With my wife I started the 1000 stroke challenge and we are now on day 5. I have had 400 strokes so far today and will have another 100 later. To keep my cock under control I wear a chastity sleeve (see attached) and she only has to reach for the keys for my cock to pump up again and start to leak. Of course she still insists on her orgasms which I provide through sucking her off, and she likes me to penetrate her just after her climax as it help prolong it for her. The trick in the middle of the challenge is for me not to cum. If I do the whole process starts again. So far so good.