Bill’s Transition to Jacqie

When I first cranked up this blog and started connecting with folks from the past in Cape, Wife Lila and I got this short message on Facebook:

Hi lila and kenny. Its bill jackson but if you have facebook, you will discover that many changes have taken place. It seems that after all these years I am more comfortable as Jacqie, my female half and counterpart. Florida is much more familiar with this than cape. The reunion should be very interesting.

Bill Jackson, Class of 1966

I remembered Bill. He played sports and was active in music. Lila, being in the same class, not only knew him, he was her first high school date. The dating thing didn’t go on long, but they became close friends working as lifeguards and swimming instructors at the Cape Pool and the Natatorium.

Jacqie in St. Louis

In October, we met up with Jacqie at the Bar 5 to see her perform Karaoke. Her story of the transition from Bill to Jacqie was interesting enough that we made arrangements to meet when we came back to Cape in the spring.

I photographed Bill on the riverfront on Saturday, then interviewed his female counterpart on Sunday. To answer the question that I know you WANT to ask, Jacqie describes herself as “a heterosexual male cross-dresser.”

Watch the video. It’ll explain a lot.

Bill’s Transition to Jacqie

Jacqie will be attending the reunion on June 25-26.

48 Replies to “Bill’s Transition to Jacqie”

  1. I have known Bill Jackson my whole life…I was invited to be friends with Jacqie Jackson thru face book from Gail Tibbles…so I say WTF and push the be my friend button…I thought is was someone I knew in High School and BOY did they change a lot! I looked at the picture again and my mind started to do one of those…wait a minute I know that person but where???
    Two days later… in the middle of the night I wake up my wife and say WTF…THAT is Bill Jackson my old grade school, high school and College buddy. I could have thought of at least one hundred people I would have thought would change to dress, act and sing as woman before Bill Jackson . Jacqie as she prefers to be called, seems to be comfortable with it so I say ” Old buddy if you like it, then if must be alright with me”.
    Bill’s mom was my Cub Scout den mother, everyone knew Arthur Jackson, Sergeant Major of the Army and I knew, taught and worked with his whole family of brothers and his sister in my growing up years in Cape. So Like Ken and Lila I have a history with the old Bill and look forward to seeing the new Jacqie. I somehow doubt she will be able to belch the 26 letters of the alphabet like the old buddy I knew but…I might have lost step or two myself.
    So I look forward to seeing all my old friends at the reunion in Cape coming up…

  2. I always enjoyed Bill Jackson, so I am anticipating enjoying Jacqie as well. It’s been a long time since those days back at Franklin School and Cape Central. We’ve all had plenty of bumps and bruises and lots of soul-searching. You don’t get to our age without dealing with lots of “stuff.” Just as Jacqie was saying, you figure out what you need to do to live.
    Jacqie, I’m so glad that you chose life!

  3. Jacquie, good for your in making the changes you needed to make and special congrats on almost four years of sobriety! I remember your intelligence and thoughtfulness from high school. Ken, excellent production. In my job I worked with some kids who did crossdressing. Madison Schools are pretty good in supporting kids in their development.

  4. Ken and Jacqie, fantastic! When I first “met” Jacqie in the newsletter, she asked me if I was shocked. No, we were not. Our family doctor in Florida suddenly left town and changed from Brian to Laura. He was a GREAT doctor, especially with our grandkids and I’m sure Laura is as well. Oh, Jacqie is familiar with Dr. Laura and her story. Life is MUCH too short to live it in unhappiness.

  5. WOW. I knew Bill in high school. I say “whatever floats your boat.” Good for you Bill/Jacqie. Live your life the way you desire. Ken

  6. It’s amazing how much more accepting we are of others’ differences when we get a few miles on the old odometer.

    Maybe some things do get better with age.

    In a scene I had to cut because of time constraints, Bill commented, “We were all not exactly as kind to each other as children as we could have been, but that’s the nature of being children. You’re learning how to be human beings.”

    Looks like my readers have done a good job passing the human being test. That’s a pretty good diploma to tack on the wall.

  7. I am very glad Jacqie has found happiness. We were in the same homeroom through Jr/Senior high school because of our last names and I always liked Jacqie. The story makes one wonder how many other people in our childhoods had issues that we never knew about but were not as lucky as Jacqie to find out what was best for them. As a side note, my wife and I had finished dinner at the Weber grill in Shamburg, Il and as we came outside the restaurant, there was this very well built gentleman standing there, he had on a dress, stocking, high heels, wig and all the makeup a women would have on. The thing that caught our eye was, he had a full black beard and mustache. It just looked so out of place with the outfit he had on. I had the urge really bad to ask him what was going on but being on the smaller size and he being on the larger size I decided not to. Now with Jacqie story I am glad I didn’t, he may have been trying to find his place in life too. The best of luck Jacqie and a very good story Ken.

