The First Ruined Orgasm Challenge
For the first ruined orgasm challenge, the goal was for Me to instruct Jack through a guided masturbation session in bed. I was not allowed to touch him, and I kept to that in the spirit of the challenge!
Guiding Masturbation
I made him start dressed and rubbing his cock through his jeans. I loved watching it grow. Then, I had him take off just the jeans, and rub through his boxer briefs. When I could not stand it anymore, I had him get naked for me. I instructed Jack to stroke to 5 edges, to lick up his precum, and finally to ruin his orgasm. He stayed hard as we went to sleep, so of course, I had to do some touching and teasing. Torment is fun!
The Next Day’s Feedback
Delia Emailed:
That was so sexy to watch. Very hot going slowly, and starting you with your clothes on. Watching you get hard in those jeans was really good... And the edging and final ruin was great. Teasing you as we cuddled in bed... Couldn't help myself.
Jack Replied:
That was hot, and an easy way to get into the challenge. You are seriously wicked. I could not sleep with your sexy ass rubbing up against my cock. I swear I was awake for an extra hour before my hard-on went down. This may be a tougher challenge than I thought. 9 more days.

Stay tuned for day 2’s report. This was a super-hot challenge!