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.
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.