Aaron Gets a Hand

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 fact. 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.