Nothing like the first time

Jimmy spent the next hour running tests well Tiffany put on her face. He found that sentences that simply stated something as a fact she would accept wholeheartedly and without resistance

For example, you are a stupid whore, would make her believe that to be a true fact, which it is but that’s neither here nor there.

On the other hand if he prefaced it with a qualifier such as I think, I believe or other things of that nature, she handled it the way she normal would.

As her make-up was almost done Jimmy went to her closet and began pulling things out and holding them up.

“would you be embarrassed to be seen wearing this in public, like at the grocery store for example.”

She mostly answered no which got thrown into a pile on the floor but every 4 or 5 things she would say yes which got them thrown in a different pile.

After 20 minutes they had 2 piles of clothes, the much bigger comfortable pile and the 10 or so dresses and skirts in the uncomfortable pile.

Next he started pulling out shoes. Tiffany had at least 50 pairs of footwear, several being sandals and flip flops. Jimmy tossed 12 pairs of sandals onto the comfortable pile without a word and then 10 pairs of sneakers followed suit.

8 Pairs of black flats and 4 pairs of short heels.

There were 16 pairs of heels left ranging from uncomfortable looking to may make her require medical attention.

He plucked up a pair of white 7 inch heels that had the steepest arch he had ever seen on a shoe. It was almost 90 degrees and would **** the wearer to be on the very tips of their toes at all times.

“you are only allowed to take these off to shower or change into another shoe I have given you permission to wear. If I ever see you out of these shoes for any other reason I will sell you to an arabian whorehouse where you will be fucked non stop until your eventual ****, do you understand?” Jimmy didn’t know how he kept a straight face but it worked well to make Tiffany terrified.

She hurriedly put on the shoes strapping them to her ankle and calf to keep them in place. She bought these shoes to go with a hooker costume she wore to a Halloween party. She only wore them for 2 hours and her feet and legs hurt for a week.

Jimmy pulled all the bras and panties out of her drawer and dumped them on top of the pile with most of the rest of her clothes. Reaching into the uncomfortable pile he picked up a particularly shiny black dress.

“if im not mistaken” he said holding it up to the light “this is the one you were earing when you told your mother I tried to **** you” his tone had the sound of wistful nostalgia but his eyes contained a fire Tiffany had never seen in them before.

She tried to speak but instead just nodded, feeling guilt and shame over the event for the first time since it happened.

“Put it on” the words made her look up as Jimmy held it out to her.

She took with with a shaking hand then stared at him for a few seconds without moving.

“do you expect privacy?” he asked sounding a little surprised. “Y…yes?” Tiffany squeeked, sounding very unsure of herself.

“im not leaving the room so my fucktoy can get changed in private, now get a move on” Jimmy said clapping his hands at the end for emphasis.

She stripped out of her sleepwear showing a level of modesty that Jimmy couldn’t help but laugh at. He nonetheless got the best view of her body he ever had and he particularly enjoyed the way her ass bounced and jiggled with almost any movement.

“the longest relationship you ever had that I know of lasted about 3 weeks and you cheated on him twice, is that right?” asked Jimmy trying to ballpark her body count.

“4 times” she said absently As she tried to hold her balance on one foot long enough to step into the dress.

“So how many men have you fucked anyway?” asked Jimmy, genuinely curious.

“I didn’t really keep count, but like 100, 150” she said finally pulling the dress up her body, needing to expose her pink nipples to do so.

Jimmy let out a whistle “I think that makes you a pretty big skank, how many did you let tap that chunky ass of yours?”

“Oh my god ew, none!” said Tiffany revulsion dripping from every word.

“None? Not one of those hundred plus men got in that ass? Jimmy was floored, a slut of her caliber, he just assumed but then he realized what that meant for him.

“I get to pop your anal cherry.” He said with a smile. Tiffany froze as she got her arms through the spaghetti straps, the dress was bought 2 years and 20 pounds ago and it showed. Too tight at the hips and waist it showed the rolls on her side in graphic detail.

