Lasshole

Olivia smiled, and Katie, though she loved her Mistress, was afraid. Olivia had elegant bones, and they were close to the surface. Her beautiful smile was peaceful, amused, deceptive. 

Olivia most often used that smile on men, submissive male clients who had misbehaved. They knew they would see it only briefly, before being ordered to turn their backs and kneel. Then they would not see her, but they would feel her. Their submission, pain and humiliation was erotic theatre, for them, and Olivia was good at it. It had paid for the Bloomsbury house she and Katie shared. 

Katie was seeing that smile because Olivia’s uncle Louis and his wife Catriona had stayed and outstayed, never hiding their contempt from Katie though they pretended to Olivia that they accepted the relationship. Their problem wasn’t that Katie was a woman, but that she was common. Her voice came from south of the river, while their accents were cut crystal, like Olivia’s. 

Katie had complained when they’d gone at last, and when she felt Olivia hadn’t listened she’d shouted at her. She’d shocked herself, let alone Olivia. It was a breach of everything in their relationship. Katie was Olivia’s property, and she loved being that, but when she had to see that smile it did not mean theatre. Something was about to happen, real and memorable. Olivia sat in her chair in their bedroom, silent, for several minutes, while Katie stood in front of her, heart thudding. 

At last Olivia said, “I never expected to hear you speak to me like that, Katherine Wrightson.” 

Katie could feel her skin chill, and she knew she was paling to ghost, bone-white though she was naturally milk-pale. Olivia only used her full name when she was very displeased. She said, since she hadn’t been forbidden to speak, “I’m so sorry, Mistress. I – No, I’m only sorry. I know it was wrong to speak like that. I have nothing to say for myself. Except sorry. Shall I fetch the whip?”

The whip rested in the second drawer of the bedside table on Olivia’s side. It was leather, about four feet long, coiled on a velvet cloth so that Katie could fetch it though she was forbidden to touch it. It was the most severe instrument Olivia used. 

Katie watched Olivia’s eyes like a dog watching a human teasing it before throwing a ball. The whip hurt, though it wasn’t necessarily a bad hurt, and the sooner she was punished the sooner she’d be forgiven. But Olivia smiled again, and Katie’s heart sank. “No, Katherine. You’ve learned to like the whip. I don’t think there’s anything I can do, that would genuinely punish you.” 

“Mistress?”

“So I’m sending you out, little one. Your punishment will come from elsewhere. Not,” – Olivia’s voice was cold – “from me.” 

*

Katie chose the Friendly Society bar, downstairs from Soho’s Wardour Street. The theme was subaqueous and the cocktails were expensive compared with her favored pub in Bloomsbury, but she was wearing a Vivian Westwood bustier and though her breasts were small she didn’t expect to have to pay for one. In the meantime she drank soda water and watched. 

There was a handsome man in tight pants and a tight shirt, dressed to pick up, with a nose-ring and little Star Trek pointed sideburns. Katie wondered if he would be her man. But he was giving his attention to a girl with larger breasts than her, and a Wonder Woman tiara. The woman was, at first, fending him off while playing amusement, and then he said something that angered her. She made the words, “Fuck off”, with her lips, and pushed him back. The man smiled and leaned forward, closer, going for a kiss. Then the woman was only pushing him away. There was a brief struggle, of unequal strengths. 

Katie was about to launch herself in the woman’s defense when an older man, in his forties with a widow’s peak and a ruined brick of a nose, put down his book, Nightmare Abbey, and went over to touch the handsome man on his shoulder, very delicately. The two men eyed each other briefly. It wasn’t clear whether either man spoke. But the younger man took his hand off the woman’s shoulder, and raised his head so he wasn’t in her space. He smiled down at her. 

Then he looked more closely at the older man. For a moment Katie thought they would fight. But the younger man got up, with exaggerated, sarcastic care, and went to another part of the bar. Katie watched to see the man follow up, saying something flirtatious to the woman he’d rescued. But he didn’t. He made a brief apologetic remark to her, which Katie didn’t hear, and went back to his seat and his book. The woman turned her attention elsewhere. She’d met a man whose attention she didn’t want and another who didn’t want hers. The bar had to offer better than that.  

