Marc was too excited to sleep that night as his mind was swimming with anticipation about his meeting with Charlene. His fearful side reminded him that he had her business card and that he should call her and cancel their meeting. His experimental side chimed in that she had discovered his secret and didn't laugh or tell his parents. She instead kissed him and then invited him to meet her on Saturday morning.

At some point, he must have fallen asleep cause when he woke the sunlight was just peaking through his window. He got up and headed to the master bath where he showered and shaved. Back in his room, he donned his newest erotic lingerie under his jogging suit, everything but the bra. He would put that on later so he didn't have to explain to his folks why he was sporting a moderate B cup under his outfit.

Thankfully the kitchen was empty as they were still asleep. So he left a note telling his folks he had gone for a run which was normal for him and headed to the garage to get his bike. Once inside the garage he shed his top and affixed the black silky bra around his chest and placed the form inserts in the empty cups. Once satisfied that it was secure he headed his bike in the direction of the high school ball diamonds.

The place was deserted save for a black sedan with Charlene leaning up against it. Marc chained his bike in the rack and approached her and was surprised that she met him halfway. She wrapped her arms around him, and he lost no time in embracing her as well. A long deep tongue kiss followed as they held each other tightly.  

She ended the kiss and took him by the hand, and they headed toward her car. Marc was pleased and excited that she wore that same sever skirt and jacket outfit that she had worn last night, and he stared at her shapely nylon covered legs as she walked. Once in the car, he was able to take in the sight of her nipples pushing against the front of her blouse.

Less than ten minutes later she pulled into a parking slot of a rather upscale and well-known motel chain. Charlene opened the door of her room and allowed Marc to enter first. Once inside she lowered the blinds and drew the curtains plunging the room into near darkness save for a courtesy light shining from the bathroom.

Charlene kissed him again before she stepped back and slowly unzipped his jogging jacket. She issued a softest and sexist moan  Marc had ever heard when his silky bra was revealed. She ran her soft hands down his neck and arms before she directed them to his bra. He watched her gently run her hands across the silky cups as she continued to moan and that caused him to become harder than he already was.

Without moving Charlene then removed her suit jacket and slowly unbuttoned her maroon blouse. It parted to reveal a black bra similar to his. She then stepped into him, and he ran his hands over her bra and the full round globes they hid. Charlene then untied the rope of his jogging slacks thus allowing them to slide down his legs and her eyes grew wide as his nylon covered legs were revealed.

She embraced him again and allowed her hands to run over his silk covered ass and down the side of his legs before they brushed the silken pouch hiding his hard cock, this time it was Marc that moaned at her touch. Charlene stared into his eyes as she reached around behind her and Marc heard the soft sound of a zipper being pulled. And a second later her tight black skirt slid over her hips and down her shapely legs before puddling around her slim ankles and high heeled covered feet.

Under her severe skirt was a back garter belt with a black lace trim that held up her nylons and a black silk thong covering her pussy and now it was Marc's turn to stare. They embraced each other, and as their tongues danced in each other's mouths, Marc could feel the heat emanating from the silken triangle and the sensation of silk rubbing against silk as Charlene gently swayed her hips.

"You have no idea how hot this makes me," she said as the kiss ended and she brushed a stray lock of hair from her eyes.

"You're not the only one that's hot," Marc responded.

They took a seat on the couch, and she offered him a Coke which he accepted, his mouth and throat were extremely dry.

"So, how long has this been going on?" Charlene asked as she slid closer.

 Marc told this attractive female everything, and she encouraged him with a gentle kiss when to continue when he felt too embarrassed to go on.

"What's your story? Not too many females are supportive of this lifestyle," Marc asked.

She told him that she had discovered by accident that one of the boys on the cheerleading squad was into cross-dressing and she encouraged it and even showed him how to apply makeup. She had even allowed him to wear her cheerleader uniform on many occasions.

"He, however,  wanted to be with a man while dressed as a female and eventually we stopped seeing each other," she said in a soft voice with tears forming in her eyes.

Marc placed his arm around her shoulders in a show of comfort, and she slid a nylon covered legs across his and was soon sitting on his thighs facing him.

"Have you ever thought about makeup?" she asked with her lips inches from his.

"Thinking about it is as far as it goes. The risk is too great, plus I don't know anything about applying it," he responded.

"Are you harbouring a desire to be with a man?" she asked.

"No way," he responded and received a kiss as a reward for his truthfulness.

"That's good. I hate to think of some sweaty jock grunting as he pushes his big cock into your firm virgin butt," she responded.

Charlene then reached around her back and unfastened her bra allowing it to fall in Marc's lap. Marc needed no invitation to caress and kiss them and suck on her extended nipples. As he did, he could feel the heat from behind her crotch increase. Charlene slid off his legs and stood up and extended her hands so he would stand also.

They were soon on the king-sized bed locked in a lovers embrace. The sensation of Charlene's nylon covered leg running up and down his was almost more than he could take and was seconds away from losing his load. She must have sensed it and ended the kiss and stopped her leg movement.

"Are you a virgin?" she asked from his arms.

"Yes," he answered with a touch of embarrassment. He then talked about the girls at school. His new status had made him popular with them, and he had received a few kisses, but that's as far as it went.

"Those little prick tease sluts don't know a good thing when they see it," she responded with a hint of anger in her voice as she kissed him on the cheek.

"Now how about you lose your panties," Charlene requested.

"Why?" he asked with a hint of hesitation in his voice.

"Do you really want to ride home in cum soaked lingerie?" she asked.

Marc slowly divested himself of his silk underwear and his cock now free from its prison spang into the air. Charlene gently wrapped her fist around it and commenced to gently pull on his rock hard cock. She moved in closer so that her tits were near his lips and he planted soft kisses and licks on them as she jacked him off.

As she worked on him, she allowed one hand to slip under the waistband of her thong and enter her hot waiting slit. Charlene then returned to sliding her nylon covered legs up and down against his. She did it slowly so they could enjoy the sensation of the warm flesh under the filmy covering.

Finally, it was all too much for Marc, and he announced through clenched teeth that he was going to cum. Charlene quickly moved so and placed both her silky knees on each side of his thighs without removing her fingers from her wet pussy. She then bent forward so that her firm breasts were mere inches from the head of his cock and began to rub its glistening head across her extended nipples.

He moaned one last time and then his body stiffened and shot his load on her silky warm breasts. Between the sight of his cumming and the feel of the warm sticky fluid spurting on her and her fingers aggressively working her clit, her orgasm arrived just seconds later.

Charlene rolled off of him and took her place at his side. She wrapped him in a warm embrace, and they planted gentle kisses on each other.

"That was fantastic," Marc said after a while.

"This is only the beginning," she responded.

"I thought you were leaving," Marc answered.

"I am, but I will be back next Saturday. Think you can free up your schedule?" she asked.

"No problem. So what's next?" he asked.

"Wait and see," was all she said before placing her lips on his and kissing him deeply.