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I was 18 and in my senior year at high school. I was not popular, but not as unpopular as the nerds. However, I was smart, with a GPA of 4.5, and I was one of the heads of the school band. I was not jacked, but I had average muscles and stood at 6’0.
Like many high school experiences, my high school had that one dream girl that girls wanted to be and guys wanted to be with. Her name was Shelby and she was a typical dream girl. Head cheerleader, nice brown hair, blue eyes, and a gorgeous body. She had 34D breasts, stood at 5’4, and had a nice body that she kept in shape at the gym. Also, she was a huge slut, known to have slept with almost every guy on the varsity basketball team. She also had two friends, Melissa and Courtney, who were equally hot. Those three were almost always seen together. I had many masturbation sessions that included the three of them, but mainly Shelby. I was one of the guys who if you said my name, she would reply “Who”? Simply put, we were not even near the same social class.
Although she was popular, she was not totally dumb and was actually in the same AP Physics class as me. Our teacher assigned us a partner who would be our main study partners for the year. Lucky for me, I was teamed up with Shelby. She really did not care and took our partnership lightly for the first two weeks. Then, our teacher assigned us a major project that she and I had to work on together. Surprisingly, she invited me over her house on Friday after school to work on it. I accepted immediately, embarrassing myself with how quickly I said yes.
Friday came along and I couldn’t wait to be with her alone. Right before the school day ended, one kid named Robert came up to me and said “Hey, you better go to Shelby’s prepared.”
“Why,” I asked.
“Because she is known to try and make deals that involve her offering sex in exchange for the ability to do less work on her projects,” said Robert.
Keeping Robert’s words in mind, I was excited when I got to Shelby’s house at 3 PM. She opened the door, wearing a short skirt with a pink shirt that revealed her breasts bulged right through pretty well.
“Come in,” she said. “I got some stuff set up in my room upstairs.”
We started working, but after about 15 minutes, Shelby was losing interest. That’s when she proposed her deal. She offered a blow job in exchange for me doing most of the work. To make the deal more persuasive, she even said that if I was any good, she would let me have full on sex with her. I was a virgin, but even I knew that the deal (just a blow job with a chance of sex) was a rip off. However, I said yes, due to my deep desire to have her mouth around my dick.
“Alright,” she said. “Let me get a little more comfortable.”
Right in front of me she lifted her shirt and took it off, revealing her 34D breasts in a hot pink bra. Then she dropped her skirt, revealing a matching pair of pink panties. Needless to say, I was getting hard right there.
“Ok,” she said. “Take off your pants and we’ll do this.”
Almost immediately, I dropped my jeans right in front of her. I was about as excited as possible, until I saw Shelby’s reaction. She was bursting with laughter, starting at my dick.
“What’s wrong?” I asked.
“Your dick is sooooooo small” she said. “You’re the smallest guy I’ve ever seen. The sad part is, you’re rock hard too. You’re hung like a little boy and I don’t suck the little pin dicks like yours.”
I was shocked. I always knew my dick wasn’t huge, but I though of it being about average. While I was stuck in shock, she pulled out a ruler and measured my dick.
“Wow, 4 inches? That’s just plain sad. You don’t even have the girth to make up for it. Smallest dick I’ve ever had was six inches. I bet you’re a virgin too, because no girl would want that little thing in them.”
“But…you said you’d suck it,” I stuttered in an embarrassing voice.
“Sorry pin dick, but I’d rather do my share than ruin my streak of man cocks. Now sit in the corner because I want pictures.”
For reasons I couldn’t understand, I obeyed her and moved to the corner. She pulled out her camera on her phone and snapped a couple pics. To make the situation worse, she forwarded them to Melissa and Courtney, along with an invite for them to come over and see it (they were about 5 min away).
A little later, Melissa and Courtney showed up with their cover ups over their bikinis, as they had gone swimming in the indoor pool at the YMCA. When they saw me sitting in the corner, they both laughed hysterically, saying how my dick really is as small as it is in the picture.
“You actually gave this loser a blow job?” said Melissa.
“No, he isn’t man enough and his little dick probably couldn’t handle it. Watch, I bet he can’t last more than 2 minutes masturbating while we pleasure ourselves together.”
Both Melissa and Courtney agreed to take the challenge and they dropped their cover ups. I was hoping they’d drop their bikinis too, but Courtney told me that little dick men don’t get to see them completely naked. Regardless, Courtney and Melissa looked ridiculously hot, with Melissa in her red bikini and Courtney in her white one. Melissa was a bit bigger than Shelby, standing at 5’6 and a slightly bigger body. However, she was still gorgeous and her breasts were almost the same size as Shelby. Meanwhile, Courtney was the same height as Melissa, but with the biggest breasts of them all and nice blonde hair.
“Ok loser, get your two fingers ready to jack your pathetic dick” said Shelby. “Two minutes starting….now.”
