Becoming Cassie Ch. 01

Money was hard to come by in our household. Being the oldest of four and my mom being a single mom put a real strain on our resources. Rarely did we ever have any extra money in our family to spend on things like eating out at a restaurant or going to the movies. If we wanted to do that, we had to save our own money to do it. Things were just tight. That said, almost any job was a good job to have.

I did not mind physical jobs like cutting lawns, shoveling snow, and painting. In fact, I enjoyed them because I got paid decent money and it kept me in shape. Nothing wrong with that at all.

But another job offer that kept coming up was babysitting. When I was first asked to babysit by one of my aunts, I was reluctant. I had so many questions like what to do, what to feed them, what if they cry, etc. Those things were never in my skill set. I did have younger brothers and sisters, but watching someone else's kid was different.

Still, if I could make $20 for a few hours of time watching TV and doing my homework after the kids were asleep, it could be a good night financially.

What I had not thought about was that babysitting was the perfect opportunity to crossdress.

There you have it. I was a closet crossdresser. Over all of my life, as long as I could remember, I had this desire to dress in women's clothes. And the older I got, the stronger the desire grew.

Growing up I had been slipping on some of my mom's lingerie she would leave in the bathroom, but I was getting tired of basic white. Popping on a white slip and masturbating into a sink was not the most thrilling thing to do, but for the longest of times it was all I had. And it was convenient.

I also some friends with older sisters, something I did not have. I could always find their bras and panties hanging up in the bathroom, but those times were limited to just short stints in their bathroom and never lasted all that long. Still, I loved being able to wear something other than white, if even for just a few minutes.

And I did get a chance sneak on a few things around the holidays and birthdays when visiting my aunts and cousins, but that was too few and far between. And with having only one older female cousin, I figure she'd start suspecting me if too many of her panties were either missing or used every time I visited.

With babysitting, the kids I was watching were relatively young and needed to be in bed early. The parents always told you where there would be and when they would be returning. Now before I go any further, I need to say that I realize that sneaking around and trying on other people's clothes is not right. It did make me feel guilty in my later years, but at the time, I did not feel the least bit bad about it.

I think at one time I had about four different couples I babysat for on a routine basis. The way babysitting worked was if seemed to like you, they would tell their friends and then the word would spread.

I first started babysitting for my aunt and her two boys. It was probably there that I got my start in serious crossdressing. It was like at a whole new level. I would first put the kids to bed, and put on her bras and panties, or nighties and wear them for hours! Masturbate once or twice, put everything back and get paid. It was a good gig.

But it's not her that I want to talk about. It was actually one of her good friends who suddenly needed a sitter one night that was the most fun.

My mom got the call from a Mrs. Warren on a Friday afternoon and asked if I would be available to babysit for their 4 year son Benjamin that night. She knew it was short notice but had heard so many good things about me from my aunt.

My mom readily agreed for me and let me know right away. It was summer and I had just finished a painting job and thought I could relax for the night, but I guess not.

I showered and my mom drove me over for the 6:00 start time. The Warrens were a relatively young couple and loved to go out all dressed up. That night they were getting together with some friends for a birthday party at a local restaurant and then going to a club for some dancing.

I met the Warrens and young Benjamin. Mr. Warren was a likable gentleman with very pleasant manners and very thankful I could come over on such short notice. Mrs. Warren was a striking woman with wavy shoulder length hair and she was extremely fit.

And Benjamin was someone who was extremely fun to be with. When I arrived I immediately started playing a game with him as his parents finished getting ready to leave.

Around 6:45 I got the briefing as to where they were going, how long they would be out, when they would call, when he should eat a snack when to go to bed, what his routine was, etc., etc., etc.

I have to say, they looked so good as they were heading out. Mr. Warren was wearing a nice sports jacket and slacks, and she had on a short empire style dress and heels. In my world, I was only used to seeing people "dressed up" in jeans and Tshirts so this was a nice change. You could tell that for them, going out was a big thing. Kind of like a date night.

