Jenny's Journey

Jenny was more than a little nervous as she watched the taxi pull away -- terrified was more like it. The bus trip had been scary enough. Never having ventured beyond her front door dressed en femme, she had ridden a bus 700 miles to a strange city, looking like a low-classed slut. Here she was, at last, on the doorstep of a man she had never met in person before, here for a week as his submissive 'slave.'

Their entire 'history' together flashed through her mind as she moved toward the doorbell. Sir Robert had made contact via Email after she had posted a comment on a 'slave' forum. She had been vulnerable, lonely and; frustrated trying to live out her T-girl dream, and not having any luck finding a Master until Sir Robert contacted her. There had been months of getting to know each other better, on-line domination, many digital photos, then phone calls, and web cam sessions. Everything led up to this moment. With a push of that doorbell, she would be entering a real world of servitude, degradation, pain, and humiliation as Sir Robert's slut-bitch, at least for the entire next week. The return bus ticket in her purse was comforting. Jenny had no doubt of her capacity to submit and suffer for her Master. Her only question was just how deep was his commitment to her training and permanent enslavement. Only time will tell, she thought with a sigh as she heard the doorbell chime.

In seconds the door opened. There He stood, her Master! Pictures had prepared her for his strong profile and broad shoulders, but not the sheer animal magnetism that radiated from this clearly alpha male.

"H-h-ello, M-Master," she stuttered, lowering her eyes and dutifully falling to her knees at His feet.

The coarse doormat prickled her legs through the black nylons.

Instantly, Sir Robert took command of the awkward situation. "Hello, jenny. I'm glad you arrived on time. I thought you might either chicken out entirely, or else stay at the bus station to suck off a couple of johns to work up your courage to present yourself for my tortures and delights."

"Oh no, Sir," she stammered, "this slut would never service anyone else unless You required it."

"Humm... we may have to test you on that before the week's over." Not expecting an answer, he went on, "Get off your knees, bitch, pick up your bags and get your ass inside. Don't worry, though, you'll be spending plenty of time on your knees."

As jenny scrambled to her feet, her lack of grace in even the moderate heels she wore embarrassed her. Blushing deep red, she scampered to obey.

Sir Robert guided her down a hallway to a small bedroom, where she set her luggage down.

"This will be your room when you are not servicing me or being used in the dungeon, cunt."

"Yes, Master Robert, Sir. Your slut will obey," she responded.

Taking her by the shoulder, he marched her back to the living room.

Releasing her, he examined her with a critical eye, "Let's have a good look at you now. Raise your arms and turn around."

Clasping her fingers together behind her head, jenny slowly pivoted, eyes, down, and blushed again as she felt Sir Robert examining her. His gaze felt like it went beneath her dress, beneath her bra, girdle and hose, beneath the tampon and pad, clear through to her very soul. That wasn't so surprising, given the length and depth of their internet courtship, she realized. This man knew all of her darkest, most perverse desires and dreams, and wanted her because of them.

The nervous bitch standing before him definitely could pass as a woman anywhere.. Professionally styled blonde hair and the makeup conveyed a somewhat trashy image, just as he preferred. The breasts were on the small side, but firm and natural. Gripping her waist, he felt the tight girdle snugging her in. The hips were also on the small side, but defined. Her leg muscles, shaped by the high heels, flexed in the black hose. Ah, those legs, he thought, her most visible erotic feature. Even unsteady in the high heels, this slave could turn heads with those killer legs. The mouth, outlined in garish, whore-red lipstick, was probably worthy of his cum, and he suspected that her 'cunt' would be too, if she had prepared and been training it per his orders.

"Are you on your period?" he asked brusquely.

"Yes, Master, but..."

Hands on her shoulders pushed her firmly to her knees. As a dutiful slave, jenny kept her hands where Sir Robert had ordered them placed, behind her head.

Unzipping his jeans, he fished out a semi-hard cock and shoved it into her gaping mouth.

A little squeal and a 'glug' escaped as he hit the back of her throat. Jenny had spent the past several weeks learning to still her gag reflex while deep-throating the thickest dildo she had. But the penetration was always slow and gradual, not a sudden full-depth thrust. Her first beauty shop hair-do was mangled as Master Robert wrapped his fingers tight in her blonde hair and held her in place as he fucked her face, smearing her lipstick all over his manhood in the process. Tears soon streaked her makeup as Master Robert worked her mouth and throat.

