Down The Road Ch. 02

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Punishment and the party.
8.6k words
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Part 2 of the 3 part series

Updated 10/29/2022
Created 11/02/2013
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Thecsm
Thecsm
1,518 Followers

I want to give thanks to Choronzonxx for editing and making my story a better-written story. Plus thanks to one of my fans who wants to remain anonymous for their input into the story.

As we started out of the driveway, began to tell me which mall we were heading to before Jake interrupted.

"Turn at the next light," he laughed.

"Sir I thought I was picking the mall?" Karen protested.

Bob was laughing now. "Yeah right. you thought wrong!"

I made the turn and started towards downtown, before Bob suddenly turned towards the women.

"Get those bras off now!" He ordered.

May and Karen just looked at Bob and Jake. They couldn't believe what he was saying. Jake was sitting next to May by the door, and he turned to look at the nervous MILFS.

Jake wasn't smiling, and he pulled his hand back and slapped May hard across the face. Then he leaned past May to smack Karen in the back of the head. "Look, you two cunts. When we say to do something do it. No questions, no hesitation."

"Now give me the bras."

Both women were dressed in their running outfits that they had worn to the garage. They were dressed in tank tops, sports bras, running shorts and running shoes. The girls slowly took off the tank tops and then the sports bras, exposing their tits to all in the car. They quickly replaced their tops before handing the bras to Bob, leaving their tits dangerously close to being exposed. Both May and Karen were embarrassed that their bodies were betraying them as their nipples were threatening to poke holes in the tops.

"Maybe we should take the panties too." Jake suggested.

"No!" May and Karen gasped. "We can't walk around almost naked in public."

"I'm getting tired of you two being disrespectful. When we tell you to do something ,you will do it. Looks like I may have to send a picture of you two fucking us to your sons." Jake yelled.

"Sirs please don't, we're trying to do as you asked," Pleaded May.

"Please don't send the pictures; we're just afraid we might be arrested if we show too much." added Karen.

"What do you think, Jack?" Asked Bob

"I think we can give them another chance." I answered, surprised by the question. "But don't expect that I will always be so nice," I said to the girls. My cock started to rise from the power that washed over me in controlling the beautiful MILFs.

"All right then, we'll let the new guy on the team call this one." Bob replied and he looked at Jake who seemed unhappy with that decision.

I looked at May and Karen in the mirror, who nervously sat waiting to see if I was going to make them strip even further. I noticed Jake's expression and decided not to overstep my bounds. "You can leave the panties on for now."

Both women breathed a sigh of relief at my answer. Even though I was enjoying the control, I still couldn't quite pull the trigger to expose my friend's mothers to the world just yet.

"Turn left at the next street," Bob said.

We entered a section of town that was noticeably seedier with dive bars, and homeless men were loitering on the corners. "Pull into the parking lot by the red building over there on the right."

As I approached the building I noticed it was a plain red brick building with blackened windows, with bars and grates over the door and windows. A neon sign overhead flashing "ADULT".

As Karen and May walked toward the door from the car, Karen looked at May nervously. Her tits were bouncing and her nipples were sticking out in plain view threatening to burst through the thin material of her top. The sides of her tits were in plain view from the large arm holes in the tank top. She couldn't believe she was in this situation, almost topless on the street walking into an adult store with young boys her son's ages in charge of her life.

As they entered the store, both of the ladies were relieved to see it wasn't busy. I followed closely behind, watching their reaction as they looked around the store. Just inside the entrance was a display of every size imaginable dildo and vibrators, followed by a large display of BDSM whips, chains shackles and clamps.

I watched Jake reach over and grab May's ass and say "I can't wait to use these on you!"

May yelped and tried to spin away, but Jake held on tightly to her ass.

"Don't you resist me, slut!" May quickly quieted down while looking at the floor, humiliated at everything around her.

Suddenly, I saw Mrs. Smith, my old English teacher. I was in her class last year. She was the hottest teacher in school. She was every boy's wet dream, especially after Christmas break last year. She had recently started to wear sexier clothes to school. Always in skirts and tight tops, and they had seemed to get shorter as the year went on.

