The longest I have gone without cumming was 53 days. I like chastity play but most of the time it's only for the night. She will get me all excited only to lock me up and have fun watching squirm.
But about 4 months ago, I was getting really distracted at work and would spend half the day jerking off. I work from home so this allowed this to be an easy feat. I told my gf about it and she had me count how many times I came in one week while I was on the clock. That Friday night she locked me up and told me that I have to wait a day for every time I came at work.
Unfortunately it wasn't very strict chastity as I don't have something that is good for more than a day to wear, but if she wasn't around I had to send her a picture with my cock locked up with a plastic lock with numbers on them so you tell if it was taken off. Normally she'd come over and let it out for a while.
She even let me fuck her on the 5th day because I wasn't sleeping and was kind of going nutty. But she knows when I'm going to cum and quickly made her body unavailable to me and slapped my balls around to keep me from cumming. 5 minutes later I was locked back up.
She probably had about 50ish orgasms of my doing in the time I had none. My cock was so hard in it's cage while I was eating her pussy. It was so painful but exciting.
The day comes where I know I get to cum. I'm so excited. My cock is out and rock hard. We start fucking, and I blow on her tits about 30 seconds in. Fuck it was amazing. But the best part about the whole experience was I had told her about a video I watched a while back that got me super horny but it wouldn't have been something I would have done on my own, but she used the main aspect of that after I came as I had told her about how hot it made me.
She looked at the gooey mess on her tits and said. "Lick it all up or you will be locked up for twice as long!" I literally shot 2 more ropes of cum just from that sentence and started to lick up my hot cum. About half way through she pulled me up for a kiss with my mess still all over my mouth. We proceeded to fuck all night.