Larissa & Jordan

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.

She stepped back and reached for her ever-present tote. Inside were a custom fitted leather harness and a nicely molded dildo. She removed her clothing before strapping the harness on and placing the dildo for best effect. It rubbed against her clit with each movement, making her shiver. It took a few tries to get it adjusted properly, but once she did so, the effect sent shivers straight through her. “Jordan, I am going to fuck you.”

His answer was a whimpering sigh. Larissa wanted his co-operation but more than that, she wanted to see just how he would react to this invasion. Would he accept it or would he fight her? She bent to grab a footstool and strode back to Jordan, allowing her cock to brush against him. He moaned and jerked but said nothing to stop her. Larissa removed Jordan’s latest probe from his ass, the largest one they sold, a little bit bigger than 6 inches. She squirted more lube into the now empty hole before slathering some on her dildo. Then, she stepped up on the stool, which placed her directly at his anal entrance.

She set the head against his hole and slowly eased herself in. He went wild, bucking and moving so frantically that Larissa had to hold on tight to his waist with one hand. The other she used to deliver a stinging slap to his cock, which was now even harder than before. Jordan’s breath rasped out of him as he forced himself to hold still. Confusion reigned as unknown sensations raged though him. Damn it, he was straight! He tried to control the need to fuck back against Larissa as she stroked in and out of him, her hand caressing his cock in tandem with her thrusts. Eventually, the pleasure over rode his need to stay still. She fucked him harder and faster, her voice a whisper in his head, her hand bringing him closer to that final place of release. A guttural cry, dredged from some primal place, echoed around the room as she came. Her sound sent him spiraling over, into his release. Even then, tears of hurt and anger trickled down his cheeks from beneath the blind. Larissa felt them as she removed the blind and then the leather cuffs holding him stationary. She stepped off the footstool and motioned him to kneel. Jordan did as bid, his body limp from his orgasm and shame. He was glad she could not see into his head. A fierce anger burned inside. He wanted release from service. He did not want this. He would not accept this. Larissa’s soft words brought him up short.

“Thank you. You did well and I am beyond pleased. I know you believe you want me to release you from our contract. You think that I have made you into less of a man. Well, I don’t think I have. I think that you are more than you previously thought. So, my pet, shall we see just how far this transformation takes us? Or do you wish to part company?”

“Ma’am, this would be easier if I knew what all of this was for.”

Larissa took a moment to gather her thoughts. After all, she did not feel as if her reasons were really that important. “Jordan, I have always wanted to take a boy and bring him out. It has been a fantasy for as long as I can remember. To know that someone respects me, needs me, craves me so much he will try anything I ask, including cross-dressing or bi-sexual encounters. My reasons are so varied; I could not list them all, even if I wanted. I choose you to discover this with me. I want you to receive the benefit of my lust, my caring, my need to be a part of this. In all reality, I don’t want to hear no from you, but I know this is not what you expected from our relationship. At this point, the choice is yours. But if you agree, then we will go all the way.”

Jordan’s words were slow but sure when he responded. “OK, Ma’am. You seem to know more about this than I do. I will follow where you lead.” Larissa’s answering smile and hug were all that he could have ever desired and more.

~The Transformation~

They shopped and Jordan spent more time in the women’s clothing section than he had ever thought possible. Under garments, hosiery, shoes, boots, dresses, pant suits. Luckily, he was almost as easy to shop for as any small boned female. The first time he slipped on a pair of boy cut satin panties; he made such a mess in the front that Larissa had no choice but to buy them. He was sure he would die of embarrassment. Larissa just smiled at him and took him to another store. They spent weeks searching for the perfect outfits, the perfect shoes and the perfect style. Each new item was a revelation for Jordan. Each new thing he touched or tried on, brought him closer to the place of complete acceptance.

After the wardrobe was complete, they began the lessons: comportment, make-up, and hairstyling. Larissa pulled so many drag queens before him, he felt like a stud for rent. His favorite artiste was Justin, a small oriental boy who was absolutely stunning in full drag. From him, Jordan learned the art of tuck and tape, gliding and wiggling. Jordan enjoyed all of this far more than he thought possible. Larissa complimented him continuously and he enjoyed the rush of going out in public with her, dressed as his alter ego. The decadent feeling of fucking her, while wearing corsets and boy cut briefs in satin and lace, was just an added bonus.

Soon, she took to calling him “Jordana” causing him to blush whenever they were out. He was unsure of the direction this would take, though he enjoyed her intentions far more than he had thought he would. At least he had until last night.

