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[Part 1 is here.]

I’ve taken the cuffs off of him and for a moment we’re equals, dropped lightly out of the scene and into a few seconds of friendly conversation, laced with compassion and care.

“I haven’t been to that place in a long time,” he tells me again. “I so needed it.”

“I’m not done with you yet,” I remind him with a smirk. “Are you ready to go on?”

The flogging wasn’t even that severe; it was something about the thuddy pressure, the rhythmic nature of it, his surrender, that made him break. His back is reddened but not welted, and I can tell that he can take a lot more. I take the four-foot singletail out of my bag and order him onto his hands and knees on the bed.

In an instant he is down again, dropped into that swimming pool I know so well, the place of buzzy-headed wordlessness. I start swinging the whip back and forth across his ass, leaving little red trails in perfect horizontal formation. He breathes, managing the pain, arching his back, rolling his hips, letting it flow up his spine. I start throwing the whip and leaving fiery vertical cuts to cross the stripes I’ve already made, throwing it harder, harder, harder, not playing at the speed of sound but getting little low-pitched thaps out of the cracker and sweet whimpers, at a higher and higher pitch, out of him.

I see him start to shiver again, the muscles tense, the breathing quicken. This is the place where I always hedge: do I keep going? I back off a little, slow down, give him more time to process each strike, but then I feel what his body wants, feel that need again from him, and I ramp back up until he breaks a second time, falling face-down on the bed.

I put the whip down and slowly approach. His back is hot, his ass scorching, under my cool hand. I succumb to an impulse I rarely have with clients: to lay my body on top of his, to hold and comfort him. Finally I turn him over, and there’s a moment when I see his cock, hard and short and thick, and think of what it would be like to suck it, to let him fuck me. It comes to mind only because he doesn’t look at me with challenge in his eyes, because his submission is so complete. From the moment we met he has been respectful, classy, considerate, and now he is opened, vulnerable, and more beautiful than I dared to notice.

The moment passes, and again we find ourselves in gentle cameraderie, sitting on the bed together and talking. I ask him if he wants to stop here, or go on with something else; we have perhaps a half hour remaining.

He had told me that strap-on play was very important to him, and I had told him that I don’t do it, but he hired me anyway. On some strange hunch I brought my equipment along, and at the beginning I laid everything out on the bed – “just in case.”

“Please,” he asks me now, not quite back in that submissive headspace but not looking me in the eyes either, “could we play with your strap-on?”

I’m still conflicted about it, knowing the boundaries I generally set for myself and feeling them pushed, but knowing, too, that I deliberately brought it and flaunted it, perhaps in the hopes that I’d get to use it with someone I found attractive. I agree to let him suck it, but don’t make any promises about fucking him.

But having my cock sucked is my downfall.

I strap on the leather harness, with my purple cock through it, and set it in place, feeling the way it connects with my body and becomes an extension of me. At these moments I never feel dominant: I feel exposed, naked and rampant. Powerful, perhaps, but flayed: unveiled in the kind of power that terrifies. With my cock on I feel like a predator in the heat of the kill, and at the same time I fear the foolishness of it, the ridiculous spectacle of a woman wearing a rubber dick. This is another of my secrets about this act, my reluctance in sharing it with strangers: what if they see that I’m like a tiger wearing a baby bonnet – or worse, like a sheep wearing a wolf suit?

But with the object of desire in place he falls into role again as easily as breathing. I put my hand back in his curls and help/force him to his knees in front of me, and he takes the purple cock – my cock – into his mouth and sucks.

Sucking my cock is a sure way to plug it even more deeply into my body: watching someone suck it, suck it earnestly and treat it like it’s real, makes it real. Some part of me extends outward, fills the space the cock occupies, ennervates it and animates it, and all at once I’m not just shoving a silicone cock I have strapped to my body with leather down your throat. I’m fucking your mouth.

