Strength, Courage, & First Impressions: An Illuminating Tarot Reading

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In mid-February, I couldn’t stop crying about boys. All in a row, I’d crossed paths with a series of people who I adored, who felt almost mystically perfect for me, who nonetheless couldn’t or wouldn’t date me for various reasons. Such is life, I suppose. And although I knew I’m worthy of desire and would find someone awesome eventually, and although I kept telling myself “This too shall pass,” tears still kept pouring down my face as I sat in bed wailing along to Missing Ember.

“It has been a year and a half since the end of my last relationship,” I wrote in my journal, “and whereas that break-up initially made me feel wonderfully free and independent, now I just feel weirdly unmoored. I miss the emotional support and consistency of having a primary partner.”

After writing some more and effectively soaking my journal with tears and snot, I fired off an email to Carly from Tiny Lantern Tarot. (Carly uses both she/her and they/them pronouns, so I’ll be alternating between those.) I had read an interview with Carly on Up, Down & Out and loved her nonjudgmental, intuitive and queer-friendly approach to tarot, and since my emotions were so tumultuous at that time, I felt I needed some direction. Some types of emotional turmoil call for a visit to a therapist, or a long phone call with a best friend, but for some reason I craved advice from someone wise and witchy. “I have some concerns around romantic and sexual relationships in my life that I would love to get some guidance on,” I wrote in my initial email to Carly.

A few more emails and a couple weeks later, I headed to Carly’s home office for my reading. They made me tea and we sat on their little couch. We talked a little bit about my concerns around romantic relationships, and then she drew some cards.

Carly uses the Collective Tarot, a deck whose illustrations are bursting with queer people, people of color, and a diverse array of bodies. This immediately felt right to me. Tarot cards are usually traditionally gendered and free of flagrant sexuality, and my life is… not those things. Carly’s calm manner, and the cards themselves, affirmed to me that this was a safe space for me to talk about my queer/sexy/kinky life, if need be – and that’s important, when you’re getting a reading about relationships!

Two of the four cards Carly drew were major arcana cards and the other two were face cards, which they told me meant the issue at hand was an important one to me. It certainly was!

The card at the center represented “the heart of the matter,” and it was the Seeker of Feathers. Carly explained that this card is about communication and assertiveness. “It’s more important that you say the thing,” she explained, “than that you say the thing nicely.” I’d gotten into a habit of downplaying my needs, of telling people I was okay with my romantic and sexual entanglements being “chill” and “casual,” when actually I wanted something more. This card told me to be more honest with potential beaux about what I want – and I interpreted that to mean honesty about not only my feelings but also my desired relationship structure (non-monogamous) and the kind of sex I want to be having. I’m not always good at communicating my needs if I think they might ruffle feathers, so this card reminded me to do so regardless.

The card on the left represented “what to do.” It was the Code, which features what appears to be a queer kinky person flagging red for fisting. (So, so, so awesome.) Carly told me that this card refers to boundaries, borders, and communities, and recommended I consider the communities I run in: in what ways do I fit into them, and in what ways do I stand out? In the places where I stand out, do I want to accept that and be proud of it, or do I want to adjust my approach so I fit in better?

This card made me think about how often I feel like a baby/newbie/impostor in the sex-positive communities I’m in. Though I’ve been running in these circles for years, it’s still hard for me to accept that I’m a valued member of the Cool Kids’ Club. I’m well-liked and respected by the members of that “club” who know me; there’s really no reason for me to feel like I don’t belong. This card reminded me that I should dive even deeper into that scene, unapologetically and enthusiastically.

Naturally, given the kinky content of the illustration, this card also refers to power dynamics. As we talked about my issues with anxiety and feeling out of place, Carly suggested that maybe I need to develop a power dynamic with myself: be my own dom, so to speak. This might involve bossing myself into doing stuff that is slightly uncomfortable for me, but will help me grow and meet potential partners – like attending social events that make me nervous, talking to new people, and entering new social scenes. I found it strangely helpful to have my anxiety re-framed in this way – as something I can challenge bravely if a cute toppy person tells me to, even if that cute toppy person is me.

