I’m in a bit of a pickle. I’ve been out for ages, but for reasons not worth getting into (for instance mostly due to lack of opportunity, not lack of interest or any deep seated issues) I’m still completely inexperienced when it comes to girl-on-girl sex. I have however had a fair amount of boy-girl sexcapades.
But now I have the opportunity to get some girl-on-girl action and I don’t want to tell her it’s my first time. I know I should, but I’m too embarrassed to admit that despite years of being out I’m a 28 year old queer virgin. I want to be a good partner and please her in bed but I need some direction. Will she expect me to go down on her the first time we go to bed together? Any websites or great tips to impart? Any help you can offer would be great.
Thank you Sinclair. You and your words have been helping me get off for ages. Now I’m hoping you can help me got off with a partner.
As a budding baby dyke, I relied on books. Nothing But the Girl and Best Lesbian Erotica 1998 spring to mind, because in 1998 and 1999 I was obsessed and barely out. I left my boyfriend of six years in August 1999 to move into a crowded little apartment on Capitol Hill in Seattle with a dyke I barely knew, eager to have my own room, my own space, a place for my own desires. It wasn’t until April 2000 that I slept with a girl. She was in my nutrition class, and we had the same birthday. “Did you just say it’s your birthday?” “Yeah.” “It’s my birthday today too!” We talked and started sitting together. I put my hand on her knee under the table, and she let me. Kissed me in front of the school after class when we went our separate way. “You’re bold, touching my knee like that,” she wrote in a note later. “I like bold.” She invited me to her house for lunch.
She’d never been with a girl either, but she like me (and you) knew she was interested and had some sexcapade experience. When we started getting undressed (awkward light from my only bedroom window that faced the parking lot, shaded by a fringed grey shall, moon poster up over my bed, feminist books stacked in every spare space), kissing, oh she was a good kisser, I had no idea what to do or what it would be like or how to please her. But when she paused and said, “I don’t know what to do,” I could feel my relief, at her admission of what we were both feeling, and knowing that she didn’t know what would to do meant I could step in and take the (gentle) lead.
Oh, I thought. I know what to do.
I didn’t, not really. But I suppose in some ways that was the beginning of me as a service top, taking some limited control and having bodily permission to touch in ways that pleased her. That’s all I wanted to do: feel her, please her, touch her in ways that she liked, connect with her.
That’s all sex is, really. Sure, the orgasm part is a really nice added bonus—but not everybody comes at all, not everybody is able to get off with a partner, and almost nobody comes with a new person the first time.
Carly, you wrote this to me in March 2012 (and I am so behind on advice/ask me anything questions, this year has been impossible, see: the Making Peace series and the last 18 months of this site), so I presume you weren’t waiting on my small piece of advice before you went for it. So hopefully, this advice comes too little too late. Hopefully this is all irrelevant. Hopefully, you’ll comment on this saying, Oh! That was me! But I totally forgot I even asked that. I’ve been fucking for eighteen months now, I have this completely different other question now.
But just in case you haven’t, and just in case there are other folks out there who read Sugarbutch and dream about queer sex but maybe haven’t had much of it yet, this is my advice to you.
Will she assume that you will go down on her? I have no idea. Depends on the person. Personally, I think going down on someone is an incredibly intimate act, and I wait quite a while after starting to date someone to do it. Also, I am STI-aware and don’t go down on someone without a barrier unless we are fluid bonded, which also often happens after a few (or quite a few) dates (or never), depending on our agreements and how in-depth we go into our own STI histories and whether or not we have other partners or whether we’re going to go get tested again. I have dealt with this differently with everyone I’ve dated, but the short answer is, I think, no, you shouldn’t assume you will go down on someone on your first date or in the first month or so, and if you decide you want to, it should be after you get to know them more and have some safer sex conversations.
Don’t assume anybody is going to come the first time. I believe you are responsible for your own orgasm—in general, not just the first time—so if you want to get off, assume you’ll be getting yourself off. And make it totally okay for her to get herself off, too. Offer to watch, if she finds that sexy. Or offer to help, in whatever ways would be helpful (lick her nipples? Kiss her? Hold her down? Whisper sexy things in her ear? Shove your cock in her mouth? To each their own …).
