by Lindy West
And finally, CAEM, there is no God—you do realize that, right? No hell below us, above us only sky, etc.
So I Just Discovered Anal Sex
MY BOYFRIEND AND I are straight college students, and he’s always wanting to try new things. Recently, he asked to put a finger in my ass while we were having sex. Someone did that to me before, but it felt uncomfortable and it kinda hurt. I told my boyfriend that he could do it once and then I would decide whether to let it continue. So we tried it. It still felt uncomfortable and still kinda hurt. But I never came so hard in my life!
Now the question: If it’s uncomfortable, but it made me feel amazing and come really hard, what should I do? Continue with it? Or tell him to find some other way of getting me to that point again?
Presently Obsessing Over Totally Extreme Reaction
You could ask the boyfriend to stick a finger in one of your armpits—or in an eye, a nostril, your toaster—but unless your pit/eye/nostril/toaster is wired the way your butt appears to be, POOTER, no amount of pit/eye/nostril/toaster fingering is gonna jack up your orgasms quite the way that finger in your butt did.
So here’s what you’re gonna do, POOTER: You’re gonna breathe deep, you’re gonna take things slow, you’re gonna use more lube, and you’re gonna spend more time warming up the outside of your butt before anything goes in. (Tell the boyfriend he can finger your butt for 10 minutes after he rims it for 20.) Do it right, POOTER, and pretty soon you won’t be able to look at those 10 fingers of his without thinking about the kick-ass, anal-enhanced orgasms you’ll be having when you can only see nine.
I AM AN 18-YEAR-OLD FEMALE COLLEGE FRESHMAN. My boyfriend is also 18. He recently confided in me that he wanted to wear my panties while I wore his boxers and fucked him in the ass with a dildo. I have been reading your column since I was 13. Had I never read your column, I might have assumed my boyfriend was gay or thought he was gross or thought I was gross for liking the idea. Instead, I picked out some panties that looked sweet on him, and we had a wonderful time. Thank you so much!
Loves Boys In Panties
No, thank you, LBIP, because every time a straight girl sticks something up a straight boy’s ass, a bigoted state representative dies a little inside.
I AM A COMPLETELY STRAIGHT GUY. I am madly in love with my girlfriend. One night, she was giving me oral and stuck a finger in my ass. I was uncomfortable at first, but in a little time I began to like it. I found it felt so good. Now my girlfriend asked if I wanted to try a butt plug. At first I said, “Yes!” But now, the more I think about it, I am starting to think it may be gay. My question: Is there something gay about using a butt plug?
Guy With Anal Interests
I’ve dedicated my life to reassuring panicky straight boys that a little anal stimulation won’t make ’em gay. My oft-stated position: If a guy and a girl are doing it during sex—whatever it is, whatever it looks like—it’s straight sex. And, yes, that includes a pair of straight girls making out to turn on a straight boy, as well as the far less common straight-boys-making-out-to-turn-on-a-straight-girl scenario.
But no more. From now on, I intend to sow gay panic when and where I can. Maybe straight men, who vote in overwhelming numbers for the various antigay shit on their ballots, won’t be so quick to strip gay people of their civil rights if they’re worried that one false move—or one finger up the butt—can turn them gay. So for the record, breeder boys: A finger in the butt can make you gay, using a butt plug can make you gay, doing it doggy style can make you gay, playing with your nipples can make you gay, fucking a woman in the ass can make you gay, wiping from front to back can make you gay, standing up to pee can make you gay, and watching dudes hump dudes on ESPN—Ultimate Fighting Championship—for sure makes you gay.
So I’ve Been Thinking About Polyamory
I’M A BISEXUAL WOMAN, age 20, and I am threesome-ing it with my best friend and her boyfriend during a stay abroad. I knew the girl (mostly straight) beforehand. She thinks it’s hot when I participate—i.e., when it’s three of us in bed—but she gets jealous when her boyfriend and I do anything without her. I don’t get jealous when she is alone with her boyfriend, and he doesn’t get jealous when she and I do things alone.