The dress was to short to properly cover her ass and the bottom quarter of both cheeks was completely visible. “please…please tell me I misheard that” she said with an edge of panic in her voice.

“sounds like you dislike the idea, I would have figured a slut of your caliber would be getting it up the pooper two or three at a time.” He responded, savoring her obvious discomfort.

“Anal is wrong, nothing is supposed to go up that way, only out…” her eyes were wide and looked unfocused as she recited a line he had heard from his wife a few times.

“The amount you clearly hate this is the hottest thing I have ever seen” said jimmy as he slowly walked toward her, closing the few feet between him and her. A blind man could see how bad Tiffany wanted to run but, jimmy was between her and the door, the only place she had to go was back and one step had her thighs against the bed.

“i…i..dont want…” she stammered as he loomed over her.

“I know” he said cutting her off before grabbing her by the throat and forcing her back onto the bed.

Using his other hand he undid his fly and let his slightly loose jeans slide to his ankles. As he stepped out of them he used his knee to hook the back of hers spreading her legs apart with him between them.

“no….” she hardly whispered looking at the man whose life she had thoroughly ruined.

She had never actually seen his cock before but her friend had at a sleepover. Going to the bathroom she had spotted him getting out of the shower, another reason Tiffany detested him, for 3 years now she had to listen to her friend yap about how much she wanted her step dads huge cock.

At least it came in handy when she needed someone to play the role of “the other woman” liz had been only too eager to volunteer.

Now though seeing it in person, knowing what he was going to do with it, it was the most terrifying thing she had ever seen. 9 inches long, half as thick as a beer can and twitching with excitement.

She had dumped 40 separate men for not giving up on trying to fuck her ass and all that was about to be worth nothing. One of her first boyfriends tried to put his pinky up there and the feeling had made her sick, this was something on a whole different scale.

He moved her ankles to his shoulders and bent her knees so he could start to find the angle. Using his free hand to grab a handful of asscheek and pull it aside, revealing his puckered prize the tip made contact sending fresh waves of horror through her.

“LUBE!” she suddenly cried. “you need lube!” her eyes were so wide and wet he was worried they might fall out.

“Good idea” he said thoughtfully before using his thumb to scoop a mascara stained tear of her cheek and rub it against the tip of his cock, then he started to push.

Tiffany tried to resist the intruder but he had the height, weight, leverage and strength advantage and after 10 seconds of increasing pressure the head vanished inside of her.

The feeling was overwhelming and awful. She had never felt more full or more violated in her life.

That changed 2 seconds later when Jimmy planted his feet and thrust harder.

Almost half of his monster cock wedged itself in her this time and the combination of the tightest hole he had ever fucked as well as the fact that it was his hated step daughter finally getting her comeuppance made him aware this was not going to be a long experience.

Oh well, gotta make sure he enjoys it to the fullest then. Letting go of her throat where he noticed he had squeezed hard enough to leave bright red marks he grabbed firm on her hips with both hands and gave her the hardest fuck he had ever managed to give.

In a few hours the muscles in his legs would make him aware of thier protest but for now he thrust hard enough to make meaty slapping sounds as his pelvis and thighs crashed against her ass cheeks.

Tiffany, for her part, did little but cry and tense up with every flash and burst of pain, unknowingly giving her **** significantly more pleasure as he tore up her insides.

In less the a minute Jimmy knew time was up and made sure to bottom out and fill her guts with shot after shot of burning hot jizz. He took a few minutes to catch his breath well tiffany sobbed beneath him before slowly pulling his cock free with an audible pop.

He panted as he spoke “get all the clothes and stuff in the big pile, take it to the firepit out back and burn it. Well you watch it burn I want you to rub your clit until you almost cum, over and over, never letting yourself cum, repeating the words “I deserve this” until there is nothing left but ash.” Then he stumbled from the room to go take a shower well Tiffany let out a wail like a wounded animal.