Right there, the three of them starting slowly making out, rubbing their hands over their beautiful, smooth skin. I felt like I was in my best and worst dream at the same time. The girls were gorgeous, with Shelby in the middle, directing the action. They’re breasts were lined up and looking gorgeous as always. I desired a touch of the action, almost drooling over them. In about 20 seconds, I felt myself on edge.
“Uh-oh,” said Melissa. “I think the loser is about to cum.”
Shortly after, I shot the biggest load I’ve ever shot. It felt great and I enjoyed it as it came on my face. However, it ended quickly and I felt embarrassed. I realised that they were not pleasuring myself in the same way I wished. I was being humiliated by them, with every bit of manhood being stripped away from me. I felt helpless, with my limp dick getting softer.
“Wave goodbye to the loser dick girls,” said Shelby. “Looks like it’s a solid 2 inches now”.
The girls playfully waved goodbye to my dick. It was slowly getting soft, to about two inches. Courtney started calling me “2 inchy” and all the girls joined in. I couldn’t take the humiliation and tried to escape, but the girls stepped in my way.
“Oh no,” said Shelby. “We aren’t done with you yet. Be a good boy and move back in the corner.”
I tried to escape, but the three, very fit girls overpowered me and forced me back in the corner. Shelby grabbed a chair and taped me down with tape as Melissa and Courtney held me down. I felt so weak because I couldn’t even escape when it was just Melissa and Courtney holding me down. Their strength surprised me and I eventually gave up resisting. Little did I know was that Courtney had a video camera in her purse and took it out.
“Now little dick,” said Courtney. “You’re going to sing a little song for us about your pathetic excuse of a dick. Make it interesting and put in some great effort. Otherwise, these pictures of your dick are going out to everyone in our school.”
With no hope to escape, I gave in and tried to think of a song.
“I’m a little dick man, here’s my dick. Small, pathetic, with no hope of girls. When I get lonely, I wank it off. But it only makes me morreeeeee of a loseerrrrr…”
When I was done, the girls were laughing hysterically on the floor. I blushed bright red and could not look up. I never felt so pathetic in my life. While I was feeling shameful, the girls were whispering something to each other. Then Shelby spoke up.
“Ok loser, you’re free to go. However you will be back in this corner at 2 PM tomorrow. We have a little surprise planned for you. If you don’t come, these pictures and video will be public to all.”
I woke up Saturday morning and knew instantly that I had no choice but to go back to Shelby’s house. I couldn’t risk the humiliation the video and pictures would bring, and Shelby could complain, saying I refused to help with the project.
So I treated the day normally and then left for Shelby’s house a little before two. When I got there, Melissa opened the door for me with a huge grin.”
“Hey there loser. Come on in and get in your corner. Shelby and Courtney will join us shortly.”
I walked up to Shelby’s room and moved slowly to the corner. I felt embarrassed when I saw a sign saying “Little dicks here” with an arrow pointing down at the corner. Yet I walked over and stood their, waiting.
A couple minutes later, Shelby, Courtney, and Melissa all walked in, fully dressed in their cheerleading outfits.
“Sorry loser,” said Shelby. “Courtney and I had to go make sure you’re surprise could still come after our cheerleading practice. It’ll be here shortly. Until then, why don’t you get you little pee-pee hard for us? It shouldn’t take you very long.”
I stripped down naked. Shelby was right. It only took me about 15 seconds to get it fully hard. Melissa kept teasing me, holding up her pinky and making a jacking off motion with two fingers. Despite the embarrassment, a part of me enjoyed it. Melissa looked even more gorgeous in her cheerleading outfit and her dark hair back in a ponytail. She was equal to Shelby right now in terms of how hot she looked. Then Shelby broke in with some news.
“You’re surprise won’t be here for a few more minutes so we’re going to have a little fun. Melissa is going to start slowly stroking you’re pin dick with one finger. Just to see how big of a loser you are, we’re going to time how long it takes for you to reach the edge of cumming. If you can last at least a minute, we’ll let you cum. But if we see you nearing the edge before that, Melissa will take her finger off you immediately and you don’t get to cum. Just to make sure you don’t get tempted to finish yourself, we’re taping your hands back.”
I obeyed, hypnotized by the girls dominance over me. After they taped me down, they placed bets on how long I’d last. Courtney gave me some sympathy and said 45 seconds, just short of the goal. Shelby said 30 seconds. Melissa gave me 15 seconds.
Melissa started stroking my already rock hard 4-incher. The thought of the beautiful Melissa “jerking” me off got me mad hard. Seeing her do it with her beautiful hands and pink fingernails made me get to the edge really fast. Melissa, seeing this, told Shelby to stop and took her hands off. I had failed.
“Wow,” said Shelby. “Exactly 15 seconds….what a looooosssseeeerrrr. Nice bet Melissa, you got it exactly right.”
A minute later, the doorbell rang. Shelby ran to answer it, saying my surprise was here early. Shortly after, she entered the room, with her ex-boyfriend Jonathan.
