Poker Loser

This time when he pulled his fingers out of her ass, she remained tense. Unfortunately for her, that just meant that it hurt more when he positioned herself between her legs and began trying to push his incredibly wide dick into that small, barely stretched hole. It felt like he was trying to shove a brick into her ass as the wide head of his dick pushed against the outside of her hole. She could feel herself stretching around the tip of the head, stretching and stretching and stretching... there was no way he was going to get that monster into her ass! He was going to tear her apart! As she began to panic, and scream behind the gag in pain and fear, she inadvertently relaxed her ass muscles, and the head of his dick finally managed to pop into her ass. Her eyes bulged.

Todd stopped for a moment, to allow her to adjust to the proportions of his dick, and also to savor the expression on her face. Disgust, revulsion, he judged he was causing her just enough pain to get back at her for all her cockteasing. He didn't want to actually do her damage after all. Running his hands up and down her smooth legs gave him something to do while waiting for her to adjust to the invader. After a moment's thought, he also turned the vibrator up another notch, give her some pleasure to help with the discomfort. Plus, there would be nothing more humiliating that having her enjoy the taking of her own ass. Even if she wasn't an anal virgin - which by her reactions he was pretty sure she was - he doubted she'd ever taken anything as thick as his dick in her ass.

Todd leaned forward a bit, pushing himself a little bit more into her ass, causing her to grimace, and her reached forward with his hands to begin playing with her nipples. As the vibrator in her pussy and his nimble fingers on her nipples and breasts began to have their effect, she began moving her hips a little again, and he pulled his dick back a bit before pushing more in. With her grimacing and groaning, he slowly worked his dick in and out of her ass, pushing more and more in with each stroke. Allison was conflicted. On one hand, the dick moving in her ass made her want to throw up, just knowing that it was there. On the other, she was starting to work her way back to an orgasm. The feelings in her ass hurt, but the pain was lessening, and even with the pain, it almost seemed to be adding to the experience.

As Todd hit bottom, he turned the vibrator up another notch, and began really moving in and out of her stretched, deflowered, perfect ass. He could feel the vibrations as he moved, her ass was so incredibly tight, he was having a hard time not cumming immediately. But he wanted to draw this out... and most of all, he wanted her totally humiliated, he wanted her cumming on camera, while he plundered her ass. With that thought, as he moved in and out of her ass, he made sure that his groin hit the bottom of the vibrator, causing it to move within her as well, and he really began pulling on her nipples, having noticed the effect playing with her breasts had on her.

Not only was the vibrator and the tugging and twisting of her nipples having an effect on her, but having him moving in and out of her ass was starting to feel good too. She felt full, completed, like everything was finally right where it should be with her body. And not only that, but she could feel the biggest orgasm in her life building up in her. Eyes half closed, she was moaning and rocking her body, completely oblivious when Todd took that gag off her that it was gone, everything was concentrated on the incredible feelings that were sweeping through her body. He was moving harder and faster in her ass, really giving her a brutal ride, pulling harshly on her nipples, the pain mixed in with the pleasure and she could just feel herself climbing higher and higher, getting ready for the great fall.

When Todd felt like he was ready to cum, he turned the vibrator up full blast, grabbed her nipples, pinched down hard and pulled them away from her body, using the leverage to slam his dick in her ass three or four times.

Allison arched her back to the extent that she could,

"OH GOD!

OH GOD! OH GOD I'M CUMMING! YOU'RE IN MY ASS AND I'M CUMMING! OH GOD TODD! OH FUCK, FUCK ME! FUCK MY ASS!"

Having those words coming out of that spoiled, pampered mouth did it for Todd. He slammed his dick one last time into her convulsing ass, and groaned her name as he began spewing his load into her dark hole. The pulsing rod in her ass caused Allison's orgasm to soar even higher.

By the time that Todd had finished spilling his load in her ass, Allison's nerves had reached overkill. She was sobbing and begging Todd to take the vibrator out of her pussy, everything was so oversensitive that when he pulled the vibrator from her, she fainted. It had all been too much.

Hours later, Allison would wake up in her own bed, still naked. Her pussy was pink and raw, her breasts had marks all over them, her nipples were chafed, and her ass hurt. It hadn't been a dream.

That didn't surprise her. What surprised her were the feelings that swept over her...

Regret that she was in her own bed... and with her virginity still intact.

One hand reached down to touch her still virgin pussy, and even though she winced at the gentle touch, insistently she began to stroke herself, fondling her sore breasts with her other hand. After a small orgasm, she finally drifted back off to sleep... wondering....

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As always, feel free to comment and give suggestions! I'm thinking about turning this one into a series, lemme know what you think!