Perverted Mistress Date for Sissy Training with the Silicone Crossdresser
He couldn't suppress the trembling of his hands. "Focus, or Sunny will be upset," he whispered to himself, taking a deep breath before reapplying the nail polish brush to his toenails. Weeks ago, she had given him the task of first applying pink, paired with sandals. After this test of his obedience, she chose a vibrant cherry red for him for tonight.
Egon was in the midst of his feminization. He was a self-proclaimed crossdresser and, as he realized late in life, wanted to become a woman. The path of recognizing and fulfilling his own needs was not an easy one. Initially, Egon lived out his longing to be a woman in secret. He sought darkness and dimly lit niches for his fetish passion, mostly in questionable establishments.
It annoyed him that his inclination still received little social acceptance. Yes, integrated into a show program, as a transvestite to entertain squares, a man in women's clothing was accepted. But these freaks shouldn't appear on the street or while shopping, at least that was the generally perceived sentiment. Hot and cold shivers ran down Egon's spine as he remembered how he had been gratuitously accosted by other people in the past.
Just because he, as a man, wore women's clothing in public. Especially when he wore his wonderful wigs and his latex woman's body suit – when the feminine illusion appeared most effective – the aggressive reactions towards him increased. Most male contemporaries showed little tolerance for his crossdressing.
Shaking off the ugly memories, Egon returned to his task. Deep red toe and fingernails for Sunny. The noble whore* who had agreed to accompany and advance his feminization. Without her, looking back, Egon would hardly have dared to step out of his hidden existence. The driving force was that enchanting prostitute he once found through an advertisement. Back then, her words had enveloped him in a good feeling. A feeling that could be described as arriving.
Sunny proceeded unconventionally and by no means gave him the impression of being a mere business transaction that was worked through. There was no alarm clock on her bedside table that rang when the paid time had expired. Almost after every session, they drank coffee together. Often she baked cakes when he visited her. Both engaged in leisure activities where Egon could wear women's clothing and unabashedly live out his fetishism.
How liberating the outings were for him every time. Just like the erotic lessons where he found himself and went on a deep soul journey. But the most beautiful thing of all - what ultimately led him to fully trust Sunny - was her listening and their mutual exchange. Like a friend who selflessly enjoys spending time with him.
This fact distinguished his chosen one from the other sex workers on the market, who didn't make such an effort or condemned him as a crossdressing freak. Hardly any female being, not even the sex workers, could completely understand his inner fire to be a woman. How could any partner ever manage it - in a relationship or marriage?
Extreme Fetishes with Anal Intercourse and Crossdresser Breasts
Egon felt tears welling up inside him. He wanted all that sadness that regularly crept over him to finally escape. But this was an inauspicious moment for strong emotions like despair and discouragement. Courage was what he needed for the hours ahead. For Egon was to be anally penetrated by a man for the first time.
He was neither bisexual nor homosexual, but desired women and loved his Sunny. Especially when she rode him and he had her bra on his silicone breasts. She awakened the desire for anal sex in him. Although he had found it pleasant in previous relationships when his respective partner put a finger in his bottom during oral sex or a massage, more in this regard had not been conceivable for him until now.
But his goddess suggested stretching games as part of his feminization. Whenever they celebrated a crossdresser session, Sunny gradually used larger vibrator sizes so that Egon's rose*** would get used to the widening. An exciting moment was when his mistress later used a strap-on dildo to dominate him.
The crossdresser had to grin as he remembered the intoxicating feeling when she penetrated him without much foreplay. Needless to say, she also took on his mouth and taught him respectable oral sex. When Egon gagged and spit out vomit during this, his mistress shoved the thick latex penis deep into his throat again. What sounds cruel brought him the highest bliss.
Sissy Training with a Penis Cage
Damn, his mental movie was counterproductive! The penis cage, which held his magnificent erection captive, painfully pulled at his shaft. An instrument to illustrate his devotion, which Sunny had imposed on him. His lust belonged to her. The shiny piece of metal had reminded him of this since the beginning of his penile captivity.
Initially, the feeling of not being able to masturbate at will was unfamiliar to him. Not only positive feelings flowed through his body and mind, but also negative ones. After an initial adjustment, however, he increasingly enjoyed the discipline and increasingly welcomed Sunny's power over him.
Driven by the circumstance of not being allowed to ejaculate and yet being sexually stimulated, he fell into a psychological subservience that hardly granted him autonomous decision-making freedom anymore. His goddess should be happy – preferably with him and through his actions. If she was in a good mood, so was he. If she was well, he was well. The intimate symbiosis between them grew day by day and gave Egon support and strength for demanding everyday life.
