It happened during the summer of 2004, when Billy was sent to live with his grandpa. Billy's dad left him and his mother when he was a year old. Susan did the best she could as a single mother to raise him. During his high school years, Billy started to hang with the wrong crowds and got himself into a few minor scrapes. Billy turned eighteen and graduated high school in 2004 and his mother thought it would be good for him to spend a summer with her father. Billy needed to learn how to be a mature young man and her father would be the perfect person to help him.
Susan drove Billy to her father's house out in the county. The two hour ride was rather quite. Billy did not say much and Susan would make comments from now and then on how this would be a good experience for him. They arrived at the house and pulled into the driveway. Ed came from the house to greet them. Ed was a rather large man; standing 6 feet weight a lean 195 pounds. He gave Billy a hug and was dwarfed by his size. Billy was rather small at five foot four. Susan hugged her father and then the three went inside the house. They sat in the family room and Ed told Billy how happy his was about him staying for the summer. After about an hour of small talk, Susan left and headed back home.
Billy took his suite case and Ed showed him to his room upstairs. He told Billy that he should take a shower and then come down stairs for dinner. Billy agreed and he headed for the bathroom. While he was in the shower gramps came in and asked he minded him taking a leak. Billy had no objections and from the corner of his eyes he saw gramp's fat cock handing out from the fly. He figured it must have hung out about five inches and figured there must have been about two more inches still inside his pants. While he glanced at gramp's fat cock, he realized his cock was getting hard. Gramps noticed from the corner of his eye Billy had a hard on. When he was done, Ed flushed the toilet and then began to remove his clothes. He turned around and looked at Billy in the shower.
"Looks like you got excited seeing gramp's cock boy. Ever seen a cock this fat boy? I think gramps needs to show you what you want and crave."
Ed pulled back the clear shower curtain and got in with Billy.
"Tell gramps why your cock is hard boy. Don't make me wait for an answer. I won't hesitate to get the strap out like I did with your mom."
Billy stood under the water with is cock sticking up at an angle. It was smaller than average and really small compared to gramps.
"I've never seen a cock that big before gramps." He said in a low voice.
"I see, you a sissy boy? Your mother told me about the type of kids you hung around with. So tell me what really happened in the park bathroom. I don't think your mom got the whole story."
"I was caught sucking off the old men who would hang around. Sometimes they would pay me a few bucks to sit on the toilet while they stood and put their fat cocks in my mouth. A few would piss in my mouth after cumming."
"Get on your knees sissy boy. I want you to show gramps how you suck cock. It's been a while since I had a hot mouth on my cock boy. Later tonight gramps is going to put his fat cock up your slut hole. Bet you're a really tight one."
Billy got down on his knees. Gramps grabbed his fat cock and slapped Billy's face with it. Billy opened his mouth and gramps shoved in it. Billy gagged at the size as he was barely able to open his mouth wide enough.
"Suck that cock sissy boy. Show gramps how much you love sucking cock. I'm going to make you my sissy bitch. From now on, you'll call me Sir. You will only speak when spoken to. You'll answer to sissy bitch. You got that boy?"
Billy nodded with his mouth stuffed with cock. Gramps grabbed Billy's head and started to give him a good skull fucking. He was ramming his eight inch cock in and out and pushing deeper each time. Billy could not stop what was happening and would gag. Gramps could feel his balls tightening and his cock swelling. He leaned over Billy and turned the water off. Sensing he was ready to cum, he pulled his cock out.
"Open that cum bucket boy." He yelled
Billy opened his mouth wide and gramps began to shoot his come over his face and into his mouth. After a good solid cum, he looked down at Billy's face covered in cum.
"Now wipe my cum up boy and eat it. Don't be wasting my time. That's a good sissy bitch. I can't wait till I have the guys over tomorrow night for poker. They're going to like having a sissy bitch for their use. Now gramps has some desert for you sissy bitch."
Gramps shoved his flaccid cock into his mouth and let go a large stream of hot piss. Billy gagged and gramps cock slipped out and Billy puked on the shower floor. Gramps still continued to piss all over Billy.
"Puking is going to get you a punishment boy. I'm going to my own shower to clean up. I want you to clean up and to shave your legs, cock and ass. When you're done, I want you in my bedroom waiting on your knees with your head down. You got that boy?"
"Yes Sir." Billy replied with a whimper.
Gramps whet into his bedroom and then the master bath, where he took a quick shower. After drying off, he slipped on a jock strap and then when into the closet. Inside the closet he removed a large razor strap from a hook and then grabbed the plastic shopping back sitting on the floor. Gramps sat down in a chair and lit up a smoke. He waited the arrival of his sissy bitch. After finishing his smoke, Billy came into the room and knelt down before gramps.
