The Crush Ch. 03

This is a story about me in high school as it played out in my dreams. Best to read the first two chapters before this to understand the mess Sam (me) has gotten himself into.

Part 7 - Getting real

I sat on the edge of my bed after my first full day in total service and submission to my beautiful classmate, Jackie. After a long tortuous day I had peeled her panties off my butt and washed them with a lot of soap hoping to get all the Capsaicin Cream as she had directed. Her requiring me to slather my ass with that cream kept my bum burning all day. Even with the panties off and me fully showered, my rear remained red, sore and very tender.

I really wasn't sure what was next for me or where this new relationship was heading. I looked over at my backpack on the floor with the panties, ginger, Capsaicin Cream, and KY Jelly that I had been required to purchase. What would Jackie have me do tomorrow? All I knew was that I needed to finish my final required task required by Jackie's, text her a thank you. I texted:

Me: Good night Mistress, thank you for letting me serve you.

Jackie: Good night PB. Are you still wearing my panties?

Me: No Mistress. I just washed them and hung them up to dry.

Jackie: Very good boy. But what are you wearing now?

Me: My gym shorts. I am about to head to bed.

Jackie: NO! No gym shorts. Put on one of the pairs of panties you bought today. You will always sleep in panties from now on.

I got up, pulled off my cotton gym shorts and then went to my backpack. I found one of the pairs of black panties, removed the price tag and pulled them on. I have to admit they felt very good and my penis responded accordingly.

Me: I put on the panties Mistress.

Jackie: First, always refer to them as YOUR panties from now on. Of course unless they are mine, or Hallie's or maybe Ms Sanford's. Just kidding :)

Was she just kidding? My English teacher's panties? I thought.

Jackie: Send me a pic now.

This was a new twist. Now I would be photo documenting this. 'How could that possibly go wrong?' I thought to myself. I sent her a pic of me on the bed in my panties. I am sure she could see the bulge this was creating.

Jackie: Someone seems to be enjoying themselves. That's OK sissy. Just remember, NO cumming.

Me: Yes Mistress.

Jackie: No more of that rough gym fabric against your sensitive little thing. No mens underwear. No gym shorts at night. Understood?

Me: Yes Mistress.

Jackie: From now on the other requirement before you go to sleep each night is to condition your nipples for me.

Me: What?

Jackie: Do you mean 'what mistress?'. Your racking up a lot of negative points here. Don't think I don't remember you calling me a bitch earlier. You will understand the consequences soon.

Me; Yes Mistress. But what about my nipples?

Jackie: A submissive like you should always have very sensitive nipples. Like a girl's. You know, that pop up when you get turned on or cold. Understood?

Me: Yes Mistress.

Jackie: So to condition them, each night before bed you will pinch them very hard, then pull them out and then twist. You will repeat this 50 times. You can take a brief break during this if needed. But alway 50. Understood?

Me: I think I do Mistress.

Jackie: Good boy. Now I will inspect you first thing tomorrow to see how you did. They should be puffy & sore if you did it correctly.

Me; When will you inspect me Mistress?

Jackie: Meet me at 730 behind the gym building over by the dumpsters. You will find a little wooden chair in the little corner area. Sit there and wait for me. Be wearing your panties. Bring the ginger and a small sharp knife. See you then. Sleep well ZZZ. REMEMBER NO CUMMING

Me: Thank you Mistress. What is the knife and ginger for?

No response. I guess she was done with me for the night.

I hadn't really been thinking about cumming with all this crazy stuff going on, but now after Jackie said no cumming it is all I could think about. I slid into bed and lay on my back. I pulled my shirt up exposing my nipples and began the nipple conditioning. At first it seemed like no big deal. I didn't really hurt, just a little sore. When I reached 15 it started to be sore producing what felt like electric shocks every time I twisted at the end.

I had to take a break after 20 reps. After a pause I could do 10 and then rest, 10 and then rest until I finally reached 50. My nipples were very sore and swollen but lightly touching them felt tingly and wonderful and my penis was rock hard tenting my panties. After tossing and turning for a long while staring at the ceiling, wondering about my "inspection" tomorrow I finally drifted off to sleep.

The next morning my alarm jolted me awake from a deep sleep. I bounded out of bed and into the shower. I dressed wearing my second black pair of panties, and hopped on my bike heading to school.

