Uncharted Territory
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Uncharted Territory free porn video
Of all the activities that Cal Markus imagined he'd be doing on his summer vacation, this was not one of them. Here he was in his longtime friend John's attic wearing an almost sheer pair of black silk panties over a pair of black crotchless pantyhose and seated in front of a large lit makeup table as his friend was busily bustling around the room depositing items of makeup on the table.
The sensation of the silky panties against his skin was unbelievable as was the sight of his cock pushing up against the thin material and he couldn't resist running his fingers over the head that was already leaking precum as he waited. He also stroked his legs covered in the filmy fabric and it sent a quiver through his body. This was a longtime hidden desire that he never spoke of or acted upon it until today.
"Now now, none of that," John said leaning down and lightly smacking his hand. "There will be plenty of time for that later."
Whenever his buddy came close, Cal could not see any trace of his buddy under the makeup. He had to admit the sight of his friend's ass under the sheer white robe filled him with the same desire he got from watching the girls at school.
Cal had accidentally discovered his friend's secret that morning when he dropped over to John's house unannounced. When the door finally opened to his knocking, he thought it was one of John's sisters that had answered the door. The uniform was not a shock as two of them were on the junior varsity squad, but it wasn't until John spoke that the truth was known.
Now, John was the youngest of four children and he was the only male child in that household. All of John's sisters were tens and were the masturbation fantasies of half the boys at school. The strong feminine genes that made his sisters so attractive made John handsome in a feminine way, he was tall and slender with perfect skin and his hair was thick and shiny.
John invited Cal in and as they sat at the kitchen table Cal took in the sight of John's perfect legs that appeared under his short skirt and the full tits filling out the sweater as his friend dug out some bottles of Pepsi.
"Surprised?" John asked as he opened one bottle and slid it toward his friend.
"That's putting it mildly," Cal responded.
"Now, no one knows about this and I'd like to keep it that way," John continued.
"If it's such a secret why'd you let me in?" John questioned.
"I really don't know. Maybe I just wanted to see my best friend's reaction to how I look," John answered.
As Cal complimented John on his appearance his friend detected a hint of envy in his voice as he did.
"What's wrong?" John asked.
"Nothing," his friend responded.
"Come on, out with it, "John coaxed.
"For as long as I can remember I always wondered what it would be like to dress up like that," Cal admitted.
"Really?" his friend responded.
"Yes really. I almost got caught when I attempting to borrow one of my sister's nighties and that scared me so bad that I never tried again," Cal admitted.
"So do you still have that urge?" John asked.
"Almost every other day," Cal responded with a hint of embarrassment.
"Good, because today I can help you with that," John said with a smile and bade him follow him to the attic.
John's bedroom was the attic of their large house. His dad had remolded and insulated and added a full bath. This was done to give his sisters and him some privacy as they had become too old to be sharing a room and a bathroom.
Once they reached the attic Cal was surprised at the appearance of the mirror with the ring of lights around it, it's a piece of furniture not often seen in someone's home.
"Is that from the school?" Cal asked.
"It was. They had thrown it and the chair out before the remodeling of the cosmetology department and I managed to bring it home where I cleaned and painted it," he answered. "Dad and I carried it upstairs."
John produced a pair of panties and pantyhose from a tall dresser and handed them to his friend. He was told to strip down and put them on. There was only a moment's embarrassment about stripping in front of his friend until John pointed out an old fashion folding dressing screen.
Cal stepped behind and despite being hidden from his friend there was still some hesitation on his part. However, his desire to wear these forbidden garments caused it to vanish and he quickly removed his jeans, t-shirt, and boring underwear. He reached for the silky clothing that he had tossed on the stool he found there.
When he discovered that the pantyhose were crotchless his cock began to stir as he carefully slid them on and then the panties over them. When Cal stepped from behind the screen he discovered that John had removed his cheerleader outfit and was now dressed in a sheer white robe and Cal was mesmerized at the sight of the bra and thong panty he wore underneath it.
"Are you ready?" John asked.
"What do you know about makeup?" Cal responded.