So Katie picked up her glass. There was a seat at the older man’s table. She took it and said, “Waiting for your girlfriend?” 

The man looked up, surprised. Then looked at Katie, surprised again. Katie had colored her short hair and eyebrows the same bright yellow as Tweety Bird. And she’d had her hair shaven at her hairline except for two close-cropped half-circles about three inches above her eyebrows. She appeared to have four eyebrows, which exaggerated the size of her eyes, which were already green-blue and huge. So that the first thing the man said to her was, “God. I’m sorry, I didn’t mean to stare.” Katie smiled at him. So the second thing he said was, “I mean, you look fantastic. Erm. In the good sense of fantastic.” 

Katie said, “Precision. Always good. My name’s Katie.” 

His was Harry, and he said he was resting between girlfriends. They talked for a while about jobs and movies and then about the décor at the Friendly Society, with countless Ken and Barbie dolls stuck to the ceiling above them. Harry shook his head, and said, “It’s like going diving below the bodies of the drowned.” 

Katie nodded. It was. But she replied, “Are you free this evening?”

“Um.” He looked at his book, and closed it. “Yes, I believe I am.” 

“Good. Because I need you to take my anal virginity.” 

“Christ!” And he knocked over his glass of red wine. “Well, if I haven’t put you off by being such an oaf, then of course. But …” He rescued his glass and dabbed at the spill, taking tissues from his pocket and making a sodden mass of purple and white in the middle of a dry-ish table. “There has to be a story to this.” He looked at her, inviting. 

So Katie explained that she had a Mistress, and she’d done something so bad that Olivia wasn’t prepared to whip her for it. This was the punishment she’d decreed instead. Harry looked at her with mild disbelief. There was silence when she’d finished explaining. 

At last he said, “So you want me to do something that you’ll only experience as punishment? So it’d be awful? I’m to be your horrible experience? I don’t think I–” 

Katie put her hand on his arm. “Please. I know it’s odd. No, it’s odder than that. But I picked you because I think you’re decent. And your reaction kind of confirms my choice. But I have to get my arse fucked tonight. I don’t disobey Mistress. So if it’s not you I’ll have to get someone else. And I trust you not to be horrible to me.” 

“I’m pretty sure that’s the worst argument for anal sex I’ve ever heard. Not that anyone’s ever had to argue before, so I’m not much of a judge. But what’s the story? Does this Olivia want to watch, so she’s sure it happened? Because I’m not–”

“No. Your place will be fine. And a photo will do. Your cock in my arse. Olivia can recognize my arse by now. Do you want me to beg? I’m told I can be quite good at–” 

Harry stood up hurriedly. “No, I don’t want to hear you beg. I think I’d find out things about myself if I did. Look, we could get a cab, but it’s only a twenty-minute walk. I live round here. And … I don’t think you’ve done anything like this before.” 

“No.”

“Well, here’s my card. You should take a photo of it and send it to Olivia. If you’re going to pick up strange men, that’s what you should do.”  

“No, I said I trust–”

“Do it.” 

Katie grinned at him. “I think you’d get the hang of this quite easily.” And she sent her portrait of his business card to Olivia, as ordered. 

As they walked up the stairs Harry held out his arm. Katie took it.

*

Harry had remained decent and sane. He had kissed her, walking to his flat, but desisted without comment once he realized Katie didn’t want to be kissed. When they entered his bedroom, he’d been complimentary when she took her dress off but not too specifically so. He said, “Look, the combined sexiness of the humans in this room is off the charts. That’s all your doing, but I hope you’ll average it out and see me kindly.” But when he took off his shirt and pants, and stood naked, erection poised in her direction, she could see, without quite desiring him herself, that most women would be pleased to see Harry naked.  

Katie grinned at him. She hadn’t expected him to be nervous. She guessed she was his first lesbian. “You bring your own temperature to the room, Harry.” She watched him relax. It had been enough. She climbed onto his bed and posed on her hands and knees. “But my arse …” 

“Waits for no man? It isn’t going to fuck itself?” 

