Drilled in the rectum

Drilled in the rectum repeatedly

Sadist and AssMaster Dennis's loyal friend had agreed to meet Analboy, and convince him to come with him for a little fun. Analboy unaware that Dennis had a new
device awaiting his next victim. Analboy was gagged and was brought to his
underground dungeon, leaving him locked there to await his fate- A totally blown out, destroyed asshole.

The masked man walked slowly around him, quietly appraising his body as
he quivered with fear. "I'm Dennis," he introduced himself, his voice
barely a whisper behind the mask. "In my old life, my slave left me, and the
next bimbo I dated had the audacity to bite my cock off just because I'd forced
it into his throat. I assure you, my men fixed him, but good. And my surgeon
fixed me, made me even better than I was." Dennis threw aside his cape with
great flair, and she saw that he was naked underneath. "Now my manhood
measures 16' long; bigger around than your arm, and remains always hard. And
my new purpose in life is to make men suffer! and destroy assholes with this cock and my weapons and tools here" His voice, tenser now, had
still not raised above a loud whisper. "Men, especially sissy men such
as you, have ALWAYS made gaymen suffer. But now the tables are turned, aren't
they, BITCH!, Im gonna mutilate your asshole, until it looks like hamburger meat!


Suddenly, he was brutally ripping off his clothes; Dennis took not on how large Analboys nipples were, and that he was completely shaved pubes balls and asshole made him look like a total slut
He threw him down on top of a large wooden table, her naked buttocks
quivering from the damp, chilly air of the dungeon. He made him sit down, legs straight out, with just his ass hanging off the wooden table. He clasped his hands in
chains, so that they were pulled tight to the wall in front of her. Next he
tied her ankles down in front of him as well , so that he was sitting upright
wrists close to ankles; all four appendages securely fastened. A wooden bar was attached to the end of the table with C clamps. It supported the his ass that was hanging off the side, but was also designed to naturally spread his ass cheeks, totally exposing Analboy open shaved asshole.
A large table was wheeled in . It contained power tools and many cock shaped objects and dildos. A power-drill, a reciprocating saw (saw-z-all) and scroll saw, and suddenly Analboy realized they were going to drill out his rectum, right there on the table!

Dennis instructed his two helpers.
"Attach the mounting brackets to the table, the saw-z-all will be first, Time to destroy another rectum!, HOT! Dennis cheered

Dennis picked up a beer can thick dildo from the cart as his assistants began to attach the brackets. He coated it with KY and came up to Analboy.

"Nice open loose asshole boy, you've been using it, I can tell. Lets fill that cavity right now, take this in your asshole boy!" Dennis slammed the dong right up analboys exposed chute. Analboy jerked and screamed

"Ohhh my asshole"

as the dong sunk to the bottom of his cavity, Dennis gave it a spin and said
"Get used to it bitch, the next larger one will be hooked to the saw-z-all and the turned on high, to destroy what's left of you well used asshole, are we ready boys?" he said

"Ready"

"The saw-z-all has been modified for a 10 inch stroke, and can do 10 strokes per second if set on high. Your rectum will never be the same again" Dennis said
"Oh yea, fuck up my asshole muscle, I'm ready" Analboy moaned as Dennis plungered the dong

Dennis and assistants mounted a 3 inch wide dong with 12 inch long shaft in the saw contraption. The device was wheeled closer to analboys exposed asshole, the saw was stroked so it was all the way out.

"Ok boys, with the saw fully extended, slid the dong up the sluts rectum. There that's it, now secure
the cart to the table, cause this thing is powerful" Dennis said
Dennis made sure the dong was fully inserted into analboys asshole, the large cocked bumped into the colon bend. He stroked the machine back and forth by hand to make sure the 10 inch stoke almost came out of his ass, then back in the full 10 inches, its bottomed out at 9 inches.

"Looks like the final inch will be popping into your colon bend boy!, Ready" he said

"Ohh just mutilate my rectum, I want it bad" Analboy said

"You heard him, hit the switch" He said

The machine lurched to life, in a matter of seconds the dong was a moving so fast it was a blur, Dennis hit the switch to full power

"Waaaaaaaaaaaaaaaaaaaa Ohhhhhhhhhhhhhh myyyyyyyyyyyy assshhhhooooooolllllllllleeeeeeeeee" he screamed

Analboys asshole muscle was mutilated in a matter of second at this speed, he hung on for dear life, his whole body shaken from the machine effects, red rectum meat started coming out if his asshole

"Stop the machine, his rectum is prolapsing" dennis said

The machine did down, the dong plopped from his destroyed asshole, followed by red rectum squirting out 3 inches.

"Nice rectal prolapse!, Hurry get a rubberband" Dennis said

One of the helpers grabbed one of the rubberbands used for his nutsack, Dennis took it and snapped around the red rectum sticking out.
"This should keep in prolapsed out for a long time"

He started fingering the red meat hanging from his hole, ordering Analboy to push out, like he was taking a shit. He did and more of the rectum came out. Dennis adjusted the rubberband to hold the new emerged rectal meat.
"Push out again, get a complete prolapse going"

Analboy pushed again, another inch of rectum came out his battered asshole.

" I think his whole rectum is about out" As he adjusted the rubberband again. His prolapse looked like the size of a toilet paper roll, with a small slit in the end. The rubberband holding the prolapse good " Come here, Ken, you've got a small pencil thick cock, think you can fuck the red meat tube?

"Sure, HOT!" Ken said, jacking his small cock hard.

Cross Dressing then Fisted hard!

Cross dressing then fisted!
It was a Friday, and I had the day off from work, and was feeling both very feminine as well as horny. So I dressed I took a shower, soaping myself up gently working my cock hard, a reached down for the lube and put a dab on my finger then worked it into my hot little hole. It felt so good. I grabbed my favorite butt plug and slid it in to the hilt with one push until it passed the widest point then quickly my hole collapsed around the small end. The butt plug was planted. I then continued my shower, washing my hair, then preparing for a shave. I grabbed the cream and a razor, feeling the plug inside me, imagining a hot stud using my bottom. With one leg with on the rail, I spread my ass cheeks with cream all around the plug. I shaved my ass good were I could reach. Then set the razor down, I grabbed the plug and pulled, my ass resisting expanding back to the widest part, my ass hole was being pulled out, until it expanded wide and quickly exited, causing me to yelp. Then I spread my ass cheeks once more and shaved the rest of my hole, my thighs and then my lower legs. I shaved my crotch area very close but not bald. I stepped out of the shower, and dried myself.
I dressed in a small red mini skirt, with a summer top, red panties and high heels. Makeup lipstick and my brunette wig, I looked passable. Deciding to hit the local area gay bar, mid afternoon, I proceeding in my car until I arrived at the parking lot, Some lesbians were outside as I stepped out of the car and made my way for the door. I could feel there eyes upon me, As I shut the door behind me. The bar was dark, my eyes had to adjust as I took a seat at the bar and ordered some white wine, which I quickly drank down. Looking around I saw a few cute black men, some drunk white guys and a few woman. It was not long before one of the black men approached me. "Can I buy you a drink , honey?" he said. "Sure, Ill have a beer and a shot this time". The drinks arrived as he was explaining that I looked great in drag and the he just loved CD's, especially anal bottom types. "Thats all me" I explained. "Oh, if you had me, you would be filled to the brim, cause I'm big!" I took a glimpse down , and sure enough a big bulge was in his pants. "10 thick inches and rock hard honey, lets go to my place?" He said.
It was a short walk to his apartment, as he patted my ass up the stairs "Your gonna get a good ass fuck, nice and deep", I cooed at this expression as he opened the door. It was not two minutes before he was taking of my clothes. Naked I stood in front of him. "On the bed, on your hands and knees, bitch and hang that pretty ass of the side of the bed so I can get it ready" I got into position, he spread my ass cheeks and applied something cold and wet. Then I felt a jab a s a finger entered followed by another. "ooohh" yes. Two fingers swirled in my ass, as I heard him jerking his cock, I turned to look, astonished when I saw the giant black monster, yes it was 10" and real thick too. "head forward you slut, dont look" the he plunged a third finger in, "ohhhh my ass". "hey bitch loosen up", as he pulled his fingers out and aimed his cock and my looser hole, quickly he pushed the hard head, to my surprise causing me to yelp from the sudden stretching in my ass. "ooo god your wide" I said, "Hey bitch just wait, just wait", then he slammed the entire length in me all at one time "ohhhh go, ohh god, oh god," I screamed as his dick tore into my widely expanded asshole. He started pumping me like a mad man, big long thrusts from head to base as quick as he could pummel my ass. The wide head expanding my asshole loosened it up quickly and as he drove to the hilt as I was screaming like a banshee. Quick ass busting strokes rocked my body, the he would slow down. I watched as he would completely pull his dick out, then slowly slide it back in the entire length, feeling the cock go way up in me. He grabbed and pulled my hips grinding his dick into me, soon I felt his head swell, then explode into my ass "Ahhh, you hot anal slut, I'm gonna fist fuck your cum filled ass!" His dick slide out with a pop. "turn over and lay on you back" he said. He left the room, and returned with some duct tape, two white socks and a big 'ol black dildo. "Put the socks on your hands and grab your ankles and lay back like your gonna get fucked missionary style. I did as I was told, my gaping asshole wide open and well exposed, he duct taped my forearms to my ankles, the greased up the 9" dong. "Now I got you, and feel this honey" he pushed the dildo in my poor ass hole, it entered quickly, "ohhhhh shit, my ass, oh yes yes" I said. He worked the dildo in and out for a while, continually lubing me more and more. "I dont need anymore lube" as it ran down my ass "You will for my FIST!" he said.
"NO!, no dont use your fist, its gonna hurt. Your gonna ruin my asshole, please, No!" He paid no attention to my pleas, as he brutally sunk 4 fingers to the knuckles "Unnnnnnhghhhhhh, oh oh" I grunted. "yes, bitch loosen up for my big fist" He folded his thumb in and pushed as my asshole expanded farther than it ever did before. "Oh god, my ass hurts take it out" Just then his hand slipped in. "There you go, lets leave it there until you get used to it you slut, I'm gonna wreck that asshole tonight, your not gonna shit right after I'm done with you!" He left it there for what seemed like a long, time, then the pain, started to go away, as my ass loosened even more. Then he started swirling his fingers around in my which sent me over the edge, moaning and groaning, babbling incoherently. "shut up you slut!", then he slide his hand deeper into me, "oooooooooOOOOO, WOW!" As I watched it disappear to the wrist. "now for the ultimate ass stretching!, I'm gonna make a fist and then pull out of your ass pussy"
I could feel every movement as he made a fist, that felt like a baseball in my ass. I shut my eyes and threw my head back, as he began to pull out of me. "Look at your asshole as in pull out of you, wow!" he said, I propped my head up to see my hole being pulled away from my body as he reached the widest part of his fist, my inside asshole lips let loose as his hand came out, a big moan and sigh as I felt empty. My ass gaping open and my cock still dripping hard. I was bound but felt a lot better, the without warning he slipped the black dong head in my ass and pushed hard, sinking it to the handle, I screamed in ecstacy, as he began to jack my rock cock in one hand, holding the dong in the other, rolling it in circles causing me to explode in orgasm "Ohhhh shiittttt I'm cumming"…….
Afterwards, he cut me loose from the tape. From that day on, we have weekly fucking sessions at his place, but I never let him fist me again….

