Chapter 1

Aaron was enjoying his summer break before college. He lived with his Mom and step dad Carl in a small town in northwestern New York State. Mom and Carl had been married for a little over a year now. They both had demanding jobs but tried to spend as much time together that they could and not make the same mistakes they had in their first marriages. This didn't leave much time for him. Aaron was already somewhat of a social train wreck. He was small and skinny but with a protruding belly starting to develop, he had the same haircut since grammar school and he was totally devoid of fashion sense. At school he was either the butt of the joke or more often than not just invisible. He never had many friends let alone girl friends but he was OK with that for now. He was pretty smart, he was going to a big school in the fall on a scholarship and he was sure things would get better eventually. Besides he didn't think there would be too many girls in his town interested in what he was interested in. From his readings on the internet Aaron knew that he was a sexual masochist and a submissive. He wanted to be in all the pictures and videos he had been watching on the internet. The sub tied over a bench being whipped by a beautiful cruel woman. The one licking the spit off a woman's dirty boot. Being fucked in the ass and mouth by large German women (Aaron loved German porn,) Ropes, leather, cuffs, whips, cbt humiliation. He wanted it all. Every night he would masturbate to visions of himself lying naked at the feet of an impossibly beautiful woman; tied, beaten and humiliated, But in his small town and at his age and with no social skills he had no chance to do any of this. But he did the next best thing. Self bondage and masturbation.

It was fine at first. He could kind of tie himself up a bit, but the need to touch himself was to great and it ended to soon. It lost its sparkle since he wasn't really bound and could release himself whenever he liked. Then one day while looking for a new forum on the internet he came across a website dedicated to self bondage enthusiast. It was filled with pictures and stories and different ideas on how to put yourself in real bondage and not be able to get out for awhile. Aaron took to this like a duck takes to water. In the year that followed became quite good at it.

With Mom and step dad not getting home until after 5 PM every day he had a couple of hours to play after school. He slowly built up the supplies he needed. Home Depot became his favorite sex shop. His next favorite place was Wal-Mart. He became quite adept at walking down an aisle and grabbing a pair of panty hose or ladies underwear and then discreetly paying for it in the self check out lane. Most days he would do some fairly simple stuff. A couple of cuffs made from small dog collars with an ice release, clothespins on his nipples and a weight hanging off his balls. He would sit in front of a mirror in his room and enjoy his confinement and self inflicted tortures delaying his gratification for as long as possible. It wasn't like in the videos but it would do for now.

It was late July. Mom and Carl had had left on a week long vacation. Aaron had been invited but declined the invitation to go. This gave Aaron an opportunity to do some more elaborate sessions he had been thinking about.

He slept late on that Monday. The last three days had been a challenge. In preparation for today's activities he had reframed from having any orgasms. He thought that maybe that had been the longest he had gone without jerking off since discovering the pleasure of it at 12. He started the day with a filling but simple breakfast and just a little juice. He did not want any bowel or bladder issues to interfere with his plans. Next he took a long bath. While in the tub he shaved off all his body hair. After his bath he "girly-ed" himself up a bit with some of his mom's bath powder and a drop of very expensive perfume on each cheek. Then he went to the kitchen and took the 4 inch block of ice out of the freezer. It had a key frozen inside of it. The house was warm so he thought it would take about 90 minutes to melt. Back in his room he started to set things up. First he put on a pair of red fishnet one piece garter pantyhose. Wearing this helped with the fantasy. Next he put a second key on the nightstand on the other side of the bed from where he was going to be. A third key was in a dog bowl sitting on a stool. The key was in the bottom of the bowl. The bowl was filled with water from the toilet.

He went back to his chair and began the bondage process. When he was done he had a chain locked around his ankles, and another locked around his knees, a third chain went under the seat of his chair and was locked snuggly in his lap. He had a wood dowel in his mouth like a horses bit it had a large rubber band running behind his head looped over each end holding it tightly inplace. And finally pair of clothespins biting down on each of his nipples. When all this was done he took the final step. He had a new pair of handcuffs he had just gotten that week from Amazon. School books he had told his mom. He put one cuff on his left wrist ran the other cuff under the knee chain and snapped it on his right wrist. The ice with the key sat on a small table in front of him just with in his reach. Once locked in there was nothing to do but watch porn on his laptop, feel his lust and anticipation grow and wait for the ice to melt.

He was about thirty minutes into it, hard as a rock entering into a realm of his own creation when he heard a sound. Someone was in the house. He froze, he thought if he didn't move, if he didn't breathe they would go away. But even if that were true the lady on the laptop was yelling loudly in German at a man crawling at her feet.

"Aaron?" a woman's voice called.

