You feel my hand between your shoulder blades.  “Breathe for me.  Deep breath in. Keep your back arched.  Ass high in the air.  Good girl.”  The warmth of my steady hand offers the calm you need.

The wheel touches the heel of your right foot.  It’s so light you aren’t sure if that’s what it is until you feel it begin to roll toward your toes.  No sooner have you begun to prepare yourself for the prickly sensation in unspeakable places, then the sensation is suddenly gone.  Replaced by the touch of my fingers stroking the skin above your asshole.  It startles you but you love the feeling of uncertainty that intensifies your submission.  Dragging my finger down, I cross your hole and end up at the base of your pussy.  You know how I love to play with your ass and your natural moisture offers plenty of juices to make the outside of your asshole shiny and slick.

You are fully exposed to me for my pleasure.  Your legs are open, your hands tied.  Your chest is firmly on the mattress.  And your cheeks and labia are fully spread for me.  The anxiety ridden freedom from being this vulnerable makes your muscles tense but your juices flow.  You know I am enjoying my play time.  Your job is to stay still and be there for my pleasure.

Smack!  You are startled by the duel slaps of my hands on your cheeks.  You feel the sting as well as the impact that reaches deep into your stretched muscles.  Multiple smacks begin to take you to your safe and secure place.  Your place of submission where you can let go. First the wheel, then my fingers.  Your juices.  The stings.  My breath and voice so close to your pussy and ass.  “I’ve got you little one.  Let go for me.”  And you hear me breathe in deeply through my nose and remember how much I love to smell your sex.

But then the click of the top of the lube.  You know your ass is about to be filled.  Which device, you wonder?  He’s talked so much about anal training. The stretching that will gradually take place. 

The cool liquid drips from the top of your crack over your hole and my fingers catch and stop the flow just before it reaches your soaking cunt.  As I spread the lube about your hole, you feel my finger begin to push inward.  No penetration yet but the muscles are reacting as they should be.

“Breathe, and begin to relax.  Use the muscles to push against my finger with your hole.  This will make the penetration go more smoothly.”  You know you are about to be opened up.

“Keep pushing out.  Do it.”  There is no turning back now and you welcome having your ass filled knowing whatever plug I insert will stay for quite a while.  Possibly through the night as you sleep.  But you love the idea.  It connects you to me and adds to your security and warmth.

With the towel over your head there is nothing in your mind but my voice and your concentration on pleasing me by accepting my finger.  Slowly but deliberately I pass the threshold.  I stop and have you relax and contract the muscles multiple times.  This is part of your training.  You are learning to relax as you are penetrated, knowing this is the only way you will be able to take the increasingly larger objects I have promised you.

Feel my finger begin to twist.  “Breathe little one.  I’ve got you.  Focus on the sensation.”  Light kisses around your cheeks offer calm to balance the tension in this vulnerable position you’ve been placed.

But then conflict. The stern voice. “Keep your back arched.  You know my expectations.”  You realize you’ve relaxed the arch in your back as you feel an upward pull of my finger to guide your ass to its proper presentation.  Smack!  The sting only magnifies the sensation inside your holes as you clench tightly around my finger.  “Keep your back arched.  Do not disappoint me.”

In and out now.  “Relax.  I want to feel the muscles let go of my finger.”  I watch and feel your body work on trying to overcome the natural tendency to “squeeze” my finger.  You so desperately want to please me and I tell you what a great submissive you are.  In and out.  In and out.  All the while my finger is going deeper, bending and feeling inside your most private part.

“It’s time to plug you darling.”  You feel my finger slowly exit and try your best to leave the muscles relaxed to perhaps give me a glimpse of your loose hole.  You so desperately want to make me happy.  A few more kisses and licks around your holes and you know it is coming.

“Tonight I’ll allow you to have the smaller rubber plug.  I know the rigid stainless can be more uncomfortable.  I want this to be a filling exercise.  I want you relaxed as I will periodically be feeling and adjusting your plug throughout the evening.

You feel more lube and the coolness of the tip of the plug.  With a deep breath, you automatically push outward having learned from your training.  You know it makes me smile when you hear those wonderful three words.  “That’s my girl.”

The tip is in now and only the gradual increase in thickness will need to be endured before that final secure slide and pop as the base glides securely to cover your hole.

“Stay with me little one.”  As my hand holds the plug and you feel my arm across your cheek; yet one more way my touch offers you security.  And then the palm of my other hand falls flat against your pussy holding it lovingly.  It’s a gentle “hug” of all your sex.  Your labia, lips, clit and vagina feel the soothing pressure as the plug rhythmically goes in and out.  Each time, just ever so slightly deeper.

We’ve arrived at the point where the final stretch is imminent.  “It will be painful darling.  Use your training.  You know what to do. Let your muscles accept me.  Push out for me.  That’s my girl.  Breathe. Keep your ass up.  Feel my hand massage your pussy.  Get lost in the sensations.”

We both realize the thickest part of the plug is about to pass into your body.  I see you begin to hold your breath and smack your ass quickly.  “You know better than that. Breathe.”  You also know I get so aroused by making you clinch up.  That dreaded sadistic side.  But deep down, you only want to please me.

I see your upper back rise from the deep breath and feel a sense of pride knowing you are following my training.  At the peak, I fill your hole with the final push.

Your gasp has a sound that tells me your breath is passing across smiling lips. Quickly, the palm of my plug hand presses along the base of the plug and the pressure from both hands gives you the warmth and connection you crave.  I know your eyes are closed at this moment as you breathe my in dominance and bask in your own submission.  Your back arches even more as your push your ass and pussy into the security of my palms.  And the pleasure mixes with the emotion to create a series of shudders.  You know I am smiling.

But we have only begun.  Once again, you recognize the prick of the wheel just above the base of the plug.  It’s a very sensitive area and your mind goes to the idea of it not only around your asshole but also around your cunt.  “Yes, little one.  You must be very still.  I don’t want to hurt you.  Not too badly…….”