Ask Mr. Sexsmith: How Do I Use My Girlfriend for My Pleasure?

Dear Mr. Sexsmith,

My butch girlfriend wants me to boss her around in bed. She wants me to think of it as just using her for my own pleasure and nothing more (just this once anyway!). I’m a bit shy about it though, and not sure how to go about it. Do you have any tips or advice for me?

Aiming to Please

I love this kind of play, personally, so I got a little grrr growl and chill-thrill when I read your question. It took me a lot of time, experimenting, sharing fantasies, and permission for me to come to loving this play, however. I have been a top hung up on whether or not to make a move in many, many scenarios.

So, my tips and advice kind of depend on where your stuck point is. Do you have trouble figuring out what you’re going to do to her, for your own pleasure? Are you worried that you’ll go “too far,” and will do something she won’t like? Or do you freeze up when you actually get to the point of actually doing the things you want to do (and know she’ll like) in bed?

I’ll give a few ideas for each of those.

And, before we go any further: A Note About Gender and Power

Just for the record, that she’s butch probably doesn’t factor into this. I love having these little details in the question, so thanks for including it, but for the most part throwing around your butch girlfriend isn’t different from throwing around your genderqueer girlfriend or your femme girlfriend or your trans girlfriend or your unicorn girlfriend. Ask yourself if, by any possible stretch anywhere in you, you believe that a necessary component of masculinity is topping or dominance, and wait to see what answer comes to your mind. Wait. Longer than the first “No of course not!” knee-jerk reaction. Maybe, somewhere buried in some crevice?

It’s okay if there is—I just want you to be able to have a conversation with that little piece, and assure yourself that this other piece of you knows that, through and through, her masculinity and gender identity are not contingent upon a certain position of power, in bed or socially.

Topping a butch (and using her for your pleasure, mmm) is only different because individuals are different.

If you’re having trouble figuring out what to do …

Do you want it to be all about your orgasm? Do you want to push her body through lots of sensation and stimulation? Would it give you a thrill to control her orgasms, not allow her to come? Do you want to toss her around physically so you can more easily get to the parts of her body you want to torture, play with, pleasure?

You probably already know these answers, if you’ve been fucking for a while, so ask yourself: Are there places she likes or doesn’t like to be touched? Which, if any, holes on her body does she like penetrated? Does she come over and over again, ping ping ping in a row? Or does she have a looong slow buildup to orgasm? Or does she not usually come, but likes being stimulated and finds sexytime play satisfying (outside of the goal-oriented limiting practice of orgasm)? Does she love receiving pain? Does she take stimulation better after she’s come a few times? Or does she crash after coming?

Once you have a good sense of the kinds of things she likes, and the things her body easily takes and enjoys, then you can go after the good stuff: what YOU like. Because yeah, it’s play, and you’re both pretending that you are using her for your pleasure, because of course it is for the pleasure both of you. But it would be even more awesome if the thing you were pretending was for your pleasure had some authentic pleasure in it for you.

So what of those things would be oh so delicious for you?

What do you want the scene to accomplish? Do you want it to be all about your orgasm? Do you want to push her body through lots of sensation and stimulation? Would it give you a thrill to control her orgasms, not allow her to come, or bark commands for her to come right now? Do you want to toss her around physically, moving her body with your body (or with your voice) into positions or placements (either comfortable or uncomfortable) so you can more easily get to the parts of her body you want to exploit, stimulate, pinch, torture, play with, pleasure?

So if you are starting to get an idea (or two or four or a dozen) of what you’d like to do (or maybe you already had a whole bunch of ideas and that wasn’t the hard part), here’s how you start to implement them.

If you worry that you might do “something wrong” …

“I love the idea of bossing you around in bed, I have been thinking about it since we talked about it. I think I want to make it all about me getting off, so you wouldn’t be allowed to. I come best when I’m strapped on and fucking you, so I’d want to strip you down, bend you over the bed, and just go at your hole until I come. So um can we have a date to do that soon?”

If you have any worry that you’d be going too far or doing too much or not doing something that she’d like, tell her about your plan. Say, “Hey, so that bossing you around in bed thing? I’ve been thinking about it. And I think I’d like to tie you to the bed, get you all worked up with my mouth and that toy you really like inside of you, then get up and go sit on your face and ride your mouth until you make me come. Would you be into that?”

Or, “I love the idea of bossing you around in bed, I have been thinking about it since we talked about it. I think I want to make it all about me getting off, so you wouldn’t be allowed to. I come best when I’m strapped on and fucking you, so I’d want to strip you down, bend you over the bed, and just go at your hole until I come. So um can we have a date to do that soon?”

(You can do this via text or gchat or email or snapchat or whatever newfangled technology you kids are using these days. It doesn’t have to be in person, if you are too nervous to say those words out loud.)

Getting her “Oh my god fuck yes please!” face in response will help you feel more bold and less shy, and figure out how exactly to go about it.

(Shoving your hand down her pants right then, just to check, you know, if she liked that idea, is not a bad idea either—assuming you have that kind of relationship where she’d be turned on by that and not triggered. Use your best judgment and smarts about what would be sexyhotfun for you and your beloved.)

You could also share some fantasies back and forth, asking her to tell you what she was envisioning, then telling her some of what you were visioning. Just to, you know, do some research. Brainstorming. Consider your options. (Getting all turned on by the ideas and having some wild sexting or actual sex right then is a bonus.)

Or, if you get stuck when it’s actually business time …

She really wants a better grade on that test, professor, and will do anything you ask to get it.

If it’s the actual bedroom time that is holding you back from going about it, consider putting it into a fantasy context. Doing some pretty simple role play scenarios (with lots and lots of dirty talk, and very minimal props and costumes) (for me growing up a theater kid, role play often seemed like way too much work because I thought it had to be theater, but I’ve found that a choice phrase here or there is more than enough to set the scene) has been an excellent way to alleviate some of my own internal nervousness about throwing someone around and topping for my pleasure. Because then, see, it’s not me doing those dirty dirty things, it’s my job as this particular character to do them, and then when it stops, I come back and get us ice cream and aftercare. Plus, a role play scenario usually should be agreed upon by both people in order to work best, so that means you and she would come up with a scenario that you would then both consent to, and all you’d have to do would be show up for your role.

For example: You’re paying her to use her for what you want, so you get to do anything. She really wants a better grade on that test, professor, and will do anything you ask to get it. You just found her getting off and are now going to punish her for it, and since you know she’s a slut already you know she’ll do whatever you want (though you might have to make her, a little bit).

You could push role play into consensual non-consent realms, too, or coercion, but that might be too much, especially for starting out.

If role play isn’t for you, you could also take a look at The Three Minute Game and consider doing it as a warm up—just three minutes of action for your pleasure. It’s excellent practice for longer scenes.

If I had to boil it down to just two things, I’d say:

  1. Communicate – tell her what you want to do, ask her what she wants to do, work out a vague rough plan on what you want to do together, and then
  2. Experiment – Do the plan, reflect with each other what went well and what didn’t go so well, brainstorm and make some suggestions for what you could do to improve it or if you want to toss it out and never do that again, and experiment some more.

I hope that gives you lots of places to start. If you’re still stuck, remember, I do one-on-one coaching sessions, and I would be very happy to help you through whatever might be in the way of getting to this particular fantasy, or fleshing out the scene in your mind, or actually drafting the email, or just talking it through. Contact me for more information and pricing.

Kristen & Sinclair Answer Your Questions, Episode 3: “How Can I Be More Open About Kink?”

Kristen & I answered Laura’s question on video this morning from Seattle … hopefully our colds don’t make us sound too weird.

Laura asks: “I am a kinky queer femme bottom/sub and have read your blog for a long time. The thing that strikes me most is how open you, and also Kristen, are about your explorations and your celebration of your gender and sexuality. I am only 23 but have known I was queer and a submissive since pre-adolescent years, and it feels like I will never be comfortable fully expressing myself or finding my voice except with my partners, because I still get ashamed/embarrassed about all of it sometimes, especially when I think about my family or straight and/or vanilla friends finding out. How did you overcome those feelings to be more open, if you ever had them?”

Reconciling the Identities of Feminist & Butch Top

Queer Memoir: Butch/Stud Through the Years was fucking EPIC on Friday night, and I’m so honored and thrilled to have been there and to be a part of it. There was the story of the kid’s game “hide and go get it” in Kentucky! There was the revelation of belonging somewhere and that “here take a sticker” moment—”because even though you’re in New York City, you might still be isolated.” There were discussions about feminist topping! There was deep appreciation for butch friends and community and support! There was a fucking marriage proposal!

This is the piece I read, slightly updated from the December 2009 version, about reconciling the identities of feminist and butch top, and what it means to be a masculine person who is also dominant. It is relevant as ever and I still struggle with the intersection of these identities. I have a lot more to say about it, and reading this piece again made me think about what I’d add and what more there is to say, so I’m working on it. Meanwhile, here’s the text of what I read.


A few years ago, a girl I dated wanted me to slap her. To hit her face. She asked for it specifically, I still remember the conversation on the subway and the precise way that she looked over at me and said, I want you to hit me. Something big swelled in me and I wanted to, I wanted to feel the sting of impact on my palm and see her recoil, to do it again before she was ready, to push something so sensational onto her experience that she was jolted to the edges of her skin and had to feel, to feel herself, to feel me, to be fully present.

This girl and I had already done some other light percussion play, using my hand, or even a paddle, me hitting her ass and thighs, the fleshy parts that I couldn’t possibly do damage to beyond some light bruising. She liked it, we both did. It made sense to escalate, at the time, to something new; we were deepening both our romantic relationship – our trust in each other – and our power dynamic, and it was time to push a little, to see where we could go.

I was terrified. After she asked, after we talked about it extensively, I even tried, a few times, when we were in bed and she said, hit me, now, please, and I couldn’t, I’d bring my hand up and chicken out.

I was terrified of what it would mean for me, as a masculine person, as a butch, to be more dominating in bed. To like it. To like to cause someone pain. To like to cause a woman pain. To hit someone in the face. To hit a woman in the face, to sexualize that act and that power dynamic specifically.

I was paralyzed by that terror – I wanted to do it, the idea, the very thought of it, the discussions with her, turned me on, the girl I was dating wanted me to do it, but I couldn’t.

Beyond wanting to do it, this was the kind of sex act that was in the sex life I was dreaming of having. This was what haunted my fantasies and what I looked for in porn that I watched and erotica that I read. And I was on a very serious quest to figure out how to have the sex that I wanted. I’d just gotten out of a bed-death relationship. I was committed to studying sex hard, to figuring out: what I wanted, how to get what I wanted, how to build a relationship with that as an element, how to maintain something sane and hot over a long period of time. That’s precisely why I started Sugarbutch.

