Cast of characters - it was always about the bets

By Mike Simmons

Published on Aug 13, 2019

Bisexual

I had a lots of crap to deal with but I wanted to deal with Ray first. I needed to get the enema syringe and get it over with as we only had 24 hours. I called him and reminded him he needed an enema. He told me we could do it as his place later that night. I promised him I would go easy, it helped as he remembered getting one around age 8 or 9. I got there after dinner and told him we should do it in the bathroom to minimize the possibility of a mess. I suggested a bet where he would have to take 5 full bulbs and hold it 3 minutes after the last build of warm water was inserted. My bet was he could not do that. I was really taking it easy this time. I wanted him to win to see where he would take this.

I told him to get naked and lay on the floor on his left side. He bitched that the floor was cold and I reminded him he did not want to lose another bet. I then instructed him to pull his right leg as far up as possible and get ready. I filled the sink with warm water and and filled the first bulb with water and sat it in the floor. I took some lube and put it on his hole and pushed it in with my finger, he screamed fuck dude you are not supposed to finger fuck me. I simply inserted the syringe/bulb in and gently squeezed the water in. I quickly refilled the bulb and inserted it in his ass and squeezed again. I did it slowly so it would be easier on him. I repeated the process till he had all 5 in is gut. I helped him up and made him stand beside for the three minutes and then told him he could release it and I went into his room so he could have privacy. About 10 minutes later he came into the room with a big smile and said now bro it's your turn. Ray said he would get me my task tomorrow. I was thrilled at the slight break break.

I went home and found dad in the den and asked if we could talk. He said sure come in and have a seat. I asked if we could go somewhere more comfortable for me like the game room and he agreed. Once we were comfortable I started by saying I had a lot going on and I needed him to have him listen and weigh in on a few things as he felt appropriate. I took the easy way out and told him about the conversation with coach. Dad agreed that I was slacking off and I was a little surprised it was that obvious. He said that college football was my decision but that education was the priority and that football at that level was not all that much fun. He wanted to know which schools had expressed interest and I told him I had no idea and that I hadn't ask. I asked about working in the business and he just laughed and said that there might not be a business as there were an number of huge offers for the business and he could easily retire. Then he said besides my company is very technologically orientated and other than computer games you have shown no interest in anything technical. So as a Junior in high school, what you thinking about doing with your life? You should add that to the list of issues running around in your head.

At that point he shocked the shit out of me and asked who are you having sex with Ray, Tammy, both or someone else? I replied, none of the above, but that my next item to talk about, was Tammy. The other night she was all over me, even opening my belt and playing with my cock, I told her to stop as if it went any further we would need a condom I did not have, her reply was come prepaid next time. Dad, I'm not ready for that and while I like her and we have fun I'm not sure I want to have sex with her. Then he sad what about Ray, and I asked where did that come from, he said not sure just a feeling. I assured him that was not happening, I was not experimenting and was not gay.

Ok that's a lot, what else is on your mind and I simply said nothing I'm ready to talk about, he smiled and said just be careful. Then he added go as far as you feel comfortable with Tammy and don't think with you penis and always use protection. Hell thats all I can say because at some point as a good looking, ripped, popular teen jock you are going to fuck someone. As for football, take it slow, have fun, work hard and I'll talk to the coach and have him direct all this shit to me. As for Ray, you guys have always been too close and those bets you do could get out of hand and I think that's where you are at this point. Find a way to control or stop them. Oh, one more thing try to figure out what you want to do with your life a college choice with or without football is only a year away.

I thanked him gave him a hug and left, only problem was he dumped it all on me, well except for football and added what did I want to do with my life. However it was good to have the conversation with an open minded reasonable adult. Fuck my head was spinning. So it was off to bed and wait for Ray's task. Laying in bed with gremlins running around in my head none of which I could control, I had to agree with dad, it was time to reclaim control of my life. Fuck!

To be continued and please provide some feedback.

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Next: Chapter 5


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