Eliza Havering Ch. 05

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Sylvia is introduced to new delights.
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Part 5 of the 6 part series

Updated 06/10/2023
Created 12/01/2020
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I followed her along the corridor and down the stairs. My mind was still buzzing with the thrill of what had just happened. My hand still tingled from the feel of the flogger sweeping through the air and hitting tender flesh and my ears were still occupied with the muffled cries and sobs. I felt alive and that I should not, and I knew it was wrong, but I was filled with new and exciting sensations. As I walked down the stairs, I was mesmerised by Eliza's shapely figure in front of me. That skin-tight leotard displayed all her charms. The way it was cut very narrow at the hip accentuated her bottom, so pale in contrast to the pitch black of the fabric. And the way that nakedness stretched across her thighs before disappearing into those menacing boots. I was sure I could smell and taste the arousal wafting from her as she walked in front of me.

I followed her into the kitchen where she carefully selected a bottle from a wine rack. She rummaged in a drawer before passing it to me along with a corkscrew.

"Can you open that while I find the glasses."

After pouring us two drinks she sat down in the oak carver chair at the head of the table and breathed a huge sigh. She girlishly fanned her face with her hand and then coyly looked at me and giggled.

"I can't deny it, but that little session got me going. I'm a bit sweaty and damp," she said, squirming a little in her chair and tugging at the crotch of her leotard. "She's such a sexy little thing, don't you think so?"

I nodded but in truth I could only concentrate on her. She was sitting in a most unladylike manner with her legs splayed and a damp patch showing between her thighs. It was hypnotic and provocative, and I had to force myself to look away. It wasn't helped by the fact that the vee at the front of her outfit seemed to have spread even wider and her breasts, small though they were, threatened to fall out at any moment. I was sure I could see a hint of darker areole and it seemed to be her nipples that were the last thing that held her leotard in place. As sexy and cute as Sylvia had looked tied to the bed, I only had thoughts for Eliza. Thoughts and hopes. But they were hopes that were soon to be dashed upon the rocks.

"I have to admit ..." she started, seemingly to have summoned up the courage to make her confession, "I find her very desirable."

She stopped and stared at me directly, letting it sink in. There seemed to be an unspoken hope that I would understand. I dumbly tried to make sense of her words.

"Usually I try to remain professional," she went on, "but there is something about young Sylvia that gets my juices flowing. They often come to me as unbroken horses and I turn them into docile animals. But she is different somehow. I know I am going to regret breaking her in. I shall enjoy the process but not the result."

"Is that how you see them ... your 'clients' ... as horses needing breaking in?"

"It's a crude metaphor but it will do. Usually I do so dispassionately. Of course, I use them for my pleasure while they are here but that is all it is. Then I pass them on to their new futures. Either back to their parents or occasionally partners who decide what to do or, as in the case of Jane, on to bigger and better things. But this little slut is different somehow."

"Different in what way?" I asked only vaguely paying attention. During her speech, my eye had been taken by a small movement and I glanced down to find that she was softly stroking her pussy through her leotard.

"That compliance that you witnessed yesterday evening. With her it is still only a temporary mask. Usually by this time I have reached past that stage and we are ready to move on with proper training, but with her the fire still burns within her, which has surprised me. In many ways I admire her spirit, her fire, her refusal to give in." She sat back, sighed, and then took a large mouthful of wine.

"I am enjoying being serviced by her. She is unpractised and inexpert, as are most girls when they first come to me. Unlike them, however, I don't get the same feeling of reluctance. Certainly, there is no horror or repugnance so often shown by girls who are being asked, or expected, to orally stimulate a woman. Often for the first time. Sylvia seems to be getting a taste for it. She is certainly improving with every tongue stroke."

I tried not to look shocked at what she said and to keep a straight face with an adult and liberal expression. In my head I was only getting disappointment. My dick had started to stir but its progress ground to a halt. Calm down, I told myself. She's a lesbian so what? I have to be ok with that. Besides there seemed to be a plentiful supply of cunt on offer.