The wonderful thing was that his lady neither selfishly nor narcissistically exercised her influence over him. As before the feminization, when they exclusively crossdressed, she always looked out for his well-being. When his beloved whispered in his ear during a walk that her satisfaction depended on his, he was completely lost to her. Then he realized deep in his heart that he would lose himself in Sunny.
Crossdressing with the Dominatrix
Egon was no fool. He was aware that he was one of Sunny's many clients. She was a sex worker and earned her money with the attention of men. Secretly, he wished she would lose her heart to him and quit her job. Move in with him and start a family. Even if his mistress wanted to keep her prostitution - which brought her joy and she treated her clients lovingly and sincerely - he would have taken her in and offered her a comfortable home.
He was an educated man with an academic degree. His bank account was well-stocked, and he owned his own house. Sunny could lead a comfortable life with him and at his side – if only she wanted to. But the question of all questions – "Do you love me?" – he dared not ask. The fear of losing her was overwhelming. No, the secret remained safely hidden in his psyche.
His goddess may have placed the key to his penis cage between her full breasts, but the lock to his innermost being, he kept behind thick walls. How influential the fear of losing a desired person was. Did he deny his strong feelings because of her?
"Enough of the merry-go-round of thoughts!" Egon scolded himself and proudly looked at the accurately applied nail polish. The intense red practically jumped out at him and encouraged an inviting mental movie. But not only he himself should be stimulated in the course of the evening, but also Sunny's selection of potential buyers. It was a filthy and depraved game.
When he started the journey of sissy training and his pretty took his feminization into her hands, they ventured onto thin ice. For if he wanted to be completely a woman, he would have to make his body openings available, as a lady would for a man. However, since he had never had intercourse with a man and did not desire it, this seemed to be the biggest challenge in this process.
He was tempted to cross boundaries and gain experience in that regard. To feel like a lady being possessed by a penis. By now, Egon was constantly dreaming of this idea.
His lady had long sensed this lost longing in him. Longer than he himself was aware of his need. One day she asked him if he wanted to act as the main character in a latex and fetish fashion show and strut around in exciting fetish clothing in front of men. Afterwards, the gentlemen were allowed to bid on how much Egon should cost.
Since he was a virgin, Sunny hoped for a high price. Of course, she would not miss the opportunity to book a wellness vacation with the money earned, to relax after the completion of his feminization. If he was lucky, he was allowed to come along as her masseur or sex slave. But his mistress had already announced to him that participation depended on the commitment he was willing to show.
And on his stamina to serve as many customer penises as possible. The more sperm** he took in, the more guys came, the better for him. If a client wanted to use his mouth instead of a toilet, Egon had to endure it. These were Sunny's rules. Her word carried weight, because he belonged to her. So he mentally prepared for natural champagne and perhaps also caviar.
Crossdresser Deflowering at the Fetish Meeting
Gradually, excitement rose in Egon. His heart beat faster, and a pleasant tingling sensation enveloped his entire body. What would his sweetie wear for his becoming a woman? Was it the hot long wet look dress or rather the catsuit? She looked incredibly breathtaking in both. He particularly liked sniffing her latex stockings. Of course, only if he was allowed to.
How hot it became when the elbow-length latex gloves were used and she pampered his anus with her fingers. It was almost unbearable with lust when his beloved used a realistic XL dildo that was inflatable by a pump and almost made his bottom explode.
After the penetration, it was the greatest pleasure and the worst punishment at the same time to lick everything clean. Having to taste and eat his own caviar was extremely humiliating. How much Sunny then savored the humiliation and enjoyed his torment. She was wonderfully sadistic.
As he reveled in exciting images, further questions came to mind. What would the chosen ones who participated in his auction look like? Were they attractive or ugly, thin or fat, bearded or bald? Did the men have manners or would they fall upon him like animals?
Then Egon admonished himself, for he could always count on Sunny's care. Whatever happened, he was safe. In every respect. Never before had he trusted another person as much as his beloved. The bidders would therefore not only be physically healthy, but also mentally.
Fetishism with Latex Mask and Sissy Wig
With a mischievous smile, Egon looked towards the bedroom. A cleverly cut wet-look long-sleeved shirt hung in the wardrobe. In front of it, on the bed, lay faux leather leggings. Combined with stylish heels, striking make-up, an attractive long-haired wig, and a full-body silicone suit, the illusion of a flawlessly beautiful woman perfectly took shape.
Sunny's suitors would lick their fingers after him. And he would beat their pricks. Grinning, the sissy made her way to the bathroom mirror. When he was with his mistress, a crossdresser silicone mask would also be added.
But he couldn't appear before her without makeup. That was an absolute taboo. And his fingernails weren't attached and painted yet either. There was still a lot to do. Egon would have to hurry not to be late for his own deflowering.
