Training Annalise Ch. 02

NOTE: All characters in the following story are over the age of 18 an are fictional. The locations are (mostly, with slight changes) are fictional as well, and the following is a story involving Blackmail and BDSM, if this ain't you thang, click away now!

Well once again it's another story involving those Roberts boys! Ok so now we get into the story. I am trying to bring out the mental aspect of BDSM training, hope you enjoy, and give your thoughts and comments!

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Annalise was in a near trance-like state. This entire experience seemed so very surreal, it did not actually seem to be real. Her day so far had been a rollercoaster of emotions, and she was ending it by selling herself to this dirty old man! As she stood, she told herself 'just go with it, A, you can do this.' To her surprise, Annalise found the old man not drooling, or leering at her, or any of the perverted things one would expect. He did have a look of total concentration, and all of it--was focused on her. Oddly, she found a tiny part of her liked that, if not finding comfort in it.

As Annalise unbuttoned her blouse, she could not help but wonder, what on Earth caused her to take a quick shower and change into other clothing...for this? Her bra and panties really weren't anything special, just a matching, pastel cotton set, but her darker skin showed through them, and she liked that. She also had simply pulled on a nice little buttoned-down blouse, and she fumbled a bit in nervousness, as she removed it.

Annalise was no virgin, but on the other hand, not the most experienced either. She had been pretty adventurous with Nick, a man more than a decade her senior, and she had really liked the way he taught her things, and did things with her that no boy her age had tried--so there was a natural attractiveness to older men--but Mr. Roberts was waaay beyond that. She would never have considered something like this in her wildest dreams, and it really did take something like this, for her to consider it. Annalise had read a few stories on the internet about 'sugar daddies', but the whole thing just seemed perverted to her. Annalise had tried to not make eye contact with him, but when she looked at Mr. Roberts, she had to admit his piercing gaze affected her. She was not used to men being totally and fully focused on her, so when he did this, part of her, well, it seemed to almost, well, melt.

It had been some years since he had been able to enjoy touching the soft, warm skin of a woman, and this young lady was quite that. he had only a few days, truth be told, and he intended to make the most of them. They say that youth is wasted on the young, and there is truth in that--because Annalise Garcia had that natural curve to her body, which she began to reveal, when she removed her blouse, and her dark areolas showed through her pastel-blue bra. This new toy was quite petite, so her breasts were solid B-cups, yet her nipples and areolas were large for such sized breasts. She shimmied out of her shorts, her hips were wide for her frame, and the high-cut panties displayed some pubic hair under there, something he was sure to enjoy shaving to his liking.

He reached up and removed his shirt, showing the classic 'wife-beater' undershirt. What he did like was that his new toy was staring at his crotch and when he looked down, he was proud to see the old boy quite erect. At this age, it took a lot to motivate the old boy, and her bod, plus the old blue pill, was quite enough, and he was currently sitting at a good three-quarters hard. He also leaked quite a bit, so his dark gray boxer briefs had a large stain on them. Any hesitation on Annalise's part seemed to be gone, as she simply reached over and began to tug them down. She was staring with a blank look, and he totally got that, and he really enjoyed this hottie pulling off his underwear. He turned slightly and sat on the couch. His new toy seemed to naturally take her cue and sank to her knees in front of him. He slumped back a good bit, sliding his hips forward, and was rewarded by seeing this young lady take his cock, give the shaft a squeeze and a pump, and then move her mouth naturally to it.

Annalise had to admit, she was impressed by the size of this older man's cock. She was really expecting some shriveled up little thing, and while his was no longer than the four other men she had been with before, this one was, in comparison, REALLY thick, and it hung generously over each side of her hand. Annalise figured she could maybe do a few things other than sex, to get this old guy into shooting his load, and she figured offering oral would be one. Truth was, Annalise kinda liked giving oral, and she knew by guys' reactions, she did it really well. Although Jason Roberts' dick was a big one, it was strangely not at full erection, so she leaned in, and opening her mouth wide, she gave him a big LICK, starting at the base at his balls, and moving up to the head. The head was good size, and being circumcised, was easy to feel, and she rubbed the base of it over her tongue before shifting forward and taking him full into her mouth, plunging his full length into the back of her throat.

