tagTransgender & CrossdressersLoraine's Quest Ch. 05

Loraine's Quest Ch. 05


As I lay on top of the vaulting horse with a clear view of Leonardo and Venus who were both still assuming the position. I focused on the sensations assaulting my body, my cock stretched by the leather cock trap, my cock and balls held in a vise like grip by the "lips" of the leather "pussy", my nipples tormented by the twist lock clamps attached by the small steel cable that threaded through my falsies to the nipple rings on my treasure chest, all pulled tight by the winch devices in the horse.

Even the slightest movement increased the pain in my tortured genitals. My head was pulled back by the chain attached to the "t" handle of the harness on my head, which was anchored to my arm bondage. This position was placing great stress on my neck and shoulders and the gag filling my mouth made it necessary to relax so as not to make breathing difficult. All this combined with the chrome butt plug that ravaged my abused ass hole reminded me that I was living fantasies I had only dreamed of a short time ago.

I was suffering the pain of submission and I loved it! I loved my wonderful Mistress Catherine, Master Aristotle, and Princess Alysse for what they were doing to me. I ached to demonstrate for all what a meritorious slave I was by performing as my wonderful Mistress Catherine had prepared me for.

I could do nothing except suffer in silence and wait for the inevitable. I was ready to get my first "fucking" both anal and oral, and I was looking forward with anticipation and mixed feelings to this new experience.

Master Aristotle and Princess Alysse turned their attention to Leonardo and Venus as I scrutinized Princess Alysse's latex cock and balls as she walked toward Leonardo and Venus, wondering how the latex dildo and balls could move in such a realistic manner.

I watched Princess Alysse walk away from me and fanaticized how enjoyable it would be to tongue the rosebud between those well rounded ass cheeks swaying in latex. Suddenly a cramp in my left hip disturbed my reverie, as I struggled to find relief I only increased the pain in my nipples and genitals.

Master Aristotle and Princess Alysse ordered Venus to stand and removed Venus' handcuffs, blouse, mini skirt and cut her thong panties off and reapplied the handcuffs.

Princess Alysse unbuckled Venus' ball gag leaving the straps hanging with the ball still lodged firmly behind her teeth. A harness like the one Loraine was wearing was strapped on and the ball gag straps rebuckled.

Master Aristotle recinched the red satin corselette on Venus and both Princess Alysse and Master Aristotle pulled the laces tightly drawing her waist in to 18".

She was beautiful in her red garterless nylons and red satin corselette. The swell of her hips, narrow waist and the fullness of her breasts combined with the red ball gag and leather head harness was an exotic picture indeed.

Loraine could feel her cock stirring from the visual stimulation and tried to suppress the involuntary reflex as it only increased her discomfort.

Venus watched as Master Aristotle and Princess Alysse set up a portable brass ballet bar that was mounted to a solid platform or dais that was about 8" high.

Princess Alysse led Venus to the dais. Venus followed, taking the short mincing steps allowed by the hobble she was wearing, and struggled to step up onto the platform. Princess Alysse positioned Venus with her back to the ballet bar which was adjusted to the exact height to be positioned in the small of Venus' back.

Master Aristotle bound Venus to the bar using rope to secure her already small waist to the bar. Several wraps around her waist, over the bar and back around her waist anchored her tightly to the bar. Another tie started with a rope placed around her back with two equal ends crossing at her waist and plunging down either side of her velvety smooth, hairless, exposed pussy. The rope crossing again at the apex of her crotch exiting behind her and pulled around either thigh below her ass cheeks and tied off to the bar. This last tie caused her pussy to "pout" and was very sexy.

There was great care taken not to interfere with access to Venus' pink rosebud or pussy with any of the ropes.

Master Aristotle removed Venus' handcuffs and replaced them with a red patent leather single glove. This caused her already prominent breasts to appear even more exposed. A winch was positioned so a cable could be connected to the "D" ring at the end of the single glove. The winch was activated and Venus was forced to bend at the waist, making standing difficult.

Princess Alysse was quick to take care of that problem as she released the chains from the hobbles and gripped Venus' right leg lifting it to the ballet bar where she secured the ankle cuff to the bar with a short piece of rope. The left leg was next and Venus was tied securely to the ballet bar with her legs splayed apart, parallel to the floor of the dais. Venus rotated forward on the bar and stopped when the limit of the winch cable attached to her arm binder was reached.

