A Sissy's Journey Ch. 01

This work is authorized by the author exclusively to Literotica.com for publication.

Introduction: A tale told in short vignettes which chronicle one young man's journey into self discovery.

Please Note: This story series contains elements of homosexuality, cross-dressing, light femdom and male feminization. All characters are fictional and portray adults over eighteen years of age.

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PART ONE

"You are so beautiful," Jesse whispered as he slid the delicate pink lace down over Amanda's hips. The whisper, so faint that it seemed he was speaking to himself and not to the wonderful creature who lay before him.

Amanda watched, entranced as Jesse put the damp fabric to his nose and breathed in her scent.

Finally, she was naked in front of the man who had been her friend all through college. It had taken so long for this moment to unfold and her pent up desire, fueled by so many fantasies, was almost unbearable. When Jesse dropped her panties aside and gently pushed her legs apart, Amanda felt like a helpless captive unable to resist the man who was devouring her with his eyes. As the closed folds of her pussy opened she moaned with pleasure just from this open exposure. The slight tingling that took over her pussy felt like a mini-climax!

Jesse knelt motionless and stared into the portal between Amanda's parted legs. Mesmerized, he couldn't lift his eyes from the delicate pink entrance, open and inviting him into her body. Despite his attractiveness in both personality and appearance, Jesse had not been very successful in relationships. It wasn't that he had never seen a naked woman, he just hadn't seen very many. And he had never seen one so beautiful and perfect. In fact, he had never been allowed to take his fill of every detail like Amanda was offering him now. His first instinct was to put his mouth on the moist lips beckoning him, drawing him like iron to a magnet.

When his tongue did touch her, it was a magical moment shared by both and in some mystical way shared as one. Amanda could smell her own arousal and knew that Jesse was breathing her most private scent deep into his lungs. Being exposed in so many ways was causing her to feel light headed! She unconsciously pulled her erect nipples, sending quick shivering tingles down to the swollen nub where Jesse's tongue was exploring.

"Please Jesse, I need you," she was just barely able to gasp out the words, her eyes closed and her head pushing back into the pillow.

Jesse seemed to not hear her as his tongue explored deeper into her body. He licked, almost frantically, exploring every exposed morsel of her flesh. Lifting her spread legs upward, Jesse's tongue continued the exploration into her other hidden crevice. Amanda gasped aloud when his tongue found the tightly puckered flesh that loved to be kissed.

Finally, unable to endure anymore of the caresses from Jesse's tongue an urgent cry escaped her lips, "Fuck me, please fuck me Jesse! I need it so bad, please do it...please."

Jesse, hearing her plea was somewhat stunned. As one awakening from a dream, he tried to hear more clearly what was being asked of him. Quickly enough, his fogged brain cleared and he knew that Amanda was begging him to mount her.

Almost as if a bucket of water had been poured on him, Jesse awakened form his stupor and panicked. He had been here before and dreaded what he knew would come next. Valiantly, he tried to quickly position himself and comply with Amanda's urgent calls. But as he grasped his cock, he already knew it was loosing the engorged fullness of just moments earlier. Trying to push his wilting flesh into Amanda's open pussy made it clear to both of them that the ending would not equal the beginning in this quest for love.

"I'm sorry," Jesse said in a defeated whisper.

Amanda felt like a bucket of cold water had just been poured on her too. Her first thoughts were ones of self doubt. Wondering if she was really that unappealing to him, she asked, "Is it me? Something I said?"

"No, your beautiful. So beautiful...it's me. I don't know why this happens, but it always does. I have never been able to stay hard long enough to get it in," the last words sending shame into the very bottom of is soul.

Amanda, had not believed what two of her friends had once told about Jesse not being able to perform. But now she knew it was true. This delicately beautiful young man was impotent. But, he was so hard before she had asked to be fucked. How could that be if he were impotent, she wondered.

Jesse mistook Amanda's silence as brewing anger and wanted desperately to say something to make it all go away. "Amanda, it's not you. Please believe me. I adore you and always have adored you. I think it is because I am so small that it makes me feel insecure, or something," Jesse repeated the excuse he had read online about being a limp dick.

"You're maybe a little smaller than most, but not that bad," Amanda replied. "I think it's something more than that."

Sitting up and putting her clothes back in order she added, "It's okay. We're best friends and if you don't find me attractive that way, I understand."

"Amanda, it's not that at all! Please don't say that. Please don't. You are the most beautiful woman I have ever known. I just want to kiss and lick all over you. You saw that I was hard earlier. I am aroused, I just don't know how to be a real man, I guess."

"Jesse, that just doesn't make any sense to me. I want to understand, but I'm not getting it."

Jesse was at a loss how to make her understand without telling her his hidden secrets. Probably best to just drop it, he thought sadly and continued putting his pants back on.

