tagTransgender & CrossdressersThe Point Of No Return

The Point Of No Return


First of all my things to ringerosie for her work in editing my piece. Her words of inspiration and her kindness are truly appreciated. Bless you Milady.

I sat there shaking my head, feeling the onset of a headache. It happened often when talking with Jonathan. He had a habit of leaving me wondering how on earth someone could be so...so...Jonathan like. I'd met him on a website. One that favored a certain lifestyle, one which we both enjoyed. He wrote wonderful stories, words which could arouse both the physical and the mental attributes of his readers. What he didn't do though was write for himself.

Let me explain. He always wanted others to live out their fantasies in his words. He was happy to let their lives come to life if only on paper. However when it came to his own desires, that was something that was not to be discussed. Every time the subject was brought up, he always managed to turn the tables. He would deflect the words, wanting to discuss something or someone else. Today had been one of those days and I had endured enough.

I knew Jonathan didn't look at me in a certain manner. I think if he might have then we could have not had to go through this in order to find a end to the means. I saw it, it was as clear as the reflection which I saw in the mirror. My eyes were set, my mind made up. I formulated a plan as I prepared for bed that evening. As I pulled up the covers I thought tomorrow was the weekend. Mark my words, Jonathan Samuels was in for a very rude awakening.

That afternoon as the phone rang, I sat on the bed, looking out at everything in place. A smile playing on my face as I thought how much fun this was going to be. When he picked up the phone, this time I made sure the voice he heard was unlike any I had shared with him in the past. "Jonathan, it's Kris. You need to come to room 242 at the Hilton downtown immediately. I will expect you shortly." With that, I hung up the phone before he could utter a single word. I laughed as seconds later my cell rang, a call I wasn't about to take.

I was impressed, he made good time. When the knock came on the door and I bid, "Enter" he did so. Tentatively looking in, finding the room fairly dimly lit by the waning afternoon light coming in through the almost drawn curtains. I sat in a chair, dressed in a short, black dress. One befitting a night out on the town. He looked at me in a bit of confusion as I said calmly, "Close the door. Come here." He did the first. Then he had the audacity to speak asking what was going on, what was happening. That was my cue.

I stood up slowly, walking toward him my eyes sparking and I saw the uncertainty in his own. I knew if I looked long enough, he would revert to his true self and within seconds, he lowered his eyes. He had told me many times a true submissive pose. My voice cut like a knife. "I am done watching you as you allow your life to pass by like petals from a rose scattered on a desolate wind. You are content to let others live while you die each day. Little by little, piece by piece. Enough."

He began to shake, to tremble a condition which he had told me of from birth but I wasn't about to let him off the hook. I was feeling the part, feeding off the raw emotion as I continued. "You hide away a piece of you, a part of you which yearns to be free. In your blindness, you allow it to simply fester, eating away at your very soul, your very being. I have tolerated it for far too long. It ends tonight. Do I make myself clear?"

I couldn't remember the number of times he had spoken to me in such a manner. How every time he did, I felt it in the pit of my stomach. I watched as he wrestled with the decision, with the words which I knew for him would be difficult to speak. This time I made the decision for him. I moved in close until he could smell my perfume, feel my warm breath against his neck and hear my whisper in his ear. "If you think this is a game, you are sadly mistaken Jonathan. Now, listen very closely and do not speak."

With that I gave him his instructions. Speaking in a calm, level voice as he listened, taking in my every word. When I had finished, I saw the look in his eyes, the panic rise. In the past, I would have tried to calm him, to soothe him with kindness but tonight was different. The past had seen him react in a manner which had allowed him safe passage. This time the journey was going to be a bit rougher as I reached up, taking him by his long hair. I forced his eyes to look into mine.

"Do you really think you have a choice Jonathan? Do you really believe things haven't changed?" His eyes grew wide as mine grew darker as I continued. "After tonight, things will never be the same for you." He cried out as I literally pulled him by the hair into the bathroom, what he would require laid out as I said, "You have fifteen minutes."

I heard the shower start. There was little I could do but wait. I poured a glass of wine, as the night fell, the stars coming out. Taking a sip, I looked at the items on the bed, the various boxes as I smiled. Opening each one would be like unlocking a door. Each door leading to another which would finally open up to show him the path I was about to take him down.

When the shower turned off, I made my way over to the table, turning on the lamp so that I could see better for what was about to happen. It took a couple of minutes for him to walk out, his face a bit flushed. His skin glistened, the silky robe I had laid out for him clinging to his skin. His long hair spilling out from it. I had to hide the smile, seeing the other unsightly hair no longer clinging to his skin. I motioned to the chair and without hesitation, he sat as I pulled out a brush. "Shall we begin?"

I had made sure all of the mirrors were turned so that he couldn't see. As the minutes progressed and I continued to work, I saw him cast furtive glances until I finally said sternly, "Sit still." My words seemed to be the calming influence he needed and his obedience was impressive, not a word of rebuttal spoken. Only a soft "Yes Miss", which I took, nodding in approval. Finally I announced I was done and motioned for him to stand up. As he did, I reached down, untying the robe and allowing it to slip to the floor in a puddle.