Master Aristotle tied one additional rope to each leg just above the knee making the position even more impossible. Venus' discomfort was obvious by her grunts and snorts -- her body angled forward from the arm binder -- her ass presented obscenely to the greeks.

Only Venus, with her supple body could tolerate bondage this restrictive. Princess Alysse finished off Venus by anchoring the "T" handle on the head harness to a "D" ring on the arm binder pulling her head back so it was positioned to receive the inevitable cock.

Venus was voicing her objections once more and Princess Alysse answered her by rubbing her latex dildo on Venus' face, turning at the hips so the dildo "slapped" Venus first on one cheek, and then the other.

Master Aristotle was poised at Venus' exposed and prominent ass fondling her ass hole while generously lubricating her to receive a chrome butt plug. The plug was inserted and pushed home.

Princess Alysse fondled Venus' breasts as they hung in all their splendor. As Venus moaned at the unexpected attention, Master Aristotle handed Princess Alysse two heavy duty rubber bands. These rubber bands were about 1/2" wide and formed a circle about 3" in diameter. Princess Alysse stretched one of the rubber bands and slipped it over Poor Venus' right breast, all the way to the base of the breast, and released the tension. The result was immediate.

As the rubber band tried to return to its normal size Venus' right breast was constricted at its base reshaping it into a spherical shape, stretching the breast skin and nipple taut. Venus reacted immediately. She jerked and bucked trying to shake off the rubber band. Her right breast hardly moved as she attempted to dislodge the rubber band, while her unfettered left breast jiggled and flopped around.

Master Aristotle and Princess Alysse laughed at Venus' attempts to free her banded and reshaped breast. Princess Alysse quickly captured Venus' remaining breast and now both were bulging grotesquely from the constantly contracting rubber bands. Her nipples and areolas were stretched tightly causing increased sensitivity from their treatment.

Princess Alysse was fingering the mistreated mammeries, pinching Venus' nipples, laughing at her muffled objections. Poor Venus, she was totally helpless and any movement only helped the rubber bands seat more firmly at the base of her tits.

Master Aristotle left the room for a minute and returned carrying a potted plant and two leather pouches. The leather pouches were opened and Venus' breasts were slipped into them and the draw strings pulled to see how they fit.

Loraine wondered what they were for, as it looked as though Venus had a sort of strapless leather bra on each tit. The leather captured each sphere perfectly. Satisfied that the leather breast pouches were the right size, Master Aristotle removed them. He than started to pick leaves from the potted plant and line the inside of each pouch with the leaves.

Catching sight of this activity, Venus really started to thrash as much as her bondage would allow and babble loudly and incoherently. Master Aristotle looked at Venus and said, "I see that your know what this plant can do. I know that you're going to love the kiss of the nettle leaves as they prick and inflame your abused tits."

Loraine had never seen nettles before, but had certainly heard of their use. It was obvious Venus wanted nothing to do with them, especially since her poor tits were bound so as to increase their sensitivity and the stinging from the nettles would be greater than if her tits were not bound.

Master Aristotle moved to Venus and gently slipped the pouches on her breasts. He closed the draw string pulling the leather with its nettle lining tight against Venus' tits. Venus stiffened in her bondage and let out a wailing sound like Loraine had never heard before. Her tits were being pricked by thousands of nettle hairs and the burning had just begun. Princess Alysse gently squeezed each pouch to insure penetration of as many nettle hairs as possible. Loraine admired Venus' control as she finally relaxed in her bondage and accepted her inevitable fate.

Leonardo was next. Master Aristotle ordered Leonardo to stand and released the handcuffs securing her hands behind her back. Leonardo was ordered to remove her hobble, shoes, lycra slacks, cock stretcher, and tight yellow latex tunic top. Only her huge yellow ball gag remained.

Princess Alysse helped Leonardo into a yellow latex unitard that had several unique features. The extremities ended in devices that placed the hands in bondage mittens with "D" rings at the ends of the fingers and leather wrist straps. The built-in 6" high heeled latex short boots with "D" rings at the toes and leather ankle straps finished out the leg sections of the unitard. The entire crotch area, including Leonardo's ample ass, was open and exposed Leonardo's cock and balls. Her cock was erect with the ever present cock ring dangling.