I now know that I’m a sadist, and a top. That means I like to dominate. And already there are conclusions being drawn by some of you out there who think well of course you like to dominate, you’re masculine, and that’s prescribed for you or in other words you misogynistic asshole, I already knew you were one of “those” butches who needs to make up for your inadequacies by dominating women. Because that’s what we think, isn’t it? Maybe not consciously, but a little bit, somewhere in our brains, we associate these particular identity alignments – butch equals masculine equals top equals dominating equals men’s prescribed gender role. We’re relieved when they line up how we think they will, or maybe we are challenged and uncomfortable – though perhaps in a stimulated way – when they misalign.

There’s something supposedly anti-feminist about wanting to dominate. There’s something in the feminist rhetoric which says we are all equal especially in bed, so that means I-do-you-you-do-me, or that means we have sex neither above nor below each other, and with no reproduced heteronormative misogynistic patriarchal power dynamic.

But I didn’t want that. I’d had that, with other girlfriends, but it didn’t keep things hot enough to sustain a relationship. And secretly, I wanted to top and control and hit and demean and humiliate and restrain and force and take.

Power dynamic theory—stick with me for just a paragraph here—has many similarities to gender theory. Like the gender identities of butch and femme are not reproductions but pastiche copies at best of prescribed societal gender roles, putting on and taking off power roles in power sex play is a pastiche reproduction of power in our lives, of which there are thousands of examples of interaction on a daily basis. And when we can put on and take off these roles intentionally, the act of adopting becomes further proof that the power positioning in our lives is not inherent, or “real,” or immobile, or prescribed, or “normal,” but part of a hierarchical society of social power that can be deconstructed. In that, we can more easily have more power and control in the beneficial ways, and less power and control in destructive ways, as we play with it and engage with it.

As in my experience with coming to a butch gender identity, when I finally came to a power identity that really deeply aligned with something inside me that just clicked and make sense, I felt like I was coming home to myself in a way I hadn’t experienced previously. Through my personality and tendencies and psychology I have my own set of quirks and workings and functions, and for whatever reason, it makes a lot of sense to me to let out some of my power and control issues in the bedroom by being dominating. It is deeply satisfying the way a glorious meal or a delicious book is satisfying, one of my life’s greatest pleasures. I’m not sure I understand why I like what I like, but what I like does not harm others, and is consensual, and I know myself well enough to accept what I like as what I like – and to let that be a simple truth.

How did this change for me? What happened between the time when I was terrified to slap a girl in the face and today, now, where I am fairly comfortable in my identity as a top, and even as a sadist, as someone who enjoys causing extreme sensation (aka hurting) someone else?

Little by little, I had lovers who pushed me, lovers who were more experienced as bottoms than I was as a top, lovers who wanted more from me and who could take more than I was able to give who made enough space for me to walk into a bigger version of myself and occupy it, try it on.

I did come to a reconciliation with my feminist self and my top self. Phrases like men should not hurt women or rather masculine people should not hurt feminine people, or even more broadly that people should not hit each other and violence is bad bad bad … I had accepted those phrases as Ultimate Truths, and I started to understand deeper the ways that sensation was not violence, and hitting was a way to be sparked into the present moment, to release whatever our musculature was holding onto, and to deepen trust between people and in a relationship.

I didn’t realize how little trust I had in others until I started playing deeper with BDSM. Because I would tell myself, it’s okay, she wants to do it, but then I would think, does she really? Maybe she wants to because I want to. Maybe she wants to because society tells her she should want to. Maybe she wants to for fucked-up reasons, like she thinks it’s okay for her to feel humiliated and less than me because of her own internalized misogyny … but that was me not trusting that what she said was true. That she wanted me to hit her face. And that was me, further controlling both myself, her, and our relationship, in unhealthy ways, because I didn’t trust her.

This was an issue of agency, in feminist terms – my not trusting my lover to communicate with me what she wanted, to explain to me how far I could go, and my not trusting that she would let me know if I was going too far or too hard, either with her physical communication or her words or both, was me not trusting in the agency of my lover. I have to trust that she will tell me, she will let me know, if I am going too far. And I have to listen, apologize, understand what I did, and trust that she will accept that it was an accident, a mistake, and that I’ll do whatever she needs to feel safe again.

When I started playing out my control issues in BDSM, in the bedroom, in sex play, the control issues I had in my relationships began to heal.

In learning my way into being a top, I had many, many conversations about consent and intention and communication, I talked to my lovers when things broke down or didn’t seem to work and I learned more about my own tendencies when things went well. I figured out that sometimes, it was really hard for me to be with someone who bottomed so well, and who I trusted so deeply, that I did harder, scarier, bigger things with them that took me even deeper into my topping and dominance and sadism and power, and sometimes that meant I needed to be comforted afterward, to be told I liked that, and that wasn’t too much, and you didn’t hurt me, and that was what I wanted and thank you. Hearing those things is always a relief.

(I give good aftercare too, of course. But top aftercare is less common in the BDSM world – we don’t frequently talk about the toll it takes for the dominant to dominate.)

I practiced, a lot, to be bold and trusting through my topping. I tried scary things and it turned out they weren’t so scary, they were in fact incredibly hot. I got to know myself, and I learned more about the things I wanted to play with, and I talked to smart people whose experiences were similar to what I was going through and who assured me it was possible to come out the other side of it a masculine, queer, butch, sadistic, feminist top.

Kristen & Sinclair Answer Your Questions – Episode 1: “I Want To Be Taken”

So Kristen and I have a new experiment …

I’m no longer writing an advice column for acompanythatshallremainnameless, so I have this spreadsheet full of questions (65 of them at the moment) and nowhere to really put the answers. Sometimes I run them by Kristen before I write about them, or just to spark casual conversation, and we have fun bantering about the advice that we’d give. So at one point we thought, hey, what if we do a little video recording of these?

In this episode: Emma asks, “I’ve just started dating someone new, and at the same time I am figuring out that I might be submissive. How do I let her know that I want to be, well, taken? Thanks.”

References from the video:

Mollena Williams
The Topping Book & The Bottoming Book (weren’t actually mentioned but I meant to suggest them)
Savage Love

PS: Isn’t Kristen pretty?

PPS: Bonus photo outtake:

Ask Me Anything: What to Wear to a BDSM Weekend?

Via email, Katy asks:

I will be going to my first BDSM convention next weekend … I have a question. I’m not particularly a fetishwear kinda guy… What would you wear? I feel like you and I have similar style and kinks.

I would probably wear jeans, a button down shirt, a tie, and nice shoes, because that tends to be what I wear. Definitely a belt, I never wear a button down shirt without a belt, I always think you need a belt if you’re going to be tucking in a shirt, and these days I wear a belt with everything, it makes the outfit seem much more pulled together.

Sometimes I fetish that up by wearing a bondage belt or wrist cuff, but generally a tie is enough. Oh, but if it were me, I would definitely get the right color hanky and flag according to the hanky code.

I’d say that you should wear what makes you feel most sexy and hot, not necessarily something fetish-y but something that makes you feel attractive and confident.

(If I was fancy, I’d do up an image for this outfit dooce-style, but I have to get some workshop prep done. Next time!)

Ask Me Anything: How to Give Blow Jobs Without Feeling Stupid

Newbie asked:

My partner and I are new to strap-on sex. We both love the idea of blowjobs, but I have no idea how to go about it without feeling supremely stupid. Help please! Could Kristen maybe give her perspective on learning to do it well?

Here’s Kristen’s answer:

How to suck butch cock: some advice.

Here’s the thing about sucking silicone cock: you have to pretend it’s real and remember that it’s not, both at the same time.

1. Pretending it’s real. This is most important: you have someone’s cock in your mouth, and you need to take care of it. Treat it like the beautiful and powerful instrument that it is, regardless of whether it came from a factory. Start slow. Put your lips on the tip. Lick around the head. Lick all the way down one side. Put it in your mouth for a minute, then take it out and lick it again. Eventually, once your mouth produces more saliva, you can suck it in deeper. Look up at your partner so they can see that you like it, so they can see the pleasure you’re giving them, even if they can’t exactly feel it. Act like you know what you’re doing, whether you actually do (hello, grateful college boys you might have practiced on) or you’re making it up as you go along. Vary your speed: don’t just repeat the same movement over and over, unless your partner gets into it and wants that. (Face-fucking is great, once you’ve gotten the hang of a basic blowjob.) Watch porn: even the free crappy stuff on Youporn is helpful here, because you can see facial expressions and technique and just mimic that.

2. Remembering it’s not. You’re not going to get physical indicators that tell you you’re doing a good job. You won’t be able to feel it getting harder (or limper) in your mouth, you’re not going to be able to feel when your partner is close to coming, you’re not going to know if you’re using your teeth too much. You have to do that work yourself: listen to your partner’s breathing, pay attention to their muscle contractions/their hands on your head/gasps of pleasure. You have to do the work of making it the most amazing blowjob they’ve ever gotten, even if they can’t feel every movement of your tongue. But that’s the fun part: you can do pretty much whatever you want to make that happen.

What do you think? Got any other advice for how to give blow jobs that don’t make you feel supremely stupid?

Ask Me Anything: What To Do With Old Sex Toys?

Q asked:

do you have any ideas for what to do with lightly used sex toys and accessories? They don’t seem like the kind of thing you just sell at a yard sale! But it seems a shame to just chuck something so expensive and that someone else could get a lot of pleasure out of. If you don’t think it makes sense to give them away (and I mean give, I certainly don’t want to sell), is there a way to recycle them or otherwise dispose of them properly?

Thanks!

Yes, generally you’re right, people don’t want used sex toys, even if they can be sterilized. There are some—glass, metal, silicone—that I would say you can offer to good friends, or people you might think could handle a little use. Some leather/BDSM gear you might be able to swap or give away, but it depends on the condition. But if they’re very broken in (you know how silicone gets after it’s been used a bunch, it kind of starts disintegrating) I think it’d be best to recycle them.

The jelly plastic or other plastic insertables or vibrators … probably there’s nothing to do with them except recycle them.

There is a sextoyrecycling.com place, but it looks like it’s not legit. I haven’t been able to contact anyone from there to get confirmation that they are running.

I did hear from ScarletGirl.com, they have a sex toy recycling program that will give you $10 credit, but more importantly, they won’t end up in the landfill.

Dan Savage has recommended sending your old sex toys to representatives in states where sex toys aren’t legal, which I think is a good idea for activist purposes, but what happens after the politicians receive those toys? Probably they will end up in a landfill. So if your purpose is to be green moreso than to have some impromptu activism, you might want to just write a letter (or an email! Save paper) and send your sex toys off to be recycled.

Some of the sex bloggers who do a lot of toy reviews have set up the Toy Swap Network for toys that are not old, broken, worn-out, etc., but are new and that you just don’t want to keep around.

It is by invitation only, so you can send in a request, and the network itself is on Ning.

Any other recommendations for what to do with old sex toys? Perhaps Folsom East has some leather swap events, anybody know?

Ask Me Anything: Strapping On For the First Time

ExperimentallyCurious asked:

What was your first time strapping like? What advice do you have for strap-on virgins? My butch just placed the online order for her first cock, and I have no idea of what to expect.