Harry’s bed was comfortable, though Katie was not comfortable. She hadn’t expected to fuck a man, even an apparently nice one, while she was with Olivia. She wasn’t prepared, in any way. She’d expected that Olivia would take her anally some time, with a strap-on. She’d expected that even that would be difficult. Emotionally as much as physically. But with a man and no Olivia, she was much further out of her depth. But she wiggled her bottom at him, and was answered in male gasps. “It’s waiting for one man. The stress is on waiting.”

“Well, if this is punishment, then we should get it over with.”

She wasn’t sure if he was joking. She said, quickly, “Look, I’m glad it’s you, Harry. I mean it. You’re not a psycho. And you seem to know what you’re doing. I think.”

“I’m honored. No, seriously. And there’s a lot of complicated stuff going on here. But also, I simply want you. Right now especially your ass.” 

“Mmm.” Katie let her head fall. 

She felt Harry’s hand caress her bottom. He meant to be reassuring. “I have to lube you. You need to be a slippery girl, for this. So that’s how we start.” 

Katie sighed. “This is true, I’ve heard. Do your worst.” 

She felt him pat her bottom affectionately, a gesture that was oddly like something Olivia would do. When his hand returned his forefinger was slick, and pressed against her little opening. “Try to relax, Katie. I know this is … new. And kind of weird. But the more relaxed you are, and the more lubed you are, the better.” He pressed again against her asshole and stopped. 

Katie frowned, puzzled. Then she realized. Olivia wouldn’t have asked permission, or waited for it, but he was. “Yes,” she said. “Yes. Lube me, please.”

The finger pressed forward and Katie felt her rectal muscles give, opening and admitting him, then clinging tight. He turned his finger in her, pressing in the dollop of lube, then withdrew. When he returned with more, she was ready for him and relaxed. It was not, she admitted, unpleasant. He thrust his finger a little deeper, and she could feel that she was slippery, being made ready for his intrusion. But he said, “This needs more lube than you can imagine. Your mistress, Olivia, she’d say you were a good girl, wouldn’t she?” 

“Usually, yes.” 

“Then be a good girl for me.” His voice was soft, gentle, the voice he would use to calm a horse. “I’m going to give you two fingers this time.” 

Katie raised her bottom, allow him better access. At a purely physical level, she had to admit, she wasn’t hating this. His forefinger and index finger entered, and this time he poured a little of the lube onto his fingers and pressed and spread the slippery stuff inside her. 

He said, “How you going? This ok?” 

“Uh.” She shook her head. “I hadn’t expected it to feel so intimate. It’s very… invasive.” 

She was staring at her pillow, focused on her sensations and not on him, except for two of his fingers. He squeezed more lube into his hand, coating his fingers and inserting more into her rectum. Then he slowly finger-fucked her. Katie tried to imagine how his cock would be, once he was demandingly inside her. The reality of the fingers, and the proximity of his cock, seemed to be good, sensual things. She made a little noise that wasn’t pain. She wondered if that was betraying Olivia. But eventually he withdrew his fingers. Katie realized that she minded their absence. 

Eventually Harry inserted three fingers at once, and Katie didn’t feel that as unpleasant either, only strange. Harry said, “I think you’re ready, Katie. And the truth is, I absolutely want to fuck your ass. Your lasshole.” 

Katie opened her eyes. Her world, visually, was pillows, white cotton. “My what? My lasshole?” 

“Er,” he sounded embarrassed, “My girlfriend used to say that. She’s studying in Japan, now.” He sounded sad, suddenly. “She liked buttsex a lot. But I like your lasshole. Uh.” He got onto the bed. “Your very beautiful lasshole.” 

Katie smiled. That had to be silly. He rolled a condom on and knelt behind her, his knees between hers. She felt his cock, level, hard, the head pressed between her buttocks. His voice was strained when he said, “I know you’ve been told you have to do this. But I want you to tell me if it hurts. Or hurts too much. I’ll stop, and I’ll withdraw. That second. Understood?” 