I fuck his mouth a little and watch his eyes tear as he looks up at me. I feel the abandon start to rise in me, the wetness and the growling and the fear, the fear of how I’ll let go, coming and snarling and shooting my energy into this person I don’t know, scaring him maybe, giving away my life force, and I pull him back by the hair. He looks at me with that pleading in his eyes that I can’t refuse. “Please fuck me,” he whispers, “just a little. Please.”

I pull him onto the bed and order him back onto his hands and knees. “Back up,” I say, and he backs his muscular ass toward the end of the bed so I can stand while I fuck. I grab a glove and the thick lube I’ve brought and my black-gloved finger finds his hole and pushes, swirls around the opening, finds him warm and ready and yearning.

I slide into him and he makes that sound, that sound that is only made by men who are being fucked in the ass because they want it. That half-whimper, half-moan, that fucking beautiful sound of abandon and pleasure and fear and yearning and taboos busted all over the floor.

He fucks back into me and I hold his hips with one gloved hand and one bare one, guiding him onto my curved purple cock, filling his guts. I start to feel it building in me again, the unreal reality of my cock squeezed by his tight little asshole, the fucking miracle of my cock disappearing inside him, the sounds he’s making – and then he’s asking me if he can touch himself and yes, of course, play with your cock but don’t come until I tell you, and I feel dizzy and tunnel-visioned and I don’t want to come, I can’t come, not here, not with him, and why not, but I want to, but I hold back and keep control, letting him find his abandon without taking my own.

“Please may I come?” he gasps, and what can I say but yes, fucking come for me, and he does, crying out, his sounds like someone dying of sex, and I fear the tears again but there’s nothing, only silence and softness and I pull out of him, humbled, a little embarrassed, happy that I had him that way and not face-up, where he couldn’t see my face, the struggle, the loss of composure.

Immediately I take the harness off and begin to bring the scene down; somehow I can’t cuddle him now, it’s too intimate, but I speak gently and let him recover in his own time. He thanks me and I thank him again, and we slowly recover our roles – or recover from them.

It’s awkward, saying goodbye. I’d like to see him again and I know that that can’t happen except at his instigation. Even if we do, it won’t be me he sees. Not the me who would like to fuck him again, without money exchanging hands, without the need to hold back, to wear a corset while I do it, to play, as I sometimes have to, at loving less.

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He was sitting at the chic hotel bar when I walked in: compact, muscular, with a tanned face that bespoke Greek heritage, perhaps, with bright green eyes. More attractive, needless to say, than my clients generally were. Younger, too. The problem with this is that such men tend to be obnoxious, to ask more of me than I’m willing to give, to push my boundaries. Like they’re doing me a favor.

Not this one. He’s kind, offers to buy me a drink, which I decline. He’s well-read, and a Burner. He has a low key but confident way about him that I like. I could tell this would be one of those rare instances where the client is someone I would have happily played with for free, but would never have the guts to approach at a party.

He’s booked me for three hours, and I can think of worse things to do with that time than explore the kinks of this rather yummy specimen. He tells me that he usually tops, but from time to time, he feels the need to let go, to let someone else be in control. I usually worry about this, again with the concern that he’ll be bratty or try to make me switch. But something tells me that this is a different sort of person.

The hotel is downtown, one of the swanker places in the Manhattan style – sleek black and silver, not ornate old wood. The room is spacious and inviting, and now that we’ve had our talk we start right in.

When he undresses I see that he takes care of himself, and also that he is one of those men who is never quite thin: shortish, barrel-chested, thick all over but not hairy. The hair on his head is short and curly and lovely to grab and pull.

There is something beautiful about a usually-dominant man submitting. The sincerity and thoroughness of the surrender, in this case, almost steals my breath. Many men have dropped to their knees in front of me and kissed and licked my boots. It’s all part of the script. Dig me, such subs seem to say, I know what it’s all about, how it’s done. This man knows both sides of the coin, and the way he gives over, drops his eyes, trembles in fear and anticipation, is immensely moving. When I grab his hair he actually whimpers, and is immediately in the headspace I want him in.

