Exploring Tabbi

You are called Tabitha, but to me you are Tabbi, my own name for you. When we first meet online you are a woman of frustrated needs. You own a never been kissed pussy, a never smacked bottom, and a virgin anus, and you desperately need to alter this state of affairs. You are a submissive without a Master, an aimless wanderer in a sexual desert, and a flower yet to bloom. I will change all that. For weeks we chat as I lead you, help you prepare yourself, direct you down the road to your fulfilment. I am your online mentor, teacher, and guide. Now you are ready, ready to turn your aches into pleasures, your needs into fulfilments, your frustrations into joys. We arrange to meet. A neutral place, a motel halfway between our homes. There I will begin to help you explore yourself.

You follow me into the room, then stand and wait as I lock the door. This is one time when 'Do Not Disturb' really counts. For a minute or so we stand facing each other, smiling silently, and then I take your hands in mine and draw you to me. We embrace, hugging each other tightly for long minutes, this moment had been a long while coming and we were going to savour it. Then we kiss, our first ever kiss, a gentle meeting of mouths and tentative discovery of tongues, becoming more passionate as our fires ignite. Your hands are holding me tightly, but mine begin their initial exploration of your body, roaming from your shoulder and neck to your bottom, cupping your cheeks and pulling you against me. I have an erection that feels good trapped between our bodies.

Eventually I break free, placing my hands upon your shoulders and holding us apart so that I can look into your eyes.

I speak. "Your safe word, this time and every time, will be 'tomato' - in honour of your blushes. I tell you now, well in time for when we get to where you might need it."

I look hard at you, trying to see what effect this first concrete evidence of our intentions was having on you. But you smile, struck by the aptness of our safe word, and I am content. "Tomato." You repeat. "Yes, I like that."

"I don't expect you to need it today, for today we will just begin to unlock your back door."

You nod, and I see disappointment and relief chase each other across your face. You had both hoped and dreaded that the beginning would be with a lesson in discipline. Discipline, humiliation, bondage, watersports, and even fisting; they will all come, but first a complete trust must be built and we will begin with anal play.

Taking my hands from your shoulders I begin to unbutton your blouse, revealing soft white skin and ample breasts held in place with a lacy white bra. My erection gets harder. Sliding your blouse from your shoulders I allow it to fall to the floor before unzipping your slacks and letting them pool around your feet. Then, taking your hands again I lead you towards the bed, waiting as you step out of your slacks. Dressed now only in white bra and panties, your blonde hair giving you a slightly angelic look, you are beautiful.

"If you are happy to do so, and only if you are, remove the rest of your clothes." This is my first instruction to you, and the only one you will get that will contain an element of choice.

You do not hesitate. Reaching round to your back with both hands you unclip your bra, allowing your full breasts to spill free. Then, still facing directly towards me and wearing a look of vague defiance on your face, you hook your thumbs into the waistband of your panties and with one move, quickly bend and remove them. Then you stand, naked and gorgeous, looking straight at me, making eye contact, your face slightly pink as I look at you. I am drinking in the sight of your body, a sight I have seen in my mind and waited to see in the flesh. You wait for my next request.

I indicate the bed. "Lie down." You comply, looking just a little nervous but with excitement evident in your eyes.

From my bag I take a box of tissues and a tube of lubricating gel, which I place on the small bedside table. I am looking at you intently as I do this. I am doing it deliberately to bring home the sincerity of my intentions. If you are not ready, not committed to our exploration of your desires, this is when it will tell, this is when your resolve will falter. But you gaze at them with interest, no alarm, no panic, just that slight nervousness still evident. Again I am content.

It is now my turn to strip. I do so quickly and efficiently, hoping that my somewhat older and time worn flesh will not deter you from our plans. Before I join you on the bed I take one of the pillows and, indicating to you to lift yourself, I place it folded beneath your buttocks, raising your bottom from the bed. You look at me and smile, believing that you know why I have done that. You are partly right.

I climb on the bed alongside you, rolling to face you and be enfolded in your outstretched arms. As we kiss my hand cups your breast, the thumb rolling your nipple from side to side. A sigh escaped your lips.