Unless you have a strong power identity established already, and do a bit of negotiating, don’t assume who’s going to top and who’s going to bottom. Just feel each other. You’re getting to know each other in a new way: physically, energetically. Go easy, take each other’s cues. It’s a complicated physical dance.
To get ready for your first girlon-girl time (or whatever—y’all know that I mean to extend that to other genders too, right?): Jerk off a lot. Notice what you do, how you touch yourself, what feels good. Try those out on her body.
And pay a lot of attention to how she responds. If you can talk, ask how to touch her, ask what feels good.
Feel into your own body, and follow the pleasure. What would feel good right now? Tell her that, and ask: “I really want to kiss you right now. Is that okay?” “I have this urge to spank your ass, would that feel good for you?” “I have some soft pretty rope just … right there … I wonder if you’d like it if I used it?” “Can I introduce you to my favorite vibrator?” “I really love using a strap-on, do you like penetration?”
As I have been thinking on this answer, I kept saying to myself, Self … damn. If only there was a Girl Sex 101 primer that I could point Carly to for more tips and tricks and ideas about communication and negotiation and following pleasure and how ladyparts are awesome and different and the same.
And then I realized that maybe there’s not a perfect one of those right now, but there’s this:
That Allison Moon and KD Diamond are building, and you’re just in time to get a copy for yourself by supporting their Kickstarter.
What is it? Well …
Girl Sex 101 is a road trip in a book! Combining fiction & comics with solid sex-education, Girl Sex 101 does what no sex-ed book has done before.
A collaboration between author and sex-educator Allison Moon (the Tales of the Pack novels about lesbian werewolves) and artist kd diamond (founder & editor-in-chief of Salacious Magazine) Girl Sex 101 is loaded with fun, color illustrations and entertaining stories that offer far more than the standard sex-ed fare.
Plus, “Girl Sex 101 is a collaborative effort of over 15 independent educators and artists, featuring fun & informative guest viewpoints by sex-ed superstars” like Megan Andelloux, Tristan Taormino, Jiz Lee, Carol Queen, Julia Serano, Tina Horn, Ignacio Rivera and more!
So clearly you should try that too.
I also recommend these books:
I wish I knew of other good resources! So I figure this is a great time to ask the readers. Hey, readers! What do you recommend? What books or websites or sources? What are your best tips for queer sex for the first time?
PS: If you asked for advice from me in the past few years, and never received it, I’m sorry. I know many (hundreds, actually) of you have emailed me questions or asked me questions, and I haven’t replied. It’s because I have not been on top of my shit in the ways I would like to be—it’s not because your question wasn’t fascinating. It probably was. It’s just that I haven’t been on a schedule or replying or corresponding in the ways that I want to be. But, I’m sorry you reached out and said something possibly vulnerable or sweet or real, and never got anything back in return.
If that question (or a different question) is still relevant to you, the way to skip the queue and come to the top of the list is to send me a donation or book a 30-60 minute session with me over Skype or over the phone. I’ll address your question, and more.
Tags: advice, ask the readers, girl sex, I miss on our backs magazine so much, I still love the on our backs guide to lesbian sex even if it is dated, kd diamond, queer, queer virgin, sex advice, sex education, some of my backstory, support cool queer things on kickstarter!
When I think about the past two years, and trying to put some sort of something together to explain how it’s been, I think in photographs. That one where he’s picking raspberries with his bare hands, crouched in his brown tee shirt, raspberry juice running down his wrists, pink staining his tongue. The one where he and his dog are surveying the moonscape of northern Yukon right before we turned past the “Welcome to Alaska!” sign. The one he called “doing important boy work” where he was sitting in a jock strap and nothing else on the porch at the ranch writing in his leather boy journal, writing reflections on tasks for me or writing about feelings of service and submission or writing a book report, I don’t know what the task was, but I’m sure it was important. The one with his dimples in that orange-red light that I looked at over and over before I really knew him.
