Today was the big day. Sandra was going to peg him. Jason knew he would remember this day for a long time, no matter how it went. They planned to take it easy today. Breakfast before going shopping. Usually, Jason didn’t like shopping, but today he didn’t mind—it delayed the moment Sandra would peg him. When they got home, Sandra would discipline him, then they’d go to the bedroom. He expected the discipline to be harsh, since Sandra had said she wanted to see the marks on him while she used the large strap-on. He was also getting an extra nine strokes.

Sandra kept reminding him there would be nine extra strokes, and that he could keep the three pictures he’d taken of her and Andre. He had hoped she would forget, but she didn’t.

Sandra seemed to be delaying the event longer than necessary. He suspected that she was savoring what was going to happen and her excitement was building. His was as well, but it was also torture.

In the early evening, Sandra said she was ready. Jason had already set up everything in the clubroom, including the cane he knew she liked.

Jason waited there naked. He still had some marks from the last caning, but he was mostly healed. When Sandra arrived, she was all business. She had him lean over the horse and strapped him down. She felt he would need the restraints this time.

As usual, Sandra stepped behind him and tapped his ass with the cane. She paused, letting him wait for the first stroke. It came hard and fast, followed by more until he was sobbing. His sobs didn’t make her stop; instead, like always, they encouraged her. She kept going until she had given him all fifty strokes, then paused.

“Remember, you’re getting nine more for the photos. It’s what you bargained for,” she said.

He could only nod, now wishing he had not agreed to the extra strokes. It was now too late to change his fate.

The last nine strokes were especially intense, and he knew those marks would last longer than the first fifty, including the last two that were delivered with an extra flip of the wrist.

Afterward, Sandra sat down, her body still buzzing. She thought about what she’d done, feeling as usual, both guilty and satisfied. From the first time she disciplined him, she knew she was drawn to it. At first, it was the thrill of control, especially over a man. She remembered her pulse racing and warmth spreading through her as she held the cane. Over time, it became more than that. It helped her let go of work stress, each strike releasing some anger, but it also excited her. The nervous feeling in her chest always grew into something deeper, something primal. She got very wet.

She didn’t see herself as cruel. She didn’t want to really hurt him or anyone else. Still, seeing the marks appear and hearing his cries sent a chill through her. The first time he cried, she expected to feel concern or shame. Instead, she felt a rush of power and excitement. It was thrilling and unsettling at the same time. She thought that was part of what she got from being in control... the power. She wondered if there was something deeper, something she couldn’t name, as if the act had awakened a part of her that wanted more than just control—something raw and close.

Sandra liked seeing the red marks on his pale skin. The contrast caught her eye and made her breath hitch. She enjoyed the lingering ache of anticipation in her own body. For a moment, she wondered what it would be like to be caned herself, to feel the sharp pain and then the release, but the idea made her stomach twist with fear and curiosity. She didn’t really want that pain. Still, the thought of a man strong enough to take control of her was tempting, sending a shiver through her. That was part of why she liked Darien. She wondered if he would ever spank her. She doubted it, but the idea curiously excited her. The possibility lingered, stirring up nerves and desire she couldn’t ignore.

Afterward, she let Jason go, and he went upstairs to the bathroom to get ready. Tears still filled his eyes as he hobbled down the hall. When he looked in the mirror, he gasped—Sandra hadn’t spared him. He had no one to blame but himself. She had stopped the discipline, but he knew she needed it, and in a strange way, so did he. Despite the pain, a warmth rushed through him at what she’d done. He couldn’t deny that, despite the pain and tears, his small penis was throbbing in its cage and dripping.

Standing at the sink, Jason let out a shaky breath. Beneath the soreness was a deep longing for Sandra, mixed with gratitude and reverence. He thought about the trust he’d given her and how her control stripped away his defenses, leaving him exposed but safe. Sometimes he wondered if she would ever know how much he needed her—not just as his disciplinarian, but as the person who truly saw him. The pain and even the helplessness were part of a bond that felt more real than anything else in his life. He loved her deeply. It wasn’t just for what she did to him, but for how she let him surrender everything and made him feel whole. He knew their relationship was very unusual, and certainly not for everyone, but it worked for them because she had taken his fear, his desires, his needs, and made everything better. Now she was going to take his anal virginity. It was another step in his surrender to her, and that thought made his heart beat with both fear and joy.

