One Step Ahead (5 page)

Unfortunately, she was at a religious school on a religious scholarship, and knew she could easily be kicked out for immoral behavior.

Her future, she felt, depended on her getting through this. Besides, she HAD already allowed him to give her an orgasm and put her hairbrush handle inside her, this was no greater a sin, and she owed it to him to return the favor.

"Are you ready, sweetheart?" he asked, “I’m going to start with the handle again, it’s not as thick as my cock.”

She felt the hard and blunt end of her hairbrush find her hole, and she winced as he pushed it in.

It didn’t hurt, exactly, not like the three fingers he’d thrust into her, but it definitely felt wrong.

“I’m going to fuck you with this,” he breathed.

She said nothing.

As she felt the hairbrush slide farther inside her, she squeezed her eyes shut and quietly hated herself.

Every lump and bump on the hairbrush’s handle seemed specifically designed to make her unhappy. It was one of those spiral handles, supposed to be cushy for a hand grip, but, she reflected, it was obviously not designed for this use.

Worse, even with some lotion to smooth the way, the surface was a little rough, and chafed her hole and her delicate passage. She shifted her hips in discomfort, but that only made it worse. She hadn’t noticed the roughness when it was inside her earlier, but she apparently the skin of her ass was even more tender.

“Do you have to use that?” she finally asked.

“Why do you want me to stop?” he asked.

“It doesn’t feel nice,” she said.

“I’m trying to stretch you, but if you’re sure you’re ready to stop and go on to my cock, that’s fine. What would you like?” he asked.

“To be done with the hairbrush,” she said.

He laughed, gently.

“Tell me you want your cock in your ass, and I’ll be more than happy to grant your wish,” he said.

Amy blushed She didn’t want his cock in her ass. She didn’t want that at all… but maybe it would be better than this, which was starting to feel like sandpaper inside her.

“Please put your cock in my ass,” she whispered.

“You want me to fuck you with my big fat cock?” he asked.

“Yes,” she whispered.

“All right, sweetheart, your wish is my command,” he said, and pulled the hairbrush quickly out of her, making her shriek as it scraped painfully on its way out.

“Whoops, sorry,” he said, fumbling around for a minute.

She didn't respond, and she felt the enormously blunt head of his cock against her tiny, already-sore pucker.

Josh grabbed her hips and pulled her backwards, spearing her slowly on his enormous, lotion-covered cock.

She gritted her teeth and took it in. The penetration stalled, and she heard him say "It'll be easier when the head is in, I'm going to pull you down past that pretty fast."

The grip on her hips tightened, and her entire body was jerked backwards, impaling her further on the shaft. Just when she thought it was too big, it would never fit inside her, she felt a pop, and her ass closed around the narrower shaft, the thick mushroom head fully inside her.

That was no better, though, with the momentum he'd built up, he slid inside her far and fast.

"Wow, you're really sucking me in," Josh laughed, "Is that better now?"

"No," she said.

"Shh, sweetheart, it's okay. I'll just hold still for a minute," he said, and gently stroked her back.

She did her best to relax, and she had to admit that it didn't feel quite so bad when he was holding still.

Sooner than she was ready, though, he started to scoot forwards and backwards, each thrust into her a little deeper, penetrating her and spreading her hole for him what felt like one awful milimeter a a time.

"See?" he asked quietly, continuing to rub her back, "Nice and slow."

She nodded. The ring of her ass was starting to burn a little, and she felt as though she were being split in two, but all in all, this was much better than when the head was going in.

Constant, low-level pain, but not the overwhelming terror of thinking it wouldn't fit.

She could handle this, she thought. It would be okay, if he took her like this, so slowly and carefully.

He did, too, for a while. It took him ages to work his cock all the way inside her.

Once he was finally balls-deep in her tight passage, he leaned over her and started to whisper in her ear.

"Every inch of my cock is in your ass," he said softly, and she nodded. She believed him.

"Your ass isn't virgin any more," he said. She nodded. She was ashamed almost beyond bearing, but she knew that it was true. She'd given up part of her virginity to this man that she barely knew.

He slipped his hand around her waist and reached between her legs, sliding a finger between her folds.

"You're wetter now than when I put the brush inside you like you wanted me to," he said.

She winced at the memory of her shame, but she couldn't deny the truth. Her rear end still hurt, but it felt amazing to have his fingers on her clit, and she could feel how easily they glided in her slickness.

He pulled his fingers away and held them in front of her face, wiping them gently underneath her nose.

"You smell amazing, sweetheart," he murmured.