Who was this? It wasn't Mom. The voice was familiar but no one comes into their home.

"Aaron are you here?" the voice was coming closer. He heard footsteps coming down the hall to his room.

"Aaron are you in there?" someone knocked on his door.

Who the fuck is this? "Don't come in, don't come in" he suddenly screamed. But he had the wooden dowel in his mouth and it came out as gibberish.

The door opened. In the doorway stood a short plump woman in her early 60's.

Her name was Trudy. She was his step-dad's mom.


Chapter 2

If Aaron wasn't in full fledge freak-out over this woman standing in the doorway he would have thought the most surprising thing about her was the lack of shock or even surprise or disgust. Just a mildly curious look as her eyes looked him over. He kept yelling for her to go away but she didn't. Instead she came closer eventually saying ;

"Shush. Let me see what you have been up to." She closely examined his locks and chains and then casually said "You smell nice. Chanel?"

Aaron didn't answer, actually even without the dowel in his mouth he was too dumbstruck to say anything.

"The things boys do to get you're their willies hard." She said to herself.

Aaron just stared off into space Trudy reached out and twisted one of the clothespins just a little to get his attention.

"Uhhh" he said through his gag. He looked at her with a lot of fear in his eye.

"Are you OK?"

He nodded his head.

She was not smiling or scowling. Just talking to him as if this was the most normal thing in the world.

She picked up the ice and looked at it. "Oh." She said when she saw the key in it.

"You lock yourself up so you can't touch yourself until the ice melts and then you can begin undoing all your locks and chains. You enjoy pain I guess." She looked at him. He didn't acknowledge him.

"I will be back in a couple of hours." She picked up the half melted ice and started to leave but stopped for a moment and looked at the computer. Three women were standing over a man and peeing on him. She picked up the laptop too and left the room.

Now Aaron was alone again. Without the computer it was very quiet. Aaron wasn't sure what was going on. Was she calling his mom to tell her to come home and see what her pervert son was doing. Was she calling the police. Was what he doing illegal? This wasn't what he planned. He was scared.

From where he was sitting he couldn't see a clock so he had no idea how long it had been when she returned.

"Are you alright." She said.

He just closed his eyes and said nothing.

"That was an hour. Your ice melted and I have the key."

He waited. Eyes open now looking at her.

"I brought you some water." She held up a bottle of Poland Springs with a straw it. She put the straw in his mouth and he drank it greedily but the bit prevented him from closing his mouth completely and much of it ran down his chest onto his groin. It was cold but it felt good. She did nothing to help him, justr watched the water run down his chest and puddle under his balls.

"Ank ou." He said.

"Your welcome. Those clothespins look like they hurt a lot. Yes?"

He nodded. Although they were kind of numb by now.

Without preamble she reached up and pulled them off without relieving much pressure. It was instant pain as the blood rushed in and revitalized the nerves. He reacted as much as he could considering his restraints, Trudy did nothing. The same look of mild interest was the only thing on her face. Or was there the barest hint of a smile.

"I'll be back in an hour." She said as she left the room.

This hour was less panicky then the first one. He was able to settle down and stay calm. He was glad the clothespins were off and was enjoying the afterglow from them but his position had started becoming uncomfortable a while ago and he was now anxious to get out of his bondage. Time went by and he started feeling very sorry for himself when just then the door opened and Trudy returned. She put the key on the little table and stepped back.

"Go ahead." She said.

He stared at her.

"Yes I am staying. I don't want you to get hurt. Oh I almost forgot.

She walked over to him and reapplied the clothespins to his nipples. He winced. He couldn't argue and he needed to get out. He reached for the key. She had put it just within his reach. His middle finger was just able to reach it and bring it over to him. Once he had it in his hand he was able to unlock himself from the chair. Trudy's eyes showed some interest in what he was doing. She started to admire how well thought out it all was.

Once out of the chair, Aaron needed to go around his bed to get the next key. This was done by taking very small steps on his knees. It took awhile. Trudy said nothing nor offer any help. She also saw that he had a full fledge erection. She wasn't able to tell how hard he was while he was sitting but now his dick stuck straight out. She had wondered if her presence would intimidate him or not. She guessed not. Once on the other side of the bed he used his chin, his hands were still cuffed and wrapped around his knee chains, to knock the key off the nightstand. It took him a few minutes to gather it up and put it in the lock on the chain around his ankle. Trudy had stayed out of his way but never took her eyes off him.

After much struggle he managed to get on his feet and still bent over some he went to the bowl of toilet water. The stool was too high for his hands to reach so he had to use his mouth. Specifically he had to stick his tongue in the toilet water and push the key out. Trudy didn't know the source of the water but suspected it was more than just plan water. The key dropped to the floor and the now all but exhausted Aaron fell down to his knees one more time and unlocked the chain around his knees leaving only the handcuffs on. He looked up at her, hoping she would see that he was safe and untied and leave but she didn't.

