I would not want any of my friends or readers to get the wrong impression that I did not always take special care for the health and welfare of the boys with whom I worked. On the contrary, I often chastise my good friend Daniel in Thailand for moving too fast with his boyfriends and thus ruining what might be a long and fruitful relationship. With each boy that I have “worked with,” I have only always encouraged the boy to bring out the very best in himself to reach and often exceed his potential. One thing I have learned over the years is that boys and young men sometimes underestimate their potential. A boy can do so much more than he thinks he can. I try to help each boy exceed his goals, hoping that he will not only develop trust in my experience and judgment but that he will see that he has more in him than he thinks he has.
Take fifteen-year-old Ryan for example. Ryan was a delightful boy whom I mentored a few years ago. Ryan had an intense anal fear. He had a very tight, tiny asshole and was terrified of healthy anal sex with an older man — especially with any well-hung man. Was I going to allow the sweet boy's irrational fear to put up a wall and destroy our budding relationship? Not on your life. I was determined to work diligently with young Ryan to show him that he had a perfectly capable asshole and that he could become a fantastic lover and companion. I began with my fingers as always, easing the boy into being able to accept one, then two, then three fingers up his tight, young asshole.
I did not hurry things. Sometimes, I used pot or pills to help the boy relax, but at the same time, I did not want to deaden the sensations for the boy. I must say that during this process, Ryan was such a good boy that I hardly had to punish him at all. I kept telling him that I recognized the UNTAPPED potential in him right from the start.
Now, I want to point out to you, that I try never to push a boy too far. This first day on the new dildo, I only made him take fourteen inches up his asshole. I am well aware that boys of different ages can just take so many inches inside before damage can be done. I feel that from my many years of working with boys, and from making some unfortunate mistakes, I now can judge how many inches both in length and girth a boy can take. Ryan, of course, wanted me to stop at eight and a half inches, which is the length of my dick to which he had become somewhat used to. However, I pointed out to him that a boy had to keep growing to reach his potential, so we started with this new dildo at a quota of fourteen inches. I know from eight and a half to fourteen is quite a jump, but I was confident that Ryan could handle it, and I had several of my friends on hand just in case the boy needed some help or encouragement.
During the process, my friends and I kept telling Ryan what a good boy he was and what a good job he was doing. This is very important for the boy. He needs to know when he is doing well as well as when he is fucking up. My buddies and I would stroke his forehead and face, gently play with his nipples and dick to help relax him. We let him go at his own pace until he stalled or cried that he just could not take any more. Then we had to lend a helping hand sometimes, although I wanted him to learn to do most of the work himself. That would come in handy when he did his webcam shows.
Ryan had a look of concern on his face when he reached ten inches. He cried that if the dildo were thinner around, he could get it in deeper. I reminded him that he had to learn to take thick dicks as well as long ones. He insisted that any dick he would take would never be this thick or long. I did not inform him at this time about dog and horse dick. I wanted to save that for when our relationship was more solid. I also did not remind him at that time that taking one or two hands up his asshole might be considerably more difficult than the current dildo. No, I simply kissed him and smiled, and then told him to keep working. For the most part, we let him set his own pace.
As I said, that first day we only made him take ten inches. The next day we went for the whole fourteen inches. And then I taught Ryan how to fuck himself roughly up and down on the massive dildo. He passed out a couple of times during that phase. He kept asking me why my buddies or I never took anything up our asses, and why he was expected to take such horrible things up his fifteen-year-old ass. It was apparently time to have the talk with him about submissive boys and their role in life. We didn't use the word submissive but substituted faggot instead. A faggot needs to do whatever the Real Man wants for his pleasure. It's really that simple. Some boys accept that more quickly than others do. Ryan put up a bit of a struggle. But all in all, he was a very, very good boy and we had a very fun relationship.
I am quite proud to say that Ryan became quite adept at taking not only this dildo up his ass, but considerably larger ones. This saved him a great deal of pain when it came time to fist fuck him. So you see, I have always taken great care that my boys received the most exceptional care for both their emotional and physical health. I still look at my photos of Ryan's training with affection and pride. He seems particularly cute in the photograph of him contemplating a twenty-four-inch dildo as he tries to figure out how he is going to negotiate the massive rubber dick into his fifteen-year-old fuckhole.