The next card represented “what to think,” and it was the Apprentice of Bottles. Carly explained that this card usually evokes a person who is very charismatic, charming and shiny, but then turns out to be shallow and disappointing. They weren’t entirely sure what the card was trying to tell me, but it made a strange kind of sense to me: a lot of my emotional upheaval at that time had happened because I was idealizing people I had a crush on. Some of these people appeared to be my perfect partner, but of course, they weren’t actually perfect, and in many ways we would’ve been a bad match if we’d gotten together. I felt like this card was telling me to take people off the pedestals I’d put them on – and also to consider what qualities I actually need in a long-term partner, rather than just the dazzling qualities that capture my attention in the short-term.

Carly told me that this card can also refer to first impressions: making a big splash, and then retreating. We talked about how I often worry that the first impression I make is misleading. “I’m a sex blogger” is usually one of the first things I tell new people about myself, and I think it gives some people an incorrect impression about my personality, my priorities, and what kind of relationship(s) I might be looking for. Carly encouraged me to experiment with the way I talk about myself – which I started to do later that night, by removing the phrase “sex blogger” from my Tinder profile. I figured it’ll be easier for me and potential matches to discover each other organically if I roll out information about my sexuality more slowly. (Preliminary results: Tinder dudes have indeed been less skeezy and more curious about me since I did this. Innnteresting.)

The final card represented “what to avoid,” and it was Strength. Carly told me this card refers to strength not in the traditional/brawny sense, but in the sense of emotional bravery and vulnerability. At first, she was puzzled that this card came up in the “what to avoid” slot, since obviously, these traits are usually a virtue in relationships. “The only thing I can think,” they said, “is that maybe you have a pattern in your dating life of being too vulnerable and open, of letting too many people in too quickly.”

I almost started crying when she said this, because it was so amazingly true and there’s no way Carly could have known that. I give far too many people the keys to my emotional kingdom, and it results in me getting hurt a lot. When I choose to invest emotionally in someone I’ve just met or barely know, at first it feels like an exciting rush, but it quickly gets heavy and painful, with very few exceptions. “Vulnerability is necessary,” Carly told me, “but not everybody deserves your vulnerability.” They were so right, and I made a promise to myself to be more careful about getting invested in people who haven’t yet proved they deserve my heart.

I left Carly’s house with an immense sense of clarity and inspiration, like I’d just been given the road map to my next stop on life’s path. The despair of feeling unloveable had lifted. I was still just as single, my life just as devoid of serious romantic prospects, but that felt less important and less permanent than it had before.

Now, here’s where shit gets weird. Two days later, I met a boy on Tinder. We went out. We hit it off. We started dating. I leapt headfirst into a relationship with him, before knowing if he even ticked all the boxes that matter to me (“Is he a feminist?” and “Is his sex drive compatible with mine?” being the two key ones in this case). I was so desperate for a boyfriend that I viewed this dude idealistically, filling in the blanks and paving over problems to round him up to a person I could date.

I should have communicated my needs more clearly, more quickly. I should have held out longer before calling him my boyfriend and pinning my hopes on him. I should have remembered that first impressions aren’t everything and people change as you get to know them better.

These are all things that Carly told me in my reading with her. But it was like the universe wanted to hammer these points home. And hammer, it did.

In the end, I learned these lessons the way I learned so many math and science concepts in school. Someone smart explained the lesson to me – and then I had to put what I’d learned to use in the real world.

Well, I sure learned quick. I won’t make those mistakes again. And if I do, maybe I’ll pull a few tarot cards to learn how to fix it.

23 Things I Learned About Sex & Relationships At Age 23

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Today’s my 24th birthday! It’s a good day to reflect on the past year, because I think 23 was my most transformative and educational year yet. I banged and dated a bunch of different people, and it was essentially a crash course in emotional maturity and sexual confidence. Here are 23 of the most valuable lessons I learned about sex and relationships over the past year!

