Masturbation Monday: Proper, good and bad

After a while of knowing nothing except the feel of Roland’s body and the need to be as closely pressed against him as possible, Teresa slowly became aware again of where she was. They were together on his desk, Teresa tightly bent over and Roland covering her.

They were still gasping like sprinters who’d breasted the ribbon and crossed the hundred-metre mark. He reached under her to hold and cup her breasts, his body still pressed tight against her arse, his cock slowly shrinking inside her.

His face was beside hers, over her shoulder after he’d collapsed onto her back. He looked at her with something soft, some form of adoration, in his eyes. His mouth opened, then closed. He had nothing to say.

But eventually Teresa said, “I felt that! You coming! Like a little splash in me. Little splash of you! It was lovely. I felt you come in me.”

Roland kissed her. “That was… amazing. You can have as much of my come as you like. Whenever you like. And wherever.”

She chuckled. That didn’t need an answer, but it was good to hear. He said, “How’s your arse?”

“You mean the spanking or the buttsex?”

“Let’s start with the spanking.”

“The proper spanking? I feel not sore. Very not sore. Warm. Lovely and toasty. And I felt all floaty, for a while. Not long enough. And while I was floating, nothing hurt. Is that supposed to happen?”

“Absolutely. Yes.”

“Then proper spankings are great! But… you’d give a girl that for being bad? How’s that supposed to discourage her? I want another one of those. Lots of them. I mean, once I’ve recovered a bit. But soon.”

”That was a good-girl spanking. A proper one. But there are bad-girl spankings, too, and I think if I ever have to give you one of those, you’d, um, modify your behaviour. To avoid me giving you another one. It’s not just that it hurts more, when I spank to punish. It’s the knowing I’m cross with you. It feels very different.”

“’If you ever have to give me one of those.’ You’re assuming a lot, aren’t you?”

Masturbation Monday: Animal sounds

Teresa paused. Jack had just asked her –told her – to ask him to fuck her ass.She paused. It turned out to be a hard thing to ask for. It made her feel shy. Also, it might hurt. But she felt committed, and more: she wanted this. It wasn’t so much that she wanted his cock in her ass, as that she wanted him in charge.

At last she nodded. “Yes, sir. Would you please fuck my – Ohff!”

Jack had run out of willpower, or won’t-power, it seemed, and with her demand half-stated he’d pushed forward and into her. Teresa opened her mouth, savouring the sensation. He put his hands on her hips, clutching hard to hold her still while he slowly took her.

The last time she’d had a cock in her arse the boy had worked his way in with a series of small advances and even smaller withdrawals, until he was all the way in her.

But Jack relied on the lube, and perhaps her assurance that he could be rougher, and he took her, slowly but in one long, continuous thrust. She felt him firmly taking her, his lubed cock hard and slick against the inside of her anal tube, nosing its way deeper and deeper until the cool of his stomach and thighs pressed tight against her blazing hot skin. She sighed then, satisfied. She was thoroughly filled.

They both breathed out audibly then, tightly joined, and slowly moved together. He reached under her to press his hand hard against her cunt. Eventually, she pushed her arse back at him, and squeezed to hold him tight. He was deliciously hard and just the right amount of painful in her, her spanked skin still blazing heat back at him. She said, “Ah. Ah, fuck.”

She could hear her own desperation. She could already feel her need gathering at the base of her spine. He moved his hands to hold the fronts of her thighs, and sped up a little, chasing for his own orgasm.

Then everything was confusion, as their bodies took control and nothing was slow or careful. They fucked as hard and fast as they could.

Debbie could feel a familiar hunger and need building in herself, while their bodies rutted, each pushing into the other, and they had no more sense of time.

A few minutes or an hour later she felt the wave she was riding break. Her eyes wide, she made her orgasm cry: “Tard! Tard-ah! Tard ah ben kit tol! Ah!”

His own sounds, just a few seconds later, made no more sense. Just a series of low animal growls, bear-like, and then he came, deep in her. She yowled with him as he spurted within her. She felt that, his liquid released in her. She was moved by it. And yes, she decided, she felt fed.

