Millionaire Girlfriend

Chapter 31: Chapter 31 - Agreement and punishment

It was the weekend, and Clara hadn’t returned home for five days. She had spent every free moment with Ashley.

But...

"Please, I already apologized to you several times," Clara begged while kneeling in front of Ashley.

"I won’t do it again, but please don’t do this to me."

" We have an agreement," Ashley finally said. "You swore that if you ever cheated on me again after what happened at college, I could do whatever I wanted to you."

"I get that, but why do you want to fuck me with that?" Clara asked, pointing at a strap-on.

"In the ass," she added.

To understand how things had reached this point, we have to go back three days earlier, when Clara took Ashley on a romantic date to her favorite restaurant: The Cheesecake Factory.

They ordered burgers with French fries and two strawberry lemonades.

"I don’t understand how you can eat like this and still keep a perfect figure," Clara said, watching Ashley devour her burger, fries, and lemonade.

"I think I’ve been through so much that my body was basically forced to adapt and reach its maximum potential. Mmm... this is so good," Ashley replied, still chewing.

It was the first romantic date they had had in years.

It wasn’t exactly the kind of romance Clara had imagined, but Ashley had insisted on going to The Cheesecake Factory, so Clara eventually gave in.

"Why does that girl keep looking at us like that?" Ashley asked.

"What girl?" Clara asked, turning around.

"Oh, shit..." Clara accidentally let out when she saw who it was.

"What?" Ashley asked, surprised.

"Who is she?" Ashley asked curiously.

"Nobody," Clara replied, quickly hiding behind her chair.

Ashley ignored the girl, even though she knew she was definitely someone.

But five minutes later, the girl approached their table.

"Hi, Clara!" the girl greeted her, completely ignoring Ashley’s presence.

"I wanted to know if you got my number. I’m still waiting for you to call me," the girl said.

Clara’s face immediately showed her embarrassment, but she noticed Ashley calmly eating her burger as if nothing was happening.

"Hiii..." Clara awkwardly replied, realizing she had forgotten the girl’s name. "I’m busy right now, but I promise I’ll call you when I can."

She had no intention of calling her, but it was the quickest way to solve the situation in public.

"Did you sleep with her?" Ashley asked calmly.

Clara knew she couldn’t lie.

"Yes. Once," Clara admitted.

"Okay," Ashley replied.

"And how many people did you sleep with during our breakup?" Ashley asked, still using the same calm tone.

Clara knew that deep down Ashley was angry, but she was keeping herself under control.

"Only three," Clara admitted.

In reality, it was three times that number, but she didn’t want Ashley to know the truth.

Besides, what were the chances of them running into more than three of Clara’s past hookups when they rarely went out?

However, two days after the restaurant incident, while they were casually shopping and Ashley had only moved a few meters away, another woman suddenly approached Clara and almost threw herself at her.

Ashley silently watched the woman flirt with Clara while Clara desperately tried to make her leave.

Once again, Clara explained that she was one of the women she had been with before getting back together with Ashley.

Ashley accepted the explanation calmly.

But when they returned to the apartment, while Clara was taking a shower, Ashley searched through her phone.

It was something many people advised against doing if they didn’t want to hurt themselves, but Ashley’s curiosity eventually won.

She wanted to know how many people had been with the woman she loved while she was suffering through their separation.

After unlocking Clara’s phone, Ashley promised herself that no matter what she saw, she would stay calm.

But when she saw the messages Clara had sent to dozens of women, she lost her composure.

She almost threw the phone away when she discovered that, on the very day they got back together, Clara had gone on a date before seeing her.

"You’re such a liar. You told me you only slept with three women, but you were actually making a fool of me," Ashley said as she threw Clara’s phone at her.

"Listen, I wanted to tell you, but I knew you would get angry, so I lowered the number a little," Clara defended herself.

"Only a little? You slept with dozens of women, damn it. Three isn’t even half of that," Ashley said before grabbing her bag and leaving.

Since Clara was still only wearing a towel, she couldn’t follow her.

Ashley didn’t return until the next morning.

Back to the present...

"Please, I already apologized to you several times," Clara begged while kneeling in front of Ashley.

"I won’t do it again, but please don’t do this to me."

" We have an agreement," Ashley finally said. "You swore that if you ever cheated on me again after what happened at college, I could do whatever I wanted to you."

