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Casey was older for a student - in her mid 30's. She had married early on - had a child, but found a loveless marriage was not for her. She felt worthless and unloved - and when she first attended my class, i knew there was something special about her.
As a Counselor, i mainly see people who come in for sessions. As I found out during my development of Casey, she would have done well in therapy, but instead, we met as a Professor and student.
I had been approached several years ago, by a friend, who said a local adult oriented business college was looking for Professors with real world experience - He asked if i would be interested in teaching a management class, and another about psychology - as part of a basic degree requirement for those to learn.
I enjoy working with people, and most of the time there are lines i cannot cross with patients, so, i eagerly agreed to put together a curriculum, and i began teaching.
What is nice about teaching at a for profit, adult based college, is that you don't have the spoiled little stupid kids who are just there to drink on mommy and daddy's dime. I teach classes for those who are either already working, or wanting to go back to finish their degree, to have an opportunity to get out of their crappy hourly pay job to get a career.
That is when i met Casey - as she came in for her first night in my Psych 101 course.
She sat all the way in the back, and after several classes, had hardly said a word. Her homework was passable, and she did ok on the tests, but nothing outstanding - but she had face and a body that attracted me, and frankly i looked forward to having her there. She had what i assume she would think is a mommy body - one that had not changed much after having a child - but she had a fine ass, and lovely firm and full tits. Two areas of a body that i enjoyed working with - to extremes.
As the semester continued on - her grades began to slip, her assignments more shoddy, and frankly i could see she was barely getting the work done, even at a passing C level.
I decided to have her stay after class, to find out why.
I must say, there was an intensity for me, as she nervously sat down in front of my desk, fidgeting, looking down, all signs of submissive behavior.
I decided to push right away, telling her i was sad and disappointed in her. That when she first attended my class, her early work showed promise - but yet it seemed she wanted to waste my time and hers with lackluster work.
She was close to tears - as she apologized, saying work, and raising her daughter was difficult, only getting time on the alternate weekends, when her daughter went to her fathers, to try to do her schoolwork. When she finally started crying, she described that she was lonely, and felt she had not life, except for raising her daughter.
I handed her a tissue, and remained quite - looking over her body. That night she had worn a skirt, and i enjoyed looking at her legs. Her tits were moving up and down with each sob, and she was lovely to enjoy - even more so that i saw she was needy and vulnerable. I waited until she had stopped crying.
Pushing her a bit - i told her that was quite a show. To start off firm, push, and then maybe give her hope.
I told her to look at me - and then began telling her that while she was a lovely woman, and i believed intelligent, that feeling sorry for oneself, being lazy, was not only shameful for her, but what was she showing her daughter. I told her she was undisciplined, and if she didn't have the ability to push herself, to set and accomplish goals for herself, then maybe she needed someone to do it for her - bottom line i told her, she was wasting her time and money, and my time.
She began to shut down again, and that is when i took a break from that, and asked her about her home life. The story poured out - married a guy, dropped out of college in her 2nd year, he ended up being a different man than she hoped - and once she got pregnant, he began cheating on her. The only good thing was he had a good job, and the alimony and child support helped, and allowed her to go to school.
I sensed a strength, and a desire for someone to give her attention, and she was perfect for what envisioned could be. So I offered rope, to see if she would take it.
I softly stated - that maybe i could help.
She looked up at me - and i have to say, the look of a tear stained cheek, a bit of ruined makeup, looked sexy to me - to imagine creating more of that - in a different way.
I cleared my throat and said, i normally don't offer help, when i sense someone has been lazy or unmotivated, but i sense that thinks have just piled on, and that maybe she has just lost her way - but maybe with the right person pushing her, she could find her step again, to find out who she was a long time ago.
Casey began noddiing.
I told her when she came to class next time - i would give her an extra reading assignment - and then a paper would be due based on that - and if she did that, and did it well, and was honest with me - maybe i would consider more personal tutoring, helping her in all of her classes, but mainly working to help her find her motivation - one way or another.
At the end of the next class - i handed her a book, an older one, classic, basically about a younger woman and an older man, how he helped her grow to be who she was - but, there were many times in the story where a firm hand was needed - where no long being a child - the woman was made to do penance for being lazy and wrong. Everything from writing lines, to being put over the man's lap, punished, hand spanked, even harder punishment when needed, and even naked corner time.
I handed her the book and suggested she read it - and write me a one page paper, a summary, and her thoughts if she felt the woman was handled properly, and if she felt that would work for her. It is always interesting when a woman reads it, how she will go. At first the thoughts are - "i am not a little girl" and then they either feel the ideas and actions are beneath them, or the thoughts and ideas become part of their waking mind, and then, if it begins to affect their body - i know that they can be developed that way - pushed to any limits.
I also suggested that she work to prove to herself how lovely of a woman she was - and that i felt she should wear a dress or skirt all the time, a blouse that showed off her figure, and to let her hair down more often - that she would no longer be a divorced mom, but a beautiful woman.
As she left, i looked at her lovely plump but firm backside, and imagined it being nice and red from a handspanking - and wondering if the bait on the hook would land her properly.
I got busy in my week and other classes - and just as Psych 101 was about to begin, and the door popped open, and in came Casey, a bit flushed due to almost being late. I smiled as she took her seat, in a nice skirt and blouse that accented her body, and her hair was done nicely - such a promising start. I had on purpose, set aside time after class, to see the reaction and the summary assignment given - i liked how it began.
After a good class, filled with thoughts and ideas and a bit of teaching about the basics of psych, class ended. Casey sat in her seat, acting like she was fumbling in her leather carry case, as the others filed out of the room. When the room was clear, she got up, smoothed her skirt and came up to my desk, i smiled, told her she looked lovely, and bid her to pull up a chair and sit.
I sat back, waiting for her to make the first step - she cleared her throat a bit, and then, opening her carry case, she got out the book i loaned her, and handed it to me, and then pulled out her summary assignment and handed it to me, blushing.
Prior to looking at her assignment - i asked her what she thought of the book.
Blushing more, she said that it was very intense, and that it seemed the woman in the story benefited from the, er, motivation.
I nodded, and began reading. The first part was just a summary of what happened to the woman, and then as i read, i saw some very good insight to her, where she stated that, in fact, while she assumed the woman was embarrassed, that she herself felt that someone who cared enough to hold her accountable, to provide guidance, in a variety of ways, would be very helpful to her.
She was a bit vague in the ways of being held accountable, but i understood it was probably the very first time she encountered those ideas - so now, to push and see if she would be what i imagined she could be, for me.
So, i looked at Casey, and told her it was a nice summary, but not much in detail, in what happened to the woman, or what she actually felt would be beneficial for her - so i pressed her.
I asked her what areas of her life did she feel that she needed guidance in.
She began by talking about time frames, to be kept on time with assignments, for work around the house, to not procrastinate, and she also said she wanted to work out, to get in better shape, to diet, but was very lazy to that - all of these things she said she needed someone to be stronger about it with her, than she was.
So, i then asked, how did she expect that someone, like me, would hold a woman, like her, accountable.
Blushing, looking down, she mumbled, "Punishment?" in the form of a question.
I firmly told her that this was a prime example of her laziness - and what a worthless answer that was.
So, i asked again, what she felt was proper punishment for a woman like her - being lazy, needing motivation. I told her i could describe my thoughts, but then that was "me" doing something to her - it needed to be her, telling me what she needed, what she deserved for being lazy and not attaining her goals.
She looked down a bit, and then looking up,said spanking..... then got quiet.
What kind of spanking - i inquired
Hand spanking was brought up. I told her does she really think that a periodic hand spanking was what she needed? She shook her head no.
What types of items can be used to punish a lazy woman i asked her.
Knowing the items from the book, she began to describe a hair brush, a paddle, a leather strap, even a cane and a riding crop.
Would those be effective to motivate you? She nodded.
I asked if she had ever been punished - and she simply said "some" as a child and into her teens, but not much.
I then told her that could be the base of the problem - that her parents stopped too soon and were too easy on her. I then asked if her husband held her accountable - and she shook her head no again.
I finally said - was she interested in having me help her. That i would not let her be lazy, and she would participate in her goal setting, but that once consequences were defined, she would have no say in them - did she want that?
Casey nodded - so i asked if she was dating someone ..
