The Waitress Ch. 2

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Sweet Ashley is taken anally... and loves it.
3.1k words
4.3
41.4k
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Part 3 of the 10 part series

Updated 10/31/2022
Created 01/01/2002
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*******

Thanks to Connie the Cunt for giving me ideas for this story. I dedicate its continuation to her and her cunt :-)

************

"Now she won't need a rise in salary!"- said Sam making mock of Ashley. She knew this was going to happen, and she hated it. The other girls were looking at her now with a sarcastic smile, and she knew things would never be the same again.

"See? It's easy!" - said Trish.

"Shut up... I feel awful"

"But you liked it, didn't you? I know you did. He's got a hell of a cock"

She thought about that. She had to admit she had never felt so much pleasure before.

In fact, what other men had given her, including her ex husband, was nothing compared to the wild sensations Harry provoked in her.

"Yes, I liked it. Are you happy now?"

The mere thought of Harry's portentous cock pumping inside her made her feel shivers.

The worst thing was that just thinking of his cock made her wet again.

*****

"Alright, Mrs. Thropp. I'll take this partial payment, and I'll wait until Friday night for you to cover the rest. Be aware that there will be no reimbursement if you aren't able to cover all of the debt"

"Please, Mr. Sanders, I need more time... Friday is too soon for another $ 1,000 dlls"

"I'm sorry, Mrs. Thropp, that is all I can do for you"

******

Thursday night, Ashley was frantic, waiting for Harry's trailer to come. It was an agony to see the trucks coming, but not Harry's. The other drivers had given her some $ 300 dlls. more in all of the week, but it was still not enough. And she just refused to swallow their cum, which meant they weren't very grateful after the frolicking.

Finally, Harry's truck parked outside Sam's. She sighed in relief. The big man came in, and took a table near the entrance.

Ashley rushed to take his order.

"Hello, pretty pussy... How's my little slut tonight? You look beautiful, baby"- he said, looking at her very provocatively. She blushed again.

"I'm fine. No, not so fine. I'm glad to see you"

"Why not so fine?"

"Nevermind. Please go out with me tonight"

He was amused by her directness.

"I like that, baby, that you ask me for a date. I have a big hard on already. Remember how big it felt inside you?"

She blushed again.

"Come here, pussy, near me"

She did. He grabbed her pussy from behind, below her waitress skirt, and grabbed it hard.

"What are you doing!"- she said, alarmed.

"I'm doing what I want, and you will consent to anything I say, pussy"

"Please don't do that. I'll be good..."

"Yes you will be good. I know that. You are my little slut and you'll be very obedient tonight. Is that right, pussy?"

By then, everybody was watching them, his hand on her crotch; everybody pretending they were doing their business, but actually not missing a move of what was happening.

"I asked you a question, baby"

"Yes"

"Yes what?"

"Please..."

"Say it, I am your little slut and I will be very obedient tonight"

"Please..."

"If you don't say it I'm going to fuck you right now over the table, pussy"

"No! I... I am your little... slut..."

He grabbed her twat harder.

"Say it all, pussy"

"Please, you're hurting me"

"Say it, pussy, or I'll fuck you right here"

"I... I am your little slut... and I will be obedient tonight with you..."

"VERY obedient"

"Very obedient. Please let go... Everybody's watching"

"You like to be treated roughly, Ashley. I made you wet..."

He let her go. Goddammit! He was right... She was very wet!! What was happening to her?

"Bring me my coffee, pussy. I'll be in the cabin. Trish told me you need $ 1000 dlls for tomorrow. I'll give them to you if you go stark naked to the cabin, except for the shoes"

"Please. I can't do that"

"Yes you can. I'll give you even more. But you'll do as I say. You'll do anything I ask you to do... and your son will be able to go to school..."

Goddamned Trish!! She had told him everything, the bitch!!

"Please..."

"Well, then I'll have to see who will please me tonight." - Harry said casually, then he shouted: - "Hey Betty, can you be with me tonight?"

"No! Please. Please don't call her..."- But Betty soon came to the table.

"Sure, baby. I'd love to be with you and that big whopper you have..." - said Betty playfully.

"Please..."- Ashley was in panic.

"Will you do as I say, Ashley? To anything I ask you to do tonight?"

There were tears in her eyes when she answered, and she was sheepishly looking at the floor.

"Yes"

"You're a slut, Ashley" - said Betty. "Never look at us again as if you were superior, because you're just a piece of shit. You're a slut..."

She was crying when Harry grabbed her crotch even more roughly.

"Yes you are a slut, so don't cry. You are soaped wet now down there! How do you explain that, cunt" - he said.

God, it was true! She was soaking wet now.

"I tell you, Ashley, you like to be dominated, and I'll show that to you tonight. When you go to the cabin, you'll go stark naked except for the shoes. These shoes..." - he

took a pair of black high heel shoes, very high, the kind used by hookers. "There, baby, these are the right shoes for you now that you're realizing what you really are"

She was crying for the humiliation and degradation he was putting her through, but at the same time very hot for being treated this way. He grabbed her pussy hard again, under her skirt..

