Thank you to everyone who has email ( and sent me pictures! ) about my story "Humiliating Bobby" Many of you made note that I mentioned Bobby still comes over to my house every couple of weeks and because of all the interest, I thought I would give you an update of our meeting yesterday.
For those of you new to me and this story, I do recommend you go back and read the origional story. In a quick review, I am a Dom Top, Master if you will. I post a few times a year on CL, offering to make "your fantasies come true" for guys 18 - 25. Bobby was one of the replies that I accepted. Bobby is a skinny 18 year old high school senior who lives here in the same town I do. Bobby has a little physical issue, max hard his little cock is only 2 1/2 inches long. His fantasy was to be humiliated, and I think I did quite a good job of getting that done for him!
This story is my property and is not to be copied for any reason.
Humiliating Bobby: Update
With the econemy in the toilet, work was sucking so I took Friday off making it a 3 day weekend for me. I slept in and got up around 9am, kicking around my too-large-for-1-person house making a mental list of little things that needed attention.
Around 11, I was upstairs here on the computer when there was a knock at my door. I heard the lock being unlocked and someone coming in. Now this isn't rare, about 10 or so of my more favorite "trainees" have a key to my house so they can come over and in when the need arrises... I instantly began to bone up a little, knowing my well planned out day was no doubt going to take a fun twist.
Up the stairs and around the corner comes little Bobby, his pale little face blushing as we both know why he is here. As he rounds the corner he, as instructed to do every time he comes into my house, begins to remove his pants and underwear. He puts his pants on the back of the couch he has been fucked on oh so many times and comes to stand at my side.
The kid has done a very good job of maintaining the pubic shave I had origionaly given him. As I reach over with my right hand to fondle the little cock, I notice he is fully boned, all 2 1/2 inches. I get a good grip on the littlest package ever and turn him to face me.
"What are you doing here today son" I say with a smile, truely glad to see him. "Are you cutting class?"
"Yes Daddy" he responded, eyes on the floor as I flicked his micro package with my finger.
"Are you free all day?" I asked as I let go of his weiner and pulled his tee shirt up, over his head and off.
"Yes Dad, untill tonight" he said still looking at the floor, face red.
I took in the sight in front of me, at 18 there was very little chance that Bobby's physical features would ever change. Just under 100 pounds, no definition on his body at all, pale little nipples that you had to hunt to find and that tiny little cock that I made him call a weiner. I really like this kid, he is a good kid. I do the most humiliating things you can imagine to him but let someone else bother him without my permition and they will find themselves in a Hospital recovery room.
"Well come here" I said as I turned my computer chair around towards him, picked him up under the arms and sat him on my lap.
His back against my chest, I wrapped my left hand easily around him holding him close. I looked over his bony shoulder to his still hard weiner and said "you know, we should tie a string around that thing because it is hard enough to find when it's hard, but when it isn't you may loose it."
Before he could comment I reached around him with my right hand and cupped his little pea like balls and flopped his little dick around some.
"Let's see who's online" I said letting the waste of skin fall from my hand and opening my Out Personals window. I grabbed my web cam and adjusted it for a good view of his little manhood. My left hand was still holding him tight and I could feel his heart start to race. While I was opening all the windows and getting everything set he said "Please don't" and began to squirm a little in my lap.
I should have mentioned that I was just wearing a sweat shirt and my red underwear when Bobby arrived and I have no doubt that my cock knew it was Bobbys tiny little ass rubbing on it because I was begining to get pretty hard.
Everything was loaded and the feed looked great! Bobby's smooth legs were clearly visable over my much larger, much stronger legs. His shaved smooth little hard on sticking out. You could see the red cloth of my underwear under him, making him look even smaller.
The messages began flooding in and I grabbed my headphones, opened my mic and opened voice chat as I knew I could never keep up with all the incoming messages.
Most everyone thought I had a little kid on my lap..well I did, what I sould have said is most everyone thought I had a 5 year old on my lap. Word spread through cyberspace and soon we had the max viewers.
"Bobby, jack off for all the nice men" I said both to Bobby and the viewers.
"No, Please NO" he said as he turned his head and looked into my eyes, begging me not to make him do it.
"Bobby is a little shy guys" I said as I reached around and began to stroke his cock with 2 fingers.
"Believe it or not guys, he is 18" I anounced "With a dick this small he doesn't like to show it off" I said as I stopped stroking him and moved his little package around so the massive audiance could see it at evey angle.
Most believed me about his age, a few didn't ( or didn't want too ) and as I had hoped, the insults were coming over my speakers so fast they were almost on top of each other.
"Please stop Daddy" Bobby said as he looked from his image on screen into my face.
"Go ahead and show the men one of your little boy loads and we will stop" I comforted.
Slowly Bobby reached between his legs and began to stroke his own little meat. Whoopes, hollars and laughter were coming over the speakers.
Bobby's heart was racing and his face was as red as it had been in Palm Springs when the old Queen was feeling him up.
