Tammi's Tales Ch. 01

The weeks of cyber-domination were at an end. Tom nervously drove along the highway out by the airport, looking for the Runway Motel. He was startled every time he caught a glimpse of the woman in makeup staring back at him from the rear-view mirror. As 'tammi', he had been dressing en fem and wearing makeup for years, but today marked the very first time he had ever strayed out his front door this way. Sir Ronald had assured him that today would only be the beginning. The whole prospect scared and excited tammi half to death.

The kids were grown and raising their own families in other parts of the country. Tom's wife and beloved Mistress of many years had succumbed to a lingering disease two years ago. Lonely, and with nothing to hold him back now that he was retired, Tom, dressed as tammi, spent most of each day on the computer. Sharing makeup and fashion tips with other cross-dressers around the country was fun, but she soon felt the need for domination to feed her pain-slut fantasies.

Mistress had not only accepted and assisted his dressing, but thoroughly enjoyed their S & M games. Because of their love, she could only rarely bring herself to give him the levels of pain he craved. Even now, just looking at the pictures she had taken of his cane-welted ass and thighs was bittersweet as he recalled their years together. But today was a new beginning. After six months of submitting to Sir Ronald's on-line domination, tammi had agreed to meet.

Through E-mails and chats, tammi had learned Sir Ronald's tastes and bared her own deepest, darkest fetishes. While their compatibility was remarkable, tammi still harbored doubts as to his potential for cruelty and her ability to submit. Talking was one thing, real tears and welts were another. It had taken tammi and Mistress years to evolve their S & M relationship. How much could be expected from a first meeting with Sir Ronald? Despite her excitement, tammi told herself not to get her hopes up too high.

At last she found the motel and parked. With each passing second, her meeting with Sir came closer, and her jitters returned full force. Would he approve of her wardrobe and makeup? Sir had specified bra, girdle, black hose, heels, no panties, and 'hooker' makeup, but left the selection of skirt and blouse or dress, hairdo, and accessories to her.

Leaving her small bag and makeup case in the car, she cautiously pivoted from the car. Unsteady in the high heels, she stood up and adjusted her skirt, trying to add phantom inches to its length.

'Well,' she thought, 'this is it. Everyone can see I'm not a real woman.' With a sigh, she squared her shoulders, plucked her purse off the car seat, and walked toward the office.

It was obviously a 'no-tell motel.' The desk clerk had seen most everything, so made no comment about tammi's 'hooker' image, but his glance lingered on her shapely legs as she entered the office. Blushing at his stare, she self-consciously checked her hose for runs. Setting her purse on the counter, she gave her name. He confirmed her reservation and gave her a key after she signed the credit card receipt. In her most feminine voice, she had to explain that her 'husband' would be following her shortly, and would stop in for a key as well, while she had to do a couple of errands. Her explanation fooled no one. The transaction complete, embarrassed beyond belief and blushing furiously, she hurried outside. Gawd, she felt humiliated, just as Sir Ronald obviously intended. Even with her voice difficulties and somewhat mannish appearance, she could have passed as a woman if not for the whorish clothes and makeup. She just knew the clerk was looking right through her and thought she was a transsexual prostitute working a trick.

Glancing at her petite wristwatch, she crossed the parking lot to a diner next door and ordered a cup of coffee. Following Sir Ronald's instructions, she sat with her legs crossed and skirt riding high to give the public a generous view of black nylon. Rather than feeling feminine, tammi felt more like a whore on display. The telltale red stain on the cup and pungent taste of the lipstick reminded tammi of her mission today. After a second leisurely cup of coffee, she looked at her watch again, and fumbling awkwardly with her purse and wallet, paid the bill and returned to the motel. With each click of her heels on the pavement, her heart beat faster. This was no longer a computer game. She was going to submit to Sir Ronald in the flesh.

Would he stand her up? No, there was the car he had described parked beside hers in front of the room.

Tammi quickly retrieved her overnight bag and cosmetics case from her car. Last chance to chicken out, she thought with a smile.

Reaching the door, she quickly fished out a compact and lipstick from her purse and did a quick touchup. The mirror reflected the face of a scared whore.

Quaking inside and out, she tapped on the door. Nothing. Tammi counted three slow breaths, then tapped again. This time, the door opened.

"Hello, tammi," Sir Ronald said, holding the door wide for her to enter.

