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Blackmailed into Humiliation

Brandon never thought making this bet would end with him losing. He was an avid football fan and it never occurred to him that his friend Maddie would ever pick more games right than him. She had probably never even seen a full game in her life and definitely didn't pay attention to who was good and who wasn't. With all this is mind he felt very secure in making a bet that whoever could pick more games correctly could then make the loser do one thing. No limitations were placed.

Now that he had lost, Maddie told him to come over Friday night for his punishment. It now being Friday, he stood in front of his bedroom mirror looking at his 5'10" slender self and wondering what humiliating task Maddie had planned.

Once he was dressed in his normal attire he sauntered over to her house which was only two blocks away, but still a good distance walking. Brandon had just turned 18 and he no longer needed permission to leave the house. He finally arrived at her house and knocked on the door. Maddie shortly answered and greeted him. She wore a white tank top covering her small, but not absent breasts and jean short shorts showing much of her tan slender legs. She stood 5'10" as well and was remarkably beautiful. Too beautiful to be hanging out with him.

"Please come in." she said smiling.

Brandon followed her in and she led him to her bedroom. Brandon didn't hear anybody in the house, he thought that her parents would be here as they usually were.

"Are your parents here?" he asked.

"Nope, they went out for the weekend for my dad's birthday. It will just be me and you tonight."

Brandon became rather excited at the thought of being alone with this beautiful girl. Maybe there wouldn't be an embarrassing task and she was planning on doing something he would enjoy. His question would soon be answered.

"I bet you are wondering what I have in store for you tonight. I can tell you that it will be slightly embarrassing, but if you are good and listen, then no one else will know. And maybe you will get a little reward."

Maddie said the last part very seductively. Brandon immediately figured she meant sex...hopefully she meant sex.

"OK so what is it that I have to do? Let's get this over with." Brandon sighed.

"It will sound weird, but remember if you do it then no one else needs to know."

"OK sounds good."

"I want you to take off your clothes and put your hand on your dick right now!" she said forcefully.

Brandon was getting excited about this and he quickly listened. As he took off his clothes Maddie walked over to her closet and grabbed something. She held it behind her back as she turned to Brandon.

"Now for the last part, I want you to put this in your mouth."

She held out a dildo to Brandon.

"What? I am not putting that in my mouth!" he yelled.

"You lost the bet, so you have to! Just do and we will be done. All you have to do is embarrass yourself a little bit in front of me."

"Fine."

Brandon grabbed the dildo and put it in his mouth.

"Close your eyes and suck it good. I want you to stroke yourself too."

Brandon gave her a glare, but reluctantly listened hoping he would get to be with her afterwards. Now he stood naked sucking on a dildo in front of the gorgeous girl.

*Click*

Brandon's eyes shot open and saw Maddie standing in front of him with her phone. He removed the dildo from his mouth.

"What are you doing?" he asked nervously.

"Getting some good blackmail." She responded.

"What?" said a confused Brandon.

"I have special plans for you. Ladies come on in."

"Ladies?"

The door to the bedroom burst open and 4 or 5 girls came in. They all started laughing when they saw him standing there with the dildo in his hand.

Brandon frantically spat out, "Why would you do this Maddie? What is going on?"

"I invited my friends over knowing that I would be able get you to do an embarrassing act. To answer why, it is very simple. Ever since you have known me I was always just a piece of meat. All you ever wanted was to get into my pants. Now the table will be turned in that you will be OUR piece of meat."

"This is crazy!" Brandon raged.

"Ohhh you just wait and see what we have planned for you." A devilish smile came across Maddie's face. That was when the girls grabbed him and pinned him on the bed. They withdrew rope and bound his wrists and ankles to the bedposts. He was now laid out in a X position. Despite all that was going on, Brandon could not help but be turned on. His penis began to swell and his attempts to stop it failed.

"Uh-uh that is not happening. That erection will just get in the way, but is nice to know that you are turned on by all this. Before we continue we must get rid of that." Laughed Maddie. She then turned to one of the girls. "Emily can I borrow one of your socks? I don't want to get a mess on my bed."

Emily hesitated a little. "I don't know if you want mine. I had softball practice today and these are the socks I wore."

"Even better..."

With that, Emily removed one her shoes and took off the white calf high sock. She handed it to Maddie.

"Ewww!! I can see the sweat marks and stains." She said. It was true, even Brandon could see it from his vulnerable position on the bed. Maddie approached him and slid the nasty sweat sock onto his erected penis. She began to stroke, slow at first, but she soon quickened her pace. Despite the fact he was being jacked off with a sweat sock while tied up naked, he could feel himself approaching an orgasm. Brandon began to moan and he thrusted into the sock shooting his massive load into it. She removed the sock, wiped up the remaining cum and then tossed it to the floor.

"Now that your erection is gone we can start your makeover!" chanted Maddie excitedly.

"No way! I am not going to let you dress me up." With everything else that happened to him so for, this is something he could not allow.

"You don't have a choice silly. If you don't do as we say, the video of you stroking it while sucking on a dildo will go on every social media site and be spread across the school."

Brandon realized that she was right. There was no choice, but to comply. Maddie asked Emily to remove her other sock.

"We don't need to hear your complaints anymore." Maddie took the second sweat sock and shoved it in his mouth. The sock was followed by the slap of duct tape. Brandon felt the vinegary taste settle into his mouth as he sucked on the sweat sock.

"Yummy yummy. That will be your dinner. I want that sock to be spotless when it comes out, so get to sucking. It was just as nasty as the other one."

As Brandon laid there cleaning and gagging on the disgusting sock, the girls went to work deciding on his wardrobe. After a while they blindfolded him saying they didn't want to spoil the surprise. He felt his bonds untied and he was helped from the bed.

