The Family Feud III

Chapter Twenty-Nine
“You can lead a horticulture, but first you have to trim her bush”

STAR COUNT:
WENDY: 36
Get out of jail cards: 1
WHORE: 1,3,1,0,0
JAMIE: 39
Get out of jail cards: 1
WHORE: 1,3,1,0,0

**Note to reader: This is Wendy’s journal from Friday Night detailing the events of approximately 7pm when she got in the car with Jerry for her first date. Some of Wendy’s journal was altered to protect the name of the corporation and some of the employee’s identities. In order to increase readability, some of the dialogue exchanged was altered to appear in a ‘narrative’ story format.

I felt impossibly small. I wanted to crawl under the belly of an ant and hide from a world that did nothing but rain piss down on me. Here I was in Jerry’s car dressed like a hoochie mama in a purple skirt, yellow tube top and red ‘fuck-me’ pumps and now shifting uncomfortably in a chastity belt that chafed in ways I was just beginning to understand.

I had my cell phone in my lap and that stinky Arby’s cup filled with my poop. I felt like my life was right inside that cup. We had been having a vicarious kind of fun earlier in the night. It wasn’t what I would call ‘traditional family fun night’ like backgammon and table tennis.

Jamie and I had been able to make each other laugh through some of what is now and will most likely forever be known as “Taylor Family Fun Nights”. Naked behind a store, Naked inside a store, we had been facing all sorts of fears and insecurities and met them head long.

Alone with Jerry in his car, the mood had changed. It had become serious and dreary, much like him.

There was a quiet pause as Jerry pulled out onto the highway to drive back towards town. He flicked on his radio, and of course it was tuned to the weather channel. What else would a boring person like Jerry listen to in his car where he could clearly see the weather outside his window than an update on the weather?

I stifled an urge to tease and ask ‘Arrrr, are ye a sailing captain. Need the latest report on the storms that arrrrr brewin’. That is something I might have done if I had discovered Bill listening to the weather. Thankfully I don’t think even he is THAT anal retentive.

Jerry flicked to another station as if he realized how lame his initial choice was. I think he had it on the AM radio band. Who still listens to AM radio? Jerry Cooper, I guess.

fa fa fa fa fa fa fa fa fa

fa fa fa fa fa fa fa fa

I keep singin' them sad sad song y'all,

Sad song is of all I know.

I keep singin' them sad sad song y'all,

Sad song is all I know.

It has a sweet melody, tonight,

anybody can sing it, any old time

The soulful sounds of Otis Redding came out of Jerry’s old radio almost as if it was narrating his sad, lonely life.

“Would you like me to suck your dick, Sir?” I offered hopefully. Bill had given me our unspoken order that I needed to finish what I started. As much as I loathe the little man, having something to do right then would have been worth the disgusting humiliation of bending over and sucking him off.

“No, I want to talk.”

“I was afraid of that, Sir.”

“I bet you were. First, I want you to drop the Sir business. You don’t’ really mean it. You don’t see me as your superior.”

It was true. I didn’t see him as my better. That was true of a lot of people I had served, but Jerry was high on the list of people low on my respect list.

I was supposed to be putting him above me and I was still willing to give it the old college try. “You are now a key holder. That makes you my handler. You are my superior in every way, Sir. If you don’t want me to call you Sir when we are alone, will you promise not to tell Bill?”

“Seems you like to keep a lot of secrets from him.” Jerry didn’t answer my question. I have always hated when people did that, especially Bill.

“I didn’t mean it like that, Sir.” I explained. “I just meant if I break with my protocols, I hope you will tell him it’s because I was ordered to stop and not get me in more trouble than I already am?”

“Sure, whatever.” Jerry fidgeted with his radio to control the static.

“So where do you want me to start?” I almost said ‘Sir’ anyway. Even though I don’t have to say it at work, it has become such a habit that it is hard to stop when I’ve been doing it for a few hours.

“You can start at the beginning and the truth, this time.” Jerry sounded like he was pissed at the world for constantly deceiving him and I felt like the personification of that deceit at that particular moment.

“Mine is a long story to tell, Jerry.” I smiled as I pictured how many chapters it would take just to tell up to this point in my life and there was so much more to go. The past few months had been the strangest point in my life. I’d probably skip all the early part and start with how I gave Bill the ultimatum to change that began this odyssey of power exchange between us.

“I heard you talking in the BDSM parlor upstairs. I understood most of it. That is all true?”

“My affirmation?” I knew what he meant, but I was stalling to give myself time to think about everything I had gone over. “I believe you heard my confession that I overstepped my boundaries at home?”

He nodded at me. “Yeah, it sounded like some kind of family feud. The girls against the guys.”

I told him that was a good way to put it. I explained how I had the best of intentions when I began. I wanted them to get healthy, take responsibility for what they did wrong. I wanted them to try harder, aim higher, and take the traditional roles of men around the house. I didn’t mind cleaning up, but I was tired of cleaning up after them and they not showing appreciation or any desire to clean up after themselves.