Sandra said she would use the five-inch device for the first pegging. That gave him some relief, because he had learned to take the longer one fairly easily. Jason went through his usual routine, cleaning and lubricating himself. His hands shook more than usual. He tried to focus, reminding himself he was used to this. Still, when he thought of the artificial device waiting on the nightstand, his pulse jumped. This was different. He wasn’t just going to wear plugs; this time, he would be penetrated by a five-inch black artificial cock. It looked surprisingly real. But she had a seven-inch one as well, which he was sure she would eventually use. That one was equal too, or slightly larger than the biggest plug.

When he was ready, he took a deep breath and walked into the bedroom, naked except for his tiny cage. He had applied the salve, which helped, but his ass still burned. Sandra was waiting on the bed, wearing only panties and pretending to read. She looked up at him with a wide smile. Despite his nerves, Jason’s heart skipped a beat. She was glowing with excitement. He watched her chest rise and fall with her breathing. For a moment, their eyes met, and they held each other’s gaze in silent understanding.

The air between them was thick with anticipation. Jason sensed Sandra’s vulnerability. Beneath her confidence, she waited for his reaction, needing to know he was as ready as she was. He realized his own nerves and exposed body matched the risk she took in showing her desire. In that moment, their excitement and uncertainty brought them closer, each feeding off the other’s emotions. It made him smile.

Sandra got up and walked over to him. They embraced, and she kissed him deeply. Her arms wrapped around his back and gently squeezed his ass, making him gasp.

“Oh my, your poor little butt is really on fire,” she said, half-joking as she looked over his shoulder and traced the swollen ridges with her fingernails.

Jason started to tremble, and Sandra noticed.

“Don’t worry, I’ll be as gentle as I can. Let me know if it gets to be too much. I won’t stop, but I’ll slow down and let you catch your breath. You’ve prepared for this and gone beyond my expectations with the plugs. I know you’re going to love this—if not this time, then soon. We’ll do this about once a week, or so,” Sandra said.

Jason took a sharp breath. He didn’t like the “or so” part.

“Uh... how do you want me?” he asked, his voice shaky.

“For the first time, I want you on your hands and knees. I want to see your welted ass as I penetrate you,” Sandra replied.

Jason shivered as he crawled onto the bed. He glanced over and was surprised to see the largest artificial cock lying on a towel next to the harness, already gleaming with lubricant. Jason gasped.

“I thought... I thought we were going to use the medium one?” he said, his voice trembling.

“I know, but I changed my mind. You’ve been practicing with the largest plug, so it shouldn’t be a problem. This one isn’t much bigger than that one. Besides, to give you pleasure, we need to put maximum pressure on your prostate,” Sandra replied.

Jason knew that wasn’t the real reason. His prostate would be stimulated either way. She constantly challenged him, and he rose to the occasion. He had no choice.

Jason moaned in surrender and moved to the center of the bed, where a large bath towel was spread out for him. He watched as Sandra put on the harness and attached the large black cock. His heart pounded faster. He couldn’t believe that thing was about to go inside him. It looked far bigger than the one he had practiced with.

When Sandra was ready, she moved between his legs. “Here, let’s put the pillow under your hips,” she said, sliding a large pillow under him and covering it with the towel to keep it clean. Sandra hoped that if she did this right, he would be leaking plenty of prostate fluid.

Sandra moved between his legs, forcing him to spread them even wider. A moment later, he felt her lube-covered fingers between his cheeks. He moaned as she slipped one, two, and then three fingers inside, bringing a gasp from him. She had never done this to him before... not even one finger, and now she had three inside him. She moved them gently in circles, then side to side.

“Relax,” she whispered. “It will make it much easier to get inside you. The last thing you want is to tighten up too much.”

Jason, of course, knew that, but it was difficult. With the plugs, he could control the force of the penetration. Now, he had no control.

“Breathe deeply, like the literature we read a million times told us,” Sandra said as she continued to stretch him. She liked this part. It felt incredibly intimate, and it was.

He thought, “Easy for you to say,” but remained quiet as he took deep breaths. He moaned as she pulled her fingers out. Then he felt the head of the artificial penis touch him, and he visibly tensed.

“Relax, relax,” Sandra said softly as she centered the head on his opening and began to push forward gently.

Jason focused on his practice sessions, breathing deeply and exhaling slowly. He grunted when the head finally slipped inside him and let out his breath.

“That’s it, you have the head inside,” Sandra encouraged. She paused for several beats before beginning gradual pressure. Her heart was beating fast, and she had to control her excitement and the urge to shove it all in at once. She watched as the long black cock began to open Jason slowly. This was even more amazing than she had anticipated. She had never had anal sex, but watching this made her rethink it. Maybe she would give her anal virginity to her black lover.