Go slow. Use lots of lube. LOTS of lube. More than you think you might need, especially at first. It’s just a little messy, which is always better than having not enough. DON’T use silicone lube, as it’ll screw up your silicone toys.

Talk to each other, be as vocal as you can—even “ooh yeah ooh yeah” type of vocalizations will help give cues to each other about what feels good and what is not quite working.

Don’t be afraid to slow each other down or stop. It might just click and work and be amazing, but you also might want to just do it as something to try and to play with, at least for now, so don’t expect one or both of you to get off, especially not at first.

If you’re not used to penetration during sex, you might want to mess around with getting yourself off (or her getting you off, using her hands on your clit I mean) while she’s inside, but without much in-and-out motion, at least for now, while you’re getting used to the feeling of her cock.

The typical porn positions are the best, in my opinion, which is why they are so frequently used—missionary, and doggy style from behind (in various incarnations, like leaning over the bed, or with your head down on the bed instead of on all fours). In missionary, also try it with her sitting up on her knees, with her thighs under your thighs, that is often a really good angle.

Don’t be afraid to touch it, kiss it, lick it, suck it—that stuff can be really hot, though that can also be kind of delicate, so see how your girlfriend feels about it. Sometimes it seems to me, as the strap-on wearer, that I am expected to be the one who does all the action once I put it on, but my point is that you can do things, too. If you aren’t sure if she wants you to touch it (or kiss it or suck on it), ask. “Would you mind if I …” “Wow, I didn’t expect to want to … , but I do, please may I?”

Personally I think just about any sex act is all the more hot with someone saying what they are doing (or want to do), regardless of what it is. Maybe that’s me—I really love language.

Most women can’t come from penetration alone, which I assume the two of you know, but just a reminder that you both might want to start practicing touching your clit while she’s fucking you, either with your hand or, if she can reach comfortably, with hers. It takes some practice to be able to fuck with a cock and use your hand at the same time, but it’s possible! And worth figuring out how.

And from her side … it is possible to get off while strapped on, but that might take some time and practice. For me, I like the harness to be VERY tight, tighter than is all that comfortable around my hips, because I like to be able to feel every stroke against my cunt while I’m fucking. I like the stimulation of a one-strap (g-string style) harness better than a two-strap (jock strap style) harness, but that seems to be the minority opinion, so your milage may vary. She can try adding bullet vibes or butt plugs or the We-Vibe to increase stimulation, though I find those are more distracting than helpful. But if she really likes a vibration on her clit or something in her ass, that might be just the push she needs to be able to fuck and come.

Other than that, in my experience, to be able to come while strapped on, just following the sensation—when you find a spot that feels good, rub up on it, over and over, and see how far that can take you.

Consider anything you do in playing with it an experiment, and collect the data of that experiment. Did it work? Would it work better if one variable was different? Would you try it again? Or was it a complete fail and did not feel good? Gather the data and figure out what you like and don’t like, what was luke-warm and what you might try later if things were a little different.

Did I mention lube?

And … the first part of that question was, what was my first time strapping on like? Well, to be honest, my first time strapping on was to peg a guy, my boyfriend of about 5 years that I was with in high school. I bought a strap-on when we broke up, and I came out as a lesbian, and it was a tiny silicone thing that was very hard silicone and black and narrow. I do still have it, actually, I keep thinking it might be a good size for anal sex, but then again, now that I have the Spur why would I use a cock that was so hard?

We then went cock shopping together and bought a cock that was roughly the size and shape of his, which was what I pegged him with. It was fun enough to peg him, but it also made me realize that I was (really really for sure) a dyke and wasn’t that into it.

I did fuck my first girlfriend with a strap-on, but we were more of the I-do-you-you-do-me type of couple, so we took turns. It took quite a few more years before I felt like I had a cock that was mine—really not until I ended the relationship with my college girlfriend and started dating femmes exclusively. Which I have widely chronicled here!

It’s been a long journey to claiming my cock-centricity and cock confidence. Actually, I teach workshops on Cock Confidence now, in case you’d like to attend one—I’ll be doing it next at Good Vibrations in San Francisco in August.

Anything else y’all would recommend? Any other tips for first-time strap-on users?

Ask Me Anything: How Not To Slip Out When Strapped On

MSE asked:

Like Tuesday, I also have a question about strap-on sex. Whenever my girl and I use a strap-on, the cock always falls out because I move entirely too much. We’ve tried numerous positions and restraints (we rarely have sex without them). Got any additional solutions?

The first thing that comes to mind is that you might want to get a bigger cock—at least a longer one. Which one are you using right now?

And maybe she would say she doesn’t want or need any more length inside her, but that’s okay—just because it is 8″ or 10″ doesn’t mean you have to put all of those inches in her. And if you have a longer shaft, you can pull out farther and move around (which is what it seems like you want to and like to do) and still not pull all the way out.

I would suggest one like this one, Bandit, which is 7″ long. It does have balls, but they are very flat, so I think it’s still about 6 3/4″ insertable. It’s made by Vixen Creations and it is one of my favorites.

But, if getting a new cock is not an option, for whatever reason (her comfort, your wallets, etc), here’s a few other ideas.

Try keeping your hand on your cock most of the time while you’re fucking. I do this a lot, also because I don’t want to slip out and can easily do that sometimes, especially when I get going. I find it’s most comfortable for me to either have my hand loosely on the base, or up against her, where the cock is going in, loosely. Sometimes it is very good in this position to be able to stimulate her clit, too (or finger her asshole, or whatever). This is so you can feel when you’re about to come out, you can feel the ridge of the head of your cock if you pull out that far, and you can keep yourself inside.

Try moving less! Seriously. I understand it probably feels good when you do that, but there are other ways to move so you can still feel good and you aren’t slipping out as much. See if you can get a side-to-side movement working well. Practice moving your hips in a circle rather than in-and-out. Or go in-and-out but use a different angle, so you don’t pull out so far. Try five quick strokes in-and-out at about half-length, not all the way, and then five excruciatingly slow strokes where you pull pretty much all the way out.

Try tightening your harness so you can feel any movements better, maybe you won’t need to move around so much that way.

You said you’ve tried other positions, but try more. If she’s on top, she can control the depth and it’s a lot harder to pull all the way out. If you’re on top, try drawing your knees up instead of having your legs splayed out straight so you have more control with your hips.

If none of this works to prevent slipping out, well, maybe you can just accept that you’re going to fuck and buck wildly, and you’re going to slip out. I mean, does that really matter so much? Just put it back in. You might want to create a script that you say—or a couple different scripts—so that it becomes part of the play, and also so that she has a way to tell you that you’ve slipped out without embarrassing you or you feeling silly for having continued to fuck without being actually inside (it’s one of the downfalls of not actually having nerves there). She can say, for example, “Wait, I want you inside me, come back, you’ve slipped, put it back in.” You can tease her and say, “Do you really want it?” and make her beg or say please. Or she can order you around and make YOU beg to put it back in, if that’s more like your dynamic.

Okay, what say you out there reading this? Any other ideas for staying inside? Any more thoughts or suggestions?

Ask Me Anything: Strap-On Positions When Someone is Taller

Tuesday asked:

What’s your advice on positions that work for strap-on sex between people of very different heights? especially taller person receiving

Well, if your torsos are different lengths, especially if the one receiving is much taller, it’s going to be pretty difficult to be in the missionary position—or just about any position where you are strapped on and fucking and also simultaneously kissing (on the mouth) and holding each other close.

If your thigh heights are different, then fucking from behind on hands and knees is going to be difficult too. If both your torso and your thighs are different heights, it’ll be almost impossible to get into a position where your entire bodies are pressed up against each other and fucking at the same time.

There are still many other positions you can fuck easily in, but that one is going to be hard, maybe impossible.

Try these:

1. Strap on wearer (giver) seated, receiver on top, straddling

2. Receiver bent over a bed which is at the giver’s hip height

3. Receiver with their knees tucked under them, but leaning forward, so they can hold themselves up at the right height by their thighs; giver behind them

4. Giver on their knees, with the receiver on the bed (or floor or etc) on their back, receiver’s thighs up over giver’s knees; giver stays upright. (I particularly like this one for rough and deep penetration because I can grab on to their thighs and move them against me.)

You may just have to try any or every position, until you find a few that seem to work most of the time, and go for those. Try glancing through one of those positions for sex books—you probably don’t need to buy it, just glance through it—and see if any of them strike you.

You also might want to think about getting some sex furniture. They’re much more solid than regular bedroom pillows, and the microsuade material means that you don’t slip or slide. Sometimes those are excellent for angles and positioning, it might be worth trying (though they are expensive). Take a look at the Liberator Wedge, Ramp (which is the best for multiple positions), or the Ramp & Wedge combo.

Anyone else have suggestions?

Ask Me Anything: Confidence & Getting Girls Off

Babybutch wrote:

My girlfriend totally knows how to get me off, but I’m nervous that I’m not doing enough for her sexually. We’re very honest with each other, but I worry that she’s not saying anything because she’s afraid of hurting my feelings. What kind of sexual activities would you recommend for the relative novice? What did you “start” with when you were just beginning your sex life with women? I think my biggest problem is (lack of) confidence.

I think you’re probably right, that more than anything it is a lack of confidence. My best advice for building confidence is: a) come up with a small script you can say when you get nervous, where she will reassure you in a way that makes you feel more confident and builds you up (this also might involve a post-fucking script with lots of praise over what you did); b) ask her what she likes, let her direct you until you get it right; c) fake it till you make it—not with the moves, but with the confidence. Just pretending you have confidence will get you pretty far, since usually confidence is actually about a mental state rather than any physical action that you do (or don’t do).

This also kind of depends on how toppy or switchy you are—it’s harder to fake topping, I think, and harder to let her direct you if you’re also trying to build dominance too. But you said she knows how to get you off, so perhaps that isn’t a factor with you two.

You also wrote: “We’re very honest with each other, but I worry …” See if you can work on that. You can flat out tell her, “Hey, I know you said it’s okay, but I have the impression for some reason that maybe you just don’t want to hurt my feelings. Now if you tell me that I’m wrong and just worrying too much, I will believe you, but I also want you to know that I can take it, and I’m interested in getting better at fucking you, so I hope you’ll help me do that.”

And if she tells you that it’s okay, then you can choose to believe her. (She can also choose to change her mind later, and hopefully you won’t take that as an affront, or that she was lying—just accept that sometimes feelings about things change, and that she’s being as honest as she can be right now.)

Another issue at play here might be the difference between how many times she wants to touch you vs how many times she wants to be touched (or how many times you want to be touched vs how many times you want to do the touching). Conventional lesbian wisdom says I-do-you-you-do-me, but that doesn’t necessarily jive with everybody. I, for example, am a top bordering on stone, so I don’t want to be touched, barely ever. Maybe 1 time out of 20. But perhaps you are a five-out-of-ten person, or an eight-out-of-ten person. It sounds like her desires—to be the one who mostly touches you—is driving your sex life right now, but that can (and should) be co-created by the couple to figure out what’s best for both of you. Maybe you want to do more of the touching, but your confidence is holding you back? Maybe she’s not so good at asking for what she wants, or giving you permission to just explore and play? Maybe you are both too goal-oriented here—just because you don’t know how to get her off in two seconds, like perhaps she does to you, doesn’t mean it isn’t still a good idea to touch her, kiss her all over, make her feel good.