"Are you kidding? I grew up with three older sisters and I've gotten so good at it that I've often applied their makeup for them," he replied as he spun his friend around in his chair so that he was no longer facing the mirror and picked up a makeup brush and went to work.
"Where'd you get the money for all this?" Cal asked.
"A small inheritance from my grandfather," came the response from his friend. "My parents think I put it all in the bank for college.
Cal lost track of time as John's soft brushes worked the contours of his face. When John leaned down into Cal's face he could still not see his longtime friend. He wanted to look in the mirror to see the progress, but his friend forbade him. Finally, John produced a long black wig and placed it on Cal's head. He did some work on it with a hairbrush before he told his friend that he could now look.
Cal spun the chair around and couldn't believe the reflection. There staring back at him was a very pretty girl, not as pretty as John but still attractive. John told his friend to raise his arms and when he did a silky black bra was fastened around his chest and some padding was inserted into the cups that filled them out nicely.
Cal was then handed a sheer black bathrobe and was asked to stand up so his friend could inspect him.
"Wow, you look totally hot. So how does it feel?" John asked.
"It feels better than I imagined," Cal admitted. "So how did this happen to you?"
"As I said, I grew up with three sisters, and when we played dress-up as kids and they dressed me as a girl and I loved it. As I grew older the memory of being dressed as a girl was still with me and I found myself constantly checking their silky lingerie in the clothes basket, Finally one day I decided to try on a pair of panties and the rest was history."
"We are going to have to do something about that," John stated as he pointed to Cal's rock-hard cock pushing against the thin nylon of his panties.
"Yeah, we are," Cal replied running his fingertips over the bulge.
"I have a suggestion that you may not like," John replied in a soft female voice as moved in closer.
"What is that?" Cal asked as the scent of his friend's perfume filled his nostrils.
"That you bend me over that dressing table and fuck me in the ass," John crooned in a female voice.
Cal's face registered surprise at his friend's suggestion. He knew all about anal sex thanks to the dozen of porn sites he visited and often wondered what it would be like to do some girl in the butt but never had the courage to suggest it to the girls he had sex with.
"You have your hidden fantasies and I have mine. Don't think of me as John, my name is Joanie and I attend a private all-girls school and I really want you to do me in the butt," John aka Joanie purred.
As Cal considered what his friend had said he noticed that a new desire had taken hold of him, it was lust. Yes, this was no longer John, this was some hottie from a private school. Cal approached John and took him by the wrist and led him back to the make-up table.
"Now how about you lose that robe and slide those panties down," Cal heard himself say.
"No, you have to undress me," John responded.
So John complied and untied the sheer covering and tossed it aside. Cal inserted his thumbs into the waistband of his panties and slowly slid them down his legs, they were tossed aside. John's cock was not as big as his but it was also rock hard and precum glistened on its head.
As Cal took a step closer John stopped him and grabbed something off the dressing table.
He then dropped to his knees and slid Cal's tiny panties down which caused his cock to spring out of their silken prison. John upended the bottle that he had snagged and squeezed a generous portion into his palm and then began to cover Cal's cock with the thick liquid.
John then stood up and placed her arms around Cal's neck and moved her lips closer to his.
"Do you want me, baby?" she asked.
"Yes I do," Cal answered.
Then much to Cal's surprise John aka Jonie placed her painted lips against his and kissed him, it was a gentle kiss that affected him the same way as a kiss from one of his girlfriends. John pulled his head back and stared into Cal's eyes for a moment praying that he had not crossed an invisible line.
Cal stared at his friend and was not revulsed, he was turned on. He allowed his hands to circle John's waist as he pulled John into him. Once again their lips touched and this time the kiss was longer and more intense. Cal allowed his hand to move down to his friend's firm butt and he gently ran his hands over it as they kissed.
Even the feeling of John's hard cock against his did not push him away, it made him kiss his friend even more passionately. The moan that escaped from John caused Cal to tighten his hold on his friend. A second later Cal felt John's tongue pushing against his lips and he parted them to allow it inside.
To be continued.
Eisley
- 17.12.2022
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- Category:
- Crossdressing