"We can still be friends," Amanda offered.

As he finished buttoning up his jeans and without thinking he blurted, "We're more than that and you know it!"

They looked into each others eyes and Amanda saw the pain. She also saw the tears beginning to overflow down his cheeks. She could never stand the sight of tears and soon she joined Jesse as they hugged, cried together and their hearts grew even closer.

Finally, with the tensions eased, Jesse felt safe enough to confess, "Amanda, I'm pretty sure I'm a queer."

Amanda looked at him like she hadn't heard him, but before she could speak he added, "Or maybe I'm Bi or something, I don't know."

"Well, that does explain a few things. I admit that I have sometimes wondered. When did you figure it out?"

"I'm not so sure I've figured anything out. I just have feelings and desires I don't think regular guys have." As the words left is lips, Jesse felt a new lightness and unconsciously exhaled a deep sigh of relief. This new honesty had ushered in an unusual calmness. He reached and gently took Amanda's hand and smiled.

Amanda, being the kind of friend everyone hopes for, instinctively started to think about how she was going to be able to help her dearest friend work through this new chapter of his life.

"I love your body," Jesse offered again. "Heck, I love everything about you!"

"And I love you too," Amanda said warmly, leaning into a heartfelt embrace.

As the two rested in each others arms, the warm bond slowly grew back into the earlier tenderness. But being young, and easily aroused, the tender feelings steadily grew into flames of passion once again.

"Let's try this again," Amanda said in a coy but playful mood as she started unbuttoning Jesse's jeans. "But don't worry, I don't expect you to fuck me... there's more than one way to do this, you know."

Before Jesse could think, Amanda's hand had already found it's mark and it felt so very warm and wonderful to him now that things were out in the open. As he felt the pleasant fullness returning to his small but perfect cock, it seemed like maybe his confusion was just a passing notion he had let become too important. For now, all he could think clearly about was the warm flesh under his own fingertips that had found their way back into her panties. She was soaking wet and clearly still in the mood even after their interrupted first attempt.

"Eat me," Amanda said bluntly. "I want you to lick my cunt until I say you can stop, do you understand?"

Jesse noticed the new firmness in her voice. It was a part of her he had never seen before, and the way he felt about it was pretty clear from the redoubled hardness he felt in his jeans. In the middle of getting into position to do as she demanded, Amanda said, "Stop. I want you stripped completely naked when you service me."

Jesse was a bit dumbfounded by this new aggressiveness, but when Amanda added, "Don't just stare at me, get up off your knees and do as I say!" Not knowing what else to do he meekly stood and obeyed her command. It didn't take long to remove the pants which were already unbuttoned and opened, he tried to quickly resume his position between her legs but was again checked by her stern command, "Stop right there. Don't think you're going to hide from me. Stand up straight, right over there. That's it, now turn around so I can see your pretty bottom."

Jesse had never felt such humiliation, or such arousal. His little "precious" was standing at full attention for all to see.

"Again," Amanda ordered, "turn and face me".

With an obedience he didn't quite understand Jesse complied once more to what was expected of him. Instinctively his hands lowered to try and retain some dignity, but Amanda wasn't having any part of that.

"No, sir. Take your hands away from your little pecker and stand there so I can see you and it."

Beginning to enjoy this new game, Amanda got up from the bed and walked very slowly toward Jesse while eying his nude body up and down like an inspector at a meat packing plant.

"Spread your legs and grab the back of your neck with both hands." The order was simple and blunt and Jesse obeyed.

Walking behind him she gently slid her fingernails down his back ending in a sharp swat on his naked bottom, "Spread 'em wider," she whispered into his ear. Jesse could feel her breath, he could smell her, he felt the warmth on his skin where she had struck him. He felt out of sorts, but was also beyond resistance as he obediently followed her command. Yes, Jesse was beyond resistance, but not beyond an awareness that this pose was for her inspection of his ass. He was also very aware that the flesh that was as limp as a dead fish moments ago was now pointing up toward his belly button...and that too added to his confusion.

Amanda was becoming more aroused by the moment. The sight before her was the most erotic she had ever seen. The pert round ass, the small sack hanging delicately, the tiny puckered hole and the pure vulnerability of the one standing obediently before her was something she had only enjoyed in the online explorations of her dominant side. She had only dominated her friend Briana in real life before tonight and had never truly thought about doing it to a man, except in fantasy.

Putting a hand gently on his right shoulder, Amanda whispered into Jesse's ear, "I want you to bend over now and grab your ankles. Spread your legs and bend over," she added a bit more firmly.

Jesse's first thought was; No, this is too much. But even as he was thinking this he was bending forward to grasp his ankles.