And yes, it’s possible that she’s overcompensating because of your nerves, being more of the actor than the receiver because you aren’t stepping up. So if you want to step up, do it. I would TALK to her about it—out of the bedroom, on a random afternoon where you’ve had a lovely morning together and you are both feeling loose and open. Say, “Hey, I know I haven’t been stepping up in the bedroom much, but that’s because I’ve been kind of nervous, but I’d really like to work on that. Can we talk about ways we can play so I can try to build my skills?”

And, speaking of skills. You asked for advice on activities for a sexual novice. Ultimately, it all depends on what you like, and what she likes. There are activities that I think are kind of basic and beginner that other people think are really advanced and edgy, and vice versa. Like cunnilingus—going down on a girl—that is something that I do not do with a new lover, mostly because it’s so intimate (and the whole fluid-bonding thing, since I much prefer it without a dam). It takes time to build up to, for me. But then again I can top someone and be dominant on a first date, spanking or using restraints or pulling hair, which some people would think is a much more advanced thing to do.

But, generally? I think to be a good lover, you should be good at these things: 1) kissing, 2) finger fucking, 3) going down, 4) toys, whichever toys you might be in to, be they vibrators or strap-ons or bondage equipment, 5) quickies.

Of course, there’s plenty more things to get good at—anal, bondage, squirting (if either of you tends to do that—or if you don’t, you can experiment and see if you can make yourselves do it), percussion play, penetration, dirty talk, role play … but generally I think those take longer to learn and experiment with, and if you get those others down, you’ll be golden.

Kissing: check out Violet Blue‘s book Seal it With A Kiss (or her ebook, How To Kiss) if you doubt your abilities. Go slow, make it luscious, make it last, don’t use too much teeth or tongue or saliva. You probably know the basics.

Finger fucking: Practice on yourself. I assume you’re good at getting yourself off already. Watch her masturbate so you can see what she does to turn herself on: does she always have her fingers on her clit, and never go inside? Does she start with a lot of fingers in her cunt and only put her fingers on her clit at the very last second? Does she use tons of force, or very light strokes? Are the strokes long and circling, or slow and jerky? Watch closely. Take notes. Try to duplicate it. Ask her for help—”There?” “No, lower, lower—YES. Harder. Left-right instead of up-down. Like that. Don’t stop!” (And then, whenever a lover says don’t stop, for goddess’ sake, DON’T STOP.)

Going down: Check out Going Down: How to Give Her Mind-Blowing Oral Sex which has some excellent tips, or Violet Blue’s Ultimate Guide. I have a whole class on this, so I have more things to say than I will go into here.

Toys: Consider adding a vibrator to the mix if you are worried that your skills aren’t getting her off. Have her hold it and use it while you fuck her, while you kiss, while you talk dirty in her ear, while your fingers are inside of her. I am not huge on vibrators myself, but I do love the Hitachi, and there are a lot of really beautiful high-quality high-class vibes out there these days. Experiment! Ask your favorite sex toy store for advice, I’m sure they can help. I just noticed that Babeland has 20% off of Jimmyjane vibrators this month—that might be worth looking into, those are beautiful (and expensive).

Quickies: For lots of reasons, this is a great thing to work on, to be able to do as a couple. For one, it says to her, “I can’t wait, I have to have you RIGHT NOW, I don’t care if we only have ten minutes,” which is flattering and good for the bond between you. But also, it is good practice for getting her (or your) arousal up to the point where you can come quickly. It takes skill and practice and enthusiasm! If it was me, trying to get better at something like quickies, I would lay it out directly: “Hey, I really want us to be able to fuck quickly. Are you game to try that? Say, every day this week we’ll try to just work in a really quick fuck somewhere other than the bed (or maybe in the bed, too, if that works). Are you up for that?” And see how she feels about that kind of thing. Maybe daily is too much, but maybe it could be daily over a three-day weekend? Or every other day? I like setting specific guidelines or goals around things like that, because then if we both consent to it, it makes it easier to follow through with. But—your milage may vary, do what feels good for you.

Last but not least, you asked how I got started, when I started fucking women. I went to a women’s erotic workshop, one of those that I have been pimping out lately because I’m now coordinating the workshops, before I’d ever slept with a girl. That most certainly helped.

But, thought I had (quite a bit of) experience fucking guys, I didn’t have much confidence and I wasn’t sure what I was doing. The first girl I slept with hadn’t actually slept with a girl ever either, so in that we kind of figured it out together. I remember very vividly how nervous I was, how we both knew what was coming, but neither were sure how to start or, once we’d started, how to proceed. She actually said, “I don’t know what to do,” which, for me, was the permission slip I needed to just go for it, to follow my instincts and to stop holding back what I wanted to do to her, how I wanted to touch her. When she admitted she didn’t know, well, then, there wasn’t much I could do that would be wrong, would there?

We only dated for about a month and slept together only about three times, partially because my mom was in town for a week and partially because I got my tongue pierced the day after our first date. Um, whoops.

Well—that was longer than I intended, but I hope that is helpful!

And now, what about you all out there? What’s your advice for this babybutch? How do you build confidence in the beginning? What were your early experiences fucking women like?

Ask Me Anything: Becoming More Dominant

From the Ask Me Anything questions from Sugarbutch’s 4th anniversary:

What are some tools/techniques that help someone to “try on” a dominant persona? … How can I help her to get into the right mindset? How would you advise a new, and perhaps, reluctant dom to become more comfortable with her power? —Sophia

Great question. Wish I had had some guidelines, or someone who could’ve given me some pointers, when I was starting to come into my own dominant/top orientation.

I think it’s important to have conversations, outside of the bedroom, about your interest in playing with domination and submission, and to do some assurance that you want to be submissive—that you really really want to be submissive, and oh aren’t you so lucky that the two of you can play with that together. You might have to continually assure them of your desire to submit—before, during, and after. I know from my own experience, it sometimes boggled my mind that someone would let me do all those things I wanted to do to them, but I still felt that twinge of guilt and worry that I was going to hurt them, somehow. Assure them that they will not hurt you—or rather, that a) you want them to hurt you, and b) if they hurt you too much, or in a way that you don’t like, you are fully capable of using your safe word and getting out of the situation. They have to trust that you can take care of yourself if things get to be too much. You have to be fully capable of saying no for the yes to have any meaning.

Talk about what might happen if they do hurt you in the wrong ways—that you’ll stop, that you won’t both jerk away and get all distant, but that you’ll have a minute to talk about it, assure each other that it was not intentional and you both know the other wouldn’t do something that was too much on purpose. Apologize, and try to understand why it was too much, if it was just circumstantial (we’ve done this other times and right now it just wasn’t right) or if it was the actual thing (you tried this new thing and it went too far), or something else entirely.

There are some exercises you can do around this, if you want to. For example, you could do some light play with the intention of safewording out of it, at some point, to practice. And when you do safeword out, practice that moment of coming back together, taking care of each other’s needs, and then getting back into the play. A safeword doesn’t have to mean “stop forever and ever I need hours to recover,” it could just mean “okay I really need a break from this for just ten minutes and they don’t seem to be letting up.”

Say things like, “I liked this and this and this that you did, but this one small part was just too much for these reasons.” Assure and re-assure, especially in the beginning. Tell them what you liked, what was working.

Remember that your safeword can also be no or “stop” or “enough” if you aren’t playing with power exchanges where those words are used to arouse.

It really helps to have some parameters when playing with dominance or topping and trying to bring about a more dominant persona in bed. Those parameters can be various things: time, clothing or costume, dirty talking, or assuming another role with certain expectations.

Using time as a parameter can be a great way to start. Put a timer on and say, “I’m going to spank you for 5 minutes, and then we’re going to make love.” Or count: 30 spanks with my hand, 5 minutes of warm-up with the flogger and then 10 really hard strokes, 5 strokes with the cane.

Sometimes certain clothes can really enhance an exchange, and sometimes just one key item can transform a scene from “us” to “play.”

Dirty talk has been key for me in getting more comfortable with my dominant persona. Not only was it key for me to hear a semi-constant reassurance from people I was sleeping with that they liked what I was doing, it is also a way for us to keep in better contact during play, because we’re engaging our brains instead of possibly zoning out.

Role play can be a fantastic way to try on a dominant persona and get more comfortable inside of it, because you can hide behind both the fantasy and the role. Most role plays requre some sort of negotiation before hand, especially if you’re talking about what you’re doing (or what you’re doing in the fantasy). Say you decide that you’ll be a student and they will be a teacher, and you’ll do anything to get a better grade on that test, even bend over the desk. You’ve established a power dynamic, it’s within these specific constraints (because you’ll just go back to being yourselves when you’re out of these roles, you don’t have to own the desires quite as much when you’re stepping into another persona), and you’ve already established some guidelines about what you’re going to do and how you’re going to yeild that power such that your partner consents (“anything” for that better grade, even bend over the desk). They know this, because you already talked about it.

That kind of scenario gives someone permission to play with variations on a theme. They know they can bend you over the desk—but what happens if they try to get you on your knees first, or to sit on their lap? They know they have permission to do these kinds of things (especially if you’re good at the dirty talk, egging them on: “What do I have to do? Tell me, I’ll do it, you just tell me what to do. I have to get a good grade, I have to pass this class, I just have to.”).

So: negotiate, talk dirty, role play, fantasize together, work on your trust.

And don’t forget to assure and re-assure. Do it sincerely, don’t push it too hard, but step up and express the things you loved, the ways you felt, what you’d like to do again or more of. Write it down in email or chat (or a shared Google document) if it’s hard to do in person. Do it in pillow talk right after, if your tongue is more loose at that time.

Hope that helps.

The Ongoing Quest to be Sexually Fulfilled

That’s where that whole online writing project (aka blog) of mine started, really: in an attempt to write myself into a better sex life, and into personal relationships about my own sexuality, gender identity and expression, and sustaining relationships. For the first three years, I was attempting to write myself into a long term, stable, sane relationship, in part because I wanted to have a better sex life and in part for all the rest of the good stuff that comes with intimacy, cohabitation, and love.

And now, I’ve found the girl I’ve been with for a year and a half, Kristen. And the longer we’re together, the longer it seems we’ll last.

So, now what? Is my quest for a fulfilled sex life over?

To some degree, yes—many of the problems and questions that plagued me as a single butch top, such as, “When am I going to get laid next?” and “Who’s it going to be with?” and “How do I know if she’ll be into what I’m into?” are no longer a factor. I love that I am with someone as open and eager to explore sex as I am, if not more so. I love that our sex drives are pretty well matched. I love that I am with someone whom I can try out new toys with (it was much harder to be a toy reviewer when I was solo, that’s for sure).

