Helping Her 2: Dress-up (M/F story)

Sequel to Helping Her.

I couldn't contain my smile as my phone rang, and I saw that it was Mary on the other end of the line. It was a few months since Mary, my best friend's gorgeous big sister, had asked me to take her over my knee and give her a good spanking. I'll admit, it was a weird idea, but I found myself enjoying it more than I would have thought possible. Since then, Mary had gone back to college, living in a small apartment she rented. In one way, this was good; since there were no parents or siblings around, she could spend the entire day getting her bottom smacked without anyone barging in on us.

 

On the other hand, Mary's college was an hour or two away by bus, meaning that we could only see each other at weekends. I spent most weekends at her place now, counting the seconds between each visit.

 

"Hey Rick, that order I placed online finally arrived," she told me.

 

"Going to tell me what it is?" I asked. She told me two weeks ago that she'd ordered something online, but she refused to tell me what. I'd threatened to spank it out of her, and she'd told me that would be fruitless, but I was welcome to try.

 

"Let me put it this way: Have you ever wanted to paddle a cheerleader?"

 

To tell you the truth, I had never given it a moment's consideration before. Yes, I know, not much of a spanko, am I? Well, I'm knew to all this. "I do now," I told her.

 

"Well, make sure you get on that bus this weekend, and I'll see what I can do."

 

She hung up, without as much as a 'goodbye'. She referred to this as 'bratting for a spanking'. Well, I was going to do my very best to oblige.

It was about six in the evening as I stepped off the bus. It was September, but still quite warm, a lovely Friday evening, and in a short while, my girlfriend was going to hand me a paddle and ask me to give her bottom a good one. Life was good.

 

She'd told me she wouldn't be answering the door, and as I entered the apartment, I saw why. She was standing in the corner, hands at her sides, with the skirt of her uniform flipped up to reveal a pair of light blue panties. I was pretty sure that the uniform wasn't standard; both skirt and shirt was a lot shorter than usual. But I wasn't complaining.

 

On a table nearby, the paddle was waiting for me. I picked it up, patting it against my palm, watching Mary squirm in the corner at the very sound. It was about two feet long, and solid wood. Quite intimidating. It looked quite professional, too. I realized that it was something of a commitment for Mary. Not to me, specifically, but to her new lifestyle. There was something obvious about it. Until now, we'd only used hairbrushes, ping-pong paddles, wooden spoons – things that can be explained away if they're left lying around. A paddle like this? There's only one use for it. I had a feeling she would keep it very well hidden.

 

There were also a couple of magazines on the table, so I sat down. She'd done this before; if she waited for me in the corner, with a couple of magazines there, that meant 'Leave me in the corner for as long as you wish'. And she was considerate enough to make the waiting easier for me. I thumbed through the magazines, but to be honest, there was something a lot more visually appealing in the room, so my concentration was elsewhere.

 

Quite frankly, I never understood her. I never understood why she enjoyed standing in the corner, showing off her panties, knowing that I was sitting here, waiting with a paddle to beat her bottom red and sore. I never understood that. But then again, I didn't need to. She had that desire, and I fulfilled it. It was simple.

 

I checked my watch. About fifteen minutes since I'd entered. I wondered how long she'd been in the corner before I'd arrived. I decided it was time to begin. I picked up the paddle, tapping it against my palm in an effort to be intimidating. I had a feeling I wasn't very good at it.

 

"Mary, come here."

 

She stood in front of me, wringing her hands, staring at the floor. She looked so vulnerable, so beautiful. I wanted to embrace, to hug her, to feel her lips against mine. But there would be time for that later. There were other matters to attend to, first.

 

"You know what's going to happen, don't you, Mary?" I said. I felt I'd gotten quite good at these lectures over time.

 

"I.. I'm going to get a paddling, sir," she said quietly.

 

"That's right. And why are you being paddled, Mary?" It was something of an unwritten rule that whenever we did scenes like this one, Mary always chose the reason for the punishment. She was a lot better at it than I was.

 

"I cheated on my test, sir." Pretty standard; I'd punished her for that more than once before. But the costume and the paddle somehow made it all more real.

 

"I think it's time we begin, Mary. Bend over and grab your ankles."

 

She did as instructed, and I raised her skirt. I decided to leave the panties in place; they fit the scene.

 

"Mary, I'm going to give you twelve strokes of the paddle, to teach you not to cheat. I want you to count them out loud. If you forget to count, or get out of position, the stroke will not count. Is that understood?"

 

"Yes, sir." I could tell by her voice that she was enjoying this even more than I was. She'd told me that I'd gotten better at this 'strict disciplinarian' act I had going on. Well, I did my best.

 

I raised the paddle, patting it against her rear, enjoying the sight as her cheeks quivered in anticipation. The paddle was thick. I had a feeling it was going to cause her a bit of pain. Good. She wouldn't enjoy it otherwise.

 

SMACK! The first stroke landed, and she cried out. "One, sir." I smiled; the paddle seemed to have more of an effect than she had anticipated.

 

SMACK! "Two, sir." She squirmed around, causing her bottom to wriggle around quite invitingly, but stayed in position.

 

SMACK! "Three, sir." She was a lot less enthusiastic now than before the punishment. She'd realized just what she was in for, I expect, and it was a great deal more than she had anticipated.

 

SMACK! "Four, sir." I kept on paddling her; she'd never forgive me if I called it off now. She'd told me more than once, that if she wanted the punishment to end, she'd use the safe word. That was what it was for.

 

SMACK! "Five, sir." Tears were rolling down her cheeks, and her voice was quivering slightly.

 

SMACK! "Six, sir." Through her panties, I could tell that her bottom was turning quite red. And we were only half done. I frowned. She was going to have some trouble sitting tomorrow.

 

SMACK! "Seven, sir." She was curling her toes, whimpering slightly.

 

SMACK! "Eight, sir." By now, she was digging her fingers into her knees, trying with all her might to stay in position.

 

SMACK! It didn't work. She jumped to her feet, both hands clutching her bottom as if she was afraid it would fall off.

 

"Bend over, Mary. That stroke did not count."

 

SMACK! She was sobbing loudly. "N-nine sir."

 

SMACK! "T-ten, sir." I felt brutal, causing her pain like this, causing her to cry. The only thing that kept me going, was knowing how much she enjoyed it.

 

SMACK! "Eleven, sir." She was grasping her ankles tightly again, trying to stay in position.

 

SMACK! "Twelve, sir." The relief in her voice was obvious. She stayed in position, waiting for me to tell her it was over.

 

"You can get up now," I told her. Her hands flew back as she tried to rub the sting out. She lowered her panties, stepping over to a mirror to assess the damage. Her bottom was red and bruised, and would take some time to heal.

 

"Rick," she said, turning towards me, "If you forgot the cold cream, I will murder you."

 

I considered telling her I had, just to see the look on her face, but decided it would be too cruel. "Of course I have it," I said, getting it from my bag. "Now, get those buns over my lap and I'll take care of it, ok?"

 

She moaned as I rubbed the cream into her bruised cheeks, and I knew she had another desire I would need to fulfil.