Masturbation Monday: Truth is rougher than fiction

Roland said nothing to that, but slowly withdrew his fingers, leaving a generous amount of the lube inside her. This time he coated three fingers with the lube, liberally, and pushed them into her. Her anus made the briefest resistance to this new, more challenging intrusion, and Teresa wriggled briefly on the desk. Roland said, “You all right? Comfortable?”

She smiled, which he wouldn’t see, then nodded. “You take a lot more care than Julian, that’s for sure. He just whacked it in. Poor Tessa. Though there was a hot side to that… On paper, anyway. And the last boy who had his cock up my arse wasn’t all that much better. So I feel cared for. Sir. You can be rougher with me if you need to be.”

“You’ll know when I need to be.” He pushed his fingers further into her muscled tube, past the second knuckle, and held them there for several moments. Then he pushed the fingers all the way inside her, as far as they would go. Her hips moved, and began to churn, back and forth, fucking his fingers while he held them deep in her.

But he withdrew at last, pressing a thigh against hers to make up for that absence, and lubed his cock. He pressed the head against her lube-glistened entrance, then held still. Teresa, still bent over his desk, raised her arse for him and tightened her hands into fists. She knew she was shaking lightly, trembling under him. It wasn’t fear. 

At last she made a questioning noise. Her anal muscles had accepted the head of his cock, and were holding it, tight but comfortably enough; but he wasn’t pressing forward. She wondered how much willpower that took. He said, “Would you like me to fuck your arse, Teresa?”

She made a gurgle of frustration and impatience. So he smacked her again. She was out of her floaty space, so the blow hurt and she yelped. She tried to push back, to impale herself on his cock, and he smacked her again, more firmly.

“Well? I asked you a question?”

Masturbation Monday: I endorse this plan

Roland put his hand on Teresa’s back. His cock pressed against her right thigh. He was very hard. Most of his mind had turned off, too, she expected.

He said, “Of course this is going to hurt. If it didn’t it wouldn’t be real, and it wouldn’t be sexy. So I mean to hurt you, Teresa O’Sullivan. Hurt you personally and particularly and deliberately. If I went lighter it’d just be mildly painful and feel kind of annoying. But if I go harder, your body responds to it. You won’t feel it as pain at all. Ok?”

He let her see his hand, suspended until she replied. She frowned. “That… might be right.” 

He held eye contact with her while his hand landed again across her arse, which was – if his phone camera hadn’t lied – already a blazing red. She could feel its heat. He leant down and kissed her ear.

He whispered, “So don’t you bother complaining that it hurts. Unless you want to turn me on.”

“Mmm. You’re such a cruel boy.”

He put his hand on her back to hold her down, and smacked her hard on the tops of her thighs, adding eleven very fast, very hard smacks while she wailed and squirmed.

“I don’t need to hear from you again, Teresa, until you thank me for your spanking when I’m finished.”

Teresa nodded, bowing her head. The explanation of why a hard spanking hurts less than a mild one was, she knew, Roland’s style. He liked a well informed submissive. But now he was being sexy billionaire Julian again, a man who never apologised and never explained. He pressed one hand just below the nape of her neck, holding her down across his desk while he resumed her spanking.

For a long time the room echoed with the sharp sound of Roland’s hard hand on Teresa’s soft, rounded, flesh and her laboured breathing and her occasional mews, which might have been little cries of pain, or pleasure, or both.

At about what she judged – she wasn’t counting – was the ninetieth or possibly hundredth spank he stopped.Teresae said nothing. She’d found herself, at last, in a strange, floating world of her own, an erotic world in which there was only a continuous heat and knowledge of her own acceptance of that.

It seemed an far away and unimportant fact, that he’d stopped spanking her.

She was aware of events – he pulled out the top drawer of the desk and took out a bottle of lubricant, pouring the gel liberally onto his forefinger and index finger – but she hardly thought of them as having importance to her. Until he pressed against her anal ring, and after a pause and a little more pressure she opened and admitted his fingers. She was still floating after her spanking, and very relaxed.