It seemed an eternity to jenny, but was only a couple of minutes before her Master yanked her hair hard, slapped her chin with his swaying balls, shoved His cock literally down her throat, and with a grunt of pleasure, came.

The salty glop spattered all over her throat, and coated her mouth as He pulled out abruptly.

"Zip my up, bitch," He commanded.

Jenny had been fantasizing about this moment for months now. She dreamed that after showering His cock with her submission, love, and devotion, Sir Robert would hold her and gently caress her while telling her she was the best cock-sucking slave in the history of whores.. Instead, He had used her mouth to cum, and now He was done with her. The tears in her eyes now weren't from her throat being ravaged, but of dashed dreams. Being a submissive slut was harder than she had ever imagined.

She deftly tucked His shrunken tool inside His shorts and carefully zipped the jeans up.

"That took the edge off nicely, bitch. You have exactly fifteen minutes to shower, get changed into your sluttiest outfit, and present yourself for lunch. We have to keep up your strength because you have a week of torture ahead of you, and I want to get started. But you have to wash that bus-station stink off before I'll touch you."

He helped her to her feet, slapped her face just hard enough to sting a little, and sent her down the hall to her room.

From the moment He helped her up, jenny was thinking just what to wear for her first session with Sir Robert. She wanted Him to have easy access to her body, but she wanted to be as alluring and sexy as possible. The more turned on He was, the harder He would work her over. Since that was their mutual goal for the week, she had packed her wardrobe accordingly.

As soon as she entered her room, jenny began stripping off her soiled traveling clothes. In the attached bathroom, she tugged out the tampon and filled the bulb syringe with hot tap water for a quick douche. Only a touchup was necessary. For the previous 3 days, she had douched to clear with hot soapy water, vinegar, and alum water to tighten up her 'cunt' for Sir Robert. A couple of minutes finished the shower because she knew that repairing her hair and makeup would take the most time, and she certainly didn't want to keep Him waiting. He had told her a few of His favorite punishments, and despite being a hopeless pain-slut, jenny wasn't eager to experience them. Besides, now that she was actually in His house with His dungeon, maybe even worse punishments and tortures were available for uncooperative bitches.

Between the electrolysis, hormones, and daily shaving, jenny decided she could skip shaving her legs and bikini area a second time today.

The lacey black garter-belt was fastened around her waist, just below her new belly-button piercing. She slid her best back-seamed stockings, in perfect black, up her well-muscled legs, and hooked all six garters. Taking a few extra seconds, jenny stroked her legs, feeling sexy, and excited by the allure of the nylon. Hose always had that effect on her. And she did believe her legs were her sexiest asset. She imagined heads turning, male and female when she walked down the street wearing black hose and high heels.

Next was the very short baby-doll gown in light pink nylon, followed by the five inch pumps in matching pink.

Despite its mauling, her hair actually cooperated with only a few brush strokes and a bit of hair spray.

Her makeup didn't take much time or thought either. She had been doing it daily for several years now, and could apply her whore-paint flawlessly and quickly. Jenny changed her earrings to her favorite pair of thick, heavy sterling silver hoops. A final check in the mirror, a misting of Poison, Sir Robert's favorite scent, and she was ready for action. The thought made her giggle as she made her way back to the living room.

As she approached, Master Robert caught a whiff of her perfume. The musky perfumes always turned him on: White Shoulders, Roses in the Rain, and of course, Poison. He was extremely satisfied with the appearance of this T-girl slave. She had none of the exaggerated mannerisms of the typical cross-dresser or gay male. She moved like a shy, somewhat insecure woman, and Sir Robert accepted her as such. To him, the approaching woman was his submissive pain-slut slave-girl, not a male in drag to engage in gay S & M sex. On the computer, jenny had needed reassurance that he considered her a complete woman.

"Fine choice," he complemented her outfit.

The impossibly high spike heels in baby-pink matched the very short gown. The light pink contrasted nicely with the true black hose and garter straps visible below and through the gown. It was definitely female, definitely slutty, and provided complete access. She had understood His desires perfectly, a very good sign.

