Professor Dave's New Hobby

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.

**********

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.

**********

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.

"Really, I hope we do this again Professor Jennings, it was great."

"You can call me Dave." he responded.

"OK, I will ... Dave."

She left a few minutes later, after fixing her makeup. She looked like nothing had happened, and Dave realized she had gotten very good at entering and exiting hotel rooms as if nothing happened while she was inside of them.

For the next week Dave thought about Alison. It had been amazing. Did she really want to do it again? Did that matter? She was going to do it with someone so why not him? Did it make it worse that he wanted to fuck her again even though he knew her as a student? Would a second time ruin the nearly perfect memory of that first time?

Teresa did not have much to say about it. The little she did chime in about told him to give it another shot, and that he over thought most things. He sent Alison another message.

She replied a few hours later, she was traveling but would get in touch when she returned. Dave took that as a sign that maybe once and done was best. He decided he wouldn't reach out to her again if she never got back in touch with him.

**********

Two days later Dave sat in his office waiting for his last student conference of the day. It was nearly five and the building was empty, his colleagues who had families wrapped their schedules up by four but he wasn't in a hurry.

He didn't know why Zoe had asked for a meeting, she was doing well in his class and he had already helped her set up an internship.

She knocked on the door a few minutes early, and they chatted about her semester in general. The only thing that seemed to be an issue was that she was living off campus for the first time and while it saved her money over all it was different having to pay rent each month instead of it being all covered by her financial package.

"So I have been reaching out to some of the other students who I know lived off campus before to see what jobs they recommend I look for." Zoe stated, trailing off a little at the end.

"So um what did you find out?" Dave asked starting to get a bit bored with this conversation.

Zoe took a deep breath "Well my really good friend has been trying to talk me into what she is doing, she really recommends it but I don't know."

Dave assumed she was about to get sucked into a pyramid scheme.

Zoe continued "but ummmm well I think I'm going to try it." She paused again and took another deep breath.

"Alison told me you might be interested in helping me make some money for my rent." Zoe finally blurted out.

Dave froze. "What do you mean by that?"

Zoe began to ramble, "Well me and Alison had been talking about doing it for awhile, but I wimped out and now I see how much money she is making and I really want to do it but I am really nervous and I really am hoping you'll be my first time but if you don't want to I understand I am sorry, but please, it would be really great if you would... And I know I am saying really too much. " Zoe stopped talking and looked at him.

Dave had no idea what to say to this young woman who was reverse propositioning him.

After a very noticeable pause Zoe spoke again. "Ummm since it would be my first time I wouldn't expect the same amount as Alison... really whatever you thought was good..." she finally trailed off.

Dave noticed her face was turning red, he still had no idea what to say to her.

That's when he heard the first whimper. She wiped her eye before she spoke again. "Oh my god, I am so sorry. This was so horrible of me. I am so sorry to put you in this position I'm so dumb." Zoe started to collect her things.

"Oh my god, you asshole, you can not reject her like that." Teresa finally decided to chime in.

"OK, OK... take a breath Zoe. You are not dumb." Dave began not sure where he was going to go after that.

"Yes I am, why would you want to have sex with me, Alison is so hot and knows what she is doing so well I am sure, and I should not have even said anything. God, why would anyone want to pay me for that." Zoe said still obviously trying to choke back tears and collect her things.

"Zoe stop I am sure every guy around campus would like to have sex with you." Dave hoped that was comforting.

"A guy called me grape tits yesterday."

Dave grimaced. Yes Zoe did have very small breasts but you would expect a college student to be a bit less childish. "Zoe, anyone who would say anything that stupid should be ignored."

Zoe smiled a little, "That is a really dumb thing to say." She wiped her eyes and laughed a little "Oh god, I am so bad at this, you should see the completely ridiculous underwear I put on for this!"

Professor Jennings felt a slight stir in his pants at that comment. "Oh I am sure anything would look wonderful on you."

