“I am not a licensed therapist, guru, or magic relationship mender. This is sex and love advice from a guy who has seen both failure and success in the relationship department.”

Nothing’s Shocking

“I am a little jaded, a little disillusioned, a little sarcastic, yet very honest. Answers may be sincere, absurd, comical, or sometimes flat-out wrong. You’ll have to consider the source, I suppose.”

What’s the best way to approach some daring sex you and your partner are both interested in but apprehensive about, such as hiring a hooker or going to an S&M club?

Well, I would never suggest you do anything illegal … in print. Let’s categorize these things as “alternative-lifestyle interests” and take it from there, shall we?

Clubs are easy. Just go, even if it’s for ten minutes to get a vibe. If you end up staying for 15 minutes, chances are you’re not as apprehensive about it as you may have thought. You can do some research on the web and ask around in online communities beforehand. The real issue is your own moral compass. If you have no problem with the issues that could come up for some people, then I say get on with it. We aren’t here for all that long, and you may as well gather your experiences while you can, provided you are safe and stay within whatever limits you have outlined for yourself.

As for seeing hookers, my advice is simple. Be safe, safe, safe, safe! And don’t get caught. If you are looking to do away with feeling apprehensive, don’t bother. Apprehension is basically a mild form of fear, and for many, it’s the fear that makes such choices alluring and hot. For some, it’s not the sex with a hooker that is a turn-on but the fact that it’s dangerous, illegal, and socially frowned upon. Personally, I am all for the idea of legalizing prostitution. I believe if it were legalized, the rate of crimes against women-would dramatically drop. I also think that the women in this line of work deserve the benefits of dental and medical insurance, probably more so than the average office worker.

How do you talk to someone who isn’t meeting your needs in a relationship without hurting her feelings or putting her on the defensive in any way?

Depends on what needs you’re speaking of. If the needs are of a sexual nature, there are a couple of ways you can go. Instead of asking, “Why don’t you ever do such and such?” try suggesting it as a joint project, as in, “Wouldn’t it be fun if we tried such and such?” it’s a little manipulative perhaps, but it could save you from an uncomfortable situation where your partner feels less than worthy.

If your needs are of an emotional nature, sometimes being an example of what you want is a great way to show someone the areas in which they are lacking. However, at the end of the day, a conversation is the best way to communicate your needs. If your fear of that conversation is keeping you from having it, you may want to look at why you can’t even meet your own needs. If you can’t I take care of yourself and say what you want, how can someone else do it?

I just started hanging out with a seriously hot rocker girl. She’s made it clear that if we go on a date she won’t sleep with me. She isn’t saying she won’t go out with me, just that she won’t sleep with me. What does that even mean? Is she trying to discourage me or trying to seem like marriage material? How do you deal with a preemptive cold shoulder?

Well, I suppose she’s saying that she is not someone to easily give up the sex, if that’s all you’re after. She’s more or less interested in seeing what happens. My advice, should you go on the date, is to just play it cool and not even think about sex. If it’s meant to happen, it will. Look at it this way: You’re already not sleeping with her. What’s the worst that could happen? You’ll still be not sleeping with her.

For me, sex wouldn’t be the issue here. I don’t like conditions set prior to a date. If I’m truly interested in the person. however, I don’t really care. You may be making a bigger deal out of this than it is. I mean, how long does a “date” really last? A couple of hours? Surely you can make it through a couple of hours, be respectful of her wishes, and not cross a boundary.

During sex, my husband often mentions daring sex, wanting to watch me have sex with another guy — or two guys. We have never had an open marriage and have never brought other partners into our bed. I have to admit that the idea of another man intrigues me, but I wouldn’t want my husband to be with another woman. (I know. But I’m being honest.) I keep asking him if he’s sure he wouldn’t be jealous and it would not affect our marriage, and he keeps assuring me that he would be ok with it. Am I asking for trouble if I agree?

I’ll tell you a cautionary tale that a friend of mine once shared. He was really interested in seeing his girl with another man. He asked and asked and asked her to sleep with a friend of his while he watched. One night, after a few drinks. she caved in and agreed. My friend watched as his girl had relations with another guy. While in the midst of watching, he realized that not only did it bother him, he was sickened and disgusted. He couldn’t handle it. When the whole thing was over, she went back to my friend and expected a warm reception. He said, “That was a test and you failed,” and broke up with her immediately.

I’m not saying that this will happen to you. My point is that sometimes our fantasies are larger than we think our feelings will be. Be careful.

I have been dating my boyfriend for five months now. We’re exclusive and it’s getting serious. Before we met, he had signed up on a few dating sites, met women on these sites (not me), and went on a few dates. No big deal, right? This is 2011. Well, I recently discovered that not only is he still a member at two of these sites, but he logs on to them regularly. When I confronted him, he said it’s no big deal; he doesn’t talk to anyone on them. I am a very trusting and nonjealous person, and I have no issue with him keeping the sites (for now). What I do take issue with is that he logs on to them every day. I can understand that every few weeks, if you’re online and bored, you would log on. But his behavior makes me worry that he is keeping his options open and not totally committed to us. What do you think? I need a guy’s advice. Is this no big deal? Is it all in good fun? If the tables were turned, would you feel strange about your girlfriend keeping a profile on dating sites?

It’s the old “online takeout menu” issue. Look, what is acceptable to one person is not always acceptable to another, and I have no idea what you’re willing to overlook. Devil’s advocate time: I have a number of sites that I look at on a daily basis, merely out of habit. I wake up, have some coffee, and look through various music sites, humor blogs, Facebook, Twitter, and the like. Even if I’m not that interested, I’ll browse through them all anyway. Granted, none of these are dating sites and I don’t have a girlfriend. Regardless, maybe it’s all just habit with him. Maybe he’s just looking for outside validation without the intention of following through. I have to speculate because I have no idea. The real question is: What is acceptable for you? If you are wishy-washy about your own boundaries, how can you expect someone else to know what they are? Perhaps this isn’t about him, but about you and your ability to speak up and take charge of what you want. He is who he is, and you chose him. Now you have to learn to navigate through this relationship as an adult.

Penthouse has taken advantage of a lot of advice from the profoundly sexually experienced. Many of you may remember Leah McSweeney from these very pages. Dave himself has two other entries chosen to highlight our Legacy section in this very site as well. If you missed them, Shocking Temptation and the original Hot Tips are both just a click away. Powerful things sometimes, those Daring Sex clicks.