~The night before~

“Jordana, come here please.” Jordan ambled slowly to her, walking seductively in the three-inch pumps she had instructed him to wear for her visit. She smiled at him as he entered the room, her brown eyes moving over his frame, taking him in from the top of his prettily curled hair to the tips of his navy blue pumps.

“You look lovely, Pet. Kneel for me.” It took a bit of doing, the tiny blue mini causing Jordan some problems, but he finally managed it. He knelt in front of her, hands on his thighs, ass resting on his pumps, eyes straight ahead. “I would like to take you out to a club tomorrow night. There is a young man I would like for you to meet. If things go well, I want to watch you two together.”

Larissa grew silent as she waited for his answer. This is why she had been training him - this test. It was one thing for him to know he pleased her when she was fucking him with her strap-on. It was completely different for another man to take the ass that belonged to her. She wanted him to take it and get off from it, because that would please her as well. Would he do it, though? Would he trust her judgment at least enough to try it?

She sat quietly, awaiting his words. How else could she revel in his submission to her if he would not trust her with the small part of him that had always remained buried in his psyche? She wanted this, but even more, she thought he needed to do this regardless of what his mind yelled at him. Jordan listened to her, his mind a jumble of thoughts. Did she really expect him to allow some unknown man to fuck him? Is that what she was asking? Could he even do it? Was there something inside of him that made her think he would do this? Finally, the answer dredged itself from his brain. It was not only about what he would allow; it was about her complete control over his sexuality. It was a form of submission to her will, not just a homosexual act. Could he submit to her in this as well? The answer to those questions was much easier.

“OK Ma’am. What should I wear?”

~A return to the present~

“Time for a drink, Jordana.” They made their way past the jostling crowds and sat down at the bar. A big bruiser of a bar tender took their orders, barely glancing at Larissa as he ate Jordan alive with his eyes. Jordan blushed and lowered his head. Larissa reached out for her boy’s hand, letting him derive strength from her grasp. Soon, a well-built, young male joined them. Jordan had to look twice before he realized that the young man was actually Justin. He smiled sweetly at Jordan before turning his head to whisper something into Larissa’s ear.

Jordan began to shake, his body finally catching up to what his head all ready knew. Larissa really was going to set him up to fuck or be fucked by a guy. It took every ounce of self-control he possessed not to leave. Larissa tightened her hold on him for a moment and then, she let go. He knew what that meant. She was telling him that he could leave, if he chose. He took a few sips of the drink that had magically appeared before him and worked to control his breathing. Eventually, Larissa arose from the bar stool and beckoned both young men to follow her. Jordan glanced sideways at Larissa’s pick for him. Justin really was sexy in a completely unobvious kind of way. All three of them sat down at a table located far away from the crowded dance floor and loud music.

“Jordana, as you must have figured out by now, this is Justin. I chose him for two reasons. The first and most important, he is attracted to you. The second reason is simple. He is amiable to training and can work as a top or bottom. I want to see him put you through your paces. Do you understand?”

“Yes, Ma’am.”

“Are you ready?”

A moment of silence and then the final confirmation, “Yes, Ma’am.” The three of them ordered another round of drinks to celebrate, before exiting the club. They decided Justin would meet Larissa and Jordan at Jordan’s apartment, so that Larissa could answer any unasked questions while she and Jordan were alone.

The car ride to Jordan’s was in complete silence. Larissa was not sure if that was a good sign or not. She hoped, for Jordan’s sake, that his silence meant acceptance. Jordan entered his house first, turning on lights as he went. Larissa noticed his slight shakiness as he bent to unzip and remove his boots. She called him to her side and waited as he joined her in the living room. “I will be there during every step, Jordan. Do not worry.” Jordan nodded and then asked with a small smile for a hug. She granted his request before pushing him gently away. “Go to your bedroom and undress. I will be along shortly with Justin.” A few moments later, the doorbell rang. Larissa motioned Jordan to move along before going to answer the door.

“Hey Justin, come on in.” Justin came in, his smile wide and dimpled. “He is waiting for you. Go get acquainted and I will be in shortly.”

~The Bedroom~

Jordan was scared. No other word described the twisting in his gut. He struggled to control his breathing but nothing seemed to work. He was overheating in every sense of the word. Finally, the door opened and Justin entered, alone. “Hello Jordan.”

Jordan’s heart rate sped up a bit more. It was almost time for the party to begin. Jordan nodded at Justin and looked toward the door, his heart calming when Larissa made her entrance, carrying a small chair. “Justin, you may begin whenever you are ready.”