I woke up early as usual got dressed and went for my morning run. The whole time thinking about my day and how I was going to change things. When I got home dad was leaving for the office and mom was, well wherever the fuck she was. I grabbed a glass of juice and went up to shower and tried to figure things out. Fuck that did not last long as my phone rang and it was Ray asking me to come over and complete my task. I told him I was busy, told me I needed to bring my enema equipment and to get here as soon as I could. I said fuck dude this has to stop and he said cut the crap and let's get this done, I'm alone for a while.
I dried off put a pair of shorts on and a tee and started over. I walked in and he asked for the enema stuff and told me to get into the bathroom and undress, which I did. He said he was going to give me the same enema I gave him and that then he would then shove a butt plug up my ass and that I had to hold it sitting on the commode for 5 minutes while he watched. I looked at the butt plug and fucking freaked out, I had never seen one and it was fucking huge. I started to get dressed. He started to get physical and grabbed my hair and I took a swing at him and hit him in the stomach. He laughed and said really dude, just fucking stop and get to it. The bet was I had to hold all that in for 5 minutes while sitting on the toilet. Just like I did he lubed my ass and stuck a finger in then started with the 5 enemas. When that was complete he said get up on all fours and now the fun starts. He put more lube on my hole set the plug in place and said breather fucker this is going to hurt and he pushed and I screamed. Get that sorry ass up and sit on the commode. He started a stopwatch and the agony slowly built. My ass hurt and was stretched and the fucking cramping started at 3 minutes. He could see I was struggling and was laughing at me. Then he reached for my nips and squeezed, I slapped his hands away and told him that was not part of the deal, but the distraction helped. At 4 minutes I was really suffering but was determined and Ray was starting to get nervous. Finally, it was over and the plug and the enema was still in place. I told Ray to reach behind me and pull the plug out, he laughed and said I'm not getting your shit all over my hand and left the bathroom. I pulled the plug out and fuck did that hurt and the enema squirted all over the toilet. I cleaned up got dressed and went to Ray's room to find him sitting on the bed with his hands covering his face sobbing. He looked up and asked, what's the next task. I told him there would be one and he would not like it as he totally wrecked my ass but I needed a couple of days to sort things out in my head. I pulled him to his feet gave him a hug and said dude " BIG GIRLS DON'T CRY" and I hope you are a big enough girl to deal with what you will have to do next. Enjoy the three or four day reprieve. Oh and clean the bathroom before you parents come home, laughing I left.
I barely made it home when I had to shit again and now I was really pissed. My hole was so stretched I was leaking. Not exactly the start of the day I had planned but it was time to deal with Tammy. I called left a message and she called right back. I told her we had to talk and asked when she would be free. She replied somewhere private and be prepared. I said somewhere public would be better and she said fine, but was clearly unhappy. I suggested Barnes and Noble's at South Hills Village. She reluctantly agreed and said noon which was great as I could get to the weight room at school mid afternoon. When I arrived she was at a table drinking iced coffee, I ordered juice and sat down. She said what up and I said we needed to talk about the other night and your new interest in getting into my pants. I told her I thought that out of the blue she was moving pretty fast and ask why the change. She said because she was on the pill now and everyone was doing it and she wanted it with me. I said what if I wasn't ready and her reply was you are the only 16 yeas old guy who isn't ready. I told her besides my car was not where I wanted to have sex for the first time. She said fine my place tonight the rents are going out and the bratty brother was at a friends place for the night. I told he no, I was not up for that, she quietly said fuck off fag and stormed out.
I was actually relieved. I went to school and worked out and was pleased that Ray was not around. In the shower our QB, Jeff, came buy and asked if I was free for a while and he wanted to chat. I was glad for the change of people around me. We went to McDonalds, I had a salad and he had a Big Mac. We chatted about things football, girls, school, very low key and relaxing. On our way out he said there was a party at his place Friday night and asked if I wanted to come and bring Tammy. I said I would be glad to come but someone else would have to bring Tammy as we broke up this afternoon. He slapped me on the back and said dude there is a line of chicks waiting for that to happen.
