Training Annalise Ch. 01 – BDSM – Erotic Story

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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! This one is a bit of a slow(er) burn in that the first chapter is dedicated more to character development, but trust me, it certainly gets us there!

***

Jason Roberts sat on his porch, looking at the Garcias’ front window across the street. Windows, actually, and wow, were they ever broken. Burst out from the inside, and a piece of furniture laying on the front porch, to boot. The Garcias had left earlier that very day, going somewhere, maybe on some sort of vacation, and had left their daughter, Annalise, in charge. Normally, it would have been a good call.

After all, Annalise was the sort of daughter fathers wished they could have. Top of her class in academics, part of various clubs, just the all-around ‘It’ girl, and he had noticed in the local news that she even had a full-ride scholarship to some Ivy League college, which would be starting in a few weeks. So, it was quite a shock when she had a ‘Post-Grad’ party that had gotten out of hand. Apparently, two boys got into some sort of fight, and the front-porch damage was the result. His front-facing security camera had captured all of it, and even today, it was catching Annalise trying to get it cleaned up, but she very clearly had no idea what to do.

Annalise was a sweetie for sure, even though she was easily young enough to be his kid…and then some. Maybe five-foot-one-inch tall, if that, she had long, straight,raven-black hair, and was busty with a nice, round butt, and that curvy, olive-colored skin of her partly-Hispanic heritage on her father’s side. Combine that with the ‘doe eyes’ and big red lips of her Asian mother, and she was quite a delicious snack,indeed. As for Jason Roberts, it had been a few years since his Wife had died, and he was just a quiet, confirmed bachelor. The Garcias knew him as just that, and he was sure she saw him as no threat.

Seeing her out there, in a T-shirt and shorts, far too tight for her to bend over properly, really got Jason thinking. He knew he could approach this one of two methods, so taking a copy of the security-cam footage on a thumb drive, he decided to walk over and offer his ‘help’. After all, nothing ventured, nothing gained, as the lawyers at his firm used to say.

You lose height as you get older, so at age fifty-nine, Jason was down at least two inches from his six-foot frame, but still tall enough for this. He was really active for a guy his age, into biking and swimming. His thinning hair was hanging in there, but even so, was fairly silver-white now, and he maintained the usual goatee. As he was striding over, he said to himself ‘She’s grandkid age, you old pervert–you really going to do this?’ He smiled as he wondered about the risk and the reward, and figuring this was the only time he’d get this opportunity, andsaid, “The hell with it,” and continued striding toward the Garcias’ house with confidence.

Annalise Garcia was so upset, she couldn’t even cry. Her parents had trusted her with the house, and now look at this. The front window wa sbroken, and one of her mother’s tables in the front yard, cracked! She was still picking up glass, when she heard Mr. Roberts from across the street. ‘Oh Shit!’ she wondered, ‘He’s on the HOA board! What’s he want?’

“Must have been a helluva party.”

“Yeah. It got out of hand,” she replied.

“Let me help,” he said, and taking a small box he brought with him, began picking up glass.

“No, Mr. Roberts,” she said, “I’ll get this. Really.”

“Look, Annalise,” he replied, “I was young once, too. Things got out of hand, I get that. Let’s not concentrate on that at the moment. Let’s get this shit cleaned up before the other neighbors see, and by the way, it’s Jason.” And with that, he went back to work. After a bit, the glass was picked up, and they had flipped over the furniture, which with the window, were pretty busted up.

Annalise looked at the table and despaired. She could feel tears rolling down her cheek. “Oh Mr. Rob–umm, Jason, what am I going to do? My parents will be back by the end of week…” her voice trailed off, and Jason Roberts knew that this was his moment.

“Annalise, you were a kid so you wouldn’t remember, but the construction side of my law firm built most of the houses in this neighborhood. Although I’m semi-retired, I am sure he can have some boys come out and fix this damage, your parents will never know.”

Annalise just stared back at her neighbor. She knew that Mr. Roberts had at all times been a quiet, laid-back man. In fact, she had rarely seen him since his Wife had passed away, maybe a year ago. And yet, here he was, offering her a lifeline. She knew that her parents would absolutely kill her, and if the HOA board complained loudly enough, her scholarship might even be in jeopardy; so a lifeline was something that she really needed, and she grabbed it as quickly as she could.

“Wow, Mr–Jason, that is too nice!” For the first time, she smiled. “But what about this table?”

He smiled, as well–she was on the hook, but she didn’t yet know it.

“Well that has had it, but no worries, we’ll stash it in my garage. This is still in production, so really just get another, again, you can get that in a day.”

Annalise replied, “Well…okay, but I’d have to clean out my college savings for that.”

“Look, no worries there,” he replied, “Let’s get the ball rolling on this, and we’ll sort it out.”

Within a few hours, Jason Roberts had two of his old crew over, to take measurements of the front window, and he explained the need for them to be discreet, and fast. They assured him they could have that work done by Friday, and he saw Annalise nodding in agreement, as she approached. The two had just gotten the smashed table over to his garage, and the other was to be delivered to Jason’s place pending finishing the window; when he decided to set the hook, and reel this catch in.

“So, Annalise,” he began, “looks like the total bill here could easily go three to four thousand dollars plus, once you figure in the furniture.” Seeing her face fall he held up a hand, “Hang on, don’t get upset…”

Annalise felt the whole world crashing down around her again, at least the third time since this all started. “But, Mr. Roberts,” she exclaimed, “I only have a bit less than twenty-five hundred dollars total!”