I was careful not to illustrate Bill’s shortcomings too much. I was sensitive to the fact that Jerry seemed to have much of the same traits Bill had before our ‘Family Feud’. This past week, instead of rushing off to Pilates, book clubs and power walking I had spent a lot of time immobile and bound up in the living room with nothing else to do but think.

One of the things I had come to realize was Bill’s addiction to porn and the internet in general was a symptom of a bigger problem. He was using the porn as a substitute for an unsatisfying and uninteresting sex life. Exercise (and surgery) gave me a fantastic body, but being in the bed with me at night wasn’t very rewarding to him.

His desire to get on the internet and argue with people about history, sports, computer games, that was another symptom. He would take out his aggression by fighting anonymously with other cyber warriors. On the internet, they could say things to each other they would never have said if they were having a beer and talking face to face.

Bill’s nature to compete and dominate had been subverted by the internet. He had used it as a conduit and a release for his desires because it was always available. Unlike me who was at my job or working out, his internet was always there when he needed it. He could turn it on with a flick of a switch and it rarely if ever refused him. Resetting the cable box was all he needed most of the time to remedy the situation.

I skirted around those observations with Jerry because I sensed it would only make him hate me more if I reminded him of his many, many flaws. I don’t know why he hated me in the first place. I was willing to suck his dick and be compliant and yet he had this contempt for me.

It made me want his approval. I am not sure why, but I could feel a desire inside me emerge to get him to understand and accept my decisions.

I began to explain how once I identified the problem, the initial solutions I tried didn’t work. Bill and Chris weren’t changing and they snuck back on the computer and were lazy whenever they weren’t supervised.

I couldn’t satisfactorily pinpoint the moment or reason things got very weird at home. At some point we went from good-natured, peer-pressure and taunting to keeping them naked and humiliating them. I think it was when they came home from Rahjid’s motel broke and begging to return home. They couldn’t hack it in the real world on their own without me to ‘mommy’ them.

They hadn’t washed any of their clothes and they were soaked in the outfits they did have on. I insisted they strip and somehow that became the new rule of the house that they stay that way. I can’t explain why. I started to justify why I did it by making them exercise and see their flabby and disgusting bodies as they did. I was going to shame them into getting healthy so they could thank me for living longer and developing better habits.

I remembered when I came up with the leash and why. They would walk around hard as if they were proud of their accomplishment, with their dicks bobbing up and down.

I felt like they were flaunting a subtle kind of disobedience. They were smiling as Jamie and I could see their throbbing member and I decided that if I could keep their balls high and tight, they wouldn’t be able to do that anymore.

Applying a leash to the cock didn’t stop their hard-ons. In Chris’s case it only intensified it. I knew they were jacking off several times a day when I wasn’t watching them even during this training. Chris had a disgusting knee-sock that he made love too several times a day.

I decided if they were going to masturbate and I knew about it anyway, I may as well make them do it often enough that they didn’t have any desire to do it when I wasn’t around. I decided to make it humiliating and shameful enough that they wouldn’t WANT to do it when I was not around.

In the process of all of these good intentions, I lost myself and became a monster. I sucked Jamie into it with me and let her pull her brother around by a leash. I didn’t LET her, I encouraged her to do it, I admitted to Jerry.

He seemed quietly turned on by my story. I considered that progress to be turned on instead of contempt.

I told him about the party and how we were busted by one of Jamie’s friends who knew exactly what was going on. He seemed particularly interested in that, but I tried to explain that our reasons for agreeing to this was to give the men closure and payback.

He did not believe me.

“Women exist to take from men, and to give them pain.”

“I am sorry you feel that way, Jerry.”

“My wife,” He stopped himself, “My Ex-wife has my house, everything I ever owned. I have to drop off a check tonight because I am behind on child support that she does not need. She is dating a guy and they live together. They won’t get married because they want my support check. That guy pushes my lawn mower, probably drives my old suits.” He was angry at the man who he felt ‘replaced’ him in his ex-wife’s life.

I wanted to joke that he was also fucking her as well, but I knew that wouldn’t win me any brownie points. I wanted to give him some advice about getting closure on his ex-wife and closing that chapter in his life. Who would take advice from a woman dressed as a whore carrying an Arby’s cup with her turd inside?

He made me continue with the story of how I ended up a slave to my son and husband. I have to admit when I tell it, sometimes I can’t even believe it.

I explained how Bill had laid out the rules very clearly and why they needed to be different than the rules for males. We had different shortcomings than they did. They had different things they enjoyed than we did. New forms of control and motivation were necessary because men and women are wired so differently.

Bill thought I must not understand that because he often used in our affirmations as a theme about the differences between men and women but I really do accept that.

Jerry seemed to understand the reason for the rules. As an accountant I suppose his world is full of very black and white issues where a rule is needed. “Every time you agree to a rule, you are both giving up control, and gaining protection and guidance.”

He sounded like he neither agreed, nor disagreed with his observation. That was one of the infuriating things about Jerry when he had attended meetings. The person facilitating the meeting was trying to get him to commit to a decision to establish a consensus and Jerry danced around direct questions.