It felt pleasant and oddly comforting, though in a sense it was far away, barely connected to her. There was nothing Roland could do, just then, that she wouldn’t accept. She had abandoned herself to trust in him. He let the two fingers enter to the second knuckle, spreading the lube inside until she was slick and his fingers moved easily. Then he removed them, coated them again, and re-entered her.

This time Teresa’s eyes opened, and she made a languorous sound. “You’re going to fuck my arse. And give me your come. I, uh, endorse this plan. Oh! And thank-you-for-my-spanking, sir…”

Masturbation Monday: Turn off your mind, relax and float downstream

Something clicked in Teresa’s mind as she bent over her desk. She opened her eyes and mouth. In the book beside her bed, Tessa’s Duties, by Cerise Nates, the dominant billionaire Julian had called virginal secretary Tessa ‘little minx’, just like Roland had called her now. And that phrase, ‘Stretch your arms out sideways, and don’t move them’: that was word for word from her favourite passage.

She glared back at him, but without rising from his desk. “Hey! You bastard, you did read my books! You read Tessa’s Task! Are you being Julian?”

“I haven’t read Tessa’s Task.” She suspected that’d be true, though misleading. He’d only had have time to read a page and a half of it.

But it was her favourite page and a half. She guessed that Roland wanted her to have the experience of something she’d thought of, magically coming true. So she was generous to him, and didn’t call him on it. He smacked her again, harder. “It’s time you had a proper spanking, girl.”

“I’ve already had one! You just spanked me, remember?” It was odd having this defiant conversation with her nipples and nose obediently pressed against the wooden desktop. “And that was on the most tenuous excuse I’ve ever heard.” 

“Teresa, I said a proper spanking. You’ve had the first half. When you’ve had the second half, then you can say you’ve had a proper spanking.”

But he followed that nonsense by putting his hands back on her bottom, and dug his thumbs into the balled muscles, reaching and pressing into tension spots.

Teresa said, “Oof”, then moaned softly. The nonsense he sometimes spoke was only nonsense, but his touch was real and it felt good.

After a couple of minutes of firm massage he stroked in the deep valley between her buttocks, very lightly touching her cunt. Teresa closed her eyes and moaned while he ran his fingertips along her lips, getting them wet. She was wetter. She asked, “Is this the proper spanking?” She tried, for comedy purposes, to make it sound as if she hoped so.  

Roland only smacked her, hard, making that pistol-shot sound of palm on flesh. “This is a proper spanking.” He smacked her again, still hard, on the other side. “Now keep your arse up, Teresa. You look hot like that, and you know it. Also, you want to give me a perfect target.”

“Please don’t hurt me. Not … too much. Sir.” Her voice was little. Her voice sounded little to her, and she was surprising herself. Teresa didn’t know, just then, whether she was play-acting or if the spanks she’d already had, and the commands she’d already obeyed, with the promise of many more of both to come, had let her drift into a smaller, less powerful state of mind. There are pleasures in helplessness. Teresa decided to let go, turn off her mind and float, discovering and exploring downstream.

Masturbation Monday: Spurning my arse?

Teresa posed, hands and knees on his bed, ass up. Sher knew what would have to hen next: Roland would reach for her, get up onto his knees behind her. Then he said, “No.”

Teresa made a protesting noise. “Whuh?”

“Get up, girl. Off the bed. On your feet.” 

Teresa looked at him, frowning. “I am dealing with a madman, who appears to be spurning my arse.”

But she rolled over and put her feet on the floor. Roland rolled off the bed too, stood in front of her and held her so that she had to look up into his eyes. “Go to my desk, Teresa.”

“You want me to bring you something?”

“And turn to face it.”

“Interesting.” But she did as she was told. It occurred to her that he was easy to obey because he wanted her and he focussed on her. He never made her feel like she was on her own. If he did, she expected that he’d find that obedience, in a sexual content, is a fragile thing. He hadn’t told her to, but to show him where she stood on matters of command and compliance, she put her hands back on her head.

Roland stepped behind her now, and cupped her breasts, lifting them a little while squeezing her nipples between the forefinger and middle finger of each hand. Teresa pursed her lips, and hissed almost silently. The pressure on her nipples was just hard enough that she could be certain that he meant to hurt her, though not too much. 

