[The pain is still present, but just the very thought that Jack is inside of him right now is enough to keep him from falling apart. Even with the latex in between them, he could still feel the heat of Jack's cock overtaking him inside, breaking him in futher as he gradually begins to move in faster.
It's a slow progress, but even amongst the aching, he begins to feel physical satisfaction in the thrusts as Jack hits spots that send jolts through his body, allowing him to moan loudly moreso from pleasure than pain.
Even if it is his first time, he wants to make sure Jack is getting enough enjoyment out of this as well. So when his leg is gripped tight above a waist, he focuses more of his energy on rocking his hips against the throbbing cock to help guide Jack along further.]
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It's a slow progress, but even amongst the aching, he begins to feel physical satisfaction in the thrusts as Jack hits spots that send jolts through his body, allowing him to moan loudly moreso from pleasure than pain.
Even if it is his first time, he wants to make sure Jack is getting enough enjoyment out of this as well. So when his leg is gripped tight above a waist, he focuses more of his energy on rocking his hips against the throbbing cock to help guide Jack along further.]