He stood untouched for a second before feeling razors dragged across his body and once that was done, something was wrapped around his torso. It tightened around him and he heard a zipper close in the back. Maddie asked for what she called "the tube" and then went to work doing something on the back of what Brandon could only assume was a corset. Then it came to him, she was gluing it shut! Immediately afterwards he felt a hand on his recently deflated penis and it was rather violently tucked in between his legs and he felt a piece of tape applied to hold it there.

"Since you like sucking on that dick so much I have one you can keep with you at all times." Scoffed Maddie. Brandon was then bent over the bed and felt a butt plug shoved up his virgin ass. A pair of panties were then slid up his legs followed by what he could feel were stockings. The next part was a skirt and then a blouse. To finish of the wardrobe he felt heels put on his feet. The straps were buckled and he heard a click. Then the blindfold was finally taken off.

Brandon looked down at himself and quickly saw he was dressed as a schoolgirl. He was outfitted with a white blouse, plaid skirt, and white thigh high stockings. The last thing he noticed were the heels and when he saw them he screamed into his sweaty sock gag. They were lock on heels! The little locks on them could only be removed with a key! Not to mention they were at least 4" high.

"You look great!" giggled Maddie, followed by her friends chanting similar emasculating things. "Now for the make up!!"

Brandon was stood up and he instantly began to hobble due to the heels and the increasingly painful butt plug. They pushed him over to a chair and mirror, then slammed him down. This shoved the plug even farther into his already aching ass.

As they began to apply make-up, Brandon was finally able to identify all the girls who were present for the most humiliating day of his life.

First was of course was Maddie. Like he had noticed when he was at the door earlier, she was way too beautiful to be hanging out with him, but now he knew why she was. Besides her natural beauty, she was a blonde with hair that went just past her shoulders and she had a perfectly tanned body. She was one of the best soccer players at the high school they went to. She was also 18, same as Brandon and the other girls.

Second was Emily, whose repulsive sock was getting washed in his mouth. She was a 5'8" softball captain who was best known throughout the school for being a model for a magazine. In Brandon's opinion she was not as beautiful as Maddie, but that definitely doesn't mean she was ugly by any standard of the word. Her black hair was the same length as Maddie's and was equally as straight when let down. Emily's most noticeable feature was her muscular build. She was not bulky, but she had a stark definition that let others know not to mess with her. Brandon knew there was no way his 120lbs could ever go toe to toe with her. She usually only hung out with the popular crowd, which is why it was surprising to see her here. It would appear these girls were putting aside their differences for the mutual enjoyment of his embarrassment.

The third girl, who was removing the tape and sweat sock and now applying lipstick, was Taylor. She had a thin build with flowing brown hair that went a good ways past her shoulder. She was around 5"7" and was also one of the most popular girls in school, thus making him believe his theory on why they were all here. Taylor was involved in no sports, yet remained at the top of the social pyramid at school. Despite her cluelessness and lack of intelligence she would probably still do well in life just because she was pretty. Brandon hated those girls.

Paige was the next girl. She was on the cheerleading squad and Brandon had a slight crush on her ever since he first met her. Now she was dressing him in girl's clothes. Her appearance, besides downright gorgeous, was that of the usual hot brunette. Long dark hair, about 5'8", and a pristine tan. To go with her slender body were ample breasts, which ultimately helped create her appeal to the common man.

The final humiliation contributor was Maggie, the volleyball captain. She was thicker than the rest, but not necessarily fatter. Being a volleyball player had given her thicker legs and a larger torso. The fact that her breasts and ass were huge led to some thinking she was just plain fat at a glance. This was not true by any means.

These 5 girls together were participating in what could possibly be the most humiliating blackmail ever. His make-up was finally done and the ladies took a step back to admire their work. Apparently satisfied they spun him around so that he could face the mirror. What Brandon saw in the mirror was not himself, but a strikingly beautiful girl. The only reminiscence of his former self was the short hair. Maddie had a read his mind and now stood behind him holding a blonde wig.

"The boys love blondes!!" shouted Maddie with a chorus of giggles from the other girls.

She again produced the glue bottle and began covering the inside of the wig with it. Brandon no longer had the sock in his mouth so he now let them know that he did not agree with this. The girls of course didn't care. The wig was placed firmly on his head and held there for a good 10 minutes until it dried on. The schoolgirl outfit was now complete. Brandon had arrived at Maddie's house a guy with the hopes of scoring, but now he was standing as a girl with a butt plug securely shoved in his ass. He had no way of getting the heels, corset or wig off without help.

Brandon looked across the faces of the girls and could tell they were deciding what to do to him now. They huddled in the corner and discussed.

"Alright Brandon we have a deal for you. If Emily's sock is clean from when you were sucking on it then we will help you get out of the outfit and you can go home. If it isn't then you still get to go home, but the outfit stays on." Explained Maddie. "We will let Emily decide."

She walked over to the side table where the sock was a handed it to Emily. She studied the damp sweat sock and then turned to Maddie. Brandon waited anxiously for her decision, though the answer was obvious.

"Definitely not clean." She said plainly.

"Guess you're going home dressed in your best clothing! One more thing before you go."

Maddie walked to the other side of the bed and grabbed the other soiled sock of the ground. Brandon's eyes got huge when he saw the cum filled sock brought his way.

"I think you need to bring this with you and clean it. Open wide!"

She shoved the cum, sweat and dirt covered crusty sock into his mouth.

"I won't tape it in, but we will be following you in the car, so we will know if you spit it out. Now let's get you home." Maddie and the girls all had huge smiles across their faces. Brandon hung his head in shame as he hobbled outside and began his humiliating walk home knowing that this was not going to be the end of his humiliation...

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