Dear Sasha: I am a straight gent in his 50s and my question is: where do all the mature (40+) transsexuals/shemales disappear to when they have outgrown the downtown scene? I'm not interested in men, but I have an overwhelming desire to get together with that woman with a package. The downtown action does not appeal to me (I've had my turn) and I'm not looking for an escort, even though they are young and beautiful. » Michael

Dear Michael,
My friend, shemale entertainer Amanda Taylor, makes some interesting points. Amanda thinks one reason it may be challenging to meet mature shemales is because those who would have transitioned about 20 years ago in a less receptive climate may have felt pressured, in order to fully pass, to go for full surgery, including vaginal construction. She also says that many older shemales may be living quietly, choosing not to reveal their status.

Add to this the possibility that older shemales "disappear" because of years of discouraging love experiences. To paraphrase Marlene Dietrich in Shanghai Express, sometimes it takes more than one man to change your name to Shanghai Lily. "So many of us have been screwed over," says Amanda. "You know, men say they're looking for commitment, but if you want to date me, I want to meet your friends and your family. You don't need to tell them I have a penis, just introduce me as your girlfriend."

Have you considered that the person on the receiving end of your attention may be interested in being perceived as more than a sexual novelty? Because of the mystique around shemales - and the fact that so many of them are visible as sex trade workers, and play on this cachet in order to finance their transition - it is difficult for people to place them outside of the realm of fantasy and fetish. The word shemale itself is most often used in the context of sex work, and is considered an insult by many transgendered women. Since we as a larger community can't seem to accept the sex trade as legitimate work, you can imagine how it fractures a smaller one in which many members work in the business.

www.ringsurf.com/netring?ring=trans;action=index is an amazing Web ring that includes links to transgendered Web sites and resources around the world. This is something I would suggest looking into if you are interested in exploring the lives and experiences of transpeople; www.tsgirlfriend.com is a site that includes articles, tips and chat rooms for people who want to date pre-op or post-op transwomen.

Dear Sasha: I'm a 27-year-old guy dating a 25-year-old guy. We've been seeing each other for about a month now. He constantly has bad breath along with what seems to be a gum infection. When we have oral sex, he insists on swallowing my semen when I ejaculate. It's a major turn-on for him. Do you think it could become a health problem later on, considering we have sex at least five times a week and that he has so-so dental hygiene? » M.A.

Dear M.A.,
I spoke to a dental hygienist who said that semen, "Should not have any deteriorating effect on his dental health." His bad breath is likely from the build-up of plaque on his teeth and bacteria on his tongue, as well as possibly from cavities. She suggested he should see a dentist, of course, as well as remembering to brush his tongue when he brushes his teeth.

If you are concerned about the possibility of him contracting something like HIV from this activity, yes, his infected gums will provide an entry point for the virus if you or any of his former lovers are positive.

On the purely sucking side of things, if you haven't taken the appropriate steps to ensure that you are both apprised of your STI status, and you are non-monogamous to boot, then you may be at risk for infections like syphilis, which is running roughshod over the queer boy community again. For more information on this, go to www.actoronto.org/syphilis.

Got any questions for Sasha? Write her at
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e-mail: pouledeluxe@yahoo.com