  1. I have a DD/lg kink. I first noticed these feelings back in late 2014 when a hot lawyer inspired some surprising fantasies in my bad little brain. In November I started seeing a dude who was muuuch kinkier and more kink-experienced than me, and when I disclosed to him that I had burgeoning DD/lg fantasies, he knew exactly what to do with that information. I still vividly remember the time I sassily asked him why I should follow his instruction to jerk off for him and he said, “Because you’re a good little girl.” It was the first time anyone had ever said anything like that to me before, and my vagina did cartwheels.
  2. Terrible mental health days are terrible kink days. At least, for me. If I’m already feeling extremely shaky, anxious, or depressed, kink tends to just worsen my mood. I learned my lesson from the time in January when an intense spanking on an already-anxious day made me burst into tears and sob deeply for several minutes while my confused partner tried to comfort me.
  3. but, kink can help with mental health. Paradoxical, yes – but for me, there’s a fine and important line between “too distraught to submit” and “just distraught enough that submitting will actually help.” Pain, punishment and praise can help shake me out of a poor mental health day, used judiciously with a trusted partner.
  4. I can have casual sex… with people I don’t really like. Sex tends to open up my emotional floodgates, intensifying any burgeoning crush-y feels that already exist there. I was able to have some casual, feels-free fuckbuddies this year, but only because we didn’t click romantically. This is useful info for me to know going forward, though it does mean I’m incapable of being “chill” with anyone I even remotely like.
  5. I like pain (in some places). I’ve dabbled in spanking over the years, but it wasn’t until age 23 that I really grasped how much pleasure I can get from pain. Getting my tits and/or ass slapped has become one of my favorite foreplay activities. I even like getting my hair pulled, a proclivity that used to mystify me.
  6. I love giving blowjobs. HOO BOY, this was a big theme of my year. My previous blowjob experience encompassed only one partner, and while he was lovely, his dick and my mouth just didn’t have chemistry. In broadening my BJ horizons, I’ve discovered how much I can crave having a cock in my mouth when the right one comes along. (I’ve gotten pretty damn good at it, too.)
  7. I’m more of a size queen than I thought. Remember when I first started this blog and dildos over 1.5″ in diameter were a stretch for me? That is certainly not the case anymore… Just ask my Eleven, Double Trouble, and Seaside Steamroller!
  8. I need to trust my intuition more. My anxiety is excellent at talking me out of what I know, deep down, to be true. When I let myself listen to my hunches, I can usually tell when someone is flirting with me, likes me, or wants to get in my pants – and it happens more often than my anxiety wants me to realize.
  9. Aftercare is important. Coming from a pretty vanilla history, I never thought much about the importance of aftercare until I really needed it. Fortunately, all my kinky partners this past year (and even the vanilla ones) gave me the post-sex cuddles and reassurances I needed.
  10. Most men like thigh-high socks. They just do.
  11. Sex is grown-up playtime. My favorite sex is the goofy, unstructured kind. I love trying stuff, experimenting, playing around. I’m happiest in sexual partnerships with people who are similarly fun-oriented, rather than goal-oriented.
  12. I like being pinned down. Have you ever had a moment where, suddenly and all at once, you noticed a kink of yours that you never knew you had? That was me last summer when a partner put a firm hand on my upper chest and held me down while finger-fucking me. I went from “huh, that feels pretty good” to “holy shit, I am coming right now!” in about three seconds flat. I’ve been pinned down during sex a bunch of times since then, with similar outcomes. Now that I know I like this, I want to get better at asking for it!
  13. Threesomes are fun, but not really my jam. I’ve gained a reputation among my friends for constantly having threesomes. I’ve only had two, but I guess that’s still more than the average person? In any case, while I enjoyed myself both times, I still prefer the intense, focused connection of a standard one-on-one encounter. (Talk to me in a month, though… I have a rather epic threesome coming up on my calendar that might get me more on board with group sex.)