I told
I put more emphasis in my tone, and told her, that i didn't want some stupid boyfriend upset with me, because you were being lazy, and i had to whip you, leaving marks.
That impacted her for a moment - and I pushed.. I told her that she read the story, and that she felt that could help her life - and that if she wanted my help, she had to understand that there would be punishment for being lazy. That over time maybe there would be rewards - but i could sense that would take time to come to fruition.
I sat back, and asked her simply, did she want my help.
She slowly looked at me, understanding the weight of her answer, but bravely nodded.
I told her to write her address down for me - and told her i felt that we should meet every two weeks - at her home. Her daughter would be away - but then i would be able to inspect her home, to see if her goals of housecleaning were accomplished, and then we would use her scale, after we defined her diet and workout goals, and then we would sit down, go over her finances, and then her school work. Once we knew the state of things, we would enter to the punishment phase of the day.
She asked, why did i assume there were be punishment?
I chuckled and then asked, if i came to her home tonight, was it clean? Laundry done? Were there clothes hanging on her treadmill? Were all of her bills paid?
She dropped her head and shook it no..
I told her that is why i felt there would usually be punishment, but then i hoped it would evolve to rewards.
When she handed me her address, and she confirmed the next weekend that her daughter would be with her father, i told her i was proud of her for this first step - ad that would be there at 11:00 on that day.
I found myself looking forward to that first Saturday - this would determine how much Casey was ready for - and good be trained and developed.
As i knocked on the door, Casey looked out of breath, but was wearing a nice sundress and white socks and tennis shoes. I like that type of spring summer mommy look. Her legs looked wonderful and her tits were nice and full, showing from the several unbuttoned buttons. I walked in and stood in her modest living room, looking around.
I smiled, and then said to her, that she should give me a tour. She walked me through to the kitchen, and was surprised when i looked in the sink, and then ran my fingers over the counter, and then told her the kitchen looked ok, not bad, but not a detail cleaning. She walked me down the hallway, and i looked in the laundry room, a pile of clean towels not folded, and several baskets of dirty clothes, not yet cleaned - i looked at her and merely said it seemed she was a bit behind.
I asked her when she dropped of her daughter to her husband, and she said on Friday night about 7:00. I nodded and continued.
We got to the bathroom - not too messy, but not detail cleaned and then i saw her daughters room, messy as a kids will be, not dirty, just stuff around. I asked her daughters age, and she told me 10. I nodded, and we went to her bedroom. Again, not bad, her bathroom was a bit jumbled with a hair dryer and curling iron, make up out - you could tell the mirror and sink had not been detail cleaned in a while, and then in her bedroom, i looked in her closet, and it was immediately obvious that she had shoved a bunch of dirty clothes in there.. and then i went to her nightstand, and she gasped as i opened it, seeing several vibrators. I laughed and said, i can see you take some time to take care of things yourself.
She blushed and nodded - i bid her to make me a cup of coffee, and to sit down so we could discuss some things - i also asked her to bring some paper and a pencil or pen.
As Casey sat down, a bit nervous, i sipped my coffee and began.
I told her that she had a lovely house, and i am sure things are hectic. But, i told her, the kitchen and bathrooms were not really clean - it was obvious there was not a regular cleaning schedule. I asked her when she last masturbated. She dropped her head and blushed.
I became more firm - i told her there would be no secrets between her and her disciplinarian - and again asked not only when she masturbated last, how often did she do it?
Trembling now, she told me she masturbated last night, and usually, she whispered, about every other day.
I sat back, sipped my coffee, and said, it seems that her own pleasure was more important than keeping a very clean home for her and her daughter, and that while she was making herself cum, she could have instead folded a load of towels, or cleaned a bedroom, or even cleaned the kitchen better. I told her we would discuss things more in detail later - but that i wanted to go through and have a list, in her writing, for her goals.
We discussed that by every Saturday that i would come by, that the house would be much cleaner, that there would only be clean and folded laundry, and that her bedroom and closet would be immaculate - i told her i would also expect her daughters room to be less messy, but that i expected her to have that discussion for her daughter to do that work as well.
Finally - we decided on a weekly goal of her walking on the treadmill, her goal for weight loss, as well as i would expect to see the bills she paid, all caught up by that same Saturday - i told her that two weeks to organize, clean, pay bills, and to workout, was very reasonable. I told her if she agreed, to sign her name and to put that up on her fridge, so she and her daughter could see it. .I told her that would be the list i would work from every time I was over.
Casey smiled, seemingly happy that there was a list for her to follow- you could see a form of accomplishment, a path forward.
I then cleared my throat, and asked her, if she was ready to take care of her punishment, to start the process of properly.
She seemed a bit perplexed, and then nervous, as she noted that we had just made her list.
I told her that i was disappointed in the house, and expected better, for my first visit, and that she also needed to learn what would happen if she decided to be lazy.
I told her she had 5 minutes to go to her bedroom, and to put on what i felt was a proper punishment outfit - a simple t-shirt, panties, and socks could stay if she wished - i told her to be speedy. I also told her to tie back her hair, that pigtails would even be best.
I found that if one was made to dress and look like a younger girl, the punishment would help drive that feeling home more, of being a naughty little girl who was to be punished.
I moved to the living room couch when Casey shyly came in to the room, her hair in pigtails. I saw a problem immediately.
As she stood in front of me - i looked at her, and asked why she ignored my request - she had a quizzical look on her face.
I told Casey that i said, T-shirt, panties and socks, then bid her to tell me where she messed up. Her face got flush as she looked down and said, "bra'
Naughty girls don't wear bras, and i told her i wasn't going to work to undress her as her punishment continued - i told her that would add to her punishment, and had her lay across my lap.
As she got across my lap, i moved a bit to get situated, and then i lifted the bottom of her shirt off, and told her, that punishment was done when i felt the lessons were learned, not after some arbitrary number - did she understand that.
She jumped a bit and yelped out a YES when my flat hand came down on her panties, and i knew offering little or no padding for her spanking.
I continued to swat her ass methodically, moving each time a bit, to cover he bottom properly, and then below her panty line, right on her plump sit spot, and on her upper thighs - my questions and spanking continued for about 10 minutes.
Then, taking a pause, i told her to get up, and to then pull down her panties, and wait for me.
I got up and went to her kitchen. After opening a few drawers, i found a nice thick wooden spoon. I knew i would have to give Casey a shopping list of proper implements - but this would do for now.
Coming back to the living room, i saw that she had complied, and i told her to hand me her panties. Once i touched them, i knew we were on the right path. I sat down, and then told her to resume the same position.
As soon as she was over my lap - i lifted up the bottom of her shirt again, and looking at her nice pink ass cheeks, i asked her, why did her panties feel wet?
She trembled, and since she didn't answer, i began firmly spanking her with the wooden spoon. I did not spare anything - and soon her ass was moving to a bright red, and i knew there would be bruises in the morning. I paused for a bit, and asked again, why her panties were wet..
As she tried to find some way to answer - i continued to spank her soundly with the wooden spoon. The the grunts and sounds of pain, soon turned to sobs, and after about 10 minutes more of hard firm swats all over her now red and purple ass, she broke down and began crying.
As i lay the wooden spoon down, i softly caressed her bottom, feeling the heat from her hand and implement spanking, knowing she still needed more to be broken, i asked again softly, why were her panties wet when she handed them to me.
As the sobbing subsidded, she simply said she didn't know why, but that being over my lap, with what has been talked about, that such a time without feeling the hand of a man on her, being exposed to me, affected her..
I rubbed her bottom softly and told her i was proud of her. I then told her we still had a ways to go - that i wanted her to fully understand. I told her to get up, and to go to the wall, to press her nose against it, and to wait for me, as i searched for what i needed next.
As she complied, i walked back to her bedroom, and then in to the spare bedroom that had a desk and chair.
I found some things that would work, but would certainly need to get her to build a shopping list.
When i walked back in to the living room, i put the items down on the coffee table, and told Casey to come to me. Her eyes glanced down, seeing an old tie, i assume from her husband, a soft supple leather belt that i found in her daughters closet, and several binder clips that i found in her desk.
I told her to look at me, and told her, as she did not follow instructions properly, to take off her shirt and bra.
