The next few days, Bill wracked his brain, trying to figure out how he was going to “work for it.” He decided he would send her flowers to her apartment. It was a Thursday and she was not subbing that day. Olivia got her flowers and read the note with them:
‘Not sure what I’m doing or why, but I’m giving it a shot. Will’
Olivia smiled. She took a picture and sent it to him saying ‘It’s a good start. ;)’
Bill read his text and gave a small smile.
‘Btw. I like the nickname.’
During Thanksgiving break, Bill texted her.
‘I’m going to a conference next week in the cities. Would you like to come?’ he asked.
‘But the school is paying for it and there will be other administrators there,’ texted Olivia. ‘Isn’t it kind of risky?’
‘Yeah, but there’s no other admin from our school and no one will know you’re here with me.’ he replied.
‘Am I going to be hiding out in the room?’ asked Olivia.
‘No….you don’t have to.’
‘Are you sure it’s not too risky for the first time?’
‘Maybe. But I think it’ll be fine.’
Olivia sighed.
‘Ok.’
The next Friday morning, Bill picked her up at 7 am and drove to the cities. After they were driving for 30 minutes, Bill finally broke the silence.
“I know it’s not the ideal situation, but I’ll have to drop you off somewhere while I’m at the conference today and then I’ll pick you up when we can check in,” he said. Olivia gave a small smile; this is exactly how she thought it would go. Bill saw the look on her face. “I’m sorry. I didn’t quite think that part through.”
“I don’t think you’re thinking any part of this through,” said Olivia, looking at him. He swallowed. “But, we’ll see what happens.”
Olivia had Bill drop her off at the mall. It had a large bookstore that she would spend her time in while he was gone. She found a comfy corner and read a book. At 3pm Bill texted her saying he would be there shortly to pick her up. They went to the hotel and Bill went in to check in. He texted Olivia when he was upstairs that it was clear for her to come up. He let her in and took her bag from her, tossing it aside. He went in to kiss her, but she put a finger to his lips.
“Ah, ah, ah,” she said. “I told you you were going to have to work for it.”
She smiled at him.
“What would you like me to do?” he asked, trying to hide his impatience. Olivia knew it was driving him nuts, but she loved playing the game.
“How about dinner?” she asked sweetly. Bill smiled.
“Ok,” he said. He found a place a little further away from the hotel, hoping he wouldn’t run into anyone from the conference that he knew.
As they sat at dinner, Olivia asked, “What exactly do you want from this, Will?”
Bill smiled to himself that she used his other nickname. A nickname only she used.
“I don’t know,” he said. “We’ll see where it goes….how guilty I feel.”
“Do you feel guilty now?” asked Olivia. She was unsure if she wanted him to say yes and they wouldn’t do anything, or no and she’d be able to fulfill a fantasy. Bill swallowed.
“Maybe, a little,” he said. “I don’t know. I don’t know if it’s guilt or nerves or what.”
Olivia removed her shoe and ran her foot up his calf. She could see his ears start to flush.
‘Such a flirt,’ thought Bill. They ate and shared a desert and soon left. On the drive back, Olivia let her hand wander across the center console and rest on his thigh. She leaned over and whispered, “What do you want to do tonight?”
Bill sighed, gripping the steering wheel tighter as she started rubbing his thigh. She got closer and closer to his member, but never touched him. Olivia smiled, loving the effect she had on him. They got back to the hotel and quickly made their way to their room, making sure no one saw them. The door clicked behind them and Olivia flipped the lever. She removed her shoes and sat on the edge of the bed and Bill followed.
He kissed her forcefully, pushing her down on the bed and kissing her neck. Olivia made him look at her.
“Slow down,” she said. “Earn it.”
“I don’t even know what you mean,” whined Bill.
“I know you want to have sex,” she said, “you haven’t had it in years. But what about what I want? There’s two people to this you know.”
Bill smirked. He knew exactly how to get back at her for teasing him so much. He took his shirt off and had Olivia strip down.
“Lay on the bed,” he requested, as he took in her naked beauty. She was short, 24 years old with a little extra weight around her belly. She had scars, stretch marks, fat dimples, but he had never found anyone more beautiful. Not even his wife of 16 years.
He started rubbing her feet and then slowly worked his way up her legs to her thighs. Olivia closed her eyes, enjoying the relaxation. Bill crawled between her legs and kissed her. She kissed back as she undid his pants and started pushing them down. Bill removed them and returned to kissing her. He kissed her chest, laying gentle kisses on her breasts, lingering at her nipples. He licked them and she gasped as he sucked her left one, his tongue making circles around it. He smiled knowing he had this much control over her. He did the same to her right one.
Olivia ran her hand down his thigh, trying to reach for his member, but he was too far away. Bill smiled. He kissed her lips as he let a finger gently stroke her dripping lips. Olivia gasped. Bill let another finger join as they massaged her vulva. He ran them up and down in her sweet, sticky juice, almost reaching her clit, but never touching it. He laid next to her, propping himself up to watch her squirm as played. He finally touched her clit. The buildup of excitement made her arch her back as she moaned.
Olivia ran her fingers down his thigh, scratching as he pleased her. She opened her eyes and her excitement grew as she saw the girth of his cock. She reached out and touched it, sending a jolt of excitement through Bill. She began stroking him as he rubbed her. Olivia sucked in sharply as he inserted a finger; she tightened her grip on him.
“Oh, Will,” she cooed. He began pumping rhythmically, building so much pleasure she could no longer stroke him. Her heart beat furiously. Bill kept going until he felt her tighten around his finger. “Oooooohhhhh.”
Source: reddit.com/r/eroticliterature/comments/gjts6e/whats_my_job_2_affair