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Author's Note: A man's kinky evening with his wife takes him much further into his fantasies than he expects.
My wife Jess and I had finally gotten away for a long weekend, a change in the routine in a different city. Although we live a pretty conventional life in our suburban home, we share a love of travel as a way to cultivate new experiences and just to kick us out of comfort zone. Our sex life was no different. Although we started out quite vanilla, our natural curious natures had us experimenting starting soon after. We've always been into trying out each other's fantasies and kinks, each one expanding the world of our sexual lives and our loving relationship.
For the start of this weekend, we were playing with my increasing fondness for stockings and lingerie, and we'd brought some of my favorite female undergarments with me. Crossdressing was something that I had played briefly with as a teenager, but having a willing partner to explore with revealed how deep this fetish ran for me. Having a wife who enjoys helping you browse online for stockings and silk nightgowns, who is willing to walk into a store and pick up a pair of pantyhose for you, and then who loves helping you get dressed up just reinforces the reality of what a lucky guy I am. I mean, how many wives would be willing to show their man how to properly roll stockings on, and then to spend the night dressed up herself as we sensually rubbed our silk-clad legs together as we made love?
To start everything, I went to shower and shave myself sexy smooth, a feeling I reveled in. The first time I shaved myself, I wasn't sure what to expect from Jess. To my surprise, she loved her clean-shaven man and showed me some of the tips and tricks women know on that topic. From that point on, I've generally kept myself hairless anywhere that doesn't show out of a business suit. Many of my fetishes stem from the tactile, and shaving makes my entire body more sensitive. There's nothing like the sensual feeling of smooth skin against bed sheets, a silk nightgown, or new hosiery. As I emerged from showering, I noticed that she had laid out my evening's wear: a bra, my pink corset, a white garter belt with white stockings, and pink silky satin panties.
"C'mon sexy, let's get you dressed!" she said enthusiastically, "You know what we have to start with, right?"
I nodded as she produced the chastity cage. I had been wearing one all week and she had been verbally teasing me every night. Despite the equal nature of most aspects of our relationship, our sexual lives had definitely tipped in the direction of Jess being the dominant and I the submissive. Not entirely, as we enjoyed switching up at times. However, she took great joy in keeping me locked up in a chastity device and controlling my orgasms, both as an exercise in sexual power and because it made for a distinctly more agreeable and polite husband. To keep the reality of the cage always forward in my mind, she would often verbally tease me, stroke me, or ask me to bring her to orgasm, knowing that there was no way I could find relief.
"Is this a new cage?" I asked, seeing that it was pink instead of our clear plastic cage.
"Yes," she said as she slipped it on me, "I thought it would look nicer with your rather girlie outfit." With her practiced hand she quickly had the device in place, slipped the ring behind my balls, and clicked the lock in place. The feeling of restriction between my legs and the weight of the cage always fills me with a feeling of anticipation, knowing that as I'm locked away, there's nothing I can do to address that sexual itch.
"There, that should keep that thing from getting in the way!"
We started dressing me with my white garter belt, a traditional wide design that stretched around my waist. As I rolled my first stocking on and carefully pulled it up my thigh, I shivered at the feel of the material against my newly-shaven legs. She helped attach each of the three garter straps, and then we did the other leg. To finish, we tightened up the garter straps to hold the stockings in place high on my thighs, the sensation of the smooth stockings being gently pulled against my skin sending flashes of pleasure to my brain.
It was stockings and pantyhose that first led me to understanding how much I enjoy the feeling of women's clothing, especially those made of soft, stretchy or smooth material. Over time, my appreciation for women's clothing grew, the way some items were form fitting, and others brushed smoothly against the skin, the myriad options of colors and cloth, the sheer variety of garments. Coming from the rather bland world of the suburban male wardrobe, exploring the female side of clothing was a revelation.
My preference for the most feminine colors, the pinks and whites, along with the most dainty and frilly of designs, came about from my submissive nature. I loved it when Jess got me dressed up and then used me how she saw fit. Forcing me, a man who worked all week in a masculine suit and tie, into the ultimate of feminine attire never failed to engage that part of my kinky brain.
The next item I donned was the corset, which she had me step into and then lifted up over my hips, where I held it in place as she began to tighten down the laces behind my back. This was a metal-boned pink corset, which we had acquired as a crossover between bondage and of women's wear. Each of her passes at tightening the laces increased the feeling of constriction, restricted my breathing a bit more and pulled in my waist further.
The process was one that I always found intoxicating. Each time she dressed me in the corset, Jess seemed able to get it just a little bit tighter, and this time was no exception. With one last set of hard pulls, she tied off the corset laces. Bending over became more difficult, but the biggest change was the narrowness of my waist. I wasn't the thinnest guy in the world, but in the corset my silhouette looked much more feminine than it had a few minutes ago.
