Fail Seven Times

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by Kris Ripper


  I couldn’t have the things I wanted. The things I wanted were too revealing to ask for, and would have taken qualities like courage and daring to request.

  So instead I took off my shirt and said to her, “You think your boy would like fucking me? I could use a good plowing.”

  It was passably something I might have said to people I barely knew.

  “Oh, are we roleplaying that you just picked us up in a bar?”

  And busted. I held my ground. “Do you want us to do this or not?”

  “What’s our goal?”

  “Alex is naked, what do you mean, what’s our goal?”

  Alex made a buzzer noise. “Repetition, no points, Justin loses Questions. Can we please have sex now? I just want both of you in bed with me. And naked. Please.”

  I sighed. “Cork, come on. Our goal is orgasms. Okay?”

  She reached out and I went very still, not quite sure what to expect. But all she did was run a finger along the necklace she’d made for me. “I think we can do that. Take off the rest of your clothes and get in bed.”

  I followed orders, as I probably would have if I’d brought home someone as effortlessly dominant as Jamie. This was where I’d be able to suspend my disbelief (or maybe where I’d suspend my belief—in them, in myself, in some stupid notion of us).

  This is where everything should have gotten good. Because it was sex, and we were good at sex. And people good at sex, and good at sex with each other, shouldn’t have had any problems having good sex with each other.

  Except we didn’t.

  Later—hours later, after they’d gone home—I decided maybe there hadn’t been enough wine. Or maybe Thai had been the wrong choice. Sex would have been better if I’d gone with Indian, or crisp vegan salads, or falafel. If I’d cooked at home instead of getting takeout. If I’d gone with a white instead of a red.

  I hadn’t worn my tight black jockeys for them, and they’d dressed up their underthings for me. (Alex had worn his butterfly boxers, which I hadn’t seen until he put them back on before they left, and by then it had all been far too awkward and terrible to risk telling him how much I liked them, how his eyelashes felt like butterflies alighting on my skin.)

  If only I’d worn my tight black jockeys, which made my ass look incredible.

  If only my bed was bigger. Queen size wasn’t big enough to fit three comfortably, though it had felt palatial after the dorm twin beds.

  They’d gone with me to the store, had tested out all the mattresses with me. I had accidentally caught Cork’s eye over the top of Alex’s reclined body and flushed with shame and exposure, long before he would know my secret.

  She’d known. Claimed to have always known.

  I buried my head under my pillow, deep in the night, and tried to stop replaying the same moments over and over again.

  Jamie’s hand on Alex’s neck, directing him again, this time to my nipples, then lower.

  Alex gripping my side with one hand, my shoulder with the other. He’d been inside me at the time, but what I remembered was his grip, and thinking, How many other men has he fucked like this?

  Fragmented impressions of coming in his hand after he’d come in my ass, broken shards of an orgasm that didn’t quite feel complete, as if we’d shattered on our way there and what was left still made up an orgasm, but it wasn’t enough to see pleasure in, a mirror with jagged missing pieces.

  Jamie hadn’t come at all. She hadn’t touched me. Hadn’t kissed him. Had touched him, yes, and even talked, sounding mostly like herself. It was only hours later, cowering under my pillow, that I remembered her offering to “facilitate” because she’d done that before, she’d taken Alex and random people, and “facilitated” them fucking.

  God. She’d turned me into a random. Which, yes, was my goal, but it was supposed to protect us, not make everything awful. It was supposed to keep us safe from trying to take things too far, where we couldn’t get them back again.

  What it had done instead was make me feel more estranged, as if what I felt for them was a cyclone in my chest, swirling and sucking me in, pulling me even farther away from them.

  Chapter Seventeen

  BY THE END of the week I was stir crazy as hell, so I went to a bar and picked up a beefy dudebro.

  Like y’do. As Eddie Izzard says. Though he wouldn’t, of course, be picking up a beefy dudebro. I didn’t actually know what Eddie Izzard’s type was. Some kind of down to earth British woman of an appropriate age, maybe? Couldn’t really see him skewing posh.