"Take the bit out of your mouth."

This was what he was dreading the most. Once he had the piece of wood out of his mouth he would have to talk to her. In the two hours he was bound he couldn't come up with any reasonable explanation. No one could have. When he started to take of the pantyhose she stopped him.

"Leave those on for now. Where is the key to the cuffs?" she asked while handing him another bottle of water.

"I froze it in another block of ice. It is still in the freezer."

"So even after you were out of all the rest you still had to spend sometime in the handcuffs.

He nodded. He did not want to look at her.

"But you're not quite finished yet are you?"

Now he looked up. She couldn't possibly mean that?

"Lay down on your bed and finish,"

"Y-y-y-ou're going to watch?" he managed to stutter.

"Lie down on your bed and finish what you started," she said coldly.

Her eyes locked on his. His erection come and gone several times in the last few minutes was starting to stir again with the idea of relief. Hypnotically he crawled into bed and laid on his back. He reached down with his cuffed hands and took his semi erect cock in his hand and started the now so familiar a routine. He closed his eyes and tried to pretend he was alone.

"Open your eyes and look at me Aaron."

He did. There eyes locked for a second. He felt her gaze deep inside of him. Then her eyes moved and was staring at his hands pumping on his erection.

"Do it know." She said in a surprisingly harsh voice.

He did. His cock spewed a large globs of his jizz all over his belly chest. It ran down his body and soiled his sheets. She approached him and reached out and gently stroked his face. After a few minutes she said:

"You probably want to take a shower."

He did. But he had to ask. "Why did you take this so well? I would think most people would have ran screaming out of the room."

"Let's just say that I wasn't always in my sixties and you didn't invent kinky sex. I'll see you later in the week"

And with that she left him. Cuffed, exhausted and covered with cum.


Chapter 3

On Thursday morning when Aaron's phone rang he didn't pick it up. It was from Trudy and he wasn't finished being freaked out over the day before. A minute after his cell stopped ringing the house phone rang. He didn't answer that one either, letting it go to voice mail.

"Aaron this is Trudy, Carl's mother. I am just calling to see if you are OK. Why don't you give me a call back? I think your mom left my number on the fridge. OK? Talk to you soon Hon."

He realized she left a pretty innocuous message in case anyone else heard it. But why was she calling? Was she really concerned about how he was doing? Contrary to what she did and what she said she must think he is a pretty sick puppy.

"How could she understand people like me?"

An hour later he was still fretting about it when his phone made the text message noise.

"CHECK YOUR PLUGGED101 EMAIL"

"Oh fuck." He said out loud. PLUGGED101 was one of the email accounts he used when corresponding with people on the forum. "How did she know?" Then he remembered she had his laptop for two hours. He didn't think a grandmother would know anything about computers and hadn't given it much thought. And then it dawned on him how much was on it. "Shit, shit, fuck, shit!" he said out loud. He went over to the computer and signed on his email. There was a new message from TRUDY1950. He opened it. It was a short message with an attachment.

"Aaron,

You shouldn't have a spread sheet with all your mail accounts and their passwords sitting unprotected on your laptop. It could be very dangerous towards your well being if it should fall into the wrong hands. Please call me now.

T"

He opened the attachment. He was pretty sure of what he would find and he wasn't disappointed. "Why the fuck did I keep this one?" The picture had been taken right after he had jerked off. He had done it while lying on the floor on his back. He was bent so that his ass was against the wall and his legs went straight up. In this position when he came the load went into his face. The picture was a self portrait from a moment after with globs of goo on his face, in his hair and some in his mouth. A regular KODAK moment. Her message was clear. She had everything. His pictures, his video's, his emails. A very dejected Aaron picked up the phone and called. Two hours later she was letting him in the door to her home.

She was dressed in a white dress. And low shoes. She never wore much make-up and if anything she wore less today. If anything was out of the ordinary it was the red polish on her nails. He had only been with her a half a dozen times before the other day but it did seem a little out of character. But then again what was her real character?

Trudy's house was like Trudy, small, neat and kind of plain looking. But once inside you get a few surprises. The first surprise was her technology. Besides the big flat screen TV and extensive audio video equipment there was a two very high end laptops sitting on the dining room table.

"A Mac and a PC? Can't make up your mind?" he said trying to lighten his mood. Trudy's was already pretty light.

"What. Oh no. I just need to have both of those. Let me show you something. She took him into a bedroom that she used as a office. The first thing you noticed were the two big led monitors sitting on a worktable. Several desktop computers were on the floor next to the table and other random pieces of hardware were scattered about. One wall had a bookshelf filled with technical manuals. "Do you know what I do for a living?"