"Feel OK?" she asked.
"Amazing!" I replied.
She helped me on with the bra, as I still haven't mastered the art of doing the hooks behind my back. The way the bra stretched around my upper torso, enclosing me in its smooth embrace, added yet another feminine layer on to my outfit. Even without the breasts to fill out the cups, a bra was such a distinctly female garment that helped complete the outfit.
Lastly I pulled the pink silky French-cut panties up my legs, the soft cloth caressing my stocking-clad legs on the way up and the material riding into my ass.
My wife inspected me to make sure everything was in place, delicately caressing my arms, retightening the garter straps, giving my chastity cage a tug to make it was secure, and finally straightening my panties. With this cascade of touches and the completion of my feminine transformation, my cock began to stir in the cage.
Or at least I though we were done. It turned out Jess had other plans.
"Now that we've gotten this far, I have some surprises for you to take things just a bit farther dear...do you think you're up for it?" When this woman says she has surprises, they are often of the mind-blowing kind, so I enthusiastically nodded yes.
"To be honest, it's probably quite a bit farther...but in a way that I think you'll find highly memorable. We would be pushing your comfort zone for sure. Of course there's nothing we'll do that is beyond any boundaries we've discussed before, but once we start down this path, there's no turning back. What do you think?"
With a disclaimer like that, I couldn't help what wonder what the imagination of my wonderful partner in kink had cooked up. Admittedly, a tinge of fear and apprehension accompanied my overall excitement, but I trusted Jess on this.
"Jess, I've never been more ready," I replied, and by now, this entire discussion had my libido bubbling.
"Excellent! This is so exciting! And good for you because I did a little shopping and I'd have hated for it to go to waste," she said, as she opened a door to the closet where she must have stashed her surprises. I could feel my breathing quicken.
"First, let's fill out that bra shall we?"
She brought out two breast forms, about C size to fit my bra. As she tucked each of the soft, silicone forms into the cups of my bra, I enjoyed the feel of the bra filling out and the weight of the fake breasts. The mass of the forms changed the balance point of my body slightly and made me even more aware of the additional curves that had been added to my silhouette. I'm sure it gets old for women, but as my first experience, I found the way my bra shifted as I moved to be exciting.
"Next she said, why don't we complete the outfit?" She returned to the closet and I could hear her removing some items from a hanger. As she emerged, I stared dumbfounded at the two garments she held. Well, dumbfounded in a good way, because this was something I had fantasized about but was too embarrassed to share, even with her.
Since I had discovered my fetish for women's clothing, I had experimented on my own a couple of times with wearing dresses. Although the look and sensation of the outfits was new and exciting, I came to wonder how much better it would be when (or if) a dominant woman like my wife was the one forcing me to dress up.
What she was displaying to me now went far beyond any of my previous explorations.
"I noticed in your browser history you had been looking over some sissy clothes web sites, and I decided we should give it a try. After looking over all of the designs - and there so many cute ones - I decided that this would be a wonderful first outfit. Let's get these on you pretty boy."
The first item was a pink petticoat with a light white lace hem. As I stepped into it, I felt the material rubbing up my stockings, the interplay between the two materials sending small shocks through my nervous system. She pulled the petticoat up to my waist, made a few small adjustments and the petticoat was in place, covering my legs about halfway down my upper thighs.
Now came the dress itself. This was a full-on sissy dress to match the petticoat, mostly pink satin with white details. It had short puffy sleeves, a white collar, and two bows on the front. As she slipped it over my head, I put my arms through the sleeves and let the dress settle on my shoulders. It puffed out gracefully around the petticoat, pulled in to be snug at the waist, and my fake bust filled out the top of the dress.
Jess gently closed the two sides together behind my neck to finish fitting me into outfit, and I was surprised to hear the click of a lock.
"Just to make sure you don't want to take it off early dear, not that you'll want to," she said, as she completed the look by tying the large ribbon around my waist into a bow behind me.
For whatever reason, being locked into the dress lifted the experience of having it on to another level. This wasn't an article of clothing that I chose to wear. This was a dress that I was being forced to wear because my wife wanted it so, and that punched all my submissive buttons.
Glancing in the mirror, I saw a sissy look that I had dreamed about trying, but had been too scared to follow through with. Having my wife be the agent of this experiment was exhilarating, and I shivered at the mere idea of ever being seen in public like this.
As Jess ran her hands over the dress, smoothing it out, I reveled in the touch of satin against my skin. When I moved, the sensation of the various parts of the outfit gently caressing my skin set off small fireworks in my brain. This was an incredible feeling, and I looked more feminine than I ever had in my life. She had me twirl around for her and I felt the dress caress my thighs as I did. The length wasn't a micro, but bending over too far would definitely put me in danger of exposing my parts underneath. Jess must have thought about that when she selected it, as it was kind of devious detail she rarely missed.
