The Pride of Jessika and her 4th Big Bang

Fri. July 22, 2005 12:00 AM
by Jessika Sterling

Over these last two months, I've had so much happen to me that I'm not sure where to start. A lot of it has been good, but some of it has been bad... very bad.

As we recover from our birthdays, Pride festivities, and 4th of July ‘Big Bangs",
I sit here thinking about the word "Pride" and what it really means to me. Of course, I'm proud of being gay and I love that the "world consciousness" has grow in recognizing all of us as "normal" and "equals". But, I think I really take pride in knowing that no matter what... I have family and friends who will stand by me... no matter what!

The reason I'm so reflective right now is that I probably had the worst experience anyone could have... being completely disowned, threatened, banished, and insulted by your very own father. I'm sure a lot of you have been through these fun little moments in life, but coming from someone who used to be my best friend... up until I "came out... was extremely emotional. Up until this climatic moment, he knew "everything" about me, we still basically got along ok... as long as it was the "don't ask...don't tell" policy when I came home to Detroit to visit. But, due to health issues, too many vodka martinis, and me getting tired of him yelling at everyone for things like not putting the milk away correctly... it exploded all over myself... and my mother.

... not good!

So, despite me recovering from being basically an emotional basket case, I have never been closer to my mother. She has supported me from the time I first came out, to when I first told her I was a professional female impersonator, to this gay/drag drama over the 4th of July Weekend... and I'm so proud of her for sticking by me thru it all... I love you more than anything mom... and I'm so proud of you to stand by me... xoxox

Another recent event that has me feeling "proud" is my recent conversations with some of the "new blood" in the performer community. I've mentioned a few times in the past how sometimes I'm very frustrated with some of the "newbies" and the over abundance of ego... and the lack of glamour and/or talent. I've really felt a shift in the "art" and fear for our survival as something creative, glamorous, and elegant... and not have it turn into a "perversion, fetish, overdone club fad, prostitution, or just a joke".

Recently, I met a budding diva named "Breathless" on who truly seems to understand what it's all about... and wanting to be the best at what she does... not the richest, not the most popular... just the best!

... that makes me proud that somewhere someone's class rubbed off on her.

[blonde segway-moment #1]

As for my story...yes, I used to be a big butch jock in high school and college... and I was a hunk...very volleyball player type body. I actually used to play summer ball with the Detroit Pistons. My sophomore year in college, I blew my knee out, and after 3 surgeries, spent the next few years trying to come back...but never had the same game and had to give it up...but, I'm still probably the only performer in Chicago who can dunk!...haha

I actually got started performing late in life, not till my late twenties and thirties
(I lived in Detroit, very homophobic and not many places to go). I started professionally in '97 after friends literally "threw me" into a halloween drag contest. I've played around a little as a kid, and even worked in a show bar on and off in college (secretly of course) but I was big in college (6'4", 205, 46 chest, 32 waist, 17 arms) and worked out a lot... so, even though my face looked good....I looked like a female body builder. (" with me puny-man!")

After winning the halloween contest, the show director backed me into a corner and forced me to join the cast Helen of Club 7301/Chicago apparently really saw something in me. I moved to Chicago in '97 (at 190lbs) and did that contest on a dare...after I agreed to perform, I lost 40 pounds in 3 months! It helps being a jock and playing basketball and ice hockey...all I had to do was not eat like a pig anymore and stay came off so fast everyone thought I was dying...or was on the "Crystal diet"... it scared my mother to death... but I had cheekbones for miles, bitch!!!!

I definitely got hooked right away...I was 6'4", 150, and a size 8!...I looked fierce ...and won my very first (and only) pageant, Miss Gay Chicago/Western Suburbs/ Newcomer 1998! Shortly after, I got a drag mom, Miss Gabrielle Giovant'e
(still my best friend, and in Miami now...checkout my SoBe tour pics to see her) ... and everything progressed from there at light speed.