"Ahh no."

"Didn't care enough to wonder I guess. I do computer security. Mostly small banks, local insurance guys that kind of stuff. Use to work for a big company but we didn't see eye to eye. So now I am my own boss and am much happier." She smiled at him.

Now the computer thing made sense. It also kind of explained why she had him bring it with him. God only knew what she was going to do to it.

"I figured you hadn't eaten a good meal in a while so I made you lunch." The kitchen was the next surprise. It was all chrome and granite. Filled with delicious smells. And she had been right about him not eating well. All pizza and sandwiches and junk food. So the idea of a good meal was very pleasing to him. They ate in the kitchen. She made a roast with potatoes, corn and salad. She even gave him a glass of wine. For dessert they had apple pie with vanilla ice cream. They talked about school and his major and various other subjects. When they were done he helped her clean up. It was a pleasant hour.

"Before we continue with some other activities, we need to deal with something." They were standing by the sink. Her tone was a bit more serious.

"What's that?...Activities?" the sudden change in direction caught Aaron off guard. He was starting to think this was only about feeding him.

"I called you twice. I know you were home. You didn't call me back until I had to threaten you with that picture. That is totally unacceptable. Do you understand?"

"Yes I understand. I am sorry. Please forgive me."

"OK you are forgiven. Open your mouth."

He looked at her. My mouth? Why."

"When I say to open your mouth I didn't mean to speak I mean to open it wide. The longer you make me wait the worse it will be."

Aaron didn't know what to expect but he reluctantly did what was asked of him. A moment later she took the sink sponge covered in soap and pushed it into his mouth. "Bite down." she said.

It tasted awful. This was certainly not the kind of thing that he had fantasized about, this was truly a punishment.

"That was 15 seconds. That's how long it would have been in your mouth if you had obeyed right away. A little while later. "30 seconds. Let's keep going."

It was a minute before she said "Open." And removed the sponge. "Spit." she said he did several times into the sink.

"May I have a glass of water." He asked.

"No. I don't think so. I want you to enjoy the taste for awhile. Help you to learn how it is. Now come along."

Aaron wondered exactly how it actually was, but didn't say anything as he followed her out of the kitchen.


Chapter 4

She led him to another bedroom. This one was a bedroom, probably a guest room, with a double bed against one wall and a dresser opposite it on another. There had been a nightstand next to it but it had been pushed aside. The only covering on the bed was a white sheet. Aaron noticed right away the ends of four bungee cords lying in each corner. The other ends hooked around the legs of the bed.

"Recognize the layout? You wrote about it in one of your forums."

He didn't respond. What could he say to the woman who read every pervy thing written by his twisted teen age mind who had thought he would be anonymous forever. He just looked down. While he did that she went to the dresser and opened a drawer.

She handed him a pink garment. "This is called a baby doll. This is just the top. It comes with matching panties, but I don't think we will use them today. Do you like it?"

The baby doll had lace cups and was very sheer. She gently forced it on him and he took it.

"I want you to get naked now and put that on." She said sitting on the bed. He tried to do it as slowly as he could. He was still pretty conflicted over what was going on. It was one thing to fantasize about BDSM with Angelina Jolie and another doing it with a surrogate grandmother. But remembering the pictures she had of him and still tasting the soap in his mouth he did what he was told. Shortly he stood in front of her wearing nothing but the pink baby doll.

"Turn around and let me see the back." He did. "A perfect fit. I asked you before if you liked it. You didn't answer. I am asking again. This time I want an answer. Do you like it?"

"Yes I do." He conceded.

She considered pointing out that his dick had already answered the question but decided to let it slide. "Lie down in the middle of the bed on your back."

As he obeyed she went and got a four leather cuffs from the dresser. Once he was situated the way she wanted she put a cuff on each wrist and each ankle. "You know what to do now. Spread them."

He spread his arms and legs out towards the four corners of the bed and Trudy went around to each corner and attached the bungee to a cuff. The cords were long enough to be somewhat comfortable and the elasticity in the cord gave him some movement but generally speaking he was locked down pretty seriously.

"I think we are just about done. Just two little details." She approached the head of the bed with a small gold tube in her hand. She leaned over and applied a bright red lipstick to his mouth and a little bit on his cheeks, rubbing it in. And then she got up and went over to the dresser. "The mirror is adjustable." She pushed on the bottom and it tilted down. When she had it where she wanted it, it gave Aaron a perfect reflection of his whole body stretched out on the bed. "I will see you in an hour." And left the room closing the door behind her. Aaron stared at the mirror. Looking at his pink covered body spread eagle on the bed with his dick pointing towards the ceiling. "Sigh."

