and I now understand the feminine feelings I’ve had since age 10 are simply that... feminine feelings.... nothing wrong with having them, but having them doesn’t mean I want to be female.

Despite such firm words of resolution on my part, in reality, I was still very confused and very conflicted! And I was very far from any true resolution regarding my crossdressing and gender identity. And I still had more female fantasies that I wanted to experience. I was unintentionally misleading and confusing all these good people because I myself was confused. Jacquelina was here to stay, no matter what Jack thought of it.

By the end of June, I dressed and went out as Jacquelina a couple more times. On June 27, I visited Dempsey’s with my transsexual friend Malaya. I wore a long platinum blonde wig, a black tunic top, tight sexy skinny jeans, and adorably cute pink pumps. On June 30, I wore my long brunette wig with a shoulderless little black dress, black pantyhose, and silver pumps to Dempsey’s. I also visited Manny’s that night in my LBD. I drove home from Manny’s early in the morning totally drunk and half asleep—snapping photos of myself as I drove. When I looked at the photos later, I saw that my eyes were closed in half of them.

I just couldn’t help myself… I simply loved loved loved being Jacquelina! And it seemed like the more I tried to push her away, the stronger she came back. I also had to admit something else: I apparently enjoyed taking risks, including drinking to the max at bars and then driving home.

In early July 2011, I had a session with Mary in which she seemed to reach the tentative conclusion that my main problem was the lack of a girlfriend—the same conclusion that my previous therapist had reached. Although I knew that was part of my problem, I was disappointed that another round of therapy ended up focusing on this, because I felt that there was nothing I could do about it. Years and years of bad luck with women had convinced me that no woman would ever want me for a serious boyfriend or husband. As I e-mailed Mary the day after our session:

Thank you for your time and help yesterday. 
I regret that the session turned in the direction that I knew it eventually would: my need for a girlfriend. I know that a girlfriend would help, but I also know that I will never find one. Plus, a series of inevitable rejections will end up making my ‘condition’ worse...
I’m very sorry that I am so terribly pessimistic on this matter, but I am. I just think it is unrealistic... In fact, it is probably more realistic to return to my idea of hormones and female transition. In other words, I would have a better chance of beginning transition (I mean, all I have to do is get hormones shot into me) than of meeting a woman who actually wants to go out with me.
The hard, cold truth may be this: there may simply be no real solution for me (unless I can find that magic wand that will instantly turn me into a beautiful female). I think the best thing for me right now is probably to just try to forget about everything for a while... The more I think about my personal mess, the more confused I get. I wish I could just get a totally blank mind for a few days (but this gender thing is always in my consciousness... it never goes away).
Anyway, I’m going to try to concentrate totally on my work today... with no thoughts about gender identity... see how it goes.

Mary responded with the following:

I hope you’re having a focused and productive day! If you have time during the hours you aren’t working, I had a few thoughts in response to your email, food for thought for our next session maybe. It is sometimes difficult to discuss sensitive topics over e-mail when you can’t see the other person’s facial expression, body language, etc. You made the comment that talking more frequently might be helpful to you, and when I have time to communicate between sessions I am happy to do so. However, I hope you will keep in mind that in any e-mail message, my intentions are to continue the wonderful work you do in sessions, and to avoid harming the therapeutic relationship in any way. I hope that if an e-mail bothers you, you will let me know and bring any concerns to a session so we can discuss them directly.
From our conversations I get the sense that you want a relationship, but anticipate rejection and are fearful of being hurt. You seem to attempt to suppress the natural desire for a close relationship, but wish that the perfect partner would somehow appear—and when she doesn’t, you use that as further evidence of the futility of seeking a partner, and as justification for not addressing a painful, anxiety-producing part of your life. Do you feel I am understanding your struggle in this area? I want to make sure that I understand you well. I would like to help you to reach your goal of joy and contentment, and I also want to be sensitive to your hesitation and fear of seeking a relationship. After we talked yesterday, I wondered if you feel your expectations for a partner are unrealistic, and if so, if that could be a complicating factor here...

