A First Class Degree in Debauchery

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He was now holding back as best he could but fighting a losing battle. So was Jude. She was so close and her new young lover had exceeded all expectations. Determined to finish with her favourite position as their tenth, she pulled him back to the bed and once more lay with her buttocks on the edge of the bed, legs in the air.

"Finish it, Kyle. This is fucking amazing. Go hard. Make me fucking scream. Get hold of those boots and fuck the shit out of me!"

He sank into her once more, her booted legs now up over his shoulders. The last two minutes of their first, utterly unforgettable fuck was a manic, almost depraved onslaught in which they both tore at each other with feral abandon. Jude turned the air blue with her exhortations, her final cry tailing off into an incoherent scream as Kyle shot load after load into her, fleetingly wishing he could see it covering her lovely face.

Kyle was on a different planet. He stayed inside her slippery wet pussy long after they had both orgasmed, chest still heaving from the exertion. Jude's eyes were glazed over, reminding him of the times he had seen Janey stoned. Except this was thanks to an enormous orgasm, not his ex-girlfriend's increasingly worrying liking for weed. Yet another thing he had conveniently overlooked in his lust for her.

Jude's body trembled and shook long after the event, her stomach muscles rippling as she came down. Kyle clung onto the spiked heels of her boots, her ankles up around his neck. His face nestled against her left instep, inhaling the aroma of the leather he was rapidly becoming addicted to. His back and buttocks bore the marks that the crossed stitches of those amazing boots had caused as they raked him, but he didn't care. It felt incredible and even the painful deep groove in his left buttock where she had dug a spiked heel in only reminded him of one of the highlights of his life.

Janey had done the same thing to annoy him in an attempt to make him stop. He knew without a shadow of a doubt that Jude had done it because she was enjoying it every bit as much as he was, spurring him on - almost literally - to greater efforts. His football coaches always had the mantra of 'no pain, no gain.' Until tonight he had failed to see the attraction. Now he fully understood it. He wondered how much more pain he could take in the pursuit of pleasure and hoped he would find out from this amazing older woman.

He was brought back to earth as she let out a huge sigh. "Fuck, Kyle - that was beyond words. I thought my dearest daughter was an idiot for cutting you loose. Now I know she must be a basket case. Oh and if you don't mind, at my age I am not so supple as I used to be. So please relinquish your hold on those boots you seem to have developed an unhealthy attraction for and give my aching legs some respite!"

Reluctantly, Kyle withdrew from her sticky snatch and gently lowered her booted legs back onto the bed. He caught his breath as he noted the huge wet patch soaking the silvery sheet between Jude's parted legs. A sense of pride welled up in him. She may have created the mess, but he had helped cause it.

And his cum was still deep inside her. Janey had never let him do that. It was always kept under wraps. It had felt so good to unload inside Jude and keep going in that frictionless passage until he had nothing left to give.

Jude's smile told him everything he needed to know. It had been utterly stunning for him, and she had loved it too. She took his now flaccid, sticky cock in her gloved hand. Once more that incredible contrast between the gauzy material and the softness of her fingers blew him away. As she licked and sucked him clean, her other hand dug deep and came up slathered in his cum.

"A taster for what is to come, Kyle."

She let his jizz drip from her fingers into her mouth, purring in ecstasy as she tasted him for the first time, the mesh of her other glove rubbing on his already stiffening cock. Kyle looked on, awestruck. It was beyond his wildest dreams. Jude sucked her fingers until they were clean, then leaned up on one elbow.

"Oh Kyle, we've only just begun. Barely scratched the surface." She ran a hand down his back and he winced a little. "Well, maybe a few scratches. These boots have drawn blood many a time!"

He could barely speak. "If you are a vampire, take all the blood you need, Jude."

She rose from the bed and kissed him. "I'll certainly take all of something I need. But before I do, I know this outfit is hot as all get-out, but it plays havoc with my bedding. I shred sheets like most people shred paper. I need to change and clean up, but your reward will be to see your next load anoint my face and drip down onto my tits." She tickled him under the chin. "Don't go anywhere. I'm still hot as fuck naked!"

