Fantasy Island – The Cheerleader

I must admit after my last trip to Fantasy Island I have been putting off another visit. It has been made very clear that my Mistress was dropping me off at the Fantasy Island Ferry today whether I wanted to or not. So – I got on the boat with my normal trepidation and fear. I sat quietly on the ferry boat trip and when we arrived I trudged up the ramp.

The Mistress of Fantasy Island was her usual happy self and was glowing as always. She was excited and told me that I was a sight for sore eyes. She told me I was just in time to fix a big problem she had.

Today was the big game with our rival and that one one of the cheerleaders had just hurt herself. She told me that I was perfect to be her newest cheerleader. I was shocked and started to step backwards.

She looked at me sternly, told me to stop and before I could say anything several of her assistants appeared and led me to the cheerleaders locker room.

I was led into a den of femininity getting ready for the big game. As I was introduced the other girls giggled and smiled and yelled a big yes – that I could be their sissy cheerleader. After all this was the Sissy Institute, a College for girls, boys and of course sissies. I would be their first sissy cheerleader. I was mortified.

Before I could complain, they got very excited and grabbed me telling me they would make me the most feminine pretiest cheerleader ever. I was blushing pink with humiliation which got them even more excited.

First came the pink feminine nail and toe polish. (The colors of the Institute were pink and blue). Only pink for a sissy.


As I stood there with pink nails and toes I was so humiliated

Next – they helped me with my makeup – and it got even more embarrassing.

Then the cheerleaders little logo. Of course theirs were dainty and feminine. Mine was big and everyone would know I was a sissy cheerleader.


Then came the complete cheerleader’s uniform. The Cheerleader Uniform always looked so pretty on the girls. I just looked liked a big sissy. I was particularly humiliated by the pink ruffled panties they put on me. I, of course, was made to put on a pink bra fully stuffed and a sheer white blouse so that my bra showed through. The girls looked sexy, but it was so embarrassing for me. Then the pink knee-highs and they looked so good in their white sneakers. I did not understand why I had to wear pink high heels, but they told me the rookie cheerleader always had to wear them to prove herself.


I was so embarrassed as we ran out on the field. It seemed like everyone (both the girls and boys) were making fun of me and calling me a sissy.

I tried to put them out of my mind as we started to cheer. I was having so much trouble jumping and bouncing around following the other cheerleaders. I was stumbling in my high heels.

Our Team started out very good and scored first. Then as the other team was driving for a touchdown I got too close to the field and fell onto the field. The official saw me and called a penalty for me being on the field. It gave them a first down and then they scored a touchdown.

Everyone was booing me and the other cheerleaders were all yelling at me. I was so humiliated. Our team got distracted and all of sudden the other team was up by 14 points.

The cheerleaders decided it was all my fault and they told me if the other team scored more points I would be spanked on the field in front of everyone so they would know it was my fault. I was terrified. Then the worst happened. They scored.

The cheerleaders grabbed me, bent me over and exposed my Rear End. Everyone immediately noticed that my as cheek also had the cheerleader logo. The entire stadium laughed as the camera showed it on the scoreboard. Then they gave me 28 spankings as every-one cheered each whack. Even the officials called a time out to enjoy it as I cried with the spankings and the embarrassment.


The other team continued to score and the spankings continued to every-one’s enjoyment. Then as the game ended and our players had to congratulate the other team (They certainly looked mad), the cheerleaders dragged me crying to the locker room.

They laughed as they said it was all my fault and that I would have to explain it the team. They took me to the boys locker room, tied my knees and hands together and told me stand in the middle of their locker room. They were giggling as they left the room and told me I better think of a good story about how I caused them to loose. They assured me that they would be very mad and that I better be nice to them. I was terrified.


I was shaking in terror as the boys entered the room. They stopped dead in their tracks and then just smiled.

….To Be Continued…


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Dear sissy billy,

I wish to say well done on this assignment.

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