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Training Penny Chapter 3 (fm:seduction, 6173 words) [3/5] show all parts

Author: Fredsledge
Added: Nov 15 2025Views / Reads: 152 / 134 [88%]Part vote: 10.00 (0 votes)
Penny is getting a little feisty.
 


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"I don't know what's gotten into you, Penny, but you're acting like a slut."

Then I don't know where this came from, but I said, "Then fuck off."

Jimmy got up and abruptly walked away. I took a few sips of my beer and looked around. A lot of single dudes. They are all looking a lot like wolves about now, I thought.

I got up and walked to the bar and was standing there when this guy came up to me, "Hi," he said.

"Hi," I said back, tipping my head in because of the music.

"I can see you're pretty insecure." He said, leaning in with a smile.

"Oh yes, I have some serious problems, so you better watch out," I answered, leaning a little closer.

He leaned in and put his hand on the small of my back and slid it down my ass and said, "Well, I kill for a living, so I've handled many a wild beast."

I laughed and looked up at him, smiling. He slid his hand under my skirt and was rubbing my ass.

"Maybe we should take this fight out back before some innocent bystanders get hurt," I said as he pulled me close and we kissed deeply.

Without a word, we walked out with his hand still on my ass under my skirt. We walked to the alley next to the bar, and he took my hands and pinned them over my head and took a handful of pussy. I was thrusting. I wanted him.

He looked at me when he felt I was without underwear and was bald. "You are a very dirty girl."

"Scare you?"

"Do I look scared?" He roughly rubbed me and pushed his fingers into me with my hands still over my head.

I was bucking on his fingers, moaning as an orgasm overtook me. "Give me your cock stud."

As he let me go and undid his pants, I dropped into a squat. I could see my pussy was fully exposed, and when I spread my legs for better balance realized I did look like a slut.

I grabbed that dick and practiced my newfound skill and sucked him as deeply as I could. It didn't take long, and he shot his load. The only problem was that he pulled out as he was cumming and shot cum all over my face and my shirt.

He abruptly pulled his cock back in his pants and walked away with me still squatting there. I was in shock for a moment. I wiped as much of the cum off my face as I could, and wanted to get to the ladies' room to clean myself up, but it meant walking back in the bar like this. My other alternative was to just get an Uber and be humiliated by only one person. It seemed the better option.

When I got back to my room, Maddy was gone again, and I looked at myself. My hair had a matted streak of goo, and my red lipstick was smeared around my mouth like a 3-year-old who got their mother's lipstick. I got right in the shower, cleaned up, and decided to read in bed to calm myself. As I lay there, I could feel the heat rising from my swollen and abused pussy. I held my hand open an inch away under the covers, and the heat was radiating.

I was a slut tonight. I acted like a slut with Gio. Am I a slut? Do I want to be a slut? I want to be a slut for Gio, that's for sure. What's the deal with this pain thing, I thought. I remembered the tour of his 'dungeon'. I squeezed my nipple hard. It sent an electric shock right to my groin. Interesting, I thought.

I drifted to sleep and woke after a deep sleep. I wanted to get to a sex shop to buy a plug to replace the one I forgot. But I was hungry.

I got dressed in my regular jeans and tee T-shirt, but no underwear. I liked how it felt, and I liked the way my breasts looked under the T-shirt.

Jimmy was there with a bunch of guys as I walked into the cafe. They and everyone looked my way as I walked in. Of course, everyone does this when anyone walks in, but I felt a lot of eyes on my chest. I'm not very big-breasted, but I do have some pretty tight nipples, and they are a little puffy, so my pokies were standing out. I didn't care. I got a tray of food and went and sat with Maddy and her friends.

" OK, Penny, who did you fuck," Maddy asked.

I smiled and said in an innocent mock southern accent, "My, I haven't the foggiest notion of what you are meaning, dear girl."

Then, of course, they knew. I leaned in and said, "I met this guy, Gio, at the library last week, and we hooked up Friday night. It lasted until Saturday. He's 29! And he was a stud!"

The girls squealed as I regaled my story.

I left and walked to the seedy side of town and mustered to courage to go into the sex shop there. Fortunately, no one was there except the girl behind the counter.

"Can I help you?" she said, like she was bored stiff.

