The male and female officers who take on the undercover assignment as a prostitute often struggle with how far to carry the "walk and talk" to make a good case. The balance is no different in vice operations than when making a good drug arrest. The undercover (UC) officer must blend into the crowd, as well as lead the conversation in a safe and lawful way.

In conversations with a target, how far can the UC go before a defense attorney can use an entrapment defense? That's the key to a good UC operative. A "business" discussion between a prostitute and a john is straightforward with sparse small talk. With a UC, the business transaction must be suggested and led by the john. He or she should name the specific sexual act and cost when talking to the UC.

Most officers have heard and seen it all, so this small talk shouldn't offend the UC. Simple questions to the john should lead the conversation in the right direction. Here are several things to say:

• What do you want today?

• Tell me what you need.

• What kind of date do you want?

These questions lead to specifics without leading the john. The cost of a "trick" seals the deal as far as making a case, so it's important to let the john name his or her offer. Again, simple questions frame the john's response.

• How much is that worth to you?

• What would you pay for that?

Try not to be offended by what the john might think your services are worth. Save that for a laugh with your team later. Like any other encounter with a suspect, maintain a reaction gap between you and the john, so you can quickly move to protect yourself or escape a grab. Nothing's for free with working prostitutes, so keeping a distance between you and the john shouldn't arouse suspicion.

What about attire? Should you dress the part of a prostitute? The UC's attire must be sufficient to fit in with the group, but also comfortable enough so the UC can move freely and not have their clothing used as a weapon against them.

I can't emphasize enough the importance of a good cover team. Remember, things happen quickly so be mindful of items that could be used against you such as necklaces, scarves, or flowing shirts that can be grabbed. Always wear a bright color that can be seen from a distance by the cover team.

Most operations of this sort occur at night, so dressing all in black can work to your disadvantage when blending in with the girls or guys on the corner. The "Pretty Woman" outfits worn by some prostitutes are not readily at hand for most officers, nor are Lucite platforms or 6-inch stilettos. You don't have to wear good running shoes, but find something in between that doesn't mark you as an off-duty officer.

The clothing should allow freedom of movement in case the officer becomes engaged in a struggle. Apply the same rules of wearing a uniform to the undercover clothing you choose. Avoid items such as dangling earrings.

Hopefully, the UC will walk away before a struggle occurs but always be prepared to deal with a wacka-doodle. Lastly, I would suggest the UC wear clothing that sets her apart from the other business women. This might attract more customers and can also help cover officers identify the UC from a distance. An agreed-upon color that all officers wear during the operation helps distinguish the good guys from the bad guys in the heat of the moment.

Another consideration is whether to carry a firearm when working UC as a prostitute. Officers usually carry semi-automatic pistols that don't lend themselves to easy concealment with casual wear, particularly for women.  There are compact makes and models with slim frames designed specifically for concealed carry ( S&W's M&P Shield is the latest example).

Whether to be armed or unarmed during a UC prostitution sting should be weighed against crime in the general area, especially whether there has been a history of violence against the prostitutes. Some officers won't go out without their weapon, and that's fine.

One option a department may pursue is purchasing several of these small weapons to be kept in the armory specifically to be used during UC operations. Most PDs can't afford multiple types of weapons for officers that may be in use infrequently, so an inventory for that purpose is certainly more affordable.

However, don't hand the new low-profile weapon to a UC on the day of the operation. The UC should be familiar with the weapon and have qualified with it before the operation. The officers shouldn't struggle to work the kinks out with a new weapon under pressure with a john.

This also applies when the UC carries the weapon in a purse or fanny pack.  Learn to quickly retrieve the weapon from its holster or carrier before it's an emergency. Practice, practice, practice.

A firearm may not be needed. Oleoresin capsicum spray is, in my opinion, the best offensive weapon during a street prostitution sting. The key to good defense is a good offense, and pepper spray can temporarily disable a john while the cover team responds. A UC can more easily carry and conceal pepper spray than a firearm. Because prostitutes carry this and blades of all sorts, this is an offensive option that doesn't cause too much concern if discovered.

Most importantly, establish a signal for arrest. This can be visual or verbal depending upon your access to technology. The most significant safety point for the UC should be "do not reach into a vehicle." This is an important note for all officers, not just in this type of operation. We never know what the client might have to lose if arrested; a frightened john might decide his or her best option is to try to flee with your UC holding onto the door frame.

Gerry Long served with the Savannah-Chatham (Ga.) Metropolitan Police Department for more than 30 years, retiring in 2011 as a deputy chief.

Related:

How to Plan a 'John' Sting