The Crush Ch. 03

"Thank you Ms. Sanford", I squeaked as I scurried out the door.

I still had 3 hours until history class with Jackie and Hallie. I couldn't get my brain off my ass being on fire and the image of Jackie walking around in that short skirt with no panties. I could still smell and taste her pussy juices that left over from being gagged with her panties. I so wanted to cum. I was getting desperate. As I walked through the halls, I barely acknowledged people saying high and just wanted to find a private place to be alone.

Finally it was time for history class. I arrived early, took my seat and dutifully unzipped my pants. I was never ever going to make that mistake again.

Hallie walked in right afterward and sat down next to me. "Hi Siss." she said. "I hear you had an early morning today and did well."

"Yes Hallie, it was a very eventful morning." Now there was no doubt she was an accomplice.

"How was it? I know Jackie can be very intense."

"It was very difficult. I do not want to do that again."

"Oh Siss, but you will, I promise you will." she winked. That thought made me shiver.

"You know I saw Jackie earlier. I could tell she really enjoyed herself. She always likes introducing Monica to new people. How was Monica?"

Now this was really humiliating. Sitting there discussing my spanking and a brush called Monica with Hallie.

"I found Monica mean and unforgiving to be honest. I do not want to see her again."

"You know Jackie really doesn't go anywhere without Monica. She is the type of friend who will surprise you in how useful she can be, always there in a pinch." With that Hallie reached down and pitched hard the side of my ass. I let out a little yelp. She smiled mischievously at me.

"Stop." I said softly but firmly.

"I don't think you want to speak to me like that Siss. It's not polite and I have a friend Barbara that has a similar personality to Monica. In fact some people say Barbara is meaner. Not many people know both of them but I would be pleased to introduce you."

"I apologize, Hallie."

"Good boy. Now when I saw Jackie earlier she looked like she was ... how do I say," she whispered, "practically leaking from that skirt. I understand she gave you a gift that left her exposed."

"Yes, Hallie, she was very kind to give me that gift."

"Now when she comes in she will need your service. I am sure you have never done this before, so let me show you what she needs. This needs to be completely discreet. No one can see. Understand?"

"Yes, ma'am."

"Good, now let me take your hand."

She took my hand and put it under the desk and up her thigh where her skirt had a slit until I reached the crotch of her damp panties. I was very afraid someone might see, but as I looked around I saw that, in the corner where we were sitting, nobody could see below the desk. She moved my fingers to just below her mound where there was a little bump. I heard her groan slightly.

"Now rub there, not so hard, not so hard. Very very softly. There you go. That's better."

She pulled my hand away and smiled at me looking a little like she might be drunk.

Jackie then entered. Seeing her for the first time since my spanking, I shuddered a little. She looked stunning. It made me crazy knowing she had no panties below her short red skirt and had a beautiful smile on her face as she looked me in the eyes. I could see the eyes of the other guys in the room following her as she walked across the room. She walked over and plopped down next to me. "Hi Siss. Miss me yet?".

I lied, "Yes Miss."

"I am so glad we came to our little understanding this morning. I think it will be better for everyone, don't you think?"

"Yes Miss".

"Do you agree Hallie?" Jackie asked.

"Oh, hi Jackie. Well I really couldn't say." Hallie said in an exaggerated tone. "I wasn't there. Maybe we could have a similar discussion soon where I get to participate also? I would really enjoy that."

"Yes of course. That makes sense. Maybe you could bring along your friend Barbara too."

"Oh, that would be wonderful. Sammy, you game?" Hallie asked.

I cringed at the thought. "Yes of course ma'am. That would be wonderful." I tried to say as sincerely as I could.

The bell rang to start class.

Jackie reached under the table, she felt my panties, or I guess hers, through my unzipper pants, massaged them briefly and pinched hard. This time I was mentally prepared for that.

"Still have that wet slutty pussy", she whispered with a smile..

Then she reached over and took my hand that was in my lap and moved it over to her lap just like Hallie had. My finger touched her warm wet pussy. I was entranced and in heaven again. She moved her hands to the top of the desk. I proceeded to follow exactly what Hallie showed me earlier while Jackie kept her eyes looking straight ahead. I kept going slowly, gently, watching through the corner of my eye how her body reacted. I could hear her breathing become quicker and shallower. Her legs started to tense. Then she squeezed her legs together with my hand trapped in place. I kept going at the exact same pace and the exact same touch. Then she grunted almost imperceptibly and relaxed. She reached down and removed my hand.

