Jessica De Leon

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Photo of the Day: AJ McLean in Drag

Jessica De Leon posted an article on - Feb 10, 2012, 4:30 pm
AJ McLean is best known as a member of the seminal boy band Backstreet Boys. All I can say about them is that my sister used to be a big fan of the group. I have no further comment about that. I spotted this photo on the Internet of the singer songwriter in a poofy-skirt
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Word of the Week: Passing

Jessica De Leon posted an article on - Feb 10, 2012, 12:38 pm
It’s time for our series of posts here at Jessica Who?, titled “Word of the Week”. In these short articles, published on odd Fridays, I will explore the various labels and umbrella terms used to label us. By doing this, I hope to educate not only myself, but also anyone who may not be...
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The Magnetic Fields' Ode to Cross-Dressing "Andrew In Drag"

Jessica De Leon posted an article on - Feb 9, 2012, 12:40 pm
The Magnetic Fields are an indie pop group that would have forever gone unnoticed in my own life had it not been for this track of their upcoming record Love at the Bottom of the Sea. The name of the song is “Andrew In Drag” and it is about a man who falls in love
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T-Girl Talk: Amnesia Sparkles Interviews Vicki Vegotta Bonus Footage

Jessica De Leon posted an article on - Feb 8, 2012, 10:41 am
Last week we presented Amnesia Sparkles’ interview with Vicki Vegotta and the clip quickly became a favorite. When I was putting together the video, there was just so much good stuff that I didn’t want to throw anything away. At the same time, I didn’t want to release a seven or...
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Family Guy: Sexy Peter Griffin

Jessica De Leon posted an article on - Feb 7, 2012, 2:39 pm
In the following Family Guy clip (“Livin’ On a Prayer” episode), Peter & Lois Griffin are about to pull off a heist so Lois checks to make sure Peter is at the various checkpoints. One of the pre-heist tasks involves Peter dressed up as a sexy prostitute in order to distract...
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RuPaul's Drag Race Season 4 Episode 1 RuPocalypse Now!

Jessica De Leon posted an article on - Feb 6, 2012, 4:30 pm
Season four of RuPaul’s Drag Race has started with the promise of being bigger and more over-the-top than before. I’ve said it before, the drag queens in this show really bring it with fashion and attitude. You can watch the first episode as well as check out my brief review after the...
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Do You Pass? Do You Want or Care to?

Jessica De Leon posted an article on - Feb 6, 2012, 12:08 pm
They are two small words that many in the transgender / crossdresser community long to hear, “you pass”. Some may argue that hearing this phrase is the greatest achievement one can strive for when moving from one gender to the other. On the other hand, some argue that...
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Iggy Pop in a Dress – Photos of the Day

Jessica De Leon posted an article on - Feb 3, 2012, 11:30 am
I must admit that I don’t know much about Iggy Pop. Okay, I don’t know anything about him. Well, I guess that’s not true, I know that he is a musician. Regardless, he looks absolutely daring and courageous in these photos of him cross-dressing. Please hold on a moment as I check...
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Animal Crossing 3DS Will Allow Males to Wear Skirts

Jessica De Leon posted an article on - Feb 2, 2012, 11:30 am
The next iteration of the Animal Crossing series will come out sometime this year for the Nintendo 3DS handheld video game system. Like always, the life sim will allow players to organize their homes with furniture, plant trees and flowers, and interact with neighbors. When you start a new game in.....
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Canadian Lawmakers Impose More Air Travel Restrictions

Jessica De Leon posted an article on - Feb 2, 2012, 10:04 am
Just a few days ago, the blogosphere was ablaze with news that transgender people could possibly be prohibited from flying in Canada, due to an uncovered regulation. Well, it looks like Canadian lawmakers aren’t done yet, as they are imposing even more travel restrictions. Here’s the...
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Amnesia Sparkles Interviews Vicki Vegotta

Jessica De Leon posted an article on - Feb 1, 2012, 11:30 am
What a great way to bring in the new month of February! The interview of Vicki Vegotta is finally here. Amnesia Sparkles of GenderFun.com had the opportunity to pick the brain of the infamous boxing cross-dresser. They spoke about the advice that Vicki gives, career, philosophies and much more!...
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Oh My! A Thinking Man's Guide to Crossplay Book Review

Jessica De Leon posted an article on - Jan 31, 2012, 11:30 am
As soon as I found out that one of my Twitter friends, blueZhift, had written a book about crossplay, I knew I just had to read it. Crossplay, a variation on the word cosplay, is the act of a person dressing up and imitating a character (of their opposite gender) from a comic book, anime
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Wife Buys Me Shoes & Gets Discriminated Against

