Should I Hit on My Best Friend's Hot Married Sister? Also: I had a one-night stand in Costa Rica, and now I feel ashamed!

I’m a 26-year-old straight female. I’m writing because I need to ask someone what to think right now. I just fucked a guy while on holiday in Costa Rica. I thought I was sex-positive and adventurous, so why do I feel so ashamed? I’m dating a boy back in the U.S. who I absolutely adore, but we’re not necessarily exclusive. The guy was a 22-year-old local—I thought he was so sweet. But he did that bullshit “fuck her and then get her out of bed and drive her home” shit. I told him it wasn’t okay, and he made excuses. I feel so fucking pathetic right now. Is this because I did something stupid? Is this a natural feeling? Or is it a result of some deep psychological self-induced slut-shaming? Why would he kick me out like that? Please help me wrap my head around this. —Truly Underestimated Risk In Sexual Tourist Adventure

You had a one-night stand, and the dude wouldn’t let you spend the night, and now you’re having a meltdown about it. Why this reaction? Because before you could give yourself permission to fuck this guy, you had to convince yourself that this encounter wasn’t, in fact, about two people using each other. Like a lot of people who want to have one-night stands—men and women, gay and straight, locals and tourists—you psyched yourself up to believe that you two had some sort of meaningful insta-connection. (“I thought he was so sweet.”) You convinced yourself that if circumstances were different—if you were single, if you lived in Costa Rica—you could see yourself dating this guy. You rounded this dude up to boyfriend material, TURISTA, but the way he treated you after the sex was over—“Okay, lady, back to the hotel”—stripped away your illusions: He was a player, and you had been played.

Was your reaction sex-negative? Yes, it was. Are you slut-shaming yourself? Yes, you are. You did something kind of sleazy on vacation, TURISTA, just like millions of other people before you, and you misjudged someone. But who hasn’t?

As for why he kicked you out, TURISTA, I couldn’t tell you. Maybe he’s in a relationship that’s “not necessarily exclusive,” and his girlfriend was coming over in the morning and wouldn’t appreciate finding a turista—yet another one—in his bed. —Dan

Never thought I’d be writing to you for advice, but here goes: I’m a straight guy with a long-term girlfriend who has a choking fetish. She needs to be choked during sex to get off. I’m more of a vanilla kind of dude, but in the spirit of being GGG, I’ve been doing this for her. The thing is, it kind of scares me. I don’t particularly get off on it, and it actually brings out parts of me that I don’t like. More importantly, I’m really scared of hurting her. Recently while on vacation, hotel security was called because our neighbors thought I was assaulting her, as she’s a screamer and likes to struggle during sex. I’m trying to be GGG, but now it feels like every fuck needs to be a rape scene, complete with choking. She doesn’t like it any other way. I don’t want to accidentally hurt her or kill her and wind up in jail, but she’s dismissive when I share my concerns. My friends in the BDSM scene scold me and say that breath play is never okay. Your thoughts? —Throat Harm Really Obsesses This Terrific Lady Entirely

Here’s what BDSM author, educator, and activist Jay Wiseman has to say about choking in his book SM 101: A Realistic Introduction: “I know of no way whatsoever that suffocation or strangulation can be done that does not intrinsically put the recipient at risk of cardiac arrest… I know of no reliable way to determine when such a cardiac arrest becomes imminent. If the recipient does arrest, the probability of resuscitating them, even with optimal CPR, is small.”

Even if choking weren’t dangerous—posts about people accidentally killing themselves during solo choking scenes appear on fetish blogs with depressing regularity—being this woman’s boyfriend/assailant has to be tedious. Even if choking were safe, THROTTLE, you need to ask yourself if you wanna spend the rest of your life with someone who’s as inconsiderate, selfish, and sexually limited as your girlfriend seems to be. —Dan

I am a 29-year-old lesbian. My best friend has an incredibly hot sister to whom I am very attracted. Let’s call her Gladys. Gladys is about 10 years older than me and happily married to a man. We talk about life on Facebook and text each other frequently. Recently, things have gotten a bit more flirtatious. I am dying to say to her, “I am super-attracted to you and I don’t want to assume anything about your agreements with your hubby. If you ever want to explore your sexuality with a girl, I would love to be that girl.” It seems like a delicate situation. I love my best friend’s entire family. I love their mom. I have spent holidays at their house and vacationed with them. I don’t want to embarrass myself. But I know she couldn’t ask me that same thing. It just wouldn’t be right from her side, since I am her little sister’s best friend. Is there a way to roll this out? —Lesbian Under Straight Tease

Let’s do a quick risk/reward analysis, LUST. By hitting on this woman, you’re risking your relationship with your best friend, your best friend’s sister, your best friend’s mom, and all future family holiday/vacation invites for the potential reward of getting into the pants of your best friend’s hot married older sister once or twice. Seems like a lot to risk if you ask me, LUST, and you did. That said, there are a lot of married bi women out there. But if Gladys has an open relationship with her husband—or if they’re actively searching for a unicorn—it would be better if they made the first move. So keep flirting and live in hope. —Dan

A girl I worked with introduced me to your podcast a couple of months ago. You must get this e-mail (or variations on it) all the time, but I wanted to say thank you for the Savage Lovecast. It has made me feel a lot more comfortable about some of the things I like to do, consensually, with my loving GGG boy. My girlfriends sometimes turn their noses up at some of the sexual stuff I’ve tried or mentioned being interested in trying. The calls and guest experts on your podcast make me feel so much more normal, and my boyfriend loves that I’ve recently become a lot more open about the things I want to do. I don’t have a question, Dan, I just wanted to let you know that I appreciate what you and the tech-savvy at-risk youth do every week. —Eager Nice Girl Living In Scottish Highlands

Thanks for the lovely note, ENGLISH, and tell your boyfriend I said hello. And remember, dear readers, if you’re not listening to my weekly podcast—check out our brand-new site at savagelovecast.com—you’re not getting your full weekly dose of Savage Love. —Dan

Send your Savage Love questions to mail@savagelove.net.

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