It's funny, her only big advice to me was "More...Darker, bitch!!!!"

Since I was a designer already (20 years experience) I knew how to contour and paint...but it's those tricks of the trade I learned that made me who I am now.

We all learn that "covergirl don't cover boy" real quick don't we?!

The scary thing was that I got REALLY into being the diva quickly...from '97 up to '01, I almost went full trannsy...I even had my nose done and was on hormones (thank god for sports bras and baggy The nose job was needed from my sports life and several broken noses and not being able to breath right....
plus, I had it done to look good as a boy and girl. I've been real happy I did that and not some tiny Michael Jackson/Trannsy nose...not that I don't have a lot of respect for someone becoming a transsexual... I think it takes a tons of guts to make a choice like that, and we should support them more... but there are those who've gone too far and look like freaks in the daytime with no make up....
I think that the thought of that and being a 65 yr. old trannsy snapped me out of it... and probably having to take a huge pay-cut in my career. (...sorry, but this boy likes his Jaguar and loft, aw'ite?!)

Plus, I get alot more compliments, and amazed fans, when I tell them that I'm all boy...and I'm such a big lazy-ass, it's nice to not have to paint up every time I want to go


Geez, I guess I just dumped my life story on you didn't I?'ve told this story so many times to so many people it just comes out on auto-pilot sometimes...sorry about that....hehe

The one big thing my Drag-mom taught me... the thing I'm most proud of... is that she taught me "class". She taught me how carry myself with pride and confidence... no ego... no competitive jealously. She taught me how to not "act" like you have "style and class"... but, truly believe in it and live it. Being nice to other performers, or even someone walking up to you in a club.

It's not charity... it's an honor for you to have them be interested in you
... take pride in that!

When I played college basketball, I used to try to play against people better than me... I always wanted a challenge... I never wanted to just settle. Drag is the same thing... there's always going to be someone better than you. Don't be jealous... take it as a challenge... learn from them... even work together.

Think of it this way...the better the performers...the better the shows...the more customers... the more clubs see how successful they can become...
more competition...more money ... and more shows for all of us!

Well, I guess we should get on to the fun stuff and what the bumper boyz and I have been up to, eh?

June started off with a lot of fun as I made an appearance at the "Pre-Pride Party" for at the fabulous, newly redesigned, Circuit Nightclub here in Chicago. As the crew and I hungout and waited for the "Chicago Gay Idol" contest to wind down... I was all moist that I finally got the chance to hear my Sweetie/Bumper Boy from Crew...
The fabulous Adam! (pictured) ... sing his little heart out... and the bitch is good!!!

Look for him and his band "16 candles" in the Chicago bar scene!!

Also in attendance was my editor extraordinaire... Steve Long... and of course his sidekick as always... our diva photographer, Emilio Alexandrov. At the door was none other than the famous Byrd Bardot, of the famed NYC "club kid" and Studio 54 crowd... too cool!

I had so much fun chatting with her out front... also did some catching up with Miss Paula Sinclair of Annex 3... and of course Miss Foozie herself joined us, while receiving a few "FOOZIE!!!" from fans passing by... and her waving back to all her little "Pineapples!". There was even an appearance by our painfully shy owner/host of this evening @ Circuit... little hottie, Mike Macharello. (... and as usual, our conversations consisted of... "Hey, how are you?"... "Good, how are you?"... ."You look fabulous!"... "I like your shirt also."... .)

[twidling of thumbs to the lull]

Unfortunately... and this being tied into the "very bad" things that happened to me... all my pictures from that evening were lost in "My Great Hard Drive Crash of 2005"... and the worst of it is... I looked fabulous that night!... lol

The next event may be considered by most as a good thing... but this year I was a "Pride Baby" and my birthday was during "Pride Week"... which is always an added bonus... and having all the out-of-town "bumper boyz" joining in on the festivities is always a good thing..."and I've been a very bad girl this year"...hehe.