Before I go too much further I need to describe their place. They lived in a nice apartment complex and had a simple one floor apartment. The kitchen was in the back, the living room in front as you entered, the bath in the middle with two bedrooms sandwiched in between the living room and kitchen. No running up and downstairs...all one level.

As the night progressed, things were going quite well with young Benjamin. Around 8:00 it was time for the little one to head to bed and he was a great sleeper. I checked on him and within 15 minutes he was asleep, just like his mom said.

After I checked on him I could not help but peek inside the parents' bedroom.

A relatively compact apartment (not small, but compact) meant that there was not a lot of room and that there were a lot of things left around. When I slowly opened her dresser drawers and they were just crammed full of all kinds of bras, panties and slips.

Sometimes I would babysit at homes where everything was neatly arranged in rows in the dresser drawers...or perfectly hung in the large walk in closet. But her approach was pure chaos. I knew this was going to make wearing her bras and panties that much easier because all I needed to do was put them back in the same messy draw.

And styles and colors? I never knew there were so many variations. She had lace, and satin, and items made from soft, stretchy material which was so much different than the boring cotton my mom had!

I carefully opened their closet door and there were several nighties and slips hanging from the hook on the back of the door. The cute outfit that she went out in that night was indicative of the clothes in her closet. She had great clothes! This was going to be fun place to babysit.

Being the first time there made it almost nerve racking because there was so much stuff just everywhere.

After getting a quick view of bedroom, I decided I needed to calm down and work out a strategy of sorts. It was only 8:30 and they would not be back until 11:00. Plus, I was not sure what type of a sleeper Benjamin really was.

I sat down and put the TV on, but within minutes my mind started racing again. I was simply too excited to sit so I got up to go check out the bathroom. That's where I find a lot of items when I visit other places so why not check here as well.

I was not disappointed. Hanging up in the shower were two bras, stockings, slips and several pair of panties. On the back of the door was a babydoll nightie. This was like being a kid in a candy store. I didn't have to go searching for things to try on, they were all just there for me.

I was not in any rush but I was so eager that it was all I could think of. But with the child's room right beside the bathroom, I had to be quiet and discreet. I slipped off my clothes and tried on the babydoll nightie. It was red...soft...with lace trim and matching panties. I no sooner had it on when I got a raging hard on. Heck, it was my first red nightie of my life. Of course I was excited.

On the back of the bathroom door under the nightie was a full length mirror, and for the first time I saw myself from head to toe. I was trembling with excitement.

Seriously, if I got this excited just sliding her nightie, I could only imagine what she must have felt like when she wore it for her husband. Does she put it on and primp in front of a mirror like me? Does she get aroused looking at herself? Does she gently stroke her body before meeting up with her husband? These are all the questions that ran through my mind in like 3 seconds.

Standing there I could see through the soft fabric that my nipples were already rock hard. I began rubbing them and squeezing them and that only heightened my excitement. Is this what girls experience with someone nibbling on your nipples?

I really had trouble containing myself and I never even got the panties on which was a good thing as I exploded into the sink. I kept stroking myself long and hard, feeling like I was having the biggest orgasm in the world. I did not want it to stop.

I was so hot afterwards, my entire body was quivering. This was one of the best and longest feelings I have ever had.

I very carefully cleaned up and returned the nightie to the back of the bathroom door along with the unused panties. It was time to go back to the living room and calm down.. My head was still spinning and it was barely 9:00.

I couldn't sit still so I figured it was probably a good time to grab a snack and relax, so I headed to the kitchen. Benjamin was still sleeping so that was great. I grabbed a soda and a cookie sat down at the kitchen table. I was trying to process all this and tried to figure out what to do next.

Realizing that I had almost two hours left before they were coming back, I cleaned off the table and headed into their bedroom. From one of her drawers I selected a black bra and the matching panties.

I loved her underwear!