Jason felt himself filling with the cock. It seemed so much bigger than the plugs and was going deeper. But that was mostly his imagination, he thought.

“Just a couple of inches more,” Sandra said, now breathless.

“Hold,” Jason said. It was his code for her to give him a rest.

Sandra paused, fighting the urge to push the last two inches inside him and get it over with.

Jason could now feel the cock pressing against his prostate. It was different from when he felt the sounding device inside his prostate, or even the plugs. But like with the sounding device and plugs, he could feel little pulses inside his prostate. It wasn’t unpleasant.

“Ready,” Sandra said almost impatiently.

“Yes,” Jason whispered.

As Sandra looked at how his rear opening was stretched, the reality struck her that she was taking Jason’s virginity, and that almost made her climax. She knew that she truly owned him sexually now. She had taken away the pleasure of a normal climax from him over a year ago, but now she felt like she was giving him something more, something better. She was inside a part of his body that wasn’t intended for normal pleasurable purposes, but she was certain that she would be giving him pleasure as he had never experienced. She felt like they were closer than they had ever been. He was giving her something more personal than any traditional sex act. It was special, and would change how they looked at each other forever. It was a good thing.

A moment later, she noticed the rear of the artificial device pressing against her clit, which felt pleasant and unexpected.

Sandra took a deep breath and gave one last push and seated the entire cock inside Jason.

Jason gasped loudly and felt Sandra’s soft thighs pressed tightly to his swollen ass.

“Oh my God, that is amazing. You have it all, every inch. I love it.”

Jason couldn’t speak because he was breathing so rapidly. This was very different from the plugs. He realized that because of the girth, the pressure deep inside was more. A moment later, he felt Sandra’s soft breasts on his back and her breathing on his neck. She was lying entirely on him. It was a unique and pleasant feeling.

“I love this so much, and I love you,” she whispered. “I’m going to start moving now. I will take it slow, then gradually increase the pace. I am going to take your ass, baby. It is mine now.”

Those words sent a rush of excitement through him. He realized that he was receiving something special, but was also giving something special. His head was spinning at the thought of being so filled. He had never felt anything quite like it.

Sandra began pulling out slowly, leaving only the head inside. She pushed back in, just as slowly. Then she did it again, and again, gradually increasing the tempo.

Incredibly, Jason could feel his excitement grow. Each time the device moved past his prostate, he felt it throb. Soon, the throbbing grew with the speed of Sandra’s thrusts.

“Yes, yes,” she whispered as she began to move even faster. The end of the shaft continued to stimulate her clit, bringing her close to a climax herself.

Jason started to groan in time with her thrusts. A strange feeling grew deep inside him. The pulsing increased with each movement. His head spun, and he felt like he was losing control. His whole body seemed to pulse. Each time she pulled out, he felt empty, and the pulsing slowed. He liked the feeling. Without realizing it, he began to push back, almost as if he needed it inside him.

Sandra gasped and said, “That’s it, baby, push back, give me everything. This is so amazing.”

Jason wasn’t listening. His head was spinning. He felt the throbbing grow faster and faster. Something was happening deep inside him. It wasn’t like a climax, exactly. He couldn’t explain it. His whole body pulsed, and his head spun. Then he felt it. He gasped, thinking he had lost control of his bladder. He began to moan louder as the throbbing and pulsing grew in intensity. His entire body was shaking.

Sandra could feel it, and it drove her to move faster, thrusting into him harder, causing a slapping sound that echoed around the room. As she did, the nub touching her was making her lose control. Suddenly, she was climaxing. She began to moan loudly, crying out, “Oh God, oh God.”

To Jason, it felt like his body was exploding, but in a very pleasurable way. He was tingling from his toes to his head. His legs were quivering. Lights were flashing behind his closed eyes. The entire room was spinning. He had never felt anything like this.

Sandra climaxed several times before she collapsed onto Jason’s back. Her still pulsing body pressed against him, the cock still deep inside him. She could feel him quivering under her. For a moment it scared her, but then she felt him moving, still pushing back against her. She smiled and got to her knees again. She grabbed his hips and began to thrust into him again. This time it was easier. He was more open and working along with her. A moment later he began to shake again, and that made her climax again.

Finally, she collapsed onto him in exhaustion. It had been quite a workout. It took several minutes before she rolled off in exhaustion, the large cock slipping out of his stretched ass. Both of them lay there gasping for breath, Jason on his stomach still, and Sandra lying on her back next to him.

After what seemed like a long time, she turned to face him.

