A few days later, I sat at my desk, watching Jacob work on another painting. Dark figures writhed on his canvas, bound in ropes against a stormy background. It wasn't the first BDSM-themed piece I'd seen him create this week.
I cleared my throat. "Your art has some interesting themes lately."
Jacob's brush paused mid-stroke. "You mean the bondage stuff?"
"Yeah, that."
"I like exploring power dynamics in my work." Jacob turned to face me. "Though I'm surprised you're asking, since you're clearly into it yourself."
My mouth went dry. "What?"
Jacob pointed his brush at my neck. "The collar? Pretty obvious tell, dude."
I touched the leather band around my throat. "How did you—"
"Know what it means?" Jacob set down his brush. "Come on, Martin. You've been wearing a BDSM collar for weeks now."
"I..." The words stuck in my throat. My face burned.
Jacob wiped his hands on a rag. "Look, you seem really confused. Want to grab a beer and talk about it?"
I followed Jacob to our usual bar on campus. The place was quiet on a Tuesday night, just a few students scattered at tables. We grabbed a booth in the back corner.
"So, you're into the scene?" Jacob asked after we got our beers.
"I'm not sure what I'm into," I admitted. "It's all pretty new to me."
Jacob nodded. "I noticed your collar weeks ago. Figured you'd bring it up eventually."
"How are you involved in all this?" I asked, leaning forward.
"We have a private BDSM party in the back of the art gallery. Small gatherings, strictly art students only. We explore the connection between art and kink." Jacob took a sip of his beer. "Life drawing with rope work, photography sessions, painting—obviously—, that kind of thing."
"So that's what your paintings are about?"
"Some of them. We focus on the artistic side—capturing the beauty in submission and restraint."
"How does it work exactly?" The words tumbled out before I could stop them.
"We meet at the art gallery every couple weeks. After it closes, of course. Everyone's welcome to participate or just observe. Some pose, others draw or take photos. It's very relaxed, no pressure."
"And people just... do BDSM stuff while others draw them?"
"More or less. Light bondage mostly. Sometimes massage or sensual touch. Nothing too intense. We're all artists exploring together. The power dynamics are just part of the creative process." Jacob studied my face. "You seem really interested."
"I am. Tell me more about these parties," I said, fascinated by this new perspective.
Jacob took a sip of his beer. "It's a safe space to explore. We draw, photograph, paint, even do some light bondage. But it's always consensual and respectful. It's not just about the kink. It's about the art. We capture the beauty in submission and restraint."
"That sounds... different," I admitted, taking a sip of my own beer. "Not what I've been experiencing."
Jacob raised an eyebrow. "Oh? What have you been experiencing?"
I hesitated, then figured what the hell. Jacob seemed open-minded, and it felt good to talk about it. "It's more one-sided. I'm the one submitting, and she's in control. It's intense, but... I like it."
Jacob nodded, not an ounce of judgment in his eyes. "That's one way to do it. But our parties, they're more about mutual exploration. Everyone's on equal footing."
"Equal footing," I repeated, trying to wrap my head around the concept. "That sounds... nice."
"It is," Jacob said, smiling. "We all talk openly about what we want, what we don't. It's a great way to learn about yourself and others."
I couldn't imagine doing any of that with Chloe. The thought of being on equal footing, of having control—it felt wrong. Our relationship was perfect as it was. She was in charge, and I lived to make her happy. That's what I wanted, what I needed.
Still, Jacob's group fascinated me. The artistic side, the mutual respect, the open discussions—it was a different world from what I knew.
"If you ever want to talk more about this stuff," Jacob said, finishing his beer, "I'm here. No judgment."
"Thanks," I said, genuinely grateful. "This was... good. Being able to talk about it."
"Yeah, it's nice having someone who gets it," Jacob smiled. "Makes the dorm feel more like home, you know?"
I nodded, feeling lighter. My life had fallen into place perfectly—I had Chloe, who gave me moments of pure bliss, and now I had both Sarah and Jacob to talk to about it. Everything was exactly as it should be.
I stood in the dimly lit dungeon beneath the Black Rose Sorority. Another release day had arrived, and I couldn't wait to see what Chloe had planned.
"Have you ever been fucked?" Chloe's question hit me like a truck.
