From the smartphone came the familiar sound of an incoming notification. Worried, she reached out her sweating hand to check who it was. Alison trembled when she saw his nickname. She was sick of the assignments he had been sending her for the past 6 months. She opened the chat.

[16:30] /MasterTormentor/ wrote: hi...

[16:31] /MasterTormentor/ wrote: you should have received a package this morning

[16:36] /Rich_cunt34/ wrote: It's really not convenient in the moment. I will have a look at it later.

[16:38] /MasterTormentor/ wrote: I am not asking. A friend of mine left it on the desk of your secretary.

[16:39] /Rich_cunt34/ wrote: Oh... fine. I will check it. But i don't have much time for playing games with you. I have an important meeting in less then an hour.

[16:41] /MasterTormentor/ wrote: I am disappointed. That only makes it way more fun and appropriate. The goal of our game is not to make you feel comfortable. After all you are only a pathetic anal pain slut, remember?

[16:42] /Rich_cunt34/ wrote: I said, I will have a look at it.

Alison van der Velden took a deep breath and left the phone on her smarthphone on the desk. She stood up and straightened the folds of her dress. With trained confident steps she made her way to the office next door where her secretary was knocked on the door and entered the room.

"Casey, дid someone leave a package for me this morning? "

"Yes Miss Alison", a well dressed man came here this morning." the secretary took out from underneath her desk a cardboard box and handed it to Alison. "He said it was from your cousin and you were expecting it"

"Yes, thank you Casey. I always expect random packages from my cousin" said Alison and left Casey a bit confused by that sarcastic comment.

Alison barely managed to return to her office when she heard the notification sound again.

[16:51] /MasterTormentor/ wrote: Did you open it?

[16:51] /Rich_cunt34/ wrote: Not yet. I just got it.

[16:51] /MasterTormentor/ wrote: Open it now. The mask inside is to wear this evening. We will be waiting for you at Norfolk Str. 34 at 8 o'clock.

[16:52] /Rich_cunt34/ wrote: But that's in the ghetto.

[16:53] /MasterTormentor/ wrote: You will like it there, I assure you. By the way you said you have your appointment now?

[16:53] /Rich_cunt34/ wrote: Yes

[16:54] /MasterTormentor/ wrote: Great. When you open the box you will find a second gift. I want you to go to the bathroom, take off your panties and shove it in your ass. Take a picture and send it to me as an evidence. Don't you dare to your pants back on or to take out my small gift from your asscunt. I want to personally extract it later. Understood?

[16:57] /MasterTormentor/ wrote: Don't make me wait. Are we clear?

[16:57] /Rich_cunt34/ wrote: Yes, master.

[16:58] /MasterTormentor/ wrote: Ok, see you later then. I am waiting for the photo though! You have 5 minutes.

In a hurry, she went into the bathroom as she didn't have much time. She unzipped her official dress and let it fell to the ground before pulling her panties slightly down. She hesitated for a second before opening the second package. It was reasonably big butt plug and a roll of black tape. It didn't seem to big, but for sure it was large enough to make her feel considerable discomfort during the upcoming meeting. She knew what she had to do. She took the eggplant like butt plug with her right hand and positioned it against her well used asshole opening. Before forcing it inside Alison van der Velden looked in the mirror to see herself - the rich and successful businesswoman biting her lip in pleasure as she pushed the buttplug inside of her own asshole. As the whole size of the plug find its way into her rectum she reached for the tape. "Very thoughtful from him" she thought while strapping her cunt and ass with the tape making sure that the plug wont just fell during the meeting. Before pulling up her panties and skirt she took a photo and sent it to him.

[17:03] /Rich_cunt34/ wrote: Are you happy now?

[17:04] /MasterTormentor/ wrote: Seems fine. You are disgusting anal whore, but you can stretch it a bit more, believe me.

[17:04] /Rich_cunt34/ wrote: Go to hell

[17:04] /MasterTormentor/ wrote: I wish you successful meeting. I hope your full rectum won't distract you that much.

[17:06] /Rich_cunt34/ wrote: As I said, go to hell

[17:07] /MasterTormentor/ wrote: Yeah, I know. See ya later. Don't be late.