She arched back so her arse found and pressed against his cock. He grunted, and she felt his cock growing at that contact, from semi-hard to absolutely, fully committed. He kissed her shoulder, then her neck, and stepped back. Debbie stayed where she was.

“Good girl,” he said. It was the first time he’d called her that. She knew, from reading books like Tessa’s Task, with the attractively domineering billionaire Julian and his submissive and virginal secretary Tessa, that those two words are more important than they might seem. Julian, in Tessa’s Task, had called Tessa a good girl after he’d spanked and buttfucked her.

People who get dominant when they’re turned on, like Julian and, it was now obvious, like Roland say that to submissive partners they approve of. If she didn’t want to be praised for submissiveness, “good girl” would only be offensively patronising. They’d be offensive words addressed to her or to any female person over the age of twelve, she thought, except in exactly this context.

SoTeresa froze for a moment, frowning. She considered whether to object, or deflect it with a joke. But part of her was simply pleased that he thought she was good. She felt Roland, behind her, freeze too. He’d be nervous, of course. It was as though saying ‘good girl’ was his job application, and he was waiting to see if he had the job. At last she smiled and nodded. She heard Roland breathe out, and he kissed her shoulder. She was still sceptical, despite the concessions she’d made on their previous night together. He might be more relieved than he should be. Still, he could have a trial period. Provisionally, he had the job.

He didn’t know about her reservations. He said, “Now put your feet well apart and bend over, Reresa. Nipples and nose touching that desktop. Stretch your arms out sideways, and don’t move them. Now, Teresa.”

This time the pause only lasted a second. Then Teresa obeyed, putting her hands on the desktop and lowering her body into that unmistakably submissive position. Obedience to that order was likely to turn out to be rewarding in multiple ways. She would be fucked, and fed. Now bent over, obedient and at risk of being called “good girl” again, she frowned, evaluating the position she found herself in.

She improved it, straightening her legs without being told, to present her uplifted arse for him.

So he stepped forward and put his hand on her bottom, caressing her left cheek fondly, then made claws of his hands, dragging his fingernails gently up from the crease of her thighs to the small of her back, and then returning to her thighs. Her skin goosebumped under that light touch. He rubbed her more firmly, then smacked her arse. 

“Are you – Are you going to spank me?”

“Of course. Would you try to tell me you haven’t been asking for it, little minx?” 

Masturbation Monday: Arguments for anal sex

Teresa kissed Roland, post-coitally lazy. “You know, if you fed your vampire girl, regularly, with your come, into my body and not into little bags that you throw away, I don’t think I’d have the urge to bite you. And then you could fuck me, face to face, without pushing my face away or tying me down.” 

“I like you tied down.” That was a compliment, one of the odder ones she’d ever been given, but she knew he meant it.

He bit her breast lightly. “And I think you like being tied down, too.”

“Yes, I do. But maybe not every time? You can tie me whenever you like, but it’d be nice to think you trusted me. That you don’t trust me – and I know you’re not completely wrong, given my record – but that’s still … kind of hurtful. ”

“Ok. Then get on the pill tomorrow. And the deal seems to be, at the moment, that we neither of us fuck anyone else. Except with the other’s permission, and then with a condom. All right?”

“Sir!” She said it like a soldier acknowledging an order. Teresa realised she only called Roland sir when she was asking for something, or she was happy with something he’d said. She knew he liked hearing it. In her own way, she thought, she was training him.

“So will you fuck me now? Without you wearing a stupid bag on your cock? I want just your skin and mine together, nothing between us, and your seed when you come in me. Sinking into me. Letting me absorb it. Feeding me. I mean, I’d kind of like that right now, sir.”

Roland shook his head. “I’m still not going to risk you getting pregnant, little Teresa. We’ll still have to wait.”

Teresa kissed Roland’s collarbone, still not quite healed from her bite. “Sir, I can suck your cock. I can swallow your come, taking it all down into me, and it goes through my body. I extract its energy while it’s in my stomach, and what I can’t use passes on into my alimentary canal. And out.”

