Teddy's Humiliation Part Two

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Status: In Progress  |  Genre: General Erotica  |  House: The Humiliation Board

Teddy's humiliation continues, as the game is brought into his home. He is also forced to entertain at a party, much to his totally embarrassment.

Teddy's Humiliation Part Two by dale10

I telephoned Teddy at home.  I made sure to call 
when his family would be having dinner. His father answered the phone. 
 I asked," It TD there?" 
His father sounded annoyed. 
"Do you mean Teddy?" 
"Oh yeah, I guess so...we call him TD .  Oh, and 
that's not short for Teddy either." 

"Well. we don't appreciate you calling during our 
family dinner.   Ted... it’s for you. Make it quick." 

When I heard his mellow fragile teenage boy voice, 
I threw and instant boner.  "Hello...This is Ted."

"Ted my little dicked friend."  I heard him hold 
his breath on the other end of the phone. 

"Eh... what do you want? " He said, trying to 
sound casual  but unable to hide the fear.

"First of all, I want you to be polite.  Secondly, 
I want you to glance out your front window. You see that blue car out 
there. Well that's one of my friends with a high-powered camera.  The 
angle is perfect, Teddy. He can see right into your dining room.  Now 
while you are talking to me, I want you to turn your back on your 
family, and then, lower your zipper and take out your pathetic dick 
and balls." 
He tried to sound at ease. He even gave a little 
laugh.  "I... eh.. .I can't do that now." 

"Sure you can, TD. You don't want to make me angry. 
Otherwise that man in the car will come right up to your house and 
deliver an envelope of pictures of you standing bare assed naked and 
shitting and pissing and doing all kinds of naughty things.

” Now, you don’t want that, so turn your back on your family 
and take out your dick and balls. " 
I waited for a few seconds. "Well, Cuntface?"

"I did it Sir, I took them out." 

"Then stand still so my man in the car can take a 
picture with your family in the background.  Do you have your napkin 
with you?"

"Ahh..yeah...can I please put my… can I please zip 
up now?" 
“Not yet. Hold your napkin in front of your little 
baby pecker and then, turn around and face your family." 

He whispered, "Please, my grandma is here."

'Oh, I'll bet her clit is bigger than your dick.  Now 
fucking turn around so my man can take a photo."

I heard Ted's father in the background, "Get a move on 
Ted, your dinner is waiting."

"OK,” he shouted to his dad. Then to me   "Ok, I did 
it. Please let me go now." 

"Now Listen to me Ted.  I called to tell you we 
changed the meeting to Saturday instead of Wednesday. More 
guys can attend to have some fun with you, and most guys your age are out 
fucking their girls on Saturday Night, since you can’t fuck with 
that miserable pricklet of yours, you won’t feel so bad if you have a 
nice party of ours to come to.  You know where to come, and 
Ted, bring along one of your little brother's jock straps, an 
unwashed one. " 

"I don't know if I can. How can I get one?"

"TED..."  his father shouted.

"I don’t give a fuck how. Ask him for one. Beg him for 
one. Steal one. Break into his gym locker. What the fuck do I 
care, but do it.  Now, hang up the phone and go back to finish your 
dinner. My man in the car will keep taking pics, so make sure you 
don’t put your prick away all during dinner. Keep that napkin over 
your cock, although a postage stamp would be just as good." I hung 
Breaking an eighteen year old boy because of his small 
dick size was as much fun as I have ever had. On Thursday, I had one of 
my guys swing by his house in the morning, just before he left for 
school, and place a photo of him bare assed and shitting, on his 
windshield behind the wiper blade. On the back of the photo I had 
scrawled, "Don’t be late for the party Saturday, and bring the 
He was early. Angry and scared and shy and pouty and 
perfect.  I took him to an upstairs bedroom of the mansion where the 
party was to be held.  "Now Ted, I want you to strip naked and then 
put on your brother’s tiny jockstrap. My, my, that is a baby pisser 
pouch, isn’t it? Just right for you. Then, when everyone is here, you 
will make your grand entrance down the staircase, looking real cute."