"Ahh, butt plugs?"

She just pointed without even looking up, "There."

I saw an assortment of 3. I paid and left. I went to the drug store, got KY, and went back to my room. I lubed myself up and slid the smallest one in which was the same size Gio used on me. I wanted to go bigger, but remembered Gio saying to go slow.

I was fairly new to my job at the library, and I loved the job. One of my favorite things to do was rounds. It is so much fun to walk up on people doing stuff in the library. It must be a thing to have sex in a public library. I would never say anything, and most times, couples would just ignore me.

There was the rare blow job or girl masturbating on the floor, I'd interrupt, where people would run away, but not often. Actually, to be fair, I'd only scared off one blow job and saw a girl getting up off the floor and pulling up her jeans as I rounded the corner. But I was sure I'd see more in this job.

Sunday night, I hit the books, and before I knew it, it was Thursday, and I was thinking of Gio. I was being diligent with my plug, but realized I needed to shave for Friday. I'm going to get waxed for him next week, I thought.

As I walked in, I immediately stripped and ran to Gio and jumped into his arms. He held me for a second and put me down. We both looked, and I saw this beautiful blonde standing there. She was impeccably dressed, and I realized I was nude and tried to cover myself with my hands.

I looked at Gio, and he said, "I ran late."

She laughed and strolled over to Gio, gave him a peck on the cheek, scanned me from head to toe, smiled, and said, "Bye, Gio; see you."

"Bye, Lisa," and she left.

"Is she your Thursday?" I asked.

"No, she's not a regular. She's a client."

"A client? What do you do?"

"Well, it's hard to explain, but I'm sort of a wealth advisor for women who don't need much wealth advice. Super wealthy women don't have husbands who are interested in spending a lot of time with their wives. Many of these guys understand and allow their wives' indiscretions. It's all very tidy and neat."

"Where does the wealth advice come in?"

"Sometimes the spending accounts get into the millions. I help them with their investments, my fee, but I also advise them on life, helping them protect themselves when their husbands get bored with them."

"And the sex with them?" I asked.

"What about it?"

"I guess I'm asking if the sex came first, the business first, or how that all happens."

Gio paused, "People know about me by word of mouth only. I have a limited number of clients and only take on new ones when one drops off."

"Oh."

I thought about all this for a minute and didn't know what to say.

"Did you enjoy yourself last Friday?"

I chuckled at being called Friday, " Yes, Gio, it was amazing. My problem was I left here very horny."

"Was that a problem? What did you do about it?"

I looked at Gio. "I don't want to make you angry or upset with me."

"Never. Come and sit."

Gio pulled me to his lap and cradled me as I talked.

"I had to masturbate, but I called Jimmy and asked him to take me out. I went out in a very short skirt and a blouse that showed my nipples through the material, and went to the bar with him. He didn't like that I looked like a slut, and I told him to fuck off. I picked up a guy, he made me cum in the alley, and I sucked him off."

Gio looked at me, smiling, and started lightly caressing a nipple as he spoke, "There's a lot in there to unpack. Have you thought about it after?" "Well, yeah, obviously, but I didn't dissect it."

"Let's. You wore a short skirt. That meant you wanted to be looked at. You've freed yourself of the self-restraint about your desire for exhibitionism. Jimmy was safe, but I suspect you wanted an adventure, and when he didn't want to play, you wasted no time moving on. Lastly, I am very impressed you sucked the stranger off. For someone who never gave blow jobs before, this was a big step to being a submissive."

"Wow, I never thought about it that way. I was worried about what you would think."

"Well, we are not under contract, so you can do anything you want."

"Under contract?"

"We'll talk about it. But tell me first, what else have you thought about since we were together last week?"

"I've thought a lot about pain, Gio. I'm still not sure I get it, but I think I might want to understand pain if it heightens the experience.

"What did you think about being called a slut?"

"I wondered if I was a slut. Am I?"

"Do you want to be?"

"Mmmm, I'm not sure. I like letting go, being dominated, but not sure how far, and the boundaries are fuzzy to me."

"OK, good. Let's talk boundaries."

His nipple play was making me horny. I guess the conversation too. I spread my legs a little. He was moving from my nipple to my very wet slit, gently stroking me while we talked. When he would go back to my nipple, my juices on his fingers made the nipple play exquisite. I nuzzled into him.