Johnathan was 6’5, with huge muscles and a rocking 8 pack. Simply put, he was a much more impressive sight than me. When we were younger, he was the school bully. Despite me not being as unpopular as the nerds, he hated me and gave me wedgies and beef stew whenever no adults were around. When he saw me, a huge grin came across his face.
“WOW, now I see what you’re talking about. Loser’s got no manhood in him.”
Shelby smiled, and said, “Now loser, I brought John here to show you what a real man looks like.” She looked to the other two girls and said, “And you two can now see why he was one of my favorite dudes in bed.”
John started to unzip his pants. Then he pushed them down and smiled in his pride. Melissa and Courtney were wide eyed, and even I could not believe it. His dick was giant, like looking at a long sausage. Shelby was also smiling proudly.
“Seven inches in case you’re wondering. And unlike you little man, he isn’t even hard yet. Gets to about 9 inches when he is. Anyways, John is going to show you a real man fucks three girls at once. Furthermore, to make sure you don’t try to wack yourself off, we’re going to lock you up in this little dick cage.”
Before I could do anything, Courtney snuck up on me and locked my little dick up. Now not only was I going to be humiliated, but I couldn’t even pleasure myself. As a result, I simply sat down and got ready to watch.
All three girls undressed themselves, this time to full nakedness. All their breasts and pussies were exposed, and I couldn’t help but stare in awe. They were like goddesses in their beauty, and I was their pathetic servant.
Melissa saw this and said, “Enjoy it, loser. This is as close as you’ll ever get to the real thing.”
Once naked, they hoped in bed, followed by John. Melissa and Courtney were excited, as they were anxious to try out John’s huge cock. He made out with Shelby, while Melissa and Courtney made out together. Then he switched to Melissa and Shelby went with Courtney. Once ready, all three kneeled down near John’s cock and started to jack him off. With their small, girly hands, they could TRIPLE fist him. Then they put on fresh red lipstick and switched off sucking John’s monster cock.
Meanwhile, I was literally hypnotized. I could not take my eyes off the sight of the girls beautiful faces giving head to John’s 9-incher. My dick was getting rock hard, but pain started to come in soon enough. The lock was squeezing his balls so tightly that it took away some of the satisfaction of the sight.
After a nice, long session of cock sucking, they got ready to fuck. John slid his dick into Shelby’s pussy and started fucking her nice and hard. Meanwhile, he was fingering Courtney while Melissa fingered herself. Shelby moaned loudly.
“OHHHHHHH YESSSSS!!!! FUCK ME YOU STUD!!!!! DO IT! DO IT! OHHHHH YESSSSSSS!!!
Then she looked at me and said:
“FUCKING LOSER. YOU’RE JUST A PATHETIC PIECE OF SHIT, SITTING THERE WHILE A REAL MAN FUCKS ME. YOU’LL NEVER GET ANY PUSSY!!!!”
After a few more minutes, John switched to Melissa. I was astonished by the sight and couldn’t stop looking. She moaned even more loudly, having never experienced John’s cock.
“OH MY GOD HE’S SOOOO BIG! YES YES YES! OHHHHHHHHHHHHH!”
Then, like Shelby, she looked at me and said:
“YOU DON’T DESERVE TO LICK THE GROUND WE WALK ON. YOU’RE TINY DICK IS THE MOST PATHETIC EXCUSE OF A COCK I HAVE EVER SEEN! HAVE FUN JACKING OFF FOR THE REST OF YOUR LIFE!”
Once John was finished with Melissa, he went to Courtney. As impossible as it seemed, she was moaning even louder than Melissa.
“OHHHHHHHHHHH GOD PLEASE! OHHHHHHHHHHH! SOOOOOOO BIGGGG!!!!!! I’M GONNA CUM I’M GONNA CUM!!!!!”
And indeed, she did cum. Instead of verbally insulting me, she just laughed and held up her pinky.
While John switched back to Shelby, Courtney came over and unlocked my cock, saying I could jack my dick with two fingers.
Over from the bed, Melissa said “I bet he comes twice before John does!”
I started jacking off and came in about 10 seconds. My dick was too hard and too filled with cum at that point. Then Melissa tossed me her bra and told me that I could have the honor of spilling my loser cum in her bra cup. This thought got me more excited, and about two minutes after the first load, I came again.
“What a loser!” said Shelby. “Came twice before a real man who was fucking 3 hot babes!”
A minute later, John said he was about to cum. All three girls lined up at his cock, ready for his load. Then he shot the biggest load I had ever seen over all three of the girls’ faces. It was incredibly hot.
After they were done, Shelby called me over and I obeyed immediately. However, I was filled with horror when she told me why she called me over.
“Now loser, clean him up with your mouth. Do it or these pictures are going to everyone in school.”
With no hope left, I licked the little cum that stayed on him. I was even more horrified when I realized that Shelby had snapped a picture of me doing it. I begged her to delete it but she just said:
“You’re done now loser. Go home and wank off thinking of this experience.”
I walked into school and everyone was laughing or looking at me strangely. I knew why immediately.