It was one of the longest weeks of his young life that Marc could recall. When he wasn't attending his regular classes he was at baseball practice where continued to amaze his coaches and team members with his prowess on the ball diamond. When he was alone he thought about Charlene and couldn't wait to see her again.

Friday night was game night and the fans filled the bleachers to cheer their home team on. From his place in the outfield, he tried to scan the crowd in hopes of seeing Charlene's face, but the bright lights made it difficult. Besides, that would be too much to hope for.

It was an easy win for his team and it during the brief celebration that followed, Marc received a text. Suddenly celebrating their win seemed unimportant to the message he received.

"You need to go for a run tomorrow morning and the earlier the better. I'll meet you at the ball diamond," it read.

Marc's heart literally skipped a beat as he replied with a heart emoji. By the time he got home and headed to his room, he was so hard that he forwent the donning of his erotic lingerie and just stripped down and grabbed his rock hard cock. After flopping on the bed, he thought of what Charlene might have in store for him and he lost his load in no time.

Saturday morning was a repeat of last week except earlier. He showered and shaved and then donned his lingerie under his jogging suit. This time, he wore his padded bra as he was sure there was no chance of running into his parents. He then headed to the ball diamond where he found Charlene waiting. They loaded his bicycle into the trunk and then headed to the motel.

Once inside the room, Charlene excused herself and headed to the bathroom, when she returned she looked like a million dollars in a long flowing peach coloured satin robe. She lost no time in wrapping her arms around him and placing her lips on his and giving him a long passionate tongue kiss. 

"I take it you missed me?" she asked when the kiss ended.

"You have no idea," Marc responded.

"Well, the feeling is mutual," she replied.

Marc's hand went to the zipper of his jacket but she stopped him.

"Later for that," she stated and took him by the hand and led him to the desk and bade him sit.

There laid out on the desk was an assortment of makeup, brushes, pencils and a long dark wig. Marc's cock became hard in its enclosure of his silk panties She had him sit on the edge of the chair as she dragged another chair over and sat on the end of her chair after parting her robe to reveal peach coloured panties and garter belt holding up sheer nylons.

Marc's knees were between her silky legs as she reached for a jar of makeup.

"Should I be taking notes?" Marc asked.

"I'll give you a list of what you need but learning to apply makeup is done by trial and error. Thankfully, I had an older sister that showed me the basics and experimented on the rest. I became so good at it that I helped the others on my squad perfect their makeup, It goes in this order. Foundation, Concealer. Blush, Highlighter, or Bronzer. Eye shadow. Eyeliner. Mascara. Lip colour," she announced as each new product was applied.

There was no mirror so Marc could not see her progress.

"So have you thought about my proposal of attending our college?" she asked as she worked.

"Quite a lot. I'm still not sold on the idea of living on campus and sharing a room with anyone," he responded.

"That's only for the first year, but star athletes are not subject to the rules of regular students. It could be arranged for you to have a room to yourself, but since I live a few minutes from campus I don't think you'd be spending a lot of time in your dorm," Charlene stated.

"So then this is not a one-time only thing?" he asked.

"I've been waiting a long time for someone like you to cross my path. So no, this not a one-time thing," she responded.

Marc lost track of time as Charlene worked on him. Finally, she slid her chair back and stood up and reached for the wig and placed it on his head. She then stepped back and examined her work. 

"Un-fucking-believable," she said in a soft voice.

She then took Marc by the hand and told him not to look up as she led him to the large mirror on the closet door.

"Now you can look up," she said as she stood behind him.

Marc slowly raised his head and was speechless at the sight before him. The reflection showed a very pretty high school girl wearing his jogging suit. Charlene then reached for the zipper of his jacket and slowly drew it all the way down until just a hint of his black silk and lace bra were visible in the opening.

As Charlene slowly removed his jacket the feeling the hair of the long brunette wig falling on his neck and shoulders caused him to shudder as a jolt ran through his body. Charlene's hands then snaked around his waist as she pushed her breasts into his back and untied the rope to his slacks and began to slide them down. 

Slowly his garter belt and tiny panties were revealed as well as his nylon covered legs. She then helped him step out of them and instructed him not to move. While still on her knees she reached into the closet and withdrew a shoebox and removed the lid. Marc glanced down and saw a pair of black patent high heels nestled in the tissue paper.

Charlene then had him lift his right leg so she could slide one of the heels on his nylon covered foot, it was a perfect fit. She performed the same thing on his left foot and finally rose. Marc could not believe how great they felt and made his legs look. High heels were an item he had not considered as they would be too difficult to hide, plus he had no idea how to walk in them.

"You look so fucking hot," Charlene said planting kiss on his cheek before she walked over to the bed.

Marc placed his hand on the wall to steady himself as he admired Charlene's work. He never imagined that he could look this good.

Charlene slowly and seductively removed her long flowing robe and then ran her hands over her body.

