Date: Thu, 2 Jun 2011 18:59:52 -0700 (PDT) From: Billy Berglund Subject: Halloween Helper Part 10 If you shouldnt be here, be gone! Enough said about all rules you know em. Obey em. This story belongs to the author and may not be reprinted without permission. It is writen solely for the readers enjoyment. This story is a continuation of the Halloween Helper series. If you havent read it yet it might be good reading for the background on these two characters. Okay, get your cocks out and lets get on with it !! This story is dedicated to all the fans for your support and suggestions. Thanks so much. I hope you enjoy this seasons installments. After a couple hours of sleep I got up. All the boys were sleeping and wouldn't be stirring for hours yet. I made my way upstairs to the room Jayjay was in. Silently I unzipped his sleeping bag and laid next to him. Hugging him and cuddling next to him I enjoyed the scent, feel and warmth of his young body. I let my right hand drift down to his Tommy boxer clad ass. Running my hand over the curve of the ass I got a good feel of the cherry ass I would soon be taking. My cock was hard and I was growing hornier. I shook him and whispered his name not wanting to wake the other boys. He didn't wake up so I shook him a little harder. Still nothing, so I gently scooped him up and carried him down to the basement break room. I kept one hand on his butt squeezing his cheek as I carried him. As we descended the stairs I called his name louder and pinched his nipple with the arm that I had draped around him. He started to awken, groggily asking me what was going on. I told him I had woken him early so we could get some practice in. He looked at me confused and I brushed the hair out of his eyes and let him down as we entered the break room. "First, get us a couple of sodas Jayjay and then I'll tell you about the practice session we're gonna have." "Okay, Billy" he said. I watched him as he walked over to the mini-fridge bending over to get the sodas out. His cotton Tommy boxers stretched taut across his skinny butt, riding into his crack. Mmm what a sexxy sight. He got the sodas and turned around and walked over to me handing one. "Okay, now what are we going to practice for this morning?" he asked. "Well Tommy, if we have the time before your parents come to pick you all up I'm thinking we would have a rematch on the hotdog walk. You didn't win but I think you have great potential and want to work with you so you have a better chance of winning. Does that sound good?" "Sure Billy. I didn't think I did that well but if you want to help me I'm up for it." "Jayjay you did very good. Don't doubt yourself. With a little practice I know you can do it and win!" "So you want to do it now?" "Yes Jayjay we can do it now before the others get up and noone will know that you were practicing." I winked at him. "Kewl!" "There's more hotdogs in the fridge if you want to grab one and take your boxers off. I'll help you get it in again, then you're on your own." He went to the minni-fridge and got a hot dog out of the package and handed it to me. "Now turn around and get your Tommys off and bend over." I watched intently as he slid the boxers off and bent over. His tight puckered hole became totally exposed to me. I grabbed the lube off the top of the fridge and squeezed some right into his crack. I rubbed it around his cherry hole with my finger applying pressure and slowly inserting my finger. When I was in to my knuckle I gave it a twist. An oomph escaped his lips. He asked if it was in and ready. I chuckled and told him that it wasn't. I was just using my finger to get him better prepared. I explained we had more time now and could do this right and he would be a sure winner. I then quickly jammed my whole finger into him. "Ow, ow, owwwwww!"he cried, "What was that?" "Nothing my sweet Jayjay. I was just testing your reflexes." I said laughing and gave him a smack on his butt and pulled my finger out. "I think you're ready now let's give it a go. Okay here it comes. It will be cold so brace yourself. A litle pressure now and....it's in." I slid the dog about 2 inches into him. He stood and I told him to squeeze down on it and walk slowly. He made it to the other side of the room and turned around beaming. "Now come back to this side but walk faster. Remember, speed counts." Of course he did'nt make it all the way then. I had him turn around and bend over again so I could get it back into place. I pushed it in and pulled it out a couple times telling him we had to make sure that it was in right and would stay in. After working it in and out a couple times I pushed harder driving it 3 inches into him. I watched him as he got better at squeezing it and holding it in. After a few more tries at it I had him bend over once again. I looked at the hotdog dangling out of his tight hole and I was so ready to fuck him whether