Background
I am in Day 7 of SR and felt like I should ejaculate. But how to do it? I went to bed wearing my SD Ultra Pro Carbon “chastity cup” but awoke an hour or two later. I had this feeling that I wanted to ejaculate. So I went on my comfortable sofa armed with only a box of tissues. I lowered my PJs and my cup and selected a nice binaural track for male ejaculation; it was about 15 minutes long. After listening, I was somewhat aroused but not enough to masturbate and ejaculate. So I went back to bed….
More Attempts
I then “swapped” the SD cup with the SafeTGard cup for a while, trying to remain in chastity. But that didn’t last too long either. I still felt the need to cum. So I “swapped” the SafeTGard cup for the SD soft cup/jockstrap which I hadn’t worn in a while. I could feel my package through the dense foam and it started to feel very arousing and good. But I still didn’t feel too close to the PONR and an ejaculation.
I then “swapped” the SD soft cup for my Duke swimmer’s jockstrap, pulled-up my PJs and put it on; then went back to bed. I suspected that this combination would eventually help me in my quest for an ejaculation. And then something magical happened…..
Fantasy
Without wearing a hard “chastity cup” it was only a matter of time before I started fondling my accessible package. Yes, it was starting to feel so good and I was sure that I would be ejaculating soon. I actually fell-into a fantasy…..I am lying in bed with a lover and she begins to give my “hidden” package the most sensuous and delicate finger-massage through the knit pouch that I have ever experienced! For about 25 minutes, she deftly manipulates my sensitive scrotum and up to the frenulum of my penis. I am not especially erect but this “tantric” massage put me in the zone and on the path to ejaculation. I was sure of it. I am starting to feel a tensing in my prostate. My ejaculatory reflex was getting ready. I felt it was only a matter of time now before the inevitable ejaculation…..
But I must have dozed-off still wearing the Duke. I remember dreaming vividly and that is usually an indication that a NPT (night-time erection) was coming. Sure-enough, when I awoke, I had a very firm erection slightly hidden by the Duke pouch. But I still did not ejaculate. Worse yet, it was time to get-up for the new day.
Ending
Not having ejaculated yet in Day 7 of SR, I am about as horny as I could be. What to do? Well, the only thing I could do was put-on my “original” chastity cup—-the SD Ultra Pro Carbon cup! I don’t know how I came “full-circle” — from chastity to near-ejaculation to chastity — but this ejaculation “experiment” certainly contained some surprising sexual elements. And isn’t that what makes sex interesting and fun? I now have no idea if or when I will next ejaculate! It now looks like I will be in chastity today! Day 7! Man, am I going to be horny!
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PS In retrospect, this “experiment” was like a classic “tease-and-deny” in male fantasy! Often, the guy in chastity has his cock cage removed by his keyholder. Then his cock is teased and stimulated almost to the PONR. He is sure he will earn a rare ejaculation. But suddenly, his cage goes back on and he is again frustrated and back in chastity! How long this time? He doesn’t have a clue…
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Source: https://www.aneros.com/blogs/i-had-every-intention-to-ejaculate-at-sr-day-7-it-didnt-happen/