One of your closer friends

"Mr. Fern"

You hear Mr. Hector call up the next name, and can't help but feel betrayed. Douglas Fern is probably your closest friend in this class, and the fact that he volunteered to help Mr. Hector humiliate you irks you a little...

You turn your head to glare, but he studiously avoids looking at you, accepting the condom and letting out his cock. You've seen - and felt - bigger, but it's still firmly into the range of 'pretty big', and you notice that it's already fully erect by the time Douglas whips it out. He seems to be rather eager as well as he's unrolling the condom down his shaft...

You're not sure what to think of that...it'll be a little hard facing Douglas later after seeing him so enthusiastic about doing you in the ass...

Douglas is considerate enough to enter your hole slowly and carefully, taking care not to hurt you too much. The slow, almost tender entrance only makes the situation more awkward though...you're not sure how you're going to calmly hang out Douglas in the future without thinking of the feeling of him gently sliding his cock into your ass.

Worse still, he shifts around inside of you probingly, re-positioning his cock until it's in just the right spot to stimulate your prostate. Your sudden quiver of pleasure makes it clear when he's succeeded.

He begins slowly, rhythmically moving his hips, making waves of shameful anal stimulation assault you without stop. You can't hold back from having one mostly-dry orgasm after another, fluid oozing from your member beneath you as your friend slowly picks up the pace.

After a half dozen of your shuddering climaxes, Douglas cums hard, only a thin layer of rubber saving your ass from a gooey fate. You feel drained as Douglas deposits his condom on the desk and leaves...

Maybe he decided as a friend to make the experience enjoyable for you? Part of you definitely did enjoy that...though couldn't he have just made it quick if he wanted to help you out...?