“Mistress LF Slave Boy. W4M, 18-28” was the title of the Craigslist add. Trey, a 25 year old beta male, had taken to perusing various personals listings. He wasn’t much of a bar kind of guy, nor did he know much about how to go out and meet women. Sifting through the postings mostly made by men Trey had managed to come across several listings by women that seemed potentially promising. Unfortunately he’d never gotten the nerve to actually try and contact one of the listing parties.
He clicked on the oddly titled formerly mentioned post. It read:
Experienced mistress looking for a new part time sex slave. Be completely STD free. Be into light to medium pain, be attractive, be between 18 and 28 years old, be ready to do anything I command without question. If you are interested you must send me at least four, face included, full body pictures (front, left, back, and right perspectives) of yourself fully naked and fully erect. Your genitals must be shaved. If you do not completely follow all of my instructions I will dismiss your request. Though none of you deserve it, I have placed a picture of myself in this post.
The picture was of a slim, pale skinned woman. She was wearing a very short sheer black skirt with a black thong clearly visible underneath it. The expanse of her torso was bare with the exception of two black pieces of electrical tape covering each small nipple atop not much more than a handful of breast. Her pink lips curled up in a slight smile were as far as the picture went to revealing her face. Trey estimated her age must be somewhere in the early 20s or perhaps even younger.
Trey was not a virgin, but his sex life was sporadic at best. To make up for his lack of sex Trey masturbated about every day. His greatest fantasy was to be submissive to women. He’d watched countless videos of professional and amateur mistresses with their slaves and had always wondered if he’d ever get the chance to fulfill his fantasies. He decided this gorgeous and mysterious mistress would perhaps be the best chance he would ever get. He followed her instructions; shaving his dick and balls, getting his cock hard and setting up the camera to takes pictures of him from all four instructed angles. He then sent the pictures and brief description of his personality and desires to the mistress.
A week went buy with Trey waiting on pins and nails for a response from the woman. He couldn’t stop sneaking peaks over and over at his phone for an email while he was at work. Every it showed he had an email his heart would skip a beat as he went to see who it was from. For a week he went disappointed and resolved himself that probably some sicko had made the mistress post just to get pictures of naked amateurs. Then, when he’d almost given up hope, he received an email from an account he didn’t recognize.
“You were the only one to follow all of my instructions correctly so you will have to do. Come to the address I’ve attached this Friday night at 7:00. From now until then when you masturbate you are allowed only to look at the picture of me I attached to my post. You are not allowed to masturbate at all on Thursday and Friday before you come to see me. Make sure you remain clean shaven and I want you to wear a thong. If you do not have one you will need to go buy one. I look forward to making you mine.”
The email was signed Mistress Ashley. Trey was desperate with anticipation the whole week. He went and bought a bundle of thongs from Wal Mart late at night so he could use the self check out. He kept his gentiles well groomed and when Friday finally came around he was so nervous and horny he spent the whole day at work day dreaming.
Trey arrived at the address at about 6:50. He went up and knocked on the door. It was a rather normal looking rambler house. The door was answered and there was the beautiful Mistress Ashley wearing very normal looking sweat pants and a sweat shirt. Even in the completely concealing clothes she was gorgeous.
“Hey” Trey said sheepishly.
“Hi, come on in Trey” she said cheerfully. “I’m Ashley.” He followed her in. The house seemed pretty normal. “Have a seat” she said. Trey sat on a comfy chair and Ashley sat across from him on a sofa. “Have you ever done anything like this?” she asked him.
Trey responded truthfully with “No, I haven’t.”
“Good” she replied. “That means I can mold you my way.”
“Before we get started I want you to say the word ‘Montana'”
Trey looked a bit confused. “Montana?” he said.
“Say it again please.” she said.
“Montana” Trey said more solidly this time.
“Good, if at any point you decide you no longer wish to participate in what we are doing you need only say the word Montana. I will stop what I’m doing to you, untie you if you are bound, and you will no longer be my slave. Is this understood?”
