Training Annalise Ch. 05 – BDSM – Sex Story

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Thanks for reading. All characters are 18 or over, and this work is purely fictional. It involves brother/step-sister incest. If that is not your thing, feel free to click away! I wrote this story for myself, but hope you enjoy.

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Special thanks to Kenji Sato for this editing help. Without him this would not have been feasible!

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Jason Robert’s little pet was doing well. She was taking to the training without even understanding that she was being trained. After he played with her sex a bit more, he lifted his hand, and spread open the palm. Then, keeping careful eye contact with his new sub, he started a new form of training–by giving her nipple nearest him a light ‘slap’. He stared at her, and did it again…again…and again, the last time just a tiny bit harder. He then smiled, as he began to use the same hand to rub outward circles from her areola, then he lowered his mouth to her waiting nipple.

She had given little surprised grunts with each pop, but not a big reaction. As he suckled that almond-shaped nipple, he used that same flattened hand to very quickly and very lightly start to brush VERY quickly across her clit. His new sub-toy reacted immediately, giving a raising wail, and Jason slowed and stopped; repeating the same process on the other nipple. By the time he was at her clit the second round, she was looking at him with a bit of a grimace, and when he again started, she began the long moaning wail all over again.

Annalise was all but beside herself. Twice, she had felt the wave of orgasm building, and twice, she had been denied. Twice, she had been in Sub-Space, and twice she had been pulled out of it. And then–this Man was doing it again. When He gave her those little ‘pops’ with his hand, she oddly did not seem to mind. She had been raised to NEVER allow anyone to hit her, of course, but she found herself so ‘open’ and trusting of Him, she knew it would be okay. And as a result, it seemed to help her remain in that loved Sub-Space. Though, when He began ‘tribbing’ her clit? Wow, that was too much, and she just let her hips naturally push into it. The second set of ‘pops’ were even more erotically excruciating, and when He did it yet again, she found herself a mess–absolutely begging to be stretched.

After Jason slowed, he raised the fingers, but THIS time, he gave the area juuust below her clit, a really light ‘pop’. His sub reacted with a loud, “UH!” Leaning over, he used his tongue to ‘flick’ her clit, then gave it a kiss…then the same ‘pop’ on the labia.

His sub cried out louder this time, but it was not from pain. Rather, she began to moan. “Pl-Pl-Pleeease…Please…” she panted, and looked quite distressed. She wanted Him.

So Jason did what any proper Dom would do. He teased her like that again. This time, though, the ‘pop’ was very slightly harder, and he liked that there was a very satisfying wetness in that finger ‘pop’. In fact, it made him chuckle with delight. He hadn’t had this much fun in years.

They had been at this for some time. It was not like he got to do this with anyone, especially a beautiful sub like Annalise, so he was, of course, flag-pole horny. That fact was, the little head was REALLY wanting to do the thinking for the big head, and to say Jason Roberts was good with that, was an understatement. The chair that they had been using was an extra-wide ‘club-type’ chair, with fat pillows inside the chair arms, perfect for his intended purposes. Standing his new sub up, she knew what was coming, so he whispered, “I’ve had a vasectomy”

“I’m on the Pill,” she countered.

Jason smiled and turned her, her arms still bound, and tugged a pillow over the arm of the chair. His sex-toy happily and quickly leaned over the pillow, leaving her beautiful ass on full display. There was no need to touch that incredible pussy to see whether it was ready, as you could see the dampness; which was fine, because his dick, at this point, was aching. Stepping forward just a bit, he felt her pussy lips wrap ’round the head, and while holding her ass cheeks open, he gave a long steady puuush. The feeling of her wet walls gripping his stiff member made him groan, and he had no intention of doing anything slow, his dick was HARD. Grabbing her forearms that were bound across her back, he pulled out a bit, then gave a powerful THRUST. She yelped. He groaned. He then repeated. He was not going for speed, he was going for power, and he pounded into her, HARD. “You like that don’t you?” –thrust, thrust, thrust– “Tell me you like it, pet…” –thrust, thrust, thrust– “Tell,” –thrust, thrust, thrust– “Me…!”