She looked at me and seemed to detect my sorrow. Her hand stopped massaging her pussy and reached out and touched my knee. My heightened senses could smell the musky odour of her pussy from her fingers.

"Yes," she said, an air of sadness in her voice, "I'm a lesbian. Sorry, if you were expecting more but I'm sure Sylvia can more than make up for that. As well as who knows who else in the future."

"Its fine," I told her trying to be sincere with my smile, "this is a professional relationship so to speak, and besides ... after last night I can't really complain, can I?"

"Speaking of which, we should release her fairly soon. I'm sure she's had long enough to contemplate the error of her ways, at least for a while before she decides to be rebellious again."

"A little quiet time-out is always helpful," I volunteered.

"Exactly. I have more training planned for her and I'm hoping you can assist me again."

I perked up at the prospect. "I'd be delighted. What did you have in mind?"

"I have to move on to penetrative sex. Previously I have done this myself using dildos or a strap-on but with your help it can be more authentic. In other words, I want you to fuck her. It certainly will not be her first time; I have the feeling that she gave herself freely in her previous life. Eventually I will need to test all three of her holes and I think she may be a little more reluctant with the final one."

"She certainly knows how to use the first," I commented, and a smile spread across my face at the memory of last night."

"I think we can take that as a certainty," she replied grinning. "You will probably find her cunt equally as ready, but we shall see. It is her anus that I am not certain about. I intend to start her off with a series of plugs, each larger than the last, until she is ready to take a full-sized cock. This may take several days but we shall see. I intend to start her on the smallest tonight. It isn't large but it is enough that you may feel it while fucking her."

"It's not something I'm new to," I assured her, "an ex had a liking for plugs and I was happy to go along. She would never let me fuck her there though," I added sadly.

I had become used to her use of down-to-earth language and it had stopped coming as a surprise. Since that seemed to be the norm, I had decided to join in.

"A word or two about attitude," she said, suddenly turning very serious, "I have learnt from past experience that gentleness should only be used as a reward and that a hard indifference works well to start with. I thought you did very well yesterday, and your attitude was just about right. This needs to continue for the next phase of her training. She can only enjoy her moments of kindness as a contrast to moments of toughness. I'm asking you to be quite hard and forceful with her. Do you understand?"

I nodded to show that I did and I thought back to last night when I had held her head far longer than she was comfortable with and how I had tried to push her beyond her limits. I could not deny that I had enjoyed that feeling of power.

"In that case I think its time to release her. Will you do the honours? You will find her collar on the chest of drawers and the leash will either be attached or lying next to it. Make sure she is wearing both before you release her wrists and ankles. If she starts playing up, I'm sure you'll know what to do. The crop will be next to the collar should you need it."

She paused to make sure I was paying attention and absorbing her instructions before she went on.

"Take her into the room next door. This is a second guest bedroom, and it is cleaner and tidier than her current one. The mattress in that one is old and badly stained as you might have noticed. As those stains have been left by previous occupants, I see no reason why I should replace it. When you take her into the new bedroom tell her to stand by the bed and assume position one. She should know what this means by now. It was the pose that she took in the cellar. Hands behind her head and feet spread wide, eyes on the floor. I will join you shortly when I have finished this excellent wine."

As I walked out and up the stairs, I felt that I bore a new weight of responsibility. It felt almost like a promotion. It certainly felt that I had gained a lot of Eliza's trust. I was determined not to let her down. Already my shorts were beginning to bulge at the prospect of what might happen.

To calm down before I went into the room where Sylvia was being held, I looked into the other guest bedroom. It was an altogether much nicer and brighter room, mostly dominated by a large bed similar in age and fashion to the one on which Sylvia was tied. The bed had a simple crisp white sheet covering the mattress but no other bedding. I wondered how long it would remain in such a pristine condition. Leaving the door open I went out and down to Sylvia's room. When I opened the door, her eyes jumped open with alarm but seeing only me she relaxed a little.

"Time to get you ready for your next session."

Her calmness drained away and nervousness took over. I found the collar and leash as well as the crop where Eliza had said they would be, and I picked them all up and went to stand looking down at the helpless girl. I remembered Eliza's words about being hard and I felt it was my duty to follow her advice. I dropped the leash and the crop on the bed beside Sylvia, making sure she saw each one clearly, then I held up the collar.

