Matt takes you gently

You sit down on the bed and let Matt gently push you on your back. You watch him taking the dildo and lube bottle from the nightstand, and placing them next to you.

"I know how you feel, but seriously, don't worry", he tells you trying to sound reassuring, "I've done this many times before and trust me when I say that with a proper warm up it won't hurt a bit."

You find this hard to believe and say as much. Matt gives a short laugh and repeats the same message that you shouldn't worry. "Seriously, I mean it. I know my penis might look a bit daunting, especially for a first timer like you, but I do know how to use it."

Matt leans over you for a one more kiss and while at it, caresses your body with his rough hands. Even though still nervous, you already feel incredibly turned on, shivering under his soft touch. Matt also slightly grazes your dick as he rises back, making you realize how hard you already are.

"Now, lift up your feet on my shoulders."

You follow the instructions and rest your feet on top of Matt's muscular shoulders. With that your ass is now raised high, giving him a perfect access to it. With Matt still exploring your body with his other hand, you feel a lubed finger pressing against your tight virgin hole. You make your best to relax and soon feel a finger slowly sliding in.

"How it feels", Matt asks you.

"Not too bad", you say. You've occasionally practiced by fingering yourself and this doesn't feel too different.

Matt keeps fingering you slowly, soon adding a finger and eventually another. With three fingers slowly pushing all the way into your butt, you feel somewhat uncomfortable, but to your surprise it doesn't hurt at all. Your dick is fully hard and begging for attention, but it doesn't get any. As you feel Matt pulling his fingers out, you glance at him and notice him currently applying lube on the large dildo.

You look at Matt and he smiles and nods at you reassuringly. You nod back at him as he brings the dildo onto your waiting hole. You gasp as the dildo slowly penetrates your tight ass.