But that is not necessarily a recipe for perfect sexual compatibility, or ongoing sexual fulfillment. Note the key word there: ongoing. A sex life is just that—a LIFE—which means it happens every day. And like any other aspect of life, it is interwoven tightly with all sorts of other aspects, and can be different, feel different, or present unique new obstacles at any time.

How does one navigate fulfillment with all sorts of other things—bills, work, health, family, projects, friends—are also vying for attention? How do you keep the spark going?

Perhaps this relates to my theories around general relationship intelligence and the lack of depiction of many stable, sane, healthy relationships in the various storytelling arts. Most romantic comedies or dramas, for example, focus on the part of a relationship story where the couple is overcoming obstacles in order to begin their life together. At the beginning of the film, the couple is not together; the dramatic action focuses around their miscommunications, struggles, possibly sex, expectations, who called (or didn’t call) who, and who can get over their issues in order to fully embark on a committed monogamous relationship; then the end of the movie shows the couple, triumphant, and we are happy, having been rooting for them all along.

But we see very little of what happens next in the relationship. How the couple communicates, negotiates, reaches consensus, struggles, forgives, fights, and maintains a balance between their individual separate selves and their collective togetherness. So rare is a film where the couple is together at the beginning and the end, where the dramatic action centers around the relationship trials or the couple coming together to solve outside problems.

Without such good models of problem solving in long term relationships, and with such high divorce rates, meaning that for folks my age it is rather rare for our parents to still be together, or even to have an older couple in our lives as mentors, how can we be expected to have the relationship skills to sustain our own long term relationships?

And isn’t it similar with sex: when we are single, we expect getting into a relationship will fulfill our sexual needs. The smarter folks among us know that getting into a relationship isn’t quite enough, but that we need to get into a relationship with a person with whom we are sexually compatible. A subtle but key difference!

Yet still—life happens. Even if you find that special someone, there is still ongoing navigation to keeping it up and getting off. And sharing a life with someone means distractions, miscommunications, unforeseen occasional tragedies, and our ever-changing bodies and lives.

This is what I have been puzzling through in my own relationship, as we are increasingly sharing space and continually sharing our lives.

My relationship with Kristen started as almost purely sexual. She lived a few hours away from me, and worked in another state, and would come visit on weekends. She’d lived in New York City before and planned to move back, which is how we met in the first place. We spent whole weekends in bed, rarely leaving my apartment, rarely leaving my room except to eat and shower and rest our bodies. After she left, I would spend the whole week playing over and over the last weekend, often writing about what we’d done, how we’d played, and planning some new ways to play when she came back.

I would pounce on her as soon as she walked in the door. Already hard packing and waiting anxiously to feel her again. Not even letting her put her things away before shoving her up against something, so eager and grateful to have someone who let me play with dominance, someone who was open to play.

It was erotic, connected, passionate, heated sex, full of longing and relief and release. Plus, we continued falling in love, discovering all the ways we enjoyed each other’s company outside of the bedroom.

It’s easy to look back and see the bliss, but equally present was the ache of longing, the fear of the fragility of a new relationship, those days when we would have given anything to come home to each other, all the fetishizing and idealizing of a shared domesticity. I brush over those feelings now because that wish was granted, I no longer have to long to share other parts of my life with her, as our lives are increasingly entwined.

Now we have the new obstacles of sustainment: Am I getting what I want in bed, in this relationship? Are we having sex often enough for me? Are we having the kind of sex I want, or am I longing for something else, something new? How do I ask for more, or different, sex? How do we keep the spark of eroticism, passion, longing, and eagerness when we are available to each other, in so many ways, constantly? How do we keep it fresh and new when we’re willing to do, and have done, so much experimenting already?

Maybe this sounds like a trite problem, especially to those who don’t have partners, don’t get laid, or don’t prioritize sex as a serious hobby the way Kristen and I do, but I suspect many people in reasonably satisfied relationships ask these questions at some point or another.

I’m sure all of our relationships have a unique set of circumstances behind these questions. For me, it seems to be that my girlfriend would like to have sex more often than we do, and in part because of our dynamic and the sexual roles we like to play with of Daddy/girl and domination/submission, she has a hard time asking for more. She feels greedy and unwarranted. I know I also have a hard time allowing myself to be seduced, so even when she does feel bold enough to make her desires clear, I don’t always respond with what she wants. I adore our dynamics and they are a key important part of this relationship, roles I have been eager to explore for years and I am grateful to do so. But precisely those dynamics erase my own desire for the chase, since she is constantly available to me, sometimes my desire runs a little low. I crave some denial, something to conquer, something to come up against in order to create friction.

We have discussed this; and of course I don’t want her denying me just for the sake of denying me, of turning me down when what she’s really interested in is playing, but we are still working out the details of dynamics we have chosen.

I’m pretty confident that we’ll figure this out, but I’m not exactly sure how. For now, we’re talking about it (though hopefully not too much), being open with each other, being honest about where we’re both at and what we want, and of course, working on our own shit in therapy. Every relationship is complicated. Every relationship has triumphs, low points, complications. I don’t know how things will get resolved, but things are improving, we are talking well to each other, still having great sex, and enjoying each other.

Really, does it get any better than that?

This post first appeared on the Good Vibrations Magazine.

Consuming Porn of Other Orientations

From the Ask Me Anything questions from Sugarbutch’s 4th anniversary:

My question is more on the philosophical/political side of things.

Do you feel that, as I am a male, it is exploitative for me to enjoy queer porn so much?

Porn is filled with many different dynamics, and it is within it’s nature to exploit the ‘exoticism’ of anyone who appears in it. We’ve seen this a thousand times, especially with Asian-American women ( forced to play up an exaggerated stereotype in order to get work ), and I wonder if I myself am guilty of such a thing. Queer porn is this amazing, foreign thing to me. I love it dearly. And I understand that, as far as the exploitation from the production side goes, it is nearly nonexistant, but I worry.

I’m always on the road to improving myself and trying to further myself from the patriarchy, and this question has kind of been tickling my brain as of late.

And, since we’re on the subject: Favorite porn star? Like, if you’re given the chance to have one night of just no holds barred fuck, who are you choosing?—Erudite Hayseed, Confessions of a Southern-Fried Kinkster

I think only you can answer whether you’re being exploitive by enjoying queer porn. I don’t think there’s anything wrong with enjoying porn where the people in it are an orientation or sexuality or gender identity that you are not—I have watched my fair share of gay male porn, and I don’t think that makes me exploitive of them or their sexualities at all.

I think the exploitation comes in perhaps about how you interact or react or treat queers outside of consuming our porn. If you look at queer people and see nothing but our sexualities, that might be a bit of a problem. If someone was consuming queer porn in secret and feeling guilty and gay-bashing, uh yeah, that’s a problem. But paired with some understanding of queer culture or history or struggle, and as an ally of this movement, I don’t think anyone should feel guilty about watching the kind of porn they like to watch.

Being the analytical & processing person that I am, I would probably ask myself what it is about this kind of porn that is so appealing. Other folks in the kink community might disagree with me about this—some people say we just like what we like and do not need to come up with an explanation for it, and in fact should not examine it too hard, nor ask others to explain the ‘source’ of where their desires come from. Plenty of desires don’t have a ‘source,’ so perhaps that’s a worthless pursuit, regardless. But when it comes to really loaded play, or the consumption of certain types of porn, like for example, as mentioned above, exclusively watching Asian-American women in porn, I think it’s probably worth asking the question of why. Why is this something that I am consuming? What do I get out of this? What am I projecting? Someone may uncover the racial assumptions or associations they are making, which may be good to untangle.

This could also be true of consuming queer porn, or porn of other orientations. Perhaps a queer person always consumes straight porn because they have some hang-ups about their own sexuality. Perhaps a lesbian always consumes gay male porn because gay male porn tends to depict no-strings-attached fucking, and this lesbian has experienced lesbian sex as too emotional and not hot and lusty enough. These are untrue assumptions, however; they are based in stereotypes, and though they may be

I don’t know if I want to speculate on what a straight cis male consuming queer porn could mean. I do know plenty of “lesbian” porn is geared toward straight men, and often those porns are pretty gross, in my opinion, and I could take a few guesses at what the straight men who consume that type of porn are looking for. But I’m not sure what a straight, kinky, cis guy consuming the recent smart queer porn means … aside from that that is some of the very best porn available, in my opinion. Don’t discount the possibility of the answer being “nothing,” too—it might just be what you enjoy, and that’s fine.

Also, take a look, if you don’t already, at Jack Stratton’s Writing Dirty, since he’s a mostly-straight kinky cis guy who does occupy some space in the queer worlds, and does it quite well, and respectfully, in my opinion. (Besides, his writing is just good, and hot.)

And to answer your second question …

That’s a tough one. Madison Young, Dylan Ryan, Carson, and Joline Parton all come to mind. How could I choose between them? Carson is pretty damn toppy, so probably I’d rather chose someone who is a bottom. Dylan is quickly becoming a friend of mine, and after a certain point, fucking a friend is kind of weird for me. So that leaves two beautiful, curvy redheads, Madison & Joline. Madison would probably be incredibly intimidating, since she’s so experienced and so into pain, so I might go with Joline, she seems a little more shy, and I like that. It seems like she’d be great to throw around, she’s got great curves, great legs, and that cute mouth. Okay, final answer.

Reconciling Feminism & Sadism

From the Ask Me Anything questions from Sugarbutch’s 4th anniversary:

How do you reconcile your feminism with your sadism and desire to (gulp) hurt women? (In a completely consensual manner, of course.)—Cold Comfort

The closest thing I’ve come so far to explaining this was in that essay from December 2009 called Reconciling the Identities of Feminist and Butch Top, but this question, about sadism, is slightly different, and I have the impression I haven’t quite answered it all the way.

“Butch top” is very much related to “sadist” for me, but that’s just because that’s my particular version of butch topping, into which my sadism is built. In fact, it’s only been recently that I’ve been unpacking sadism from topping, being with someone who is much more submissive than she is a masochist. Point being, much of that essay is exactly about reconciling those identities.

Yet still, I don’t feel like that is an adequate explanation on this topic. Besides, the culmination of that essay is basically, “How did I reconcile these identities? I don’t know, I just thought about it a lot and then it was better.” There must be something more articulate to say about that.

I hit on it a little more in the essay Yes, No, and Consent too, about agency, in feminist terms. It has to do with the very simple distinctions between BDSM and abuse, even if they are equated by many anti-porn feminists. And it has to do with the Platinum Rule—not the Golden Rule, the “do to others what you would like to be done to you,” but the “do to others as they would like to be treated,” and the acknowledgement that how you want to be treated and how another wants to be treated may not be the same thing, especially when you add in the complexities of relationship through sex, BDSM, sadism, and masochism.

But, if someone wants me to treat them a certain way and something about it feels funny to me, I trust that, and I take a break and pause and ask questions (hopefully without over-processing or projecting), until I feel like we have resolved whatever was coming up or until I decide there’s too much there to open up without adequate containment or backup.