  8. When Jacqie and I met three years ago, we developed a special bond. So much has happened in our personal lives since then. Jacqie has blossomed into an entertainer and realized happiness on a level that couldn’t have been imagined. My transition from Steve to Stephanie was also “life saving”. I totally get Jacqie. What a warm, intelligent, articulate, and talented person she is. And did I mention, fearless? As others have said, life is too short not to be happy.

  9. okay, i am a fairly tolerant “live and let live sorta person, been there, done that, and survived alot, BUT, i gotta ask, why the hell would a fairly good looking male want to turn himself into an ugly woman?? by the way womens clothing isn’t all that comfortable. after chicago, the dresses, hose, heals and bras, arizona, with boots, jeans and tees. that is happiness.

  10. It is always a specious argument to make about another person being somehow wrong because they choose to do or enjoy something that doesn’t float your own boat. The inability to get out of your own way and understand another person for the unique way that they feel comfortable or even compelled to express their identity is the basis for so much intolerance in our world. All that said, I am very moved by Bill’s courage to be who s/he truly is, walk proud in those high heels, and hold up a mirror to all of us who grew up/live in the conformist Bible-belt atmosphere of Southeast Missouri: We are a diverse clan! Thanks, Ken, for once again promoting our dialogue and to you Bill, I say: “You Go Girl!”

  11. first i want to thank ken for all of the hard work he did to make this interview/video possible. when i was contacted by gail last august, i told her what was happening and she listened. as i met more people on line/facebook and conversed with them i received many positive comments and support. ken started the interview idea when several people urged me to do what made me happy. i have been gloriously happy for the last year and a half since i got my life organized so that i could live in a manner that makes me content and at peace with myself. i am heartened and overjoyed at the majority of the comments so far and not deterred by any of them. i realized a while back that no one is going to like all of what anyone else does, so i will satisfy myself first. i thank you all and will see you very soon.

  12. Before joining the WAVE on this pursuit of happiness, it must be asked if any tax dollars contributed to the transformation.

    1. I give folks a fair amount of latitude here, but I’d like to know where you are going with this question.

      As far as I know, the only tax dollars going in any direction are sales tax dollars headed back to the state.

      Jacqie owns more shoes than I’ve owned in a lifetime.

      Some folks buy boats; some people spend their time trying to get a small round ball into a hole in the ground; I spend my discretionary income on bicycle toys and computer gadgets.

      Would you ask your tax dollar question of any of us?

  13. i wonder if mr redpath took the time to hear that i am as physically the same as i ever was. my changes are within and cost no money. like ken said, my external changes have boosted the economy lol.

  14. I wasn’t going to bring this up, but I am somewhat jealous that Jacquie’s legs look better in boots than mine ever did! LOL

  15. Ken,
    Thank you so much..because of this video, I got to meet Bill. In the last years or so, Jacqie has become a big part of our family here in St Louis. For those of you who knew here when, all I can say is as someone who knows her now..she is one of the most giving, loving, supportive and positive people I have the honor to have in my life..I hope you all come to love her as much as we do.

  16. Thanks, Ken and Jacqie, the video was great. Jacqie, the only thing is I am having trouble remembering how to spell your name, I guess Miss Sadler’s King’s English didn’t rub off on me as well as I had hoped. See you both, and Lila, at the reunion!

  17. I’m not a Cape Central alumnus, just someone who was pointed to this page by a Central alum, so I’ll remain anonymous.

    Anyway, I think some of the comments here reflect the common confusion between the terms “transvestite” and “transsexual.” A transvestite (or cross-dresser) is someone who occasionally enjoys wearing the clothing and adopting the traits of the opposite gender but who does not desire to permanently change his or her gender. A transsexual, on the other hand, feels that his/her body does not match his/her gender identity and therefore desires to change genders, often via surgery and hormone treatment.

    If I’m not mistaken, Bill is a cross-dresser, not a transsexual, and wishes to remain a male. The use of the word “transition” may have caused confusion, since one usually speaks of a transsexual’s “transition” to another gender.

    And that’s our gender lesson for today!

    1. Anonymous,

      Thanks for the clarification. I used the term “transition” because Jacqie described herself as being “in process” and not knowing where it was going to take her.

      In a part that was cut from the video, Jacqie said that the Rainbow Community makes assumptions the same way that the straight community does. “If they see a man dressing as a woman, they are automatically gay… Then, the transgender community comes up with such finite names… Are you a drag queen? Are you a cross-dresser? Are you a transvestite? Are you a transgender? My own sisters will become offended if you just call yourself something that they don’t think you should be calling yourself.”

