Shy Beginnings

Nervous, I check my watch. Just fucking great. I'm going to be late for my first appointment. I straighten my short black hair and smooth my plain khaki skirt over my knees. Maybe I should have just driven myself instead of taking the DART. If I wasn't such a prude, I wouldn't have cared if anyone saw my car sitting outside her place. I try to look innocent as another group of people load onto the train. I feel as if, even though I'm dressed conservatively, in a khaki skirt and white button down shirt, people can see what I'm about to do. Why am I even attempting this? It's something I've always wanted to do but I just don't know about this...

The train slows to another stop... my stop. I gather my briefcase and head towards the door. I check my watch again and start to walk the two blocks away to her house. The walk is excruciating. My nerves are on edge. I arrive at her doorstep and take in a deep breath. Letting it out slowly, I knock on her door softly. I check my watch. Right on time.

I can hear the faint Clack! Clack! Clack! of high heels approaching the door. It swings open and she greets me with a tender smile. Her sweetness surprises me. I follow her inside. She is an exotic beauty, with dark brown hair that flows long and soft past a firm rear, big brown doe eyes peering from under long eyelashes, soft plump rose lips pouting. Her skin is caramel colored and begs to be touched. She appears innocent and sweet wearing barely any make-up and a pretty white and pink rose bud patterned dress to right below the knee. Her black leather boots with zippers up the inner leg breaks the innocent persona.

I jump when she lightly grabs at my hand and leads me upstairs. Her place is exquisite and beautiful, decorated in a classic Victorian manner. As we climb the stairs, I find myself staring at her plump round ass. The room she leads me to is decorated similarly with a four poster canopy bed and expensive antique armoires.

After closing the door behind us, she stands facing me. "Unbutton your shirt." Her voice is heavenly. I obey and start to unfasten my shirt. "Slower!" she snaps. I jump at her sudden harshness and continue to release each individual button from its trapping. After my shirt is open, she reaches towards me and pulls the sides apart to examine my breasts still captive in a cotton white bra. Knowing that she is looking at me this way begins to excite me and my breath starts to shallow. My heart is pounding and I'm sure she can hear it.

"Pull your skirt up."

I oblige and she looks me over.

"Turn around."

I can feel her eyes on me even after I have turned. I can sense her looking at my ass peeking out the bottom of the pair of plain white bikinis. She clicks her tongue in disapproval. "Take those off this very instant," she instructs. I drop them to my ankles and kick them softly off. I hear her step closer.

WHACK! A sharp spank of her hand to my right cheek causes it to burn. Even though it hurts, it exhilarates me and makes my senses come alive. The sharp sparkling sensation of my flesh sends an electric shock through my body. Suddenly I smell her perfume, rich with the scent of rose and sandalwood. Another rough spank to my ass and I hear the sounds of birds outside and her breath, heavy but smooth. I taste a faint taste of blood and wonder if I bit my lip. I see the grains of the wood in her door.

She circles around me eyeing me up and down. "Undress... slowly. Fold your clothes and lay them neatly on the chair." I start by sliding the white shirt off of my shoulders. The feel of it sliding off is titillating. I fold it and put it on the chair. I reach behind my back and unfasten my bra. I pull the straps off my arms, not quite ready to expose my breasts. Finally, I free them from their cups and blush knowing that I am exposed to an almost perfect stranger and that my little pink nipples are rock hard. I place the bra with the shirt. I undo the buttons of my skirt and slide it slowly down over my now bare ass and legs. I step out of it and fold it neatly as instructed. It joins the other clothing items. I stand now finished. "Pick up your panties as well." I bend over to pick them up and feel another hard smack on my bare ass. Without a word, I pick them up, fold them, and place them on top of the pile of my clothing.

She leaves me standing there a minute, naked and alone. I can hear her footsteps and want to look to see where she is but I know that if I do, I might break some sort of rule. Even though this is my first time, I knew before coming here almost what to expect. I hear her open one of the doors, retrieve some items, and then come towards me. She appears in front of me and places small metal clips on my nipples. She also puts a metal collar with a chain around my neck and then leads me to the soft, inviting bed. "Lie down in the center." I obey once again. She pulls several lengths of white cording from the bedside table. She ties each wrist and ankle to a post tightly causing me to be in a spread-eagle position.