"I get that, but why do you want to fuck me with that?" Clara asked, pointing at a strap-on.

"In the ass," she added.

Ashley had found a rather original way to get back at Clara. Clara had already told her there was no way she’d ever agree to anal penetration, and that was exactly what Ashley demanded as compensation for the trouble Clara had caused.

"It’s this or nothing," Ashley said, knowing full well that Clara would do anything to earn her forgiveness. Besides, she was far too furious to show any mercy.

But in truth, she had always fantasized about taking Clara anally.

She had harbored that fantasy for years, ever since the times Clara would step out of the shower and casually walk around their bedroom with her bare backside on display, completely unbothered.

As Ashley’s eyes lingered on Clara’s ass while she bent over to pick something up, a sudden rush of excitement coursed through her at the sight of Clara’s curves.

It was true that she had pounced on her afterward, but she had never been able to fulfill that fantasy.

At last...

"Ah... ah... ah..." Clara muttered, scratching her head as she cursed her own stupidity. She never should have messed up so badly. Now, she had no choice but to pay the price.

"Okay..." Clara whispered, her voice barely audible.

"What? I can’t hear you," Ashley said, secretly smiling to herself in triumph.

"Okay. But you’ll stop if it hurts too much," Clara said as she got to her feet.

"Ahhh, yes!" Ashley exclaimed, throwing herself at Clara in excitement.

Clara couldn’t understand why the idea of fucking her ass appealed so much to Ashley, but now she couldn’t back out anymore.

"Wait," Clara said.

"How do you even do this? Aren’t buttholes extremely dirty?" Clara asked.

"Don’t worry, I have everything planned," Ashley said as she pulled out a bag full of things Clara had never seen before.

"Wait, what do you mean you had everything planned? Since when have you been planning this?" Clara asked suspiciously.

"Only since tonight, when I was crying my eyes out over your betrayal," Ashley lied.

Ashley pulled out an object from the bag. It looked like a small rubber or silicone bulb with a smooth plastic or silicone tip.

"We fill it with warm water, then gently squeeze it to let the water enter your cute little..." Ashley said with a smile, showing the object to Clara.

"No, no, no, absolutely not. I changed my mind. I don’t want to do this," Clara said, suddenly terrified now that she was about to go through with it.

But Ashley said nothing. She wiped the smile off her face and put everything back into the store bag where she had bought it.

She was about to stand up when Clara grabbed her hand.

"Okay, okay, we’ll do it."

" Damn, I can’t believe I’m actually going to do this," she complained as she took the bag.

"Wait," Ashley said as she turned on her phone.

"Here’s a video showing how to do an enema," Ashley said, handing her the phone.

"A video? Since when... since when?" she said, taking the phone before heading to the bathroom.

Ashley was overjoyed.

She eagerly waited for Clara to finish.

Clara stayed in the bathroom for about two hours before finally coming out.

"Alright, it’s all clean. Come on, let’s get this over with," she said before heading toward the bedroom.

Ashley jumped for joy on the way to the bedroom.

"Put on the god belt and fuck me in the ass quickly so we can get it over with," she said while on all fours, wearing only a T-shirt.

" Stop acting stupid. We’re going to do the whole thing so we can enjoy ourselves, you and me," Ashley said as she turned her over onto her back and threw herself on her to kiss her passionately.

She leaned toward her chest and kissed her with a tenderness that made her partner shiver.

She caressed her nipples, teasing them and sometimes biting them gently.

Then she slowly slides her hand along Clara’s hip, before moving it toward her crotch.

She gently caresses Clara’s pussy, and Clara begins to feel like she is almost forgetting that Ashley is going to sodomize her soon.

But Ashley knew exactly what she was doing to make Clara feel comfortable, as she always did.

"Wait," she said before opening the bottle of lubricant and pouring it onto between Clara’s legs.

"Oh my God, I can’t believe I’m going to lose my anal virginity," Clara said, trembling.

"I’m going to enjoy fucking your pretty ass," she said with a laugh to Clara before putting on the strap-on harness.

Clara was lying on her back with her legs spread, waiting for Ashley to insert the sex toy into her, but Ashley did not do it right away.