The Cottage

The Cottage:
The air between us was as it always is--comfortably charged with an intense sexual energy. I love being with him like we were this afternoon. I feel so alive, so full of the world. It is almost as though there I have a greater understanding of life, the workings of the earth and everything around me. Above all, he has taught me to revel in these things, to appreciate myself and where I am in my life. These silences are more significant sometimes than any words that might pass between us. Ten minutes from the corner where he collected me, I found us in front of a bank. He held the door and I walked in before him, marveling at the exquisite architecture. It was an old bank, centered downtown in the midst of newer, tall skyscrapers. I have walked by that building on many occasions but never had a reason to go inside that particular bank. I was awed by the high domed ceiling which was decorated in a light-colored fresco pattern. I followed him blindly to the back of the bank; I was too distracted by the magnificence of that turn-of-the-century treasure. Four grand chandeliers hung from lower sections of the dome. Large dark cherry wood desks with busy bank employees were nestled amongst several tall marble support columns. Along the far wall were the teller desks. I was amazed to see that there was no bullet-proof glass separating the tellers from the customers. He was presenting his identification to the handsome man behind a desk to the side of the teller windows. The plaque on the desk read, "Safety Deposit Boxes." That piqued my curiosity and I went to stand next to him. I watched him sign the necessary paperwork and then followed as the man led us into the bank vault. I was already in such an excited state and she was very attractive. I wondered briefly if she had looked at me and found me attractive. She led us through one vault and into another--this time a room lined in safety deposit boxes. I watched as he produced a key and handed it to the woman. He inserted both keys into a box close to the door. She slid the box from its place, handed the box to him and turned to lead us out of the vault. I didn't stare at the man so intently that time. I was too concerned about what was in that ominous box. I couldn't figure out why he had brought me there. I kept wondering what was so important that he would keep it secured at the bank. Was it a gift for me? Papers for me to sign? The carpet beneath our feet was a high pile plush in a deep plum color. I love carpets like that; they have always reminded me of the house where I grew up. When my father built the house, he had plush lime green carpet installed in the room I shared with my sister. During the first week we lived there, my little sister and I used to walk around in our bare feet, feeling the squish of the new carpet, breathing in the slightly plastic aroma and hearing the slight squeak as it was crushed by our tiny feet. The carpet at the bank, although it had no smell or squeak, gave me a sense of recognition and the comfort that went with that feeling. The man stopped at a tall door. He led us into the room, pausing briefly to light a floor lamp in the corner of the room. The table and two matching chairs that dominated the center of the room were constructed in the same dark cherry wood as other furniture I had seen as I walked through the bank. The man laid the box on the table, told us to take our time, then left, flipping a small switch next to the door. I felt the door shut behind me with a slight whoosh of air against my ankles. The look on my face gave me away. I stood near the door, unsure of what was expected of me. He gave me a slow smile and said, "No one will disturb us. I see you are wondering about the switch near the door. It turns on the occupied light. We have an indefinite period of time to conduct our business. adornments on your nipples, Clamps were attached. Do it. Now. Against the wall!" I struggled to comply, pressing myself against the cool dark wood paneling. My nipples screamed in protest and I could feel the instant reaction between my legs. The wall was cold against my cheek, my palms and my thighs. I had a deep fear that someone, probably that beautiful man, would knock, or worse, open the door, finding me in this unlikely position. The room was silent for a short while. I thought that he must be admiring me.
"This key, is the bank presidents personal cottage. He is really into anal, and has built his own place especially for opening up slutty boys asses. You'll be amazed at the things he's got in there. I have agreed to take you there. You will meet him, and you will also submit to his anal desires. I will also be present, assisting him, and gratifying myself as well, now lets get going" I was escorted out of the bank, into John's Van. I was instructed to sit in the back bench seat, and remove my pants and panties. "Grease up your asshole boy and finger fuck your asshole loose, then slide in this plug, I want you ready when you meet this guy, Joe. He will probably want to enema you first so be prepared" I did as instructed and two finger fucked my asshole loose. I was not 10 minutes and the Van stopped at a small cottage in the woods. I slide my pants on without the undies this time clamping my asshole tight around the plug and zipped them up. The cottage was beautiful, German looking green and white. Strange the windows were completely sealed. John knocked on the door, he must used a special knock, because he hesitated and did it twice. A muffled voice inquired from with, "Its me, John with the boy". The door opened and a elderly gentleman greeted us with a smile, inviting us in. I was shocked guys he was naked, and was perfectly comfortable with me, a total stranger. "John, this is Joe, the guy I mentioned, and this is his anal sex shack" The elderly gentlemen must have been 65 maybe even 70. "your cute!, John has told me all about you, and I saw your analboy ass openers site on the web" He shook my and nad squeezed my ass "So you love it in the ass huh?, well your gonna get it good!. First the are to many Johns, lets either Call you Johnny or Analboy, what do you think john??, yea, lets use analboy. Ok analboy, strip naked and Ill give you the tour of the place. When I took of my pants the plug popped out, Joe looked at John, then at me. "We better do a deep cleansing enema right now" he lead me to the bathroom, where the shower had a built in enema station, bend over boy, show Joe that pussy." I did as instructed "Jesus, that is on of the most beautiful asshole I have every saw, just a little loose and of so round. The long enema probed slide deep into my ass and the water began to flow "Take as much as you can, expel, and do it one more time. Sometimes I go really deep into ass, 14-16 inches, so you need to be real clean" " Oh my god that's deep" I shrieked, expelling the water violently. He filled me again and I blasted another hard stream into the toilet as he watched. "good boy!, now the tour" he said.
The cottage was only 1 floor. Every decoration was phallic shaped and porn was everywhere, mostly female and male anal insertion shots. This is the entertainment area, large TV and VCR with plenty of movies. The TV was on showing some naked guy getting sucked. Over here we have a small bondage area, basic stuff ropes, ball stretchers, etc. This area here with the bed and chair is where I do most of my work, Like the nice chair with stirrups????, I wanna be eye level as I enter your asshole. This Video recorder on the tripod will not only record us mutilating your asshole, but it is also hooked to this TV so you can watch us ruin you. This closet holds all of my dildo's, and toys. We will use alot, but we will also do some veggie stuffing and use some bottles to expand your asshole. Then after a couple hours you should be getting some nice ass lips, then I will vacuum pump those ass lips until your asshole turns inside out or your asslips are just huge, Are you ready analboy?" "Yes Daddy" I replied. And thats when the ordeal began.
Old Joe knew exactly how to open my asshole, within, 15 minutes he was 3 finger fucking my asshole. He really loved it, and John was egging him on for a 4th finger. He did and rotated the 4 in my asshole in and out, kneading my asshole into submission and relaxation. "Ok dildo time, John get that black one, 11" long 2" thick massive head" Ok analboy get up in the chair, legs in stirrups and lets open that ass!" I did and he made all the adjustments to the camera and switched on the TV, there was my asshole, close up and bigger than life. The black dildo came close to my hole and Joe slid it deep into me, "Ohhh gawd thats good" I moaned " You like that don't you baby" as he thrusted it in and out, going deeper with each thrust, "Hey slut, no problem with that one, lets go bigger" This continued for some time, slowly he was working up to bigger and bigger things. At 3" wide (75 mm) and 13" (330mm) I was at my limit. Slowly he was sliding this one in, very carefully, "ohhhh good boy, your taking it, this is soooo Hot. " he was pulling my balls, "These are in the way, lets tie them off tight" He tied off my balls with a velcro band. He snapped it shut TIGHT as my ball sack and nuts where really tight. "Good now lets try that eggplant. They greased it up and placed the small end at my hole prodding and pushing my asshole open. He flipped it around, the 3.5"(88mm) wide fat end was being pushed into my ass "Open up babe" he pleaded, I relaxed, my asshole expanded and the eggplant popped in. "WooooooooW, oh my asshole, oh gawd!" "Fuck yea, slut take it!" the guys yelled. I was filled to the max. In the TV all I could see was the green nub of the eggplant outside my asshole. He had completely inserted the whole thing into my ass! He had his palm on the small green end and slid the nub inside as my asshole closed around the end. "Dont worry, hon, this thing will come out, in fact if I remove my hand I know your ass is going to reject it immediately, watch" It did just that I watched my asshole push the eggplant out, it popped out, revealing a very lippy huge asshole "ohhh boy look at that asshole" he was stroking and petting my ass lips like he was in love with my hole (I believe he was). "ok back in eggplant" He pushed, this time my hole opened up for it and it sank in, then he pushed and I watched it disappear into my asshole again, "ohhh fuck I'm filled to the rim"
"I think he's ready for something bigger and thicker. Boy, hold that eggplant in your asshole, DONT let it come out" he left for the toy closet, he found a double dong dildo that was a little fatter than the eggplant and 18" long. "ok boy let it out, I moved my hand and the veggie plopped out of my open asshole. Joe placed all 4 fingers in my ass and slid his hand in, "ohhhhh fuck, your fisting me!", "oh yea, nice and slow", he rolled his hand in my ass wrist deep and then removed it, the Super dong he had slid into my asshole "ohhh thats even wider!" he stroked it back and forth ten inches in depth. 'Boy, its going to go 16" into your bowels when we are done, but at this point your getting some major asslips and your super loose, so lets start vacuum pumping your asshole"
The small cock pump was brought out, my analring greased around the small asslips and it was popped on. 'Im going to draw a small vacuum until your ass lips pop in the tube, we will hold for 2 minutes then break the seal and inspect those lips, then repeat until they are huge!" Joe snickered. He began to pump the bulb as I watched. He pumped and pumped , nothing happened, but then a strange sensation I felt, then "POP", my lips sucked into the tube "Ohhh fuck!" I screamed. "Ok hold it baby, a little longer, here they come, look at those lips!" 2 minutes passed and the seal was broken. and my huge asslips were exposed. Both guys felt them, stroked them, then Joe lightly licked my quivering asslips. The were as thick a drinking straws now. "Ok lets pump them once more, then back to the dildo work" Joe was ecstatic, almost in an anal trance, as the tube went on, the bulb was pumped. This time it only took a few pumps as my ass lips got sucked in "Ohhh gawd, that feels weird" "ok hold for one or two more pumps" Joe said, I could feel my asshole being sucked into the tube, then something let loose and the tube filled with my asshole, "ohhh gawd your ruining my asshole!" I thought I was ruined for good "Just hold on honey, all youve got is a nice big rosebud in that tube, dont worry", after two minutes the tube was removed, revealing a huge asshole turned inside out and the drinking straw thick lips were even bigger "Hot damn, that is amazing. John get that big dildo, I'm really gonna work the huge rosebud now. The superballsy dong was a solid 3 1/2" (88mm) x 13" (330mm) long, he greased the monster up and started sliding into my ruined asshole. "ohhh gawd, that ones gonna make my sissy cock squirt" I moaned as the massive head pushed my rosebud into my asshole and then he drove deep into me "I want you to cum, you slut, squirt your cum all over" He started ramming hard and fast deep inside me, "oh oh oh fuck yea, oh yea, make my sissy cock squirt!, ruin my asshole!, oh that feels great" Joe did a huge thrust hammering it the entire dong length, the started twisting in my ass "Ohhh here I cum!" I cried, Joe, now punch fucking the dong in my asshole, slammed into my prostrate "Ohhhhhh fuck Im cummmming!" a huge load shot from my cock and ran down my balls, Joe scooping the cum and using it as lube as he kept hammering at my asshole " I want to cum in your wrecked asshole boy right NOW" He pulled the dong out and slammed into me with his cock, I could not feel anything but light thrusts Joe yelled "Im going to cum, cum right in this sissies asshole, here I go!, Ohhhh fuck yea, take the cum you slut!" he fell on top of me. John was just wide eyed "Joe you really worn my analboys asshole out, he need a rest" They both agreed to give my pussy a 1 hour break, but then after that........... Ill let you imaginations wonder about what happened next, much more intense, look for the cottage2 soon

