March 8th, 2012
And a special, bonus post, by special request of him, just in case two posts isn’t enough to fulfill your craving this week.
The movie was over, they hadn’t really watched it, too distracted by each other, but they had to go now. They had to get back to her dorm for bed check before midnight. The all-girls, private prep school she attended had very strict rules about being out of bed past curfew. She was eighteen years old, but her parents were not quite ready to let her go to college out in the real world, yet. So they’d sent her here, where she’d met the man of her dreams, and broke every rule to see him.
Heading back to the school, they crossed through a wooded area before the wide open grounds. He grabbed her, wrapping his arms around her waist from behind and kissed her neck. She leaned back against him happily. They had a few minutes before they had to be back, she decided.
“You’re such a bad girl.” He breathed into her ear.
“Yes, sir.” She smiled at his mock stern tone.
“Wandering through the woods at this time of night. Good girls are all in bed. But you’re out with a man in the forest.”
“You know what we do with naughty girls, don’t you?”
“Yes, sir.” She shivered as his belt slid free.
He turned and put left foot up on a fallen tree and bent her over his knee. Pulling up her skirt, and down her panties, he exposed her bare ass. Stroking it with his folded belt, he put his hand on her back to hold her steady. Then brought the belt to bear.
She yelped, and he swung again. Her yelping soon turned to moans of pleasure as she writhed over his leg. He reddened her pale skin, with harder and harder strokes. Until she began to beg.
“Please, oh please, sir.”
“Please, I want you.”
“Please, sir, please.”
He stopped and let her go, she dropped to her knees in front of him. Pulled his pants open the rest of the way and eagerly took him in her mouth. He gasped and entwined his fingers in her hair, guiding her eagerness. She moaned as he groaned, and when they were done, he pulled her to her feet, and held her tight.
After a moment to breathe, they were off again, racing towards the dorm, and up the fire escape to here room. Her roommate was in the infirmary for the night, so they had it all to themselves. She shooed him under the bed until bed check came through a few minutes later, and then pulled him back up. Collapsing on the bed, he pulled her close.
“Such a bad girl, pulling a man’s pants down out in the open like that.”
“Yes, sir.” She expected him to be sleepy, but he seemed far from it.
“And now, you’ve snuck him into your bedroom, into a girls only dorm.”
He sat up and pulled her over his lap, keeping her skirt down to muffle the noise, he took his hand to her this time. Spanking the already tender flesh. She buried her face in the blankets to cover her moans. She squirmed against his lap, but he held her tight, spanking her tender bottom until her moans got so loud, the blankets could not stop them.
“Please, sir, oh gods, please sir.”
“Please, take me, sir.”
He gave her a few more swats that nearly made her scream before flipping her around and back onto the bed, shedding his clothes and then pulling her free of hers. He joined her back in bed and covered her mouth with his to keep her moans of pleasure from waking her dorm mates while he rode her to exhaustion.
The alarm went off early the next morning and she shooed him under the bed again for morning check. Then she got ready and went down to breakfast. He snuck out the window while everyone was eating and she spent the rest of the day in a happy haze. Until the end of her last class, when the teacher stopped her.
“Headmaster wants to see you. Come with me.”
He led her towards the dorm, however and up to her room, where she saw the headmaster waiting. The hairs on the back of her neck stood on end, and she dreaded what was to come. He must have been seen leaving.
“Come in. Tell me, is anything amiss?”
“Is anything missing? Anything at all?”
“No, headmaster.” She knew better than to lie. If she said yes, her boyfriend would be arrested for theft.
“Strange. A man was seen climbing out of this window this morning, during breakfast. We assumed he was a thief. Are you sure that nothing is missing?”
“Did you know the man who left here this morning?”
“I see. And did you know he was in your room?”
“Would you mind telling me what he was doing here?”
“Yes, headmaster.” She blushed furiously and glanced at the teacher in the doorway.
“Thank you, that will be all.” The headmaster dismissed the teacher and closed the door before turning back to her. “What was he doing here?”
She stared at his shoes, too embarrassed to answer.
“We could continue this conversation in my office, with a cane, if you would prefer?”
“No, headmaster. I.. I invited him up, headmaster. We had a date last night and I brought him back here.”
“I see. Tell me about it.”
“We… we went to the movies, and then we came back here to sleep.”
“Is that all? You saw a movie and you slept?”
“We… um… on the way back, he put me over his knee and spanked me with his belt and I went down on him. After bed check, he spanked me again, with his hand, and then we had sex before we went to sleep.”
“I see. You like that do you?”
“Yes, headmaster.” She was mortified, but lying would only make things worse.
“But you chose to continue the conversation here and not in my office with the cane?”
“Yes, sir. I don’t really like canes, sir.”
“I see. Well, let’s see how he did, then. Turn around and show me your bottom.”