Feeling her Man’s dick invade her in a continuous puuush, and his immense girth made her call out. The yell was more from passion than pain, although there was pain. The difference was, she liked that pain. The very thing that she had been taught should never happen, that of having pain applied to her, was proving to be incredibly erotic. So much so, that the well was full, and she was needing to cum. The orgasm was there, and her hips were tightening. His commands bought a few moments, and she answered Him. “Ye-Yes…I DO like it!” Annalise said between pants. “I LIKE YOUR DICK!” she yelled. She was shrieking, and she felt His pumps getting faster. “C-Cum in me…PLEASE let me cum!” Annalise called aloud.

Jason heard his sub beg, and truth be known, he was about to blow his load as well, so he loudly said, “Cum, girl…I,” –thrust, thrust– “said,” –thrust, thrust– “CUM…!” And when he pushed at that time, he grabbed her hips and dumped his load with a mighty lion’s roar–okay, an old lion, but a lion, nonetheless. He DID manage to hold just long enough to hear Annalise scream and start shaking uncontrollably, as her orgasm washed over her, so he knew he had truly done his best work.

He was wheezing and had to stay in her for more than a minute, just to steady himself. The ‘pipe’ was now a ‘hose’, softening as it slipped out of his sex-toy. He was able to regroup enough to release and completely unravel the ropes from ’round her arms. Aftercare is very essential. He guided Annalise over to a small antique daybed against the far wall, where he laid her on her stomach. He was careful to take care of his new property, rubbing the shoulders, biceps, and back. Using the one unstained pillow from their activities, he moved over and behind his toy. Spooning up to Annalise, his flaccid dick at the base of her ass. She may have been much younger, but she apparently had the same submissive link tied to the Sub-Space, because she not only relaxed into him, she pulled one of his arms in closer to hold her.

Annalise had matched her Man’s breathing, and he was tired. But then again, so was she. She felt his sticky manhood pushed against her, and pulling his arm in close to her, she snuggled back into him. NONE of the boys or young men, who were really boys, had ever done this, and she decided she liked it. Being under His control meant also being under His protection. As she laid there snuggled with her Dom, her mind was both shutting down, and racing–all at once. ‘WHY do I like this?’ she asked herself, ‘and HOW do I hit that orgasm level again?’ She knew she couldn’t have a real relationship with a man that was more than twice her age, but she pushed that out of her mind. He was lightly sleeping, and she felt herself relaxing, too. Annalise, at last, shut down, and sleep overtook her.

***

Jason woke up to the wonderful smell of his sub’s hair, the result of snuggling before and during the nap. Opening one eye, he noticed by the clock, they had been out for a little more than an hour, and he liked the feel of his cock nudging the underside of her ass. His sub seemed to still be asleep, but when he shifted as he woke, he knew it would in turn cause her to shift. Jason hadn’t gotten laid this much in a long time, but then again, he hadn’t been with such a lovely beast either, especially one that he could literally ‘show the ropes’ to. The old dick was feeling the wear, but had stiffened just a tad. Truth was, he needed a break. Jason had an idea, a ‘loose plan’, if you will, but he would just have to see how it went. He slowly pushed his hips forward, and felt his dick slide to just behind his sub’s pussy, and she did stir.

Annalise awoke in her lover’s arms, and it felt very nice. A very big part of her wished he was younger, and that she was older; she could get used to this. She had pushed that out of her mind several times already, but the difference in ages, and what her Man had been doing to her, was weighing heavy on her mind. Annalise’s last boyfriend had tried to tell her she wasn’t gonna discover better than him, that she deserved no better. That was bullshit, but it really cut deep, so being appreciated like this was a nice change, but it all brought with it–its own set of emotions. Feeling the mushroom head rub against her ass, was certainly a unique way to wake up, she had to admit.

Shifting a bit, Annalise and her Dom both sat up on the little daybed, naked, facing each other. “I need to know something,” she asked.

Jason knew this was coming and smiled. “Go ahead.”

“How do you know my body so well, that you can make me do these things?”

