by Brina Brady
Jesse flipped over onto his stomach with enthusiasm. Master Andrew put a condom on and climbed onto the bed. He pushed Jesse’s legs apart and kneeled between them. Master Andrew squirted lube onto his fingers and massaged Jesse’s hole. He wiggled his finger in but didn’t touch his prostate. He applied more lube and pushed a second finger in, then a third, fingering Jesse fiercely.
“Like that?” Master Andrew asked.
“Yes, Sir.” Jesse’s cock stood fully erect against his stomach, trapped against the bedsheets, ready for pleasure.
Master Andrew eased his lubed cock into Jesse’s opening, and in one long, slow stroke, he pushed in. A burning pain shot through Jesse’s legs, ass, and up his spine. He wasn’t sure if it was from the pressure or his hip hurting.
With his body weight on Jesse’s back and his hot breath in his ear, Master Andrew whispered, “My cock is where it belongs. Your ass was made for me. Just relax and enjoy me.”
He used the same firm but gentle voice as when he’d collared him earlier. Jesse slowed his breathing and relaxed his ass muscles the best he could. Master Andrew gave him a few more seconds to adjust before he pushed his cock in and out of his ass. He slowly thrust and filled him, inch by inch going deeper. Every part of Jesse screamed with delight. Master Andrew stopped moving, and Jesse realized he had settled in as deep as he could go. He had given Jesse all he had to offer.
“You’re mine, Jesse. All mine.”
“Yes, I want to be yours and only yours, Sir,” Jesse panted.
Master Andrew’s cock was large in length and girth. He took full strokes in and out, leaving only the tip of his cock in Jesse’s ass before driving back all the way in. Without any warning, Jesse tensed up, and pleasure morphed into pain, almost unbearable. But just as he was going to ask Master Andrew to stop, something amazing happened. Every time Master Andrew drove his cock into Jesse, it punched his prostate like a hammer on a nail. Each hit sent an outstanding feeling to his balls, and the pain turned to ecstasy as he pounded him.
Master Andrew slammed inside him, and his special spot ignited a fire of desire inside him. He rocked his body and moved with Master Andrew, who slipped his hand under Jesse and rubbed his cock. Jesse wanted this blissful feeling to last forever, but in seconds, he blasted his cum onto Master Andrew’s hand. Master Andrew continued pumping until he came as well, spilling his cum into the condom.
“Jesse, Jesse, you feel so good.”
“Hmmm.” Jesse was lost in his afterglow.
“Don’t move.” Master Andrew pulled out slowly, opened the drawer of the bedside table, and took out a butt plug. “You’re going to wear this plug. It will hold the place for my mark for now.” He inserted the plug into Jesse’s ass, then fell beside Jesse and rolled him over into his arms.
“You were as good as I’d imagined. No, even better.”
CHAPTER SEVENTEEN
Jesse
Master Andrew woke up from his nap and kissed Jesse on the lips. He smiled without opening his eyes. Everything was too good to be true between them, almost dreamlike.
“Are you awake?”
“Yes, Sir.” Jesse cracked his eyes open.
“Want to see the playroom?”
“You know I’m dying to see it, Sir.” Jesse’s stomach turned over with anticipation.
Master Andrew sat up and swung his legs over the side of the bed. “Get up, then.” He stood, stretching his arms, and waited for Jesse to make his way over to him.
“How is your pain level?”
“I feel fine, Sir.”
“I’m going to take you to the doctor to make sure you’re healing properly.”
“I don’t need to see a doctor, Sir.”
“I’ll make that decision, not you.”
“Yes, Sir.”
“Take a shower and meet me in my office first. Do not remove your butt plug unless you need to.”
“Yes, Sir.”
After Jesse showered and dressed, he entered the study. A large desk formed in a long L-shape dominated the space. It held a laptop, a printer, and an array of colorful folders stacked with papers. It was obvious Master Andrew graded papers in here, plus whatever else he wanted to do.
