Authors: Lisette Ashton
Russel groaned with excitement, wondering how close he was to climaxing again.
‘Not yet, though,’ Helen told him, a mischievous smile twisting her lips. She rubbed his cock once more against her pussy lips, delighting in the hot, wet friction. ‘You haven’t dressed up yet,’ she reminded him. ‘And according to the rules, I can’t make love to you unless you’re another female.’
‘Do I have to do this?’ Russel asked unhappily.
‘No,’ Helen said, her finger still playing with the lips of her vagina. ‘You can refuse to dress up and play my game if you want to. It will just mean you don’t get to screw me, and you spend some time in the black room.’ Her smile was as cruel as any Vanessa had ever graced him with. ‘The choice is yours, Russel.’
Blushing furiously, Russel stepped from the bed and began to sort through the discarded pile of Helen’s clothes. ‘Which items?’ he asked dully.
‘All of them,’ she said. ‘Knickers, stockings, bra, skirt and blouse. And don’t ladder my stockings, or you really will upset me.’
Mortified that he was obeying her, Russel picked up the knickers and tried to decide which way they went on.
‘Sniff them first,’ Helen snapped crisply. She flopped on to his bed and smiled up at him as she issued the command. One finger toyed idly around her moist lips whilst the other teased a nipple between the index finger and thumb. ‘Sniff them and tell me how good I smell.’
Russel’s length hardened furiously. He sniffed the gusset of Helen’s pants and inhaled the enticing aroma. Maddeningly, he felt his balls tighten with anticipation and he sniffed them a second time, without her having to command it. The fragrance was soft, sweet and musky. It was a reminder of the scent he had caught on her finger, before licking it clean. For a moment he felt intoxicated by her bouquet.
‘Put them on then,’ Helen instructed lazily, still playing with herself. ‘There’ll be plenty of time for you to enjoy the source of that scent later on.’
Reluctantly, Russel moved the pants away from his nose and stepped into them.
Helen watched him critically as he dressed, her finger moving with a quickening tempo as her appetite for him increased. He was not the handsomest of men. His thin frame and boyish looks gave him an androgynous appearance that was unremarkable, save for the huge cock between his legs. She watched as he tried to conceal this huge member in the skimpy white-cotton panties she had been wearing, and suppressed a smile when she saw how impossible this was going to be. Unmindful, Russel rolled the stockings on to his legs and then fastened the bra around his narrow chest. He slipped into the blouse Helen had worn, before pulling her skirt on.
Helen bit back a sigh of delight as she studied him. His cock was still twitching at the front of the skirt, creating a give-away bulge that was far from discreet. However, she had to concede that he made a fine-looking woman. His legs were too shapely for a man. Clad in the sheer black stockings, they looked desirably good. She glanced at his face and saw that he was crimson with a combination of humiliation and embarrassment.
‘There’s some lipstick in my blouse pocket,’ Helen told him, her fingers tickling frantically on her exposed clitoris. ‘Put some on,’ she gasped between deep breaths.
For a moment, Russel could not move. He was captured by the vision of Helen masturbating as she watched him. An expression of eagerly anticipated delight strained her features as the first trembling of an orgasm swept through her. Every muscle in her body seemed to tense and she bit back a groan of deep, guttural excitement as she climaxed.
Russel felt his cock stiffen hungrily as he eyed the glistening slickness of her wet hole. A part of him wanted to grab his cock and jam it into her as vigorously as she would allow. He did not doubt it was something Helen would want, and he felt sure they would both enjoy it.
However, Helen had not asked him to do that and Russel was already beginning to learn his place in life. It was a place where such impulsive desires were not allowed, not for him anyway. His role was to do as his superiors told him and even though she was just a fellow trainee, Russel realised Helen was still superior to him. He watched the last tremor shake itself from her body, then moved to the mirror at the room’s dressing table. Without studying his reflection, he applied the lipstick to his mouth, coating the lips adequately with the garish red colour.
‘What a lovely young woman you are,’ Helen said, giggling nastily. She climbed off the bed and walked swiftly over to him. Without shoes on, they were the same height and she had no trouble planting a kiss on his painted lips. Her tongue explored his mouth as her hands went behind him. She cupped his buttocks with her palms and squeezed him against her. The swell of his jutting dick pressed rudely against the flat of her stomach. Lasciviously, she rubbed her naked stomach against him, feeling the length throb hungrily against her.