I found the chair in the alcove behind the gym, right where Jackie said it would be. The air was cool leaving a lot of dew on the seat which I wiped off so I wouldn't get my pants soaking wet. I sat staring at the concrete support wall and the grassy knoll right above it running all along the small road in back of the building. It was quiet and peaceful this time of the morning.

"Good morning Panty Boy" came from behind.

I practically jumped off the chair. Jackie had snuck up behind me.

"Good morning Mistress." I said softly.

I turned towards her voice, and she was standing right inches from my face. I was looking straight ahead at the top of her high waisted short red skirt. Tilting my head up I could see the outline of her breasts and nipples against a soft white button down shirt.

"Ready for your inspection and punishment sissy boy?"

"Yes, Mistress. But really I wish you wouldn't call me sissy. That pretty humiliating."

"Oh, poor dear. You are still getting to understand who you are and your role. I predict you will totally embrace 'Sissy' soon. Maybe you'll even beg me to call you that someday. Think so, Siss?".

"No Mistress, I will never want to be called a sissy." I said as firmly as I could given my situation. I started to get up. Jackie put her hand lightly on my shoulder.

"Stay seated for your inspection, now raise your arms."

I slowly raised my arms over my head looking up quizzically at Jackie. She quickly bent down, pulled my tucked in T-shirt up over my head with the collar remaining around my neck. Then she touched my two raised hands with the fabric and said, "Hold it right there".

Now all I could see was my shirt all around me and feel the cool early spring breeze on my chest. Suddenly she grabbed my two nipples pulled and twisted hard.

"Ouch", I yelled without thinking.

"Very good. You did a nice job conditioning for the first time. All red and puffy and sticking out. Good boy. But keep your voice down."

The next thing I felt was Jackie's mouth on my right nipple, warm and soft sucking and tweaking with her tongue. That put me into ecstasy, and I moaned louder than I intended. She moved to the second nipple saying "good little sissy" on the way. Again, ecstasy. She stayed there for a couple of minutes. My entire body was awash in warm pleasure. I could have stayed like that forever. I felt her hand go to my crotch groping around. Then, POW, she suddenly punched my groin.

"Ooooh, what are you doing, Mistress? That hurt." I couldn't see anything through the curtain my shirt created.

"Didn't I tell you never to have a barrier between me and your panties? Your zipper is up. And why didn't you send your morning text thanking me? You really wanted to see how bad a punishment you could earn, didn't you?"

I was frozen. "Didn't you Panty Boy? Answer me!".

Oh boy, I knew this was not going well.

"Mistress, I was distracted. So many things, I didn't sleep well, my nipples hurt, my rear end still hurts a little from yesterday, the panties, the ginger, the knife. I have all those. I just forgot. Please understand Mistress." I was almost crying, and still couldn't see her through my raised shirt. "I will do better, I promise. I promise Mistress." I had really become a blubbering wimp.

"Stand up." she said curtly.

I started to stand and lower my arms to help.

"Keep your arms over your head."

I raised them again and unsteadily slowly stood up.

"Now I want you to take your punishment that you deserve like a man."

"Yes, Mistress."

"Good. Now where is the ginger and the knife."

"In the outer pocket of my backpack Mistress."

I heard her rustling around. "Good boy. I found it. A very nice large piece of ginger. This will work well."

I heard her sit in the chair and then the sound of carving. I guessed it must be the ginger. I stood there for what felt like forever.

"There, all done. Perfect." She said seemingly to herself.

"What's done Mistress?"

"Definitely not you. Now get over here and lay across my lap." She guided me with her hands leading me to lay my pelvis across her firm lucious lap. I felt like I was in heaven for the moment, though I still couldn't see much with my hands now planted on the ground and my shirt still around my head.

"Lift your hips. Yes, just like that.".

I felt her unbuckle my pants carefully with some difficulty given the position. Then she unzipped them and lowered them to my knees gently, almost with a touch of kindness. She patted my panty clad ass and then grabbed the edge of my panties lowering those to my knees as well. She delivered a few quick swats with her hand. I felt very comfortable and natural in this position across her lap.

She then said "This is going to sting a little." I readied for a big smack, but instead I felt her spread my ass cheeks and start to insert something cool and moist in my asshole. It felt rather large and I had never had anything stuck up my ass before, maybe a thermometer when I was a kid.