  14. When you’re sad, sometimes you just gotta feel your feelings. A couple of painful rejections left me in emotional shambles at times this year. I spent a lot of time crying on friends’ shoulders and saying things like, “I’m just so sad! I don’t know what to do!” My friends are fantastic and a lot of the advice they gave me boiled down to this: it’s okay to be sad when sad shit happens. Don’t try to run away from those feelings or distract yourself from them; just live in them for a while. It’s so much easier to move on when you’ve processed your feelings properly.
  15. You can like someone very, very much and they can still be wrong for you. You are not obligated to try to “make things work” with someone who’s a deeply bad match for you. Even if they’re a good person. Even if you adore them in many ways. Even if they don’t understand your reasoning.
  16. Platonic kink is a thing. I learned so much about kink this year, including that it can exist independently of sex. I have friends who fuel me by calling me a “good girl” when I finish my work; I have friends who phone me and speak to me in commanding, daddy-dom tones to calm me down when I’m anxious; I have friends whose kinks I know intimately and (consensually) use to guide them into healthier and happier behaviors. Kink is more than a sexual interest; it can be a psychological tool, a powerful motivator, a framework in which to understand yourself and your place in the world.
  17. Twitter is a great place to meet sexual partners. Half of the new people I banged at age 23 are folks I met on Twitter. Obviously it’s a problematic space and women receive a lot of harassment and abuse through tweets and DMs, but I’ve also built an audience there of clever, compassionate sex nerds, some of whom are pretty great sex partners.
  18. When you like someone, it’s okay to act like you like them. My anxiety makes this tricky, because even the smallest braveries feel like ballsy overtures to me. But I’m working on it. More people should know that they’re cute, and I should tell ’em.
  19. Don’t stake your mood on other people’s behavior. Most of my miserable-est days this year were the result of me believing, “If [person] would just [action], I could be happy right now.” I learned that I need to either change my expectations, or try to make things happen myself; waiting for someone else to read your mind and do what you want them to do is a fool’s errand.
  20. Anxiety-friends are invaluable flirting sherpas. This is no joke: I owe most of my romantic and sexual success this past year to Bex. Any time I didn’t know how to interpret a romantic interest’s flirty behavior, or couldn’t parse a cryptic text, or needed a push in a flirty direction, I went to them for advice. I have other “anxiety-friends,” too, who are willing and able to answer texts like, “[Person] said [thing], are they into me?!” and “What do I wear to a date-that-might-not-be-a-date?!”
  21. I like anal sexI wasn’t sure how I’d feel about it, because my past adventures with butt plugs and anal beads had been inconsistently pleasurable. But, holy fuck, I was into it and I want to do it more.
  22. I don’t need (or want) monogamy, but I do need to feel special. I don’t mind having partners who have other partners. (Yay, #PolyLyfe and compersion!) But I do need my partners to make me feel valued, seen, and focused on when we spend time together. I received a few propositions this year from folks who date/bang a lot of people, and I learned that that only ever feels okay to me if they clearly like me for me – not because they like dating/banging whoever. I’m definitely not anti-promiscuity and there’s nothing wrong with being slutty! I just need a side order of emotional connection with my sluttiness.
  23. Life is too short for bad sex. I believe there are two main ways to be bad at sex: you can be bad at technical skills (“He kisses like a snake!” “Her fingering rhythm is inconsistent!”), and you can have a bad attitude about sex (“He refused to use toys on me!” “She got all sulky when she couldn’t get me off!”). I’d rather be with an enthusiastic newbie than a mopey pro any day. If you’re fun to bone, I’ll probably gladly teach you how I like to be fucked so you’ll know for next time – but if you’re a sad and draining lay, there probably won’t be a “next time.” I’ve raised my standards enough to say no to bad sex – because, frankly, I’d rather just masturbate.