She bent over and whispered, "Good boy, I needed that."

I felt very proud that I made her happy, at least I think I did. I sat there feeling very satisfied and at peace for the rest of class. When the bell rang, Jackie stood up and left without speaking or looking at me. She looked like a true goddess as she walked away.

After school I rode my bike home being careful not to let my butt touch the seat to avoid the pain. On my way I stopped at the store to buy the new frilly panties as Jackie required. This time I walked in with confidence, knowing I was doing what my goddess wanted and no one else really mattered. It had been only 5 days since the fateful night at Brad's party, and now Jackie totally and completely owned me and I was thrilled. I had never felt like this before.

I was a little anxious about what was ahead, but in many ways I really didn't care as long as my mistress was happy. Life seemed simple for the moment.

For the rest of the week I followed the same routine. Every evening, daytime panties washed, my night time panties on, my end-of-day text to Jackie, my 50 pinch-pull-twist nipple conditioning. Every morning, my morning text to Jackie, and meeting her at 7:30 am for my inspection. Monica made no more appearances so far.

Jackie seemed pleased with how my nipples were getting more sensitive and visible through my shirt. It was the highlight of my day when she tested my progress with her mouth on my nipples. Strangely, I started to think more about my nipples than my dick. I just kept imagining the feeling of her tongue on them when I thought about cumming. She was shifting the center of my pleasure to my nipples. Of course she hadn't let me cum yet, so I was obsessed over the idea of how and when I would be allowed. It was getting a bit difficult not to just start rubbing my nipples or my cock. And I was leaking precum into my panties which added to the distraction and humiliation.

My history class was also the same, with Jackie probing and pinching my open fly. She had not asked for my "services" again since the morning with Monica.

After just a few days this felt like a normal natural rhythm of a high school senior. I felt I could happily go on like this forever.

Part 8 - The Weekend

By Friday evening I still hadn't heard from Ms. Sanford. I had hoped she decided to let my embarrassing incident in class pass, though she had sounded pretty determined to meet Saturday. I couldn't meet her if she didn't tell me where and when.

I ended my Friday evening with my text to Jackie.

Me: Thank you Mistress for letting me serve you

Jackie: Hey Siss. Tomorrow is your day off from my inspection. But I guess you and Ms. Sanford are going to spend some time together :)

Me: I think she must have forgot - I haven't heard from her

Jackie: OMG - you didn't contact her! She is going to be soooo pissed.

I panicked, why would I need to contact Ms. Sanford? She said she would contact me. How could this be? This made no sense. The last thing I needed was Ms. Sanford to be mad at me. Geez.

Me: Jackie - she said she would contact me and tell me where to meet.

Me: I didn't do anything wrong.

Jackie: Oh. Maybe I forgot. She gave me her cell # and asked me to pass it to you. You know, after she texted me with your phone and all.

Me: Great. Then you can let her know that I didn't know.

Jackie: I don't think so. You want to blame ME!!!!!

Me: But you did it. I didn't know. She is going to be very mad at me otherwise.

Jackie: Do you remember the RULES? You are here to serve me, not blame me

Me: This isn't fair.

Jackie: Who said anything about fair. Her number is 808-555-0213. Text her now, but DO NOT mention me. Got it.

Me: Yes Mistress.

Jackie: Siss, are you going to really get it. Sweet dreams :)

That was cruel. How could Jackie put me in this position? That wasn't right. But I tried to put my anger out of my head. I needed to get to Ms. Sanford immediately. I texted the number.

Me: Hi Ms. Sanford. Sorry for this late text. I was wondering where and when you wanted to meet tomorrow?

No response. I sat there staring at the phone. 20 minutes passed so I decided I should finish my routine and go to bed. I had finished my nipple conditioning and was just dropping off to sleep when my phone buzzed.

Ms. Sanford: Tomorrow, 930 am sharp at 11 Oak Street. Walk to the front door. Just stand there. Do not ring.

Me: Yes Ms. Sanford. I am so sorry for the late text. I really apologize.

Ms. Sanford: Don't worry. I will enjoy administering the consequences tomorrow. Nothing makes me happier than giving disrespectful boys their comeuppance. Sleep well, if you can.