Jenny stopped in front of Sir Robert, lowered her head, crossed her legs, and did a little curtsey, holding out the hem of the gown just below her slit. Despite their conversations, and agreed upon conditions and limits, jenny was still a little frightened. This wasn't make-believe, or cyber-fantasy anymore. This was real. Her tears and pain would be real too. Could she truly trust this man? Was he a closet axe-murderer? Would he really hurt her?

As if reading her jumbled mind, His calm voice cut through her mental fog, "I want to hear you list the 5 'no-never' limits I allowed you, and; the one conditional one we agreed on."

Keeping her eyes on the pointed toes of her pink pumps, jenny quietly recited, "No blood, no scat, no kids, no weapons, no breath-play, Sir, and no bondage until this slut becomes comfortable and learns to trust her Master with her life."

"Yes, my bitch, that is what we discussed. I have no problem with the 'no-never' list. It's short and sensible. Before this week is up, however, I want you to get over the 'no-bondage' idea with me, though. I don't think even a pain-slut like you can take some of what I have planned without being tied down. You did request to be broken, as I recall, and that is impossible unless you are restrained. However, since I'm quite secure in my own power as a Master, I'll wait for you to tell me when you are ready for restraints."

"Yes, Master, thank You, Sir Robert. Your slut-cunt will do her best to not disappoint, and to serve Your needs," jenny said quietly. Inside she was seething with desire, wanting, needing to be strapped down and broken until she was screaming for mercy, for the promised brand and piercings of ownership Sir Robert had told her of. But their agreement was practical and realistic, giving her time to acquire more trust in Him. This was necessary for her descent into absolute slavery to this man, and they both recognized it.

Taking her hand, Master Robert drew her into His strong arms. As he tasted the lipstick on her eager lips, his hands slid over the gown, feeling the swell of her hips, the taper of her waist. When his hands squeezed her breasts, jenny moaned deep in her soul. He was quick to probe her open mouth with his tongue, which inflamed her more. Soon he slid his hands down her body and cupped her ass cheeks. Pulling the tight globes, he ground his growing cock against her.

Breathless, jenny broke the deep kiss, "Oh please Master, whip me, use me, take me."

"Yes, bitch," he replied, "it's time to begin your real slut training. Are you still sure you want this? Because once we begin, there's no turning back, you are committed."

"Yes, Sir, please train this slut to be your perfect pain-bitch. Make me the cunt of your dreams, the whore I want to be for you!" jenny answered.

"Then it's time to take you to the dungeon."

Holding hands like teenagers, they went through the door he unlocked, and down the basement stairs.

Jenny could only gape in amazement. The large room was painted white, had recessed lighting, and displayed an array of serious bondage equipment. She was conscious of her spike heels clicking across the tiled floor as she examined each item. There was a floor-to-ceiling whipping post at least eighteen inches in diameter, complete with chained shackles dangling from it. A sturdy wooden armchair had no seat, but wrist and ankle straps. A wall shelf held an array of plugs ranging from petite to monsters as thick as her forearm. Jenney shuddered and turned to touch the table complete with stirrups and restraints. A 'horse' with dildo attachment occupied one corner while a short stanchion topped with another dildo stood a short distance from what was obviously a 'spanking bench.' Along one wall was a stainless steel double sink and seatless toilet as well as cupboards and racks of very scary-looking clamps. A display of whips and paddles caught her eye and her fingers lightly caressed the wicked strands of the whips.

Seeing her obvious interest in the flogging tools, Sir Robert told her, "Pick out 3 of them, my dear."

Jenny understood instantly, and examined them more critically. With the tip of her finger, she delicately selected a broad plywood paddle with large ventilation holes, a thin leather cat, and finally a limber fiberglass cane.

"Excellent choices," she was told as Master Robert led her to the spanking bench and draped her over it. He nudged her legs apart with his foot. Even with the bench supporting her, she instinctively gripped the handholds beside the thick leather cuffs as her legs were spread even wider.

"You may squeal and scream, my sweet bitch, but you are not to move your legs. Do you understand?"

"Y-Y-Yes, Master," the trembling voice betrayed her excitement and nervousness as a thousand thoughts swirled through her mind.How hard would Master whip her? How many strokes? Would he only beat her ass or would he work her thighs too? Could she hold discipline? Would she disgrace herself and beg him to stop during this, their first dungeon session?