He didn’t do it artfully like Vicky and I did to play a political game of one-upsmanship. We could wait for someone else to put forward a plan and then pick it apart just to see them squirm and agree with our plan.

He did it because it seemed like Jerry’s nature to bumble through life without ever really making his mind up.

Now that I say that, that was my observation about Chris before our ‘family feud’ began.

I think it is probably more fair to say that Jerry is afraid to commit to an idea because he doesn’t want to anger anyone. He is such a small man, he thinks that taking a side is going to seem rude. That probably sounds harsh, but I wonder what is worse? A guy who is too ignorant to know when he has to make his mind up or a guy who is too afraid to make up his mind because he doesn’t want to disagree with anyone?

Stores and buildings were becoming familiar to me as I looked out the window. The past week I had so seldom rode in the front seat of the car and always to and from work. I was usually putting something in my ass or pulling it out at the same time, and it felt weird to sit there quietly and talk. I hate to admit I felt like I was ‘cheating’ and getting away with something I shouldn’t be allowed to do.

I didn’t tell Jerry that. I need to hold some things close to my vest even though I told him I would be honest.

He came to the part he wanted to ask about my daughter. I wanted to clam up completely. Steve had asked me about my daughter earlier in the day and I had been fool enough not to leave it alone. I stirred the hornets’ nest by asking him why he wanted to know. I would try to be more circumspect with Jerry.

“She isn’t really eighteen is she?”

I thought about lying. “She isn’t quite just yet. She is a junior.”

Wow, my son is a freshmen. She goes to Cherry Lawn or private school?”

I didn’t feel comfortable talking about Jamie with him. It is funny that I could suck off two strangers in front of a homeless man and swap cum in her mouth, but when talking about personal details like this my instincts were to clam up.

“Cherry Lawn, my husband is bringing her to the football game tonight. She is a cheerleader.”

“My son used to go to private school, but my ex-wife decided it would toughen him up to put him in public school. Private school was good enough for me!”

I almost laughed and told him I could see why his ex-wife would say that. I suppose despite it all, humility training, obedience, I can still be a sarcastic bitch.

“How do you feel about your daughter serving with you?”

His question was so broad and open ended that I wanted to correct him. Bill and Chris asked me direct questions that I could answer to the point. I was being judgmental and harsh on Jerry and I knew it. I sighed to summon my patience for this conversation with him.

“Okay, sounds like that is a sore topic with you.” He observed.

“It is just that how you ask, I don’t know where to even begin with that question, Sir.” I had slipped in an accidental Sir, but he ignored it.

He was quiet as he thought about his question. “You have sex with her?”

He had gone from very vague to very personal in the blink of an eye. I am sure he could tell from how he caught me off guard that I was reeling from his question.

“No, we don’t” I said without any confidence behind my claims of innocence.

He laughed at my words. I could hear him call me a liar under his breath.

“Okay, obviously we do some things together.” I clarified “For the amusement of my betters!”

“Okay, if that is what you say.” He was infuriating me by not believing me.

“We suck cock, playing with ourselves around each other.” I couldn’t see it but I felt him rolling his eyes in disbelief. “Bill isn’t fucking Jamie, if that is what you mean.”

“Why draw a line at all?” His question was more rhetorical than curious.

I answered anyway “There have to be some limits!”

“Why?”

Damn him, I thought to myself. Why does he always ask those questions? Just a blanket “Why?” and then you are expected to blab away until you think you may have satisfied his question. To make matters worse he won’t confirm whether he agrees or disagrees so you are left wondering if you blabbed long enough to make a convincing explanation.

“I know it seems strange that we have limits. We probably seem disgusting and willing to do anything. I admit, I’ve done some things this past week I didn’t think I would ever be willing to do, but Bill knows without limits it would just be chaos. Consequences wouldn’t matter for our behavior if he could beat us for no reason at all. We wouldn’t even bother to try.”

“If you say so.”

It was sapping all of my patience to remain in a submissive role if he wasn’t going to give me a chance to explain. Sure, if it had been Bill he would have shoved something in my mouth if he was tired of listening to me and I would have accepted it. I have to admit, I just have a bias against Jerry. He brings it on himself though.

“So why did you make up all that stuff about being a nymphomaniac at work?”

“Bill needed someone to watch me at work. He was afraid I would work late hours and use it as a way of getting out of the hard work and training I have to do. We made a deal at work that if we could find someone to supervise me, I didn’t have to admit everything I am doing. It’s very embarrassing!” I probably could have left that last sentence off, that should have gone without saying.

“So why Steve, because he is ‘Handsome’?” Jerry said the word ‘handsome’ as if he had just smelled rancid butter.

“It isn’t like that. I don’t know that many people at work that I thought I could trust. Bill offered me to Steve and he became my handler at work.”

“You keep using that word ‘handler’, what does it mean?”

“Bill came up with a hierarchy. He and Chris are at the top, naturally.” I snorted in laughter but humorless Jerry failed to pick up on my little joke (or he ignored it). “Then handlers. People he trusts with a key. If you have it, I am supposed to answer directly to you. Steve can punish me and he sends home reports on my failings at work. In exchange, I gave him my office, do his work and I will help him get promoted.”