Right before she left after spring break you could tell she wasn't wearing bras any longer, and the skirts were so short you could see her ass when she bent over. All the guys would rush to get to class to get a front row seat, especially in front of her desk as she sat on her desk at least part of every period. Every guy in class always had a hard on that wouldn't quit.

After spring break we suddenly had a new teacher, and Mrs Smith never came back. It was rumored that she had an affair with a student and the school board had received a video of it, but it was kept pretty quit.

Now there she was in front of me at an adult store dressed in an extremely short skirt that barely covered her ass and cunt. With a white button down transparent top that was so tight her tits seemed ready to burst out at any moment. If I wasn't hard enough already after being around our two MILF's, my cock was about to burst out of my pants by now.

And then Mrs. Smith walked up to Jake .

"Sir, I see you have two new sluts with you today," she said.

Jake grabbed her and pulled her to him and gave her a big kiss. "Yes we do, and I need you set them up with what we talked about last night. You do have everything ready?" said Jake. "I want them to have the proper slut wear when they are with us."

"Yes sir I do, I just need to make sure I have the correct sizes for them. Why is Jack with you?"

"He is now one of us. From now on you will also call him Sir."

As I approached them Jake said, "Jack this is Pam, and she is one of our sluts. Go ahead and cop a feel."

This was like a dream come true. My sexy English teacher, the one I had beat off to so many times, standing in front of me waiting for me to maul her tits. I reached out putting my hands on her tits, squeezing them and pinching her nipples.

I was lost in my fantasy when Bob walked over with the two women. "Okay Jack. You can have fun with Pam later, but right now we need her to take care of these two."

"Follow me," Pam said, looking at the two women.

May and Karen looked at each other nervously and then followed the ex-teacher. She led the women to the back of the store where she had a couple of bags ready on a table.

I couldn't help but I follow them and watch the three beautiful and sexy women walk down the aisle in front of me. I wanted to see what Bob and Pam had planned for them. I kept a little distance but I was close enough to hear them talk.

Pam Smith looked at the two women. "I remember you two. You're Dave's and Tim's Mothers, aren't you?"

"Yes we are." replied May as she looked at the ex-teacher and wondered what happened to her to end up here.

"I don't know how you got involved with these two assholes, but believe me you, don't want to piss them off. They can be very nice, but once you piss them off you're in trouble and you will feel pain."

May was smiling and trying to be confident.

"We're just having fun right now," she said. "They got the biggest cocks we've ever had. I don't think they would do anything. I'm sure they're all talk and no action."

"I'm just going to tell you this once, and you better listen up ladies. Those two are not just talk. I made a foolish mistake. When I saw their cocks I became infatuated with them, and it has cost me everything. It took control of my life."

May and Karen rolled their eyes at Pam's last statement.

"It started slowly at first," continued Pam, "like wearing only skirts to school. But then they became more demanding. Every time I would resist they would eliminate something I would be allowed to wear, or force me to wear shorter skirts, or forbid me to wear bras or panties. And if I really refused to obey they would discipline me with spankings, whippings, clamps, bondage. Eventually I had to succumb and give into their demands."

"Oh, my!!" Karen yelped.

Pam just looked at her. "All the while I was a sex toy for them or anyone they wanted to share me with. The school couldn't help but notice how I dressed. Hell by the time spring break arrived I was almost teaching my classes naked. Then I resisted one time too many. They sent the school board one of their videos they had of me. That was how they got me fired from my teaching job. The Friday before break I was called into the office and fired."

"What assholes!" May broke in sarcastically.

"I'm just lucky my husband understands and didn't leave me," Pam said. "He realizes that if he interferes I could go to jail. Sometimes they even invite him over to their parties to watch and participate in fucking me and their other sluts. They also got me this job last summer. I'm telling you: don't piss them off. I don't think you know what you have gotten yourselves into."

I watched as Karen and May looked at each other with a little apprehension on their faces. Karen quickly recovered and said "Don't worry about us. We'll be okay." All the while thinking, that slut teacher shouldn't have fucked her students. We don't have that problem we aren't teachers.

