It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted.

Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in any light and he couldn't have been happier. It happened one afternoon that Kyle's secret had been discovered by Rusty, his sister's boyfriend. Kyle was wearing a school girl outfit he had purchased at one of these functions, it was the kind of outfit that one might see in an X-rated Anime movie. It had a very short blue pleated skirt and a low cut tight white shirt and a tie.

Kyle was made to perform a striptease while Rusty watched and jacked off. It was either this or exposure and he couldn't have that. After awhile Rusty gently placed Kyle on the bed on all fours and took his anal cherry. As he pumped Kyle's virgin ass his large warm hand jacked Kyle off.

Kyle was surprised when Rusty showed up at one of his little getaway weekends a few weeks later and offered to be his escort. They laughed, drank and flirted and at the end of happy hour they headed to Rusty's room.

True to the promise he made during their first meeting he had purchased several pieces of the most erotic lingerie that Kyle had ever seen. As Kyle modeled them Rusty sat on the bed jacking his rock hard cock as he watched. The session always ended with him being placed on all fours and Rusty pushing himself into Kyle's tight ass.

Soon Rusty began to show up at all the get togethers. Sometimes Kyle never made it to the bar for happy hour as Rusty always wanted him. When he was at home it got worse. Rusty seemed to know when Kyle's sister was not going to be at home and he invited himself over for sex. Kyle barley had time to complete his makeup before Rusty appeared at his door.

Anytime he didn't wish to submit the threat of exposure was always issued. It was about three months later and while Kyle was registering at the desk Rusty showed up. When Rusty discovered that the room next to Kyle's was vacant he requested that room. This time, however, Rusty wanted to attend the happy hour, so Kyle took his time dressing and applying his makeup.

Kyle was treated like a Princess the whole time they were there, Rusty didn't even pitch a bitch when Kyle left his side to meet some friends. Between the wine and attention, Kyle became horny and Rusty was so gentle on the walk back to their rooms Kyle decided to treat him.

Using the door that connected the rooms Kyle returned to his side and decided he would don a few new pieces Rusty had ordered and then model them. As usual, Rusty sat on his bed and stroked his cock as he watched Kyle slowly strip off his cocktail dress to reveal his newest gifts underneath.

"Oh baby, you are so hot. I would really love to see you in that new nightgown," he informed him.

Kyle headed back to his room where he stripped off his cocktail dress and lingerie and donned the nightgown Rusty had purchased. The gown was made of softest black silk and sheerest lace he had ever seen or felt. It so short that it barely covered his ass, it came with a tiny black lace thong that did a pretty good job of hiding his manhood.

When he swung the door to Rusty's room open he discovered that Rusty was not there. Sitting in his place on the edge of the bed was a handsome older gent with head full of steel gray hair and a deep tan.

"Who are you?" Kyle questioned.

"My name is Giles, I'm your ten o'clock appointment," he said with a smile and a look of lust in his eyes.

"There must be some mistake, I didn't have an appointment," Kyle stated in a nervous voice.

"Your friend arranged it and stated that you were okay with it. Now come closer and let me see you in the light."

Kyle turned to leave and found Rusty in the doorway blocking his path.

"What's this all about?" he hissed at Rusty in a whisper.

"We met during happy hour while you were visiting with your friends. He confided in me just how hot he thought you were and how bad he wanted to fuck you. So I accepted payment and guaranteed performance."

"I am not some hooker and you are not my pimp,"Kyle responded.

"You will be whatever I tell you to be. Now get over there and service him," Rusty growled.

Defeated Kyle returned to the bed and the man stood up as he approached.

"Is everything all right? Giles questioned.

"Yes, everything is fine."

"You are so pretty," he said as he took Kyle in his arms and placed his lips on his.

Kyle was surprised at how gentle he was and how great he smelled. Giles's hands ran down Kyle's back and began to rub his silk covered ass and he gently pulled him closer. Soon Giles crotch was against Kyle's and he could feel the erect cock pressing against the front of his thong.

"Get on your knees and undo my slacks," Giles softly requested as he removed his suit coat and loosened his tie

Kyle slowly knelt and removed the expensive Italian loafers before he undid Giles's belt and drew down the zipper. The suit slacks slid down to reveal box briefs and a small but very hard cock underneath.

From the kneeling position, Kyle slowly slid down the boxers which allowed his hard cock to spring free.Before he could stand Giles then placed his hands on the back of Kyle's head and gently pushed it toward his hard shaft.

Fear clutched at Kyle's heart as he had never performed oral sex before. His mind recalled the blow jobs the cheerleaders had given to him when he as a member of the swim team.He recalled how their lips and tongues played on his hard cock and he now mimicked the movements.