“When this is over in a week, you are going to drop him like a sack of potatoes?”

“Not on your life. He has photographs of me sucking off coworkers, and worse. I am going to try my best to keep Steve and everyone I’ve come into contact with through this very, very happy.” I felt cheap and disgusting for saying that, but it was the safest course of action to avoid angering them and stay under the radar.

“Even me?”

“Especially you, you are my handler.” I smiled. I wasn’t sure if it was a fake smile or a genuine one. It could be hard to tell sometimes. “After this is over, I am going to be a changed woman, at the office anyway. I will put my family before my career. I may step down from my role and take something less challenging.”

“Vicky Larson is going to like that.”

He knew about my rivalry with Vicky at the office. I would imagine most people who work there do.

“She is welcome to it. I am trying to re-evaluate my priorities, Sir.” I apologized this time for calling him sir.

“That is okay, I am your handler after all.” He smirked.

I was pleased that his mood had improved. We were almost to 42^nd street. “I should call my son to find out the rules for this date.” I announced as I began to scan through the older phone for my son’s number.

“Don’t you think you should ask me permission?” Jerry was amused and he was testing the waters to see if I would let him have authority over me.

“Oh I am sorry Sir, may I please call my son to find out how he wants me to behave for my date, so that I am not a rude girl?” I sounded submissive but like someone who was over-acting the part. I was being playful with him.

Jerry laughed and nodded. He was lightening up his mood. “I thought somehow this was an elaborate joke on me. I guess you are for real. Am I a permanent handler?”

I held up a finger the way people do when they clearly have their phone to their ear and need to talk. I hate when people do that. I didn’t even want to think about his theory that somehow we had gone to a porn store, stripped naked, been humiliated in front of him and done all of this in order to play a joke on HIM?

“Hello?” Chris answered the phone.

“Hi Sir, I am on 42^nd Street for my date. Can you give me my instructions?”

He told me the address and who I was supposed to see. He went over Bill’s new rules that we added today and said that he had spoken to the guy who was taking me out.

I asked how Jamie was doing but Chris cut me off. “If I wanted you to know, I would tell you Cunt.” After a short pause he finally said, “We’ll find out soon enough.”

“May I throw this cup away, Sir?” I didn’t even want to look inside the Arby’s cup I was holding.

“Your lemonade and chocolate Sundae? Why would you want to do that?”

“Very funny, sir.” I didn’t answer his question because I honestly didn’t know what to say to that.

“You will carry it for the duration of the date unless you are told otherwise, by your date. I am promoting him to handler for the duration of your first night. I think he gets the jist of things.”

Chris wasn’t particularly filling me with confidence that he had gone over all the ins and outs with me or my blind date. “How do I get home, Sir?”

“Excellent question, He doesn’t have a car and it is going to be late. So he is going to take you to Cambier Park and drop you off.”

“I am just supposed to wander around the park at night, Sir?” I was worried.

“Heavens no!” Chris assured me. “You will thank him for the date, and surrender your clothes to him, so that you aren’t tempted to do that.”

I was hoping Chris was kidding. I am sure my eyes had gone as wide as that young guy who was too afraid to kiss me at the fair.

“He will secure you at the park some place secluded and Dad or I will pick you up before it’s light out. I assure you, no dog walkers will find you.”

“Sir, that is fairly extreme.”

“You want to earn those W’s don’t you slut?”

“Yes Sir” I didn’t sound convincing I am sure.

“I think we are here.” I had been scanning for the street address my son gave me. I asked Jerry very politely to stop and let me out.

“Ask Jerry for the key so you can give it to your date.”

“He wanted to ask you about that.” I was going to ask Jerry’s question about the nature of his being my handler, but my son told me something was going down and he had to go. The line went dead right after.

“Talk about a small world. Your date lives right near my ex-wife. I sure hope it isn’t her boyfriend.” He laughed.

“If it was she would probably leave him. That is good news for you, Sir.” I laughed in response.

He got very serious as if I had just stepped on his toes as he pulled into the drive way of the house I needed to go too.

“If I offended you, I apologize, Sir.” I wasn’t sure what I had said to offend him, but I was genuinely sorry for hurting his feelings which I can honestly say I am not sure I have always been that worried about Jerry’s feelings.

“You make it sound like I can’t get my ex-wife back unless her boyfriend is a total jack ass who cheats on her.” He said wistfully.

As little confidence as he exuded I was inclined to say that might be a true statement. Instead, I diplomatically apologized again as we stepped out of the car.

“You are carrying that cup to your date?” He chuckled.

“Yes Sir, my son’s orders.” I shrugged to imply I wasn’t sure why he wanted me to do it either. I knew it was to humiliate me, that much was obvious.

“You never met this guy?” He seemed to be dragging out the conversation as we stood on the driveway of my date’s house.

“No Sir, it’s my first ‘date’. Jamie has been on several, but I didn’t have to until tonight.”

“What changed?”