Jesse sat on one of the two padded chairs positioned in front of the desk. Dark walnut bookcases lined the entire left wall. A brown leather sofa with a colorful, striped Mexican Serape blanket draped over the back stood in front of the fireplace with bookshelves on either side at the far wall. He walked over to the mantle and picked up the whip that was sitting there. Was it for decoration or serious punishment? Sam had had one, which he often used, in anger. But it was nothing like this one. This whip was beautiful, made of genuine leather, and had a powerful handle with a loop for easy grip. Master Andrew wouldn’t be using it on him, or at least he hoped he wouldn’t. He couldn’t imagine Master Andrew whipping him when he was angry. He hadn’t seen him angry like Sam often had been with him.
Master Andrew entered the room, dressed in jeans and a T-shirt. He kissed Jesse before sitting behind his desk. He opened the top desk drawer, removed a blue folder, and set it on the desk. He pulled out their contract and the submissive checklist and pushed them across the desk to Jesse.
“Be honest about what you like and don’t like,” Master Andrew said.
Jesse pushed his hair out of his eyes and picked up a pen. “I promise to be honest, Sir.”
“Good. Check the things you’re okay with and leave the ones you’re not okay with unchecked.”
Jesse checked all the spanking implements except a whip and a hairbrush. He was okay with all types of bondage. He also marked all the alternative punishments such as corner time, time-out, revocation of privileges, and writing lines. He left scat, water play, and a few other things unchecked. He declared he was a bottom and had no desire to top in a written statement and wrote berry for his safeword.
“Our contract is for two weeks. We can upgrade it at any time.” Master Andrew signed the contract. Then he handed it back to Jesse, who read and signed it. Master Andrew filed it in the folder and put it into his briefcase.
“As for my expectations of you. Read these rules to me and sign at the bottom.”
Jesse read the rules:
“1. Obey Master Andrew.
2. No back talk.
3. Do chores.
4. Be respectful.
5. No dangerous behavior.
6. No illegal activities.
7. No lying.
8. No cheating.
9. Accept your punishment.
10. Master Andrew has the final say.”
“Do you have any questions about my expectations of you?”
“I’m not sure what you mean about dangerous behavior, Sir.”
“It could be skipping meals, going places that aren’t safe for gay men, and really anytime you put yourself in an environment where you’re at risk. Always ask if you’re unsure.”
“What happens if I break one of your expectations?”
“You’ll be punished as I see fit.”
“Do you have any hard limits, Sir?”
“Yes, I do. Would you like to read my list?”
“Yes, Sir.”
Master pulled out his laptop, searched for the list, and printed it out.
“I’ll read it to you.”
“Thank you, Sir.”
“1. No scat play.
2. No blood play.
3. No public humiliation.
4. No photography or video without your express permission.
5. No marks you can’t cover with normal work clothes.
6. No watersports.
7. Never punish you when I’m angry.
8. Never let anyone play with you. So, what do you think of my hard limits?”
“I approve, Sir. Your hard limits make me feel safe.”
Jesse signed the paper and pushed it across the desk to Master Andrew.
“Let’s check out the playroom but remove your clothes here before we do.
”
“Thank you, Sir.”
“Fold your clothes and put them on the other chair.”
Jesse unlaced his boots in record time, then kicked them off. He slowly unzipped his jeans, the way he did when he wanted to entertain, hoping Master Andrew loved every minute of his little strip tease.
“You know, you’re very sexy when you undress.”
“Thank you, Sir. I wanted to give you pleasure.”
Andrew led Jesse up the stairs and unlocked the door to the upper floor. When he opened the door in the navy-blue brick wall, Jesse gasped. The room smelled like leather. The large space had two smaller rooms off the main room. Shelves filled with all sorts of toys covered one wall. Glass doors encased each shelf and were locked with a padlock. Immediately, Jesse’s attention went to the doghouse against the wall. He did a double take. It had a sign on it, which read Pup Jesse. On the other side of the room was a huge cage. The usual dungeon furniture was scattered around the room. His eyes caught the spanking bench and the St. Andrew’s cross. Across the room stood a swing. The setup of the room was similar to the individual rooms at Leather Paddles. He twirled around and gasped at the hooks on the wall, displaying every spanking implement possible.