  When you’re following a beefy dudebro back to his place and you’re trying to imagine who Eddie Izzard takes to bed, you know you’re in trouble.

  I was only in a little bit of trouble, and I didn’t let it bother me. BDB let me into his apartment and barely got the door closed before he was pulling off my clothes.

  I endured this with as much enthusiasm as I could muster, reminding myself that it had been just short of fucking forever since I’d gotten appropriately laid by a beefy dudebro, and that this experience was going to be the answer to all my prayers, because I didn’t know him, and I didn’t have to like him. I just had to fuck him.

  Not like had to. But that was the big plan. Start fucking randoms again in order to cleanse myself of the never ending ache of desiring non-randoms. Seemed like it should work. It’d be like a restart. Yeah. Like a forced shut-down and subsequent reboot that would, you know, reset me.

  Oh, right. I was supposed to be making out. Or blowing this guy. Or something.

  “You got a condom?” he breathed in my ear.

  Uh, we’re in your apartment. You have a BYOC policy? “Sure.”

  “Good. Put it on me.”

  Oh, sigh. I fished a condom out of my wallet while he shoved his jeans just over his ass—because that’s the kind of classy encounter this was going to be—but when I went to rip it open, I kind of…stopped.

  “You forget how to use that?” BDB said, tone caught clumsily between teasing and mocking. He probably wasn’t a bad guy. He was youngish. And he carried his body in a way that made me think Beefy Dudebro was a relatively new persona for him. I could be compassionate.

  But I really wasn’t about to fuck him.

  “Look, you seem really—uh—hot and everything, but I just realized I ate something bad back at the bar, so unless you want things to get unduly messy, I’m gonna take off.” I pressed the condom into his hand. “But here, have one on me.”

  I was out the door before he’d even closed his mouth.

  Down the hall, down the stairs, on the street. I wondered if he was staring out his window. Or if he knew that was a lie. Probably most people have too much self respect than to lie about having the runs to get out of an undesirable sexual encounter.

  Not me. Justin Simos: will lie about anything.

  But I still wanted to have sex. Just not with Beefy Dudebro. I’d wanted random, but as it turned out, he was a bit too random.

  I ran down my very short list of friends. Paul and Ally were exclusively committed to one another. Avery was a bottom. Madison was a woman. And Miguel…

  I lingered over Miguel. Queer. A switch. A guy. Except he’d once hit on me in a somewhat non-casual sense. And I knew he was looking for a relationship. Not a hook-up with a guy who’d turned him down.

  No. I was low, but I wasn’t that low.

  Of course, I could always—

  But no. Not them, either. For obvious reasons. Been there, tried that, still felt nauseous thinking about it.

  I looped back to Madison. Sure, she was a woman. But she was dominant as hell. And I wanted more than my ass fucked. I wanted a spark of something that at least lived in the same universe as submission. Not Put it on me. Not eye-rolling porn lines delivered by a dudebro who wasn’t sure how to acquire a condom in his own apartment.

  Fuck it. I dialed her number as I walked back to my car, without any idea what I’d say if she answered.

  “Hey, Justin. What’s up?”

&n
bsp; “I, um.” Yeah. Good start. “I was wondering if.”

  “You okay?”

  “I’m fine. Are you busy?”

  “I’m finishing a beer and cleaning my apartment. Sorry, I meant yeah, I’m in the middle of a sex party.”

  Christ, she wasn’t even interested in men. I’d called like I could ask her to…to just…

  “Come over. I’ll text you the address. Cool?”

  I sighed. “Yeah. Okay. Thanks.”

  “See you in a few.”

  Click.

  At least she wasn’t an awkward conversation-ender. My phone buzzed and I plugged her address into the map, then set it to tell me how to get there.

  * * *

  “Do you think Beefy Dudebro went back out?” Madison asked at the end of my story.

  “I probably dented his ego a little. I didn’t mean to. I just wasn’t feeling it.”

  “That’s the worst. But sometimes that’s why I stay in the club. If I go back to someone’s place, I get too judgy. I once got totally turned off by this girl’s DVD collection. Like, she had all the seasons of The L Word. Just no.”

