8:08 P.M.

He pushed. He pushed and pushed and pushed...

He broke the seal and in he went, robbing her of her anal virginity. He heard her squeal. He wasn't deep -- perhaps only two inches, but he felt how tight she was. How hot she was. If compared, her pussy was a firm handshake and her ass was a vice grip with a hundred tons of pressure on it.

He pushed deeper. He moaned. "Fuck me, you're tight."

She grabbed the pillow beside of her and bit into the edge.

Deeper. She trembled.

Deeper.

As he hilted, he saw tears in her eyes. "It hurts so bad." She managed. "It hurts so...good."

She laid her calves onto his shoulders and in he went. He pulled out a few inches and then slowly back in. She tensed and squeezed on his cock as the lube coated her rectum. Once more. More lube.

Pulling all the way out, he coated it with another layer of lube and then made his way back in a little easier this time. With each thrust, it began to slide in and out easier.

He picked up the pace. She cried now, but stayed silent. She was his, after all. It hurt -- but she sickeningly loved it. Through the pain, she felt the vibe still in her and concentrated on that.

He picked it up even further, jiggling her tits each time he made his way all the way in.

He was anal fucking her now.

Pushing, shoving -- destroying her insides, he fucked her lube coated asshole like there was no tomorrow. He grunted with each thrust, his cock being sucked into her and suffocated as he pushed deep into her rectum.

She moaned. Tears down her face, vibe in her pussy, she moaned. She could feel him deep in her.

"Why do you have to be so fucking big?" She asked, smiling as another tear ran down her face. "I'll literally never walk the same."

"I don't want you to." He grit his teeth as he pounded into her. "You should walk like you've just had your ass fucked by your lover."

"Not my lover, no." She began to rub on her own clit, the vibe helping her out. "I'm getting assfucked by my husband."

He grinned. "Oh, so I'm your hubby now, huh?"

"Even if we stick together with Tom and Kait, you're my only one, baby."

He felt himself on the edge. Laughing, he kissed her leg. "You virgins fall so easily in love with the first thing to put their cock in your ass."

She tensed and Tyler moaned, her little asshole suffocating him as she came from the vibe, riding her orgasm out even longer as the vibe refused to stop.

He pulled out and flipped her over, getting her on her knees.

He spit on her ass and made his way back in. She screamed and buried her face into her bed. He felt himself on the brink.

"I meant what I said, Tyler." She mustered, her fingers still working on herself as she let herself be taken. "You're my last."

He was almost there.

"So I want you to finish claiming me."

He felt more blood rush to his cock.

"Cum for me, please."

With one final thrust, he fired his last thick spurt deep into her. She could feel him pulsing, the hot feeling of his cum in her, filling her ass. He dug his fingers into her cheeks as he fired once more, then pulled out, finishing on her asshole. She dripped.

She fell to her side and looked up at him, smiling. Tears down her face, she opened her mouth to speak.

"Sorry I wasn't very h-hot. I didn't want you to hear me crying so I didn't talk much."

He came up and lie next to her, worry in his eyes.

"Was it that bad?"

"I'm just glad you didn't take too long."

He grinned. "It's not like I had a choice. Your pussy got me about 85% there."

"So my pussy is still A1, huh?"

He kissed her nose, smiling. "All of you is. And I don't ever want to see you cry again, okay? We won't do that again."

She looked sad. "Why? How are you going to train my ass if you don't use it?" She broke into a smile.

"Are you sure?"

"I'm never going to love anal if you don't."

He rolled her over onto him and they cuddled to sleep, exhausted.