Bondage Princess May: Boytoy Jay/Chapter 2

Index

• Chapter 1
• Chapter 2
• Chapter 3
• Chapter 4
• Chapter 5

Jay sat on their queen-sized bed, waiting for Jennifer to return. She instructed him to wait there until she returned from giving Ben and Kevin their instructions for the night. He still smelled of sex from earlier, when he and Ben had their own private session. After a few minutes of waiting patiently, Jennifer stepped calmly into the room and shot the door with a click behind her.

“They’ll be busy all night in the guest room.” She said. She was in her early forties, but looked very good despite passing a kid through her body. Like Jay, she was also naked.

“It looks like you’ll have to keep me entertained tonight all on your own, little one.” She sat on the bed beside Jay and bent down to kiss him softly on the lips. Jay leaned into the kiss, making sure to keep his hands at his side.

“Ok, Mistress.” He replied. “What do you want me to do?” he was still learning how to please Jennifer, and since he was mostly subject to the antics of Kevin and Ben, it was harder for him to learn how to adjust for girls. Jennifer smiled and bent in to kiss him again. Her tongue dipped into his mouth to taste all of him as her body guided his down to the bed and pinned him lighly against the mattress. Her bare, heavy breasts pressed into him, and her hands wrapped over his and guided them together to pin them above his head.

“Mmnnhhh! Nhhhh!” Jay moaned loudly as she became more forceful in the kiss. He struggled around in her grip, feeling her large breasts bumping into his chest. They were so warm and soft, he wanted to squeeze them, but he needed permission from Jennifer first. His cock slowly erected between their bodies, pressing against his Mistress’s pubis. She broke the kiss and laughed softly at him. One hand kept his pinned above his head as her other reached down and teased at his shaft.

“I’m going to torment you, little plaything, until you’re begging me for permission to cum. Then you’re going to please me with your tongue and your hands and your cock. Do you understand?”

Jay moaned loudly and nodded quickly. His hips slowly thrust into Mistress’s hand.

“Uuuhhh! Y-yes!” he cried out, his legs quivering under him. “I want to please Mistress!”

“Then be good and stay perfectly still.” She said, releasing his shaft and hands. She stood up and went to retrieve some things from a trunk at the foot of the bed. After a moment, she came back with two strips of soft cloth in one hand. She bound his wrists together to the bed frame with one of them. Jay looked up at the binds, then back at Mistress. He didn’t understand what she was planning to do. How could he make her feel good if she tied him up like this? Jay’s cock bounced as he shifted around on the bed, standing straight up and throbbing gently. Jennifer took the second bit of cloth and wrapped it over Jay’s eyes to blindfold him. Once the light was gone from his vision, she bent down and kissed him on the cheek.

“Good boy. Now I can torment you good and proper.”

Jay jumped when he felt her lips press against his cheek.

“Y-yes, Mistress!” he exclaimed, a little unnerved by being blinded and immobilized. Mistress knew he was afraid of the dark. Was she going to prey on his insecurities tonight? He felt her shift off the bed, then come back after a moment. The soft tip of a feather tickled along the top of his foot, then over the heel and across to the other. Jay jumped and kicked his feet as he felt the tickling sensation from the darkness.

“WAHA HAAHAHAHHA! It tickles! Stop it!” he giggled, squirming about in the bindings. Jennifer laughed and pinned his ankles down with one hand.

“Terrible, isn’t it? You want me to stop?” the feather danced over his restrained feet.

“WAAAHAHAHAHAHAHAHAH!!! STOP IT!” he screamed. “It’s too much!” He thrashed about even more, trying to pull his feet out from under Mistress’s grip. The feather soon vanished into the darkness from whence it came, and Jennifer pulled his feet out to lay him out flat on the bed. The next time the feather came back, it was teasing along his cock, working from his ball to the tip and back again. Jay’s reaction this time was a loud shiver. He arched his back and twitched violently in the binds. His cock erected to full length again, throbbing as the soft material brushed up against the sensitive skin.

“Mm-Mistress…” he moaned, trying to cross his legs. Jennifer pulled his legs back out so he couldn’t block her access to his cock and began tickling around the tip and head of his member.

“You’re so cute, Jay.” She whispered. “Your little dick is twitching for me. It’s like I’m making it dance.” She laughed softly and flicked the feather across the very tip. Jay’s Kegel muscles instinctively contracted. Jennifer was probably going to continue this until he came, which wasn’t permitted until he was given permission. He moaned and wriggled back and forth, trying to lean away from the feather. Jennifer drew the feather away and shifted around on the bed.

The next thing Jay felt was her breath on his cock, blowing teasingly over the underside of his shaft in a tight stream of air. Jay didn’t twitch as much in response to this, but instinct told him Mistress’s mouth was only inches away from his dick. This made his cock throb in anticipation, wanting nothing more than to feel the warm interior of her hot wet mouth. To tease him even further, Jennifer traced the very tip of her tongue on the same path as the feather; along the entire underside of his cock and then around the head. Jay’s eyes widened, and he moaned louder than before, trying not to thrust upward and blow the chance to feel pleasure.