"Let's talk in general terms before we go into the dungeon. That's a whole other thing, and I want you to have a better basis for discussion.

So, you asked a question about being a slut. Slut is a word. It can have a few meanings. One of those meanings is a term for a submissive who craves sex to the extent she has no regard for her surroundings or who is using her. As a submissive slut slave, you are owned as described in the contract we will talk about.

You will be my property to do what I wish with you. In a way, how you discovered anal play feels good."

"Mmmm," I responded and pelvic thrusted a little.

"In a way, you enjoyed that; there is a level of trust that binds us so we both can enjoy the play without worry that you will be mistreated or damaged."

"Damaged?"

"Physical harm. Permanent physical harm. Like broken bones or blood."

"Does that happen?"

"Not with me...ever. I'm into inflicting pain for the sake of pleasure, and I am a master at it, but I am not into torture.

"Anyway," Gio continues, "because I own you, you will surrender your life to me to do whatever I please with you, and you will obey everything I say without question or complaint. Failure to do so will result in punishment."

"Like the paddle?"

"Like the paddle."

Let's talk about what I might consider doing. "Exposing you in public."

"Yes."

"Making you walk naked in public."

I hesitated with that one, "Yes." I whispered, embarrassed with myself for the daring. I hoped I had the nerve.

"Being nude in front of another man besides me."

"Yes."

"Two men having sex with you at the same time, with one of them possibly not being me."

"You mean you're watching me have sex with two men."

"Yes." He said.

"Yes, I said, with a little hesitancy.

"Masturbating for me."

"Yes."

"Masturbating for others."

"How many others?"

"As many as I say."

"Yes," and I thrust at his fingers again.

"Being gang banged."

"That one I don't know. Can I say it's a boundary and then later change my mind?"

"You can, but that's a two-way street. If there is a gangbang planned and you want it, and we've agreed not to do gang bangs, then you will be denied. No matter how much you want it."

"Public punishment," he continued.

"Wait, about gang bangs, what about diseases?"

"It will be an arranged gangbang, Anyone having sex with you will have been tested. Furthermore, anyone using you will know the rules and know the consequences for breaking them."

"What are the consequences?"

"Maybe someday in your life, you may choose to be on the other side, and then you will know. Just know that no one has ever been diseased or harmful in any way."

"Can I wait until the end to give you that answer?"

"Sure. Public Punishment."

"Yes."

"Naked public punishment."

"Oh God! I will die!, Yes!"

"So you now know a few..."

"A few?"

"Yes, a few of the areas we will explore. You will also, from now on, not be allowed to have sex with any other person, male or female, without my consent. If you disobey. You will be severely punished. If you do it a second time, you will be banished."

"OK."

"And lastly, here."

Gio handed me a bright pink color with a Gold charm attached that said 'Gio's Pet'.

"You will wear this at all times."

I gasped when I saw it. I can't imagine what people will say and what they will think about wearing this around campus. The library! Oh man. That's going to be interesting.

He put it on me.

"Come into the dungeon and I'll explain some of what we will use."

Gio spent what must have been at least an hour explaining all of the pleasure and pain 'tools' as he called them. Many I was familiar with, and some I was not. Some were scary, and some were intriguing.

"May I fuck you now, Master?" I asked.

Gio took me by the hand and said, "Soon," and led me out into the kitchen.

"I have something for you on the table I want you to look at."

"What is it?"

"Your contract."

"My contract," I parroted.

"Yeah, it's not what you think. The idea is to memorialize our relationship and spell out our goals. It's not legally binding. It is just a written statement of understanding, allowing me control.

I looked at it and sat down to read.

1.0.0 Slave's Role

The slave agrees to submit completely to the master in all ways. There are no boundaries of place, time, or situation in which the slave may willfully refuse to obey the directive of the master without risking punishment, except in situations where the slave's veto (see section 1.0.1) applies. The slave also agrees that, once entered into the Slavery Contract, their body belongs to their master to be used as seen fit, within the guidelines defined herein. All of the slaves' possessions likewise belong to the master, including all assets, finances, and material goods, to do with as they see fit. The slave agrees to please the master to the best of their ability, in that they now exist solely for the pleasure of said master.

