“Ahh, ahh,” is all I can say. He wriggles his fingertip around my sphincter, which feels more sensitive now than ever before, probably because my pussy is not there to distract me anymore.
“Tell me, Elizabeth, has anyone ever fucked this particular orifice?”
“Ahh, no, uhm, just-” I gulp breaths. “One boyfriend, uhm, stuck it in by accident one time.” Kevin. Literally the only thing I remember about him.
Mr. Keene chuckles. “That was not an accident, whore. It never is.”
“Ungh, ahh,” I reply, too overwhelmed by sensations to hold a coherent thought, least of all about a long-long-ago, long-irrelevant ex-boyfriend.
“How many improper orgasms have you had in this hole?” Colton tickles said hole.
“Ah! Ungh! None, Sir! Please!” I try dancing out of the way. My range of motion is severely limited. The acute feeling of helplessness drives up the temperature inside of me.
Mr. Keene grabs my left butt cheek hard and uses it to hold on to me like a handle. “And how many did you have with your whore slit?” he asks, then cavalierly adds, “roughly. Rounded to the nearest hundred.”
“I… I don’t know,” I stammer. “A… A thousand?”
“An estimate so conservative that it would be justified to call it a barefaced lie,” he chides me and sinks his digit deeper into my rectum, then pulls it out again. The sucking noise becomes louder. “I told you to keep it out, Elizabeth.”
“Hah! Hah! Yes, Sir!” I whine and clasp his finger as hard as I can. It feels uncomfortable and strenuous, and it makes his finger feel so much larger.
“My son has been brought up by me to never be satisfied with hand-me-downs,” he tells me. “Which is why he accepts it as propriety to forego the secondhand things and claim only the unused ones. Do you understand what I am telling you?”
“Uhn, uhm.” I try so hard to collect my thoughts. “Dylan — he, he will… uhm.”
“After you’re married, he will not be using your cunt, Elizabeth. Because your cunt is sloppy seconds material.”
“Nooo,” I wail. I’m sure my pussy is squeezing so hard right now, but it is so muffled that it is barely there. “No, please, I- Dylan and I- That can’t be right!” I remember his longing looks between my legs when he ties me to the bed at night. He’s always looking at my pussy. I was so sure… I was looking forward to… “He said he wants me to have his babies!”
“There are alternatives to impregnate you, don’t you worry about that,” my father-in-law soothes.
I believe him. The moneyed always have alternatives, and the Keenes are definitely moneyed.
“As Dylan’s spiritual guide, I have advised him to not indulge in improper things. Your cunt has stolen thousands of orgasms from him already. It is the very epitome of improper, and I am sure Dylan will punish it for all those past transgressions… one… by… one.” His finger slides into me fully and out fully with each word, pumping.
All of them? There have been so many… so very many. I have taken unmeasurable amounts of pleasure and extasy with my- my whore slit. “I’m sorry,” I sob, so out of my mind with sensation and emotion that I forget one of my very first lessons for a second.
“I’ve told you; apologies are worthless. Also, you’re not sorry yet, but you certainly will be.” And he chuckles as though he has made a very clever joke. “Dylan will see to it, make no mistake.”
I shudder. My restraints pull hard on me.
“Given that this little hole” — he twists his finger and teases my entire crimped rim — “is the one that my son is planning to use most, if not exclusively — your mouth and throat are perfectly serviceable, after all — I thought it proper to help you get over any significant resistance beforehand. Get all the hysterics out of the way. Wouldn’t want my son to have to console you and forgo his well-deserved pleasure on his wedding night, would we?”
“Ah, no, Sir.” My voice sounds resigned.
“You will learn how to keep this hole clean and healthy for his use. Starting today, you will use enemas regularly.”
“Yes, Sir.”
“You will wear plugs and vibrators to stretch you and to strengthen your sphincter so that fucking you will feel good to him.”
“Ungh. Ungh! Ah! Yes, Sir.”
“Good. Now breathe.”
I barely have the time to before he adds a second finger, somehow increasing the pressure and the sensations by a magnitude. I moan. “Too much! Please, please, slower, please, pull it out!”
“I am not your accidentally-on-purpose poking-your-shitter-once ex-boyfriend, Elizabeth.” He swats my ass hard three times with his free hand. “Do not presume to treat me like him or talk to me in the same way. Now behave and breathe, whore, and tighten your ass. Try to push me out. Massage my fingers with your muscles.”
I whine and beg, receive several more stinging swats, and then do as I am told as best I can. His fingers feel like a 2×4 each. “Too big,” I cry.
“I’m going to plow this ass with my cock shortly,” he says. I wail at his words and hate how my nipples harden perceptibly. “I promise you, my fingers won’t be too big any more soon. In fact, you’ll be begging me for them.”
I don’t know how much time he spends priming my asshole with his fingers, adding so much lube that I make farting noises and feel the cool, oil-slick wetness all over my goosepimply cheeks and the backs of my thighs. He adds a third finger and stirs me up more, and every thrust into me is like he’s squeezing in next to all my intestines, every pulling out feels like someone is suctioning my lower body out of me. Shower after shower of tingles rush through me.
“Your ass is gaping like a fish mouth, Elizabeth.” He sounds so amused. I wish the ground would swallow me up. “Your insides are so slimy and pink. Your ass truly is a second vagina.”
Horribly, the sensation of his fingers stays when he pulls them out. I feel my sphincter twitch uncontrollably around the ghosts of his digits. I groan. I swear I can feel the breeze inside of me. Everything feels chilled and loose and too… open.
“One of the members of the Vow’s ecclesia is a tantric sex coach.” Mr. Colton’s voice is a little distant. He has gone next door to wash his hands. I am endlessly grateful that he didn’t make me lick him clean.
“He teaches the receiving partners the art of pompoir. It is a technique in which the receiving partner massages the giving partner’s cock with their inner muscles and brings them to orgasm. It requires strength, stamina, focus, and resilience.”
“I will learn it.” What else can I say?
“Yes,” he agrees, stepping behind me, grabbing my ass. “Yes, you will, so that you can masturbate a cock with your asshole.”
The nudge of his fat cock against my hole makes me hold my breath. Oh God, oh God…
“Breathe,” he commands, waiting, waiting endlessly, patiently, like a cat hovering by the mousehole. All the time in the world. “Push, like you’re on the toilet taking a shit.”
Shaking, groaning with shame, I do.
The pressure grows and grows and grows, until the crown of his meat slides into me with a pop, my sphincter closing around the ridge.
Although it is slick with lube and possibly pre-cum, it still feels the size of a tree trunk.