"I can't do this, Sir, I just can't. I was a fucking wreck 
all week. I even flunked a test. The first time in four 
years. Please!" 
I took his handsome face in my hands. 'Now,  now, 
now... none of that TD. We've been over all of this before. You just 
do what you are told to do for six months, and you're home free.  Oh 
by the way, from now on, tell everyone your name is TD. They will 
think it’s short for Teddy, but we all know it’s for Tiny Dick." 

He stripped. When he was finally totally naked and turned 
away from me, so his fine young teenage ass was on full display, ass 
globes dimpled and smooth and pale, he held the very small jock in 
his hand.  " I don’t know if this will even go up over my hips,"  he 
said rather pathetically in a hollow, lost voice.

"Wait. Wait, before you do that TD, turn around so I can see 
that clit of yours again. " 

I could see his legs shake. He turned around to face me.
'Holy Shit,I had forgotten just how small it is. That is 
amazing. You should go in the Guinness Book of Records or something. I 
fucking can't believe it. An eighteen-year old boy with the dick of a 
four-year old. Fuck it TD, I don’t know how you can call yourself a 
boy at all.  I mean, Jesus, a dick is what makes a guy a guy, and you 
fucking haven't got one. You just got a little nub. "

He stood there bare assed naked, tears forming in his beautiful 
young eyes.  'It's not my fault. What am I supposed to do about it?"

"There isn’t much you can do, I guess, except get used to the fact 
that you are a freak.  Maybe, what you should do is resign yourself to 
the fact that instead of ever fucking girls, you should provide laughs 
to real man. Let them enjoy what a loser you are. Have you thought 
about what I said, about how you might be happier as a queer?"

'I'm not queer sir. I like girls."

"I know, but that's bound to be a total loss for you. You'll just 
get made fun of, whereas with guys, sure they'll make fun of your 
dicklet, but then you could blow them and take it up the ass, and 
probably impress them with your boycunt skills. At least if you were a 
good assfuck, there would be some respect for you. " 

Teddy frowned, made fists and stood his ground.  " I am not 
queer, and I never will be." 

"Suit yourself kiddo, suit yourself. Okay, get into that 
peanut pouch and wait here until we call you." 

We made him wait up in that bedroom for two 
hours. Imagine what a naked eighteen year old boy thinks about while he 
sits there on the edge of a bed, knowing that a dozen or more men are 
soon going to be looking at him bare assed and laughing at the size of 
his dick. Imagine what goes through his head. he must have been 
freaking out.  Can you imagine the low level of his self-esteem? 
Finally, we sent one of the guys up to call him down. We 
had the lights dimmed except for the stairway light, and some real 
raunchy music on. The guys cheered and whistled as the almost naked 
boy came down the stairs. He walked slowly and unsteadily on his big 
bare feet, like he might collapse any minute.  He chewed his nice 
full lower lip.  His fine young pink titties were hard.  And the jock 
strap was perfect, so small it barely came up below the prick 
root, but still there was little or no telltale boy dick lump. He was 
almost flat, like a fucking cunt in a thong. 
"Ain't she pretty?"  one of the guys yelled, and everyone 
"Look at her cunt," Art shouted and got applause. 
Ted's mouth twitched like he would start bawling any 
second. .I directed him to stand three steps from the bottom, where the 
stairway curved, giving him a little show platform 
'Here's our favorite high school star now…TD. TD, tell the 
guys here what your name TD stands for." 

His lower lip trembled. He made fists and then relaxed them, 
trying to maintain control of himself.   "Tiny Dick."  he said 
finally, quietly. 

"Louder TD. There are twenty-four guys here and the ones in the 
back can't hear."

"TINY DICK"  he said louder and received catcalls and hoots in 

Now, tears rolled down his sweet young face.  'Cause my cock is 

"Right, but no one has to find that out, as long as you are a 
good boy and let us play with you...right?"

"Right Sir." he said, his toes curling on the stair carpet. 
"So, how about dancing to the music for us, and then stripping 
off that pathetic little pouch and giving us a nice glimpse of the 
"Wait, wait," one dude yelled, 'let me get out my magnifying 
glass first." 