"That was an hour." Trudy as she came through the door. "Are you doing OK?"

"I am a little stiff, My right arm is cramping up a bit. But I am OK."

Trudy came over to him. She set down a bottle of water next to the bed and released his right arm. He flexed it a little and she rubbed it a bit. "Better?"

"Yes. Thank you. I don't know what to call you. Mistress? Grandma?"

She had re attached the right arm, slightly disappointing Aaron who was hoping for a reprieve and she was now repeating the process on the other arm. While his left hand was free she handed him the bottle of water and held his head up so he could drink.

"Not too much. You don't get to pee for awhile. Well certainly not Grandma and I am not your Mistress so I think a either Trudy or Ma'am will suffice. Are you OK with that?"

"Yes Ma'am." He said. He was finally starting to get into this. Yes she was a 62 years old and 5'4 and about 160 lbs but he was starting to love submitting to her.

After he finished drinking and was reattached Trudy sat down on the side of the bed. Her fingers ran over his belly and then just barely brushed his cock.

"Would you like me to squeeze you penis? She said casually looking at his groin.

"Oh yes Trudy, Ma'am. I would certainly want you to do that."

Turning her head and looking into his eyes. "It will cost you. No free rides."

He was taken aback by that. "What do you mean.?"

"Time and comfort. I plan on releasing you in about an hour. If you want me to give your penis a nice hard but not very long squeeze than I will extend the time to 90 minutes and I will do something painful to you. And it will be a long time before I make the offer again. If ever.

"And you will do it now?"

"Yes now. Pain first, then your squeeze and then 90 more minutes of bondage."

"Yes. I want that. Please touch me."

She reached into her pocket and pulled out a clothespin and bent down and put it on the head of his dick. "One minute." It seemed like an hour, He tried to roll around but he couldn't move. And it hurt even more when she took it off. "OK let's give you a minute to recover. After a while she reached down and took his semi erect member and held it firmly in her hand for. "If you come you still lay here for an hour and a half. I imagine it would be pretty uncomfortable" She held it for about 20 seconds and let it go. She switched position and bent down and kissed him gently on the cheek and left him for the next ninety minutes.

By the time Trudy returned Aaron had had enough. Most of his self bondage had been for around an hour and he had the porn to keep him company. And while he had the anticipation of what would come next it still was a long time.

She had changed her clothes. She was now wearing a black skirt and a white blouse. The blouse only had the bottom buttoned and she wasn't wearing a bra. Aaron had been noticing her large breast but with the swinging free like they were he was even more impressed. This was starting to get kinkier all the time.

"I am not going to leave you bound a bit longer. I know you want out but we can't always get what we want can we?"

When he said nothing she reached down and took his nipple in hand and gave it a hard twist. "You have to start learning to answer my questions."

"Yes ma'am! Yes Ma'am!"

She continued twisting. "Yes Ma'am what?"

"You can't always get what you want."

She held his nipple another couple of seconds before letting it go.

"Don't get lazy on me."

She had a small foil package in her hand.

"Open your mouth and bite down on the corner." she said putting the pack between his teeth. When he bite down she tore it and removed the condom. And then she did something amazing. She put it in her mouth and bent down and slowly pushed it down the length of Aaron stiff cock. He groaned loudly.

"Don't come yet. I have something else."

He heard her turn it on. It was an unmistakable buzzing sound. She ran the end of the vibrator up and down his erection gently. Pausing to hold it on his balls. And then using both hands she held it tightly lengthwise against his dick and pumped vigorously. His orgasm was not like any of the previous hundreds. It was long and deep and painful in a way, but a good painful. He couldn't breath or see straight all he could think about was the intense pleasure emanating from the center of his body. He wanted to cry, he wanted to sing, he wanted to swear but all he do was put out a barely audible moan.

When his head cleared enough to know his place in the universe he looked up and saw Trudy. She was not smiling or frowning just that look of curiosity. After a minute she released his hands and feet and allowed him to get up. "Hold the condom on so it doesn't leak out, go to the bathroom and wrap it in tissue and put it in the wastebasket. Do not flush it. Then take a shower. There is a clean towel in there. Come back here when you are done and wait for me." No warmth just very matter of factly. He did what he was told.

He waited for her for 5 minutes. When she returned she had a bag with her. "Lie down on the bed. Have your bottom at the edge let your legs hang down." When he did this she sat down next to him and started handling his cock and balls. He couldn't see what she was doing but after a second he knew. He heard the click of the lock before she sat up. He could see himself in the mirror wearing a pink plastic chastity device.

"You can get dressed and go home now. Your folks will be back Sunday night, so I suggest you be a good boy between now and then. Answer the phone when I call and do whatever I say. Is that understood?"

