Driving home that night, James felt very satisfied with his day. He'd made some money, he'd soon be making more, he got a blow job, and his girlfriend was now officially also his whore.
James and Kerry didn't talk that night, but James did have a short conversation with Jake, Kerry's old boyfriend from 8th grade who was interested in Kerry.
"So how much are we talking about?" asked Jake in a nervous tone.
"Well depends what you want?...What do you want, don't be bashful..haha"
"Umm...well, I want her to suck my cock, and swallow, and fuck me..."
"Alright, that can be arranged."
"And what Jake?" inquired James.
"What about her ass?"
"What about it?"
"Can I fuck it?" questioned Jake tentatively.
"Well that will cost you a little more...I'd wanna break her in a little before you get her there, you see I've never fucked her ass."
"No...I mean, I would like to be the first one."
"Well, that will cost you quite a bit, foreplay, a blowjob, and anal sex (in which you take her anal cherry) will cost you about 250...I know it's expensive but being the first in her ass is a big deal..."
James laughed at Jake's eagerness. They agreed that this Saturday would be good.
The next day (Friday) James called Kerry and informed her of her plans for tomorrow. She wasn't too happy.
"I have to fuck Jake? I dumped him cause I didn't like him..."
James didn't respond.
James didn't mention to Kerry that she had to give him her anal virginity, that would have to be saved until the last minute or else she'd definitely back out...
On Saturday, James drove over to Kerry's house. He found her doing her hair. He was happy that she was trying to be as appealing as possible. She felt a little queasy but held it inside. She slowly put on the outfit that she had worn last time. The thong slid gently up between her ass cheeps. The sweater slipped on and tightly held her tits. Her nipples were hard, was she cold or getting a little excited, wondered James. She then slipped into the skirt which James had to help her zip up the back cause it was so tight, this gave James an opportunity to feel up her ass, an ass that he knew in a few hours would be ripped open. Then she pulled her boots up to her knees and stood up. She had an air of confidence, James didn't like that.
They got into the car and drove towards Jake's house.
"Listen, there's something I've got to tell you" said James quietly but with firmness.
"I know, I know, do a good job so he wants me again"
"No, more than that...Jake is paying a lot for this because you're going to let him fuck you in the ass"
"WHAT!? NO I'm not" cried Kerry.
"Yes you are, he's paying for it. It won't be bad, you just have to accept it and do it."
Kerry was panicking a little, she felt betrayed. How could he sell her like this?
"and you better not give him a hard time, I'll be pissed...very pissed" he said in a tone that scared her a little.
They got to his house. James went in first, got the money without exchanging a word with Jake and went back out to the car. Kerry got out, and walked over to James. She was clearly shaken. James told her to call him when they were done.
"You mean you're not staying here?"
"I figure you'll be in there for a while"
James got back in the car and drove away...
Walking towards the door of the house, Kerry looked down. She looked at her boots, still brand new looking, and thought "this isn't me, but I'm doing this" As she approached the door her heart rate went up. She was filled with dread and a feeling of helplessness, that no matter what, something big and probably painful and probably pleasurable was going to happen in this house.
Jake opened the door before Kerry got there and invited her in. He offered her a drink, but they both knew this was just a way to try to break the tension.
"Umm, let's just got upstairs then"
No one was home it seemed. On the stairs, Kerry felt a hand from behind her grope her left tit. She squealed from shock for a second but realized she better get used to being touched. She goes into his room, it hasn't changed much since 8th grade when she was last here, but then they didn't do more than kissing then.
Kerry took a deep breathe, I can't do this, she repeated to herself. Suddenly she sat down on the bed and spread her legs revealing her black thong panties to Jake, she began to pull down the zipper of her sweater revealing more tit. What am I doing? she asked herself. It felt like she was no longer in control, but she definitely was. The sweet little innocent Kerry that Jake had dated years before was doing all this. He walked closer, leaned down, and kissed her deeply, probing his tongue around her mouth. This was the first time in three years Kerry had been kissed by a guy besides James and it excited her even though she didn't want to be. The kiss ended, though Kerry wanted it to continue, and Jake stood up, Kerry remained sitting on the bed.
Jake was nervous, this was what he always wanted and he almost couldn't believe it was happening. He began to undo his jeans, they fell to the floor and his hardon was now a few inches away from Kerry's face. She pulled down his boxers and thought to herself, I better do a good job cause he's a paying customer. She licked and sucked his balls for a second, getting the dick hard, and then she took the whole thing in her mouth in one movement. She started to bob her head, and suck it gently.
