I hope somebody can really tell me I'm wrong, but I don't know of ANY illegal business that would be tax deductable.

But, I'm always willing to learn.

Re:can we "write-off" escort expenses?

Well I have a newsflash for you . I know someone who is an escort who DOES have a business account set up for her "Johns"
for a corperate account set up for all her married men  who need to cover thy ass. I can give you the  details if you Email me  she would not  want to post how she does it but she is legal.

Ordinary & necessary biz expenses? LOL. The audit should be fun.

Well, sahib, there are three sides to this question:

1/ First you could set up a mechanism and entities that made it appear that the money was going out as a reasonable and necessary business expense, say for catering, temp secretarial & other help, and the like;
2/ It would be even more  slick if the escort herself had a corporate setup that provided receipts and invoices;
3/ So long as there is no outside audit that digs deeply, you might get by with it. IRS investigators go talk to the people at every level to see if they really are temps and caterers. The IRS crim investigators show up unannounced.

The problem overall is that it is felony tax evasion and money laundering at both ends. The cases I've read about were criminal prosecutions by the feds & states, against some fairly slick setups, escort services with lots of shell corporations and accounts all over the city.

Maybe, sahib, you should just pay substantial taxes and sleep well at night. An IRS prosecution would probably screw up your life forever. I remember one classmate in tax from NYU who thought he could outsmart the IRS. He did federal time in the prime of his life. Your post doesn't sound like you're very experienced at this either, so all the more likely you'd slip up and not know it until they come in with the search warrants and cuffs.

It's patriotic to pay your taxes, so Dubya can pass it along to the richer guys and huge corporations who paid for his election.

If you want to boink beautiful women for the rest of your life and be free, play by the rules and pay your taxes.

Sure, if you regard her as an independent contractor or as a service that you purchase. In the former case you need to submit a 1099 at the end of the year (she might be hesitant giving you her SSN, though); in the latter case she needs to be incorporated or an LLC and she needs to invoice you for services and would need to provide you with an EIN or TIN, although you could probably fill out a non-reportable I-9 in that case (only a factor in an audit, really).

You would only have problems in the case of an audit, not because of the criminal nature of the business (the Treasury dept couldn't care less) but because the service you have written off is a personal, not business service... in this case it would be better if you have bought the services to entertain clients.

Of course, the provider could bill you via a shell company providing "consulting" or "business plan development" or something but if an audit ever turned into an investigation, then you are looking at tax fraud charges which will make charges for dallying with whores look like a walk in the park.

In weighing options remember: "johns" never go to prison, but tax fraudsters often do... and you'd be surprised how canny those fraud squads can be.

O.

Re:can we "write-off" escort expenses?

If you own your own business, you should be able to write off "theraputic massage" as a medical expense -- I would definitely give it a go.  Also, there is an agency I've seen pop up on this board that specializes in supplying "sexy secretaries" -- look like another potential write off.  I'm not an accountant, however, I only play one on TV...

Your best strategy is to write off the legal massage, whereas anything beyond that is between consenting adults.

For more information on writing off the massage, see page D1 of the Wall Street Journal 11/5/2002 ("Getting Uncle Sam to Cover Your Massage").

Personally, I don't want the paper trail of paying by check.

I'm not an accountant, but I wouldnt reccommend it unless you are willing to do some serious time if you get caught. Can we say, tax evasion, fraud, money laundering, conspiracy to defraud...It wouldnt be a pretty picture.

If you are seriously asking if it would be legal, it would be in about the same category as a junkie trying to deduct the cost of his heroin as a medical expense (not counting the money laundering and conspiracy angles)

Al Capone!!  He's the Chicago mob boss from years ago that the Feds couldn't bust...except for the IRS, that is.  Tax evasion=prison time.  Just gnash your teeth & pay your taxes like the rest of us do & you'll be far better off.

As you see in the web advertising for so many of the providers you are paying for her company. If you take her or him for that matter to a company function or have them help you at a trade show it is certainly deductable. What the two of you decide to do beyond that is your business and does not concern the IRS ot the law for that matter.

Truthfully, you can do anything you want until you get audited and the chances of that are low depending on your income level.

I may pay ladies $ to model for me as part of my start-up business.