“I really do have to go, Sir.” I needed to excuse myself. I could be punished by my date for being late.

He offered me an awkward hug. I accepted and it felt like he was being clingy which only made me pity him a little more for his loneliness.

“I hate to ask this, Sir.” I swallowed.

“You want me to punish you before your date?” He laughed.

“No, sir.” I tried to be sensitive to how I was about to say what I had to say.

“You want to suck my dick real fast?” He was in a good mood and I felt he probably would have let me this time.

“No Sir, I have to ask for the key back. My son wants me to present it to my date.”

I saw his smiling face evolve from happy, to confused, to ‘what the fuck?’ to disappointed and then to angry for a brief moment before returning to the wounded and skeptical Eeyore he presented to the world.

“I tried to ask him if you could be a permanent handler, Sir. I promise I’ll ask him in the morning. I’d rather you than Steve!” I promised him. “It’s just that without the key, I can’t pee or shit if I need too.”

His skepticism remained and he asked “You would really rather have me than Steve?”

The question made me feel like he needed constant reassurance. “Please Sir, let me get to my date before I get punished.”

“Sure, fine.” He handed me the key as we walked up the steps to my date’s door.

“You don’t have to escort me all the way to do the door. It might make him nervous, Sir.” I was clutching my cell phone and the Arby’s cup. If anyone was nervous, it would be me.

“I thought you were walking me to the door.” Jerry looked at me as if by staring intently he could discern whether or not I was lying.

“Is your wife’s boyfriend named Sheldon?”

“Sheldon!?” he exclaimed.

The door opened and out came a boy who couldn’t be much older than Gerald. I should have known Chris would set me up with one of his friends from school. I thought perhaps he had some craigslist hook up that he had advertised me on.

I am sure the smile on my face looked ridiculous and fake.

“My son?”

Sheldon looked at his Dad and then back at me. The thought that ran through my mind was a vision of the two nerds who had invented a hot girl with their computer in the movie ‘Weird Science’. She was supposed to fulfill their every wish.

Sheldon looked every bit the part of Wyatt. He was the one with the sadistic older brother who said “You spit in this?”

It makes me feel old to say this but that movie came out when I was still in high school. My older sister whose name just happened to be Lisa like Kelly LeBrock’s character in that movie used to dress and sometimes even act just like her. She always had so much confidence and sex appeal, but what I remember most of all was the big hair and shoulder pads.

My younger brother would quote the movie, usually the lines from the older brother. “Looks pretty good, now make your own! Dick Weed.”

My brother could be where Chris gets his strange sense of humor from. I can’t imagine a quote like that making me laugh now that I am older. That isn’t true I suppose. Chris can crack me up with some of his crude jokes.

Sheldon’s mother was at the door along with what must have been her boyfriend. They were more interested in why Jerry was running behind with his child support check and launched into a shrewful tirade about how he had made them wait for the check and he should have mailed it instead of bringing it over this late.

I felt a little sorry for Jerry, but considering what awaited me tonight I probably should have wished to trade places with the poor little man. I stood there feeling completely out of place, but being ignored by their domestic squabble. I suppose I should be thankful to have never gone through a messy divorce.

Sheldon led me away from his house by my hand like a perfect gentleman.

“Won’t your mother wonder why a woman her age is leaving with you?”

“I told her you were taking me to a birthday party for your daughter.” I rolled my eyes, but he didn’t see. I could picture my son’s face picturing my face right now. I bet he had a pretty good laugh at my expense.

I felt disgusted to be involved in that lie. I suppose I should be realistic, it’s not like his parents would be as dumb as Gerald’s parents to think a much older girl like my daughter would be interested in their son.

Their older son, now that was a catch and a half. I probably shouldn’t be such a shallow person, but if Chris had brought a girl like Jamie home when he was in 8^th grade I would have known something was wrong immediately.

“So where are we going, Sir?”

“Hand over your key.”

I was reluctant to give it to him. I had never met him before and part of me suspected once he got it he would just say, “Ha ha, I got you now bitch!” as he showed it to me and then ran for who knows where to leave me stranded all night.

The security blanket of having a purse and knowing I have my house keys and can get into my house, or the ATM card so I can get cash as I need it is a wonderful thing. I felt vulnerable without them.

“Chris said you would be like this. He told me to establish who was the boss right away.”

I hid my smile. This pimple faced kid was telling me he was going to establish who is boss? Only if I let him. He had just told me what he was going to do before he did it. I didn’t get to my position at work by being easily manipulated and out negotiated.

He produced a thin aluminum rod he must have shaped from a coat hanger. He must have been carrying it with him and sliced into the back of my leg with it several times.

I yelped in surprised and tried to block the surprise attack to my rear with my hands.

“He said you would do that too.”

“When my son punishes me, it is because I did something bad. It isn’t just a random attack.” I rubbed my sore leg.

-Swack-

“That is for not calling me Sir!”

He had me there, I hadn’t called him Sir. I nodded my acceptance of that swat as we walked down the sidewalk on 42^nd street.