Unfortunately, this was also a very momentous year... yes, I was turning 28! (... you believe me right?)

Anyways, I am very proud that I can still pass for 28... so take that. [snap]

Now, the big news was the "Chicago Pride Parade" itself... and yours truly was definitely living up to her "Media Goddess" reputation by having none other than JAGUAR/Chicago be my official sponsor this year!!!! And gurlfriend, Miss Thang rolled up to the crowd in a $100k Sterling Silver XKR Convertible and
"let that crowd have it" with my floral Betsey Johnson, Diamond/Pearl accessories, and a Black Hat worthy of any afternoon at the Palm Beach Polo Matches...

("Oh, Ralph... how's your collection doing this year, dah'link... please tell Karl, Liza, and the Hiltons I said hello and I'll see them in the Hamptons next month ... .tah!")

[wave... smile]

[Blonde segway-moment #2]

An amazing thing happens everytime I do a parade... I kind of have this "signature wave" that is very "Princess Di meets the Pope"... it consists of locking your arm at a 90 degree bend, hand straight-up and flat, and basically pivoting only at the wrist. Good posture, big smile, and being able to shift positions and arms at will is a must-skill. Now, the bizarre thing about this is... it is extremely infectious. I swear I had everyone in the parade waving back at me with this... I even had little children and the horse-mounted policemen giving it back me...
it really appeared that everyone was going "alllllright bitch... you work it... give me that wave of yours!"... I even had the cameramen from QTV and the local channels give the wave back as I passed by their positions... too funny!


As I had my fabulously hunky Bumper Boyz, Zack & Robert (pictured above), to either side of me... we lead the float down Halsted thru the 400,000+ adoring fans. Also as part of the Jessika Sterling/Jaguar Team, were Barry, Jenn, and Jessica from Howard Orloff Jaguar looking extra fabulous in their "Official Jessika Sterling Bumper Boyz" black tank tops with polished silver metallic lettering ... lol ... and passing out all of our Jessika Sterling/Jaguar/CP/ justcircuit promotional cards... I'm not only the media goddess... I'm a "Media Whore" also... hehe

AND... we won the "Best of the Parade-Honorable Mention Award" for what the committee stated as "... for a very elegant and well-dressed entry".

Thank you to Richard Pfeiffer, President from the PrideChicago Committee (, Steve Long @ CP (, Phil/Barry/Jenn/and Jessica (pictured) from Jaguar (, and my sweeties down in Florida, Shane & Victor @ justcircuit (

As for July, we won't go into my family drama... or revisit me losing my entire world with my hard drive crashing on my iBook. But, I did however attend the "Miss Charlie's Drag Factor Pageant" hosted by the ever fabulous, and friend... Miss Lauren Jacobs.

With my "Original Bumper Boy" Rolando and Mr. Velvet Rope himself, Jason Paul (... DYKWIA!!!), in tow... Lauren and the cast of Charlie's Angels
(Aurora Sexton, Monique Moore, and Regina Upright) proceeded to put on a really entertaining event.

Believe it or not, but I think they have the best show in Chicago right now!

The contestants this year were... Monique Marquette (1st runner-up), Remy Martin (2nd runner-up), Michelle Fighter, Mercedes, and the new "Miss Charlie's-Erania Stone". I'll tell you, for what is basically a small bar title pageant... these girls really "threw-down". From the cast to the contestants, the jewels, gowns,
the up-dos (... and some up-don'ts) and the talent were all very well done.

[gay golf-clap]

I especially liked Erania's talent number with multiple costume changes going from Tina to Aretha to Patty LaBelle... fabulous. And, Monique Marquette's Catherine Zeta-Jones' "Chicago" dance routine had me exhausted just watching it... nice job Mo'... xoxo

I also have to mention how Lauren Jacobs (pictured) was just "on fire" that night on the mic... the bitch is just ruthless and so quick with putting hecklers and other loud (rather large) divas in the crowd in their place... absolutely hysterical...
well done girlfriend!... you're the best MC in town in my book!