As she did so, my pleasure was complete. I had been looking forward to seeing her tits in full view - and they did not disappoint. Full and firm, very lovely. But not to get her feeling good about herself yet. I looked down, and saw she had hair around her pussy - trimmed - but not good for the mental effect that i needed. Plus i could use the opportunity to break down any modesty.
I sat down on the sofa again, and then told Casey to get on all fours in front of me, but facing the other way. I told her to back up close to me, and then to put her head down on the floor. I then told her to spread her legs wide - making her stretch, until very spread apart, so her pussy lips were slightly open as well. I knew it was humiliating for her, considering until now, she was dressed and sitting in my classroom. I looked down, and using my hands, i felt her warm red ass again, and then worked down the back of her thighs, and then going down to her inner thighs, i turned my hand over and began cupping her pussy.
i could feel her wetness - and her shivers.
I told her - i see i still must not have been firm enough, as she must believe this is some kind of foreplay. I would never give her the satisfaction of knowing that at this point, it became aware i could make her body react from pain, and pleasure.
I also told her, that from now on i expected her to be shaved smooth and bare. I asked her if naughty little girls deserved to have hair - and she whispered "no".
Good girl - i told her, and with that, i began working a finger inside of her - telling her to keep her legs open, i wanted to see how naughty she was - i told her, that i wondered if she masturbated too much, and was more worried about self pleasure - and i told her, if she came in under 3 minutes - then there was going to be more punishment, but that if she was going to lose control, she had to tell me if she was close, and to ask for permission.
With her ass in the air, her legs spread, and her head on the floor, i quickly worked three fingers in to the her soaking wet pussy, and began fucking her with them, as a finger on my other hand found her hard clit, and began rubbing that firmly as well.
I glanced at my watch and at about the 2-1.2 minute mark Casey yelled out - i need, i am, can i cum please?
I kept fingering her firmly, and said, that didn't seem to be good enough of a request - try again.
PLEASE - sir, can i please cum.
How bad do you want to cum naughty girl?
Sir - VERY much - can i please cum.
I smirked and told her she could cum, and as the damn broke and she was bucking on my fingers, i kept up the sensations and told her if she was going to cum for me, to do it right - to cum again. I kept fingering hard.
I knew she was very sensitive, her clit was rock hard, and she then screamed and bucked again, cumming hard - i took my fingers out and away from her, as she collapsed to the floor - her body shaking in the aftermath of her orgasm.
i reached down and patted her bottom - and asked, are you going to be properly shaved as i asked?
She whispered "yes sir"
Good girl - i told her, but time to pay for your earlier transgression - and also, remember, you came a second time, but did not ask for permission.
The look of realization on her face was wonderful.
I told her, she got wonderful pleasure, but if she was going to break the rules, we would have to do something about it. I asked her if she normally masturbates by hand - and she said that she cannot normally cum that way - she needs a toy of some kind.
I logged that memory.
I asked her if she wanted to handle the punishment for the bra first, or for the climax with no permission - she lowered her head and said, "for the bra first"
She had a half-wall between the living room and the kitchen, with a post at each end of the wall, going from the floor to the ceiling - i brought her over to one post, and told her to reach her arms up over her head. I took one end of the tie and tied it around one wrist, then i took it around the post, and tied her other wrist firmly as well. At that moment, her arms were now out of the way and as i walked around to face her, her wonderful full tits were on display for me - and she was helpless.
I looked Casey in the face and told her, that not only punishment for wearing the bra, but that it seemed that she was flirting a bit in class, and it seemed that she always had an extra button or so open. Did she like when other men, and especially me, look at her tits?
She nodded nervously.
I am proud of you - they are beautiful - but they also are part of your body, and that means they are subject to punishment just like your ass, or even your pussy.. Don't you agree?
She was still working to process my comment, or maybe to hear her pussy could be punished also, but she spaced out, so i slapped one of her tits firmly, from one side, then i backhanded her other tit coming back -
I asked her if she agreed.
"Yessss" she blurted out.
Good- i told her - as i began slapping her tits slowly- back and forth, then up and down, for over 15 minutes until they were nice and pink. I knew they were tender already, and that wearing a bra even by Monday would make her feel the punishment.
When i felt she needed a break, her breathing becoming quicker - i told her to spread her legs again - as far as she could.
I felt between her legs and she was soaking wet still. I smiled and told i guess she was enjoying her punishment.
She moaned as i rubbed her nearly raw but sensitive clit. I got my hand wet from her pussy and rubbed it over her pink tits, working her nipples, rolling them between my fingers. Softly at first, but then harder, then pinching them, and pulling and twisting them harshly - hearing her cry out - but knowing she was reacting to it.
I knew i had a budding pain slut on my hands. She would be delicious to develop and train.
Letting her catch her breath a bit more - i walked over to the table and picked up the two binder clips.
I walked back to her, and told her, that i would be getting her a list of things she needed to buy - she could either buy online, or go to a local adam and eve store, but still, she would have a list of things to be required, as our sessions would continue. But, i told her for now, these would work just fine.
How i was going to use them finally registered, and her eyes flew open wipe, she began to say no, and i stopped, and she shut her mouth.
I said, "NO?" - ok..
I walked over to the table and got the wooden spoon that had been used to punish her ass - and i began swatting her now tender tits slowly and firmly with the wooden spoon. after about 15 swats on each tits, with her nearly in tears again, i put the spoon down, and kissed her cheek and told her, that No isn't an acceptable comment. She could say More, or thank you, or harder, but not no.
She wimpered
I got the binder clips - and started with one nipple. i leaned over, and licked one wet, sucking on it, watching it get hard from the sensation. Then i took her tit in my hand, squeezing it, to highlight the outstretched nipple, and then opened the binder clip, placing it over the soon to be punished nipple, and let the binder clip close down cruelly on her tender nipple.
The scream was delicious, and a sensation she had never had before. Women are used to boys or men treat the tits and nipples like some special wonderful thing, when really it was perfect for harsh discipline like any other part of a woman's body.
While her mind was reeling from the first binder clip, i repeated the process and soon she was howling from the second binder clip closing down on her other sensitive nipple.
I walked over to the floor, where her panties were, and i walked back and told her to open her mouth, and i then stuffed them fully in to her mouth. Her eyes were glazing over from the binder clips, and yet the screams were now muffled.
Much better - i told her.
To really affect the mind- the key is to offset pain with pleasure, and pleasure with pain.
I put my hand between Casey's legs again - and began rubbing her clit firmly. then cupping several fingers in her, i worked her g-spot while my thumb worked her clit. I know she must have thought it took forever, as the pain in her nipples were intense, but soon she was bucking on my fingers again - cumming just as hard as she did previously.
I was cute, that when she was about to cum, but with her panties in her mouth, i could hear grunting and the sound of words, probably trying to ask for permission.
I took the panties out of her mouth, and smiling said, i will give you a pass on asking for permission this time.
She began pleading for me to remove the clips.
I asked if they hurt, she said the pain was unbearable.
I stepped back and slowly strummed the binder clips up and down, sending more pain sensations through her nipples and tits.
I then asked her - how many times she had cum today.
She cried out that she had cum 3 times.
I asked her, wasn't that generous of me?
She said yes, thanking me desperately, but to please remove the binder clips.
Almost there i thought - we had never discussed any pleasure for me - but it was in the back of my mind, and so i thought now would be the time to discuss it properly.
So, i told her, you have cum three times. I wonder what i should get in return.
It hit her what i was talking about - but the pain was incredible, and there is a strong bond between the one being punished and the disciplinarian.
She eeked out -"anything"
Anything? i asked of her.. be more specific. What could you offer me,to thank me for all of this hard work to help guide you.
Anything - she repeated. I didn't move to remove the binder clips, and i said, that anything is pretty broad, but i would like to hear more in detail what you feel would properly thank me for helping you so much, and even giving you so many orgasms.
Whatever you want - she pleaded.
Hmm - i told her.. Will you want to suck my cock?
Yes she cried out.
Well, how much do you want to suck my cock? I mean, you have been without a man for a long time, are you any good at sucking a cock?
Please - she begged. .I want to suck your cock. I will suck it for as long as you want. I want to please you any way i can.
Will you take me all the way, even if i force it down your throat? Will you be a good girl and swallow all of my cum?
yesssss - she begged.
So, tell me i said.
Please - i will suck your cock anytime you want - i will suck it so very good, i will take it all in my mouth, you can choke me with it - and i swear i will take all your cum.
