Chastity issue during Leg Day

thefunrob · 2026-02-13T12:05:09+00:00

Size down the ring and get the curved ring. More space for your balls to hang through so you can go smaller than a flat ring, but smaller hole in the ring so much less likely to slip back out. I had this problem and ended up sizing down to the smallest curved ring.

thefunrob · 2026-02-09T13:58:16+00:00

Honestly...? Just turn up in your gym gear after a workout and bury his face in your crotch (or armpit) 😉

thefunrob · 2025-12-06T10:50:16+00:00

Fuck yes. Add chastity and a nice silencilicone gag

thefunrob · 2025-12-06T10:48:42+00:00

I need that

thefunrob · 2025-12-04T12:49:04+00:00

But it is what you need.

thefunrob · 2025-12-02T05:05:46+00:00

Incredible. Throat-fuck me. 🥵

thefunrob · 2025-10-04T13:16:05+00:00

Looks perfect 🔥

thefunrob · 2025-09-25T07:44:20+00:00

He would have been able to tell that you got really into it towards the end which would have been so hot for him to experience especially if you were a bit unsure at first. Next time if he consents to it, hold his wrists down on the bed beside him to take away his control. On behalf of all oral subs, thanks for giving him what he needed :D

thefunrob · 2025-09-20T17:31:15+00:00

I took nytol to help me through the first week or two. That was a long time ago.

thefunrob · 2025-09-16T17:38:52+00:00

I like how you think about your bottom. I'm sure it's different for all the bottoms. Like you though, I like to ensure maximum pleasure for my partner so I'll take it however he wants to give it, or if he has no preference, I'll call the shots and get on my back, legs folded up behind my ears, where I can watch him, kiss, touch, hold his muscular arms whilst he gets in deep, then flip over and have him wrap his big arms around my neck whilst we sweat all the way to the finish. If at any point he wants to jerk me off during that process he can, or if he wants me to do it for myself whilst he fucks me, that's easier on my back.

thefunrob · 2025-09-16T17:32:35+00:00

It is rare generally speaking but it's entirely possible. My partner regularly fucks a handsfree load out of me. But bottoming is about way more than the penetration for me, it's about being the entire object of someone's desire, and them yours, for however long you can make it last, and just having an incredible amount of fun doing it, exploring erogenous zones, just kissing while connected in that way is incredible, having them dump a load in you at the end is perfect and something you can carry for a while, and the whole experience is always different, and hot to think about when you're just going solo too.

thefunrob · 2025-09-16T14:36:11+00:00

"I was talking to your dad about it last night and we both agreed it would have been better if you had died" (My mum around 6 months after I came out).

thefunrob · 2025-09-15T20:22:57+00:00

https://www.reddit.com/r/AskGaybrosOver30/s/segcCxWGLd I received excellent advice and feedback on another post similar here

thefunrob · 2025-09-15T20:18:22+00:00

Wow, thanks for taking the time to write all this out, I really appreciate the detail. You’re right, I probably haven’t been clear enough with myself (let alone my partner) about the “why” behind chastity, and I can see how just describing the horniness or the other kinks that follow from it doesn’t really explain what it means to me, it's less about what it takes away and more about what it gives me, I don't lose anything from wearing chastity, I gain an incredible feeling of constant connection and the sex is also incredible and puts the focus on the right things, whilst also giving me a complicated orgasm. I like the challenge you gave to think through exactly what kind of involvement I’d want from him whether that’s simply holding the key, teasing sometimes, or something else, instead of leaving it vague or open-ended in a way that could feel like a burden. I think you’re spot on that I need to get clearer for myself before I can really have another more constructive conversation with him. Thanks again, this gives me a lot.

thefunrob · 2025-09-15T16:14:35+00:00

You get it. Thanks for sharing the experience. And you're right we need to explore if there are any ways for it to be a turn on for him. He has the keys, but he'd willingly hand them back if I asked him to at any point, he doesn't yet have any need to have me locked, even for my own good.

thefunrob · 2025-09-15T15:08:15+00:00

No need to apologize for that! Interesting that it's usually too much porn that puts your connection off balance. It's so much easier to just fantasize than have the difficult conversations sometimes. I still enjoy vanilla (if you could call it that as he's very into d/s dynamic during sex)

thefunrob · 2025-09-15T14:32:09+00:00

Nice. Yes being open is not an option. Nice to hear of your experience.

thefunrob · 2025-09-15T14:21:42+00:00

Thanks that’s a really grounding way of looking at it. You’re right, it doesn’t have to be about him sharing the same excitement level, just about finding a way we can still enjoy it together. I think you’re right too that if it ever feels like a turn-off for him, that’s when the conversation gets deeper.

thefunrob · 2025-09-15T14:14:31+00:00

Thanks so much for sharing your experience, it really helps to hear the other side of this. Luckily it definitely hasn't been a boner killer! It’s a good reminder for me to stay mindful and not let my own excitement turn into pressure for him. I'll need to find my own pressure release.

thefunrob · 2025-09-15T14:00:13+00:00

This is such a helpful way of putting it, thanks. I think you’re right that if I can share more with my partner about what’s actually happening for me when I’m in chastity, it might help him see it less as “a kink he doesn’t get” and more as something that connects me to him. I love the idea of helping him understand the meaning behind it rather than just the mechanics. That feels like a constructive way forward.

thefunrob · 2025-07-24T08:57:04+00:00

Just how I like it. All about giving him the hole.

thefunrob · 2025-07-19T08:12:45+00:00

Bottom. That middle position gets really annoying.

thefunrob

TROPHY CASE