I love boot worship when it’s done well; when it’s not, it’s a total bore. It’s hard to say what it is that makes it well-done: I only know that when it is, it makes me wet. It’s something about the way the sub becomes absorbed in the act, doesn’t always have, literally or figuratively, one eye on me to see how I’m reacting. The boots in that moment are me, and the truly gifted bootlicker isn’t doing it only for my pleasure. His head is swimming with desire, his vision is blurred with only the blackness of leather or vinyl in its scope, his nose and tongue are full of the scent, his mouth working slowly and with focus. Most importantly, he doesn’t have that puppy-dog approval-whore thing going on: none of that aren’t I a great submissive? crap. I’m not interested in how well you play your role. I’m interested in you, and how your desires mesh with mine.

This man is with me, in the way that clients rarely are. We have seen each other, in this conversation that we shared. There is spark, here. His need for submission is great, and yet the expression of that need is specific. He is both well-trained – the way he moves is graceful yet without pretense – and totally responsive.

I’m loving this, but it’s time to move on. I’ve found a way to jury-rig dog leashes over the bathroom door and I string him up with cuffs, standing, and begin to flog his broad brown back.

I love to flog, but it’s the rare client that loves it like I do. It becomes clear, quickly, that he is one of these gems, and I go at him with a zen-like yet ever intensifying rhythm. I don’t know how long I stand there, swinging my right arm in figure-eights, harder and harder, watching his back redden and his muscles tighten and loosen, listening to him gasp and whimper and moan. Fuck. Now and then I ease off, rub his back with a cool hand, press my body into his back, my thigh against his ass, between his legs. I think, at one point, that I’ve gone too far, and I check in with him.

“Please,” he whispers as I hold my head next to his, run my nails down over his ass. “Please, more.” He doesn’t, can’t, look at me, but his body tells the whole story and it’s true. I back up and start swinging again, a few strokes to work back up to the level I’d stopped at, then harder and harder. He starts to shake, muscles spasming, hands clenching at the cuffs, and I can feel the energy flowing between us, the way his want draws the blows from me, the way I feel his need, the need I’ve so often felt myself, for just one more, one more, one more…

And then he breaks, and he’s sobbing, half-hanging from the dog-leashes and barely holding himself up. I stop swinging and move to him again, my arm wrapping up under his arm, around his chest, pressing his heart. My body against his back, feeling the waves of his tears passing through me. There is no shame here. Only release. Only love, in that strange sense that it can happen in one encounter, the true exchange between two people in a moment.

When he calms down, he tells me, “That hasn’t happened in a long time. Thank you.”

“Thank you,” I tell him, and we take a rest. But there is still so much time to go…

[Part 2.]

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So it may come as a surprise to no one that now that I’ve quit the pro-domming business, I’ve been having wicked fantasies about doing terrible, terrible things to lovely boys and men. I mean, it’s like the old joke about the gynecologist, right?

Well, sort of. See, I’ve had a thing about Not Doing Strap-On Sex At Work for the entirety of my tenure as a pro. It was just something I didn’t do. Now, part of the reason I didn’t do it was because it crosses the line into sex: in the state of Massachusetts, if you penetrate an orifice with anything, it’s defined as sex. Good law, for a lot of reasons: it was developed in order to make rape cases where some Neanderthal fucks stuck a shot glass into a woman prosecutable. But problematic law for people doing domination, where one of the most popular items on the menu is being fucked in the ass with a dildo.

For the most part, though, the legal thing was more of an excuse for me not to have to address the real issue, which was that doing strap-on sex was too intimate for me. It was one of the boundaries I set for myself early on, because I didn’t want to be having sex with my clients. I was aware that the other things I was doing were sexual, but I didn’t realize until later the subtle effects that it would have on me. I was prescient enough to know, however, that having strap-on sex with clients would be too much for me.

