The Sim - Custom Scenarios Pt. 02

Disclaimer: This story is, as always, set in a simulated virtual reality revolving around free use and heavily anal focused. This particular chapter describes rough, abusive anal sex with an older woman, if that's not your cup of tea, you should probably skip this. This is all pure free use fantasy fulfillment; don't expect realism or normal behavior.

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While I liked how things were in this world, the attitudes and norms that existed here, I got curious about what the world would have looked like in the early days of Free Use when it was just implemented.

So with that idea in my head, I asked,

"Well, I was thinking of going back to the early days of Free Use, right around the time it went into effect. Specifically, I want to meet the female politicians that helped make it law," I said aloud, knowing Simone could hear me.

Replying briskly as always, "Of course James, one history lesson coming right up, do you have any place in mind to form in at?"

"Yeah I do actually, could you put me right at parliament?"

"We can arrange that, compiling now," Simone replied.

When the world swam back into focus I found myself standing outside parliament. Things looked... Normal, there weren't people fucking in public or anything crazy like that, it was just a regular day; either because the law wasn't ratified yet or normal sensibilities kept people from fully utilizing it, it was hard to tell since I didn't know exactly when Simone had put me but I trusted she had an entertaining story set up for me.

Just as I was getting my bearings I noticed a tour group pass by and head toward parliament itself. I decide to attach myself to the group to learn a thing or two. The tour guide takes the group and myself inside and offers us a light history lesson while walking in, specifically regarding the Free Use Act; how it was proposed, the push and pull of its support, it's limited implementation, its current controversy and the shaky position it's in etc, answering my question of when I was, I guess I'd have to restrain myself for now.

We entered a corridor lined with portraits and office entrances next to them, the portraits had on them the various local politicians that worked in the parliamentary building. As we passed each, the tour guide lady gave us a brief description of the accomplishments of each politician. Most were men but one of the portraits was of a woman, Judith Hamill, one of the few women that voted in support of the Free Use Act so the tour guide tells us. Despite being in her late 50's Judith was a very handsome woman, the various wrinkles and lines on her face did little to detract from her features or beauty and her grey hair gave her a very dignified appearance, she reminded me of an even more attractive Lindsay Duncan. Credit where its due, Simone really had me pegged.

I peeled off from the tour group and headed into Hamill's office. I was greeted by a stern looking receptionist in the waiting area who opened her mouth and was about to say something when Mrs. Hamill opened the door to her office and came into the reception area. She dressed conservatively in a simple grey business skirt and jacket with a white dress shirt, her jewelry was tasteful but modest, she looked nice more than anything.

Hamill spoke quietly and quickly with her receptionist before turning back to her office. As she turned around she noticed me for the first time. Giving me a genial smile, Mrs. Hamill said, "Hello there young man. I don't often get visitors from your demographics so this is a pleasant surprise; can I help you with anything?"

"Hello Mrs. Hamill, uh, yes actually I came in because I was hoping to have a chat with you, about our laws and how they were put into effect, one in particular actually."

Before Mrs. Hamill could reply her assistant cut in, "I'm sorry, appointments with the MP must be scheduled beforehand. You'll have to come back another day if you want to speak with Mrs. Hamill or any other representative for that matter."

That made sense, but I didn't think the rules applied to me. Hamill vindicated that belief when she spoke up, "Actually that's quite alright Marsha. Young man, you've caught me at a good moment, I don't have anything particularly important on my plate right now and have about an hour free. If you'd like, you can come into my office to chat right now."

Smiling back I reply, "Yes that'd be perfect," and follow Hamill into her office to take a seat.

Taking the initiative, Hamill asked with a knowing smile, "I presume the law you were curious about in particular was the Free Use Act, correct? Young men typically are interested in it."

Smiling again I nod, "It's just interesting is all, you're one of the only women who voted in favor of it, the question on everyone's mind is why?"

"Well, to be frank Mr...?"

"Jacobs."

In an unrealistic display of honesty, Hamill admitted, "Well, to be frank Mr. Jacobs, it was just arithmetic, it was a popular proposal with widespread grassroots support in my district. It was either vote in favor of it and retain my seat where I could continue to serve my country and have a say in the governing of this nation or against it and lose any opportunity to affect further change."

