Road Trip 2 Remember
- 2 years ago
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With trembling fingers, he began to pack his large suitcase. First, he started with some of the silkiest and sexiest lingerie in his extensive collection. At least a half dozen silk and lace bikini panties along with tiny silky thongs were placed inside first along with their matching bras.
Garter belts made of satin and silk came next. A half a dozen pairs of black nylons that were either seamed or patterned shared a spot along with crotchless pantyhose. Four long silky full slips each boasting delicate embroidery on their hemlines followed. He wanted to pack them all as he was not sure of how many would be needed.
A half a dozen of the sexiest nightgowns he owned were folded and added to the suitcase. Some were full length and the others were short. Then came the silky robes to match the nighties. The last items were shoes, all were high heels and all were black. Just handling the silky garments began to work their magic and he became excited and was forced to stop and take a break.
He covered his trim naked body with a short silk robe before he headed to the kitchen and took a seat at the kitchen table As the soft garment settled in against his hard cock and balls a shiver ran through his body. He managed to ignore it as he poured a cup of coffee and lit a cigarette. As he began to relax and once again question his actions. For close to fifteen years Gary Mason had indulged himself in dressing in women's clothing. He never knew where this desire came from and he never ignored it.
Maybe it was the collection of Playboy magazines that he had discovered in his teens sitting on the curb on trash day. He recalled sneaking them into his parent's house and hiding them in his room and would peruse them in the dead of night. While the models were attractive and made his teenage dick hard, it was what they wore that really turned him on. He began to wonder what they felt like against his skin.
Gary recalled the first time he purchased an ensemble through the mail order. The internet was in its infancy and there was no online shopping as of yet. In an act of self-preservation, he had the package sent to his Grandma's house to avoid questions on what he got in the mail. The black bra, panties, garter belt and nylons arrived within a week and actually fit him considering he had to guess on the sizes. He remembered the fact that he lost his load in the tiny bikini panties just as soon as his hard cock and balls touched the silky material.
Knowing the taboos and prejudices of the day he kept this practice a secret. The final year of high school came and went and so did college. He did all right with the ladies but only a few dressed the way he liked as far as lingerie and not very often. So late at night, he would don a sexy ensemble from his hidden collection and stroke himself through whatever garment he had chosen to wear.
Gary wound up accepting a position after graduation with a local investment firm and shortly thereafter moved out of his parent's house and into a condo. The internet now featured online shopping and a dozen sites that catered to those that embraced this addiction.
He spent hours reading the blogs in between ordering lingerie. It seemed not a day passed without a package arriving at his residence. Gary soon began to experiment with makeup. It took a few months but he eventually became skilled at looking like a female. The long wigs he purchased helped to complete the illusion as did the breast forms used to fill the empty cups of his bras. His nights and weekends soon became devoted to dressing and learning how to walk in high heels.
His time in the gym also changed. He no longer lifted the heavyweights to force his muscles to grow larger. He used light weights and high repetition to give him a plenty of lean muscle mass. His legs leaned out and took on a total female appearance. He shaved all his hair off his arms, legs, chest and crotch and kept them smooth. He had seen too many pictures of hairy legs, back and butts in female attire and he believed it ruined the illusion.
It was by accident that he discovered the Lush Stories site. From that point on he spent many a night reading the stories about crossdressers while dressed in his most erotic ensembles. He left compliments on the stores that turned him on and even found the courage to friend a few of his favourite authors.
He soon began to chat with one member know as "Silky Shorts". They shared their stories of dressing and how they felt when dressed. It seems they had started dressing at around the same age and endure the strain of keeping this practice a secret. The months passed and the chats became longer and that's they admitted they were attracted to each other.
"Those pictures on my profile page are not of me, I have to be very careful," Gary admitted.
"Same here," Silky responded.
"No one has ever seen me when I'm dressed up," Gary confessed.
"And I've never had the desire for anyone to see me dressed up except you," Silky admitted.
When Gary admitted similar feelings, Silky suggested that he come down for a visit. Gary countered the suggestion and asked that his friend drive up to his place. It was with embarrassment that Silky confessed that his car was on its last legs and couldn't handle a road trip. Then he suggested that if Gary waited a month he would take delivery on a new vehicle by then. Gary didn't want to wait and neither did Silky.
It took another week for them to assure each other that they were not serial killers or some hairy sex-crazed maniacs who only wanted to force their hard cocks in each other's virgin butts. Silky surrendered his address and phone number and Gary promised that he would be there at dusk.
Finally, calm Gary returned to his packing. His makeup and wig case was next to be inspected and packed so all that was left to do was hit the road.
Gary left in the wee hours of the morning and drove the three hundred miles non-stop. He arrived in his friend's city and located Silky's house, it was as he had described, a beautiful ranch house. He then located a motel close to it as he didn't want to present himself to Silky until he was fully dressed and made up. Gary fired up his laptop and requested a chat with Silky, seconds later he got a response.
"Where are you?" Silky asked in an excited voice.
"I'm close but I didn't want you to see me until I was dressed and made up," Gary responded.
"When shall I expect you so I can be ready?" Silky seemed to moan the question.
"At sunset. I'll call when I'm heading your way," Gary replied.
