Dear Di, I cannot orgasm. I just can’t. My boyfriend thrusting inside of me feels good, but I always go to sleep really unsatisfied. I’ve tried rubbing my clit while we bang but it doesn’t help, which makes me think masturbation won’t work either. This is really frustrating and I’m worried I won’t ever be …
Dear Ty
Dear Di, My boyfriend has lost all interest in sex. We’ve been together for 10 months, so we’re out of the honeymoon phase, but I have reason to believe it’s more than that. I was on his laptop a few days ago and found a gay porn site in his browsing history. I can’t help …
Dear Di, My girlfriend is a fake and bake addict. Recently we were doing it doggy style and I noticed something: She has three white spots developing on her body, one on each of her shoulder blades and one on her tailbone. They’re not raised or anything like normal moles would be, but I’m still …
Dear Di, I am a PhD student in my sixties and am doing my best not to be perceived as a dirty old man, but I just don’t know how to behave around younger female students. I’m looking for a real relationship full of romance and eroticism, but I need some advice about what is socially …
Dear Di, You know how it’s really difficult for some women to orgasm? Well, I have the exact opposite problem—whenever I ride the bus, I climax. In the amount of time it takes me to get from my apartment on Lees Avenue to the Laurier Avenue bus station, I will have reached orgasm. If I’m …
Dear Di, My boyfriend made me a cake for my birthday and he put his ejaculate in the mixture. The cake tasted amazing and it led me to start fantasizing about what it would be like to eat cake out of his ass. What are the logistics of putting dessert in someone’s rectum and eating …
Dear Di, I want nothing more than for my girlfriend to give me a blumpkin. You know, suck my dick while I take a shit. How can I ask my girlfriend to give me one? —Blump King Dear BK, You want a bathroom blow job and I want someone to locate my G-spot without …
Dear Di I want to make things more festive in the bedroom this December, but my Santa hat just isn’t enough anymore, so I came up with a new idea I’d like your opinion on. I want to use a candy cane as a dildo and masturbate in front of my boyfriend. My pussy will …
Our resident sex columnist spreads a little cheer I THINK IT’S safe to say Old Saint Nick won’t be visiting me this Christmas Eve. I’ve been naughty this year—in countless different positions, three provinces, and with more than a few partners. Santa won’t be leaving any presents under my tree, but I do have high …
Dear Di, I’m a gay man who came out of the closet at eight years old, so imagine my surprise when I started a new job one month ago and promptly became sexually infatuated with one of my female co-workers. I have never been attracted to a woman, so I’m really confused and I think …
Dear Di, I know this isn’t technically a sex question but my roommates and I feel you’re the right person to turn to. This summer, a new guy moved into our house. We all share one shower and take turns cleaning it. Recently, the drain became clogged and we discovered the blockage was caused by …
Dear Di, I am boy crazy, but the guys I tend to like are white and I’m not. I’m so scared to go up to a guy who is a different race than I am. How can I figure out if a guy is attracted to non-white women before I approach him? —Looking for a …
Dear Di, I’m in my early 20s and still a virgin. I’ve had the opportunity to have sex, but it didn’t feel right. I’m still holding out for when I feel ready, but the older I get, the more left out I feel. I’m starting to feel like a huge loser. Am I weird for …
Dear Di, I have a problem: I’m sleeping with two guys right now, which is great, except for the fact that they both have tiny penises! Nothing turns me off more than when a guy’s pants fall to the floor and I find a little baby carrot staring me in the face rather than …
Dear Di, My friend and I write a role-play story together and things can get pretty hot between my character and hers. The more our characters have sex, the more I want to get it on with her. We live in different cities and she’s told me she doesn’t do long distance, so I know …
Dear Di, My girlfriend has a huge clitoris. It’s probably an inch in length when she’s aroused. I’ve seen a few vaginas in my day, but nothing like this. Should we be worried about it? —Pretty Huge Clit Dear PHC, In a word, no. Chances are everything is A-OK with your lady love. Clitorises are …
Dear Di, I know this guy who is hot, funny, ambitious, and we have the same interests. Lately the sparks have been flying between us, and I was pretty sure we were going to hook up, but then I was hit with the “girl code.” My friend basically forbade me from ever getting with my crush because …
Dear Di, I have a huge crush on my roommate. He’s sexy, funny, smart, and we have the same taste in music and television. One problem though: He’s straight. I’m just so crazy about him and I think we would be such a good couple if he would just give me a chance. Do you …
Dear Di, I usually talk to my friends about sex, but I have a secret I could never reveal except under the guise of anonymity. To put it bluntly, I’m really turned on by Gee-Gee, the school mascot. I can’t explain it, but I just find him really sexy and I feel aroused whenever I …
Dear Di, My girlfriend is a virgin and has a really tight vagina. We have to stop every time we try to have sex because she says her vagina is too small and it hurts. This makes me feel awful because I love my girl and don’t want to hurt her, but we’re both getting …
Dear Di, My girlfriend has a dildo she likes to use during her alone time. I’m curious as to what it would feel like in my asshole. My girlfriend will think I’m gay if I ask to borrow her dildo, so I’m planning on grabbing it when she’s not looking. I know you encourage experimentation, …
Dear Di, I am obsessed with my roommate. I can’t sleep, I don’t eat much, and I can’t study. I constantly refresh her Facebook profile to see if she’s been talking to other guys. She doesn’t like me back at all and sees me as her “little brother.” I’m looking for a way to get her …
