SYNOPSIS
When a twenty one year old man bumps into the woman that used to babysit him when he was thirteen, he confesses that he fantasized about her and told his friends she was a MILF. He owns up to the fact that on a few occasions when she fell asleep on the sofa he came into the room to look up her skirt. The older woman gets turned on by the confession and asks if it is still something he dreams of. When he says yes she offers to let him play it out and his fantasies of fucking his MILF babysitter come true.
CHAPTER 1
Sean almost spilled his drink as he turned in the crowded bar and bumped against the woman behind him. He automatically apologized without even looking up as he worked to steady his glass and was about to turn back to his friends when the laughing stopped him.
“Not even going to say hello to me,” the woman said and he took a closer look at her face.
“You have got to be kidding me,” he finally said when recognition struck and he joined in the laughing.
“So you do remember after all,” the woman said.
“Of course I do,” the twenty one year old man answered. “I wouldn’t forget my favorite babysitter now would I. How are you Millie?”
“I’m good,” she replied, “how about you?”
“Yeah I’m doing good too,” Sean answered. “I thought you left town.”
“I did,” Millie went on. “I’m just back to see my family for the weekend and meet up with a few old friends.”
Sean looked down and saw that her glass was almost empty. “Can I get you a drink?” he asked.
“Yeah sure,” the older woman answered. “That would be nice. I’ll have a white wine.”
Sean elbowed his way to the counter and tried to catch the attention of the barman to order the drink. He stood thinking as he waited for it to be served. Millie was his babysitter when he was thirteen and she’d always teased him that he was way too old for a sitter. At that age he was just starting to take an interest in girls and he remembered that even though she was more than ten years older than him, he spent a lot of time fantasizing about Millie. It brought a grin to his face and he felt a quick rush of excitement at the thought, but as the drink was served he shook the images from his mind and returned to hand over the wine.
“Cheers,” Millie said and clinked his glass. Even though they were there with other friends, the two of them spent much of the night chatting about old times. As the alcohol flowed their inhibitions lowered and they started to tease each other. “So anyway…,” Millie suddenly said with a grin. “Did you ever get over your crush on me?”
Sean’s mouth opened wide and he was suddenly a little embarrassed. “I did not have a crush on…” he started, but the words stopped when he saw the expression on Millie’s face and he laughed. “Yeah OK,” he confessed. “But what did you expect. I was thirteen years old and you were cute. Can you blame me for having fantasies?”
“Oh…,” went on the older woman. “So you thought I was cute and it wasn’t just a crush. You were having fantasies about me you dirty little pervert.”
“Well…, I…,” stammered Sean. “Hey c’mon, it was eight years ago. You’re not going to hold it against me are you?”
Millie laughed. “No I won’t hold it against you. So what did you think about doing?”
“What?” he exclaimed. “I can’t tell you that.”
“Did you try to get any sneaky looks at me?” she pressed on and grinned. Sean’s face reddened slightly and the older woman was quick to notice. “You did you little pervert,” she teased. “Tell me.”
“Umm…, well there were some times when you arrived late and seemed to be a little tired. On a couple of occasions you fell asleep on the couch and I kind of looked up your skirt. I told my friends what I did and said that you were my MILF.”
Millie laughed, but Sean noticed that she moved closer so that her arm touched against his. “I wasn’t exactly a mother at the time so could hardly be a MILF.”
“Yeah I know that…,” Sean replied. “Do you have any kids now?” “One daughter,” Millie replied.
“And a husband?” asked Sean.
Millie shook her head. “He’s long gone and I’m single and free again.” “So now you definitely are a MILF,” he teased.
“So little Sean is still having fantasies about his cute babysitter,” said Millie. “It’s a shame you are too old for me to babysit.
Maybe I would fall asleep on the sofa!”
Sean could sense his excitement growing as the flirting continued and he wondered if there was a chance that his fantasies might actually come true. “Well my parents are gone for the weekend so I do have to stay at home all alone.”
“Really?” Millie said and he could hear the interest coming through in her voice. “Maybe I could come and have a look around your house, just for old times sake.”
“Sure, you would be more than welcome,” Sean replied quickly. He could feel his erection coming to life and tried to hold it down. It seemed as if
things were moving towards some fun with an older woman, but he didn’t want to jump the gun in case he was mistaken. He looked down and saw Millie’s almost empty glass. “I was just about to leave,” he went on. “So if you really do want to come just let me know.”
The older woman put her glass down on a nearby table and turned to her friends to tell them she was leaving. Sean did the same and the pair of them headed for the exit to leave. They chatted on the taxi ride to his home, but when they finally stepped out and moved up to the house the tension between them grew. Sean unlocked the door and let them in then led Millie to the lounge. She laughed as she walked in.
“I am pretty sure the wallpaper has changed,” she said, “but the furniture looks the same.”
“It is,” Sean said.
“So this must be the sofa where a little teen pervert was trying to look up my skirt,” she said. “I better make sure I don’t fall asleep.”