“You want to suck me off? So that I come in your mouth? And that would feed you? All right.”

“No. I mean, yes, but not right now. That’s not what I want us to do. I’m just pointing out that you don’t have to think only of my cunt. You can fuck me hard, come in me and not get me pregnant. I’m amazed you haven’t taken my arse so far. You obviously like it.”

“I like your arse a lot.”

“So we’ve got the answer, sir, haven’t we? Fuck me up the arse, and I won’t feel I have to feed on your blood. And I won’t keep biting you. Your seed, my lover and my sir’s seed, that’s got to be even stronger than blood.”

Roland stared at her, as if she’d said something strange. Perhaps she had. She could see him waking up from his post-orgasmic stupor.

He said, at last, “You know, you’re right. I come in your perfect arse, and you won’t bite me. So that’s how it’ll be, the very next time.”

“No. Idiot.”

He said, “Idiot?” She glanced at his cock. It was still mostly down, but it was becoming engaged again, starting to take notice and thicken. He noticed her glance.

Teresa still looked at him as if he were a slow child. “Roland, I’m not talking about the future. I’m saying, fuck me up the arse. And come in me. I mean now, sir.” She rolled over and lifted herself onto her hands and knees. As she’d expected, the sight of her, presented, her arse up, inviting and demanding his desire, made the difference she wanted. He woke up.

“Your arse,” he said, “is perfect. And perfectly poised. And you’ve just made the weirdest argument for buttsex I’ve ever heard. But I endorse the no-biting project. Also, your arse has the sexual pull of about a thousand ships, I’d say.”

“So?” Teresa shook that arse at him.

Masturbation Monday: Taking his full weight

In Roland’s bed, Teresa rested her bottom on the sheets, finding the heat and slight soreness from her spanking unexpectedly pleasant, and lay back. Roland was only seconds behind her, and he said nothing. He lifted her knees and then parted them, his body pressing urgent between her thighs.

He still said nothing as he entered her, not slowly or gently. He fucked her energetically though warily, pushing her head to the side whenever she got her teeth too close to his chest.

Pleasure built within her, steadily and then suddenly, so she felt as if she’d been caught by a huge wave and she knew no way of getting down safely before it crested.

She opened her eyes, head resting back on the pillow, and gazed at him almost in terror.

Something gave in her, then, with Roland still riding her hard, held firmly by her thighs, his hand on her mouth to stop her from biting. Teresa struggled against him, making frantic, incoherent noises. He grazed her nipples with his teeth, and when that sensation reached her cunt and her brain she came. Her mouth wrenched open and she cried her orgasm syllables, “Tard ah! Ahh! Kit too!”

Roland grunted, as if he were pleased with her and himself, and sped up, while Teresa still felt aftershocks, a series of smaller orgasms. He tensed, making his own high-pitched sound through his nose when he came. They lay together, Teresa taking his full weight on her body, looking up at him tenderly and hoping to find that tenderness reflected back at her.

But Roland still had his hands under her arse, holding her tight and still moving in her. He was spent but not yet tender. At last he slipped them out and used them to support himself. Teresa took a deep breath, now that she could.

He smiled down at her. There it was: tenderness. Her heart was still pounding.

At last he rolled off her and lay on his back. Teresa took another hard breath, to celebrate, and let it out slowly. She kissed his shoulder. They were peaceful, and they had nothing to say. She turned onto her side and curled towards him, her leg over his, for comfort and possession. 

Masturbation Monday: Gentlemen take iPhotos

Roland had just told Teresa that he wasn’t going to let her into his flat any more, or not with clothes on. She wasn’t sure he really meant that. There were practical objections; she was sure she could think of several. But there was only one sexy answer, and just then the sexy answer was the only one possible. Teresa said, “Yes, sir.”

He knew, his grin said, that he was being silly. But at the same time, he’d meant what he said. He said, “My bedroom’s down that corridor. First on the left. Bed, Teresa. Now.”

Teresa turned to obey. She took a step, then stopped. “You should take photos of my arse.”