  I laughed. “Oh fuck. Good call.”

  She lifted her water glass to my beer. “It’s so nice to be understood. So what, you turned down a beefy dudebro and your pal the toppy dyke was next on your list? I’m honored, Jus.”

  Madison had never shortened my name before, but Avery had. Given their friendship, it was only a matter of time before both of them were doing it. And then it would spread. Especially if they met Alex and Jamie.

  I cleared my throat. “I know you’re not into men.”

  “I’m not turned on by men. As far as I know. But I’m pretty sure you want a scene. And I’m turned on by scenes.”

  “Not— I didn’t say— I don’t think—” God, I was blushing. “I should go.”

  “Why?”

  Because this was a stupid idea. Because I’m ridiculous. Because you’re a goddamn lesbian. Mostly, anyway. “Because this won’t work.”

  She set down her water, then took my beer. “It’ll work if you let it. I know you don’t want cuddling for aftercare, but will you eat something with me before you go?”

  I groaned. “God. You actually do that. You really are teacher’s pet.”

  “It works! I mean, you know, in that it’s a really good transition. Which we don’t need, probably, but has actually been helpful to me with other people. Five, ten minutes. No big deal.”

  “I’ll finish my beer. That’s your aftercare.”

  “Deal. You want to come?”

  “What kind of terrible lesbian are you? I don’t have to come, Madison.” I couldn’t call her Maddy, even though I was certain she’d welcome the intimacy.

  “I’m not afraid of penises, even on men. I could execute a handjob. I think.”

  “Thank you, that will not be necessary.” God, this was almost as bad as Beefy Dudebro.

  She giggled. “I was going to have to call a time out so I could google ‘how to handjob.’ Though now I’m super curious and I kind of want to try.”

  “I’m just going to—”

  She grabbed my upper arm. Tightly. All traces of levity gone. “Paddle, whip, or crop?”

  “I…” My heart kicked up a notch. “I hate crops.”

  “That sounds like a request. Restraints?”

  I really hated crops. I could tell her no. She wouldn’t push it, not even if she thought it’d be good for me. Except now that we were here, now that we were negotiating like good little graduates of BDSM and Dating, I thought it might be good for me, too.

  Not the crop so much as the fact that I didn’t want it. Maybe a good helping of something I didn’t want would do that whole reboot thing I’d been thinking would save me.

  “I hate crops. And no restraints. I can hold position.”

  “It’s not about whether you can hold position. It’s about if this will be better if you don’t have to.” Her hands circled my wrists. “Bind them in front of you, bend you over the couch, hurt you with something you hate. Maybe get you off. Then you get to finish your beer. Does that sound better than whatever Beefy Dudebro had to offer?”

  I couldn’t look up from her fingers around my wrists. “Yeah. I kind of hate that it does, but yeah.”

  “So can I touch you? I grasp the principles of the plumbing and I’m not totally inexperienced.” She gave the slightest squeeze. “I’d like to. Unless you mind. I like playing sensations off against each other, seeing what I can wring out of someone.”

  If she’d tried to make it ornate—about me being at her mercy, or about her bringing me to my knees, or worse, showing me where I belonged, which was a line I’d heard more than once; something about me made people itch to put me in my place, apparently—I would have dropped it and left.

  But this didn’t feel that way. It felt, for lack of a much better word, friendly.

  “Yes.” I swallowed hard. “Please.”

  “Awesome. Now let me just get out the four page questionnaire I make all new play partners fill out and sign—”

  I elbowed her and she laughed.

  “This is way more fun than cleaning my apartment. I’m glad you came over, Jus.”

  There it was again. I searched myself for annoyance and found none. “Me too.”

  We did the usual things. Blah, limits, safewords, yes, marks are fine, blah blah blah. I didn’t particularly feel the need to be naked beyond shoving down my pants, and she didn’t demand nudity. Neither did she step out of the room to slip on something tight and leathery.