"Time to get you dressed," I taunted.

With a fistful of her hair I pulled her head up and slipped the collar behind her neck. I fastened it carefully and clicked the tiny padlock shut. I assumed Eliza must have the key as it was not with the collar. Then I clipped on the leash, stood back, and smiled down. For some reason, my smile did not seem to reassure her, and she tried in vain to shrink away from me.

"How are you feeling after your flogging?" I asked, "do these hurt?" I grabbed a handful of her right breast and squeezed. I tried the other one and she whimpered.

"You know you only have yourself to blame. You get no sympathy from me. You deserved every stroke. And how is your cunt?"

I let go of her tit and felt between her legs before giving her a couple of hard smacks. This got a full yelp! I was amazed that the little tramp was still wet down there. She opened her mouth to protest.

"P ... please, Sir ..." she started to say.

"Silence!" I barked at her, "I don't want to hear from you. I'm going to untie you now and I'm sure you won't cause trouble. Just in case, remember I have this."

I picked up the crop and held it in front of her face. It seemed to have the desired effect as she clamped her mouth firmly shut. I started by releasing her ankles. The leather cuffs were attached to permanently fixed leather straps which made things easier. When I unclipped her wrists, she made no sudden move but gently flexed her limbs to rid herself of the stiffness. I picked up the end of the leash and tugged it sideways. She had no choice but to follow its urging and slide to the side of the bed. A little unsteadily she sat up and I pulled again, heading for the door. She was forced to follow me and stumble along behind. I led her to the second bedroom and stood her at the side of the bed facing the door.

"Position one!"

She gave me a puzzled look. Not because she didn't understand but she was shocked that I knew. She tried to stand as straight as possible and spread her legs apart. Placing her hands behind the back of her head had the same effect as before. It pushed out her tits, displaying them quite prettily. I unclipped the leash and tossed it onto the bed before grabbing her nipples and rolling them around and then I squeezed and pinched them. I thought her tits would look much better for being crowned by hard nipples. I was right. They looked so much better. A nicer way to present to Eliza when she arrived. I looked around and found a simple chair by the dressing table, so I pulled it out and sat down facing Sylvia. She was swaying slightly, trying to keep her balance after having been tied to the bed most of the day. Silently we waited for Eliza.

Every so often I would have to ease the ever-swelling force that was my dick. It felt good to the touch and I wondered where it would end up tonight. I knew where I hoped it would be, inside the naked girl standing in front of me. I watched as moisture oozed slowly out of her cunt and spread down her thighs. She was ready for the taking.

In the distance I heard the click clack of heels coming up the stairs and I saw Sylvia try and stand taller and thrust her tits out even more. She seemed determined to make an effort. I felt no such need and stayed sitting. There was a moment of tension when the sound of those menacing heels went past our door. And then silence. There was almost relief but then they started again, heading in our direction. When Eliza came in, I quickly noticed that her face was flushed and was covered by a sheen of perspiration. I smiled inwardly, guessing that she had been amusing herself in the kitchen. She had been playing with herself when I left and had looked intent on carrying on. She was carrying a small red box that she put down on the bedside table.

She walked over to Sylvia and walked around her inspecting her from all sides. She made a few minor adjustments, pulling her elbows further back and kicking her feet further apart. When she got to the front again, she reached out and slipped a finger along her pussy. Then she lifted it up, smelled it and then put it in her mouth and savoured it.

"This seems to be your usual state, girl," she said with a mocking tone.

Sylvia blushed but managed to maintain her stance although it looked like her knees were about to give way. Then she reached out again and flicked at her nipples. She turned to me.

"These look pretty. Do I detect your handiwork here?"

"I just thought she should look her best for you."

"I agree. They look at their best when hard. Was she any trouble?"

"I made it clear to her that trouble was not a good idea and she seemed to agree with me. She was docile throughout."

