tagTranssexuals & Crossdressersjenny Trains Her 'Slut-sis'

jenny Trains Her 'Slut-sis'

byslutty_jannelle©

Although each story will stand on its own, the reader will enjoy the series more in sequence: "jenny's Education," followed by "jenny Gets a 'Sister."




It seemed like she'd just gone to sleep when jenny shook Kay awake.

"Time to get up, girl, We've got a big day ahead. Lots to do," jenny said, unceremoniously pulling the blanket off.

Instinctively, Kay crossed her arms to hide her bruised breasts. "It's a little late for modesty, don't you think?" jenny teased.

Rolling over with a groan, Kay's body reminded her of yesterday's indignities compounded by sleeping on a chaise cushion on the floor at the foot of Master's bed. She had lain awake last night, excited by the prospect of being trained by Master and becoming part of this household. Obviously there was love here in addition to the necessary pain. She'd heard jenny thrash beneath Master, making the bed creak.

Absent a nightie, she'd been permitted to take off her high heels, sleeping in hose and garter belt. She stood up, the butt plug reminding her the training was real. Slipping on her heels, Kay whispered to jenny, "I've gotta pee."

With a smile, jenny told her, "No, not until we get Master's coffee started, then we get to go."

There were a lot of rules Kay was going to have to learn.

By the time they got the coffee maker loaded, Kay was in distress. She nearly had an accident from the sound of the water filling the coffee pot. Finally they made it to the bathroom. Producing the key, jenny unlocked Kay's 'training belt' with its crotch strap, and bending her over, removed the plug. They both giggled at the sucking sound it made as it left her sore anus. Then Kay gratefully collapsed onto the toilet. Her bladder found relief as the stream gushed, but only gas came out the back.

"This is when we do our daily douche and enema," jenny told her, removing a pink douche bulb syringe from under the sink. She kept talking as she filled it with hot tap water with a healthy squirt of hand soap, "We do this every day unless Master orders something else. You'll have to do both holes. Tehehe, I've only got to do one," jenny laughed at her own joke. "We don't share anything that gets inserted without proper cleaning. So you get excused from douching today. We'll get you your own bulb syringe when we go shopping."

Kay watched, fascinated, as jenny slid her panties down, pulled out her overnight tampon, and used a little soap to lube the thick nozzle before pushing it home and squeezing the bulb.

"Come on. Master's coffee should be ready," jenny guided Kay back to the kitchen. While filling three cups with the aromatic coffee, jenny answered Kay's unspoken question. "Since it's only one bulb-full, I can hold it easily. Master says that carrying it a while does a nice job of cleaning me. Besides, if He want's a morning fuck with His coffee, He likes the feel of the hot liquid sloshing and heating me up inside."

They carried the coffee to the bedroom. Having showered in His private bathroom, Master was standing at the sink, shaving. Wiping traces of shaving cream from His lips, He took a sip of the steaming brew. "Ahh, very nice. I've got an early tee time today, jenny. I want you to take Kay out. Get her the things she'll need. That includes a couple of girdles, tight ones, and four inch heels, cosmetics, toiletries. You know what I like." Not needing an answer, He continued shaving, drinking coffee, and dialing a business associate on His cell phone.

Tapping the mesmerized Kay on the shoulder, jenny led her back to their bathroom. Sitting to release the flow, jenny sipped her coffee, "No douche for you this morning, but we'll have to make up for it later on . Now wash that plug so it can go back in. We've got places to go, girl!" jenny said with a grin.

Although she'd been parading around semi-nude for almost twenty-four hours, Kay still felt a little self-conscious cleaning the sex toy in jenny's presence as though it were a toothbrush.

She watched silently as jenny used a large plastic medical syringe, minus the needle, to inject a couple of ounces of red colored mineral oil into her empty 'cunt', then wet a tampon applicator tube in her mouth before putting one high heeled foot on the toilet seat and inserting the tampon with practiced ease. Peeling the soiled pad off her panties, jenny disposed of it as any woman would, in the wastebasket. Watching her stick a fresh pad into her panties, Kay realized that jenny could put most genetic females to shame handling her period.

"For our periods, we only wear 'super' tampons and maxi-pads, start to finish. A 'lite' day is when Master doesn't whip us," jenny again revealed her perverse humor.

Without a word, Kay handed her the clean plug, turned around and bent at the waist, fingers parting her cheeks for the impalement. She heard the jar opening, then smelled the menthol chest rub before the plug reached her.