What could she do, she turned around, bent over and lifted her skirt and pulled down her panties.
“It’s barely red at all. He must not have tried very hard.” The headmaster patted her bare ass. “I’ll have to see what I can do about that. Don’t you think?”
“By rights, you should be expelled and a letter sent home to your parents.”
“But that won’t do anyone any good, so how about this. You’ll march down to my office with me, and I’ll redden that ass of yours properly, you can even thank me for it, like you did him in the woods. And once I’m satisfied, we’ll forget this ever happened. Is that alright with you?”
“Go on then.” He pulled her up and opened the door, motioning her to go ahead of him.
She walked down the hallways, her face bright red and her eyes on the floor. Those she passed knew she had been caught out, but very few of them knew what for. When they got to his office she went inside. He followed and locked the door behind him. Walking to his desk, he pulled off his belt and put it on the left side, then pulled out a paddle and put it in the middle and then a cane on the right hand side.
“You’ve been a very naughty girl.” He told her and sat down, motioning her over. “Take off that skirt, it will only be in the way, and the panties.”
She did as he instructed and then he pulled her over his lap. He started with his bare hand, spanking her equally bare ass.
“This is for sneaking out last night.”
He started out soft and built up, harder and harder. Gauging her moans and squeals, occasionally checking to see how wet she was. She squirmed on his lap, embarrassed but increasingly aroused. He spanked her harder and harder until she was gasping and screaming for him.
“Please, headmaster, please!”
“Please, stop and let me thank you.” She begged, remembering his words.
He gave her a few more swats and then let her up. She dropped to her knees under his desk and fumbled his pants open. His erection was waiting. She took him eagerly, and he let her, fingers in her hair, but stopped her short of finishing him off and pulled her roughly back over his lap.
He picked up the belt next, but paused, giving them both a few moments to breathe.
“This is for having oral sex in the school forest.”
He swatted her ass with the belt, pulling a gasp, and then another. He beat her already red ass into a deeper shade of crimson. She moaned and writhed harder against him, but he held her tight. His strokes slower than the first spanking. Enjoying the fullness of her reaction. When he had her screaming again and begging, he let her up a second time. And she sunk to the floor, moaning against his cock as she sucked on him.
He only gave her a few minutes this time before pulling her back up and picking up the paddle.
“This is for sneaking a boy into the dorm.”
He struck hard and firm, leaving it against her ass as she cried out. He smiled down at her. Loving the sound of the paddle the most. He struck again, and again. She arched and cried and tried to get away. Her ass sore and bruised already. He counted down from ten, and she screamed with each one. Then he dragged her to her feet and bent her over the desk, picking up the cane.
“And this is for having sex in your dorm room.”
He took the cane to the back of her thighs and her highly abused ass. Counting down from twenty, he held her in place by her hair. Giving her time to process each strike. Screaming into the desk and stamping her feet. She cried as she dug her fingers into the wooden edge.
When he was done, he pulled her back down to the floor beneath his desk and she took him a third time, this time to completion. And then collapsed into a puddle on the floor. He redid his pants, put away his tools and let her come back to herself before sending her back to her room.
“Next time you want a spanking, just ask.” He said as he opened the door and sent her on her way.
January 6th, 2011
Describe your weirdest/most interesting sexual fantasy.
I had a lot of trouble with the words “weird” and “most interesting” while considering this question. Thought about a variety of angles and scenes and potential fantasies. Discarded some for not being all that weird after all. Discarded others for having been written about before. Wondered what would be “most” interesting of all the thoughts in my head. Then I remembered my Monday post. It seems these first few are building on each other.
My best friends and I used to look at each other randomly and pose the question “Jack or Spot?” In fact, a few weeks back, I got that in a text from one of them for no apparent reason. My answer was always Spot. Spot Conlon, head of the Brooklyn newsies, in Disney’s live action musical about the newsboys strike of 1899. Shorter than Jack, more wiry, but tougher and more feared than any other newsie in the city. And those eyes, clear and sharp.
So, my weirdest fantasy that still persists to this day? Being Spot Conlon’s girlfriend come submissive. I didn’t know the latter term when I was young, but all the fantasies hinted at that type of interaction. A look from him and I would immediately still, unable to move under his gaze. A pointed finger and I would stand where he directed. Any order, I would immediately follow. If I did something wrong, he’d put me over his knee right there on the docks in front of everyone. Spanking me by hand, with a belt or with his cane until I sobbed. As I grew up, the fantasies turned more sexual. He’d take me off the dock, to a private room in the back of a warehouse to put me over his knee, so he could toss me down and fuck me afterward. Even then, we tended to have an audience, a few newsies would follow to listen and make sure I was being punished.
Perhaps the weirdest part of the fantasy when I was younger, I’d incorporate Star Trek, the newsies either being a holodeck program, or a favor from Q, taking me back in time.