I knew better than to react. Picking up the first box, handing it to him and with trembling fingers he fumbled to open it. It revealed a set of matching undergarments, his face blushing as I took the items out. I handed them to him one at a time and when needed it, helped him with them. The entire time I kept a close look at his eyes, watching closely. With each subsequent offering, he allowed himself to fall further and further under the spell I was weaving. Something I had hoped might happen, never daring to dream it would do so to such an extent.

And so it went, piece by piece I created a look. I'd caught glimpses into his desires, momentary lapses in which he'd allowed his true fantasies surface only to quickly quell them. I watched him flourish before my eyes, I had to fight not to smile, not to allow my own personal feelings for him to surface. It would have been easy to lighten the mood, to show him my own pleasure. To do so would have broken the spell and we had come this far. I wasn't about to give him a moments pause, continuing until finally I said, "Done."

I walked over, turning on a light, motioning for Jonathan to draw closer. He walked carefully in the heels I had purchased for him, my heart soaring to see what I had done. It took a lot for me to keep my voice calm as I said, "Jonathan, meet Gabrielle." It was the look on his face, the look which in my wildest dreams I could never have dared imagine might be that made it all worthwhile.

The woman who stood next to me was dressed in a simple, but elegant black dress. Her hair in curls framing her face, her makeup done for evening's wear. Her dress accentuated her curves and the promise within. I knew underneath, she wore the decadent clothing that she had always dreamed of. To me it was a look that ran the gamut somewhere between evening chic and high priced escort. I could see it in her eyes. Eyes which threatened to fill with tears of happiness.

"If you cry and ruin your makeup, I will not be happy." I saw how the words stung and how quickly it brought her back to reality but it was a necessary evil. "Now, turn around for me." As she did so slowly, I looked carefully, wanting to make sure I hadn't missed anything. I took in the subtle touches, her nails which I had painstakingly done. The earrings which dangled, sparkling with gold. The lace choker around her neck. I nodded, knowing the next part of the plan would be one she would possibly have a difficult time with.

I handed her a small clutch purse and then turned, opening the door. I saw her eyes widen, her red lips open as if to protest and I was ready. "It really is quite simple Gabrielle. Jonathan is gone, his clothes in case you haven't noticed are no longer here. Eventually you will have to go through the lobby to leave the building. I am going to the bar, you can meet me there or you can take your chances outside. You have no money, no identification, no credit cards. Only what you are wearing. Now, make your choice", and with that I walked out the door.

As I sat down at the bar, I saw mostly men, a smile coming to my face as I asked the bartender for two glasses of wine. I knew it might take a minute or two but the plan had worked flawlessly so far and just as the drinks arrived, so did my companion. I nodded as she sat down, my eyes watching as the dress rode up, leaving the tops of her stockings visible. The sight was not lost on her as she tried to no avail to correct the matter until I said, "Sit still Gabrielle, now."

Once again I was pleased to see her obey without hesitation, without pause. Her hands moving to her lap, her eyes lowering as I hid my pleasure behind a glance which took in the room. It was interesting to see how many had turned their attention to the two women sitting alone, enjoying a glass of merlot together. I saw one in particular taking a particular interest as I reached out, letting my hand trail down Gabrielle's face. Her eyes closed as she accepted my touch and I smiled at the gentleman.

I knew it was only a matter of time and when I next looked up, two fresh glasses of wine were being delivered. Moments later, they were followed by the stranger who approached. Introductions were made and I watched as Gabrielle seemed to shrink before my eyes, her fears of old rising quickly. Little did she know I was about to turn her world upside down.

"Before this goes any further, I need to make something very clear. The girl is mine, I am her Mistress, she is my submissive. If you wish to speak to her, you do so through me. No questions, no comments, I wish that clear from the start."

The man looked taken aback, a smile threatening to overtake my face as he too played his part to perfection. He was a long time friend who I had associated with from the site where Jonathan and I had first met. He had been only to happy to assist me in making this night happen. I could see the look on her face, see how once again she was being drawn into the web I was spinning. I however wanted more, I needed to make sure she knew how far I was willing to go.

"I can't blame you for desiring her. She is shall we say, quite talented at what she does. She is five hundred dollars for you to use her as you desire on the condition I accompany her and if I so desire, I partake as well. She is an expensive whore, but she is my expensive whore." I laughed, watching as her face turned a bright red even under her makeup.

"Why don't you dance with the dear girl, inspect the merchandise. I'm sure you'll find her special in many ways." The man smiled, extended his hand as the auburn haired beauty lowered her eyes and mine turned dark before coldly replying, "Do not make a scene young lady, you will dance now."

As she extended her long red finger nailed hand he took it, smiling at the blue eyed beauty. The music played softly as he pulled her body into his. The dance was a slow one and I saw her partner's hand slip a bit, cupping her lovely bum. I almost laughed as she ducked her head down onto his shoulder. He moved her across the dance floor, his mouth next to her ear, saying sweet nothings. Nibbling on her neck, fanning the flames of a libido which I knew was already on the edge.

