Training the Sissy Virgin - Crossdressing Virgin

David nervously cupped his pink padded bra, adjusting his fake cleavage. His short white skirt was hiked up just enough to flash his pink and white striped panties. .

It was time to fulfill his end of the bargain and strutt his sissy persona across the crowded shopping mall. 

The sissy virgin rummaged through the bag of women's clothes shaking his head in astonishment. It was mere hours ago when David had sought the services of a high class escort to finally lose his cherry. 

But his choice of escort had led him down an unexpected journey. 

Lexi skillfully concealed her two sides, playing the role of a sensual submissive escort at times, and at other times.She unleashed a dark and dangerous side as she transformed into a cruel and dominant dominatrix, teasing and tormenting the unfortunate males caught in her web of pain, punishment and humiliation. 

The stunning escort learned of the virgin’s crossdressing and chastity fantasy during their first dinner date together. The mere thought on flaunting her naked body in front of the virgin, before cruelly locking him in a steel chastity cage and forcing him to dress himself in her underwear awoke her hidden Domme. 

And as the evening progressed, the cruel and sadistic side of Lexi paraded the naive virgin around, forcing him to seal himself in a painfully restrictive chastity cage and donning her pink underwear, tending to the Domme’s pleasures. 

And once she had stripped him of his dignity, Lexi left her male client naked and stranded in the alleyway behind the hotel with a bag of her clothes and her a number scrawled on a piece of card. . 

Bruised, humiliated and feminized, David remained the naked virgin he was at the start of the night. His cruel mistress has dumped her used clothes in a bag black with instructions to dress himself in her pink underwear, short white skirt and pink high heels and then to call her. 

The sadistic Mistress assured David she would eventually relieve him of his virginity. But first he would need to earn the right to be released from his steel chastity cage in order to free his arousal.

And in order to prove his worth, David’s first task was to dress up as a mature schoolgirl on her way losing her own cherry and parade her sissy ass across the crowded shopping mall.