“Good, now stand and strip down to the thong.” Trey slowly stood and started to take off his clothing. “Faster” Ashley said curtly. Trey quickly disrobed down to the thong which was a pink plaid woman’s thong. He couldn’t find any men’s thongs at the store. “Follow me” she said as she stood.
Trey followed Ashley down her stairs into an unfinished basement. In the basement were many implements of what appeared to be BDSM equipment. “As you can see, I am an experienced Mistress.” Ashley said. She led him to a point where a large metal eyelet was attached to a cross section of the ceiling. Ashley placed hand cuffs on Treys wrists and raised his hands above his head. She attached a large padlock to the cuff chain and then to the eyelet, holding Trey’s hands above his head. She then went to a table and grabbed two metal clothespins attached to each other by a metal string. They were obviously never intended to hold cloths. “These will get your nipples nice and sensitive while I go change.” She placed the clips on Trey’s nipples and he let out a bit of a scream. “They grip tightly don’t they?” she asked in a seductive voice.
“Yea” Trey answered in pain.
“Hmm, we haven’t gone over the rules yet so I’ll let that one slide. But from now on every time I ask you a question you will either reply ‘No mistress’ or ‘Yes mistress’. Is that understood?”
Trey looked at the gorgeous dark haired girl in front of him. “Yes mistress.” he said.
“A quick learner, we’ll have fun Trey. I’ll be back.” With that, Mistress Ashley left Trey hanging with a rather substantial pain in his nipples.
After about a half an hour Ashley came back into the basement. She was wearing the short black skirt and nipple tape she had on in the picture. She also had on dark eye liner that drove Trey crazy. During this time his nipples had almost gone entirely numb.
“First the rules.” She said. “You will not speak unless I ask you a question. When I do ask you a question you will answer Yes Mistress or No Mistress. Do you understand.”
“Yes mistress” Trey answered.
“You may not cum unless I allow you to cum. The only other time you may speak besides answering my questions is when you ask me if you may cum. Do you understand?”
“You will do everything I tell you to do without question. Do you understand?”
“Any disobedience will be punished with varying degrees of severity. Do you understand?”
“Then let’s get started” Ashley said. She went to a wall and pulled off a whip that had several small lashes on it. Without warning she grabbed the chain connecting Trey’s two nipple clamps and yanked them both off. Trey’s nipples were instantly on fire. He opened his mouth to scream and it took about two seconds before any sound even came out. “That hurt butch?” Ashley said. She quickly went in and bit down with her front teeth onto Trey’s right nipple. “I ASKED IF THAT HURT BITCH!?” and she moved over and roughly bit his left nipple
“Ahhhh, YES!” he yelled out.
“Yes what bitch?” and she raked her fingernails over his nipples up and down very quickly.
“YES MISTRESS!” Trey screamed. Ashley continued to scrape his nipples for a few more seconds before finally stopping and saying
She then started lightly whipping Trey’s chest, making sure to hit his burning nipples over and over again. She gradually increased the power of her strikes until Trey was letting out yelps with each stroke. “Stop complaining so much bitch, this is nothing. We need to gag up that mouth of yours.” She looked down to Trey’s cock which was growing rock hard from the abuse, it protruded stretching the fabric of the pink thong. “This will work.” She grabbed the back of the thong and started pulling it up into Trey’s ass. She pulled and pulled until finally something ripped and the whole thing came off. She held it up to his mouth. “Open.” Trey did so. Ashley stuffed the thong into his mouth and told him to close his mouth. Trey closed his mouth as much as he could with the panties. Ashley grabbed a roll of duct tape and put a few pieces over Trey’s mouth. “That’ll do the trick.”
Ashley started whipping Trey’s ass. Over and over, harder and harder until his ass was as red and sore as his nipples. With each crack of the leather against his skin he let out a muffled yelp through the panties and duct tape. She walked up to him and pressed her sexy, almost naked body against his red and fully naked body. She reached down and gently wrapped her soft fingers around his stiff cock. She slowly started to pump his dick and leaned her head against his shoulder. “Good job bitch, you took that like a man.” The feeling of finally having something touching his aching cock was enough to almost send him over the edge right then.
“Misssrrss, muh aaahh uummm?” he tried to mumble through the gag. Ashley knew what he was asking, but saw this as a great opportunity to torment her slave.