I then selected the first three dresses in her closet, remembering the exact way they were hanging. What I liked about her clothes was that they had some stretch to them in the bodice. She was not a buxom girl, but because she seemed athletic, she had a great swimmer's back and needed that extra width up top, just like me.

I had a chance to put on a pair of her slip on heels and just loved that slightly raised look. I was not expecting to get this excited this quickly, but with every outfit brought a new level. Being such a small place I would walk around the house and catch myself in different mirrors.

It was just then that the phone rang. It was Mrs. Warren asking how everything was going.

"Well let's see Mrs. Warren, I am standing here in your black bra and panties, and wearing that cute purple dress of yours. So I think everything is just fine!"

Of course I did not actually say that but I did have trouble speaking normally because I felt I had been caught. It's amazing how that adrenaline kicks in. I was able to give them a nice report and that everything was going just fine...and the Benjamin was awesome.

"Perfect, we will see you in an hour!"

I had already designated 10PM as my Cinderella time so I hung up the dresses exactly the same way as I found them, slipped over the bathroom in her black bra and panties, and masturbated one more time. It really was not hard at all when you are looking at yourself for the first time in a full length mirror in a sexy black bra and panties.

And I still had an hour to check and recheck everything.

They arrived home and told me a little about their evening and I told them about one of the shows I watched on TV and how good Benjamin was.

We settled up, they gave me my fee and a nice tip. Mr. Warren agreed to drive me home as I had the feeling that Mrs. Warren had a little too much to drink. I felt good about that part so in case anything was out of place it might be overlooked. But I knew I was real careful. On the drive back home, Mr. Warren and I talked about Benjamin, how cool he was and of course, sports.

I could not help feel a bit self-conscious on the drive home knowing that just an hour ago I was wearing his wife's clothes, but I tried not to let it show.

He thanked me again and said we hope you'll be able to babysit again for us.

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

It was about two weeks later I got my second call to babysit for the Warrens. Apparently they liked my style and Benjamin liked me. And better yet, there was no suspicion raised at all about me wearing some of her clothes. That was always in the back of my mind.

When I arrived this time, things were a bit more chaotic. They were running a bit late so I immediately started hanging with Benjamin and let them finish getting ready.

Little did I know at the time that watching the little things, like the mom putting on her final things...the rings, jewelry, perfume and jacket, and then slipping on her heels would impact me as much as it did. I loved it.

Too often all I ever saw was someone all ready to go out. I missed all the fun it must have been shopping, putting on the make-up, deciding what clothes to wear...all with the expectation and thrill of going out and looking good.

Never really seeing that going on in my own home, but on television only, made the real life experience of watching her doing it made it something I wanted to do. I wanted to be her so bad.

So here I was again, hanging out with Benjamin and waiting for the 8:00 bedtime hour. He had a snack, played some calming games and then off to bed. After I had tucked him in I did a quick tour of the bathroom and only real change is that there were two nighties hanging on the door.

But this time was going to be different. I had already crafted out my plan of what to do in case I got the call again. My plan was basically...more clothes early on and less nighties. Her nighties were simply were simply too deadly.

Within about 15 minutes Benjamin was asleep and I already had on Mrs. Warren's pink bra and matching panties. I covered up the lingerie with my polo shirt and jeans for a few minutes just in case the little guy woke up.

With a little more time behind me, I headed into the bedroom and looked to see what dresses I wanted to wear. Tonight Mrs. Warren wore a short, flared dress, and it was real cute. I wanted to find one just like it. After a few minutes I found a similar one and I was real pleased. I carried it out into the bedroom and tried it one. Her clothes fit me sooo well. I found a pair of heels that I could slide my feet into and they gave me the lift I needed.

I just loved the look. And loved the fact they had a full length mirror in their room. I was having so much fun being her, pretending that I was dancing the night away with Mr. Warren and everyone was watching us. The mere thought of it made my nipples hard. While watching myself in the mirror, I worked on my arm movements, my walk, my demeanor, and carried on make believe conversations with my friends at the dance. It's so much fun, especially when you can fantasize about being with a perfect mate.

