My boyfriend is a crossdresser

Plus, caught up in the Chatroulette craze.

I'm a straight girl who started dating this straight guy six months ago. Three months in, he told me he is a crossdresser. I'm a fairly open-minded person, and I was curious what it would be like to have sex with him dressed. It brought our sex life to a new level that is very pleasing to both of us. The problem is that I find myself very sexually attracted to him dressed. I'm not as attracted to him when he isn't dressed, and the sex isn't as exciting for me. He said he's happy to dress for sex, and although I like that, now I'm afraid of getting into a routine where we will only enjoy sex in that way and down the road I may grow tired of the dressed sex and crave a regular guy. I think we both lower our inhibitions when we have sex while he's dressed. I guess I don't understand why.

Confused And Curious

When he's dressed, he's giving himself permission to live out his fantasies (with an assist from you); when you see him dressed, your inhibitions lift because, hey, there's no way you can freak out or outfreak the boyfriend. Routines can be deadly, of course, but I wouldn't worry about being stuck in a rut. You've only been doing this for a few months, and his crossdressing is still a shiny new toy. And you can't simultaneously worry that you'll come to only enjoy sex while he's dressed up and that you'll grow bored with sex while he's dressed up. If you continue to enjoy dressed-up sex, you won't get bored; if you get bored, then you can go back to non-dressed-up sex.

I assume you've heard of Chatroulette by now. I discovered it about four weeks ago, and I am strangely turned on by all the dudes on there jerking off. I have started to show my tits to some of these dudes because it is such a massive turn-on for me (who knew I had this exhibitionist streak in me?). My husband doesn't know about any of this. However, all sexual arousal is redirected his way in the form of really hot, passionate fucking!

I feel bad about not telling my husband. Do you think this is cheating? If you say it is, Dan, I will stop.

Clever Acronym

I don't want to call what you're doing — flashing random Chatroulette pervs — cheating, as cheating is such an ugly word, but odds are good that your husband would call it that.

Even so, CA, I'm reluctant to tell you to stop. Spend a few weeks reading my e-mails, and you will come to regard anything — anything at all — that lights a fire under the marital bed as a universal good. So talk to your husband. Tell him that — like everyone else on earth — you "discovered" Chatroulette about four weeks ago. Then tell him you were surprised by (1) just how many dudes are jerking off in front of their computers at any given moment and (2) just how turned on you were by their exhibitionism. Confess that you've been a bit obsessed with the site, add that it's why you've been so horny lately, and then invite him to join you for a session. If he seems into the idea, or gets into it once you're online, sheepishly confess that you've been flashing a little skin yourself.

Then fuck the husband's brains out.

I wanted to satisfy my curiosity of getting a blowjob from a guy. I found one online willing to do the deed, and we met and he started. After about 15 seconds, I stopped him. It was not for me and did not feel right. Now, in reality, what are my chances of getting a disease? Low? Medium? High? He did not use a condom. I know you are going to say to get tested, which I probably will. But in your opinion, are my chances so great that I should run to the clinic? Would it matter the time length of the BJ? Say, if it were 10 to 15 minutes instead of seconds?

Sent From My iPhone

It only takes a moment to contract a sexually transmitted infection you could have your whole life long, SFMi. If the guy who blew you — however brief the blowjob was — had syphilis or chlamydia or herpes or all three, you could've contracted any or all of them. You can't contract an STI from a guy who doesn't have any STIs, of course, but what do you think the chances are that a guy who blows strangers he meets online has an STI? Low? Medium? High?

Go get tested, SFMi.

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