Author's Note:
Thank you for clicking on my story! I hope you enjoy it, but before you begin I wanted to mention one thing. This story involves people participating in sex work but in a VERY lighthearted way. I do not know much of anything on this topic and I did not intend on writing a story that tried to accurately portray this lifestyle. Everyone has a happy ending today.
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The pictures were gorgeous. The soft, young, smooth skin against the black thigh highs, thong and lace bra. He loved the brown hair with the amber highlights. Her breasts looked much smaller than his wife's had been, her legs longer, her hips narrower.
He missed his wife. It had been two years but he could still hear her voice in his mind, she seemed to chime in on all his important decisions. He was nervous about sending this message. The money was nothing, he had plenty of money, the settlement left him with more than he would ever spend. He was only still teaching because he didn't know what to do with his time if he retired.
God this woman was beautiful. Her profile said she was 26, less than half his age. It couldn't be real, only three hundred dollars to actually be able to have sex with her? There were so many reasons not to do this.
On the other hand, there was one big reason to do it. Every time he hesitated and didn't send the message he had drafted his wife's voice called him a pussy.
Professor Jennings had married Teresa when he was twenty three years old and had been thankful every day after that. Teresa had constantly pushed him to try new things, take risks and generally keep him from spending all his time reading.
He remembered when she had made him drive for three hours to an apparent "apple tasting festival" that turned out to be a farmhouse with three different varieties of apples sliced up. Teresa knew he would be upset so she stole a can of whipped cream from a table that was selling cobbler, lead him out to a secluded spot behind these huge crates of apples and licked most of a can's worth of whip cream off his cock. He didn't complain about the long way home.
He knew he should be getting out more, doing anything. He hadn't realized how many events felt awkward to go to alone.
He could feel his wife rolling her eyes at him. She would say something sarcastic like "OK I understand, making love to that musty book is so much hotter then fucking that twenty something year old who can probably spin herself around like top."
He actually said "fine" outloud before sending her the message.
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Three days later Dave sat on the couch of a decent hotel room. He was nervous but not nearly as nervous as he thought he would be. His wife's voice told him it was ridiculous that he was wearing a tie, but he had no idea how he should have dressed.
He took a swig of water when he heard the soft knock on the door. He felt silly once he had opened it. She was so beautiful, he had not seen her face in the pictures and he was not disappointed. She wore much more eye makeup then his wife ever did, and he had also never seen his wife in heels that tall. That's when her voice came to him and told him to stop thinking about her and to enjoy the next hour.
"So hello." She said warmly.
"Hi, ummm do you want something to drink?" Dave asked before realizing he didn't have anything to give her if she said yes.
"No, I am good." she said. "It's nice to meet you...Matt."
Dave started to correct her before realizing that was the name he had given to her.
"Same here. Ummmm so..." Dave trailed off.
She smiled and took her coat off. She was wearing a short tight beige and black skirt with a white blouse. He didn't know what to expect her to be wearing, she obviously wasn't going to be wearing the same lingerie from her pictures, but she looked much more professional then he had expected.
"You haven't done this before have you?" She asked.
"Is it that obvious?"
"Ya kinda." she said smiling wider. "You can call me Mandy. Why don't you sit in that chair, I'll help you relax."
As he sat she stood behind him and rubbed his shoulders. It felt amazing, she seemed to calm and gentle, no one had ever touched him like she was now. She ran her hands through his hair and eventually kissed his neck.
"Is that good?" She asked him.
How could it not be he thought. "Yes very."
"Maybe this will be nice also." She said as she slid herself onto his lap facing him. She nibbled on his ear and ran her tongue down his neck. Her hands pushed themselves under his shirt and rubbed his chest. He was in heaven.
When her hand dropped down and began rubbing his cock through his pants he thought he would have a heart attack. This woman was so far out of his league this should be impossible, yet she seemed to be having fun. If he had thought about it longer he would have guessed that wasn't true but she was certainly fooling him in the moment.
"Lets make you a little more comfortable." she said as she undid his pants.
Her hands felt like they were made of silk as they caressed his rapidly hardening cock. She rubbed it so slowly, and carefully, as if she truly cared for it.
"See trying new things is great." It was his wife's voice again. She had always been right.