Mary was trying to be helpful, but she just could not understand my pessimism regarding relationships. Nobody has ever understood that. Only I do. I know it is real, though I cannot explain it adequately to others. I feel that I cannot explain it adequately in this book. I know as sure as I know anything that women simply do not want me as a boyfriend or husband. I don’t understand why women feel that way, but I know that they do. It is a basic, time-proven fact of life for me. There will be no Hollywood ending for me in which the beautiful woman comes into the life of the troubled man to save him at just the right time. The only way I could get a beautiful woman is to pay for her.

In the long course of writing this book, I wrote the previous paragraph before I met Selena—a woman whom I initially paid for but whom I now (as of this writing in early 2013) am dating on a regular girlfriend-boyfriend basis. But that relationship has just begun… Hollywood, stay tuned.

Another fact of life for me was that—contrary to Jack’s chronic lack of success with women—Jacquelina was having great success with men. Success in terms of sex. That’s all Jacquelina wanted from a guy—someone with a cock for her to suck or someone to bang her in her ass. She had absolutely no interest in a “boyfriend.”

Jacquelina’s drunken sexual conquests—which almost always happened with no condoms or other protection—had long had me worried about AIDS or other sexually transmitted diseases. On Friday night, July 22, I dressed up like a Barbie girlie girl—in a long wavy blonde wig, a lacy pink cami, a short frilly black skirt, nude pantyhose, and my pink pumps—and I drove to Manny’s looking for some action. While I was there, I took advantage of the free HIV-AIDS testing that a guy did in a private room on the second floor. After I handed him the swabbed sample from inside my mouth and he started the test, I nervously chatted with him while we waited a couple minutes for the color change. The results were negative.

I breathed a big sigh of relief! And, as I stocked my purse with free condoms from a bin in the room, I made a mental note to be more careful. Unfortunately, such mental notes do little good when your brain is clouded with alcohol—as mine always was when I got together with a guy for sex.

After I got the good test news, that night at Manny’s started out promising for Jacquelina and her sexual pursuits. A young, muscular guy took an interest in me, and we talked as we sat on stools by the bar. He gave me the usual line—which I had heard so many times—that he was really straight and into girls, but he was curious about guys, and he was very attracted to a sexy trannie like me… However, after a chat of about 30 minutes, he seemed to lose interest in me, and he disappeared. Probably a good thing for Jacquelina and her wish to maintain her negative HIV status.

By the end of July, my anti-Jacquelina feelings of early June—from when I first saw Mary—had swung in the opposite direction. I now had Mary trying to find a local endocrinologist for me so that I could start getting female hormones. That’s the way my gender duality had usually operated—with wild pendulum swings from one side to the other. I still have no idea why those swings happen. But they do, they always have, and maybe they always will.

In e-mail exchanges in late July, Mary told me that, after making several phone calls, she was unable to find any endocrinologists in my southwest suburban area who were knowledgeable about hormone therapy for transgenders. She told me I would likely have to travel further if I really wanted hormones. Although she was trying to comply with my latest desires as I expressed them to her, I sensed that she wanted me to think harder about those desires. Is that what I truly wanted? She asked me if I thought crossdressing was a “need” for me.

Honestly, I didn’t know what I wanted or needed… those wants and needs seemed to change from week to week. But I thought that I at least wanted to talk to an endocrinologist. I e-mailed Mary the following:

…crossdressing is a definite need for me... it is really the only way I find peace, happiness, contentment, and fulfillment. But I would phrase it this way: identifying as a woman is a definite need for me... sometimes just thinking of myself as a woman brings me peace, but I have got to do more than just think about it... I have got to be a woman in the real world. For now, that means dressing like one. But I wonder if what I really need to do is become a woman physically in order to finally find a ‘cure’ to my problem. I’ve kept denying it, but I think I may not be able to deny it much longer.
That’s why I need to talk to an endo. Too bad there is not one in my area. I hate having to go downtown because the train schedule out this way means that I would need to be gone the entire day, even if just for an hour meeting. And I would never consider driving downtown. Isn’t there anyone in the western suburbs at least... somewhere where driving would be a little less of a hassle? [Note: I’m obviously not a big fan of driving long distances.] When I was seeing Diane Williams, I believe she told me that she refers her clients to an endo in a northwest suburb.