She turned back to Sylvia who was still standing as she had been instructed, her eyes fixed firmly to the floor. She reached out and lifted her chin, forcing her to look into her eyes. She planted a soft kiss on her lips.

"You are a lucky girl," she informed her, at which Sylvia looked puzzled and very nervous. I suspect she had heard such comments before and not enjoyed the outcome. "Tonight, my good friend Duncan is going to fuck you. Provided that is that you continue to behave. Won't that be nice for you?"

I saw Sylvias head try to nod but her chin was still pushed upwards.

"I also have a special treat for you which we must deal with first."

Even I could detect the hidden menace in her voice. She let go of the girl's chin and her head dropped back to fixate on the floor once more. Eliza stepped sideways to the small red box she had brought in with her. She clapped her hands to get Sylvia's attention and the girl looked at her sideways. Eliza reached into the box and delicately picked out a single object. She held it up for all of us to see.

"Do you know what this is?" she asked and then she tapped her foot impatiently when she got no reply. Sylvia swallowed and summoned up her courage.

"A butt plug, Miss?"

"Well done."

Eliza turned away again and placed the plug carefully on the bedside table and then reached back inside the box. Without any need to speak she pulled out a second plug, a little bigger than the first. She placed it next to the first one then reached inside again. Like a magician pulling rabbits from a hat, a third one appeared. This was obviously the next size up. She placed it, almost reverently, in a row with the first two. Slowly a fourth and fifth joined them and she stood back a look of triumph on her face. I must admit the final one made even me nervous for Sylvia. They looked like a row of perverted Russian dolls. A sex-toy babushka.

Her final pick from the box was thankfully not some monster plug but a squeezy bottle of lube. She held that and the first plug, the smallest, up before the girl's frightened face. I saw her blanche and shiver. I guessed that her bottom was not something she was used to being violated. I also knew that not only would be but that she had no choice in the matter. Personally, I couldn't wait to see what happened. My dick was already reacting to the prospect.

"Turn and get on the bed," she was ordered, "And get on your hands and knees!"

For the briefest moment I saw a hint of rebellion returning on Sylvia's face. I slapped the stinging tail of the crop against my palm and she instantly knew she was outnumbered. She released her hands from behind her head, turned, and clambered onto the bed, presenting her pert bottom to us. I could see her anus peeking from between the cheeks of her arse. It was a lovely sight, and I could hardly wait to see it abused. I was a swirl of mixed emotions, but I decided I would deal with those later. For now, I was fixating on that dark little pucker.

I watched as Eliza liberally coated the smallest plug with lube and spread it around. She then stepped over to the bed and let a long stream of it fall and seep between Sylvia's arse cheeks. Then she turned to me.

"Will you join us? I need someone to hold her cheeks apart." As I stood up her eyes widened. "I see you are already eager for the next stage of training," she commented. It was true, my shorts were struggling to hold my hard dick in check and there was nothing I could do to hide that fact. "It hardly seems worth staying dressed. You might as well take it all off."

I felt suddenly free as I pulled my shorts down. My dick sprang free and pointed proudly in their direction, especially while I tugged my t-shirt over my head. Although Sylvia had her back to me, I hoped that Eliza, despite her sexual preferences could admire what I had to offer.

"Nice," she commented, "I'm sure Sylvia will appreciate it later. But now we have her first plug to deal with. Could you spread her cheeks for me, please?"

I sat on the bed beside the kneeling girl and, using both hands, pulled her cheeks apart. We now both had clear sight of her waiting arsehole. It was slightly darker than the rest but shone from the lube that already covered it. Eliza reached in and spread the lube more carefully and started to push a finger inside her. I felt Sylvia flinch and I gripped her more strongly. I watched in fascination as Eliza's finger slowly disappeared. First one knuckle then the second, until she was as far as she could go.

"She is very tight. I think this might be her first time."

She pulled her finger out but there was to be no respite. This time two fingers went in, again all the way, and then stayed in place. Slowly Sylvia seemed to accept them, and I felt her relax. Perhaps she was almost starting to enjoy the sensation. I know from experience what a warm feeling it can bring, and how it can heighten the excitement and pleasure.

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