Requesting Best way to sissygasm?

[sissysteph121]

Hello everyone,

I've been a closeted sissy for years. I love to dress, play, take tasks, be submissive. I love cross dressing and public play.

Most of all I love anal and chastity. I've played with my dildos a million times before. I have an XL, M, and smaller one that attaches to a sex machine. I've gotten close but never really close enough to achieve a sissygasm. I want to cum hands free. I find good tasks and foreplay help me get very aroused. However, PLEASE help me by giving me/telling me your best method to a sissygasm?

Thanks

 

[puppers]

My advice would be it's something that you need to build up to, it's kind of like expecting to be able to ride a bike for the first time without having tried before, it's a a skill that needs practice.
Can you cum in a cage from other methods of stimulation? If you've never came whilst caged, I'd say start with that as your goal, use a vibe or play with your cage or balls or whatever works for you until you cum to get used to the feeling of being caged whilst cumming (it's great, you'll be hooked and never want to cum any other way again!) When you've done that, introduce anal play whilst making yourself cum caged however feels right for you. Then you can introduce edging, get yourself close but once you get close stop whatever method of stimulation normally makes you cum and just focus on anal play. Keep doing this until you eventually finish from just anal play alone whilst edging with the other stimulation, the first time it might be more like you were teetering so close to the edge from your other stimulation that you would have came regardless of the anal play, and that's fine, your body is still learning. Now your body knows what it feels like to cum from anal play. Slowly remove the other form of stimulation until you can cum from anal play alone.
The way I learned to cum hands free whilst caged was to learn multiple ways to cum whilst caged (vibe, nipple play, ball beating etc) before introducing anal so that I could use other forms of stimulation to either accelerate my orgasm or to help tip me over the edge when struggling to finish, it all helped my body get used to orgasming from anal play predominantly. Now I can cum caged in lots of different ways, but my favourite of all is to edge and deny myself, part of the excitement early on was learning how to orgasm in different ways, now the excitement is knowing that I can cum but choosing to frustrate myself instead.
Hope this helps, good luck on your journey!

 

[Kinkyclusterfck]

My advice would be it's something that you need to build up to, it's kind of like expecting to be able to ride a bike for the first time without having tried before, it's a a skill that needs practice.
Can you cum in a cage from other methods of stimulation? If you've never came whilst caged, I'd say start with that as your goal, use a vibe or play with your cage or balls or whatever works for you until you cum to get used to the feeling of being caged whilst cumming (it's great, you'll be hooked and never want to cum any other way again!) When you've done that, introduce anal play whilst making yourself cum caged however feels right for you. Then you can introduce edging, get yourself close but once you get close stop whatever method of stimulation normally makes you cum and just focus on anal play. Keep doing this until you eventually finish from just anal play alone whilst edging with the other stimulation, the first time it might be more like you were teetering so close to the edge from your other stimulation that you would have came regardless of the anal play, and that's fine, your body is still learning. Now your body knows what it feels like to cum from anal play. Slowly remove the other form of stimulation until you can cum from anal play alone.
The way I learned to cum hands free whilst caged was to learn multiple ways to cum whilst caged (vibe, nipple play, ball beating etc) before introducing anal so that I could use other forms of stimulation to either accelerate my orgasm or to help tip me over the edge when struggling to finish, it all helped my body get used to orgasming from anal play predominantly. Now I can cum caged in lots of different ways, but my favourite of all is to edge and deny myself, part of the excitement early on was learning how to orgasm in different ways, now the excitement is knowing that I can cum but choosing to frustrate myself instead.
Hope this helps, good luck on your journey!

I didn’t know about the training aspect and I’m still working on an anal sissygasm myself (so you’re not alone steph.)

However, a useful bit of advice I was given was to paradoxically go slow and target the p spot (since I would always go too fast.) Good luck