Features > The Guidance Counselor

by Doug McClelland

[Editor: See here for our standard note on confidentiality and anonymity.]

(posted April, 2006)

From: Randy
Subject: Cucumbers
Question: Every so often I use a cucumber to open my ass up. I've been using some very big and thick ones lately. Sometimes I see some red when I wipe off the cucumber. I assume that's blood. How dangerous is what I'm doing? What about bacteria on the cucumber? I wash it before of course. Also I know several men with nine and ten-plus inch cocks, I let them fuck me pretty hard and deep enough that it causes discomfort and even pain. How much do I have to worry about them rupturing my colon?

Dear Randy: Cucumbers are a great natural dildo. You can go into the grocery store and choose exactly the size and shape of your cock substitute. Plus, they have a very cock-like feel to them. Using a well-washed cucumber should be no problem. To be extra careful you could put a condom on the vegetable.

Shoving anything up your ass can cause small tears inside you. This is why we sometimes see a bit of blood in these situations. Such tears are prime entryways for HIV and other diseases, so I hope you are using condoms with your large friends. But ideally there would not be any blood. Maybe you need to be gentler, or perhaps work your way up to the large size. Your ass will stretch to accommodate large sizes. So why not splurge and buy two cucumbers: your usual large one, and one half the thickness to insert prior. Proper, gentle stretching should help prevent tearing.

If you begin to experience pain and discomfort your body is telling you something. Back off at that point. If it hurts you may be doing damage.

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From: Another Doug
Subject: Trannies
Question: I enjoyed your recent column advising guys how to get a good response from their personal ads. One of the things you said was to list what type of guys you are into. That got me thinking about something that I have noticed in many ads. I find it odd how so many guys include trannies in their lists. No one ever says they are into trannies in real life, but there it is in many profiles. What's up with that?

Dear Doug: I think that guys are often much more frank in their online profiles that they would be in person. I’ve noticed a similar thing regarding foot fetishes (a personal interest of mine); no one mentions it in person, but it is widely listed online. Talking about your kinkier sexual interests is just not something that comes up easily in face-to-face conversation.

I recently read an interesting breakdown of what falls under the general term ‘trannies’. Transvestites are straight men fetishizing women’s cloths; transsexuals are women trapped in male bodies who are changing their sex; drag queens are gay men who are ‘celebrities trapped in normal people’. Clearly the first two are not of interest to gay guys.

I think that most of the ads you refer to will fall into two categories. Guys looking for men into drag would be many of them. Then there will be some who are more into the transgressional thrill of breaking typical norms within their sexual escapades. Getting into a bit of lingerie may just be a way of getting a different kick; something to include from time to time, but not a requirement. A great buddy of mine had an experience in this area. He had found a guy who he adored. The guy built furniture, played the harp, and was a muscle bear. My buddy told me that he said a little prayer in which he said ‘lord I’d do anything to have this man as my lover’. That night, as if a test from god, when they began to get sexual the new man proposed that they both get into pantyhose. My friend just couldn’t go there and his image of the guy was ruined. Needless to say, they did not become lovers.

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From: Conner
Subject: Confusion over sexuality
Question: I have been looking at gay porn for a while and I wank over it but I wank over girl porn as well. I’m confused. I mean I want to try guys one day but if I don’t like it does it still mean I’m bi?

Dear Conner: Whether you are gay, straight or bi is really all about what is going on inside your head and not about who you’ve had sex with. There are gay men who suppress their sexuality their entire lives, but they are still gay inside.

You say you are confused. I’m guessing from your letter that you are young and I don’t think being confused is very unusual when you do not have a lot of experience. Just do what feels good to you. Lots of people experiment along the way. I think you will find that eventually you’ll get to a point of comfort in the sexual spectrums.

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