I was awakened very early while in my jockstrap and cup. I had a hard, arousing erection and I knew it wouldn’t go down anytime soon. I am involved in another “living fantasy”. In this one, my “keyholder” will allow me to trade-off my hard cup for a regular jockstrap. The only catch is that I must receive a prostate milking (since I am now in Day 7 of SR). I agree and put-on the jockstrap.
The next thing I know is that I have received the HIH 950 prostate massager and it goes to work in about 10 minutes. {I know it is just a massager but it looks and feels like a lubricated finger of my keyholder}. I am tossing and squirming on the bed, trying to find a position that isn’t too stimulating. I can’t find one! I lay on my back with my knees bent up in the air. I am starting to pulse my hips as my prostate continues to give me immense pleasurable sensations. At some point, I am performing very rapid but light contractions and feel my cock get hard and then soft. I lost track of the time……
After about 50 minutes, I knew that the “milking” was over and my keyholder removed her finger very gently. I then had a choice: I could either put on my chastity cup again or put on my chastity cage (the CB-6000S). I chose the cup. After that, while still in the fantasy, she wanted me to watch some porn videos of guys getting cock massaged until they cum. Oooh! If only that could have been be my cock! I can’t even touch mine!
I like playtime while in chastity!
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Source: https://www.aneros.com/blogs/playtime-in-chastity/