It had been a long week for Lance. He didn't think the weekend would ever arrive. It was his summer job and kept his mind occupied during the seemingly endless days. He worked for a small company in their shipping department. The job was not very glamorous, but it paid well and kept him clean. Even as we worked his mind thought about what Saturday would bring when he visited Cassandra's house.
Wearing the silky lingerie that Cassandra had provided got him through the long evenings. He considered himself lucky to have found someone that was not judgmental about his wanting to wear female underwear. He also considered himself lucky that he was slender and did not look like those hairy guys in gym.
Once in his room and locking the door he donned these forbidden garments. As soon as their buttery softness touched his skin his cock sprang to attention. As he jacked his rock hard teenage cock he recalled the events of the last weekend.
Cassandra had dressed him in a stunning white lace bra, waist cincher and panties. White nylons and heels were also added along with a wig. He recalled being tied to a bed while she whispered in his ear. She told him to vanish the boy he was and become the girl he wanted to be, and it worked.
He relived the feeling of Cassandra lowering her hot pussy onto his rock hard cock. He once again heard her instructions for him to imagine it was just the opposite. So in his minds eye he was a virgin teenage girl having her cherry taken despite her protests. Lance recalled the massive orgasm that engulfed him and how he moaned in a female voice when it arrived.
Back in the present he lost his load in his tiny silky panties. As he laid there feeling his cum begin to cool he thought about the invite to her house. He would be able to spend the whole day dressed up with her.
Finally Saturday arrived. Lance showered and then donned his garter belt, nylons and panties under his jeans. He was feeling bold that morning and wore the bra with its foam inserts under his t-shirt and covered it with a windbreaker. He left a note saying he had gone riding and was out the door long before his parents got up.
Less than twenty minutes later he pulled into the driveway of a modest ranch house. A sign on the side door directed him to park on the patio and knock on the sliding glass doors. A minute later he was admitted and found himself in Cassandra's embrace. They stood there for the longest time locked in a lovers embrace while sharing a long passionate kiss.
"I have missed you so much," she said softly.
"Me too. I thought that Saturday would never arrive," he admitted.
"Today will make up for that long week," she promised.
Cassandra took a step back and untied her belt and then slowly opened her robe. Hidden underneath was a stunning bra, panties and garter belt combination in purple. Her long slender legs were covered in black nylons and high heels were on her feet. She then began to slowly remove Lance's outerwear until his silky lingerie were revealed. She loved seeing him in these garments as much as he loved wearing them. They took a seat on the couch where she poured him a cup of tea.
"Now if at any time today you feel uncomfortable and wish to quit, you have to tell me," she said in a serious tone.
"Okay," Lance responded, not totally understanding.
"I'm serious. You have to tell me that you have had enough in your strongest voice. I read about this not too long ago, it's called a safety word, " she informed him.
Lance nodded that he understood. Cassandra then stood up and beckoned him to stand. Hand in hand they walked down a hall and she pointed to a closed door as they moved.
"That is my room. It's where you will report after you get dressed," she informed him.
Cassandra then stopped at another closed door at the end of the hall.
"This is where you will get ready. You will find everything you need inside and your surprise is in the closet," she told him before giving him a kiss and walking away.
Lance opened the door and entered one of the most feminine rooms he had ever seen. It was complete with lace drapes, shag carpeting and a satin bedspread on a four poster bed.
Against one wall he found a dressing table with a wig and wig cap waiting for him. There was also lipstick, eye shadow and perfume. He wasted no time in applying them. Once complete, he then headed to the closet.
He opened the door and a look of total surprise and pleasure crossed his face. There on the hangers a French Maid outfit waited for him. Lance ran his hands over the hanging uniform and discovered it was made of heavy satin, his cock twitched as he ran his fingers over the short skirt portion.
On the hanger behind it was a short white petticoat and a pinafore. In a plastic bag on the third hanger were a pair of patent leather high heels, black seamed nylons, fingerless satin gloves and a velvet choker.
He quickly removed his nylons and slowly slid on the fishnets, he loved the texture against his skin. He then stepped into the frilly petticoat and drew it up. It was an effort not to lose his load as he did this. Lance then slowly stepped into the uniform and pulled up the zipper. The bodice was tight and hugged him like a lover. The puffy sleeves were trimmed with lace and the elastic bottoms hugged his arms.
The short petticoat was full and pushed the short skirt out. He could see glimpses of his panties and stocking tops as he twirled in front of the mirror. He then put on the gloves, affixed the choker around his neck and tied the pinafore around his waist.
Lance then sat down on the bed and slipped the high heels on his nylon clad feet. He wobbled a bit as he stood up but didn't stumble as he walked to the mirror. He could not believe how good he looked. The sensations of the nylons and petticoat against his legs were beyond his wildest dreams. He then headed down the hall to Cassandra's room and knocked on the door.
He was told to enter and Cassandra greeted him once inside with a long kiss.
"You look fantastic," she told him.
"I feel fantastic," he replied.
She directed him to the padded bench in front of her makeup table and bade him to sit. She sat next to him and took his gloved hand in hers.
"Do you want the blindfold or are you ready for the next step?" she asked.
"I'm ready," he responded.
"Good, now close your eyes. You are not Lance, you are Lana the maid. You are young and pretty and have just been summoned to your employers room," she informed him.
Cassandra spoke in a soft hypnotic voice and repeated herself a few times. Slowly Lance began to vanish as Lana took control. When she judged that he was ready she had him go outside and come in again. Cassandra noted that he did not tetter as he walked. Once in the hallway he knocked on the door and was told to enter.
Lance noticed that Cassandra was wearing a man's smoking jacket and silk lounging pants. Her long hair had been slicked back and tied in a ponytail, she looked quite like a man.
"You summoned me, Master?" Lana asked.
"Yes I did. There is an issue we must address," Cassandra answered.
"What issue is that?"
"The fact that you have been drinking on the job again. You promised me that it would never happen again," Cassandra responded.
"I have no excuse," Lana responded.
"You will have to be punished," Cassandra informed her.
"As you see fit," Lana replied.
Lana was told to approach her Master. As soon as she was standing in front of her chair Cassandra reached out and took hold of her wrist. With a slght pull Lana found herself face down across her Cassandra lap. She felt her short skirt and petticoat being flipped up and exposing her panty covered butt.
Lana felt the skirt and petticoat being held flat against her lower back. A second later Cassandra's hand made contact with her butt cheeks.
"Bad girl," Cassandra said bringing her hand down again.
"Master, please. That hurts," Lana whimpered.
"Good. Maybe this lesson will sink in," Cassandra replied.
Over and over Cassandra hand made contact with Lana's silk covered bottom. The reflection in the mirror showed a cute girl in a French maid uniform being spanked. Cassandra grew hotter with every whimper that escaped Lana's lips. Finally she stopped and allowed Lana to stand up.
"Straighten your skirt, " Cassandra ordered.
Lana quickly smoothed her skirt.
"Will that be all, Master? Lana inquired.
"Hardly. Spanking you has gotten me aroused," Cassandra replied.
Lana was grabbed by the wrist and pulled toward the bed.
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<a href="https://www.lushstories.com/stories/crossdressing/taking-that-first-step-part-4.aspx">Taking That First Step. Part 4</a>