"Relax Panty Boy, it will be much easier."

I tried to relax as she slowly worked the ginger in my hole, the deeper it went the bigger it felt. She gently caressed my ass to help me relax as she filled my ass with this large piece of ginger.

""You are being a good brave boy. I almost have it all the way in. There, now all the way to the neck. Perfect. That will help it stay in place during your spanking. You definitely do not want to let it pop out. I would be very angry if that happened."

"Yes, Mistress. What is it you are doing? It feels weird."

"It's called 'figging'. It was used back in Elizabethan times to discipline young women caught masturbating. You will start to feel its effects soon. It seems fitting to use it on you, doesn't it?"

"I guess Mistress. But I haven't masturbated since you took control. I have tried to be a good boy."

"I know. I know you have tried. But it is not about trying. It is about succeeding. This punishment will ensure you never accidentally make those mistakes again or you at least will really understand the consequences. Do you agree?"

"Yes, Mistress".

"Good. Now time for your punishment. I do not want you to make a sound. No speaking unless I ask a question. We don't want people popping around the corner do we?"

"No Mistress, definitely not."

"Good boy. We will begin in a few minutes once the ginger begins to take effect"

"How will I know that it is working Mistress?" I ask.

"First, didn't I just tell you not to speak?... don't answer. Of course I told you not to speak. You really want this to be quite a punishment. With the ginger, let me say you will definitely know when it's working."

I lay there and a warm almost vibrating feeling started in my anus. It was tingly and stingy and made me feel full. Also it made me feel a bit like I was peeing. Then it got stronger and stronger and stronger. It became overwhelming, not painful but it felt like it was signaling my body I had been very naughty. I know that sounds stupid but it's hard to explain the feeling. And it made me hard, not in a pleasant way but an out of control way. Jackie must have felt my penis get hard against her lap and said, "Seems to be taking effect Sammy, doesn't it?"

"Yes Mistress." I said almost in an almost sobbing voice. I really felt like I was going to cry.

I felt her shift around in the chair and reach, and then she sat straight up. I felt a cold piece of heavy wood touching the middle of my naked butt.

"This is my favorite wooden hair brush. I call her Monica. Sammy, say hello to Monica."

"Hi Monica. Good to meet you."

"Oh, you and Monica are not going to be friends. She is very mean and will only show up when you need to be punished. But you will be respectful of Monica, always. Now ask Monica to give you the punishment you deserve."

"Please Monica, give me the punishment I deserve."

In a squeaky cartoon voice Jackie said "My pleasure Panty Boy, I love spanking naughty boys" giggling. Back to her normal voice she said, "Monica truly enjoys giving spankings. You have really made Monica's day with your repeated disregard for the rules. This first part of the spanking is for speaking right after I told you NOT to..."

Whap, whap, whap.

Three smacks so hard they made me convulse and yelp. I hoped there wouldn't be too many more of those.

"Stay quiet and still. No moving. Now what do you say to Monica?"

"Thank you Monica for my thorough punishment. Thank you."

"Oh Sammy, we haven't even begun. Now here we go. Remember, stay still and quiet, so you don't make it worse."

Whap

"Now, as I said before, this first part is for speaking right after I told you not to."

With that she unleashed a torrent of hard spanks on my ass with Monica. Soon, it was so painful I stopped really thinking, I was just concentrating with everything all my might to stay still and quiet. After what felt like forever she stopped, but firmly held me in place. We just sat there for a minute as she traced my butt with her fingers so gently. It felt really good. I felt really special.

Then she said, "Next for forgetting to call me Mistress and questioning my orders".

Again the torrent of spanks began again with her strong swimmers arms driving Monica into my ass with the power of a slamming door and the regularity of a metronome. My eyes were now watering uncontrollably and I had to concentrate to breathe regularly. I focused on deep breaths, in and out. I also needed to remember to keep my butt muscles relaxed. When I tightened them instinctively, it made the ginger too much to bear. Then Jackie stopped again and began lovingly massaging my sore ass. Even her light touch hurt, but it still felt good.

I thought, it must be over. I really couldn't take any more.

Then she said, "Now Sammy this will be the real spanking. You know what for? For calling me a bitch. After this next part, you will never want to use that word again for anything."