Keeping her eyes on his shiny black boots, tammi managed a "Good afternoon, Sir," as she walked in, all too self conscious of her lack of grace in heels.

Turning to lock the door, he asked if she had any difficulty finding the motel or renting the room. It all sounded like a normal conversation between two friends. Making no move to help with her bags, he gestured toward the table in a corner.

Placing her purse and luggage on the table, tammi turned to face her Master.

As her eyes adjusted from bright sunlight to the dimmer room, tammi got her first in-the-flesh look at Sir.

The pictures were accurate. At a solid six feet, 200 lbs., Sir definitely filled the tight jeans, and his muscled arms made the leather vest look natural. While not movie-star handsome, Sir Ronald emanated the power and confidence of a mature Master rather than a kid playing at BDSM. Tammi shivered in anticipation of submitting to this strong, alpha male.

"Turn around, bitch."

Tammi obeyed his command without hesitation. Her 'no-never' list was short: no minors, blood, weapons, scat, breath play, or unprotected sex. Since those were her only limits, Sir Ronald had agreed to accept her as a pain-slave to train.

Bending her at the waist, Sir ran a hand up her nyloned leg to her crotch.

"What's this?" He gave her panties a painful tug "You were ordered to be bare-assed I thought you wanted to be my submissive slave, and here you can't even follow simple orders!"

"I-I, Oh Sir, forgive me. I've never been outside dressed before and it just felt funny to wear a skirt with no panties underneath," tammi stammered, as she hurriedly removed the offending panties.

His anger showed but was controlled as he picked up the fiberglass cane and gestured toward an upholstered arm chair, "Raise your skirt and bend over that chair, slut."

"Yes Sir," tammi meekly replied. It was hard not to crack a smile. This is what she had dreamed of, submitting to a stern Master who would train her with pain. She had displeased him already, and their agreement included punishment for disobedience or failure to please.

Bunching the tiny skirt around her waist, tammi draped herself over the back of the indicated chair. Without being told, she reached down and gripped the arms for support. She didn't know how hard

Sir Ronald would swing that limber cane, but she sensed it packed a real sting.

"You disobeyed, slut."

The cane whistled through the air before landing with a loud smack. With clenched teeth, tammi squealed as red stars exploded inside her closed eyelids. He held the cane in place for a couple of heartbeats before pulling it quickly away to raise a masterful welt.

"One, Sir, thank You Sir," tammi recited the mantra Sir Ronald had specified for any whippings.

"You disobeyed, bitch." Again the cane raised a welt on her ass.

"Two Sir, thank You Sir."

The ritual continued for two dozen slow, measured strokes, each preceded by a different humiliating epitaph.

When Sir Ronald stopped, tammi knew she would never again wear panties in his presence unless ordered to. She quickly fell to her knees at his feet and kissed the hand and implement that caused her tears.

"Thank you, Sir, for punishing your slut. How may Your whore serve You, Master?"

"Take off your blouse and skirt. Let me examine my little slut," he replied.

Quickly her blouse and skirt joined the offending panties in a heap in a corner

Posing like a lingerie model, tammi slowly turned around so Sir could see everything: the black B-cup bra she proudly filled, the delicate necklace at her throat, the shimmering black long, open bottom girdle, matching seamed stockings, and her best 4 inch black patent pumps.

"Nice, very nice indeed," Sir Ronald liked what he saw. Handing her a tissue and her purse, He told her to wipe her eyes and fix her makeup.

As she gratefully complied, he told her, "Your next whipping will be bare-assed. No girdle to shield you."

Sniffling, tammi answered, "Yes Sir," and winced at the thought. She realized that she was in for a real workout if Sir thought her girdle had protected her during the caning.

"Present your tits, slut."

While tammi thought of herself in those terms, it was definitely humiliating to hear herself called a bitch, whore, slut, cunt, or any of the endless list of names Sir apparently had for her. Crossing her arms, she slid the shoulder straps down and peeled the cups.

After fondling her breasts to test their firmness, he began working her nipples, pinching, pulling and twisting them. Fingernails pinched the very tips. Tammi squealed and rose up on her toes until her high heels left the floor.

With a chuckle, he released her.

The perked up buds were easy prey for the clamps he applied. Though strong enough to take her breath away, she had used harsher ones by herself. But they did hurt, and she was careful fitting them into the bra cups.