 

Here’s to another sexy, educational year!

It’s Okay to Break Up Because of Sex

It’s funny how you can entrench yourself so firmly in positivity and still get sucked into the vortex of shame from time to time.

I’m a sex-positive person. I live and work and socialize with almost exclusively other sex-positive people. So I know that having sexual desires is normal and acceptable.

And yet it only took a few weeks of constant sexual rejection to send me back to square one: profound embarrassment about being a sexual person.

Let me explain. I dated someone recently who was way, way lower on the sexual-desire-o-meter than I am. In fact, he seemed to conceptualize sex in a totally different way than I do. He talked about it as if it were a favor he did for me, that gave him no direct pleasure except in the way that it’s satisfying to give a loved one a backrub or make them dinner.

In my lifelong path of learning about relationships, one trick I’ve picked up is that it’s usually a bad idea to use “blame language.” It would be fallacious of me to say that this man “made me feel bad about myself,” since he wasn’t actively, maliciously choosing to do that. He was just living his truth – which happened to involve a far lower libido than what exists in my truth – and that took an emotional toll on me. I certainly don’t blame people with low desire levels for being that way. I just think that folks should be paired up with partners whose frequency and content of desire is roughly equivalent to their own.

When my relationship actually started to make me feel ugly and unsexy, that’s when my friends drew the line. “You have to break up with him,” they all told me, one after the next, when I shared my story privately on coffee dates or nights out at the bar. They saw my situation with the clarity and objectivity that I could not. I kept making excuses: “I like him so much, other than this one little thing!” “I think I can get him to come around!” “We’re non-monogamous, so I can always get sex elsewhere!”

I see now that part of me believed it’s not okay to break up with someone over sex. That it’s too small a reason, too unimportant a factor. That “the actual relationship” should be weighted more heavily in your decision than the sex ever would.

That is such bullshit, though. Sex is part of “the actual relationship.” Because it’s a fucking huge factor – for some people. And if sex is important to even just one person in a relationship, it matters in the grand scheme of things. Don’t let anyone tell you sex “isn’t a big deal” or “shouldn’t be that important” if it is to you. Only you get to decide the role and significance of sex in your life, and in your relationships.

The language my boyfriend used about sex started to creep into the way I thought about it, too. His go-to initiation (the rare times he did initiate) was, “I think we should get you off tonight.” The way he phrased it, it was like he didn’t view sex as a shared experience, a mutual delight, a bonding tool; it was merely a means to an end, and the end was my orgasm. Basically so that I would be satisfied, shut up about sex and quit bugging him for it. Or at least, that’s the feeling I got from him.

There’s nothing wrong with giving orgasms, or with wanting them. But this paradigm started to make me feel like it was selfish for me to want sex, because the only end result of our sex together was my pleasure. Viewed in that light, it seemed ridiculous for me to end the relationship in search of greater sexual compatibility. Did I just want to get my rocks off wherever I could? Was my nymphomaniacal hunger so great that I would throw away an otherwise good relationship to get that need met?

The more I thought about it, though, the more I realized how wrong this view is. For me, sex with a partner isn’t just about getting off – if it were, I’d simply masturbate instead, since that’s a more reliable way to make that happen. No, sex is one of the main ways I connect with partners, express my affection, and feel that affection mirrored back at me. It is absolutely crucial to my experience of romantic intimacy. Without it, I just don’t feel that I’m truly giving love, or receiving it. You can flood me with attention in all four of the other love languages, but without sex, it feels to me like a portrait that’s missing its subject. All of the pleasant peripheral details, with no central focus to hold the image together.

Viewed this way, it seems obvious that my relationship needed to end. Our problem was more than a fixable breakdown in communication; it was a full-on, hard-wired mismatch in the way we communicate. If we stayed together, “giving me” sex would continue to make him feel resentful and awkward, and being chronically denied sex would continue to make me feel rejected and unattractive. A pairing like that is destined to shatter. No one can or should suppress the ways they express and experience love; they should just seek out other people who express and experience it in similar ways.

Through this whole process, no one ever actually said to me, “Sex isn’t a good enough reason to break up with him.” In fact, my friends continually pointed out that sex is a good enough reason, even if there were no other reasons (and there were). It was just the slut-shamey voice inside my own head that parroted this sentiment at me – and, to a lesser extent, the words of my boyfriend, when he said judgmental things like “It seems like sex is the most important thing in a relationship for you” and “I wish you wouldn’t make everything about sex all the time.”

Since I’m conventionally unattractive (i.e. chubby and kinda weird-looking), there is a part of me that believes I should “take what I can get.” That a good-enough relationship is good enough. That I shouldn’t push for all the things I want in a partner, because there’s no way I’ll get them. That I should feel blessed when any man is attracted to me, even if our relationship is a daily trainwreck.

It was only once I surfaced from this shitty relationship, and looked at my life with fresh eyes again, that I remembered: Oh yeah. Lots of people are attracted to me. Many of whom are pretty damn compatible with me, including in the way we think about sex. And I do deserve good sex. And it is okay to make that a priority. And that doesn’t mean I’m a pathological perv – it just means I’m a human with a sex drive.

