I am a straight female and have been in a loving relationship with my boyfriend for three years. I'm also a politically connected woman, a very "in control" type, and when I say "no" I mean "no." A little more about me: I was born in Alabama, play the piano, and was a professor at Stanford University for a while. I currently hold a high-ranking position in Washington, D.C., and I have a tattoo of George W. Bush on my right breast. Other than that, I've always been an average gal, especially in bed, but now I'm in a real "state."
My problem goes back to the beginning of the relationship. In the very beginning, my boyfriend tried to lick and finger my ass. I very firmly told him to stop and that anal sex totally disgusted me and that I would never allow anything—his cock included—into my butt. Needless to say, I hurt his feelings, and for a couple of years he respected my demands.
However, during the past year I've allowed him to perform anilingus on me, finger me there, and have even let him insert a narrow vibrator. At first I found this disgusting, but I let him play there just to avoid hurting his feelings. Soon I came to enjoy the sexual stimulation it gave me, but I didn't tell him that I liked it.
Now the problem: Last month, after way too much to drink, he tried to slip his cock in my ass and I finally let him in. OH MY GOD! What a fantastic experience. Talk about fireworks! Just thinking about it turns me on. But at the same time I feel guilty for having done it because I think it's dirty and that only sluts do that. I never told him how much I liked it. We've made love since then, but he avoids my butt like he used to. I'd love to do it again, but can't bring myself to ask for it. Is there any way that I can have the best of both worlds? Thank you, Dan.
Can't Openly Naturally Discuss Interest
P.S. If possible, could you please print this letter? He reads your column faithfully, and if he sees it he just might get up his courage and try again.
Here's your letter, CONDI. Hopefully your boyfriend will read it, recognize you, and find the courage to bang away at your ass without making you beg for it first, thereby preventing you from having to admit what a dirty little butt-sex-obsessed slut you are.
Well! It looks like my work here is done.
Oh no, wait: Before we move on, a word of warning to others out there who think they recognize CONDI. This butt-sex-obsessed slut included tons of identifying details in her letter: age, height, weight, profession, hair color, location—everything short of a Google map to her apartment. CONDI did this, of course, because she wanted to make damn sure her boyfriend recognized himself and her when he read the letter. What CONDI didn't anticipate, it seems, were the odds that her friends, family, and coworkers might also read the letter and recognize her. Since I'm pretty certain CONDI didn't intend to out herself to everyone she knows as an ankle-grabbin', pillow-chompin', butt-sex-lovin' slut, I changed one or two identifying details in an effort to preserve her anonymity.
Unfortunately, there is now a small risk that CONDI's boyfriend won't recognize himself or her, which would defeat the whole purpose of running CONDI's letter in the first place. (Hint for CONDI's boyfriend: She doesn't really have a George W. Bush tattoo on her right breast—I made that part up!) There's also a chance that the details I invented to throw CONDI's friends and family off her musky, musky scent might match some other woman out there, someone whose personal and professional history, by sheer coincidence, just so happens to match the one I've invented for CONDI. This could result in that person being on the receiving end some unwanted anal attention.
But that's a risk we're just going to have to take.
I'm a gay guy who has had a crush on a straight construction worker who has been working on a building across the street from where I work for a year now. I've left him notes telling him how hot he is and he is clearly flattered. The next step in my lustful enterprise is to give him a jock strap, ask him to wear it for a day, and return it to me. My question: Would it be appropriate to include a $20 bill with my request, or would he be offended?
Hard For Hard Hats
However flattered this straight construction worker is by your attentions, HFHH, up to this point he has been entirely passive. He's out there doing his job—constructing shit or whatever—while you stare. But when you ask him to wear a jock strap, get it all sweaty, and return it you, HFHH, you're asking him to play a more active role in your sexual fantasies. You're asking him to become a participant. Include the $20, and you're asking him to become a paid participant, and he may resent being treated like a whore—and a cheap whore at that.