Mary replied that she would check into endocrinologists in the northwest suburbs. She also asked me what I wanted from hormones.
I e-mailed her back:

I specifically want breast growth and reduction in body hair. I am not concerned about side effects, which I think are minor in most cases. The only thing to be concerned about, I have decided, would be the practical matters of day-to-day life... which is why if I do hormones, I will have to also do three other things to enhance my feminine appearance: get an orchiectomy, get my beard hair removed, and get facial feminization surgery (particularly on my nose). If I do all these things, I believe I will be able to “pass” as a woman. And unless I do all these things, there is not much sense in doing any of them. Do you know what I mean? If I am going to do these things, I want to be able to actually live in the real world every day as a woman—which I now feel is the only real “cure” for my condition.
But I also want to know this: If I do these things, would you support me in my decisions?

I think—I know—that I was driving this poor woman totally insane!! She e-mailed me back:

Only you can make these decisions related to the possibility of transitioning from male to female gender. I would like to support you in pursuing a life that is fulfilling to you, whatever that entails. Because your thoughts and feelings on this subject have varied widely in a relatively brief period of time, I think it may be beneficial to have some discussion and clarification so that I can be most helpful to you. Should you decide to transition, we can also discuss the standards of care that guide the process (which you are probably familiar with) and develop a plan. We will have much to discuss on August 9, as always!

On August 9, I went dressed as Jacquelina for a three-hour nighttime session with Mary. I wore a blonde wig, purple chiffon blouse, denim skirt, pantyhose, and wedge shoes. Mary called me “Jacquelina” throughout the session—just as she called me “Jack” whenever I was dressed as a guy. We discussed my new goals for transitioning from male to female. I had met with a local dermatologist a couple days before the session to talk about permanent removal of my beard hair. I got a prescription for Vaniqa, a cream designed to suppress facial hair growth in women. (Of course, since I wasn’t a woman, the cream never worked for me. But the physical fact of my maleness didn’t stop the dermatologist from writing the prescription for me, nor did it stop me from buying the useless cream and trying it like an idiot.) I had also made an appointment for October 3 to begin laser hair removal on my face. I would later cancel that appointment when my crazy pendulum swung back to my anti-Jacquelina side.

So Mary and I discussed these steps. We also discussed an endocrinologist in a northern suburb named Dr. Geisner, the fellow whom Williams had originally told me about. But he was farther away from me than I had remembered from my talk with Williams. I would end up making a couple appointments for consultations with him—and canceling them both. And Mary and I talked about rhinoplasty—getting reconstructive surgery on my nose. I later made an appointment with a plastic surgeon for a consultation on this—another appointment that I did not keep. Finally, we talked about an eventual orchiectomy.

Oh yes, I was so full of gender transition ambitions in August 2011! All these ambitions would fade over the next couple months as my gender feelings changed again. My mind was in such a crazy, chaotic, confused, contradictory state! I was obviously not mentally healthy.

After my three-hour session with Mary ended at 9 PM, I went to Manny’s for a couple hours to celebrate my transition plans with a few drinks—even if those plans were fucked up and temporary. For me, drinking and crossdressing always seem to go together.