"These shoes and nothing else, do you understand, pussy?"

She heard herself saying yes.

*******

She went to the dressing room and took off her clothes. She could not believe in what she was about to do. I'm doing it for the money only, she repeated to herself countless times. "Yes, but you are soaking wet and you can't help it, you bitch" an inner voice told her.

All naked, then she put on the high heel shoes, breathed deeply, and with little hesitation now, she went out of the dressing room and into the night. She was very conscious of the truck drivers whistling at her and shouting obscenities at her. This was making her terribly self- conscious but extremely horny and excited at the same time. A bit wobbly, because the high heels were really very high, but she managed to look gorgeous and sexy, naked in the parking lot, with nothing but the high heel shoes on...


She found the cabin's door closed, and had to ask Harry to let her in.

Harry took his time, and meanwhile told her how she was going to be treated tonight.

Roughly, just as she liked it, he explained.

"Please, let me in" - she begged.

Finally he let her step into the cabin.

"You got a gorgeous body, pussy, you know that? You should be a hooker, really"

She blushed again.

"Get rid of the shoes, little bitch, and get on all fours, cos I'm going to fuck you in the ass tonight"

Anal sex was not unknown to her, but the thought of his monstrous cock inside her bowels made her tremble in panic.

"No, please, I can't do that. You'll hurt me terribly..."

"Yes I'll hurt you, and you're going to love every inch of it in your ass, baby. You'll even beg for more..."

"I won't do that"- she said defiantly.

"Yes you will. Get in all fours now"

"I won't!"

"Then get out of my truck at once! And tell Betty to come..."

She started to cry again.

"Please... I'll do it..."

"You're making me angry, bitch. Now you'll have to beg for it... or else get out and go. And never ask me to have a date with you again!"

"Please... I'll do it. Please let me stay"

"Get out!"

"But why... I am begging... Please let me stay..."

"On your knees, you little cunt"

"Please. Don't make me do that. I'll never be able to look at myself in the mirror again"

"I said on your knees, bitch!"

Crying, she fell to her knees, and implored.

"Please let me stay. I'm sorry I made you angry. I'll be good"

"That's better, baby. That's my sweetheart" - he switched to fake tender mode, and she loved it. She sighed in relief and almost wanted to kiss his boots. She was startled by her own thought.

... And he thought the same. He took our his boots and said:

"Kiss my feet repeatedly and ask for forgiveness, cunt"

She felt incredibly turned on by this command. She did as ordered, and felt her pussy lips very irritated with sexual tension.

"Get on all fours, Ashley. Now. And open your ass cheeks with your hands"

She did as ordered. She started to breath heavily, wildly turned on by now.

"You like it the rough way, eh? You're a little bitch, honey. And I'm helping you discover who you really are. You're going to love me more than you have ever loved, and you'll beg me to be rough on you. You should feel pity for yourself, because I'm going to give you pain and humiliation... and you will love it..."

While saying all this, he was grabbing her cunt roughly again, now naked for him, and Ashley started to moan out of control. He then slapped his cunt a few times, hard, and grabbed her hard again there. She came in his hand, moaning wildly.

He then started kissing and licking and sucking her asshole, until she felt like coming again.

"Oh no, not yet. You have no self- control at all. You need to be disciplined, bitch"

He took a jar of jelly and put a lot of it in her asshole. Then he inserted two fingers in the tight hole, and probed it in all directions. She started to moan wildly again, this time shaking her hips involuntarily.

"No control at all. You're like a little baby. You need to be disciplined" - he said.

He shook his fingers inside her ass very violently, but she was even more turned on by it. By then she had been reduced to be a moaning sex fiend.

He took his enormous cock out and went inside her anus in a very rough way, and Ashley cried in pain and tried to escape, but he pulled her by the hair with one hand and by the hips with the other hand. She cried and tried to escape, but he then slapped her ass cheeks hard and ordered her to stay still.

"Next time you do that I'm going to spank you real hard, you won't be able to sit in a month! Understand, bitch?"

"Yes. I'm sorry. Please don't be angry. You scare me" - she started to cry again and even talked baby- like.

"I won't, baby, but you have to be a good girl with Daddy. Ok, honey? And I'll be sweet with my little girl..."

"Yes, please!"

"Please, Daddy. Say it, baby"

"Please... Daddy" - she heard herself saying.

He went all the way up into her tight ass with a savage movement, and little drops of blood appeared around Ashley's asshole. She howled in pain. Now all of that formidable cock was inside her bowels, and made her feel a strong need to take a shit. He started to pump in and out of her tight ass making her see stars even with her eyes closed. Now her fingers were clinched in the pillow even much tighter than the other night because the pain was bigger... but soon left place to the more intense sexual pleasure she had ever felt.

The feel of his pulsating, huge cock pumping inside her tight asshole was delicious. She didn't know such a big pleasure existed. She had only been taken anally a few times before, and his ex husband had a little dick that never could make her feel filled as only Harry could. Now she wanted to be torn apart, and her hips were involuntarily swaying, trying to impale herself even more in Harry's cock.