When they returned, he held the chair out for her and she sat down. I favored him with a smile as he opened his wallet, placing five hundred dollar bills on the table. His voice suddenly took on a different tone, confident as he stated which room he was in. That he would expect the as he called it, "merchandise" to be delivered in fifteen minutes time. I nodded and he was off as the trembling figure beside me began to glance around, looking for a possible escape.

"You are free to run dear, I have my money. Of course, you have nothing but the clothes on your back and in the freezing temperatures of winter with nothing else, dressed as you are. I'm sure some stranger off the street would gladly take pity on such a poor girl as yourself...", once again the words hanging there, the veiled threat evident as she succumbed to my plan for her. I stood and made my way toward the elevators. Hearing the sound of her heels following behind me.

My plan had many facets. From her transformation, to making her feel like she wasn't capable of stopping it. Of feeling like she was being "forced" to participate. In reality it was like having a dream which had long been kept hidden away in the darkest recesses of her mind finally come to fruition. I was keeping her off balance. Not giving her time to process the mounting wave which from the moment we began was threatening to drown her.

As we arrived on the gentleman's floor, the doors to the elevator opened, the sight of a younger couple waiting to get on. I took advantage turning to the blue eyed beauty saying. "The next time you decide to act like a cheap whore in front of me, flaunting yourself to any man I suggest you think long and hard about who owns you. Who you belong to. Is that clear bitch? I say who you favor, who buys you, who pays me for the night. You would be wise to remember that." I strode off the elevator, my quick strides taking me down the hallway as I didn't turn to look. Knowing the crestfallen girl would be just behind me, having been thoroughly shamed.

The door to the suite was slightly open, the man standing before the large window looking out into the night. The lights of the city providing the only illumination. As we both entered, I turned, locking the door as I heard his voice say, "Gabrielle, come to me, now."

She looked at me, her eyes now wide as I replied, "Do not keep the gentleman waiting girl. He has paid handsomely for his time with you. Now, give him what he desires."

Like the condemned taking the final steps, she approached, as I watched the poor dear until she stood just behind the man. His drink in hand, he took a swallow before turning and circling her. His hand reached out, the zipper being pulled down as seconds later the black dress she wore laid at her feet. She stood there, dressed in the remaining garments befitting a woman of the oldest profession in the world.

The black lace garter belt, the silky stockings, the shadows showing the possibilities of the pleasures to be found with such a body left my own beginning to stir. I watched as the man allowed his hands to roam, the only sound the soft moans of a woman in need. As he gently pushed her shoulder, she slid to her knees. Her head still slightly lowered, a submissive to the end showing her true self. In supplication before not only I but the stranger as well.

As the time progressed, it was like watching a film noir. A black and white image as eventually she ended up with his hands in her hair. Her mouth filled with his need, his moans now to be heard. I watched like a voyeur from across the room, finally allowing my dress to join hers on the floor. I moved to the bed, my eyes drinking in the sight. My fingers soon finding the place between my legs, as my own need found its way to the surface.

The final act of the play found Gabrielle on all fours, her face buried between my legs. Her mouth granting me my guilty pleasure, the thanks for my actions as the man took her virginity. He had been kind, gentle but now with his own release imminent he simply used her. I looked into her eyes. I saw where she had found her sub space. The place where a submissive goes when not only her body but her mind as well gives up the fight and accepts the outcome. Her place in the world precisely where she was at this very moment in time.

As the three of us danced, our bodies in motion it was he who finally broke first. His guttural moan announcing his release. I felt Gabrielle shiver with delight, her mouth, her actions becoming more frantic as my body responded. My hands gripped her auburn locks tightly, my head falling back as my pleasure flowed forth. Her face quickly a mask of it. Her eyes gleaming with lust, knowing she had given me this gift as I trembled with the power of my own orgasm.

It was a few minutes later that I stood behind her, zipping her dress back up as the man approached. He handed me an additional one hundred dollar bill, a tip for services rendered. She listened as he said that when he was in town the next month he would require Gabrielle's services again, though he wished to be a bit more creative. "Does she do bondage?"

I laughed saying, "Anything is negotiable when it comes to your use, isn't that right pet.?" All she could do was hang her head as I opened the door and we took our leave.

Back in our room, I walked over, pouring myself a glass of wine. I let her stand there, knowing this would now be the most crucial time of the entire event. Turning, I spoke calmly saying, "Kneel." By the time the word was spoken, the action was carried out. The lovely young thing on her knees before me, assuming the traditional submissive pose. I towered over her, as I put my fingers under her chin, forcing her to look me in the eyes.

"I told you this changes everything Gabrielle. You see the possibilities, you see the promise in your own reflection. You can embrace this. You can accept the gift I am offering or you can go back to watching as life passes you by. Slowly dying minute by minute. The choice is yours, serve me or", as I pointed slowly toward the door.

I saw it in her eyes, I heard it in her whispered response as I allowed the smile I had been hiding all night to come to my face. I extended my hand, pulling her to her feet. My mouth found hers, demanding my right of entrance. She eagerly accepting it as my hands played over my new toys body and our time together began.


As with all my works I do hope that you will take the time to not only vote but also comment. Good or bad it helps me to realize my potential as a writer by the feedback I get. I do hope you enjoyed.

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