"Wait, so you don't agree with the law in principle?"

Shrugging, she replies, "I don't have to agree with a law to obey it or respect it." She pauses for a moment before adding, "Besides, it might not even matter, it's not certain the Act will survive in its current state. This is something of a dry run for the Act. As I'm sure you're know it's only been implemented at the local level, it still has to make its way through the House of Representatives if it's to be ratified nation-wide. That's a big if; it's still rather controversial at the moment so there's a considerable chance it'll die on the House floor, and if that happens, even the local variant will be repealed."

"So, will you be fighting for it?"

Hamill lilts her head, "I'll make a token effort but there's no need to tie myself to a sinking ship."

"I see... Well, thank you for that."

"You're welcome Mr. Jacobs."

"I'd like to have sex with you now."

"W-what?" Hamill replies in complete shock. She seemed to be caught utterly off guard by what I said, eyes wide with surprise.

"I said I'd like to have sex with you now, the Free Use Act applies here doesn't it? You're subject to them same as everyone else right?"

"W-W-Well yes they do but... but..."

"Well great. Do you mind pulling your skirt down for me?"

Hamill seems to be in total shock, but after several long moments, she takes a deep breath and calms herself. When she speaks again, it's with much more poise and composure.

"You know Mr. Jacobs, I had always understood this could happen at some point, intellectually I knew exactly that, and yet having it actually happen to me is all together a different thing. But I respect and obey the law." With that, she unclasps the front of her neat grey business skirt and lets it fall to the ground. It's a pleasant surprise to see that Mrs. Hamill didn't wear granny panties but had on these small briefs instead.

I make my way around her desk and over to her, "Those too now."

She hooks the sides of her briefs with her thumbs and pulls them down with a great deal of gravitas which tickled me. I then slipped the jacket off her shoulders, tossed it onto her chair and stood back to look at her, she looked good in just her dress shirt albeit slightly embarassed; she really was fantastically attractive for a woman her age.

"Please turn around and bend over your desk Representative Hamill," I got a kick out of saying it like that. Hamill dutifully obeyed.

Fishing out my cock from my pants I thought I would definitely need some lube for what I planned but didn't have any on me, nevertheless I reached into my pocket expecting to grab some anyway. Just as expected my fingers wrapped around a bottle, 'Thanks Simone' I thought to myself. Opening up the bottle of lube, I generously pour it over the length of my stiff cock and onto Mrs. Hamill's ass too. Shuffling up to her I use the tip of my cock to smear it around her little brown hole, she jumps when I do.

"W-what are you doing?" She asks again in shock.

"I'm going to fuck your ass, like I said."

Hamill yelps out, "What?! You just said you wanted to have sex with me"

"Yes, anal sex. Mrs. Hamill, the law is very clear on this, any and all types of intimacy are allowed."

Hamill spends a moment thinking furiously before seemingly settling down, she replies after a moment, "It's just very unusual is all," then with sudden uncertainty, "very few people have sex that way. Don't they?"

Getting an idea, I tell her, "Actually Mrs. Hamill, this is quite common, practically every girl these days does it regularly. Wasn't that the case in your time?"

Recoiling Hamill says, "No, absolutely not, it was-it was extremely unheard of from anyone other than sex workers or in pornography. God, I've certainly never done it much less thought about it... And you're saying now everyone is? I can't believe I've become so disconnected."

Shushing her I say, "Relax Mrs. Hamill, this is perfectly normal. You'll get used to it soon enough." I slowly apply pressure on her asshole. She may have been an anal virgin, but time had taken a toll and I slipped past her ring suddenly with relative ease, eliciting a gasp from Hamill. I slowly worked my way deeper and deeper into her ass, quickly sinking in down to the balls within a minute, hardly giving her any time at all to adjust to my size. Hamill only just manages to maintain her composure with deep, slow, controlled breaths in and out.

I stay still once my balls are resting against her; Hamill takes the opportunity to ask me with concern, "You're saying women often have sex like this?"

"Yes, regularly. It'll just take some time to adjust is all, don't worry." It was too fun giving Representative Hamill all kinds of wrong impressions, I felt a bit guilty of taking advantage of someone ignorant but it was a small thing. I wondered how much of a wrong impression I could give. After giving Hamill a moment to adjust to having my cock fully inside her ass, I pull out all the way. Hamill exhaled in relief and I felt her body relax.

