Q: A guy I had a huge crush on in high school took me out once our senior year. We didn't have sex (though we came close) and he never called or really talked to me again. I always thought it was because I didn't let him "go all the way," but maybe it was because I was kind of chubby and wore glasses and stuff. I saw him a few weeks ago and I'm quite different looking. He didn't remember my name—or that we dated that one time—but he sure is interested now. What should I do?
Anne: Well, that stinks, but really, high school is over and done with. It all depends on how you feel now, as an adult. If you met up with him and find you want to go out, do it. I would say though, that if you have any kind of idea of revenge for the wrong he did you in high school, forget it. If he's still the same jerk he was back then, just don't go out with him again.
Dee: What can we say? Guys are jerks often enough when they're grown up. In high school there's no hope at all. They're totally hormone driven, with fucking on the mind morning, noon and night. If you didn't give it up, he might well have been stupid enough to forget about you. If he pulls the same shit now, blow him off—and I don't mean in the fun way you both will enjoy. Good luck.
Showing posts with label casual sex. Show all posts
Showing posts with label casual sex. Show all posts
Monday, March 28, 2011
Monday, August 16, 2010
Virgin No More?
Q: I am nineteen and still a virgin. I'm determined to fix that. However, I don't really have a boyfriend and I'd prefer not to just grab someone off the street. Is there a sex toy I can use?
Anne: What in the world are you thinking??!!? Why are you determined to give up your virginity? Is your hymen hurting you, vexing you, embarrassing you? No! It's just sitting there, secretly waiting for the right time, the right person to come along. Leave it alone until you find a man you love and want to share the experience with.
A sex toy! Of all the silly questions.
Dee: I agree with Anne although for different reasons. Sure, you can buy a dildo and technically end your virginal state. But I think doing the deed yourself would be very hard. Bring a friend if you decide to go that route, keeping in mind a guy would most likely choose to help in a more personal manner. My advice is do not attempt this at home.
Personally, I think there's nothing like the feel of a real man. Nothing like the stroke of his fingers up your leg, or his knee nudging yours apart. A dildo won't make your breath hitch like feeling a man's weight, or the wetness of his cock on your thigh, or his hot kisses trailing along your jaw to your neck and nipples. And when a man penetrates you, filling you, stretching you, heating you from the inside out, you'll know no dildo could ever do the job right. Don't forget, there's likely to be pain involved in breaking your hymen. A man will take you past that, letting you know why you went to all the trouble. Trust me on this.
Where the hell is Jack??
Anne: What in the world are you thinking??!!? Why are you determined to give up your virginity? Is your hymen hurting you, vexing you, embarrassing you? No! It's just sitting there, secretly waiting for the right time, the right person to come along. Leave it alone until you find a man you love and want to share the experience with.
A sex toy! Of all the silly questions.
Dee: I agree with Anne although for different reasons. Sure, you can buy a dildo and technically end your virginal state. But I think doing the deed yourself would be very hard. Bring a friend if you decide to go that route, keeping in mind a guy would most likely choose to help in a more personal manner. My advice is do not attempt this at home.
Personally, I think there's nothing like the feel of a real man. Nothing like the stroke of his fingers up your leg, or his knee nudging yours apart. A dildo won't make your breath hitch like feeling a man's weight, or the wetness of his cock on your thigh, or his hot kisses trailing along your jaw to your neck and nipples. And when a man penetrates you, filling you, stretching you, heating you from the inside out, you'll know no dildo could ever do the job right. Don't forget, there's likely to be pain involved in breaking your hymen. A man will take you past that, letting you know why you went to all the trouble. Trust me on this.
Where the hell is Jack??
Monday, June 28, 2010
My Sister's Fiance
Q: I'm eighteen and old enough to know my own mind. I'll start off with that. My sister, twenty-four is engaged to a man I'm in love with. From the moment I saw him I knew he was the man for me. He's twenty-six, smart, handsome and sexy as hell. A few weeks ago we found ourselves alone and I flirted a little. Before I knew it, we were kissing. He touched me in places no one else ever has and I he let me give him head. Since then, we've had to be careful around others, but we've had the chance to kiss and fondle without anyone knowing. I decided not to go to college, choosing to work instead. He's finishing up his Ph.D. in psychology, and could use a wife willing and able to help support the household until he gets on his feet. My sister wants to stay at home and start having kids. We went shopping for her wedding dress last week and as soon as I saw her in bridal white I knew it should be me walking down the aisle instead. How do I tell her with the least amount of drama?
Anne: I respect that you are working instead of going to college if that's what you want, but here are a few words you might need to look up: fidelity, trust, loyalty, sister, love. Or how about SANITY? I mean really. You flirted with your sister's fiancé, had sex with him and then continued finding ways to cheat with him behind her back. As despicable as I find his behavior, he's an outsider. You're family. She can get rid of the jerk (and should), but she's stuck with you. More's the pity. Here's my advice: Back off, little girl. Keep your hands (and mouth) off your sister's man. And if you really want to do some good, find some way to let her know what a scumbag she's about to marry before it's too late.
Dee: Well, damn. I sure hope you received some compensation for the blow job(s) you gave Asshole because otherwise you're going to be left shit out of luck when this little cluster fuck becomes known. And believe me, it will come out, if not from you to your sister, then from him or someone else. There's no such thing as the perfect secret, don't you know? And if you pointedly explain to your sister how you deserve Asshole more than she does (and I happen to agree about that), you'll lose Asshole and your sister. In fact, I'd be surprised if you were invited to Thanksgiving dinners if you do that.
