Chapter 29.
There really was no way out of it. The women shooed him aside while they prepared an armchair for Lavinia. He took a seat as far away as he could and observed proceedings. Lavinia’s breeches looked like fabric, but the way they stretched when she moved… He wondered if she actually wore them to go riding. She noticed him looking at them.
“Do you like them, Bobby?”
“They’re not…rubber?”
“Yes. They look like regular breeches, but they’re latex moulded to look like fabric.”
“Have you ever worn them out?”
“Yes. When it’s wet or muddy.” She gave him an arch smile. Maybe I’ll even wear them tomorrow, to set off my nice shiny boots.”
For some reason Bobby found the idea remarkably exciting. He shivered slightly, and he felt another drop of juice ooze from his pen-is into the teat of the condom. His ears started to burn. But he didn’t know the half of it. Just as well. Nicole herself had been instrumental in obtaining two pairs of latex breeches for Lavinia from Fantastex, these and a second pair in petrol blue. At Lavinia’s request, both pairs were equipped with an internal integral rubber dil-do, of medium length and girth, with a smooth enlarged head and raised ribs, and a small stalked anal egg. Whilst not much interested in men, Lavinia possessed a powerful and somewhat perverted sex drive. She regularly went out riding with groups, usually all female, and she loved the feeling of secretly riding herself into orgasm without the others realising, especially as, in her latex breeches, all eyes were usually on her. At a walk the dil-do just moved gently round and round, back and forth, inside her. At the trot the movement became more pronounced, and if she wanted to feel it actually fuc-king her she would go into a rising trot. Once or twice she had been unable to supress a cry of pleasure as she climaxed, but had managed to explain it away by claiming she was suffering from cramp. She always returned from these rides totally sated – at least for a while – and at peace. Sometimes, reflecting on the day, should wonder if a certain member of the group had realised what was going on. That thought was in itself enough to have her masturbating furiously. She thought of herself as a “secret exhibitionist”, someone her colleagues might be suspicious of without being able to be certain about anything. And now, her latest deviation. She was already excited about the evening’s venture. Her heart was beating fast, and she was having to resist the desire to squirm on her dil-do. Having Bobby on his knees going at her boots had multiple attractions. It would be like having him make love to her, but in a way that she, as a fellow fetishist, was sure would be more to his taste as well as hers. Once he overcame his initial nervousness she was sure he was going to put up an enthusiastic performance; it would be so hot having him down on his knees like her little slave boy; and finally, the whole thing was completely off the wall, and such things always appealed to her.
As for Bobby, he was in a state of panic. This wasn’t happening, was it? But it was. The ladies had pulled forward an armchair and covered it with a wide sheet of natural latex, which extended a metre along the floor in front of it. Lavinia put her glass on the mantlepiece and lowered herself into the chair, her breeches squeaking slightly on the latex sheeting. She placed her hands on the arms and snuggled her well-rounded behind as far back as it would go, so that her boots rested neatly against the front of the chair. Then she looked at Bobby and smiled invitingly.
“I’m ready,” she purred, seductively.
Nicole and Sarah had taken their places on either side of their friend, Nicole on a chair, Sarah sitting cross-legged on the floor, each with her phone at the ready. Sarah, staring brazenly at the plump gleaming sausage projecting from the front of Bobby’s pants, wore such an expression of delighted expectation that he put his hands down to try to hide it. Nicole misinterpreted the gesture.
“Good boy, Bobby. Yes, you can take the condom off now.”
“No, I…”
“Please hurry up. Lavinia’s waiting. Come on!”
He made his way slowly to her chair, looking anywhere but at her, and suc-king his lips between his teeth.
“Come, on, Bobby… Really! On your knees, quickly!”
He sank slowly to his knees. Nicole, impatient, reached out and pulled off the condom by the teat. It came off with a snap, making his pen-is flick back in the opposite direction, sending a little shower of Bobby-juice over Sarah’s jeans, and leaving a string of it hanging from the tip..
“Ooops! Sorry darling!”
She dropped the condom onto the latex sheet. Lavinia was smiling affectionately at him. He was kneeling back on his haunches, his knees just touching the toes of Lavinia’s boots. His could smell the pungent boot rubber. He was trembling, his heart was pounding, and his swollen prick felt as though it would burst. Lavinia leaned forward and took him by the forearms. She slid her hands up to his, and pulled them towards her until they were resting on her thighs. The end of his oozing member was inches from her boots; he was thrusting out his bottom to prevent it actually making contact. Lavinia held his hands tight.