"You look better in that dress than I even imagined," she declared as she hugged me from behind and ran one hand over my chest while the other snuck underneath and rubbed my satin-covered behind. "Seeing you this way makes me think I may enjoy having a 'girlfriend' around the house." For a fantasy that I had feared to share, this one now seemed to be as much my wife's as mine.
But Jess wasn't done.
As my mind continued to process my newfound sissy look, she ordered me to sit on the edge of the bed. She returned with a shoebox, and pulled out two sets of high-heeled shoes. But these were not just any ordinary shoes. Baby pink with matching pink ribbon laces, the heels themselves were about 5 inches high. As befitting shoes for a sissy outfit, they had pretty bows on the sides, front and back, with white lace around the ankles. To prevent the shoes from being removed, an ankle cuff was attached to each shoe, with two buckles in back with slots for locks. To complete the humbling nature of the shoe, three pairs of bells hung daintily from the sides and front, so that any movement while wearing them would make a delicate ringing sound.
As she slipped them on, Jess told me how challenging it had been to find these in my size, as I have reasonably large feet. However, the shoes fit perfectly, although a bit of worry crept into my thoughts as she locked first one shoe, then the other onto my feet, placing the key on the dresser with those from the rest of the locks.
"Stand up," she ordered, "and walk around the room." I quickly complied.
These weren't the first heels I had ever walked in - I had dabbled once or twice before with Halloween costumes - but they were quite easily the most elaborate. Although my stride wasn't very elegant, the shoes were not uncomfortable and the small bells jingled as I walked. As part of a sissy fantasy they were wonderful, but I couldn't imagine what it would like having to walk in them for a distance or to wear them for a long time.
"Do you like them?" Jess asked.
"They are amazing!" I exclaimed, "They aren't something I would have ever had the courage to buy for myself, but they really go perfectly with the rest of this outfit."
As much as I was enjoying this part of my fantasy, I had no illusions that being locked into high heels was anything but forced feminization. I had no choice but to wear them for as long as Jess desired. The bows and lace accents were an incredibly sissy touch, something that only a truly submissive man would have allowed himself to wear, much less find exciting.
And as for the bells, well, besides my skin being a sexual organ, I also have find that what I hear turns me on as much as what I touch. Sounds, from the clink of chain or the snap of a lock being closed, to the sound of Jess moaning in pleasure, to her sweet whisperings as she described what she was going to do to me in a bondage session, had always been a foundational part of my sexual consciousness. These sounds had deep and sensual associations in my mind, and the bells were no different. On a number of previous occasions, Jess had enjoyed using nipple clamps on me with small bells,, because she loved actually hear me struggle - the bells would jingle - and I found that I too found that sound intoxicating. These shoes were the feminization equivalent of that, a decisive signal to me each time I moved my feet that I was under her control.
"As much as I know you're enjoying your sissy clothes," she said, "I thought we'd add a bit of bondage. I'm assuming you're up for that?"
Recently, I had begun to fantasize about being dressed up and then bound, left to struggle in an feminine outfit like a damsel in distress. In that sense it was coming full circle, for it was the books, comics and movie scenes with a woman bound and in peril that had opened the door in my teenage mind to my hardwired fascination with bondage.
"Yes, definitely yes," I replied. Was I finally going to be turned into damsel-in-distress? Or maybe even a sissy-in-distress? The prospect of struggling against restraints while wearing these layers of sensual clothing would be the fulfillment of another of my fantasies.
"Excellent. In that case, we aren't done yet dear," she said, "not by a long shot."
She returned to the closet and brought out two long leather gloves, pink to match the rest of the outfit.
I recognized these from my online explorations of BDSM gear - they were bondage opera gloves. The hands had no fingers, just a steel ring attached at the end. A zipper ran from wrist to the shoulder, and there were three sets of straps and buckles: one at the wrist, one at the elbow and one at the shoulder. Each of these points also sported a steel ring, all as attachment points for being bound.
Jess pulled the first one on. When my hand was in the glove, the top nearly reached the sleeve of the dress. Zipping it up drew the leather more tightly around my arms, but once she had tightened each of the straps and buckled them, it was clear that this glove was not coming off.
"Are the straps OK?" she asked, "not too tight?"
"Just fine - no problems at all with circulation." I replied, moving my arm and feeling the leather tight against my skin.
After repeating the process with my other arm, she asked me to put my arms behind my back. As I did so, I heard snaps being attached to the rings, and felt my arms being slightly pulled together. Looking at my back in the mirror, I could see that each ring on the glove was paired up to its corresponding ring by means of short chains with snaps on each end.