To go back to the Platinum Rule: for a pop-culture simplistic example, consider the Love Languages! Which, cheesy as they are superficially, I think are a very useful system to think about the ways that myself and my partner may be seeking the same things (like love, comfort, security, passion) but may be in different ways (through words of aspiration, quality time, physical touch, acts of service, and receiving gifts). I think we all have some relationship to all five of those ways (and possibly more), but many of us are more focused on some of those ways than others.

All of us are seeking similar things, like love and sex and companionship, but we may be seeking to play with those things in different ways. And figuring out what my own preferences are in playing with those things, and in being in a relationship, figuring out how I best communicate, who I’m attracted to and what qualities I most prefer in someone else, and how to reconcile differences or misunderstandings between us, has been a huge journey, and has been a huge piece of being able to articulate that I want to play with deeper, heavier BDSM, like pain or humiliation, and to trust someone enough to believe that when they say they want to play with that on the receiving end, they mean it, they know themselves well enough to know what they want, they are experienced enough to understand what they’re asking for, they are in touch with themselves enough to tell when they have reached a limit, and they are strong enough to be able to communicate with me around whatever is going wrong (or right).

I’ve worked a hell of a lot on my own issues, particularly on being able to say what I’m thinking, to stand up for myself, and to not get swept up in someone else’s psychology and psyche. I’ve been in therapy for about four years now, and that has helped me greatly with my communication. I’ve also done all sorts of “alternative” methods of healing, such as massage therapy, physical therapy, acupuncture, tinctures, supplements, nutritional counseling, bodywork … I’ve done a lot of work on myself and my own issues, and I am continuing to work hard to improve the ways I communicate and relate.

So, this is how I would reconcile feminism & sadism:

  1. Acknowledge that people want different things. For example, your desire to hit someone is bad when the person you are hitting doesn’t want to be hit, but when the person you are with wants to be hit, in a playful, controlled, conscious way, that’s called consent and it’s (probably) great. Consider the distinctions between BDSM and abuse, and trust yourself when you know you are on one side or the other. Listen to your lovers when they give you feedback about how your behavior affects them.
  2. Play with people whose consent you trust, and don’t take responsibility for other people’s consent. And, if they consent, then later uncover that it was actually bad for them, they didn’t like it, or blame something on you, you can certainly apologize and take responsibility for whatever your part of it may have been, but it was not your fault that they consented to an act that you then did. Be willing to process a scene after playing, and listen carefully, but know that trying to retroactively revoke consent is a dangerous move.
  3. Seek out and understand the background and history and texts on BDSM. Find mentors (if you’re in a city big enough to have a BDSM scene) and take classes, or join online BDSM groups and learn. There is a rich history of writings and teachers who discuss what it’s like to go into these deep, dark realms of physical sensation and psychology, and many of them hold important explanations for how this play works. Studying these arts makes us more aware, which can make us more conscious, and more intentional, and better able to be present in our play.

I’ve always, for as long as I can remember, had a deep connection to feminism. And I believe in it the way I believe in psychology or democracy—that even though there are plenty of people out there fucking it up, there is a kernel, a spark, a rawness at its core that I believe is important, necessary, and is deeply aligned with me and my sense of purpose in this world. I don’t believe that because some people are taking these things and claiming them to mean some things that I disagree with that I need to then step out of the ring and let them take it over. I’m glad that there can be multiple perspectives coming from one singular idea, it strengthens the idea to have multiple angles, I think (even if sometimes I believe they are so very wrong).

I know there are plenty of people who say they are not a feminist, especially those who work in various aspects of sex, and that there are plenty of feminists who would probably say that I am “not a feminist” because of my BDSM play or my masculinity or whatever. But I have enough sovereignty around my feminist identity that I know that their version of feminism is simply different from mine, and that mine is no more wrong than theirs is.

So that’s my last prescription for reconciling feminism and sadism: Ask yourself what your definition of feminism is. If you start digging to discover that you think feminists never, ever hit someone, or humiliate someone, or call someone a bitch, or shove a cock down a girl’s throat, well then, you are going to have some trouble reconciling those two identities. This is where the #3 Research on BDSM will come in handy, because BDSM circles know the difference between play and real life. We know that rape is absolutely not the same thing as playing with consent, as someone yelling out “no no no” during a scene. We know that the things that we play with during scenes, like pain, like giving or receiving pain, are not fun to experience in real life. I would never want someone to spank me or beat me or slap me in the face for real! I would never want someone to do that to my girlfriend! But under the umbrella of play, it takes on other qualities. It might look the same, a slap across the face vs a slap across the face, but the motivation, intention, control, and outcome are completely different.

Growing involves seeing more than the black or white definitions that labels, identities, and systems of thought often prescribe. Lots of feminists have written about how oppressive the sexual culture surrounding the subordination of women is; and that’s important to learn. However, equating ALL acts of some kind of sex, happening between consenting adults, that you or “feminists” deem inappropriate with oppression or non-consent is denying a key part of sex play: agency. Hurting someone, especially sexually, is something (some) feminists shun, but when you add consent into that mix, you’ve entered into something that is not black or white. And perhaps not even gray, since consent puts any act in a whole new category.

Did that adequately answer your brief but loaded question? Are there other follow-up questions from what I’ve posted here?

Anal Week Wrap-Up

Even though I started Anal Week way back in April, I’ve finally gone through all the posts and toys and reviews and things that I intended for it, so here’s the wrap-up.

Reviews:
The Ultimate Guide to Anal Sex for Women, the guidebook by Tristan Taormino
The Tristan Butt Plug
The Silk anal dildo

Quick Anal Interviews:
Charlie Glickman
Dylan Ryan
Bailey
Tawny
Madison Young
Sophia St. James
Erudite Hayseed
Your turn: answer the questions yourself

Queer Porn:
Dylan & Madison on Everything Butt
Best Anal Scenes in Queer Porn with JD Bauchery
Best Anal Scenes in Queer Porn with Essin’ Em
Best Anal Scenes in Queer Porn

Thanks so much to everyone who let me interview them about queer porn and anal tips! I had a good time doing a slightly more in-depth exploration of this, and I hope it was helpful to you too.

Quick Anal Interview: YOU!

Okay folks, Anal Week is coming to a close, you’ve had a chance to read Quick Anal Interviews with Dylan Ryan, Bailey, Tawny, Madison Young, Sophia St James, and Erudite Hayseed. Perhaps you read through some of those thinking, jeez, they left out this really important thing!

Well, here’s your chance: I’d like to hear YOUR answers to the quick anal interview questions! Here are the questions, add your answers to the comments.

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?
2. What lube do you recommend?
3. What position do you find excellent?

Any bonus perspective, tip, story, or thing that you’d really like to share?

Anal Week has been a really fun project, I’ve learned a lot in collecting all this data, Kristen and I have had some great conversations, and I’ve had some great comments and emails from folks saying they have had similar reservations, but that these tips and perspectives are encouraging.

Please do chime in, if you’d like to add something.

Quick Anal Interview: Erudite Hayseed

This is the last of the Quick Anal Interviews! Anal Week is coming to a close … just one more thing to go, and it’ll be all done. Thanks so much for reading. This quick anal interview is with Erudite Hayseed, author of Confessions of a Southern-Fried Kinkster.

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?

Tongue work, all day tongue work. Look, the prospect actual anal penetration, be it finger or otherwise, is pretty intimidating. Of course you have to ease into it that’s basic info and all. But the tongue, the actual art of analingus, is like a soft slippery key to a whole new facet of lovemaking. I’ve yet to find a partner that doesnt like it. Sure, one’s who thought it was strange of me to do it ( at first anyway ), but everyone tends to like it. That can lead to more play later. When people say “go slow,” folks have a tendency to think that means the actual act of preparation leading up to the actual fuck. There needs to be more “go slow” in relation to easing your partner into the idea of play.

While I consider anal sex to be a “No surprises” zone for most things ( and any guy who says that he just popped his dick in and went to town is either fulla shit or nursing some bruises around the head and face ), the odd surprise tounge swipe is a great way to get into the swing of things. Heck, sometimes it feels even better than the actual penatrative act, if my Lady is to be believed. But it does relax things, and it definetly shatters some hangups your partner might have.

2. What lube do you recommend?

Boy Butter. It was developed by Eyal Feldman, this brilliant gay businessman who owns and operates his website and who personally worked to create what he figured would be the best anal lubricant on the market. It’s silicone and coconut oil based, washes off with water, and just seems to last so much longer than any other lube I’ve tried ( and I’ve tried extensively ). They even make a desensitizing blend ( good for those who are just starting out or those who are working with a larger size ), water based if you’ve got any sort of silicone allergy. The price is fair, especially for such a groundbreaking idea, and the packaging is just adorable. Seriously, give it a try.

[ Quick note from Sinclair: silicone based lube does NOT go with silicone toys, so DO NOT use it if you’re using butt plugs or strap-on cocks that are silicone. Also, many sex educators are really against desensitizing anal creams, they can be dangerous. ]

3. What position do you find excellent?

Depends on what I’m doing. For rimming, I likefor Lady to basically lay down with her knees under her stomach, kind of sitting on her feet–it gives the best access to everything, the entire themepark of waist-southernly delights. Thats good especially for kinkier fare, and the application of bondage tape and an eager tongue tends to add up to a very, very fun time.

For the actual act of lovemaking, I tend to use a position that is popularly referred to as the “Prone Bone” wherin your partner lays flat on his/her stomach with legs closed. I will warn that this position should only really be used if you know what exactly your partners limits are. My girlfriend likes it rougher than most, with almost no way to get out of her predicament, so that position is just the best. Doggystyle is okay, but I feel like I sacrifice a bit of my actual thrusting power with it, and if we’re doing it, daggone it we’re doing it.

Any bonus perspective, tip, story, or thing that you’d really like to share?

Toys can be an intimidating thing, but if you’re comfortable enough with rocking the whole vibe/dildo set, I have to suggest a butt plug. For one, they come in just about any size, and for two, they are the ultimate in preperation. A good, small buttplug for the first time user is excellent. For one, it’s something you can slide in and not worry about holding, which is a big hurdle for a lot of people, myself included: I dont mind taking the time and all, but just sitting there with a couple of fingers up your partner while she adjusts can get a tad boring. If your partner is especially tight, like mine, it turns into this whole waiting game atmosphere. I’m a decent hand at dirty talk, but I can only keep it up for so long.

Another great benefit is that the butt plug is a good bridge between vaginal and anal sex. Trust me, it makes everything on the pussy end of things much, much more fun. The space that is normally afforded to your invading fingers or cock is filled up, creating a tighter feel and angling whatever you’re doing upwards, which can really up the chances of ( or the intensity of ) a pure penetrative orgasm. If you’re already past the first couple of stages of involving anal play ( discussion and light teasing/fingering ), this is honestly the next step to go.

Thanks so much!

Best Anal Scenes in Queer Porn

According to me, anyway. Essin’ Em and JD Bauchery also gave their opinions for Anal Week (which has extended longer than a week, but is still tagged, so it works. You don’t mind, do you?), but at this point, I’ve done enough queer porn watching and research to have gone through the scenes I wanted to and picked a list.

