(Special thanks to Busty Jessica my eternal muse and Pennlady for making me a better writer each time. All mistakes are mine and mine alone though! Enjoy!)
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Busty Jessica was still a little bit sore from her double anal escapade at the truck stop. She decided that she was going to stop all anal sex for at least a day. It had gotten her a ride far away from her home town, though. She felt amazingly liberated when she hopped down from the big rig, causing her large breasts to jiggle, and looked around at the big city she was now in.
It was just her now, and she was in complete control of her own life. It was a daunting feeling; Jessica had no idea what she was going to do. She had no money and just the clothes on her back. It looked like it was going to rain soon so her first priority was to get inside. She saw a sign for a bar down the block and made her way to it. Not being twenty-one yet, she hoped whoever worked there wasn't a hardass. It was getting dark and there wouldn't be too many other places she could hang out in this late.
Upon walking into the bar, Jessica was pleased to see that it was quiet, dark and seedy. They generally didn't card at the door at places like that and she could relax and plan out her next step. She settled into a dark booth in the corner after freshening up in the bathroom. She felt better already. It wasn't long before one of the servers brought over a drink.
"Compliments of the gentleman at the end of the bar," the waitress said and then walked away.
Jessica glanced over at the bar and raised her glass in a gesture of thanks. The gentleman at the end of the bar was middle-aged but reasonably, handsome and in good shape. He was definitely a step up from the truckers she had been hanging with for the last few days, even if he did look like a used-car salesman.
Jessica wasn't surprised that she had caught his eye. She was the best looking woman in the bar by far and with her large breasts straining against her tight top, she had every man in the joint staring at her. A free drink is a free drink, she thought and downed it in two gulps.
The man who had send that drink sent over two more in quick succession and the waitress told Jessica that they were Long Island Iced Teas. She had never been a drinker and was feeling quite tipsy after the third one, when the gentleman suddenly appeared and slipped into the opposite seat in the tiny booth.
"Hi there," he said. "My name is Sherm and you looked like you could use a drink and some company."
"Thank you for the drinks," she replied. "I was really thirsty."
"You're welcome, honey," he replied with a big smile. "What's your name?"
"I'm Jessica. I'm new to the area," she said.
"I could tell. Let me show you something," Sherm said and stood, waiting for Jessica to do the same. His eyes never left her chest.
Jessica followed Sherm past the juke box to the back of the bar. There were pool tables and video games and a little community bulletin board advertising local businesses. Above that was an aerial picture of the city.
"Wow, that's really cool." Jessica grabbed Sherm's arm to steady herself. Those drinks were really doing a number on her.
Sherm opened a door beside the display and pulled Jessica through it.
"Where are we going now?" She was giggling.
Sherm didn't answer her. He closed the door behind them and she saw that they were in a little supply closet. Off to one side there was an empty desk. Sherm reached out and cupped one of Jessica's large breasts. She smiled.
"Time to pay for those drinks, eh?" she asked, dropping to a kneeling position in front of Sherm.
"Oh, I like you already, sugar." He reached down to unzip his pants. Jessica did the rest, pulling his pants and underwear down to his ankles. She let out an appreciative gasp; Sherm was hung like a horse. Jessica started to get wet just thinking about how that monster would feel between her legs.
Jessica wrapped her hand around his giant cock and started to stroke him. Then Jessica parted her lips, taking his cock head inside her mouth. He moaned and laced his fingers in Jessica's hair. She slowly worked her mouth down his cock, taking as much as she could.
Sherm wasn't a patient man though, and was soon thrusting his hips forward, fucking Jessica's mouth. She gagged with each thrust, drooling around his cock. He was fucking her mouth furiously and Jessica was upset with herself that she wasn't able to handle him better.
Sherm pulled out and picked Jessica up off the floor, then walked her over to the desk. Jessica had been waiting for this and hiked her short skirt up exposing her lace panties to Sherm as she sat on the desk, legs hanging over the edge. Sherm licked his lips and smiled as Jessica pulled off her panties.
"Let me have that thing, Shermy," she said huskily.
Sherm moved forward until the tip of his large cock pressed against Jessica's sopping pussy. He lifted her legs until her feet were resting on his shoulders and then he pushed his cock all the way in. Jessica's eyes rolled back into her head and she squealed. He was huge. She had never felt so full. This was completely different from when she had two cocks in her ass at the same time back at the truck stop, but it was just as wonderful. Sherm waited until Jessica came back to earth and looked up at him with those big wide eyes.
"I'm ready," she said.
Sherm pulled his cock almost all the way out slowly and then pushed back in just as deep as before. Jessica wiggled beneath him as Sherm repeated his slow methodical thrusts. He was teasing her and she couldn't take it. She needed to be fucked hard and fast now. She was ready and she could handle his massive cock.
"God, fuck me hard, Sherm. Please!" she pleaded with him.