"Is that it? Is it ov-" Hamill was choked off mid reply as I suddenly drove my cock back inside her ass, almost managing to bottom out in one fluid stroke; Hamill's head drooped down into her folded arms and she let out a muffled groan as I took her ass. I began fucking her with deep strokes in and out at a moderate pace. Hamill gasped often as my cock pushed and pulled at the walls of her asshole, occasionally even swearing uncharacteristically. After a minute Hamill finally manage to catch her breath enough to talk, "That, Mr. Jacobs, was spectacularly uncomfortable."

"What was?"

"When you drove yourself inside me so suddenly after pulling out."

Giving her a look of fake confusion I tell her, "Really? Women typically love that, it was practically all my last girlfriend would ask me to do. Maybe it's the position, try turning over onto your back."

Hamill gave me a skeptical look but again, dutifully obeyed and twisted on her desk onto her back to face me, her face was beet red and she looked deeply embarrassed. I resumed my deep strokes into her asshole, though punctuating them occasionally by bottoming out and pulling entirely out as quickly as I could manage. Those seemed to be what Mrs. Hamill had the most trouble with. As the minutes ticked by the 'punctuations' got more and more frequent until I was doing nothing but rapidly plunging into her asshole only to tear it out, leaving her feeling empty and gaping before repeating the process endlessly. Hamill twisted and turned on the desk, struggling to manage the massive cock pounding into her only recently virgin asshole.

It was fun to watch Mrs. Hamill face as I did this, almost without fail, every time I took out my cock there'd be this slight look of relief that quickly passed across her face only to be replaced by a grimace a moment later. Looking down at her, the sight of such a dignified older woman taking it up the ass so brutally sent chills down my spine.

Mrs. Hamill spoke almost pleadingly, "You're certain? You're certain this is normal? It doesn't feel normal Mr. Jacobs, in fact it's a rather uncomfortable sensation."

"Perfectly Mrs. Hamill, all modern girls do this. It's simply expected of ladies these days and quite unusual and old fashioned for them not to do anal."

Nodding solemnly, Mrs. Hamill went quiet again. After a few more minutes, Mrs. Hamill's embarrassment seemed to have been overcome by her desire to lessen her discomfort so she reached down and began to play with her pussy finally. I got the feeling she had resisted the urge to do so because it would've made the act more participatory, I had enjoyed it either way and wanted to keep her hands away from her pussy.

"Please, Mrs. Hamill, none of that."

Hands freezing, Hamill replied, "What? Why am I not allowed to masturbate?"

"It's not that you aren't allowed, it's just these days it's considered extremely rude for a woman to touch herself that way while a man is using her asshole."

With her hands slowly retreating away from her vagina, Mrs. Hamill replies, "Oh. I see, we'll I'm very sorry for that young man," I timed one particularly hard thrust to her apologizing.

"It's alright, you just didn't know any better."

Grimacing hard at the relentless sodomy Hamill replies, "Yes, it seems there's quite a bit I don't know these days." Adding in a smaller voice, "When did I get so disconnected?"

"I don't know Mrs. Hamill, but there's always time to change that." I reassure her. She gives me a strained smile as I continue slamming into her that thrills me.

Eventually Hamill endured as much of my abuse as she could before finally speaking up. I was very impressed she had managed to this long though, she definitely had grit.

"Please, Mr. Jacobs, that... thing you've been doing, I don't think I can get used to it, I've given it time, but it's been half an hour and it's still uncomfortable and painful every time you enter me, it doesn't give me enough time to adjust. Couldn't you just stay inside please?"

"I'm almost done Mrs. Hamill, I'm almost done." I was lying, but politicians lie all the time so I didn't feel too bad. Though I wasn't completely heartless, I had an idea to distract her.

"Mrs. Hamill, have you considered this might help you in the polls among the youth demographic?"

The topic of politics did seem to perk her up a bit. "How do you mean Mr. Jacobs?"

"Well, it's just, seeing how surprised you were at anal and modern sexuality in general, I figured the rest of the politicians here would probably be much the same. And I was thinking with the Free Use Act now in effect..."

