My favorite assignment happened over two days starting on 8/31. The first thing Mistress had me purchase was an Aneros prostate massager. I was a novice at anal play, so at first I grumbled about spending $45 on something to stick in my butt. When it arrived I was told to spend the day researching it online, and in the morning to try using it. I read all I could find and thought I had a pretty good idea how it worked.
In the morning I received an email granting me permission to orgasm as long as it was caused by the Aneros. I followed the instructions and over the next half hour changed my opinion about that magnificent toy! I felt things that I'd never felt before. When I reported the results to Mistress she laughed and said "Now you have a better understanding of what a female orgasm feels like." If that is true, Women are damned lucky
After using the toy three or four times, i noticed changes in my body. Overall I felt more alive sexually than I'd ever felt before. My nipples also became incredibly sensitive, so much so that just the friction of my shirt rubbing them made them stiffen. One day on "Write for me" I found a task where you put clamps on your nipples and type "I will remain locked in chastity until I learn to orgasm from nipple stimulation alone." 25 times. When it is over you remove the clamps and rub you nipples for 10 minutes. I completed the task and sent a message of thanks to the creator asking if it was really possible to orgasm just from nipple stimulation. She responded that she knew of two guys that could, and teased that she new ways to make me cum without laying a hand on me.
I told her that I was already serving someone, and that I would ask Mistress's opinion. I told Mistress my story and asked her if she thought it possible. Her reply sent shivers down my spine "No I don't, but imagine the fun we will have finding out." The next day I received the instructions "Try to orgasm from just nipple stimulation." I spent 4 hours laying there that day rubbing and tugging. I would get to the point where it felt really good, but that was all. That evening I reported my failure and asked if I could try again in the morning.
That morning I received another email from the task creator asking how it was going. I told her about the day before and she encouraged me to keep trying, suggesting that i ask Mistress to keep my chaste until I succeeded. I agreed. and a message from Mistress to continue my explorations.
I laid down on the sofa, on my back with my feet flat and my knees bend and slightly apart. I started with some deep breathing to help me relax. After about 10 minutes of breathing I was relaxed enough that I felt I could fall asleep. I started to gently rub my nipples, the feeling was nice. I began to slowly run circle each nipple with just the tip of my index finger. The pleasurable feeling from last night began to return, I began to swell, my erection straining against my shorts was too much of a distraction, so I removed them.
This was only the second time I had been permitted to have a full erection in two weeks, and I sighed with pleasure, reveling in the freedom. The feeling of warmth was flowing from my lower body, my breath coming in pants. I pinched my nipples between thumbs and fore fingers and began to gently roll them. The effect was incredible, a stream of pre-ejaculate began to flow down my shaft, and my nipples hardened.
The urge to thrust my hips came upon me but I resisted as I slowly increased the speed of my fingers. My lower body began to twitch, and I moaned with the pleasure. It was feeling incredible, but not good enough to send me over the edge. I remembered reading in a submissive's blogs about a guy that could resist havong an orgasm during intercourse until his wife squeezed his nipples, she referred to them as his “cum switch”. Out of curiosity, I began to pinch and tug a little harder. The effect was incredible, I could feel an orgasm building. I squeezed and tugged harder, and when I thought I was close to the edge, I squeezed even harder. The pain seemed to shoot from my nipples straight to the head of me penis, it began to spasm, and I had one of the most intense hands free orgasms ever.
I lay there gasping for breath, my body shaking. I was smiling unable to believe that I had actually done it. I wasn't sure if it was a fluke or not, but have been able to do it again on two other occasions. It's like knowing a really cool trick, but not being able to tell most people about it.
Madden
