I’m a straight female who’s been in a loving relationship with my boyfriend for three years. I’m also a politically connected woman who’s very much in control; when I say no I mean no. A little more about me: I was born in Alabama, play the piano, and for a while was a professor at Stanford University. Currently I hold a high-ranking position in Washington, D.C. I have a tattoo of George W. Bush on my right breast, but apart from that I’ve always been an average gal, especially in bed. Now, though, I’m in a real state.
My problem goes back to the beginning of my relationship, when my boyfriend tried to lick and finger my ass. I very firmly told him to stop, that anal sex totally disgusted me and I’d never allow anything–his cock included–into my butt. Needless to say, I hurt his feelings, but for a couple of years he respected my wishes. During the past several months, however, I’ve relented and allowed him to perform anilingus and to finger me–I’ve even allowed him to insert a narrow vibrator up there. At first I found this repellent, but I wanted to avoid hurting his feelings again. After a while I came to enjoy anal stimulation, but I didn’t tell him I liked it.
Now the problem: Last month, after we’d had way too much to drink, I finally let him slip his cock up my ass. OH MY GOD–talk about fireworks! Just thinking about it turns me on. At the same time I feel guilty for having done it, because I still think it’s dirty and that only sluts go there. We’ve made love since then, but he avoids my butt like he used to. For my part, I’d love to try anal intercourse again, but I can’t bring myself to ask for it. Is there any way I can have the best of both worlds? –Can’t Openly Naturally Discuss Interest
PS: Please print this letter if at all possible. 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 saving you from having to admit what a dirty little butt-sex-obsessed slut you are.
Well! Looks like my work here is done.
On second thought, perhaps I should offer a word of warning to those out there who think they might recognize CONDI. This butt-sex-obsessed slut included tons of identifying details in her letter–she wanted to make damn sure her boyfriend recognized her when he read the letter. What she didn’t anticipate, it seems, were other people recognizing her, and since I’m pretty certain CONDI didn’t intend to out herself as an ankle-grabbin’, pillow-chompin’, butt-sex-lovin’ slut, I changed one or two details in an effort to preserve her anonymity. Unfortunately, there’s now a slight chance that CONDI’s boyfriend won’t recognize her, which would defeat the whole purpose of running the letter in the first place. So here’s a hint for him: she doesn’t really have a George W. Bush tattoo on her right breast–I made that part up! I suppose there’s also a chance that the details I invented might match some other woman out there, someone whose personal and professional history, by sheer coincidence, just happens to match the one I’ve invented for CONDI. I also suppose this could result in that person being on the receiving end of some unwanted anal attention. But that’s a risk we’re just going to have to take.
I’m a gay guy who for a year now has had a crush on a straight hard hat who works on a construction site across the street from where I work. I’ve left him notes telling him how hot he is, and he’s clearly flattered. The next step in my lustful enterprise is to give him a jockstrap and 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, HHH, up to this point he’s been entirely passive, just someone out there doing his job while you stare. But when you ask him to wear a jockstrap, get it all sweaty, and return it you, you’re asking him to become a participant in your sexual fantasies. Include the $20 and he may resent being treated like a whore–a cheap one at that.
Still, it couldn’t hurt to ask. I suggest that you leave another note confessing your desire to have one of his dirty jockstraps. Don’t include money, but do offer to pay him something–you know, for the cost of the jockstrap and a little for his trouble (more than $20, for God’s sake). You’ll still be asking him to take a more active role in your fantasy (which might be a problem–he seems to get off on working you up), but he’s likelier to say yes if you can avoid making him feel like he’s working for you.
I wanted to say thanks for your donation to Planned Parenthood. I’ve always been pro-choice in concept, but other issues like the environment ranked higher on my political agenda. However, when earlier this year I was faced with an unplanned pregnancy, I was grateful to be able to make a decision based on what was the best thing for me, my partner, and my two children. Without Planned Parenthood I couldn’t have done so, and I find the nonstop efforts to shut it down very frightening. Thank you for your battle to protect sexual and reproductive rights–you’ve helped me wake up to what’s at stake.–Grateful Tucson Girl
Thanks for sharing, GTG, and thanks for the strokes.
But making a donation to Planned Parenthood isn’t heroic–really, anyone can do it. Just write out a check to Planned Parenthood, put it in an envelope, and mail it to Planned Parenthood Federation of America, 434 W. 33rd St., New York, NY 10001, or go to www.plannedparenthood.org and make a donation online.