One of my coworkers and her husband want to have sex with me. They are a little younger than me and newly married, but do this “all of the time” according to her. She told me that I’m the one they want, but I can bring another woman if I want, or they know another woman if that would be easier. This started with them inviting me to their place for a drink after a work event. I turned them down, and she said I should come because they gave the best “team head.” I didn’t even understand what she meant at first. Since then he has emailed me detailed pictures of them having sex with another guy who is like 40. What is really embarrassing is that the idea has started to really turn me on. I have been single for a while now and am not one to just hook up with a girl I meet out. I oftentimes don’t even have sex for the first month or so that I am dating a new girl. I have never had sex with another guy and never thought I would, but in a threesome it’s not as gay sounding, I guess. I don’t know what I should do. She is always flirting with me at work and winking. I am really an average guy and this is not me, but this fantasy has worked its way into my reality and I want to know what to do.
— Curious About Being Caught in the Middle
P.S. They are both very attractive and she is what I would consider out of my league.
Dear Curious About the Middle,
If she wants to have sex with you, even if her husband is there, it means she is not out of your league. That being said, it doesn’t mean you should sleep with them, it just means you should recognize that you are as attractive to them as they or she is to you. If nothing else, at the end of the day recognize the compliment and feel good about yourself.
You are not the first straight man to consider having sex with a couple or another man. I am not saying their proposition is the standard at company picnics, but it does happen. It is nice that your reaction has not been one of judgment. Even if it’s not your cup of tea, you need not be going around condemning them for their personal choices. That’s what the 700 Club and reality TV are for.
If her advances are bothering you, ask her to stop. Politely tell her that the flirting makes you uncomfortable and you would prefer she kept things professional in the workplace. If she refuses, and it continues to bother you, that is sexual harassment and you can always file a complaint — but keep that to a last resort as it is rough on everyone, including you.
If you think you might really want to try out a little swinging with the Joneses, proceed with care. Try to imagine you have already slept with them and ask yourself how you feel about it. The last thing you want is to be left feeling dirty or guilty. You need to ignore the will of your dick and read your personal moral stance on this.
If you decide to go for it, you might research “the lifestyle” on the internet. Learn a little about what you are getting yourself into before you jump. Let them know you are interested and want to have a drink and talk about it so you can be more comfortable. Ask questions, let them know if you have limits in advance, and be clear that if you become uncomfortable that you can exit at any point, no fuss, no drama. Though one hopes that experienced swingers are taking precautions to protect themselves and their partners, be certain that safe sex is on the agenda. Let your coworker know that it is an experiment for you, you prefer to keep your private life discreet, and don’t want this to be shared with anyone. Then have fun.
Or not. Life goes on, and yours is more interesting than a lot of others. Hooray!
Much love and a good time either way,
Your Uncle Mat
Uncle Mat answers questions about relationships, sex, pets, and art. Email him at email@example.com, myspace.com/yourunclemat, or check out the Dear Uncle Mat Page on Facebook. Your true identity is safe with him.