“May I ask where we are going, Sir?” I had been enjoying the silence and the night air, but my mind was buzzing with questions. I think most of all, I was worried about what was happening to Jamie at the high school right then.

“I am going to set the tone for who is boss.”

“How are you going to do that, Sir?”

-Swack- Another strike to the back of my legs.

“When I want you to know, you will know.” He was pretending to be tough, possibly even sophisticated. This was in stark contrast to his father’s lack of confidence. I was surprised such a skinny and nerdy kid had developed that much swagger. When I was growing up, he would have been labeled a geek and ignored by everyone except other geeks. My generation was more into labels and cliques I suppose than this one.

You know you are getting older when you start to refer to it as “my generation”.

“How will I learn, if I don’t ask questions about my lessons, Sir?” I was using that ‘submissive, but over-acting’ voice I had with his father earlier in the car. It felt a little patronizing but he seemed to buy it.

“Okay, I concede your point. Chris told me you were different than your daughter. He said I would have to handle you a little differently. I see what he meant.”

“You have dated my daughter, Sir?” I wondered if he was a repeat customer. I had a hard time believing this kid knew how to handle a razor and shave his chin hair, much less a woman. That is the funny thing about age – When you are young you think you know it all. This kid was full of his own bravado.

Then look at his father. Jerry has the experience with women and he lacks the confidence. I suppose that is the irony of life. You think you will succeed before you try. Then fail a few times and you think you will fail before you try.

“No, but I took pictures of her playing with herself, and she sucked my dick today.”

I saw where the swagger was coming from. One thing that hasn’t changed since my generation is the confidence a boy gets once he gets a little attention from a girl for the first time. Unless I missed my guess, from how he bragged just now, my daughter was the first girl who paid him any attention at all. Now he was King shit, the cock of the walk, a legend in his own mind. I wasn’t going to rain on his parade and burst his bubble that it wasn’t going to be that easy with pretty girls for him in the future. Why should I? He will find out on his own, in his own time.

The community I live in is built around a gorgeous 18 hole golf course. We were walking past one of the fairways along the sidewalk when he directed me behind some bushes over to a wooden shed.

It was decorated like a cabin and inside was probably some electrical switches or whatever it is they want to hide from golfers to avoid spoiling their illusion. I had a feeling this is where he was going to ‘lay down the law’ and establish who was the boss.

“Strip”

I wasn’t sure what the rules were about public indecency. “I don’t think you can order me to remove all of my clothes, Sir.”

He struck me with that damned wire hanger again. I almost laughed because I thought of that movie Mommy Dearest where the woman is running around “No more wire hangers!!”. Damn right, no more of those, please! Lol.

“Do you want me to call your son?”

“No sir, this is my first date, and I don’t know all of the rules.” I pulled off my tube top. It was dark, secluded and we were alone. He was going to see my tits anyway, I was sure of that.

-Schwack- the next hit was harder than the last few.

“Do you think I am going to order you to do something you aren’t supposed to do?”

“No Sir” I was stepping out of my skirt. I could see the look on his face as he looked at my naked body, lit up by moonlight. We were only about 30 feet from the road and while the bushes blocked the view from cars that might drive by, the street lamps overhead offered some light as well.

“When this is all over, I can recommend how many letters you get. So you be good to me, and I’ll see what I can do for you? Is that understood slut?” Now that my skirt was completely off he aimed much higher on my ass cheeks with his metal rod.

“Yes Sir, thank you Sir”

“Turn around so I can unlock your chastity belt. Interlace your fingers behind your head.”

Interlace. That is a word I hadn’t heard before in this context. He was a smart kid.

“May I set down my stuff, Sir?”

“What is it you brought, slut?”

It was dark so I wasn’t sure if he saw the shade of red I turned in embarrassment. “My cell phone, my clothes, and this cup, Sir”.

“What is in the cup?”

“My piss and shit, Sir” I couldn’t believe I managed to say it so cool and collected.

He stifled his laugh at my expense. “Why do you think Chris made you bring that?”

I wasn’t sure but I went with an answer from my affirmations since he seemed to be asking questions along those lines. “To remind me that my ass and cunt are not precious gifts, and how full of shit I can be Sir.”

He nodded at my answer as if he expected to hear that. I wondered how much my son had told him about me and what to do. “Put the cup between your fat tits, don’t hold them with your hands. What is the command? Clench?”

“The first command is ‘Spread’, Sir.” I told him politely as I pulled my tits apart so he could put the Arby’s cup right between my boobs.

“Clench” he ordered and I closed them around the cup, praying my cleavage would hold it in place or else it would splash me in the face.

“Turn around, get your hands behind your head. I want to inspect the goodies.”

I waited while he fidgeted with the key that unlocked my belt. Even if I managed to get the key, there would be no way I could unlock it myself. The lock had obviously been placed in the center of my back and I’d probably pop my arm out of joint trying to reach back there.

Once he had it, he pulled hard forcing the first three bulbs of the metal plug out of my asshole. “eeyow!” I let out a small yelp. “Please Sir, go slow.” I begged him.