"Yes Trudy." He squeaked out.

"One more thing. I set up better security on your computer. If you are going to use it for porn sign on under user Aspen. Otherwise sign on under Aaron. When you are under Aspen you will have a icon on your desk top labled SAD. That stands for Search and Destroy. If you ever need get rid of every thing quickly click that and it will remove all your files in 20 seconds. But don't worry every time you sign onto the internet you will be uploading all your data to my server. Keep posting in your forums. They give me such good ideas. With that she closed the door.


Chapter 5

"Hello Aaron." Trudy said stepping aside and letting him enter the hotel room. It had been several months since he had seen her and a lot had gone on since. College was turning out to be better then he had hoped for. He had more friends now than ever before. Only part of this was due to some passwords that Trudy had given him to allow free unlimited access to a variety of on-line games which he shared with his friends. He also had the opportunity to reinvent himself. His experiences with Trudy had somewhat emboldened him. Living in the dorm had forced more social situations on him and to his credit he worked hard at being just one of the guys. Sure every girl (and some of the boys) he saw he had kinky fantasies about. But it was under control.

He hadn't seen Trudy since the morning of Mom and Carl's return from their vacation. To his disappointment she had met him at a diner and had given him the key to the chastity collar he had been wearing for 4 days. She told him that she was going out of town on a big job and wouldn't be back until after he went away to school, but she was sure they would have some more time together in the future.

And apparently that time was now. She had e-mailed him earlier in the week telling him she would be in his area this evening and he should visit and plan on spending the night. That was the best news he had gotten in awhile. She has staying in a hotel suite with a kitchen, living room and bedroom so they would have everything they would need "for a special evening."

Trudy was looking good, something different about her that he couldn't put his finger on. Maybe a little more makeup and her hair was different? Maybe. He didn't know but she seemed...younger? Prettier? Something.

"I made us dinner." she said after an initial hug. They ate baked chicken breast and Cesar salad. They had a bottle of white wine and Italian pastries with coffee for desert. Their conversation covered a lot of ground eventually getting around to something Aaron had been wondering about.

"You once said something about me not inventing kinky sex and implied you had done some stuff when you were younger."

"The 60's" she said smiling "and the sexual revolution. I wasn't a hippie or anything like that. More like I was trying to live the Playboy Magazine fantasy. Martini's and orgies." She laughed. "I wasn't as pretty as the girls in their magazine or in movies. But if you were willing to sleep with people ..." her voice trailed off.

"You went to orgies?" felling a little stirring in his groin

"Well just a couple. I was more into partner swapping and three or sometime foursomes."

"You did ménage trios. Like you and another woman and a guy." Starting to get really aroused now.

"Sometimes. Sometimes me and a couple of guys. And sometimes no guys at all.

Aaron thought he might faint. He never met anyone like her.

Eventually as his excitement and anticipation grew she threw bit of cold water on him "We haven't talk about school. How is it going?"

"Oh great. I've been to all the home football games. They're crazy. Lots of chants and songs. And our teams pretty good. Maybe even get to a bowl game. I like living in the dorm. My roommate has a girlfriend. She goes to school nearby so he is out a lot. Sometimes he brings her back to our room, but I have a few places I can crash.. Foods OK. Mom was never a great cook so I like what they have."

She let him go on for awhile before asking "And what about your classes?"

"Oh...aaa... I'm doing OK. I think I will probably get all B's. I haven't seen my mid-term marks yet. But I should be OK."

"Good. All right" Trudy said as they finished their dessert. "I need a little time to set things up in the bedroom; maybe about 15 minutes or so. So why don't you clear the table and put things in the dishwasher. And when I come out I want to find you sitting naked on the floor in front of the sofa, looking straight ahead." With that went into the bedroom and closed the door.

Aaron jumped up and did a mad dash to clean up the room. It took him about 10 minutes and when Trudy came out of the bedroom she found as she had instructed naked and waiting for her.

She came up next to him "How do I look Aaron." He turned his head to look at her and once again he was rendered speechless. She was wearing a cupless black lacey corset with a black see through blouse unbuttoned only barely covering her large breast. She had on a pair of leather pants, black of course and a pair of hi-heeled boots. Her makeup was more than he ever saw her wearing before, but subtle, not over the top. His erection started to grow.

"I see you let your pubic hair grow back. Do you get any privacy in school?"

"Sure. Showers and things are private. If I had kept it shaved no one would see it. I just haven't shaved it.

In her hand she had a pair of thumb cuffs and a manila folder, which she put down on the table next to the sofa, She knelt down next to him and brought her face very close to him, her nose brushing her cheek. She smelled of leather and spices.