Why, you might ask? Well, here’s where I break from the crowd completely. I fully appreciate Bitchy’s complaint that strap-ons are not only weird because they imply that power and sexual dominance = having a cock (which I agree is a crock of shit), but that they don’t provide any pleasure to the wielder. I also am pleased with Eileen’s reply wherein she sings the praises of strap-ons as separate from gender identity and recommends them as a tool of dominance comparable to a singletail, a needle, or a fist. But nobody I’ve yet stumbled across (except for, perhaps, Sinclair, but the butch perspective there isn’t one that gets a lot of play in BDSM circles) has gone into anything resembling my own experience of the act.

That is, I fucking love it and it makes me come, in a way that nothing else can.

Because get this: I have a cock. I always have a cock, whether I’m strapping one on or not. It’s non-corporeal, of course, but it’s part of, if you will, my energetic anatomy. Without getting too deeply into spiritual experience, it is a simple fact that at times, I can feel myself penetrating another human being, even when I am not physically doing so. And yes, they feel it too – the force of my will and intention pressing into their bodies, invading them.

For me, the energetics of topping someone will sometimes bring out the hidden masculine in me. I suppose if I wanted to be all Jungian about it, I’d call it my animus. I become more aggressive, my voice deepens, and the desire to possess rips through me. When I strap on a cock, it becomes a very real extension of my body, and when I fuck with it, I don’t want a vibrator inside the harness or anything penetrating me – I just want to fuck. It’s usually not too long into the action that I start to come and come, in a way that even feels distinctly masculine: unlike the internally focused waves that thrash through me when, say, I’m being fisted, I feel energy shooting out from me, into the other person, as white lightning shoots up my spine.

Now. I’ve been reluctant to talk about this, in part because it seems a bit woo-woo, but also in part because I don’t want to give the impression that I think dominance is essentially male, or that penetration is essentially dominant, or any of those bugaboos that come up when we talk about female dominance and try to separate it from gender.

But I do want to record my experience here, because I don’t see a lot of women out there talking about how intensely pleasurable strap-on sex can be for the woman wielding. I also know that my experience is not every woman’s experience – far from it.

But I am out here, feeling this, experiencing this genuinely as part of my rather complex sexuality. For the record, I also often come sympathetically when fisting someone. But this experience is entirely different, separate. It is, at least in part, about awakening my masculine self, my butch self, which is buried deep in a seriously femme facade.

And this is why I didn’t do it at work. I couldn’t fuck men I didn’t know any more than I could let them fuck me. And there weren’t many men (not any, by my last count) that wanted me to fuck them while I wore jeans and a leather vest and boots.

But incidentally…if you are such a man, comment here. I’ve been having the most remarkable fantasies lately…

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Apologies for missing the usual Monday advice column; I hope I can make it up to you by posting it late today. Remember – send me questions at delilah@dommedelilah.com, or comment here on the blog!

I had a question long ago that went simply like this:

I would love to hear your recommendations on the best dildos to use in a harness – double-ended or one-sided, either way.

First of all, definitely see my previous advice on getting the right harness. Much of your success in using a dildo in a harness is going to be about the harness itself.

But picking out the dildoes is the fun part, right?

The thing is, though, different dildoes are going to work differently for different people, depending on what you’re trying to achieve. What size cock do you want to have? Are you identifying with that cock as your own, or are you just using it as a toy? Are you able to come or at least get a good amount of stimulation just by wielding the strap-on, or do you need the double-ended action to keep things interesting for yourself?

I happen to be one of those lucky ladies who has enough guy in her that when I strap one on, it becomes part of my body, and I have incredible, outward-reaching, masculine-feeling orgasms when I use one on someone. Much of this has to do with how I am able to use my mind and my energy bodies during sex, I think, and little to do with physiological factors. If you’re like me, though, you might find using a double-ended dildo to be too much, or even to be distracting from the sort of masculine nature of the act.

If you’re not like me, you may or may not want to use a double-ended dildo.

