Teacher's Assistant Part 3

"So, uh. What is Round 2, exactly?"

"It's quite simple," Vanilla says, standing up and retrieving her half-full glass from the side table. "You're going to lay down and not move, and I"m going to sit in that chair over there, drink wine, and finger myself while I watch my daughter ride your dick until she physically can't anymore."

Mister Happy likes the sound of that.

Vanilla trots off, leaving you with a last look at her ok-hand-emoji ass and a very scary young rabbit between your legs, kissing and massaging your cock to get it back to full power again.

Cream grins as you reach critical mass, standing up and positioning herself over you as she prepares to - holy shit, girl, that thing's bigger than your forearm. Stop this before you get hurt. You're pretty sure cervix penetration isn't a real thing but damned if you're not about to find out.

Cream lets out a gasp as squats down, pressing your cockhead to her nether lips, spreading as wide as she can to accommodate you. You wince as she lets out a half-pained, half-pleasured moan as your rod stretches her more and more -- your head's barely halfway in. You have a bad feeling about this.

Abruptly, she pulls away and hops off the bed.

"Hang on, Anon. This isn't gonna work."

"I was about to say," you grumble, sitting up. "This doesn't seem like a-"

"Lay back down," Vanilla snaps. You can see her in the back corner of the room now, booze in one hand and clitoris in the other, lazily rubbing as she waits for the show to get started. "No one said you were stopping."

Cream clambers back up, bottle in hand, and starts drowning Kilgore the Mighty in cherry flavored personal lubricant. Satisfied that the rod of ages is sufficiently polished, she sets the empty bottle down and reassumes the position. You get a glance at the label and recognize it from a stand up comedy bit you once heard. Something about parking a Cadillac inside a bird house.

Cream squats down again, already making far more progress than before. Your head pops into her with a wet noise and a muffled yelp, as she bites her lip to keep from crying out. Still, she shimmies and presses down, the excessive lube helping her impale herself on your obscene phallic euphemism.

You're torn. On the one hand, Cream's pussy is like a warm, wet, velvety vice around your dick, and she feels amazing to be inside. On the other hand -- well, there's no way around it. You're barely above average size, and you're scared of tearing the girl in half. Not that she seems to share your concerns.

Her hips meet yours after a good half minute of squeezing and shimmying and sliding. She lets out a breathless giggle, patting her belly and the subtle bulge visible there.

"G-gosh, Anon. You're huge!"

"How does it feel to be hilted, dear?" Vanilla asks.

Cream lets out a quiet moan, biting her lip as she squirms back and forth on the rod buried inside of her. "Mmnf... h-hot. And hard. It hurt at first, but now it feels really, really good."

You have to second that sentiment. Cream is so tight around you you can feel her pulse, as well as every twitch and clench around you as her passage tries to deal with the throbbing six-inch-plus intruder inside it.

"It's not sex if you just sit there, honey," Vanilla chimes in.

"Yeah," you add. "Your mom needs to see you riding a cock the size of your leg so she can rub one out."

"Hush, Anon. Up and down, sweetie. Just like we practiced."

Cream bites her lip, struggling to get her feet back under her. Once she finds her footing, she slooooowly drags herself back up your length, before letting herself fall back down onto you. She gasps. You definitely bumped into a cervix just then.

She keeps up this pattern, lifting herself up as far as she can go before letting gravity do the other half of the work, the sheer strain of accommodating your (relatively) monstrous length causing her knees to wobble and her chest to heave, even though you've barely started.

Her tiny frame glistens with sweat in the dim lighting as she picks up speed, letting out short nonsense words as she hilts herself -- tightly, impossibly soaked -- over and over on your dick. She hikes her arms behind her head as she catches her second wind, thrusting herself downward with renewed vigor. It's the ideal pose to show off a bouncy pair of jubblies. Shame, then, that she's sub-A-cup at best.

She keeps hilting herself on you, over and over, soaking your nethers in a mix of cherry lube and her own juices. Despite starting out almost unable to fit you, she seems to only be gaining speed. You can feel her tiny body clenching around you, shuddering every time she lifts up, only to slam down even harder. Even you can tell she's getting awfully close.

"M-mom...!"

"Aww. Are you cumming already, sweetie?"

"I c-can't hold it anymore!"

"It's okay dear. You can let it out. Show Mister Anon how much you love having his cock inside you."

"I... d-don't...!"

"Cum for me, honey. Mommy wants to see you cum as hard as you can."

Cream lets out a ragged scream as she falls down on you, muscles clenching, milking your rod with a thirst, her body trying to get yours to orgasm in tandem. She falls forward, bracing herself from falling with both hands, beads of sweat dripping from her frame and landing on you.

Her aftershocks last a good while, each one running up her body and causing a noticeable shiver. After her orgasm runs its course, she attempts to lift herself off your cock... and fails.

"M-Mom," she moans, squirming around your length. "My legs..."

"You can't feel them?" Cream shakes her head, still panting from exertion. "Did you get Anon to cum inside you, at least?" She shakes her head again, still dizzy from the ride. "Oh, that'll never do. You have to get the entire lesson we planned for tonight."

"Vanilla, there's no way..."

"Sit up, Anon. Pull out of her for now." You do so, leaving Cream catching her breath on the bed and Vanilla rummaging through the small chest at its foot. "If Cream can't get you to fill her up on her own..." She pulls out a very scary looking silicone instrument. "...I suppose I'll just have to help her."

It's a feeldoe.

You're very worried for Cream's safety.