Blown out asshole and rectum

Blown out asshole and rectum

Dan, Chris and Brian were halfway thru a hot Analboy session. They were reaming him out everyday for the past week.
He had really loose and open asshole.
"Wow... he's got one big butthole!" Dan said: "Had enough, bitch? Keep
dreaming.
You're nowhere NEAR done." Dan got up to look for something else...

he laid eyes on their bags... rifled through Chris's.... "Ooohhh... look
what YOU brought!" From the bag, Dan produced a smoothed wood rolling pin
with it's handles missing. "How about a big log going up instead of out,
slut?" Dan proceeded to slide it, greasy, up Analboy's greasy & gaping ass
channel. "Mmmm...." "Ohh, you like that, don't you!" Dan began pushing &
pulling, fucking Analboy's rectum with a will. After a while,
Brian nodded his desire to move in, & Dan withdrew the wooden roller.
Brian stepped up to bat, holding a plastic hair dryer like a gun. He'd
removed the nozzle cap, & covered the blower with two condoms. He slipped
it into Analboy's asshole with ease, dilated as it was. Brian really
got into pumping it in & out, as Analboy wiggled & play fought, powerless
under the other two. "Mmm! MMmmm! MMM!!!" he quivered & shimmied, his
creamy bottom wiggling in time with Brian's rapid reaming, unable to hang
on to the super smooth & nicely wide nozzle for anything. It plunged &
slipped in & out, out & in, in & out.... Suddenly, Analboy felt the hair
dryer disappear, & something cold, wet, & metallic touched his cheeks.
Before he knew it, a soda can had dropped into his waiting rectum cavity. He
closed up over it, pushed it back out an inch, drew it in & out a few more
times, & finally expelled it from his anus. "Not enough? Here's more!"
He felt the base of a 20 oz soda bottle slid up. Chris pumped it in &
out like a man possessed.

"OoooooooOOOOOOO!!!!!!! YEAH! That's it! OOOOOoooooooo......" He
became delirious with the intensity of the anal invasion, as Chris
continued his assault on Analboy's anus with the soda bottle. Chris said, "Looks like he's
getting tired, men; think he needs a pick me up?" He pulled the bottle
out, opened it, & tipped the open end into Analboy's tush without spilling
a drop. The soda drained into his colon in moments. "!!!!!!!!!!!!!" His
body absorsbed the caffeine & sugar, & got serious wired. "What a rush! More!" Dan got
another bottle of Wild Turkey & tippled four fingers worth behind the soda.
"Rye & cola enema! Better than drinking it!" B: "he's FLYING!" D: "Yeah,
he's in no position to object to ANYTHING, now!" D: "C'mon, men, what
else ya got? C:"You bet that super-loose ass, we will!" B: "How about
some food with that drink, bitch?" Brian'd produced a bag of cucumbers.
"Hmm..." he slid one into Analboy's waiting asshole. Way loose. One's
not gonna do it." The first was backed out & a second one joined it, both
going up together. Chris took hold of one. "Hold on," called Dan,
"me, too." They pulled Analboy over the arm of the couch, & Dan plowed
Analboy's asshole with a third cuke while Brian & Chris plied Analboys rectum
with the first two. Analboy was delirious. "Ohhhyeahhh...
ohyeah....OHEAYHH........" he nattered over & over.

Finally.... D: "Men, he's so loose, we gotta ramp things up a
notch!"

"What else have we got?" asked Dan. "BIG stuff. His & ours," replied
Chris. "He's almost wide enough to be double fisted again, well Almost." "You'd better believe it!" crowed the drunken Analboy. "I've got that feeling... wind whistling through my ass!" "Well,
we'll just have to stop it up, won't we?" asked Chris. "I've got just the
things!... I just love these spreading my asshole..." he trailed off as
he produced two dildos from his bag, both resembling two baseballs on a
stem with a base. "They look like softball insertions we did last week!"

commented
Dan. "Right!" "You use both?" Him, however...." he
greased one up, & found the paddle Analboy used for plug spankings. He
touched the nub to Analboy's butt. "He's tightening up again. He needs
CONSTANT attention to keep his width." Chris tapped on the base of the
dildo with the paddle. "Ooo!" The first ball popped inside Analboy's
bottom; & his muscles pulled it in until the top of the second ball was
between his cheeks. WHOP! "OOOOOO!!!" The second ball forced it's way in &
Analboys sphincter slammed shut behind it, the base of the dildo showing.
Chris pulled one out... pushed in... out... in... "He's loosening...
the other one..." The first ball of the second dildo pushed behind the
first dildo's first ball... "OOOOOHHHHH!!!!!" Analboy wailed as it pushed
deeper & stretched his assring back to the size it had been shortly
before. As Analboy tried to move them around inside his body, to accommodate
them comfortably, he pulled the other two in together!
"NNNYYYEERRRGGHHH..... OOOOOOOOOHHHHHHHHHH!!!!!!!!! OHMIGODIMSOFULL1 Get
'em out!... Nyyerrrghhhh.... OW! OO! OO! OOO!!!" Out they came, one by
one. The torturous ecstasy put him out.

"He's ready." "Not just yet." Dan slapped Analboy awake. "Wake up, bitch.
We've just begun to torture your rectum." He went over to the recording
studio, & returned with sawed off end of a wooden bedpost. Dan covered the post with vaseline, & then, angled one end
into Analboy's anus, the balled end popped in. "Ooohhh... SOO... FULL...." "Yeah?" "Ow! OW!" Dan
pulled on the post, plowing his anus. "THIS'll make
you feel even fuller than those rubber balls." He got into position and with both hands on the
post he began pushing... "Ooo...
OOOOOHHH... Ohmy... ohmi... OHMIGAAWWWDD!!!!!" Analboy cried out as the post
stretched his over-dilated sphincter wider yet. "ooOOOOOOOO!!!
Ahhhhhh...." The upper edges had pulled him open enough to enter... "a
little farther..." the widest point was moving inward... SCHOOOMPP!!!
Analboy's elastic anus regained control & pulled the into his rectrum, a
good 6" in girth. "OOOoooo--OOOO!!!" He wailed. "OH, Wow! So Big! So
BIG in my Ass! Mmmph! Mmmph! OW! OW!" Dan pulled the post out again.

"Don't look now, here it comes!" called Brian. Before Analboy knew
what hit him, "ooooOOOO! OOOOOOO!!! AHHH!" Chris had grabbed him by the
hair, pulled his head up, & by force of action, pulled the rest of him
backward to where a 7" wide by 9" tall buttplug was waiting on the couch
cushions below. Gravity did the rest, & the plug forced it's way in
easily. "You! You'll pay for that! Get this thing out of my ass!"
"When I'm ready, slut." Brian rolled him roughly onto the floor. Rolling
over on him stomach, what Analboy saw made his eyes bug out. "EEEPP!!"
Dan grabbed him by the hair. "Play time's over, bitch. Now, you pay for
the no shows and the no good, too loose sloppy ass fucks. You've been
having WAY too much fun." "NO, NOT THAT! ANYTHING butmmmmphhhhh...."
Brian cut him off by wrapping a ballgag in place. On the floor, standing
upright, were a number of extreme sized dongs. "Ooohhh, yeahhh. Destroy your asshole boy!."

POOOOPP!! Chriss pulled the plug out. Analboy screamed through his gag.
"THAT got his attention. He's bleeding from the sphincter a little.
Looks like you tore him just a little, Chris. Too bad for him. Booze!"
"!!!!! Mmmm..." Analboy whimpered, as another shot of whiskey cleansed his
ripped rear entry & was absorbed into his bloodstream. Chris grabbed a
10" long x 5" wide pyrex dildo that was a bit wider in the middle of the
shaft than at either end. After applying a jar of vaseline & a tube of KY
to Analboy's wrecked asshole, he plunged the rod home... "!!!!!!!!" The
dildo was so hard & slick, Analboy's bottom couldn't get a purchase on this
ramrod. In & out, it went out fast & back in faster. Chris battered him
mercilessly. "My turn!" called Brian. "Wait!" FLASH! Dan got a pic of
the rod up Analboy's ass. "I've got a better idea, before we get to the
good stuff," piped up Chris. "Let's all fist him on before we use
ones we have to hold him down, or open, for. But first..." Chris poured
another few fingers worth of whiskey into Analboy's butt. Then, he capped
the bottle, & worked it into Analboy's cheeks. A little pressure... and
his anus opened to let the bottle inside. Chris wiggled it around a bit, &
then pulled it out again. "Okay, NOW he's flying. He'll enjoy every
cheek stretching second of it." "I'm up to bat," said Dan. "No. All of
us at once; each of us gets a turn on his asshole. Men, choose your
dildos." Dan grabbed the 19" x 5" rambone, Chris took the 15" x 5" smooth
& bumpy, & Brian grabbed a 4' x 6" doubleheader. "Up his asshole by order of
length. I'm first. Dan, take his asshole; Brian, ram it down his throat."

Over an hour, they 3 on 1'd Analboy. Analboy got his ass fucked deeper
& deeper, his rectum prolapsing on every pull out. As Chris continued
on brutalizing Analboy's behind....the asshole ring muscle completely gave out.

Analboys's rectum looked like a cave. "He's wide enough for stage 3!" Chris commented.
Analboy, looked at the condition of his asshole in the mirror opposite of Chris. "You
fuckers have RUINED my ass! I'll never be able to have an empty ass again!
"D: "You've had it deep, bitch. Now, we're gonna widen you even more!" C:
"Which one's next? There's still a lot more!" B: "That one. My turn."
Brian indicated a 6" wide, veined dildo with a prominent head that curved
upward, & was really firm. C: "Good thing we brought enough lube!" D:
"Enough? We're putting OUT a lot, too. We're all half covered with
vaseline." They proceeded to grease him heavily; & then
Dan & Chris held Analboy's cheeks open. D: "You're closing up, again, bitch.
Time for a severe rectal reaming!" Brian moved the 6' wide meaty dildo
into place & began pushing. Analboy wriggled more & more with pleasure as
his ass opened widely. He was getting off on the relatively difficult
dilations; & loving the eternity it took for the rods being used on his to
probe deeply into his lower colon. He shook as one orgasm after another
took him.