If any cum spills out, will you clean it up?
Yes, i swear i will - i wont waste any of your cum.
I had to admit i was so hard at that point - but there was more to negotiate.
So, we have your mouth being offered. That will be good for today. What about your pussy? I was so good to your pussy today - will i be able to enjoy that as well?
Yes - please - you can have my pussy.
Tell me what can i do with your pussy?
My god, the clips hurt so bad - you can fuck my pussy however you want.
Can i fuck you hard? Can if cum inside of your naughty pussy?
Yes, please - fuck my pussy - cum in it.. Whatever you want. whenever you want.
Good girl - now, one last thing - has you ever had a man fuck your nice little perfect tight asshole?
GODDD - no, no man has ever done that..
So, tell me, here and now - what do you think about offering me your ass virginity?
Please, she sobbed, you can have anything - you can fuck my ass if you want.
Tears were rolling down her face from the pain - so as i undid each binder clip, massaging the blood back in to the nipples, knowing that this at times is the most painful part - i then wiped away her tears, and leaned in and kissed her deeply.
I enjoyed hearing her moans. I pulled back and told her she had done well.
I untied her wrists, and i held her - but i also whispered a reminder that she still had one more punishment left - and that was for not asking for permission for the second orgasm.
She nodded properly, and i told her to get on the ottoman, on her hands and knees, then to lower her head again, but to spread her legs wide.
I knew she couldn't take much more at this time - but she had shown me a bit of what she could take, I would continue to be creative going forward.
She looked so amazing on the ottoman - Her punished ass sticking up, legs spread wide, her red swollen pussy so tender from her multiple orgasms.
I told her, we needed a proper leather strap, but that this belt of her daughters would work. As i folded it over in half, i told her now whenever she saw her daughter wearing the belt, she would remember our first day.
I raised my arm and struck her perfect ass with a hard flat stroke.
She yelped.
I whipped her again, and told her, in the summer time, with all the windows open, she would have to decide if she wanted the neighbors to know she was being punished - but for now - she could make all the noise she wanted.
I gave her a total of 10 strokes from the first side i was standing at, then i went to the other side and slowly added 10 more.
Rubbing her ass - i ran my finger down between her legs, and after getting it wet, i brought it up, and told her to reach back, and hold her ass cheeks apart.
After she complied, with her little tight puckered asshole on display - i slowly rubbed it with my wet finger, and then hearing her gasp, i slowly worked it inside of her ass, all the way past my second knuckle.
I loved hearing her grunt as i slowly worked my finger in and out for a bit - telling her i was going to look forward to being the first man to take her there.. That i looked forward to hearing her describe the sensation of a man's cock in her ass, feeling his cum up in her bowels.
She moaned as i pulled my finger out.
Almost done with your session my dear - i told her, as i raised my arm and gave her a slow 10 strokes from each side again.
The portrait that had begun on her perfect plump and pale ass, was now a wonderful picture of red, purple and growing bruises from her days discipline.
It was good that our meetings would be every two weeks, as it would give her time to feel the punishment, and for the bruises to fade, just in time for her next session.
But there was one more final step.
Telling her to keep her legs spread wide, and her ass up in the air, i took her daughter's belt, and holding on to the buckle, and wrapping the belt around once, so there would be a loose end, i swing the belt up and it struck right between her legs. She jumped and howled.
Remember - i told her, you can be punished all over your body.
Now - 5 more and you are done.
One after another, striking perfectly on her swollen pussy - she took all five better than i expected.
There would be no place on her body that wasn't sore tonight. She would now understand how important it was to accomplish her tasks promptly for me.
Not that i would decrease her punishment every two weeks, but there was more that i could do if she didn't improve on her procrastination and cleaning and such.
I put the belt down, and told her we were done - and that i was proud of her, and hopefully today would motivate her to work on the list we had compiled.
When she looked me in the eye, she was a different woman. She smiled, proud of what she had endured, and how she felt, and that she was with someone who cared about her. The change from before was dramatic.
She came up to me, hugged me, and leaned up, wanting another kiss. It was deep and slow. I stepped back and told her to turn around slowly for me.
i told her she had done so well, and that i was very proud of her, and she looked so sexy at that moment. She walked over to a full length mirror in the hallway, and looked at herself, turning to see everything, touching and feeling the tenderness. A smile formed on her mouth.
She turned and came back to me in the living room.
She took my hand and led me to the couch - she slowly unbuttoned my shirt, and took it off, then she undid my belt, and undid my pants, pulling them and my underwear down.
She whispered that i was larger and thick than her husband - she looked up and smirked and said she may be in trouble for the promise of taking me down her throat. I smiled as she pushed me down in to a sitting position.
She then took off my shoes, and socks, and after putting them to the side, slip off my pants and underwear, then taking them and my shirt, she folded then neatly over the arm of the chair.
Coming back and kneeling down between my legs, she took my cock in her hand, and slowly began working me hard.
She asked, while she stroked my cock, if i had imagined this when I first saw her in class. I told her honestly, no, but tat i did admire her body, and her mind, and that was why i felt she was slacking in class, and knew she had more potential.
She told me she was glad that i pushed her - and that while the idea of punishment made her scared, she said she never has felt so alive.
As i got very hard, she asked what types of things would she be required to buy?
I began to go through the list in my head. I told her at least a good paddle, a wooden hairbrush, for sure a trip to the leather shop to get a proper leather strap. I then said a good bamboo rod would be key, for special punishment, and then several plugs for her ass, to help her be trained to take me that way, as well as proper nipple clamps, unless of course she wanted me to just use the binder clips.
She glared at me, telling me they were evil. I laughed.
I then told her that probably a good set of handcuffs, especially with fur or such - and then i told her probably i would look in to a good remote vibrator that she would be required to wear in class. So i could see how well she could concentrate while i had the vibrator in her pussy turned on.
She took me in her mouth, just a few strokes, and then stopped and said that was evil - to tease her during class, so she did poorly, and then to probably punish her at her sessions for not concentrating in class.
I told her she caught on quickly to how she would be developed.
As she took me again in her mouth, now slowly taking me all the way down to my balls, i told her i wanted her desperate for me every two weeks - and very sensitive in class. That when i left her house, i would take all of her sex toys - and that she was not allowed to cum without my permission - but that she would be required at times to touch herself at home, to edge, to bring her self close, so she would be very needy when i was with her every two weeks. I told her she would find her orgasms far more intense.
As she increased the pace and pressure with her mouth, i asked her if she sucked her husband like that - she lifted her head off my cock, and said No, he didn't deserve it. She then took my cock back in her mouth all the way down again.
I told her she had potential - that her mouth was very good - but that i didn't want to cum for 30 minutes, nor could she take her mouth off me - and she wasn't allowed to use her hands. I told her if her mouth came off of me, or if i came in less than 30 minutes, i would use the belt on her ass again.
Casey spent the 30 minutes, increasing and decreasing the speed of her mouth, gauging how close i was to cumming and then slowing down.
Finally, after seeing her glance at the clock on the wall, i nodded, and she began sucking my cock with more intensity. Soon, based on the day, and seeing her body, and with the feeling of her mouth, i told her i was cumming.
I grunted and arched my back, and she pulled her mouth to the end of my cock, and as i began to cum, her mouth filled up and she was swallowing quickly - finally, as i began finish, she pulled her mouth off of me, smiling as a bit more cum left the head of my cock, and spilled on my leg.
She smiled, and leaned down, licking the cum from my leg, and then licking her lips said, I guess i will have to be punished later for that.
She start to get up and asked me if i would stay for dinner, that she wanted to cook for me. I told her that would be wonderful, but to realize that she wouldn't be allowed to get dressed. She smirked and said she assumed there would be some rule like that - but could i please go to the walk in closet by the kitchen, and get a good bottle of wine and open it.
She laughed and said she assumed i would be able to find the wine opener in the drawers that i was looking at earlier.
As i headed to the kitchen, i swatted her tender bottom, and she turned and kissed me again, then reaching down, she worked her hand around my cock and told me, I hope he is able to fuck me properly later.
No worries i told her, i was already getting hard. That unless she was quick with food, she might get fucked over the dining table.
As she went to the fridge, looking at the list already hanging there with a magnet, she said, that will be another good memory for me to have in between sessions.