“Hi, sweetie,” she murmured, her lips brushing his neck. “I love you. How did you like it?”

He hesitated, unsure how to articulate his experience. He had enjoyed it far more than he ever expected. An incredible wave of pleasure had washed over him, yet it hadn't been a climax, nor had it diminished his desire as a true climax would. Even now, as Sandra continued to kiss his neck, he felt his penis stir. “It was different, wild, hard to explain,” he finally said. “Pleasant, but not like a… an old-time climax.”

“I noticed the towel was very wet,” she countered, a knowing lilt in her voice.

“But it was stronger than when you sound me,” he echoed, recalling the sensation of expelling something, a sensation he’d feared was urine.

“From what I’ve been told and read, it gets better the more we do it,” she continued.

Jason didn’t say, but he wondered how that would be possible; he trusted that if Sandra thought she could do it, then she could.

She said, “I loved it, so we’ll be doing it often now, as an alternative to teasing and denial and sounding. Are you sore?”

“Not too bad, I don’t think,” he replied. “It felt like it stretched me more than the plug, and the plugs certainly didn’t move inside me.”

“Can we do it again?” she asked.

“Now?” he questioned, surprised.

“Yes.”

He was about to refuse when she kissed his neck again, her plea soft. “Please, please.”

He couldn’t deny her. “Okay,” he relented, “but not so hard, please.”

Sandra giggled. “I’ll be as gentle as possible.”

“How do you want to do it?” he asked.

“Just turn on your side,” she said, snuggling closer. “But I want to do something different.” With that, Sandra rose and removed a key from around her neck. To Jason’s astonishment, she unclasped his cage. His penis instantly sprang to attention, as it most always did when she removed the cage.

“Are you sure about this?” he warned. “I might get the bed wet, or… climax.”

Sandra smiled, retrieving the towel and sliding it beneath his hips. “Now you can get it as wet as you want,” she said, her tone playful but firm. “But you’d better not climax.”

“Uh… okay,” he managed, a knot of uncertainty tightening in his stomach.

He felt her lubricating the device again before positioning it at his opening. He was already stretched so he knew it would be easier than the first time. As the shaft moved in again, he felt incredibly full. His prostate began pulsing as the head slipped past until it was all the way inside him. He felt her pause when it was seated.

She reached over his body, her hand covering his erect penis.

Jason moaned in excitement and fear. He wondered if she was going to let him actually climax. Incredibly, he realized he didn’t want that.

Before he could say anything, Sandra said, “I’m not going to stroke it,” she whispered, her voice low. “I just wanted to feel you hard.”

“Uh, okay, but do it lightly, please,” he almost begged.

She giggled. “I love this so much.” She breathed against his ear as she held his small but very hard penis. “I feel closer to you than I ever did when we had penetrative sex. It almost feels like your penis is a real extension of the one I have inside you.”

Again, Jason found himself at a loss for words. He was worried that he wouldn’t be able to control himself.

“Tell me when you are ready,” she said.

“Okay. You can start,” he replied, almost eager now.

Sandra’s movements were slow and deliberate at first, a gentle withdrawal and re-entry, repeated until a slow, steady rhythm was established. Gradually, she began to speed up. The room echoed with the sound of her thighs slapping the backs of his legs. They were both groaning now. Instead of easing up, she was doing it harder than the first time.

After five minutes or so, Jason felt the familiar vibration, the pulsing, returning. This time, he knew what to expect and didn’t resist. With each thrust, the pulsing intensified. He heard Sandra’s heavy breathing, then soft moans of pleasure. She was clearly enjoying herself, and so was he. He hadn’t expected to like it so much, so soon, but he had trusted her when she said he would. He found himself moving back into her thrusts as her pace quickened. Moments later, her climax began, and he felt his own body vibrating, more fluid rushing out.

This time, it was even more intense for both of them. Sandra’s cries of pleasure seemed to make his own feelings stronger, his head spinning as his whole body responded. It wasn’t a climax, and he didn’t feel complete sexual relief. Still, it was intensely satisfying in its own way. She had been right; he was going to enjoy this.

They spent a quiet evening, Sandra being especially affectionate, to Jason’s delight. He could never get enough of her. It seemed that after the pegging, Sandra was even more insatiable. The act and the idea had really turned her on, and she was more demanding sexually than she had ever been. Not that Jason minded, but he was only human.

After their bath, she practically dragged him to the bed and straddled his face. She was soaked already. Jason, caged again, felt his penis pulsing inside. Her domination of him was complete. She owned his entire body and his mind. Every time he thought he couldn’t love her more, he did. They fell asleep in each other's arms.