For several minutes, the three slowly worked the monster cock, pushing
up, pulling out, tormenting Analboy's anus ever higher to new heights of
pleasure, ones he'd never known before. he was building...
buiLLLDDIINNGG.... "Hey... where'd it go?" he thought. They'd taken it
out. "Okay, ready for the next one!" "OHHHhhh, miiGOOdddd," he thought,
"I'll never be able to close my ass again, once they're done! I've been
fisted loose a dozen different ways; & they're STILL not done! "My
turn!" called out Chris. He produced a 2' tall firm black dildo with
no head, just rounded off at the top, 7" inches in girth. "Now that the
last one's prepped you..." How glorious it looked, Analboy thought, as it
stood straight up, greasy & nasty. "Sit on it!" all three chorused. They
pulled him up & bent him forward onto the couch cushions. Then... "!!!"
They'd moved it into place under him. pushing him upward a bit as the
rounded off top nestled into his assring. "OOOoooOOO, it's wide!...
ooo...ooooooOOOOOO.....ohyeah... OHHHHyeahhh...." His sphincter was
dilating deliciously, being required to open farther than before. He bent
forward a little more, & got his hands to where he could open himself
more. He felt their hands on his behind, spreading & stroking. "You can
do it..." said Dan, "spread it open & shove it in..." "Ooooyeah., stick it
in your asshole!" chimed in Brian. "C'mon, you can take it," piped up
Chris, "take it, take it.... Ooohhh!!! There it... goes!!" "MMMM!!!"
Analboy felt gravity take over as the wide tip opened his assring far enough
to start it's journey into the depths of his rectum. He sank downward....
"Oooo... OOOOhhh...OO! OO! OOOO!!! OOOOOOOOOO!!!!!!!!!!!" Analboy cried
out as he took the mighty meat 12 inches into his rectum. "C'mon... I wanna
ride this... lube me up... KY it good.... GOD! I'm turning into such an
anal whore..." As the other three started slicking up the black monster,
Analboy started humping up & down on it, moving all the way off, & then
taking it up a foot again. As it began banging into Analboys'scolon bend, he
lost control of himself & went wild. reaming his rectum out, determined to mutilate his
own asshole.

Next, the trio produced another soft, pliable 'Mr. Softy" which was
twice as big as the one he'd used on them! 2' long & 6" wide!
ImPOSSible! Analboy thought; but in a few moments, he was thinking
"OOOOOooooooo........feels SOOO good..." He sat on the tapered head, & it
bent & fell away. "Put me on the floor..." On the floor he went. "Put it
in... oooo...OOOOOOHHHH!!!!" he called out as they pressed it into him.
Under him, it wiggled & re-formed itself to adjust to his rectal passage,
filling him so fully & deliciously, that when it hit home against his colon bend & he clamped his butt muscles around it, he didn't even WANT it to
come out again. The dongs head popped into the bend. He grunted & squeezed; & it tickled & teased his slutty asshole so ecstatically that when they finally pulled it out a while later,
it slipped right out, & he cried "NooOO-huh-hooo!!! Put it back!" C: "If
it doesn't pound, it doesn't stay long! Still a few more to do!" B: "Is
he wide enough?" D: "You bet he is!" Two rambones appeared, & Analboy
felt both press against his anal cavity... TWO?!? I don't know if...
.OHMYGOD!!" Amazingly, with only a little pressure, he'd opened up & let
them both in. Both shafts sank inward, up to about 9". "Not too far,
together these could hurt him." After many minutes of holding them in
place, finally, these, too, left his tormented anus. "Now?" "Now." The
three moved him back to the couch.

Now, the trio let Analboy be for the moment. "Well, men; I don't
know about you; but I need more plowing of his asshole," said Chris. "Well, let's see if
he's got enough for everyone." Checking out the gear in Analboy's dungeon,
the threesome found four sex pistons, two of which rotated as well as
penetrated. They were taken back to the main playroom. Brian took one
that only pounded, set the 'pound only' up for Analboy. The set the machine to insert up to 1',
the speed to tormentingly, torturously slow, greased the massive dong up, &
spread Analboy's asshole wide open...
"mmmmmmMMMMMMMMMMMMMMMMMMMMMM!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!" Analboy hummed through his gag as his sphincter stretched it's
widest yet. In moments, thought, the tapered tip pried his assring open &
the thickest point achieved entry into his anus. "Mmmmm...." Analboy
wiggled & squirmed as his rectum cavity filled up.
"OHHHhhmyGOOAAAWWDDDTHISISSOOOOOGOOOD!" his mind cried out to itself, "this
is un...fucking...beLIEVEable!! SoooOOOO... GOOD! OOHH!! Deeper...
DEEEEPPERRRR!!!! Deeper, girls! DeepinmyassDEEPINMYASS!!!" BANG! The
mighty meatus banged into Analboy's inner ring. He peed all over the
place, as the massive dong straightened out the boys colon bend over and over.

"Slow? Nah, make it a bit faster. Enough where it won't hurt; but
where it WILL blow his mind." Analboy felt it withdraw to where the widest
point came out.... & then it abruptly pushed in again, tormenting his
sphincter with each hard, medium-speed thrust, which was wrecking his
muscle control. He hung on for dear life, trying to wrap himself around
the exquisite torment; but he finally detonated with rapture. He
submitted to the extreme anal pounding, & took a two-hours rectum wrecking
before he collapsed, overloaded.

Finally, when all three had come back down & had gotten enough (for
now), they pulled out the tree trunk lodged up Analboy's butt & freed him.
Analboy's butt was leaking everything; but wasn't bleeding. "How you
doing, slut?" Dan asked. "You... have...RUINED... me!! I... have to
have... something... INCREDIBLY huge... up my asshole... all all times
from now on!" D: "Well, we can cure you of that, for now. One last
humiliation, you bitch. AND... when you're done... if you tell your
doctor about this... every picture we've taken will be ALL over the 'net."
"Be my guest,' Analboy replied. "Bring it on... EEP!"
D: "Hold the bitch down!" Dan produced the biggest, baddest dildo ever
made, 4' long, with the shaft going from 12" wide to 16" wide at the back
end, a tapered head that began at ½" to 14" at it's widest, where it flared
out before the thinnest point of the shaft. "Get him on the floor. Lie
across his back, Brian. Pull his legs apart." Dan edged out the other
leg... "OHMIGOD! IT WON'T FIT! NO! NO! OOO! OOOOHHH!!!
OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!"

Analboy 'oooh'ed non-stop as Dan forced the mega-penis against his
destroyed assring. Hhe opened handily, letting it in until the flare of the head met his
buns. "Grease him, Chris. Every bit we've got." "OooooOOOOHHHHhhhh...
too much grease... OHMIGAAAHHHDDDD IT'SGONNAFIT! ITSGONNAFIT! PUSHIT!
PUSHIT!POOSHIT!!!!!OOOOO!!!!OOOOOOHHH!!ITSGOING! IT'S GOOIINNGG!!
IT'S....GONNNA!!! FITTT!!!! GONNNNAAAAA....FIIIIIITTTTTTTTTTTT.........."
Analboy's face reddened against the excruciating pressure on his
sphincter.... & suddenly beamed in rapturous pleasure & pain as the
pressure on his assring became too much. His sphincter gave way & was
ripped as the super-huge dildo passed the point of no return. The
flare popped inside, & the trunk sank up Analboy's butt, stopping when it
could go no further, with the dildo stretching his bottom open to a 8" in
width. "OOOHHHHHHMIIIIGOOODDDDOHHHMYASS, OHHHMYASS!!!! SOOGOOD
SOOGOOD...." & Analboy cried out in ecstasy one more time as his cock
detonated while he rocketed to the highest heights of anal ecstasy.
"THANK.... YOUhhhhhh...."

When he came around again, the trio was gone. "Bitches," he thought.
It took him hours to get to the phone, his every movement exploded with
rectal orgasm, violent rectal spasms hit him. He hated the thought of it coming out. Finally....

"Hello, doctor? This is Analboy, how are you?... Me? I'm in a
predicament. To make a long story short, some friends & I got together
for some fun, & we REALLY got carried away... We've spent... fuck, what
day is it? Holy cow... the last 36 hours into... my fave... Yes...
Yes... Do I HAVE to say it? Yes, they spent the ENTIRE time putting
everything but the kitchen sink up my asshole... Uh-huh... They got me real
drunk & finished me off with the biggest dildo on the market stuffed up my
rectum... Can't get it out... sure don't want to try.... Yep, anything you
can do.... You're REALLY enjoying this, aren't you?....."

The End

Anal Annihilation- "I did it"

Anal Annihilation- "I did it"