Ashley gently caresses Clara’s pussy before sliding a finger inside her. Clara’s back arches from the familiar sensation of pleasure that she loves so much. Ashley lies on top of her to kiss her passionately while fingering Clara with a back-and-forth motion, and Clara moans with pleasure.

Ashley wanted to get Clara as aroused as possible so that the pain of anal penetration wouldn’t be too intense for her. She gently removed her finger from Clara’s pussy and slowly inserted it into Clara’s ass.

"Oh my... oof," Clara says, trying to catch her breath after the first moment.

For now, she wasn’t feeling any pain, as everything was still manageable.

"He he, how do you feel?" Ashley asks, looking like she is enjoying herself, unlike Clara, who seems frightened.

"Everything is fine for now," Clara quickly replies.

"Then Ashley pushed her finger deeper and deeper, before beginning a slow back-and-forth movement.

Clara breathed heavily and had almost forgotten her fear. Without realizing it, she began to enjoy it.

She even moaned with pleasure a few seconds later.

Then Ashley removed her finger and applied lubricant again to Clara’s intimate areas.

"Are you ready?"she asked before penetrating Clara with the strap-on.

"’Do it " Clara said, already anticipating the pain that the 4-inch (10 cm) fake penis was going to cause.

Ashley began to push just a small part inside Clara’s ass, and thanks to the lubricant, there was little resistance, but it was clear from Clara’s face that it was hurting her.

" Just tell me when it hurts too much, " Ashley told her.

"’Fuck you,": Clara said to her.

" I prefer it when you’re the one I’m fucking," Ashley replied, as she pushed the strap-on deeper and deeper without Clara even realizing it.

She then removed it before putting it back in, and her body gradually became more relaxed, making the penetration easier.

Clara was starting to feel pleasure, but she didn’t want Ashley to find out because she feared Ashley would enjoy it even more.

She was already smiling constantly whenever she saw Clara moan from time to time. And it didn’t matter whether Clara was moaning because of the pain or the pleasure.

She then kissed Clara passionately, and without meaning to, Clara wrapped her arms around Ashley’s neck, which means that she is feeling pleasure from having her ass fucked.

But it was too late to regret it now, because Ashley began to speed up her hip movements as she penetrated Clara.

" Hmmm, " Clara moaned loudly."

" Go easy, you’re going to destroy my ass," Clara said, but Ashley didn’t listen. She slowly intensified the movement of her hips without breaking eye contact.

Clara fell silent because her moans made it difficult for her to speak properly.

"I want to take you from behind, " Ashley said as she pulled away, and Clara complied, getting on all fours without protesting.

Her ass was burning, but she was now feeling pleasure.

Ashley applies a large amount of lubricant before taking Clara from behind. She starts slowly at first, then gradually increases the pace.

Clara could only scream because being penetrated that way was both painful and pleasurable at the same time. It gave her a contradictory feeling, like people who enjoy rough treatment in order to reach orgasm.

Clara’s legs gave out when she finally reached orgasm. She collapsed onto her stomach, her ass burning.

But Ashley didn’t want to stop there; she climbed on top of her to continue."

"Hmm... what are you doing? I think that’s enough. I can’t take it anymore, " she said, but Ashley started moving back and forth again while sitting on Clara’s butts."

"’Ash...ley... stop... now... I... can’t...’ she stammered as Ashley continued.

A few seconds later, tears even began to stream down her face, but Ashley kept going.

So, she stays silent and only moans while biting the sheet, lying on her stomach and waiting for Ashley, who is on top of her, to be satisfied.

A minute later, Ashley got tired and pulled away from Clara, whose face was wet with tears.

Ashley rolled over next to her and then tried to kiss her, but Clara turned her head away to avoid the kiss.

Ashley moved closer and insisted a little, and Clara eventually accepted.

" I will never cheat on you again. Never, " she announced after a few minutes of silence, still lying in the same position on her stomach.

" We’ll see about that, " Ashley replied before leaving the bed to go take a shower.

" Oh my God... it hurts so much, " Clara said, unable to walk properly anymore.

" I advise you to eat very little because it won’t be pretty when you go to the bathroom," Ashley warned her.

" How do you know that?’ " Clara asked, but Ashley didn’t answer. She couldn’t tell her that she had researched the subject because she had been planning to do that to her for a long time."

The next day, Clara went back home for the first time in 7 days because Ashley kept insisting that she wanted to fuck Clara in the ass.

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