"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?"
"Yes."
"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.
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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.
