As our story opens we find sixteen-year-old Ken almost naked and laying at Vanessa's side enjoying the slow descent from his orgasmic high. The wonderful feeling is made even better by the fact that Vanessa's body is pressed against him and one of her satiny smooth legs is on top of his leg.

He smiles to himself as he glances over at her and recalls her asking him not to tell anyone. It was a request that was not really necessary. Being jacked off by your buddy that was dressed and made up as a girl was not something you shared with the boys in the locker room. 

Hell, Ken couldn't believe it himself. It was just a few hours ago that he had stopped by his friend's house to see if he wanted to play some online games. It was the third day of the Summer vacation and he was already bored. When the knocking on the door went unanswered he went around to the back of the house to tap on Van's window. He knew his longtime buddy was a heavy sleeper.

Although the drapes were drawn and the blinds were down but there was a tiny gap at the bottom just enough for him to peer inside the room. What he saw made his heart race. For there in his buddies room was the most attractive girl he had ever seen, clad in a schoolgirl uniform in front of a large mirror checking her appearance.

She attractive brunette would occasionally spin around which caused her tiny skirt to flare up to reveal her smooth thighs as well as the white thong she had on underneath. Ken stood outside the window unable to move and afraid to blink lest he misses something. It seemed his buddy had snagged a total hottie from a private school based on her uniform and the fact that he knew most of the hot girls at school. 

He knocked on the window pane causing the pretty girl to jump as though she had received an electric shock before she came over and raised the blinds and opened the window.

"What are you doing here? You're supposed to call before coming over," the girl said in a voice he knew well. The voice belonged to his buddy, Van.

Seconds later he was admitted inside the house where he followed Van back to his bedroom. He watched as Van took a seat at the head of the bed and he joined him sitting at the foot. As Ken stared at the pretty girl sitting there he saw no trace of his sixteen-year-old buddy.

With a trembling voice and an occasional tear streaming down her powdered cheeks, he listened as Van confessed his obsession with Magna, Anime and the Hentai videos. For reasons unknown he wanted to see if he could duplicate the looks of the girls featured in these videos as he found them so sexy. 

"Most of the boys at school think I'm a girl anyway because of the way I look. My features made my transformation very easy," Van continued

"You look even better than some of the girls at school," Ken stated.

"It took a little practice," Van replied.

Ken could see that his friend was still upset so he slid in closer and placed an arm across his shoulder in an attempt to comfort him. Van responded by embracing his friend and burying his head between Ken's neck and shoulder as she began to weep again. The perfume that Vanessa wore filled his nostrils and the breasts pressed against him felt very real, and against his will, he began to get hard.

"Van, please stop crying," Ken said in a soft voice.

"Please call me Vanessa. That's the name I've chosen for myself," his friend responded.

Vanessa raised her head so that her face was less than an inch from Ken's. Even this close he saw no trace of his buddy and a strange desire came over Ken, he wanted to kiss those red lips and the thought about it the stronger his desire became.

"What are you thinking?" Ken said to himself. "You're not gay." 

"Are you okay?" Vanessa asked when she saw him staring.

Ken mumbled a response.

"What's on your mind?" the pretty brunette asked.

"I'm thinking I want to kiss you," Ken answered as he stared into her eyes.

Van was taken aback. It was one thing to look and dress like a girl, but was he ready to act like one? The part of his personality that was Vanessa responded to her friend.

"I wouldn't stop you if you tried," Vanessa answered shyly.

It started out as a gentle touching of his lips against Vanessa's cherry red ones. It quickly progressed into a long and passionate tongue kisses. As Ken ran his hands over Vanessa's body her hands strayed to his groin where they gently rubbed the hard lump they found there causing Ken to shiver to run down his spine.

Ken allowed his hands to run down Vanessa's slender arms and over the firm breasts that felt as real as any girl he had been lucky enough to feel up. Eventually, they strayed to the hemline of her skirt and then up under it. He was amazed at how smooth and silky her legs were and how she shivered at his touch. Vanessa stopped his hand from moving past her knees.

"I think we better stop," she said with no commitment in her voice.

"Why? You feel and smell so good," Ken responded.

"So, you like the way I feel?" she asked.

"Oh yes," he responded as the bulge in his jeans became harder.

"I imagine those jeans are becoming uncomfortable," Vanessa responded.

"A little," Ken admitted.

"Lose them," came the response from the brunette.

Ken slowly removed his jeans and Vanessa was amazed at the sight of his erection pushing against his briefs. His friend was really hung. She made him lay on his back and she then pressed herself against his body. Her small hands moved the waistband of his briefs under his balls and then gently took hold of his rock hard cock.

She commenced to gently masturbate her friend in between kissing his neck. Any hesitation that Ken felt about his friend touching him quickly vanished and he moaned with pleasure. Vanessa placed one silken leg over Ken's leg and began to slowly move it up and down.

Ken was surprised at the fact that the hard cock under Vanessa's skirt was pressed against him and it didn't repulse him. Vanessa stopped only long enough to tear off Ken's t-shirt before she began masturbating him again. Now she ignored his lips and neck and commenced to kiss and lick his nipples.

Ken was ready to shoot his load and told her. All she did was increase the speed of her hand on his cock and the movement of her leg against his. A second later Ken issued a grunt and let loose his load all over Vanessa's thigh. The sight of his cock spewing its contents and the feeling of the warm sticky fluid hitting her thigh pushed her over the edge and a second later she let loose in her silky thong.

As they lay there holding each other they wondered what was next for them.

To be continued.