They arrived on time and were ushered into the living room by the Professor. Heather explained why they both came and he had no objection. He started to ask Jenna about her studies and grades. Jenna explained that her grades were fine but that she had issues concerning guilt and thought she would feel less guilty if she were properly punished for the things she had done in the past. She was surprised at the answer she received.
"I hear that a lot," said the Professor. "After needing help to self-motivate it's the next most common reason that people want my services. Many people strongly believe the only way they can move on from feelings like yours is to pay a price in pain and suffering. They are tired of emotional pain and want to have physical pain instead. Does that sound like your situation, Jenna?"
"Yes. That's it exactly," she replied. "I know it might sound weird or crazy or whatever, but I just want the hardest spanking I've ever had in my life. I want it to hurt for days. I want it with a belt or strap or something really serious."
Heather put her hands over her face. Jenna saw her and asked, "What? What did I say?"
Heather smiled nervously, "Be careful what you ask for, Jenna. The Professor has implements that hurt more than you can imagine. You might think you want it but when it's happening all you want is for it to stop."
Jenna seemed unconcerned. "I'm serious. I want it to be severe. But there is one thing I need to ask you about, Professor. Heather told me how you get paid for your service. I'm cool with that. But I'd prefer to do it at the beginning of a session instead of at the end. Is that okay with you?"
"Why do you want to do it at the beginning?" asked the Professor.
"I don't want to keep any energy in reserve. I don't want to have to stop the discipline session when I think I can still give you a blow...y'know...pay you. Because then I have to be thinking about stopping earlier than I could. Do you know what I mean?" said Jenna.
The Professor answered, "Frankly, I think it's astute of you to think this through the way you have. I can see that you are earnest in your desire to be, shall we say, firmly punished. I will agree to let you perform oral sex before the session, but I have a condition to which both you and Heather must agree. My stipulation is that Heather remain in the room for the duration of your session and that she agrees to help you get home afterwards."
Heather didn't say anything. Jenna asked, "What for?"
"As you said, you will not be trying to preserve your energy. At the end of the session you will be in no condition to simply walk out of here like you just left a spa. You might find it hard to walk. You'll be weak and feel very drained. I need to know that you will get home safely and I trust Heather to do that," said the Professor.
Heather was immediately flattered to hear him say that he trusted her. It was such a compliment that she didn't consider what it would be like to witness a session before she blurted out her acceptance of the condition. Jenna just shrugged and said, "Okay, fine with me if she stays."
"Very well," said the Professor, "remove all your clothes and stand in the middle of the room.
Jenna hadn't realized, or wasn't paying attention when told, that she would be completely naked during her session. Her mind's eye had automatically pictured her teenaged spankings where she had her skirt raised or her pants lowered and was spanked over her panties. That was always plenty embarrassing but she had two reasons to be more embarrassed now. Firstly, her pussy was completely shaved and she had a tattoo of an angel holding a heart right above her pussy. The tattoo included the word 'Heaven.' It was something that only her lovers ever saw and the thought of the Professor and Heather seeing her somewhat boastful and slutty tattoo gave her pause.
Secondly, Jenna had outrageously large natural boobs that she always kept tightly corralled inside full bras and under clothes that never showed cleavage. She wasn't used to people seeing her naked breasts. She considered protesting but realized she had already negotiated everything and all three of them had agreed. She had a vague recollection of both Heather and the Professor using the word naked when telling her about the sessions and figured she had just been too focused on all her other concerns to allow the word naked to register. Now she was committed.
She dutifully removed all of her clothes and and stood as instructed, albeit while blushing. The Professor was very happy at what he saw. Jenna had wonderful curves, a tight, flat stomach and a firm, rounded ass that would be perfect for paddling. Her medium length hair was too short for her to sweep in front of her breasts to cover them. She noticed both Heather and the Professor were staring at her boobs.
The Professor deliberately took his time and made her stand in the center of the room during uncomfortable silence. Finally he said, "My, my, don't you have a wonderful body. I'll bet that body got you into a lot of trouble when you were a teenager, didn't it?" he asked.
"Yes, Professor," she answered, as she had been told to address him during sessions.
"You told me about your drinking and drug use but you never mentioned anything about sex. Did you let boyfriends play with those big tits just to get back at your parents?"
Jenna blushed more and looked at the floor, "Yes, Professor."
The Professor was pleased at her embarrassment, "And did you let them touch your pussy for the same reason?" he asked.
"Yes, Professor."
"And did your desire to have revenge on your parents also drive you to suck cocks as a teenager, Jenna?" he asked.
"Yes, Professor," she admitted.
"Are you ashamed of all the cock-sucking and fucking you did behind your parent's backs, Jenna?"
Jenna's eyes began to fill with tear. "Yes, Professor," she answered.
"Say it," he prompted her.
"I'm ashamed at all the cock-sucking and fucking I did as a teenager behind my parent's backs," she replied while choking back tears.
The Professor stood up and said, "Well, let's see what you learned. Come over here now and put your mouth on my cock and show me how much you've learned from your years of bad behavior."
Jenna got on her knees in front of him and unfastened his pleated pants, lowered his black, silk boxer shorts and feasted her eyes on the best cock she had ever seen. She gripped it loosely with both hands and there was still room for her mouth to take in the head and part of the shaft. She slowly licked and sucked at the head of his cock and a small moan escaped her throat.
