i keep a diary

a thing in 40 photos

cross dress

appears with…
newest
cross dress
Going for it!
hans and ellen get married - part two
October 05, 2014
cross dress
Gigi and Tomina.
seventies porno new year's eve
December 29, 2011
cross dress
Psssst! You flirting with me?
seventies porno new year's eve
December 29, 2011
cross dress
I got sunburn on my chest and it hurt to rest my book on my chest so I fashioned my napkin into a tiny protective shirt and Meredith kept (rightfully) laughing at me.
honeymoon in bali part two
September 06, 2009
cross dress
Awesomeness.
the may roundup
May, 2009
cross dress
I was flipping through a magazine that Leigh had (V Magazine maybe?) and Greg's ex boyfriend Martin was in one of the shoots looking like a sexy lady!
the may roundup
May, 2009
cross dress
So good / upsetting. (Keep in mind, this is like a full two years BEFORE that girl turned herself into Jared Leto. Hahaha.)
halloween 2008
October 25, 2008
cross dress
Mandy as George Michael makes me feel funny.
halloween 2008
October 25, 2008
cross dress
Yep, there we go. Perfect. Hahaha. I love John's expression in this photo so much.
the june roundup: part one
June, 2008
cross dress
Speaking of ONE LEG....ha! The best part about Hanger Bar (which has since closed down after not renewing the lease, noooo!) was that our friends owned it so after it closed at 4am, we'd usually hang around and keep on partying. After closing time, it it came out that John has really small feet, which of course led to him putting on Alana's shoes and showing off his MOVES! (Doing the sprinkler here, obvs).
the june roundup: part one
June, 2008
cross dress
And it totally showed off my guns!
the july roundup
July, 2006
cross dress
...pink is totally my color! (If you look closely you can totally see my nips playing peek-a-boo!)
the july roundup
July, 2006
cross dress
If any casting directors read this, keep the Grizz in mind for America's Next Top Cross-Dressing Model! He's got sass and he's not afraid to show it!
the april roundup: part two
April, 2006
cross dress
There was even a saucy spin-move at the imagined-end of "the catwalk!"
the april roundup: part two
April, 2006
cross dress
...and showing us all his runway strut!
the april roundup: part two
April, 2006
cross dress
Later that night after we'd finished Cranium, Niki the Roommate came home and Grant reminisced with her about how awesome it was to get to meet Molly Sue from ANTM. Which then led to a conversation about how different girls on the show did in recent episode where they had to walk down a runway in heels...which then led to Grant talking about how good he would've been at walking down the runway in heels...which then led to him suiting up in a pair of Niki's high-heeled boots...
the april roundup: part two
April, 2006
cross dress
...Grant, who was (predictibly) dressed up as a woman! The best part about Grant dressing in drag is that everyone thinks he's dressed up as...
halloween 2005
October 29, 2005
cross dress
Um, yeah. Then apparently I dressed up in a pair of Leigh's (??) jeans and a vest that Mayim Bialik must have left at the apartment that time she stopped by to hang out after she'd finished a taping of Blossom.
teaching english in korea: part one
July 28, 2005
cross dress
PS: Check out my sweet lil' dumper. No wonder the gays love me.
teaching english in korea: part one
July 28, 2005
cross dress
...left out. Hahahahah. (OMG, no matter how many times I look at this photo it makes me laugh EVERY SINGLE TIME).
the july roundup: part one
July, 2005
cross dress
Nothing cheers up a convalescing friend like a summery blouse! I was only happy to oblige!
the june roundup
June, 2005
cross dress
"I'd fuck me."
the june roundup
June, 2005
cross dress
Then I let Sarah put make up on me.
the june roundup
June, 2005
cross dress
We were both shocked to realize that with make up on I sorta look like an older blonde version of Greg Krelenstein.
the june roundup
June, 2005
cross dress
Thai tranny Marilyns!
thailand part one: nyc to bangkok
April 11, 2005
cross dress
...wanted to get in on some of the runway struttin' action.
siege's white trash birthday bash
March 02, 2005
cross dress
Fierce!
siege's white trash birthday bash
March 02, 2005
cross dress
Ready?
siege's white trash birthday bash
March 02, 2005
cross dress
So sometimes I like to dress up like to dress up like a sexy lady when I'm high. What? What's the big deal?
accidental vacation in jamaica
February 16, 2005
cross dress
Here's what Grant thinks of me. Hahah.
fiasco's first show at the delancey
December 17, 2004
cross dress
...this. So you were right, Siege. I guess I am a size one. (PS - Hey Leigh, is there a PONY on my dress?). Afterwards, we ended up betting that I wouldn't run down Broadway buck naked for two blocks. We got down to street level and as we walked outside there were two police cruisers on the corner just hanging out. Saved by the NYPD.
the july roundup: part one
July, 2004
cross dress
Grant had been wearing jeans and when it started getting hot out, Emily, who'd stripped down to her bathing suit, offered up her skirt to Grant.
the may roundup part two
May, 2004
cross dress
Who them graciously gave me the sweetest "peek-a-boo package" shot of his orange man-panties (or "manties," if you will).
the may roundup part two
May, 2004
DSC04500.jpg
original not copied to this machine yet
"I'd fuck me. I'd fuck me so hard."
em and lo's book reading
November 25, 2003
DSC04498.jpg
original not copied to this machine yet
After the performance, we were treated to the video version of Grant dressing up as a woman for his "I Did it For Science" column.
em and lo's book reading
November 25, 2003
cross dress
Cross-Dressing Time! (Grant & Jen Crowe).
grant's 26th birthday
November 04, 2002
cross dress
Grant poses with what can only be described as the Prom Queen. (Ba-dum-dum Cha! Thank You! Thank you! I'll be here all weekend! Don't forget to tip your waitresses...)
a second prom
September 14, 2002
cross dress
After a little bit of drinking and various other card games, we decided it would be fun to play "Truth or Dare." I chose "Dare" (hoping that someone would dare me to hook up with one of the girls), but instead I got "dared" to let the girls put make up on me. It was like 8th grade all over again.
nh vacation part three: there is no such thing as nh nightlife
July 27, 2002
cross dress
Hardee-har-har. So now I'm wearing girly make-up and I figure that if I choose "dare" again, they'll reward me for being a good sport and this time I'll get to make out. Too bad I was half right. They wanted me to make out, but they wanted me to make out with Joey. When I informed them that I wouldn't kiss him with tongue, the girls conferred in the corner and then came back to announce that in lieu of us kissing, they'd decided that they'd prefer to watch us have what they called "A Sword-fight."

For a brief moment, it sounded like a win-win alternative until I realized that there were no actual swords in the vicinity.
nh vacation part three: there is no such thing as nh nightlife
July 27, 2002
cross dress
As hot as I looked (yeah, that's right - "I'd fuck me, I'd fuck me so hard."), Joey wasn't really into the sword-fighting thing either. So instead we had to bump naked asses.
nh vacation part three: there is no such thing as nh nightlife
July 27, 2002