Becoming Cassie Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Oh no, did I leave her bra out on the bed? Did her nightie fall off the bathroom door? I was dying a thousand deaths. I thought I was so careful.

As I walked out of the living room, I realized she was in the kitchen...that was a relief. With her hands on her hips she said in a bit of a stern voice..."Who did this?"

"Did what?" I asked nervously.

"Straightened up my kitchen, that's what."

I looked down at my feet and said, "I did. After my snack, I just felt like I was at home and cleaned up a bit. I know you and Mr. Jones were running late, that's all. I hope I didn't offend you."

She then smiled and laughed, "I'm just teasing you. I love it. When I first walked in, it looked so nice, but I wasn't sure why. But I knew something looked different."

"You had me going there Mrs. Warren. I really thought you were upset."

"Me? For cleaning up my kitchen? You were so sweet to do it and I really appreciate it...Do you do laundry as well?"

"Ummm, I can but..."

"Just kidding again. I guess we had a little too much fun tonight when we were out. I'm just in one of those moods."

She handed me the money and actually gave me a little thank you hug.

++++++++++++++++++++++++++++++++++

During the summer, I babysat for them a total of five times! This was getting to be a routine. I also began to have more of a rapport with them. I would always compliment them both on how nice they looked. I'd asked them where they were going or what it was like when they returned. I think they liked me as well.

There was even one time when Mrs. Warren was there alone with Benjamin and she was catching up with her husband at an office event. As I was playing with Benjamin she popped out and asked me if I liked a certain outfit she had on. I told her it looked nice but maybe a dress that was a little longer would be better for an office function.

She chuckled and said, "I was thinking the same thing. We're alike, you and me."

I almost suggested to her a different one from her closet, but I bit my tongue at the last second. True to form she came out with the longer cobalt blue dress I was thinking about and it looked perfect. I wanted to say, "And it looks so much better on you than me", but kept my comments to "That looks perfect for this evening."

"Would you be a dear and zip me up? It's the only thing I don't like about this dress."

I tried to feign embarrassment but I walked over, held the fabric just below the zipper and pulled it up nice and gently. She smiled and said, "Thank you. You did that like a true gentleman."

At each time babysitting I felt more and more comfortable with the surroundings. I now knew that only two or three pair of her 20 pairs of heels would fit me because those had an open back and would just slide on. And I did not need to paw through all her bras and panties because I had several favorites that fit me perfectly.

And nighties, I had a couple of babydolls that always worked well because they were short and frequently had that split front so I would never get them messy. Plus, she always kept them hanging on the bathroom door for me. How cool was that?

But my most fun was still going through her closet and trying on her dresses. One thing to say, she liked them short, or at least above the knee. They looked awesome on her especially when she slipped on her heels just before stepping out the door. I always waited for that moment.

On one of my closet excursions I also found a wig in one of her boxes in the back of their closet. It was a shoulder length auburn wig, somewhat similar in color to Mrs. Warren's but straighter and a tad longer.

I had never had a wig on so finding this was huge. I loved the feel of it on, especially at the end of the night when I would put on a babydoll nightie and could feel the soft hair on my shoulders. Girls are so lucky!

It was a summer to remember. I could not wait until the fall!

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
EnjoyBothEnjoyBothover 4 years ago
Rediscovered

I had actually read a few of this series when I first joined literotica and am glad to have run across them again. I will enjoy all of the series }; )

dacoach44dacoach44almost 9 years ago
A start

Nice beginning to a young boys' start. I do hope that as this develops he gets into a 3 way with this cute couple.

zetjester1zetjester1almost 9 years ago
Excellent

Really enjoyed it, look forward to reading more, thanks very much xx

AnonymousAnonymousabout 9 years ago
Good start

I hope you finish this one.

DaveXX80DaveXX80about 9 years ago
Good Story

An enjoyable read. Hope you write some more.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
How I Became a Cheerleader Guy changes schools, life and sex to fit in.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Changing Room Prank Mark and Greg help me discover myself with a harmless prank.in Transgender & Crossdressers
More Stories