tagTransgender & CrossdressersTruth or Dare Sissy

Truth or Dare Sissy


It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy.

It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, and a great opportunity to catch up and have fun with friends.

On the night, it wasn't long until everyone got into a big game of truth or dare. We had all been drinking, and we were all picking dare, a recipe for disaster. After a while my friend Emma asked me, and I said dare. She said "I dare you to let Isabel put her makeup on you!"

There was no way I could refuse, and being a bit drunk I really didn't care anyway. Everyone was really excited about this dare, and it was recorded on many snapchat story's. Isabel did a very good, realistic job, and left my face looking very girly.

It was all in good fun though, and we kept drinking and playing the game as a group for longer. About an hour later many of us were absolutely smashed, and the game was getting exciting.

Next up was Isabel, "Maxy! I dare you to let me pick out some of my clothes for you to wear for the rest of the night! It'll suit your sissy makeup!" She said laughing.

This was the first mention of the word "sissy" for the night, but not the last.

She proceeded to take me up to her room, and stumbling around she picked out her slutty French maid Halloween costume. I thought it was funny, and reached to take it.

"Oh not so fast maxy! You need to go all the way!" She said laughing as she passed me black lacy panties and bra, and thigh high stockings with the matching garter belt, it must have all been a set.

I refused, causing her to push me on the bed, sit on top of me, and promise a blow job later if I did it. I was stating the night along with 7 other friends, so hastily agreed. Isabel then continued to pass me all the lingerie which I put on (with some struggle with the stockings).

I then put on the slutty dress, which barely reached the tops of my stockings. Isabel then got on her knees in front of me and slid on a white piece of fabric around my thigh while rubbing my leg all the way along.

Isabel then led me by the hand back downstairs to everyone. I was expecting large laughter, but was surprised to hear more of a collective gasp. I was even more humiliated, simply by the fact that everyone thought I was actually passable.

I hurriedly continued the game by sitting down and giving lachie a dare to do something stupid. He quickly went straight back to me, and dared me to kneel in the middle of the room with my eyes closed and my mouth open.

I knew that was too far, and quickly refused. But all of a sudden the whole room of about 20 was getting annoyed and letting me know that nobody had refused a dare all night, and that I had to do it.

So I did.

I knelt down in the middle of everyone on my stockinged knees, closed my eyes, and opened my mouth weird. I knew what could have happened, but it didn't. What did happen was close though.

As everyone in the room was recording on their snapchats (as I later found out), lachie held a banana at his groom and thrust it into my mouth, holding the back of my head onto it. He was much stronger than me, and wrapped my long hair around his hand and thrust my head back and forth on the banana, forcing me to suck it. This came to loud laughter and even some applause as everyone enjoyed what they were seeing.

Finally lachie stopped, and it was my turn again. While the game continued I went on my phone quickly and saw the many Snapchat story's of me sucking lachie's banana while wearing this outfit and makeup. The captions of these snapchats included "lol what a sissy max is", "max is lachies bitch", and "max looks like he's done this before!"

I was beyond humiliated, but in my drunk state the reality of it still had not quite set in. After another 15 minutes, I was dared by Isabel again, to let her handcuff me. I was already in deep, so just agreed and let her handcuff my hands behind my back.

She then sat by me as the game continued and whispered in my ear, "there's definitely going to be some cock-sucking tonight sissy boy", before moving away again.

I didn't know what to think about what she had said, but before I knew it, it was 12:30 and everyone was leaving. I must have taken about 10 photos with different people dressed like this as they were so keen to remember this.

I was just glad to end this night, and looked around at who was staying over at Isabel's. it was me, Isabel, Lachie, Emma, Nick, Alison, and Matt.

It wasn't long before we found our beds for the night, with me on a mattress on the floor with Isabel and Emma either side of me, and Alison on the couch behind me.

It made sense that I was put with the girls, as even though I had repeatedly asked to get changed nobody would I cuff me and allow me to get changed. The night seemed doomed as I got ready to sleep, before Isabel whispered in my ear next to me.

"Meet me in my parents room at 1:30 baby, you'll get that blowjob you were promised" she whispered.

Those words had turned my night around, and as she got up quietly at 1:15 she told me to wait 15 minutes, and not to wake the girls around me. It finally reached 1:30 as I awkwardly got up (because of my handcuffs), and went into her parents room.

It was pitch black as I walked in, and I heard somebody close the door quietly behind me. I turned around, expecting to see Isabel but was shocked to see Lachie!

Before I could react he shoved me onto my knees and forced his already hard cock into my throat. I was gagging instantly, and unable to save myself with my hands tied and his strong hands on my head.

The lights were then turned on by Matt, and I turned to see that Nick and Isabel were also sitting on the bed, with Isabel recording on her phone. "Aren't you happy sissy? Here's the blow job I promised you!" She said happily.

