The Inevitable

I closed the door behind us.

"Are we alone now, miss Diamanti?"

"Why would you ask something like that, sir?"

Oh God. She was really playing this up. That needed to stop now.

I placed my backpack on the floor. I wouldn't come all this way without all my newly bought implements.

I took a couple of forceful steps towards her. She didn't move, just looked at me with feigned wonderment. I placed my hand around her throat. Her widened eyes told me that she didn't expect that. I pushed her on to the bed, on to one of her stuffed toys. I leaned in closer.

"I asked. Are we alone, miss Diamanti?"

She nodded quickly. I guess it was hard for her to talk like this. Good. I let her go.

She got up and coughed loudly. Didn't matter, sound wasn't going to be an issue here.

"Urgh... Hey, don't... No throat stuff, okay?" What? Did she really think she had any negotiating power here?

Just for that, I grabbed her throat again. She gasped.

"Get naked, little missy. You have a lot of apologizing to do."

This time I just threw her on the bed, and walked back to my backpack. She only coughed one time, and rubbed her throat a little.

"...Fine, sir. Are you... going to spank me again?" (GLORIA: +2SP) (+25SP) She said as she carefully stood up, fingers on her blouse's little buttons. Seems she was back in roleplay-mode again.

"No. Not exactly. This time I'm going to whip you.", I said, pulling out my black, leather riding crop from the backpack. She stopped her undressing as she saw me make swishing sound with it through the air.

"W-What?" I'm sure we were already good levels above the moderate spanking she was expecting here.

"You see, a bitch like you needs to be trained like an animal that you are. I went way too easy on you in the basement." I touched her chin with the crop. She was terrified, but I'm sure I could practically smell her arousal from across the room. And was that a wet patch forming in her pants? "You need to learn. Your. Place. And I'm going to make damn sure that you do."

She swallowed hard. Her eyes kept following the end of the crop, as I moved it subtlely from side to side.

"Why aren't you naked yet?"

"...Sorry, sir." She hurried up now. First the blouse fell to the floor, and then her pants. She was now standing in front of me, in her underwear. "Are you... going to punish me for not picking up all those candy wrappers?" No doubt about it, she was really getting into this now. And she knew it. This was a new experience for me, this girl definitely had a submissive streak inside her already. Which made things easy, and also kinda hard at the same time. It was harder to humiliate someone who wanted to be humiliated. That just meant I had to be more inventive.

And I don't know if I would call her actions as being truly submissive. From another point of view, we were playing this game the way she wanted it to be played. Like she was weirdly in charge.

I didn't like that.

"No. I'm going to punish you for being you. An arrogant, rich, worthless waste of DNA, who doesn't yet realize that her only reason for existence is for my pleasure from now on."

She seemed offended. And not in the way she liked.

"Hey, that's-"

"Take your fucking underwear off already. I'm getting bored here."

She looked grumpy, as she finally slid of the final pieces of her clothing. This was the first time I actually saw her little B-sized tits. My only other experience was groping them in the kitchen a week ago. Her bubble butt was no revelation to me, but I still loved the sight of it. Definitely her best quality. I think she was trying to act brave, not covering up anything with her hand, but the blush on her face told me that she really wanted to. Little girl tried acting like a big girl.

I sized her up lecherously, hiding none of my intentions. I got close to her and squeezed her titty. She was trying to act nonchalant, but that stopped once I pinched her nipple. She made a small eep-sound.

"Just as I remembered. Still developing. I'm sure you'll have your mother's huge mammaries some day."

Before she could say anything to that, I squeezed her ass too. That made her back away from me a little.

"Still sore, huh? Well that's going to be a light memory for you after today."

I placed the crop in front of her mouth.

"Let's start your education, then. This is Mr. Ouch. Kiss Mr. Ouch, and tell him that you look forward to working with him"

She was shooting daggers at me, but I could also see that she was slowly adjusting to being treated like this. She gave Mr. Ouch a nice little peck on its end.

"I look forward... to working with you, Mr.... Ouch." (GLORIA: +1SP) (+26SP)"

"Good. Now get on the bed. Ass up."

She assumed the position with very little hesitation. Her voluptuous ass was pointing straight at me again. That's an ass that you just wanted to make as red as possible.

All of this... It was getting me very little points. She was so accomodating. I knew my crop was going to be a lot more painful than my hand or the paddle, but there was no guarantee that even this would work. This was all fun for her. So let's just reverse that.

