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Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser. Like so may others he doesn’t know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister’s room and wearing them behind closed doors when the house was empty. But it wasn’t enough.
To his delight he discovered that there were literally hundreds of sites on the Internet that catered to those that shared his passion. He must have joined a dozen sites and spent hours on line reading the blogs, chatting and asking hundreds of questions. Kyle had obtained part time employment while still in high school that paid a great wage and it allowed him to order lingerie and makeup from various supply houses. That was after renting a box at one of the mailing services to ensure that there were no questions as to what it was that he got in the mail on any day.
He hid his collection in the back of his closet in an old hard sided Samsonite suitcase from the forties that still had a working lock. Kyle wasn’t really worried as he never given his parents any reason to search his room. His collection and passion grew and he dressed up whenever the opportunity presented itself, but he still looked like a guy in lingerie.
Now years on the swim team had kept him lean and pumping iron in the school gym gave him great deal of lean muscle tone. One of the rites of passage for acceptance to the swim team was to have all his body hair shaved off by a group of cheerleaders, and he was required to keep it off. It was the Summer that he turned eighteen and had graduated high school that he finally summoned up the courage to attended his first weekend event. He had read about it on one of the sites he had joined and was assured it was for those that shared and supported this lifestyle.
It was being held at a beautiful and somewhat isolated hotel out of state. After chatting with a few of his new friends and being assured of learning new skills he registered on line. He packed up his collection and after giving the excuse of visiting some friends that he had made at a swim meet he left on Friday right after work. A three hour drive later he finally met all the wonderful people that he had been chatting with on line. They made him feel welcome and accepted, he no longer felt like an outcast. All were eager to assist him in learning the aspects of looking female.
Kyle was adopted by a stunning older attendee named Sylvia and he became her student. They spent hours together and she shared all her knowledge with him. The lessons included how to walk in high heels and the antalya escort bayan proper way to apply makeup. Kyle soon became a regular at these events and eventually conquered his fear of being seen in public as a female. He was finally able to walk from his room to the main salon in heels for the nightly gatherings without fear of falling. He was even able to sit in the bar and flirt with some of the men.
As time passed many of those he met at these events could not believe that he was not a GG (generic girl), his skill at makeup and dressing had become that good. It was at one of these weekends that he purchased a skirt and blouse combo that was not unlike a school girl’s outfit seen in an erotic Anime feature and he couldn’t wait to try it on.The house was going to be empty the next weekend as his parents were going camping and his sister was spending the weekend with her boyfriend. Kyle even waited an hour after they had departed in case they returned to pick up something they had forgotten…
A shower and shave were followed by two and a half hours of makeup before finally he was ready to dress. It started with a blue silk bra that already had breasts built in it. He then placed a matching garter belt around his hips and slowly slid up the sheer nylons and attached them to the ribbons.As he slid up the silky blue panties he was already as hard as a rock and the illusion was ruined by this pole straining against the silky material. Now he had learned dozens of ways to hide this protrusion, but tonight he settled for his favorite solution.
Kyle slid the panties down just enough so his cock could spring free and then he moved to the full length mirror on the wall. As he stared at the pretty girl staring back at him he began to stroke himself. He then leaned into the mirror and kissed the cold reflection and as soon as the head of his cock touched the cold surface he shot his wad on the mirror and the reflection of the pretty girl there.
Now totally limp he cleaned up and finished dressing. The outfit he had purchased had a very short blue pleated skirt and white blouse, white lacy ankle socks were thrown in as a bonus. He finally slipped on the heels and stood in front of the mirror again.
Perfect was the only word that came to mind. He was so busy admiring his reflection that he did not hear anyone enter the house.
“Who are you?”
Ky;e spun around and there stood his sister’s boyfriend, Rusty. He stood there in the doorway just staring at him before he stepped into the room. Rusty was tall and tanned with the build of a wrestler, plus he was very handsome.
“Who are you?” he asked again as he approached.
It wasn’t until he was inches escort antalya from his face that he put two and two together.
“Kyle? Is that really you? Dammed if you aren’t hotter looking than your sister,” he stated as he continued to stare.
Then without warning he took Kyle in his massive arms and placed his lips on his and gave him a gentle kiss. He tasted like tobacco and alcohol and Kyle could feel his erection pressing against his nylon covered leg.