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Casey was older for a student - in her mid 30's. She had married early on - had a child, but found a loveless marriage was not for her. She felt worthless and unloved - and when she first attended my class, i knew there was something special about her.As a Counselor, i mainly see people who come in for sessions. As I found out during my development of Casey, she would have done well in therapy, but instead, we met as a Professor and student.
I had been approached several years ago, by a friend, who said a local adult oriented business college was looking for Professors with real world experience - He asked if i would be interested in teaching a management class, and another about psychology - as part of a basic degree requirement for those to learn.
I enjoy working with people, and most of the time there are lines i cannot cross with patients, so, i eagerly agreed to put together a curriculum, and i began teaching.
What is nice about teaching at a for profit, adult based college, is that you don't have the spoiled little stupid kids who are just there to drink on mommy and daddy's dime. I teach classes for those who are either already working, or wanting to go back to finish their degree, to have an opportunity to get out of their crappy hourly pay job to get a career.
That is when i met Casey - as she came in for her first night in my Psych 101 course.
She sat all the way in the back, and after several classes, had hardly said a word. Her homework was passable, and she did ok on the tests, but nothing outstanding - but she had face and a body that attracted me, and frankly i looked forward to having her there. She had what i assume she would think is a mommy body - one that had not changed much after having a child - but she had a fine ass, and lovely firm and full tits. Two areas of a body that i enjoyed working with - to extremes.
As the semester continued on - her grades began to slip, her assignments more shoddy, and frankly i could see she was barely getting the work done, even at a passing C level.
I decided to have her stay after class, to find out why.
I must say, there was an intensity for me, as she nervously sat down in front of my desk, fidgeting, looking down, all signs of submissive behavior.
I decided to push right away, telling her i was sad and disappointed in her. That when she first attended my class, her early work showed promise - but yet it seemed she wanted to waste my time and hers with lackluster work.
She was close to tears - as she apologized, saying work, and raising her daughter was difficult, only getting time on the alternate weekends, when her daughter went to her fathers, to try to do her schoolwork. When she finally started crying, she described that she was lonely, and felt she had not life, except for raising her daughter.
I handed her a tissue, and remained quite - looking over her body. That night she had worn a skirt, and i enjoyed looking at her legs. Her tits were moving up and down with each sob, and she was lovely to enjoy - even more so that i saw she was needy and vulnerable. I waited until she had stopped crying.
Pushing her a bit - i told her that was quite a show. To start off firm, push, and then maybe give her hope.
I told her to look at me - and then began telling her that while she was a lovely woman, and i believed intelligent, that feeling sorry for oneself, being lazy, was not only shameful for her, but what was she showing her daughter. I told her she was undisciplined, and if she didn't have the ability to push herself, to set and accomplish goals for herself, then maybe she needed someone to do it for her - bottom line i told her, she was wasting her time and money, and my time.
She began to shut down again, and that is when i took a break from that, and asked her about her home life. The story poured out - married a guy, dropped out of college in her 2nd year, he ended up being a different man than she hoped - and once she got pregnant, he began cheating on her. The only good thing was he had a good job, and the alimony and child support helped, and allowed her to go to school.
I sensed a strength, and a desire for someone to give her attention, and she was perfect for what envisioned could be. So I offered rope, to see if she would take it.
I softly stated - that maybe i could help.
She looked up at me - and i have to say, the look of a tear stained cheek, a bit of ruined makeup, looked sexy to me - to imagine creating more of that - in a different way.
I cleared my throat and said, i normally don't offer help, when i sense someone has been lazy or unmotivated, but i sense that thinks have just piled on, and that maybe she has just lost her way - but maybe with the right person pushing her, she could find her step again, to find out who she was a long time ago.
Casey began noddiing.
I told her when she came to class next time - i would give her an extra reading assignment - and then a paper would be due based on that - and if she did that, and did it well, and was honest with me - maybe i would consider more personal tutoring, helping her in all of her classes, but mainly working to help her find her motivation - one way or another.
At the end of the next class - i handed her a book, an older one, classic, basically about a younger woman and an older man, how he helped her grow to be who she was - but, there were many times in the story where a firm hand was needed - where no long being a child - the woman was made to do penance for being lazy and wrong. Everything from writing lines, to being put over the man's lap, punished, hand spanked, even harder punishment when needed, and even naked corner time.
I handed her the book and suggested she read it - and write me a one page paper, a summary, and her thoughts if she felt the woman was handled properly, and if she felt that would work for her. It is always interesting when a woman reads it, how she will go. At first the thoughts are - "i am not a little girl" and then they either feel the ideas and actions are beneath them, or the thoughts and ideas become part of their waking mind, and then, if it begins to affect their body - i know that they can be developed that way - pushed to any limits.
I also suggested that she work to prove to herself how lovely of a woman she was - and that i felt she should wear a dress or skirt all the time, a blouse that showed off her figure, and to let her hair down more often - that she would no longer be a divorced mom, but a beautiful woman.
As she left, i looked at her lovely plump but firm backside, and imagined it being nice and red from a handspanking - and wondering if the bait on the hook would land her properly.
I got busy in my week and other classes - and just as Psych 101 was about to begin, and the door popped open, and in came Casey, a bit flushed due to almost being late. I smiled as she took her seat, in a nice skirt and blouse that accented her body, and her hair was done nicely - such a promising start. I had on purpose, set aside time after class, to see the reaction and the summary assignment given - i liked how it began.
After a good class, filled with thoughts and ideas and a bit of teaching about the basics of psych, class ended. Casey sat in her seat, acting like she was fumbling in her leather carry case, as the others filed out of the room. When the room was clear, she got up, smoothed her skirt and came up to my desk, i smiled, told her she looked lovely, and bid her to pull up a chair and sit.
I sat back, waiting for her to make the first step - she cleared her throat a bit, and then, opening her carry case, she got out the book i loaned her, and handed it to me, and then pulled out her summary assignment and handed it to me, blushing.
Prior to looking at her assignment - i asked her what she thought of the book.
Blushing more, she said that it was very intense, and that it seemed the woman in the story benefited from the, er, motivation.
I nodded, and began reading. The first part was just a summary of what happened to the woman, and then as i read, i saw some very good insight to her, where she stated that, in fact, while she assumed the woman was embarrassed, that she herself felt that someone who cared enough to hold her accountable, to provide guidance, in a variety of ways, would be very helpful to her.
She was a bit vague in the ways of being held accountable, but i understood it was probably the very first time she encountered those ideas - so now, to push and see if she would be what i imagined she could be, for me.
So, i looked at Casey, and told her it was a nice summary, but not much in detail, in what happened to the woman, or what she actually felt would be beneficial for her - so i pressed her.
I asked her what areas of her life did she feel that she needed guidance in.
She began by talking about time frames, to be kept on time with assignments, for work around the house, to not procrastinate, and she also said she wanted to work out, to get in better shape, to diet, but was very lazy to that - all of these things she said she needed someone to be stronger about it with her, than she was.
So, i then asked, how did she expect that someone, like me, would hold a woman, like her, accountable.
Blushing, looking down, she mumbled, "Punishment?" in the form of a question.
I firmly told her that this was a prime example of her laziness - and what a worthless answer that was.
So, i asked again, what she felt was proper punishment for a woman like her - being lazy, needing motivation. I told her i could describe my thoughts, but then that was "me" doing something to her - it needed to be her, telling me what she needed, what she deserved for being lazy and not attaining her goals.
She looked down a bit, and then looking up,said spanking..... then got quiet.
What kind of spanking - i inquired
Hand spanking was brought up. I told her does she really think that a periodic hand spanking was what she needed? She shook her head no.
What types of items can be used to punish a lazy woman i asked her.
Knowing the items from the book, she began to describe a hair brush, a paddle, a leather strap, even a cane and a riding crop.
Would those be effective to motivate you? She nodded.
I asked if she had ever been punished - and she simply said "some" as a child and into her teens, but not much.
I then told her that could be the base of the problem - that her parents stopped too soon and were too easy on her. I then asked if her husband held her accountable - and she shook her head no again.
I finally said - was she interested in having me help her. That i would not let her be lazy, and she would participate in her goal setting, but that once consequences were defined, she would have no say in them - did she want that?
Casey nodded - so i asked if she was dating someone ..