Me: Thank you Ms. Sanford.

Needless to say I didn't sleep much that night. I was worried about Ms. Sanford, but she was a teacher, how bad could it be?. 'She wouldn't do anything crazy, right?' I thought to myself. And I was very mad at Jackie for putting me in this position. In fact, I was starting to think if she might have even done this intentionally.

I tossed and turned in my black panties. I wished I could cum. I gently humped my pillow with my panties which felt good and took my mind off my impending meeting with Ms. Sanford a bit. But I wanted, no, I needed Jackie's approval. I couldn't cum now. It would make it all much worse.

I saw the sun start to show through my window after not barely sleeping a wink and I knew it was time to face the consequences.

I got up and showered and started to get dressed. Then I realized I didn't know what to wear for underwear. Do I wear the frilly panties Jackie required and risk Ms. Sanford discovering them. Or do I wear normal jockey shorts again this one time.

I sent my morning text.

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

Jackie: Good morning Siss. Did you connect with Ms. Sanford?

Me: Yes Mistress. I am meeting her this morning.

Jackie: Good. What panties are you wearing today?

Me: I think I should not wear panties, Mistress. What if she finds out?

Jackie: Are you really thinking of disobeying me?

Me: But Mistress, I really can't wear panties. She might be going to spank me.

Jackie: Would you prefer Manica and maybe Barbara do it instead?

Me: No Mistress.

Jackie: Good boy. Now let me see.

I put on my robin blue panties with the white lace and sent Jackie a pic.

Jackie: Very cute :). When you are done, I want you to tell me all about it.

Me: Yes, Mistress. Talk later.

Jackie: Good luck

This was quite the mess. I really couldn't believe I was in the situation. Deciding whether to wear panties or not to a teachers house on the weekend for a disciplinary session. What world had I entered? I didn't feel good about this day. I had decided I would make a little change, split the difference so to speak. I took off the blue panties and put on the black ones. They were still panties, like Jackie required, but being black they could almost look like fancy mens athletic underwear. I felt good about taking a little control of the situation rather than being just a simpering wimp. After what Jackie did by not giving me Ms. Sanford's number until it was too late, this was the least I should be able to do.

11 Oak Street was only about 2 miles away so I jumped on my bike at 9am giving myself plenty of time to get there. It was a beautiful early spring morning with a nip in the air. Riding made me feel better, settled my nerves a bit. I arrived about 15 min early. Ms. Sanford's house was a modest stone construction with small leaded framed window panes. It wouldn't have been totally out of place in a horror film. Her house stood out from the rest of the neighborhood which all felt bright and cheery, typical ranch designs.

Given I wasn't allowed to ring the bell there was no point in standing in front of it for 15 min. I walked up the street with a purposeful stride to kill time and keep my mind off what might happen next. I headed back when I had 8 minutes left so I could be certain to arrive at Ms. Sanford's house on time. Many people were out in their front yards gardening, cutting their lawns, or cleaning. Everyone seemed to be going about their business without a care and no idea about my bizarre travails. As I approached Ms. Sanford's yard again and was just about to head for Ms. Sanford's front door when I heard.

"Hey Sammy"

I turned and it was Mrs. Herbert from my church jogging toward me.

She stopped a foot away from me and hugged me. "Good to see you. I was just out for my morning run."

Mrs. Herbert was a hugger. She was also drop dead gorgeous. She conducted the church choir and I often found myself staring at her beautiful ass as the service droned on. She always wore tight pencil skirts to church. Today she was glistening in a sheen of sweat in her yoga tights and loose fitting translucent white shirt with a black sports bra beneath that showed off her beautiful large breasts..

The sweaty hug, her aroma and her standing a couple feet away gave me an instant hard on that I glanced down and saw created a small tent. She also glanced down and smiled knowingly like a mother would do. I couldn't take my eyes off her breasts, they were just so perfect and I was so so horny. Very embarrassing.

"Sam, Sam..." She said, clearly realizing I was distracted, "What brings you to these parts?"

I looked up and I said "Oh, I have an appointment with Ms. Sanford. I am working on some extra credit stuff."

"Sam, what did you do?"

"Nothing Mrs. Herbert, I am just trying to stay ahead of things."

