Lately he's been very vocal about needing "fresh pussy." Those were his exact words. He is very honest with me, and I think honesty is better than being lied to and cheated on. My last boyfriend -- whom my friends loved -- lied to me all the time; this boyfriend -- whom my friends hate -- at least doesn't lie. He's also great in bed and makes me feel beautiful, but I'm afraid if I don't pick up other women with him, he will start cheating on me. My sister says that he is a gigolo (I frequently bail him out of financial difficulties), and that he gives me nothing. She's wrong: He gives me great and frequent sex, and makes me feel beautiful.
Also, he won't wear a condom, but we've both been tested for all STDs. I am attracted to women, but I'm afraid if we get involved with someone else, she'll take him away from me. I don't want to lose this guy! Should I stop lending him money? I rarely had sex in my last relationship, so maybe I'm placing too much importance on sex now. How can I get assertive without losing him? Am I a sucker?
Lovesick in La La Land
You are a total sucker. You're such a sucker that people in New York City can hear the slurping. You couldn't be a bigger sucker if there was a white stick in your ass and your head came wrapped in cellophane. He takes your money, tells you he wants "fresh pussy," and won't wear a condom? That makes him an ASSHOLE, and makes you a fool-flavored, all-day, capital S, capital U, capital C, capital K, capital E, capital R -- SUCKER.
Your friends and your sister are right: This washed-up porn star is using you. Can't you see that he's preying on your battered self-esteem, and counting on the emotional damage done to you by your last boyfriend to keep both your legs and your checkbook open? OF COURSE he goes out of his way to make you feel beautiful. OF COURSE he fucks you on a regular basis. If you were paying my bills, I'd tell you that you were hot and fuck your brains out on a regular basis, too. Since this guy is in it -- in YOU -- for the money, there's no way to "get assertive" without losing him. The moment you stop lending him money, or tell him you're never going to help him pick up other women, he'll be out the door faster than you can say, "No, I can't make your car payment this month."
You've set up a false choice for yourself -- a bogus choice between assholes like your last boyfriend and assholes like your current boyfriend. But there are good guys out there (and good girls) who aren't users, who won't insult you ("fresh pussy?" Is your pussy stale?), and who can pay their own bills. There are even guys who can have the occasional three-way without dumping their sexually adventurous girlfriends. Actually, there are good guys out there who would kill for a bisexual girlfriend who's game for the occasional three-way -- don't sell yourself short; you're in demand!
By the way, if you're inclined to stick with the porn star, consider this: He's probably already fucking other women. I felt it in my gut reading your letter, and no doubt you feel it, too. Dump the loser, save your money, and find someone else.
About a month ago, I hooked up with a "skater-boy" (a boy who skateboards). I never thought I'd be into this kind of boy, but now I'm hooked. He hasn't called me back since he dropped me off the next morning. What kind of girls are [skater-boys] into? How should I comport myself? Where would I meet more of them?
Gee, thanks for the clarification on "skater-boy" (a boy who skateboards); couldn't have worked that one out myself. Second, since most skater-boys are just that -- boys -- I suggest you comport yourself like any other pedophile. Fill your pockets with candy; drive slowly past parking lots popular with skater-boys; offer to buy them beer if they'll let you take pictures of them with their shirts off -- that sort of thing. Good luck.
I am a 30-year-old woman. I've been dating a recently divorced Catholic man for over a year now. While I am in love with him, I have a difficult time with a "habit" of his during our physical intimacy. He won't come, finish, orgasm, or whatever you want to call it. He claims that for religious reasons he won't have intercourse, but we do everything else. We engage in this type of "anti-climactic" play two or three times a week. (He doesn't come, but I do.) To make things even more perplexing, HE is usually the initiator. He is 42 years old, and has six children with his ex-wife. Is there some kind of serious problem here? How should I approach him about this subject? What do you suggest I do?
Frustrated in Fremont
The man you're in love with has a sexual hang-up, but not all hang-ups are serious problems. Here's a hypothetical situation: A man with a hang-up about rimming -- he doesn't like to have his ass licked -- marries a woman who doesn't enjoy licking ass. Is his hang-up a problem? No, he doesn't like to be rimmed; his wife doesn't like to lick ass. What's the problem? He doesn't get his ass licked; she doesn't lick ass -- everybody's happy! But if his wife loves to lick ass -- if she lives to lick ass -- then his rimming hang-up would be a very serious problem indeed.
But problematic hang-ups can be overcome, and most are overcome at the insistence of an annoyed partner. So what to do? Insist. Confront your boyfriend about how absurd this hang-up is; point out the hypocrisy of this doing-everything-but for "religious reasons"; tell him it annoys the fuck out of you; and then call his bluff. From now on you're an all-or-nothin' gal. Either you're having sex -- both of you, with orgasms and everything -- or you're not. If he's not ready, willing, and able to come, then he shouldn't initiate anything.
Finally, there's an off-chance his problem isn't a hang-up at all, but a lame stab at Catholic-style birth control. The man has six kids and some rather large child-support payments to make. Fear of more kids may be why he's reluctant to come in, on, around, or near you.
Confidential to Craig B. on the Coast Starlight: Work the dining compartment? No thanks. While I enjoy a yeasty Portland microbrew as much as the next guy -- to say nothing of the cello -- there's a limit to the kinds of yeasty things I'm willing to put in my mouth.