As I don’t use them myself, I will pass along reviews I’ve heard from others. The favorites seem to be the Feeldoe and the Share, but how well either of these is going to work for you is largely dependent on your body shape and what kind of angle you like during penetration. Some folks I know love a dildo that you can only get custom made by Whipspider Rubberworks:

This one looks great in the sense that it has a long piece that separates the penetrating end from the penetrative end, allowing for good positioning for thrusting even when the other end is inside.

Some of these say they can be used without a harness, but I can only imagine that controlling the dildo during serious fucking would be problematic without it. If you like double-ended dildos, make sure that you get a harness whose hole goes all the way through, rather than a ring attached to a closed front panel.

For myself, I love single-ended dildos. My main criterion is that it be made of silicone (which is fully sterilizable and has a good level of hardness while still being somewhat yielding), and that it look at least somewhat realistic. That is, I’m fine with a dick-shaped dildo that’s purple with sparkly swirls, but I’m not going for the dolphins and diving Virgin Marys.

My favorite go-to dildo is Vixen’s Woody, which is a goodly size without being huge, has an upward curve, and a nicely ridged head. I also own a Mistress – not for the name, of course, but because it’s a nice slender one for folks who need a little working up. Vixen’s a great company in general, and makes toys of many shapes and sizes for any taste. (They’re not paying me to say this.)

So, the short answer? Get something in silicone, that you can sterilize. Make sure the insertable end is the right size for your partner, and if you’re getting a double, make sure the end that’s inside you is a good shape and angle, and at the right distance from the thrusting end for you to be able to thrust well. Because, I mean, yikes:

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I was reading back in Bitchy Jones’ Diary last night and was again stirred and moved and amused and made curious by it. I have to be careful over there, as her blog never fails to draw me in to several hours of reading.

When I first picked up on her blog nearly a year ago, it made me start to think hard about the image I put forth as a pro domme – and, frankly, about whether I wanted to continue being a pro domme at all. So much about the culture of pro domming has always been ugly and alien to me, and I spent a lot of time trying to put my finger on why. Is it the exploitation of men? Of women? Is it the obvious fact that most of the men who see me are, in essence, cheating on their wives and partners? I spent a lot of time in my first couple of years of domming figuring out what things made me feel icky and what things don’t, and how to minimize the former and capitalize on the latter.

But Bitchy – looking from the outside of the industry as she is – was able to outline the problem for me perfectly. She writes well on many topics and at length, but her central thesis, if her blog can be said to have one, is something like this:

The image of the dominant woman and the submissive man are broken. The prevailing submissive male culture dictates that said men are worthless, less than men, unworthy to be touched by Women who are Superior, and deserve punishment, enforced chastity, and feminization at the hands of Dominas, whom they should worship as Goddesses. This image, rather than empowering women, pedestalizes them and robs them of their sexuality, locates their power in their appearances rather than in their total persons, and suggests implicitly that femininity is actually inferior, seeing as 1) “forced” feminization is reserved for submissive “sissies,” and 2) dominant women are only allowed to have sex with submissive men if they use a strap-on cock and fuck them up the ass.

Add to this the prevailing notion that certain things germane to being female (getting penetrated being the biggest example) are by their nature submissive, and you’ve got one fucked-up image system going on.

The major problem, that Bitchy goes over and over against the protests of many (especially pro dommes), is that the image of the Big Bad Dominatrix is the only mainstream image of dominant female sexuality there is. As such, it robs women like her of any recognition of their sexuality.

Essentially, the idea of dominant female sexuality – that a woman could actually be in control during fucking, or that she could come from taking a burly, masculine man and causing him pain – is so scary that it needs to be desexualized, dehumanized, the sweat and blood and come taken out of it, and turned into a high-heeled, latex-sheathed, small-penis-humiliating freakfest where a woman’s stilettos are a more powerful seat of sexuality than her cunt.

As she so trenchantly points out, Sometimes I think femdom is like a horrible warning. This is what can happen if you replace actual women being turned on with women’s whose job it is to pretend to be turned on.