"I want you to apologize, Gloria. For every shitty little thing you've done in your whole life that made you such a prissy little bitch. I want to hear 'I'm sorry, sir, for being Gloria Diamanti, a self-entitled bitch!'!

"No! I won't!" She shouted, wriggling her butt around, waiting for the crop to land on it. Her pussy was already dripping on the bed.

"You will apologize 10 times. There will be a whipping after each apology. Now, start."

That threw her off. She was supposed to start? She turned her head and looked at me. I just stood there, with the crop in my hand, waiting for her.

This wouldn't start before she made the first move. It must've been very confusing.

"No! You can't make me, sir!" She shouted, wriggling her ass temptatingly around and around again. But I stood still. Crop in my hand. Waiting for her.

She once again turned her head to me. "Umm... Aren't you..."

"Do I need to repeat myself? Apologize."

She must've reached that humiliating thought by now. This whole thing could end right now, if she didn't apologize. No spankings, no whipping, no... fun. She had to admit to how much she wanted this to happen.

"I'm... Okay, I'm sorry sir." (GLORIA: +3SP) (+29SP)

"The whole thing. And no added words."

She sighed. "I'm sorry, sir. For being Gloria Diamanti." She took a small break there, hoping she wouldn't have to finish. But she did. "A self-entitled... bitch." (GLORIA: +6SP) (+35SP)

WHIP! SLAP! WHIP! SLAP!

I gave her two hard licks with the riding crop. She screamed out in pain. She grabbed one of her big teddy bears on her bed and held on to it tightly, to try to think away the pain. It didn't last long. It was pretty easy to see the change in her face, as the first sting of pain was now over and was turning into pleasure. Another drip out of her pussy.

The crop marks were appearing on her derrier canvas now. Beautiful sight, if I do say so myself.

"Second time."

Any sane person wouldn't say the phrase at this point, knowing what followed it.

But hey, this was Gloria Diamanti.

"I'm- sorry, sir. For being Gloria Diamanti. A self-entitled... bitch" (GLORIA: +2SP) (+37SP)

WHIP! SLAP! WHIP! SLAP!

"AAAAAA!" That was quite the scream. More than proof to me that nobody else was in the house, because I would have been arrested that instant. Also I didn't think I'd have to worry about the sound escaping to the neighbours, their houses were sufficiently far away.

Gloria bit into her teddy bear, which was kinda hot in a weird way. I was almost starting to get that stepfather feel.

"Good, little missy. Again."

And she did. And I whipped her. This went on the whole way through to the tenth whipping. I didn't get any more points out of her, but it was pleasureable to see how it actually got harder for her to say the phrase every time. But she was a trooper, and got to the end of it. There were a couple of tears that fell from her eyes on to her teddy, but her pussy was a true waterfall.

At the end of it she was rubbing her ass, desperately trying to soothe it. I noticed her hands kept getting nearer and nearer her pussy lips. Was she about to masturbate in front of me? Did it take all of her strength not to do it?

I could've just told her right there and then, that only I could make her cum now, but I wanted to keep that secret to myself for a while. I had sort of grown to like the idea that my women found out this fact for themselves. That they slowly realize, that only my dick gets them there, and had to accept it.

"Keep your hand from there, little missy. That's not proper behavior." fuck. I don't know where that came from. Was this stepfather thing actually getting into me?

She resignatedly moved her hand away from her pussy lips. (GLORIA: +1SP) (+38SP)

"The proper thing here is for your educator to get rewarded." I said, as I took down my pants. My huge erection sprang out of my pants. Gloria turned her tear-filled eyes towards it, and couldn't hide the look of excitement.

"Wait..."

"I think your pussy is begging for it, don't you think?"

"B-but it's my first..."

"Or I can leave you like that. It's up to you. Hurry up. I got places to be."

She was angry. She wanted to shout at me and tell me to get out, but at the same time she couldn't deny how hot she was. This was the horniest she had ever been, including yesterday too. And yesterday she couldn't get a release now matter how hard she tried. Was this it? This was the moment she would lose her virginity? To me, a complete asshole?

"Just... Be gentl-" (GLORIA: +5SP) (+43SP)

I grabbed both of her red cheeks, making her scream in pain. "Girl like you never needs to know what gentle even means."

I slid my dick into her more-than-well-lubricated crevice. She screamed again, as her hymen broke. Definitely a more pleasureable scream this time. And luckily she didn't seem to be bleeder. I didn't want to leave those kinda marks on her bedsheet.