"What?" I stammered, my mind spinning. "What does that even mean?"
Chloe laughed. She reached into a nearby drawer and pulled out a small dildo. My eyes widened as I watched her, confusion clouding my thoughts.
She wasn't done. Next came a harness—a strap-on harness. I watched, frozen in place, as she stepped into it and secured it around her waist. She inserted the dildo into the harness.
My mouth went dry. "Wh... what are you going to do?"
She continued laughing. "Did you think only girls could get fucked?"
I couldn't form words. My brain struggled to process what was happening.
"I'm going to show you that boys can get fucked too," she said, her voice dripping with amusement. "Strip and bend over."
Despite my shock, I felt my erection straining against the chastity cage. My hands trembled as I removed my clothes and followed her command.
I gripped the edge of a padded bench, my knuckles white. Behind me, I heard Chloe applying lubricant. My heart pounded against my chest.
"Relax," Chloe said. "Take deep breaths."
I tried to follow her instructions, but my body remained tense. The cool touch of the lubricant made me flinch.
"Stay still," she commanded.
I felt pressure, then discomfort. My breath caught in my throat.
"Remember your safeword," Chloe said. "But I know you can take this."
The initial pain made me want to pull away, but Chloe's firm grip on my hips kept me in place. Tears formed in the corners of my eyes.
"Good boy," she praised. "You're doing so well."
Gradually, the discomfort transformed. New sensations flooded my body, ones I'd never experienced before. My erection strained against the chastity cage, more intense than ever.
"See?" Chloe's voice carried a hint of triumph. "Your body knows what it wants."
She was right. Each movement was more pleasurable than the last. I gripped the bench tighter. My initial fear melted away, replaced by an overwhelming need for more.
"Please," I gasped, though I wasn't sure what I was begging for.
The chastity cage felt impossibly tight as my arousal grew. Every thrust brought new heights of pleasure I never knew existed.
My breath came in ragged gasps as Chloe finished with me.
"So," Chloe said, cleaning up. "Tell me how you liked that."
I turned to face her, my legs still shaky. "I... it hurt at first. A lot. But then..."
"But then?" Her eyes sparkled with amusement.
"Then it became amazing. The pressure, the fullness... I never knew I could feel like that." I felt my face flush. "Every thrust ignited waves of sensations. When you hit that spot inside..."
Chloe nodded, encouraging me to continue.
"I liked how you held me in place, how you controlled everything. Even the initial discomfort felt right somehow." I shifted my weight. "The only thing I didn't like was not being able to see your face."
"Would you want to do it again?" she asked.
"Yes," I admitted without hesitation. "It was incredible once the pain subsided. I've never experienced anything so intense."
Chloe's eyes dropped to my chastity cage, and she giggled. "Oh, I noticed how much you enjoyed it. Your little cage was straining the entire time."
My body still tingled from the intense experience with the strap-on when Chloe pointed to the St. Andrew's Cross.
"Get on," she commanded.
I knew what to do. My legs spread naturally as I positioned myself against the wooden frame, my arms extending toward the upper corners. The touch of cold metal encircled my wrists and ankles as Chloe secured the cuffs.
She held up something new—a small silicone object shaped like a cone. My confusion must have shown on my face.
"This is a butt plug," she explained. "Similar to the dildo, but this one stays in place. No thrusting, just... plugging."
I felt her move behind the cross, out of my sight. The cool touch of lubricant made me shiver. Then came the pressure as she worked the butt plug inside me.
"There," Chloe said, stepping back to admire her work. "Now you'll stay like this for a while."
She walked away, leaving me bound and filled, wondering how long 'a while' would be.
My thoughts raced as I hung there. What just happened? Everything I thought I knew about sex had been turned upside down. Girls were supposed to be the ones getting fucked, right? That's what porn always showed, what everyone talked about. But here I was, still tingling from Chloe fucking me with that strap-on.
And the craziest part? It felt amazing. Once the initial pain faded, pleasure unlike anything I'd experienced before took over. My chastity cage had never felt tighter, straining against my erection as Chloe thrust into me.
Now this butt plug filled me completely. The pressure was strange—like I desperately needed to use the bathroom, but different. Every slight movement reminded me of its presence. I couldn't ignore it even if I tried.
