Until You Cry

I used to imagine how hard a spanking might have to be to get me to cry.
 I remember the things I used to fantasize about when I was a young teen. It must have been some kind of spin-off from feelings I had as a small child. I hope no one freaks that I'm going here, but I want to be able to go anywhere when it comes to thinking about spanking. I was a good kid, and discipline didn't happen often. (And I would say it often happened when it shouldn't have, and didn't happen when it should have.) However, I knew the secret---cry soon, cry hard, cry loud. It makes the person stop a ton sooner everytime.
In my fantasies, however, I'd tell the man about to discipline me, "I'm not going to cry."
And he'd say, "That's perfectly fine. You don't have to."
It was always like this in my head, in the stories I'd make up in my mind. And in those stories, she (I) would always end up crying. But not because it was a must.
I cried with College Guy the second time I met up with him.
 My vanilla ex had recently been trying to get back together with me, and my emotions were all over the place.
There was a punishment spanking we had planned. I remember being sorry for the thing I had done. It was something that had caused undue stress to College Guy and something that had been irresponsible--I had not answered my phone for hours and hours knowing full well that I had agreed to talk to him, and that I had just flown back to college and he would want to know if I'd arrived safely.
The punishment spanking didn't make me cry though. I told him, "If I cry, it's because I'm so tired and stressed. It's not because of the spanking."
Afterwards, I told him I was worried about hurting him. I was afraid he was getting too close, falling in love with me.
He told me that I was a great friend and person. That I don't hurt my friends, at least not often. I was lolling on the hotel bed with just a hoodie and boy-short panties on.
" I don't think I'm a good person." I mumbled, running my fingertips in little circles on the bedspread.
"Do you want me to put you back over my knee?" He  threatened warmly.
I looked down and mumbled, "No...I mean..No, I'm not a good person." It was my story and I was sticking to it.
"Get over."
"What? Nooooo.." I grumbled as he grabbed my arm and dragged me over his lap, his back propped up against the headboard.
Between smacks, he asked me, "So, how are you a bad person?"
I hemmed and hawed. "Uhh..it's really just a feeling. I don't know. Ow. You already spanked me..."
He slapped each cheek harder and harder. Then paused, "For someone who keeps saying, 'I'm a bad person', you really don't have much to defend yourself with."
He spanked. He lectured. And I argued right back.
"Alright," he said. "Get up for a minute." He stalked off to his backpack and returned with Gepetto, the bath brush.
"No, no, no, you already used that on me." I whined.
He stretched out on the bed and patted his lap. "Now, Bonnie-jo."
I placed myself resignedly over him.
"I'm going to spank you until you cry, okay?"
But the question was not directed at me. It sounded like he was thinking out loud to himself.  But I put in my two cents anyway.
"No, no no! Please. You know I can't cry. Besides..ahhghghgh...no! I'm just depressed right now. About my ex and all. I know how to deal with this stuff. When I'm depressed, I have to distract myself until it passes. You can't fix it."
"I'm going to spank you to tears."
And then he started.
College Guy is right-handed, and yet I was positioned in the opposite direction over his lap. Not my fault. He'd pulled me there. And yet, that bath brush hurt unbelievably. If a bath brush spanks well with the weak hand/arm, you know you've got yourself a bath bruth that needs to get lost somehow. Or to be used as some kind of ceremonial incense.
I still had my hoodie on. But then it somehow came off. I must have been flailing about a bit. So now I only had on a black bra. At one point he asked me one of those "Yes, Sir" type of questions. I responded with an angry-as-I-could-make-it "Yes!!"
"Is that hostility in your voice?" He unecessarily asked.
Then he promptly undid my bra and slipped it off my shoulders. I had never been completely naked in his prescence before. "Noo..." I begged. But I didn't try to struggle.  It made me feel smaller, more vulnerable. And I lay still, as he smacked and smacked and talked and talked. I argued back at times, but I didn't feel like arguing as much as it progressed. It seemed like it would never end.
The smacks were very slow though. Hard. But slow.
He kept spanking and checking my face for tears. Spank, spank, spank...and then he would incline his head to the side to catch a glimpse of my face. Kind of adorably attentive now that I look back at it....
At one point, I began to struggle really hard again. It was the worst of the storm before the calm. He stopped the bathbrush, and I stopped the struggling. Had I won?
Then, "You are a good person, Bonnie-jo." Smack! "This is a two -way street." Smack! "You don't have to be perfect here." Smack! "It's about trust. It's about trusting your friends with the friendship you offer. You can trust your friends--"
And I lost it. It was because he said the things about trusting. I think that trust is one of the most baffling things about relationships. You're supposed to do it with God. And I never could much. You're supposed to do it with your friends. And I don't especially.
I began to sob deeply, but almost silently.
He spanked a little more. That helped me stop crying. It was a nice distraction from the tears.
And then it was over. I rolled off his lap and curled up in a little ball. And just breathed. He held me for a bit.
And, it didn't fix things exactly. But I felt better. And excited. We had crossed a boundary in our spanking relationship. It was a first for both of us.