How to hands-free cum/sissy cum

[bobui]

Hey! That is my first post on here, though I've been registered and been reading RoseButtBoard for over a year now and  been into anal fisting for about a year or so. So far (not a lot of regular sessions unfortunately..) My mistress suggested we start anal stretching and that's how I got hooked up. I started off with hardly getting 2 fingers in on a 1st session, now I am able to take a 7,5cm (diameter) hard plug. It took about 14 sessions in total to get to this stage, and 5 sessions to insert a fist. So I was kind of happy with the way stretching was going and really love the play! It's the best thing I ever tried and I no longer interested in the classic sex I was having before.

The only problem I have- I can't cum from anal only. I was told that tensing (like if I were to push the hand/toy out) and trying to push out "prolapse" (I don't yet have it) while fisted/pegged should help me cum handsfree (also known as sissy-gasm in certain subcultures/roleplays). I've been trying that for a few months, but can't seem to find a way to cum hands free, maximum what I managed to produce was a table spoon of pre/cum (after 2 h non stop fisting session, and 5 h before play time). We tried poppers, but that mainly helps to get anal orgasms, and not on regular bases either, only when my anal turns into a swollen mess and starts itching/hurting then I can get anal orgasm. 

After using poppers - penis orgasm is not possible (as it's always flaccid during fisting and usually is in the sissy cage, so removing it takes a while), getting it up is extremely hard after poppers and requires A LOT of hard hand job (last time the frenulum was torn from all the effort to make it hard). Also in the nearest 6-7 months I wouldn't be able to use hard jerking method, as penis is being heavily modified and will be bandaged most of the time (the head and base are being split-meatotomy, so it looks like a clit/labia and will fulfil the overall look, then it will be pierced with rings and tattooed with a "stockings lace" type of pattern,  big and existing project!), so I need to learn to cum handsfree from fisting. 

I would really appreciate your advice! And  I am always happy to chat to people with same interests, so feel free to say hi (especially if you are from UK and you are into fisting/crossdressing/sissy play).

Thank you and have a wonderful prolapse! 

[bud111]

Hi Friend 

I have a short answer 

More anal play and more anal orgasms 

Enjoying ..... Thanks for attention 

[Tractor]

Direct pressure on the prostate, play with angles, toy shape and firmness, speed etc, you will know when youre there

[Rosebutt]

36 minutes ago, Tractor said:

Direct pressure on the prostate, play with angles, toy shape and firmness, speed etc, you will know when youre there

I have, after DECADES of anal play, discovered the (almost) hands-free cum. And it’s all thanks to the Square Pegs toys Happy Hour XL plug. When it pops in, it triggers a geyser of semen. I only have to lightly touch my cock and it explodes. There’s something about the size and shape of it that hits my prostate in a way no other toy does. I’m obsessed with this thing. In fact, gotta go…

[Sinan]

Ok here is alot of extreme anal players, expecialy when we talk about diameter of dildos and plugs...do you have pain in prostate after years of inserting big objects in your ass?

[Rosebutt]

2 hours ago, Sinan said:

Ok here is alot of extreme anal players, expecialy when we talk about diameter of dildos and plugs...do you have pain in prostate after years of inserting big objects in your ass?

Not at all. If you take your time and relax, that kind of thing generally doesn’t happen.

[bobui]

On 5/8/2023 at 8:33 PM, bud111 said:

Hi Friend 

I have a short answer 

More anal play and more anal orgasms 

Enjoying ..... Thanks for attention 

Thank you! How many times a week would you recommend stretching? 1-2? 3-4 and for how long? And what would be the best technique for stretching? E.g. Cone shaped plugs?

[bobui]

On 5/9/2023 at 1:22 AM, Rosebutt said:

I have, after DECADES of anal play, discovered the (almost) hands-free cum. And it’s all thanks to the Square Pegs toys Happy Hour XL plug. When it pops in, it triggers a geyser of semen. I only have to lightly touch my cock and it explodes. There’s something about the size and shape of it that hits my prostate in a way no other toy does. I’m obsessed with this thing. In fact, gotta go…

Very good point. I noticed that only large (the maximum my anal can take) toys make me enjoy the process and get anal orgasms, small toys don't work that well. Also if a toy is extracted very very quickly so the are anal "turns out" then it brings the orgasm closer..