Gary took his time applying his makeup and dressing as he wanted to look perfect. He selected a short black silk and lace nightie with a matching garter belt. The hem of the nightie was short enough to reveal the tops black nylons that were attached to the ribbons of the garter belt as he moved.
As the sun was beginning to set he threw a topcoat over his nightie and slipped his high heels on his feet He then grabbed his suitcase and makeup case before he headed out the door while praying that no one saw him. He placed a call to Silky to tell him he would be there soon and with is hear thumping hard in his chest he pulled into Silky's driveway and exited his car.
His knock on the door was answered by one of the most gorgeous creatures he had ever seen outside of his beloved Playboy magazines. Silky was clad in a short mint green silky nightie under a mesh robe. Black nylons covered her long legs and stiletto heels adorned her tiny feet. Silky's makeup was flawless as was the long wavy dark hair that fell to just above her pert breasts.
As Gary took in the vision before him he was shocked at just how young Silky looked. Once inside they embraced and then Gary dropped his topcoat to reveal the black silk and mesh nightie hidden underneath. Silky's wide eyes and intake of air confirmed that Gary looked as good as he thought.
Silky took a hold of his hand and she led him to the kitchen where they took a seat at the table. Gary accepted an offer of a Coke and could only stare at the light of the refrigerator as it lit up her face, she was really young looking and he began to get nervous. As they sat there enjoying their beverages her appearance began to bother Gary.
"Just how old are you really? You're not twenty-one," he finally asked.
Silky's face lost its smile and she hung her head for a moment. When she raised it again he swore he saw tears forming in the corners of her eyes.
"I'm sixteen," Silky admitted.
"Where are your parents?" Gary asked.
"They are travelling abroad and will be gone for a month or so, "Silky answered.
"I take it that you don't have a car either?" Gary continued,
"I do have a car, but only a learners permit," Silky continued.
"You do know that I am a lot older than you?" Gary stated.
"Really? You don't look it," Silky responded.
Gary smiled and reached across the table and took hold of Silky's hands, they were smooth and boasted perfectly polished nails.
"Relax, I didn't travel this far to let a little thing like age make me leave," Gary said in soothing tones.
Silky stood up and came around the table to briefly embrace Gary before leading him through the house to his bedroom. A dozen scented tea candles were placed around the room and their scent was pleasant and calming. They soon laid down on the king size bed just inches apart from each other.
As Gary smoothed his nightie he became aware that his cock was pushing against the fabric of his panties and he could see that Silky's cock was doing the same.
"I'm not into blowjobs or taking it in the butt," Silky explained.
"That's good because neither am I," Gary responded as he watched Silky shyly attempt to adjust his package hidden under his tight panties.
'Why don't you lose those panties," Gary suggested.
Gary watched with wide eyes as Silky's hands disappeared under the hem of her nightgown and slowly pull off his panties. He issued a moan as he tossed them on the floor.
"Now my cock is against the fabric of my nightgown. It's cool and buttery soft," he said in a soft feminine voice at Gary's questioning look
Without being prompted Gary slid his tiny panties off and also threw them on the floor. He too made a similar moan as his cock was released from its tight prison and was now pressing against the cool and smooth fabric of his nightie.
"I am so horny and hard "Silky admitted as he raised his hemline up allowing his cock into the air.
"Then take care of it while I watch," Gary responded as he slid closer and kept his eyes on Silky's cock.
Silky responded my gently seizing his erect manhood and commenced to slowly tug on it while staring into Gary's eyes.
"I love dressing up all sexy and jerking off," Silky admitted.
"Same here," Gary responded.
"Am I pretty enough? Silky questioned.
"You are very pretty. What about me?" Gary asked with his face mere inches from Silky's.
"You are very sexy. More than I could have wished for," Silky added.
Suddenly Gary was overcome by a new sensation. He leaned into Silky closer and pressed his fake boobies against his arm. He then took hold of Silky's hand and removed it from his cock and gently took hold of it and began to jerk his new friend off.
"Let me do that, pretty girl," Gary said in a soft voice.
Silky issued a long moan as Gary commenced to work on his cock. Then overcome with desire Silky then pushed the hem of Gary's nightie up and gently seized his new friend's cock. Gary had not planned on doing this and he was a little concerned about STD's, but the feeling of Silky's warm cock in his hand vanished all concerns.
"I'm going to cum," Silky moaned while looking into Gary's eyes.
"Then go ahead," Gary responded as he increased the speed of his hand.
A second or two later Silky's cock spewed its contents onto Gary's nightie as he issued a long moan. A heartbeat later Gary announced that it was his turn as he let loose onto his friend's nightgown.
As they laid there on their sided enjoying the sensation of falling back to earth from their orgasmic high Gary noticed the look of concern on his friend's beautiful face.
"There is no need to worry. I've been tested and am clean. Plus I never did any girl without protection," Gary said softly.
"I know that I'm clean as I've never been with a female," SIlky responded.
Then for reasons unknown, Gary planted a kiss on Silky's cheek and received a kiss a second later.
"We need to get changed and refresh our makeup," Silky stated.
"All I need is a place to change," Gary responded.
"The master bath is yours. I'll take the half bath," SIlky responded as they climbed off the bed.
As Gary recovered his suitcase and makeup case from his car he wondered what the weekend had in store for him.
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