Most of my tips are for guys who are actually planning to meet the other woman for (whispering) s-e-x. However, some are appropriate for you online-only prowlers as well.
In no particular order:
- Don't be a jerk. Be polite. Remember that it is a real human being you are dealing with. It's very easy when chatting with someone online and via email to objectify her and forget that she's not a paid prostitute; she's a woman (likely married) who has her own needs and concerns. Don't use any of the pickup lines that don't work when you first start chatting, but don't use them later, either. "Wanna fuck?" isn't very alluring or sexy at any point in the first few conversations. Just today, I was chatting with a guy for about the third time, who started off the conversation with "I wanna see your ass." Oh, come on.
- Have realistic expectations. You are not perfect yourself, ya know. Be aware that your new partner will be overlooking a few things, in your favor. Be nice and do the same. Keep in mind, too, that there is a gap between the fantasy of sexy online chat and the reality of real people. Sometimes it's a big gap. Sometimes it's not, but if you keep your expectations realistic, everything will be fine.
- Take care of the hotel room. Here's how I expressed this to a guy recently, "I'm going to lick your ass, suck your cock, and swallow your cum - probably several times - and you want me to take care of the room, too?" Get the point? Now, I don't think sharing the cost of the room is unreasonable, but don't assume that.
- Get a pre-paid credit card. It just makes things easier. You can find hotels that don't require a credit card, but if you leave one do not assume that they won't charge it, even if you are paying cash. If in doubt, ask. I've paid cash and still had an authorization charge (that was reversed) showing up on the bill. Not cool.
- Talk about preferences and other important things in advance. The time to ask her if she likes anal sex is not when you are entering her ass and she's screaming and wiggling trying to get away. Know in advance what positions she likes, and which she doesn't. If she's ok with oral, will she let you cum in her mouth? And please talk about condoms in advance. If you're too embarrassed to talk about these things, then you're not ready to fuck around. Period.
- Be responsible. Condoms are your responsibility, not hers. (Ladies, my message for you is not to trust that he'll have some. Always have some hidden in your purse.) Only teenagers end up hard, hot, and bothered and don't have a condom. As for whetehr or not you'll be using the comdoms, the two of you need to discuss that. You're adults. If the discussion does not happen, condoms are the default. That means plan on using a condom unless you discuss it and agree not to.
- Be a man. Please forgive me for being politically incorrect here, but the truth is that most of us have a whipped, wussy of a man at home (even though we love him dearly and he's a great provider or whatever, blah, blah, blah....). That's not what we're looking for when we're on the prowl. For the most part, we're looking for a man who's going to take charge of the situation, if you know what I mean. It doesn't mean we want to be completely passive, but we don't want to run the whole show. So, step up. Take charge. I had a phone conversation yesterday with a man I will be meeting tomorrow for the first time. It was a very nice and polite conversation. As we were talking about the logistics of meeting, he said, "Well, we could meet at a restaurant for coffee first, if you'd like, but there are some hotels right there. How would you feel about just getting a room and getting to know each other intimately? I already know that's what I want with you." Wow. That was a panty-dampener if ever there was one. Did you notice how he gave me the option of backing up and meeting in a public place, but he made it clear what he wanted? Very nice. Then he went on to say that he would arrange it and contact me with the location (See? Refer to "Take care of the hotel room" tip, above). In our previous chats, he was very clear about what he wanted, what he didn't want, and what he was looking for - all while being very polite, funny, and charming. Also, he led the conversation (and the chats) the whole time. He was ready with relevant questions and responses. That, grasshoppers, is how it's done. The odds that he will take charge in bed, too, are very good (lucky me!)
- Don't ask us about our kids during sex. I know, this seems like a no brainer, but there's a reason it's on my list. Understand? Just don't do it.
- Focus on pleasing her. Trust me, you will have so much more fun and pleasure if she does. Some of you do this naturally, but I'm sorry to have to tell you this, most of you don't. This tip would change slightly of you are in a BDSM relationship, but then many of these tips would a bit different in that situation.
- Know what you want. If you are conflicted about having an affair, don't do it. Wait until you know. If you only want a one time fling, don't hook up with a woman who has made it clear that she wants a long term thing. It's just not fair to her. As far as sex is concerned, it's cute when the young ones don't know what to do (See Teaching a Young One), but it's not as cute when a full-grown man is indecisive. I guess this goes along with the "Be a man" tip above.
- Don't freak out if the unexpected happens. Plan for unexpected events. What are you going to do if your wife calls? If her husband calls? If one of the kids calls? What if she gags when you're in her throat? What if you can't get it up? Seriously, it's normal to be really nervous, especially if this is your first time cheating. A touch of ED is not as uncommon as you think. I know, I know, that would never happen to you, but what if it does? What's your contingency plan? Hint: Getting dressed quickly and running from the room is not an option.
- Communicate in-between meetings. You may think that you have a meeting set up for four days from now and that's good. So you don't need to talk or chat with her between now and then, right? Wrong. The online world functions at a much faster pace than the offline world. No communication in 24 hours online is like a week's worth of silence in the offline world. I saw a movie yesterday in which one of the characters said that women are like horses; they spook easily. It's true. Even the most confident among us need to hear from you. Keep in touch. Don't think you have closed the deal, so to speak, until your dick is buried deep in one of her soft, tight warm places. Until then, you need to stay alert and keep communicating. Another experience I had was with a man I had met with twice. I got a nice email from him the next day (the same day would have been nice), but nothing else for about a week. WTF? Needless to say, I was not very receptive to his next booty call email. Hey, if that's what he wants, fine. I made it clear that I was looking for a little bit more communication than that.
- Communicate after the meeting. Make sure you send her an email soon after you've had your fun. It's just a matter of being polite. In that communication, don't lie and say things that are not true. Don't say you're looking forward to seeing her again if you're not. If you do want to see her again, tell her so. Most importantly....
- Say thank you. I don't care if you said it in the room before you left. Say it again after the fact, in writing, when you are fully clothed and not asking her for anything else.
Do you think I missed any important tips? Tell me in the comments or send me a note on Twitter.