"Stand up sissy bitch. Gramps wants to make sure you shaved really well. Put your hands behind your head and spread those legs."
Gramps ran his hands up and down Billy's smooth legs. Billy's cock started to stiffen as he felt the large rough hands run up and down his legs. Gramps then fondled Billy's cock and balls.
"Looks like you were last in line when cocks where given out boy." Gramps said with a laugh.
"Not big enough to be called a cock. From now on we'll refer to it as a pee pee." Again laughing at Billy.
"Now turn around and show me your slut hole." I'm going have fun ripping it open with my fat cock."
Billy turned around and bent over.
"Pull it open for me sissy bitch." Ever had cock up there?"
"Great, then I can take be the first to ream your slut hole."
Gramps spit on his middle finger and then pushed it deep into Billy's slut hole. Billy winced as the large finger slid it. Gramps moved it around and then pulled it out.
He looked at his dirty finger and uttered to Billy. "Looks like you got another punishment sissy bitch. Now turn around and kneel before me."
Billy complied and gramps slid his dirty finger into his mouth.
"Suck it clean. That'll teach you to have a dirty slut hole. Better keep in clean unless you like the taste of your own shit."
Billy grimaced as he cleaned the soiled finger. When he was done, gramps told his to stand at the foot of the bed, legs spread and to lean over.
"Time for gramps to punish his sissy bitch. You're going to get five licks of the strap for puking. The sooner you learn to be a good sissy bitch the better it'll be for you."
He stood next to Billy and with one swift move, brought the strap down on Billy's ass. As soon as the strap was brought back up for the next one, a red welt appeared. By the time the fifth one landed, Billy was crying and screaming.
"Cry all you want sissy boy. No ones going to hear you. Take your punishment like a good sissy bitch."
When it was over, gramps put the shopping bag on the bed. He dumped the contents on to the bed. It was filled with an assortment of items, one of them being a butt plug. Gramps lubed up the plug and stood behind Billy and pushed it in one motion. Billy gasped as the plug spread his virgin slut hole. Once the plug was seated, he felt like he had to shit real badly.
"Stand up sissy bitch." Gramps ordered.
He picked up a large Kotex pad and a pair of pink cotton panties. The strip was removed from the pad and was stuck to the crotch of the panties.
"Put this on sissy bitch. The pad is to make sure you don't soil your new panties."
Billy took the panties and slid them on. They were really tight and gramps told him to stick the tip of his pee pee out and to have the elastic band just below the head.
Gramps went into the closet and retrieved his digital camera.
"Ok sissy bitch. Time to show gramps how cute you look wearing those panties. I'm going post them on the web tonight for my male friends. I want one picture with your panties pulled down showing your Kotex pad and another showing your plugged hole and strap marks."
Billy was now being humiliated for the please of others. He posed as he was told. Gramps also took some of Billy on his knees licking gramp's jock strap.
"Good sissy bitch. Now for being so good, I'm going to let lick my ass. I want to feel that tongue in my ass."
Gramps bent over slightly, reached back and spread his hairy ass. Billy eager to feel the strap again eagerly licked gramp's ass. Gramp's cock began to harden feeling the warm tongue up his ass.
"Ok sissy bitch, it's time to eat. I want you to crawl to the kitchen and wait on your hands and knees while I make dinner."
Gramps walked behind him as he crawled downstairs to the kitchen. Gramps fixed a simple dinner of hot dogs and when they were ready, he cut two of the up into small pieces and put them in a bowl and put in on the floor along with a bowl of water.
"Eat up sissy bitch." He said with a laugh.
After finishing his brief dinner, gramps got up from the table and went over to the closet. He opened the closet and removed a leather collar and leash.
"Get over sissy bitch, time for you to wear your collar and leash. One other thing I forget to tell you. You're not allowed to use the toilet. Gramps will take you off the back porch and watch you do your business. When you need to go, you'll crawl to me and say leash. Now do you have to do your business sissy bitch?"
Billy nodded yes.
"Take your panties off sissy bitch and let gramps take that plug out."
With his panties gone, Billy crawled over and gramps leaned down and pulled the plug out in one swift move. He's slut hole was agape about a half inch. The collar was put around his neck and the leash was attached. Gramps opened up the back door and led his sissy bitch out the door.
"Now don't forget your going to do your business like a good sissy bitch. You're going to lift a leg to pee and squat to shit."
He walked Billy to a tree in the back yard and watched him lift his leg to pee. When he was done peeing, he squatted down and grunted as he pushed out a load of shit.
"You done with your business sissy slut?"
Gramps tugged at the leash and they headed back inside. Once inside, gramps took him into a spare bedroom. Billy noticed a chair in front of a computer and a camera.