This is my advice to you: keep your mouth closed from now on, mostly when Asshole has his zipper open. Stay away from him and grow up. The only man in the world you're interested in is the one guy your sister supposedly loves? To me that speaks more of sibling rivalry than a true feeling on your part. Come to grips with the fact that he's eight years older than you and studying psychology, a surefire way to find out how to manipulate people, especially immature, younger sisters who are willing to suck cock. Stop being an idiot and remember your sister is your sister forever. Assholes come and go. Trust me when I say that as soon as you tell your sister that you love her man—and he loves you back—you'll lose her trust and love and he'll drop you like an STD.
And oh yeah, talk with someone and determine how to warn your sister that Asshole is just that. If you continue on this path and/or let her marry him when you know what kind of man he really is, you'll make sin even worse.
Anne: I respect that you are working instead of going to college if that's what you want, but here are a few words you might need to look up: fidelity, trust, loyalty, sister, love. Or how about SANITY? I mean really. You flirted with your sister's fiancé, had sex with him and then continued finding ways to cheat with him behind her back. As despicable as I find his behavior, he's an outsider. You're family. She can get rid of the jerk (and should), but she's stuck with you. More's the pity. Here's my advice: Back off, little girl. Keep your hands (and mouth) off your sister's man. And if you really want to do some good, find some way to let her know what a scumbag she's about to marry before it's too late.
Dee: Well, damn. I sure hope you received some compensation for the blow job(s) you gave Asshole because otherwise you're going to be left shit out of luck when this little cluster fuck becomes known. And believe me, it will come out, if not from you to your sister, then from him or someone else. There's no such thing as the perfect secret, don't you know? And if you pointedly explain to your sister how you deserve Asshole more than she does (and I happen to agree about that), you'll lose Asshole and your sister. In fact, I'd be surprised if you were invited to Thanksgiving dinners if you do that.
This is my advice to you: keep your mouth closed from now on, mostly when Asshole has his zipper open. Stay away from him and grow up. The only man in the world you're interested in is the one guy your sister supposedly loves? To me that speaks more of sibling rivalry than a true feeling on your part. Come to grips with the fact that he's eight years older than you and studying psychology, a surefire way to find out how to manipulate people, especially immature, younger sisters who are willing to suck cock. Stop being an idiot and remember your sister is your sister forever. Assholes come and go. Trust me when I say that as soon as you tell your sister that you love her man—and he loves you back—you'll lose her trust and love and he'll drop you like an STD.
And oh yeah, talk with someone and determine how to warn your sister that Asshole is just that. If you continue on this path and/or let her marry him when you know what kind of man he really is, you'll make sin even worse.
Monday, October 19, 2009
Bridesmaid Blues
Q: Anne and Dee, I am 35 and once again being asked to be a bridesmaid. A friend I had in high school and with whom I've had only a brief acquaintance since, has asked me to attend her in her wedding. This is her second. I've yet to have one. If I had had one, I don't think I would have thought to ask this woman to be my bridesmaid--we just haven't been that close in the past few years. However, I'm still of the opinion that bridesmaids have the best shot at meeting men at weddings, so I'm considering her offer. What's the cost of one more hideous dress if there's the chance of meeting a single guy--especially one willing to go to a wedding?
Anne: Go easy on yourself. You're a mature woman who wants a meaningful relationship with a mature man. There's nothing at all wrong with that. However, why go to weddings to meet men, especially a wedding for a person to whom you don't feel any real connection? Develop hobbies where you might meet men, join church or social clubs. Get a dog and walk it to strike up conversations with men--it sounds cheesy but evidently works. Be open and friendly and patient. Princes are still out there, and they're not all hanging out at weddings.
Dee: I detect the whiff of desperation, and if I do from a note, your dates do across the table. Relax. Take a deep breath. There's nothing magical about the age of 35 that means the world has curled up in the hand basket rolling its way to Hell. Stand straight, woman. Hold up your head and show a little confidence in yourself. Nothing intrigues a man more than a woman who shows some spine. Remind yourself that not all men acting single at a wedding are single…or straight. There are better ways and places to meet men. Try acting less like you need or want a man. Perhaps then one will be willing to take the leap.
Or…go to the wedding and screw the night away if you find someone interesting. No need to waste an opportunity where there will be flowing booze and guys seeking a chance to get laid. Who knows what might come from a little casual sex?
Anne: Go easy on yourself. You're a mature woman who wants a meaningful relationship with a mature man. There's nothing at all wrong with that. However, why go to weddings to meet men, especially a wedding for a person to whom you don't feel any real connection? Develop hobbies where you might meet men, join church or social clubs. Get a dog and walk it to strike up conversations with men--it sounds cheesy but evidently works. Be open and friendly and patient. Princes are still out there, and they're not all hanging out at weddings.
Dee: I detect the whiff of desperation, and if I do from a note, your dates do across the table. Relax. Take a deep breath. There's nothing magical about the age of 35 that means the world has curled up in the hand basket rolling its way to Hell. Stand straight, woman. Hold up your head and show a little confidence in yourself. Nothing intrigues a man more than a woman who shows some spine. Remind yourself that not all men acting single at a wedding are single…or straight. There are better ways and places to meet men. Try acting less like you need or want a man. Perhaps then one will be willing to take the leap.
Or…go to the wedding and screw the night away if you find someone interesting. No need to waste an opportunity where there will be flowing booze and guys seeking a chance to get laid. Who knows what might come from a little casual sex?
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