I’d put together a collage post, an essay in photographs, but that doesn’t feel good enough, because who knows what you’d see. Maybe you’d see what I see, all the sweet boy tasks and dimpled smiles and creating art, but you wouldn’t see so many of the other things: the quiet contemplation, the complexities, the intensity of inner landscape, the artistry, the precision, the majesty.
It’s not easy, this intimate loving. I don’t know how it could ever be easy. It’s a practice of stripping away blocks, stripping away defenses, reminding myself over and over to let in, take in, open up, drop that protective layer. What a horrible thing to do, and how beautiful. What else is there, really, than to let someone see who I am as true as I possibly can.
This is my best truth, I whisper to him over and over, with each breath, while I sleep, while my lips touch his fingertips, while my key fits his lock. Right now, I am ruined. Right now, I am running. Right now, I am ruminating. Right now, I am rubber bouncing away. Right now, I am rumbling. Right now, I am rushed. Right now, I am a ruby shining. Right now, I am rusted through and I fear one touch will crumble everything. Right now, I just need you to hold me, take your hand and put it there, hold me from inside.
I have loved enough to know not to make grand declarations while I fall. I know I have said the same things, again and again. Falling always feels like that: brand new, awakened, like nothing else ever before. And it’s true. This time, it’s green green in all her shades, babygreen and lime and chartreuse, fresh mown grass, pine and spruce, fern and jungle, tea and olive, so many options. Let’s spend the life of our relationship cataloguing all of the hues and saturations, all of the chroma and light, every kind of value there may be. Let’s memorize the hex and RGB codes and recite them in each other’s ears when we need to remember the secret language in which we speak. This green that is growth and renewal, from budding seed to moss covering the old growth. Every stage, none more valuable than the other. None needing to be hidden. No forest does their mourning in silence, hidden away in holes or caves. Trees fall out in the open, unapologetic. This is my direction. I will now lay down to rest. We heard that great snap on the outer point trail and both looked to the canopy: which one would it be? The clear sound of tree death echoed, but it took a moment before falling. Like a ball bouncing tall tall tall and then less and less until the sound waterfalls. The tree was a waterfall as it descended, mortal, unrooted.
This is what happens. Unrooted I descend, mortal, and no one to be worshipped. And yet he does it anyway. So devoted, he whispers, and I whisper it right back. My noblesse oblige, my responsibilities, the placement in his life I continue to earn daily as I am to be and act from my best self. The deepest of forest greens. Living with him seems small compared to owning him.
I don’t know why I crave the power I do, nor does he know why he craves the submission he does. We puzzle, we theorize, we study, we muse. And we give to each other in these ways that we have always craved. Something in me didn’t know what I wanted was to own, to master. The verb, the job title—not the honorific, not yet (maybe that will come later). But as I study this path, I realize I’ve always been on it. Always been trying to encourage something more, and making do with my own limitations.
I’ve been making offerings my whole life, holding up gifts, looking at paths and asking if they wanted to walk it with me. This is the boy who has taken my hand and said yes. This is the boy who showed me paths he’s discovered, too, but had not yet walked, knowing the essentiality of having another with him. This is the boy who has been offering, over and over, to take more if they wanted it. I want more. I want the edge. I seek the razor on which we can both balance. I seek the calling to be my own best self. I seek one who will stay at my feet not because it serves him, but because it serves me. That is a fine line of difference, but makes everything change.
Right now, I am shining in the oldest forest, crackling descent to the earth, digging up rubies. Doesn’t green shine brighter when there’s red around? Isn’t my heart just oh so ready to pour this blood into the earth? Isn’t there so much more to love than heartbreak? Isn’t there so much possibility, when puzzle pieces find each other? Aren’t we so ready, so prepared and ready, to live our way to the answers, live our way to the creations of our quiet, deepest callings?
I don’t know what happens next. But I know this is the beginning of year three, and I’m listening. I choose.