I turned and walked back to the front of the store with Jake and Bob. My mind was reeling with all the possibilities of what is to come. My cock was slowly taking control of my mind. I was becoming intoxicated at the thoughts of complete control of the two MILFs and my ex-teacher.

The reluctance of humiliating the two women was quickly evaporating. I chuckled to myself as I thought, "my cock runs over, and I can't wait to run it all over these three women."

About 30 minutes later Pam walked over to Jake. "Sir, we're done," she said. "As always, I will make sure it's all paid for. I take it you haven't broken them in yet."

Jake smiled and looked at the sexy teacher. "Their training is just starting; those two bitches are going to get a rude awaking real soon. Now, I want you to give Jack a blowjob. Go on. Make his day."

"Yes, sir." The slut teacher said.

Pam walked over to me dropped to her knees. I looked down at her as she unzipped my jeans, and her skirt rode up high above her cunt. I could see she wasn't wearing any panties as she spread her legs. I could see her labia wet with her arousal. She pulled out my cock and started to lick the head and down the shaft. The feeling was intoxicating. After it was wet from her saliva she took the head into her mouth and started to suck on my cock.

I don't think I have ever been as aroused as I was at that moment. I struggled to keep from blasting my sperm into her as she continued sucking more and more of my cock. But I couldn't wait any longer; I put my hands behind her head and started to fuck her month with a vengeance. As I felt my cum start boiling nuts I looked up and saw May and Karen watching.

May was reaching into her top and pinching her nipples and Karen had moved her hand inside her shorts. She was slowly moving her fingers over her clit as she was watching Pam take all of my cock down her throat. Looking at all three of them, I exploded into an intense orgasm blasting my entire load down her throat.

Then I heard Bob say, "See how well she obeys? You two better get into the program, or else."

May and Karen didn't reply but they quickly removed their hands from their clothes as Jake walked behind them and smacked them both hard on their ass. They both jumped. "Yes sir."

It didn't take me long to get my cock put away as I looked at Pam. She was still on her knees stroking her clit and working herself to a climax. As we departed the store I looked at Karen and May who were still aroused but both had a look of apprehension as neither of them was certain what they had gotten themselves into.

We jumped into the SUV and went back to the garage. When we arrived, Bob had the two women put the bags into the garage. Pam had confirmed their sizes and the ladies watched as she had gathered several outfits from the racks in the store but didn't show the clothes to the new sluts. What else was in there they didn't know?

Jake said with a firm voice, "remember sluts, keep your cell phones with you at all times. When we call or text you, you will answer or respond immediately. Understand?"

Both women nodded their heads. "That's all for now sluts, get out of here. We'll text you later."

...

The next morning I get a text from Bob that said "get over here fast. May did not answer a text last night. Jake finally got a hold of her and she will be here at 9."

All I could think of was what Pam had told the sluts yesterday. As I was thinking that I noticed that the two women were no longer my friend's mothers; they were our sluts. Sluts to be used for our pleasure and used in any way we wanted.

I knew Bob and Jake were going to punish her and all of the possibilities were going through my head. I got dressed in record time. My cock was already getting hard just thinking about what was about to happen. I quickly ran over to the garage, making sure to get there before 9. Bob and Jake were waiting when I got there.

Jake said looking at me, "glad you're here, we want you to see what we do when one of the bitches don't follow the rules. We have been nice to these two and it hasn't worked. After today they will be obedient, though."

I looked around the garage and noticed on one side there was a bench with cuffs attached to each leg. On the pool table was a couple of paddles a riding crop, and a 4 foot long cane. Off to the side were the bags the cunts brought back from the store yesterday.

I then heard a soft knock at the door. I opened it and May was standing there looking very nervous. She was again wearing and outfit similar to what she wore yesterday, shorts, tee shirt, bra and panties. I guess she uses running as an excuse to get out of the house.

As she entered the garage, she saw Jake and Bob looking very pissed and she took a step back and gasped.

The two of them didn't beat around the bush making their displeasure known. "You seem to have a problem following instructions, don't you bitch? You didn't answer our text last night," Jake snapped.

"I'm sorry sir, my husband was home and I couldn't come here then," May apologized. "We had just finished dinner and couldn't get away to answer you. Time just got away and I forgot about your text until much later. I don't mean to cause trouble."