Sir Ronald bent her over the chair again and used mentholated chest rub to lube the medium sized butt plug that was unceremoniously stuffed up her. Over the years, tammi had used bigger plugs and monster horse-cock dildos, but the insertions were slow dilations that didn't hurt. This time, it did. It wasn't the plug's size. It was the abruptness and the menthol lube that got her instant attention.

The ball-gag he buckled on her showed deep teeth marks. How many other sluts had suffered at Sir Ronald's strong hands, tammi wondered.

She was ordered to unfasten her back and side garters so she could roll the girdle up above her hips. The preparation unnerved her more than the prospect of another whipping as she fumbled to comply. She stood meekly as Sir snapped a snug, red leather harness around her 'clit.' It also had straps to separate the balls. Those were especially tight, and hurt as he fastened them.

"This will keep your clit and labia out of my way, in addition to disciplining you, cunt," Sir Ronald explained, giving the grotesque, purpling orbs a light spank.

Tammi moaned, and lay face down on the bed as ordered.

A wide leather collar circled her neck and was cinched tight before her wrists were cuffed to the thick ring at the back.

Sir began with the more gentle whips, slowly increasing the force of each lash. Even though the gag muffled the sounds, tammi continued her counting ritual. Soon her ass was a warm, glowing pink. Then he switched to a thick paddle. Any thoughts of delightful S and M sex vanished as tammi bucked and cried out with each blow. The strikes to the backs of her thighs hurt the most, causing her to bounce on the bed. She had momentarily forgotten the clamps biting her nipples until then. Now her tortured breasts felt each jiggle of the bed as she thrashed around under Sir Ronald's expert torment, crushing her clamped nipples.

Prone on the bed, her ass and legs were supple meat under Sir's tenderizing. When he was satisfied with her color, she was ordered to roll over so he could work her mound and the front of her thighs.

This was worse for the now-sobbing wench. True, the pain was less, but she could see the descending whip and paddle as they seared her body, shuddering with each fresh impact. Sir Ronald alternated slashes between her thighs, tender mound below her navel, and her clitty itself. In no time, everything hurt and tammi's tears continued to wet her face. When the paddle smacked her clamped breasts, tammi shrieked and came bolt upright in agony. A second strike sent her back flat on the bed of pain. She was certain the clamps were tearing her nipples right off as he repeated the sequence at least a dozen times.

With the gag-induced slobbering, tammi's counting the lashes was soon reduced to mere gurgling as she tried not to drown in her own saliva.

When the discipline was over, Sir Ronald helped tammi sit up. Unbuckling the dripping gag, he soothed her with soft words and softer caresses until her crying stopped. She was grateful when he unsnapped her cuffs from the collar and she could bring her hands down to rub some of the pain from her ravaged thighs.

"This is part of your fantasy, isn't it? I gave you what you wished for. "

"Y-yes, Sir," tammi sniffled, "I need your discipline and punishment, Master. It's been a long time since I was taken to tears."

"Don't worry, my slut, you'll shed more tears before we are through today," He promised, pulling her bra straps down.

Tammi moaned as the nipple clamps were removed. She gasped when he massaged her tortured boobs. It hurt nearly as much as the clamps themselves as the circulation returned.

Giving her a few minutes to recover, Sir Ronald took some digital pictures of her reddened breasts and thighs. Ordering her to stand, he remarked that the cane-tracks were still visible from her first punishment session as well as the bare-assed whipping. The camera's flashes guaranteed a record of her suffering.

Setting the camera aside, he said, "Shall we continue, little whore?"

"Oh yes, Sir," tammi meekly replied, "As you wish. I'm yours to use."

"Don't worry, I'll use you, all right," he said with a wicked smile.

Pinching the tips of her nipples with fingernails again sent her up on tiptoes. Then he applied different clamps, ones with vicious, toothed jaws.

Biting her lip to stifle the scream, tammi accepted the fresh pain as her bra cups put additional pressure on the clamps.

"Sometimes, just changing the clamps can make things hotter," He said, "Now undress me, you cunt."

It was awkward, with her wrists still cuffed, but tammi hurried to obey. Then he handed her a condom.

"Put it on me, bitch, it's time you started being the female whore of your fantasies."

With her wrists cuffed, and never having put a condom on someone else, tammi was embarrassed by her clumsiness, but soon had the rubber smoothly sheathing Sir Ronald's erection.