I pulled against the restraints, testing them despite knowing it was useless. The metal cuffs held firm, keeping me spread-eagle against the cross. I couldn't do anything about the butt plug inside me, couldn't adjust it or remove it. I was completely at Chloe's mercy.
Maybe that was the point. My body belonged to her now—not just my orgasms through the chastity cage, but everything. Every hole, every sensation. The thought should have terrified me, but instead it sent another wave of arousal through my trapped cock.
I shifted slightly, causing the plug to press against something inside me that made my knees weak. Was this what girls felt during sex? This vulnerable fullness, this complete surrender of control? No wonder they seemed to enjoy it so much.
After what felt like an eternity, I heard Chloe returning to the dungeon.
"Look what I have here," she said, stepping into my view. In her hands, she held another butt plug. My eyes widened—this one was massive, at least three times bigger than what was currently inside me.
My heart raced. "I... I can't..." Panic gripped me as I stared at the intimidating object.
Chloe laughed. She turned away and placed the enormous butt plug back on a shelf.
"Don't worry," she said, a mischievous smile playing across her lips. "It's not time for this." She paused, her smile widening. "Yet."
Chloe's hands moved to the butt plug, gently pulling it out. The empty feeling hit me immediately, but before I could process it, she was already unlocking my chastity cage. My cock sprang free, harder than I'd ever felt it before.
"Look at me," Chloe said, and I met her gaze. Those blue eyes captured me completely. Her hand wrapped around my shaft, and I gasped at the contact.
She started slow, her fingers barely touching me. Just light, teasing strokes that made my whole body shiver. Her hand was so soft, so perfect. Each stroke brought me closer to an orgasm.
"You're so hard for me," she whispered, increasing her pace slightly. "Such a good boy."
I couldn't look away from her eyes. They held me captive just as surely as the restraints did. Her hand moved faster now, building a rhythm that had me panting.
"Are you ready?" she asked, her grip tightening just right.
"Almost... almost..." I moaned. Her hand moved faster, and I felt the pressure building. "Yes, yes, I'm ready..."
Just as I reached the edge, just as I was about to explode, her hand disappeared. My eyes went wide as I felt myself spilling over, but... something was wrong. The pleasure I'd been chasing vanished. My body jerked as I ejaculated, but there was no release, no satisfaction, no climax. Just emptiness.
"W-what..." I stammered, confusion and frustration overwhelming me. The horniness that had been building for days was somewhat weaker, but I hadn't experienced that wonderful high I always got when Chloe let me cum. My body had released, but my mind felt cheated.
"That," Chloe said, "was a ruined orgasm. The first of many to come."
I stared at her, still trying to process what had happened. All that build-up, all that anticipation, just... gone. Not satisfied, not denied, but something worse—cut off right at the crucial moment. I'd never felt so frustrated and confused in my life.
I sat on my bed, staring at the small butt plug in my hand. Chloe had given it to me after our session, along with strict instructions—wear it for at least an hour every day. My ass still felt tender from earlier, and the thought of putting anything back there made me nervous.
"And don't forget to research ruined orgasms," she'd said before sending me away. "Not just reading about them. I want you to join a forum and talk to people about their experiences."
My head felt foggy, different from my usual post-session high. That ruined orgasm had messed with my mind in ways I couldn't explain. The physical release happened, but the pleasure... it just vanished. Like being pushed off a cliff right before reaching the summit.
I opened my laptop, fingers hovering over the keyboard. How do you even start a conversation about ruined orgasms? The thought of discussing such intimate details with strangers made my stomach churn. But Chloe's orders were clear.
The small butt plug sat next to my laptop. My ass clenched involuntarily at the sight. An hour every day... what was Chloe planning?
I felt lost, confused. Usually after seeing Chloe, everything seemed clearer, brighter. But now? My thoughts swirled in a jumbled mess, unable to focus on anything except that moment when pleasure turned to frustration.
I opened my laptop and typed "ruined orgasm bdsm forum" into the search bar. Several forums popped up, and I clicked on the first one that looked legitimate.
"My Mistress ruined my orgasm for the first time," one post read. "She edged me for hours, then when I was about to cum, she let go completely. I ejaculated but felt no pleasure at all. It was torture!"
