Got questions for Little Bobby? Send them to dearlittlebobby@pyragraph.com.

Dear Little Bobby,

I love my boyfriend a lot and he is great in bed yet I am interested in having sex with another person. I am thinking about putting an ad on Craigslist for this. My boyfriend says he is okay with this, and might even want to watch. I believe him but I am not sure if we both know what we would be getting into. How can I know if this is right for me? I want to avoid jealously, remorse, STDs etc.

—Frisky In Frisco

Dear Frisky In Frisco,

To start with, think about this a LOT. Think about it when you are stone-cold sober. Frequently communicate your thoughts on the subject with your boyfriend. To better understand what you would be getting into, ask him how he would feel AFTER you had sex with someone else. Do you trust his response? Do you trust yourself? These are primary questions. 

Test your boyfriend’s resolve and tease him at the same time by discussing this when you are apart, maybe through text messages and over the phone, and also while you are together. To gauge the possibility of jealously, explicitly tell him want you want to do with this other person. Tell him during sex. Also tell him these details when the two of you have not recently been sexual. Give him details about this fantasy shortly after the two of you have been sexual.

Many people, especially guys, might feel like they want something (like watching their partner with another) UNTIL they have an orgasm. After an orgasm, sometimes our fantasies immediately become “Oh no, I would never ACTUALLY do that” but then time passes and the fantasy creeps back in. Sometimes this cycle repeats endlessly though our life, or at least through our sex life.

For some people, some fantasies should remain fantasies. For others, I recommend living the fantasy out, but doing it safely and with wide open eyes and a wide open heart, knowing that we can never really know an experience until we know it. 

If time passes and you really do want to experience this, and you are comfortable with where your partner is on this, then perhaps you can begin the process of exploring it. Yes, Craigslist is one possible avenue for this. You can also check out SDC.com (Swingers Date Club), a website for couples looking for other couples or single men/women in their area. There is a little more of a “menu” feeling on SDC. It is set up much like a dating site where you are able to search for singles or couples in your area. You can search for similar likes and certain fetishes and even specific ages, hair color, etc. If you truly are in “Frisco,” you should have plenty to choose from.

As far as Craigslist goes, it is a little more a shot in the dark, but you might (or might not) be surprised at what is offered on there. If you find someone you are interested in meeting, I would suggest that you try to get to know the potential person, even just a little, before you meet up. How is that possible, you ask? You can ask for photos. You can ask for verification of the photos (where they write your name on a piece of paper next to your face). You can trade emails—but you may want to consider setting up a separate, new email for this. If you are comfortable with trading phone numbers, do that. Text and/or call each other. Try a video call.

No matter how you go about it, you need to follow your gut and trust your instincts. If someone feels wrong, creepy, rude, gross, etc., trust that feeling and go no further. At no time do you ever owe anything to anyone. 

If you like the energy of the prospective person and you want to meet them, do it in public at a neutral place. Meet for drinks or appetizers. I would suggest that you meet them with your boyfriend, which would be much more safe, open and honest. If you are meeting for drinks, keep the drinking moderate. Do not let alcohol affect the decisions you make or do not make. If the feeling and conversation warrant, discuss details. What kind of activities are you both (or all three) comfortable with? Will the first time be an “all the way” experience or just testing the waters? Will there be condoms used? Are there expectations for afterwards? More sex? Friendship? Relationship? These things might be awkward to discuss over drinks, but it could easily be more awkward to not discuss them until it is too late.

If it is a “go,” go carefully. Your place or theirs? A hotel? And again, do not let alcohol affect your judgement. Stay aware at all times. This of course is just common sense when potentially having sex with anyone, whether there’s an existing relationship or not. 

I will not tell you “good luck” if you decide to do this, as luck is for fools, so instead I will tell you to be safe and careful, to stay clearheaded and to trust your intuition. As for remorse, even if the person is amazing, beautiful and great in bed, you might still feel remorse unless you truly are ready for this experience. If you are ready you might find it incredibly erotic and want to do it again and again. If you are not ready, you will hate it no matter who it is or what happens. Only you can, and will, answer to your self. 

—Little Bobby Tucker

“Sister lovers, water brothers and in time, maybe others | So you see, what we can do is to try something new.” —The Byrds, “Triad” 1967