She gripped his cock a little harder and increased the speed of her strokes. With a sickeningly sweet voice she asked “What was that baby? I couldn’t understand you.”
“Peeeees misssssttrrrssss, mmmay, aaaahhh, uuuummm?” Ashley could see the frustration on her slave’s face as he tried to hold back the orgasm that was just waiting to burst from his balls. She jacked him off even faster.
“Nope, still don’t know what you’re saying.” She could tell he was getting very close to orgasm. “Wait, are you about to cum?” Trey attempted to say ‘yes mistress’ through his gag. “Now slave, I told you that you are not allowed to cum unless I give you permission, and I did not give you permission.” She continued her movements on his cock and now added her other hand in, cupping and gently massaging his balls. Trey’s mind and body could barely take the sensations being forced upon him. His ass and chest burned bright red, his arm, still stretched over his head, felt like they were about to fall off, and he was holding on to the very last threads of control trying not to orgasm as his gorgeous mistress was giving him the hand job to end all hand jobs. “Now if you would like permission to cum you must ask me clearly and articulately so as I can understand you.” She looked at him, waiting.
Trey gave one last futile effort to scream out “PEEEES MMMMAAA AAAHHH UUUUMMM!?” He pinched his eyes closed and used every last bit of his ability to hold off his orgasm from his mistresses sensual onslaught.
“I still just don’t know what you’re trying to say.” she said with a light voice. Trey’s orgasm was now upon him. Instead of being able to try and ask a question he just started letting out high pitched chirps as the muscles that allowed him to hold back his cum quavered and bean to give out.
“Oh no you don’t” Ashley said sternly. She quickly stopped her motions, dropped to her knees and squeezed Trey’s cock hard. Trey’s orgasm was right on the brink, unable to be stopped but unable to be completely satisfied without any stimulation and with a tight squeeze blocking the passage for the cum. Trey felt a pain in his balls as his orgasm was denied. He felt a burning through his dick as his balls attempted to push a few streams of cum out. He screamed out in agony as he experienced something that was not an orgasm but a slow, painful release of semen. It dribbled out the end of his cock. His balls never pumped, his cock never pulsated in that way so familiar to all men. Instead he went completely unrelieved as the cum leaked onto the cement floor. Trey needed to cum so badly that he felt it everywhere. He felt thirsty, he felt hungry, he felt like he itched all over; but it was merely his need to cum that was taking over his body and mind. He felt an incredible need to relieve pressure but it was impossible. His cock stayed hard, completely unsatisfied.
“You’ve made a mess my slave.” Ashley said as she looked at the small drops of cum on the floor. Trey just hung his head, his eyes closed. Ashley stood and quickly ripped the tape off of Trey’s mouth. The sharp pain on his face waked him from his hazy state. Ashley reached up and unlocked Trey’s hands. Trey immediately fell to his knees. “I’m glad you’ve already assumed that position my pet. You need to clean up that mess you’ve made. Lick it all up little bitch. Lick up every last drop.” Trey looked at the mess on the floor and then up to his mistress. She looked angrily down at him. “You are already going to be punished for cuming without asking permission, do you want to also be punished for disobeying my orders?”
“No mistress.” Trey managed to say through gritted teeth.
“Then clean that mess.”
Trey put his lips to the floor and started to gingerly lick his own cum. “Hurry up now, we don’t have all night.” Trey started taking bigger laps at the cum. The taste of it wasn’t so bad, it was just knowing what it was that made Trey’s stomach start to churn. He pushed through and managed to lick up all of his mess. “Good boy slave. Now I want you to lay on that bed over there, on your back.” Trey looked and saw a bed in the corner of the basement. He slowly started to stand and Ashley pressed her food into his shoulders. “Bitches walk on all fours slave.” Trey crawled over to the bed, pulled himself upon it, and layed down on his back.