His girth surprised Annalise. She had looked up at the old man with those doe eyes. She had to admit, his look of total concentration was oddly alluring. Annalise had almost no gag-reflex, so she expected his face to change, as she took him this way; it was what everyone had done, yet his face barely changed. He did groan a little, but that was it. No grabbing the head, no pumping of her face, he just stared at her with that same, mesmerizing look.

Annalise had been at it for some time. She was impressed with the way his girth stretched her mouth, but more so, the way it plugged the back of her throat. What impressed her most, though, was this man's incredible control. He was not pumping his hips as she expected, but was rather ever-so-slightly moving his cock and hips in a way that matched her movements. It was strangely intoxicating; in that it made her feel somehow connected to him. Plus, there was that look. She might be the one doing the work, but without so much as touching her, he seemed to be in control...and she liked it.

He had taken time to think this out, and he knew what he needed to do. Far from a quick goo-dump, he was 'going for broke.' Were it a lady closer to his age, he would have done the goo-dump and been happy about it, but he knew he wasn't going to get this opportunity twice in the years he had remaining, so he kept his concentration up, and it seemed to be working. This girl knew her stuff, because it really felt incredible, the way that he could feel his dick sliding into the back of her throat. The top of his mushroom-head felt the ridges on the roof of her palate, then he felt it go smooth. He was back in the back, all right. He had already matched her breathing, a little technique he had learned long ago, so as she moved he moved slightly with her, and his dick began to 'pump' the back of her throat slowly and slightly. He had plans, yes, but it was best not to rush them.

He knew he was having the desired effect when she put his hand on the back of her head. It told him she was really getting into this, which was the plan. he more than obliged, he began holding her head with himself in as far as he could possibly go, tightening his grip, then a series of very fast hip-pumps, but loosening that grip and moving her head up slightly, gripping her hair to actually pull it as he turned her head, then moved her down to make his cock push out on her cheek. Her drool, along with his cock again going to the throat for another round, made a wonderful 'slurp', followed by the rapid pumps, her vocal cords producing a 'gah-lack...gah-lack...gah-lack...mmmph' sound back there.

Having done this for a bit, he now unexpectedly let go of her. She stopped for a second, waiting, but then the message that he was silently 'instructing' her got through, and she began the same head movements without his touch. That was a good sign indeed, he had her closer to sub-space and he bet she didn't even know what that was, which was all the better. He finally broke face, and smiled, as he lifted her mouth off him. After all, he was enjoying this.

Annalise liked that he finally smiled. Oddly, she felt very connected to him, and she did not understand why. Seeing him smile like that, gave her a sense of approval, in a manner that was more than sexual. The sexual part was nice though, to be sure. She had struggled a bit to get his cock to the back of her throat, and that had never happened. Annalise was giving first-class head as a teen, more than a year before she gave up her virginity, but she had yet to encounter someone who had so filled her that she had to breathe through her nose, and had been so in control. She had figured she would do this for maybe a minute, then he'd spurt and that would be that--but this guy had gone a LONG time. She wasn't sure, it's not like she kept a timer on him, but she was pretty sure he had gone for nearly ten minutes. It was long enough that the back of her throat became sensitive.

Annalise had decided earlier that she would just do this; she wasn't going to actually fuck this old man. Hell, she might kill him, and she didn't need that! But a long face-ride had her, she had to admit, excited. Annalise had kept her underwear on to this point, but she had to admit that, several times as she gave this guy head, she had rubbed herself through her panties, and by the time he lifted her off, she was thoroughly wet. The thought had crossed her mind, as to what a big thick one like this was going to be like, and that, plus the feeling of approval, was enough to convince her.

Annalise did not require any prompting, the natural 'connection' they had going, told her what to do, and she obligingly tugged his shorts the rest of the way down. She kept eye contact with him, as she removed her panties in one swift motion. Taking his hand for balance, she stepped up, and placed one knee on the edge of the couch, her foot on the other, she began to straddle him. She moved forward, and she felt an incredible sense of affirmation, as this Man leaned forward, paused, then gave her a full kiss. She gave a slight moan of approval, enjoying how, unlike other boys and men pawing at her, this one simply took his time, and enjoyed allowing their tongues to explore each other. She felt him unclasp her bra, as they released their kiss, and in a quiet tone she nodded and smiled at his prompting, "Go slow, pet..."