He took his time and watched as each of the remaining anal plug bulbs passed out of my ass. I am not sure what it looked like, but not having been permitted to wipe and having jelly back there I felt ‘slimey’ and crusty. He set my chastity belt down in the grass.

“Legs apart. Let me see position one.” He sounded a little less confident as he gave me that command. It could have been that he was surprised I was actually going along with all of this. Then again he had seen what my daughter did and so he probably wasn’t too shocked I would do it all too.

I stood up straight and pushed my shoulders back. I was careful not to drop the cup that was precariously staying in position between my chest. I put my hands on my ass cheeks and pulled myself apart as I bent at the knee slightly. I could already feel my asshole was very sore from wearing the chastity belt and it felt very different to be without it. I wouldn’t call it a “free” feeling as much as it was vulnerable.

He got very close to my asshole. I don’t know exactly how close because I couldn’t see him but I could feel his breath on my sphincter.

“Nice butter cup.” He commented. “Just like your daughters. You should be proud.”

“Thank you Sir.” I answered wondering just how many of these I’d have to go through next week. I was exhausted from the fair the night before and a full day today. I just wanted to go home, even if I had to sleep tied up on the floor.

He touched my ass very delicately and ran his finger down my crack. “Is this poop?”

“It could be Sir. I wasn’t permitted toilet paper earlier when I shit.” I couldn’t see his face but I hoped he was suddenly grossed out. I added, “It could also be lubricant from the plug I wear up my ass, Sir. Taste it, if it tastes like strawberry, that is what it is.” I offered in as sweet a voice as I could muster.

“You think I want to taste your ass?” He sneered from behind me.

“You might Sir. Some guys enjoy it.” I had learned that at the Office. Some guys are complete ass men.

“Gross.” He declared. I had a tiny smile on my face at how naïve he seemed about the body. “You want to taste it?”

“If you want to know what it is Sir, please stick your finger in my mouth.” I knew I’d have to be nice to him anyway. I might as well be compliant. He wasted no time sticking his finger in.

I sucked his finger like I would a dick. It was strawberry coated that was for sure. I didn’t let go, I kept his finger in my mouth greedily. I thought if I could get him to cum this way, he might stop being so cruel. He came around to face me as I puffed his finger in and out of my mouth swirling my tongue around.

“Your body is good, but you have a horse face.” He said bluntly. That really hurt my feelings. “You look like Sarah Jessica Parker.”

I had never been told that. If anything I would prefer Kim Cattrall. In the face, I am definitely more of a Samantha than a Carrie any day. What a horrible little snot to call me a horse face and ruin the sexy mood.

I stopped sucking his finger, but I remained submissive in attitude. “It’s strawberry, Sir.”

“What if it was your poop?”

“Then I would taste myself, Sir.” I answered honestly. I was going through all the celebrities I’d ever been compared too. I’ve heard Bree from Desperate Housewives and back when I was a full brunette I heard the wife on “Everybody loves Raymond”. I have never heard Carrie. That was a low blow.

“Did you enjoy getting those piercings?” He asked changing the subject.

“May I ask if you are trying to give me an affirmation, Sir?” I asked. You notice I said “Trying”? I was willing to give the little punk his ‘moment’ of authority. Calling me Carrie though, I thought I would throw a tiny little dig his way by inferring he wasn’t very good at giving an affirmation if he was doing so.

“Chris told me you need affirmations to adjust your attitude and make you think about your place. I’ll give you a choice, twenty swats with the rod” he dangled the wire hanger in front of me and cut the air with it menacingly. “Or you can choose affirmations, but if you bore me while we do it, I’ll give you fifty swats.”

“Which body part, Sir?” He asked me to clarify what I meant and I said “Which part of my body would receive the twenty strokes?” I sounded much more brave than I really am I am sure. It was part of my strategy to not let him see me squirm too much.

“Your boobies, I guess.” He named the part of my body he was looking directly at.

“Could I set down the cup before you start, Sir?”

“No.”

“Then, I will take the affirmation.” I would have picked the affirmation anyway. I felt that was far less painful. I just wanted to make it seem to him that maybe he was not intimidating me. He shouldn’t have been able to intimidate me, but naked as I was in the night air with my hands behind my head, he was doing a fair job of it.

“What is position two?”

“I bend over at the waist, and keep my hands behind my back holding my ass apart Sir.”

~swack~ He gave me another swat on the ass. “I want to see it, not hear about it.”

He hadn’t told me to get in the position, he had asked me what it was. I felt like he was playing a game of sexual simon sez with me and I was losing even though I was following the rules.

“I need to put down the cup, Sir.”

“By all means, set it on the ground and when you bend over, get your nose right above it.”

“If you wish Sir,” I was very flexible from Yoga and exercising for years. I could bend over and get my nose right above the cup. I was regretting having that skill as I inhaled my own stink.

“You don’t like doing what I tell you?”

“I am your obedient date, Sir. I will be well mannered and behaved tonight. I don’t prefer to be standing here like this, but if you want a good look at the tattoo my son bought for me last night, it would be greedy of me to want to deny you as long as a look as you want.” I figured it would be best if he did take a long look and get the curiosity out of his system.

