whispered.
"Okay, I promise I won't if I cum inside you," he said, and she nodded.
"Where do you want me to cum in you?" he asked.
She shrugged.
"Do you want me to fuck you in your pussy or in your ass?" he asked.
"Please not my virginity," she whispered.
"So, you want me to fuck you in the ass?" he pressed.
She held perfectly still, and finally, after five agonizing seconds of him squeezing her nipple, she nodded.
"Say it," he said.
"Please," she whispered.
"I want you to say the words ‘in my ass,’” he said.
“Please, in my ass,” she whispered.
“Well, if you insist,” he said cheerfully, and she felt the blunt pressure of his broad fingertip press against her reluctant hole.
Amy squirmed and winced as Josh’s lotion-covered finger pressed ever so slightly into her virgin ass.
She knew that she had to agree to this, the alternative was too humiliating, but she was terrified. Ten minutes ago, she hadn't even known that people had sex there, and now she was going to let a man she barely knew put his penis inside her, inside her tiny bottom, somewhere she knew in her heart of hearts that it was not meant to be!
"You want this, right?" Josh asked, as his finger pressed deeper inside her.
"No," she groaned. It felt alien and strange and she just wanted to hide under a pillow and hope it went away.
"Oh, sure you do," he said, "Or, at least you want this more than me telling people what a slut you are, right?"
She nodded.
All her life, she'd been a Good Girl, and done the right thing, and said the right thing, and never dreamed of violating her purity, letting her family down. She wasn't quite sure how she'd sunk so far so fast, but she knew that she would be ashamed for the rest of her life.
"My finger's all the way inside you," Josh told her.
She nodded. She could feel the knuckles of his other fingers where they were curled against her tender behind.
The intruding digit itself felt pretty awful. It wasn't at all fun or satisfying, even compared to the hairbrush she'd let Josh put inside her earlier, which had felt like something was missing. Nothing about Josh's finger in her butt felt right or comfortable, and it was already starting to hurt a little.
She thought of his cock, over seven inches long and so thick she could barely get her mouth around it, and held back a sob.
"What do you think?" he asked her.
Amy shook her head.
"Tell me," he insisted.
"It feels wrong, and it hurts, and I hate it," she said, petulantly.
"Oh, sweetheart," he said, sighing, and rubbed her ass comfortingly, "It's okay, I'm just stretching you."
He held still for a minute, and she tried to relax around him, until she felt him press a second finger inside her.
That definitely started an ache in her virgin hole, and she started to shiver, hiding her head in the blankets and breathing deeply.
Three fingers inside her, and Amy was panting in pain and considering just letting everyone find out how far she had fallen, rather than allow this to keep happening to her.
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