Like Craig’s List Roulette, she hadn’t planned on doing this more than once. And like Craig’s List Roulette, she was hooked after the first time. The next day, she did it again. She opened the motel door for another stranger; she dropped her robe; she lay on her back and spread her legs when he told her to; she let herself get fucked. And when he left, she took the Do Not Disturb sign off the door, and waited for the next one.
She did three guys that day. Seven the next. After that, she slowed down a bit: kept it to once a week, and usually no more than three or four in a day.
Some of them were simple. They just wanted a girl on her back with her legs open. And that was fine. It had a certain primal, meat-puppet charm. Some were more imaginative. And that was better. She liked being told to sit on the guy’s dick and face away from him. To straddle him on a chair like a stripper and give him a lap dance that turned into a fuck. To lie back on the cheap motel desk, her butt scooted all the way to the end, her fingers spreading her cunt apart, her face turned to the wall. She liked being told to lie face down on the bathroom floor, her tits getting scraped by the cold tile as she got fucked from behind.
Sometimes it was hard. One of them told her, “I want to fuck you in the ass.” She’d never done that before. Somehow, by a statistical freak, it had never come up in Craig’s List Roulette. But the habit of compliance had become strong, and it didn’t occur to her to say No. She gestured to the lube and the condoms on the nightstand, and said only, “Slowly, please. I’ve never done that before.” And she got on her hands and knees on the bed.
It hurt a little. He wasn’t as slow as he should have been. But that was kind of okay. Again, she pictured where she was, what she had done to get here, what she was doing now. She remembered that she was being fucked in the ass for the first time, in a sleazy motel room by a man she’d never met: a man she’d undressed for and offered herself to the moment he walked in the room. She remembered that she was face down on the bed and that her ass was being pushed open, too fast and too hard, because she’d invited any man who showed up at her door to fuck her any way he wanted. She remembered what a slut she was, that she’d asked for this, that she deserved this. She buried her face in the bed and whimpered: a genuine cry of pain and fear, blending imperceptibly with a moan of abandon.
She’d pictured her first time getting fucked in the ass a hundred times. She’d never pictured it happening like this. It was a hundred times better than she’d ever imagined.
She loved Motel Slut. And again, she kept the game up longer than she would have… because she was putting off the third one. She was more than a little afraid of the third one.
• • •
The third game, she called Pick the First.
It required a lot of courage. She was glad she’d put herself through Slut Boot Camp first. And it required strict honesty with herself. She couldn’t rely on the randomness of a number generator, or the randomness of which man happened to be reading Craig’s List at the moment she placed her ad.
In Pick the First, she had to read the ads on Craig’s List. Casual Encounters, Men Seeking Women. She had to pick the first ad that turned her on; the first ad that made her want to masturbate. And she had to send them this email. She wrote it ahead of time, before she started looking, so she couldn’t cheat.
I don’t want to negotiate. I just want to do what you tell me. Please tell me what you want me to do, and what you want to do to me. Please tell me everything you can think of, now, so we don’t ever have to talk about it again. If what you want is okay, I’ll be at the Java Jive Cafe on 4th Street this Saturday at noon, with a black carnation in my hair. Please meet me there, and then take over.
It took longer than she’d thought to find the right ad. She considered “Submissive women needed for thick cock,” but the poorly-lit photos of his torso and cock made her flinch with distaste. She thought about “arrive, bend over, submit, leave,” but the scene he laid out stopped at sex and went nowhere interesting. She regretfully passed on “Cruel, Humiliating, Abusive and Sadistic”: the headline make her clit jump like a kangaroo, but the ad was a letdown, with no juicy details, and an equivocating manner that put the lie to the promise of the headline. She kept an eye out for her spanking friend, but he wasn’t on Craig’s List that day. She saw “Brutal M Seeks Submissive W,” and opened it. It read:
“I am a hard and unyielding man seeking a woman to whom I can do things. The things I want to do are not nice. I will want to use you sexually, humiliate you, hurt you, make you helpless. I will want you frightened, and suffering, and willing and compliant throughout. Am not looking for either brats or doormats. You should have desires, so I can deny them. You should have spirit, so I can break it.”
