Sissy Stepson 10 Stepmother s Sissy
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Taking That First Step Part 3 free porn video
Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen.
Upon exiting Cassandra reappeared clad in black leather, she looked tough and demanding. She escorted him to one of the couches where Cassandra revealed that it was, in fact, a pullout bed. She then sat him on the bed and placed a blindfold across his eyes before placing him on his back.
He was informed that he was no longer a teenage boy. He was now a beautiful teenage girl named Lana that was about to have sex for the first time.The lovely Cassandra repeated her commands in a silky hypnotic voice and Lance began to feel a change. He no longer felt confused or nervous, felt sexy. It was as though her words were pulling his female side to the surface.
Despite the blindfold, he knew her face was inches from his, he could smell her fragrant perfume and sweet breath.
"So are you ready to lose your cherry?" she asked.
"I've changed my mind," Lana responded in a soft feminine voice.
"Changed your mind? After I purchased that outfit for you?" Cassandra questioned in a manly voice.
"The outfit is beautiful, but I have changed my mind".
He felt Cassandra straddle him and place her lips against his ear.
"It's too late for that. I'm going to push my cock into your virgin pussy," she informed him.
Lana tried to sit up but Cassandra pinned him down. Less than a second later he felt something being placed around his wrists. A moment after that he felt his arms being pulled flat against the mattress and was unable to raise them. He expanded his senses and discovered that his bonds on his wrists were nylon stockings.
She stroked and kissed his face and his gloved arms. Lance felt her hands and lips on his chest and his hard flat abdomen as they moved slowly down.
"Such pretty panties you're wearing," Cassandra said as her hands drifted to the waistband.
."No," Lana whimpered.
Cassandra's soft hands began to slowly slide lace panties down his legs. Soon his hard cock was exposed to the air.
He felt Cassandra's fingers run up and down his legs.
"Your legs are so soft and look great in your nylons," Cassandra informed him as she planted gentle kisses on his neck,
Lana struggled against her bonds, it was no use. She continued to plead but to no avail. Lana then heard the sound of a zipper being pulled down and she knew that Cassandra was removing her leather pants. Lana then felt here silky knees against the sides of her legs as Cassandra's small hand circled his cock.
"Are you ready? Here it comes," he was informed.
The head of his teenage cock was placed against the entrance of Cassandra's pussy. he felt heat and wetness. However, in his mind's eye he saw a large cock poised at the entrance of his virgin pussy.
Cassandra then slowly began to lower herself on his erect shaft, she moaned as it moved deeper inside her hot tunnel. Lance's senses returned for a moment and he revealed at the sensation of his cock sliding into Cassandra's hot wet pussy. It felt better than all the stories the older boys had told.
A second later Lance vanished again and Lana returned. She felt this large cock being slid into her tight untouched pussy and she moaned.
"Stop, Please stop. It's too big for me," she begged.
Cassandra only laughed as she began a slow rhythmic ride up and down on the hard cock inside her. She occasionally stopped to plant kisses on Lana's cheek, lips and neck. Lana eventually stopped begging and began to moan with pleasure.
"Fuck me. Please fuck me," she requested.
Cassandra responded by increasing the speed of her movement on the cock inside her. It caused Lana to moan louder.
Lance felt a familiar feeling in his lower belly and balls, he knew his orgasm was moments away.
However, it was Lana that began to moan that she was cumming. It caused Cassandra to raise herself up and then slam down on the teenage cock inside her. Less than a second later a thunderous orgasm shook Lana's body and a long sustained moan of pleasure escaped her painted lips.
Cassandra's orgasm followed a heartbeat later. Lana felt her arms being freed and she embraced Cassandra after she crawled off of her. They cuddled and kissed for the longest time.
"It's time to put Lana to sleep and wake up Lance," she heard Cassandra whisper in her ear.
A few minutes later the blindfold was removed from his eyes and Lance was back. He embraced the sexy older female at his side and they shared a long passionate kiss.
"That was fantastic," he finally managed to say.
"Yes it was. It was even better that I expected," Cassandra responded.
"So what happens now?" Lance asked.
"So many wonderful things. This was just the opening act," she told him.
"Today?"
"No, not today. I will have to open the shop soon and you will have to leave. However next week I made arrangements to have my shift covered."
"Why is that?" he asked.
"So I can invite you to my house, I don't live far from here. That way you can spend the day as Lana and time won't be a problem," she said, kissing him again.
Lance could not have been happier and they continued to kiss and touch. Soon his teenage cock was hard again so Cassandra laid on her back and invited Lance between her legs. He required only a little help and was soon pounding Cassandra's pussy like a pro and Cassandra moaned with every thrust.
The sensation of her nylon crossed legs against his back sped Lance toward another orgasm. At the point of completion, he felt something hard being pushed into his butt. It seemed to increase the intensity of his orgasm tenfold as he shot his load inside her.
He crawled off her and laid there panting with her arms around him. They once again gently kissed as his heart rate returned to normal.
"What was that?" he questioned.
She held up what looked like a miniature cock, it was about three inches in length.
"Did you like it?"
"It was incredible. What is it?" he responded.
"It's called a dildo. You can call it a preview of what's in store for you," she responded with a smile.
Cassandra gave him one last kiss and then rolled off the bed. She returned with two plastic bags and withdrew a sheer black baby doll nightie complete with tiny bikini panties from one of them.
"This will look great on you," she commented before she set the bag down and returned to his side.
"What's in the other bag?" he questioned.
"Some bra and panties for your collection. She then placed a sales receipt on his chest between his bra cups. Lance looked at it and it was less than he expected.
"We need to get moving. I have to open up the shop soon," she informed him as she left his side.
Lance returned to the dressing room and removed the beautiful white combination and the wig. He then donned the lingerie he had worn there, exited with the discarded items and bumped into Cassandra as he exited. She was dressed in her work clothes and had redone her make up.
"Leave them here and I will take them home and wash them. Plus it will something less you have to hide," she informed him.
Lance then dug a wad of bills out of his pocket and handed half to her. She took the money to the cash register and rang up the item and placed the bills in the drawer. Cassandra then handed him a business card, her address and phone number were on the back.
"I want you to call me during the week," she said as she escorted him to the back door.
They shared one last kiss before he mounted his motorcycle and headed home. As he rode he thought about what had happened and pondered what the future held in store for him. It was the promise of spending a whole day with Cassandra while dressed up that made him smile and helped him endure the week ahead.
Lynne
- 14.10.2021
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