Jason was in the kitchen when Sandra got up the next morning. He moved a bit awkwardly after last night, but he didn’t mind. He was surprised by how much he enjoyed it. Sandra clearly liked it too, and he knew it would happen again, often.

“How are you feeling?” Sandra asked, sounding a bit shy. “You know, after last night. I got a little carried away, as you probably noticed.”

Jason smiled. “I’m okay. I think I want to wait a few days before we do that again.”

Sandra smiled back. “Of course, I get it. But I’ll be needing your tongue even more now.”

Jason wasn’t surprised. As she sat down, he felt her eyes on him while he made breakfast. The tension between them was obvious. He knew it wasn’t just about last night, but also about Friday, when she’d finally meet up with Darien. He’d never seen her so excited or nervous.

“So, which hurts more, inside or outside? I think I did a good job on both,” she said, grinning as she looked at him.

“It’s hard to say,” he replied. He realized he’d enjoyed both, but in different ways. Somehow, it all felt deeply satisfying. He’d given himself to her more than ever before, and felt closer to her, even if he couldn’t quite put it into words.

The pegging had been transformative for both of them, yet what was coming- Sandra going to bed with Darien- was even more significant. Neither could think about much else.

Sandra found herself fantasizing about what was to come. She knew their marriage would change. Of course, Sandra felt grateful for Jason’s patience and devotion, and for how their relationship had grown. That deep sense of gratitude was tinged with worry. She worried that she was somehow betraying her marriage vows, which she was, but what choice did she have? She could risk it all and take a lover with Jason’s consent, or stay the course and grow even more restless. She had chosen a lover and would have to live with the consequences.

At the same time, excitement grew, pushing past her worries. She reminded herself that she and Jason had talked about this for months, and he had agreed. This wasn’t about betraying him, but about something she needed for herself—something she’d denied herself since she had gotten married. She was crossing a line, not to rebel, but to follow her own deep desire. Friday was the day she would finally, irrevocably, consummate a relationship with another man. She would take a lover, with her husband’s full knowledge. Everything else, all of the other candidates she had pleasured with her mouth, faded away. It was wonderful, but there was nothing like having a real hard cock inside her.

It excited her to know that Darien was different. From the beginning, there was a strong connection she couldn’t ignore. He was confident, but also attentive, making Sandra feel wanted for who she truly was. When he called during his business trip, their conversations were easy, sometimes exciting, but always genuine. It wasn’t always about sex. With Darien, there was laughter, a hint of risk, and a sense of possibility she hadn’t realized she wanted.

For Jason, dread and longing battled inside him. He tried to picture life after Friday. They had promised to talk about everything that happened, no matter how hard it was. There might be questions, confessions, tears, laughter, or even regret that they hadn’t reached this point sooner.

When Sandra arrived home from work the following evening, Jason was waiting for her with a glass of wine, a bowl of warm water, and massage oil. She sighed as he led her to the sofa, where she sat down. As he began his routine of washing and then massaging her feet, she said, “After dinner, you can bathe me, and then we can have our check-in. A very important check-in.”

Once Jason had cleaned up the dishes, he met Sandra in the bathroom, carrying a chilled bottle of wine and two glasses. She was already naked, and the water was running, steaming up the bathroom. Jason helped her in, and then she invited him to join her. He stripped with a smile and slid into the bubbling water. He sat behind Sandra and pulled her back to his chest. They both moaned as her bare skin touched his. He wrapped his arms around her, picked up a sponge, and began to wash her breasts gently. He kissed her neck and ear, bringing a satisfied moan to her lips.

“I love this,” she uttered softly. “Let’s never stop it.”

Jason didn’t answer as he dropped the sponge and began to massage her breasts with his hands. He slowly trailed his hands down her stomach and between her legs. When his fingers reached her lips, she moaned loudly and lifted her hips. He couldn’t believe how quickly she was turned on again.

“I couldn’t think about anything else today,” she admitted.

“Me either,” he said.

“Oh, before I forget, you remember we have a meet and greet at the Center Club Saturday night. We have a bunch of prospective legal service clients to wine and dine,” she said.

Jason moaned and said, “Oh, I almost forgot about that. Do I have to go?’

“Of course. I expect I'll be tired if this works out with Darien, but we still need to go. I need you to charm our prospects. I can only do so much, especially with the ladies. They love you,” she said.

“Okay,” he said.

Then Sandra relaxed back against Jason again, and he brought her to several climaxes with his fingers. They both had vivid dreams about what would happen tomorrow evening.