The Tutor

By Anon.

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, lovely 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, mainly Shelby.

I was one of the guys who, if you said my name to her, would reply, “Who?”

Simply put, we were not even near the same social class. Although she was popular, she was not dumb and was actually in the same AP Physics class as me. Our teacher assigned us a partner who would be our main study partner for the year. Lucky for me, I was teamed up with Shelby. She 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 to 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. 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 she would let me have full-on sex with her if I were any good. 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.”

She lifted her shirt in front of me 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. 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 excited as possible until I saw Shelby’s reaction. She was bursting with laughter, staring 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 thought it was 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. The 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.”

I obeyed her and moved to the corner for reasons I couldn’t understand. She pulled out her camera on her phone and snapped a couple of pics. To make the situation worse, she forwarded them to Melissa and Courtney and an invitation 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 laughed hysterically, saying how my dick was as small as it was in the picture.

“You 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, 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 with a slightly bigger body. However, she was still gorgeous, and her breasts were almost the same size as Shelby’s. Meanwhile, Courtney was the same height as Melissa but with the biggest breasts of them all and lovely blonde hair.

“Ok, loser, get your two fingers ready to jack your pathetic dick,” said Shelby. “Two minutes, starting now.”

The three started slowly making out, rubbing their hands over their beautiful, smooth skin. I felt like I was in my best and worst dreams simultaneously. The girls were gorgeous, with Shelby in the middle, directing the action. Their breasts were lined up and looked beautiful 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 realized that they were not pleasuring me 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 inches,” 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 into 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 lookup. I had never felt so pathetic in my life. While I was feeling shameful, the girls whispered 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 videos will be public.”

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 usually and then left for Shelby’s house a little before two. 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 there, waiting.

A couple of minutes later, Shelby, Courtney, and Melissa walked in, fully dressed in their cheerleading outfits.

“Sorry, loser,” said Shelby. “Courtney and I had to make sure you’re surprised could still come after our cheerleading practice. It’ll be here shortly. Why don’t you get your 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 surprised I won’t be here for a few more minutes, so we’ll have a little fun. Melissa will start slowly stroking your pin dick with one finger. 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 immediately take her finger off you, and you don’t get to cum. We’re taping your hands back to ensure you don’t get tempted to finish yourself.”

I obeyed, hypnotized by the girl’s dominance over me. After taped me down, they placed bets on how long I’d last. Courtney gave me some sympathy and said 45 seconds 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 fast. Melissa, seeing this, told Shelby to stop and take 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 eight pack. Simply put, he was a much more impressive sight than me. When we were younger, he was the school bully. Despite 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, “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 with 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. John will show you a real man fucks three girls at once. Furthermore, to make sure you don’t try to wack yourself off, we will 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 I would 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, 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 hopped in bed, followed by John. Melissa and Courtney were excited, 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 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 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 the pain came in soon enough. The lock was squeezing his balls so tightly that it took away some of the satisfaction of the sight.

After an excellent, 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.


Then she looked at me and said:


After a few more minutes, John switched to Melissa. I was astonished by sight and couldn’t stop looking. She moaned even more loudly, having never experienced John’s cock.


Then, like Shelby, she looked at me and said:


Once John was finished with Melissa, he went to Courtney. As impossible as it seemed, she was moaning even louder than Melissa.


And indeed, she did cum. Instead of verbally insulting me, she 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 three 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 most massive load I had ever seen over all three girls’ faces. It was incredibly hot.

After they were done, Shelby called me over, and I obeyed immediately. However, I was horrified when she told me why she had called me over.

“Now, loser, clean him up with your mouth. Do it, or these pictures are going to everyone in school.”

I licked the little cum that stayed on him with no hope left. I was 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.”

(On Monday)

I walked into school, and everyone laughed or looked at me strangely. I knew why immediately.


The End.


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Remember, even with limited editing. It doesn’t mean any possible major flaws in this story were fixed.

One comment

  • Mark

    Hi I’m pretty surprised by this stuff and I’m just hoping to wish I could meet this John guy cause I was never supper athletic, I was called a plow boy in school defensive linemen but always got in between the bullying because I was bullied and cause it wasn’t cool to me but I used to take the biggest guys and just put them on there ass that’s when people quit. I have always stuck for people and this story kinda pissed me off that they do this shit. I would love to meet these people so they don’t do this stuff, just because they are seen as perfect they have no reason to do these things.


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