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Dear Di

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...
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Dear Di

  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 fl...
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Dear Di

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 differ...
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Dear Di

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 ...
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Dear Di

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 t...
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Dear Di

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 b...
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Dear Di

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 e...
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Dear Di

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...
deardi

Dear Di

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 plann...
deardi

Dear Di

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...