Another user wrote: "My Goddess gives me nothing but ruined orgasms now. She says full orgasms make me too satisfied and lazy."
I found a lengthy thread titled "Why Ruined Orgasms are Superior to Regular Ones." People described how regular orgasms left them feeling drained and uninterested in submission, while ruined ones kept them desperate and eager to please.
"A ruined orgasm releases the physical pressure without the mental satisfaction," someone explained. "You stay horny and submissive instead of getting that post-orgasm clarity where you question your choices."
That made me think about my own experiences. After regular orgasms with Chloe, I always felt reluctant about going back into the chastity cage. But after today's ruined one, it felt right, natural even.
I discovered the term "refractory period"—the recovery time after an orgasm when men lose interest in sex. Several posts explained how regular orgasms triggered this period, making submission harder. Ruined orgasms apparently bypassed this response, keeping the submissive in a constant state of arousal and compliance.
I shifted in my chair, the chastity cage growing tight as I processed this information. The ruined orgasm Chloe gave me had felt awful in the moment, but now I wanted to experience it again. I needed to understand this new sensation, to explore why something so frustrating could be exactly what I needed.
The next morning, I grabbed my phone and stared at it. My thumb hovered over Chloe's contact. Before I could talk myself out of it, I typed: "Would you like to have dinner with me again?"
My heart raced as I hit send. The minutes crawled by with no response. I tried to distract myself with homework, but kept checking my phone every few seconds.
The buzz of an incoming message made me jump.
"Yes, that would be lovely. Pick me up at 7?"
I read her message three times to make sure I wasn't imagining it. A smile spread across my face as I confirmed the time.
At 6:30, I stopped by the campus flower shop. Like last time, I picked up a red rose, but this time I also added a small box of fancy chocolates. I wanted to show Chloe I put thought into this.
At exactly 7:00, I stood at the sorority house door, gifts in hand.
The door opened, and my breath caught. Chloe wore a black dress, her hair fell in soft waves around her shoulders.
"These are for you," I said, holding out the rose and chocolates.
"How thoughtful." Chloe's eyes lit up as she accepted them. "Shall we?"
She hooked her arm through mine, and we headed toward the restaurant.
The waiter led us to a quiet corner table. Chloe glided into her seat with grace while I fumbled with my chair.
"Tell me about yourself," I said after we ordered. "What made you choose this university?"
"Oh, that's not very interesting." Chloe's lips curved into a mysterious smile. "I'd rather hear about your classes. Are you enjoying literature?"
I talked about my coursework, but my mind was full of questions about her. Every deflected question only made me more curious.
"What about your family?" I tried again. "Any siblings?"
"Family is such a broad topic." She sipped her wine. "How are you finding the assigned reading for your Victorian literature class?"
My heart beat faster. The way she redirected every personal question drove me wild with curiosity. I wanted to know everything about her, but she remained an enigma.
"You're very good at avoiding questions," I said.
"Am I?" She raised an eyebrow. "Perhaps I just prefer to maintain an air of mystery." She giggled.
"The mystery suits you," I admitted.
"I'm glad you think so." She reached across the table and touched my hand. "Now, tell me about your creative writing assignment."
I found myself spilling details about my classes, my professors, my thoughts on various books. All while Chloe listened, offered occasional comments, and steered clear of revealing anything about herself.
Professor Callaghan dimmed the lights in the Film Studies classroom as scenes from classic romance movies played across the screen. My eyes fixed on the display, drinking in every detail of the tender moments between lovers.
"Notice how the director uses lighting and camera angles to heighten the emotional impact," Professor Callaghan said.
I scribbled notes frantically, hanging on every word about symbolism and visual storytelling in romance films.
Sarah glanced at my notebook, then did a double-take at my detailed observations. She raised an eyebrow but stayed focused on the lecture.
After class, Sarah bumped my shoulder as we packed up our bags. "Since when are you so interested in romance films? You barely took any notes last week during the action movie discussion."
I felt my face flush. "I guess I'm developing new interests."
"Clearly." Sarah grinned. "You practically had hearts in your eyes during that montage."
"Want to grab coffee?" I asked. "We could discuss the lecture more."
"Sure." Sarah hoisted her backpack. "I'd love to hear your suddenly expert opinions on the romance genre."