She stood by the bed and pulled a face, pointing downwards. "Look what you did, dirty boy!"

Kyle smiled as a dribble of cum slid from her still puffy pussy lips and trickled down her inside thigh. Jude scooped it up and swallowed it with a flourish then turned, waved her shapely butt at him and left the room. He sighed deeply and waited for her return.

She was gone a few minutes. At least the kit was easier to get out of than into. Janey's old room was now her overflow wardrobe and bit by bit, she was bringing her stuff back from Greta's and adding to her collection. No way was the toxic bitch getting her room back even if she begged. Jude had big plans for that room and with Greta's help, she would soon boast a dedicated sex room of her own.

Once divested of her finery, she did a quick clean-up in the communal bathroom. Nothing too elaborate -- after all, she was going to get dirty again very soon. A quick dash back to pick up something from her dresser, then she stood in the doorway of her bedroom, leaning nonchalantly on the doorpost, hair now over one eye in a coquettish pose. It was time for her little teaser.

"Will I still do?"

"Oh yeah!" Kyle groaned as he saw her fully naked for the first time. She did a little twirl, laughing as her hair flew and he caught a glimpse of her tramp-stamp that had been hitherto covered by latex. She held the vape pen she had picked up across the hallway to her mouth and his stomach did a little flip as she blew out a long, thin stream of vapour.

She held up the vape, a look of concern on her face, barely able to conceal her amusement. Janey's summation of his reaction was for once accurate. He looked like a puppy about to have his tummy tickled. "Sorry, you don't mind do you? Still have a few bad habits to go with all the good ones."

He shook his head. "No, used to it with Janey, don't stop on my account."

Inwardly, he screamed at her.'Please don't stop on my account. Come and lie next to me and do it where I can see it properly.'

To his delight, she did exactly that and lay down next to him.

He had loved watching Janey vape, although he hated her smoking - especially the weed which she seemed to consume in ever-increasing amounts. He was sure she was occasionally on something else as well but couldn't be certain. But as everything with Janey, if Kyle didn't like her doing it, she did it all the more. She took delight in smoking close to him even though she knew he hated it and seemed to revel in telling him she had just fired up a joint before they met. Of course, it was as if she had a sixth sense that he liked watching her and her friends vape. There was just something so sexy and alluring about it. He couldn't put his finger on why but seeing their pursed lips as the thin streams emerged just turned him on for some reason.

But she did it almost surreptitiously, sneaking outside with her friends or on her own for a quick vape almost hiding it from him as if taunting him with it. He would have given anything for her to vape on his erection and now there was a chance it might happen. Jude had already said nothing was off the agenda. Maybe he would get to fulfil another dirty little fantasy. But not tonight. He had enough to contend with as it was, so lay next to her and watched on contentedly as she blew little puffs of vapour into the now gathering gloom of the evening.

Making out with her naked was every bit as good as in her fetish gear. Their second time was more leisurely and less frenetic -- at least until the end - as they alternated between mouth work and slow, languid fucking. In that blissful half hour, they used a few more positions but his favourite was with Jude on top, grinding down on him in a circular motion as he tweaked her nipples and tugged on her clit stud. She was so expressive -- her hair tossing, nostrils flared, eyes blazing as she switched between gentle caresses and tirades of sheer, unadulterated filth. It was so good to be fucking without a condom, but she insisted on using one when she offered him her darker passage after the longest and best fuck of his life.

She took him effortlessly -- none of the nervous fumbling and tentative prodding he and Rosie had gone through, despite her liking for anal sex. Jude was obviously well-versed in the art and of course had the correct lubricant, which Kyle and Rosie had never even considered. It made for a much more pleasurable experience and the way she squirmed in delight as he fingered her, spouting whispered obscenities, filled him with joy.

She came hard as he thrust into her, rutting like a stag at her insistence, spitting the words out through gritted teeth, urging him to 'fuck my fucking arse' or 'fuck me harder.' He did as he was so politely instructed and her fingers joined his on her slippery snatch as he hammered into her until she screamed out in ecstasy, her face buried in a pillow, the silky sheets balled in her right fist. He kept going until she released the crumpled sheets and held up her hand.

