Clancy was trying to do his best with pleasuring his girl with his fingers, but there was not much more he could do. Despite this, she wanted more judging by the sounds she was making. Thus, Clancy took a gamble. With one more push in, deeply exploring her internally, Clancy withdrew his fingers. His hand began to fumble at the belt, button, and zipper of his pants until finally they were undone. But, instead of sliding Bri off of him, his hand around her waist tightened a bit and Clancy stood, showing off his strength in the process. His pants hit the floor and his member was freed, allowing it to move up and slap against Bri's taint and ass. Clancy gingerly sat back down, guiding Bri to sit just in front of his cock, allowing it to stay behind her as a reminder. It felt bigger than it had been all that time ago, but whether that was because of faulty memories or because of the incident was unclear.<br/><br/>After sitting there for a few moments, enjoying each other's nudity and trading a few more kisses, Clancy finally spoke. "Are you ready, Bri?" Clancy asked, getting only a sheepish nod in response. Clancy lifted Bri up a bit, allowing his cock to move to where Bri was sitting. With his free hand, Clancy stroked his member, wiping off a bit of Bri's fluids onto it. He then held it upright, positioning it to slide in as he lowered Bri back down. He lowered her slowly, making sure that if she put up any resistance, he would be able to tell and stop immediately. However, there was none and Clancy lowered Bri's folds down to his other head.  This is where they encountered a problem. Clancy didn't want to hurt Bri, but judging by his dick and her opening, that was something that was going to be unavoidable. "I'm sorry, Bri," Clancy said, before pushing Bri further down.<br/><br/>Clancy's head forced it's way into her opening before Clancy screeched to a near stop. His hand left his cock and moved to the opposite hip with his other hand. He waited there for a moment, before he breathed out another apology and slowly began to lead Bri's hips closer to his own. It was slow but it was steady as Clancy tried his best to ease himself into Bri. At any point his girl showed resistance, he would stop. However, he wouldn't let her off at simple resistance. He had seen enough porn to know that she had to get used to him. Immediately hoping off at the first sign of pain was going to get them no where. But if she wanted to stop all together, and told him that, Clancy would be more than willing to oblige. But for the time being, Clancy slowly worked Bri onto his cock until, eventually, his cock became fully sheathed inside of her. His hands immediately left her hips and moved to her back, embracing her as she got used to his girth and length, a few more apologies escaping forth as he sat there.