She didn't want to smell herself like that, she didn't want to admit to herself that even some small part of her was enjoying this, but she knew it was true. Her clit was aching to be touched again, and she almost considered reaching her fingers between her legs to take care of that.

Her shame outweighed her desire, though, and she kept her hands balled in the blankets.

"You're so wonderfully tight," he said, "I've never felt something so amazing on my cock."

She breathed in and out, deeply.

"I'm going to start thrusting, sweetheart. Taking it slow, but you feel so good, so fucking good, I can't hold myself back much longer," he said.

She tensed up as he started to pull out of her tight passage, and then eased back in a little.

Apparently finding less resistance this time, he started thrusting in and out of her passage, hands around her waist, pulling her back onto him over and over.

She'd hoped he would hold still longer, but he only started moving faster and harder.

Amy felt as though she was being entirely split in two, her ass felt like it was on fire, she couldn't even believe how much it hurt. She hadn't known that it was possible to make her body feel so awful.

She started to cry, silently at first, and finally out loud. It didn't affect his rhythm at all, or his constant stream of obscenities that shocked her almost as much as having a cock inside her.

"Oh, goddamn, Amy, you feel so good, you feel so fucking good, I'm fucking you and you feel so amazing, my cock is so goddamn deep inside you," she heard, and it went on and on.

Finally, she sobbed, once, so loudly and hard that her body shook, and Josh slowed down, and stopped fucking her.

"Honey, I stretched you plenty," he said, in his calm and patient tone, "I know you're a virgin, but it can't be hurting you that much. You need to relax."

She nodded.

"Please, please," she gasped, "Please stop for a minute. Please just give me a minute to breathe."

"You want my cock out of you for a minute?" he asked.

"YES," she said.

"Don't you remember how it felt going in? Don't you want me to just go ahead and finish now?"

She shook her head. She couldn't take it. She couldn't take his cock for one more minute.

“You’re so tight, I could probably use some more lube. You’re almost hurting my poor cock,” he said, and laughed.

She said nothing.

"All right, sweetheart, let me pull out and lube up again, and I'll come back and see what we can do to kill some time before you're ready to try again," he said.

She sighed with relief as she felt the cock pull out of her. Even the mushroom head stretching her poor pucker yet further was better than the hard pounding that she'd been getting.

“Do you want to put more lube on my cock, or should I do it?” he asked.

“You, please,” she whispered. She was still crying a little, tears leaking out of her eyes and running down her face, but she wasn’t sobbing any more. She supposed she was grateful.

The feeling, of fullness, of tightness beyond bearing, went away slowly. She relaxed more and more as her abused pucker adjusted to normalcy again, although it still burned and ached.

To her shame, she found that her belly still stirred with desire when she looked at Josh. They had sinned together, she should want nothing more than to be rid of him forever, but he was so attractive and charming, she wanted to be with him, wanted to touch him and be close to him.

"All right, princess, I'm all lubed up!" Josh said cheerfully.

She gulped. She'd hoped that her break would be longer than that, but apparently he was ready to go again.

"Do you want to try another position?" he asked.

"Like what?" she whispered.

"Well, some girls say it's easier if they're fucked over a bed or something. Would you like to give it a try? All you'd have to do would be to come stand with your feet here, like I'm doing now, and then bend over the bed and hold still, I could get right in your little pucker," he said.

"I don't know," she said, shrugging slightly.

"Yeah, let's give it a try!" he said, enthusiastic now.

"All right," she said slowly, and, moving a little at a time, wincing as her sore asshole was pulled and stretched when she moved her legs, got into the position he'd shown her.

Without warning, he grabbed her hips, lined up his cock, and slammed it home.

She screamed out loud, once, as he started to move inside her, setting up a punishing rhythm.

“Hey, hush!” Josh hissed, “Do you want the maid to come find you like this?”

She shook her head and tried to calm herself.

“Good girl,” he said.

She whined softly as he continued to work away inside her tight passage. The new position allowed him to move more quickly and get even deeper inside her, it was worse than she could have imagined.

With every thrust, it felt like she was being torn apart. She didn’t know how much more she could stand the pain, but she knew she had no choice. All she could do was grip the blankets tightly in her fists, sob, and wait for Josh to be finished with her.

“You like this?” he grunted, “You like me fucking you?”

She didn’t bother to respond. She knew he could hear her crying, he had to be able to, but he just didn’t seem to care.

“Hey, sweetheart, you need another break?” he asked, when she didn’t say anything.

She nodded.

He slowly pulled out of her again. She sobbed until the head was out and then gasped with relief as he walked away from her for a minute.