Troy O’Leary’s Ex-Wife Moonlighting As Escort?

When you think of stereotypical athletes’ mates, a few generalizations spring to mind: gold digger, baby mama, soccer WAG, model…and those are just the nice ones. Sure, there are plenty of women out there romantically linked to pro athletes who are not vapid, money grubbing harpies, but they’re smart and usually stay in the background, living their lives out of the spotlight.

Troy Annette Gray O'Leary

Unfortunately for the genre of athlete wives, the attention whores tend to bask in the limelight, so that has become the stereotype. Notice we said “attention whore,” not the actual derogatory term for a lady of the night, which is not usually what one thinks of when one things pro sports wives. So that made it all the more shocking to learn that ex-MLBer Troy O’Leary’s elementary school principal ex-wife is actually selling her body sex companionship for cash. Hot for teacher, anyone?

(More pics of the former Mrs. O’Leary after the jump.)

(Click on the pics for larger versions.)

Annette Gray OLeary

OK, well, she’s not an elementary school principal anymore. Everyone’s lips are sealed, but perhaps her June resignation had something to do with the near-naked pictures of little Johnny’s principal plastered all over the web’s escort service ads? From AZCENTRAL.COM:

Annette Gray O’Leary, who served as an assistant principal at Kyrene Del Cielo Elementary School until June, is also believed to be Taya Taylor, an escort who advertises her services on her website, according to 12 News’ sources.

Annette Gray OLeary

Taya Taylor’s website advertises $450 per hour for a “girlfriend experience.”

According to court documents, O’Leary is the ex-wife of former Boston Red Sox left fielder Troy O’Leary. The couple has two children, one with special needs. Last year, Annette O’Leary went to court to request additional child support.

Kyrene del Cielo parents question why an educator would turn to the escort business.

Annette Gray OLeary

Well, parents, have you seen the salaries they’re giving educators these days? Unless Kyrene del Cielo (down the road that I must travel) is offering its assistant principals $500 per hour, then the escort biz looks pretty darn ritzy by comparison. That’s right - Ms. O’Leary/Taylor is charging $500 an hour for her services. Her website is down, but her ads are still plastered all over BACKPAGE.COM (NSFW, unless you work from home on your own computer like we do):

Annette Gray OLeary

Any money exchanged is for my time. What happens during our time together are the choices of consenting adults. By contacting me via phone or text or email you agree with these terms.

**upscale and passionate gentlemen ONLY!

DONATIONS
600 1HR
1000 2 HR
1500 3 HR
3000 Overnight (10 hours)

Hope to see you soon!

XoXo Taya (480) 229-2108

Annette Gray OLeary

Poster’s age: 30 

Poster’s age: 30? Interesting, that means she graduated from high school at the age of 8, according to her CLASSMATES.COM profile. Donations? Ah, yes, it’s probably all for charity. How selfless of Taylor/O’Leary to give herself up like that. A truly remarkable woman indeed.

11 comments

  1. GravatarSmokehouse
    11:55 am on August 6th, 2009

    I’ld do her. If she paid me. $500 for an hour with that battle axe I don’t think so

  2. GravatarSmokehouse
    11:57 am on August 6th, 2009

    Well I looked at the big pic of her I’ld probably give her $25 or a bag of crack

  3. GravatarJd
    2:54 pm on August 6th, 2009

    Things that could turn ya gay

  4. GravatarJoe Smoke
    3:16 pm on August 6th, 2009

    I’d rather pay a little more for Spitzer’s call girl.

  5. GravatarBrooksBigForehead
    6:33 pm on August 6th, 2009

    Is she part of the ‘Cash for Clunkers’ program Community-Organizer-In-Chief Barry is running?

  6. Gravatardank
    8:00 pm on August 6th, 2009

    None of the fat guys on here want to do you. hahhaaahahha. poor lady.

  7. Gravatarstugod
    9:19 am on August 14th, 2009

    yes xucking please from stugod

  8. Gravatarstugod
    3:14 am on September 9th, 2009

    all i can say is anyone who would not a least give her one time must be a fag

  9. GravatarMoparDave11
    7:22 pm on July 24th, 2010

    You’re all very judgemental and childish and this article is not only slanderous, but it bashes someone who does the same thing a ton of other ladies are doing to get by. I do not care what she used to do, what she DOES who she was married to or anything else. SHE IS A HUMAN BEING. She is a mom. She has bills to pay just like any of us do. SHe is not hurting anyone or doing this for drugs, and I see no reason to put her down.

    ALMOST ALL guys would do the exact same thing if you were a female and could. I think you’re all jealous. You’d “tap that” any chance you could, too. BE HONEST.

    Most of the time you PAY without shelling out the cash and just go, (which is priceless). Instead, you USE someone and she either gets PG or gets attached and drags on your ankle, or YOU get some disease. These upscale ladies who sell their companionship are classy (YES SHE IS CLASSY) use protection always, are tested regulaly and are not looking to mess up anyones life. Get a clue here, guys.

    More power to her and I wish her well in all of her future endeavors, no matter what they may be.

    Dave

  10. GravatarMeThinks
    9:56 am on April 26th, 2011

    Dave should go to hell cause’ he gives me a headache with all that mamby pamby chatter…go find a boyfriend if you need to complain that much, bro…..

  11. GravatarWhoIsThisIs
    4:29 pm on April 26th, 2011

    “SHe is not hurting anyone or doing this for drugs”

    ORLY? U NO DIS HOW?