"You guys want to see more of the package" I asked than moving my cam down to show more of Bobbys skinny leges on top of mine. I moved the cam up to show his skinny upper body as I rubbed it for the viewers. Bobbys eyes were wide as I moved the image up his body, I am sure he was scared that I was going to show his face to the entire world.
"Please NO Daddy" was all Bobby could say as he jacked his little cock and watched the image up his body move up on the screen.
I stopped just below his chin and played with the nubs on his chest that are his nipples. More laughter came through the speakers as I lowered the cam back to his busy hand between his legs.
"DADDY! Is this really your boy" was offered as a question.
"Answer the nice man Bobby" I said.
"Yes sir" Bobby replied.
"Does he fuck you" was the follow up question.
Before Bobby could answer I lifted him up by the armpits and spun him around and centered him so his flat ass was now on display. I put my hand on his back and leaned him onto my shoulders so his flat ass was now sticking out toward the camera....well, as much as it could. Bobby felt my hand go between his legs and he knew what was coming next!
"Randy, Please don't, not in front of all these men" he begged moving his head so he could look into my eyes.
Now a couple of things here, he has NEVER called me by my name, it is either Sir, Dad or Daddy. All the things I have done to him or made him do with others....sometimes MANY others, he has never begged like this. This is Southern California and the weather is quite nice and warm, but his little body was shaking almost uncontrolably I guess at the thought of haveing his ass fingered while hundreds of men are watching on cam.
The other thing any of you slaves in training, submissive wanna B's or slut boys should keep in mind is IF you are with a true Dominate man, you do what he wants and then he will move on. Once you beg to not have something happen, it WILL be worse than is would have been in the first place.
Back to the shaking Bobby bent over ass out, in went my middle finger. No lube, no spit, just right up his little ass. It was about a week ago that Bobby had last stopped in so I knew he would be a little tight, but still easily could take a finger.
"OH GOD NOOOOO" Bobby screamed in both lust and overwhelming humiliation. Here was this high school kid with his ass getting fingered on cam, on display to hundreds of strangers. My speakers srackled with comments from the viewers as well as laughter. I had to block IM's because I was aftaid my computer couldn't handle the volume..
Bobby was flat out crying uncontrolably as I stuffed a second finger in his ass for the pleasure of the horny men watching. The volume of cheers was something I have never seen before as I began to fuck my 2 fingers in and out of Bobbys ass.
Those of you who have emailed me and asked qustions know that I am 47 and have been dominating boys for over 35 years. ( yes, do the math...that is right ) and I have excellant control over my body. What I didn't notice is that I was now hard as a rock, my man cock pushing hard against the red underwear I had on. On my cam feed was Bobby's little ass being expertly finger fucked and a very clear image of my own hard cock confined.
One of the viewers pointed that out over my speakers and the others then picked up on it. I had my right hand busy in Bobbys ass while my left hand was holding the crying teen in place. I have been invoilved in thousands of quite erotic scenes with hundreds of guys, but even I had to admit looking at the camera feed, this was one of the hottest. I was so turned on by it that my dick was in full leakage, making a very visable dark spot in my underwhere.
I wispered into Bobbys ear "You should have just taken it" as I pulled my fingers out of his ass and turned him around to face the camera again, little dick hard as ever. I grabbed ahold of it again, shacking it around as the laughter continued. With my other hand I removed my underwear, my own leaking cock standing out straight.
Bobby was still crying at the utter humiliation when I reached down and picked him up behind the knees. In this position his upper back wasresting on my chest, his ass was hanging down at my crotch, his upper legs angled up and as I said I was holding him under the knees. At 90 something pounds he is nothing for me to move around, I have swallowed that much cum in one night at some parties, so maneuvering him around isn't any big deal.
"What do you guys say I make the boy cum for you" I inquired.
The response was overwhelmingly positive as I am sure the viewers knew what I was going to do, but Bobby didn't have a clue yet.
Still holding the crying figure I sat back down in my chair sliding forward a bit. The second I began lowering Bobby he knew what I had in mind and began screaming "No, No" and struggling. In the position we were in it was a bit of a challenge maintaining control of his body but I did lower him down enough so the tip of my man sized cock entered his recently fingered hole.
Had he done as he was told, I would have entered him slowily. Instead, once I was far enough into him I simply let go of his legs and his slid nicely all the way down my cock to my balls. Bobby let out a scream that would turn milk sour. I had fucked him enough ( and had let others fuck him enough ) I am sure it was not from pain. Although I am sure is wasn't all that comfortable to have a dry cock slammed into him. No, I am sure it was the humiliation of being force fucked on cam in front of hundreds of strangers.
Not one to miss an oppertunity I said "Bobby adjust the camera for all the nice men." The still crying boy put his hand over the camera, turning the feed to black for the viewers.
"Bobby, these men all want to see you cum and you know you always cum when you are fucked. Remember in Palm Springs when you came so many times when those men fucked you" I reminded the boy to further his embarassment. Now, take your hand off the camera and adjust it so these men can see my Daddy dick up your little ass and so they can see your little cock spurt."
I humpped into Bobbys ass as I said that, causing him to have to catch his breath.
