I have been toying with chastity on and off for a few years. My longest lockup was 7 days, until this month. I had the goal of achieving anal orgasm while caged but could never send myself over the edge, and I decided that this locktober would be the one. I was on a trip the last week of September so my last Jack-off orgasm was Sep 28th. At midnight on October 1st I locked the lock. Today, October 9th I had my first anal orgasm, here’s what I learned:

1. My general life productivity diminished, I’d find myself spending hours browsing Reddit and Twitter just enjoying the sexual frustration. I haven’t made it to the gym, or gotten anything productive done around the house since I started.

2. I have made a lot more impulse buys that I shouldn’t have made. None super expensive, but they add up.

3. Anal masturbation sessions have a peak, and they don’t always end in climax. I had 5 anal masturbation sessions and felt sexually satisfied even though I didn’t cum.

4. I was a LOT more open about chastity and this journey with people and had a good number of “doms” indulge for a day or so and then ghost, which is annoying.

5. I focused on not touching my dick. I stayed in chastity a majority of the time, but I would remove it if I needed a good night sleep or if I was going to be active. I didn’t make it to the gym but did yoga a few times. So the focus wasn’t on being locked, rather, orgasm denial.

6. I learned a lot about sexual shame. For all of my adult life I’ve been openly and proudly gay, and have been cautious about STIs. I’m on prep and play safe, but the fear of STIs still gets to me. Often I would get horny, talk with guys, and then Jack off and think of a reason to not meet up. During this time I had a heightened sense of sexuality, and met up with 2 guys and enjoyed the sexual experience without any type of “shame” if that’s the right word.

7. You will leak, a lot. I found that using an ankle sock, over the device helps absorb leakage and also provides protection against chafing. With the balls tightly in the cage there’s a tendency for rubbing which causes pain. Pop a sock over it and I could walk perfectly normal and didn’t have any visible leakage.

8. The grand finale. I wasn’t expecting this to happen today. I was playing with an anal toy. It’s a metal curved toy with a larger and smaller tip on each side. I like the metal toys over a traditional dildo because you can use silicone lube which stays wet longer in my opinion. I found the spot, and used my bed to anchor it in place and I rode it while watching porn. This is the part I think sent me over the edge… I had to pee. Not bad but it was on my mind. That sensation added to the pleasure and I think it was key to sending me over the edge. If you’ve struggled getting there, give it a try? Riding the toy caused my caged junk to bounce which I think did add a little external pleasure but I kept my mind focused on my ass. Then it happened. This was the longest orgasm I’ve ever had. Whole body shaking, just incredibly intense orgasm. The cum shot wasn’t massive (for 11 days) but the orgasm itself was incredible.

9. Satisfaction? Well, it’s different. There wasn’t the hormonal crash that happens afterward, no post-nut clarity, or empty feeling. I still felt the same heightened sense of sexuality that I did during and before, but it was a different kind of satisfaction. Kinda like wow, I didn’t know my body could do that!

10. Is this sustainable? Probably not. But I would like to rotate in periods of semen retention and anal orgasm again in the future. I’m not locked currently, giving my skin a break as there is some irritation.

Should I maintain not touching my penis for the remainder of locktober? What do you all think?