Katie said nothing. Then she realized that he wouldn’t continue without permission, so she said, “Of course I understand.” She’d expected the strangest thing about him would be that he was a man. But in practice it was that he wasn’t a dom. A man who was like Olivia would not be asking for all these permissions. 

He said, “And you should take my cock, I mean take it in your hand, and line it up against that lasshole, so the angle is most comfortable when I enter you.” 

Katie felt a moment of rebellion: she wasn’t going to put her hand on some man’s cock. Then she remembered that that cock was going up her ass, and she laughed at herself and him. She took his cock in her right hand, feeling its hardness and the way it moved convulsively when she touched him. She guided the head to her entrance. “You’re being– You don’t have to be quite so fucking careful with me all the time. I’m just a dyke. A dyke submissive. Doesn’t mean I’m made of glass. Fuck me.” 

He laughed, and kissed her shoulder blade. Then his cock pushed forward, and her muscle opened for him. 

She said, with the head of his cock just inside, aware that it was probably her last chance to say something coherent for some time, “Harry, I want you to do whatever you like. So long as you do it hard.” But she had one more thought. “Still, remember … this is my first time.”

She frowned, wondering if even she understood what she’d just told him. He said, “There’s a speech I should make now. It’s that I’d hate it if anything hurt you, apart from good hurts that don’t count. So tell me at once if anything doesn’t feel right. And you can set the pace, as slow and gentle or as hard and fast as you feel comfortable with. And that bit about me stopping if you say it hurts, that still applies. I know you’ve got your orders. But those things are still true too.” 

Katie said nothing. His cock began to move back and forward in her rectum, a strange object but somehow right. Each thrust and withdrawal took him a little deeper into her. She yelped, not displeased. 

She spread her knees as wide as they’d go, which lowered her ass a few inches closer to the bed. It allowed him easier access and made the connection between them more comfortable. Katie said, again, “Fuck me.” She pressed her forehead into his pile of pillows. She felt him hold her hips. Olivia, or a male dom, would be smacking her bottom while she or he took her. 

But Harry said only, “Perfect, girl.” He reached under her belly. Katie sucked her tummy in and spread just a little wider, to give him better access.

She felt him touch her cunt, then squeeze gently. She realized she was utterly, sopping wet to his fingers. He was doing enough things right. He whispered, “You should keep still for a while, if you can.” She held herself tense, ass still enticingly in the air, and her face was set. She yearned for orders, for authority when she was aroused. 

He didn’t give orders, but it seemed that she liked feeling invaded. She only said, “Ohh.” And she left her mouth open after she’d said it. 

Then he moved a little deeper still and her ring tightened on the shaft of his cock, clasping him. She trembled under him, on his bed on her hands and knees, with most of his weight on her back and his cock half-buried in her ass and thrusting forward. At last he was fully in her and their bodies pressed together, her buttocks and his upper thighs and groin. 

He said, “Are you all right? Comfortable?” She didn’t answer. She shook her head, meaning that she felt good, but he should stop asking.

Katie could feel certain emotions she had only expected to feel with Olivia. Harry was a vanilla lover, and diffident, always asking for permission, but when he was buried in her like this she felt submitted. She wanted to abandon herself, surrender to him. No, it was too late for that, she had to admit. She’d already surrendered. 

Harry moved back a little, inside her tight, slippery tube, and then pushed forward. This was so intimate, Katie thought. She’d expected it to hurt more, but she hadn’t known how invaded she would feel. Harry began to move in her, taking her, and she heard him sigh with pleasure. 

She passed him her phone, then. She said, “Proof. For Mistress.”

She could feel his slight awkwardness as he twisted his body a little, to allow the pics, with his cock buried deep in her, and then another pic with him partly withdrawn but still in occupation. He said nothing. Deb guessed he was silenced by the complexity of his role: he wasn’t her lover, let alone her Master, and yet something powerful was happening between them. 

He put the phone down and reached under her, and slid his fingers along her cunt again, and then into her. Katie’s eyes widened; that was intense, and good. She knew she was going to come from this, and that was something she hadn’t expected. Harry sped up, and she followed his lead, fucking hard, no longer gentle. Katie could hear herself puffing as if she’d run a mile. A sex mile, with Harry riding her back. 

