In a previous post ('Summer Camp') I described the masturbation activity at camp when I was 12, going on 13. My best friend, Billy, was incredibly shy about showing his body, except for one strange event at camp that year, and very mysterious about his masturbation habits. I found proof that he did it, but despite several hints over a period of months I could never get him on the subject. For some reason I really wanted to do it with him, but to no avail.
However, that Fall something equally arousing happened, unfortunately as the result of a near-tragedy. Billy was in an accident and hurt very badly. He broke his thigh bone, and after being in traction for quite some time, they put him in a body cast. When he came home in that cast, he was pretty out of it for about a week, since he was still on pain medication. I visited him every day after school, and he'd drift in and out of sleep. When he was asleep I kept a close eye out at the piece of gauze that was all that covered his privates. The cast had a triangle-shaped opening in both the front and back of his crotch so he could go to the bathroom, and the hole was just covered by a loose piece of gauze that would slip a little bit while he was asleep. I got a few good peeks at him that way, and enjoyed seeing his private parts. I'd go home and masturbate at the memory. Occasionally he'd get a partial boner in his sleep, and it would stick up obscenely. He was circumcised like me, but the skin seemed looser, so when soft his head was about half covered, but it would pull back when he was hard.
Going to the bathroom redefined his modesty, I can tell you. Though he could reach his crotch, the cast was so big that he couldn't hold himself to aim into the bedpan when he peed, so someone had to hold his penis for him. Usually it was his mother (I would have died, and I'm sure he died a thousand deaths at that!). Doing a BM was even worse, since the helper also had to wipe him, a humiliating experience.
His mother knew I would come over every afternoon, so asked if I'd take care of Billy while she shopped, took his brother and sister to things like piano classes, etc. I was happy to, and that's how I got to touch Billy's penis for the first time.
After about three weeks, I wondered how he could stand not being able to masturbate, then began to think how embarrassing it would be if he had a wet dream inside his cast. Yuch! So one day I was holding him while he peed, and he got hard in my hand. I have to admit that I held on a little longer than I had to, pretending to be careful to get all the drips out. When he got hard, he kind of blushed a bit, and I said, with my heart in my throat, 'I can take care of this for you.'
He asked what I meant, and I stammered a bit and finally said I could jack him off so he wouldn't risk having a wet dream. He hesitated a bit, then said, 'that would be a good idea.'
So I went to the bathroom and got some hand cream and a hand towel. I spread the towel over his crotch under his penis and over the cast so as not to get semen stains on it, and gently started to stroke his lubed penis. He looked tense at first, but then he relaxed and closed his eyes. I did it to him as smoothly and gently as I could, and asked if it felt good. He just said a simple 'yeah,' and I kept going. After a while he said, 'harder and faster,' and I complied. By this time he had a smile on his face, and I could tell he was getting close. Then he started to come, and I could feel his penis pulse twice, pause, then pulse several times rapidly as his semen shot out onto the towel. I just held my hand still, gripping fairly hard, as his penis jumped in my hand as thought it was alive. Billy just lay there with his eyes still closed, with a happy look on his face, breathing hard. After a minute his penis was getting soft, so I let go, and he whispered, 'Boy, I needed that. Thanks.'
I replied, 'Anytime, anytime' as I began to clean off is penis and squeeze the last dribbles out so he wouldn't have a mess in his crotch the next time his mother helped him pee.
I was highly turned on, and had a boner like stone, but I waited until I got home to masturbate, and I still had the towel with me, so I felt the wet spots as I jacked off.
The next day I brought the towel, and after his mother left, held it up with a questioning look. When Billy saw it he blushed, but nodded his head yes, so I did him again. And that started a nearly daily routine. The only difference was that after a couple of days I decided not to wait until I got home to masturbate, but sat down in a recliner chair in Billy's room and did it as soon as I had him cleaned up. Billy watched me with interest as I pleasured myself.
This went on for nearly 5 months, until Billy got his cast off. I never tired of doing him, and it always turned me on so much I had to do myself right there. The funny thing is that as soon as he got his cast off and could do it himself, he wouldn't let me do him, and again was just as secretive about it as he had been before. The fact that I had masturbated him nearly every day for 5 months didn't seem to count - when he did himself, he kept it completely private. I could never figure that out. But I still had the towel!