"Now lay down sissy slut. Gramps is going to go on line and post those pictures I took earlier."
He logged on to a chat room called "Sissy Boys." He then turned on the web cam. He noticed a few of his buddies on-line and they started chatting. A lady was in the room and asked to view his webcam. He gave her permission and soon saw him sitting in his chair with the camera focused on his jock strap. She sent him a message telling him about her sissy boy and then sent an invite to view her camera. He clicked on the invite and saw her in a chair naked wearing a strap-on. She appeared to be in her late fifties and looked pretty decent. He sent her a message to watch his cam.
He stood up and removed his jock strap. He large fat cock hung low over his hairy balls. He sent another message "Wanna see my sissy bitch take his first cock up his slut hole?" She replied yes and then activated her microphone. He did the same and them he spoke.
"Suck my cock sissy bitch. Get it nice and hard so I can ream your slut hole with it."
Billy got up on his hands and knees and started to suck his cock.
"My what a good sissy boy you have there." She spoke.
"Thanks. Today is his first day. He got a strapping earlier for puking after using his mouth for a urinal."
He heard her say "Get over her sissy cocksucker." He watch as a small framed boy entered her web cam view. He had a very small cock that was covered in a metal tube.
"Now suck momma's cock for the man. Show him how you like sucking momma's cock."
The boy started to suck and deep throat the fake cock.
"Get it nice and wet so momma can show the man how you like it up your boy pussy."
By now gramp's cock was ridged. He looked at Billy and said "Get up, bend over and spread that slut hole.
Gramps was watching the ladies cam as her boy got up and bent over. He watched her large fat strap on push open the boy pussy. Soon the ten inch cock was up his boy pussy.
Gramps grabbed a bottle ok KY lotion from the table and greased up his cock. He put the tip on his cock against Billy's slut hole. Billy squealed when the first 3 inched entered his tight hole. The lady watch as Gramps pushed his fat cock all the way in.
"Oh fuck it hurts Sir. Please take it out Sir."
Gramps slid it out and waited a moment before shoving the entire length back in. Billy winced and started yelling. "It fucking hurts Sir."
"Shut your mouth sissy bitch. It's supposed to hurt. Nothing feels better than raping your slut hole."
The lady spoke up. "Very nice, I like the look on his face with his hole stuffed with a fat cock. All sissy boys like being raped by big cocks real or fake." She said with a laugh as she continued to fuck her sissy boy hard.
Gramps grabbed Billy's hips and continued to rape his slut hole. "Jesus, this is one tight hole. Your tighter than your mother when was she was your age." Ed reached around with his right hand and began to slap Billy's pee pee. Ed looked back at the computer screen to see the lady giving her sissy boy a serious fucking up the ass. He could see the fluid leaking from her cunt and figured she was enjoying the hell out of it.
Gramps felt his balls tighten up and yell. "Gramps is gunna fill that slut hole. Be a good sissy bitch as take my load. You better not shit after I pull or they'll be hell to pay." Gramps emptied the contents of his balls into his sissy bitch. His slut hole was so tight that cum started to leak out before gramps emptied his balls.
"Watch this." He told the lady.
Gramps pulled his cock out and Billy's slut hole was still opened about one and a half inches.
"Nicely done." The lady replied.
She then pulled her fake cock from he sissy boy and gramps saw the boy's hole spread about two inches apart.
"Sissy slut, I don't want you to leaking cum and shitting all over the place."
Gramps handed him a disposable diaper and told him to put it on.
Now get on your knees sissy bitch and show this nice lady how to clean off my cock."
Billy got down on his knees, he's slut hole still on fire, leaking cum and feeling like he had to take a shit. He's grabbed gramp's dirty cock and began to lick it clean. The taste of his cum and shit almost made he puke, but he held back knowing he didn't want the strap again.
Almost done with cleaning gramp's cock, Billy let go a loud fart and then messed his diaper.
"You just mess your diaper sissy boy."
"Did I give you permission to use your diaper sissy bitch?"
"When you're done cleaning my cock, hold open the front of your diaper so gramps can piss in it. Hope you like the smell of a messy diaper because you're gunna be in it all night."
The lady spoke and said. "He looks cute in his diaper. Next time after you cum in his slut hole, give him a piss enema."
"That's a wonderful idea." Replied gramps.
"Thanks for the show lady. Hope to see you again and perhaps one day we can get together to trade sissy bitches."
"You're welcome. I like the idea of trading sissy bitches."
Gramps turned off the video cam and closed the window on the lady's cam.
"Gramps is going to take some more pictures of you sissy bitch. The guys are going to love this tomorrow night!"
Billy was still kneeling in front of gramps in a messy diaper with a hard-on. He though "Why do I like this?"