Those three simple words made her gush in delight. She knew she would need that gushing though, as she felt the invader begin to penetrate her. She was sure her face was contorting, as she felt her sex being str-et-c-h-e--d, and it made her whimper. It was not comfortable at all; yet, she oddly wanted it. Both the feeling, and what He was doing to her. Annalise bowed her back in response to the thick cock now moving into her. She whimpered and had to slow, twisting a bit, but the smile of satisfaction on His face made it worth it, and soon, it was fully inside her.

He liked how his new pet winced, as her pussy accepted his shaft. She grunted and whimpered, but he let her take her time. After all, she was doing what he wanted, and that was the goal. Once she was fully 'pegged', as it were, he kept eye contact and barely whispered, "Sit...sit still..." She had her hands on his shoulders, and he now began to squeeze and play with her breasts. Taking them fully into each palm, he gave them a squeeze, then moved to her nipples, and gave them a tugging turn and twist, much to her delight. He stopped her a second time from moving her hips, telling her, "Not yet, pet..." then resumed his activities. He accepted a kiss from her, and moving his hands to the small of her back, he ground her clit against himself, and the result was a desperate moan. Breaking the kiss, he took a nipple into his mouth, and suckled it. It was good and firm, and when he did this, she moaned again, and at last, he began to s-l-o-w-l-y move his hips, pushing up into her, making her squeal in delight.

Annalise felt an odd mixture of pain, pride, and most of all, lust--as the invader stretched her as it slid in. It felt SO good to be filled like this, and knowing that this Man approved, was just icing on the cake. 'He may be old, but my goodness,' she thought, 'he wasn't like anyone her age.' She really liked that he wasn't trying to slam himself into her--which would have never worked--but that he really took his time with her, to see and touch and feel her body, and his stare was like he was looking inside her. This was the first time she felt her body was appreciated, and she loved that he took time with her breasts...particularly the way he tweaked and twisted her nipples. There was a certain 'naughty' side to that stimuli, and she liked it.

He was now ever so slightly moving his hips, but it felt like he was going a hundred miles an hour. Just as she reacted to his cock with moans, whimpers, and wincing, feeling her fit around him, squeezing his shaft made him grunt as well. In a quiet, forceful whisper he reminded his pet that she was doing so well, and that she felt great. He kept his hands on her hips, keeping her moving very slowly. Speed was not the issue here, at least, not yet. He was also sometimes holding her 'balls deep', making sure her clit rubbed against him, and when he did this, he pulled her just a bit closer, enabling him to take one of her wonderful nipples into his mouth, then he would let it go, and begin to slowly fuck her. Shifting his hands to her ass, he began to lightly tug them apart, and this gave him the additional 'bit' to let his mushroom head rub what had to be her cervix, and that was the final piece that pushed his toy over the edge.

Annalise had never been fucked like this before. The feeling of a cock filling her up like that was really something, and the way he made her move in a deliberate slowness was incredible. She may have been on top, but this Man was clearly in control. She wanted to move, to feel its thickness push her open again and again, as she moved on him, but--he made her wait! The anticipation was killing her, and so FINALLY, when he let her move, she made a light shriek, as she felt Him push into her. That, along with the nipple suckling and clit rubbing, was making her moan out loud. She wanted to bounce, to move her hips, to FUCK Him, but most of all, she oddly wanted to please him, so she bit her lip, and let him control the pace.

He had both hands on her ass, and he would lightly turn her cheeks apart, and that let her go down just a bit further. 'Oh no...' she thought, as the invader was now rubbing her cervix, and she cried out loud. She kissed him in a hungry manner, she winced and whimpered, but he let her go no faster. She could feel her climax coming on, something she never dreamed this old man would give her, but there it was, and it was both powerful and fast. This had always been hers to control, but not this time, and all because this Man controlled the pace. Screaming, "Ohhh Gaaah-- I-I-I--!!!" she threw her head back, as the orgasm flooded her, making her tremble and shake uncontrollably. Her muscles had been tense for quite some time, and this release caused her to fall against this Man, gasping, the powerful orgasmic wave at last spent.

Little did Annalise know, it wasn't over.

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