Leonardo's breasts were exposed by 2 circular cut-outs in the bright yellow latex unitard. The unitard zipped up the back from the small of the back to the crew neck.

Master Aristotle guided Leonardo to a spot near Venus where several winch cables had been positioned. Princess Alysse attached winch cables to each bondage mitten's "D" ring and activated the winches until Leonardo's hands were about shoulder height and spread about 4' apart. Princess Alysse then attached two other cables to Leonardo's toe rings.

Winching the left toe first and then the right, Leonardo was suspended, toes pointed, facing up with legs and arms spread 4' apart. Princess Alysse adjusted the winches until Leonardo's ass was at the correct height for the upcoming activities. Master Aristotle moved to Leonardo's head and strapped on the now familiar head harness after unbuckling the yellow ball gag and then rebuckled the ball gag.

Master Aristotle produced two heavy duty cloverleaf nipple clamps and attached them to Leonardo's nipples. These clamps have soft rubber pads at the inside of the clamps that do not slide off, and are designed so that a pull on the cloverleaf portion causes the clamp to tighten and pull the nipple away from the body.

Master Aristotle attached a small chain to each of the cloverleaf clamps and pulled up on the chains until Leonardo had to do a sort of 1/4 pull-up with her arms to keep from stretching her nipples too far and to keep the clamps from tightening too much. The chains were then anchored to the "D" rings it the end of her bondage mittens.

Leonardo must now keep her arms bent slightly supporting her upper body weight to keep from stretching her nipples any more.

Princess Alysse, standing by Leonardo's crotch attached another winch cable to Leonardo's cock ring. Activating the winch she stretched poor Leonardo's cock until she had to bend her legs at the knees to avoid the excruciating pain of overstretching her cock.

As if all this strain were not enough, Princess Alysse worked Leonardo's balls, massaging and squeezing them until she had worked them through a 1 1/2" brass ring that had a short chain attached.

Poor Leonardo, she moaned and complained as well as she could, but Princess Alysse worked at getting her balls through the tight ring until the last testicle "popped" through the ring capturing and confining Leonardo's balls with the 1 1/2" ring. Her balls were now a sphere of glossy stretched skin bobbing at the base of her stretched cock. What a sight!

Alysse took the chain and passed it through her crotch attaching it to a 4" brass ring that was positioned to provide access to Leonardo's anus. Another chain on the opposite side of the 4" ring ran up her back and attached to the "T" handle on the harness pulling Leonardo's head back, positioning her mouth to service her tormentors.

Leonardo was now under great stress, she had to support her own weight with her arms and legs or suffer agonizing pain from overstretching her nipples and cock. To make matters worse her head was pulled back and anchored to her own balls causing another portion of her genitals to be stretched if she moves her head too much.

Leonardo immediately started to perspire and begged through the ball gag for relief. Master Aristotle and Princess Alysse laughed at her mewing as Master Aristotle lubricated her ass and sent home another chrome butt plug. Leonardo was in for a very difficult time.

Venus was cramping from the severe "splits" position and rocked back and forth on the pole as she tried to get relief. All she did was to cause her tits to move slightly in their bondage and therefore to "nettle" her nipples and tits more, creating additional discomfort.

Master Aristotle and Princess Alysse stood back to admire their work. They embraced and kissed passionately several times while fondling one another. As they started toward Loraine, she could see that Master Aristotle's cock was bulging more and straining to get out of the posing pouch.

As they passed Trevor, still hanging in his latex cocoon, they removed the latex blindfold allowing him to stare wide eyed at the scene in front of him. They stopped to stroke his latex imprisoned genital area while telling him that his time was coming. The breathing through the tubes seemed to become louder -- as though he were trying to say something.

Master Aristotle and Princess Alysse moved to stand in front of Loraine. Princess Alysse said, "Time to break your cherries Slut!" Princess Alysse reached down and stroked the bulge in Master Aristotle's posing pouch. She unbuckled the pouch and his cock was freed.

Loraine could see that his cock was standing erect and of average size.

She thought to herself that she would be able to manage Master Aristotle okay, but wondered about Princess Alysse's 8" oversized latex dildo. Princess Alysse knelt down and kissed Master Aristotle's cock and smiled at Loraine as she did so. "You are about to experience one of life's great pleasures" she said, as she encouraged Master Aristotle to rock hard erection.

