Ken felt himself being shaken and heard a voice urging him to wake up. When he opened his eyes he didn't know where he was for a second until he turned his head and saw Vanessa next to him.

"Hey babe, you've got to get up and moving. It's getting late and my parents will be home," she said softly.

Ken was out of bed like a shot and quickly redressed. He must have been so deeply asleep that he was unaware of Vanessa leaving the bed. She was now dressed in a short terrycloth robe and he still saw no trace of his buddy in the pretty face before him. He apologized for falling asleep.

"Not a biggie," she replied. "I dozed off too, but I need time to remove all my makeup and make myself look like Van again."

They kissed goodbye but not before Vanessa extracted a promise for Ken to be here tomorrow around nine.

"This time you call first," she scolded.

As Ken walked home he thought about what had occurred and he didn't feel strange in fact he was excited. He did alright with the girls at school, but nothing went beyond kissing and some caresses of budding breasts and pantyhose covered legs. Van or rather Vanessa allowed him to go further than he ever imagined.

The following morning he called his friend as promised and was instructed to be there as soon as possible.

"The door will be closed but unlocked. Just call out when you arrive and head to my room," his friend instructed.

So that is exactly what he did. When Vanessa appeared she was once again her schoolgirl outfit  This time she had omitted the white knee socks in favour of thigh high nylons whose lace tops were visible under her short skirt as she moved. Once again, Ken could not believe that this lovely creature was his longtime buddy.

He stood up as she approached and they embraced each other and shared another long tongue kiss as she gently brushed her body against his. Ken could not believe how fast he started to get hard, even the girls at school didn't excite him this quickly. The fact that he could feel Van's own hard cock hidden under her skirt and panties pressing against him didn't turn him off.

Ken once again allowed his hand to caress Vanessa firm body, only this time he allowed both hands to cup and squeeze her firm backside.

"You are so pretty," Ken said when he finally found the words.

Vanessa blushed and thanked him for the compliment.

"So what happens next?" Ken asked.

Now Van aka Vanessa had seen enough Hentai features to know exactly what was to happen next. In his beloved videos, the main female character was usually mounted amid issuing moans of pleasure as some male pushed his hard cock in her tight teenage pussy.

Vanessa had no tight pussy to offer and he found that depressing. Then he recalled that in some of the videos, the pussy was ignored and the hero went straight for her lead female's ass. The sight of some pretty girl's schoolgirl skirt being pushed up and her panties being pulled down were always a turn on. The following images of the male pushing his hard rod into her tiny butt always got him excited.

 Vanessa wondered if she ready to take that final step and would her friend comply.

"Do you know about anal sex?" she asked in a timid voice.

"Yes, I do," Ken answered as he felt his heart begin to beat faster and his body temp heat up.

"You have to be very very gentle, You will be the first cock I ever had inside me and you're so big," Vanessa told him with a look of concern in her eyes.

She helped Ken removed his clothing and was once he was totally naked she was astounded by the size and look of her friend's equipment. Vanessa grabbed a bottle of lube from the nightstand drawer. She then dropped to her knees and began liberally coat the hard cock before her with the slippery substance.

Once her task was completed Vanessa stood up and got on her bed. She then took a position on her hands and knees and then lowered her upper torso and rested her head on her crossed arms and then looked over her shoulder as she wiggled her bottom.

"It's all yours," she said quietly in almost a female voice that she didn't know she had.

Ken also mounted and knelt behind her. He pushed the hem of her tiny schoolgirl skirt to her waist and a black silk thong was revealed. Ken admired it as well as her nylon covered legs before sliding the thong down. He placed on hand on her waist and the other around his shaft that he pointed to the crack in her butt.

A jolt shot through Ken's body as the head of his cock made contact with the skin of her ass. He paused for a second and then slowly pushed himself inside. The pain of this large intrusion caused Vanessa to stifle a cry, but she said nothing and gritted her teeth.

Just as Ken was attempting to push the head of his cock past her the tight ring of muscle the pain became too much for Vanessa to deal with and she yelled for him to stop. Thankfully her friend was a gentleman and withdrew.

Vanessa pushed her skirt down and laid on her side and began to cry. Ken laid next to her and gathered her in his arms.

"I'm sorry," she said between sobs. "It hurts too much."

"It's all right, I don't want to hurt you," Ken responded,

Vanessa pushed Ken on his back and commenced to jack him off. The slippery substance made it even better than the last time and he quickly lost his load in Vanessa's grip.  They lay together for quite some time and then to Vanessa's surprise, Ken pushed her on her back and slowly slid his hand under her skirt.

The feeling of her nylon cover legs to his fingers was a turn on. Ken then allowed his hand to encircle Vanessa's small swollen cock.

"What are you doing? she asked.

"I can't be the only one to enjoy an orgasm," Ken responded as he commenced to gently masturbate her.

Vanessa was about to protest but the feeling of her friend's hand around her tiny shaft felt so good that she said nothing. Now she had masturbated many times, but this was the first for this act to be performed on him. She moaned as the girls in his videos moaned.

Ken was sure that touching another man's cock would turn him off, but seeing and hearing her reaction to his ministrations was a turn on and he slowly increased the speed of his hand.

"Come on, pretty girl. Cum for me," Ken said softly as he commenced to plant kisses on her neck and red lips.

Vanessa moaned her pleasure out loud in between returning his kisses. She also became aware that her friend was rock hard again and she allowed on hand to gently encircle it. She commenced running the head the swollen head of Ken's cock against her nylon covered leg and this time he moaned aloud.

"Baby, I'm going to cum," Vanessa said between moans.

A second later Vanessa exploded under her skirt and her whole body shook. She heard Ken's breathing increase as he announced that it was his turn and he emptied himself against her nylon covered leg. They released each other's equipment and shared more gentle kisses as they felt their semen cool against their skin and their cocks shrink.

"Not bad," Ken said after a while.

"No, sir, not bad at all and this is only the beginning," Vanessa responded.

To be continued...