"Put your hands behind your back" she said in a stern voice. When he did she put the cuffs on him. They were a little tight and pinched but that was OK for now. He put his head down and closed his eyes and waited to see what she had planned for him next.

Trudy sat down on the sofa. "Look at me Aaron." He slowly raised his head enjoying the anticipation.

"So do you know what I have here?" she said picking up the folder and held it up for him to see.

"No." he said trying to repress a smile.

She opened it and pulled out a sheet of paper and held it up. His stomach dropped when he saw what it was.

"According to this transcript your all B's are really 2 C-'s and 2 D's. What do you have to say about that?"

"Oh....I....a....thought I was doing better than that."

"Really? This transcript was sent to you last week, here is the time it was sent out and here is the time you opened it." She said holding up another piece of paper. "And here is a copy of an e-mail from a professor telling you that you were in danger of failing his class and offered you some help; which apparently you didn't take." She had an angry look on her face. He had not seen her like this before.

"College is a lot harder than I though. I do try hard but it just doesn't seem to be enough..."

"Shut up." She cut him off. "You are just going to sit there and look me in the eye and lie over and over again? Look at this." She said pulling another piece of paper from her folder. "Two weeks ago you spent 43 hours on line playing a fucking game. If you had spent half of that time studying you would be getting all B's. Wouldn't you?"

His head down, almost in tears he squeaked out a very pathetic "Yes, Ma'am."

"Tonight will be much different than it would have if you had done what was expected of you." She took him by his ear and pulled him into the bedroom. The bed was set up the same as last time four cuffs attached to the bed frame. Three of them were bungee cords, but one was a chain and padlock. The other difference was that the pillows were all piled in the center of the bed. "Get in the center of the bed and lay on your stomach." He quickly complied, resigned to the fact he had no real choice. When she was done he was spread eagle, with his midsection lying on top of the pillows raising his ass into the air. He was unable to see what she was doing but he felt her pull his cock back and was gripping it in her hand. After a minute she released it and came to the head of the bed.

"Open your mouth."

He did and she shoved his own under pants wet from his pre-cum into his mouth. She sat in a chair at the end of the bed and waited. After a few second it felt like something was pinching his dick. Like there was a clothespin on the shaft that he didn't notice to just know. But soon the sensation changed from a pinch to cold and then he realized it wasn't cold but the beginning of a rapidly building burning coming from inside. After a minute it felt like his cock was on fire from with-in. The little squirming he could do offered him no relief. He pushed the underpants out of his mouth with his tongue and said

"Trudy, Ma'am. Can you please make this stop."

Trudy got up and came back to the head of the bed. She picked up the underpants and pushed them back in his mouth. "Don't push them out again. And no I can't stop your discomfort. There is nothing I can do. I put a drop of an Indian spice into your urethra. I read about it on a gay mans cock and ball torture blog. I didn't give you very much and it should be peaking about now. There is nothing either of us can do except ride it out." And with that she went back to her chair.

And after a couple more minutes Aaron did notice a decrease in the sensation. Eventually after what seemed an hour but was really only 20 minutes all that remained was an annoying itch.

"Is it over?" she asked.

He shook his head.

"Have you learned to never ever lie to me? Because you must realize that the punishment will be much greater than what would happen to you if you just tell me the truth when I first ask you something." She took his underpants out of his mouth "Do you understand?"

:Yes Ma'am. I am truly sorry I..."

"Shhhh. That's enough." She pushed his underpants back into his mouth. "We have a lot more to do tonight and I want you to save your breath." Standing next to the bed she took off her blouse and picked up a 3 ft long cane. "I am so disappointed in you on so many levels Aaron. You fuck up in school, you lie to me, you abuse the gift I gave you." As she said this she was tapping the cane on her hand. His eyes were wide looking at the topless woman with the cane. He had often fantasized about receiving a whipping from a woman but now faced with the reality of it he was very scared.

She tapped his ass once, twice and then brought the cane done hard,

"One."

Tap tap swat.

"Two"

Tap tap swat.

"Three"

The first hit was like fire. The second an inferno. The third was hell.

Tap tap swat

"4"

Tap tap swat

"5. One more"

Tap tap swat.

"That's 6." She left him in the dark for awhile.

As soon as the first hit came he burrowed his face into the mattress. Between the garment in his mouth and the mattress his cries were muffled. He had no idea how much it would hurt, his first thoughts were that whatever erotic thrill he got out of it was lost in the searing pain. Well at least that was true at first. But as he laid there and the initial burn started to subside he couldn't deny the beginning of pleasure starting to build. He had been limp since he realized what was happening, that he was in for harsh treatment from Trudy. But now that it was over, or at least he hoped it was over, he felt a small but definitely noticeable stirring in his groin. Although the original beating made him cry he knew this was something he would need to explore in the future. As he thought about this he heard the door open and Trudy came in. He couldn't see her, but she sat down on the bed.