If you’re thinking about breaking up with a partner because the sex is bad, infrequent, or otherwise unsatisfying, I hereby give you permission to do so. Consider it carefully – because, as my slightly shamey ex-boyfriend told me repeatedly, there are other factors to consider besides sex – but also consider that a bad sexual connection can be the bad apple that spoils the barrel. If sex is a baseline need for you, you’re not going to be truly, fully happy in a relationship where the sex doesn’t work. That doesn’t mean you’re selfish or fucked-up or have a one-track mind, so don’t let anyone tell you it does.

You are allowed to want sex. You are allowed to want a partner who wants the same kinds of sex that you do. You are allowed to pursue that kind of partner, even if it means making a radical shift in your life. Like Oprah says: live your best life now.

How to Have Anal Sex For the First Time (If You Are Me)

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Begin innocuously enough. Go out for dinner with the crush/bang-buddy/friend to whom you’ve just given a blowjob. Get a little drunk with him, on big pints of locally-brewed beer, and laugh at all the jokes he’s making because weed and BJs make him cheerful.

While talking about your sexual goals for the year, suddenly have a brilliant idea – but the kind of idea that maybe only seems brilliant because you’re drunk. Start to tell him, but think better of it. Cover your mouth with your hand. Blush a lot. Shake your head. Let him pry it out of you, because the more that you keep it inside, the better an idea it seems. Finally: ask him if he wants to be the first person to fuck you in the ass. Because you want it. Because you trust him. Because he’s been on both sides of butt stuff plenty of times before and knows what he’s doing.

Be pleasantly surprised when he immediately agrees, and yet also not surprised at all, because he’s sweet and chill and adventurous and seems to genuinely like you. Concoct a plan with him, involving a hotel room and hours of slow, luxurious warm-up. Nod sagely when he tells you, “Let’s sleep on it and decide tomorrow,” while knowing in your heart of hearts and butt of butts that you’ve already decided and the answer is yes. Pay the cheque and tipsily stumble back to his place together. Give him one more BJ for good measure before saying goodnight.

The day before, text all your friends and tweet to all your followers about your sodomous plans and get their advice. Put your favorite butt plug in and leave it in for hours on end, to re-acclimatize your ass to penetration after a long stretch of none whatsoever. Masturbate idly while the plug is inside you, savoring that weird mix of pleasure and unfamiliarity. Wonder idly if you should’ve invested in an anal thruster for a more realistic warm-up.

Send dude a link to a cheap hotel listing, which is your indirect-and-yet-very-direct way of saying, “Yes, I still want you to fuck my ass.”

Pack a bag full – and I do mean full – of toys and other sexual accoutrements. Two Pure Plugs, the Ryder, and the large Ripple. Two bottles of lube. Black latex gloves. A zillion condoms. A tightly-folded Throe. The Pelt, incase of spanking. Salsa, Tango, and Hitachi. Put the Uncut #1 in there because you’ll want something roughly the same size as the dick that’ll be going in your ass, and when you put the Uncut in your mouth to test its size, you think, “Yeah, that feels about right.” Start getting real fucking excited.

While tipsy at a Valentine’s Day party, hide in the bathroom and sext the dude: “Very much looking forward to doing things to you with my mouth tomorrow.” Because you’re slightly obsessed with blowing him. Squeal when he texts back, “Bring toys.” Later, actually scream, at a totally inappropriate moment during the Valentine’s party, when he sends you a picture of a woman getting DP‘ed with toys. Because, holy shit, he’s going to DP you. Go home and add the Eleven and Double Trouble to your already-bulging toy bag because you suddenly want him to ram you with something big and heavy.

The morning of, do what you usually do when you’re anxious: journal a lot, listen to soothing music, and worry disproportionately about how to do your makeup. Have a breakfast of 3 Oreos and a cup of coffee, because you’re too nervous to eat real food and also because coffee will help clear out your system. Go about your day, running errands and writing and doing chores, while inevitably unable to focus on any of it.

As the sun starts to set, glaze your body in coconut oil so you’ll be nice and soft for him. Get in the shower and shave your legs, your armpits, your vulva, your butt. Like most lengthy femme rituals, this is more about the way it makes you feel than the way it makes you look: eliminate some of your anxiety by eliminating all of your body hair. Wash your body with Lush’s “The Comforter” shower cream, because smelling like berry candy makes you feel like the hottest, beautifulest babe. Fill a bulb syringe with lukewarm water, squirt it into your ass, jump up and down a bit, then let the water flow out of you. Do this a few times, until you feel confident and clean.