After we finished the night at the club, we headed to the car and he ravished me, at least in my fantasy. I pretended that he couldn't keep his hands off me. I loved the feeling of it and I could sense myself getting aroused just by the thought.

I leaned up against the wall in the bedroom and fantasized that I could feel him pressing against me. I was now breathing heavy and could barely contain myself. I placed my hands on my breasts and ran them up and down my body. This only heightened my pleasure. I told him to wait and I changed into my black nightgown hanging in the bathroom.

I was now bouncing between fantasy and reality. I quickly removed all my clothes and put on the nightie. The black babydoll had an open front and I was afraid of even trying to put on the panties. I had been so erect for so long, that when I barely even touched myself Icame into the sink with a huge load.

I needed to hold onto the sink with both hands. I was shaking and trying to come back to my senses. How can her clothes transform me so much? I ran the hot water into the sink, and with the face cloth cleaned myself up and returned the babydoll to its position on the door. I needed to recover.

It was now time to put her bedroom back in order before I went any further. I first put the bra and panties back on. It had gotten to the point where the bra and panties just felt so normal on. The immediate rush that was there at the beginning of the night was replaced with a calm. It felt just right.

I picked up her dress, hung it on the hanger the same way I found it and returned it to the closet exactly where I found it. I picked up the heels and lined them up in the closet as they were before. I checked and double checked the bedroom and bathroom and felt confident everything was in its proper place.

Checking the time, it was only 9:30. I still felt I had 30 minutes to do something safe if I wanted to. I looked around and saw a short black skirt folded on a chair by her bed so I tossed that on and went looking for a top to compliment it. I found a real cute, low scooped soft white jersey top and popped that on. Wow, not only did it feel great on but I could see the pink bra color through it. This was another good look.

All dressed I headed for the kitchen for a snack and this time I was ready for their phone call. Almost at 10 on the button, the phone rang. "Yes Mrs. Warren, Benjamin is sound asleep. I read him Paddington Bear and he drifted off before we got through 5 pages. Someday I'm going to have to read that book myself to find out what happens!"

"How is your evening going?" I asked her, " I can hear music in the background. It must be fun."

She replied, "It is, but sometimes the music is a little loud even for us. We should be home by 11PM. Is there anything you need?"

What a loaded question. "I'm good right now, thank you. I just had a soda and one of the cookies you made. They were delicious. I will see you and Mr. Warren a bit later."

With that I got up, cleaned up the table of my crumbs and moved the glass into the sink. When I did, I looked at the whole kitchen for really the first time and realized it was really messy. Not dirty, but messy.

I still had almost an hour to go so I tossed on her apron over the white top and skirt, and wiped down the table with a hot cloth and some cleaner, re-arranged the items on it, tossed out some empty soda cans from on the counter and basically straighten that up and washed that as well.

I found about 5 unwashed dishes and a few glasses and cups between the kitchen and living room. They were mostly just things that were not put away into the sink before they rushed out of the house. Some were Benjamin's and some were theirs from the quick bite they must have grabbed before they left.

There was still plenty of time left so I filled up the basin with hot water and washed the dishes and glasses and left them in the rack to dry. To be honest, I had never done this this before while dressed. To be honest even more, I had never done much of anything dressed, but I was getting to like this.

At 10:30 I returned the skirt and top and said goodnight to the pink bra and panties. I was still so exhausted from my earlier time, I figured that masturbating once was good enough for tonight. I turned the television back on and watch the baseball game until the Warren's came home.

11PM came and went. At around 11:15 they arrived. They apologized and I told them, no problem, it was a west coast ball game and I would be watching at home anyway. I updated Mr. Warren on the game as Mrs. Warren went into the back to settle up with me.

From the other room I heard Mrs. Warren say, "Matt, would you come here for a minute."