"Are you alright?"

He thought about the first time she asked him that question. He was tied and gagged by his own hands, She had caught him doing something that was his deepest secret and not only was she not judgmental but she was supportive. She even participated in his fantasy and he was feeling pretty guilty about the stuff he had done. He hadn't had a lot of nurturing lately and when given some he fucked it up.

"Yes." He eventually said. "Better than I deserve. I am so sorry..."

"It's over. You were bad, you were punished. It's over. I am going to release you from some of your bonds. But stay on your stomach."

She first released his ankles and had him lift himself up so she could pull the pillows out from under him. Next she went to the top of the bed and released his left hand had him roll over on his side and reattached it to the chain with the other cuff. The room was dark but Aaron could see that Trudy was naked except for a scent of spice that enshrouded her. She adjusted the chain so there was a little slack and had him lay on the edge of the bed on his left side. And then she got into bed with him. She spooned with him. With her soft breast and rock hard nipples pressed against his back she ran her long fingers along his body down to his bottom and gave it a hard squeeze. It took a deep breath with the renewed pain but he did not cry out and in a moment the pain transformed itself into a pleasurable feeling. She withdrew her hand and made a slight rearrangement of her body and turned on a vibrator. Aaron waited to feel its touch but that wasn't her plan. Instead he realized she was using it on herself. He could hear the buzzing grow louder and softer as she worked it in and out of her pussy. He felt her body stiffen as she concentrated it on her clit. He felt her heat grow as her moans became shallower and shallower and then the sudden explosion of movement as she reached her orgasm. He felt the wetness as it squirted out of her and onto him. Both her hands were busy pleasuring herself but she included Aaron in her orgasm by biting and licking his back and neck. Aaron had never been with a woman when she came. He didn't know what to say or do. He was pretty well trapped chained as he was between her and the edge of the bed. He wanted to touch himself but his hands couldn't reach his own groin. So he just laid there and waited. After her orgasm subsided she lay shivering next to him and then reached up and slid her wet hand across Aarons face pushing her juices into his nose and mouth. Then he heard her turn the vibrator on again. It was a long long night.

In the morning she got up and showered leaving Aaron still chained. After awhile she came into the bedroom dressed in normal clothes "Did you cum?" She asked as she unlocked his wrist.

"No." he said.

"Too bad. It may be awhile." She told him to roll over onto his back. When he did she took out a new chastity device. This one was made of clear plastic. She slid it on him and snapped on the lock. "Go shower. You smell bad."

Somewhat dazed with all that happened in the last 12 hours, almost no sleep and now his cock locked away again. He dragged himself into the bathroom and stood in the shower for a very long time. When he came out he realized that all his clothes were in the other room. He went to the living room to retrieve them. Trudy was sitting at the table drinking a cup of coffee. She wasn't alone. Aaron froze in place.

"Aaron I want you to meet Melissa." She was a girl about Aarons height, a little plump with short red hair and chunky black glasses. She wore jeans and a black t-shirt. The shirt had the three sectioned BDSM symbol printed on it. "Melissa is a Junior here at your school and someone who has a similar outlook on life as you. That is women are superior to men, and need to be controlled. Melissa this is Aaron."

"Hi." She smiled.

"I have asked Melissa to be a key holder for your chastity lock. I will have the other one. She has one only for emergencies and hygiene so don't be expecting her to release you. I will continue to monitor your grades. I know you have two major papers do in two weeks and a major test coming up. So you have a chance to do well. If I am pleased with your progress I might send you the key. If not well, there is always next semester."

Aaron was dumbstruck again. The red hair girl had been grinning at him the entire time.

"One more thing."

"Oh God. Now what? Aaron thought to himself.

"You can't expect Melissa to take on this responsibility for free. Why don't you explain dear."

"Sure. Aaron I live in apartment off campus with another girl. You will be coming to our apartment at least 2 hours each week to clean our bathroom and kitchen, dusting and vacuuming and maybe sometimes amuse us. My roommate is even more into this stuff than I am so no problems there. We will also have a cleaning routine to wash your penis. It will involve a lot of cold water so there be no accidents."

"Well Aaron, I need to go." Said Trudy "But I booked the room for another night so you and Melissa or should I say Mistress Melissa can have a little time to get acquainted. We'll be talking."

With that Trudy walked out the door.

When they were alone Mistress Melissa said holding out her foot "Aaron I think it is time you properly greeted me."

And they all lived happily ever after. Although we might here from Mistress Melissa and Aaron again in the future