It all started about 2 weeks before graduation.

This was before I was done with high school forever!

I couldn’t wait that is until my parents told me they were going away for six months.

I would be staying with my old babysitter and current principal.

She was always really nice to me and I got out of a few tough spots in school because of her.

However, the longest I had ever stayed at her house was a weekend.

Six months there was going to be a long time.

The fact was, my parents just didn’t trust me in the house by myself for that long.

So the day they left was a school day and I went to school like it was any other day.

Everything was normal until I got a message before last period to see the principal after school.

I went to her office and she told me to sit down.

She said she just had a few more things to do then we would go home.

On the way home though I realized I didn’t have any clothes at all for the next 6 months.

Everything I had packed was still at my house.

I asked her if we could stop at my home and pick them up.

However, she said no.

She continues that it would be fine as she had some things at her house that I could wear.

This would be until this weekend and we could go shopping.

I agreed because I didn’t really have anything for summer packed anyways and it was already starting to get really hot during the day.

When we got to her house she told me to go take a nice hot shower while she prepared dinner so I did.

When I got out though I noticed my clothes were missing and called out for Mrs Peters.

She told me to come to the bedroom at the end of the hall, as that was where my clothes were.

I went down to that room and took a step back when I saw it.

It was a pink room with Hello Kitty and Care Bears all over the place.

It looked like a room for a girl of about four or six.

She told me this had been her daughter’s room before she went off to college.

This was where I’d be staying for the next 6 months.

She went over to one of the drawers and produced a pair of pink hello kitty panties for me and told me to take the towel off of my waist.

I was a little hesitant until she reminded me that there was nothing to be ashamed of.

She reminded me that she had changed my diapers until I was 4 anyway, as I was a late trainer.

When I thought about it didn’t really make a difference.

However, I did still want to dress myself at least.

However, on second thoughts I guess letting her do all the work is easier for me anyways.

Reluctantly I let her pull the panties up to my waist.

Then she went to another closet and produced a pair of white knee-high socks with little pink bows on top of them.

She told me to sit down.

She then slid them up to my legs.

She then led me to the closet where she produced a pink miniskirt and a pink hello kitty t-shirt that said the princess.

I told her in no uncertain terms

“No way am I wearing that”

I continued to ask

“Why can’t I just wear jeans and one of the normal shirts in there.”

Her reply was simply

“Because I am your guardian now and what I say goes”

“I’m telling you that this is what you’re going to be wearing it’s either this or nothing”.

So I let her pull up the miniskirt and put the shirt down over my head.

After that was all done she led me over to the vanity mirror and sat me down.

She did my make-up and tied my hair.

At that time was still halfway down my back, and blonde

Mrs Peters continued to tie it into 2 little pigtails.

During and after dinner she explained the rules to me.

She told me that I would be in her daughter’s clothes for the next 6 months.

She then taught me how to sit like a lady, how to act, and even how to talk like a lady.

She told me that I would be attending the senior dinner dance like a girl.

As well as this, she told me that this weekend, while shopping, we would be getting a formal gown for me to wear at the dance.

She continued to tell me that this week, I was to find one of my male friends to accompany me to the dance.

I told her I don’t think anyone will agree to take me but I’ll try.

So the next day at school,I was wearing pretty much the same outfit except no hello kitty on it, it just said princess.

I went up to my normal group of friends.

It took them a minute to recognize me.

The second I greeted them they all gasped with puzzled expressions on their faces.

“Roland,”

“What in heaven’s name has happened to you?” They all enquired.

I told them that according to Mrs Peters my name is now Rosey.

I continued to tell them that she was making dresses like this until my parents get back from their vacation.

I told them that I could still have a normal life, however, I would just be in different clothes.

Mind you, it is not too bad, as the skirt is really airy and feels really good during the summer.

“By the way,” I said,”

“Mrs Peters wants me to ask you guys if one of you will take me and Charlotte to the dance next week.”

My buddy Toby agreed to this.

Anything to be with Charlotte all night.

Other than the new sissy attire the rest of the week was pretty normal.

Saturday morning I was awoken pretty early by Mrs Peters so we could got shopping.

Mrs Peters purchased a lot more panties for me, a few tops, and a couple of handbags.

As well as this she bought me a few pairs of shoes.

However, the main thing was the formal dress for the dance.

it was a pink backless silk dress with 13 rows of petticoats underneath.

It was just really beautiful.

It actually made me look forward to going to the dance, even if I was to be dressed like that.