Her voice was hoarse. "Fucking hell, I do love a good arse full, and that was a fucking good arse full. Now let me think, how can I possibly repay you, young Kyle?"

She repaid him by tugging off the condom with her teeth, then blew his mind with the ferocity with which she went down on him. After a couple of minutes of absolutely feral cock-sucking she grabbed his hands and put them on each side of her head as she had done earlier. Her eyes blazed up into his, her voice coming in gasps. "Just fuck my face like you did my arse, Kyle. Hard as you like. Pull my hair, slap me with that lovely cock. Come all over me."

Once more he did her bidding, this time holding her head in a vice-like grip, twisting her hair and pulling it. He was reluctant to slap her, until she pulled off him. It took some effort, given the way he thrust into her mouth. She took hold of his cock and slapped it around her cheeks and mouth, great gobs of saliva dripping down her chin as she gasped for air. It was all too much for Kyle and he let go with a guttural roar and shot his load over her flushed face and hand as she jerked him, tugging on his balls with the other hand.

He gazed down in wonder as for the first time, he saw a woman's face coated in his jizz. Rosie had never let him do it, although she and one or two girls had let him come in their mouths, and of course Janey had barely touched the thing with her precious lips.

But this was on another level and Jude grinned up at him, her left cheek glazed, fingers dripping with it and sucked the last from him as he shuddered under her tender ministrations. She opened her mouth, tongue and lips coated with it and sucked on her sticky fingers. As she had promised him earlier, she let it slide down from her chin onto her tits, hanging in long strings before breaking away and landing on those magnificent orbs with a satisfying plop.

She played with it for long minutes, telling Kyle how good it felt to be covered in his mess, how good he tasted and how she wished Greta was there to share the spoils. He watched her in sheer disbelief as she rubbed it around her face and breasts until they were glistening in the candlelight. A hank of long hair stuck to her face as she blew one last cum bubble and with a cute, girly little giggle, ran into the en-suite bathroom to clean up.

Two minutes later her smiling face appeared around the door frame. "Did I miss any?"

Kyle pointed to her shoulder with a grin. "Bit there and there's a blob in your hair just above the ear."

Jude merely shrugged. "Never mind. I've driven home from parties with more left on me. Besides -- plenty of time to gather more before I'm done with you!"

She lay back down on the now rumpled bed and the manic ferocity of the last ten minutes gave way to soft caresses and she kissed him tenderly. "Kyle, you are a remarkable young man and we both obviously enjoyed that and share some mutual tastes. How's about we continue this on a casual basis? At least until you're in a relationship once more. Janey may not like wearing leather in bed and her guys going at her like porn stars, but her mother... yowza!"

Kyle stroked her hair. "I'd be honoured, Mrs Coughlan. However long or short, sign me up. That was just incredible. So come on, how the hell do you know my dark little secrets?"

She hooked a thumb towards the window behind her. "I overheard Janey a few weeks ago as I lay in this very spot. She was down in the garden on the phone to a friend. Heard her say a few things that pricked my interest and made me hope I'd get to meet a hot young guy again who wanted to fuck a girl in boots. Then she said she was leaving and going to live in Edinburgh. Let's just say I was quite happy that evening and even happier when you turned up the other day."

They made out again before they fell into a deep, satisfied sleep and Kyle woke to the blissful feeling of soft lips caressing his morning glory. It was a long, languid, gentle fuck that made him wonder if he had dreamed the previous night and the ferocity with which they engaged each other.

This time when they reached the front door and Jude hugged Kyle, he was quite happy to let himself harden against her and she ground into him as they kissed. No embarrassment this time -- just a complete euphoria at what they had done together over the last twelve hours. It had been a revelation to him and despite her words the night before, he prayed it would not just be a one-off.

Jude broke from their clinch and stroked his hair, still damp from the shower. "Fuck, Kyle that was a great night." She grinned. "This morning wasn't half bad either. There's no way I want that to be the one and only time." She held out her hand. "Still wanna be fuck buddies?"

Kyle took it, his heart singing. "Absolutely, but I think I still have a lot to learn."