She doesn’t want to be possessive, but she’s got alarms going off. Which is odd because in two months I’ll be gone and they’ll both be staying in Europe. It feels like she’s suddenly setting a lot of limits. We have a blast when we’re all together, but we have no real ground rules. I want this to work!
Bi Girl Interrupted
Gee, BGI, I’m shocked things aren’t going well—I mean, you have “no real ground rules,” and as everyone knows, neglecting to establish ground rules is the secret to threesome-ing success.
Wait, did I say the secret to threesome-ing success? I’m sorry, BGI, I meant failure. To ensure the failure of a threesome—whether you’re threesome-ing your way through an evening or a summer abroad—it’s crucial that you refrain from establishing ground rules. Don’t talk about your expectations, just make assumptions; don’t make sure everyone’s on the same page, just stomp around the minefield of love and lust until the whole fucking thing blows up in your faces.
I trust you’re detecting sarcasm, BGI.
Here’s what I suspect the problem is: You’re operating under the assumption that you’re an equal partner in this threesome, BGI, and that this is a sort of quasi-poly arrangement you’re enjoying with your best friend and her boyfriend. Share and share alike, right? But your best friend views you as a side attraction. She sees you as something—pardon me, someone—that she and the boyfriend brought into their relationship, not someone who they’ve brought into the relationship itself.
In other words: They’re the couple—they were a couple before you came along, and they’re planning to be a couple after you’re gone. If you’re unclear on that concept, BGI, it’s because the three of you failed to establish clear ground rules and expectations and now you’re confused, she’s jealous, and he’s either taking advantage or feeling caught in the middle.
Luckily it’s not too late for the three of you to sit down and establish some ground rules. It may be that your friend, while comfortable with the idea of you and her messing around without the boyfriend, isn’t comfortable with the idea of you and the boyfriend messing around without her. You may regard that limitation as unfair and irrational; the boyfriend may regard it as unfair and irrational; I may regard it as unfair and irrational. But if you want this to work, BGI, then you’ll make allowances for your best friend’s comfort levels and security and honor her limitations. And if you don’t wanna honor ’em, you’re free to go.
I’M A STRAIGHT COLLEGE GUY, age 21, and I share a house with some buddies and a couple. This couple has been together for four years. They’re both quite sexual, but she’s got more libido than he does. I’ve got a big sex drive, too. Both of them have stated an openness to polyamorous situations. She started flirting with me, and flirting turned into no-sex threesomes with her and her BF every few nights.
I’m perfectly fine with poly, or I wouldn’t be doing this, but it feels a bit awkward fingering her or sucking on her nipples while her boyfriend is in the room, or even the same bed. Both of us guys are straight and have no desire to see the other naked, so there’s none of that going on. I’ve got no beef with guys who like beef, but being in a sexual situation with another guy—like the one going on here—makes me uncomfortable. And anyway, I feel like he’s the “primary” one, the one she loves and kisses, so I move over whenever he shows interest. This is reinforced because she said that she didn’t feel comfortable kissing other guys—although fingering is fine (?)—and I get the impression that he’s not entirely happy that I’m cuddling and/or fingering his girlfriend while he plays Dawn of War five feet away from their bed.
I’m fine with being the “secondary” guy. But I’d much rather have some privacy if we—meaning me and her—are gonna try to get each other off, particularly
if this arrangement of ours should progress to actual sex. But this is tough, since there’s nowhere else in the house to go other than their room. Incidentally, we haven’t told our other friends/housemates about this, although they could probably put two and two together; she screams in orgasm, and half an hour later I say good night and go back down to my room.
Any advice for making the situation more comfortable for all involved?
Can’t Think Of A Clever Name
You’re fingering her, you’re sucking her tits, you’re getting her off (screaming orgasms induced dicklessly), she’s getting you off (your orgasms induced somehow or other)—which means, CTOACN, that this can’t be described as a “no-sex” arrangement. You’re not having vaginal intercourse, you’re not kissing the girl, but you’re having sex, and a lot of it.