He kissed her shoulder again, but his movements weren’t gentle. He fucked her ruthlessly, driven. She still couldn’t manage words, but she nodded. He leaned down, his whole body tightly pressed onto her back, and kissed her neck. She saw his face, and she made a kissy gesture with her mouth, to let him know they were good. 

She wanted to say, “We’re good,” but things inside her rose suddenly and she screamed it. Then they both forget about words and breathing, and fucked in grim hurried silence, with Harry’s hand still on and in her cunt. Katie screamed again, a second little peak of pleasure, though she knew something bigger was imminent. 

Harry released her and dropped his hands to support his weight on the bed, still fucking her hard and fast. Katie fell forward onto her breasts and shoulders, arching her ass up at him. She put her hands on the backs of his hands and held tight, affectionate, while he sped up, even faster. 

Katie stopped still, suddenly, pushing herself hard against his cock, getting it as deep into herself as possible. Then she felt contractions inside herself. She was coming again, but harder. There was power as well as surrender. She rocked slowly now, making high-pitched noises, and then at last a loud, low wail. Harry made a sound that might have been laughter, happy for her. 

She’d have fallen flat on the bed once she’d come that last time but he wouldn’t let her go. He held her ass tight up against him and fucked her until he’d come too. Then they fell forward together onto his bed, with his arm around and under her and his cock still hard inside her. For a long time there was no reason to move or speak.

Eventually he said, “Would you like to stay? I mean, the night.” 

Katie opened her eyes. In a way it was tempting. She said, “God no. I have to get back to Mistress.” 

“Mission accomplished?” There was a slight hint of petulance in his voice. His cock was still hard in her. 

Katie turned her head to the side so he could see her. “O yeah. That’s one virginity I definitely don’t have any more.” 

“Are you sorry? I mean – Christ, men aren’t supposed to ask this – but was it ok? Or did I punish you?” 

Katie wanted to be back to Olivia now. But he’d been as kind to her as he could be, and deserved kindness in return. “You’re a very skilled lover, and you take care and you’re passionate. From what I hear most men do one or the other. You do both. And you know how to make a woman, well, enjoy herself.” 

“But ..?” 

“I haven’t finished. There’s something in you that you haven’t explored. Remember when you said you were afraid to hear me beg? I think you should explore that side of yourself. You could be to some woman what Olivia is to me, and she’d be a lucky woman.” 

He nodded, slowly. Sober. “Yes, I felt that. You might not be my submissive, but you did call out something in me. I might explore it. Carefully as well as passionately.” 

“You should.” Then Katie stopped. She didn’t want to say what she had to say, but she owed him truth as well as kindness. He kissed her shoulder again, and withdrew slowly, reluctantly from her arse. She said, “You mind if I borrow ‘lasshole’? I mean the word? I think Olivia would like it a lot.” 

“Of course. I suppose that lasshole actually belongs to Olivia, doesn’t it?” 

Katie nodded. “What’s mine is hers. And … I don’t mean this unkindly, because you were very good to me. But the truth is that I’ve just been punished. Badly.” 

“I made you come!” 

“I’m not hard to make come. Anyone who knows their way around the body can make me come. I meant what I said about you being a good lover, but that’s true too.” 

He nodded, chastened. “This is so.”

“But I belong to Olivia. I love her. And even the thought that she needed to punish me, that’s enough. That’s the punishment, in itself.” 

Harry got up from the bed. He shook his head, looking down at her. “Katie, you’re a lovely woman. Not just beautiful, though you are, but just a really lovely person. If Olivia comes anywhere near deserving you, then she must be one of the wonders of the world.” 

Katie rolled onto her back and smiled up at him. She’d hurt him a little and she was sorry. But she said, “Yes, she is.”

Harry sighed. “Katie, there’s a bathroom just to the right, on the corridor. There are spare towels, soaps, whatever you want. So clean yourself up, and then you can have a drink. Or a taxi. Whichever you’d prefer.” 