Tags: anniversary, babygreen, green!, happy anniversary my dear boy I love you, heartbreak, love, love letter, m/s, mastery, my boy rife, ownership, poetry, ruby red, so weird to make such public declarations but I also love it (maybe not so secretly), the r in rife doesn't have to be lower case but he always writes it that way so I do too
Tags: butch vs daddy, conversations, deepening my relationship with you readers, enhancing conversations, femme oriented butch, I suck at blogging sometimes, making peace, making peace with the readers, maybe a mini-interview, my boy rife, my cat!, social anxiety, why my readers are the best
It’s that time of year again … I am about to get back on the road and do workshops at colleges.
This year, I’ve narrowed down my workshop offering seven academic workshops:
- Fucking with Gender
- Build Your Own Gender Toolkit*
- Identities in a Label-Free World*
- Becoming A Queer Leader*
- Flirting Fundamentals
- The Dating Toolkit*
- The Sexual Politics of BDSM
* Starred workshops are brand new for 2013-2014, though frequently built upon other workshops I’ve offered in the past.
I also have some kink workshops, but I’m still working on gathering all of those together into a PDF.
I will continue to do talk about custom workshop requests, and I’ve got a Big List of All The Workshops I’ve Offered over on mrsexsmith.com in case there was this one workshop that caught your eye but you can’t remember what it was and it’s not on this new list.
Currently, I have these trips planned—and I have many more in the works that are just not quite finalized! If you are going to school somewhere near these places? I’m looking to add on gigs while I’m already going to be visiting. Get in touch with me or my intern Lori at email@example.com.
10/6-7, Claremont Colleges, Claremont, CA. Writing ourselves into existence workshop, queer theory class, spoken word performance!
10/16 NYU, New York City, Best Sex Ever workshop
11/14 Wild at Heart, Seattle, WA – Cock Confidence
11/15 The Foundation for Sex Positive Culture (FSPC), Seattle, WA – Advanced Cock Confidence
11/16 The FSPC, Seattle, WA – Leaving Marks
11/17 Wild at Heart, Seattle, WA – Queering Power Dynamics
My appearances calendar is always updated at mrsexsmith.com/appearances.
Here’s the PDF for this year’s workshops (which you can download here if you prefer):
I’m really excited to get back out there and have more conversations with all of you. Did I mention that Pink & White gave me a box of porn for me to bring to you for giveaways?
Tags: college gigs, I'm especially excited about the queer leader class, pink & white, things I'm teaching, tour, workshops
Tags: abortion, alphafemme, breakups, business, commentators, highlighting reader comments, I'll probably password protect this later but for now it's open, in praise of femmes, kristen, lightbulb moments, making peace, marketing, mike, misogyny, my boy rife, my readers are the best, options, queer cultural wounds, thank you thank you thank you, there's so much more, things I need to still think about, whining vs musing
In my last apartment, none
of the doors shut completely. I
hung hand towels over the tops
to make the seal tight enough not
to open with just the slightest
push. In this new apartment,
the doors all latch firm shut, but
I keep crashing into them, throwing
my shoulder into the wood, touching
them with my toe, a small kick,
an elbow, a slight push, expecting
them to open. Though the truth is,
they would all open, eagerly,
with trembling pleasure, if ever
I uttered the softest request.
Tags: character study, doors, drafts, integration aka integrity, making peace, maybe it's all too obvious, pushing, request, things I'm playing with, trembling pleasure, when things change, work in progress, work with a capital w
Tags: alphafemme, altars, building a new home, butch baking, check-in, comments, I still fantasize about femmes, I still love femmes, important objects, making peace, my boy rife, never make a protocol that you will not enforce, power dynamic, protocol, queer community wounds, sacred storage space, stone fruit, turn annoyances or frustration into protocol, work with a capital w
After the workshop. I haven’t had enough of you (will I ever get enough of you) and strip you bare, glove my hand, slide two fingers inside you, sideways on our huge bed. The lamplight is different than the bright white of this room during the day, more warm, orange-yellow-gold and more full of shadows, and the shadows and the gold fall onto your skin like paint. In the car on the way back I couldn’t resist (can rarely resist, it’s so hard to resist when part of our dynamic is built around taking what I want) and slide your small fingers into my mouth. You miss the exit. Your fingers are blunt and I trace your jagged nails with my tongue, suck the salt from the pads, taste the day on your skin. I pull your wrist down to your pelvis and take two fingers in my mouth again when my two fingers are inside you, gently pressing, not a lot of motion, and I start to suck you off. Up and down your fingers like a cock. I hold your g-spot and feel it quiver in my fingers. I let your fingers out of my mouth so you can touch your clit, and keep my tongue on the back of your hand. You shudder and convulse against my mouth, your cunt grips my fingers. You slide your fingers back in my mouth, eager, and I taste you, just a little, at the tips, and I do it all over again.