Ashley had him stretch his legs and arms out and she securely attached them to the foot and head boards with rope. “Since you got to cum, it is now my turn.” Ashley said. Trey resented that more than anything she’d yet said as what had happened to him was one of the most frustrating things he’d ever experienced, far from an orgasm. Trey’s frustration slowly began to dissipate as the feeling in is cock and balls went away. He was also beginning to feel reinvigorated as he saw Ashley slowly start to take down her black thong. She hooked her thumbs onto it and let it slide down her beautiful legs. What she revealed was an amazing pussy. It was entirely hairless and completely smooth. It looked so youthful and pure that for a brief second Trey wondered if she was a virgin but such a thought was certainly preposterous.
Ashley stood on the bed straddling Trey, giving him a perfect view of her gorgeous snatch. She then lowered herself, kneeling over Trey’s face with her vagina hovering just above his lips. His mouth was literally watering at the amazing site. “Do you want to taste this bitch?”
“Yes please mistress!” Trey immediately answered.
“Good boy, enjoy.” she said as she lowered her pussy onto his mouth. Ashley commanded Trey to lick up, down, in, out over and over. She directed him exactly how she wanted to be licked. At the same time she was playing breath games with her slave. She would lower her pussy onto his mouth and, though for only a few seconds at a time, pinch his nose closed. Trey found the complete loss of control even over his own breathing to be absolutely intoxicating. He was now finally truly starting to give himself over to his mistress in a way he hadn’t realized even existed in his most vivid fantasies.
He fervently licked his beautiful, pale skinned, dark haired young mistress with everything he was worth. Soon he was bringing her to orgasm. Ashley screamed out as her slave expertly licked her to a powerful orgasm. With her juices covering Trey’s face she slowly came down off of her high. She lay back on top of Trey, feeling his breathing underneath her. Right next to her face was Trey’s penis, yet again rock hard and desiring contact. “Does my little slave want a real orgasm?” Trey’s eyes lit up with animalistic desire.
“Yes mistress, please mistress.”
“You’ve been a good slave, you’ve earned your orgasm.” Ashley knelt over Trey’s cock, aiming it up at her vagina.
She slowly started to lower herself onto his dick. It was like having several tiny orgasms that totally took Trey’s breath away as he, inch by inch, entered into his mistress, feeling her tightness and warmth. Soon she was all the way down to his pelvis, her vagina totally engulfing his rock hard cock. “Remember, you must ask me when you wish to cum.” With that Ashley started riding her slaves cock. It felt large, warm, and fulfilling inside her. As she moved her hips back and forth Trey did what he could in his bound position to compliment her movements with his own. It wasn’t long before the sight of his gorgeous mistress and the feeling of her pussy riding his dick while he was still mostly immobilized brought him to the brink of orgasm.
“Mistress, may I please cum?” he asked.
“Yes you may slave, cum in me. Fucking cum in me slave! Fill me with your bitch juice.” Ashley rode Trey hard and he soon felt the cum burst through his dick into the womb of his mistress. Trey screamed in pleasure as the most powerful orgasm of his life shot through him and entered Ashley. She rode him fast and hard until his body finally stopped spasming
“Mmmm, very good slave. Now…” she said as she removed herself from his rod. “You must clean your mess.” She again knelt over Trey’s face and instructed him to clean his load out of her pussy with his tongue. As Trey licked Ashley spun around so that she was facing towards his feet. He continued licking as he felt Ashley playing with his now flaccid cock. He wondered if she’d want him to go again. He wasn’t sure if he’d be able to get it up again. After a while Ashley was again entering into her own orgasm. She came on her slaves face once more before she climbed off and Trey was able to see what she was doing with his cock.
As he looked down he saw his penis in a plastic cage. He’d seen these before, he knew it was a male chastity device. “From now on you will only cum when you are with me slave. You are my slave and you are not allowed to enjoy your body without me present.”
Ashley untied Trey and sat on the bed next to him. She dropped the character of Mistress Ashley and was just back to being Ashley. “So did you enjoy your night Trey?” she asked.
“Yes.” Trey said. “I feel like I should say more, but, I don’t even know what to say. It was the most amazing experience of my life.” Ashley let the words linger in the air. She leaned in and gave Trey a big hug and kiss.
“Good” she said. “I look forward to seeing you next weekend. I have many more things planned for you and I.”