My confidence in wanting to transition to female was fueled by a number of “successful” outings as Jacquelina in early August. By successful, I mean that wherever I went, people were very friendly and talkative to me. Sometimes, people just tend to ignore me. I’m not sure why people were so nice to me in my August outings. Maybe I looked better than usual? Or maybe I just felt better about myself, and I transferred those good feelings to my interpretation of others’ reactions? Who knows…

One night at Polk’s Place—when I had on a dark blonde wig, denim miniskirt, and brown tank top—I was particularly struck at how nice people were being to me. That’s the same beer joint where I had almost gotten into a fight with fat, insulting Tito in June. Even he was as sweet as could be, explaining that there had just been a “misunderstanding” before. The bartender told me that Tito was extremely drunk the night he was so mean to me. I could tell that another guy at Polk’s was interested in me, and I talked to him most of the night. But I also sensed that he was afraid to pursue anything.

The next morning, I went to Barnes & Noble, where I enjoyed a coffee and a nice conversation with an elderly woman, who was very sweet to me. She complimented me on the dress I was wearing—a flowery pink, red, and black wrap dress that I had bought at Kohl’s. Then I went to the shopping mall (where I bought a new dress and flared jeans), a tea and craft shop (where I bought a cute purse decorated with images of Picasso paintings), and the local art museum. People at every place struck up friendly, cheerful conversations with me, and they never mentioned anything about me being a guy dressed like a girl. It all made me feel so good and confident and happy! I honestly did not recall ever before experiencing such good “vibes” from other people when I was Jacquelina.

In mid-August, I felt extremely strong and sure about starting female hormones and beginning the physical transition process to become female. But even then, I suspected that those feelings might eventually change with my mood swings. And always in the back of my mind was this question: How the hell would I ever explain my obvious physical changes—such as boobs and a nose job—to my parents?

My confidence was aided by messages from friends, such as Malaya, the transsexual who had encouraged me to start going out in public in May 2010. After I told her of my transition plans and sent her some recent photos of me in August, she e-mailed me back:

Hi Jacquelina,
I’m glad to hear you’re taking those steps. You know I want what’s best for you. You’re looking better and better, Jacquelina. Thanks for sending your pictures and keeping me updated, too.
All the best,

My confidence in my femaleness—partly fueled by alcohol—reached a peak on August 24, 2011, when I went downtown dressed as Jacquelina to meet business clients. It was the first time any of my business associates had ever seen me crossdressed, other than the time Adriana visited me at my home. The night before my bold downtown adventure, I had gotten extremely drunk at Manny’s with a post-op (had her penis turned into a vagina) transsexual escort whom I had hired off of my favorite website. As was usually the case when I hired escorts, I was already drunk when I phoned her, and I agreed to pay her an outrageous sum for her company that night—$2000. But that was only the first of many times that I would pay an escort or a stripper money like that for a few hours of her time and company.

This particular post-op escort was named Gloria. She happened to be social acquaintances with Malaya. Gloria was pretty, blonde, and 100% passable, but quite overweight (which was not apparent in her online photos). She wore bland, unexciting clothes—a black, v-neck pullover top and black pants. I, by contrast, was in my finest slut attire—a long blonde wig, a shiny low-cut leopard-print minidress designed with sexy rips in the three-quarter sleeves, leopard-print pantyhose, and leopard-print pumps. Lots and lots of wild pussycats! Gloria told me she was in her early 40’s and had undergone sex change surgery when she was in her teens. She had been legally married to a man for a while, but was now divorced.

Gloria was nice and sweet to me, and we had a great time at Manny’s. Despite her bland attire and large size, a young guy kept hitting on her, telling her that he wanted to take her home. He had no idea that she was a trannie. She told me that kind of thing happens to her a lot. Must be her pretty face and warm personality.

After several drinks, I told her that I had to go downtown the next morning for a business meeting, and I really wanted to go dressed as a female because I felt I really was a female. But I added that I was kind of scared to do it. Somehow, by the end of the night, she convinced me that I should do it.

After Gloria left my house, around 3 AM, I napped in a chair for a couple hours. Then—still feeling confident, emboldened, and drunk—I touched up my makeup and selected my wardrobe for my business meeting downtown. I went with the most appropriate and professional businesswoman look I could put together—a black pencil skirt, black hose, black heels, and pink blouse, along with my long blonde wig.

