Should a woman call it quits after finding out her husband-to-be once had a wild time with a transvestite? Q: Recently a long-time mutual friend told me that my boyfriend of four years paid to receive oral sex from a transvestite during a spring-break vacation back in college. I cannot put this new information out of my head. I don't see how I can marry my boyfriend now and bring children into this situation. I confronted him (not about the transvestite, so as not to break my promise of confidence to our friend) and asked if he is gay. He swore he is not. But I am lost and confused. Why would a good-looking, confident, intelligent and successful man who could get any girl choose a transvestite? A: Do the words back in college and spring break not mean anything to you? If we judged all potential spouses on what happened on Padre Island, we would conclude that marriages consist of boob-flashing, chugging beer through plastic hoses and waking up next to people we know only as Michigan State. Why did he receive oral sex from a transvestite? Who knows. There have actually been some studies to show that most men who do are straight, not gay. According to Erick Janssen, a researcher with the Kinsey Institute at Indiana University, it could have been an experiment. What it means in terms of this persons sexual orientation is not a simple matter. Maybe he got a thrill from breaking a taboo. Maybe he thought he might be gay, did not want to admit it to himself, and figured oral sex from a man dressed as a woman avoided his fears. Or, suggests Janssen, it could be the other way around, that a person dressed as a woman makes it easier to fantasize that [the transvestite] really is a woman. Or maybe he just swilled too much Jägermeister. Many people have all sorts of sex in their pasts. You never fooled around with a guy you wish you hadnt? Half the women I knew in college at least the English and art majors had a lesbian experience. Didnt necessarily make them lesbian. But you are clearly upset by the thought, so maybe you just have to ask your boyfriend directly about the incident, and be willing to hear his explanation/denial/confirmation. Whether his response becomes a deal-breaker is entirely up to you. Oh, and this mutual friend? Hes a schmuck. IMHO this girl is a priss with a major stick up her butt. Her boyfriend got a bj from a tranny on spring break. Apparently she didn't know him back then and it hasn't happend again. They've been dating for 4 years so they both should have been tested for STD's a while ago. So why break off the engagement? I know I can sometimes be naive; perhaps I am too cavalier in my assessment of this situation. :redface: Are certain sexual skeletons a deal breaker?