Slowly Bobby took his hand away from the camera and I guided him in it's movements to get the best angle. All outloud so the watchers could hear that I was making him manipulate his own humiliation.
Once he had the angle right, the visual was quite good! You could clearly see Bobby's hard little cock with just the hint of pre-cum on the tip. I had spread his legs nice and wide and there was a clear view of my cock burried in the tight ass, my full balls just below and resting on the chair.
"Bobby, tell the men what is in your ass"
"sniffle...sniffle...your cock" He said no longer crying hystericaly.
"Yes son, thats right. Tell the men how often my cock gets in your ass" I forced him on.
"Every week" he said dropping his head down with the admition.
I went on to make Bobby confess to the watching crowd that I never call him to come over, that he comes over on his own to get fucked. I made him tell the crowd that he comes almost everytime he gets fucked without even touching his cock. I had to force him to tell them some of the stories he had told me about how crewel the other kids were to him when he was younger. I made him describe how little his cock and balls were. I made him tell all the men how he couldn't shoot cum like real men but rather how his very small loads kind of just came out. His crying fit had passed and he just sat on my cock answering the questions I gave him. After everything I had put him through in the past months, he was at last 100% broken, and 100% my toy.
All this time my rod was shoved up his ass but I was only occasionaly pumping into him. Bobby has amazing ass muscles and was milking my cock all on his own.
"Let's show these men the little load your little cock puts out" I said to him as I began to pich the nubby little nipples on his chest.
Bobby braced for the frucking he was about to get and when it didn't come he turned to look at me with questioning eyes. I said for the benifit of the "no more viewers allowed" crowd, "Now Bobby you know better. I have the man cock and you don't so it is your job to get me off"
I wasn't sure Bobby would pick up on what I was telling him so I gently lifted him under the arm pits and then relaxed the lift. Bobby was still looking at me and as I did this he got the most perfectly wicked smile on his face.
"OK Daddy" he said. His eyes were gleaming for the first time in the months I have known him and I don't think anything was going to wipe that evil grin off of his face! After all I had put this kid through, he not only turned the corner, he ran down the street...and I kinew he as mine for as long as I want him!
He turned his head back around and put his skinny hands on the arms of the chair we were in. He used his arms to lift himself up and began to fuck himself on my cock like a bitch in heat. This kid rode my cock like few ever have and even with all the control I have I was having trouble not shooting in his ass after just a few minutes. I am glad I am in pretty good shape but even then I had to hang onto the chair because of the ride.
His eyes were closed and he didn't notice that I had adjusted the aspect of my camera so now the viewers hot only had a good view of my big cock slipping in and out of him, his little hard cock, but a full view of his face as he rode me.
Those watching the event who had voice were going insane. They were screaming "Oh Fuck, Oh Fuck" and yelling that they were coming, etc. Bobby was hammering his entire body down on my fat cock riding me hard and I wispered in his ear " Hear those men moaning and cumming boy? They are cumming because of you!"
The noise coming out of his throat was amazing. It was truely an animal growl and he got louder he more he slammed his ass onto my cock.
That was all it took for his little brain to overload and he bagan shooting....yup, my boy SHOT cum out of his little dick. I watched as 3 distinct small loads shot out of his little weiner and splashed just above his belly button. Quite a distance for him with that little cock!. Bobby screamed when he came " AAAHHHHHGGGG.....FUCK, FUCK, FUCK....AAAAHHHHHGGGG" As he began to unload his ass muscles tightened down on my cock and in that instand I began to fill his ass with 8 or 9 loads of my man cream.
We were both breathless and my hard cock was still in his ass and he was out of control. He was now lifting himself high enough so only the tip of my dick was in him then he let go and fell hard onto my crotch so that my just slightly softening cock was balls deep in him. The amazing thing to me was that this non muscled teen was doing this in rapid fire sucession.
Finally I had to reach down on his up stroke and pull my dick out of his warm hole. I was afraid that he might accidently pull up to far and my dick would pop out then on the downstroke do some damage! As I pulled out I put both of my arms around him and held him tight. Even then he was still humping is body up and down.
"Slow down little man, slow down" I said to him as his breathing began to slow and he stopped pumping his body up and down.
I had moved my face around to look into his as he calmed down and opened his eyes. The first thing he saw was our images on screen now including his face, his identity now out in cyberspace. He turned to face me and I braced for more tears but was surprised when he leaned in and gave me a peck on the cheek.
"Thanks Dad" he said with that grin on his face that I hoped I was able to see more and more.
I became more aware of the voices on the speakers, most claiming that was hot, do it again, etc.
"Thanks for watching guys, I have to get the boy cleaned up" I said as I cut the cam feed and closed out the site.
I wrapped my arms around him again and said "We need to get you cleaned up son, your leaking on me." I stood him up off of my lap and we headed off for the shower, less than an hour to spare before he had to be home.
End Update
Feedback always welcome and send a pic too, I like to know who I am talking too! My other stories are Humiliating Bobby 1 and 2 as well as Training Brad.