Loraine watched as Master Aristotle did something totally unexpected. He hooked his thumbs in the waist band of Princess Alysse's latex dildo pants and started to slowly take them off. Under the dildo pants were white latex crotchless panties. Much to Loraine's surprise out popped a beautiful chocolate colored hairless cock and balls almost identical in size to Master Aristotle's. The surprise was obvious in Loraine's face.

Princess Alysse was a pre-op TS like Leonardo!

As Loraine stared at the mocha cock in front of her, she realized she was not going to have to deep throat a latex dildo, but rather the real thing.

Master Aristotle and Princess Alysse laughed at Loraine's surprise and realization that this hairless, chestnut brown cock would soon be inserted in her mouth and down her throat.

Master Aristotle walked around Loraine and removed the chrome butt plug as Princess Alysse deflated the cock gag and extracted it from Loraine's mouth. Moving into position, Princess Alysse told Loraine, "Use that worthless tongue and caress my cock slut!"

Loraine gently started licking and gently sucking the head of Princess Alysse's cock, flicking her tongue on the sensitive frenum area anticipating the inevitable insertion. Master Aristotle was already penetrating Loraine's ass hole and she could feel the warm feeling of a real cock sliding into her anal canal! He stopped after about one inch and moved his cock in and out a little, teasing Loraine who was shuddering in anticipation.

Master Aristotle slowly pushed on and soon was buried to the hilt. As this throbbing, living member forced its way into her "pussy" she was surprised that it actually felt good! A "real" cock--it felt warm and alive and wonderfully natural. Loraine suddenly realized that she had crossed the line and was actually loving this bi-sexual activity.

Princess Alysse was starting to push with more authority and in no time both cocks were all the way home. Master Aristotle was pumping and Loraine could feel his balls slapping against her ass while Princess Alysse's cock was already sliding down Loraine's throat and she could smell the wonderful odor from the latex panties combined with Princess Alysse's musky crotch scent.

As Loraine responded to the intruder, her training from the night before helped her perform. She fought to control the gag reflex and fought for air as Princess Alysse pumped in and out. The pumping action both fore and aft caused Loraine to bounce around on the horse further punishing her nipples and cock and balls even more.

Loraine was truly enjoying the intense sensation of being fucked at both ends while in stringent bondage. The associated pain from the bondage seemed to become profoundly pleasurable and consumed her whole being as she worked to provide all the satisfaction possible to these two beautiful people. She was incredibly excited and could feel her cock growing until the cock trap reached its limit, increasing her discomfort once more.

She constricted her anal muscles to heighten Master Aristotle's pleasure and swallowed as best she could to intensify Princess Alysse's pleasure. The new sensations created by the two throbbing cocks were extraordinarily exciting and enjoyable. She had crossed the line to bisexuality and was loving her forced circumstances.

Master Aristotle and Princess Alysse exploded into Loraine almost simultaneously -- she could feel Master Aristotle's cum being injected into her ass and she was swallowing Princess Alysse's cum as fast as she could. Both Master Aristotle and Princess Alysse were in the throes of orgasm and ramming their cocks as deep as possible, pumping their cum into Loraine.

Princess Alysse recovered first and said to Loraine, "Lick it clean slut!" Loraine fought her bondage to catch the remaining drops of cum with her tongue, licking and cleaning Princess Alysse's still erect cock savoring the sweet taste of the cum spurting forth from this beautiful sepia cock.

Satisfied, Princess Alysse jammed the cock gag back into Loraine's mouth and pumped it up to once again fill her mouth.

Master Aristotle relaxed and pulled out wiping his excess cum on Loraine's ass. He picked up the chrome butt plug and rammed it back into Loraine's ass. Loraine reflected on the experience and smiled behind her gag at the pleasure she had provided these two wonderful people. Not to mention the pleasure she derived from her experience. Her Mistress Catherine would be proud.

She watched as Master Aristotle and Princess Alysse walked toward Venus and Leonardo. Loraine noticed that Master Aristotle and Princess Alysse were still as hard and erect as they were just a few moments ago -- the intense orgasm had not caused them to go flaccid. Loraine made a mental note to ask Mistress Catherine what their secret was.

Report Story

byloraineveritas© 0 comments/ 19264 views/ 6 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: