Will goes to Jackie and Amber's house, thinking they invited him over for some sexual fun. Jackie wants to train Will, if her Sub Amber, insists on having him as her boyfriend.
The black hood fell loosely to Will’s shoulders. His pulse began to race, and his breathing became strained. Initially Will thought the hood might be suffocating him, but he realized as he made a concerted effort to slow his breathing, the hood had very little effect on his oxygen intake. He was momentarily frightened when he lost his ability to see his surroundings, but as nothing else seemed to be happening, his fright eased and his curiosity began to take over. After all, he thought, while Jackie didn’t exactly say it directly, she did invite him over to have sex with Amber, and now that he was there with four women in the house, this could get very interesting. The hood and wrist cuffs must be part of a game they want to play with me, he thought. Jackie gave me a safe word, what was it… Primo. She said I could get out of whatever situation I was in by saying Primo. That thought seemed to put Will’s nerves at ease.
“Alright girls, listen carefully,” Jackie was now fully embracing her role as the Dominatrix she was. Amber, Kim and Anne gave their Mistress their full, undivided attention.
“Now that there is a man in the house there will be some new rules. First; you are not to touch his body—anywhere. If he asks you to touch him, for something as simple as scratching an itch for him, you do not do it without my permission. Will, if and when your hands are free, you do not touch the girls unless I give you permission—and you do not get to ask me to touch them, only they have the right to ask to touch you. You are here for their pleasure, not vice versa. I presume you will experience some satisfaction yourself, but that will only occur as a result of pleasuring the girls.”
Upon hearing this from Jackie, the blood started to flow into Will’s cock, and a slight bulge formed in his shorts.
“Girls, under no circumstances are you to get any of Will’s cum, or even his pre-cum, on you or in you, without my express permission. As a courtesy, I will tell you that for your first offense, you will be harshly punished. I will treat the parts of your body that get cum on it by pouring hot wax on them, and then you will spend two hours in the cellar. Repeat violations will result in more severe wax treatments, and increased time in the cellar. I hope I will not be forced to punish any of you.”
The cellar was the name of the space between the floor of the dungeon, and the ground below the house. While all of the girls had been shown the cellar, only Kim had spent time in there for punishment. The cellar was a actually a small crawl space under the dungeon floor. It was roughly eight feet long, six feet wide, and four feet high. The walls were built with mis-matched boards, and during the day time, a small amount of light could seep in through various cracks. At night, it was pitch-black. The floor was rock and dirt, and there was a small, very worn rug for the occupant to sit on. Fortunately, Hawaii has no snakes and few biting insects, so the only real concern was for the cockroaches that traveled under the house. When Kim had been locked naked in the cellar for four hours, she had gotten very cold, and had no choice but to urinate in the corner. When Mistress Jackie freed her Sub, she smelled the stench and made Kim pour two pots of boiling water on the spot where she pee’d. That didn’t entirely remove the smell, and any subsequent occupant would now have that to deal with as well.
“Girls,” Jackie continued, “this will be an educational process for each of you. I will show you various ways to give pleasure to a man, and I will instruct Will to use his hands, mouth and cock to pleasure you in ways only a man can. While you each of have done a superb job in pleasuring me, as well as each other, you will learn that the hunger and desires of a man can create intense feelings that you have yet to experience.”
Again, hearing Jackie speak about the pleasure he would be giving the girls, Will’s cock was getting harder and pressing firmly against his shorts. Then came the not so good news.
“To reduce the chances that these rules will be violated, Will must wear a cock cage when he is in the house. I do not yet know whether Will intends to follow the rules, or if his carnal desires will overcome him and he will need to find release, using one of your bodies to satisfy his cock. Once he proves himself as an obedient Sub, he may get to spend some time without his balls and cock under lock and key.”
Hearing this, the strength of Will’s erection began to falter.
“Lastly,” Jackie wanted to explain to her Subs. “As I stated earlier, Will is here for your pleasure, not his. Will’s eyes must remain covered unless I state otherwise. You three are very beautiful young women, and Will does not deserve the pleasure of seeing your sexy bodies, feasting his eyes on your necks, round breasts, pink nipples, firm asses, smooth pussies, and bare feet. Will, you are to remain quiet and keep your words to a minimum. If you start talking too much, I will not hesitate to place a gag in your mouth.”
Will’s thoughts were lost in Jackie’s list of the girls’ body parts he wanted the pleasure of seeing and touching. He had a fairly good mental image of Amber’s and Jackie’s nude bodies, but his imagination was running wild with what the tall, slender, Kim and the little cherub, Anne, would look like when they shed their clothes. His erection surged, and he then felt the first drops of pre-cum leak from the tip of his cock, immediately absorbed by the fabric of his shorts.
Jackie had been staring directly at Will’s crotch when she spoke about the girls’ bodies. She knew this young stud was as horny as he could be, fantasizing about having sex with four women now. It was time to lock-up his cock.
“Kim and Anne, take Will by the arms and lead him to the dungeon. Place him against the wall, where his arms and legs will be secured.”
The girls did as they were told and took hold of Will’s arms above the elbows. With his eyes covered, Will noticed his other senses had begun to compensate for his lack of vision. Kim’s and Anne’s fingers felt so soft. They held him gently on the arms, and put very little pressure on him as they guided him down the hallway to the dungeon. In Will’s excited state, he began thinking about these strange girls’ hands touching him all over his body.
Jackie stayed in the living room with Amber. She needed to balance her own desires to force Will to submit to her, against Amber’s romantic feelings towards him. She could sense Amber’s apprehension and saw a bit of disappointment in her eyes. Jackie needed to reassure her Sub that things were on the right path with Will, and that Amber would be involved in his training.
“Amber, I want you to secure Will’s wrists to the wall, and remove his shorts. You can touch his body in the process. Here is the cock cage,” she said, dangling the metal device from her left forefinger, offering it to her Sub. “You can lock-up Will’s cock and balls, and make sure nothing gets hurt in the process. Because this is Will’s first time in the dungeon, you may speak to him throughout tonight, but do not encourage him to talk, or I will gag him. And as I said, do not get any of his pre-cum on you while you are working. I saw his erection and the wet spot it made on his shorts."
Amber was pleased her Mistress was giving her some authority in Will’s training. It was the second time today she was getting to do some of the training, versus being the trainee. She believed it all had to do with her role in providing Jackie’s explosive orgasms earlier in the day. If that is what it takes to keep her Mistress in a good mood, she would have to find a way to keep it up.
Jackie turned to walk to the dungeon and Amber followed directly behind her. There Kim and Anne had placed Will against the wall, in front of the large wooden X that had many metal loops affixed to the wood. There was a lot of track lighting installed on the ceiling of the dungeon, but only two lights were on, and they both were targeted on the spot Will was standing. When Will came into the room, through his hood he thought he saw a large chair, and three smaller pieces of furniture in front of the chair. As soon as the girls positioned him with his back to the wall, the lights, shining on the hood, although not too bright, obscured his view of the room.
“OK girls,” Jackie made her entrance known. We are going to be in the dungeon for a while, remove your clothes and place them in the basket where they belong, you too Amber.”
Will could hear the sound of the shorts and tops coming off. He heard the clothing hit the basket as the girls followed their Mistress’ order. Nobody spoke.
“Sit down and let Amber go to work on our friend here.” Kim and Anne took their places on their velour-covered, foam lounges on the floor. The lounges were shaped like a wave, with the back rising high enough to rest their head, providing support to their legs with the smaller wave in the middle. The lounges were conducive to multiple body positions, and the girls had just about explored all of them.
Will could see Amber’s shadow approach him, and in a moment could smell the perfume on her body. Amber was going to take full advantage of her Mistress’ permission to touch Will while she executed the order to place his dick in the cock cage. She placed the palms of her hands on his bare chest and gently brushed them over his nipples. His body flinched and his erection throbbed against the inside of his shorts.
“Hi baby, welcome to my world,” Amber said softly.
Before Will could respond, Amber went on. “Shhhh… don’t say a word. I’ll take care of you and everything will be fine. This is a good start for you. Mistress Jackie is in a great mood with you in the house. I think we are going to have a lot of fun tonight.”
While speaking to Will, she unclipped the cuffs from behind his back. She lifted his right arm and clipped the wrist cuff to the board to the right of his head. She crossed in front of him and clipped his left wrist to the opposite board.
“I’ve secured your arms so you cannot touch us, or attempt to protect your body as Mistress Jackie instructed. I am going to remove your shorts, and then I will secure your ankles to the wall with another set of cuffs. You’ll fine baby, trust me.”
As Amber unbuttoned the top of Will’s shorts, his cock throbbed with the impending freedom. As she pulled the zipper down, his cock flinched with such force it immediately rose to the top of his shorts, and Amber smiled when she saw the blood-engorged, mushroom shaped head. She immediately noticed the clear pre-cum oozing from the tip, some of which had already run down on to the shaft. She was very careful as she peeled the opening of his shorts to the sides, as not to get any of the pre-come on her. Kim and Anne were trembling in anticipation of seeing what was concealed in Will’s shorts. Both of them were salivating and had to force a swallow to prevent them from drooling.
Amber pulled Will’s shorts over his muscular ass, and once clear, let go of them and gravity took over, and they fell to the floor. She stepped back from him, yet her body still blocked the view of Will’s cock from the other girls.
“My, my… your cock is even bigger than it was the day Jackie and I jacked you off above the Cove. It’s really beautiful Will. I can’t wait to feel you deep inside my pussy. Mmmm…”
Hearing that, Will’s cock pulsed, and another load of pre-cum emerged from the tip. Now that his dick was pointed-up, waving in the cool air, the pre-cum ran the short distance to the bottom of his swollen head, and dripped to the floor, producing a thin, long, clear string of liquid. Amber watched it happen, and began to wonder how she and the girls were going to be able to obey their Mistress, and not make contact with it. Amber stepped aside, revealing Will’s cock for the first time to Kim and Anne.
“Oh wow!” exclaimed Anne. Her eyes grew in size as she tried to absorb the view. She quickly glanced at her Mistress to see if she was watching her—and she was. Anne’s pussy had been getting wetter ever since she had been told to pull down her shorts and bend over in front of Jackie, and then when the butt plug went in, her excitement went to the next level. She just wanted to touch her clit a little bit. She could feel that her clit had swollen large enough to be peeking out from under its hood, and a few soft strokes would feel great right now.
“Oh my word, it’s huge!” shouted Kim. She swallowed hard, and stared at his cock. Her mind was trying to make the connection from Will’s thin, toned body, to the large, thick cock standing upright between his legs. Kim’s nose twitched, as she had a very sensitive sense of smell, and she could smell the earthy scent of Will’s pre-cum, and it made her involuntarily lick her lips.
Amber was smiling from ear-to-ear as she heard her friends’ reaction to Will’s nude body and his raging erection. She bent down on one knee to secure Will’s left ankle, then moved to his right, avoiding the drops of pre-cum that had fallen on the tile floor. Her head was at Will’s waist-level, and she noticed his large balls hanging from his body. She wanted to give him a little reward for being such a good sport so far, and she reached up with her right hand and took his sack in her palm. She gently rolled his balls around in her hand, and pulled them up to his body, where she slid her index finger over his perineum, and up to his asshole. That move surprised Will, and made his whole body flinch. It was the first time he felt the restraints holding him to the wall. The muscle contraction forced a burst of pre-cum out of the tip of his cock, and without pause, it dripped in a long string to the floor.
“Amber, get you hand off of his balls. I did not give you permission to touch him there. His balls have nothing to do with my instructions to you.” Jackie had no idea that Amber had groped his asshole or she may have punished her for the indiscretion.
Amber knew it was not prudent to disobey Jackie, but she had one more thing she was going to do before she took her seat between Kim and Anne. She stood, carefully leaned forward, and kissed Will on the collar bone.
“Good boy. Enjoy yourself tonight,” Amber whispered so the others could not hear.
“Sit down young lady!” Jackie barked. While she really wasn’t angry with Amber’s actions, she needed to demonstrate to the girls that she was firmly in control of everything that happened in the dungeon. Jackie was very turned on by the sight of Will’s naked body and his dripping cock. As she thought back to the orgasm he had given her with his mouth and the release she felt squirting at the peak of her climax, she felt the muscles in her pussy involuntarily contract, once, twice, three times. She thought it might be the start of a small orgasm, but the contractions subsided.
Jackie stood and walked around where Amber was seated in her lounge in front of Jackie’s larger chair. She turned and faced the three girls who continued to staring at the naked man chained to the wall in their house. Jackie looked at the cock cage Amber was now holding again. Suddenly, a problem dawned on her. The four inch cage was meant to prevent an erection, and therefore, a full-on, eight inch erect cock was not about to fit into the device. Now what was she supposed to do?
Jackie slowly approached Will, careful not to cast a shadow across his hood. Even through the fabric of the hood, Will could smell Jackie’s perfume upon her approach. Will suddenly felt her fingers on his hard dick.
Jackie took Will’s cock between her thumb and forefinger on her right hand. She lifted it up and looked at the tip. It pulsed once, and more clear, slippery pre-cum oozed out. She slid her finger and thumb up the shaft and pinched the tip of the swollen head, catching the pre-cum on her thumb like a drop of honey. The three girls stared at her, wild-eyed, as she slowly raised her hand to her mouth and licked the liquid from her thumb. Jackie’s pussy started pulsing again, and she had a fleeting thought that she would just hike up her skirt, turn around and bend over, and impale her wet pussy on Will’s erect cock.
“Mmm… girls, this is good. It might be some of the best I’ve ever tasted. Judging from the small puddle on the floor, it seems Will here can just keep cranking out his pre-cum. I want you three to taste it too, but just to caution you, the taste of it will make you very horny. It might make you think about sucking it straight out of Will’s cock, or slipping his rod deep in your pussy. That’s what the pre-cum is meant to do to you, release all of you inhibitions. So again, I caution you. You can taste it, but you will need to control yourselves.”
“Mistress Jackie, may I touch my clit now, and when I taste the pre-cum?” Anne had to ask as her juices were running out of the bottom of her pussy lips, down over the jeweled plug still in her ass.
“No Anne, you may not touch your clit. Sit still.” Jackie knew her girls were wound-up like never before.
Kim was visibly sweating in the cool environment of the dungeon, and she was straining to keep her hands on her knees. Jackie looked at her and thought that if she told her to stand up, there would be a large wet spot under her ass. Luckily the velour covers zipped off those lounges and could go into the washing machine.
“Amber, since you claim Will as your boyfriend; you will provide Kim and Anne with a small taste of your boyfriend’s pre-cum. Come over here.”
Amber stood up and joined Jackie, standing in front of Will. Jackie lifted up Amber’s right hand and sniffed the back of it. It smelled of the pussy juice that she gotten on it earlier in the night. Jackie thought quickly.
“Amber, I’m going to put some of Will’s pre-cum on the top of your thighs, and the girls will lick it off for a taste. Put one leg between Will’s’ legs.”
Amber did as she was told. She placed her right leg between Will’s legs and Jackie grabbed his dick near the base and squeezed it hard enough to made Will flinch. The result was as Jackie had hoped, and more of the clear liquid appeared at the tip. She directed Will’s cock down to meet Amber’s leg and wiped the pre-cum on her upper thigh, just below her hip bone. Amber stepped back and then placed her left leg forward.
“Good job Will,” Jackie said. “Give me another dose of your pre-cum.”
Jackie squeezed the base of his cock like she had done previously, but nothing came out. She reached for his balls and began massaging them in her hand. Amber knew she was taking a big risk with her Mistress, but she leaned forward and began kissing Will on his right nipple.
“Nice move baby. Make your boyfriend to pump out some more of his pre-cum for us.”
Amber was happy her Mistress approved. She tenderly bit on Will’s erect nipple and licked on it in hopes he would respond with more of his slippery liquid.
As Amber’s body was very close to Will’s, Jackie’s view of the two of them was somewhat obstructed. Knowing that, Amber reached around Will and grabbed his right butt cheek with her left hand. She gave it a light squeeze, but was really trying to pull his butt cheek to the side so she could fondle his asshole with her finger. She succeeded with hitting her target, and Will’s body flinched in surprise. That was all he needed to send another load of pre-cum oozing out of his cock. Amber felt Jackie wipe the slippery liquid on her leg and she let go of his ass and stepped back.
“Ahh… that’s good. Go stand between Anne and your lounge. Anne, you and Kim sit on the top of the lounges, and you will be able lick Will’s juices from her legs. You may put your hands on Amber where ever you like, but you may only lick her thighs. I don’t want any wandering tongues.”
The two girls did as they were told. They perched themselves on the small wave of the lounges, and they each took Amber’s thigh in their hands. They wasted no time in licking Amber’s thighs clean. They behaved as if they were starved for the liquid. Both of them moaned in delight, and they both ran one of their hands up over Amber’s ass, caressing it softly. They ran their other hand up the inside of Amber’s thigh, and the back of their hands met as they approached her pussy. They stopped when their fingers made contact with Amber’s wet lips. While continuing to lick Amber’s thighs, in an effort to make their Mistress believe they were still enjoying Will’s pre-cum, they played with Amber’s wet lips, her juices now running down their index and middle fingers. Without speaking, they both had the same thought about their next move.
Kim and Anne slowly inserted one finger each into Amber’s pussy. Her pussy juice was warm and slippery on their skin. Their fingers went deep inside of Amber’s wet pussy, and at that point, each of their thumbs made contact with her swollen clit, and began brushing over and around the hard bud.
Amber didn’t know what hit her. The girls’ tongues felt great on her thighs, but their fingers attacked her pussy, and now she was feeling immense pleasure. Her knees got weak and she grabbed the girls’ heads to support herself. The two fingers were swirling inside of her pussy, she could feel the massaging on her excited clit, and she knew she was about to come.
“Girls, how does that taste?” Jackie asked.
Kim and Anne did not take their mouths off of Amber’s legs to respond.
“Girls, I asked you a question!” Jackie was furious that the two of them failed to respond.
They both heard the anger in their Mistress’ voice and stopped licking Amber’s leg and placed their cheek on Amber’s hip and looked at Jackie, standing behind Amber, next to Will.
“It is wonderful Mistress Jackie,” Anne replied. “May I have some directly from the source?”
The girls had worked their fingers around to stroke Amber’s G-spot. They both found the same rhythm and were rubbing their fingertips into the slippery, spongy flesh. Amber bent forward at the waist, placing her hands on the girls’ shoulders to support herself. Her orgasm was eminent.
“Amber,” Jackie said, “are you cumming?” As Amber bent over farther, Jackie could see the girls’ hands pressed tight against her pussy.
“Oh fuck! Yessssss…” Amber reached her orgasm. She lifted herself up on her bare toes, and her entire body contracted and the muscles inside her pussy squeezed down hard on the fingers inside her. Amber inhaled, trying to catch her breath.
“Alright girls, get your fingers out of Amber’s pussy. Amber, you are lucky I do not punish you for that orgasm. Your friends took a little liberty with my direction, but they did not directly disobey me. She looked at Will, who maintained his erection listening to the activity in the dungeon.
“Come over here and let Will clean your fingers.” Jackie needed to get control of the situation yet again.
Kim and Amber walked to over to Will and stood on either side of Jackie.
“Kim, you first. Put your hand inside the hood and find Will’s face. Rub Amber’s pussy juice where ever you want.”
Kim did as she was told. She started at Will’s chin, ran her finger up over his lips, and smeared some of the pussy juice on his nostrils. To Will, the smell and taste of Amber was intoxicating and only served to heighten his arousal. He moved his head around in an attempt to capture Kim’s fingers in his mouth. He finally won that battle, but not until Kim had sufficiently smeared the slippery pussy juice on his mouth and cheeks. Kim pulled her fingers from Will’s mouth.
Anne was interested in playing a game. She had been staring at Will’s erect cock, and when it was her turn, she slipped two fingers directly into Will’s mouth and felt his warm , soft tongue lick the length of her fingers. She shuddered and knew her clit needed immediate attention. She thought she was going to die if she didn’t cum soon. She moved her body slightly and placed both of her legs around Will’s muscular thigh. She pushed her bare breasts against Will’s torso and grabbed his ass with the hand that was not being sucked deeply into his mouth.
“What do you think you are doing young lady?” Jackie demanded.
Anne was on her way to her climax, and even if her brain wanted it to stop, her body could not.
Jackie stepped to the wall next to where Will was shackled and retrieved her crop from its hook. She moved back behind Anne, who was fiercely humping Will’s leg, sweating and out of breath. Kim and Amber had each taken a seat on their lounges.
“OK Anne, you started this and you will not stop until you climax. Jackie lightly tapped the leather end of the crop against Anne’s right butt cheek, then quickly slapped it against her left cheek.
“Ahhh…” Anne exhaled, feeling the peak of her pleasure nearing. As her muscles contracted in her pussy and ass, she could feel the butt plug pushing against her insides.
Jackie again tapped the crop on her left butt cheek. “How do you like Will’s tongue licking your fingers? Imagine how that tongue feels on your clit.”
“Mmmm,” Anne moaned. She squeezed Will’s thigh tighter, and tilted her hips to put more pressure on her clit.
Jackie began to alternate firm, but not harsh slaps, on Anne’s butt cheeks as her rhythm intensified.
Slap. Slap. Slap. Slap. Slap.
“Oh shiiit… I’m cumming!” Anne screamed.
Will had been sucking hard on her fingers, and he had bent his thigh slightly to improve Anne’s angle to pressure her clit. He heard her moans and felt her body, first tighten up on him, then convulse in her orgasm.
Jackie stepped back and let her Sub cum. She then noticed there was a bigger issue.
Anne’s pumping up and down on Will’s thigh had unknowingly made her right hip come into contact with the head of his cock, and Will’s pre-cum was smeared on her body.
Anne’s full body contractions slowed until they stopped, and she took a step back from Will’s, then fell to her knees, enjoying the after-effects of her powerful, and much needed orgasm. Her heart was pounding, and she tried to catch her breath.
Will was standing chained to the wall, seeing nothing around him, and could only faintly hear Anne’s breaths, yet his erection did not subside. He was turned on, and the only thing that would relieve him was to release the pressure he felt in his balls.
They all heard Jackie speak. “Get up Anne. You have violated the rules and you will be punished.”
“What? What did I do? What are you talking about?
”
“Look at your hip! It is covered with Will’s pre-cum. That is a violation of the rules.”
“No! I didn’t touch his dick… It touched me.” Anne was realized she was in trouble and didn’t know what to say.
“Go to the bed and lay face down!”
“But… but…,” Anne stuttered.
“Be quiet! Get up and go lay on the bed.” Jackie was disappointed she needed to discipline one of her Subs this early in the night.
Anne got up and made her way to the upholstered mattress that was on four wooden legs, in the middle of the dungeon.
“Amber, Kim, secure Anne’s wrists and ankles with the cuffs on the bed.” Jackie felt the rush of her power now. The girls got off of their lounges and performed their duties as directed by their Mistress.
“No… please don’t.” Anne verbally protested, but knew better than to physically resist.
First, using a remote control, Jackie turned up the dimmers for the track lights over the bed, shining a warm light on Anne’s body. Then she picked up two twelve inch white tapered candles and lit one with a lighter, then lit the second candle from the wick of the first one. She approached the bed.
“Put a pillow under her right hip, I need it tilted up towards me,” she said to Amber.
Amber lifted Anne’s hip and stuffed a pillow between it and the mattress.
The candles burned, and they created a pool of hot wax at the top. When Jackie thought there was sufficient melted wax, she held the candles about four inches from Anne’s hip and began dripping hot wax over the dried pre-cum on her hip.
Anne held still for the first few drips of wax, but she began to feel the heat, and each drip felt like it was burning into her skin. She clenched her fists and held her breath. She took a deep breath only when she needed to.
Jackie skillfully covered Anne’s hip in wax, drip by drip. The heat was intense on the one spot on her body, and Anne just wanted it to stop. She was holding back her tears, and did not want Jackie or the other girls to see her cry. Without a word from Jackie, the dripping wax stopped, and Jackie blew out the candles.
Anne started to feel relieved that the dripping, hot wax had stopped. Jackie reached for a small towel on the table next to the bed. She covered her hand with the towel, and in a swift move, put her hand on Anne’s ass, and dug her fingers and thumb into her crack, grabbing the rim of the jeweled butt plug. Jackie tugged on it, expecting to free it from Anne’s tight little hole, but it did not budge and she lost her grip on it.
Anne immediately felt her ass lift slightly off the bed as her Mistress tried to remove the butt plug, and her sphincter tightened on its own.
“Release your ass and give me your plug! Jackie demanded of her Sub.
“I’m trying Mistress. It’s just tight… ahh… I might need a minute to relax…”
Jackie was not about to give her Sub another second. She pushed her hand hard into Anne’s crack, spreading her cheeks apart, and got the tips of two fingers and her thumb under the flared end. She pulled with all of her strength. It started to move, the wide center of the plug stretching Anne’s sphincter to its limits, and once the widest part had passed the tight muscle, Anne’s ass quickly expelled the smaller end of the plug.
“Shit!” Anne shouted as the plug came free. She immediately sensed the feeling of her gaping, empty ass, cool air flowing inside, blood retreating from her swollen anus.
Jackie set the plug on the table and then directed the two girls that had been watching. “Release her!” Jackie commanded. Kim and Amber did as they were told.
Once the cuffs were removed from Anne, Jackie gave her the next command.
“Get up and walk to the door to the cellar.”
“What? Where am I going?” Anne seemed confused.
Kim took Anne by the arm and led her to the door in the floor of the dungeon. Jackie was right behind them. Jackie bent down and grabbed the metal ring, lifting the door up. The sun had already set, and it was dark in the cellar.
“Get in there,” Jackie ordered.
“But Mistress…” Anne tried to protest.
Jackie hit Anne firmly on her calf with the crop. Anne’s knees bent in response to the pain, and when she did so, Jackie gave her a soft push into the opening of the cellar. Anne fell in, and went all the way down to her knees. Before she could stand up and continue her protest, Jackie slammed the heavy door above her. The door was thick, and there was no sound from below.
Jackie turned and looked at Will, seeing he still had his erection. “OK, time to get that boy’s cock in his cage so we can release him from the wall.”
Jackie went to one of her special “toy boxes,” the one where she kept all of her LELO brand toys. She had plugged-in the toy to charge it when they arrived home hours earlier. She had never used this particular toy before, but had certainly fantasized about putting it to use one day. She pressed the “On” button on the remote control, and the curved, black toy in her other had immediately began to vibrate. She quickly shut it off; satisfied it would function the way it was intended to. She walked back to her chair, and placed the toy and its remote on the seat.
“Girls, Will is going to need to bend-over to start the next part of the process of putting his cock cage on him. Each of you release one of his wrists, and hold his arms, while I set the bench in front of him.”
Amber and Kim approached Will, and did as they were told, and unclipped his wrist cuffs, lowering his arms to his sides. They each had two hands on him, one holding him on the triceps, the other on his forearm.
Will could smell Amber on his right, and he turned his head towards her. He whispered, “What is going to happen to me?”
“I don’t know,” Amber whispered back. “As far as I know, you’re the first man that’s ever been in here. If Jackie wants you to bend over, she probably wants to do something to your ass.”
“Like what?” Will quickly replied.
Jackie appeared out of the dark, wheeling a large wooden bench with a black leather, upholstered top. While it offered some padding, the top was very firm. She placed it length-wise in front of Will and scooted it closer to him, until the end was about a foot away from his body.
“Bend him over girls. Put his chest right here,” Jackie was patting a spot near the center of the bench. “Secure his wrist cuffs to the bottom of the bench legs.”
The girls lowered Will forward, and once his torso was supported by the bench, they dropped his arms down where his hands didn’t quite meet the floor. Amber and Kim clipped the wrist cuffs to the metal loops on the legs of the bench.
Jackie noticed Will looked very uncomfortable, still supporting his lower body with his feet on the ground.
“Bend your knees and lower your body onto the bench. Don’t slide too far forward or your dick will hit the bench. You are in a good spot, just lower your stomach against the top.” Jackie place her hand at the top of Will’s ass, not really pressing it down, more like guiding his body with it.
Will lay on the bench, knees bent and ankles still clipped to the wall. He propped his chin near the end of the bench, supporting the weight of his head. It actually felt good to put his arms down, improving the blood flow into his hands.
“Amber, put a latex glove on your right hand, and get the lube. Come stand behind Will.” Jackie walked to her chair and retrieved the toy she left there. As Amber followed her instructions, the two of them convened behind Will, standing between his slightly spread legs.
“May I touch Will’s body?” Kim asked her Mistress, from where she stood, next to his left shoulder.
“Yes Kim. You can rub his back and distract him from what will likely be a small amount of discomfort.”
Kim immediately placed both her hands on Will’s back, and began tracing the muscular ridges under his skin. Feeling Kim’s soft hands, Will momentarily forgot about the vulnerable position where he lay, and felt pleasure in her caresses.
Just then, he felt another pair of hands pull his butt cheeks apart. “Pour some lube in there,” Jackie directed. “We need to get his ass loosened up a little. Work it in there with your finger.”
Amber stared at Will’s exposed asshole. It looked as masculine and muscular as the rest of his body. She had played with few butts before, but they had all been women. This was the first male ass she was about to explore, and she knew Will’s ass was likely a virgin. She first put some lube on her index finger, then poured an adequate amount directly above his little hole, catching the excess on her fingers before it ran down on his balls.
Amber switched back and forth, massaging Will’s asshole with the knuckle on her index finger and her thumb. She pushed firmly, but noticed Will’s ass was rock solid, and the muscle surrounding his firm hole held stiff. Jackie had released Will’s butt cheeks from her grasp and stepped slightly behind Amber in the tight space between the bench and the wall. Amber wondered if Jackie was touching herself. The sight of Will bent over the bench, balls and erection hanging from his body, was quite erotic, and Amber knew Jackie liked to watch people giving each other pleasure.
Will was surprised that he was enjoying Amber’s gloved fingers on his ass. He fully realized she was going to try and penetrate him, but was considering she may not have the strength to do so. Kim continued to caress and lightly massage his back, and Will thought he started to feel the muscles in his ass begin to relax.
Amber certainly felt Will’s sphincter relax as she was holding her finger against the opening while massaging his perineum with her gloved thumb. She immediately pushed the tip of her finger in, up to the first knuckle, and felt Will’s sphincter tightly contract. She thought if it stayed that tight it would cut off the circulation in the tip of her finger.
Kim had felt Will’s lower back muscles tighten and knew Amber penetrated him. She put a little more pressure on his muscles, and felt them relax under her touch.
When Will relaxed a second time, Amber pushed her finger in deeper, up to her second knuckle. Will let out a small gasp, and his muscles flinched, but did not hold tight. Amber started to slip her finger out, and felt Will’s muscle’s instinctively try and push it on its way.
“No Will,” Amber said to him softly. “You have to resist the urge to push down. Let my finger slide in and out, no pushing on it either way.”
Amber gathered Will’s balls in her bare hand and lifted them away from his body. She wanted to give him some pleasure, and maybe massaging his balls would help him to relax. She glanced over her shoulder, hoping to get the approval of her Mistress, and saw that Jackie’s eyes were squeezed shut and she was biting hard on the side of her lower lip. They were too close together for Amber to look down and see what Jackie’s fingers were doing, but she had a pretty good idea they were rubbing on her clit.
She kept massaging Will’s balls, and his ass really began to relax. As long as she didn’t move too quickly, she could slide her finger all the way in, from top to bottom, and Will’s ass muscles would stay relaxed. His cock though, was a different story. She held her fist with his balls in it, tight against Will’s body, and could feel each flinch of his erect cock. She felt a little disappointment that all of his pre-cum was dripping on the floor, not on her lips and tongue, where she could savor the earthy flavor.
Jackie, who had drifted off into her own world and climaxed, now came back to life. She stepped over Will’s leg and went to her chair to retrieve the toy for Will’s ass. She returned to the bench and stood near Will’s ass, facing Amber. She held up the smooth, black, toy, shaped like an elongated “C.”