He couldn’t believe how turned it got him and he kissed him back. The gentle kisses soon turned into a passionate tongue sucking frenzy.
He ran his hands all over Kyle’s smooth body and then moved up under the skirt. He tried to stop him but was unsuccessful, soon his powerful hands were caressing his thighs and silk covered butt.
“Dammed if you don’t even feel better than you sister,” he commented.
“Where is Delilah?” he asked softly.
“Who knows, we had a fight and she took off. I thought she was heading back here,” he answered as he moved toward the bed and sat down.
“What do you want from me?” Kyle asked.
“I want you to strip for me.”
“No,” he responded in a shocked whisper..
“No? You want everyone to find out about this?” he asked.
Kyle shook his head and slowly began to unbutton his blouse. Rusty unzipped his slacks and freed his rock hard cock and began to stroke it as he watched. Kyle was actually getting excited though he hid it.
Rusty stopped Kyle only once and ordered him not to move as he exited the room. He returned a minute later and told Kyle to continue, soon Kyle was down to his lingerie and heels. Rusty stopped stroking his large cock and called Kyle over to the bed and and asked him to sit. He then took Kyle’s hand and placed it on his rigid member.
“Stroke me,” he said in a husky whisper.
Kyle began to gently pump Rusty’s cock as he kissed his neck, ears and lips. Again he could not believe how turned on he was and how hard his own cock was straining against its silky prison.
Rusty then ordered him on to get on all fours on the bed. He pulled the silky panties down to the knees and Kyle felt something wet and warm being applied to his backdoor. He looked over his shoulder to see that Rusty had a tube of KY in his hand. He then applied a generous portion to his cock.
Kyle shook with anticipation as he did this.
“Do you want me to stop?”
Kyle surprised himself by answering, “No”.
Rusty slowly began to push his hard cock into his virgin backdoor. Sylvia had talked about this but he never believed that it would happen to him, or that he would be such a willing participant. The pain lessened as his body antalya escort accepted this intrusion and soon he felt Rusty’s balls banging against his butt cheeks as he began to increase his pumping.
“Oh yes,” Kyle moaned over and over.
Rusty took one of his hands off Kyle’s hips and grabbed Kyle’s cock and began to stroke it, Kyle’s pleasure increased tenfold. Rusty’s rapid breathing and thrusting told me that his orgasm was approaching.
He released Kyle’s cock and withdrew his before he flipped him over on his back.. He issued a low moan and shot his load on the satin garter belt. A minute later Kyle released his load there as well.
He collapsed next to him on the bed and stared again.
“I took your cherry didn’t I?” he asked as he gasped for air.
“Yes you did.”
“How was it?”
“It was great,” Kyle responded.
“Can we do it again sometime?” Rusty asked.
“I’ll think about it.”
“I promise to buy you the sexiest outfit you have ever seen,” he stated.
“What about Delilah?”
“What about her? She never lets me do her in the butt and what she doesn’t know can’t hurt us.”
The sound of Delilah’s car coming up the driveway spurred us into action. Rusty and Delilah eventually made up and later that evening the muffled sounds of Rusty pleasuring her caused Kyle to recall what had happened earlier.
As Rusty did her Kyle did himself, they all finished at the same time.
A month later Kyle was at one of the out of state functions and and dressing for cocktails. The evening gown he selected fit him like a glove and was slit from thigh to the floor so it showed plenty of leg with each step. He greeted those lingering around the entrance with hugs and kisses and was about to enter when I heard a familiar voice.
“May I escort you inside?” the voice asked.
He looked up and there was Rusty looking like a million dollars in his suit.
“What are you doing here?” Kyle asked kissing him lightly on the cheeks.
“I am looking for this totally hot brunette I met once and was hoping she would join me at my table.”
Kyle took his offered arm and we sat together at a table. As they drank and chatted Kyle felt Rusty’s hand caress his silky leg. He allowed his hand to drift to his lap where I could feel his erection growing under his suit pants and gently rubbed it.
“How did you find this place?”
“I followed you.”
“For two hours?”
“It would be worth it to find this female.”
“So what happens when you find this totally hot brunette?” Kyle asked.
“I will ask her if she has a fondness for black leather and silk.”
“And if she does.”
“I will tell her I am in five thirty seven and that I purchased several pieces of lingerie made of those materials,” he responded.
Two hours later we were heading to his room. It was the beginning of a great weekend.
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