It made her uneasy. To say the least. But it was the one she kept coming back to. The one she knew she’d be jerking off to. So bolstered by weeks of rigorous self-training in impulsive carelessness, she copied and pasted her pre-written reply, and hit Send.
He replied with a torrent of obscenity.
Implements he was going to use to beat her ass until she cried. Objects he was going to insert into her. Degrading positions he was going to force her into. Other men he was going to lend her to. He said he was going to wrestle her onto her back, pin her arms to the bed with his knees, and force his cock down her throat until she gagged. He said he was going to tie her hands so she couldn’t fight, gag her so she couldn’t scream, tie her legs apart, and whip her pussy before he fucked it. And then he was going to do the same to her asshole.
He said he was going to punish her righteously and ruthlessly for serious offenses. That he was going to punish her cruelly and unjustly for trumped-up offenses. That he was going to punish her for no reason at all except that he felt like it. He said he was going to make her spread her asshole apart for him with her hands, make her beg him to punish her by putting things inside it, make her apologize tearfully for being a bad girl while he did it. He said he was going to slap her face and call her a filthy whore while she sucked his cock.
He said he was going to rape her.
He went on for three pages. He apparently took “tell me everything you can think of” seriously. He finished with the words:
None of this is up for discussion. You will comply with all of it. You may show reluctance—I like reluctance—but you may not show resistance. Except when I rape you. When I rape you, I expect you to resist. I will see you on Saturday.
He scared the crap out of her.
She knew this was a bad idea. Even with all her other Craig’s List adventures, she hadn’t done a third of the things he was talking about. She knew she was in over her head with this one. But she’d known that Craig’s List Roulette and Motel Slut had been bad ideas, too. And they had been the best bad ideas of her life.
She put the date in her calendar for Saturday. And cleared the rest of her calendar.
View from the Fourteenth Floor
HUMILIATE ME
If you’ve ever wanted to humiliate another woman, here’s your chance. Bring what you need on our first date—if we click, I’ll want to do it right away. One night stands only.
Dana read the ad on Thursday. She masturbated furiously and then called the number. They made a date, and she spent most of Saturday making arrangements.
They met in a bar on Sunday evening. Dana arrived on time, and found Elizabeth already sitting in a corner booth. She was blonde, with an expensive haircut, dressed in a crisp white blouse and a single strand of pearls. She already had a drink in front of her. Dana settled into the booth. “So how long have you lived in New York?” she asked.
“Six days,” Elizabeth said. “Look. Here are my limits. I don’t like extreme physical pain, but keep it reasonable and we’ll be fine. Psychologically you can do almost anything. My safeword is ‘safeword.’ And I mean it about the one night stand. After tonight, we’re done.” She took a sip of her drink. “You?”
Dana bit her lip. Elizabeth’s tone offended her,
made her want to slap the woman down. She noticed her clit thumping, and wondered for a moment if she was being played, if the girl was pissing her off on purpose. She stared rudely at Elizabeth’s tits, and decided it didn’t matter. “Your limits are fine,” she said. “And mine aren’t relevant to you. Do you want to do it?”
Elizabeth looked at Dana like she was appraising china. Finally she gave a small nod. “Yes. Let’s do it.”
“Good,” Dana said. “That’s the last word I want to hear from you until… well, ever, I guess.” She strode out the door, leaving her drink untouched, and whistled for a cab. Elizabeth followed, eyeing her suspiciously as they got in the taxi. “Lester Hotel,” Dana told the cabbie. “The one in midtown.” She stayed silent all the way to the hotel, where she led Elizabeth to the fourteenth floor and pulled a key from her pocket.
Elizabeth looked around as the door closed behind her. The room looked untouched, except for an armchair sitting at an odd angle in the dressing nook off the bedroom. The decor was elegant and unpretentious, with tall windows that took up most of the outside wall. Dana switched on all the lights, switched off the one in the dressing nook, settled into the armchair, and began to speak.