But I wouldn’t slap a 10-dollar word like “polyamorous” on what you’re doing. You may be in a polyamorous relationship someday—with this couple, with some other couple—but all you’re really doing at the moment is “messing around.”
Okay, CTOACN, it sounds like this girl is pretty up front about what she’s comfortable doing—no kissing, no vaginal intercourse (for you)—and clear about her boundaries. You need to be similarly assertive. Tell them both that you’re not comfortable messing around while he’s in the room. So instead of playing Dawn of War while you two mess around, her boyfriend could head to the library, go for a walk, do some reading in the communal space of your shared house, or—hey—go play Dawn of War in your room for a while.
If he balks, CTOACN, then you may want to reconsider the assumptions you’ve made about him. You’re not comfortable with any hint of guy-on-guy, but he may want to be in the room while you’re messing around with his girlfriend because he digs that hint. I’m not saying that he’s bi, or that he wants to get with you, as the kids were only too recently saying—but I’m not saying he isn’t bi or doesn’t want to get with you, either. I guess what I’m saying is …
Considering (1) his presence every time you’re messing around with her (surely the library, the living room, or your room would’ve occurred to him if he were uncomfortable being in the same room while you fingered his girlfriend), (2) the limitations she’s placed on the kind of sex she’ll have with you, and (3) his tendency to suddenly “show interest” after you’ve been messing around with his girlfriend (at which point you “move over” and, presumably, out), I’m thinking this girl’s boyfriend is into cuckolding-lite.
Not that there’s anything wrong with that, of course. But it could mean asking for quality time alone with his girlfriend would bring the messing around to an end.
I’M A 21-YEAR-OLD WOMAN with bi-curious tendencies who’s been in a committed relationship for four years. He’s sweet and kind. We share a lot of interests and get along very well. Thing is, I don’t know if I’m meant to be in a committed relationship. For the past year and a half, I’ve been thinking about what things would be like with another man. I also frequently imagine what it might be like to sleep with another girl. In fact, whenever I’m masturbating, I get more excited by lesbian scenarios than straight scenarios—although I’ve never been able to come. I’ve never experienced an orgasm. But that’s another can of worms.
I’m open to the possibility of a threesome, but my boyfriend isn’t. He’s completely against the idea. From the start, I’ve never hidden the fact that I’ve never reached orgasm, and he’s never created any macho drama about that.
I’ve slowly come to the realization that I’m no longer sexually attracted to my boyfriend. I don’t have the motivation to improve our sex life anymore. I just go through the motions. At the same time, my boyfriend remains my best friend, and I’m not willing to give up my best friend over sex. I want to keep him in my life, as he is my most important source of emotional support.
Have My Cake
You can have your current boyfriend, HMC, at the price of a lousy and uninspired sex life with a guy who doesn’t give a shit about your pleasure—excuse me, a partner who hasn’t created a lot of “macho drama” about the fact that you’ve never had an orgasm and isn’t interested in helping you realize your fantasies—or you can find a new boyfriend and/or girlfriend and perhaps discover that orgasms are easier to come by when you’re with someone who (1) turns you on, and (2) gives a shit about your pleasure, and (3) hasn’t come to symbolize the death of sexual possibility.
Giving up the current boyfriend means you’ll have to find a new emotional tampon—excuse me, a new “source of emotional support”—but that’s a price that you should be willing to pay, HMC, particularly at your age.
And if you don’t want to find yourself boyfriendless and best-friendless ever again, HMC, in the future keep those roles separate.
I AM A 21-YEAR-OLD MALE in a loving and committed relationship. The sex is great; the evenings together are great. It’s a perfectly happy relationship except for this one thing: I can’t get enough change. I want to be having sex with someone else. One girl is never going to be enough to make me happy.
I have asked her about the possibility of having a threesome. She said she would never go for that, not MMF or FFM, and she is utterly against it and always will be. But I NEED more. Sad fact.
What do I do?
Coming Up More
Look, CUM, you’re 21 and you’re not ready to settle down—or settle for one person—not yet anyway, maybe not ever. However lovely this girl is, however pleasant your evenings together are, you’re not sexually compatible. There would be fewer divorces and less heartbreak if people were encouraged to view sexual incompatibility as the deal breaker it inevitably becomes over time.