Warning: these photos are NSFW. I don’t post a lot of explicitly nude photos here, I know, I try to keep it at least kind of safe for work, but I just can’t resist putting some really great screenshots in this post, so you know what you’re missing, if you haven’t seen ‘em.

All screenshots were snagged by me through Hot Movies for Her, and reprinted only to promote the films.

1. Dylan, Jiz Lee, & Jo in The Crash Pad (Scene 1)
Directed by Shine Louise Houston for Pink & White

I have a special place in my queer-porn-lovin’ heart for the original Crash Pad. It’s the project that launched The Crash Pad Series online, and has raised the bar for queer porn production everywhere. Shine Louise Houston set up a wonderful premise—that there is this mysterious apartment called the Crash Pad, which you can acquire the key for, and go there to fuck—that has led to scenes that are real, not campy, not bogged down in falsified plot, but still capable of some twists and turns.

Like this one: Dylan & Jo are having a good time fucking in The Crash Pad until Jiz and Jiz’s date show up too. Jiz joins in, while her date watches, and the resulting threesome is hot. The Crash Pad also sets up the porn careers for Jiz, Syd, and Dylan, and thank goodness it did. Isn’t the world a better place because we get to watch these beautiful, skilled queers fucking? Absolutely.

2. Syd Blakovich & Jiz Lee in The Crash Pad (Scene 3)
Directed by Shine Louise Houston for Pink & White

Syd Blakovich (credited as Shawn) and Jiz Lee are popping off the screen with chemistry in this one. I’ve heard some of the backstory (some of it they explain in the bonus features of Superfreak), that they hadn’t had sex in a few weeks and weren’t sure if they were going to continue fucking, so this might be their last hurrah. Thankfully for us, it wasn’t, and they’ve gone on to making a ton of queer porn, with each other and on their own.

In this scene, they both look very boyish (boiish?), lean, and super-short hair, and the intensity is riveting. Syd’s rimming is pretty amazing to watch, as is Jiz’s squirting all over Syd, later.

3. Rozen Debowe, Syd Blakovich, Jiz Lee, & Donny in No Fauxxx Roulette (Scene 5)
Directed by Courtney Trouble for Reel Queer Productions

Yeah, it’s Syd & Jiz again—I want diversity in this list, but they are just in so much good porn! So: here we’ve got director Courtney Trouble (who runs No Fauxxx) in a great video collection of scenes. This one is my favorite by far (I don’t even remember the others in this film), I’ve watched it quite a few times. Rozen Debowe—who I think is so incredibly hot and who, I’ve heard, has retired from porn, and who I think should make more—approaches a bartender, spreads her beautiful long legs, and proceeds to get fucked by three butches. Or, three masculine-ish-queers, if they don’t identify as butch.

In this screenshot, Rozen is on top of the bartender, Donny, Syd has a Pure Wand in her ass, and Rozen sucks Jiz’s cock. And, it gets better. Plus, they’re on a pool table.

4. Lorelei Lee, Princess Donna & Dana DeArmond in Superfreak (Scene 5)
Directed by Shine Louise Houston for Pink & White

Lorelei Lee and Princess Donna have done quite a bit of hot queer porn also, appearing in The Crash Pad Series and on various other sites. In this one, they’re joined by Dana DeArmond, and Lorelei is topped with some really hot anal, mostly with fingers and rimming. They’re sexy and clearly very skilled (though I have to kind of ignore all the whimpering of Lorelei and humming that the two top girls do. Maybe you like that kind of thing, I find it distracting). In some of the interview scenes, Donna and Lorelei say, “I wish we could’ve gone all the way,” in discussion of anal fisting. It’s illegal to show fisting on video, did you know? Not on the web, though, so you can find some great stuff in The Crash Pad Series.

5. Dylan Ryan & Trucker Cash in Roulette Dirty South (Scene 2)
Directed by Courtney Trouble for Reel Queer Productions

I couldn’t leave out my favorite porn couple! Dylan Ryan and her real-life partner Trucker Cash are so damn hot in this scene. I love the bright colors, the clothes they’re both wearing, that slightly rickety table that they fuck on, the way Trucker warms up her ass before taking out his cock and fucking her until she comes hard, shaking and swearing.

When Trucker unzipped and I saw he was packing the Goodfella, I thought, wtf? That cock is so small! But then, turns out it is a very good size for anal. Note to self.

6. Nicole Chatte & Peter Danger in Heartland: A Woman’s POV (Scene 1)
Directed by Madison Young for Reel Queer Productions

This last one comes from director and porn star Madison Young. She introduces the scene and explains that she found this couple because they’d contacted her online, and they agreed to be filmed.

I had a crush on Nicole the second she came onscreen. It’s filmed by Peter, I think—or, if not by Peter himself, than from Peter’s point of view of seeing Nicole, so we don’t get too many shots of him (too bad, cause he seems really hot and skilled, I’d like to watch him more), but I did like watching Nicole. It starts off with a beautiful blow job by Nicole, and leads into her getting fucked hard while she’s backwards in this beautiful worn-in leather chair. It’s a bit more amateur-ish than the others, but I especially love the way Nicole guides her lover, saying, “will you start out with the small one, then use the bigger one?” and then, later, “faster, go faster,” which Peter happily obliges. The scene is really sexy and goes on for a while, with various different positions. Nicole even asks Peter to fist her, at some point, but since that can’t be shown on the video, we don’t really get to see it.

Whew! Okay, that covers it, my current favorite anal scenes in queer porn.

While porn isn’t the best place to learn how to do a certain act, it can certainly be inspiring to watch and recognize how much pleasure everyone is having from the things they’re doing. It’s definitely been inspiring to me to try more.

Did I leave out YOUR very favorite scene? Which one looks like the one you’re going to rush out and watch right this minute (or, as soon as you can)? Got any must-see recommendations for me from Essin’ Em or JD Bauchery‘s lists that I haven’t included?

Anal Scenes in Queer Porn with Essin’ Em

Who comes to mind when I say “queer porn expert”? For me, it’s Essin’ Em, aka Shanna Katz, queer femme and porn lover extraordinaire. Since I’ve known her, she’s worked at Hot Movies For Her, Eden Fantasys, and now Fascinations, and she’s traveled the country doing workshops—even recently one on feminist porn. She was glad to offer some suggestions for anal scenes in queer porn; here they are.

Photo of Essin' Em by Half Moon Studios

There is the Vai/Jiz Lee scene in CPS that I LOVE because it’s Vai’s first time giving anal play (especially strapping it on and fucking someone) to someone, and it’s just fabulously fun to watch her love it and experience it.

Then of course, there is that super hot queer gang bang in Roulette with Rozen DeBowe, who just takes it in all three holes (including using the Njoy Pure Wand) from three hot andro/butch/genderqueer studs, on a pool table, in the middle of the Mission. Hot hot hot (especially because I’ve now met half the cast AND been to there it was shot).

I LOVED the sceen in Couch Surfers: Trans Men in Action where Dex Hardlove DOUBLE anal fists two of his greedy pigs…with lube boy coming it, bandana on the face and all to add lube as needed. It inspired me so much that I re-enacted it, with vaginal fisting with two bottoms and my lube girl (bananda and all) during a fisting class in Denver last year.

I love Dylan Ryan and Madison Young’s “Spa Day Gone Horribly Wrong” type of scene on Everything Butt. Is it technically a queer porn producer? No, but Madison and Dylan made it hot and sexy queer porn regardless, and really queerifyed kink that day.

Of course, how can we forget the hot anal in the original Bend Over Boyfriend with Carol Queen? This often gets left out of queer line-ups, but to me, it’s some of the first, hot queer porn, and in this case, specifically anal. Pegging your lover’s ass really fucks with so many expectations and binaries, and Carol was doing it years before people were even talking about it.

Thanks, Essin’ Em! Whew—I’m almost done compiling my own list, I will have that to share with you all soon. I’ve got a few more things to watch first.

Anal Scenes in Queer Porn with JD Bauchery

I’ve been compiling and asking around about the best anal scenes in queer porn, and I’ve got a bit to report.

If you’re one of those folks who thinks that lesbian porn is generally oriented toward men as viewers and producers, I encourage you to think again. Yes, there is plenty of bad lesbian porn, but the amount of queer and feminist porn that is getting made these days is a bit mind-boggling. Personally, I can’t keep up. I’ve got a long list of films to watch that I still haven’t seen, and directors like Courtney Trouble and Madison Young and producers like Good Releasing keep making films faster than I can keep up.

I asked JD Bauchery over at Hot Movies 4 Her for some of her personal recommendations for butt scenes in queer porn, since she is WAY more of a pro at queer porn than I am.

And here’s what she recommends:

Which of these have you seen? Any in particular that you recommend?

Quick Anal Interview with Lissa

1 – Tip – I’d say the most important component of anal sex is trust. Trust your partner, trust yourself. If it doesn’t feel right, for either partner, stop, pause, back off a little bit, try again. Change positions, move around. Don’t be afraid to make a mistake. Don’t be afraid to make a mess! Trust is key.

2 – Lube – I’m not sure I have a favorite. Whatever we happen to have on hand, really. I like Probe for an all purpose lube.

3 – Position – On my side, with one leg up. For me, anal sex is very intimate. Being on my stomach takes away some of that intimacy for me. I love being able to see my partner’s face, reach out to her, talk to her. For more power/control exchange situations, bent over any piece of furniture is glorious, especially if there is a vibrator nearby and my hands are behind my back. Two favorite positions for completely different reasons.

Thanks Lissa! Follow her on Twitter at @swtlissab.

Quick Anal Interview with Sophia St. James

Sophia St. James

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?

I think a person needs to be mentally ready for anal sex. Many go into it thinking it’s not gonna be the much different than vaginal sex and the feeling IS much different. And though anal sex can be quite enjoyable, the feeling can be uncomfortable for many. Personally, when I first started having anal sex it wasn’t my favorite. It was a little hard to get pleasure from it. But over time, I have become a huge fan of anal play/sex. Another thing that can help is anal play. Rubbing, touching, and licking can all be very erotic and stimulating. It can also help relax the muscles and allow for easier insertion.

2. What lube do you recommend?

I personally love Liquid Silk and Pink. They are the least irritating to my tissues and they last much longer than any lube I have used.

3. What position do you find excellent?

My favorite sexual position for anal sex is doggie style. I am more on the rough side of play, so I find that in the position, more BDSM/fetish play can take play that I enjoy. Plus it seems to open things up a little bit better.

Any bonus perspective, tip, story, or thing that you’d really like to share?

I like the ‘work-up’ approach. Start with playful touching and rubbing, then licking, then fingers, eventually working up to something larger. It’s sensual and erotic, not mention it helps me to get into it more and relax.

Hope that helps some!

Thanks Sophia! You may remember her from such films as Bordello, which is where I first saw her. Visit her site at sophiastjames.com.