He smiled. “Annalise, it’s like I said, it starts with trust. You had to let me do these things. I know that what I have shown you is counter-culture to the world, but really, have you ever had a more powerful sexual experience?”

“Well, honestly? No. And I’ll even admit, I liked it and wouldn’t mind doing it again before this time, um, ‘ends’, but part of me worries about the ‘how’. Know what I mean?”

“Yes, what you are experiencing is called ‘reactance’, and it is a bit of guilt, tinged with the powerful feelings you just experienced. Here are a few things to know, my pet. THIS is strictly between you and me, yet if you wanted to be in public with me, then that is fine, too. But this emotion is natural. What you just experienced in that sexual moment was a true ‘Power Exchange’. And admittedly, it is a lot to handle, but I would think you can handle it, no problem.”

“I have to admit…I have enjoyed it. But, WOW, is this intense.”

She played into his hands perfectly. “Tell you what. Our time together is now short, but we can slow it down just a bit. Why don’t you head over while the workmen are on break, freshen up, and come back, maybe in something casual. We’ll go grab a quick bite to eat. I have to make a stop, then we come back here, and see how things go. Okay?” Her smile told Jason she was good with it. And quite a smile it was.

***

In a while, Annalise was back, this time, wearing some simple shorts and a button down button-down shirt. They then made their out, and had a light lunch. It was all going well. His pet appeared to be enjoying being in public with him. The ‘causal glancers’ wondered her to be his child, which was fine, as Jason didn’t give two shits what other people wondered. He decided it was time for a new little test, as he steered the car right into the parking lot of the local sex shop.

Annalise’s eye popped WIDE at the location they had just pulled into. ‘Make a stop indeed,’ she wondered, and started, “Umm…”

“Well, I figured as long as we’re rolling by…” he interjected, with a sly grin. Opening her door, he said, “Besides, I figure as long as I have you for another day or so, I might as well get one or two naughty/sexy things to have some fun with, and see you in.”

Annalise entered the store with some trepidation. She and her friends had joked about the place, and now, here she was in it! There was bondage gear, a whole slew of dildos and lubes, but it turned out that her Man was really just there for the lingerie. It was definitely ‘sluttier’ than anything at a mall, but what he picked out was really sort of nice, all things considered.

She was actually flattered that someone had spent money on her like this, especially when he saw her eyeing a rather expensive silk robe. It had a print on it she fancied, and it was rather tame compared to the other items in there. He insisted she have it, and it went in the bag as well…along with a nondescript box. She enjoyed the joking, as they rode back to His place, and getting out of the car, she noticed the workmen were nearly done.

Those feasible workmen, damn their hides. The ONE thing Jason forgot to do, was to tell them to do this slowly. The job did look good, though. Annalise slipped into his house while he spoke to them. They let me know that they would have it ‘distressed’ by tomorrow and done. That just meant the furniture delivery, and then they were done, dammit. Actually, he was pretty sure the Garcias would be home in a day or so at most, so it would be all about done anyway. Damn. Jason Roberts was really enjoying himself, too.

Annalise had just exited the car and made a beeline inside Jason Roberts’ house. She didn’t need those nosey-ass workmen seeing her carrying a bag from a sex shop, especially headed into her neighbor’s house. Seeing the work nearly done was both good and bad. Good that she did not have to face the consequences of her actions via her parents, bad that she was really starting to enjoy exploring her sexuality this way. Alas, it would soon end, but she could enjoy it for the moment, right? Annalise smiled at that wondered, and pulling one item in particular out of the bag, along with her robe, Annalise pulled a barstool to the center of the door entering the hall, and left a note on it, then went immediately to the guest bath off the hall, to take a quick shower.

It excited and disappointed him to see that his pet was getting into this, as their time together was coming to an end, but hey, might as well make the most of it. Jason smiled as he took out the item in the box, and gave it a quick wash. He then took it back to the bedroom, noting along the way, that the shower was running in the hall bath. He placed the same stool in the hall, flipped the note over and simply drew an arrow on it. He then stopped, just long enough to pop another blue pill, quietly thankful he had not yet had a heart attack, and got a quick shower, getting mentally ready for the afternoon’s activities

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