Anyway. There I was, belted and bound to that insidious, evil chair, (I love how that sounds, for that's the only thing it's there for, is to restrain me and pull my ass chute (literally) onto the pole that's waiting there) knees knocking, body trembling slightly with the effort of staying erect. I wanted to, I didn't want to. I knew my asshole would never be the same after these series of sessions. The anticipation was killing me (so to speak). Greg had really put all this together, apparently (and especially) with this in mind, to totally break down my assring muscle with a series of large dildos, combined with rectal pumpings and piss slit soundings, and I had this feeling that it was going to be a rough session for the ass chute. He'd amassed all that lube, readied it for deep injection into my colon bend, and set the dildo on the chair and lubed it while I laid on the bed concentrating on holding that huge expanding fuck toy deep up my rectum, with all the might I could muster, from inner sphincter to outer. I'll say this, he must have been boiling for days waiting for this opportunity to wreck my sphincter rings. I knew he wanted to make my ass chute open and hanging rectal tunnel from the outer assring all the way into the colon bend, one huge tunnel.
I could barely hold myself up with the anticipation and the action the restraints were having on me. With the restraints in place, well, seat belts like that, you know how they work. Pull them out of the holder, lock them into the buckle, and any excess you pull out gets pulled back in. You can't pull them back out until they've rolled all the way back in, which you know of course means that where the chair's concerned, I couldn't (can't) stand farther up. Once downward motion's in place, those belts are slowly going to pull me down.........wait for it....I know, I know, dear reader, you can almost taste the anticipation of the asshole annihilation . I want you to enjoy this journal like I enjoy experiences in the 'rocking' chair. Don't gobble it up, savor it.
At this point, all my energy was going into trying to both stand up and keep my rectum from coming out and prolapsing, forming a huge rosebud. Greg liked to watch the red meat come out from my worn out asshole, large red flowering rectum would comout and then he would rubberband it off and play with it, often times sliding his cock head in the rectum slit, coming all over it for his climax. Often, he would use a vacuum tube and pump out the red rectal meat for fun and pleasure. I don't know what flashed across my mind as I stood there against the edge of the chair, but whatever it was but my assring relaxed and I pushed/strained and it came out ...you get the picture.
I didn't know how long I'd been holding myself off the edge of the chair, huge rosebud hanging, let alone how long it had been since Greg had first come home and caught me, starting this latest session of "timeless' fun. I also knew I didn't want to wait anymore. Before I could stop myself, I eased my knees a little and gripped the chair's arms in preparation of what was to come. I felt my rosebud slide back into my chute, but my assring muscle still yawned openly, non closing ring. A slight jerk on the belts as my body sagged downward brought me out of my reverie. Time to concentrate on my rectum. It was literally wobbling in anticipation, searching for the dildo that stood gloriously erect below. It had to be, with all the grease in and on my ass and undoubtedly on that dildo, too, it wouldn't be staying in place unless there was a solid suction cup base holding it firmly in place for my rectal opening, down on the wood of the chair seat many inches below.
Another jerk. How far was I off the chair? I'd surely be touching the head momentarily unless it was a plug, Or was he playing with me again? As that thought crossed my mind, my assring was introduced to Greg's (my) new dildo. My first thought as it brushed my cheeks was it was obviously really firm, and rock hard. It was wood; it was snaded real smooth, but not rough, assertive, and offensive, but definitely a rude intruder. It was one of those mighty three foot ramrods made of the harder kind of latex, my rectum was in real trouble, big wooden shaft in the ass. All that flashed across my mind in a splitsecond, along with the certainty I was probably still 10-11 inches off the chair! AND IT WAS BIG! REALLY WIDE! My asshole was telling me just from the way my cheeks were spreading already that it had to be a good 8-9inches in circumference, bigger than the width of a fist! I jerked up. 'I can't possibly take that much in my asshole! No!' But the jerk on the belts pulled me back down firmly and somewhat rudely. Before I realized it, the glorious head was lodged firmly around my ring and knocking on my backdoor. I wanted it, but I didn't want to let it in! I'd be split! "Yes! No! No! Yes! No!" ran through my head. It was either me or the dildo. Something had to give, and of course, the dildo had the advantage. I relaxed, and my ring flowered open; but that mighty monster wanted inside my cavity (or should I say, my booty!) A wail of need and desire ran through my head as my need ruin my rectum excelled. I could help myself anymore! I had to have it! My bowels trembled in need, my hungry assring trembled with desire. 'I'm gonna prolapse again! Ohh, no!' I lost the battle of wills as I started to lose control of my rectum. My asshole opened to try and let the rectum squirt out; but physics and that greasy monster cock outside my backdoor won out. As my hole dilated, that mega-dick peeked inside.
Slippery and greasy, that mighty monster had won the right of entry and was meaningfully asserting itself. I could feel my rosebud being pushed into as my ass widened to accommodate that gloriously huge dildo. Feeling that took me into a zone of nothing but feeling as all my senses focused on what was happening to my asshole.
'Oh, my God! It's huge! It'll never fit! I'm gonna split wide open! Eeeeee-uhhh! Ahhh! Ooooo!Oh! Oh my hole! It's really widening! It's REALLY dilating! This things actually going.........OHHHHHHHH! oH MY....MY ASSHOLE! Oh my God! It's actually going in! No! Shit it out! Don't! I can't push it out! It's going in now! It's gonna go all the way in, I can't keep it out anymore! IT'S GOING IN! OH MY GOD!
(At this point, while I knew I was slowly sitting down, I would have sworn on a stack of bibles I was lying on my side again. All I could feel was that mighty tool pushing itself slowly, so deliciously slowly, up my rectal cavity.) Aahh! Oh, my god. Oh my ass! I can't believe my ass is accommodating this thing! (Note:though it never consciously occurred to me, I was feeling no pain whatsoever. It didn't even feel like that monster had injured my sphincter in any way! Well, why should it have? There was probably a gallon of lube to ease the initial entry (nevermind the lube waiting to grease the ways inside!) Slowly that mighty monster made its way deeper into my hole. 'Shit! ARrrrrh! OOOOOO! Oh my, oh my, ohmi, ohmigoooooooooddddddddddddddddd!!!!!!!!!!!! Holy cow this things just slipping right up there! Hell, boy, it should, there's enough vaseline in your ass to lube a hundred dildos! Oh gaaaaaaaaaaaaawwwwwwwwwwwwwwddddddd! When's this thing gonna stop? Feels like a foot in there already!!! (At that point, it was about halfway up(or was I halfway down?)) Slowly I kept sinking onto that dildo and it kept sinking into my asshole! At that point, I couldn't even think clearly. My ass was happy, and I wanted to just hold that ass jamming pole right where it was and just wait for the orgasm to come. But I couldn't! I tensed and tightened the muscles in my asshole, but the ring had lost all elasticty and could no longer clamp down tight, but that dick was just too lubed to stop. I knew it was going to go all the way to the hilt, right into the colon. When it did, it'd bang right into my anal g-spot and throw me over the edge. I wanted it. I didn't. If I did, I might hurt something inside. 'What the hell, slut, you're probably going to need a butt doctor to take this mighty monster out, anyway! I can't hold myself up anymore! I gotta sit down! All the way down! Just relax........oooooooooooooOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH HMMMMMMMMMMMMMMMMMMMMMMIIIIIIIIIIIIIIIIIIIIIIIIIIIIGOOOOOOOOOOOOOOOOOOOOOOO OOOOOOOOOOOOOOOOOOOODDDDDD!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!' As I relaxed, that rude dude in my chute slid all the way in for a home run. I was finally able to clamp my ass cheeks firmly around the base, and the impact when I hit bottom (literally!) was so GOOD that I involuntarily had to pee. Water everywhere. Meanwhile,that pole slammed into my anal g-spot. It threw me into another dimension. All I could feel was that tree trunk lodged more deeply than anything that had ever been up my ass before. I had to move! I rocked back and forth, riding that mighty shit-fucking pole for all it was worth. Then i heard a humm of an electric motor. The mighty rectum wreck dong, lurched forward, opening the colon bend muscle and popping into the colon, then it reversed it course quickly and plopped out. Faster and faster the pace picked up, nailing my chute at high speed.

Oh my GOD it was great! 'Oh YEEEEEEEEEEEEEEEEEEEAAAAAAAAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHHH!!!!!!!!!SO GOOD! SO GOOD! SO GOOD! UP MY ASS, BABY! ALL THE WAY! RUIN MY ASSHOLE! UP MY RECTUM !FUCK MY ASS! Fucking my asshole soooooooooo goooooooooddddd! Deep in my asshole! DEEP IN MY ASS! Can it get any deeper than this, right into the colon! Oh!Oh!Oh!Oh!Ohohohohohohohohohohhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh hhhhhiiiiiiiiiiiiiiiiiiiii'mmmmmmm coooooooooooooooooommmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmiiiiiiiiiiii iiiinnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnngggggggggggggggggggggggg!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!

All I could feel was waves and waves of lightning ecstasy pouring from my cock and that mighty pole all the way up my chute, reaming me out. Another massive thrust into the colon, another ooonnnnnnnnnnnnnnnnnnnnnnne!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHHHHH HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHGOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOODDDDDDDDDDD DDDDDDDDDDDDDDDD!Ah!Ah!Ah!Ah!Ah!Aaaaaaaaaaaaaaaaaaaaaaaaahhhhhhhhh!!!!!! OOOOOOOOOOooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo ooooooooooooooooooo!!!!!!!!!!!Oh god my bald cock is shooting so hard! NNNNNnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnggggggggggggggggggggggghhhh! Oooooooooooooooooooooooooooohhhhhhhhhhhhhhhhhhhhhhhhhhhhmmmmmmmmmmmmmmmmmmm iiiiiiiiiiiiiiii reecctuumm !Oh my aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaasssssssssss hole!UUUUUUUUUUUUUUUUU UUUUUUUUUUUUUUUUUUUUPPPPPPPPPPPPPPP MMMMMMMMMMMYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYBUUUUUUUUUUUUUUUUUUUUUUUUUUTTTTTTT TTTTTTT!!!!!!!!!!!!!!!!COOOOOOOOOOOOOOOOOMMMMMMMMMMIIIIIINNNNNNNNNNNNNNNNNN NNNNNNNNNNNNNNNNNNNNG!'

I lost track of how many times that dildo reamed my chute with full 14 inch strokes, Somewhere in the middle of the 50 or 60th time, I was so blown out with pleasure I lost consciousness. Butt, it wasn't over yet, diary. Greg left me there for heaven knows how long. Somewhere much later, my body clock said probably three or four hours had passed altogether (wow! that much time with almost all but the first several minutes with one or another HUGE thing shoved up my ass!!) Greg woke me when he was freeing me from the belts. I felt his hand on my arm. I weakly pushed on the arms of the chair and tried to stand up. That mighty monster asserted itself, reminding my I still had a major pole up my hole. I clenched it in and stood. Greg marched me over to the bed and sat me down. Oooh! Felt good when that dildo made contact with the mattress. Slamma ramma jamma in my ass, baby! I lay back, and Greg wasted no time in ripping the monster out and slamming his dickmeat home in my wrecked asshole. From his perspective, I'd put on one hell of a show. He was so turned on, he couldn't wait to get in there. When he entered me, my ring was in bad shape, i could feel nothing until he slid his hand inside my chute as well, and jacked off inside my rectum, sending me over the edge again! Oh!oh!Oh!OH!OH!OH!OH!OHOHOHOHOHOHOHOHOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOHH HHHHHHHHHHHH!!!!!!!!!!!!!!!
He shot a huge load into my poor asshole, and continued the fisting assault, alternate hand fisting, left, right, left, right one after the other. I lost it again a third time as I felt my rectum prolapse and flower out the chute. More hot cream shooting all over the rectal meat again. "I DID IT!" was the last thing that passed through my mind as I passed out again, Greg continued punching and prolapsing my rectum over and over.