She started to beg for an even rougher treatment, and he pleased her, hitting her ass cheeks even harder with each thrust. His long and thick dong completely disappearing inside Ashley's asshole was an extremely exciting view. He then started to fondle her big ( though a bit sagging ) breasts, and she couldn't help coming strongly. She heard herself begging for more. Harry took his cock out, and the huge penis left Ashley's anus wide open with a pop. Now Ashley's anus looked like a crater. He fucked her ass with his tongue then, while she begged for his cock to come back into her ass.

He sucked her open asshole very hard and fast, and then put all of his hand inside. His hand disappeared up to the wrist inside her asshole. Then he started to fuck her ass with his fist inside. She was moaning wildly and came again. When he took his hand out, her asshole was a big open crater. She kept begging to have his cock again.

"But I'll fuck you hard, bitch"

"Yes! Fuck me hard! Rip me apart! I don't care! Give it to me!"

He went into her with his cock again, and fucked her really hard, deliberately hurting her with each thrust. Her response was that she came several times in a row. When he was pulling her tits roughly to the sides, she had the most intense climax of her lifetime. She was swinging her hips, totally out of control, when he came inside her rectum, filling her with hot cum. He then went out and put a big ass plug into her hole.

"Keep that there, bitch. I wanna show my friends how much of an easy bitch you are"

He then pulled her by the hair to make her sit on the bed.

"Ok, now tell me, who's the boss here, bitch?"

"You are"

She blushed again.

"My cock smells of your shit now. Lick me clean, bitch! And swallow it!"

She went down on him.

"On your knees! Kneel on the floor! Do it!"

He snapped his fingers. She obeyed immediately. She licked him clean.

"Ok, put on the high heels. I'm going to show you something"

Pulling her by her hair he took her out of the cabin, with only the shoes on.

Still pulling her by the hair, they went inside Sam's.

He went to the table where his friends were having dinner.

"Get on all fours, bitch"

She blushed again. She did as commanded.

"I can't believe it, Harry" - said, Charlie, one of his pals, and handed him a collar. It was a dog collar- "She seemed to be a decent girl"

"She's a little slut" - he said, proceeding to put the collar on her neck. Amazingly, Ashley consented in silence to be treated in this humiliating manner.

Sam was watching from his place and he couldn't believe what his eyes were telling him.

"What do you think you're doing, Harry? The Highway Patrol officers will come to have dinner soon. You'll put me in serious trouble"

"No, they won't come tonight. And this will only happen tonight, so watch, old man. You may not be able to see something like this ever again!"

"You're taking this too far, Harry" - said Trish with a frown - "Leave the poor girl alone"

"She likes it. Isn't that true, baby? You like to be treated like the slut you are?"

"Yes" - she said simply.

"You're a little whore. You'll be my slave, bitch"

He took out the plug from her asshole. His cum came out of her ass and slid down into her cunt.

"Look! I told you! She let me fuck her in the ass!"

"I envy you" - said Charlie.

"You want her? You want her ass? How much would you give to have her that way?"

"You're kidding me"

"No. You may have her. She's my little slut and she'll do as I command her. Isn't that so, sweetie?"

She shivered, and felt embarrassed that Trish and the others would hear, but said:

"Yesss..." - a tinge of passion in her voice that didn't go unnoticed.

"Hey she really is getting hot. She really likes it, Harry"

"I know. She's my little bitch. Fuck her, Charlie. And I'm sure she'll come and moan. She's a slut at heart"

Charlie took his penis out. It was big too, but not as big as Harry's, she thought.

"It's $ 300 for her ass, Charlie... if you want it"

"Hell, yes I'll pay!"

He went into her ass without any lubrication, and she cried in pain, but then her asshole had been opened wide before, and she soon and easily accommodated the new guest in her intestines... and just as Harry had predicted, Ashley started to moan with pleasure, and came again, unable to control her instincts... Charlie sent a huge load of cum up her asshole and into her bowels.

"Lick him clean, bitch"- ordered Harry then.

She went on her knees and obeyed the command. There was a strange gaze of manic passion in her eyes. Harry had transformed a modest girl into a cock craving bitch in heat!

"On all fours again, bitch! She will be nude for some time tonight... I am showing the little bitch who's the boss. Who's next?..."

Paul, another driver, came with his cock already in his hand.

"I want her... How much for a blow job?"

"Mhh... That's $ 150 for you, Paulie"

"I'm in!"

"On your knees, bitch!"- he pulled her by the collar - "... and take all of it in your mouth. He's not as big as I, so I know you can do it. If I see the smallest piece of his cock out of your mouth, I'll punish you very hard. Perhaps I'll spank you all night long, until your ass is bleeding, and you ask for mercy!"

She shivered in delight, and took all of Paul's cock in her sweet mouth, and proceeded to suck him gently. She heard herself moaning even more than Paul was...

To be continued...

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