And she began again only even harder. I hadn't thought that was possible, I was starting to panic, I couldn't take this.

"Please, please, please Mistress stop. Please. I can't take it." I was full on, sobbing and crying now, totally out of my control. "Please."

Jackie stopped.

"Sammy, you know you have this coming. You know it is for your own good. Monica is just getting warmed up. What do you have to say for yourself?"

"Mistress, it hurts so much. I really don't think I can stand any more." I sobbed.

"Now Sammy, didn't I say, you need to take your punishment like a man. That means being strong and taking what you have coming. Can't you do that for me?" she said with a firm voice, not angry just firm.

"But Mistress, I am a sissy, not a man. Please I am a sissy. I can't take this."

"Oh Sammy, are you asking me to call you a sissy?"

"Yes please Mistress. Please call me a sissy. But just make it stop please."

"Sammy, stay still, but let's get your shirt off so I can see your face." She reached down and pulled the shirt collar over my head until the shirt soaked with my tears lay in a clump on the asphalt.

"Sammy, Sammy, you have been crying like a little girl haven't you?"

"Yes Mistress."

"Now look me in the eyes and say, 'I am a weak sissy who wants to be trained to be a good boy by you and serve you."

"Mistress, I am a weak sissy who just wants to be trained and serve you. Now can I get up?".

"Sissy, you just asked me to train you and then you ask me to get up. Really? Sissy's get punished just like real men, but we know they need help. So here is what I am going to do."

She reaches over me and under her skirt, grabs the crotch of her panties, lifts her butt with her athletic legs with me still in her lap, and maneuvers her panties off. They are beautiful pink ones with lace along the top and deeply discolored around the crotch with moisture.

"Here, put these in your mouth like last time so you can keep quiet. No sounds."

I took them from her hand and stuffed them in my mouth. The scent, the taste, were intoxicating.

Bang. She resumed the spanking with Monica delivering blow after blow. At some point I just stopped doing anything but surrendering to the fact that I deserved this and never ever wanting to make those mistakes again. I quietly sobbed waiting for it to end.

Finally she stopped. "Good boy for taking your medicine. I am proud of you, Siss. Now what do you say to Monica?" She pulled the panties from my mouth.

"Thank you for spanking me Monicaa. I deserved it."

She said, "Good boy." as she returned the panties to my mouth.

She patted my ass with her hand and then slowly and carefully removed the ginger. I was throbbing. Then she helped me to my feet and I wobbled a bit. She motioned for me to leave the panties in my mouth and be quiet.

"Now, I want you to go in and put my panties on. No more black panties during the day. I want you to buy 3 more sets of panties in nice bright colors with lacy trim. You can wear the black ones to bed if you want, but during the day, you always wear pretty feminine ones. Understood?"

I shook my head, yes.

"Good. Now pull up your pants. I am going to leave first. Remember, because of YOU I am going to go through the day in this short skirt with no panties on. After spanking you I am super horny. I feel like grabbing the first guy I see who has a REAL cock and having them fuck me silly. Of course I won't. But... by history class, I may need some help. Be prepared. Understood?"

I looked at her dazed.

"Don't worry, I will lead. Just be ready." with that she turned and walked quickly away.

I looked at my watch and saw I had 10 minutes to get straightened up, settled down and into class. I pulled up my pants and the jeans stung as they pulled over my ass.

My phone buzzed, "Be sure to have my panties on before first class. Send pic."

I decided, better to do it here rather than trying to get to a bathroom stall and change there. I took Jackie's panties out of my mouth, pulled my pants back down creating more pain and slid her panties on. I texted a pic, straightened myself up and went straight to class.

My first class was uneventful, other than my ass was burning like a forest fire. I kept shifting around in my seat and my jeans looked a bit wet given the panties were full of my saliva.

My next class was with Ms. Sanford. I hoped she would let the other day' s events go.

As I walked into English class, Ms. Sanford stared silently at me in a weird way. The bell rang as I sat down. She did the roll call. When she got to me she said, "Sam, still having trouble keeping your pants dry I see. Maybe a little more discipline will be helpful."

This had everyone in the class laughing hysterically but I don't think anyone knew what she meant. In fact, I wasn't sure I knew what she meant. It did have me wondering if she and Jackie were communicating. As I was leaving class she looked at me and said, "Sam, remember Saturday morning. I will send the details soon."