“AHHUUHHHH!! MISTRESS!” he cried out. “It feels so good!”

“I’m glad you’re enjoying yourself, Jay.” Jennifer said with a soft laugh. “Just remember, you’re going to have to pay me back for this, and you better not cum without my permission.” Her tongue swirled faster around the head of his shaft and teased at the tip. Jay quickly nodded his head. Since they began, Jay’s Kegels never relaxed once, trying to hold back the orgasm that had slowly been building up within him.

“Mmnnn… can I please cum, Mistress?” he asked. Right after he asked, he twitched even more, feeling her tongue coil around his dick like a snake. Mistress continued to tease and flick at him with her tongue, tormenting him relentlessly. She pulled back and blew softly over his cock again.

“Hmm... I don’t know. I mean, I’ve barely been touching you with my tongue.” She said, tracing over his stomach with long fingernails. “Surely you can hold out a bit longer, can’t you, toy?”

Jay slowly nodded his head.

“Y-yes, but I don’t know how much longer I can hold it.” He whimpered. “I want to at least ask for permission before I cum. I don’t want to be punished, Mistress.”

“Well, you did ask. I’ll think about it while I lick you.” She said, flicking her tongue over the underside of his cock teasingly. A hand gently brushed over his balls and grasped them. Jay shivered even harder, feeling her hand massage his balls. He thrust his hips up slowly against her tongue, trying to be as gentle about it as possible.

“M-misssstrreeeeeeessss…”

Mistress bent back and kissed and sucked and licked down over his member.

“Pet,” she whispered, her tongue teasing at his balls. “I’m going to count down from three. When I get to one, you have permission to cum.” Her hand wrapped over his dick and stroked him swiftly.

“Three.” Her hand moved faster, every few strokes gently contracting around the head. Jay grit his teeth and thrust up into her hand.

“Two.” She kissed at his balls and once on his inner thigh. Jay’s breath left him and he could feel the sperm already leaving his balls.

“One.” Just in time, Jay opened his mouth in a mute cry, cumming in a hot thick stream, firing somewhere into the darkness. Whether he wet the bed, or splashed Mistress in the face, he couldn’t tell. All he knew is he felt relief now, the pressure finally released.

“Mmnn… I feel so good now.” He sighed, relaxing for the first time since the session began. Jennifer pulled the blindfold off his eyes.

“You made a mess of the bed, boy.” She scolded coolly, pointing at the thick globs of his seed on the sheets. “Go get a towel and clean that up.”

“Oh! I’m sorry, Mistress” he apologized, quickly grabbing a towel on the other end of the room and dabbing the cum off the bedsheets. His legs almost gave out from underneath him as he was still a bit tired from his orgasm. Mistress, meanwhile, hauled herself up to lay at the head of the bed, legs spread.

“When you’re finished cleaning up, come lay with me.” She said, patting herself lightly on the chest. Jay nodded and folded the towel down where he took it from. He climbed back on the bed and lay down on top of his Mistress. He felt very awkward doing this, as he never got this close to Mistress’s body before.

“What do you want me to do, Mistress?” he asked with a shaky voice. Jennifer held him softly in her arms and stroked from his neck to the top of his soft rear.

“I want you to just lay with me for a bit, pet.” She answered. “You were quite adorable and you made me very excited, but I’m going to let you rest before I have you please me. I want you to be fully capable of it.

“O-ok!” he said, resting his head against her breasts. He felt very secure, if not a bit awkward, in her arms. He couldn’t help but smile, in a way, Jay saw her as a mother he never had. “I want to make you feel very good, Mistress.” He sighed, looking up at her. Jennifer kissed him softly on the firehead. She felt a motherly attachment to him that matched his comfort with her, and she saw no reason to resist it.

“I know you do, Jay. You’re a very good boy. I’m proud of all the progress you made.”

“Thank you, Mistress!” Jay exclaimed. “Now… what do you want me to do for you? I still have to fulfill my part for tonight.” His head rested on her breasts, feeling the warm soft flesh rub all up against his cheek.

“Do you still remember what I taught you about using your tongue?” she asked gently. “Start here with your lips,” Jennifer pressed a single finger to her collar bone. “and work your way down to my cunt.”

Jay nodded and moved up to first nip at her flesh before licking at her nape. She tasted nice to him; soft and sweet like a marshmallow. He slowly moved downwards, licking at her cleavage, then her navel, and finally the pubic region just a few inches above her pink nether lips. Jennifer gasped and moaned softly at the feel of his gentle tongue. Her legs spread wide in offer for his lips. He was already wet with anticipation, and the smell of her hovered close around her bare cunt.