"Now get those garters fastened again. Your stockings look like hell."

Tammy rolled her girdle back down and secured the side and back garters.

She gave a little sigh as he laid her down on the bed.

This was part of her fantasy coming to life, but she was nervous and a little scared. Before putting on the condom, she had never even touched another man's cock, and here she was about to suck on one like a cheap street whore.

Lying beside her, Sir Ronald began kissing her while his hands caressed her neck, and followed her contours downward. Not really knowing what to do, tammi put her cuffed wrists over his head and held on. She groaned into his mouth when strong fingers mashed her clamped tits. Getting the desired response, he worked them harder until her moans were continuous. Then he found and stroked her strapped clitty and squeezed the aching balls. The pain was deep and dark.

"Oh please, Sir," she mumbled around his tongue.

Biting her lower lip hard, Sir Ronald broke the kiss, "'Please' what, cum-whore? Don't tell me you're begging for mercy already! We haven't even started, you stupid slut. Remember that you protested the pain. There will be severe punishment for that infraction later. Don't forget it."

After refastening her wrists to the back of her collar, he moved up the bed to straddle her head, and presented his penis to her mouth, "Now suck my cock, you cow."

Tears of humiliation wet her eyes. Apparently the romantic foreplay was over.

"Y-yes, Sir. I'm sorry Sir. I've never sucked a real cock before, Sir."

Opening her mouth wide, tammi took the spongy head in and swirled her tongue around it. As a male, she had experienced blow jobs from girls, so tried to imitate the techniques she recalled as the most pleasurable. From his encouraging sounds, she was doing it right! She wished her hands were free to stroke the stiff shaft and bulging nuts. But the simple bondage did make her feel like a common tramp being used, as he pushed an inch of solid cock beyond her slurping lips.

Working ever deeper, he wiggled around, knees grinding her earrings into her head. Then he grabbed a handful of blonde hair and shoved, burying her nose in his bush and hitting the back of her throat. She had been practicing deep throating on bananas and sausages as ordered, in preparation for this, so she was able to stifle her gag reflex and take him all the way into her throat.

Concentrating on not gagging, it took her a little while to settle into his rhythm. Tammi began to notice and savor the sensations. His musk, the taste of bitter rubber mixing with her smeared lipstick, the wet, slurping noises, her tiring jaw, the thick shaft pummeling her throat - at last, she was a woman, servicing her Man. She would have cried for joy, but for the punishing hands working her shrieking breasts and spanking her aching balls. So she cried because of the delicious torment he inflicted.

Increasing the tempo, he began slapping her hollowed cheeks as she sucked like a pro.

It seemed an eternity, but wasn't, before he grabbed two handfuls of hair, shoved in deep and held on as she felt His cock swell even bigger, and the pulsing jets delivered to the condom.

As he shrank, her tongue resumed its swirling until his tip retreated to meet her searching lips. Even with the cum-loaded rubber, it was too sensitive for much of that, so with a groan, he pushed her head back into the pillow.

Uncuffing her wrists, he lay beside her. Bodies entwined, they sank into the warmth of the afterglow.

Her jaw ached from the effort and her throat felt bruised, but tammi beamed like a new bride at her Master's satisfied smile. It surprised her that even without any touching of her 'clitty', she had felt a mini orgasm when Sir Ronald had cum. The constant pain in her purple orbs, nipples throbbing with every heartbeat, jaw muscles exhausted, none of it mattered, only that she was now a woman who had pleasured her Master!

Seeing her 'cat-napping-in-the-sunshine' look, Sir Ronald tugged her bra cups off the aching clamps. Removing the torture devices, he sucked both nipples in turn. Being clamped so long, it took a moment for the returning blood to awaken the numb nerves.

Tammi moaned as Sir Ronald unsnapped the brutal leather straps from around her balls. The tied off cum of her orgasm oozed out, coating her in stickiness.

To his probing questions, tammi had to admit that yes, she had truly enjoyed her first sexual encounter as a woman. Yes, despite, or maybe, because of the flogging and clamps, she had cum. She supposed it was a female orgasm, but wasn't sure. Yes, she looked forward to sucking him off again. While it had initially seemed a bit strange to be sucking a man's cock, she felt she was a woman, so servicing a man was hetro, not homosexual. She shyly admitted that she hoped someday, with monogamy and testing for both of them, she could swallow the hot cum when he squirted in her mouth.