Drilling his Asschute

Drilling his asschute

Analboy arrived at master Jeff house right on time, It was noon on a Wednesday, Sunny and warm. Jeff greeted him at the door. Analboy was stripped naked immedialty once the door was shut. He had already cleaned out his ass before arriving. Jeff doubled a large rubber band in two, then snapped it around the boys nutsack, nice and tight. Jeff had worked over Analboy at least 7-8 times already in the past two weeks, and new he was making his asshole even larger, today was the day to take his hole to a new limit. He led him down the basement stairs to a small bedroom with a nigh stand Analboy went along meekly as Jeff fixed his ankle to the restraints, then pulled on the rope attached to a pulley in the ceiling bring his ankles way above his head. He let go, twisted the rope and tied it off secure. Analboy on his back, ass hanging of the bed fully exposed for a good rectum wrecking. Jeff's eyes were big as saucers and fully dilated as he began setting things up for this hot anal session. With both hands he made short work of it and soon the dildos were greased and placed in a pan right below his exposed open asshole. Analboys Asshole has been used so many times, it really does not tighten up and remain always slightly gaped. His asshole ring must have lost some of its elasticity after all those 845 sessions. Head bowed in shame, his dull eyes watched him slide the slippery dildo back and forth in his hands. Nevertheless a gasp came from his lips as he drove the large dildo right up his rectum in one had push . One hand cupped his rubberbanded nuts while the other reamed his asshole out. Jeff slide a finger of his nut hand straight in along side the large dildo in the boys asshole, "UNNNH!". He pulled the dildo out and he bunched his hand into a full fist and began pushing steadily against his open used asshole, "OOOOOOOW!". Analboy began to respond to the intruding fingers and fist. His asshole unable to resist or clamp down anymore, Jeff's balled slide into his rectum with ease, his arm lunged into the slick, red rectum tunnel.
Maintaining him in this fully exposed position and pulling on the nut rope, he pulled the boy nutsack up and out of the way of his asshole, he forced his fist in deeper still into analboys rectum chute. Analboy moaned again and then suddenly snapped his head up in shock, Jeff had just lodged his fist into analboys colon bend. He watched transfixed as Jeff's arm went in farther and farther, Analboy's cheeks now butting up against his elbow. He was in deeper than the previous ass-fister had been earlier and I knew from the boy's look that his fist, like a massive cockhead had reached his damaged sphincter. Gritting his teeth with effort, he kept up a hard steady pressure, twisting as he pushed to work his ass grease onto his fist for lubrication. Pumping the rectum with his fists produced all kinds of ass juice. Jeff began to ease his second hand along side the one already in the boy.
Analboy's eyes bulged half way out of their sockets and his mouth began to contort in a painful grimace as his massive asshole began surrendering to Jeff's slippery twisting pressure. He had it halfway in now, the slut was about to get double fisted to ruin. Doubling over limply, Analboy's knees sagged and his stomach spasmed violently. His slippery anal muscle gave way completely as Jeff's hands popped through his back door with a mighty heave. So complete and sudden was his surrender that Jeff nearly lost his balance as his forward thrust carried him into him another five inches, his arm disappearing into his rectum beyond the elbow!, past the colon bend and up into the colon.
Jeff recovered and, spurred on by the shear depth in the colon, begin to fuck Analboy's ass with his arm. A wet suctioning noise filled the room as he pulled out to the elbow, keeping his balled fist just inside his anus. Still bound, he began to gasp quick breaths of relief, but shuddered over again as Jeff shoved it back in. He slid out again, held it a second, and pushed it back in. Then he started pumping slowly as his bowels began to loosen and coat him with assjuice. Bound, limp, blood rushing to his head, Analboy flopped around like a rag doll on the driving fist sliding up and down inside his colon. But the giant arm-phallus was beginning to have its effect on his well used asshole and he began grunting in rhythm with the slowly pumping arm. I couldn't believe after all he'd been through that he was responding to something like this!, Jeff was destroying his assring muscle and he loved every minute It was absolutely filthy, but watching it only made him more excited.
Analboy began grunting loudly, eeeeuunnnnh! nnyyyyyuh! unh!, his face alternately straining and relaxing as he forced himself back onto Jeff's arm with each inward stroke. It looked as if he was taking a hard shit, grunting to expel the log buried inside him, but every time he tried he slid it farther in. He was driving right into the lower colon and out with each thrust, straightening out the inner bend muscle for good. His worn out ass muscles helpless as the have lost clamping ability, Jeff could drive into him at will with little resistance. His anus acting like a cunt approaching orgasm. Analboys asshole spasms violently when he cums, causing the asshole to clap down in its meager way. he knew that if he came, while being fisted his asshole ring would be torn to shreds Jeff knew that too "Come sissy boy come!, come from anal you slut!" he barked
Hands locked on bent knees, he buck out of control on Jeff's jerking limb, his hard sissy cock bouncing hard against his stomach. Jeff kneaded his balls for a moment. The grunting stopped and his mouth began to contort into the familiar orgasmic stare. Sensing his begin to tremor and stiffen, Jeff socked his fist in and out of him like lightning, hammering the rectum at high speeds. Jeff was getting excited for the orgasm, hoping for huge spasms from the boys asshole Analboy was just beginning to shake He let out a huge scream, as cum shot from his cock and setting the violent spasms shooting through his rectum. Jeff went wild nailing his spasming asshole at high speed, determined to ruin the assmuscle. In a mater of 10 to 20 seconds during the orgasms, Jeff ticked off 50 plunges of the dildo into his rectum, Lube spewed from his open asshole. As his anal orgasm died, the plunges slowed in place to a very slow stroke. Jeff worked his tied off nuts, slowly reaming his ass, preparing him for a second round. His other friend, Tom was due to arrive any second, and just as he was thinking, Tom stood in the doorway
"Looks like you just got done, mutilating the sluts asshole" Tom smirked"Yep, and was about to take him to the absolute limit again, until he losses all control of his asshole muscle" Jeff stated"Let me help you. Hey look how big the whores nipples are?, His piss slit also looks like its been used several times" Tom said"Yep, been rodding out his piss slit, and working his nips too, please go get that metal pan on wheels and the urethral sound collection ok" Jeff told TomTom wheeled the metal tray table over to Analboy, Jeff was still stroking the rod in his asshole, working his nuts "Here lets clamp off the large nips with these clothes pins, Nice!. Tom, you should rubberband off each nut individually, like this" Tom removed the one large rubber-band around the nuts and banded each nut individually, it separated and lifted analboys nuts "Nice!, move the metal pan right under his sloppy asshole and have him push out the dildo for rectal inspection"The pan was moved into position, and the large dildo fell out of analboys asshole into the pan with a plop. His asshole red, open and hanging. Jeff eased four fingers from each hand to the knuckles in his asshole and pried the assring apart to the maximum"Nice rectum chute, give it a good fisting, Ill concentrate on the sluts nips and piss slit at the same time. Look the whores cock is coming back hard, round 2 begins!" Tom saidJeffs hand formed a fist and was eased into analboys asshole, and approval groan came out as he sank to the wrists. Jeffs other hand went back to the banded off nuts on the string. Tom, on the other hand, attached some clips to Analboys protruding girlish nipples. Tom then selected a pencil thick metal urethral sound, Analboy took it right in the piss slit with ease, as Tom pushed the rod to the base of the boys cock, then placed a rubberband tightly around the cockhead keeping the rod secured deep in the slit." Now its rectum destruction time boys!" Jeff said"Hey I got an idea, hold on, Ill be right back" Tom saidTom left the room, and soon returned with a power-drill and some mounting brackets."If we use the brackets, we can attach the biggest dildo to this power drill, and just core out his rectum, like cleaning a drain. His asshole muscle will never close again" Tom said"Great idea to break down the sluts asshole muscle, put this dildo on it, lets get started"A large 3 inch wide dildo with a nasty flared head was fitted to the drill, Tom hit the trigger to test the new rectum rooter. The drill whirled to life and spun at such a high speed, it was a blur."Now you straddle him and hold him down, while I drill him. Yes that's it, now spread his asscheeks" Jeff said Tom held down Analboy in a doggy position this time. He spread analboys cheeks wide revealing and extremely loose and open asshole"Ohh shit!, look at his asshole, he has to have one the of largest asshole I have ever saw!" Tom saidThe drill was brought forward and the flared head of the dildo popped into the boys open rectal cavity. "Ready, set go" Tom yelledTom hit the trigger, the drilled spun to life, at full RPM. Analboy lurched forward, and screamed but Tom held him tight, The flared head battered the asshole muscle, sending Analboy's body into convulsions, twisting and shaking as the drill damaged his asshole muscle in a matter of seconds. He began to whimper and scream as Jeff slowly sawed the contraption in and out of his rectum, dropping the drill a little slower in speed. The whore shot off a big cum shot even with the metal sound buried in his piss slit. Cum oozed from the side of the pencil thick rod, his cock head deformed from the rod, his piss slit was not a slit, but now a round hole. The drill stopped and the dildo left his asshole, it created a giant rectum tunnel all the way to the colon bend. Each man wanted to cream his new cavernous tunnel. Jeff was first. His 7 inch rock hard cock sank in Analboys battered rectum with no resistance."I cant feel anything, his asshole is too loose" Jeff said "Work the walls of his rectum or go in circles" Tom suggested Tom began pumping his dick in and out of Analboy at various angles and positions" Ohh found a good spot!, Fuck yea....feels great!, Take it boy..fill you up" Tom saidAnalboy's open asshole was making noises as Tom, let loose a huge cum shot blasting his open asshole with cream. He pulled out, wiping his cock head on Analboys Hamburger hole"My turn, hope my cock finds the same fold in his rectum as yours" Jeff said Jeff prodded and poked his cock around in the wrecked asshole"There it is ...oh baby thats nice" Jeff saidIt was only a matter of minutes when Jeff pulled out his cock, as a huge white spurt creamed the outside of the hamburger hole. The men cleaned up, leaving Analboy rest up for the next session.The end

The Competition

The Competition

When the announcement regarding a competition for deepest dildo impalement and ass ring width stretching, Analboys Sadistic Daddy Dean new Analboy should be signed up and could probably take 1st place in the width category. Daddy Dean new a kinky doctor that could prepare Analboys rectum for the competition. He had an appointment set up for Saturday morning to see the Doc. The same doctor that had prolapsed his rectum repeatedly during the last visit. They drove over that Saturday. Daddy Dean waited in the makeshift waiting room filled with all kinds of porn and kinky sex things to get off on.

Analboy first scream had come from the immensely large 3 inch wide rod that had been impaled upon him as he was set on the table top. The second was caused by the sudden expansion of that rod, stretching his already worn out asshole to a new size. His first cum shot flew from his sissy cock, he then slumped over to one side as his ass was locked to the middle of the table by the anal locking rod. The doctor turned the boy around, twisting the skin around his rectum, pressed a button on the table, and the rod tilted back, allowing the boy to be laid flat on his back. The doc hit the green button on the side and the massive rod lurched forward into a series of violent 10 inch thrusts deep into Analboys rectum sending him screaming The doctor had to test Analboy's body to make sure it would be able to withstand the upcoming competition. For all the experiments, he needed the boy to be sexed up and able to receive brutal analwork, so he gave the boy an injection in his butt, awaiting the reaction. Within seconds, Analboy asshole ring went completely loose and he was moaning loudly reaching for the huge object lodge tightly is his ass.
The doctor proceeded with the tests. Directly across from Analboy's outspread thighs stood an instrument against the wall with two cables hanging out of it. There were clamp looking attachments on the ends of the two cables which were snugly fitted to each of Analboy's rubber-banded off balls. The boy groaned loudly again as the clamps around his balls totally lifted and separated the nut sack. Bring attention to his smoothly shaven well used asshole. The doctor pressed a button on the machine and the slack was taken up by two winch like mechanisms operated by the computerized control panel. Once all the slack was taken, the winches began to tighten the cables and pulling Analboy's balls away from him. Analboy stared at his naked, hairless crotch as the balls were out of the way for the doctor to work his rectum. The skin was pulled so tightly that a song could be played on it like it was a guitar. Analboy didn't have to look to tell that the pull on the cables was increasing even more. He felt like he was also being pulled harder onto the rod that was packed in his ass, driving it deeper and deeper. The doctor, having no concern for the boy's discomfort, seized the balls from him and kneaded his balls and cock in his hands in his right hand. He continued to roll the large balls around in his fingers, testing them for signs of swelling. Satisfied with the results, he released the hairless balls once again.

