Cumming in Chastity

Perfectly normal as long as you are comfortable. You should work on cumming without touching your clitty. A hallmark of a good sissy cuckold is when she can do a hands off sissygasm from being analized. It is the preferred method for servile sissies to show their commitment to the lifestyle.
such good advice Sandy, and it'll help the sissie know she's learning her craft and is a good gurl. xxx
 
Unable to jerk off I have started sitting on a small dildo wile watching IR porn. I start squirting through my chastity now. I have never jerked off this way. It makes me feel so guilty and is confusing. Is this normal?

Sort of the same thing here except i'm not sitting on the dildo but have been pegging myself from behind with it while watching IR porn... I can make myself drip a lot but have yet to be able to achieve a actual squirting orgasm, our goal, yet..
 
Sort of the same thing here except i'm not sitting on the dildo but have been pegging myself from behind with it while watching IR porn... I can make myself drip a lot but have yet to be able to achieve a actual squirting orgasm, our goal, yet..
Step up to IR cuckold porn. Wear your best lingerie and get all sissified. Use plugs or stand up dildos but no touching your clitty. Focusing on the Black Mans performance and you will achieve a sissygasm. Showing complete identification as a sissy cuckold!
 
Step up to IR cuckold porn. Wear your best lingerie and get all sissified. Use plugs or stand up dildos but no touching your clitty. Focusing on the Black Mans performance and you will achieve a sissygasm. Showing complete identification as a sissy cuckold!
Already watch IR cuckold porn.....don't wear lingerie nor get sissyfied... use a stand alone bbc dildo already... Just have not been able to crest that peak yet
 
i tend to agree with dildo with no vibe, a cock shaped one or a moderately aggressive butt plug. a buzzing vibe on your prostate can get you to ejaculate without the orgasm more often, if ruined orgasm is your goal though - you got it. i can only speak of my experience, the stretching and full feeling of some plug or dildo slipping and popping in and out works for me. though i go soft when i have something in my ass, it still gets me to pleasant orgasms. conditioning and practice.
I think most guys do go soft when something in ass. I know I do
 
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