Jessica De Leon posted an article on - Jan 30, 2012, 11:30 am
Last week I posted about getting the opportunity to host an all-female comedy show as my female alter-ego, which entailed a couple weeks of preparation. Part of this was choosing my outfit for the night, as I wanted to make a statement while looking my best. I had the dress, a pink off-the-shoulder....
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Hoover Didn't Crossdress – Crossing The Web

Jessica De Leon posted an article on - Jan 29, 2012, 8:16 pm
It’s time for this week’s installment of Crossing The Web, a weekly series posted each Saturday featuring news and happenings from around the TG world. In many cases, these stories aren’t much more than a headline but in others there is much more depth to be found. One major goal...
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Word of the Week: Crossplay

Jessica De Leon posted an article on - Jan 27, 2012, 11:30 am
It’s time for our series of posts here at Jessica Who?, titled “Word of the Week”. In these short articles, published on odd Fridays, I will explore the various labels and umbrella terms used to label us. By doing this, I hope to educate not only myself, but also anyone who may not be...
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Portlandia: Fred Armisen in Drag

Jessica De Leon posted an article on - Jan 26, 2012, 5:30 pm
Portlandia is a quirky sketch comedy show on IFC. Now in its second season, the series features Fred Armisen (of Saturday Night Live fame) and Carrie Brownstein playing a variety of characters. Because they are the main performers, this IFC Original frequently  calls for Armisen to do drag. You can...
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Comedian Jessica Who? Hosting All-Female Stand-Up Comedy Show [VIDEO]

Jessica De Leon posted an article on - Jan 25, 2012, 11:30 am
As promised, today I am sharing the video from my comedy show as Jessica. This took place last week and it was an all-female comic lineup. Like I said, it wasn’t my best night of comedy and the crowd was a bit rough. Still, I had fun and came away with some positives. Pretty soon
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American Dad!: Stan's Transgender Avatar Escapades

Jessica De Leon posted an article on - Jan 24, 2012, 4:30 pm
In the “Virtual In-Stanity” episode of American Dad!, Stan Smith realizes that he doesn’t have many cherished memories with his son Steve. To rectify this, he uses the CIA’s Avatar-esque Virtual system to control a robotic girl who will take Steve’s virginity....
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Hosted an All-Female Stand-Up Comedy Show

Jessica De Leon posted an article on - Jan 23, 2012, 11:12 am
One. That is the amount of times, before last week, that I had done stand-up comedy as Jessica. When I began my journey in the world of comedy in 2010, I didn’t know how to incorporate my feminine side into, but I knew that I wanted to. The fact is, though, that it is tough
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"Work It" Doesn't Work Out

Jessica De Leon posted an article on - Jan 23, 2012, 12:56 am
This news broke about a week ago, but ABC’s Work It has been fired, which comes as no surprise. The controversial sitcom that ignited a firestorm online goes out with a whimper after only two episodes. What’s funny is that not only has it been canceled, but the two episodes that did air...
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"Real Breast" Breast Forms Review

Jessica De Leon posted an article on - Jan 22, 2012, 6:52 pm
Today I’m going to review a pair of breast forms that I picked up from MyRealBreast.com about a month ago. It’s hard to believe, but this is now the fourth pair of breast forms that I’ve owned. Since I’ve had some time to use these, I have done a written and video review....
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A Serious Talk About Suicide

Jessica De Leon posted an article on - Jan 16, 2012, 4:02 pm
As you all know, most of my blog posts are laced with humor or at least lighthearted and whimsical. Well, today I have something very important to share with you, something that should not be ignored and shared if possible. Recently, I came back from Christmas vacation to find a shocking message in....
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RuPaul's Drag Race Season 4 Full Trailer

Jessica De Leon posted an article on - Jan 12, 2012, 3:45 pm
Season 4 of RuPaul’s Drag Race premieres January 30th on LOGO, but you can check out the trailer now! The drag queen competition reality show is entering its fourth season with a loyal and growing audience. Watch the video after the jump. Tags: RuPaul’s Drag Race, RuPaul, Logo: Fierce TV
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Dear Customer Who Stuck Up For His Little Brother

Jessica De Leon posted an article on - Jan 11, 2012, 3:02 pm
I came across a wonderful blog entry on The Huffington Post the other day that I’ve been wanting to share with you. The author tells the tale of a young boy who wanted to buy a video game that featured a female character as well as a controller colored for girls. His father wasn’t too...
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The Cleveland Show: Cleveland Jr Rocks a Wig and a Dress

Jessica De Leon posted an article on - Jan 10, 2012, 3:31 pm
The Cleveland Show, once a controversial show in its own right, is now in it’s third season. The “Sex and the Biddy” episode features Cleveland Jr, shown above, dressing up like a girl for a covert mission with younger brother Rallo. They are trying to spy on their buddy’s...
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2012 Changes Coming to the Jessica Who? Blog