I told
I put more emphasis in my tone, and told her, that i didn't want some stupid boyfriend upset with me, because you were being lazy, and i had to whip you, leaving marks.
That impacted her for a moment - and I pushed.. I told her that she read the story, and that she felt that could help her life - and that if she wanted my help, she had to understand that there would be punishment for being lazy. That over time maybe there would be rewards - but i could sense that would take time to come to fruition.
I sat back, and asked her simply, did she want my help.
She slowly looked at me, understanding the weight of her answer, but bravely nodded.
I told her to write her address down for me - and told her i felt that we should meet every two weeks - at her home. Her daughter would be away - but then i would be able to inspect her home, to see if her goals of housecleaning were accomplished, and then we would use her scale, after we defined her diet and workout goals, and then we would sit down, go over her finances, and then her school work. Once we knew the state of things, we would enter to the punishment phase of the day.
She asked, why did i assume there were be punishment?
I chuckled and then asked, if i came to her home tonight, was it clean? Laundry done? Were there clothes hanging on her treadmill? Were all of her bills paid?
She dropped her head and shook it no..
I told her that is why i felt there would usually be punishment, but then i hoped it would evolve to rewards.
When she handed me her address, and she confirmed the next weekend that her daughter would be with her father, i told her i was proud of her for this first step - ad that would be there at 11:00 on that day.
I found myself looking forward to that first Saturday - this would determine how much Casey was ready for - and good be trained and developed.
As i knocked on the door, Casey looked out of breath, but was wearing a nice sundress and white socks and tennis shoes. I like that type of spring summer mommy look. Her legs looked wonderful and her tits were nice and full, showing from the several unbuttoned buttons. I walked in and stood in her modest living room, looking around.
I smiled, and then said to her, that she should give me a tour. She walked me through to the kitchen, and was surprised when i looked in the sink, and then ran my fingers over the counter, and then told her the kitchen looked ok, not bad, but not a detail cleaning. She walked me down the hallway, and i looked in the laundry room, a pile of clean towels not folded, and several baskets of dirty clothes, not yet cleaned - i looked at her and merely said it seemed she was a bit behind.
I asked her when she dropped of her daughter to her husband, and she said on Friday night about 7:00. I nodded and continued.
We got to the bathroom - not too messy, but not detail cleaned and then i saw her daughters room, messy as a kids will be, not dirty, just stuff around. I asked her daughters age, and she told me 10. I nodded, and we went to her bedroom. Again, not bad, her bathroom was a bit jumbled with a hair dryer and curling iron, make up out - you could tell the mirror and sink had not been detail cleaned in a while, and then in her bedroom, i looked in her closet, and it was immediately obvious that she had shoved a bunch of dirty clothes in there.. and then i went to her nightstand, and she gasped as i opened it, seeing several vibrators. I laughed and said, i can see you take some time to take care of things yourself.
She blushed and nodded - i bid her to make me a cup of coffee, and to sit down so we could discuss some things - i also asked her to bring some paper and a pencil or pen.
As Casey sat down, a bit nervous, i sipped my coffee and began.
I told her that she had a lovely house, and i am sure things are hectic. But, i told her, the kitchen and bathrooms were not really clean - it was obvious there was not a regular cleaning schedule. I asked her when she last masturbated. She dropped her head and blushed.
I became more firm - i told her there would be no secrets between her and her disciplinarian - and again asked not only when she masturbated last, how often did she do it?
Trembling now, she told me she masturbated last night, and usually, she whispered, about every other day.
I sat back, sipped my coffee, and said, it seems that her own pleasure was more important than keeping a very clean home for her and her daughter, and that while she was making herself cum, she could have instead folded a load of towels, or cleaned a bedroom, or even cleaned the kitchen better. I told her we would discuss things more in detail later - but that i wanted to go through and have a list, in her writing, for her goals.
We discussed that by every Saturday that i would come by, that the house would be much cleaner, that there would only be clean and folded laundry, and that her bedroom and closet would be immaculate - i told her i would also expect her daughters room to be less messy, but that i expected her to have that discussion for her daughter to do that work as well.
Finally - we decided on a weekly goal of her walking on the treadmill, her goal for weight loss, as well as i would expect to see the bills she paid, all caught up by that same Saturday - i told her that two weeks to organize, clean, pay bills, and to workout, was very reasonable. I told her if she agreed, to sign her name and to put that up on her fridge, so she and her daughter could see it. .I told her that would be the list i would work from every time I was over.
Casey smiled, seemingly happy that there was a list for her to follow- you could see a form of accomplishment, a path forward.
I then cleared my throat, and asked her, if she was ready to take care of her punishment, to start the process of properly.
She seemed a bit perplexed, and then nervous, as she noted that we had just made her list.
I told her that i was disappointed in the house, and expected better, for my first visit, and that she also needed to learn what would happen if she decided to be lazy.
I told her she had 5 minutes to go to her bedroom, and to put on what i felt was a proper punishment outfit - a simple t-shirt, panties, and socks could stay if she wished - i told her to be speedy. I also told her to tie back her hair, that pigtails would even be best.
I found that if one was made to dress and look like a younger girl, the punishment would help drive that feeling home more, of being a naughty little girl who was to be punished.
I moved to the living room couch when Casey shyly came in to the room, her hair in pigtails. I saw a problem immediately.
As she stood in front of me - i looked at her, and asked why she ignored my request - she had a quizzical look on her face.
I told Casey that i said, T-shirt, panties and socks, then bid her to tell me where she messed up. Her face got flush as she looked down and said, "bra'
Naughty girls don't wear bras, and i told her i wasn't going to work to undress her as her punishment continued - i told her that would add to her punishment, and had her lay across my lap.
As she got across my lap, i moved a bit to get situated, and then i lifted the bottom of her shirt off, and told her, that punishment was done when i felt the lessons were learned, not after some arbitrary number - did she understand that.
She jumped a bit and yelped out a YES when my flat hand came down on her panties, and i knew offering little or no padding for her spanking.
I continued to swat her ass methodically, moving each time a bit, to cover he bottom properly, and then below her panty line, right on her plump sit spot, and on her upper thighs - my questions and spanking continued for about 10 minutes.
Then, taking a pause, i told her to get up, and to then pull down her panties, and wait for me.
I got up and went to her kitchen. After opening a few drawers, i found a nice thick wooden spoon. I knew i would have to give Casey a shopping list of proper implements - but this would do for now.
Coming back to the living room, i saw that she had complied, and i told her to hand me her panties. Once i touched them, i knew we were on the right path. I sat down, and then told her to resume the same position.
As soon as she was over my lap - i lifted up the bottom of her shirt again, and looking at her nice pink ass cheeks, i asked her, why did her panties feel wet?
She trembled, and since she didn't answer, i began firmly spanking her with the wooden spoon. I did not spare anything - and soon her ass was moving to a bright red, and i knew there would be bruises in the morning. I paused for a bit, and asked again, why her panties were wet..
As she tried to find some way to answer - i continued to spank her soundly with the wooden spoon. The the grunts and sounds of pain, soon turned to sobs, and after about 10 minutes more of hard firm swats all over her now red and purple ass, she broke down and began crying.
As i lay the wooden spoon down, i softly caressed her bottom, feeling the heat from her hand and implement spanking, knowing she still needed more to be broken, i asked again softly, why were her panties wet when she handed them to me.
As the sobbing subsidded, she simply said she didn't know why, but that being over my lap, with what has been talked about, that such a time without feeling the hand of a man on her, being exposed to me, affected her..
I rubbed her bottom softly and told her i was proud of her. I then told her we still had a ways to go - that i wanted her to fully understand. I told her to get up, and to go to the wall, to press her nose against it, and to wait for me, as i searched for what i needed next.
As she complied, i walked back to her bedroom, and then in to the spare bedroom that had a desk and chair.
I found some things that would work, but would certainly need to get her to build a shopping list.
When i walked back in to the living room, i put the items down on the coffee table, and told Casey to come to me. Her eyes glanced down, seeing an old tie, i assume from her husband, a soft supple leather belt that i found in her daughters closet, and several binder clips that i found in her desk.
I told her to look at me, and told her, as she did not follow instructions properly, to take off her shirt and bra.