Quick Anal Interview with Madison Young

This Quick Anal Interview comes from Madison Young, feminist, art gallery owner, and porn star. If you haven’t seen her come on camera, you are missing out, it is a glorious thing to watch.

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?

When doing anal play its important to remember Jane Fonda’s advice “Don’t forget to warm-up.” Stretching isn’t just for yoga or before a morning jog. If I’m planning on doing anal play with my partner or for work I like to warm up before hand. First I like to warm up with lube and a finger or two. Slowly insert into your anus and relax your sphincter muscles and let you anus suck in and relax around your fingers. Then start to slowly move your fingers further into your rectum. This also helps to lubricate the inside of your anus and rectum. I also really love butt plugs and feel like it is a great way to turn on your partner in public as a form of foreplay to wear a buttplug on your date. This also gives your anus plenty of time to warm up and get stretched and ready for different types of anal play when you get home. I highly recommend the silicone b-bomb from GoodVibes.com from Tantus.

2. What lube do you recommend?

I’m a big fan of lots of silicone lube. Swiss Navy is my preferred brand right now. It provides the the perfect slick lubrication for anal play that doesn’t dissipate too quickly. They also have a neat pump so you don’t have to fumble with the cap to the lube when you are in the moment.

3. What position do you find excellent?

It depends on what type of anal play you are engaging in. If I’m fisting my anus, which I love to do, I like to be standing and raise one leg onto a table or chair so it opens my bottom up more and makes it easier for me to reach around. I also like a standing doggy for anal sex with a partner or doggy style. Usually I like to back up onto the hand or cock to adjust myself and have my anus relax around the hand or cock before lots of fucking ensues. Anal play can be incredibly pleasurable and is much easier for me to orgasm this way than through vaginal penetration.

You can see Madison’s work on many sites, including NoFauxxx, Hot Movies 4 Her, and her own domain, madisonbound.com. Thanks Madison!

Quick Anal Interview with Tawny

Tawny calls herself an enthusiast, and says, “It’s my favorite form of intercourse.” Here’s her quick anal interview.

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?

-Masturbate a little, or have a vibe in place on your clit if you’re being penetrated and are nervous. You’ll relax easier, and be less focused on whether or not you’re freaking out (as the penetrated, obvs.)

-Breathe slowly and steadily. Anal can almost be meditative in the right mindset, and if you’re focused on your breathing and relaxing your rectal muscles, you probably will feel pleasure rather than pain. That’s been my experience, anyway.

2. What lube do you recommend?

Maximus is great.

3. What position do you find excellent?

The best position for me has always been doggy style. If whatever cock/toy I’m taking is rather large, I prefer to be bent over something so I can relax as much of my body as possible and have a hand free for the masturbation I mentioned above. (My ex-boyfriend preferred to lay on his back, but that never worked as well for me.)

Any bonus perspective, tip, story, or thing that you’d really like to share?

Honestly, one of the coolest and most zen-like experiences for me has been getting better at anal stretching. It’s erotic, trust-building, and requires great concentration. I’ve never been much of a meditator before, but I can tell you that I definitely prefer my blank slate states with something in my ass.

And story-wise: One of the most ridiculous sets of orgasms I’ve ever had (and I’m easy to get off, so we’re talking a LOT of orgasms) was being fucked in the ass with a Crybaby vibe in my vagina and my boyfriend (doing the fucking, obviously) holding the remote. We were yelled at by the neighbors, who were inside their house next door. So, I definitely recommend combining anal with vaginal penetration and a vibrator, if you’re comfortable with that.

Quick Anal Interview with Bailey

These tips are from Bailey (@bailey21975), who wrote to me after seeing my call for interviewing anal enthusiasts on Twitter. More quick anal interviews coming up!

1. What one tip would you suggest (aside from the obvious: lube, communicate, go slow)?

I’d suggest gloves (or condoms, if you are using a toy instead of fingers/hand), for several reasons. Safety, if you aren’t fluid-bonded with your partner. Gloves make certain that any scratchy nails are not going to cause even incidental damage. In my experience, wearing gloves makes the lube last a bit longer without being absorbed. Also, wearing gloves means that if you decide to go from anal sex to vaginal sex on a whim, you strip them off, toss them aside and have at it! No risk of putting bacteria where you certainly don’t want it, and you don’t have to head to the bathroom to scrub your hands, potentially killing the mood. I’m a big fan of gloves for anal play, myself.

2. What lube do you recommend?

If you’re planning on buying just one lube for all purposes, my recommendation is Liquid Silk, all the way. It doesn’t get tacky, it lasts a long time, doesn’t have an unpleasant smell, taste or texture — which is important to me, because I never know where I might want to put my mouth later. Liquid Silk is best if you’re looking for an all purpose lube, but if you’re going to have a separate lube for anal, Maxxximus is the way to go.

3. What position do you find excellent?

Whatever position is the most relaxing for the bottom, ideally. For me, whether top or bottom in this activity, my preference is on hands and knees, head down, ass up. It makes for great visual presentation, and you can see exactly what you’re doing.

Thanks Bailey—follow on Twitter @bailey21975.

Quick Anal Interview with Dylan Ryan

The second quick anal interview features porn star Dylan Ryan, one of my favorite people to watch fuck on camera, and anal enthusiast herself. When I started brainstorming queer porn scenes to feature here (upcoming!), two of hers came immediately to mind. Here’s what she had to say about anal sex.

Photo of Dylan by Aslan Leather, as featured on Dylan's website
Lube:

Maximus. Hands down the best one I’ve found. Stays cushy without getting gummy. I feel like most people don’t know it… which is funny because it’s sooo good.

Position:

This is hard to describe, but I’ll try. Technically it’s doggy, BUT my upper body and chest is completely on the bed. And then the boy is on top, but he actually puts his legs on TOP of my legs, and moves his cock up higher, in a more downward and less directly into the ass angle. His hands are on the bed on either said with most his lower body on top of me. We call it the SUPER DOG!

Basically, it puts more of his body weight on me. And the angle … it feels less OOMPHy. That’s the one thing about anal, I love it really hard, but the direct right-into-the-ass feels too much like poop, like “I’m filling you up with air.” But with more of an angle that feeling goes away, and there’s more sensation, less blowing up like a balloon.

In this position I feel very mounted, too, which I personally dig. It feels nasty and taboo.

Tips:

I like to do anal after I’ve already cum. So, stick to what you know, get off, and then give it a shot. Usually I’m raring at that point: the body is relaxed, the adrenaline and serotonin are flowing.

I’m really into rimming these days, and I don’t see that suggested very often. Rimming is an AWESOME way to start anal. It feels AMAZING and relaxes everything, and there can be some tongue penetration to get things started.

People tend to get really cerebral about anal, and I understand that, but internalizing all the stuff about it hurting sets people up. If anal was more a regular part of sex in people’s lives, it would be easier to do. Approaching with caution helps with injury, but the anus is pretty damn elastic. If it was something that was less associated with pain, I think people would practice and explore it more. Especially for women, the concepts around it are “oh no, thats going to hurt” as opposed to, “lets find out what I do and don’t like about it.” Just like vaginal or oral sex, everyone has different likes/needs, and exploring those can be icky and painful and weird and not hot, but it can also be amazing and sexy and hot and illuminating. Anal should be part of that package in a positive way!

Dylan Ryan is making the world a better place, one porn at a time. Follow her on Twitter @thedylanryan and check out her new website, dylanryanx.com.

Quick Anal Interview with Charlie Glickman

In the spirit of Anal Week, I’ll be doing some quick interviews with sexuality educators, porn stars, and anal lovers to get the conversation going. Here’s the first one, with sexuality educator Charlie Glickman.

A few tips:

1) try it out on yourself before doing it with a partner. If you’re going to be the giver, it’ll help you understand how sensitive and delicate the anus is. If you’re going to be the received, it’ll give valuable info about how you like to be touched.

2) do something else (simultaneously) that you enjoy. A vibe on the clit, a hand on the cock, whatever. Arousal makes anal play easier and it helps your body connect a familiar pleasure with new sensations.

3) pay attention to your mood. Anxiety and fear can cause the anus to contract, making anal play more difficult.

Lube: silicone, especially for external massage or getting started. Eros or Swiss Navy are nice. Thicker gels work better once you’re in the rectum because they give a bit more cushioning. Please Me Gel is a good one.

Position: hips above the head. Elbows and knees is good. Or on your back with a pillow or a Liberator Wedge under the hips. In that position, it can also be helpful to prop the knees up with pillows so the muscles can relax. Remember- anal penetration is about relaxing the anus, so the less work the other muscles are doing, the easier it’ll be.

You might find these useful: Anal Sex and An Introduction to Anal Play at Good Vibrations

Charlie Glickman has been a sexuality educator since 1989 and joined the staff of Good Vibrations in 1996. He holds a doctorate in Adult Sexuality Education and is certified as a Sexuality Educator by the American Association of Sexuality Educators, Counselors and Therapists. See more about Dr. Glickman or read his work at his blog, or on the Good Vibrations Magazine.

Anal Sex Week Starts Today

It’s long overdue, I know.

Remember back in September, I posted something about how I’d like to fuck Kristen’s ass? Then there was a bit of controversy, people thinking I was trying to use the Internet to get her to do something she didn’t want to do. Clearly that is not the case.

(Not to open an old can o’worms or anything.)

Even so, there was a follow-up post with some more details about what this meant for us and what I was intending when I put the first post up. There are some great tips from commentors for folks interested in getting started or having more anal sex, too, which I do recommend you read.

We are far from pros at this whole anal sex thing, but it’s been working quite well between us, and we’ve both got comfortable enough with it that I can slip it in (ha, ha) at various times when we’re doing other things, already playing, and we do that somewhat regularly.

I did get out the lovely Tantus Silk cock, that I got from Babeland, and strap it on and fuck her ass with it, but so far that’s only been once. We both express interest in doing that again, I guess from my perspective it just takes a bit of warm up, and preparation, and I tend to stick with what works. I get impatient, is what I’m saying.

But clearly that should change if I want to continue to help push our sexual explorations into new territory.

In the past six months since I first put that post up, I have collected a host of anal toys and resources that I want to share with y’all. Some of them I’ve already mentioned or written up, like the Njoy Fun Wand and Tristan’s famous butt plug, but there are more goodies that we’ve explored since and I want to share them with you, too.

So, in the next week, I’ll have for you a review of the Tantus Silk cock, perfectly sized for ass fucking; a beautiful glass butt plug from Good Vibes; and Tristan Taormino’s legendary book The Ultimate Guide to Anal Sex For Women, sent to me by Eden Fantasys. I’ll write up some lubes that are particularly good for ass play, some tips for beginners, some of my very favorite anal scenes in queer porn, and write up a dirty story or two about what the anal exploration has been like here at Chez Sexsmith.

What about you out there? What are your favorite anal scenes in queer porn? What are your favorite toys to use? What’s your favorite lube? What position do you just love to be in? Let’s get the conversation going while I focus on the upcoming posts.