Humiliating Step Forward - What Next?
Background - Had a great Scottish girlfriend who after many years of role play took the plunge and cuckolded me.... was great and ticked all of the boxes.... exceeded all my expectations and her thoughts was i should be careful of what i wish for.
Unfortunately, life outside of our great sex life had a few challenges and the relationship ended.
Now i have a great very vanilla new girlfriend (f54) for past two years. I (m57) confessed my fantasies and she's very understanding but going through peri menopause and lost her libido. But the relationship outside the physical challenges is sensational. Her comment was that at least i fantasize about her and other men and i don't fantasize about other women (positive spin).
Unfortunately, I'm also suffering ED due to probably the diabetes medications and high sexual drive disparity with her low libido. Got myself into a funk where i get hard but cant maintain it. I guess i was also a pounder whilst she prefers to go on top and slow grind.
I've asked her to roleplay but she lacks that experience or desire to do so (very innocent vanilla lady). But she does climax from PIV and prefers that to anything else (like oral which is my forte).
Anyway, i bit the bullet and purchased a cock sleeve - since I'm not hard enough or get fully erect.... well finally got the courage to use it and it makes me about 8mm thicker and 3 inches longer... used plenty of lube and she went on top.... wowsers... talk about climaxing fast, she ground down on me and probably got an inch or two more than ive ever been able to get hard to.... she climaxed in no time - she really enjoyed it - i felt humiliated (in a good way as it scratched my itch).
It puts me in a weird place, as it was very humiliating, feeling inadequate, started thinking that maybe she's a size queen and doesn't know it. She isn't interested in other guys or cuckolding me. Which i accept and okay with, as she is a terrific partner, confidant, friend and i enjoy sharing my life with her.
I've asked her to be more dominant (i can see a strong woman desire in her as she is very independent successful woman)... but she just doesn't think that was sexually. But is very understanding and not judgmental.
So my current plan is to get her to read two eBooks so that she understands the way my mind works.... and hopefully go down the dominatrix / humiliation side.... which turns me on.
* DNA of a Cuckold - Wife Version
* The Hesitant Mistress - Guide to Claiming your feminine power
Any thoughts on how else i can get her into role playing cuckold, stepping up into being more dominant and is there any psychology eBooks around humiliation play/cuck role play without involving a 3rd that people can recommend.
Posted Mar 8, 2026, 1:18 PM UTC