The lights on Elm Street were amazingly bright. Larissa walked slowly, her brown eyes darting side to side as she kept her boy within her line of sight. His small boned frame encased in a black leather cat suit and knee high boots looked entirely feminine from the back; especially since she had told him long ago to let his blonde hair grow out into a mass of curls. She smiled to herself, watching as he made his way unsteadily toward their destination. He had no real idea what she had in store for him on this night. She was sure he would meet this little challenge. After all, she had been preparing him for months. Larissa reached her boy’s side just as he arrived at the club’s entrance. The doorman gave their ID’s a cursory glance before waving them through.
Inside, all was noise and laughter, smoke and music. Bass throbbed through speakers located through out the small club, making conversation difficult at best. She snagged his hand with her own and tugged him forward. “Time for a drink, Jordana.”
~Eight months earlier~
Larissa awakened to the feel of her boy curled around her backside, his body donating his heat to keep her warm. She yawned and stretched before prodding him awake with a fingertip. “Get up, you overslept, again.” He jumped and she laughed to herself at his wide-eyed appearance. His body was lithe and trim, covered with a fine sprinkling of pale blonde hairs over lightly tanned skin. Even his green eyes gave every appearance of innocent young androgyny. She mused for a moment before deciding that today would begin their next phase in his training. After a shower and breakfast, Larissa gave him a list of tasks to complete before her next visit. Most of these were as per usual but Larissa added a new one: the task of complete bodily hair removal. Well-trained, he knew not to second-guess her. However, Larissa could see the questions in Jordan’s clear green eyes. She left him with a kiss and a grin. This was going to be fun.
Jordan was more than curious about Larissa’s new order. It offended something deep down inside of him. Knowing his small stature and delicate bone structure gave him every appearance of almost femininity; he had always kept himself as well toned and masculine as possible. Yet, here she was giving him the order to remove one of the few things that actively showed his gender. He debated not doing it. The thought was almost more than he could bear. In the end, he had two choices. Do as she commanded or ask for release from service. He could not ask for a release for such a small thing. With a heavy heart, he went to find out the best types of hair removal for himself.
Two days passed before he arranged for a complete body wax. The procedure was both more and less painful than he expected, but took hours. Two girls worked on him, giggling lightly as they applied the warm wax and ripped it off again and again. His entire body ached by the time they were finished. There was absolutely no hair left, even his sparse groin hair was gone. He was tremendously embarrassed and flabbergasted at the amount they charged to cause him such discomfort. Once home, he stripped out of his jogging suit and gave himself a thorough once over in the mirror. He felt gay and not in anyway that could be considered happy or joyful.
He made his way slowly to the bathroom and ran a nice cool shower. He got in and allowed the coolness to calm the burning of his skin. He ran his fingers along his body as he lathered up. He felt like a girl for God’s sake! It did not take long for him to realize that he was more sensitive as his soft cock slowly raised to attention beneath his soapy hands. He knew better than to get off. That pleasure was for Larissa alone, but that did not stop him from enjoying the smoothness of his own skin beneath his hands.
Larissa arrived the next day. Together, they explored his new sensitivity. She was delighted by his new look and let him know it countless ways: a stroke along a hairless belly or quivering flank, a kiss on smooth legs, a smile as she looked into his green eyes framed by beautifully sculpted eyebrows. By the end of their visit, Jordan was as pleased as she was. Waxing became a monthly occurrence and the only thing added to Jordan’s list of duties. Soon, he began to believe it was really his own idea. Larissa just smiled and enjoyed the feeling of hairless boy flesh quivering beneath her hands.
The next stage was a little more difficult for all involved. Larissa had given her boy two months to become accustomed to the idea of being completely hairless. It did not take nearly that long, but she wanted him to be at ease with it before she introduced her next step. Jordan was bound across a small ottoman, his taut butt pleasantly welted by an earlier strapping. She massaged his ass using scented herbal oil paying special attention to the crevasse, sliding her fingers along the crack before easing first one finger then two into his virginal ass hole. He jumped and moaned slightly but never moved a way from her hands.
With economical grace, Larissa stood and walked to her tote. A tiny tube of lubricant and a small anal probe soon offered themselves up from the tote’s depths. She moved silently to her place behind him enjoying the sight of his red, welted butt.
“Ok. Relax, this won’t hurt a bit.” Larissa smiled as she watched him struggle to control his immediate reaction. He wanted to see what she was doing. She knelt behind him and spread his ass cheeks apart, squirting lube deep within his puckered brown hole. Jordan began to squirm, fiercely. She stopped her attempt at once and stepped away.
“Look, Boy, we can either do this my way or I can untie you and leave. I have done things your way for far too long. If that is the type of submissive you want to be, one who doesn’t want to test his boundaries, a bottom that thinks he is a top, that’s fine with me. I won’t be happy about releasing you, but I will.” Larissa grew silent as she let her softly spoken words sink in. “Is the problem one of trust, Boy?”
“No, Ma’am,” was Jordan’s solemn reply.
“What is the problem?”
“I don’t want to be a bitch boy, Ma’am.” He spoke with a bit more spirit.
“Would you prefer I do these things with someone else?”
“No, Ma’am.”
“So then, what am I to do, Jordan? I want to do this. I want you to let me. Your only choice is whether I release you from service or you let me do what I choose to do. There are no other choices.” Larissa waited silently, her body thrumming with repressed anger at the denial. She swallowed it down with some effort and waited for Jordan to speak. Five minutes later, he did so.
“Please Ma’am, continue.”
Larissa smiled but made no move to finish her plans. “I have decided to release you instead. I don’t have time for little boys who can’t make up their minds.”
Jordan’s response was to ask again. When denied, he begged to remain in her service, finally breaking down completely into sobbing. It was at that precise moment, that Larissa squirted lube on the anal probe and leaned forward to insert it. He jerked and groaned in response. Jordan was lost in sensation. The feeling of fullness was one he had never before experienced. He felt as if she had turned on a switch inside of him. Part of him wanted to protest this invasion. Yet, the throbbing in his cock spoke far more of his excitement than any words he could say concerning his unease or anger. Larissa soothed him with kisses and praise untying him from the ottoman and pulling him into her arms. Wrapping a hand around his throbbing cock, she jerked twice and allowed him to cum on her hand before making him lick it clean. Phase two was now in motion.
Jordan soon became used to the feeling of the probe. It pressed against something inside of him that provided all sorts of illicit thrills. She had told him to remove it only during bathroom breaks and bedtime. The first few days had been uncomfortable, but that passed, eventually.
When she introduced him to the next size, he wasn’t sure it would fit. The period of adjustment was a bit longer, but he grew accustomed to it as well. He laughed to himself whenever he saw the big tub of lube Larissa had provided for him. Inside he felt different, no less masculine than before, but something was changing. He was too scared to bring his fears to Larissa’s attention. Anyway, his worries seemed unfounded.
The Final Phase ~ three months ago~
Jordan was trussed tightly, a velvet blind covering his eyes, his arms stretched above his head and anchored to a small steel hook. Larissa circled him, her fingernails tracing designs on his skin. “Do you know what I want from you, Jordan?”
“No, Ma’am.”
“Well, I would love to see you take a cock.”
Jordan’s body jerked as her words hit him and his thoughts raced. ‘Get fucked? Like a girl? Like some homo? Oh hell no!’ Larissa continued her circling, teasing him by lightly stroking him, cupping his scrotum in her tiny hands. His cock began to harden instantaneously from her ministrations, his body thrusting forward against her palms. She stopped. He moved toward her, his movements hampered by the length of his restraints.