1.0.1 Slave's Veto

The slave, where appropriate, holds veto power over any command given by the master, at which time they may rightfully refuse to obey that command. This power may only be invoked under the following circumstances, or where agreed by both master and slave: Where said command conflicts with any existing laws and may lead to fines, arrest, or prosecution of the slave. Where said command may cause extreme damage to a slave's life, such as losing their job, causing family stress, etc. Where said command may cause permanent bodily harm (see 4.0.0) to the slave. Where said command may cause psychological trauma to the slave, such as scenes involving significant sexual distress.

2.0.0 Master's Role

The master accepts the responsibility of the slave's body and worldly possessions, to do with as they see fit, under the provisions determined in this contract. The master agrees to care for the slave, to arrange for the safety and well-being of the slave, as long as they own the slave. The master also accepts the commitment to treat the slave properly, train the slave, punish the slave, love the slave, and use the slave as they see fit.

3.0.0 Punishment

The slave agrees to accept any punishment the master decides to inflict, whether earned or not.

3.0.1 Rules of Punishment

Punishment of the slave is subject to certain rules designed to protect the slave from intentional abuse or permanent bodily harm (see 4.0.0). Punishment must not incur permanent bodily harm or the following forms of abuse: Blood may not be drawn at any time. Punishment must stop immediately if blood is drawn. Burning the body Drastic loss of circulation Causing internal bleeding Loss of consciousness Withholding of any necessary materials, such as food, water, or sunlight, for extended periods

4.0.0 Permanent Bodily Harm

Since the body of the slave now belongs to the master, it is the master's responsibility to protect that body from permanent bodily harm. Should the slave ever come to permanent bodily harm during punishment or in any other slavery-related activity, whether by intention or accident, it will be grounds for immediate termination of this contract, should the slave so desire. Permanent bodily harm shall be determined as: Death Any damage that involves loss of mobility or function, including broken bones. Any permanent marks on the skin, including scars, burns, or tattoos, are not accepted by the slave. Any loss of hair, unless accepted by the slave. Any piercing of the flesh that leaves a permanent hole, unless accepted by the slave. Any diseases that could result in any of the above results, including sexually transmitted diseases.

5.0.0 Others

The slave may not seek any other master or lover or relate to others in any sexual or submissive way without the master's permission. To do so will be considered a breach of contract and will result in extreme punishment. The master may accept other slaves or lovers but must consider the slave's emotional response to such actions and act accordingly. Under no circumstances should the master allow such actions to unbalance the slave emotionally, or allow such actions to result in ignoring the slave. The master may give the slave to other masters, provided the rules of this contract are upheld. In such a situation, the master will inform the new master of the provisions stated herein, and any breach by the new master will be considered a breach by the master as well, subject to all rules stated in this contract.

6.0.0 Secrecy

All physical evidence of slavery will be kept in total secrecy, except where both master and slave agree. Any violation of this clause shall be cause to terminate this contract, should the injured party wish it. The materials and physical evidence shall be kept under lock and key in a place acceptable to both parties.

7.0.0 Alteration of Contract

This contract may not be altered, except when both master and slave agree. If the contract is altered, the new contract shall be printed and signed, and then the old contract must be destroyed.

8.0.0 Termination of Contract

This contract may be terminated at any time by the master, but never by the slave, except under special conditions explained within this contract. Upon termination, all physical evidence of slavery, including this contract, will be destroyed, and all materials and belongings shall belong to the master, to be shared or kept as they see fit. The slave, owning nothing and having agreed to give up all worldly possessions and body to the master, shall once again own their body, but nothing else, unless the master decides to give back their possessions. 9.0.0 Slave's Signature

I have read and fully understand this contract in its entirety. I agree to give everything I own to my master and further accept their claim of ownership over my physical body. I understand that I will be commanded and trained, and punished as a slave, and I promise to be true and to fulfill the pleasures and desires of my master to the best of my abilities. I understand that I cannot withdraw from this contract except as stated in this contract.

Signature:____________

9.0.1 Master's Signature I have read and fully understand this contract in its entirety. I agree to accept this slave as my property, body and possessions, and to care for them to the best of my ability. I shall provide for their security and well-being and command them, train them, and punish them as a slave. I understand the responsibility implicit in this arrangement and agree that no harm shall come to the slave as long as they are mine. I further understand that I can withdraw from this contract at any time.