“Kneel upright, darling,” she murmured gently. “Let the tip just brush my boots. Come on, sweetie, don’t be shy. That’s right…a little more… There.”
Bobby gave a gasp as he felt the head make contact with the rubber. It was smooth and cool. He looked down. The string of pre-c-um had attached itself to Lavinia’s right boot, and the head of his pen-is was pressed gently in the furrow between the two.
“Now, darling, I want you to push forward…very gently… See if you can slide it between my boots… There should be a little gap there… That’s it… A little more… Well done!”
Lavinia’s heels and knees were pressed together, but at her calves there was a little gap, just big enough to accommodate the slippery head. As it slipped between the two columns of smooth rubber he caught his breath, and a sudden flow of juice helped to lubricate its passage. Lavinia had let go of his hands and was now stroking his bare arms comfortingly. He gripped the tops of her rubber breeches and tried to master his agitation. He bit his lip, and allowed his coc-k to slide out.
“There, darling….take your time. Now again…?”
He felt dizzy. He hesitated, trying to regulate his breathing. Blinking, he looked up at Lavinia. She was smiling reassuringly. She patted one arm.
“You’re a sweet boy, Bobby. Relax a little, if you can. Don’t feel pressured. Remember it’s only my boots you’re making love to…not me…for the time being, anyway…”
What did that mean? Making love? “S-sorry, Miss Lavinia…” He blinked with embarrassment, and took a deep breath to calm himself. Obediently, he pushed forward again. It slipped in easily, a little further this time, and a spasm of exquisite pleasure ran through his body. He gulped. A third thrust, and a fourth. It took so little effort, and the sensation was breathtaking. Within less than a minute it was as if all his nervousness had evaporated, overwhelmed by sheer sensual bliss. His thrusts became controlled and regular, in and out, in and out, of that smooth, slick cleft. He was lubricating freely now, the steady movement working his juices into a lather, clear juice and white froth trickling down the insides of both boots. He began to lose all his self-consciousness.
“M-miss Lavinia!” he gasped. “Like this? Is this right?”
“Bobby, yes! I knew you could do it. Does that feel all right?”
“Oh, yes, miss! It feels amazing!”
And for me, thought Lavinia, pressing her posterior down onto her dil-do as hard as she could. It was really like he was fuc-king her. She had a nice fat little coc-k in her pussy, and another thrusting desperately at her best boots, its owner hanging onto her thighs for dear life. This was better than ordinary sex by a long way. She watched Bobby’s face intently. His eyes were tight shut, his mouth open in ecstasy – the face of a boy having proper sex for the first time. She knew from what Nicole had told her that for him also, this was the pinnacle of his desire. Fetishism always trumps straight sex – she of all people knew that only too well.
But he mustn’t c-um – not yet, anyway. She wanted it to last as long as possible, and for her to c-um at the same time..
She leant forward and stroked his cheek lingeringly with her hand, touching his lips with her latex-sheathed thumb.
“You’re doing a very good job, Bobby… But I want you to enjoy your work – that’s very important to me, because I want you to go on being my personal boot boy – so please do what is most pleasurable for you, at a pace which is comfortable. Then not only will my boots be well attended to, but you will want to work for me on a regular schedule. I hope you agree with me.”
Bobby stopped his thrusting.
“Oh, yes, Miss Lavinia,” he said excitedly. “I would love to be your permanent boot boy, of course. It would be an honour. Please don’t concern yourself about me – I love working for you so much!”
“I’m so happy to hear that. We should draw up a contract, too. Well, please continue. Please take your time, and by all means be creative!”
Thus encouraged, Bobby resumed his task. Having taken on board Lavinia’s advice, he removed his right hand from her thigh, took hold of his erection, and rubbed the oozing head all over the fronts of her boots, smearing them with his slimy juices!
“Bobby!” admonished Nicole. “That’s disgusting. You’re supposed to be cleaning Lavinia’s boots, not, making a mess of them!”
Bobby, revelling in the feel of the cool, smooth rubber against his overheated coc-k, took no notice. A strange new sensation was creeping over him - a feeling of power and importance, quite different from that a submissive boot boy should feel.