On the side of the bed, but you’re not supposed to be coming that day, and you do. It sneaks up on you in a moan, but before you can really come you stop yourself, blurting out, “fuck!” again, and it’s the second time you’ve come without permission, and you’re in trouble. You back off and look at me shyly; I am laughing at your distress, you just feel so bad for defying the rules, and the guilt is more than enough punishment. I can feel how bad you want to please me. I am enjoying this too, too much: your attempts to do things just right and your scrambles to fix it when you are so happy, so pleased to be serving me, servicing me, kneeling before me, my cock in your throat. It’s enough for you to see that look on my face, that ecstasy you’re causing, that overwhelming lust and adoration as your tongue hits the head so soft and slow as you suck it down, which makes me want to pulse and shoot, makes me feel my balls (as if I had them) contract and swell, cocked and loaded. You move back toward my dick with your lips parted and I push you away. “No—I think you’re done sucking my cock. You lost that privilege when you came without asking. Down. Kiss my boots.”
Long slow aftercare. I let the beating settle into your body—the belt, my hands, the restraints on your ankles and wrists. After some time on the bed I move us to the chair so you can sit on my lap. You wrap around me, sink down. You quiet and calm and I ask, “Ready to suck my cock again?” You say yes, quickly, in a whisper, and kneel between my knees. I loosen the harness and touch my clit under it while you suck me down. (You’re not supposed to come today, still; one of us may as well.) “Good boy,” I breathe as I watch your mouth, tongue, lips, my cock down your throat. I let you guide it. I let you slide it however deep you want. I push a little, because that’s what I do, but mostly I just concentrate on the feeling and the sight. I almost come but it’s too much, I get overstimulated and don’t have the right angle so I get up and take my jeans off, my socks and shoes and briefs, and spread my legs wider, get a better grip under the harness. You start in again and I imagine what your mouth would feel like. I know every inch of it, know every ridge of the roof and every tastebud on your tongue and every valley of your teeth with my fingers and my tongue, but fuck how I wish I could feel those with my cock. We are making do with what we have and you are an expert at sucking me down, swallowing, and I think about how I’d get tight and build up pressure, ready to shoot. You moan around my cock and I feel it in my pelvis and I feel you squirt on my ankle and foot, you’re straddling my leg. “Ohh fuck you’re in trouble,” I manage. You whimper a little, give me those eyes, those sweet little boy eyes like you would do anything for your daddy, you’re sorry, you didn’t mean to, you couldn’t help it, and it doesn’t take long before I’m over the edge for you, coming in your mouth, yelling out and curling my spine and feeling how I’d shove and come to the back of your throat. I breathe, my body stills. You sink down onto your belly and put your tongue to my foot, clean it off, suck my instep. With your head still down low, you say, “Am I still in trouble?” and I laugh.
You walk over to me with your cock on, hard and thick and fitting you, jutting out from your hips. “Can you stand?” I ask. You nod. I sit on the edge of the bed. You let me feel it, with my hands and along my lips, my jaw, getting to know its new contours. I put my tongue on it, kiss it, and you shudder. I like feeling how hard you are in my mouth. I can’t take it as deep as I think I can, but I try, again and again, wanting you so far inside.