As she did so, my pleasure was complete. I had been looking forward to seeing her tits in full view - and they did not disappoint. Full and firm, very lovely. But not to get her feeling good about herself yet. I looked down, and saw she had hair around her pussy - trimmed - but not good for the mental effect that i needed. Plus i could use the opportunity to break down any modesty.
I sat down on the sofa again, and then told Casey to get on all fours in front of me, but facing the other way. I told her to back up close to me, and then to put her head down on the floor. I then told her to spread her legs wide - making her stretch, until very spread apart, so her pussy lips were slightly open as well. I knew it was humiliating for her, considering until now, she was dressed and sitting in my classroom. I looked down, and using my hands, i felt her warm red ass again, and then worked down the back of her thighs, and then going down to her inner thighs, i turned my hand over and began cupping her pussy.
i could feel her wetness - and her shivers.
I told her - i see i still must not have been firm enough, as she must believe this is some kind of foreplay. I would never give her the satisfaction of knowing that at this point, it became aware i could make her body react from pain, and pleasure.
I also told her, that from now on i expected her to be shaved smooth and bare. I asked her if naughty little girls deserved to have hair - and she whispered "no".
Good girl - i told her, and with that, i began working a finger inside of her - telling her to keep her legs open, i wanted to see how naughty she was - i told her, that i wondered if she masturbated too much, and was more worried about self pleasure - and i told her, if she came in under 3 minutes - then there was going to be more punishment, but that if she was going to lose control, she had to tell me if she was close, and to ask for permission.
With her ass in the air, her legs spread, and her head on the floor, i quickly worked three fingers in to the her soaking wet pussy, and began fucking her with them, as a finger on my other hand found her hard clit, and began rubbing that firmly as well.
I glanced at my watch and at about the 2-1.2 minute mark Casey yelled out - i need, i am, can i cum please?
I kept fingering her firmly, and said, that didn't seem to be good enough of a request - try again.
PLEASE - sir, can i please cum.
How bad do you want to cum naughty girl?
Sir - VERY much - can i please cum.
I smirked and told her she could cum, and as the damn broke and she was bucking on my fingers, i kept up the sensations and told her if she was going to cum for me, to do it right - to cum again. I kept fingering hard.
I knew she was very sensitive, her clit was rock hard, and she then screamed and bucked again, cumming hard - i took my fingers out and away from her, as she collapsed to the floor - her body shaking in the aftermath of her orgasm.
i reached down and patted her bottom - and asked, are you going to be properly shaved as i asked?
She whispered "yes sir"
Good girl - i told her, but time to pay for your earlier transgression - and also, remember, you came a second time, but did not ask for permission.
The look of realization on her face was wonderful.
I told her, she got wonderful pleasure, but if she was going to break the rules, we would have to do something about it. I asked her if she normally masturbates by hand - and she said that she cannot normally cum that way - she needs a toy of some kind.
I logged that memory.
I asked her if she wanted to handle the punishment for the bra first, or for the climax with no permission - she lowered her head and said, "for the bra first"
She had a half-wall between the living room and the kitchen, with a post at each end of the wall, going from the floor to the ceiling - i brought her over to one post, and told her to reach her arms up over her head. I took one end of the tie and tied it around one wrist, then i took it around the post, and tied her other wrist firmly as well. At that moment, her arms were now out of the way and as i walked around to face her, her wonderful full tits were on display for me - and she was helpless.
I looked Casey in the face and told her, that not only punishment for wearing the bra, but that it seemed that she was flirting a bit in class, and it seemed that she always had an extra button or so open. Did she like when other men, and especially me, look at her tits?
She nodded nervously.
I am proud of you - they are beautiful - but they also are part of your body, and that means they are subject to punishment just like your ass, or even your pussy.. Don't you agree?
She was still working to process my comment, or maybe to hear her pussy could be punished also, but she spaced out, so i slapped one of her tits firmly, from one side, then i backhanded her other tit coming back -
I asked her if she agreed.
"Yessss" she blurted out.
Good- i told her - as i began slapping her tits slowly- back and forth, then up and down, for over 15 minutes until they were nice and pink. I knew they were tender already, and that wearing a bra even by Monday would make her feel the punishment.
When i felt she needed a break, her breathing becoming quicker - i told her to spread her legs again - as far as she could.
I felt between her legs and she was soaking wet still. I smiled and told i guess she was enjoying her punishment.
She moaned as i rubbed her nearly raw but sensitive clit. I got my hand wet from her pussy and rubbed it over her pink tits, working her nipples, rolling them between my fingers. Softly at first, but then harder, then pinching them, and pulling and twisting them harshly - hearing her cry out - but knowing she was reacting to it.
I knew i had a budding pain slut on my hands. She would be delicious to develop and train.
Letting her catch her breath a bit more - i walked over to the table and picked up the two binder clips.
I walked back to her, and told her, that i would be getting her a list of things she needed to buy - she could either buy online, or go to a local adam and eve store, but still, she would have a list of things to be required, as our sessions would continue. But, i told her for now, these would work just fine.
How i was going to use them finally registered, and her eyes flew open wipe, she began to say no, and i stopped, and she shut her mouth.
I said, "NO?" - ok..
I walked over to the table and got the wooden spoon that had been used to punish her ass - and i began swatting her now tender tits slowly and firmly with the wooden spoon. after about 15 swats on each tits, with her nearly in tears again, i put the spoon down, and kissed her cheek and told her, that No isn't an acceptable comment. She could say More, or thank you, or harder, but not no.
She wimpered
I got the binder clips - and started with one nipple. i leaned over, and licked one wet, sucking on it, watching it get hard from the sensation. Then i took her tit in my hand, squeezing it, to highlight the outstretched nipple, and then opened the binder clip, placing it over the soon to be punished nipple, and let the binder clip close down cruelly on her tender nipple.
The scream was delicious, and a sensation she had never had before. Women are used to boys or men treat the tits and nipples like some special wonderful thing, when really it was perfect for harsh discipline like any other part of a woman's body.
While her mind was reeling from the first binder clip, i repeated the process and soon she was howling from the second binder clip closing down on her other sensitive nipple.
I walked over to the floor, where her panties were, and i walked back and told her to open her mouth, and i then stuffed them fully in to her mouth. Her eyes were glazing over from the binder clips, and yet the screams were now muffled.
Much better - i told her.
To really affect the mind- the key is to offset pain with pleasure, and pleasure with pain.
I put my hand between Casey's legs again - and began rubbing her clit firmly. then cupping several fingers in her, i worked her g-spot while my thumb worked her clit. I know she must have thought it took forever, as the pain in her nipples were intense, but soon she was bucking on my fingers again - cumming just as hard as she did previously.
I was cute, that when she was about to cum, but with her panties in her mouth, i could hear grunting and the sound of words, probably trying to ask for permission.
I took the panties out of her mouth, and smiling said, i will give you a pass on asking for permission this time.
She began pleading for me to remove the clips.
I asked if they hurt, she said the pain was unbearable.
I stepped back and slowly strummed the binder clips up and down, sending more pain sensations through her nipples and tits.
I then asked her - how many times she had cum today.
She cried out that she had cum 3 times.
I asked her, wasn't that generous of me?
She said yes, thanking me desperately, but to please remove the binder clips.
Almost there i thought - we had never discussed any pleasure for me - but it was in the back of my mind, and so i thought now would be the time to discuss it properly.
So, i told her, you have cum three times. I wonder what i should get in return.
It hit her what i was talking about - but the pain was incredible, and there is a strong bond between the one being punished and the disciplinarian.
She eeked out -"anything"
Anything? i asked of her.. be more specific. What could you offer me,to thank me for all of this hard work to help guide you.
Anything - she repeated. I didn't move to remove the binder clips, and i said, that anything is pretty broad, but i would like to hear more in detail what you feel would properly thank me for helping you so much, and even giving you so many orgasms.
Whatever you want - she pleaded.
Hmm - i told her.. Will you want to suck my cock?
Yes she cried out.
Well, how much do you want to suck my cock? I mean, you have been without a man for a long time, are you any good at sucking a cock?
Please - she begged. .I want to suck your cock. I will suck it for as long as you want. I want to please you any way i can.
Will you take me all the way, even if i force it down your throat? Will you be a good girl and swallow all of my cum?
yesssss - she begged.
So, tell me i said.
Please - i will suck your cock anytime you want - i will suck it so very good, i will take it all in my mouth, you can choke me with it - and i swear i will take all your cum.
