Satisfying Mistress Ch. 02

It's taboo and it's unknown. There's a guilty pleasure in that.

Even though you're 700 miles away, I will be there to guide you. I will be there to witness you losing your virginity and, vicariously, take great pleasure in your pleasure, uncertainty and, yes, a bit of pain. After all, isn't pleasure so much better when it is not so easily attained? Yes!

You might want to read Allergic's story about anal sex before you proceed and before you even read the rest of this email. It's extensive and answers several questions from hygiene to climax, the former equal to or more important than the latter.

I suggest you do the following before you contact me at 10 pm tonight. You need to be comfie and relaxed. If you need to go, take care of business and if you're unsure or uncomfortable with the idea that there may be roadblocks stop off at CVS for a couple of disposable enemas. Good thoughts now. Think about being over the knee of mistress or on all fours while I fill you with a warm, aqueous solution. No, not that. Salt water silly.

Take your shower now. I suggest a hot one. Skin tingly. Clean feeling. Relaxed. That's right, forgot for a second, you're a cold-climate creature. Mistress is still in shorts, tee shirt and sandals with the a/c on. Turn up the heat in your home an extra degree or two.

Get your dildo ready. I should have directed you to get a flesh-colored one instead of a garish color but, then again, you won't be in a position to notice the color. Or care. Get your lube ready.

Two setup options, and I'm already regretting not flying out to personally orchestrate the entire process: on your bed or on a very comfortable rug or mat on the bathroom floor. I mention the bathroom floor because you might want to position the mirror so you can watch yourself getting fucked. . . that is if you can keep your eyes open from the pleasure.

Here's the thing. There are, I believe, several rectal muscles in play that are not quite used to a semi-rigid artificial cock pushing its way past. You won't force anything but you will apply gentle yet constant pressure. Don't think with your cock . . . plunging in and out. You're going one way because if you pull out the muscles will seek their original position. Muscle memory.

All fours now with your knees exaggerated inward. Head lowered. Oh, I hope you're not on that expensive Egyptian Cotton comforter. Your wife will kill you. Be safe. You're on sheets now or the beach towel positioned correctly. Not sure about lube stain. The cum stains will come out in the wash.

Squeeze a very healthy amount . . . now double it . . . onto three fingers and work it around your rectal opening (no I'm not going to say "asshole", silly), slightly in, more in, all the way in. Gently but with authority. Those are key words and a key thought that will be repeated. All around. Imagine those fingers are long and soft. My hand.

Squeeze lots more on your hand and apply it to the dildo. It's entire length. Use the same method you would use when you masturbate. Remember that? Lots. Think for a second. It's not your cock. You would normally be on the receiving end. It's going up your ass.

Now, brace yourself with your left hand and rest your head on the bed, knees as forward as you can, hold the dildo at the very base, and put the head by your rectal opening. You will only get a half an inch before you will face resistance . . . your first obstacle. Remember, constant but gentle pressure . . . push. . . let the rectal muscles relax . . . maybe pull out a tenth of an inch but push back immediately. It may be a minute or two or more before more length slides in. Gently. Next obstacle. Push back against the head. A little harder.

Got it? Don't stop until you have taken the entire length. Hold it in. Be still for a moment. You enjoy being filled. You enjoy that you have pleased your mistress. You enjoy what you have accomplished.

Only now may you seek relief. It will be a tiny challenge but your left hand may be used.

First say, "I love you Mistress."

I find myself speechless ...not in shock, but in happiness.

I read the words again and again.

My task may be clear, but what's even clearer to me is how you feel about me. You care for me, more than you might wish. More than maybe you should.

I read your words and I feel you within me, I feel you around me, and I feel holding me. I feel special.

I look at the clock on my PC and wait...

9:57pm

9:58pm

9:59pm

My screen comes to life as you sign onto webcam at exactly 10:00pm as I knew you would.

You are stunning....you've done your hair, your make-up and are even wearing earrings. You look like your heading out on the town, but I know it's just for me.

I hear your voice...

"I'm here for you Hon...feel my hand, the warmth of my skin against yours...I'll be here next to you tonight for as long as you wish...your doing this for me and that pleases me and I know pleases you as well. Go slow, we have all night..."

I feel safe as you are here with me, next to me and holding my hand ... I will do this for you... I will please you, for it's what I crave to do ... I do love you Mistress.