Heather's mind was reeling. She had never been in a room with two people having sex before. As she sat on the sofa she had an unobstructed view of Jenna performing oral sex on the Professor. She could also she how much the Professor was enjoying her efforts, a view Heather never had when she was the one doing the sucking. She felt strangely jealous and realized she had feelings for the Professor that went beyond what she had been aware of. She wanted to be the one giving him pleasure. Her blowjobs had always been at the end of her discipline sessions and she cried and sputtered the whole time, mostly aware of the pain of her burning ass and nothing else. But Jenna was enjoying her duty. She was hungrily sucking and slurping and working his thick shaft with both of her small, slippery hands. She was moaning and quite deliberately wagging her ass in every direction as she knelt in front of him.
Seeing her ass begging for attention was perfection for the Professor. Jenna had no idea that the more she gyrated her little ass, the more it was going to get whipped raw. The thought of it pushed the Professor passed the brink and he pressed her head deep against his cock and yelled "Take it!" as he released his load into her mouth. Jenna swallowed what she could and licked and sucked the rest of his cum to ensure he was cleaned as he had instructed.
Heather was mesmerized by the vision of the Professor standing tall over Jenna and arching his muscular neck and back as he unloaded and moaned. She wanted it to be her that serviced him. She wanted to jump off the sofa and yell, "Please fuck me, Professor. Or spank me. Or whip me!" Anything. She wanted his undivided attention yet knew she would not be getting it. The Professor had not even looked at Heather the whole time Jenna was sucking his cock.
As he zipped his trousers he moved to his chair and said to Jenna, "Now come over here and place yourself over my knee for a spanking."
"Yes, Professor," she replied while getting up from being on her knees.
When she was positioned as required, the professor began to spank her. After only a few smacks he increased the temp and the force of each blow. Jenna did not make any sound nor any defensive moves. She just took it. Heather was surprised at how loud the spanking was and how hard the Professor was landing his blows.
After nearly one hundred spanks the Professor told Jenna to stand. Her hands instinctively moved to her ass cheeks and she could feel the heat from them. They stung but it was not as painful as she thought it might be. From across the room Heather could clearly see two pink circles on her ass cheeks.
"Thank you, Professor. Are we done?" asked Jenna.
The Professor smiled and almost laughed. "That wasn't even a warm-up. I'd say we're a couple of hours from being done, Jenna."
For the first time, Jenna began to wonder what she had gotten herself into. A couple of hours? Her teenaged whippings consisted of a dozen or so good licks with a belt. What could take two hours? Then she saw the Professor open a drawer and remove a red, leather strap. It was only about a foot long but it was very thick leather and had a black, wooden handle at one end. "Resume your position over my knee," the Professor told her. Jenna obeyed. She was only in position a second when the first stroke landed with a sharp snap.
The pain was much more than the Professor's bare hand. It was beyond a sting. Before Jenna could calculate what made it feel so much worse she had received several more applications of the leather. The Professor was alternating between each cheek and every stroke felt harder than the last. Jenna began to squirm on his knee only to be told to keep still or he would start over. He continued with a steady cadence until he administered fifty strokes and Jenna began to cry quietly. Without a moment's rest the Professor told Jenna to get on the floor on her knees and elbows.
Jenna complied but mistakenly positioned herself on her hands and knees. "I said elbows," corrected the Professor. Jenna adjusted so that her forearms bore her weight instead of the palms of her hands. In that position her heavy breasts pulled downward so her nipples grazed the carpet of the Professor's living room.
The Professor looked at Heather, "Would you be a dear and fetch my number three paddle from the wall of the other room?" he asked her.
Heather was shocked to hear him use the word dear but sprang up and trotted to the dungeon room. On one wall there hung a dozen paddles of different shapes, sizes and types of wood. Each was in its numbered place. She removed the paddle from the number three position and hurried back to the living room. When she handed it to him he gave her a sly smile as if he was secretly sharing his amusement with her. She could tell that he enjoyed her being there. Heather beamed.
The Professor walked in front of Jenna and held the paddle in front of her. "Now you're going to get thirty with this before we move you into the dungeon and get serious. I want you to think about all the things you need to confess tonight."
"Confess?" she asked.
"That's right. I want you to be clear about what you feel guilty about doing and that means you need to confess it out loud. And then, of course, be punished for it. So start thinking about that right now," he told her.
Before she could reply he swatted her across the ass with the heavy oak paddle. Jenna shrieked for the first time. The pain was deep and enduring. The Professor used a much slower cadence so she would feel the heat and pain of each stroke before the next one landed. Each blow drove her body forward and caused her nipples to scratch across the carpet, forward and back. By the end of the strokes her ass was deep red and her thick, swollen nipples were rubbed raw. She cried openly without trying to hide it from either witness.
The Professor told her to stand up. "Heather, please take her into the dungeon and put her on the bench," he said. Heather helped Jenna get to her feet and then ushered her into the dungeon. She quietly whispered to Jenna, "Are you alright?"
Jenna looked into her eyes and answered quietly, "Yes, it's amazing. I just need this," then she cried again. There was a long bench in the room. It tapered lengthwise so Jenna's hips pressed against the broad end and her head rested at the narrow end. The Professor pulled one of her ankles wide and fasted it to the heavy leg of the bench with a leather cuff. He told Jenna to spread her legs and then fastened her other ankle in a cuff. She was bent at the waist with her torso resting on the bench and her buttocks and pussy in full view.