Or, as an excellently smart commenter puts it,

Inside kink we have a sexist, distorting, repressive culture which tries to make people like me believe the norm of my sexuality is play for pay, tries to make men believe their submission is shameful and unattractive, tries to make dominance appear unsexy to women.

If you are working as a pro dom, how is it in your interest that this distortion gets changed? It creates a great deal of your demand.

And this:

[T]his is not about deriding sex workers for being sex workers.

Example. If a prodom said “I can’t have sex with clients because it would be illegal where I live” or just “I prefer not to have sex with clients”, this would be from a perspective of sex work. Nothing to make fun of.

But: “A female dominant can’t have sex with a male submissive, because it would upset the power dynamic / they’re unworthy of our sacred shrines / these wimps can’t satisfy a woman anyway”… Are these lies? Do they sound familiar? Are they ridiculous? Do they have harmful effects?

…This is about prodoms knowingly telling lies about sexuality with harmful consequences, and profiting from these consequences….This is about people who claim that their pompous facade, i.e. their sex worker persona, represents female dominance as a personal kinky sexuality. And that is not okay.

As should by now be obvious, all of this is making me think like crazy. I have long been repulsed by the trend in prodommery toward the apparently sexless ice princess who treats her feminized, submissive wiener-men like shit. And it’s taken me a while to figure out exactly why, but I think I know now.

I want to continue to be a pro domme in addition to continuing to live out my personal kinky sexuality. But 1. I want to be more open about who I am as a total person – partly because it makes my life better to do so, but partly to contribute to dismantling this horrid pro-domme stereotype. And 2. I want to restructure how I market myself to reflect the things I love to do in sessions, not the things I’m expected to do as part of this culture.

This is a long time in coming, and I’ve written about it elsewhere in great angsty detail. But Bitchy, as usual, you’ve caught me out. It’s time to stop perpetuating false images that define female dominance as sterile and male submission as shameful. And it’s time to start putting out there what I truly find hot.

And for the record: me? Totally a sex worker. Let me say it here and now: what I do is sex work, it is a sexual service, and I don’t have manual, oral, vaginal or anal intercourse with my clients because it’s illegal and I don’t want to. A post is brewing about strap-on sex, which Bitchy tends to write about as part of the problem, but which I count as a sex act for the reason that it totally turns my crank. One day soon I’ll write about the one time I broke my no-strap-on-sex-in-sessions rule…one of the hottest sessions I’ve ever known. But that’s for another day.

For now, picture this: a new site by me that highlights my friendliness, my viciousness as a sadist, my sensuality with touch and voice, my wrestling fetish, my work as a healer and therapist, my human connection with my clients, and yes, my sexual desire.

It’s very likely that I’ll never have the guts to do videos where I play the submissive. That part of my sexuality is too private, too precious to me to share with the world in that way. Probably this is also the result of the sickness in our sexual culture: while I experience submission as powerful, I have the fear that others won’t see it that way, and am still haunted by the notion that taking my clothes off and going into that space strips part of my power. (Is it any wonder, when most of the images we have in porn of female submission are all about humiliation and conquest? Again – another post for another day.)

But I think you can safely stay tuned for more vulnerability from me as a domme. More clear expression of my desire. More scenes with models I care about, or am at least hot for.

And more stories here about the kinds of scenes that actually make me wet.

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This past weekend’s video shoot was a smashing success, and I can’t wait to see the results. We shot with the voluptuous Madeline, who at nearly six feet tall with a stunning fall of naturally red hair is quite a match for me. (Good thing, too, since I happen to love her something terrible.) While she’s chiefly played the sub to me in the past, this time we let her flex her inner domme a bit, and she really shone.

We performed various tortures on a video slave I like.

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Be on the lookout for some harsh high-heel trampling with verbal humiliation, some shoe, boot, stocking and bare foot worship, dirty feet cleaning, panty and stocking washing (by mouth, of course), cigarette torture and glove fetish, and a good old-fashioned ass-kicking.