"Can you help me with this." Mandy asked now standing and facing away from Dave. It took him a moment to realize she meant the zipper on the back of her skirt. As he began to undo it she pulled her blouse off. As he tugged her skirt to the floor he was face to face with her very round ass which was just partially covered by a pair of very lacy and see through red panties.
Mandy looked over her shoulder. "Do you like them?" she asked, running a finger under the edges of panties, straightening them.
He looked up at her, "Yes, they... you are beautiful."
Mandy smiled. " Thank you so much." She then turned and kneeled in front of him. "Tell me if you want me to stop and we can have sex, or we can do anything else you want."
She cupped his balls into her hand and ran her tongue around the underside of his cock head. The site of this young gorgeous woman servicing him in this way was almost too much for him right then.
She went slow, wrapping her lips around just the head of his cock, sucking her cheeks in and then releasing and licking up and down the sides. She kissed his stomach, and rubbed the inside of his thighs, she looked up at him and stroked his cock.
It seemed like hours went by but when he glanced at the clock she had only been kneeling in front of him for eight minutes.
She noticed him glancing at the clock. "Would you like do something else? We can get on the bed together."
Dave nodded and they moved the three feet. They laid next to each other, his hands exploring her body. He had never been with a woman who shaved her pussy before. He touched her arm and run his hands down her side and her hip. She eventually put his hand over his and slid it between her legs. She felt wet and smooth. He rubbed her, hoping he was touching her clit, hoping she didn't hate this. She let out little moans and closed her eyes and Dave was pleased with himself.
She sat up and straddled him, his cock so close to her warm and inviting opening. She leaned forward, her breasts pressing against him. She kissed him all over, her breath warm on his body and her tongue made his skin tingle. She kissed all the way down to just above his cock and effortlessly slide a condom onto him. He had not worn one of those in three decades.
She reached her hand down and maneuvered his cock into her. She grinded herself against him, sometimes up and down, sometimes in small circles with his full length inside her. He had never dreamed it would be this good.
She seemed like she could sense when he was getting close, her pace picked up, she put her hands on her chest and began thrusting her hips up and down his shaft faster and faster.
As he began to feel his cock spasm he grabbed her tits and she put her hands over his and pushed then against her firm mounds even more forcefully.
His cock went limp with it still inside her. She rode him until he was completely flaccid and had fallen out of her. She laid back down next to him, she almost seemed sleepy.
"That was amazing. It had been a really long time since I had been with anyone, thank you so much Mandy." He said enjoying the afterglow.
"I'm sorry about your wife." She said, almost equally as groggily.
Dave sat up, "What do you mean by that?" He asked.
Mandy's eyes opened back up. "Oh god, I am so sorry Professor..." She stopped.
They both looked at each other, Dave suddenly realizing that "Mandy" did look a bit familiar.
She pulled away from him and stood up. "I'm sorry, I'm really sorry, I should have kept pretending, I just... I AM really sorry about your wife."
Dave's head started to spin. "No really what do you mean?"
Mandy paused, "You really don't recognize me do you? It's me, Alison, I was Professor Ellison's TA two years ago."
Dave wanted to throw up. "Oh my god, Alison I am so sorry. I never would have... I'm really sorry."
Alison's tone changed "No no no, Professor Jennings, it's all ok, if I had a problem with this, I would have left as soon as you opened the door. I thought you recognized me as well. I'm the one who is sorry."
She paused "Professor, I'm not going to tell anyone about this, you were like my favorite professor, you helped me so much. I actually hope we can do this again sometime." she smiled at him, and he believed her.
He took a deep breath. "You were such a good student, why are you doing this?"
She laughed a little, "Well I kinda thought I was good at it"
He cut her off "You are very good at it."
She smiled and continued. "School is expensive and I have bills, this is a lot better money for a second job then waiting tables or something like that. I would actually recommend it!"
"Well shit, I didn't see that coming." His wife's voice chimed in.
Dave tried to ignore the voice in his head. "Ok well I guess I need to give you this, and hold on." He handed her the envelope he had put on the nightstand with the money in it. He then went to his wallet and took out the other eighty dollars that were in it. He handed that to her as well.
She smiled at him, "You are so sweet." She kissed him on the cheek, then gave him a hug. "Really though, don't worry about me...you look like you are worried about me."
He didn't respond, he didn't know what to say to that since he was.
