Taking That First Step - A New Chapter Begins free porn video
The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra.
It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his stunning transformation he spent many hours in his room at night working on his skill at makeup. Over time they improved one hundred percent.
The results of all the practice became evident and he was passable in any light. Even Cassandra could not believe that he was not a generic girl.
Cassandra had introduced role play and spankings into their meetings and Lance soon became a willing participant. She selected the softest and silkiest lingerie from her supplier's catalogs which he purchased for his collection. The assortment of slips, bras, panties, nylons and garter belts grew quickly.
Now to avoid the possibility of detection he kept only a few of Lana's things in his room at his parent's house. He took great pains to ensure that these silky items were so well hidden so they could not be accidently discovered. That would lead to too many embarrassing questions.
Lance did a great job at hiding his alter ego from his buddies. Sans lingerie and makeup he looked like an average teen. He still played baseball and football with them and they went to the community pool as a group. They checked out the girls from school in their bathing suits and made comments about getting them naked and receiving blow jobs from them. Lance laughed inside when he realized that Lana was better looking than most of them.
It was during a Friday morning get together that Cassandra sprung a new idea on him. He had just settled down next to her on her under the satin sheets of her king sized bed. He was in full makeup and clad as she was in a black bra, thong .nylons and garter belt.
"So are you ready for the next step?" she asked.
"There is more than this?" he responded.
"Yes there is, but only if you feel you're ready for it," she answered.
Now during their role play, Cassandra attempted to look as masculine as possible. It was done to give Lance/Lana the illusion that he was with a real man. However due to her looks and figure she was not real convincing.
"I have an acquaintance that is really into cross dressers," she began.
"You never mentioned that before. Is he a lover?", Lance responded with just a hint of jealousy.
"No, not at all. I never mentioned him before as you were just starting to explore your feminine side. Now If you feel ready I'll invite him over on Saturday," Cassandra responded smiling at the jealousy in Lance's voice.
Lance wasn't sure if he was ready for such a leap as he didn't consider himself gay. So why was he getting excited at the prospect of being with another male?
"Yes,invite him over," Lana responded.
So on the following Saturday Lance arrived early and proceeded to apply his makeup. As he sat at her dressing table Cassandra laid out his clothes on the bed. It was a short pleated black silk miniskirt and a matching top. This would be the first time he would be dressed in street clothes.
"Now if at anytime you feel uncomfortable you need only to say the word stop," she informed him.
About two hours later his makeup was complete and he placed the wig on his head. Once it was brushed and sprayed it was time to get dressed. As Cassandra watched she could not believe the change in the appearance of her friend. There was no trace of Lance as he to began don the black bra, panties, garter belt and nylons.
His cock began to twitch as it always did as he slid the nylons up his legs. He then donned the black silk and lace garter belt and attached the stockings to the ribbons. A matching bra completed with foam inserts was next followed by the silky panties. It was the moment that the silky blouse touched his skin that he became hard. The hardness only increased as he stepped into the miniskirt and zipped it up and then placed the heels on his feet.
"So? How do I Iook? " he asked doing a slow pirouette as he entered the living room.
Cassandra responded by taking him in her arms and placing a long and slow tongue kiss on his lips.
"You look one hundred percent fuckable," she said softly.
A moment later the doorbell rang and Cassandra went to answer it. When Lance heard a male voice coming from the side door his heart rate increased and he lost his hard on. A second later Cassandra led a handsome young man into the living room and Lana was blown away by his looks.
He was tall, well built and quite handsome. He was dressed in dark slacks with a matching dress shirt under a leather blazer, he looked like a make model.
"This is my friend Lana. Lana this is Bert," Cassandra said in the way of an introduction.
"It's a pleasure to meet you," Lana said softly.
Bert stepped away from Cassandra and gave Lana a kiss on each cheek.
"The pleasure is all mine," Bert responded.
Lana and Bert took a seat on the couch while Cassandra went to the kitchen to make coffee. They made small talk as they took in each other features. Bert stared at the slender legs encased in her black stockings that appeared from under her miniskirt and the high heels on her feet. He stared at her ruby red lips and his head swam as he inhaled her perfume.
As Lana started into his dark brown eyes she felt the same excitement she felt prior to making love to Cassandra. Lana pretended not to notice the bulge in the front of his dress slacks. She hid the fact that she had become excited and a little confused.
Lance was pretty sure he wasn't gay based in the way he looked forward to making love to Cassandra. But now here was was all hard and excited at the sight of another man's erect cock.
"You are so pretty," Bert finally said.
"Thank you. You are incredibly handsome," she responded.
They both laughed at the corny lines they delivered. Bert slid in closer to her and placed one arm across her silk covered shoulders.
"Can I kiss you?" he asked softly.
