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This is a library! (Fish and Candira)

He laughed and put his hands on her hips, his cockhead poking at each hole. "So what are your thoughts on anal?" He asked, slapping her ass a bit to help her wake up and hopefully turn her on.
 
She jumped a little as his hand landed on her rear with a resounding smack. It certainly did serve to wake her up a little. "I...I can honestly say I've never tried it," she said, propping herself up on her elbows.
 
His shaft slid over her ass, between her cheeks, teasingly. "Is it something you think you would like to try?" He asked, giving her ass another slap as his hard member grinded against her body more, smirking as she positioned herself and seemed to stammer.
 
"I guess I could try, but if I don't like it, you have to stop, okay?" she asked, the way he teased her starting to turn her on.
 
"D-deal.." He was surprised he had been so bold, when other times he would object to the thought of anal sex, but for some reason, right now, he really wanted to try it... To put his cock between those big round cheeks and feel her ass. "R-ready?" He asked, moving her hips up, he got on his knees on the couch behind her, reaching and throwing off the pillow for more room, and slid his cock's head up along her pussy's opening and poked her ass with it.
 
She shivered as his head passed over her entrance and to a new much much tighter hole. She wondered if she could take him in and she started to wonder if trying was the best of ideas. "Ready," she responded nervously, hoping that he would touch her while he was pushing in.
 
(Touch her? As in...?)

He bit his lip and put his hands on her cheeks, spreading them apart a bit. "You have such a tight, round ass.." He said, thinking back to admiring it as she'd walked in front of him in the library to make copies. He slowly slid his cock forward, the head of him brushing the entrance to her hole, he let out a light moan and looked up at her to make sure she was okay, holding her hips steady.
 
He felt so much larger to her than she imagined. It made her nervous, but she was willing to let him try.

((Just rub her back, her ass, anything gentle.))
 
((Mkay. If you're not comfortable with this we can stop.))

He felt how tight she was and went slowly. "Ahhh... Fuck... You okay?" He asked, pausing a bit and letting his warm hands rub over her ass and lower back.
 
((I'm fine, but it's not particularly something I would enjoy, hence the reluctance of the character. No big though. She'll get over it.))

Her body felt like it was stretching an amazing amount. A little groan of pain escaped her and she clenched her fists. "Give me a minute to get used to it," she said, her ass in some serious pain.
 
"O-okay.." He gasped, hating to give her undesirable pain, but it felt so good to him, and it was so hard to not just plow her tight hole for his own gain. He rubbed her ass slowly, holding his cock where it was, feeling her getting used to it and her hole expanding a bit more for his thick member. "S-sorry I'm this big.." He laughed a little.
 
She smirked and when the pain dulled she took a deep breath and said, "Push all the way in. Just do it quickly and leave it there for a little while. I think it'll be easier that way." Her eyes closed and she looked straight ahead while she waited.
 
He knew it shouldn't, but hearing her whimper kind of turned him on, in the most carnal of ways. "Okay.." He reached up and grabbed her body, tensing for a moment. "Here goes.." He slid his cock forward quickly, his whole shaft being buried within her now as he let out a loud moan of both pleasure and pain. "Ahhhhh! FUCK!"
 
She yelped in pain and arched her back clenching her fists and grasping at the air for a few moments. "Ah, ha, oww...." she bit her lip and closed her eyes. "Just a minute..."
 
"S-sorry.." He gasped, apologizing for the pain he'd caused her. He rubbed her ass, trying to hold as still as possible for her, his hands running up and down her back.
 
"Keep rubbing me," she said softly, slowly letting her body get used to him. After a few more moments she got used to it. "Mmph....okay, now you can try," she said, tossing some blonde hair over her shoulder.
 
He kept rubbing her. Slowly and warmly, he was pretty good at giving massages despite having no teaching about it. He caught her hair in a mirror across the way and focused his gaze on it for the moment, his eyes ocassionally glancing down to the curvy, perfect body the was bent before him. "I'll be gentle..." He said, his hands gently grabbing her hips as he pulled back to his cock's head and pushed all the way in again.
 
Veronica smiled at the warm, gentle touch that helped her forget the pain of him inside of her. Her eyes closed for a moment as the soft, warm touch was replaced with a harsh awakening, despite his intention of being gentle. It hurt quite a bit but the pain passed as he came back into her. She kept breathing and smiled softly. "Keep going if you want me to get used to it," V said softly.
 
He watched her face writhe in pain and scrunched his face up, wishing there was some way he could make this easier. He figured that it was like popping a cherry and every time after this would feel wonderful... At least, he'd hoped. "Okay.." He said, massaging her hips and buttocks, as he began to slowly move back and forth, fucking her tight asshole.
 
After a while, it did start to feel better, the pain wearing away. "Oh! It's starting to feel better," she said, hoping that he didn't feel bad for putting her into this situation. After all, she'd been the one who'd offered to try.
 
He gave a light moan. "G-g-good.." He gasped, going a bit faster, still rubbing her back, but getting more into it now.
 
As he stopped rubbing her back, her ass started to loosen up just a bit and she started to moan as he pushed in and out of her like that. Her body swayed as he pumped into her and she wondered if he would want her again like this...she wasn't sure what to think of the experience, but she had to be insanely tight--it was her first time taking it that way, after all. She wondered how much longer he could last.
 
The sensation was new, and he couldn't decide where to rank it on the different holes he'd tried on Veronica already, but it definitely felt good. A little too tight, but it was definitely a good feeling. "I-I'm getting close..." He said, grabbing her hips more roughly now as he fucked her, her ass slapping up against his body.
 
She moaned and yelped as he started to fuck her harder and harder. It didn't feel anywhere near as good as when he took her pussy, but it was alright. She would definitely have prerequisites for this in the future. She moaned softly and hoped that he'd cum and pull out of her soon. It was starting to hurt again.
 
Matthew removed one of his hands from her hips and slipped it down, underneath her, and slowly slid a finger into her pussy, using both of her holes. "H-how's this?" He gasped, going harder and harder with both, trying to focus so he didn't lose control.
 
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