“I’d love to stay longer, Harry. But Olivia is calling me. I can feel it. So taxi, please.”

At his front door, when the taxi arrived, Katie kissed him one last time. “Thank you for looking after me. And the next time you have a woman here, you should give her an order. In that voice of yours. You might be surprised by what happens.” 

He grinned and kissed her back, and put his hand on Katie’s arse. But that would be the last time, they both knew.

*

Katie let herself in, and took off her dress. She kept her phone in her hand, but dropped to her hands and knees. Her protocol was that she crawled, after punishment, until she’d been formally told she was forgiven. She said, not too loudly, “Mistress?” 

“I’m in the bedroom, little one.” Katie felt relief. ‘Little one’ was a good sign, far better than ‘Katherine Wrightson.’ She scampered to the bedroom. She needed Olivia badly just then. 

Olivia sat in the chair she’d been in when she sent Katie away. She wore a simple blue dress, which meant she’d done no professional domming that day. Her riding crop leaned against the chair, the handle in reach of her right hand like a badge of office, but Katie was certain she wasn’t going to use it. 

Olivia was not always as fearsome, to Katie, as she thought she was. Katie loved her, and needed her and understood her too well for that to be possible. So she said, as her protocol demanded, “Thank you for punishing me, Mistress.” 

She approached the chair, still on her hands and knees, and passed up the phone, with the pics showing Harry’s cock in her. Olivia looked at it and smiled at Katie. This wasn’t a frightening smile. “You’ve been obedient. And you’ve been punished. Tell me, how was it? Was he good to you?” 

“He did his best, Mistress. I picked him because he seemed to be … kind. And he was.” 

“I knew you’d pick wisely, Katie. And you are lovable. No one sane would want to do you harm, and you’d find someone sane.” She smiled again. “And it’s over. You’ve taken your punishment and you’re forgiven. Would you like to sit on my lap?”  

Katie made a glad noise and climbed, still naked, onto Olivia’s knees. They kissed, Olivia’s hand in Katie’s hair. At last Olivia pulled Katie’s head back and looked at her. “Katie, I’m not sorry I punished you so harshly. You will never speak to me like that again, and if you did, I’d do the same. Only worse.”

Katie couldn’t imagine what could be worse. “I know, Mistress.” 

“But I got a call from Louis. Uncle Louis. He wanted to advise me to get rid of you. To do better. He never said anything like that to me when they were here. Now I have a better idea of what they would have been like, to you.” 

Katie nodded. “They weren’t fun.” 

“Believe me, darling, I went full Domme on him. He’ll never speak to me like that again. And I doubt if he’ll ever have the privilege of meeting you again.” 

“Thank you, Mistress.” 

“I’m sorry I didn’t see it, or I’d have stopped it earlier. And Katie, darling, I do know your worth. You’re a wonderful, beautiful woman, and your gift to me is the best thing that’s happened in my life. Ever. I love you. I beat you, my love, but I’m besotted.”   

“Ensorcelled. Wise Mistress.”

Olivia laughed and kissed her again. “Next time I punish you, it’ll be in this room. Just the two of us. Unless you are very bad. But tell me: you said he was a nice man, and I’m glad. But was it an effective punishment?” 

Katie thought. He’d been nice. And she’d come. But … “I know what theists mean now, when they say hell is separation from their god. It’s not all those comicbook torments and little guys with pitchforks that the fundamentalists like to imagine. It’s just silence. And my god actually exists, my Goddess, and I was separated from her. That was hell.” 

Olivia kissed her again, then smacked her bottom fondly. “I suppose I should get a strap-on for you. Would that be punishment or reward?” 

“Reward, Mistress. The actual sex was surprisingly … not punishing. You can have my lasshole whenever you like.” 

“Your… what?” 

“I’ll tell you later. But, my yummy bossy Goddess, shall we do something nice? You bed looks kind of … heavenly.” 

Olivia looked at her, still with nothing scary about her smile. “Heaven, then.” She took her girl to her bed. But, as an afterthought, she brought the riding crop.

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