Will wrote a list of emergency numbers on the chalk board in the kitchen for the babysitter and left her to watch TV, the kids already being asleep. She was a definite cutie before, and since she had come back from college, a big flirt.
Madi often teased him by dressing provocatively. She knew that Will thought she was attractive, and that he must have had a crush on her.
That night, Will came back from poker night very late ... about 2am. The house was dark, and the babysitter had changed from her baggy shorts and shirt into something / someone else! As she stood up, she put down a drink ... she had obviously taken liberties with the liquor cabinet.
She was wearing a black leather mini-skirt, red pumps with about a three inch heel, no stockings, and a white blouse with only the bottom three buttons done, revealing her red push-up bra. Will knew she liked to dress up to tease, but this was the hottest he'd ever seen her.
She put her hands up to have Will stop where he was. She held him at arm's length and asked if he was worthy enough to kiss her.
The way she was dressed had him hard as a rock. "What do I need to do to become worthy?" he asked.
A slow smile crossed her lips. "Move the big arm chair into the kitchen, undress, and then sit in the chair," she commanded.
"Will you help?"
"Do it _now_!"
Will could picture himself pulling her panties off and taking her right there on the table, still mostly dressed. Lust had the better of his brain, so he complied. He carried the big over stuffed armchair into the kitchen ... away from the front window.
He unbuttoned his shirt and slipped it off his shoulders and dropped it on the floor next to the chair. Will was already barefoot, so he made ready to remove his pants.
"Are you sure you're ready for this?" Will joked and slid his zipper down.
She didn't reply, Madi just rolled her eyes. Shrugging, Will dropped his pants, stepped out of them, and stood there in his briefs. The top half of his circumcised cock was peeking out the top of his briefs. Will longed to grab her by the shoulders and pull her head to his crotch, forcing himself into her mouth and thrusting between her lips, shooting his cum down her throat. Just the thought caused him to twitch, and a drop of pre-cum formed on the tip.
Ignoring his painful lust, "Drop 'em and sit," Madi commanded.
Will had just about enough, but his lust was still more than I could think through. He dropped his briefs, and while he was bending over to unhook his foot....SMACK. She had given Will's ass a mighty whack.
He lost his balance and grabbed onto the chair, sitting heavily. The babysitter stood in front of him, slowly licking her lips. "I'm going to tie you to that chair and then give you the fucking of your life."
The smack was forgotten as my cock lurched again, and his hands found their own way over the huge arms of the large chair. She tied him tight enough and well enough to prevent escape, but still had circulation. Letting her hair tease his cock, she leaned over and tied Will's ankles to the legs of the chair. She checked the ropes on last time, went to the table, and grabbed her purse.
"I knew I could humiliate you," she said. "I just didn't think it would be this easy."
She then walked down the hallway to the bathroom and closed the door. A few minutes later, she returned ... back in her normal clothes.
"I told you that you would be fucked tonight," she grinned and walked out.
Will sat there stunned for a moment, then tried to work himself loose. His erection had faded with desperation.
"What if someone finds me like this?" Will asked myself. That thought caused him to work even harder at getting loose. The more he struggled, the worse he felt. There was no way Will could get himself untied.
He was stuck, and even worse, someone was here already! Will heard the clip-clop of feet on the walkway, the click of the door. The door opened, then shut. Madi walked into the kitchen with her mother.
"Oh Will, you are sooooo busted," said Madi's mother.
"Mom!" Madi squealed. "See what I have to put with! He's always leering at me!"
"Yes, I know, Madi," June said. She was faced with an interesting situation, one that could play out in all sorts of ways. She was already envisioning one way, a way she hadn't been able to explore for some time, but which pleased her enormously.
She turned to her daughter.
"Madi, I think I can come up with a punishment that will guarantee that Will will only treat you with respect from now on it. In fact, when we're done with Will, he'll take you to the mall whenever you want, do your chores around the house and probably even do your laundry for you."
Madi was goggle-eyed. Everything was happening so fast, setting up her pervert neighbor, then hearing all of this from her mom. The attention he gave her wasn't so bad ... he was kind of hottie, even if he was twice her age. Could she really punish Will so that he would be her slave?
As the thought crossed her mind, her pussy gave a tiny spasm that made her flinch, and she realized she was turned on by the thought of punishing her big neighbor, of making him hurt, or whatever June had in mind.
"Let's do it, mom! Let's punish him!" Madi was astonished at the enthusiasm - blood-lust even - in her own voice.
His babysitter's eyes were glowing like some little girl possessed by Satan in a horror movie, and his was making threats that sounded pretty heavy, and he was trapped, with no way out.
"OK, I'll take my punishment," he said meekly.
"Very good," said June, and her eyes glistened. "Now, what happens here next stays among the three of us. We don't tell anyone, we don't tell friends. This is discipline, and I am the disciplinarian, and that's my rule. Got it you two?"
Will and Madi both nodded. Will was starting to get sick with fear, and to his puzzlement, his cock was stirring again, starting to get hard. Madi's heart was beating faster and her palms were itchy.
"First, I want you to tell us both, have you ever masturbated thinking of Madi?" June asked.
"Uhhh, um, you know, I, uh...." Will trailed off, deeply humiliated. He stared at his lap.
"Not a good start," June snapped.
"OK!" Will shouted. "Yes. I do! I love jacking off thinking of her, alright?"
"Tell me the fantasy right this second."
"OK, I was pretending that I was in the shower with Madi, and she'd given me her sweaty underpants, and then she was uh, uh, uh sucking me."
Madi was shocked! Shocked and turned on, she realized. Why would she get turned on by her neighbor's fantasy about her, she wondered.
June turned to Madi. "You and I need to talk briefly in private," she said. "Come with me."
Will was left to wonder what June had in store for him.
In the hallway, June was outlining just that.
"Now Madi, Will's punishment is going to be very rough, brutal even. But I don't want you to shrink away. I want you to participate. If you just stand and watch, then when I leave, Will will only associate the punishment with me. But if you punish Will along with me, he'll be putty in your hands from now on. Now will you go along with me?"
"Yes, mom," the 18-year-old beauty answered, enthralled with her and the sense of power that was building between them.
"Now there are two ways to control men," she explained. "First, you can be a cock tease. I know you've heard the term. It means getting a boy all excited, but then not letting him have an orgasm, so that he gets very frustrated."
"And the second way to control a man is through causing him pain? Can you help me with this?"
Madi swallowed. God, she didn't know what to say. She'd never even considered it. But then suddenly she did know what to say. "You bet I can!"
"Oh my goodness, Madi, you are one fast little learner." The mature woman and the teenager looked at one another, and perfect understanding passed between them.
"I'll be in charge of the teasing," June said, "and you can watch. If you feel like you want to get in on the fun, I'll let you. You can be in charge of the pain, and I'll supervise."
"I feel strange, kinda turned on," Madi said.
"I'll bet you do, honey. And you ain't felt nothin' yet. OK, take off your bra so he can see your nipples through your t-shirt. Time to tease!"