"Ah-h, o-o-o," she moaned as the greased plug sank home and the menthol stung her tender flesh. Shortly, the worst of the stinging passed. It seemed to Kay that the sting alternated with the cold sensation

Pointing to Kay's blouse and skirt laid over a chair, jenny told her to get dressed, then turned to the endless series of built-in drawers in the cavernous walk-thru closet. She chose a long open-bottomed girdle in black, that went from below her black bra, to just below her 'clit.' Clean stockings were hooked to the girdle's garters. The thin summer dress didn't conceal the outline or color of the bra, and girdle, or her black hose. White pumps, matching purse, and jenny was ready.

Kay scanned her scuffed three inch heels, drab skirt and blouse in the mirror and felt ashamed of her appearance. As the tears formed in her eyes, jenny understood instantly and hugged Kay tightly," It's okay, girl, we're going to get you the kind of clothes Master wants to see you in. You'll see. By the time we get home, you'll be a dream-slut."

Having such a wonderful slut-sis was going to make life so much better, Kay decided as they drove in jenny's little car to the mall. It wasn't the usual one she shopped at, but the upscale one farther out, anchored by a national department store.

They marched in, and exited three hours later, staggering under a mass of shopping bags.

"Wow, that was fun," Kay exclaimed, "but expensive. I hope Master doesn't mind how much you spent on me."

"Well, if we overspent, Master will cane both our asses," jenny laughed, confident she had fulfilled His orders. As always, He was right, Kay did need a complete, quality wardrobe to build her self-esteem if she was to become the slut Master envisioned.

After piling the bags in the hatch back, they stopped at a fast-food place for a snack. Kay looked forlornly at the pictured sandwiches as jenny ordered them salads and bottled water.

"Master says you're going on a diet," jenny said. "Actually we both are. I try to watch what I eat, and I do exercise to try to keep a waistline, but it's hard. Anyway, you'll look better and feel better loosing some of the extra weight. Plus, you'll be more limber to serve Master," jenny reminded her.

As they ate, jenny told Kay about her exercise class and that Master had ordered her to enroll Kay. "He's serious about this, slut-sis, so you'd better be too. Otherwise my ass is going to suffer," jenny reminded her.

They signed Kay up at the fitness center for jenny's aerobics class before they stopped at a pharmacy.

After leaving her prescription for hormones and Kay's for birth control pills, they went up and down the aisles. The shopping basket Kay carried was soon piled high with cosmetics, brush and comb, shampoo and conditioner, bottles of vitamins, a mesh bag for laundering dainties, deodorant, hair spray, body lotion, a bleach blond hair coloring kit, shaving gel, razors, toothbrush, and a large bulb douche syringe on the very top. Then they selected a large cosmetics caddy to keep Kay's things separate in the bathroom.

Unloading everything at home, jenny announced they were to swim twenty laps in the backyard pool before starting supper, "So strip, girl. We're going swimming," jenny ordered, with a sigh of relief, peeling off her damp girdle and hose.

Kay was surprised, but glad when jenny removed the waist belt and butt plug. Noticing that jenny retained her tampon, Kay asked, "Do you swim with that in?"

"Oh yes," jenny replied, "Just like you will when you get your monthly 'visitor.'"

Recalling the discomfort and crampy feelings a tampon gave her during normal activities, Kay wondered what it felt like wearing one swimming, but jenny reassured her that with extended training, "you get used to it, believe me. And it's nice to swim nude."

After swimming their exercise laps, they splashed and frolicked like kids, enjoying the water and sunshine. When they climbed out, jenny wrapped her arms around Kay's waist and pulled her close for a sloppy, pool-water kiss. The new sensation of jenny's firm breasts against hers was surprisingly exciting and Kay parted her lips to the probing tongue. Water dripped from their hair as hands caressed and explored. Never having touched another woman sexually, let alone a transgendered one, Kay jerked her hand back in embarrassment when she instinctively stroked jenny's 'clit.'

"Here, let me show you," jenny soothingly said, leading her by the hand and lying back on a chaise. She spread her legs wide and pulled Kay down beside her, guiding her hand to that special place.

Rubbing jenny's wet 'clit,' Kay was surprised to feel it stiffen as jenny moaned her approval, but it didn't grow bigger. Seeming to read her mind, jenny explained amid gasps of pleasure, that the hormones and some specialized surgery had eliminated the problem of erections, but that she did get excited and could experience orgasms, "Oh use your mouth, sweetie! Oh, oh yes, just like that!"

Wrapping her thighs around Kay's head, jenny held the girl close. Kay began with timid darts of her tongue, but jenny's moans and thrusting hips encouraged her. Soon she was licking, sucking, and nibbling until jenny stiffened and cried out her orgasm.