“What is that Mistress?” asked Amber, having never seen anything exactly like it.
Still holding the vibrator above Will’s body, she replied, “It’s a prostate massager. When inserted properly, and operated at the correct speed, it will cause Will to ejaculate. Hopefully, after that happens, his cock will shrink to a size that will fit into the cage.”
Taking notice of the vibrator’s girth, Amber realized Will’s ass was going to need to be more than relaxed, it needed to be stretched a little. She began the process of inserting the tip of her middle finger, along with her index finger, and while Will’s ass muscles squeezed on her fingers twice in the process, she had a second finger in his ass in no time.
Jackie took the lube and poured it on the vibrator, coating the outer skin with enough of the liquid until it was shiny and dripping. She handed it to Amber, who released Will’s balls and took the vibrator. She was studying the shape, trying to figure which way it went in.
Jackie could see her Sub’s mild confusion. “The top of the “C,” the pointed end, goes into his ass, and the bottom of the “C,” the blunt end, rests against his perineum, behind his balls.”
Amber smiled, partly because she now understood how the vibrator was meant to work, and partly because she thought it was going to give Will a lot of pleasure.
She slowly slid her slippery fingers out of his ass, and placed the tip of the vibrator against the opening. She immediately noticed the size difference between her fingers and the toy. The vibrator was closer to the diameter of four of her fingers, and she began to push it in.
“Mmmmmm…” Will began a long grunt as he tried to relax his ass—but couldn’t.
“It’s Ok baby,” Amber tried to comfort him. “You can take it. It’s really not that big. Your ass is going to love this.”
“I… don’t… know…” Will said between breaths.
The first two inches of the vibrator were in, but Will’s tight ass was halting any further penetration. Amber suddenly recalled the first time she had a large dildo inserted in her ass, and the trick that put it deep inside her.
“OK Will, I know how this feels. If you just relax, I’ll take it out for a minute. Take a deep breath and let it out. On your second deep breath, relax all of your muscles when you exhale, and it will be over.”
Amber watched Will’s body rise and fall with his first breath. His back expanded with the second breath, and as he exhaled, she felt his sphincter and muscles inside relax, and she instantly shoved the vibrator deep inside his ass, forcing the blunt end against his perineum.
A pained sound escaped Will’s mouth, “Ahhhhhh…” his arms and legs jerked against his restraints for the second time tonight.
Amber let go of the vibrator with her gloved hand, and patted his left butt check with her bare hand. Will thought he might have forced small tears out of the corners of his eyes when the vibrator hit bottom, but since he couldn’t reach his face with his hands, he wasn’t sure.
Jackie stood with her arms crossed, smiling at her Subs. “Stand him up girls. Chain his wrists back up to where they were. They helped Will get to his feet; his huge erection apparently enjoying the pressure of the toy against his prostate gland. There was a small puddle of pre-cum on the floor where his dick had been dripping. The girls were careful not to step in it.
Jackie moved the bench while the Subs secured Will to the wall. She returned to stand directly in front of Will. With her heels on, she was exactly his height.
“Amber, take my blouse off. Kim, take my skirt off.” The subs did as they were instructed, and knowingly place Jackie’s clothes in the basket with their own. Jackie was left wearing her thigh-high black stockings, her strappy heels, and a black-jeweled choker necklace at the bottom of her neck. Amber stared at her mistress and reflected how lucky she was to have this beautiful woman in her life.
Jackie stepped forward and placed her bare tits against Will’s chest. The very slippery tip of Will’s cock pressed into Jackie’s flat stomach, just below her belly button. Ever so slightly, Will moved his body back and forth, making his cock slide against Jackie, and he felt the pleasure in the nerve endings where his cock touched her. Her nipples were hard against his chest, and he craved to have them in his mouth.
“Well young man, your erection will not fit into the cock cage, so we are going to have to do something to get the swelling to go down. Your girlfriend happily inserted that prostate massager in your ass, and now I’m going to use it to make you come. Jackie reached down and grabbed Will’s erection. She had to lean her hips back to point it down, and placed it under her wet pussy lips. She let go, and Will’s cock was trapped under her pussy, pushing up into her wet folds. Jackie rocked her hips, stroking the top of his cock. It felt good, but it wasn’t going to make either of them cum.
Seeing this, Amber’s first thought was that Jackie had placed Will’s cock inside of her pussy, and she felt a sinking feeling in her stomach. She stepped forward and was within four feet of Jackie. Jackie slid backwards off of Will’s cock, and she felt the head move up through her lips and brush over her swollen clit. Will’s cock slapped against his own abdomen when it was finally freed. Jackie turned and was blocked by Amber standing behind her. She knew what her Sub had been thinking.
“No I didn’t fuck him,” she said looking into her eyes. “And if I had, what would you do about it?”
Amber knew there was only one right answer, “Nothing Mistress.”
“Good, let’s all sit on my chair and watch the show!”
Jackie sat in the middle of her curved, large chair, about the size of a love seat, with a high back on it. It was the perfect space for three petite girls, and since Anne was still in the cellar, Amber and Kim would get to watch Will’s climax, while snuggled naked with their Mistress. When they all got comfortable, Jackie hit the button on the remote control. They each saw Will’s body jerk, and heard the clanking of metal the restraints holding him to the wall.
