Anna was very nervous, but she didn't let it show. She enjoyed looking at the fear in Jimmy's eyes as she stood on top of him, and she wanted to enjoy every second of the growing dominance she inflicted on him.

She knew that she'd lose half of the battle as soon as Jimmy's fat penis went in her, because it truly was too big for her to handle, which was driving her nuts already. She'll lose control very quickly, especially if she managed to put the whole thing inside her.

For that matter, as she kept her hips above his penis, she got two inches closer, grabbed Jimmy's dick, and started rubbing the tip across the entrance of her wet, tender pussy. She rubbed it back and forth, and watched him dance with insanity itself as soon as he felt her warm pussy on his tip.

This was a battle that he was going to lose. He was sure. Nevertheless, he tried his best to assert dominance over his own blood, and prevent the inevitable for as long as he could. If impossibility had a sexual definition, his goal would be a good example.

Anna teased him with her pussy for two whole minutes, stacking the odds to her favor, in her own demented way. She enjoyed watching him twitch, and groan.

"Please… Anna… this is cruel." He pleaded.

Unyielding, she asked, "Will you be a good boy if I put your cock in me?"

"Yes," He lightly nodded.

"Say it." She demanded. "Say that you'll be a good boy."

"I… I'll be a good boy." He whispered, embarrassed. "I'll behave."

"Let's see then, shall we?" She said, and slowly lowered her hips.

The first problem, or barricade, was a predictable one. She was very tight, so she struggled to even put the tip of Jimmy's dick in her pussy. It almost seemed impossible, on account of her small figure.

She had to try four times before she made some progress, and each time she jumped up, because her vaginal walls kept being stretched. It was painful, to say the least.

When she did make progress, she only managed to put a bit more than half of Jimmy's tip in her pussy. This was the best she could do right now.

As his tip suffered through immense pressure, and of course, pleasure, his dick started twitching! His blood wasn't listening to him as much as he wanted it to, this was obvious, so he was forced to take more drastic measures. He grabbed a handful of dirt from the ground, and shoved it in his mouth!

This almost made him choke, he had to spit several times afterwards, but it did calm him down. It turned him off, just slightly, and now he felt confident that he could endure at least five minutes of Anna riding him, if she managed to ride him, that is.

"The clock is ticking," He said, counting every second. "You have thirteen minutes."

"Not fair!" She exclaimed. "I haven't even put it in me yet! Those two minutes don't count."

"Nope, they count." He stretched a disgusting, proud look across his face. "Your deal had many gray areas in it, princess. Technically you started riding me as soon as my tip went in your tight little strawberry pussy. You dug your own grave."

"Fine!" She gasped, "I gotta speed things up then."

Infuriated by the fact that she was losing, well, kinda losing, she then decided to push herself to the limit. She tried to ignore the pain this time around.

With such boundaries out of the way, she managed to put the entire tip of Jimmy's dick in her pussy! This hurt her quite a lot, she could literally feel her vaginal wall opening up, for the very first time, and it was a harsh experience!

Anna put the entire tip inside her about four times, as she tried to make progress, and she was already bleeding. It would appear that she had been a virgin in both worlds, and her virginity met its bitter end tonight.

Vaginal blood covered the tip of Jimmy's penis, he could see it, and Anna could feel it, but she didn't care. She didn't even wipe it away!

She lost her virginity now, it was official. This fact kicked a mental barricade right out of her brain, increasing her confidence to take even bigger risks.

This time, she let gravity do its thing. She lowered her hips even further, and didn't strain her legs as much.

Through quite a bit of pain, she finally managed to go past the tip of Jimmy's dick!

Nervous, and in pain, she kept taking quick breaths, to make her experience easier. She was close to hyper-ventilating, though, so she jerked herself up just seconds later.

"Aah… hah! God!" She gasped. "Why does it have to be so fat…"

Anna took a deep breath afterwards, and tried to regain her composure. She did not want to lose this battle.

Then, she went down on him again, and managed to put half of Jimmy's dick in her pussy! This was when things started getting a little bit easier for her, despite the pain.

The blood acted as a lubricant, so she managed to slip it in a bit easier this time, but furthermore, her vaginal canal was finally opening up! This time, as she took deep breaths in, she could feel a hint of pleasure coming from her pain, rather than just sharp pain alone.

"Heh," She grinned. "I got you now, pretty boy. Just wait!"

Soldiering through, she sat on his dick, at that exact position for twenty seconds, allowing her vaginal canal to open up even further. The pressure she felt was immense, but she was loosening up, bit by bit.

Jimmy on the other hand, was one quick thrust, one imbalance, or a clumsy slip away from going absolutely insane!

Anna's pussy felt beyond tight while it took his dick hostage! The pressure he felt now was stronger than what he felt when he fucked Nechi in the ass, even though in hindsight, that sounded impossible!

It was possible, because Anna clamped on his dick every time she took a sharp breath, and every time she moved by an inch! When she clamped on him, he considered eating dirt again, and by the sixth or seventh clamp, he did.

"You have eleven minutes." He coughed through a mouthful of dirt.

This only served to upset Anna, so without being ready for it, she slammed her hips on him, and put Jimmy's entire dick in her pussy! The whole nine inches!

"Aah!" She screamed.

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