... although, her gracious shoutout to me was somewhat tainted with a follow-up comment about my Faith Hill-esque look/outfit of the evening, consisting of my cowboy hat, vest, and jeans. Painfully seeing it coming, I let it hit me as she went on her way to setting me up for the line... Jessika Sterling!... or is that Faith Hill ... or maybe that should be "Over-the-Hill"?!

I have to admit... that's funny... and I know better to go toe-to-toe with her... so I just smiled, laughed and told her how much I love her... lol

(... I'll kill her privately!... hehe)

Finally, seeing that we are talking about "Pride", the other thing I am very proud of is my "Bumper Boyz". These guys are all my friends, some I've known for years and go out with every weekend, while others are people I just met in some other city and just enjoyed chatting with them so much that we decided to stay in touch. Believe it or not, I have over 200 names on my personal email address book for my Bumper Boyz... and I'll honestly say that I keep in touch with everyone of them, and enjoy hearing about what they are up as much as they enjoy hearing about me getting into trouble every weekend...

So, to finish this little novel I've been writing here... I thought I'd give you a compilation from some of my very own lists, and some from all my Bumper Boyz (... especially my sweetie Rick V.!!!... xoxox) of what makes my boyz so unique and why I'm so so proud of them...

Jessika's 100 Best Things About Being a "Bumper Boy"

1. You understand the difference between 43 brands of imported vodka.

2. You can call anyone "honey"... including pets.

3. You know someone who definitely was in the emergency room with Richard Gere and the gerbil.

4. You understand the immense importance of good lighting.

5. You can be at a crowded nightclub the size of two football fields
and can still spot a toupee.

6. You can recognize knock-off Prada from 200 paces.

7. You can explain the nuances between steady date, boyfriend and lover.

8. You really have "been there, done that."

9. Your women friends will tell you everything you want to know about their boyfriends... and that means everything.

10. You're the only type of male who gets to say "fabulous."

11. You know how to handle your cell phone like a Stradivarius.

12. You understand why the good Lord invented spandex.

13. You understand why the good Lord didn't intend everyone to wear it.

14. You know how to get back at just about everyone.

15. You can smile to let someone know you can't stand them.

16. You can freeze a troll from 20 feet away with a raise of your eyebrow. (... or what's left of it.)

17. You're good pals with women and other people you can't stand.

18. You've always got an opinion.

19. You've read the book, seen the movie... done the musical.

20. You know how to dress strategically.

21. Your car has an amusing female name.

22. You're the only one at your high school reunion who looks a lot better than you did in high school.

23. You've got at least one framed picture of a pet.

24. If your mattress could talk, it would be Joan Rivers.

25. You know that sex complicates things... So?

26. You know that being called a "cheap slut" is actually a compliment.

27. There's a married guy somewhere who is terrified of you.

28. Nobody tells you what to do in bed...unless you tell them what to tell you.

29. You have a medicine chest stocked for any occasion.

30. You have at least one movie musical on video.

31. You're not embarrassed to sing in a piano bar.

32. You're embarrassed by people who sing in piano bars.

33. You never hold a grudge for longer than a decade or two.

34. You know the difference between Champagne vs. Sparkling Wine.

35. You know how to make an entrance.

36. You know when to make an exit.

37. You worry about people you don't even know - like Liza Minnelli.

38. You've got sunscreen at every conceivable SPF level.

39. You have a cologne/perfume display worthy of Bloomingdales

40. You understand Joan Crawford... viscerally,

41. Some of your best friends are your ex lovers.

42. You know when to play dumb.

43. You know what to do for a hangover... but forgot how you got it.

44. Yes, you do have a condom.

45. You've called someone "girlfriend" who is neither a girl nor a friend.

46. One or more of the following apply to you:
a) You adore Judy Garland
b) You hate Judy Garland
c) You hate people who adore Judy Garland.
d) You hate people who hate Judy Garland.
e) You don't give a damn about Judy Garland.
f) Where's Liza?