“I suppose so. This is your first spanking, at least from me­–”

“No, that makes it the first. At all. Don’t forget that you’re a weirdo. Statistically speaking.”

“But it’s not going to be the last, is it?”

Teresa looked back at him. “I’ve got a feeling it might not be.”

“So, hold still. You’re right: you should have a photo of your first. Put your hands on your head.”

“Yeah? Why?” 

Roland looked surprised. “In all honesty, I don’t actually know. It just makes you look sexy.”

Looking sexy was no bad thing. Teresa obeyed, and watched him gawk at her. Then he took her in with his phone camera. “Yeah. First photo. Teresa spanked. The day your life changed, and you became accountable to me.”

She turned back to face him. “Oh?”

“Don’t you think?” Then he suddenly looked much, much less cheerful. “Sorry, I should have said that better. I wasn’t really thinking, and I just blurted out what I feel. I’m sorry. So this is a question: do you feel that you’d like to be accountable to me?”

Her eyebrows lifted. “You mean you’ll beat my ass if I don’t do as I’m told?” She tried to make that sound absurd. She knew that in this room, with just the two of them, it didn’t sound absurd at all. It didn’t even sound wrong.

“That’s exactly what I mean. And more. Well?”

“Then yes, ok. I do. And more.” She thought for several long moments about what she felt like saying, and then said it. “Sir.”

“Also, I should take more photos of your arse right now because you look incredibly sexy. Now stand in the corner.”

Teresa moved to the corner, glancing facing back at him. “This better?”

“You look spectacular. Just … debauched.”

“Heh. I’m ‘debauched’. You’re the pervert. Can I move now?”

“No. Stay there. And look pretty. And… hold.”

She heard him taking photos, from different angles.

Eventually he smacked her bottom, lightly, with his phone. “Off you go, spank-victim. Bedroom on the left.”

Masturbation Monday: Dazed and bizarrely comfortable

Back in the taxi Roland had promised Teresa, into her ear so the driver wouldn’t hear, that her spanking would be the “can’t sit down” kind.

That was probably true, not because of pain but because sitting down would be the last thing she’d want to do when this spanking stopped. If it ever was going to stop. For now she was content to lie over his legs, tightly held, his hand landing over and over on her bare ass.

His hand was warm, comforting as well as mildly painful. Her arse felt glorious: warm, sexy, teased. She was in no hurry for this to stop. Neither was he, it seemed. 

But at last he rested his hand on her arse, and she could feel her own heat, and his. She expected her skin was the brightest red colour it had ever been. She’d never felt quite so confident that a man liked what he saw, as she did just then.

He said, “All right, Teresa. That was your lesson: once you’ve started calling a man sir, it’s not safe to brat him. Not without consequences. But you’re done now. Up you get.”

But Teresa was too dazed and too bizarrely comfortable to want to move.

She watched her hair brushing on his carpet, and wondered again what colour her ass was – scarlet? crimson? somewhere around that part of the spectrum – and what it would take to get him to start again. And then, suddenly and treacherously, he pushed her and she tumbled onto that carpet.

She slid her hands under her bottom and squeezed tight, glaring up at him. He only smiled down at her. “Stand up, Teresa, and take your clothes off. All of them.”

Teresa considered defiance. But the spanking part of the evening, though it had been hot, and fun, was over. And undressing was something she’d been meaning to do anyway. So she removed silks and velvet, finally dropping the long skirt he’d pushed up to her waist, and stood facing him in just her corset, feet slightly apart, hands at her sides.

Roland regarded her gravely. He was still seated, still fully dressed. Finally he said, “You are amazingly beautiful. And completely, utterly desirable. I’m going to take that corset off before I fuck you. Because it’s more comfortable for me that way.” He looked her in the eyes.

Debbie decided not to fight on the corset issue. For now. Because when he’d claimed to want it off solely for his own comfort he’d been winding her up, and, she guessed, hoping she’d rise to the challenge. “Yes, sir.” But she didn’t take it off.

So he raised the stakes. “I don’t think I’m going to let you wear clothes in this flat again. From now on, you strip when you get in the door. Understood?”