‘Why, tell me, young woman,’ she began theatrically, ‘what is that bulge at the front of your skirt?’
Russel frowned uncertainly. He did not know what to say and knew he was just the plaything in Helen’s game. He tried a hesitant smile and a half-shrug, then watched helplessly as Helen knelt down and began to lift his skirt.
‘My God!’ she exclaimed in mock-horror. ‘It looks like you have a cock down here,’ she told him. ‘It looks like a cock, and…’
Russel felt her fingers teasing his rigid member from the cotton panties it was stuffed in. She gripped it firmly at the base and allowed her fingers to roll slowly back and forth along the entire length. He bit his lower lip in anguish, fighting to stave off the impending climax.
‘…and it feels like a cock,’ Helen told him. She paused for a moment.
Russel felt her tongue tracing lazy circles around the head of his knob. Her hot breath warmed his length with a slippery wetness that he knew was as good as her pussy would be. The tip of her tongue teased its way into the hole at the top of his prick, then she took him in her mouth and began to ride him with her face.
‘Good heavens!’ she gasped, standing up to face him. ‘It tastes like a cock, too. It really must be a cock. You’re a man!’ she declared.
‘You know I’m a man,’ Russel replied sullenly. ‘It was your idea to dress me up like this.’
Helen slapped him sharply across the face. ‘How dare you suggest such a thing?’ she said sternly. ‘You’re a man dressed up as a woman, and you need punishing for that.’
‘No,’ Russel began quickly. ‘That’s going too far. You’re not punishing me. I’m not having that.’
‘You’ll have whatever I tell you,’ Helen told him menacingly. ‘Unless,’ she added with forced sweetness. ‘Unless you want me to get one of the mistresses to punish you instead? I could enjoy that just as much.’
Russel watched helplessly as Helen moved towards the door of his room and reached for the handle again. Let her go, a part of his mind encouraged him silently. Let her go, and get the punishment over and done with.
And never see Mistress Vanessa Byrne ever again, he thought miserably. He was left wondering how he could have been so stupid as to let her get so close to the door again.
‘Wait,’ he hissed angrily.
Helen turned to face him, her sly smile broadening. ‘Wait? Why? Do you want me to punish you, rather than one of the mistresses?’
He nodded dumbly.
‘Say “Yes please”,’ Helen told him.
‘Yes please,’ Russel replied sullenly.
Her smile widened and she moved away from the door. ‘I think there’s a reason why you want me to punish you, rather than one of the Mistresses. I’m right, aren’t I?’
He nodded.
‘You probably think I’ll go easier on you than they would, don’t you?’
‘No,’ he began. ‘I just…’
‘Well, I won’t,’ Helen assured him, not listening to his reply. ‘If anything, I intend to punish you as severely as I can.’
Russel trembled inwardly. He wished his cock would behave normally when he was subjected to news like this. He thought it would have been appropriate for his excitement to dissipate at the threat of punishment. Instead, he found his dick standing harder than ever. Miserably, he realised that a part of his mind was eagerly anticipating the correction Helen had planned for him.
‘What are you going to do to me?’ Russel asked warily.
Helen smiled and rubbed her hand against the thrusting stiffness of his erection. It was a huge cock and she found herself unable to resist the urge to touch it and play with it. ‘I could do a lot of things to you, if I wanted,’ she told him. ‘But I wouldn’t do anything that would stop this cock from being hard, you do know that, don’t you?’
Unhappily, Russel nodded. Helen wanted him as desperately as he wanted her. The only difference between their desires was that Helen wanted to humiliate him before they did anything. It was a difference that he did not particularly like, but he was happy to accept it, considering the prize that awaited him at the end of the evening.
‘Now bend over, raise your skirt, and drop your knickers,’ Helen told him crisply. ‘I want to see your backside.’
Russel’s cheeks burnt so fiercely it felt as though they were ablaze. Ashamed by his own servility, and mortified by the arousal which it inspired, he did as he was instructed and bent over. His nose was close enough to the hem of Helen’s skirt for him to detect the faint aroma of her perfume on the garment. Again his cock twitched hornily. He had not bothered to remove the pants and he felt Helen’s fingers tease the fabric away from his buttocks and tug them slowly downwards.