Jessica De Leon posted an article on - Jan 9, 2012, 11:30 am
Last week I mentioned that there would be some big things coming to this website in 2012, and today I’d like to start revealing what they will be. I want to make this an amazing year and in order to accomplish that I have several plans in the works, some of which must remain secret
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Saturday Night Live: Charles Barkley in Drag as Joann

Jessica De Leon posted an article on - Jan 9, 2012, 7:00 am
Charles Barkley hosted the first Saturday Night Live of 2012. In this episode, he dressed in drag for a sketch that I found very funny. He plays a woman named Joann who is coming out as gay to her group of friends. You can watch the video after the jump. I really enjoyed the episode
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Family Guy: Joe Swanson's Fiona Apple Tribute Video

Jessica De Leon posted an article on - Jan 8, 2012, 9:22 pm
Family Guy, no stranger to crossdressing or transgender content, is in its tenth season. Episode nine of the current season features Peter’s friend and Quahog police officer Joe Swanson emulating Fiona Apple. Check out the video after the jump. Lois’ father is in the hospital and the...
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ABC Work It "Pilot" Episode Review

Jessica De Leon posted an article on - Jan 7, 2012, 3:26 pm
The controversial sitcom Work It debuted this week with its pilot episode on ABC. Despite the firestorm that it caused, the show has survived for the time being. We checked it out and wrote up a quick review. Is it offensive? Does it suck? Both? Find out the verdict below. Synopsis: Lee & Angel...
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Led by the Child Who Simply Knew

Jessica De Leon posted an article on - Jan 6, 2012, 5:30 pm
Last month the Boston Globe published a story about Nicole & Jonas Maines, twins who were both born boys. However, Wyatt knew from an early age that she was a girl. It’s a feel-good article that I highly recommend. You can read the article here.
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Latina Magazine: 9 Latinos Who Have Cross-Dressed

Jessica De Leon posted an article on - Jan 6, 2012, 3:09 pm
To coincide with the debut of Work It (which co-stars Puerto Rican actor Amaury Nolasco), Latina posted a feature highlighting nine Latinos who have cross-dressed in movies and television. As expected, John Leguizamo is listed for his role as Chi Chi in To Wong Foo. They also highlighted Salma...
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Happy Halloween 2011 from Jessica Who?

Jessica De Leon posted an article on - Oct 31, 2011, 4:40 pm
Today’s the day, though you may have already celebrated over the weekend and gotten it all out of your system. I wish you a fun, safe and happy Halloween. Today’s a great day for watching horror, and so I leave you with all my horror-comedy videos from YouTube. Transgender Monsters: The...
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Utah Church Says No to Halloween Crossdressing

Jessica De Leon posted an article on - Oct 28, 2011, 11:30 am
A church in Utah is having a Halloween party, but seem to be clueless as to the fun of October 31st, as they have banned both masks and “cross-gender” costumes. The picture below, published in the Dallas Voice, is of the flyer for the shindig. The cross-gender ban doesn’t surprise...
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How NOT to Crossdress for Halloween

Jessica De Leon posted an article on - Oct 27, 2011, 4:04 pm
Over the past couple of years, we’ve talked about Halloween a lot here, perhaps more than usual for a weblog. However, what hasn’t really been covered is how NOT to crossdress for Halloween. In my time, I’ve seen some very well done male-to-female costumes. However, for every well...
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Interview With the Crossdressing Vampire

Jessica De Leon posted an article on - Oct 26, 2011, 4:58 pm
This year’s edition of Transgender Monsters gives us a rare interview with two actual vampires. Alabaster Monrovia thinks he’s seen it all in his two to three hundred years on this planet. However, all his preconceived notions go out the window when he meets a crossdresser. Thanks for...
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Gilette's Guide to Men's Body Shaving

Jessica De Leon posted an article on - Oct 25, 2011, 11:30 am
Believe it or not, Gillette actually has a guide to body shaving for men. It’s an interactive webpage complete with video, voice over and sound effects. This struck me as rather interesting since I’ve never actually seen Gillette talk about men shaving anywhere other than the face. The...
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Do We Hide Behind a Mask?

Jessica De Leon posted an article on - Oct 24, 2011, 11:55 am
We wear masks for many different reasons. Sometimes, it is to scare people during a prank and other times it is to celebrate in the festivities of Halloween. On a deeper level though, masks are used to hide our true selves from the rest of the world. Have you ever dressed up in a way
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Male to Female Makeup Transformation

Jessica De Leon posted an article on - Oct 19, 2011, 11:30 am
Well, I’ve done parodies and spoofs of it before, but finally I’ve made a real male to female transformation video. Through the power of makeup, video editing and a little magic watch me transition from boy to girl. I had a lot of fun making this video and I might make another one in...
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Do You Have Crossdressing Halloween 2011 Plans?