Signature:____________

I looked up at Gio and back at the paper. "I need to sign this to fuck you?"

"You don't need to do anything. If you enjoyed our last session and would like to begin slave training, this would be required."

"I'm ok with everything except turning over all my worldly possessions. Do these other women sign this?"

"Their contract is different because they are clients. You are not."

"How would this work, Gio?"

"First, you are to be available any time I call and to be here promptly, no matter what you are doing. Now, I know you are a student and your studies and degree are important to me."

"Thank you."

"But I will need a copy of your schedule and may have a task for you during the school day."

"On campus?"

"Maybe."

"So then everyone will know I'm Gio's slut! Maybe that's what this should read!"

"That can be arranged."

"If I do all of this, then you will fuck me?"

"If you sign this, I will own you, and you no longer get to make decisions about how or when you get intercourse or release. I will determine when and how I want you to cum. Not you."

"Gio, this is a lot to take in."

"I understand. Maybe you want to go and think about it. We can start next week if you decide this is what you want."

"Can you just play with me more while I think about it?"

Gio walked out of the kitchen and came back a few moments later with my shirt and pants.

"I see you bought a plug. Good girl."

"Yes, sir, I wanted to be sure not to miss my training."

"Let me see."

I turned and bent over for him. He put his hand on my back and gave the plug a twirl. It felt so incredible.

He got up and walked out. I stood up to follow.

He said in a very commanding tone, "Did I say you could move?"

"No, sir!" And I bent right back over exactly as I was.

He came back with a tube of lube and a different plug.

He put his hand back on my back and spun the plug in my mouth. It popped out easily. He then squeezed lube in my ass crack and proceeded to finger my ass, lubricating my hole. I moaned and thrust. It felt so good. He then took the plug, which I saw was larger, and gently pushed it into me. He put lube on his fingers and reached under me and rubbed my slit and clit with his greasy fingers.

He sat and spread his legs. "Sit here."

O sat on the edge of the chair between his legs, and the plug went deeper, making me gasp. He took one hand and put it on my pussy and one on my tit, and was massaging me with the oil. It made me thrust my pelvis. It was so hot. "Don't you dare cum," he said.

"Oh oh, mmm, yes mmmm Master."

He brought me to the edge and started just barely touching me. I was wild.

"Please let me cum, Master!"

For this, I got my tit slapped pretty hard. It sent a jolt through my whole body. He then took that nipple and squeezed it hard as he pushed his fingers into me and started thrusting in and out.

I was going to cum, and he stopped. I thrashed so violently that I fell off the chair. I was whimpering and crying. "Please," I barely whispered. "What??" He yelled.

He picked me up, put me across his lap, and started spanking me. Hard! It hurt. I positioned myself, though, so my clit was on his knee and I was humping him as he hit me.

"You are too smart for your own good, you little slut," he said.

He then took the plug in my ass and started pushing and pulling it in and out as my clit crashed into his knee. "Do you think I wasn't going to know what you were doing?"

I thought he was going to push me over the edge, and he stopped again, pushing me onto the floor. I lay there flailing, moaning, and whimpering, legs spread, and went to touch myself, and he said,

"Don't you dare. Get dressed. You are not allowed to cum until next week, when and if you return to sign the contract. If you make yourself cum, I will know."

"I'll sign. Please, I'll sign now!"

"No, I think you should think about it, go on," and he tossed me my jeans and T-shirt.

As I stood, he said, "Come here." And I stood in front of him, still thrusting. "Hands behind your back."

I immediately complied. "If you move, I will beat your pussy raw." And he slapped my other tit so hard I saw stars. "Please, Gio, I need you," groveling desperately.

He slapped my clit with the back of his hand with a pain that made me want to cum worse than I had ever experienced in my life. I just stood in front of him, thrusting for stimulation, crying.

"Go! You may dress on my front porch."

"Yes, Master." Sniveling and crying out the door. My need to orgasm far outweighed anything I might be feeling about having to dress on a public street. Walking was difficult. I wanted to hump a tree. I was so horny. How would he know? Was I willing to risk that? Should I go back? Call?