Leaving your mouth for the moment, I move down a little to suck your nipple, drawing it into my mouth, my tongue swirling around it. All the time I am playing with your other breast, squeezing and moulding it, tracing your aureole with my finger tips, round and round your rapidly hardening nipple. Your breath is now becoming a little ragged, the attentions paid to your breasts having their effect. It is time to move on.

My lips remain fastened around your breast, suckling at it, nibbling at it, gently biting it, but my hand begins its journey south. It is an uphill journey because of the pillow, but you enjoy the feel of my finger tips dragging over your skin, tracing the outline of your navel, meandering back and forth from there to your bikini line, gently, so gently tracing a path across your skin. Your breath is coming faster now as you are becoming aroused, ready for what I have in mind for you. I know you will enjoy it.

Soon my hand has made the journey all the way to your pussy and two fingers are travelling down its length, one down each of your labia, descending, ever descending, until they meet again on your perineum where they circle randomly, teasing you by wandering first close to your vagina and then your anus. The return journey takes my fingers over the entrance to your lovely moist tunnel, to catch upon your clitoris, the little button standing like a little sentry under its hood, guarding your pussy. I flick it with a finger tip and you gasp.

Now you are ready for the main event to begin. I rise from beside you and move to the bottom of the bed, kneeling on it to raise your legs and fold them back and wide, your knees beside your shoulders. Without being asked you hook your hands behind your knees, taking over from me and leaving my hands free for their purpose and spreading your legs a little wider in the process. For a few long minutes I do nothing but gaze at your most intimate parts. Your lovely wet pink pussy, its newly shaven lips swollen, its entrance gaping and its clitoris peeping back at me. Below is the puckered entry to your anus, tight and virginal, waiting to be used as another way in to your body, another way of pleasing you and your lover. You are blushing now, bright cheeks of shame adorn your face. You are not used to such an intimate examination by a comparative stranger, especially for the reason you have in mind, but the humiliation of it excites you anyway.

Now I surprise you. Instead of using a finger to play at your back door as you expect, I kneel before you, lower my head and plant a kiss upon your clitoris. The surprise is complete, you gasp aloud from surprise and pleasure. Now you realise that I am intent on giving you oral sex, intend on licking and sucking you to climax, on initiating you into the beautiful oral sex club. Shuffling myself into a more comfortable position and with my hands on the back of your thighs I begin.

Using the tip of my tongue I begin to trace out the journey begun by my fingers. Down alternating sides of your pussy and up via the middle, sometimes pausing to dip my tongue into the honey pot of your vagina, sometimes licking and flicking your clitoris. As I do so your breathing becomes faster, heavier, you are beginning that beautiful climb to orgasm. I know that you have not experienced an oral orgasm before. I know it will blow your mind. But I don't want it to come too soon. I have things I wish to do, so I lift my tongue from your pussy and brush your inner thighs with my lips, sometimes gently kissing them, very occasionally licking them with tiny dabs from my tongue. It is erotic enough to keep you high, but not enough to make you cum. Slowly your impending orgasm backs away and I am able to return to your pussy.

This time I begin long sweeping strokes up and down the length of your cleft, sometimes with the tip, sometimes holding my tongue flat against you. Then, as I reach the end of your cleft I begin to investigate your perineum with my tongue tip. You wonder. You wonder if I really am going to do what you are beginning to believe I will. I am. All of a sudden my tongue has made the journey and is playing around your anus, licking it, skating over it, prodding at the entrance with the tip. You cannot believe it is happening to you. You have wanted to taste the pleasures of oral sex, you have wanted to try anal play, and now, without warning you are getting both. The very intimacy of the act triggers your climax, pleasure rolling through you in unending waves, you hips rising from the bed and falling back, spasmodic thrusts into nothingness. My mouth cannot keep contact with such a small target in these circumstances, so I clamp it tightly over your clit, sucking the little bud into my mouth and holding it there, the suction adding to the intensity of your climax. I keep it there until your orgasm subsides.