"Ahead of things I bet. Not many young men emerge from her house looking like they are 'ahead of things' Sam."

"No really, just trying to stay out of trouble."

Mrs. Herbert suddenly looked over my shoulder and waved yelling "Hey Joan".

I turned around and there was Ms. Sanford standing in her doorway waving at her.

"I will send your young charge over to you now, Joan. Be firm with him. His mother is a friend and I am sure she would appreciate it."

"Thanks Fran. I will see you later at Fred's." Ms. Sanford yelled back smiling.

Ms. Herbert turned to me and said quietly, "I am going to see your mom at choir practice this afternoon. Don't worry I won't mention I saw you with that cute tent in your pants. Good luck with her."

She smiled, turning away to continue on her jog.

I really began to feel there was a whole parallel universe women lived in that I knew nothing about. But... it seemed I would be learning a lot more very quickly.

I began to walk toward Ms. Sanford. Her smile had disappeared and was replaced with a grim emotionless stare. As always she was dressed a bit over-the-top relative to the moment. She had a pleated block skirt that reached down to the middle of her thighs but flared slightly from the curve of her hips with a soft gray silk blouse draped across her breasts that clearly had no bra in between. Her shoulder length auburn hair framed her face, angelic beauty even with her scowl.

"Come inside Sam, you are late."

"Yes, ma'am." This time that phrase 'yes ma'am' felt perfect for the moment.

I followed her into the living room that had dark leather traditional furniture with an intricately designed Persian rug beneath. She pulled forward an ottoman from one of the large arm chairs and plopped down on it and pointed me to the floor. I carefully sat down on the floor in front of her. She leaned forward with her arms wrapped around her bare thighs and said, "Sam, you do know why you are here don't you?"

I said, "I think so. I think you felt I was not being sufficiently respectful in class and you wanted to speak to me about it."

"Hmm.. well you got a little of that right. Your behavior in class was abominable, playing with your phone and addressing me inappropriately. And then here we sit, you were late to text me last night making me wait, you were late this morning making me come find you. What do you have to say for yourself?"

She leaned forward more, and stared intimidatingly at me, put her hands on her knees that were now six inches apart, looking like she was about to stand. That movement created a clear view of her naked shaved pussy less than a couple feet from my face. I tried to look away and back in her eyes.

"SAM, what are you doing? Are you going to answer my question?"

"Sorry ma'am. It just... just that well Jackie didn't give me your number till late yesterday and when I got here Mrs. Herbert was there and I couldn't break away."

"And just now???"

"Well, I... I ... when you moved your legs.."

"Stop, stop, stop with the excuses. So you are telling me it was Jackie's fault because she was careless, Mrs. Herbert's fault because you can't stop staring at her breasts and you make me feel like a cheap whore because I accidentally moved so my pussy was exposed. Everything that happened is the three women's fault, none is your responsibility. Do I have that right?"

"No. You're putting words in my mouth Ms. Sanford."

"You will be lucky if that is all I put in your mouth. Now stand up."

I tentatively got to my feet which left her face right at the level of my crotch.

"So let's get on with it." she said, and reached to grab me by the belt and pulled me closer. She then proceeded to undo my pants and lower them to my ankles. She looped my belt around them another couple times and buckled the belt again, trapping my feet close together. As she began to sit up straight her head bumped into my penis which was poking straight out into my black panties.

She looked me in the eyes and said, "Well... somebody came here with a loaded gun. Nice panties. I had no idea. We are going to need to do something about that inorder not to distract from the corrective measures I have planned."

This was getting pretty strange, so I decided to ask, "What do you mean? What do you have planned?"

"I mean we need to have you get rid of that load so you can fully focus on and appreciate your punishment. Now I suspect you're a virgin, right?"

"Yes ma'am."

"OK, then you probably have never experienced a Fleshlight either, right?"

"A Fleshlight?"

"Yes." she said as she got up abruptly and walked over to the cabinet by the bar and returned with a canister that she was seemingly unscrewing as she walked. "This is a Fleshlight and probably the closest thing to a pussy you will have for quite a while."

I looked at the end of the canister which appeared to have what looked like a flesh colored rubber vagina. I definitely understood now.

"Ma'am, I am afraid I am not able to, or ... ah... not allowed to cum."

"You are not allowed to cum? What does that mean? Care to explain."