He preps you

"Have you ever been with another man Pretty Boy?" he asks, glancing away from your manhood and to your face.

You shake your head. No reason for you to lie. "Never like this." you say, embarrassed at how your voice cracks with the admission.

"Then I better get started prepping you." he says, his hand leaving your cock to circle around your hole, "Rather not blow this by killing you on this mammoth."

You whimper, both out of fear and arousal. That thing is definitely big enough to tear you apart if he isn't careful. You want to back out, say this is all a mistake, but your horny, submissive side takes control again. It wants cock and it wants it now! You've been waiting too long and who knows how many attempts it's going to take for his seed to catch? It begs you to relax and let him do his job, he's an older man with way more experience than you. He can make you feel good in ways that the younger wolves could never do.

Eventually you relax and Dakota picks up on it quickly. He wastes no time, covering three of his fingers with the lube on the bedside table. "Just stay calm boy." he says, eyes locked onto his prize, "It's gonna hurt a little bit, but once I find your spot you'll be begging for more."

You close your eyes as you feel his first finger circle your rim once more. It feels so strange, having another person down there, exploring your most private areas. Especially someone you had only met a few minutes prior. You can't help but clench up as he pushed in, the intruding finger feeling much bigger than you imagined.

"Relax." he says, his free hand moving up to stroke your cock, "I warned you it was gonna hurt. Just let me in, it'll hurt less that way."

It takes a minute for you to calm down, but between his coaxing and the warm hand on your cock, you relax once more. His finger continues it's journey deeper inside of you, but you don't fight it. Soft whimpers escape your mouth as he probes, looking for something very specific.

"Maybe if I add another..." he mutters and you feel the second finger pushing alongside the first. It causes your rim to burn and you can't help but try to pull away. Dakota doesn't let you get far though and soon you have both of his fingers deep in your hole. You can feel him scissoring them, forcing you to stretch to accommodate them both. You are really starting to doubt his words about this feeling good eventually.

Suddenly, one of his fingers brushes up against... something inside of you. You buck into his hand and gasp for breath. What in Luna's name was that?!

"Looks like I found it." he says, grinning as he begins to focus all of his attention there. You cry out, out of pleasure instead of pain, surprised at how good it was making you feel. Your entire body is tingling now and that feeling of impending orgasm is back again. You barely even notice the third finger entering you until it joins the **** on whatever was inside you.

Before you can warn Dakota about you incoming orgasm, he hits that spot particularly hard. You scream out in pleasure, your ass contracting hard around his fingers as your cock covers your chest in semen. He pauses in his **** to let you ride your orgasm. You can feel tears streaming down your face from the intensity of it all.

"It think you're ready now Pretty Boy." he says, withdrawing his finger, "If your reaction to my fingers was any indicator, you are absolutely going to love my cock."