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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?
From the Ask Me Anything questions from Sugarbutch’s 4th anniversary:
When you were a teenager, how did you feel about your body? Can you tell a story about coming out as gay to friends or family members when you were younger? Did you ever go to summer camp?—Dora
1.
As a teen, I think I was mostly just confused about my body. I developed breasts early and was curvy, though a bit heavy-set, as I still am. When I hit middle school, suddenly my friend circle shifted away from the ones I’d grown up with, as our different class backgrounds became a problem. They could suddenly afford things I couldn’t, and somehow understood this world of being a girl that I didn’t. I was a reader, on my own, a little bit of a loner, and started hanging out with more and more marginalized crowds, like the girls who also developed early and then, later, the drama kids and the smokers.
It was around then I started getting made fun of for my clothes and lack of “style,” I started getting bullied a little, I started getting made fun of extensively for my breast size. So I got a little obsessed with girl culture, whatever there was of it in the early 1990s, which certainly looked different than it does today. I subscribed to YM and Sassy and then Seventeen, obsessing over makeup and style and shoes, always completely unsure of what I was doing.
It’s only recently I’ve been revisioning this part in my own history a bit, seeing it anew. I kind of figured that was a typical process, this obsession with femininity, these attempts to fit in, the obsession with shoes, the way I hoarded makeup so I could claim to have an extensive collection and know all about it but never used it, my extensive dangling earring collection. Recently, a friend said to me something like, “That makes sense: you’ve always been dapper, even if it wasn’t as masculine.” And I think there might be some truth to that.
I think, too, there is truth to the outsider complex I felt around femininity, especially as a teen. I was terrified of what my life would be as a grown “woman.” I remember having panic attacks when I considered what my life after high school would be like. Not that I loved high school—I just couldn’t understand what was next. That was why I ended up in a very stereotypical hetero relationship, one where we both reproduced everything on TV we thought we were supposed to, which was very comforting: at least I knew what was expected of me.
But that’s a different story.
After a certain about of obsession over clothes and hair and makeup and femininity, and after the teasing and bullying just kept getting worse, I kind of just gave up. I cut my wardrobe down to black, and that was basically it. Black turtlenecks, black jeans. Which I wore year-round. Which I could do, in Southeast Alaska, where it’s mid-60s and 70s in the summer.
The new solid black wardrobe was a bit of a hit, and I fell in with the drama crowd, with more nerdy outsiders like myself, with the folks who were interested in sex and psychology.
I started feeling better about my body. Perhaps because I was covering it up, perhaps because I was getting a bit older (fourteen! fifteen! so different than twelve) and things were evening out, I didn’t feel quite so awkward in my own skin. But I did, of course, and continued to, for years really, until finally arriving at this gender identity, and getting rid of my dresses, moving on from undies that never quite fit my ass, non-apologetically donating my (few) pairs of heels.
I think most teens have awkward relationships to their bodies. Most of us don’t know what to do with ourselves for a while, and need time to grow into the changes. I certainly was no exception. I wonder if I’d stumbled on butch earlier, if I would have been happier.
2.
It’s strange, I don’t really have any specific coming out stories. I definitely told my crew as early as middle school that I was pretty sure I was bisexual, and I don’t remember it being a big deal. We didn’t talk about it, but they knew, and sometimes I would talk about kissing a girl or other classmates who were known to be bisexual. Some of my teachers were gay, a few different women I can think of, though no men that I know of. My band teacher for three years had a flat-top haircut and never wore skirts. (I wonder if she was out, happy, partnered. I don’t know anything about her personal life.) There was a lesbian couple who lived across the street from me, and another down the street. There was quite a bit of gayness around, I guess.
I came home one winter holiday and wore a rainbow necklace with two intertwined woman symbols—you know the kind. I remember my mom asking, “Are you trying to tell us something?” I laughed and said no. It was just what I wore, every day, constantly, at that time. But I guess I was telling them something … perhaps I thought it wouldn’t really matter to my parents, so I didn’t need to make a big deal out of telling them. So I didn’t. I probably should have. It was probably a way to avoid confrontation, even if I didn’t expect it to be negative.
Not as though it was a secret—I told them as soon as I was dating someone new, my mom and I especially remained quite close and knew a lot about my life and what I was doing. We started having elaborate, extensive conversations about feminism and women’s history as I worked on my Women Studies degree.
I feel like I should have some better coming out stories than that! I’ll keep thinking. But I think that was the extent of it: I never made a big deal out of it, and nobody else did, either.
Well, somebody did: my ex-boyfriend, Mike. Late in our six-year relationship he became a bit obsessed that I was going to leave him so I could come out, and, well, I did. I don’t recall any specific conversations about my sexuality, but once I did leave him, he and I both knew I was coming out.
3.
Yes, I attended fine arts camp for a few different summers, maybe three, which isn’t quite what most folks think of as “summer camp” but is the closest I’ve got. It wasn’t residential, and was at the high school, so it isn’t quite what most people’s sense of summer camp is. I studied writing, art music, singing, drama, and dance, and attended a couple different summers. In other summers I took a theater intensive only, then later started working at my dad’s store during the summers.
I don’t remember a lot of kids going to summer camp—perhaps it was the isolated nature of my hometown, which is land-locked and only accessible by boat or plane, or perhaps my friends, especially later in high school, were from families who weren’t particularly well off financially—but I (and other kids) did attend the Methodist Camp that was out the road. I never attended it through religious organizations, it was rentable by others and the only time I was there was through school.
Camping is just The Thing people do in the summers in Alaska, especially in my hometown, so I spent a lot of time hiking with friends, camping out, renting cabins for the weekends, building fires on the beach, and much of those other campfire summer camp activities that it seems are common for you lower-48-ers.
And what about you all? Did you go to summer camp? How did you feel about your body as a teen? What was it like to come out to friends or family or both?