I could only gag in response as my head was continually pushed up and down Lachie's large 10 inch cock.

"Look sissy, if you don't want anyone to see this recording, you'll suck Lachies cock by yourself, okay?" She told me. "Matt here will even unlock your hands, if you just suck Lachie's cock by yourself."

I knew I was sucking Lachie's cock regardless tonight, so decided it would be better to have some control anyway. That was my reasoning at least, when really I was just doing it because I couldn't have anyone see that recording.

I couldn't talk with the long cock stuffed in my throat, so just nodded rigouressly until Lachie withdrew, and Matt unlocked my cuffs.

"Lick all the way up the shaft bitch, then take it in and suck it you slut" Lachie told me, "and I want eye contact the whole time".

I was in no position to disagree, and did what he said. I slowly licked all the way up his monster cock, staring into his eyes the whole time, before starting to suck it. This continued for about 10 minutes, with Lachie occasionally ordering me to suck deeper and Isabel recording. The thing I liked the least was the hungry looks on Matt and Nick's faces.

After 10 minutes I could feel Lachie start to tense, before he quickly took his cock out of my mouth and exploded all over my face. By now Isabel had walked over with her camera, ensuring she captured the best camera angle possible.

After 4 or 5 bursts of cum, I was left on my knees with my face drenched in cum as Lachie left the room.

"You're a silly sissy Maxy" Isabel started talking, "now that I have this video of you sucking Lachie off like that I own you bitch, and unless you want people to see this video you'll do what I say, ok?" She asked.

"Yes"I replied sadly, resigned to my fate.

"Yes Mistress Isabel" she forcefully stated, "you will always refer to me as Mistress bitch" she concluded.

"Yes Mistress Isabel" I responded.

"Good sissy! Now, these two lovely boys here have given me $30 each to have their way with you, and you don't really have a choice do you?" Mistress Isabel told me.

"No Mistress" I sadly replied.

"Good!, now we've already discussed this, you'll be blindfolded sissy, and one of these boys will take your mouth and the other gets your mouth, of course you won't even know who has what" Mistress Isabel told me.

What happened next was all a blur, as Mistress Isabel blindfolded me and forced me to bend over while on my knees, and to open my mouth.

I then took a cock in my mouth for the second time in 10 minutes. This one was shorter, but I could instantly tell that it was thicker as it stretched my mouth. I started sucking the cock, as I felt my dress get pulled up, and my panties pulled down. A lubed pair of fingers proceeded to prepare me, before a cock was slowly shoved into my ass. It was initially an intense pain, but as he began thrusting continuously it became more and more pleasurable.

In my drunk state I let the pleasure take over, and before I knew it I was thrusting back and forth on both cocks inside of me, all while Mistress Isabel recorded. It was the cock in my ass which erupted first, as I felt the cum drop from my ass and the cock withdraw. Shortly after the cock in my mouth exploded, as Mistress Isabel yelled "hold it in your mouth sissy!"

I held the cum in my mouth, as I heard Nick and Matt leave. Mistress Isabel then took off my blindfold and told me to get on my knees vertically. I did so dutifully, before she aimed her recording phone at my face and stated "open your mouth and swallow it all bitch".

I did what I was told as I showed all the cum to the camera and gulped it down, cringing at the taste.

"You're such a good little bitch Maxy" Mistress Isabel told me, "now I did promise you a bit of pleasure didn't I?"

I nodded, unsure what to expect.

"Well I'm not a cruel Mistress, so why don't I give you a nice handjob? It looks like that big fucking has got you close up cummimg already anyway!" She continued.

She then stroked my "small dicklet" as she called it, which exploded in her hand after 20 seconds. After losing my hormones I was even more embarrassed about what had happened, and shyly looked at the ground.

"You looked like you enjoyed that cum load before sissy, so as generous as I am, I'll allow you some more!" She said as she raised her hand to my mouth.

Mistress Isabel then just laughed as she pored my cum down my throat, before she simply got up and walked to the door.

"I own you bitch, I'm already showing this video to my friends, just pray I don't show it to anybody else, sleep well slut" she concluded as she closed the door.

So I was left there on the floor, cum covering my made-up face and long hair, wearing lingerie and a maids dress which was pulled up at my ass, where cum continued to drop out.


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by Anonymous

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by Anonymous05/11/19

Damn it

Wait this isn’t YouTube

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by Anonymous04/23/19

easy fix.

I would have just dared lachie to do everything I was dared to do. Right after the banana thing starting with that of course. That would have kept it a little more fair.

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by Anonymous03/21/19

my fantasy

I love that story I wish I was a little submissive sissy slut and made to swallow

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by 4yourpleasureiam11/26/18


I was not reluctant however this story touches me in so many ways. Love it when I had friends like these. Being one of the girls is the best

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by Anonymous09/05/18

My fantasy

I would love for that to happen to me

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