Again the rest of the week was just like any other week.

We had our final exams then off we went to graduation night.

This was to be held at Disneyland.

That day Mrs Peters took me and got me a full make-over.

My hair was streaked and styled.

I got acrylic tips put on and painted pink.

My toenails were also painted pink as well, and my make-up was done professionally.

I got home got into my dress and waited for my date Toby to pick me up.

When he finally arrived he put the corsage on my wrist and we went and got into the limo.

Amanda was already waiting for us.

When we got to the dance we gave the attendants our tickets.

Suddenly, Mrs Price came out of nowhere.

She told Toby that he had to dance with me tonight whether he wanted to or not and the same goes for me.

She continued to tell us that she would be keeping an eye on us both.

Furthermore, she told me I would get punished when we got home if I didn’t do as she told me.

I had no idea what more Mrs Peters could do to me.

She was already dressing me like her daughter, so I didn’t think there was anything else.

However, I didn’t really want to find out.

After the dance though we went and all got into the limo.

Amanda was the first to be dropped off.

Toby actually came over and sat next to me and even tried to hold my hand.

I backed away though and he just looked at me like he was mesmerized.

I reminded him that I was still a dude and I could still kick his ass and he still came closer to me.

When we got to Mrs Peters’s house he got out of the limo and led me to the doorstep.

He told me that he had a real good time tonight

I think he drank some of the spiked punch or something,

He then kissed me on the cheek and got back in the limo.

When I got inside I just went straight upstairs and took off the dress.

I was so tired and shocked I didn’t even bother putting on any jammies on and just went to bed.

The next day was graduation.

I was awoken early so I could once again get my hair and make-up done.

Then I got into this really short curve fitting dress and three-inch heels for the ceremony.

I thought it was a shame my parents had to miss this even

Even dressed like a sissy.

It was really amusing when the crowed went silent after hearing Rosy Ann’s name called, and then seeing what looked like Rosy Ann go to the stage.

After that night Mrs Peters and I went out to dinner at a nice restaurant.

Whilst having dinner she told me that Amanda, her daughter, would be returning home from college for the summer.

At that I nearly spit my food right back out.

There was no way I wanted her to see me dressed like this.

Amanda was the girl I had had a crush on since I was young.

Now she was coming back and going to see me dressed as a girl.

That night, due to all my anxiety, I actually wet the bed for the first time in about 15 years.

When I woke up I immediately changed my jammies and took the sheets off to be washed.

When Mrs Peters finally came downstairs though she asked me why I was doing laundry.

My reply was just that I wanted the sheets clean for Amanda when she got home

I then heard her go upstairs and a few minutes later came back down and just stared at me.

I wasnt sure what was going on.

Mrs Peters told me the mattress upstairs was soaking wet.

“You werent lying to me and wet the bed last night did you? she sternly asked.

I said

“No of course not”

“I haven’t done that in  years”.

That night though I woke up to find Mrs Peters standing over me.

“I knew you were lying to me last night,” She told me.

“So I waited by your bed all night until I saw it get wet.”

“Now get out of bed, at once.”

Not wanting to make Mrs Peters anymore angry, I did as I was told.

Mrs Peters immediately pulled off my wet pajama pants.

She then removed her carpet slipper.

She put me right over her knee and gave me the spanking of my life, just like she used to if I lied or misbehaved.

She let me up and put a clean pair of panties on me.

She told me to get into the spare bed and go to sleep while she put these in the laundry.

Nursing a freshly slippered bottom I did as told.

I was soon asleep

The next day when I woke up, I went and put a pair of pajama pants on before going down for breakfast.

We both had breakfast and did not speak of the previous days events.

The day continued as normal.

I went and met up with some of my friends

I didn’t want to lose touch with them just because we weren’t seeing each other every day anymore.

That night I went to get ready for bed.

Once again found Mrs Peters in my room.

However, this time she had something in her hand.

I couldn’t tell what it was at first but eventually, I realized it was a diaper.

She told me to lay on the ground.

I did as told.

I was used to it now and I didn’t want another spanking.

She took the towel around from my waist, lifted my legs up in the air and slid the diaper under my bottom and brought the front up between my legs, and tapped it tightly and snuggly.

I have to admit it did feel good to be diapered again but also very embarrassing.

She pulled the pajama bottoms up over the diaper.

She then pulled the shirt down over my head and told me to get into bed.

That night once again I wet the bed although this time it stayed dry thanks to the diaper.