I walked a long way to calm down before I called an Uber. As I walked, the plug in my ass was a constant stimulant. The collar around my neck was a mental stimulant, making me feel delirious with a desire to be his slave. I would do anything just to be owned by him, I thought. I was a mess. I didn't care about anything except Gio and cumming, and so I floated through all of my classes that week, not really there mentally.

I spent the week in a constant state of arousal. I kept touching myself and bringing myself to the edge and stopping. The plug and even my nipples against my T-shirt were putting me close to the edge. I needed to cum so bad, I was not sleeping well. I almost came a few times, taking the plug out to evacuate. I also bought an enema bag to clean myself out before next Friday.

I came to the realization that this was all I wanted, and I couldn't wait to sign the contract and didn't dare question the gangbang idea. I went to the cafeteria to get a banana.

______________

Penny didn't look so great when she walked in. Maybe I was a bit too rough on her, making her wait a week, but I knew she did. I saw her disrobing on my front porch. It was funny because I didn't ask her to, and she was being so obedient. A very quick study.

When she walked in, I smiled at her and she ran to me without a word and jumped into my arms and started kissing me everywhere while she humped at me. I kissed her deeply, which made her whimper in my mouth.

She didn't want to let go. I gently lowered her to the ground and said, "Go ahead, you may cum." Completely without any sense of dignity started stabbing her fingers into herself and in a matter of seconds, was thrashing on the floor in front of me, screaming. "Thank you, Master. Thank you. Thank you."

Penny climbed to her knees and looked me in the eye as she rushed to get my cock out and took me in her mouth. The next thing I knew, and to my surprise, I was down her throat. I was so amazed I didn't even realize she was holding me there until she made herself panic for a breath before releasing herself from my member. It was the pulsing of her lips on the base of my cock that made me explode in her mouth. She drank me down with determination.

"Where do I sign?" She said.

I pulled her up by her armpits and stood her in front of me. I looked her up and down and gave her a huge hug. She shuddered in my arms. "You are the best student I have ever had."

"Thank you, Master."

I was so taken with her and her effort, after signing, I carried her to my bed and slowly fucked her to another orgasm. She was purring like a kitten.

"God, I needed that." She said.

I was pretty taken with this girl. I decided to break protocol. I went and got her contract and tore it up I walked back in so Penny could see me throw the pieces in the air.

"Why don't we just play with each other during our visits? We can experiment with anything you want to try. If you just want to have straight sex, that's ok too. You can have Saturday nights as well. I would love to spend time with you, Penny."

Penny almost flew through the air into my arms, wrapping her body around mine and kissing me all over my face. It made me laugh out loud.

"Thank you, Master. I want to be your slave to be used and to serve you as long as you want me." She said, "Can I try nipple clamps?"

"Ssss! Ahhh!" Owe!"

"Let's not leave them on too long."

"No! I want to wear them!"

"On your hands and knees," I said calmly and softly.

Penny immediately dropped to the floor and wiggled her ass at me. I put my hand on the small of her back and gently pulled the plug from her body. I saw she was nicely stretched. I started fingering her ass hole, and she moaned and groaned as she pushed to fuck my finger.

"Stay right there," I said.

I went and got my lube and the 3rd size plug. I walked back to her, and she wiggled herself at me again. So hot. I thought. That ass hole looked like it was totally ready to accommodate a cock. But I wanted her first anal to be pleasurable. I greased her up with some difficulty with her thrusting at my fingers, and lubed the new plug. As I gently worked it in, Penny pushed impatiently, sucking air between her teeth.

After it was in, I said, "Come here." She crawled to me instantly. I took her chain between her clamps and pulled them a little. This made her yelp. I pulled her up on her knees by her clamps, and she had no choice but to follow the tug against her sensitive nipples.

I released a clamp and looked at her face. She pulled back and grimaced as the blood rushed back. I knew that was painful. I put the clamp back on, and she couldn't help but turn her shoulder away, wincing.

"Stand," I said.

I walked to my bookcase and got 2 pretty heavy textbooks and said, "Hands flat out."

She did as she was told, and I put one book in each palm. "Don't you dare move, or you will be punished. If you drop a book? Your punishment will be worse."

"Yes, Master."

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