I had a few calls from Ray but was ignoring them and even though I knew it was probably too late I called the school guidance office, I wanted to set up an appointment. To my surprise the secretary answered and I told her who I was and that I would like an appointment. She said Mr. Durham would be available tomorrow in the morning and if I could stop in around 9:30 that would be perfect, she would pull my records and have that ready for him in the morning. Just two thing more to do, Coach and Ray. I called coach first and told him I had talked with my dad and that football next level was an interesting thing, but that education was the priority. I asked which schools had contacted hi, and he said WVU, Pitt and Penn State, IUP and Cal I was blown away, local interest and that made sense for an unproven junior. I asked that he refer all that stuff to my dad and provided his work number. I told him I was all about having fun working hard and having a great season. He said one mort thing, think about moving to linebacker, fuck the gremlins keep coming without stopping. Coach why would we do that? His reply was that the interest was because of size and physical play not my running ability, I was very fast for a linebacker but only fast for a HB. I asked what's best for your team and he said we will see.
Now I had to deal with Ray. I called and he picked up on the first ring, dude where have you been. I replied busy what's so fucking important. He said we have to talk and I said I have been doing a lot of that today and I needed a break. If he wanted to hang out and chill I was cool but nothing serious. I told him my parents were home and we had to cool the drinking. He said fine and I told him I was not discussing anything serious, especially the stupid fucked up bets. He agreed and I told him I had a Tammy story to tell hi. He said he would stop over after dinner.
Ray came around 7:30 and we just sat and had a friendly chat. I told him About Tammy and he laughed out loud. So you turned down sex with her tonight to be with me, you are a sick puppy, I laughed and said I was just not into her that much. We played videos for a while and around 11:00 he got up to leave. He said he enjoyed the stress free night, but that we needed to talk, I said I know and we will but you started this shit with the uncomfortable bets. He smiled and said I know but on a weird and sick level it is fun. I had to agree on some level but I needed a break and it was going to get real serious. I told him I had a 9:30 meeting at school and we could talk after we worked out. I told him I would be there earlier around 11:00. He said that worked and we could go somewhere where we would not be disturbed after the workout. Dude, just pick a place and let me know, I can't deal with much more.
The next morning I ran ate breakfast and went to meet Mr. Durham at school. When I got there he came out from his office to greet me and said damn, what happened to you your so much bigger. He open my folder looked over my grades and activities. He said excellent grades, football and not much else you need volunteer work and extracurricular activities. Basically you can do whatever you decide. He ask about my interests and I discovered I am very limited. He suggested we schedule an aptitude test first week of school and go from there. I thanked him for his time and left for the workout.
Ray and I drove each other hard and pushed each other, I was fucking exhausted. We showered and Ray suggested we just sit in the stadium. We were alone, most certainly, and he asked what his next task would be. I stopped him and asked how comfortable he was so far and did he want to stop. He replied he didn't. I asked again if he wanted to end this and simply have sex. He said no that would not work for him. I said fine but after the butt plug thing, I was raising the stakes quite a bit. Romantic sex would be easier on him but I was willing to just do it and not care about his feelings or comfort or lack of comfort. He said fine but that would also apply to you, Mike. I told him I was less comfortable with these games and I understood but needed to slow the tasks down time wise, once a week at the most. He agreed, I asked agin are you sure and he said yes what's the task. I told him he would be naked on all fours on a bed or on his back holding his legs up, I would lube his ass and fuck the shit out of him. He would have to give himself an enema to clean out and I was not using a condom. Finally, when I shot my load in his ass my cock was going right to his mouth. He just sat there a minute then said when and where. I reminded him he needed to be sober. Then I asked what his thoughts were. His reply shocked me, dude I knew it would get to that eventually and as long as it is something I have to do to keep my word and not my choice, I am good. So I said you are going to just take it hard up the ass when there were other options. I asked, what if the task was romantic sex and he said the same thought process applied. Time and place to be determined.j
To be continued and please provide some feedback.
Please contribute to the continuing operations of the Nifty Erotic Stories Archive website using a credit card or other methods of donation, we encourage our supporters to make a donation to the Nifty Archive Alliance