We settled into our usual spot at the campus cafe, steaming cups of coffee between us. Sarah leaned forward, a knowing look in her eyes.
"So, spill. Why the sudden interest in romance?"
I traced the rim of my cup. "I had dinner with Chloe last night."
"How did that go?"
"She was... amazing. Beautiful. Mysterious." I couldn't help smiling at the memory. "I bought her roses and chocolates. We went to that Italian place downtown."
Sarah's expression softened. "Martin, I need to say something."
"What?"
"I know you're falling for her. But I have to repeat myself. From everything you've told me, this doesn't look like a love relationship."
My stomach tightened. Yes, Sarah had already mentioned this before.
"Don't get me wrong—I think it's great how she's introducing you to BDSM, teaching you about yourself. But has she ever shown any romantic interest? Does she share anything personal with you?"
I stared into my coffee. "Well, no, but—"
"Just... be careful with your heart, okay?" Sarah stirred her drink. "Now, tell me about your latest adventures. What new things has she shown you?"
My face lit up despite the warning. Sarah's eyes sparkled as I started describing dildos and butt plugs. She leaned in closer, completely absorbed in every detail I shared.
I sat at my desk, staring at the black silicone plug Chloe had given me. My "homework," she called it. An hour a day, those were her instructions.
I checked the time—9 PM. Jacob was at his evening art class. Perfect.
The first few times had been awkward and uncomfortable. Now, a couple days in, I had a routine. Lube, deep breaths, slow insertion. The stretch and fullness made my chastity cage feel tighter.
I set a timer on my phone. Sixty minutes. Not a second more.
I tried to focus on my English Lit reading, but the constant presence of the butt plug made it difficult. Every shift in my chair was a reminder. My mind kept drifting to Chloe, to the dungeon, to her promises of larger sizes to come.
The timer beeped. I removed the plug immediately, cleaned it thoroughly, and stored it in its black velvet bag. Back in its drawer, hidden under my socks.
I'd done my homework. But only because Chloe demanded it.
The next time I saw Chloe in the dungeon, I gathered my courage.
"I know this might sound strange," I said. "But could you give me another ruined orgasm?"
Chloe's laugh was a pleasant surprise. "Well, well. Someone's been doing their research. I can't resist such a delightful request."
She secured me to the St. Andrew's Cross, the metal cuffs cold against my wrists and ankles. The butt plug slid in easily—all that practice had paid off.
Silence filled the dungeon. No words, no movement, just the weight of the plug and the strain of the restraints. Minutes stretched into what felt like hours.
My muscles ached. The butt plug's presence was constant, impossible to ignore. The chastity cage felt impossibly tight.
Finally, Chloe's fingers worked the lock. The chastity cage came off, leaving me exposed and desperate.
Her hand wrapped around me, stroking with precision. My hips jerked forward at her touch, my breath coming in short gasps. The edge approached fast—too fast. Just as my muscles tensed, her hand pulled away.
My body convulsed against the restraints. Pleasure mixed with frustration as I spilled weakly onto the floor, the climax ruined by the sudden loss of contact. I pulled against the cuffs, desperately seeking the touch that would push me over properly.
I whimpered as my body spasmed, release without pleasure, frustration mixed with need. Unlike a full orgasm, my mind stayed clouded with arousal. No clarity, no satisfaction—just an aching desire for more. The butt plug pressed against me from behind, while my softening dick twitched with aftershocks.
The chastity cage went back on, leaving me in a state of confused arousal. Frustrated, yet somehow pleased. My mind hadn't cleared like it usually did after release. The constant need remained, exactly as I'd read about on the forums.
I hung limply in the restraints, my breath still ragged.
"How do you feel?" Chloe asked.
"Somewhat frustrated," I managed to say.
"Only *somewhat *frustrated?" She giggled. "I can definitely help with that." That mischievous smile spread across her face again, and my stomach dropped. I had no idea what to expect next.
She removed the butt plug, then released me from the restraints. While I cleaned up and got dressed, she spoke casually, as if discussing the weather.
"To help build up that frustration, your next release won't be in three days like before, but in seven. That'll be the new norm from now on."
My heart stopped. Seven days? My mind reeled at the thought. Three days had been okay, bearable even, but seven?!