She leaves again for a few moments. When she returns, she brings with her a short black wide end riding crop. She taps it against her hand. It's hard for me to see her so provocative when earlier she seemed so virginal. I smile at the thought and immediately regret is as she frowns at me. "What is so funny, bitch?" she asks and with that smacks me hard with the crop on my thigh. I put the straightest look on my face as I ever could have. She spanks me again, this time a bit higher. She smiles and runs the crop up my thigh, over my labia, and along my stomach until she crests the peak of my left breast. She pops me hard on nipple. It throbs with the impact and the tightness of the clip. As she circles my nipple with the end of the crop, she pulls a cigarette out of a pack sitting on the table and lights it. I watch her smoke the cigarette seductively and long to be that cigarette pressed between her luscious lips.

She puts her foot up on the bed close to my head. "I want you to lick my boots. Lick them like you would lick my sweet pussy," she commands of me. I cup my mouth over the inside of her boot and lick a small spot in a circular motion. I then lift my mouth and leave a small trail up the side as far as I can reach being tied down. I strain to reach further and swirl my tongue down the boot again in little circles and end this trail with a soft, long kiss. I hear her moan slightly as she watches me.

She steps down and rewards me for my obedience by opening a few buttons of her dress so that I can see the black corset she is wearing underneath the dainty dress. Her breasts, firm and round, peek out the top and I imagine that the nipples are only barely beneath the top hem. I feel my snatch moisten with her sight. She pops it with the crop upon seeing my excitement swell.

"Beg me to see more, my pretty little slut."

"Please, Madame Jessalyn, let me see more of your beautiful body. I need to see it, please. Oh my god, I need it."

She smiles sweetly, bringing back that virginal appeal, and unbuttons the dress a little further and slips it off to let it drop to the floor. She is stunning in the black satin corset and tiny black g-string. I can see the black string barely starting to creep in between her perfect lips, the faint amount of soft pubic hair only just above her sweet slit. I can also see the tiny droplets on her lips like morning dew upon rose petals. My clit begins to throb in response. I want to taste those lips along with every part of her perfect body.

She slides the crop over her body seductively and follows immediately with a sharp smack to my crotch. I grumble in excitement deep in my throat as my twat twitches deep inside. She steps onto the bed again, this time straddling my face, but not yet sitting down. She rubs her clit and tilts her head back moaning. I see her get even wetter. I long to taste her. She slips two fingers into her juicy hole and starts to finger herself slowly. Every time her fingers withdraw from her cunt, I see the slick wetness deposited on them. "Beg me for more, slave."

"Please. Oh fuck please. Let me taste your sweet lips. Lets me kiss your sweet spots. Anything. Please let me do anything you want!" She lowers her sweet slit over my face no more than an eighth of an inch away from my nose. I smell her sweet smell and inhale it deeply. I wonder if I would do wrong by tilting my face into it so I could taste it just once.

"Please..." I beg. She slams her pussy, dripping wet, onto my face and I hungrily gobble at it, swirling my tongue in tight circles and sucking on her sensitive clit. I work in circles and suck the skin of her labia all around, working from clit to vaginal opening and back again. I swallow her sticky, sweet excitement as she moans and rocks into me. She thrusts her hips into my face. She yanks my hair and pulls my head deep into her cunt and gushes intensely on my face. Her body shakes with the throes of mind-splittingly vicious orgasms. I can feel my own orgasm building deep inside just from the excitement of it all.

She climbs off of me, breathing heavily and glistening with perspiration, and strolls over to the bedside table and lights another cigarette. She comes back to my side and unties my binds, freeing me from her bed. She pulls out a clear, double-headed device and slides it into my cunt and ass, takes the metal collar off, and whips at my breasts once more before removing the clips. "Get dressed. Come back tomorrow. Same time."

I go to stand and get dressed as she adds, "And do not touch yourself or masturbate in any way... just leave that in until tomorrow."