Analboy groggily watched the doctor walk toward him carrying a latex dildo with measurement increments on it. The base read fourteen inches, the width was marked at 3 inches. Analboy's butt suddenly was empty as the lock holding him was released, but his hole never shrank to a size that was more natural. But this was quickly replaced with the dildo which was crammed in all the way to the 11" mark. "Uh-oh!" the doc said. "This may disqualify you here. You must be able to take the entire fourteen inches to qualify. Let me get your master." He walked out of the room, leaving Analboy there and returned with Dean and Macaulay following close behind. The doc looked at Dean. "I wanted you to see the disqualification for yourself, Dean, so there would be no mistake. This is as far is it will go." "No! No, no, no! I want to do this! Is there something you can do?" Dean demanded angrily. "I'm afraid I can't. The boy is simply not able to take the whole fourteen inches and he must be able to in order to compete." We'll see about that! That boy is going in and I'll see to that right now!" All at once, Dean placed his hand on the end of the dildo that was still hanging out of Analboy's butt and shoved with all his might. Suddenly, something gave and Analboy let out a terrified scream as the rest of the dildo went right passed his colon bend and was buried to the base in his abused hole. "There," Dean bragged. "He can take it. He's in, right?" Dean pumped the whole thing in and out, each time meeting resistance at eleven inches, but shoving it on in anyway. "That's it!, work the colon bend..ruin it. Keep working the colon, there are still a few more tests." Without bothering to take the fourteen inch dildo out of Analboy's ass, the doctor brought another, more flexible dildo out of a drawer and poked the end in Analboy's mouth. He shoved and the boy had no choice but to swallow the monster or have his brain pushed out through his neck. The dock shoved the rubber dick into the face of the terror stricken boy who could not scream from the lack of air. The entire twelve inches of the oral dildo was now buried in Analboy's mouth. The boy could not breath and the doctor was timing him with his watch. After several seconds of no air, Analboy was becoming genuinely horrified once again. It had been a minute and a half and the dick was still in his throat, blocking his air flow. The boy was becoming dizzy as the watch reached two minutes and thirty seconds. The doc grasped the end of the dildo, and as soon as his watch reached three minutes, he pulled the dildo out of the boy's mouth. He instantly sucked in his precious air only to be let out again by an animalistic ,moan as a long tube was pushed into his pisshole. "Yea working both holes whore" The doctor said "Might even induce a complete rectal prolapse in you if I get my way" He looked down to find the doctor slowly inching the lubricated tube into his rock hard dick. He could feel it now entering the base of his cock. The doctor inched it forward about two more inches, then stopped. He attached the other end of the hose to a strange looking machine on which he flipped a switch. Analboy felt the tube fuck his piss lit back and forth. After the doctor worked on his findings for a few seconds he prepared the large penis pump for the boys rectum, he called Dean and Macaulay back in and told them that Analboy was almost qualified for the competition except that he must ruin both colon bend and asshole ring so his rectum will prolapse. He could get most of his rectum out using the industrial strength vacuum system here in the office."I need him to prolapse out because boys who can't pull there rectum out, can't be in the competition. It would be unfair to the other competitors."With that, he reached up from the ceiling and brought down an Large penis pump hooked the a large vacuum tube attached to the wall the tube was fitted over Analboys open assring. Huge ass lips formed instantly as the Doc pushed a button on the apparatus and a vacuum formed inside, causing his ass ring to get sucked inside. Analboy felt the great pleasure the tube started milking his rectum in the suction. The quick pumping action brought Analboy close to orgasm as the rectum started into the tube and in less than three minutes. The tube was filled with his rectal meat as ropes of cum splattered Analboys chest The doctor noted now many squirts came out of the kid's jerking dick and the approximate amount of cum, which was about five tablespoons. "My," the doc said, "he is a real whore, isn't he. Look at all that cum! All caused by his rectal meat coming out" his cocked jumped; the pump still pumping hard on Analboy's rectum. The boy could feel a second orgasm building inside him. The doctor saw this in the boy's face and dropped the vacuum from seven p.s.i. to two p.s.i., almost a total vacuum. The boy's rectum swelled inside the tube, and in an instant, the vacuum caused a complete rectal prolapse into the tube. Analboy moaned louder in great pleasure but also gaining pain as the suction on his rectum seemed to be trying to explode his chute. The doc increased the milking speed as well, sending Analboy over the edge. He quickly shot another load of cum as a series of anal spasmed shook his whole body, filling the chamber even more with his red rectum. Analboy was now having slight involuntary spasms from the overdone pleasure that his sensitive rectum was being subjected to. the doctor let the machine run at it's current speed, but then started a pumping action on the vacuum as well. Analboy's rectum swelled and shrank to the rhythm of the vacuum. This brought even more pleasure to the boy and he already felt a third orgasm boiling inside him. His rectum was slick and shiny in the clear tube as the machine mercilessly pumped the helpless boy's rectum over and over. Analboy rolled his head back and forth as waves of fantastic ecstasy coursed through his crotch and throughout his body. He felt a short contraction under his balls followed once again by a rocket of cum splattering against the top of the rectum tube. The doctor stared in disbelief at the amount of rectal prolapse made by the vacuum tube, but he made note of it and let the pump continue. Analboy's eyes were now glazed over as he lay there, totally giving up on trying to cum. As the fourth orgasm came around, Analboy did not react since his energy was lost. He felt the throws of agonizing pleasure but made no reactions at all as his dick shot yet another load of cum. This load was much smaller than the last, but a few drops did spill. The doctor stared wide-eyed and amazed at the boy's drooling dick. "I have to keep this up until nothing comes out and your entire rectum is in this tube, you know. I have to know how much rectum can come out." "No problem," Dean said. "He can take it, looks hot..would love to slide my cock in the red meat when your done doc. He's had a prolapse fuck before." "All right. I don't think anything else will come out though. He's completely prolapsed now, the entire rectum is out..Good boy." The doctor was right. Analboy found the strength to arch his back in a painful position as the vacuum tube pulled a dry, fifth orgasm from his body. The boy was now sweating madly from the calories burned trying to stay conscious throughout the whole ordeal. The doctor didn't bother to take the pump off and it was still pumping as the he filled out the rest of the paperwork. Finally he turned the machine off and pulled the tube off the boy's rectum. The tube had deformed his prolapsed rectum into a long red tube shaped like a toilet paper tube with a small slit in the end Analboy knew someone was down there playing but he didn't care as he recuperated from his orgasms Mac was jacking his hard cock and when Analboy went to take a look, Mac was poised to slid his cock right into the prolapse slit. Mac straddled the boy's body, the doctor held slid a rubberband around the boy exposed rectum right near the asshole ring, so that Mac could fuck the red meat tube and not push it back into him. Mac slid his cock head in the boys rectal slit, the right to the base in one fluid motion "Oh his rectum feels great like this guys"Dean and the doctor both watched Macaulay perform with smiles on their faces as the boy picked up his pace. He was humping the smooth, red meat tube feverishly now and was breathing heavily. The six-pack of muscles in his belly were ballooning in and out with his lust for the young boy. He continued humping up and down, reaching an incredible sexual high as he felt a string of cum reach the end of his dick. The second string pushed the first out and it landed right in front of Analboys tube, all strung out for several inches. Macaulay rubbed his erection in his own cum coating Analboy's rectum, as he spilled the rest of his load, rubbing his dick and balls in that as well. Macaulay enjoyed himself a few more minutes before finally jumping down from the table. Analboy laid there a few minutes and was finally removed from the table by Dean who immediately removed the rubberband and pushing his rectum back into him using his rock hard 7 ½ incher . The boy made no sound when the cock was pushed in, but once again a whimper was heard as it was stretched to fill him up and restrain him from wandering further than the end of the chain connecting him to his master. After the doctor filled out the rest of the paperwork, they took it back out to Grady who reviewed the results of the exam, then signed the paper qualifying Analboy to participate. "What contest?" Analboy suddenly asked. "Is that why I just went through all that? So you could enter me in a contest? "It sure is." Dean stated, not caring whether Analboy liked it or not. "You're going to be in a contest and win me some money!" He sounded overly excited. Analboy looked back at Grady who was standing in front of him holding a horrifying looking piece of something. It was long, thick and hollow with a tube sticking out of the middle of it with a stainless steel tip on it. The tip was round and hollow as well. There were a few other things hanging off of it with buttons and plugs. Coming off the long section, there were two straps, one on each side, with Velcro and a padlock with steel heavy duty grommets. Analboy watched Grady and knew that he would be the one wearing that gadget. Grady started towards Analboy. "Whoa!" Dean started. "What's that for?" "It's to keep little Analboy here from cumming and the asshole always open, that's what" Grady replied somewhat coldly. "Oh! He can't cum for the next three weeks?" "No. And if he does, we will be able to tell, believe me, the asshole will be stretched out daily to a 3 inch width over the next 3 weeks as well. This will insure that his asshole never closes again." "Well, why can't he cum?" "Because it wouldn't be fair to the ones who don't cum but need to, that's all." With a sigh, Dean finally said, "All right, put it on." Grady grasped the end of the tube and sent the plastic tube with the metal tip careening down the boy's dick hole. Analboy tried to hunch over, but was held in place by his master who was grabbing him around the chest. Grady had the whole tube in now and then the 3 inch wooden shaft was inserted and the apparatus was closed The unit was small enough to fasten it around his waist which they did hurriedly, followed by locking it into place. It was then that Analboy realized that he would not be able to even touch his own dick until after the competition and that his asshole ring would be made useless. The shroud covering his boyhood made it impossible to jack off or be sucked off or anything. Everything was in place. Dean, Macaulay, and Analboy were all on the way back to the mansion and Analboy was in the back, tied down with his balls back in the ring, a the huge wooden shaft in his stretched out asshole, and a case around his dick that was keeping him from touching himself. He already had an itch down there that needed to be scratched. He would just have to live with it for the next three weeks.
The end

Chuck Manahandles the Rectum

Chuck Manhandles the rectum

Chuck wanted nothing more then to slide his whole hand up my asshole with no resistance, so that his whole arm would sink in my rectum right up to the elbow in one smooth stroke. We agreed it would take several sessions to destroy my assring enough to reach his goal, I was hot to see it happen as well and document it for the website. Today would be BDSM Rectal training session #1

Session #1 I arrived at his house, clean out my rectal cavity, as he prepped the playroom. Massive dildos the size of 1 liter water bottles (3 ~ 4 inches wide) lined the shelf next to the small medical examining gyno chair. He also set up some incredible long (14+ inches), but skinny dongs for colon bend work. He wanted my pubes freshly shaven baby smooth at all times for the rectal training. I emerged from the bathroom, ready. He was totally turned on by the way my pubes were shaved"So slutty looking, ready to get your asshole destroyed boy?, Climb into the chair whore and let AssDaddy get into your rectum good" He saidI climbed into the chair, placed my ankles in stirrups. He grabbed my hips and slide, my ass down until, it almost huge of the edge. He then lifted my ass off the chair my grabbing both but cheeks and lifting. H spread the ass cheeks wide and let my but down, so my asscheeks were spread, with hole fully exposed hanging off the edge. he took a seat on the stool wheeled close to my exposed anus. "Nice shaved asshole..look you a little gaped already!, lets isolate off those nuts now" he saidChuck grabbed my nuts with thumb and forefinger right above the top of the nuts, isolating off the nuts. He snapped a thick rubber band around my nuts and removed his hand. Then he took a piece of string tied it around the rubber band, then feed it thru an eye hook in the ceiling, then down to him where he held the end in his hand. I pulled the string"Ohh gawd my nuts!" I said. "Yep, this will keep your nuts isolated off and up out of the way as I destroy your asshole today and for the next 10 sessions" he smirked I then put on a set of latex gloves on each hand and coated his hands with KY jelly, two fingers slipped into my loose asshole."Yea, let Daddy in that ass, you whore", as a third finger slipped in and swirled right on the assring. Then a watched in the mirror on the ceiling as he took a finger from the other hand, slid it along side of the other three, I could feel my assring muscle stretch taught"Relax that asshole, whore, I'm going wide into you first, then will work on depth in round two. Here hit these poppers, they are very strong"I hit the poppers hard, my asshole muscle went limp, as another finger found it way in"There goes your asshole, Nice" he said, pulling one hand way from my asshole, and slowly sliding the entire hand from the other into the asshole, The ring muscle accepted the widest part of his hand, then it sunk in to the wrist"My whole hand is in your rectum, slut" he said, pulling on the string to my nuts, pulling them"Hold on for dear life, time to trash out your hole real good" as he spun the closed fist in my asshole, then tried to pull it out, pulling the assring out with it, then closed fist was nearly out, right at the ass-ring muscle"Oh gawd my ring" I cried , then PLOP, the hand left my asshole, the asshole gaped out obnoxiously, as he picked up a dildo equal in width to the fist that just left my asshole, he plowed the dildo right up my ass chute with ease, right to the bottom of the rectum, knocking on the colon bend that was beginning to loosen up too. I grabbed my thighs and pulled my legs and ankles as high and way back as possible, giving him greater access and ability to nail the asshole good and hard. He began to pick up the pace, nailing the rectum on smooth powerfull strokes. You could feel and hear the assring muscle popping over the head with every pull out.


