I love pegging and bottoming in chastity. Anal orgasms are out of this world and getting into that head space is seriously addicting. I've come in chastity before, but only 2 or 3 times where I fully felt that feeling of total explosion and losing all control while cumming. I'm getting better about being able to have what I call rolling soft orgasms. They feel pretty nice but they aren't as explosive. But i certainly know that i've had a prostate orgasm.

I don't wear chastity often, maybe only for some hours or overnight when my GF is in the mood. And i'm 7.5" hung. I recently got the S kink3d cage to try a smaller cage. I have a S and R.

I have only been trying the S as of late, however when bottoming I feel like it's so much harder to cum. I usually am hard in the cage and I've noticed usually when I get close enough to cum (with or without a vibrator), it feels like nothing can exit.

I really love that sensation of squirting helplessly but am curious if anyone has had this problem as well. I guess this would be the ultimate chastity cuck scenario where it's almost impossible for me to cum in chastity... but i'm not strong enough to willingly to suffer through that. My GF would need to encourage me lol. But I love being so hot and horny to beg to get satisfied by cumming while being fucked.