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That First Halloween Part 2

"Princess Jasmine and Zorro spend the night together"

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They parted company long enough for Guy to reach his own car and pull up behind the SUV that was already on the street. As he followed it to the Carriage Hills condos, he was unsure how the evening would end.

 

Carriage Hills was a gated community and the SUV stopped long enough for Zorro to address the guard on duty in the shack.They proceeded to an underground parking garage and parked their vehicles and boarded elevator.

 

They rode the elevator attached to each other lips and their bodies pressed tightly together until they reached the eleventh floor. Hand in hand they walked to Zorro's condo where Guy was bade to have a seat on the couch while Zorro got them some refreshments.

 

A bottle of wine was opened and poured, they clinked glasses and toasted Halloween. As they drank, Guy checked out Zorro's makeup. It was perfect, Guy was unable to see any trace of the woman under it. After a few swallows, Zorro set down his glass and began to talk.

 

"My name is Andrea and I have always enjoyed dressing up as a man. Even when playing as a kid I was always the male. I went to that party looking for a girl but I chickened out and was going to leave until I spotted you," Zorro stated as his voice lost its masculine tone.

 

"Are you gay?" Guy questioned.

 

"Not really.I had a brief fling in college that I enjoyed and have missed, I wanted to relive those glory days. I figured Halloween was the best night to indulge myself."

 

"My name is Guy. You could tell I was a male?" Guy asked.

 

"Not at first. Are you gay?" Andrea asked.

 

"No. Like you I have always enjoyed dressing up and I wanted to see how passable I was."

 

"You look one hundred percent female,"Andrea responded as she moved closer.

 

Guy set down his glass and embraced Andrea. Their kisses were even longer and filled with more wanting. Andrea's hand drifted to Guy's small crop top where she rubbed the phony breasts underneath.

 

"They feel so real," she commented.

 

"The best that money can buy. So what happens now?" Guy asked after a bit.

 

"Zorro is going to fuck Princess Jasmine. She is going to resist at having a cock inserted into her tight pussy but will lose the battle."

 

Guy became excited as she revealed her plan.

 

"Can you stay in character? I mean totally forget that you're a man in costume and makeup and believe that you are the Princess?" Andrea asked in low voice.

 

"Yes," Guy responded in his best female voice feeling his heart begin to race.

 

Zorro stood up and drained his glass in one gulp.

 

"Enough of this," the bandit said in a deep voice as he grabbed the Princess's wrist and forced her to stand.

 

"What is the meaning of this? Princess Jasmine asked in an aggravated voice as she attempted to break free of the gloved hand holding her.

 

"I have had enough of kissing and touching, it's time we had sex."

 

"Absolutely not. I am a virgin and intend on staying that way until I am married," the Princess retorted.

 

Zorro only laughed as he withdrew his sword.

 

"You will submit or I will run you through," he stated holding the sword against her flat belly.

 

Zorro marched her into a massive bedroom. He held the sword on her with one hand and unzipped his trousers with the other and produced large cock.

 

"Kiss it and lick it," he ordered.

 

"No," she whimpered.

 

Zorro pressed the point of the sword tighter against her and reluctantly and slowly, she dropped to her knees. Now, Guy knew that it wasn't a real cock but he was reluctant to move. Once again the female that Guy had become took over and she gently grasped the phony cock and began to kiss and lick it.

 

"Suck it, you perfumed bitch," Zorro snarled.

 

Tears appeared in Jasmine's eyes as she took the cock in her mouth and began to gently suck on it and Guy became excited as he did. Finally after a bit Zorro ordered her to stop and stand up.

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"It's time to banish your virginity," he snarled again.

 

Using his sword he pushed Jasmine backward toward the bed until she fell on her back.

 

"Please stop," Jasmine begged.

 

There was some unseen movement under Zorro's voluminous cape before he mounted the bed and held the sword on her again.

 

"Now little silk covered desert flower. I want you to remove your bottoms," he said quietly as his free hand went to her waistband and began to pull on them.

 

Both of Jasmine's hands went to her waist it an effort to prevent her bottoms being removed. She begged him to stop and offered him a reward from the Sultan.

 

"I have anticipated this," Zorro snarled.

 

He moved up and pinned Jasmine's arms with his knees and he reached behind the bedposts. A restraint made of pantyhose was removed and the ends were placed on Jasmine's wrists.

 

"Struggle all you wish. These chains are very strong," Zorro said with a laugh.

 

Zorro then placed the sword on the floor and with both hands slowly removed the silky harem pants and the brief underneath them. Guys swollen cock now free of its silken prison sprang into the air.

 

"What a beautiful looking pussy. I can't wait to shove myself into it," Zorro stated.

 

Jasmine continued to beg him to not do this thing. He continued to ignore her.

 

Andrea (Zorro) placed the head of Jasmine's (Guy's) cock at the entrance to her pussy.

 

"Are you ready, Princess?"

 

She shook her head, 'no' and continued to beg.

 

Andrea slammed herself down on Guy's cock. However, in their fantasy world, Zorro had just slammed his hard cock into Jasmine's virgin pussy and began to grind himself against her. For just a moment Guy allowed himself to be in control and he couldn't believe how hot and tight Andrea was. Andrea was happy that Guy's cock was the perfect size, not too big or too small.

 

Zorro kissed the Princess's neck, ears, lips and eyelids as he continued grinding himself.

 

"It is time to finish," he announced as he increased his grinding.

 

"No. Please don't shoot into me," she begged again.

 

Zorro only laughed as a massive orgasm shook his/her body.

 

"Too late," was all he said as he emptied his load in her.

They held each other for the longest time gently kissing.

Finally Guy stood up and collected his costume and headed to the bathroom that they had passed enroute to the bedroom. He cleaned up the best that he could and redressed before he headed back to the bedroom.

Andrea had removed her Zorro costume and was now clad in a thin silk robe that showed off her figure.

"Do you really have to leave," she asked as she stood to embrace him.

"Yes. I have no space change of clothes as I never expected to get lucky."

"You could go home in the morning and no one would look funny at you. You'd be someone just getting home from a Halloween party," she responded.

"This is the first time that I have ever been in public dressed as a female. At night is one thing, but in the daylight is another. I'm not ready for that."

"How about you coming over tomorrow night and bringing a change of clothes?"

"You really want to see me again?"

"More that you know. With you I have the best of both worlds, " she responded shyly as she handed him a business card with her name and phone number.

Andrea kissed him one last time and Guy drove home. Once there he removed his costume and stepped into the shower to remove his makeup. It had been one of the greatest Halloween nights he had ever experienced and signaled a new chapter in his life.

Once back in his bedroom Guy packed a small suitcase with a spare change of his clothing and makeup remover.He then laid out the lingerie and outfit that he would wear to Andrea's tomorrow night.

"Finally a female that understood and supported this lifestyle," he said to himself.

He had difficulty falling asleep as he couldn't wait for tomorrow to arrive and spending another night at Andrea's.

 

Published 
Written by ThePhantom
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