You start on your knees at the end of the bed after I have kicked you, hit you with my belt, after I told you to pick a number and you picked three, after you took more than you thought you could, after you crawled for me, after my hands in you at the edge when I said come on and shoot that load for your daddy, little faggot and I shove in, impatient and hard, to the back of your throat. You gag. I keep going. I hold you by the hair and work my hips so it goes in and out of your mouth. You gag again. I keep going. I stand over you and you rise up a little higher and I keep fucking your mouth. I wrap my hand around your throat. I pinch your nose closed and shove in. You look up at me, pleading, in a rare moment of eye contact. I don’t let up until I count to ten. I take my dick out and let you breathe and do it again. Count to ten. Sometimes I hold my breath with you, but I always let mine go before you do. I fist your hair and shove in deep. My hips shake against your mouth. Come on, little boy, take it, that’s right, that’s how I like it, fuck, yeah, give me that pretty little mouth, take it deeper, you can do better than that, fucker, do it, suck it down, yeah that’s right, nice. You stumble back a little and my fist holds you up.
Tags: blow jobs, butch cock, cock sucking, coming without permission, daddy, daddy/boy, faggot, faggotry, gagging, I always spell ecstasy wrong, my boy rife, orgasm restriction, pinching your nose while you suck my cock down, records of the times my cock was in your mouth, strap-on
My girlfriend and I have been looking for a decent pack ‘n’ play cock but can’t seem to find any that seem decent, and it’s hard to choose over the internet.
I read your 101 on packing cocks, which was useful and helped me know what to look for. Unfortunately, all your recommendations have been discontinued.
Do you have any more recent cocks you could recommend? (If it’s a UK website, that would be a huge plus as postage can be really expensive to get it over here.)
Thanks very much. Regards,
In recent years, there have been generally three cocks that are considered “pack and play”: The Silky (aka the Bendy), the Goodfella, and the Tantus VIP Supersoft. All of those are outlined in my Cock Confidence: Pack & Play article here.
Not to be all dramatic about it, except that OMG IT IS JUST BASICALLY THE BEST THING THAT HAPPENED TO PACK AND PLAY COCKS EVER, a company called New York Toy Collective rolled onto the scene in 2011 and they are producing a brand new pack n play silicone cock called the Shilo.
And it is really, really good.
I think it’s so good, in fact, that I have teamed up with NYTC and I have a few of their cocks that I carry around with me and sell myself. That started because I kept RAVING about them in my workshops, but they weren’t in toy stores yet. Now, they’re in many stores, like Good Vibes and Babeland and Smitten Kitten. I don’t know if they’re in the UK yet, though (I don’t think so).
So, wait, backing up. Let me introduce you to the Shilo:
Made out of silicone, with a “proprietary core” (which apparently means “we can’t tell you what’s in it, but it has layers of silicone and other plastics”) that makes it bendable. BENDABLE. So you can tuck it down into your pants and then bend it back up straight and fuck with it well. I mean well.
It is 6 inches of insertable length, and 1.5 inches in girth. Which is a great size. A really really good size. A slightly larger than average size when it comes to cis penises, but perhaps slightly on the small side when it comes to strap-on cocks. Let me assure you that it is excellent for a) blow jobs, b) anal sex, and c) um all the other holes and fucking too. I often switch to a slightly (or massively) bigger cock when I want to really go at it for a while, but it is excellent for fucking. And because it’s very bendable, you can get it right to the g-spot or p-spot really easily.
Clean it like you’d clean any silicone: place in boiling water or on the top shelf of the dishwasher (no soap!) or wipe down with a 10% bleach solution.
Shilo is available in 4 skin tone colors, because more choices help you pick a shade that is closer to your skin tone. AND it now comes in blue/black, pink/blue and fierce pink!
So you can buy them online from various stores now, or from nytoycollective.com, or you can buy them right from ME. I’m selling them for $135, and I would much prefer to sell them in person, but I am willing to mail them to you. That’ll be $135 plus shipping (which varies depending on where you live. If you’re in the US, it’ll be flat rate priority mail).
Email me, firstname.lastname@example.org, if you want one with the color and your address, and I will bill you via Paypal.
Or, of course, you can pick it up at your local queer feminist sex-positive sex toy store, which hopefully you already patronize frequently and support in many ways, or online from NY Toy Collective directly.
Tags: advice, anal, ask me anything, ask mr. sexsmith anything, blow jobs, butch cock, I'm selling them! you can buy them from me, new york toy collective, pack and play, recommendations, seriously guys just go buy this, shilo, strap-on cock, toys