Pic @ Matthew Stone
1. My boyfriend of 2 years just admitted that he fantasizes about dressing up like a woman and being fucked in the ass by a man. He also said he has a female counterpart called ‘Michelle’, and that he wants me and Michelle to hang out/have girly time together, and for me to give him a makeover, i.e. shave his legs and do his makeup. He says he’s still sexually interested in me, and I’m pretty open to trying stuff out, but this was totally unexpected and I don’t really know what to do or where to begin. Jessica, London
Well Jessica, as someone who has fucked many guys in nighties–and has even forced boys into lingerie on a couple occasions–I can tell you that crossdressing and sex mix very well. Also, what’s important to remember is, if you want to date a freak–and why wouldn’t you?–then you have to deal with the fact that sometimes he’s going to act like a freak. I always fall for weirdos and then get all flustered when they suddenly break into a seizure right before I’m about to cum, or want me to call them Dad. But in those sorts of situations it’s best to take a step back and say ‘This is what I signed up for.’ Relationships are about compromise. It might be awkward at first, but I think you have to just suck it up, slap some lipgloss on Michelle, and fuck him/her in the ass with the same zeal and passion as Tyra when she walks down a runway.
Also, I guess we have to acknowledge the fact that your boyfriend might be gay, and that this might be the first stages of his coming out. Don’t panic, this isn’t necessarily a bad thing. I mean if he’s gay and he still fucks you, you’ve basically got the best of both words. But just be aware that someday in the not so distant future he might leave you for someone without a vagina.
2. I’m 19, straight, and really enjoy sex with my boyfriend. I cum every time. The thing is, I cum because I do it myself. He can make me cum with his tongue or fingers, but not from penetrative sex, even if he uses his fingers during it. I know in the past you’ve written that this is pretty common, but sometimes I still feel like there’s something wrong with me, or that I’m cheating. Help! Carla
Last weekend I was hanging out with my new friend Rachel from the sex blog Rabbit Write, and she was talking how (most) women can’t expect men to get them off with just their dicks. She kept saying, “Girls have to own their orgasms!” And I realize this may sound like some crazy feminist psychobabble, but it’s kind of true. Penetrative sex just isn’t as conducive to the female orgasm as it is the man’s, because the female orgasm isn’t necessary for reproduction or whatever. Evolution has fucked us, basically.
But as long as you’re cuming, and your bf cares enough to help out in any way he can, then it doesn’t matter how you get there. Also, if you’re 19 and are cuming during sex, that’s a good sign! I didn’t cum during sex until I was 21. It blew actually. Most girls take a while before they master it. But once you teach yourself the way that works best for you–whether that be masturbating on the guy’s dick, or a certain position that allows you clit to rub against his pelvis, etc.–then from there it just gets easier and easier until eventually you can cum from just looking at a penis. (Yeah right.)
3. Can I have sex even though I am “fat”? I am considered “obese” (just), according to the lovely BMI, and am new to being this size. I have always been an Aus 10-12, but now I’m a 16. I am fine with my size, but I haven’t had sex in MONTHS. I am going crazy! I feel like guys don’t notice me anymore, I don’t flirt, and I don’t come onto guys anymore. The closest thing I have had to anyone taking an interest is my friend’s boyfriend asking me for a threesome (I denied, my friend is a twig, I look like the pentagon next to her). I masturbated like 8 times today! Where can I find sex? Please help! Love, “Becky”
If you’re just looking to find guys who are into bigger girls, that should be pretty easy. There are dating sites that cater specifically to BBWs (big beautiful women, obvs). Like BBWCupid is one–maybe Google search sites specific to Australia. Also, fetish sites always have sections for heavy girls and those who love them, although there will definitely be more “freaks” PMing you if you go that rout. Up to you.
However, I think in your question you contradict yourself. You said you are fine with your size, but you also said you’ve stopped flirting and approaching guys, which means something about your personality has changed since you’ve gained weight, and you’re less confident. If you feel better about yourself at a smaller size, I think you should work on losing weight. And I’m not saying that in a ‘no one will love you because you’re fat’ way, I just think you should make an effort to look the way that makes you feel most confident. Because, why not?
To quote Elle Woods, “Exercise gives you endorphins. Endorphins make you happy. Happy people just don’t shoot their husbands.” The last part doesn’t really apply to you, but the first part does. It’s a no brainer, but exercise makes you feel SO good. I always feel irrationally good about myself after I go running. Like even though my body obviously looks no different directly before a workout than it does after, something about just knowing I went running makes me feel hotter. Weird but true!