      Here’s the best line (and I wish the written word could deliver it as well as Jacqie in person):

      “And, it’s like, who cares? We’re all dressing like women.”

      Her message is one of inclusion, not of splitting hairs.

  18. Anonymous makes many good points. Clairfications are necessary for those new to the concepts. I guess I have moved past caring about the what’s and just concentrating on being whatever I am.

  19. I have never met Bill but, am very familiar with Jacqie. I have not watched the video yet as I read these posts first and want to comment on how moved I am. I grew up in both st louis and rural Mo. I am so moved at the positive responses. Growing up different is hard! It does not matter what the difference is. If you can change what you do not like about yourself and be happy, God bless you for figuring it out and having the courage. 16 years ago, this page would not be full of the love that is spoken here today. For that I say thank you Jacqie for removing yet even more ignorance in our progressing world of tolerance! I love you and enjoy your reunion.

  20. Hello,I love reading through your blog, I wanted to leave a little comment to support you and wish you a great continuation. Wishing you the best of luck for all your blogging efforts. Thank you

  21. I really enjoyed this video! GREAT JOB! That really took some testicles! LOL! Sorry, couldn’t resist. Really though, how brave to come back home at all! Most people never do! I think it probably helped many people better understand something so foreign to most around here, and hopefully helped make the class reunion a bit more comfortable. : )

    I’m writing mostly with questions about how this has affected your family? You mentioned divorcing, yet, it sounds as if you are still with your wife somehow. And how have your children, assuming you have any, responded to this new change? I’m also curious as to how the reunion went! Just how ‘downhome’ was Southeast Missouri?? 🙂 I’m sure there was a bit of awkwardness and strange looks at first.. again, there I go assuming.. that you went as Jacquie.. lol.

    I really sincerely want to congratulate you on your sobriety! My husband has almost 22 years now! I know very well about the struggles of alcoholism! Your Dr was right, I think, (maybe a little too Dr. Phil style) but, suppressing these type of things, also like homosexuality, does tend to lead to earlier death! The suicide statics for homosexual teenagers are through the ROOF!

    Personally, I’m a very devout Christian woman, and I have always said, that if we as a church, were even HALF as accepting as the gay community, there wouldn’t be enough churches on the PLANET! Blessings and much love! jilldwan

  22. To jilldawn: I have not read these comments for several months. The reunion was fantastic. We had a fun weekend. Many of us are meeting monthly now for lunch in Cape.
    It is my hope however, that all of the references to gay and homosexuality are to point out that people and religions can be cruel and narrow about differences,and that you realize that these preferences have NOTHING to do with my choice to dress and live as I do. We MUST separate the concepts of sexual preference and gender preference.

  23. I remember Bill from days at Cape Central, yet never met him. I’m just now getting around to watching the video & may I say its very nice to get to know both Bill & Jacqie! “Life is a stage”, & aren’t we all playing a role, many times far removed from who we really are within? The self-work that Bill/Jacqie has done & his/her acceptance of what makes life worth living for both entities, is successful healing. That’s successful living!

  24. Glad to hear you are doing well and coping in your own way. Will try to make the July lunchion. I hope you are there.

  25. My husband and I first met Jacqie in February of this year (2011). She was picking up her karaoke equipment at a local restaurant that we were eating at. We both enjoy singing so we started talking with her and began attending her shows.

    I wish everyone in this world could be as courageous as Jacqie has been. We’d all certainly be a lot happier with ourselves. When we are truly happy with ourselves, we tend not to belittle others.

    I applaud her efforts to do what she needs to do for her! I admire Jacqie and consider her a top notch quality person and a friend. We attend Jacqie’s shows almost every week. I look forward to getting to know her even better.

  26. I had a similar experience with a friend from college (Rich/Rachel). At first it was, “wow, I didn’t know” and after a while it became “oh, well it kinda makes sense.” And I am happy to say that it’s like having two friends sometimes…and both personas are awesome people. Thanks for sharing the video with us Bill/Jacque (and Ken), it has put into words what my friend can’t explain, it’s a fairly new outting for him/her. But makes perfect sense. Native americans called such people Berdache, which means two-spirited, which usually indicates a person whose body and mind reflects and identifies with both male and female characteristics, often times thought of as a warrior and clan mother, or in animal spirits such as the crow and the wolf. They were thought of (for the most part) as being very spiritual people, in touch with both sexes. Just like today, some tribes embraced these people and some tribes did not, but overall they were mostly respected and sometimes feared. Thank you.