Jessica De Leon posted an article on - Oct 17, 2011, 11:30 am
Halloween 2011 a.k.a. National Crossdressers’ Day, is just two weeks away. As per tradition, I have been watching my favorite horror movies all month as well as browsing the local costume shops. As we know, October 31st is far and away the best day to crossdress as there is a very low...
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5 Things I Love/Hate About Being a Crossdresser!!

Jessica De Leon posted an article on - Oct 12, 2011, 11:30 am
Hi there, I apologize for the sparse amount of blog posts lately. I’ve really been trying to push my YouTube channels to the next level. Here’s a new series I started, called “5 Things I Hate & 5 Things I Love”, pretty self-explanatory . In the first episode the topic...
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Commercial for New CD Ken Barbie Doll!

Jessica De Leon posted an article on - Oct 5, 2011, 2:18 pm
My friends, I am happy to share with you a great find! A new Barbie doll is coming out, a male doll named Glenn. The special thing about Glenn is that he is the first and only male doll comfortable enough in his own masculinity to wear women’s clothing. Check out the commercial below!!
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How Far Would You Go for Your Crossdressing?

Jessica De Leon posted an article on - Oct 3, 2011, 2:04 pm
We purchase clothes, set aside time for makeup application and read articles to help us better understand our nature. However, some of us go way beyond to achieve our desired look and lifestyle. I’m not talking about actually transitioning, but rather going to great lengths to be the...
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Jessica Who Featured in Frock Magazine!!

Jessica De Leon posted an article on - Sep 27, 2011, 11:45 am
Friends, I am very proud to announce that for the first time, I have been featured in the print media as a comedian. Frock Magazine, a transgender lifestyle publication, approached me a few months ago with the idea of featuring me in an upcoming issue. If you’re a fan of my writing then you...
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Are Women's Shoes More Comfortable Than Men's?

Jessica De Leon posted an article on - Sep 26, 2011, 11:30 am
A couple of weeks ago, we discussed whether or not women’s clothing was more comfortable than men’s. Now that we’ve all had time to think about it and respond, let’s look at it another way. Are women’s shoes more comfortable than men’s? I suppose it’s a bit...
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Bruce Campbell in a Skirt

Jessica De Leon posted an article on - Sep 24, 2011, 12:49 pm
Bruce Campbell, star of stage and screen, is easily one of my favorite actors of all time. From Evil Dead to Burn Notice, I absolutely love everything that he appears in. He’s also done some Old Spice commercials that were very funny. Would the macho superstar ever wear a skirt? Find out...
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Lea T. Poses for Swimsuit Photoshoot

Jessica De Leon posted an article on - Sep 16, 2011, 11:30 am
A new ad campaign for a swimsuit line called Blue Man features male to female transsexual model Lea T. in a gorgeous swimsuit. The photos are set against the predictable backdrop of a beautiful beach. The photographer is Terry Richardson. What do you think of this photo of the Brazilian model?
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Glenn Close Playing the Lead in Albert Nobbs

Jessica De Leon posted an article on - Sep 15, 2011, 11:30 am
Acclaimed actress Glenn Close undergoes a female to male transformation for her upcoming role as the title character in the film Albert Nobbs. The premise of the movie is that a woman pretends to be a man in Irish society. Albert Nobbs will debut at the Toronto Film Festival and some are saying...
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Crossdressing Husband Caught & Confronted by Wife!

Jessica De Leon posted an article on - Sep 14, 2011, 11:30 am
You may remember that I promised some new and exciting content for my JessicaWhoHD YouTube channel. I am pleased to present something different, a sketch with some drama, some comedy and a lot of honesty. It is about a husband who comes home to a wife who begins questioning him and eventually...
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Female Stars in Male Drag

Jessica De Leon posted an article on - Sep 9, 2011, 11:30 am
Inspired by Lady Gaga’s appearance as Joe Calderone, The Daily Beast put together a feature showcasing female stars who have dressed up as men for a performance. Above you can see Cate Blanchett as Bob Dylan. Some of these women have been highlighted here before, though this is a nice...
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Misty Crossplay at PAX 2011

Jessica De Leon posted an article on - Sep 8, 2011, 11:30 am
I love it when fans don’t let gender stop them from paying tribute to their favorite characters. Girls do it all the time, dressing up as anyone from Mario to Superman, but when a male dresses up as a female character, it’s sure to make an impact. Enter a dedicated Pokemon fan at this...
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About Me

All was normal in my world until the day I put on a dress. Since then, I have been dealing with life as a crossdresser. I blog about my experiences, post advice and just general ramblings.

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