“Woah!” Will exclaimed. When the muscles in ass tightened down, the vibrations felt more intense. His cock stared to flinch in a slow rhythm, and his pre-cum began to flow again.
“Just let it go,” Jackie coached Will. “Feel those vibrations in your ass and just let it go. You are going to love your orgasm tonight. Give us your cum. We want to see it.”
In addition to his uncontrollable pulsing cock, Will began twisting his body side to side. That didn’t do much, other than to slightly move the hard object in his ass, briefly shifting the intense vibrations on his prostate. Will had thought that Jackie was operating the vibrator on its highest speed, just then, he felt the vibrations speed up.
“Geez!” Will said, his knees failing him, causing him to fall the short distance until he was hanging by the wrist cuffs. He tried to regain his footing, but the muscles in his groin and abdomen were starting to contract, and it was difficult to lift his legs. The head of his cock was dark red, with the ridge around the head, a deep purple. Will thought if any more blood flowed into his cock, it would explode.
“Let me stand up!” Will pleaded. The pulsing in his cock quickened, and the pre-cum was nearly a solid stream from the tip to the floor.
Just as he got his left foot planted on the floor, Jackie turned the vibrator up to the next speed.
“Ahhhh!” Will’s foot slipped and he hung from the wrist cuffs, his feet were positioned against the base of the wall, his body was arched outward, towards where the girls sat.
Will’s stomach muscles tightened, and that showed off the cut of his muscular abs and obliques.
“Ready girls?” Jackie asked a rhetorical question. “Let’s see what this boy can do.” With that, she turned the vibrator to the fastest speed.
“Woahhhh… woahhhh…” Will could not speak. The muscles in his throat clamped shut.
His cock stood nearly straight up against his body. The first drop of real cum appeared at the tip.
“Here it cums girls! Watch it cum.” Jackie didn’t need to say a word; the girls’ eyes were already fixated on Will’s cock.
The muscle’s holding up Will’s cock released for a split second, and his cock almost fell perpendicular to his body. Then in an instant, it shot back up, spewing the first, long, white rope of come almost four feet from where he stood. There was a slight delay before his cock repeated that motion, and the second shot of come went farther than the first. Then the contractions sped up, and the cum from the third, fourth, fifth, and sixth explosions, each traveled less than the previous one. Jackie pressed the “off” button on the vibrator, and it went quiet in the room.
Will took in a big gasp of breath, but did not speak. The smell of fresh cum filled the dungeon, and coupled with what their eyes had just witnessed, the girls were extremely aroused. Even the slight shifting of their legs gave their swollen clits pleasure.
Jackie stood up and walked slowly to Will. She slid two fingers over her clit, and was quite surprised that so much wetness had worked its way that high up between her lips. She was careful to avoid Will’s spray of cum on the floor. She stood to the side of his body, and as she had done earlier, she took his cock between her thumb and fore finger, and slid them to the top, expelling a large drop of pure white cum. She wiped it off with her finger, and while she wanted to taste it, she quickly moved her hand up under Will’s hood, and smeared the liquid on his lips and tongue. As Will was distracted by Jackie’s cum covered finger, she reached under him and yanked on the slippery vibrator in his his ass. It had served its purpose. Will flinched hard, and involuntarily assisted Jackie by squeezing his ass muscles, nearly thrusting the device out of her hand.
“Every time you cum in this house, you will taste your own sperm. It may be delivered by a finger, a tongue, or a pussy, but mark my words, you will taste the product of your own pleasure.” Jackie was delivering a new rule to Will.
“What do say to that?” Jackie demanded.
“OK,” Will weakly responded, trying to relax after his orgasm and the abrupt removal of the vibrator.
Jackie raised her knee and it collided with Will’s ball’s, quickly ending the afterglow of his orgasm.
“Ouch!” Will screamed as he twisted his body in response to the pain.
“The only acceptable answer is ‘Yes Mistress.’ Do I make myself clear?”
“Yes… Mistress.” Will nearly forgot to specifically follow her direction.
“You will taste your cum after every orgasm.”
“Yes Mistress.” Will did not hesitate, wanting to avoid a second knee to the groin.
“That’s better. Amber, come over here with the cage. Kim, you can kneel here beside Will and watch the process. Be careful, there might be some more cum in Will’s shaft, make sure you don’t get it on you.”
Jackie stepped back and let the two girls kneel next to Will. Amber unlatched the cage, and opened it up to where she could slide Will’s cock inside. She held it up to Will’s slowly shrinking cock, and could see that it would just now fit inside. She slid it up under his balls, then over the length of his cock, her hand never touching him in the process. Once Will’s cock was inside the metal frame, she folded the latch shut on top. At that moment, Jackie appeared from above her, reached down, and placed a small padlock through the loop in the latch. She snapped the lock shut. Amber released her grip on the cage, and it hung on its own from Will’s cock and balls. She had a fleeting thought that it looked sad in there, if in fact, a cock could show emotion.
“There we go girls. We now are safe from this cock. Unchain Will from the wall and lay him on the bed. Cover him with a blanket; he might need a little rest. Once he’s on the bed, we are going to have a little fun ourselves. I’m guessing you two are as excited as I am, and you poor Kim, you are the only one that hasn’t cum yet tonight, so you are going to be first!”
Kim smiled as she stood up and embraced Jackie, their bare breasts pushed together, meeting nearly exactly on the nipples. Jackie initiated the kiss, so Kim was permitted to willingly participate. After nearly a minute of their two tongues darting inside of each other’s mouths, Kim whispered, “Thank you Mistress.”
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