“It’s okay, it’s okay. Just have a seat here, let’s talk this out,” he responded, having hoped that this would be the case. “Now look, you know I’m on the HOA board, so I can make sure they never know about all this.You know what pests they can be, and the fact is, I’d be willing to foot this entire thing.” He looked at her and said, “Annalise, I know how something like this can snowball, and really put a dent in your future, and in how you interact with your family, and neither of us want that.”

Annalise blinked back tears and said, “Yes, you’re right…Mr. Roberts. I can pay you what I have, but even then, my parents will know something happened. I’m just amazed. You’ve been so helpful!”

Time to pull this fish in. “Well, it’s my pleasure,” he said, with a warm smile. “I’ll tell you what, though; nothing comes for Free, Annalise, and neither does my help. I don’t want to empty your bank account, so I’ll tell you what. You just agree to my terms, and I’ll foot this total bill. No one will ever know. Or, you can try it your way, and everyone knows. I’d really hate to see that happen.”

Annalise was only eighteen, but she was no fool. She understood what was being implicated, but she had never wondered it would come from aman older than her dad! She could feel her face go cold at his suggestion, and stammered, “Bu-But…you were so nice…surely you’re not…you’re not suggesting–“

Jason sighed and cut her off. “I’m afraid so, Annalise. My terms are this. I get to have you at least once a day, every day, until the day your parents get home. I’m not as young as I used to be, so I should be pretty worn out by then. In return, your parents will never have any idea of what happened, and the HOA will never know.” I could see that her mind was churning, as she tried to wrap her head around this. “Remember, I can be totally discreet. I should also tell you that my security cam that looks over the front, caught the whole thing; so I think this is a small price to pay.”

Seeing one of the contractors waving, he pointed to him and said, “Looks like they need you over there for some questions, one of which is payment. So you either go over there and beg, or tell them I have it, the choice is yours. If you choose the latter, then think it over and be back over here in two hours, and we’ll finalize everything.”

Annalise realized that she was truly in a tough spot, and the wildest part was, she found herself actually considering selling herself. She told herself ‘What choice do you really have? Her parents had forbidden her from having even a small gathering; so in her insolent defiance, she had a full-blown party, and here she was. Although Mr. Roberts bordered on old, while his hair was white, he at least had a decent body, from what she had noticed of it. Annalise had at all times wondered this guy just to be the sweet, old man across the way–so this turn of events was unexpected, to say the least.

No matter what, she knew she couldn’t let her parents figure out what had happened, much less the HOA. At least one or two of those people had feuded with her dad for years, so having them getting that information would be all she wrote.

At last, the contractor asked about payment, and as Annalise stuttered and pointed with her thumb, the man didn’t so much as bat an eye, as he said, “Okay, ma’am, we got it. In fact, for Mister-Rob, we’ll have it done a day early.” As he walked off, speaking rapid-fire Spanish to his other two men, Annalise sighed. She now knew, the die was cast, and she was gonna have to make the best of it.

As soon as his new Sex-toy left, knowing she would be back in a couple hours, Jason did what any guy his age would do–he took a nap. Rising from an hour’s doze, he grabbed a Shower, both to be properly clean, and to wake his Ass up. He had deliberately not given her his phone number, knowing it was show up or wimp out. He had just finished taking a Viagra and some water, when he saw his new Sex-toy walking across the street, albeit rather slowly, and fifteen minutes late, to boot. Opening the door, he ushered her in. Smiling he said, in a calm voice, “Glad you made it, now hand me your phone.” And taking that from her, he placed it, along with his phone, in a small empty cooler he kept on the bar. Pointing, he walked her over to one of the barstools, and Annalise took a seat with no prompting, so he sat in the next one over.

“So I’m glad you decided to go with option A,” he said.

“I can’t believe I’m doing this,” she responded.

He smiled. “Would you like some wine?” Jason gestured towards a pair of glasses beside her. Annalise was technically three years underage, but he knew she needed this to calm her nerves.

Mumbling something, Annalise grabbed the glass and drank it all in about three gulps, hardly ladylike, but understandable. “I have a few questions.”

“Of course,” he replied, “fire away.”

“Just this week, right? I mean, it’s all over when Mom and Dad get here.”

“You said they were coming back Sunday, so yes, through that morning. And before you ask, no, no one will ever know. No, I am not recording any of this, and yes, I am a man of his word.” He took a sip, as his nerves needed calming, too.

After a moment, Annalise, knowing the answer, asked, “So what do I do? What is, um…expected of me?”

“As I stated, you are going to make yourself available to me for about two to four hours each day. You will be doing things fully and willingly; you are to hold nothing back, and short of the toilet or pain, no limits.”

“And no pictures or film.”

Jason knew she would say this, which was fine, he wanted her to feel as though she had negotiated something, so he replied, “We will set the time the previous day, and you are to come over dressed as requested, nice and fresh, as it were.”

“How about I dress here if it’s, you know, risqué.”

Again, he figured on that one, and at least her response told him she was accepting it in her mind. He poured a small amount of wine into the glass, handed it to her, he said, “So let’s have one last sip…” to which they did, and then he took and set both glasses down. Standing, he took her hand and walked her to the nearby couch. The bedroom (and more) would come soon enough, and finishing he said, “We should get started, hmm?”

****

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

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