"Yea!, Nail that asshole, punish it Daddy" I said, as I rotated my hips on very downstroke, allowing the dong to begin to penetrate that inner ring. "Oh gawd there it goes up into me" I screamed as he slammed the dong home into my lower colon, my whole body shaking and convulsing as he worked it, my little cock swinging as he pounded the colon bend to ruin.

Bondage Anal Friday

Bondage Anal Friday

A true story of Analboys antics

The assmaster picked me up in his van. It was a cold rainy day, as I watched the windshield wipers scrape the windshield. Bobby asked me " How's it goin' boy, ready for some fun". "yes" I replied, "I'm hot, and its been a long day". "Good as I'm gonna really work that asshole tonight slave" Booby sneered. The van moved down the hill and closer to Bobby place. "what's all that stuff in the back" I said. I looked in the back of the van, it was stuffed with all kinds of electronic equipment, lumber carefully cut and nailed together, various rubber hoses and antifreeze bottles. "stuff made especially for you and tonight's ass intrusion session. Bobbies hand was now patting my knee as we entered the driveway, "It's been a while, babe, since Ive seen your gaping asshole, I'm gonna eat it up tonight. Help me get the stuff out of the back of the van, we will take everything to the basement. Bobby opened the back of the van as we unloaded things in the wet rain. "Here take this video equipment first, we don't want to damage it". I carried the tripod and video camera downstairs as Bobby struggled with the antifreeze bottles. Down the stairs I set the camera and tripod down, and proceeded upstairs. "Wait!", he said, "I want you to stay down here, Ill get the rest. I want you to strip naked" He threw me a crumpled up shower curtain "The once naked, set up the video camera, spread out that shower curtain. In those antifreeze bottles is baby oil, coat you naked body with it, paying particular attention to your cock, balls and asshole". "OK". I proceeded to set up the camera on the tripod and plugged it in. The shower curtain was spread flat as I removed my work clothes and soon was naked.

Bobby returned carrying the rubber hose, looking closely, it really was not hose, it was more like a solid piece of rubber maybe 10 feet long and 2 1/2 to 3" wide. He had several of these all about the same length, but various widths, I had an Idea these were going in my ass, but was not sure what the really fat one were for, certainly not my asshole. Although I can open up wide, could never go 3 1/2 inches wide, he threw them on the shower curtain "Come one boy, oil up your body, you might as well do these black rubber things too" Bobby was ordering me now. I proceeded to lube my entire naked well shaven body, and was bent over doing my lower legs when Bobby was back carrying the wood structure "Nice ass" he commented. I was then lubing up these strange rubber objects as bobby was putting together what looked like a tree fort in the basement. I sat naked sliding on the shower curtain "This, my analslave, is you ass dungeon. You will be placed in there, your asshole eye level, and I will violate your asshole all night with the ball gag in your mouth to muffle your moans. The next trip down bobby bought all the restraints and the dildo collection. "OK, slut go clean your self out and shove the butt plug in your asshole". I proceed to the bathroom, after two large enemas, I greased my asshole again and began to slide a big butt plug in my ass. Slowly I slid it in wider and wider until it got to the widest point and "ohhhhh" it sank in, my sphincter closing around the 1" wide base.
When I returned Bobby was naked with a raging hard on, "Come her slut and suck you assmasters cock" he said. On my knees I could feel the massive plug stretching my inner anal ring. I licked and sucked his rock hard 7" cock, the without warning deep throated him, I could here his moans of delight as he grabbed my head and started facefucking me. I could taste the precum, he stopped "No not yet slut, I want this to last" Bobby said. "Now on you knees, face down ass high for you master. More baby oil was rubbed on my ass. "Lets pull out that plug and start hammering that asshole" he grabbed the plug and pulled, the plug expanded my asshole "unnnggggh" I groaned as he stopped at the widest part "Before I put you in the dungeon, some powerfucking with a dong is in order" My hands and feet were bound, Bobby greased a 10" x 2" thick dong and slid the entire thing in to my ass, "Ohhhhh gawd, your going deep into my ass, shit!" I was spreading my ass cheeks as he began to pick up the pace on the thrusts "Oh Oh Fuck Fuck, yea, work my asshole" I screamed. Bobby picked up the next widest dildo and slammed into mercillesy into my ass "Oooooouuuuu, oh gawd, oh my asshole", "Take it slut!" as he worked my ass, my moans got louder and louder. "Im gonna ball gag you bitch". Bobby got up and the red rubber ball was placed in my mouth and secured. Now Im gonna RUIN your asshole with my new rubber probes, get in the dungeon slave" The video was turned on, as I was made to pose for it, by shamlessly showing the camera by raw open asshole. Bobby walked up dipping his cock into my open asshole, me muffling into the gag as he pumped it. "Up into the dungeon, slut and face your asshole to the camera. Good, now spread your ass cheeks and stick that asshole between the bars" I did as told, the smooth wooden bars holding my ass checks open, fully exposing my loose asshole. Bobby picked up the rubber cylinders and criscoed it up. It was amazingly flexible and would not stick straight out on its own and on the side was printed 2.5" Gates. It must indicate its width, as it seemed that big across, it was about 4 feet long. With two hands he pushed into my wanting hungry hole. Its slid in far "Mmmmmppphhh" I gagged through the ball. "oh yea babe, 10" already!". He began to stroke the soft rubber in and out of my ass hole each time a little deeper " Thats it 11", 12", shit its bottom out slut!" He said. "Ohhh my asshole" I screamed silently. Watching the video of this thing violating my asshole. I watched Bobby work it. He spun it in circles and swirled around, it still bottomed out, around and around until, he suddenly stopped "Ok there's the bend" he said. With that he pushed and the thing snaked way up my colon. "Mummmmpphhh, MMmmm" I cried. "yes bitch 20" way up in you!, what??? your muffling I cant hear you???, Ok let me take the gag out".. He undid it, leaving the tube buried. "Ohhh bobby my asshole its too deep, it feels so weird" "that's The idea slave, wait Ive got a 3" and 3 1/4" diameters to snake in you next!". Please, Bobby my asshole, you'll ruin my asshole, its all red now". "ok, ok, lets take a break, Ill get the speculum" he said unwillingly.
The large speculum was warmed with Bobby hands and lube was applied. The large blade a full 4" long were inserted into my rectum. He twisted the screw as I felt my asshole being pried open. Wider and wider my asshole was spread, as Bobby compared the size of my ass to the objects that was just inserted. "oooh shit my asshole its loosening!" I moaned in ecstasy as the magic 2.5" width was met, and passed. The 3" width was approaching . "Ohhh Bobby thats wide enough, you'll ruin me!", "ok, ok, now just lay there, Im going to get a beer, be right back". Bobby left as I squirmed to get comfortable in the wooden dungeon, my anal ring fully stretched tight. 15 minutes had passed, with each minute, feeling my ass expand and loosen to accommodate the large speculum. Bobby returned with a beer in hand, and began to remove the speculum, "My god!, look at those ass lips you have now! I think your ready for the 3" diameter black rubber anal tube. I watched in the video as Bobby greased up the 4 foot monster, I could see my asshole in the video, it was wrecked!. Huge red asslips parted as the 3" hose started sliding in my asshole. "Ohhhhhhh, gaaawwddd!" I screamed as 8" slid in my ass, Bobby did not stop there, he was counting "9, 10...11 inches, fuck yea deep in your fucked up asshole!" he stopped. He stepped back to look at the scene, a 4 foot hose, 3" diameter buried 11 inches and a ruined asshole, with my contorted face of pain and ecstasy. "ok slave. Lets go back to the speculum, stretch you out a little more for the largest 'rubber snake', 3 1/4" babe, let really stretch that limit!" , I hesitated. "Ok master I will try". "Good, if you can do this wide, Ill fist out your asshole alot!" He grinned as the blades of the speculum entered my ass, Bobby adjusted the screws "ok your at 1, now 2 almost three!" "Oh I feel my hole expanding master, ohhhhhh" "ok almost 3", there 3, how does that feel?" "my anal ring feels stretched tight" "hold on a little more" "Ohhh gawd stop, its getting to wide". "ok let its stand there and let your ruined asshole expand even more. I sat the doggy style with my asshole stretched wider than ever. I was sure it would never get small again. 10 minutes passed, Bobby greasing up the largest snake. "ok lets doit, make mincemeat of your anus!" The speculum was removed and the big tube was pushed at my ass "Its not going master, its too wide!" I said. Bobby pushed harder, my asshole expand and the tube slide in. "Unnnnghhhhh, oh shit, you ruining my asshole, ohhh fuck!, ohhhhhh" is all I could say as I watched inch after inch sliding into my ass. "ok Im going to hold it I want you to turn around, lay on your back legs over your head. As I did the rubber snake slid deeper into my asshole, "good, its going deeper!" On my back, Bobbie swirled the thing in my ass, thrusting it in and out, determined to go deeper in my asshole. "thats it your taking it like a real analslut, look at that ass!, Now jack off, and cum I want to see that asshole spasm!, but tell me right before you come, so I can pull out" I started jacking my hard 6" cock, Bobby was playing with his own too. I was not long "Im gonna squirt!" I cried. Bobby yanked out the tube, and spread my asscheeks "Oh Im cumming!" With that my asshole spasms started. Open then shut, open and shut. Bobby seized the opportunity and sank his cock in my asshole as long continuous anal orgasm milked his cock. "Ohhhh fuck yea, that feels great!, Im gonna shot my load into your ass!" It took only three thrusts as Bobby blasted a huge load on the downstroke. It was the end of a long ass opening session.......

The end