Her smile was wicked as she stroked him down below. "Oh you have, but you learned very quickly last night. I'll be in touch, I promise. Let's just take this nice and easy, yeah? No pressure on either side and if you get a new girlfriend and want to call it a day, I'll be a big girl and understand. I'll be disappointed, but I'll be cool with it. Just nice to have a fine young man who shares my dirty little predilections for a change. Now go before I drag you back inside and knock that big boy down again!"

She went back into the living room and crashed down on the sofa desperately wanting a glass of wine, but more pertinently, Kyle's cock in her mouth once more. But even ten-thirty was too early for Jude to open wine. It was no good, she would just have to wait.

For another eight hours at least.

She would miss Greta at the little soiree she was about to attend up in London later that evening. She had just ravished a twenty-one year old hunk - and probably changed his life - but she was still jealous of Greta. The Berlin club where she would be strutting her stuff later was a notorious den of iniquity and it was highly likely the woman would get to engage with more partners than Kyle's number of years on the planet.

Jude's planned six-up seemed tame by comparison. At least she wouldn't be in danger of drowning in cum and piss like Greta.

She made coffee and tried not to think about sex, but it was no good. She went out on to the patio and made her plans for Kyle for the forthcoming week or so. She would need some new equipment to fulfil her plan. Luckily she was a long-term customer of a very a discrete and reliable website and now Janey was out of the picture, she could attach shackles and restraints to her bedhead to her hearts content. She drank her coffee and dialled up the website on her tablet. Fifteen minutes later, she had ordered a few little treats for Kyle.

And of course they would be treats for Jude as well because Jude just loved that kind of thing.

She threw herself into her soiree with such abandon that she almost missed her stop the next day on her way back home on the train. She then texted Kyle. His workplace was only half a mile from her house. There was a long, potentially unpleasant conference call planned for the Wednesday morning.

She would need a little stress relief after it.

Kyle would provide that stress relief with a hard, fast rabbit fuck over her desk.

Things were looking up!

Five

Kyle was thrilled to be called back into action so quickly. He spent the weekend out with friends and was called a lightweight when he refused to go on to a local club where he had been lucky on a few occasions previously. He had to admit that there was the thought at the back of his mind that if he did score, he may cross a line somewhere. He just hoped such an incredible time with Jude had not spoiled it for the future and that 'normal' sex would seem mundane.

It was certainly not mundane on the Wednesday lunchtime when Jude leaned over her office desk, lifted up her short skirt and Kyle got to work. Luckily his employer allowed casual dress and his habitual shorts made things a little easier as he slammed into her from behind, the desk rocking with their efforts. Her hair was held up in a big plastic clip and she wore dark rimmed glasses and seemed a million miles away from the woman who had taken him to new heights only days earlier. But she was still absolute dynamite, from the first few minutes on her knees, getting him 'fit for purpose', to rolling on a condom with practised ease. She apologised for using it, but as she said, cleaning up before an afternoon of work was not a pleasant prospect. But fucking before an afternoon of work was a very pleasant prospect and, keen to preserve her voice for her afternoon meetings, Jude's whispered obscenities were almost more of a turn on than her loud screams.

He left her, slumped across the desk, fingers white where she gripped the far edge of it. Her glasses hung from one ear and her hair needed to be pinned back up. The condom hung from her document holder and she hoped she would remember to remove it before her next call. She spoke one breathless word as Kyle reached her office door.

"Friday?"

Kyle nodded his agreement. "Friday."

Beginning with that very day, they settled into a nice little routine over the next couple of weeks. Depending on Jude's commitments, they would have a steamy evening session which usually left Kyle reeling with its intensity.

But he also relished their lunchtime quickies, which were announced by text message in the course of the morning. It was a five minute drive to her house, with Kyle desperately trying not to break the speed limit, followed by a memorable copulation, the style of which was dictated by her text.

It always began with a GIF of a stress ball being squeezed. The number of 'kisses' that followed it determined the intensity. One kiss was a slow-burn grind with her on top. Five was a table-trembling rabbit fuck and three meant a mutual oral session. They were the worst for Kyle, despite her skills in that department. He almost had to scrub his beard off afterwards to ensure he went back to the office not reeking of her musky scent.

123456...8