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She has denied my a penis orgasm the month of September. She has pegged me at least 7 times rhos month and has used a vibrator on me close to 10 times. She will play with my penis to get me close to orgasm sometimes. I’ve in a chastity device probably 10 days this month.

The goal is to see if I can “orgasm” from anal penetration. I’ve gotten close many times this month but it has not happened.

I brought up the subject last night if she wanted me to be in permanent penis orgasm denial and she said she did not because she likes when I orgasm.

I’ve had PIV sec with her twice in the last year or so. Shes had more PIV sex with both of her boyfriends that she has had with me the past year.

CoupleFun555 wrote: ↑

Sat Sep 27, 2025 3:42 pm

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I’ve had PIV sec with her twice in the last year or so. Shes had more PIV sex with both of her boyfriends that she has had with me the past year.

That is really hot. That turns me on when that is in my situation. I don't know why it is.

Is She participating with pegging you because it is Her "goal" for you to orgasm from anal penetration OR was it your "goal" and she is participating to make you happy? Also, are you masturbating to the point of jerking off and ejaculating when not in a chastity device the other 20 days of the month? I think it would be more beneficial towards the "goal" if you refrain from ejaculating. I know there might be some set backs if you can't help it but I believe the "goal" can be achieved with patience. Sometimes, it could also just be the right dildo She wears when pegging you. You can experiment with different shapes, lengths, girths, etc.... Maybe its the verbal element during a pegging session that is lacking?