“Did you know that every week, dozens of telescopes are sold in the city of New York? Hundreds even, on a busy week. Interesting statistic. Nobody seriously thinks all those people are stargazing in Connecticut on weekends. Everyone knows exactly what all those New Yorkers are doing with all those telescopes. And yet everyone goes on with their lives, in front of their open windows, as if they actually had privacy.
“Open the curtains.”
She could see Elizabeth flinch before she obeyed. Good, she thought. This could work.
“It’s Sunday night,” Dana continued, “so a lot of people are home. And bored, and looking for something to do. When I scoped out the room earlier, I estimated about five thousand windows with a direct view of this one. Probably about fifty have telescopes. More if you count binoculars. So I’m guessing we’ve got anywhere from ten to thirty people in the audience tonight. Maybe more.
“Now take off your blouse and wander around the room. Act like you’re a normal human being who’s just changing for dinner, but keep turning to face the window.”
Elizabeth stopped in her tracks. She turned from the window and looked Dana in the face, dismayed, her arrogance slipping off like a discreet partygoer escaping a bad soiree.
“Don’t look at me,” Dana snapped. “Face the window again. Now.” Elizabeth complied, her shoulders slumping, and Dana went on, calmer. “See, I placed this chair very carefully. I can see you, and your reflection in the window, but people outside probably can’t see me. So don’t look at me again. I don’t want our audience to know I’m here. I want them to think you’re doing this on your own.
“I was going to build this up nice and slow, give you some time to get used to it. But now I don’t think I’m going to. Strip down to your bra and panties, and start doing jumping jacks.”
This was good, Dana thought as she crossed her legs. She could see Elizabeth squeeze her eyes shut as she wriggled out of her skirt and stripped off her shoes and pantyhose; she could see the reflection of the woman’s blushing face as she tentatively began to jump up and down. She could see Elizabeth’s butt jiggling through her panties, her breasts bouncing in her white bra, like a jiggle girl in a music video. She cleared her throat.
“Right about now,” she said, “your audience should be figuring out that something’s up. They’re realizing that you haven’t just forgotten about the curtains. By now they know you’re doing this on purpose.
“Open the bedside drawer.”
Elizabeth complied. She looked inside and cringed, arrogant revulsion arguing on her face with shame and disgrace. Dana hadn’t picked the toys to be tacky on purpose: she just hadn’t wanted to mess with condoms and stuff, so she’d picked up a few cheap things she could throw away. But now the choice seemed serendipitous. Inspired even. She loved the thought of making this arrogant bitch put these sleazy things into her body in full view of midtown Manhattan.
“So let’s get started,” she said. “Lay the toys out on the bed. Take off your bra and panties. Then lie on the bed with your cunt facing the window. Put the pillows under your head so people can see your face, and spread your legs.”
She could see Elizabeth breathing hard. The woman was obeying, but she was doing it slowly, hesitantly, and Dana wasn’t sure if she was genuinely scared or drawing things out on purpose. Either way was fine with Dana. She pressed her thighs together as she watched Elizabeth display her new toys and spread herself out.
“So we’ve shown them you’re an exhibitionist,” Dana said. “Now let’s show them that you’re a pervert. Put the ball gag in your mouth. Stick the buttplug in your asshole. And then spread your cunt lips apart with your fingers. Don’t touch your clit. Not yet.”
Elizabeth stared fiercely at the wall as she bit down on the pink rubber ball and fiddled behind her head to buckle the straps. She turned over to insert the buttplug, but Dana snapped her fingers. “No,” she barked. “Stay on your back. I know it’s awkward. That’s what I want.” She felt a warm glow in her stomach as she watched Elizabeth struggle, groping for her asshole with her feet in the air. She could see Elizabeth fighting to regain some dignity as she settled back into place; she could see that dignity slip away again as the girl remembered her instructions, put her fingers on her pussy lips, and slowly spread them apart. Dana paused for a moment to enjoy the view: the city lights, the wall of high-rise windows shining in the night sky, with Elizabeth’s debased reflection superimposed over it all. She let Elizabeth lie quietly for a minute, let her exposure sink in. Then she spoke again.
