Chapter 7 | Bottoms Up

The next few days at Gracely House were a blur for Gwen. The tempo of each day was the same. Morning and afternoon were for private time, which often meant one-on-one tutoring from Mrs. Gracely, and evening was for group lessons.

After lunch each day, Mrs. Gracely instructed the students about subjects such as safe sex, avoiding diseases and pregnancy. Her curriculum was intended to prepare the teens completely.

Gwen's cocksucking skills improved, and soon she could skillfully milk a male into her mouth. And she loved the taste of semen. Staff members at Gracely House were allowed to avail themselves of oral services from the students. It wasn't unusual to walk down a hallway and see a student kneeling before a butler or waiter with a penis in her (or his!) mouth.

It was a week after her arrival that Mrs. Gracely planned to deflower Gwen's bottom. Gwen had been dreading this experience since watching Jackie take it anally for the first time. Jackie's torment seemed extreme, and Gwen didn't want the same experience.

For several days beforehand, Mrs. Gracely worked to prepare the girl for losing her final barrier. No matter how much a girl welcomed her first vaginal penetration, nearly all of them feared the breach of their bottoms. But it was a mandatory part of Mrs. Gracely's curriculum, and she knew how to get them ready.

With fingers and a succession of toys, Mrs. Gracely accustomed Gwen to having her anal flower stretched and entered.

One night she caused Gwen intense humiliation by making her take her own rectum with a dildo while the other students watched. They saw her push a small phallus into herself while lying on her back. Then she had to masturbate to orgasm while stroking the dildo in and out of her rosehole.

To perform the ultimate honors in Gwen's rear portal, Mrs. Gracely selected Dalton, a student who'd arrived a few days earlier. Dalton enjoyed his first romp in a girl's derriere when he and Jackie were coupled two days earlier. By then, Jackie had warmed to having her bottom taken, and she'd come while Dalton fucked her back there.

So the barely experienced Dalton and the anally virgin Gwen would be put to each other that night after dinner.

Mrs. Gracely felt particularly good about the forthcoming union because she thought Dalton's cock was truly magnificent. He was slightly larger than average but not excessively so. His erect cock was straight and proud. It rose from his belly with confidence, and the mushroom tip flared nicely. He was a handsome lad with thick dark hair.

Gwen knew what was inevitable, but she didn't know this was the night. When Mrs. Gracely summoned Gwen and Dalton to the divan and explained their assignment, Gwen didn't think she was ready. She very strongly didn't think she was ready.

"No, Mrs. Gracely. Please. I don't want to," the girl pleaded.

The teacher glared at her reluctant pupil. She pointed to the divan with a stern look toward Gwen.

On impulse, Gwen chose this moment to make a stand. "No. I won't."

"Are you refusing, young lady?"

"Yes."

"Gwen, this is your last chance. Get on the divan and put your bottom up for Dalton."

"No."

Mrs. Gracely gestured to the servants. Two large butlers stepped toward the trembling girl. She didn't struggle much, for she knew it was useless. But at least she could have the satisfaction of knowing she didn't go willingly.

They carried her to the divan and turned her face down as she squealed. One lifted her hips while the other pressed her shoulders down.

Quickly, they pulled her arms down to her sides and tied her wrists to her ankles with silk neckties. Gwen was immobile on the bed with her bottom thrusting up and completely vulnerable.

And a beautiful bottom it was. Everyone in the room admired the firm globes with their flawless skin pulled taut. Her legs were apart, and it was easy to see into her nether regions... the puckered, virgin ring above the swollen, moist lips.

Mrs. Gracely reached in and fingered the scared pupil. Her finger slid into Gwen's channel and then spread lubrication all the way to her anus.

"It's too bad you resisted, Gwen. I think the butlers deserve a reward for having to deal with you. Don't you?"

"Yes, ma'am," Gwen replied with meek resignation while her face pressed against the furniture.

"Very well. We'll let them have a little pleasure before we return to our original mission."

Mrs. Gracely signaled to the butlers. They stepped toward Gwen, unzipping their trousers as they went.