Whoosh, CRACK! Her ass exploded in pain as the stout wooden paddle made contact. Caught by surprise, she didn't have breath to scream, so sucked in air as her head shot up in shock.

Lowering her head in submission, she softly began the count, "One, Master."

Sir Robert had an expert's pace and patience, allowing her to savor all the pain from each stroke. Jenny counted and suffered as the thick paddle hammered her ass. The squealing didn't begin until his aim lowered to her thighs. She was close to tears when the paddle was exchanged for the fiberglass cane. Since her ass and thighs had been warmed up, the cane felt like it was literally shredding her flesh as she cried out her agony. White-knuckled, she held on as Sir Robert plied her thighs with welts that instantly purpled on impact. She was truly sobbing when he laid the cane aside.

"You liked the cane, didn't you," a statement, not a question.

"Y-y-y-yes, Master, but it hurts so much," jenny choked out between sobs. "Your slut needs the pain, and to prove my love for you by suffering anything you give me."

"Is this exciting for you? Do you really like it?"

"Oh yes, Master. This is a dream come true for your slut. She needs your pain. Beat her for your pleasure, Sir," jenny condemned herself.

The 'cat' was knotted leather boot laces, and after the second lash, Jenny was sobbing again as crimson streaks filled the spaces between the cane's welts. The knotted end of each tail left its own deep bruising punctuation mark.

Flicking the leather on the inside of her thighs wrenched a satisfying scream from the crying bitch.

"Oh, don't worry, slut, I'm saving the insides of your thighs for a real punishment session. That was just a taste," Sir Robert told her with a chuckle.

Jenny wasn't doing any of the laughing as he helped her stand, and walked her over to the table. With a wooden step-stool, she climbed up. Positioning her, Sir Robert had jenny kneeling close to the edge, sitting back on her spike heels and whipped ass. Reaching down her neckline, he attached strong nipple clamps to her. A low moan was her only response. They hurt, but her nipples had suffered much worse, and she knew there'd be more to come. Each clamp had its own chain which he threaded through her hoop earrings, and hooked the chains back on themselves. The chains were short enough that her head was pulled down to her upraised tits. She could have practically sucked her own nipples.

"This position is for when I choose to whip the front of your thighs, and tits, you cunt. Not only does it stretch the thigh muscles, and rub your worked ass and thighs, but it allows you to watch the cane and whip as they mark the fronts. Then you can see the welts actually form through your hose."

Hands clasped behind her head again, jenny watched in fascinated horror as the cane whistled down on the taut nylon. The red line appeared almost instantly, then after another couple of strikes, the first one swelled into a raised, purple welt all too visible through her black stockings.

The clamps helped divide her attention between breasts and thighs. Pain from each stroke caused her head to jerk up, torturing her nipples even more, just as Master Robert had intended.

When he was satisfied with the quality and quantity of welts on her thighs, Sir Robert had her remove the short pink gown. He whipped her breasts until the clamps were pulled off by the force, then gave her ten measured strokes with the cane across her mounds.

Sobbing quietly afterwards, nestled in his arms, jenny admitted she had never experienced pain on the level Master Robert had been able to give her in such a short time. She shuddered in anticipation when Sir Robert told her that when she consented to restraints that he could beat her harder and longer, to actually break her as she had dreamed of so long.

Gently pushed to the floor, she sucked him in deep and began to work on the growing rod. Tears, makeup, drool, and pre-cum combined to give Him a flavor Jenny was quickly learning to love. Eager to please her Master, she was disappointed when he pulled out at the last moment and pumped the sperm all over her face.

He led her back upstairs and was still taking pictures of her cum-streaked makeup when the doorbell rang. Jenny gave him a quick 'caught-in-the-cookie-jar' look.

Laughing, he told her, "Oh, that's the pizza guy. I called earlier for a 5 o'clock delivery."

The doorbell sounded again.

"Well, go answer the door, slut. The money for the pizza is on the stand beside the door, even the tip. Maybe next time you'll have to give him a blow-job for the tip. Blow his tip for a tip!" he teased her.

With a burning blush on her face, jenny crossed the room on unsteady legs. Tensed by the high heels, welted legs were chafed by her nylons. She raised an arm to wipe some of the slime off her face. The growled warning told her to wear her shame as she answered the door.