Put on some cute underwear, a comfortable outfit that’s easy to remove, and minimal makeup that won’t flake off if you end up face-down on a bed. Take deep, calming breaths and then dance your ass off (no pun intended) to energizing songs for a last-minute burst of confidence.

Walk to the streetcar stop, carrying your heavy-as-fuck toy bag. Ride the streetcar and wonder what the other patrons would think if the bag accidentally spilled open and they saw all your butt plugs and fancy dildos. Get off where Google Maps tells you to, and walk toward the hotel. Start feeling intensely dizzy, partly from anxiety and partly from the exertion of toting sixteen pounds of sex toys through snowy city streets.

Arrive at the hotel, which is small and strange and reminds you of The Shining if it was shot on no budget. Schlep your stuff up to the second floor and find the room number that the dude texted you. Smile when he opens the door for you, because he’s cute and you like him and you’re happy you’re gonna do this with him of all people.

Tell him you’re anxious. He is too. Assuage your nervous hearts with weed for him, gin and chocolate for you, and giggly makeouts for both of you. This is a never-fail prescription.

Give him a beej. For two reasons. One: his dick is excellent, and having it in your mouth turns you on faster than just about anything else. And two: if you get nervous and back out of your buttsex plans, you won’t feel as bad about it if he’s already come. This move is strategic. Or… strabeejic, if you will.

Lube up a Pure Plug and slide it into your ass, while he gives you sage advice on technique and angle, like some kind of butt sherpa. Laugh a lot, because he’s doing silly impressions and voices for your amusement, and think: yeah, I definitely chose the right person to do this with.

Let him do stuff to your nipples and clit and G-spot, because holy fuck, he has talented hands. Do your best to give directions, because sometimes you get too shy to boss people around but you know you’ll need to be a top-notch communicator tonight if he’s gonna fuck your ass. Don’t come yet – you wanna save that for later.

Bend over and let him take out your Pure Plug and switch it for the Ryder. Recall when you first bought your Ryder, years ago, and tried to put it in with no warm-up and not enough lube, and how goddamn awful and stupid that was. Enjoy the contrast between that moment and this one: the slick way he slathers lube on the plug and lines it up just right. The utter ease of taking a big toy when you’re really ready for it. The encouraging words in your ear as you back up onto it and it slides in, pop, no pain, no problem.

Make out some more. Touch each other. Giggle. Play. This isn’t a race. There’s no schedule. No marks to hit. No obligation to follow through. Just do what you feel like. Teach him how to spank you. Show him how you like your clit touched. Tug on his chest hair. Kiss his cute face.

Recognize your readiness by how relaxed you feel. Anxiety dissolved and apprehension bested, grab a condom and some lube and get him hard in your mouth. Pull the plug out, slowly. Bend over the edge of the bed with a Hitachi pinned between your clit and the mattress. Smile against the sheets, because this feels like a game.

As he slides into you, breathe deep, cleansing breaths of calm focus, and then fast, heavy breaths of unexpected pleasure. Moan, writhe, bite your lip, grind against the Hitachi. Think about how easy it was for him to push into you. How hot, hard and slippery he feels inside you. How good this is, how much better it is than you even expected. Feel completely safe, and taken care of, and respected, and filled, and fucked.

Stop him after a couple minutes, because the sensation is… a lot. Curl up beside him and high-five him when he announces, “So, you’ve officially had anal sex now!”

When he asks how he can get you off, let him choose between the Eleven and the Double Trouble. Smile as he weighs each in his hands, taking the decision as seriously as you knew he would. And then lay back and let him fuck you so perfectly with the DT while the Hitachi’s mashed against your clit, until you come in the long and loud and wild way that you only ever come with partners who make you feel unashamed. Kiss his big lubey hands when he wraps his arms around you afterward and says, “That was hot.”

Once you’ve come back to earth, put your clothes on and go out for celebratory dinner and drinks at a nearby pub. Because, hell yeah, good sex is worth celebrating.

 

This post contains a sponsored link. As always, all writing and opinions are my own.