“Read the rules to me.” Master Andrew pointed to the poster.
“Rules for Master Andrew’s Playroom:
1. Do not speak without permission.
2. Enter naked, kneel in the middle of the room.
3. Use safeword when needed.
4. Clean playroom and toys after each session.”
“We’re here together, so you don’t have to kneel in the middle of the room. Walk around the room and familiarize yourself. You have permission to talk.”
“Thank you, Sir.”
A large box filled with rice sat beside the open door.
“What’s this rice for, Sir?”
“Punishment. You kneel on the bed of rice. Look at the poster above the box.”
Jesse read Punishment time
Minor punishment 10 - 30 minutes
Major punishment 30 - 60 minutes
“Can I try it, Sir?”
“Sure, you can, but I think you should only kneel until it becomes uncomfortable. I’ll time you.”
Jesse rushed over to the box of rice and got to his knees. After about two minutes, the rice cut into his skin and pain set in. Within five minutes, the pain increased, and he became irritated and desired to move.
“Sir, can I get out of the rice box now?”
“Yes, Jesse.” Master Andrew helped him brush the rice off his knees.
“I can see why this is punishment.”
“What do you think of the swing?”
“Can I sit in it?”
“Go ahead.”
After Jesse sat in the swing, Master Andrew strapped him in and pushed him back and forth.
“It would be fun if you fucked me in this swing, Sir.”
“And that might happen when I decide to.” He stopped the swing and unbuckled Jesse.
“I can’t wait to play in here. Is there something we can do now? Please, Sir.”
“I have something, but if your hip or anything else hurts, you tell me.”
“What are we going to do, Sir?”
“Stand by the St. Andrew’s cross.”
Jesse stood before the blue X that was attached to a cage behind it. There were hooks on the ends.
“What do you want me to use on you?” He pointed to the wall of spanking implements.
“The blue flogger, Sir.” Jesse’s cock jerked at the sight of the flogger, something he had wanted since the last time Master Andrew had tested one on him in the office. Jesse was sure Master Andrew was pleased with his choice by the smile he displayed.
“Good choice. I made that flogger with you in mind.”
“Thank you, Sir.” Jesse’s face warmed into a blush.
“Face the St. Andrew’s cross and spread your arms and feet wide so I can cuff you. I don’t want to hit your balls.”
Jesse’s nerve endings tingled with eagerness. For a moment, he didn’t understand why Master Andrew told him to stand before the St. Andrew’s cross. He had no reason to complain or be concerned, but he had expected Master Andrew to flog him on the spanking bench. However, it was a big issue. Sam had never allowed him on the St. Andrew’s cross.
“I’m going to fasten you up. If you hate it, then use your safeword. Are you sure you’re ready to be flogged?”
“Yes, Sir. I’ve been thinking about that blue flogger since you used one on me in your office.”
“I bought that one to entice you because I know you like the color blue. I’ve thought about that flogging too. I knew you wanted more of that.”
“Sir, it worked. I’m a sucker for anything blue.”
“Tonight I’ll test your sucking skills.”
“Yes, Sir. I can’t wait.”
“Spread your arms and legs.”
Jesse did as directed. Master Andrew fastened his wrists first, leaving his feet hanging about half an inch from the floor. He clicked the leather cuffs to his ankles on both sides of the cross, then wrapped a few more belts around his body to take the pressure off Jesse’s wrists and ankles. Jesse tried to move but couldn’t. His ass cheeks clenched at what was to come; the anticipation was killing him.
“What’s your safeword?” Master Andrew asked.
“Berry, Sir.” Jesse felt trapped, out of control, just the way his cock liked it.
“Why am I flogging you?” Master Andrew whispered.
“I asked for it, Sir.”
“When I ask you what color you are, please respond with one of the traffic light colors. If you are good, say green. If you need to pause for any reason, say yellow. If you want to stop, say red or your safeword berry. Either will work.”
“Yes, Sir. I understand.”