In seconds, Jake moaned and cum started to spew into her mouth. At first she gagged, she couldn't believe how much there was. It just kept coming like a waterfall. Kerry began to swallow fast, to make room for the next squirt. As the cum slid down her throat, she began to feel her pussy tingle. I think I'm starting to like this, she thought.
After he was done, he pushed her back onto the bed and took off his shirt leaving him naked. He began to slowly unzip her sweater, revealing her tits slowly. Jake had never known that everyday beneath the shirts she wore, Kerry had a perfect pair of tits. He began to squeeze them very hard, and pinch her nipples, and then he settled in on sucking one of the. Kerry let out her first moan, she felt embarrassed that she was getting so into a fuck that she was being paid for.
Then her skirt and thong came off, faster than she even realized, leaving only her boots on. She was now very wet and hot and wanted a dick in her pussy badly, and very quickly Jake's cock sprung back up, and this time she knew it would last longer. But then she remembered that he wasn't going to fuck her pussy, but was going to rape her ass.
She didn't know what to do, she was horny but she wanted this all to stop.
He began to tit fuck her, something she had never had done before, which she enjoyed immensely. It took her mind off the agony that was to come, she knew that because he paid for her ass he wasn't going to be gentle.
"You better get it wet" said Jake forcefully.
"Where it's going it'll be easier wet."
"NO!" screamed Kerry.
"Fine, it'll just be harder"
Kerry whimpered and realized she'd better get it wet. She took the whole thing in her mouth and licked it all over, making sure to coat saliva everywhere. Jake let out a moan of pleasure.
Then he pulled his cock out and told her to turn over. As she did, Kerry stuck her finger in her pussy so it was all wet, then ran her finger around the outside of her ass hole, trying to lubricate it slightly. She had no idea what she was in for.
She spread her ass cheeks. She was crying a little now, but silently, and she was still quite horny.
Jake's cock came to the opening of her ass, Kerry bit her lip and Jake's cock entered. It was worse than she could have imagined, she felt her ass stretch and she knew that no matter what, Jake's cock wasn't stopping.
"I'm gonna rip" she cried through her tears. She really felt as though her ass hole would tear like paper. Jake stopped. Finally, he's in all the way, thought Kerry. But when she looked back she saw he was barely halfway in. He then plunged the rest of the way in. Kerry buried her head in the pillow and Jake moaned. He pulled out, and then pushed back in. This time it hurt even more because her insides were raw.
He got a rhythm going, and each time Kerry felt her ass warp and stretch agonizingly. The pain didn't seem to subside, it was still very intense and seemed to overtake her whole body, but she began to control her crying. I can do this, she thought, I'm a big girl, I can handle this pain. She started to push her ass against his cock, hoping that would make him cum faster. He seemed to enjoy it.
Soon, Jake was grunting and pushing harder. She knew he was close and was glad this would be over. She felt his cock in her ass begin to swell, then he put it deep in her and didn't pull it out. He began to squirt. It was unlike anything she'd ever felt. Deep in her raw and ripped ass she began to feel an amazing and beautiful warm sensation. As his cum filled her she felt like there was a fireplace in her body, she couldn't get over the awesome experience. He kept cumming and soon Kerry felt something in her pussy. She suddenly exploded in orgasm. Her whole body quivered and shook and she screamed like a little girl. This was the first time she'd ever come without any vaginal stimulation.
Jake pulled out his cock, quite satisfied. Kerry laid there face down, still feeling the hot sensation deep in her ass. She leaned her arm back and ran her finger over the opening of her ass; she got a little cum on her finger and put it in her mouth. The warm sensation in her ass and the intense taste in her mouth made the pain of her ripped ass hole a little easier to bear.
Jake had fallen asleep. She checked the clock, she'd been there for an 40 minutes, she couldn't believe how fast it went. She sat up and looked at her body, she laughed cause she had never taken off her boots. She brought her knees to her breasts and hugged her boots tightly as if they were her new friends.
Her ass still dripped a little when she texted James to come pick her up.
She slowly dressed and very gently pulled up the thong, careful not to hurt her very sensitive ass hole.
She went downstairs, not even saying goodbye to her client, moments later James was there to pick her up....