"Yes," Lana responded in soft barely audible voice.
Bert used his free hand and gently turned Lana's pretty face toward him. He then placed his soft lips on her cheeks where he planted light kisses on them. He then moved his lips toward hers and gently made contact with them.
A spark of desire shot through Lana that she had never felt before and she returned the kiss.The gentle kisses became much longer and she allowed his tongue to slip into her mouth. Lana twisted in her seat to allow Bert the opportunity to hold her as they kissed.
Lana allowed her hand to gently circle the protrusion in the front of his dress slacks and she gently slid her hand up and down it.It wasn't very big, but it was as solid at steel.
"Oh my," she said softly as she continued to gently jack his hard cock.
"Does that bother you?" he asked.
"No, not in the least," Lana responded.
"I'm glad because I want you so bad," Bert finally admitted.
"I want you too," Lana responded.
"Do you think Cassandra will mind if we use her guest room?" he asked.
"Let's find out," Lana said as she rose from her seat and took him by the hand.
"I'm going to give Bert a tour of your house starting with the guest room," she informed Cassandra.
"Enjoy," she responded from her place at the kitchen table.
Once in the spare room down the hall, Bert took Lana in his arms and held her tightly as he kissed her. Lana embraced him and returned the kiss and allowed her hands to slowly trail down his back. They each cupped and squeezed the firm buttocks of the other as kisses and licks were applied to ears and neck.
"This will be a first for me," Bert admitted.
"Really? Cassandra mentioned that you had a weakness for crossdressers," Lana responded.
"I do. I buy them drinks and flirt with them, but none of them ever got me this excited," Bert continued.
"This will be a first for me too," Lana admitted.
"You're a virgin?" he enquired
"Only to the aspect of being with a real man."
Bert led her to the white leather chair in the corner and then stood behind her. He reached under her skirt and slowly slid the silk panties down her legs. Lana softly moaned at the feeling of his warm hands against her skin. Bert then had her place one foot on the seat cushion as he dropped his trousers and boxers.
He reached for the small bottle of lube on the nightstand and coated his fingers. He softly applied the slippery oil to her little pucker before coating his own rock hard cock. He then moved in closer and placed the head of his cock between Lana's butt cheeks
. Again she issued a low soft moan at the sensation of the warm cock at the entrance to her back door.
"Are you ready?" he asked in a gentle voice.
"Oh yes, but please be gentle," she responded in a hoarse whisper.
Bert placed his hands on her hips and slowly thrust his pelvis forward and moaned at the feeling of his hard cock entering her tight entrance. He didn't go to far in before he pulled out and then slowly pushed himself into her again. Each time he did he allowed himself to enter further inside her.
"Are you OK, pretty girl?" he asked.
"Oh yes, "Lana moaned as her hand dropped down and circled his own swollen cock.
As Bert continued to slid himself in an out of Lana her moaning became louder. Lana commenced to jack her own cock as Bert worked on her rear. Finally Lana sensed the end was near.
"I'm going to cum," she said in between moans.
"So am I," Bert responded.
She felt his body stiffen as he shot his load into her. Lana moaned and shot her wad onto the chair. Bert withdrew his now shrinking cock and they crumpled to the floor and held each other.Lana's knees were weak and her body was shaking as they gently kissed.
"That was absolutely the best I have ever had," he informed her.
"Same here" she responded.
Bert headed to the bathroom to clean and redress. Lana didn't bother to clean up, she simple slipped her panties back on and straightened out her outfit. She joined Cassandra in the kitchen for coffee. Bert reappeared about ten minutes later looking pretty much like he did when he first arrived.
Lana's body was still vibrating as they drank their coffee and she felt Bert's cum begin to leak out of her butt. Bert finished his coffee and rose to say goodbye. He kissed both ladies before stepping out the door.
"So, how was it?" Cassandra asked when she returned to the table.
"It was fantastic," she responded,
She then went into great detail as she told Cassandra everything about the encounter.
"I wish you could have seen it," Lana stated.
"I did, You were both so busy you didn't see me open the door and peak in. It got me very hot." she admitted.
"Just telling you about it has gotten me hot again," Lana admitted as she pulled her skirt up
He revealed to Cassandra that his hard cock straining against the fabric of her panties.Cassandra stood and came over to his chair and asked him to stand. She kissed him long and deep as her hands slid the soaking panties down. She then bade him to sit down again.
Lance/Lana watched as she removed her panties and hiked her skirt up. Cassandra then straddled him and directed his hardness into her wetness and they fucked in her kitchen.
"You wait until you see what I have planned next," Cassandra told him after they finished.
"Better than this?" he asked.
"A lot better," she answered.
Elle
- 11.12.2020
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- Category:
- Crossdressing