Torturing the slave boy was amusing; causing anguish and embarrassment to someone who loves it is entertaining and fulfilling to me, but can be somewhat tiring as well. By the end of it I generally feel drained and have sore feet, back and legs from walking around in heels all day. My creativity is tapped by improvising witty dialogue and focusing all of my energy onto the object of my torment. It’s the same reason I can only do four sessions a day, tops, without actually making myself sick: I take it seriously. I focus my energy. I pay attention, every second. And when the camera’s rolling, it’s just that many more things to pay attention to.

But for me, the coup de grace was the final scene, which Madeline and I shot together after the slave went home. I rediscovered, as I so often have the opportunity to do, what really turns my crank versus what I just find amusing.

First, I got my guy on a bit.

I got into some good old blue jeans and a Nasty Pig rubber belt. I wore a leather halter on top and some Diesel men’s briefs underneath, and I was packing with a leather harness and a nice slim cock that Vixen makes. I topped the whole thing off with a buttery leather racing jacket, and dressed my girl up in a floofy little skirt and tank top.

As soon as the camera started to roll I just did what came naturally: grabbed her by the hair, slammed her against the wall and kissed her, holding her nose shut with one hand. Pushed one thigh up between hers. Brought her to a chair and made her kneel down in front of me, told her to take my cock out and suck it, make it nice and wet and ready. She undid my belt and reached in, letting it spring free. Her beautiful mouth wrapped around that cock was heaven, and her enthusiasm plugged me right into it, made that cock mine. It wasn’t long before I was dripping underneath the base of it, all of that sexual energy running right through the silicone and into her. I grabbed her, reluctantly pulling her off of me, and made short work of her little lacy panties. Her sweet little cunt, tight and more bud-like than most, is covered with sweet red hairs, and inside it was wet and ready for me, as my black-gloved hand quickly found out.

I sat her down on top of me and let her rock.

I often lament how little really good lesbian porn there is: the mainstream stuff that’s labeled “lesbian” is all too often two pneumatic blondes with dragon-lady fingernails making me fear for each other’s shaved clits while they delicately finger each other and flick their tongues in each other’s general direction. The Crash Pad Series is so far my favorite answer to this problem, and I adore DarkPlay for lesbian BDSM. I hope that with this little video, and future clips I do with beautiful women, I can add to the collection and maybe give people more of a taste of what (some) real sex between women looks like.

I’ll let you know when it goes up.

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Well, this weekend was a blast – I’ll certainly be writing about it later, and posting links here when the videos go up. Suffice it to say for now that I worked hard and I’m still not fully recovered, but I think we got some great material.

But now, to your questions! This week, I’ll be answering only one: it’s a big question about which I could go on at novel-length, but instead I’ll try and keep it around a thousand words.

Dear Delilah,

My partner and I have recently started experimenting with some new flavors of kink. Among these, we’re playing around with me fucking him in the ass with my silicone cock. This is something we both want to do, a lot. But we have a hard time talking about it, and also a hard time doing it in a way that won’t hurt my sweetie. I’d like to get better at both breaking out the toys and segueing into this kind of scene, and at being a gentle, competent top in the scene. Any suggestions?

Yours,
Aroused, Sensitive, Sweet – Frustrated, Underprepared, Cautious, Kinkster

First of all, ASSFUCK, you win for the best acronymic nom-de-plume yet. So right there you’re ahead.

But your question, right! For those of you playing along at home, our gentle reader is referring to “pegging,” a term coined in a Dan Savage column in 2001. A pretty good wiki article about it is here. Specifically, pegging refers to the act of a woman fucking a man in the ass with a strap-on. It may be done in a sweet, loving way or in a brutal way, in a dominant/submissive context or not. And it has a lot of baggage attached to it: heterosexual men often associate being fucked in the ass with being gay. So it’s little wonder that it’s difficult to talk about. In my experience, even men who really love it either find it hard to talk about wanting it, or feel the need to couch it in a “sissifying” context, where their desire to be penetrated is a ritualized removal of their manhood.