"Wow, this cunt thinks we care about her husband," Snarled Bob. "You seem to be the troublemaker out of the two of you. Pam told us what you said yesterday. I guess you didn't listen to what she said and noticed how she obeyed. One would think by now you'd have learned there are consequences for not following our demands, but we intend to drive that point home today."

"Did you think we would just forget and forgive?" Jake yelled. "You were told to answer all text and calls immediately! If you can't make it you tell us why and we will decide if is a good enough excuse, but in this case we've encountered a problem!"

"No, no, no, no, no!!" screamed May. "Please." was all she got out when Jake grabbed her by the hair and pulled her over the area where the bench was.

It was only a little over foot wide and four feet long. He bent her over the bench and Bob took her hands and cuffed one to each leg on one end of the bench. Jake ripped her clothes right off her. May was now almost in a panic. She was naked and cuffed to the bench with her ass and cunt completely exposed as her legs straddled the bench.

She looked up at Bob in front of her and begged, "Please Sir! I won't let it happen again. Please don't punish me. I promise to do better."

Bob just looked down at her with a wicked smile and said "after we're done here I guarantee you won't disobey us again!"

"You do remember the rules?" Demanded Jake. He walked up behind the cuffed and helpless slut and slapped her ass.

"Yes sir. I remember what you told us" May quietly answered.

"I think you are just saying that, or you think we're stupid. Remember Pam told us everything you all talked about."

"No sir, I don't think you're stupid."

Jake took the paddle that Bob had handed him. "After each time I smack your ass, you're to say 'thank you sir can I have another!' You understand?"

"Yes sir."

Jake pulled back the paddle and brought it down hard on May's left ass cheek. May jumped and screamed as the pain shot through her body "OH MY GOD," she gasped, then quickly added "thank you sir, can I have another?"

Jake smiled as he took careful aim and then pounded the next shot on the other cheek. May screamed again but did as she was told and thanked him and asked for another.

Jake looked at both us then and started to really pound May's ass. May was crying uncontrollably as the pain reverberated thru her body and straight to her cunt. Bob kept it up smacking her ass with her asking for another one each time.

May was in another world. She was so confused. Her ass was screaming at her in pain, but something else was happening. She was becoming increasingly aroused. Her pussy was wetter that she had ever experienced. Her juice was leaking out in copious amounts. The bench upon which she lay had a puddle of her juices. Each time Bob smacked her ass with the paddle the pain shot to her brain and excitement shot to her cunt. And each time he smacked her ass, she found herself begging for another.

After about 30 whacks, Jake stopped. May was crying uncontrollably, hopeful it was over. Then Bob who was still in front of her watched as Jake grabbed her hair and pulled her back. Her hands and cuffs raised up the legs of the bench as she was pulled so her tits were now off the table.

Bob reached out with both hands and started to pinch her nipples and twist them until she yelled out in pain. May cried out as the pain in her nipples began to overtake the pain from her ass.

She thought she might climax when Jake let go of her hair and she fell back down on the bench, her tits mashed underneath her.

I watched her as she lay there crying and rubbing her crotch against the bench. Begging to do anything to please her new masters, if only they would stop the punishment and let her cum.

Looking at me Bob said, "it's your turn. Grab something from the table and let her know who the boss is."

I walked to the table and grabbed the riding crop and walked behind her.

"Please stop," she moaned .

I didn't hit her as hard as Jake, but my strike was more precise and right on the puckered rose of her ass. May's body went totally rigid when the shot landed. The pain was concentrated in a very small area that the paddle hadn't touched. Her eyes were like saucers and her breathing became labored. Then we heard a guttural moan that came from deep within her soul. But she didn't thank me, or ask for another.

"Slut, that one didn't count. You didn't ask for another!"

May quickly started apologizing and begged to be hit again but I just bent down next to her ear and said, "The punishment will continue until we are certain you will never disobey again. Slut."

I watched as her body slumped against the bench totally defeated. All the fight was gone. The next swat was directly on her cunt. May's body again went rigid but this time she screamed "Thank you sir, may I have another!"

Thecsm
Thecsm
1,518 Followers