47. You can supply the last names to the following list:
a) Bernadette
b) Chita
c) Barbra

48. You made Donna Summer a star.

49. You made Donna Summer a has-been.

50. Tanning salons were invented for you.

51. You've made sunbathing a performance art.

52. You know when the party's over.

53. You know where to go after the party's over.

54. You're fearless about fighting the elements, especially gravity.

55. You know that pigs, chicken, beef, cows, fox, and bears are not necessarily animals.

56. You know that the most important part of a party's decor is the catering staff.

57. If your cat is a female, you'd swear it's a lesbian.

58. If your cat is a male, you'd swear it's a lesbian.

59. You sing along heartily with songs that make most females cringe... like "Stand By Your Man."

60. You've been to a bris, a bar mitzvah, a christening, a first communion, and too many weddings... and you have a carefully considered evaluation of the food and men after each.
(... and they are surprisingly similar.)

61. A two-seater convertible seems perfectly practical to you.

62. You have a favorite Disney character, and it's usually a nasty one.

63. You've left someone totally speechless.

64. You've shaved something other than your face.

65. All your friends do not have to "get along".

66. Your love handles are actually used as such.

67. When someone turns his back on you, you actually consider it an

68. You've got a large assortment of movie-star biographies

69. At some moment in your life you've envisioned having back-up girls.

70. You know your enemies... and have probably slept with some.

71. You're Barbra Streisand's biggest fan.

72. You know that Barbra Streisand's biggest fan is Barbra Streisand.

73. Not only have you added spice to your life... sometimes you've added side dishes.

74. You know that "small talk" can be about spirituality or politics...
and "important issues" can be about hair.

75. You've actually lived out some of your fantasies...
and have the pictures to prove it!

76. Unlike most straight women, you have no problem being treated
solely as a sex object.

77. You know, by heart, every line in:
a) All about Eve
b) Steel Magnolias
c) Your face

78. You are ALWAYS ready for your close-up.

79. You have 9412 ways to tell someone to get lost. 8136 are

80. You can lip-sync to at least one Supremes song.

81. You have a carefully selected Yiddish vocabulary.

82. You know exactly how many martinis it takes.

83. When throwing a party, you know how to put out quite a spread...
sometimes after the party too.

84. You can drive a Stick-shift... and yes, the term "four on the floor"
turns you on.

85. You know the difference between "Tighty-whities", Boxers,
Boxer-briefs, Thong, or "Commando"... and dated men in all categories.

86. "Chicken or Fish?"... has you think sexual partner... not food.

87. You use the term "Baggage" as an excuse to punish current

88. You consider the term "Ex" as anyone you've slept with more
than once.

89. You consider the terms "Bi-curious", "Bi-sexual" and...
"Bi-me-another-cocktail-B'yotch!" as GAY.

90. You own at least 3 different colored belts... and have at least three
pairs of shoes to match each.

91. You consider "Vibrators" a "power tool".

92. You define "Cuddle" as a disappointing sexual activity with no
exchange of bodily fluids.

93. You correct straight people for using the term "go straight" while

94. You have used one credit card to pay for another credit card bill.

95. You consider the term "pumping iron" as repeatedly pushing the "steam button" to get that perfect hem.

96. You physically want to hurt "Jared" from the subway

97. You now know why you owned more than one GI Joe as a
child... and why they were always naked.

98. You wonder why "If Barbie was so popular, why did you have to
buy her friends?"

99. At a point in your life you have awoke and screamed from
a face in the pillow next to you... then realize it's from you falling asleep in full make-up.

100. You own matching luggage... and couldn't live without it!

Be proud of who you are... and share that pride with others!!!

... and now the photos to prove it! Jessika's Full VIP Photo Spread