In your case, though, it sounds like you both know that you want it, and so perhaps the more difficult project is not talking about it but getting the party started. You used the word “top” in your letter, and I’m not sure whether you mean it just as in you being the “active,” penetrative partner, or in a D/s kind of context. Either way, though, one of the difficult things for some women is that you are probably the one who needs to initiate this kind of scene – and this can be difficult, as women are not socialized to initiate sex. What with this type of act being such a delicate subject for many, it’s even more difficult. You need to accept that you might bring it up at the wrong time, when he’s not in the mood for it or ready to try it. But it’s still likely that you do have to bring it up, and you may have to do it more than once.

I do have some suggestions, and would be happy to share. First, there are the ways to work up to the actual pegging part. Then, there’s how to initiate a scene.

If you’re worried about hurting your partner – and it’s good that you are – then you should work up to the actual silicone cock part. Besides the fear and pain that can accompany anal penetration, there’s the problem that your cock is, well, synthetic, and it doesn’t have nerve endings that connect to you and help you know what’s going on with your partner. Start with fingers. Or rather, start with one finger. Slip on a latex (or polyurethane, if he or you are allergic) glove, get plenty of lube, and gently work it around just the outside of the anus to start. Little by little, you should be able to work it in, though there’s no need to rush. Words of encouragement are good here. Eye contact is great, too. I recommend starting with him lying on his back, knees up. You’ll feel when the sphincters relax and allow you to move in a little more.

When you’ve comfortably got a finger inside (which may take more than one session!), try a small toy. This could be a wearable toy, but it should be narrow, and you should start by holding it in your hand. You’re probably a lot better at using your hands to feel your way places than you are at using your pelvis. Lube the toy well, and ease it in with the same care you used with your hands. Make sure at all stages that you give him the option to make it stop or slow down.

When you’ve done this a few times with good success, and are at a stage where you can move the toy in and out and have that be a good thing, you’re ready to strap on. I’ve found that a great way to work with a strap-on cock is to have whomever I’m planning on fucking suck my cock first. The visual component of that, plus the receptive partner’s acknowledging of the cock as a cock and not an inert piece of silicone, helps me connect with the toy and feel it as more a part of me. Once you feel “plugged in” to the cock, find a comfortable position (again, I recommend having him on his back at first), and guide yourself in. Don’t move at first; just give him a chance to relax and adjust to the feeling of fullness. After enough practice, you should be able to go to town. And remember: there is no such thing as too much lube.

You might also try working with a buttplug, especially if you do want to add a D/s component. Once you’ve reached the point where you can comfortably get a finger inside him, having him wear a buttplug for a while before he comes to see you can be a great way to get him both revved up and relaxed for further action. (Incidentally, my favorite source for these types of toys is Blowfish.)

Now the second part of this is: how to initiate all of this? Well the good news is, if you start with just a finger, all it takes is grabbing a glove from the bedside table, dousing it with lube, and beginning. If the project progresses well over several dates, then eventually the rigamarole of strapping on won’t seem quite so difficult to transition into.

What I recommend is this: when you’re planning on going from fingers to toys, have the toy on the bedside table, out and ready, before you start playing around. Giving the toys that you’re going to use a presence in the room is a simple way of raising the subject.

When you get to the part where you’re going to strap on for the first time, have everything you need laid out on the bed. Lee Harrington once wrote brilliantly about strap-on sex being a very deliberate act of love, more intimate than almost any other kind of sex or play. Playing up the deliberateness, rather than trying to escape its inherent awkwardness and interruption of action, ritualizes the experience and adds to its sexiness.

There is much, much more information available about this, in books like Anal Pleasure and Health and countless other titles: if you’re a bookish sort, do your research beforehand and enjoy!

Also, I’m a horrible voyeur, so please do write back and let me know how it goes!

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