he was ready or not. "Ya know Jayjay what we need is something bigger. If we had a Plumper hotdog we could use that and then you would easily be able to hold the regular dog. Too bad we don't have any Plumpers. Hmmmmm. Let me think a minute maybe I can come up with something." I toyed with the hotdog in his ass for a few minutes then pulled it out. I spread his ass cheeks apart and used a finger from each hand to pull apart his hole. I slowly slid my right finger up into his well greased butt hole. So hot and tight I couldn't wait any longer to get my monster cock up his virgin boy pussy. I withdrew my finger and smacked him on his ass exclaiming I think I got it Jayjay! "Let's go over to the chair I have an idea I think will work." "Kewl Billy what is it?" he asked while walking over to the chair. "First bend over the arm of the chair so I get your little butt in the right position." I spread his long, slim legs and stepped between them. I reached down and lowered the front of my boxers freeing my cock. "Now reacch back here with your hand." I grabbed his hand and took it and placed it on my hard cock. "What do ya think? Does that feel like a big ol' Plumper?" "Yeah it does and it's hot too!" I moved his hand up and down my throbbing member. His tiny, long fingers felt good wrapped around my cock but his boy pussy was going to be absolute heaven. "What is it Billy?" "It's the perfect Plumper substitute and it will get your little butt stretched out just perfect too." I placed my throbbing cock at his entrance and warned him it might hurt a little at first. Then I gave a hard push popping his cherry and breaking through the ring with my head. At last I was inside this boys hot little ass. I let out a loud groan as his ass encased my cock, grippping it so tightly. Jayjay screamed and pleaded for me to take it out. "No whining Jayjay. You know the saying, no pain, no gain. I'll have it all in ya in just a little bit and then it will get better." "No, no! Take it out. I give up. I don't care if I win the contest." "Shut up Jayjay. I don't like losers. Just try to relax and take it all so we can get this over with." I bore down on his tight ass inching my cock into him. I don't know how he was going to take it all but I didn't care either. It looked so massive wedged between his little butt cheeks. I continued pushing, forcing my cock further into his delicious boy ass. I grabbed my cell phone and took shots of my hard cock into his tight little ass. I grabbed his slim hips and pulled him back as I thrust forward. My cock throbbed in the warm confines of his ass as I began pound him harder. I brought up the pic of my cock penetrating his ass and held it by his face so he could see it. "See that Jayjay? That's my big ol' fat plumper up in your butt. Gonna make you a prize winning ass!" "Oh my god Billy! Y-y-you put your thingy in my butt. Please take it out it hurts so much. I don't care about the contest." "No, Jayjay it's staying in. You agreed to the practice and now that I got my big plumper in you it's staying in until your good and stretched out." "Noooooooooo! Oh please Billy I can't take it and I don't like it in there." "Way too late for that Jayjay. Your tight little butt makes my cock feel so good. We're going all the way." With that I slammed my cock deep inside him and started rotating my hips. Little Jayjay was getting the fuck of his life. I picked up my speed ignoring his cries of pain. I was almost all the way in him and drilling his tight ass for all it was worth. My hard cock was throbbing wildly as I fucked into the boy towards my climax. "Oh fuck yea Jayjay your butt feels so good. Nice and tight. We're going to be practicing a lot. Keep taking it baby. Oh yea I'm gonna bust my nut up your sweet ass Jayjay." I slammed into him, pile driving his little boy ass. Watching his body lifted then pushed back down into the chair. I let out a gutteral moan as my cock swelled up and then unleashed a torrent of thick, hot cum in his bowels. I continued moving my cock in and out of his abused hole spreading my burning seed in his cavity. Finally collapsing onto him and holding him tight to me. I helped him clean up and promised him he would be alright. I carried him back upstairs and layed him in his sleeping bag, kissing him softly on his cheek. **This will complete the series until Halloween rolls around again. I will be working on some other stories I've got in the works. Thanks to all who have written in and for the pics you've sent. Keep writing to me and be looking for some of your suggestions in upcoming stories** Other stories by this author: /nifty/gay/young-friends/first-camp/ /nifty/gay/young-friends/eating-hotdogs-and-stuff /nifty/gay/adult-youth/halloween-helper/ /nifty/gay/adult-youth/at-the-concert Thanks for reading and I hope you enjoyed it. E-mail me with comments or suggestions to the addy listed above.