I assumed he had his cell phone out and was probably taking pictures or video of me. When this began I was worried about Bill’s affirmation videos ending up with my parents, but we had done dozens of dares and been captured on people’s cell phones. I stifled the urge to beg him to keep the video for himself and his friends, because I knew it would be pointless. Chris had probably talked to him about it anyway.

“Why did my dad drop you off tonight?” I wasn’t sure if he knew why or he was genuinely curious.

“I didn’t know he was your father until after we arrived at your house, Sir. I met him at a porn store where we bought the chastity belts and he agreed to bring me here so I wouldn’t be late for our date. He works with me at my Office during the day.”

“Cool, dad hangs out at porn stores?” His question seemed rhetorical and I didn’t answer. I realized I had goofed and let the cat out of the bag about his dad’s night job. The less I said about that the better for him and his father I thought.

He got right up next to my pussy lips and I could feel his hot breath on them. He took a picture with his cell phone and asked, “Who has the prettiest pussy, you or Jamie?”

He wasn’t making me feel as embarrassed and thoughtful as Bill and Chris did with the affirmations. They could make my head spin and swim with impossible questions where nothing was black and white. These seemed more random. I cut him some slack, he seemed to be doing better than his father probably would have in the same position.

“I don’t know Sir. You saw both of our cunts. Whose do you think is prettiest?”

“Your lips are nice.” He said and I smiled. “Jamie’s pussy though is perfect in every way. The only thing I don’t like is that wad of brown flesh that has been pulled out of her otherwise pristine pink pee hole.”

Once again he insulted me and once again I let it hurt me. I think when Bill and Chris do it, either I know they really love me or it feels like I deserved to be called “Cow Tits”. When this little bastard did it, it just hurt my feelings and self-esteem. “I am glad that my pussy lips are pretty to you, Sir.”

-thwak- a rod lashed out against my ass cheeks. “What kind of lips?”

“Cunt lips, Sir.” I had goofed that time. It was difficult to call it a cunt all of the time. It was a word that still felt alien to me to say about myself. I was getting much better about it. “Thank you for reminding me that other women are allowed to call it a pussy, but because of where I am in life, I just have a fat cunt.”

“Is it wet?”

I wondered if he would even know what a wet pussy felt like before. “It is not yet, Sir. I was a little wet from the French tickler in my chastity belt when we were walking but I think I am over it now.” I could have put on a little girl voice like my daughter and pretended to be gushing over him, but he had called me a horse face with a pussy that wasn’t as pretty as my daughter’s. I would comply with his orders but I wasn’t going to overdo it.

“This is boring me.” He announced and just began whapping my ass with the coat wire hanger. I wanted to tell him how to do affirmations with more bite. I wanted to tell him to slow down between swats and let me thank him and count. I didn’t do any of those things. I just let him wail on my ass as hard as he wanted. I thought he had drawn blood because the pain was unbearable, but it was just my sweat.

When he finished he must have done at least 40 swats. I felt like I was hyperventilating I was breathing so heavy. I had not even bothered to try to count he had done such a brutish job. I wasn’t going to remind him he had promised them on my tits for fear he might start over. “Thank… (huff)… You… (huff-huff)… Sir” I wheezed.

“Why do you thank people who hit you?”

“In this case, because you are trying to teach me to be more entertaining and for your time and attention to deliver a painful lesson, Sir.” That was a variation on something Bill had asked me earlier in the week and I was ready with a response. It seemed to impress him that I was so prepared with answers. I think he thought I had everything figured out. I was really flying a lot of this by the seat of my pants (metaphorically, obviously I don’t get to wear pants).

I hated not to plan, but I was in no position to make plans. I just had to hope Bill and Chris had planned things. My mind wandered back to Jamie’s plight. I wondered if half-time was over already and if she would end up suspended from school. It seemed inevitable that would happen if she went through with it. Knowing Jamie as I did, I didn’t expect her to give up once she set her mind to it.

The pain had already subsided and was now an afterthought. I felt like I was this big oversized toy to a boy I had never met.

I was surprised he was so bold with me. He put his pinky finger through the hood ring on my clit and twisted it around from behind. He seemed to have no inhibition about touching me any place on my body and no sympathy what so ever for my feelings.

Chris had coached him well.

He finally let me get dressed and I thanked him for his attentions. “Would you mind spitting on my asshole, Sir?”

I want to say I hate to ask, but I have to admit I got a charge out of seeing his reaction. His expression said “really? You are that nasty of a slut, you’ll ask me to hock a loogie on your ass?” That is what I read into it anyway.

I probably could have just spit on my hand and rubbed it into the plug before pulling myself back onto the backdoor penetrator I would be wearing from now on. He had already seen me humiliated.

Who am I kidding? I was going to deny him the pleasures of watching me beg and squirm moments earlier. I hate to admit this but I think the sudden pain of the spanking had turned the tables on me and I was looking at him through eyes that saw my superior. I was treating him like Bill and Chris.

Isn’t it funny that all it took was one little wire hanger?