“I notice you keep your eyes away from the window. You keep focusing on something else, or else you close your eyes. So look out the window now. Think of the people watching you, and look them in the eye.”
Dana waited patiently as Elizabeth squeezed her eyes shut, shuddered, and reluctantly turned to face her reflection. She caught Elizabeth’s eye and saw her whimper; her pussy clenched, and she pressed on. “Now take the dildo in one hand,” she said, “and the ruler in the other. Stick the dildo in your cunt and fuck yourself. Every few strokes, pull the dildo out and smack your pussy a few times with the ruler. Then do it all again. And keep your eyes on the people watching you.
“Here’s the picture they’re getting. They see a woman who goes into a hotel room and puts on a free sex show. They see a woman who opens her curtains, strips, jumps up and down to get their attention, then opens her legs, puts a gag in her mouth and a plug in her asshole, and spanks herself on the pussy while she fucks herself. All for them to see. And they’re looking you in the eye. You can’t hide from them. They know who you are.”
The dildo was a squishy plastic one, a lurid pinky-tan with prominent veins. She could see Elizabeth cringe as she slid it into her visibly wet pussy; she watched her flinch as she pulled it out, gripped the ruler, and gave her clit a few hesitant smacks. It was all gone now, the arrogance, the composure, the sense of entitlement. She had stripped the woman down to a trashy slut giving a free sex show to strangers with nasty toys from a corner porn shop. Dana took a deep breath and delivered the final blow.
“I’m leaving now,” she said. “I have another hotel room across the street, with my own telescope. I expect you to keep up the show for another hour. You can do any nasty degrading thing to yourself that you like, but keep the ball gag in, and keep your eyes on the window. If I don’t like what I see, I’m coming back, and you won’t be happy about that.” She paused. “If I do like what I see, I won’t be back. In an hour you can shut the curtains and do what you want. The room’s paid up for the night. Checkout’s at noon. It’s been lovely.”
Dana dropped the room key on the floor and left Elizabeth on the bed, violating herself, alarmed, shivering, near tears. She whistled quietly as she shut the door and rode the elevator to the lobby. She
caught a cab in front of the hotel, and told the driver to take her home.
His Hands
This is what she thinks about, when she thinks about him. She doesn’t think about his eyes, like she likes to tell herself; or about his lips, like she’d tell her friends if they knew about him; or about his cock, like she tells him when she’s in a good mood. She thinks about his hands.
When he wants her, it’s always his hands that go first. Brushing lightly against her face. Sneaking up on her thigh. Massaging the back of her neck, and then inching down over her collarbones to entice her breasts. His hands are smart—smarter than he is, probably—and his hands are sweet when they want to be, and they can make her feel calm and drifty, safe and befriended.
But it isn’t these nice sweet things she thinks about. His hands also do things that make her blush when she remembers, things that make her flinch and quickly look for something to stare at on the floor, convinced that anyone who sees her can read her mind. When she thinks about his hands, these are the things she thinks about.
She thinks about his hands pressing her against the wall, one hand pinning her shoulders, the other sliding up her skirt, pushing between her legs, reaching for her clit like it belongs to him. No, not like it belongs to him. Like a thief. Like he knows it doesn’t belong to him and is taking it anyway.
She thinks about his hands pressing her thighs apart, again like a thief, like a catburglar, opening a window and climbing inside. She thinks about his hand on the back of her neck, his fingers coiling in her hair and tightening; she thinks about his other hand gripping her by the wrist, guiding her own hand between his legs, making her feel his swelling crotch. She thinks about his hands on her arms, shaking, impatient, maneuvering her body into place.
She thinks about his fingers spreading her lips open down there, prying her apart, exposing her clit and studying it fervently like he’s reading her soul. When he opens her up like that, she feels like he is revealing her soul, like her soul has been hiding in her clit and he’s discovered it at last: her true soul, the selfish one, the dirty one, the one that wants to quit her job and abandon her friends and family and spend the rest of her life on her back, on her hands and knees, pressed against the wall, with his hand between her legs.
Bending: Dirty Kinky Stories About Pain, Power, Religion, Unicorns, & More Page 2