"Do you want me, pretty girl?" she asked.

"Very much," Marc responded attempting to make his voice sound as feminine as possible.

"Then all you have to do is walk over to me," Charlene responded.

Marc reached down to remove his heels and Charlene stopped him.

"Leave them on," she requested.

"I'm afraid I'll fall on my face," Marc answered.

Charlene hissed instructions and Marc began to slowly walk across the room. Charlene was even more turned on than she believed possible at the sight of Marc approaching her and her panties became wetter by the second. Soon he was at the foot of the bed and Charlene slid down her wet panties and Marc removed his.

The sight of his once constrained cock springing into the air was more than she could handle and she quickly flopped on her back and spread her beautiful legs. Marc walked on his knees between her silky legs until his cock was at the entrance of her pussy and stopped.

Charlene took hold of his hard manhood and placed it at the entrance to her wet cave.

"I don't have any protection," Marc managed to stutter.

"You don't need any, not with me anyway. Now I know this is your first time and I want you to relax," Charlene purred as she pulled his body into her and his cock slid into her wet flesh.

All the locker room stories he heard about sex did not do justice to the feeling of pushing his hard cock into Charlene's wet and hot pussy. She gave him encouragement and brief instructions between her moans and gasps. The feeling and sight of his bra bumping hers as well as the sensation of her nylon covered legs on his back sped Marc's orgasm arrival. 

With a small moan he emptied himself into her and a second later, she informed him that she was cumming and she clamped her legs tighter around him. He got off her and laid next to her and they shared soft kisses. Charlene excused herself and headed to the bathroom to clean up and Marc was hard again when she returned.

Charlene allowed Marc to place her on her back and plant kisses all over her face and neck before mounting her again. This time Charlene was a little louder with her moaning and that seemed to cause Marc to ride her even harder. It was when he announced that he was going to cum again that Charlene ran her hands down his body and came to rest on his firm butt.

Charlene listened to his breathing and when she knew he was a heartbeat away from his orgasm she pushed a slender finger into his butt. Marc responded with a loud moan and he swore that his orgasm was even more intense because of that finger.

"That was unbelievable," was all Marc could say.

"Yes, it was," Charlene responded.

"I better get moving before my parents become concerned," Marc replied sliding off the bed and removing his high heels.

Charlene showed him how to remove the makeup and then left him to clean up on his own. He emerged from the bathroom and removed his padded bra and placed in his backpack. In his absence, Charlene got redressed and soon they were heading back to the ball diamonds.

She gave him one long and passionate kiss before driving off and confirmed their meeting for tomorrow. When Marc arrived home he found his Dad at the kitchen table drinking coffee. They greeted each other and Marc was about to head upstairs when his Dad stopped him.

"What's this?" he asked as he stood and approached his son and pointed to the corner of Marc's mouth." Looks like lipstick."

Marc's heart began to beat faster and he felt a sick feeling in the pit of his stomach.

"What's this?" he asked running two fingers across his cheek."It looks like makeup."

Before Marc could respond he saw his Dad's hand reach for the water bottle holder in the side of his backpack.

"And what have we here?" he asked as he removed a tiny pair of peach coloured bikini panties from behind the water bottle and stretched them between his two hands.

"What was Charlene thinking?" Marc asked himself.

"I can assume that you have not been running?" his Dad questioned.

"Yes," was all Marc could say.

"Marc, have you been with a girl?" his Dad asked.

"Yes," Marc responded again.

His Dad smiled and stuffed the silky panties behind the water bottle where he found them. A smile and look of relief crossed his parent's face. He had been worried about his son's sexuality due to his feminine appearance, but this confirmed that it was a needless concern.

"Does she go to your school?" Dad asked.

"No, she's a college student," Marc responded.

"OK then. But no more lies about going running. Just leave a note that you'll be back later," Dad stated.

"I will," Marc responded as he started to relax.

"And you don't have to leave early in the morning. You can go out later as long as you're home before midnight. Just do a better job at cleaning up afterwards and please don't let your Mom find those panties," his Dad continued.

"I will," Marc promised.

"This will be our secret. Now go and shower before your Mom sees you," were all he said before taking his seat.

Alone in his room and behind a locked door, Marc stripped off his jogging suit and admired the sight of his lower torso clad in their silk and nylon in the mirror and he grew hard again. He flopped on his bed and slipped his panties down just enough so that his cock peaked over the waistband and he took hold of it.

As he jacked his hard cock he thought about Charlene making him up. He recalled how good he looked and how great it felt when he pushed his rigid manhood into her tight pussy. He also recalled her finger sliding into his butt at the moment he was about to shoot his load and he shot his load on his stomach.

As he headed to the shower, he couldn't wait to tell Charlene about this episode and much as he couldn't wait for her to dress him up again.

"Yes, college life was going to be better than he imagined," he thought to himself.