Most crossdressers/transgenders confront difficulties in going out in public dressed femme for the first time. Of course, another big step is coming out to your coworkers and colleagues about your femme side. I know some people who have had bad experiences with this. Fortunately, I work in publishing, which is a very liberal profession dominated by women and gays (at least in my experience). Before I started freelancing at home as a writer, editor, and artist, I worked as a staff editor for a major educational publisher in the city. Because of my conservative/libertarian politics, many of my colleagues at the time thought I was a bit of a right-wing kook. So when I told them about my feminine, crossdressing side in 2010, I think their opinion of me actually improved, like, “Hey, he’s not so bad after all. He’s one of us!” Thus, when I came out, it probably benefited my freelance career. That publisher continues to be my main client. But I think they are probably disappointed that my politics remain in the Ron and Rand Paul libertarian camp!

Although I told the folks at that publishing company about my crossdressing, and they expressed support for me over e-mail and telephone conversations, they never met “Jacquelina” until that August 2011 day when I went downtown for a meeting at the company. At the time, I was toying with the notion that I might be transsexual. So I wanted to present the “real me” to my business client. Before I left in the morning, I e-mailed one of the managing editors that I would be coming as Jacquelina. I wanted to warn them ahead of time so they would not be shocked when I showed up in a skirt.

I rode the commuter train for the hour ride into the big city. Then I walked the 20 to 30 minutes from the station to the central downtown area—an unexpectedly difficult task in my heels, not to mention the uncomfortable summer morning heat. Before I went up to my client, I had my photo taken by the giant, 26-foot-high Marilyn Monroe statue that was in the city at the time. Then I went into a restroom at McDonald’s to wipe the sweat off my face, reapply my makeup, and adjust my wig and clothes.

Despite still being a little sweaty and rumpled from the long hot difficult walk, it felt truly wonderful and liberating to walk into that meeting dressed as a woman. Everyone was very nice, friendly, and professional to me, and they all referred to me as Jacquelina. I received a number of compliments on my clothing and jewelry from the women. One woman said she liked my “bling.” In between sessions, we went to lunch at a classy place. I had a salad—as any weight-conscious lady would, you know.

After my meetings ended at that client, I took a cab a few blocks north to return some items to another client. In the building’s lobby, I ran into a graphic designer whom I knew. When she saw me, she didn’t recognize me at first. The look on her face when she finally realized who I was... that was priceless! We hugged and chatted a bit. Then I rode a cab back to the train station to return home.

As I was walking to the train in the station, a black railroad worker (I think he was a mechanic) hit on me. He started walking with me, he asked my name, and he said he hoped to see me again. Wow, you never know where or when you might run into a trannie admirer!

So my business trip into the big city was an unqualified great experience for me. I had fun, and I got some business done at the same time. I later heard that one of the women at the first client said I inspired her to start dressing better at work! But I also found out that the designer at the second client (a holy roller Catholic lady) was rather disturbed by my trannie appearance. Oh well, you just can’t ever please holy rollers.

Since that first (and only) trip downtown dressed in drag, I’ve concluded that I’m a crossdresser, not a transsexual. When I went to the same client for meetings a year later, in August 2012, I went dressed as Jack. I’m sure this must have confused some people who thought I was now Jacquelina, but they rolled with the flow, called me Jack, and we again took care of our business together. Frankly, I don’t think they care how I dress or what I choose to call myself. As long as I get the work done for them, they’ll be happy.

Although I’ve found that crossdressing/transgenderism have not hurt my career, I acknowledge that my situation might be somewhat unique in that regard.

Jessica Sayyida is the author of My Transvestite Addictions—The Story of One Individual’s Odyssey Through Crossdressing, Alcohol, Escorts, Strippers, Sex, and Money
(ISBN: 978-1-62646-325-7), published under the name of Jack/Jacquelina A. Shelia, by