Dump the nice girl, be single, fuck around, and keep your eyes peeled for a girl who wants what you want, change and all.
So I Have These Parents
I NEED YOUR HELP. I have entered into a period of my life where I am devoting all my mental resources toward my academics—grad school—and am not interested in dating. Thus, I bought a Real Doll so that I may enjoy fantastic masturbation during this loveless period. Unfortunately, while my parents were visiting, my mom discovered it and she reacted very, very badly.
You see, my dear mother is a feminist.
She is very upset by the doll and believes that it is an indication that I have lost all respect for women. I do not feel this is true. I view myself as a feminist, and I realize this society sexually objectifies women. But I also believe that I can masturbate with a rubber woman and have wild fantasies and then come back to reality and respect everyone—men, women, others. My mother, however, is extremely upset, and we haven’t been able to have a civil conversation since. I am hoping you can possibly give me some perspective.
Dolled Up
My perspective: Your masturbatory routines—including your masturbatory aids/aides—are none of your mother’s fucking business. And if your mother wants to be shocked by something, DU, it ought to be that her son-the-grad-student had $5K to plunk down on a sex toy.
Your options at this stage are pretty limited. You can apologize to your mother and tell her what she wants to hear (“You’re right, Mom, I’m making an appointment with a therapist and donating my Real Doll to sex-starved grad students in Africa …”). Or you can tell your mother to fuck off and butt out (“It’s my dick, Mom, and I’ll stick it in whatever I want. You remember that ‘my body, my choice’ stuff, right?”).
That said, DU, your claim that you bought a Real Doll so you could “enjoy fantastic masturbation during this loveless period” doesn’t quite pass the smell-of-day-old-spunk-moldering-in-the-lifeless-orifice-of-a-silicone-dummy test. Most guys manage to tough out their loveless periods with the help of the porn industry and their own right hands. And most guys who opt for insanely expensive, life-size, hard-to-hide sex dolls do have issues with women—most are plagued by feelings of inadequacy, not superiority—so you may want to entertain the possibility that your mother might be right.
But even if you do have i
ssues with women—still an if—they’re still none of your mother’s fucking business.
I AM A 21-YEAR-OLD BISEXUAL FEMALE. I’ve never really been close with my mum, and since I moved away from home three years ago it’s gotten worse. I know that she loves me because I’m her daughter, but I don’t think she likes the young adult I’m growing into. Yet she insists I visit her and stay at her house for weeks when I have time off from college so she can talk me out of liking anything she hates. When I’m with my friends, I’m quite witty and outgoing, particularly about sex. But when I stay with her, my personality becomes crippled and stunted by her authority. I seem to just end up not saying anything at all for fear of offending her. Last year I stupidly told her that I like watching porn; now it’s something that she’s always bringing up. For example, I got into a conversation with her about a recent breakup and asked her if all men were like my cheating ex. She told me that she thought his cheating was my fault—because I watch porn, she said, I must have been sending out subliminal messages that I approve of women being sexually exploited.
She raised me to be a feminist, but I can’t bring myself to ask her if she would kick up this much of a fuss if I were a 21-year-old man who watched porn. I don’t know what to do to make her happy, short of having some sort of porn-aversion therapy. I feel really conflicted: Away from my mother, I feel like a confident, empowered young woman; when I’m with her, I feel like this mute, angry, introverted little victim.
I know exactly what I’d do if this were a relationship, but how should I resolve a difficult mother/daughter relationship?
Can I Dump My Mother?
If hanging out with your mother makes you miserable, CIDMM, don’t hang out with your fucking mother. You’re a 21-year-old adult—not a young adult, not someone “growing into” adulthood, but an adult already—and you’re in no way obligated to spend all of your free time under your mother’s roof. Head off with your friends over college breaks, travel, watch porn. Head home for the holidays if you must. And since your mother is inclined to use the details of your personal life that you share with her against you, don’t tell her anything about your personal life.