"Master will give you yours tonight," jenny told the twitching woman as she swatted Kay's hand away from her own throbbing clit.

After showering, jenny once again inserted Kay's training plug and locked the restraining belt. In her own tight girdle, new nylons, and her first pair of four inch heels, Kay wobbled uncertainly into the kitchen to help prepare supper.

After the meal, Master ordered jenny to take Kay to the dungeon and 'prepare' her.

As she buckled the leather restraints on Kay's wrists and ankles, jenny told her, "This is going to hurt, but Master wants you to begin your 'pain-orgasm' training. I wish He was working me over tonight instead though, if that's any consolation,"

"Well, after licking you out by the pool, I've needed a biggie. I'll do anything Master wants, as long as He gets me off," Kay replied as jenny approached with the thick cock-shaped gag.

Once gagged, her wrists were hooked overhead like yesterday, and with her new four inch heels, Kay stood taller. But her calves soon protested the enforced posture. She'd grow used to those wonderful heels, but not tonight, she decided.

The waist belt was unlocked and removed. Kay's anus tried to pull the plug back inside as jenny tugged it free with a wet 'plop.' Instead of relief, Kay missed the now familiar full feeling.

Fetching a fearsome dildo, jenny showed it to the bound woman before attaching it to a steel stanchion positioned just behind Kay.

'That's an elephant dick,' Kay told herself, 'it'll either split me in two or come out my throat!' But she spread her legs enough for jenny to insert just the lubed head into it's intended target.

Squealing around the gag, Kay tried to stand taller, but jenny adjusted the stanchion so she couldn't escape the intruder.

She watched in amazement as jenny put fierce looking clamps on her own nipples, gasping from the pain. "That's to keep me focused and remind me that I'm to give you real boob pain," jenny told her.

As she moved, the connecting chain between the clamps brought additional gasps as she came to Kay with a limber fiberglass switch in hand. "Master ordered fifty strokes to your breasts, and if He can't count fifty stripes, I get a full hundred on mine," jenny told her, the switch whistling through the air.

Kay cried, she squealed, and eventually screamed, but took the entire fifty.

With soft words and gentle hands, jenny caressed and kissed the inflamed, welted globes.

When Master entered the room, she immediately fell to her knees, head bowed, her hair tickling Kay's sopping slit. "Well Kay, did jenny give you the entire fifty strokes on your tits?" He asked. Kay nodded. "Good, then we're ready to begin."

Begin? Kay had been beaten most of the way to orgasm already.

Wide-eyed, she watched Master direct jenny with a minimum of words as the TG slut climbed onto the gyno table and hooked her spike heels in the stirrups. Strapping her firmly in place, He forced her knees toward her shoulders, spreading her wide. Shuddering in pain, jenny cried out when He pulled on the nipple clamps. He picked up the cane still wet with Kay's pain-sweat and began marking jenny's inner thighs. She moaned and soon began squealing, but He made no move to gag her. She didn't scream until He raised His aim to her chest, hitting the tender flesh and the biting clamps.

Her own pain forgotten, Kay watched in fascination as jenny's tears soaked her face. Holding the tit-chain in one hand, He yanked on it viciously while striking her madly humping slit. After no more than twenty-five strokes, she went rigid, began quivering, shrieked, and came.

Dropping the chain and turning away from the sobbing woman, Master fixed another pair of clamps to Kay's buds, tightening them down until the wicked teeth brought Kay up on her toes. He adjusted the dildo's pole upwards until she had at least six inches of the cunt-splitter inside. The now-familiar vibrator stand was placed against her clit. Then He snapped a leash to the clamps' chain. Running the leash through a ring-bolt between jenny's legs, He dropped His pants, straddled jenny's head, and began fucking her throat while mercilessly pulling Kay down farther onto the dildo by her nipples alone.

Savaging jenny's mouth, He jerked the chain to inspire Kay. "You'd better cum before I do, bitch. Otherwise, you get another fifty on the tits, and we begin again," He muttered through clenched teeth.

With the approach of orgasm, her ass began to spasm around the silicone cock. It would have felt divine except for her shrieking tits, but her body wouldn't be denied and she came. Her stressed legs gave out. A strangled scream escaped the gag as she sank another two inches on the pole that impaled her.

Master kept the nipple chain taut until He groaned His orgasm into jenny's throat. As He came, He let go the chain. Kay thought she would faint with relief, although her nipples felt torn off. Every heartbeat was agony. But it had been a glorious orgasm. Master was right, To experience that level of orgasm, she would gladly learn to cum only with pain.

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