Justin

You don’t. In polite society, masturbation is not a casual act to be performed with every Tom, Dick, or Harry you know. Life is not a porn movie. While masturbation can be a healthy expression of one’s sexuality (if it doesn’t become an obsession), it is proper for you to conduct that activity when you are alone or with someone with whom you share a mutual love that transcends friendship. You described the relationship you share with the gentleman in question as friendship. Like all worthwhile relationships, friendships appropriately have boundaries that are not to be crossed. People with a healthy sense of self understand that feature of friendship and conduct themselves accordingly. It is clear from your question that you have sexual desires for your male friend, whom you understand to be straight; but if you are committed to respecting healthy boundaries that will successfully promote the health and longevity of your friendship with him, you will not act on your first sexual impulse. If you cross that boundary, what’s next? “Hey, Boss, wanna join me in my cubicle for a session of simultaneous masturbation to porn on our company provided computers?” Please, if you have an irresistible urge to perform some sort of socially acceptable act with your friend, shake his hand; and let that friendly gesture suffice.

Given your unresolved issues about your sexual orientation, I would guess that you are somewhat young; but whether you are young or old, you have grown up immersed in an ever increasingly toxic culture that has produced ubiquitous pop icons characterized by a decided lack of probity. Madonna, for example, had no qualms about peddling a book comprising a photograph that explicitly depicted her engaged in an act of anilingus with male model Tony Ward. She probably made a lot of money from that book. She is often praised by pundits in the mainstream media for her keen business savvy, but there are loftier ideals to which one can aspire. You won’t often see those ideals extolled in the mainstream media, however. Be aware of what messages you accept as valid from the mainstream media and our culture in general. Do not buy into every message being sold to you. Learn to sift through the mainstream media’s messages about what is acceptable social behavior. Discard the ones that do not elevate your consciousness – like the notion that masturbation is a casual act to be performed with every friend in your social circle. Refuse to be “dumbed down” by the culture in which we live.

Your question also prompts me to remind you to live your truth. We are all capable of clinging to self-deception to protect ourselves from emotional pain. We all need to be more aware of this weakness, and your question is teeming with clues that you have been overtaken by it recently. For example, your friend is straight; and you have convinced yourself that you are permitted to disrespect his sexual orientation in your capacity as his friend. I, however, will remind you that you are not permitted to do so. Whether one is straight, gay, or bisexual, he always needs to respect a friend’s sexual orientation. The outlandish, manipulative scheme you have contemplated clearly comprises an ulterior motive that is disrespectful of your friend’s sexual orientation. You harbor the secretly held hope that your friend will discover he has previously unrealized homosexual tendencies if you can only arrange for him to be in a sexually charged environment that will promote that realization. If your friend is straight, however, the truth is that he cannot be converted to a different sexual orientation. Your boyish good looks and masculine charm cannot convert him; alcohol cannot convert him; votive candles cannot convert him; a sexually charged environment cannot convert him. Now is the time to abandon the self-deception you have conjured in order to convince yourself that you can convert your friend, for any attempt to do so is wrong. Your friend is as entitled to his sexual orientation as you are entitled to yours. Moreover, you should think more highly of your friend’s evolvement. Don’t be so eager to assume that he has such a poorly defined sense of self that he will overlook it if you make an inappropriate invasion of your friendship’s boundaries. I would also gently suggest that you reevaluate your current description of yourself as straight like your friend. It is true that your current understanding is that your friend is straight. It is, however, untrue to say that you currently possess such a clearly defined understanding of your own sexuality. The truth is that you are uncertain about your own sexual orientation. You are currently experiencing profound curiosity about your own possible bisexual proclivities. After all, you are having sexual daydreams about a straight male and envisaging a misguided stratagem to lure him into a homo-erotically charged environment even though your relationship with him is categorically defined as a platonic friendship by both of you. Claim your truth. Verbalize it, and live it. The truth is that you have unresolved issues about your sexual orientation. Your statement that you are straight is not reflective of someone who is living his truth. You may be straight. You may be bisexual. You may be gay. Your intuition is telling you to further explore your current understanding of your sexual orientation. Abide by your intuition, and undertake the exploration of your sexual orientation in the light of truth. In the eighties, Cyndi Lauper artfully sang these beautiful lyrics by Billy Steinberg and Tom Kelly: “I see your true colors / And that’s why I love you / So don’t be afraid to let them show / Your true colors / True colors are beautiful / Like a rainbow.” I hope that from this day forward, you will begin to relate and infuse the story of your sexual exploration with your true colors. It’s the only way that your story can ever truly have a happy ending. I wish you fair winds and following seas.