Posts Tagged ‘coming while strapped on’

Ask Me Anything: Strapping On For the First Time

June 1, 2011  |  advice  |  5 Comments

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?

Her dirty talk got me off. Twice.

March 31, 2009  |  dirty stories  |  8 Comments

“So,” Kristen said, arms around my neck, looking up from under me, my legs between hers but bent and wrapped around each other, both of us naked, skin to skin, sheened with sweat and still a little bit out of breath. “I guess we figured out what gets you off.”

Not that I – and she – and, let’s be honest, the entire fucking internet – didn’t already know what I like: blow jobs, strapping on, fingering a girl until I make her squirt. But this was different: I came twice in the few recent hours we’d been fucking. Probably mostly thanks to what Kristen was saying.

We’d talked about it the day before. “I want to be used,” she’d said. “Just … fucked with no regard for my pleasure.”

And so I did. And we liked it, a lot, both of us.

“Fuck my hole,” she whispered, “take me, fuck me hard, pound your big cock in me deep. I’m your slutty little girl.”

Just typing that makes my knees go a little weak. Why does that turn me on so goddamn much? Makes my head spin. I feel guilty for it, really, somewhere, just a little, a small piece of me that fears that treating a beautiful, smart, strong woman like that – objectifying, humiliating – is bad and wrong. I know fantasies and role play are so much more complicated than that, that the problematic power play and gender play that we oversexualize for pleasure is just that – oversexualized – in a very specific context, and it doesn’t mean I would ever do those things outside of that context. In fact, the context is what makes them hot at all – the consent – the way she asked for it, explicitly and specifically.

I’ve known this is what deeply gets me off. This isn’t new. I discovered that I could come while strapped on and fucking with Callie, and this is precisely what we used to play with, precisely the language we used, precisely the kind of thing she wanted. I had trouble with it, sometimes, partially because I wasn’t sure I could trust her (go figure) and because of how she demanded it, and that if I didn’t deliver correctly there were consequences.

So this kind of play does open me up in sensitive places, triggers me a little bit, pulls on old wounds of trauma.

I’ve known how much these concepts, this play, turns me on, but I haven’t really brought it up with Kristen before. Well – no, that’s not entirely true. We’ve been building to this, been learning each other and building trust and playing with consent and dirty talk and power play. We’ve been building to this, and it’s of course I wouldn’t have come to her on the first date – or in the first month! The first three months! – and say, I want to take you down like this. I want to fuck you until I get off and disregard what you feel, whether you like it or not. I wouldn’t say that! Even now, I have trouble writing it out – it’s more complicated than that being what I want, what I crave, because while it is, I just can’t get there to do that until I know for certain that my respect and honor for her are in place – and that I know she knows that, too. That I know some of her history and why she craves to be degraded in these ways. I need the trust to be there, and a deeply feminist understanding of sex and power play such that the issues of consent and degradation are clear, understood between us, and ultimately irrelevant to the way we play.

So I didn’t say it first. Honestly, it never occurred to me to this extent – if it had, I might’ve brought it up. We have played with elements of this, but nothing quite so specific or elaborate as we did yesterday. But I so needed that extra little piece of consent, that explicit permission which came from her – so I know I didn’t coerce her into it – that says take me. Overpower me. Use me.

We talked about this a bit recently – I wrote about it – about how hard it was for me to get off and how much she wants – we both want – me to get off more, and one of my major conclusions in exploring that has been that I pay so much attention to her, how she feels, what I can read from her tones and moans and body language, that I forget to pay attention to myself. It’s a strength of mine, to be observant, thoughtful, to pay attention to the person I’m with, I think it makes me a good lover and friend, but it doesn’t always serve me well: I loose myself sometimes, in ways even that I don’t always recognize at the time.

(I wonder how this relates to my history with Callie too, the ways I lost myself so totally and terribly with her. Maybe my getting off (easily) with her wasn’t actually deep connection with myself – or perhaps that’s unfair, since honestly that’s precisely the benefit that I took from that relationship: knowing that I needed to learn to deeply trust myself. But maybe the ways I came with her were about something else. Regardless, whatever connection to myself I began culminating with her was so challenging to keep while dealing with her neuroses and insecurities.)

And that’s precisely what Kristen brought up when we talked about it later: it makes sense that it is a big relief, and release, for me, when I stop doing that. When I no longer put someone else’s needs above my own, and in fact allow myself to override theirs with mine. I never do that, sometimes to my own determent. So being able – and being asked explicitly – to do that sexually is a huge, huge turn-on.

What I’m trying to say is, Kristen & I opened up something deep and wounded and complicated and beautiful and fucking powerful yesterday evening. It brings up guilt, it triggers some old wounds, brings some of my issues of overattentiveness to the surface, and makes me feel so strong and powerful, like the king of the world.

I know you want to know more about what it was we actually were saying, those dirty, filthy things that got me to come inside her twice while strapped on, during a blow job, during a punishment spanking for her being such a dirty girl, during some intense fucking with her ass in my hands and her legs in the air. It’s taken me all day to get through this, unfortunately, so I’ll have to write up the dialogue tonight and get it to you tomorrow.

Did I mention how much I am just totally loving my life? I can’t believe what an amazingly dirty filthy sexy hot freak I’ve found. And? She likes me as much as I like her. Grateful, grateful, grateful.