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She's Putting Herself Through Med School Doing Sex Work—What Does She Tell the Doctor She's Dating?

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I’m a 30-year-old female in my last year of medical school. I’ve been a full service sex worker for the last three years to support myself through school. I’m out to all my friends and family, and they're all supportive, but I’m not out to anyone at the hospital or who could have any influence on my future job opportunities. I’ve been single this whole time or had casual FWBs who didn’t care that I was a sex worker.

I’ve recently started seeing someone I like and could see myself being with long term. I haven’t been in a proper relationship for a while and it’s nice to finally find someone I feel this way about. I haven’t told him about work. He’s also a doctor at the hospital so he’s not in the category of people I can just tell and then if they don’t like it then too bad for them, since I don’t want people at the hospital to know. We are in our early days and we haven’t discussed being monogamous yet but I know that’s what he wants. I’ve been "kicking the can down the road," as you say, to avoid saying "Yes, we’re monogamously boyfriend and girlfriend!’ and then by extension be cheating on him every time I accept a booking.

I'll be a doctor in less than a year and already planned to stop doing sex work after that. So should I tell him about the sex work and risk the consequences? He might not have a problem with it but more likely he will have a problem with it and then there will be a doctor at my hospital who knows. Or should I stop working and be with him? That option would involve moving house and getting some probably more stressful and time consuming job in my final year of med school. Or should I lie to him for another year about the one booking I accept a week or should I stop doing full service and do massage or something else instead and get tested regularly and always use condoms with him and every client?

All of these seem like shitty options to me. Can you think of another?

What Do You Think?

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Navigating a Newly Open Relationship, More Advice for Lonely Gays, and a Cute Pup in an ITMFA Hat

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Savage Love Letter of the Day: A letter writer suggests "let's make racism so gay the racists can't stand it anymore" (no), a letter writer's boyfriend won't let her go to HUMP! without him, no more death-gripping, and this letter writer's group sex with her fiancé is great but she can't come during it and feels guilty after. And, as always, last week's column and Savage Lovecast.

Regarding NOPE:

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Group Sex With Her Fiancé Is Great But She Can't Come During and Feels Guilty After

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I’m 30, a cis female, romantically attracted to men and sexually attracted to men and women. (Whatever that is? Heteroflexible?) Anyway, I’m engaged to the absolute love of my life, it blows me away everyday how compatible we are, he’s the fucking best person I know.

My question is in regards to this: we are both sexually attracted to women and have been interested in exploring other people together. We’ve had a number of experiences, threesomes/orgies and while on the whole I feel like they were positive experiences, I always walk away with a certain degree of troublesome negative emotions from it. I feel a fair amount of shame/guilt when I participate in what society tells me is slutty/a-typical sexual behavior. I was also shamed as a kid for “playing doctor” with both boys and girls which has contributed to my feeling guilty about experiencing sexual pleasure in general. I’ve also been with plenty of guys that affirmed that my sexual pleasure was not as important as theirs, so it's safe to say I have some emotional baggage when it comes to sex. (Doesn't everyone? Thanks, religion and patriarchy.)

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Another Sufferer of Death-Grip Syndrome

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Hi, Dan. I'm looking for some advice. I'm 26 years old. Never had a girlfriend or even kissed a girl before. But a few months back I met a girl started dating and eventually having sex. Before her I used to masturbate a lot, like four or five times a day. Everyday. But since we started having sex she hasn't been able to make me come — or should I say, I haven't been able to come. She's doing all the right things but it feels like nothing. Maybe I've been desensitized to the "light" touch. I don't know. But it's really starting to bother her, even though I assure her it's not her, it's me. Do you know of any steps I can take to alleviate my ejaculate situation or any way I can calm and reassure her that her efforts are "valued" (for lack of a better word)?

K From Queens

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Her Boyfriend Won't Let Her Go To HUMP! Without Him

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New to Savage Love. My SO and I love porn, so I was really excited when I discovered HUMP! Film Fest. We cleared our schedules and I purchased tickets. Unfortunately, his schedule with his children changed and he is no longer able to go. But he has made it clear that he does not want me to go without him. He doesn’t believe this will be an appropriate event for me to attend solo because I have a history of infidelity (in previous relationships), I’m almost always down to fuck, and a total babe. I understand his concerns, but I really want to go! Should I lie about going? Should I tell him to get over it and go anyway? Or should I stay home and use my tears as lubricant while I masturbate? (I don’t have a penis. Tears would be for my vagina).

Tell Him About The Hump! Occasion

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The Gay Community Already Has a Flag, Thanks

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Please consider this idea. It sounds batshit crazy, I know, but let's make racism so gay the racists can't stand it anymore.

I'm tired of the Confederate battle flag. It represents the worst in white people, and is a banner for those who would take pride in toothless cousin-fuckery. It also represents the ability to openly proclaim a belief that a group of people should be enslaved, tortured and quite possibly murdered not only for the color of their skin, but for the financial gain of said toothless cousin fuckers. So let's get off our ass and fix it because Walmart banning cakes ain't going to cut it, and frankly you running your mouth about the racism of white people or Trump supporters or people that own guns doesn't do a damned thing either.