  I told her, somewhat churlishly, that since she was using a fucking crop, she may as well not go easy on me. I consider it a positive sign when the person I’m with says, with no perceptible nervousness, “I seriously didn’t plan to, but thanks for the permission” and slaps my ass.

  Madison had decent restraints, objectively speaking. I admired them less as she was buckling them on me. “This really isn’t necessary.”

  “When you talk about your people, you always sound as if you don’t have any choices. Like your hands are bound, metaphorically. Maybe you need to be reminded what it feels like.”

  “You’re doing kink therapy on me now?”

  She rolled her eyes. “Yeah. I’m pretty sure one scene with me is gonna cure you of being a dumbass. I’m just that good. Bend over. I want you to really feel this.”

  I bent over, and suffered the indignity of Madison adjusting my shirt so it wasn’t in the way. Goddammit. “Feel free to start any fucking time.”

  The shaft of the crop ran over my ass and I shuddered. For a second I fantasized that it was Jamie behind me. Why had we never done this? It didn’t have to be all tangled up in the rest of everything. It could just be…simple. Transactional. Give and take and take and give.

  Except then I’d want to kiss her. And I’d want to hear the sounds Alex made watching.

  I shook my head restlessly, pushing back into the goddamn crop, which hadn’t even struck me yet. My bound hands braced on the seat of the couch and god help me, I liked having them right there, where I could see them. Where I could observe as well as experience my own helplessness. “Madison—”

  Her hand, flat on my back. “I know. Anticipation is worse than pain.”

  “Fuck you.”

  The hand pressed down and I breathed into it. I knew how to do this, how to find the space in my head that made it work. I didn’t always get there the same way, but I could get there if I tried.

  I wouldn’t have, with BDB. I wanted to with Madison.

  She warmed me up much more slowly than I would have wanted, but even then, it didn’t feel like a concession. Madison probably warmed everyone up slowly because she liked the pacing, she liked the action of it. And we weren’t doing anything more intense than this, so in a way, the pressure was off.

  I still couldn’t enjoy a riding crop hitting my ass. And I actively gnawed on my tongue when she went at my thighs. The bitch about a crop was the
flare of it. Done with intent, the crop was a concentrated force on a small area of skin. I knew how to handle thud a lot better than sting, and sting-plus-fire was a crappy combination.

  “Spread your legs a little more.”

  I didn’t have the energy to snark, so I shuffled my feet apart as far as I could and braced.

  And oh, fuck, fuck, the unholy wrongness of the tress snapping back and forth on my inner thighs, laying down fire that only intensified, never ebbed. I couldn’t get on top of it, couldn’t ride the sensation (no pun intended). My back hunched, my legs went rigid, and I leaned toward the couch, away from the crop, but of course it followed unrelentingly. The fire became liquid, spreading, hotter and deeper than wax, a bruising, burning thing I couldn’t control and couldn’t master.

  Until it stopped.

  Madison’s hand reappeared, higher up, between my shoulder blades. “You don’t have to be quiet. I like sounds. I want to hear you.”

  “I don’t like to give people the satisfaction.”

  “The satisfaction of knowing they’re pleasing you?” Her hand slid down my spine, over my ass, curled around my hip.

  “You don’t have to,” I whispered, and all the defeat, all the loneliness, all the grief from having tried to do something and failing, hit me at once. I missed Alex and Jamie terribly, but they felt as distant as the moon. I was empty now of all the words that usually insulated me from feeling. My thighs throbbed, my head hung, and I was torn between pulling away and holding very still, as if I could go invisible.

  She shifted behind me, legs pressing against mine, and the shaft of the crop ran up the front of my thighs with excruciating slowness. I felt it approach my cock and trembled, arms shaking with the effort of holding me up.

  “I want to.” The shaft of the crop made gentle contact, nudging my cock. She could have used it to hurt me. Or to degrade me. To mock my vulnerability at her hands. But the crop, which I hated, became something else. She slid it with agonizing care along the length of my cock, pinning it to my stomach, leaving me feeling weirdly exposed, as if more than fingers or lips, the crop laid my desire bare.

 

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