“You’re such a good boy.” Jennifer said, breathing heavily. “Get into me good and deep with your tongue.”

Jay’s face came down to eye level with her cunt. He took in her sweet musky scent before licking the entire length of her slit. It felt much better than taking in Kevin’s dick. His tongue swirled around the edge before sliding inside her folds.

“Mmnnnmmm…”

Jennifer moaned sharply, her fingers digging into the soft blankets under her larger body.

“Good boy!” she gasped as she relaxed beneath his intentions. “Don’t forget to lick my clit, too!” She took hold of him by the back of his head to help guide him. Jay placed his lips over hers and “kissed” her, moving his tongue around inside her cunt. His arms wrapped around Jennifer’s legs to hold his head close to her pussy. Remembering to treat her pearl right, Jay moved his head up and licked at her clitoris. His lips closed around it, nipping at the sensitive nub of flesh. The woman groaned and tensed beneath him. Her hips rocked up to meet his probing tongue, and her clit hardened quickly in his mouth, growing more sensitive. Juices flowed smoothly and steadily out to meet his soft muscle, and her hands pulled him tighter against her wet folds. Jay drank in as much of her pussy juice as he could, his face glistening with her cum in no time. His attention came back to her clit, and he unwrapped his hands from around Jennifer’s legs and gently grasped the tiny nub. He used his fingers to pull back the foreskin and expose the raw nerves underneath. It was hot pink and clearly erect. Jay took the tiny thing into his mouth, gently clasping it between his lips and suckling on it. Jennifer moaned loudly in lust and gripped his hair. Her heels dug into the bed as she pulled him against her slit, a wave of powerful bliss passing over her, before she tugged him away and grinned drunkenly down at him.

“Jay, you’re such a wonderful pet.” She whispered. “That felt just exquisite. Now, come show me what you’ve been practicing with the other two boys. Fuck me good and hard.” One finger slid down his jaw and flicked softly at his chin before beckoning him closer. Jay sat up, his heart racing. He always got to see Kevin and Ben fuck Jennifer, but he never got a chance at it himself. In fact, he was always the catcher, never the pitcher. He was only ever allowed to get sucked off, and only at the discretion of the other three. Even now, with Mistress’s permission, it was difficult for him to even move. His body, however, said differently. His cock bounced up and down with even the slightest movement, ready to drill into her tight hole.

“R-really, Mistress?” he asked, feeling the blood rush to his face.

“Yes, pet. You’ve been very good since I got you, and you deserve a reward. Now, don’t expect that I’ll let you do this all the time, and you had better do a good job of it.” She laid back and spread her legs again, still beckoning him to her with one finger. “Now hurry up and fuck me. I need a nice, hard cock.”

“Yes, Mistress. I’ll make sure I do good.” Jay slowly lowered himself onto her mature body. He held his dick with his right hand and guided it to her pussy. With great trepidation, he slid it inside, moaning and clutching her body tightly.

“Mmn! Mistress!” he moaned, it was nothing like he ever felt before. His entire cock was being squeezed by her cervical muscles, creating a sensation he never felt before in his life. His entire cock was being squeezed by her cervical muscles, creating a sensation he never felt before in his young life. Jennifer shuddered and clung to him as he slid into her wet folds.

“Oh, Jay, you’re just as big as Ben.” She cooed softly. Her fingers slid over his soft skin slowly as she held him closely. “Now show me how much they’ve taught you about fucking.” Her grasp on him tightened, and she grinned hungrily at him. Jay nodded and thrust his hips against Jennifer’s. He spread his legs apart for support, and quickly picked up the pace. Because of his inexperience, he was a little slow on the draw, but this did not hinder him in any way. He liked it so much he didn’t want to stop! Jennifer rocked her hips up to meet his, taking his shaft deeper into her with each thrust. She moaned deeply and gripped the sheets, trying to keep her body steady for him. He wasn’t very good at this, as she expected, but he was packing some pretty decent heat, and his vigor was more than enough to stimulate her.

Jay pressed his face into her chest, taking in her musky scent. He liked her smell. It relaxed him and brought him comfort. He enjoyed thrusting into her, even if he felt a little uneasy about it. Several more thrusts and he shivered as he blew his full load into her pussy. After riding the orgasmic wave, his mind suddenly flashed back into reality, and he dissolved into a panic.

“Ahhh! I’m sorry, Mistress!” he apologized. “I couldn’t control myself!”

Jennifer hummed disappointingly, and gently patted Jay on the head.

“It’s okay, Jay.” She consoled. “You’re not very experienced yet, it’s only natural you would cum too soon.” Jennifer rolled over to let Jay down on the bed and pulled the covers over him. “Just relax and sleep here with me tonight. I want you to be well rested for what I have planned for you tomorrow.”

Jay nodded his head and buried it in the pillow. He was exhausted, and it wasn’t long before he drifted off to sleep, safeguarded by the mother figure watching over him.