The fastest and most permanent fix is if you got the most overt and flamingly gay man you can find to wear a Confederate flag proudly — shirt hat belt buckle, doesn't matter. March in the next pride parade waving one. Remake them in rainbow colors. Tell gay men to lay those flags down, turn a camera on, and fuck all over them, then use that flag to mop up the santorum and wave it around on Xtube and Pornhub for other gay men to fap to. Every dic pic on Grindr should have a confederate flag backdrop. Jump in the back of a pickup with confederate flags waving and go to town on each other while you drive around. Instead of protesting old confederate monuments and statues, just have gay orgies at them and turn them into the preferred cruising spot in any city dumb enough to leave the statues up. See another guy wearing some sweet confederate gear? Tell him he's got a tight ass and you want a taste. Truck parked with one? Leave him a sexy note about how hard that flag makes your cock. Sky is the limit, just have fun with it.

You won't like this, no gay men will like this, black people aren't going to be huge fans either, but no one, NO ONE, is going to flip shit like everyone who currently loves that flag and all those racist god damned confederate war memorials will. When they say, "The south will rise again!", one gay dude telling them back, "Oh yeah, I'm getting hard again", is going to completely shut them down. Instead of antifa throwing rocks in Charlottesville, just start fucking in the streets. An onslaught of gay guys in Confederate hot pants might actually bridge the divide between other minority groups and the gay community.

The Cocks Shall Rise Again

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Letter Writer: Stop Assuming You Know What Women Want

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Recent Savage Love Letters of the Day: A teenage boy's girlfriend comes easily—but not during sex. Teenage boy asks: What's wrong with her? A letter-writer's ex sucked at sex but she usually came. Her current is AMAZING at sex but she never comes. Help! Another letter-writer didn't actually cheat—almost did, but didn't—but her husband is sure she will cheat sometime. So why punish her now? And this letter-writer is into guys but not into dick, so...? And, as always, last week's column and Savage Lovecast.

For TLB, the teenage boy who doesn't know why his girlfriend isn't coming during sex:

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He's Into Guys But Not Into Dick

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I'm a 24-year-old mostly gay male. While I've had sexual experiences with women in the past, I find myself much more attracted to men. I only came out and started dating men when I was 20.

Lately, I've been having a hard time thinking about what turns me on in the bedroom. I've realized I really just don't like dick. I hate the smell of dicks, the taste of dicks, the look, shape and feel of dicks. The thought of giving head makes me gag (not in a good way), the few times I've tried bottoming, there was no pleasure in it for me, and the one time I tried topping I went soft immediately. That being said, I've learned to give incredible handjobs that gets the job done, but at that point I just want them to cum and be done with it. I really only get turned on when someone does things to me—like gives me head, rims me, jerks off on me, or puts me in mild bondage and jerks me off.

Obviously, this aversion to dick doesn't make my dating life too easy. I do great on first dates, but once things move to the bedroom, my reluctance to give head or have anal sex is a dealbreaker for many guys, and things end there. My question is, what is up with me? Am I just a lazy lay who needs to gain motivation to do more in bed? Recently a friend suggested that I may be asexual, but that doesn't feel right. I feel like I'm attracted to everything there is about men, all except what's between their legs. Have you heard of queer men like this?

Wish I Liked Dick

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She Didn't Actually Cheat—Almost Did, But Didn't—But Her Husband Is Sure She Will Cheat Sometime. So Why Not Punish Her Now?

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I’m a 25-year-old female. I’ve been married to my husband for two years, together for a total of four. I had an emotional affair, admitted it to my husband but downplayed it, and came clean about everything a month later. Suffice to say that my husband was furious. He doesn’t believe he can trust me (I don’t blame him) and mentioned divorce. I have cut off communication with the other guy and started therapy to deal with the issues that led me to the decision I made (crippling insecurity and a pathetic need for validation from the opposite sex). I know I screwed up, perhaps irreparably. I hate the thought of being such a young divorcée but here I am. I never thought I’d be one of those people.

More than anything I guess I’m looking for an opinion on whether you think we can push through this. Given your years of experience in this field I’m sure you could make an educated guess. To be honest I’m also looking for some encouragement from fellow readers who have been here. I acknowledge my major fuck up but don’t want to believe that I am the scum people will see me as if and when we separate. Besides apologizing profusely, giving him space, and promising not to let this happen again while taking steps to better myself, what can I do? This is killing me.

Young And Fucked Up

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Her Ex Sucked At Sex But She Usually Came. Her Current Is AMAZING At Sex But She Never Comes. Help!

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I am newly divorced and have started a relationship with a man I’ve known and deeply cared about for decades. I am more open and honest with him (both about sex and in general) and trust him more completely than my ex-husband or any prior partner I’ve had. We are in a long distance relationship which means we’ve only been able to fuck a dozen or so times, but our sex is amazing—from start to finish I feel better than I ever did even in the best moments with my ex. And in the most intense moments? He makes me see stars. He has remarkable oral skills and is a very generous lover—plenty of foreplay and great communication. He turns me on like crazy and I regularly cum during sexting with him. But contrary to all this, I have yet to have an orgasm with him.