After it is over and your breath returns to nearly normal I begin once more licking at your clit. It is extra sensitive now because of your orgasm and sometimes your hips jerk in reaction to my tongues touch. Now I move on to your vagina, probing it with my tongue, exploring as deeply as I can reach, licking at its wetness, drinking its juices. You taste wonderful. I need help, so I bring my hand into play, using two fingers to spread your pussy wide and allow me to reach further into your tunnel. Your gasps and moans tell me you are enjoying it.

Eventually my tongue tires of being fully extended and it aches. I move back to your clit with my mouth, just gently nibbling it with my lips, sometimes gently, very gently, biting it with my teeth. But my fingers are still there, now delving into your vagina, softly finger fucking you with first one and then two and eventually three digits. You are still softly verbalising your pleasure.

Suddenly I remove my fingers from your pussy and instead begin using my forefinger to circle your anus. Round and round the rim, never trespassing but never going away. You pull your legs even further back to present yourself more openly, and I know you are ready.

Leaning over I take the lubricant from the table, flip open the cap and squeeze a little blob onto two of my fingers. Now, leaning myself on one elbow to see what I am doing I apply the gel to you, spreading it gently around your back door, making it slick and slippery. You are holding your breath, knowing what is about to happen, worried that I will hurt you, scared that after all the waiting you will not like it, and wondering how you will look me in the face again afterwards. I can see your misgivings in your eyes, but I know they are all groundless. I would not hurt you for the world, and I know you will love it. Mentally I will you to relax, knowing that to say so aloud would simply have the opposite effect right now. My fingers and your anus are now thoroughly coated with gel and I begin the exploration, pushing gently at your sphincter with my index finger. Pushing and withdrawing, pushing and withdrawing. All the time I can see what you are not yet aware of. My finger is gradually gaining entry, each move forward takes it a little further in, and each withdrawal is not quite so far.

"Ok. Tabbi?" I ask, knowing what the reply would be.

You nod hesitantly. "So far, but I'm not sure how I will feel when you go in." You say.

"But I am in." I reply truthfully, for my finger is now buried up to the first knuckle. "See, it wasn't so difficult, was it, now relax and enjoy it."

You look surprised, then a grin of delight spreads a cross your face and I know everything will be all right. You lie back again and close your eyes, revelling in the feeling of your first anal penetration. Now I can gradually begin to explore deeper, and I push a little further, the finger now sliding easily past your relaxing sphincter. Soon I am going in the full depth of my finger and once more your breath is becoming ragged.

But I haven't quite finished yet. Twisting my hand around palm up I introduce a second finger to your entrance, gently wriggling it alongside the first, and gradually expanding your anus to accommodate both. At first you look a little concerned, but I hush you and you relax again, letting me continue. Soon I have both fingers inside your anus, thrusting gently but firmly into your rectum. To me the sight is beautiful, so enjoyable, so erotic, and so very intimate. Now by resting the ball of my hand against your pussy I am able to finger fuck your anus and at the same time use my thumb to manipulate your clit. You are going to cum again.

As you get closer to your orgasm I gradually increase the speed until my fingers are pistoning in and out of you and my thumb is rubbing madly at your clit. You begin to moan and thrash your head. Your orgasm will be a big one when it comes.

And it is. You lift your entire body from the bed, hauling back on your legs, trying desperately to get me into you deeper, harder, and faster. I resist the temptation to try harder. Your involuntary movements could easily dislodge me if I wasn't in control and the last thing I want is for your first anal orgasm to be spoiled. I want it to be perfect, the most exciting and satisfying ever. Why? Because the next time we meet I want to fuck your arse properly, I want to put my cock were my fingers now are. Today I am forgoing my pleasure for yours, but only for the selfish reason of guaranteeing my greater pleasure the next time, not to mention, and more importantly, greater pleasure for you next, and every, time.

When it is over you lie gasping, your legs back on the bed, your arms resting alongside you. You are spent, fully satisfied, and with the smile to beat all smiles fastened firmly across your face. Our first meeting has been a resounding success. You are a good pupil who now trusts her teacher. From here we can go in any direction we choose. You will not forget the word 'tomato' but it is unlikely that you will ever need to use it.