  27. Somehow I missed this story when it first ran and just saw it today. Ken, it was a great video,very informative, and it was good to see all the positive and open-minded comments from your readers. we are often so quick to “judge” something we don’t understand rather than being willing to simply listen and try to relate to some one else’s struggles. Truth be known, probably the majority of people have “issues” that they have lived with and maybe never really faced. Best wishes to you, Jacqie!!

    1. We’re talking about doing an update. Jacqie has moved down to Florida and is picking up business quickly, didn’t miss cold wind blowing up her skirt this winter (hasn’t been through hurricane season here, though) and is more polished than when I did the original.

      This was the first major video project I tackled, so the audio and some of the cuts are a bit ragged. I’m hoping the next iteration will be cleaner. Stay tuned. My to-do list is pretty long.

  28. Kudos to Jacquie…To me this is the most interesting clip of how someone’s life gets turned around from all the stress’s in the world to a very happy unique individual.
    I had the opportunity to meet Jacquie will vacationing in Florida… What a fun, intelligent person I have had the pleasures of meeting… Loved this clip on Bill’s transition to Jacquie… You are my hero and I look forward to seeing you more when I finally move down to Florida full time..
    Keep up the singing, dancing and your love for life..
    Til we meet up again next year…

  29. Jacqie is a contribution to any gathering I’ve ever seen her at, fun, generous, supportive, courageous in more ways than dress. Thanks for the video. I figure Bill was too and from these comments it looks like I’m right.

  30. This is a great story I only saw Jaclyn two times I fell in love with her been following on FB and think she/he has it going on life is what we make and you did it good for you

  31. I go to as many shows as possible hear in beautiful south Fl, and love every one of them, Jacquie is a breathe of fresh air. Kind and wonderful person and great performer.

  32. I have only started going to Jacqie’s venues but have fallen in love with her way of making everyone feel comfortable in his presents.He real showmen. He makes it a pleasure to do karaoke. Thank You, Jacqie

  33. You are an amazing person and a wonderful entertainer! Thanks for being brave enough to share your thoughts and struggles with us all. I’m going to share this, because I know there’s a chance it might make someone else out there feel less alone and better understood. I hope you continue to bless us all with your charisma and fun shows for years to come!

  34. Jackie is an amazing happy and free person that harms no one and I am a better person for having meet her. Who is anyone to criticize or judge. All I need to know is she is happy and makes other happy thru her happiness and harms no one. You go Jackie, glad to be your friend. Just pissed you get more than the regular 15 min of fame. lol

  35. I love watching Jacqie perform and sing and dance to karaoke at David G’s Neighborhood Bar and Grill on Wednesday nights. She entertains the crowd, makes sure everyone has fun and looks like she has fun at her job. Who are any of us to judge her? Life is too short to live it unhappily, I say Jacqie you go girl! Even as I change the words in “volcano” to Barack Obama you are still smiling! I’m glad you’re happy with who and where you are at this point in your life, how many of us can say the same thing! You are blessed!

  36. First let me begin by saying I originally met Jacqie the summer of 2013 at Lil Munich on Lake Ave in Lake Worth, FL then again at South Shores on Lucerene the same summer. I recall her warmth as a person and her full confidence on stage with her microphone, each time I see her she’s so elegant and warm and true to herself. A few months ago I watch Stonewall on July ( Showtime) it just made my heart crumble and my stomach turn for what they did to those poor people, they weren’t hurting anyone, they just wanted to be who they we’re/as they we’re to be as people and the police not only shunned them but burned them, beat and persecuted them till one night the community at Stonewall attacked back. Any ways, I believe in my heart and soul that we all have a certain path we are meant to follow, a specific life we are to lead and if one isn’t happy where, and or as they are living whatever that may be, then it’s their right and place to choose whatever it may be that will bring them happiness and self fulfillment. If it isn’t hurting anyone else and it’s in our best interest in order to lead a good life then make it happen. I truly believe that this interview / video will lead to helping more people realize their true selves and go on their journeys just as Jacqie is doing, to live the lives they desire to live and love living.

  37. Jackie you are awesome. I’m glad you found your happiness sometimes people don’t want to read the red flags their mind and heart is giving them and they live life in a block hole trying to figure out what its trying to tell them when all along it has been there. I’m glad that you found your happiness and hope that many more read the signs and see that life is short and your happiness means more then anything in the world. Keep being you and be happy that you found yourself! See you Sunday!!

  38. I love your shows and think you’re a great person!
    I’m married,so don’t get to your shows as often as I would like,but have a ball when I do!
    I’ve been to Burning man in Nevada,which is quite an Experience.
    Everybody with an open mind should go at least once!!

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