Humiliated, he just stood there bent over and exposed for what seemed an eternity. What was she doing? Then a cool hand cupped his balls and gently took possession of them, tugging and exploring them like a child with new toy. He felt so stripped, so vulnerable, and so wonderful at the same time. It was in this exact moment, the moment in time when he mentally acknowledged his liking of this game, that he felt the finger on his butt hole! The place no other person had ever touched was now open and being explored.

Amanda could sense Jesse's nervousness and saw him tense up, but cooly said, "Don't even think about it. You just stay right where you are until I say you can get up. Understand?"

"Yes, okay." But it sounded so small and weak even to himself, and he felt ashamed for his weakness. Yet despite his shame, weakness and vulnerable, Jesse was unable to resist this small petite girl who he didn't know as well as he had imagined.

It was in that moment of surrender that Amanda began to gently explore him. With some saliva and in small increments Jesse soon had the full middle finger of his best friend in his virgin hole. It had all happened so unscripted, so spontaneously that neither of the lovers fully realized the significance of what was happening. But now that it was happening, each was also fully alive as never before. Jesse started rocking back and forth on her finger. Watching in fascination, Amanda enjoyed her greatest thrill yet as the young man she only thought she knew slowly fucked himself on her hand. Curious, she reached around and found a smallish but rock hard cock. It was just the next obvious thing to do when she began to milk the hard flesh between her fingers. It wasn't long in time, but long enough for lives to be changed, and when that short span of time ended Jesse lost all control and all care as he emptied himself uncontrollably at the hand of this bewitching woman!

Jesse cried out as he started to cum. An animal like cry the like of which had never escaped his mouth. He was spent physically and emotionally. Amanda had stripped away every piece of armor he had so carefully crafted over the past several years. For the first time in his life he was truly exposed and vulnerable as she milked the essence of his manhood onto the hardwood floor while fingering him like he was a girl.

Emotionally and physically drained, he staggered toward the bedside but slowly sank to the floor with only his head resting on the bed. He could feel the crumpled bedding on his face, the aftermath from his earlier failed attempt at making love. He could smell her sex in the air and on the bed. He smelt his own scent which had been involuntarily milked from his body and was copiously sprinkled around the room and smeared along his thighs. But as the high began to wane, the old doubts and denied shame came creeping back out of the shadows that they had temporarily retreated to. Oh my, what have I done, began the small nasty voice in his head.

"Oh Jesse," the sweet, but breathless voice sighed close to his ear, "that was the best thing I have ever experienced in my life."

She was now laying on the edge of the bed with her arm over his back. As he sat naked on the cold floor, his cum still pooling slowly beneath him, Amanda nuzzled her face into his neck. They stayed there without words until Amanda whispered, "Now, you need to do one more thing. Don't you remember that I said you were supposed to get on your knees and eat me until I say stop?"

Oh, how unthinking could I be, he thought to himself! Coming back to life Jesse was more than eager to do what was expected of him.

"Wow, what an idiot," he groaned as he hastily regained his feet. "Like I said, I'm not very experienced with the all of this and I was kinda woozy after all that."

Attempting to lighten the mood, Jesse saluted saying in his most knightly voice, "I am at your service, my lady." He was, however, seemly unaware of his less than knightly appearance as he knelt like a true knight and quickly removed Amanda's clothes again.

"If you will now kindly lie back and spread you're legs. Ah, perfect. Now, just remember that your wish is my command." Jesse continued in his shining knight charade feeling more relieved and confident, since he knew just how to satisfy her needs with his mouth.

Her passions fully aroused after the intensity she had experienced in dominating him, Amanda fell into a state of physical sensation bolstered by feelings of control and power. Jesse did his duty with his mouth and fingers, unaware of the thoughts going through Amanda's mind. Her thoughts were not of a knight between her legs, but a servant whose sole job is to pleasure his mistress. It was with these thoughts flowing freely that she arched her back and pushed her cunt harder to his mouth, fully savoring this newfound way to enjoy sex. And enjoy it she did. "Lick my asshole," she barked at one point and smiled as her new Jesse quickly moved to obey. "Deeper, push your tongue in deeper".

It was obvious to both how exciting this new reversal of roles was. Yes, it felt a little weird at first to Amanda being the one in charge with a man. And it felt kind of embarrassing to Jesse to be so submissive, but those feelings remained unsaid. It was too perfect of a moment to spoil with details. And the truth is, it was exactly what both needed, to set the wild horses of desire free to run on the wind.

Amanda, exhausted, finally collapsed and spread her legs wide. "Finish it! And do it right!" she added in a stern voice,

Jesse obeyed, all the while wondering why he was so aroused by this, he felt humiliated yet knew he wanted more. And with those thoughts racing around in his mind, he did Amanda's bidding and finished her in a way she had demanded.

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End Part One