In the past I have only had an orgasm with a partner from oral or occasionally digital clit stim (but even when it worked, playing with my clit during sex was rarely appealing). My ex-husband was not skilled at oral—very lackluster and repetitive. I always had to fantasize pretty hard to get there (and regularly chose not to bother with an orgasm during sex with him). My new partner has amazing moves I didn’t know existed and has me screaming out pretty much nonstop. He has made it very clear that he is willing to keep at it for as long as it takes to get me there, and I believe him. But regardless of how amazing I feel when he’s going down on me, every single time I eventually hit a wall out of nowhere where I am just done with oral and want to fuck. (And the fucking is absolutely incredible, too.)

I haven’t had a single session with him where I’m left feeling unfulfilled, regardless of the lack of orgasm. In contrast, any sex with my ex that didn’t end in an orgasm left me feeling frustrated or worse yet, bored. (There were also times when I’d ask my ex to leave the room so I could masturbate after sex. It was easier for me to do myself. But I have no desire to to that with this partner, because the orgasm isn’t the fun of our sex—being with him is.) I don’t necessarily feel the need to cum. He isn’t pressuring me or making me feel guilty for not getting there—he gets that responding that way would only make it more unlikely. But I feel like an orgasm is the gold standard for sex. It feels almost disingenuous to say he is the best I’ve ever had if I’ve never managed to get there.

Do you have any ideas as to why I can’t get over that hump? I wonder if I just need him to be more boring and repetitive so that I can focus, but if that’s the case, is it even worth it? Why would I want to make the sex worse to make it “better”? Or should I just be satisfied with the mind-blowing sex I am having, even if it means I don’t have an orgasm? Is it ok to give myself permission to give up on partner-based climaxing?

No Orgasm Possibly Ever

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Teenage Boy's GF Comes Easily—But Not During Sex. Teenage Boy Asks: What's Wrong With Her?

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Originally published July 19, 2007.

I'm 18 years old and my girlfriend and I have been engaging in sexual acts. She has no problem coming, but when it comes to sexual intercourse she can't orgasm. Is my penis not doing the job correctly? She says she feels good, but can't climax. Could there be something wrong with her? I don't know what to do.

The Lost Boy

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CelebDeath

Burt Reynolds

Dead.


Reader Advice on Jerking Off and Eating Too Much

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Recent oldies: His wife says he can't jerk off, but it helps him focus! This guy is up to his eyeballs in covet—Is it time for a divorce? She's turned on when she forces her boyfriend to eat, but is she forcing him to eat too much? And, as always, last week's column and Savage Lovecast.

First, jerking off:

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I'm Turned On When I Force My Boyfriend to Eat, but Am I Forcing Him to Eat Too Much?

Originally published on Oct 15, 2009.

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I'm a 25-year-old girl dating a 26-year-old guy. My boyfriend identifies as sexually submissive. He likes to be tied up, put in women's underwear, and locked in a chastity device, and he has a strong urge to please. I hate the term, but I suppose you could call me a "feeder." I am turned on by the idea of someone eating a lot of food, usually junk food, and putting on weight.

It's probably related, but I'm also a bit of a fitness nut. Consequently, I feel somewhat guilty about indulging my fetish, but I figure every now and then shouldn't hurt. Thing is, he's started to eat too much to please me. He's put on weight, and while the libido part of me finds it hot, the logical part of me wants him to be healthy and stop before he gets, like, actually fat.

Thing is, it's hard enough to convince your partner to work out when it will lead to your being more attracted to him. It's nearly impossible to convince your partner to work out when it may lead to your being less attracted to him. So what do I do? I could say he knows the risks, and I'm not forcing him to do anything. But I would still feel bad knowing that he was essentially worse off—less healthy—for having dated me. I don't want to give him a complex.

Fat Admirer Troubled

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Savage Love: Shooting Stars

Joe Newton
Joe Newton

I'm a cis woman in my mid-40s, and my significant other has a cuckolding fetish. My first response was "Oh, hell no!" But if I'm willing to have a threesome, how much further of a stretch is it, really? He does have some experience with this varsity-level kink, so he knows what to expect. I've asked him some questions, but some things I prefer to research on my own. My questions for you: (1) I don't get cuckolding. I've read all about it, but nothing about it resonates with me. My SO really wants me to be into his fetish if I am going to act on it, but what if I'm just into being GGG? Can't that be enough? (2) How should I go about finding appropriate candidates who would be into sharing this experience with us? I'm not really sure that I'd want someone with experience as a bull, because I don't feel good about this playing out the way I've seen it in porn. (3) We enjoy cross-dressing and chastity play. How do I find someone who will be cool about my SO sitting in the room in a cock lock and lingerie? (4) I kind of have a "type" (don't we all), and I'm not certain my type plays into this kink. I prefer someone who is very dominant in public but submissive to me in the bedroom. This doesn't seem to align with your typical bull behavior. However, I do not enjoy being dominated. Do you think this matters?

Can't Understand Cuckold Kink

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