As expected she wasn't feeling comfortable at all during the meeting. Every time she stood up to talk or to show something on the charts, she had to be really careful not to make too many strange movements that could give away that something was a bit off with her. The meeting ended and she was relieved that nobody seemed to notice anything. Once she was in her own office she finally took a deep breath. For a brief moment she forgot everything from the last few hours enjoying the cool air in her office. Sudden pain in her gut, threw her back into the reality when she sat too fast into her expensive office chair effectively pressing the base of the butt plug further against her overly streched sphincter. She looked at her watch. It was seven o'clock and she had to hurry.

Despite the uncomfortable fullness of her rectal fuck hole she somehow managed to drive with her expensive car almost to the address she was given. As a precaution she stopped at a paid parking just a few blocks from her destination. She locked her car and headed towards Norfolk street. Тhe sound of her heels echoed off the pavement and buildings around.

For the untrained eye from across the street, she was a well dress woman just passing casually through the neighborhood, but for him it was fully obvious, not only because he already knew her well, but also because he had trained dozens of anal whores and he could recognize from distance that a woman is walking around with something big shoved in her anal cunt. He waited a minute, just to ensure she was alone and went after her behind the corner.

Norfolk Str. 34 was a dead end street between two apartment blocks. There was hardly any light around but when he had almost caught up with her he saw her opening her purse and putting the leather mask on. After only a few seconds he was close enough too say something to her, without the need of raising his voice.

"I sincerely didn't expect you will come on time"

Instead of an answer she lifted up her dress. Despite the dim lightning he saw that she was up to her promise. She turned around showing him her taped fuck holes. Her pink tight panties stood strangely on the black tape covering her labia. He reached with his hand and ripped the delicate fabric from her body. Not satisfied he Pulled off the straps of her dress and dragged the expensive clothing down.

"How much you paid for that dress" he asked while unstrapping her bra.

" Two tousand"

"Only two tousand? What were you thinking when you were buying it? Did you think of you being anally fucked on a dark street with your dress halfway down?" her bra fell on the ground.

"No I haven't"

"That's bad, but maybe you can think of that the next time. Right?" he forced her to turn against the wall and pressed her masked face and naked tits against the rough surface of the brick wall. The decaying ceramic almost sliced into her flesh from the pressure he was using.

He looked at the black tape between her butt cheeks and pulled it roughly away. А short and quiet cry escaped her mouth. Suddenly freed from the tape her poor sphincter started to clench trying to expel the strange object. With his hand he initially held the plug inside of her rectum before starting to pull it out completely before inserting it again inside of her bowels. Since she met him her rear hole was becoming gradually looser and looser. This evening wasn't any different. Just after a short two minutes in the exercise her anus was already gaping obscenely. He didn't wait any other invitation. He dropped the plug on the ground, unzipped his pants and shoved his rock hard dick into the welcoming softness of her asshole.

He fucked her rough and hard without releasing any of the pressure holding her against the brick wall. Once all of his cum was well spread inside of her bowels. He withdrew his member and zipped his pants again.

"Hold your butt cheeks apart and stay like that. I have not finished" once he said that he took a dirty beer bottle from the ground. He rubbed part of the dust from the bottle on her wet cunt, this way greasing it. The wetness of her cunt was not enough to clean the bottle but it only made it look the dust muddy. Seconds later the disgusting abandoned bottle was forced into Alison van der Velden's asshole. He made sure it went as deep as possible before taking it out completely just to force it again back inside. With strong and merciless movements he fucked her ruined rectum until suddenly she came.

"I knew you from the beginning that you are needy anal whore" he said watching her body shaking in an uncontrollable orgasm. He moved away his hand which was holding the bottle still buried inside of her body. With the last few muscle spasm of the orgasm, the bottle fell back to the ground where it belonged anyway, leaving her asshole gaping. As her breathing stabilized, the emptiness of her anal crater was suddenly filled with her prolapsing muddy rosebud.

"You know what? You are really sexy that way. Why don't you go home with your prolapsed asshole underneath your dress? You can also send me a photo as usual" he grinned.

She didn't answer. For a brief moment he thought he saw a spark of hate in the corner of her eye while she was putting her dress back in place. She didn't even bother to take her bra and thorn panties from the ground, but instead walked away. It was fun watching her almost walk out onto the lights of the main street with the latex mask still on. At the last moment she got startled and took it off and put it in her purse.

...

With no surprise a bit later this evening he received a photo from her. She was naked in her bathroom and she had just made a selfie of her back in the mirror. Nor her face or shoulders were visible on the picture, but between her buttocks was still visible the dirty rosebud. He smiled to himself.