Bigger, Braver, Younger, Older: My Sexual Goals for 2016

The new year is upon us, my loves! Mmm, dat sweet-ass blank-slate feeling. I love it!

This is the time of year when I start new notebooks and calendars, make new income spreadsheets and checklists in Evernote and Google Drive, and deep-clean my desk. #dork

Along with all that, of course, comes one of my favorite activities: GOAL-SETTING! This year is gonna be a big one in lots of areas, including sex. Here are some of my big, delicious, exciting sexual goals for 2016…

 

1. Get fucked in the ass.

You know, I was gonna write “Have anal sex,” but somehow that phrasing didn’t feel jazzy enough. Plus I would never lean in close to a partner mid-bang and whisper, “Would you have anal sex with me, please?” Nah. It’s much more likely I’d brush my lips against their ear and softly coo, “Would you fuck me in the ass?”

I just got tingles up and down my arms while writing that, which is how I know this is a goal I should pursue.

I’ve done plenty of Butt Stuff over the years. Plugs, dildos, fingers and tongues have all broached my ass, often with ecstatic results. But I have yet to be fucked in the ass, with either a flesh-and-blood cock or a strap-on. And that seems increasingly like something I should do.

For a long time, I had a partner who got squicked out by “gross” sex things like butts and blood, so while I felt comfortable with him, I didn’t feel comfortable asking him to fuck my ass. After that, I had a series of short-term or one-off partners, and didn’t have enough time with any of them to build the trust I’d need for anal stuff to feel okay. But now I have a stable fuckbuddy who I trust enough to let him spank me and restrain me on a regular basis, so this seems like a good time to start planning anal adventures.

 

2. Get fisted.

Ambitious? Yes. Intimidating? Certainly. Attainable? You bet.

I have had an interest in fisting ever since I first heard what it was. Hell, I’m wearing my Fisting Day shirt right now, as I write this. But despite the erotic intrigue it held for me, I always thought my vag was too small to manage it. It seemed like something I could’ve attempted in another life, under different circumstances, like winning the World Series or performing on Broadway.

While I’m still tight as hell down there (as my bang-buddy seems to remind me every time he fucks me – hnnng, yes, this is a nice thing to hear), I’ve also gained some mastery over my vaginal muscles. They’ve grown more flexible and resilient. Just as you get more range of motion in your hamstrings with every downward-facing dog you do in yoga class, your vagina also gets more versatile the more that you cram giant-ass toys into it. I can take the large end of the Eleven with no lube or warm-up (?!?) so I’m probably ready to work toward being fisted.

The aforementioned fuckbuddy has relatively small hands for a dude. There are ways in which this is less than ideal (my A-spot is pretty deep in there), but it might make him my perfect first fister. We shall seeeee!

 

3. Bang someone 20 or younger, and 35 or older.

Relative to my own age, the oldest person I’ve boned was 8 years older than me, and the youngest was (wait for it) 4 days younger. My sexual partners have been, on average, a few years older than me – somewhere around 28 to my 23.

That’s fine and good. I like sleeping with people who have more experience than me; I think it appeals to my submissive streak, since they’re generally more confident in asking for what they want and having their way with me (consensually, of course). I’ve also always been mature for my age, so I tend to click with older partners emotionally and mentally as well. That’s why I want to push the envelope a bit and try sleeping with someone who is 12+ years older than me, to observe the differences and broaden my sexual palate.

But… I have a bit of a kink for teaching people how to get me off. Plus there’s something so viscerally hot about those early sexual experiences when everything feels new and fresh. So I want to sleep with someone a few years younger than me, too. I don’t necessarily want to be someone’s first – that seems like a lot of pressure – but maybe their second or third. Hmm…!

Of course, both of these goals require the caveat that I’m looking for compatibility and not just a particular age bracket. I won’t sleep with some random 18-year-old douchebro who I loathe, or some skeezy 40-year-old creep, just to put a checkmark on my to-do list. I want to connect with people who are at different life stages than me but who are nonetheless in sync with me in the ways that count: we should make each other laugh, enjoy each other’s company, and have plenty to talk about.

And if the sex isn’t good, well, at least it’ll be educational.

 

What are your sexual goals for 2016?