When a Young Man's Fancy Turns to Trans - OZY | A Modern Media Company

When a Young Man's Fancy Turns to Trans

When a Young Man's Fancy Turns to Trans

By Eugene S. Robinson


OZY’s Eugene S. Robinson addresses queries from the love-weary in “Sex With Eugene.”

By Eugene S. Robinson

Trans Turnaround?

EUGENE, SIR: I have an attraction to trans women and had escapades with some of them in my early 20s. The last time I did it was back in 2008. Now I am 40 and in a firm relationship since 2011, but [as of] about a year ago, I am struggling to resist the desire for a transsexual again. This is even causing a relapse of my depression, which has been controlled for the last three years or so. Do I dive into my desires — don’t wanna hurt my partner so if I take this route, we must split — or drown them? — Help Me

Dear I Think I’m Falling: A friend of mine once tried to explain his attraction to trans women to me thusly (not that I needed an explanation): He liked sex partners who looked like women but had the sex drives of men. In a surprise none too surprising, he eventually moved into a roommate situation where his roommates were all trans women. So, for him: heaven. So while trans might have been on his palate of “Likes,” he gave himself over to it and realized that the heart—and other body parts—want what they want, and if it’s not criminal, why not yield to his enduring temptations? I mean isn’t that the coolest part of dealing with temptation? Yielding to it? In noncriminal ways?

YOU, however? In a very different place precisely because you’re in what you describe as a “firm relationship.” Presumably with a non-trans woman. Meaning? This has less to do with trans issues and maybe more to do with monogamy. Now, I don’t know that I know precisely what about trans women has made you a “fan,” but whatever it is, it is making itself known through the firmness of your seven-year relationship.

Have you ever see the movie The Seven-Year Itch with Marilyn Monroe? Maybe it’s time that you do. Because it seems to me this has less to do with the spell-casting powers of trans women and much more to do with the fact that for some, seven years might be a long time to keep the home fires lit. And add into it the fact that you’re now 40. I suspect there’s a lot going on in your head that’s not so organically connected to sex and maybe much more connected to the What’s It All About, Alfie? vicissitudes of aging.

Which is to say exercise extreme caution before doing anything radical since a permanent solution to what could be a temporary problem will help no one, least of all YOU.


The Long + Short of It

EUGENE, SIR: How much length is required to satisfy a woman? — Kanwaljit

Dear K-Man: Length of time spent luxuriating in the cool of easy conversation? The comfortable conviviality of well-prepared meals that you’ve prepared? Or how much time you invest in more than capably applied cunnilingus? Am I getting warmer?

Maybe. But I’m going to take a swing here and guess that what we’re talking about is PENIS SIZE. Rather than duck the penis discussion, let’s face it full-on — especially since I have zero interest in parroting the typical sex column crap about it not being the meat and it being the motion. Partially true, yes, but the reality is micro-penises are a reality and the likelihood of them generating the requisite level of motion to provide a satisfactory sexual experience decreases with a decrease in size.

It’s not nice to say that, but while your partners might feel obliged to lie to you, I don’t. But wait … I’m not saying that size is a cure-all. I AM saying that, in general, no matter how large the penis is, many women are not orgasming purely/solely from penile-vaginal contact. 

Which brings us back to ”capably applied cunnilingus.” Make a friend of this and your issues/interests in length will be mere memories. Good luck.

And Yet Even MORE Penis

EUGENE, SIR: Hi, Mr. Eugene. Sir. I had a question that I had been asking myself but I had not been able to answer, but I am hoping you are going to help me. If so, I’ll be very happy. So, my question is: Can penis enlargement surgery have side effects? And if so, what are they? I’m writing from Kenya. Thanks, Mr. Eugene. — Amos

Dear Famous: Thanks for writing, Mr. Amos. This is very clearly a good news/bad news scenario. The “good” news? Penile enlargement surgery IS a very real thing. The bad news? Gift of the Magi style, the bad news is also that penile enlargement surgery is a very real thing. With exceedingly serious side effects. 

Like? Like a man with a perfectly functioning but smallish penis deciding that he needs a little bit more than the 5.5 erect inches G-d had given him. He got some of his fat removed and reinjected into his penis, increasing the girth, at least until his body reabsorbed it, for a cosmetic bump that by all accounts he felt to be worth it. Immediately followed by an infection so bad that they had to amputate half of his penis. To save his life. 

So, to help you with the math: He went from 5.5 erect inches to half of that. Sort of G-d’s way of telling you, “Don’t be bothering me with this foolishness.”

Sure, this is anecdotal, but the anecdotes go on and terribly on. If you want my opinion, it’s this: The risks way outweigh the “benefits” and you’d be, overall, better off following the advice I just gave to K-Man above. Honestly.

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