Cassie Begins her New Life

My first story "It was inevidable" gives some background but not necessary to read first.

All comments and suggestions are always welcomed.

After her first sexual encounter with a man, Cassie realized she never wanted to return to her life as Charles. She started by collecting all of Charles' clothes and dropped them off at a clothing bin for charity. She dressed fairly conservatively in a blouse, jeans and sneakers with just a little makeup and her favorite wig. Satisfied that there was no going back, she went back home to deal with the first of many issues.

Her most pressing problem would be her job at the billing department at a local hospital. She couldn't fathom they would understand her transformation to Cassie. She also hated the job and although she didn't like not giving notice, she would call her boss Monday morning to resign. Fortunately she had quite a bit in her savings account which would buy her time.

Satisfied with at least making a start on her new life, she moved on to some fun stuff.

Dan was her first and only sexual experience consisting of her giving him two blowjobs. Unfortunately, he was away for a week on business and she didn't want to wait. She had registered on a web site for cross dressers and checked her email for responses.

There were a few stupid emails of one or two words, a couple of dick pics and an invitation to meet at a local bar that was frequented by cross dressers. She has just enough time to get dressed up and get an Uber to meet Mike at 9.

She had shaved earily so didn't have that chore. She glued on her new breast forms. They were expensive but she loved the way they felt so worth the price. Followed by a sexy lace bra. Then a garter belt and very sheer stockings. Just pulling up the stockings caused her cock to start getting hard. She then decided to add a pair of pantyhose, maybe strange because of the stockings but they helped to hold his cock in. Followed by a full nylon slip and black dress that she loved. Two inch heels and her favorite wig that came down to her shoulders. She had been practicing applying makeup for months and considered herself good enough to pass.

She requested an Uber and had a quick gin and tonic to calm her nerves.

Short trip to the bar and Cassie took her first steps out in her new life. She was both excited and nervous as she headed into the bar. She was about to take out her phone when a guy walked up to her and said, "hi Cassie, I'm Mike." All she could do was nod because the guy standing in front of her was incredibly handsome. tall muscular and extremely sexy. Even better looking than Dan!

He took her hand and led her to a secluded table. He got her a drink and told her that he knew it was her because she was dropped dead gorgeous. Cassie blushed and said, "right back at you."

They talked for a while and had a few more drinks. Cassie explained her decision to live full time as a woman and Mike told her it was a great idea. She caught him staring at her legs and it was Mike's turn to blush. Cassie had always felt it was her best feature and was pleased. Then she surprised herself and asked if he wanted to touch them. Mike didn't hesitate and put his hand on her thigh. Immediately Cassie loved the feeling and started getting excited. After about 5 glorious minutes of Mike rubbing up and down her thighs Cassie blurted out, "please take me to your apartment Mike."

In the Uber ride over Cassie concluded that she was already a slut and that the only variable going forward would be how slutty she would become.

None of that mattered when they got to Mike's apartment. He was a perfect gentleman getting her a drink and sitting on the couch not too close. They talked a little while longer and Mike asked if he could kiss her. Without thinking, she yelled out " it's about time!"

The next few minutes flew by as they made out like crazy with Mike rubbing her legs again. Cassie was turned on and wanted nothing more than to please Mike.

She dropped to her knees in front of him and pulled down his pants. He was completely hard and Cassie immediately began licking the head, down the shaft and his balls. Thinking about her porn viewing and the two times with Dan, she took her time licking up and down, trying to drive him crazy. From the sounds coming from Mike, Cassie knew she was doing a good job. Starting to feel powerful and loving the fact that she controlled his pleasure. Cassie kept starting and stopping and Mike was begging to finish him off. She smiled and said, "how do you like your sexy slut now?"

He screamed, " You're the best slut ever!"

Cassie took his cock in her mouth and started to bob up and down. She almost got it all in but that didn't matter. Mike exploded into her mouth and Cassie had to work to swallow it all.

They both were trying to catch their breath but had big smiles on their face. Mike recovered and gave Cassie a big kiss and telling how awesome that was. Cassie agreed but she said had to leave. Mike was dissapointed but insisted on ordering an Uber for her and getting her to promise to see him again. She had no problem with that, just needed time to plan for the following week.

To be continued....