"Oh it's so cliche professor you would laugh at me, they are black and go around my hips but there is nothing in the front because I thought it would be sexy to be able to leave them on... Oh and this bow on top." Zoe was smiling again now.

Dave was glad she wasn't crying anymore but he was also now realizing what he had passed up. "OK so ummmm what will you do for rent?"

"Oh I guess I can ask my brother, I'll pay him back after I get a job during break. I won't have any money going into next semester but who knows, maybe Alison will give me a lesson so I don't come off like a blithering idiot with another guy." Zoe finished collecting her thing. "Again I'm sorry professor, this was terrible of me."

As she stopped talking Zoe bent over to pick up her bag. Knowing what was under those jeans covering her exquisite ass, Dave was suddenly feeling a bit generous.

"Well, let me at least give you what you paid for the ummmm panties, or underwear or whatever." Dave offered.

"Oh that's sweet of you... They were sixty dollars."

Dave was shocked "I'm sorry, sixty for one pair?"

"They are really fancy..."Zoe smiled at him, "You want to see them don't you?" She teased.

"I mean... I do not think I have ever seen anything that expensive."

Zoe smiled and slid her her skirt down her hips, just enough to show the top of the black bow. Dave could also see her tight stomach, she had a small birthmark on her right hip.

"I don't want any money from you professor, but just tell me, would a guy like these, or should I get a different kind?" And with that she slid her jeans further down, clearly just above where the missing crotch would show her pussy.

Dave wanted so badly to see what was just below the top of that denim. "So your for sure going to do this Zoe?" He figured that if she was really going to try to get paid for sex it really might be the right thing to do to be her first.

His wife's voice reappeared in his head "Well that's maybe a bit convenient for you isn't it hon?"

"If I can Professor- I really don't want to owe my brother anymore money, and my parents didn't want me to live off campus anyways."

"And ummm how much do you need?" Dave asked, adjusting his now hard cock below his desk.

"I need two hundred."

Dave has been walking around with at least four hundred in cash just in case Alison had gotten in touch with him and he could get together with her right away.

Dave took out his wallet and put two one hundred dollar bills and three twenties on his desk. "Here, I want to help you with your rent and I feel bad about the panties so take this."

Zoe smiled "Oh Professor! I'm so happy! What do you want to do first? And do you want to do it here or go somewhere else?"

Dave wanted to fuck her so badly.

"Be a good guy and offer one more time hon, and if she doesn't take it then you can have your way with her and not feel bad." His wife told him. She always knew what to do in any social situation.

"Zoe, you don't have to do anything. Just take it." Dave tried to sound sincere but prayed she would refuse.

"Oh no Professor! I don't want a favor, I should earn what I get." Zoe said, maybe a little more confidently then he expected her to be.

"Ok go get her." Teresa said, even though she was just in Dave's head he still loved her sense of adventure.

"Ok Zoe, I won't argue. How do you think we should begin?"

Zoe pauses, she hadn't planned that part. "Ummmm, should I take my clothes off?"

Dave nodded and Zoe unzipped her Northface jacket and pulled off the light sweater that was underneath it. She had on no bra and her breasts were tiny but her nipples pointed directly at Dave. She looked at him as she put her arms to her sides, she shivered a little.

"Zoe we can stop if you want, the money is yours."

Zoe didn't reply but he saw her swallow.

"Let me guess, you hope that's not the last swallowing she's going to do today right?" His wife mocked him. That is the kind of joke he would have made to her.

Dave finally got a full view of those panties. She looked spectacular, just like Alison her pussy was shaved bare and her tight little lips looked delicious.

Dave was ready, "Come sit on my desk Zoe." He said taking control.

She seemed realized to be told what to do, and she pearched herself on his desk, her feet resting on the arms of his chair.

Dave hadn't tasted a woman in years, and his first small lick of her cunt didn't disappoint. He worked his tongue in and along her folds, enjoying her body as much as the small noises she made as he did so.