Mistress Requires her Slave to Wear the "Ring" on a Saturday Night Out.

Dear Mistress,

Our weekend was busy, with parties, football and various activities, but we also seemed to fit in a good bit of the activity that has been fodder for our blog. And Saturday night deserves its own entry, and illustration.

After the big family get together Friday night, we had plans for some holiday socializing Saturday evening. You consulted with me on how to dress (not that my opinion should count) then settled on something you knew would make me particularly attentive and determined to unwrap you at the end of the night: a silky flowing dress, with black tights and boots to complete the look. You pointed out that you would not be wearing panties. (I took the accompanying photo before you put on your dress, and wished we had time for worship then and there).

You had me wear my cock ring that evening, knowing the effect it would have on me. The ring is this little device made of hard, barely flexible plastic. It’s a bear to put on, causing no inconsiderable amount of pain as I squeeze each ball through the small opening, and then shove my flaccid penis inside. Of course, if my cock even gets semi-hard, it’s impossible to fit into the ring, requiring a good deal of mental discipline. That can be hard to maintain when I also have to watch you parading around the room, semi-nude, laughing at my discomfort, with an “aww, poor Slave” thrown in, from time to time.

It usually takes me ten or fifteen minutes to finish the job, since my balls do not readily co-operate. But once on, the ring has a rather dramatic and arousing effect. Its like I am gripped tightly by those well manicured fingers of yours. I knew my cock would be in a semi-hard state all night, unless you decided to enhance the problem with some personal attention.

With the ring gripping me, and you so enticingly dressed, I was probably more focused on getting you home than on the social small talk the evening required. You allowed me to stroke your inner thighs as we drove to and from our events. And I tried to stay close through the evening, using opportunities presented to fondle your lovely ass through your silky wrappings.

I do remember our conversation with that cute lesbian couple. When one of them mentioned being in bed for a while on doctor’s orders, and how attentive her partner was, you said “Mick likes to wait on me in bed, don’t you?” And my response confirmed that your desires always are something I am happy to fulfill. They laughed, but I wondered if they picked up our little clues about my new status on your life.

Finally it was time to get home. You shed the dress, but left on your black hose and boots and lay face down on the bed, as if you were too tired for me. I spooned against you, my hand sliding between your legs, and began to gently rub you there as I kissed your back. Of course, I was naked, as you prefer in these matters . When you are dressed, and I am naked, it particularly enhances my subservience to you, Mistress. (Something I tried on you Sunday afternoon in our switch time).

As I slowly built your arousal, I verbally reviewed some of the applications you had received via email from gentlemen who want to dominate you. Of particular interest was the narrative description of one encounter that had been proposed. (Whether you would ever allow this to occur is something only Mistress can decide.) But the thought of you being required to surrender your hose and panties to him in a public place seemed to help bring you to a shuddering climax as my hand slid across your cunt, sheathed by your black tights.

By now my cock was at level red alert, tightly gripped by the cock ring. You allowed me to pull off your boots and tights and enter you, marveling at how hard I was. Quite literally I was painfully hard, because as my cock and balls swell with arousal, the ring becomes all the tighter.

After a few moments you decided to get on top, and proceeded to take your own sweet time to build to an orgasm of very dramatic proportions. What we talked about (and I recall only that it involved themes that would make even the two of us blush) is lost to me now. What I do remember is that how desperate I was to come, how you were reduced to sobs and tears by the time you shuddered to a climax on top of me, and that my cock and balls seemed to be on fire with that strange combination of arousal and pain that only the cock ring produces.

Of course the other effect of the cock ring is to restrain my moment of discharge. It presses against the little channel that would otherwise happily deliver my sperm to its proper destination. As a result it takes a good deal of extra arousal and effort to complete the task. As I tilted back and forth on the brink for what seemed like an hour, you seemed to enjoy my increasing desperation. I lost track of your orgasms after We had flipped over, me on top, one of your legs between my thighs.

Finally and with a loud groan, I came inside you (with permission of course).

It was another remarkable Saturday night with you, Mistress. Though it did take me a while to wiggle that damn thing off me.

Your Slave.