She stroked the downy hairs that covered his arse with a tenderness that bordered on being loving. Her fingers played carelessly around his anus, touching the rim heedlessly, before delving into the feathery swatch of his pubic bush. She cupped his balls in her hand and squeezed them gently in her palm. ‘I wouldn’t want to hurt these, either,’ she told him earnestly. ‘Although I could, if I wanted, couldn’t I?’
‘Yes,’ Russel murmured quietly. For the first time, he was beginning to realise that the threat of pain was almost as powerful an aphrodisiac as the actual experience. Being rolled between Helen’s fingers, his balls felt decidedly vulnerable, yet he felt his excitement mounting.
She moved her hand away and began to stroke his long cock. Her wrist brushed against his arsehole as she did this, thrilling him with the unexpected stimulation.
‘You like that, don’t you?’ A dark smile crossed her lips. ‘I can see why.’ ‘I’m tickling your bum-pussy, aren’t I?’
‘I…I…’ Russel faltered. His cheeks felt bright red with shame and he could not have thought of anything sensible to say even if Helen had not interrupted him.
‘Don’t bother denying it.’ She laughed gaily. ‘The clothes suit you, just like they suit your desires. You want to be screwed up there, don’t you?’
‘No,’ Russel denied furiously. He tensed himself against the threat of an orgasm which longed to burst out of him. Every muscle in his body tightened in anticipation of the climax but, for the moment, his willpower seemed to have the upper hand. The moment passed without him ejaculating. Russel realised it had been close.
Helen appeared not to have heard him. ‘Mistress Stacey has a strap-on dildo in her rooms,’ Helen told him in a discreet whisper. ‘Perhaps I should go and get that, then come back here and give you a good hard shagging.’
‘No’, Russel gasped, wishing her words were not so arousing.
‘Perhaps I should ask her to come back here and use it on you,’ Helen suggested coyly. ‘She’s had more experience of wearing it and I bet she’d know just how to use it up this tight little bum-hole of yours.’
‘Please! No!’ Russel implored her. ‘Don’t get Mistress Stacey. Please?’ There was a pathetic, faltering note in his voice as he finished this last sentence, turning it from a request to a plea.
‘But feel how eager you are for it.’ She slid a finger smoothly into his arse, parting the hole easily.
Russel groaned as he fought against his climax again. His cock felt as though it were about to burst, and he knew that if Helen deigned to touch it at that moment he would shoot his load all over the skirt she had made him wear.
She slid the finger inside him as deep as it would go. When she slowly pulled it from him, the movement forced a shiver of delight to course through his entire body. ‘Sniff it,’ she commanded, holding her finger in front of his nose. When Russel moved his head disobediently away, she grabbed his hair and forced his head close to the finger. ‘Sniff it, I said. Now!’
Tears of shame pricked at the corners of Russel’s eyes. Obediently, he did as Helen told him and sniffed the finger she had used inside him.
‘Recognise the scent?’ Helen asked softly. ‘It’s the aroma of a hole that needs satisfying, isn’t it?’
Russel groaned and stammered a reply. ‘It…It is,’ he agreed.
‘Do you want me to fuck your bum-pussy?’ Her lips were a whisker away from his ear and Russel felt the delicious warmth of her breath against his neck. ‘Do you want me to use my fingers, and fuck your bum-pussy?’ Helen asked again.
‘Yes!’ Russel gasped excitedly. ‘Oh! Please! Yes!’ he implored her, wanting this more than anything he could recall.
‘OK,’ Helen said obligingly. ‘I guess I can do that for you. Move over to the mirror and stand in front of it: Legs spread slightly, hands on either side of it.’
Russel moved as she asked, shuffling his feet in small steps because Helen had not given him permission to step out of the panties that pooled around his ankles. He stood in front of the full-length mirror, the raging force of his erection lifting the skirt he wore so that his penis pressed against the cool glass surface.
‘You’re very obedient,’ Helen observed quietly. ‘I’m going to enjoy having you around the hostel.’
Russel sighed, knowing this had all seemed too good to be true. ‘I thought you promised it would just be this one night,’ he said softly. He could see her in the mirror behind him and was aware of the cruel tinge to her smile.
Helen’s grin widened. She caressed the cheeks of his backside before replying. ‘Are you telling me you don’t want to feel this again?’ She asked the question as she slid her index finger slowly into his wanton arsehole.