“Oh, he has to mess them up a little first,” said Lavinia sympathetically. Let him have his fun, Niccy.
“Yeah, miss,” gasped Bobby, pulling back the foreskin and slapping his coc-k on the sides of her boots, “I’m just being creative! I’m painting spunk pictures on your boots!”
Sarah covered her mouth and snorted with amusement. Bobby carried on enthusiastically with his occupation, stopping every now and then and biting his lip when he got too excited.
“Wow, he’s really into it,” she thought, refocussing her phone. “What a little pervert! Hmm… The perfect companion for Lavvy!”
After a while he reverted to thrusting into the cleft, holding onto Lavinia’s knees and looking brazenly into her eyes as he did so.
“Look, miss. I’m really fuc-king you properly now. Does it feel nice?”
Lavinia was quite surprised by his impertinence. He seemed much bolder now he was aroused. A bit too much, she thought. He really needed to remember his place. He was her boot boy, not her lover. Nevertheless his behaviour was making her aware of the throbbing of her filled pussy, and pushing her nearer and nearer to orgasm.
By now the latex sheet was slippery with Bobby’s secretions. Lavinia allowed her feet to slide forward a couple of inches and leaned forward to get a better view. She pressed her legs together to thwart his thrusting, and remind him of his duties.
“You’re doing a good job, Bobby. My boots are going to look so good tomorrow when you’ve polished them up and made them nice and shiny.”
“Not gonna polish them up,” grunted Bobby, pulling back and masturbating vigorously. He had lost all his nervousness now, and was feeling annoyed with the women, but also with himself for having been so compliant and subservient. He was feeling empowered and rebellious. How dare they rent him out to the neighbours like that? He determined to get his own back.
“Sorry?” exclaimed Lavinia, raising an eyebrow in surprise.
“Not gonna…” Suddenly he stiffened. “Shit! I’m c-umming!”
In a last-ditch attempt, he thrust forward at Lavinia’s tightly closed, slightly inclined calves. The head made contact, failed to penetrate, and slid precipitately upwards in the lubricated cleft. An instant later an enormous jet of sperm shot from it, splattering Lavinia’s hat, face and shirt! She gave a scream of shock and anger, shut her eyes and turned her head sideways, but before she could react a second jet of milky fluid had decorated her left cheek. Bobby, regaining his presence of mind, grabbed hold of his erupting member and directed the remainder of his sticky c-um onto Lavinia’s boots, smothering them from tops to toes, without much regard for the knees of her breeches. And having milked out the last slimy drops onto her ankles, he collapsed sideways onto the floor, quite exhausted!
Lavinia was furious, not least because he had ruined her own anticipated orgasm, Nicole and Sarah merely gobsmacked. Even they hadn’t escaped a few stray drops – Sarah in particular was trying desperately to wipe blobs of Bobby’s spunk off her jeans.
“Wow! That was a big one!” exclaimed Nicole. She glanced at Lavinia. She was white with anger, more so because she could see a faint smile of satisfaction on Bobby's lips. He lay there, curled up, eyes closed. She glared at him, speechless, until the sperm tricking down the side of her nose reached her lips.
“Ugh!” she cried, hurriedly wiping her mouth with the back of her hand. Nicole passed her a tissue. She took it and dabbed delicately at her face. “That little brat!” she hissed. Bobby stirred, and sniggered. “Yes, you! You can laugh! I knew it all along. You’re not a proper boot boy. You don’t care about your mistress’s boots. Do you? No, you’re the opposite of a good boot boy – you get off on the very act of defiling them – and me! Did you know you got c-um all over me as well? Well, did you?” Bobby stifled a laugh. “You did! Of course you did! You’re just a horrid, disgusting little masturbator with a boot fixation. Right. Well, In that case, my boy, I’m not going to clean your c-um off my boots – I’ll wear them to the show just as they are, and tell everyone what you did!”
“Lavinia…” began Nicole, doubtfully.
Bobby rolled onto his back and opened his eyes.
“Yeah?” he cried, gleefully, revelling in his new power. “Bet you won’t. You wouldn’t dare!”
“I will! Just you wait and see!”
Nicole and Sarah said nothing, but exchanged nervous glances…