Crying pretty hard, Teddy danced and stripped. Like the 
previous week, there was lots of laughter and jocularity at the sight 
of his baby prick and marble sized balls.  We had him stand still with 
his legs spread and his hands behind his head. 
"You know Ted, you're getting hair down there. Prick 
hair, and its only making your dicklet look smaller. if we shaved off 
your pubic hair, your dick might look larger." 
"No, please don't do that,." he burbled, but the guys 
outvoted him, so we got shaving cream and a razor and shaved off all 
the kids just sprouting pubic hair. His nuts were already 
hairless, and his hole was pretty smooth, but we ran a razor over 
those areas too just to make sure.  Then we looked at him again. 

"You know, Ted, I owe you an apology. Without hair down 
there, you look even more like a baby. That prick looks like a 
three-year old's dick now. He stood there like a big baby, except a 
baby with a well-toned, muscular teen body, head hanging, hair hanging 
over his cute face, crying, while guys took pictures of his hairless 
little boy prick and balls and of course of his face too.  
I put my arm around his shoulder, rubbing his soft smooth 
skin.  'You know what Ted, I'm going to give you a chance to prove to 
these guys that you are a real man after all. Not some little 
baby. Real men jerk off. So, why don’t you jerk off for us and show 
us that you got what it takes to be a man?" 

"I'm begging you, please, please, don’t make me do that. Not here 
in front of all these men, please!" 
'Maybe she can’t get a hard on,"   one guy yelled.

"Maybe she is hard, and that's all she’s got"

"Ask her to rub her pussy and she might agree."  The guys were 
getting wild. 
I lowered my hand farther over Ted's shoulder to play with one 
nipple on his nicely formed boy chest.  "You see, Ted, you don’t want 
to make these guys angry. Now spread your fine, strong young legs a 
little and beat your meat for us. Shoot a nice big load, and we 
might gain some respect for you." 

Well Teddy tried his best. For twenty minutes, he tried his 
best, but he was so scared, he couldn’t even get it hard.  My God, you 
should have seen those grown men laugh until they were 
crying, pointing at the sobbing kid and calling him names. You should 
have seen him jerking and yanking that tiny nub of meat between two 
fingers, and still the fucking thing wouldn’t respond. He choked back 
tears and cried to us that it does get hard, that it gets bigger, but 
that he was scared and embarrassed, and it wasn’t working.

"I can see him on his wedding night. ‘I'm sorry honey, it’s just 
not working.’" 

" What fucking wedding night? .Who would marry that?"   Waves of 
laughter rolled over the room.  I knew then that Teddy would never 
marry. That the scars would stay with him his entire life. And that's 
just what I wanted. That thought would give me a pleasant hard on for 
some time to come. After out fun and games, poor young handsome Ted 
would never risk trying to fuck or even date a girl.  He'd be fucking 
alone, trying to beat that thing his whole life. Unless, he broke and 
became a cocksucker and an ass boy, and that was my plan for him. 
We spent the next hour taking pictures of Ted's dick next to 
things like pencils... measuring tapes... rulers... kitchen 
utensils… coke bottles… anything to show how small it was. Then, 
some of the guys took out their huge slabs of fuckmeat, and had their 
pictures taken with the crying teen. Their big fat pricks held up next 
to his little worm… big smiles on the faces of my friends, arms 
around their young buddy, prick to pricklet.

Then, I announced coming events.   "Next week guys, to try to 
give young TD here a chance to prove himself, I am springing the one 
hundred and fifty bucks, to bring in a first-class hooker. A real nice 
looking cunt, and we will have Ted here try his hardest... (pardon the 
pun)   to fuck her. " 
Ted fell apart. His legs gave out and he crumpled there on 
the steps, burying his head in his arms.  "Nnooooooooooooo"  came 
from somewhere deep inside him. 
"Save your cum this week Teddy boy, cause next Saturday, you are 
going to be a fucking stud!" That for sure would seal the boys doom. 

Submitted: July 05, 2021

© Copyright 2022 dale10. All rights reserved.

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Add Your Comments:



This is one of the best stories I've read. Is it going to continue?

Tue, August 3rd, 2021 2:29pm

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