This was going to be different since he’d be flogged on the St. Andrew’s cross. Jesse was unable to pull his hands or feet in any direction. Sweat poured down his face. He had told Master Andrew he wanted him to use the blue flogger, but he had never been on the St. Andrew’s cross before. Sam had told him he wasn’t ready for it, making him feel less than other subs by failing his Dom. But Sam had been wrong; he was ready. With Master Andrew beside him, he no longer feared it. Why hadn’t Sam encouraged him to move forward? He felt just fine secured to the cross. He wanted to tell Master Andrew how much he had already helped him getting more self-confident, but he didn’t want to bring up Sam’s name.
“What’s wrong?” Master Andrew asked.
“I’m surprised how much I like it up here, Sir.”
“Is this the first time you’ve been on a St. Andrew’s cross?” Master Andrew asked with disbelief in his tone.
“Yes, Sir.”
Master Andrew stood to the side and rubbed Jesse’s back in small circles, and he spoke in a soft voice. “From here on in, if I ask you to do something you’ve never have done, tell me. You don’t have to do this if you don’t want to. Do you want to do this?”
“I want this, Sir. I need it.” Jesse wanted to experience a flogging on the St. Andrew’s cross. Yet he continued to twist his wrists and ankles as if he needed a plan B.
“Stop trying to wiggle your way out of the handcuffs.”
Master Andrew’s hand cracked against Jesse’s ass. He jerked from the unexpected blow landing so hard. The loud thud pierced through his pathetic shame and worrisome thoughts. Master Andrew’s hand packed a fucking bite as it pelted his unprotected skin. Jesse chewed his lower lip as the pain exploded right through him from only his Dom’s hand.
“What color are you?”
“Green, Sir.”
Master Andrew picked up the flogger and ran it along Jesse’s back, ass, and legs. He stepped back and wielded the flogger against his back.
That stung like a motherfucker.
Master Andrew swung the flogger against Jesse’s ass. Each blow stung more than his hand, leaving a burning sensat
ion. He lost count of how many times Master Andrew wielded the flogger on his sore bottom and back, striking him over and over again in the same areas.
With what seemed like nonstop swatting, the heat and the sting moved deep inside his muscles and nerve endings. Tears blinded Jesse’s eyes, caused by the exhilaration at his success and the physical pain, and he sported a hard-on. Jesse felt lightheaded, and he disappeared into a warm cloud. Master Andrew tossed the flogger to the floor and removed his restraints. He carried him to one of the small rooms and laid him on a cot, covered him with a white sheet, and waited until he came back from his subspace, softly stroking his back and shoulders. Then he handed him a bottle of water.
“My beautiful Jesse. You were perfect. I’m so proud of you.”
“Thank you, Sir.”
“How’s do you feel?”
“Okay, Sir.”
“Turn over. I’m going to remove your plug. I want you again.” Master Andrew undressed, put a condom on, and lubed himself.
As soon as Jesse turned over, he pulled the plug out and placed it on the stand.
Master Andrew wrapped one arm around Jesse’s waist. His other hand circled his cock and aimed for his target. Then he shoved his gigantic cock inside. The burn melted his insides. His ass throbbed as Master Andrew slammed in and out, and once again, he banged his prostate. His cock was oozing precum. Jesse bucked his body, needing even more contact. Master Andrew immediately saw to his need by taking his cock in his hand, stroking to the same rhythm of his own cock thumping inside him.
“Damn, Jesse. You’re so hot with that cute red ass of yours.”
Jesse couldn’t answer, could form no words; only faint whimpers left his lips. With a jerk, Master Andrew exploded into his condom. The vibration of his cock ignited Jesse into shooting his cum, spurt after spurt.
Jesse collapsed facedown onto the sheets, panting, still feeling the aftershocks of his orgasm. Master Andrew rested alongside him, turned his head, and kissed him hard on the lips. His tongue entered Jesse’s mouth, and both tongues played tag.
“You’re a damn good fuck, boy.” Master Andrew pulled away from Jesse’s lips. Sweat dripped from his hair and ran down his face, his beautiful bearded face.
“Thanks, Sir.” Jesse pushed his hair away from his eyes.