Uncharted Territory
- 4 years ago
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Uncharted Territory. The Conclusion free porn video
Cal was up earlier than normal for a vacation day and was in and out of the shower long before his parents woke. As he waited for the coffee to finish brewing, he wondered what the day would bring. He also thought about the dreams he had last night and hoped it was a premonition of things to come.
In his dream, he was clad in the softest and silkiest lingerie imaginable. Cal saw himself in a black bra trimmed with delicate black lace and a garter belt that matched. The garter belt held up a pair of black seamed nylons and over them was a tiny pair of panties. His makeup was flawless and he felt one hundred percent feminine.
He wondered if he had gone too far. At first, all he wanted to do was wear these sexy garments; he never envisioned himself made up as a girl, just as he never imagined himself tonguing his buddy and then fucking his best friend in the ass. When he heard his parents heading to the kitchen, he forced himself to calm down in order to lose the erection that just thinking about yesterday had given him.
A minute after his folks left for work, he literally ran to his buddy Johh's house. His friend answered the door in the same white outfit he had worn yesterday and he greeted Cal with a long kiss once inside before they headed to the attic. A week ago the idea of kissing another male would have made his skin crawl, and now he looked forward to it.
Upon reaching the attic and locking the door behind them, John asked Cal to strip again and handed Cal the sheer black bathrobe he had worn yesterday. Cak surprised himself by not stepping behind the dressing screen as he disrobed and donned this long see-through robe.
"Just a robe?" Cal asked.
"For now," his friend responded with a shy smile.
Cal was directed to the chair in front of the makeup table where all the makeup had already been laid out. Cal picked up the elastic band used to keep his hair out of his eye and face and placed it around his head as his buddy had done to him yesterday and a moment later, his buddy went to work on his face.
"I thought about this all night," Cal confided in his friend.
"So did I. Did you get hard?" John replied.
"Yes I did, "Cal replied as the soft brushes moved across his face.
"Me too," John answered.
It was about two hours later that John handed the long dark wig to his friend to placed it on his head. Once again the male teen that had been Cal had vanished and in his place was an attractive teenage girl.
"Let's get dressed," John said as he handed a pair of black seamed nylons to his friend.
Cal was shown how to roll the stockings onto themselves and place his toes in first before carefully unfolding them and covering his legs. The sight and feeling of his legs covered in the silky nylons caused Cal's erection to appear. Cal watched as a black garter belt was placed around him and he was given instructions on how to attach the ribbons to the stockings.
Cal was then handed a pair of black bikini panties and he slowly slid them up his legs and he noticed that John's erection appeared as he watched his friend dress.
"You are so fucking hot," John admitted as he handed Cal a matching bra and the inserts for the cups.
Cal stood up and lost the robe long enough to fasten the bra around his chest and placed the padding into the empty cups. He donned the robe again and then turned to face his friend.
"Welcome back, pretty girl," John commented as he stepped into Cal's open arms.
They shared long slow tongue kisses as their hands roamed over each other's bodies and Cal grew hotter and harder with each passing minute.
"What happens now?" Cal asked as he stared into John's eyes.
"That depends on you," John responded."Any suggestions?" Cal asked.
"Well, I could bend you over the makeup table and take your cherry if you want," John suggested.
Cal's heart began to pound in his chest and his cock began to leak precum in his panties at John's suggestion and his man nipples harden under the padding for the bra as John said this. Was he ready to go all the way he wondered? He looked and felt like a female and it was better than he imagined it would be, but was he ready to be taken?
Suddenly the desire to explore this unknown territory came over Cal as he looked into John's eyes.
"Promise me you'll be gentle," Cal said in the softest that he could summon.
"I would never do anything to hurt my best girl," John replied as he gently spun Cal around and escorted him to the makeup table.
John had Cal bend at the waist and place his hands on the top to steady himself. John then dropped to his knees and slid his hands under Cal's sheer robe until he found the waistband of his panties and began to slowly draw them down his legs. The feeling of John's hands on his legs and butt caused him to suppress a moan, but he lost the battle when John stroked his throbbing erection.
John then reached around Cal and snagged the bottle of lube and proceeded to cover the length of his small hard cock with the slippery liquid. He then covered his fingertips with more of the lube and slid them between Cal's butt cheeks and proceed to cover his virgin pucker with the warm fluid.
The feeling of John's fingertips spreading the lube on his anus filled him with a desire that he had never known before.
"Now, spread your legs for me," John requested and Cal adopted a spread-eagle stance.
Cal felt the greased head of John's cock slide between his butt cheeks and then pause when it encountered the tight ring of muscle.
"Are you ready, pretty girl?" John asked in a soft voice.
"Yes," Cal responded in a voice that trembled with anticipation.
John kissed Cal on the neck and then pushed himself gently into Cal's virgin backdoor.
Pain and pleasure washed over Cal's body and mind as his friend pushed his hard cock into his tight hole and he moaned.
"Are you OK?" his friend asked.
"Yes," Cal hissed in response.
Before Cal knew it, he felt John's body heat and padded chest against his back and he moaned again. The reflection in the mirror showed a stunning blonde behind an attractive brunette and there was a look of contentment was etched on the brunette's face and the next thing Cal saw was his friend's hands on his fake breasts.
"My cock is all the way in you," John said.
"Then fuck me," came Cal's response.
John placed both hands on his friend's waist and began to gently side his cock in and out of Cal's ass; his friend moaned with each thrust. Cal moaned even louder when one of John's hands left his waist and encircled his cock and began to masturbate him.
Cal stopped his soft moaning long enough to announce that he was going to cum and John said that he too was on the verge. Cal felt his friend's body tremble and a second later, he heard his name being called as John emptied the contents of his balls into Cal's ass. Cal swore that he could fell it and let loose in John's hand.
They both slid to the floor, where they cuddled and shared gentle kisses as their rock-hard members softened.
"So, how was it?" John asked.
"That was fantastic," Cal said after a long time.
"As just think we have the whole summer to play and this is just the beginning," John responded.
That evening as Cal laid in bed, he felt a small burn around his anus. He banished the pain by thinking about what the summer held in store for him.
Kaylin
- 29.08.2022
- 13
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- Category:
- Crossdressing