If any cum spills out, will you clean it up?
Yes, i swear i will - i wont waste any of your cum.
I had to admit i was so hard at that point - but there was more to negotiate.
So, we have your mouth being offered. That will be good for today. What about your pussy? I was so good to your pussy today - will i be able to enjoy that as well?
Yes - please - you can have my pussy.
Tell me what can i do with your pussy?
My god, the clips hurt so bad - you can fuck my pussy however you want.
Can i fuck you hard? Can if cum inside of your naughty pussy?
Yes, please - fuck my pussy - cum in it.. Whatever you want. whenever you want.
Good girl - now, one last thing - has you ever had a man fuck your nice little perfect tight asshole?
GODDD - no, no man has ever done that..
So, tell me, here and now - what do you think about offering me your ass virginity?
Please, she sobbed, you can have anything - you can fuck my ass if you want.
Tears were rolling down her face from the pain - so as i undid each binder clip, massaging the blood back in to the nipples, knowing that this at times is the most painful part - i then wiped away her tears, and leaned in and kissed her deeply.
I enjoyed hearing her moans. I pulled back and told her she had done well.
I untied her wrists, and i held her - but i also whispered a reminder that she still had one more punishment left - and that was for not asking for permission for the second orgasm.
She nodded properly, and i told her to get on the ottoman, on her hands and knees, then to lower her head again, but to spread her legs wide.
I knew she couldn't take much more at this time - but she had shown me a bit of what she could take, I would continue to be creative going forward.
She looked so amazing on the ottoman - Her punished ass sticking up, legs spread wide, her red swollen pussy so tender from her multiple orgasms.
I told her, we needed a proper leather strap, but that this belt of her daughters would work. As i folded it over in half, i told her now whenever she saw her daughter wearing the belt, she would remember our first day.
I raised my arm and struck her perfect ass with a hard flat stroke.
She yelped.
I whipped her again, and told her, in the summer time, with all the windows open, she would have to decide if she wanted the neighbors to know she was being punished - but for now - she could make all the noise she wanted.
I gave her a total of 10 strokes from the first side i was standing at, then i went to the other side and slowly added 10 more.
Rubbing her ass - i ran my finger down between her legs, and after getting it wet, i brought it up, and told her to reach back, and hold her ass cheeks apart.
After she complied, with her little tight puckered asshole on display - i slowly rubbed it with my wet finger, and then hearing her gasp, i slowly worked it inside of her ass, all the way past my second knuckle.
I loved hearing her grunt as i slowly worked my finger in and out for a bit - telling her i was going to look forward to being the first man to take her there.. That i looked forward to hearing her describe the sensation of a man's cock in her ass, feeling his cum up in her bowels.
She moaned as i pulled my finger out.
Almost done with your session my dear - i told her, as i raised my arm and gave her a slow 10 strokes from each side again.
The portrait that had begun on her perfect plump and pale ass, was now a wonderful picture of red, purple and growing bruises from her days discipline.
It was good that our meetings would be every two weeks, as it would give her time to feel the punishment, and for the bruises to fade, just in time for her next session.
But there was one more final step.
Telling her to keep her legs spread wide, and her ass up in the air, i took her daughter's belt, and holding on to the buckle, and wrapping the belt around once, so there would be a loose end, i swing the belt up and it struck right between her legs. She jumped and howled.
Remember - i told her, you can be punished all over your body.
Now - 5 more and you are done.
One after another, striking perfectly on her swollen pussy - she took all five better than i expected.
There would be no place on her body that wasn't sore tonight. She would now understand how important it was to accomplish her tasks promptly for me.
Not that i would decrease her punishment every two weeks, but there was more that i could do if she didn't improve on her procrastination and cleaning and such.
I put the belt down, and told her we were done - and that i was proud of her, and hopefully today would motivate her to work on the list we had compiled.
When she looked me in the eye, she was a different woman. She smiled, proud of what she had endured, and how she felt, and that she was with someone who cared about her. The change from before was dramatic.
She came up to me, hugged me, and leaned up, wanting another kiss. It was deep and slow. I stepped back and told her to turn around slowly for me.
i told her she had done so well, and that i was very proud of her, and she looked so sexy at that moment. She walked over to a full length mirror in the hallway, and looked at herself, turning to see everything, touching and feeling the tenderness. A smile formed on her mouth.
She turned and came back to me in the living room.
She took my hand and led me to the couch - she slowly unbuttoned my shirt, and took it off, then she undid my belt, and undid my pants, pulling them and my underwear down.
She whispered that i was larger and thick than her husband - she looked up and smirked and said she may be in trouble for the promise of taking me down her throat. I smiled as she pushed me down in to a sitting position.
She then took off my shoes, and socks, and after putting them to the side, slip off my pants and underwear, then taking them and my shirt, she folded then neatly over the arm of the chair.
Coming back and kneeling down between my legs, she took my cock in her hand, and slowly began working me hard.
She asked, while she stroked my cock, if i had imagined this when I first saw her in class. I told her honestly, no, but tat i did admire her body, and her mind, and that was why i felt she was slacking in class, and knew she had more potential.
She told me she was glad that i pushed her - and that while the idea of punishment made her scared, she said she never has felt so alive.
As i got very hard, she asked what types of things would she be required to buy?
I began to go through the list in my head. I told her at least a good paddle, a wooden hairbrush, for sure a trip to the leather shop to get a proper leather strap. I then said a good bamboo rod would be key, for special punishment, and then several plugs for her ass, to help her be trained to take me that way, as well as proper nipple clamps, unless of course she wanted me to just use the binder clips.
She glared at me, telling me they were evil. I laughed.
I then told her that probably a good set of handcuffs, especially with fur or such - and then i told her probably i would look in to a good remote vibrator that she would be required to wear in class. So i could see how well she could concentrate while i had the vibrator in her pussy turned on.
She took me in her mouth, just a few strokes, and then stopped and said that was evil - to tease her during class, so she did poorly, and then to probably punish her at her sessions for not concentrating in class.
I told her she caught on quickly to how she would be developed.
As she took me again in her mouth, now slowly taking me all the way down to my balls, i told her i wanted her desperate for me every two weeks - and very sensitive in class. That when i left her house, i would take all of her sex toys - and that she was not allowed to cum without my permission - but that she would be required at times to touch herself at home, to edge, to bring her self close, so she would be very needy when i was with her every two weeks. I told her she would find her orgasms far more intense.
As she increased the pace and pressure with her mouth, i asked her if she sucked her husband like that - she lifted her head off my cock, and said No, he didn't deserve it. She then took my cock back in her mouth all the way down again.
I told her she had potential - that her mouth was very good - but that i didn't want to cum for 30 minutes, nor could she take her mouth off me - and she wasn't allowed to use her hands. I told her if her mouth came off of me, or if i came in less than 30 minutes, i would use the belt on her ass again.
Casey spent the 30 minutes, increasing and decreasing the speed of her mouth, gauging how close i was to cumming and then slowing down.
Finally, after seeing her glance at the clock on the wall, i nodded, and she began sucking my cock with more intensity. Soon, based on the day, and seeing her body, and with the feeling of her mouth, i told her i was cumming.
I grunted and arched my back, and she pulled her mouth to the end of my cock, and as i began to cum, her mouth filled up and she was swallowing quickly - finally, as i began finish, she pulled her mouth off of me, smiling as a bit more cum left the head of my cock, and spilled on my leg.
She smiled, and leaned down, licking the cum from my leg, and then licking her lips said, I guess i will have to be punished later for that.
She start to get up and asked me if i would stay for dinner, that she wanted to cook for me. I told her that would be wonderful, but to realize that she wouldn't be allowed to get dressed. She smirked and said she assumed there would be some rule like that - but could i please go to the walk in closet by the kitchen, and get a good bottle of wine and open it.
She laughed and said she assumed i would be able to find the wine opener in the drawers that i was looking at earlier.
As i headed to the kitchen, i swatted her tender bottom, and she turned and kissed me again, then reaching down, she worked her hand around my cock and told me, I hope he is able to fuck me properly later.
No worries i told her, i was already getting hard. That unless she was quick with food, she might get fucked over the dining table.
As she went to the fridge, looking at the list already hanging there with a magnet, she said, that will be another good memory for me to have in between sessions.