In a few seconds all formalities were over, and I was pounding her like a jackhammer. She still tried to talk, but could only make weird sounds as her whole world lit up like a christmas tree. I squished her head hard against her teddy to get more leverage for my rough fucking. It looked like she was starting to leave this planet and zoom into another atmosphere as I really let her **** pussy have its first true dicking.

We changed positions multiple times. I fucked her doggystyle for like ten minutes, pulling her hair and shouting insults at her. All she could do is moan. Then I lifted her up and fucked her against her boyband poster. The poster became pretty scratched after she gripped it with her nails in a moment of passion. I held her up by cupping her tits as I entered and exited her canal multiple times. Then we finished in the cowgirl position, with her riding me up and down like a woman possessed. She was losing strength now, and her movement got slower and slower. It was time to stop.

"This.... Is... the... best..." she moaned with her eyes rolled up inside her head.

"Cum."

She came so hard, that for a moment I was afraid that the pressure would blow off my dick. She fell on the bed and convulsed like crazy, which left me ample time to finish my own orgasm on top of her stomach. I came a little on her face too, for good measure. This was still the very first time she must've come in contact with a man's cum, so I didn't want to make it too excessive. Not that she would've noticed anyway. After one minute of endless orgasm, she blacked out.

I tapped her head. Nothing. I tested her breathing. It was fine. She was just in a true cum coma.

Which was excellent.

As useful and fun all of this had been, I still had a mission to do.

Oh yeah. ACTA first. Oh wow, nothing new. Probably the first time I checked with nothing new. Rare.

Anyway. I began by wiping Gloria down of all my cum (good thing I brought a towel), and put her clothes back on. She woke up a little during all of this, but mumbled only something delirious. I placed her on the bed, and pulled the blanket over her. I made sure her room looked the same as before I entered it, took my backpack, and left. If Maria really wanted to check her daughter's room, she would find no proof of someone having stolen her daughter's virginity. Other than the smell of sex and the broken poster, of course. But the poster could've broken for any reason and the smell wouldn't last that long.

Now, I had the house to myself. Which one of these billions of rooms was going to have Maria's secrets in it?

Well, that involved me checking every single room. And I did. I had still good time here. Maria was most likely at the office and usually left only like three hours from now. Of course I couldn't trust that fact alone, I still had to be fast.

Alright. This looked like her study. I deciced to devote my efforts to this room.

The next three hours went by fast. Luckily Gloria spent the whole time sleeping off her life-changing experience, so I could focus on this alone. First of all, there was no getting to her computer. Wouldn't even try, it was password-locked and a tough businesswoman like Maria surely wouldn't use an easy password like "Gloria" or "Giovanni" or something. No, the room was filled with papers, deals, agreements, receipts, anything any reasonable, smart investigator would have a field day with.

I don't think I was a smart investigator, though. It was all just fucking numbers. Everywhere. I really tried to make sense of them, but couldn't. Math was never my strongest points. I tried comparing the numbers. Were there some tax fraud here? No idea. Were these payments suspicious? No idea. Were these deals illegal? No idea. But little by little, I was getting some sort of a bigger picture. That still had no illegality to it as far as I knew. Just all the transactions Maria was making... it did seem like proper business stuff. Fuck.

Until there was one receipt. The receipt itself wasn't that special, it was for some ground work or something.

The important thing was what was written behind it.

"Frank. Rain. 14th. Frogs will bloom."

What the fuck was this? Password or something? For her computer?

I tested it out. No luck. Not a password reminder. What was it then? Some riddle? Some way to memorize something?

Unfortunately, my time was up. I still had to clean up and get the fuck out of there before Maria came in. If the only thing that I got out of this was going to be this small receipt, then so be it. I memorized the phrase and put all the papers back to their original places.

I checked on Gloria before I left. Good, she was sleeping. No need to know I was still here. And the smell was gone too. Just don't let your mom see you red ass now.

I exited the front door. Good thing it was starting to get darker now. I escaped the mansion.

As I walking home I kept thinking about the phrase. ...It was probably pointless to devote more time to it. The more concrete plan was now to fully own Gloria by the end of the week and **** Maria with her somehow. I didn't have time for anything else.

Well, that was the plan. Until two big guys with sunglasses suddenly stopped me.

It happened fast. One of them pulled a duffel bag over my body, and they threw me into a waiting van.