Mrs. Hamill certainly was a political animal, she picked up where I was going with this and cut me off mid-way, "...I could make a name for myself, stand out and gain popularity among the youth demographic by embracing the laws first and foremost publically... Mr. Jacobs that actually is a good idea, the youth voting turnouts are generally low, but they were spectacularly high for the Free Use referendum, I could tap into that enthusiasm. I could make the fight for it my whole platform." The fact my cock was pistoning into her asshole, leaving it a gaping mess between her every word no longer seem to hold Mrs. Hamill attention, her thoughts elsewhere. I took advantage of the distraction to pound her ass even faster and harder than before.

It was taking a toll on Hamill but she didn't seem to notice. Because there wasn't just wasn't enough lube left to let me slide in easily anymore, the walls of her asshole hugged and gripped my cock every time I pulled out, I was turning her guts inside out and she didn't care. The minutes dragged on while she talked aloud and considered options, all the while I continued to churn her guts, turning her asshole into puffy, red, raw meat as I dipped in and pulled out. It was a sick and perverse look for so dignified a woman.

"And you could help me," she said brightly.

That got my attention, now it was my turn to ask, "How do you mean?"

"Well it's clear I'm woefully unexperienced with modern sexual norms, but you aren't, you could act as an advisor, telling me what would or wouldn't work among youth voters. Even now you could give me ideas. For example, we're currently in the middle of an advertising campaign, we're about to release a slew of posters and TV spots, they haven't been finalized but I'd like your input."

Considering it for a long while, I finally say, "Well, the focus is on the Free Use Act. It would be important to emphasize your role in getting it enacted locally, your continued support of it at the national level and foremost your modernity. Young voters see politicians as a sea of older, disconnected men, but you could be different. You could be someone relatable to young women and men everywhere. For the TV spots, I think you should have someone freely using you while you did the spot."

With an enthusiastic glint in her eye Hamill says, "Yes, that's exactly the kind of idea I was looking for Mr. Jacobs. I like it, it wouldn't even need to be unpleasant, with the camera on my face and the man behind me it wouldn't have to be anal."

Frowning, I try to flip her, "Well no, it wouldn't have to be if you shot it like that. But I think you should have to hit on the modern part again and again and again, really nail the message. You aren't some old fashioned politician, but someone who appreciates the times they live in who doesn't pine for old days, you take it up the ass. Anal, and lots of it needs to be tied to that message. Shoot the spot unconventionally, on your back with someone very visibly assfucking you filmed from above."

Thinking about it hard, Hamill nods more and more to herself, "Yes, yes that's right. If I might add something, if anal is as important to modern sexuality as your saying, I should avoid ever having anything in my vagina publically, my political persona could be exclusively anal, I could go so far as publically denying some confederates vaginal. What do you think of that Mr. Jacobs?"

"Mrs. Hamill, that's a perfect idea. This would make you very popular with the male demographic. You could exploit that further."

"Campus, town hall or rally meetings with Q and A's where the public can question and use me?"

"Yes!"

During our whole conversation, I continued to violently pummel into Mrs. Hamill asshole without her concern. The relentless assault on her asshole had taken a toll, it had been feeling looser and looser, every time I ripped my cock from her ass it would gape lewdly and massively for long moments. The meat around her hole was an angry shade of reddish pink and swollen badly, it was extraordinary Mrs. Hamill was able to take such abuse on her first attempt. The sight contrasted incredibly with her neat hair, prim makeup and beautifully classy look, the sight of the contrast was what drove me over the edge. I felt the pressure building in my balls as I started to cum. Slamming in one final time, I spewed a burning hot load of cum into her Representative Hamill's ass as deeply as I could manage. I continued to lightly fuck her until I grew soft.

Pulling out and stepping back, I take a moment to enjoy the aftermath I left Hamill with. Smiling with another lewd idea in mind, I take out my phone. "And for the posters, I have an idea."

I turn on the camera and snap a series of shots of Mrs. Hamill's visibly ruined asshole, the cum that leaked slowly out of her abused hole and onto her desk where it pooled into a substantial puddle beneath her, it worked well in the shot. Seeing my intention, Hamill gave the camera a proud and steadfast look that belied her condition as she leaned back on her elbows.