His small hand took a hold of the cock before him and his cherry red lips planted kisses on the head that was already glistening with precum.

Kyle took the head into his mouth and began to gently suck it for a few seconds. He then released it and returned to planting kisses on it.

Each time he allowed more to enter his mouth and struggled not to gag. All the while Giles moaned with pleasure. Kyle was surprised when Giles asked him to stop and helped him to stand up. Giles then took a seat on the bed and held out his hand to Kyle.

As soon as he took it he was pulled off his feet. He wound up face down across Giles's lap and felt the nightie being flipped up exposing is lace covered bottom.

"Next time you pleasure me I expect you to take the whole thing in your mouth," Giles said softly as he brought his hand down on Kyle's firm butt.

Kyle moaned aloud and received another swat.

"Silence," Giles commanded and brought his firm hand down again.

Kyle whimpered softly and that seemed to please the older gent. Having never been spanked before he discovered that he actually began enjoying it. Just as he was starting to get into it, he felt Giles's body stiffen and a low moan escape his lips.

Kyle felt the warm sticky fluid against his skin and realized that Giles had lost his load on him.

"I apologize for that. I thought I could hold out longer," he said softly, as Kyle stood up and sat next to him.

"That's all right," Kyle responded and gently kissed his cheek.

May one pose a personal question?" Giles stated as he began to redress.

"Sure".

"Could one assume that you were not aware of my coming up here?"

"Yes, you could."

"Then this whole thing was your boyfriend's idea?"

"He is not my boyfriend and yes, it was all his idea," Kyle admitted.

"Then why are involved with that Rusty character?"

Keeping his voice low in case Rusty was in the next room with his ear against the door he told Giles the whole story.

"So if you refuse him he will expose you to your friends and family?"

"Yes."

"Then perhaps I can be of assistance," Giles stated with a smile.

"Really?"

"Yes. There will be a cost for this assistance, but in the long run, you will be happier."

He gave Kyle a kiss and left. Kyle washed off his makeup and turned in. The following day was spent poolside sunbathing, swimming and chatting with the others. He didn't see Rusty or Giles all day. As the afternoon waned people began to say their goodbyes and head back to their respective rooms to change for happy hour

After a shower and shave and the usual two-hour makeup session Kyle was ready to dress for happy hour. Clad in a short and tight black leather miniskirt and a blood red silk blouse and heels Kyle headed to the lounge. He spotted Giles sitting at a table and headed there ignoring Rusty sitting at the bar, he and became upset at Kyle's ignoring him and slid off his stool and followed.

Kyle had just slid in next to Giles when Rusty approached. He took a chair opposite them and glowered at the couple.

"Didn't you see me at the bar?" Rusty questioned.

"I saw you," Kyle replied simply.

"Yet you passed me by without so much as a hello. What gives?"

"What gives is that you are finished with her," Giles responded.

"Oh really? How about I pull you out of your seat and kick you ass? And you, he said addressing Kyle.Do you want everyone to find out about your lifestyle?" he said.

"My dear boy, you shall do neither," Giles stated and snapped his fingers.

Suddenly two very large ladies appeared and pulled up chairs so they were seated at Rusty's sides. One pressed a small gun into Rusty's side while the other placed her hand on his shoulder. Rusty felt the point of a knife just touching his neck.

"You are going to leave here and never show your face at any of these events ever again. If you tell anyone about Kyle's secret life it will probably be the last thing you do. Do we understand each other?"

Rusty nodded as sweat rolled down his face.

"Good. Now my friends are going to accompany you to your room and help you pack. They will then walk you to your car. Resistance will not be tolerated and will be dealt with rather violently."

It was about twenty minutes later that the two large ladies reappeared and announced that Rusty was gone. Giles gave them both a roll of one hundred dollars bills.

"There, now you nothing else to worry about," Giles stated.

"That's a lot of money," Kyle managed to say.

"That is nothing. I am a millionaire," Giles responded.

"How will I ever repay you?"

"Letting me spank you while you're wearing that stunning skirt will be a start,"Giles stated as he gently kissed Kyle's cheek.

"That's easy," Kyle responded.

"With your wrists bound?"

"Sure."

"The other thing is secrecy. No one can ever find out about this."

"You keep my secret and I'll keep yours," Kyle responded.

Later in his room with his wrists bound together by Giles's expensive tie he was laid across Giles lap.This time he did not keep his boxer briefs on but allowed his naked cock to make contact with Kyle's firm flat stomach.

Kyle was spanked until Giles shot his load on him again. He then placed Kyle on his back and asked him to jack off while he watched. Kyle obeyed and hiked up his skirt and allowed his manhood free. As he pumped his hard cock Giles gently kissed his neck.

It was the beginning of many wonderful weekends together.