With my hands trapped in the fingerless leather mitts, there was no way I was getting out of this without her help. Because my arms weren't bent very far backwards, there was little danger of them getting sore or numb, so these were restraints I could wear for hours. Knowing my physical limits as well as she does, Jess she was well aware of this also.
The combination of these elements of bondage with my sissification was even better than my fantasy. Lightly struggling against my arm bondage, I felt the warmth of the sensation of helplessness wash through me. Jess would have her husband as sissy for as long as she desired.
"As long as we've done your arms, let's make sure you can't run away either," Jess said as she brought out two pink leather straps with soft linings. These she fastened on me above each knee, thoughtfully taking care not to damage my stockings.
As she snapped a short length of chain between the two straps, I realized my movement would be limited to small steps. I should have been wondering why she cared about slowing me down, but that this point my brain was in such a deep well of kinkiness I was just going along with whatever she did.
"Let's get that head of yours taken care of, shall we?" Jess said, and brought out a pink leather hood. She was really going all out tonight, and this truly was farther than we had gone before.
This hood had two eyeholes, which had a feminine slant to them, and an opening for the mouth. After sitting me down on the edge of the bed, she pulled the hood over my head. Making sure the eye and mouth holes were lined up, as well as the nose holes for breathing, she zipped up the back and I felt the leather being stretched tightly over my head and face.
Double-checking the fit, she ran her hands across my face, and I could feel her touch through the tight leather. Looking at my image in the mirror, I saw that my face, the last vestige of my masculinity and identity, was almost entirely covered. There was no part of me that wasn't covered in pink satin, leather or nylon.
After verifying the fit of the mask and that I could breath properly, she produced a pink leather bondage head harness with penis gag attached to the inside of a leather muzzle that covered my face from nose to chin. Pulling this on and inserting the penis gag into my mouth, she tightened each strap so that the chinstrap kept my jaw from opening, the gag was forced fully into my mouth, and the muzzle would keep me from making any meaningful noise. Satisfied she locked the harness onto me. As I shook my head, testing the tightness of the inescapable harness, I noticed that it too jingled with bells attached to the front and sides.
"One more thing and we're done," she said.
She pulled out a leather collar, pink with white lace trim and series of bells sewn around the outside, a perfectly sissy piece of bondage gear. A single steel ring was attached to the front. Wrapping it around my neck and over the bottom of the hood, she tightened it to be firm but not too tight, and with yet another click, locked it in place.
Jess now stepped back to admire her handiwork.
Where her husband had stood there now was her sissy slave, dressed in pink and white frills and bows from head to toe, unable to speak, arms and legs bound. Locked into a dress, shoes and hood, there was no way for me to escape.
"Wait here," she said and went to open our hotel room door. Horrified and panicked at being seen like this, I shook my head and begged her with my eyes not take this any farther. "Wow, you really are scared of being exposed as a sissy, aren't you?" she said with an amused smile. I could not believe that she would expose me in public. Admittedly, in surfing the sissy sites, I found that a part of me found the fear of being publicly humiliated very exciting. Face like this with the imminent reality though, my mind balked.
"Still, as fun as it might be, I don't think I want to be seen with someone dressed like you in this hotel or anywhere else in public for that matter. So, no, I'm just going to grab something from outside the door."
Inside the hood, I released my anxious breath in relief.
What that, she opened the door, glanced to make sure the coast was clear, and then wheeled in a hotel luggage cart that she must have parked there earlier. What exactly she had planned for it I didn't know, but I was pretty sure it wasn't hauling suitcases.
Placing a pillow in the middle of the cart, she told me to kneel on the cart, holding me steady and helping me keep my balance as I did so. She produced three lengths of chain with snaps. The first she snapped onto the ring at the front of my collar and then angled it downward to attach to one of the crosspieces of the luggage cart. The second she used to attach to the ring at the top of my head harness to a loop above me at the top of the luggage cart. The last she snapped onto the two rings at the end of the bondage gloves, pulling it taut before locking it to the other end of the cart.
I grunted from behind my gag as I tested my bondage, the chains and the bells jingling in the quiet of the room. Although I had some movement, I was unable to stand up, unable to kneel further, and unable to move much either forward or back. I was a sissified slave, helpless.
"Wow aren't you a sexy sight, my little slave!" Jess said gleefully, as she slowly circled the cart looking her sissy up and down.
Grabbing hold of the cart behind me, she pushed it forward and spun it sideways so that I could see myself in the mirror. With my entire body encased in pink and bound, I had become like the sissy in the bondage fantasy photos I had admired.
After moving the cart just a bit more, she whispered to me, "Hmmm...maybe I WILL move you outside the door, just roll you down the hallway and leave you there."
Despite my panicked fear of such a prospect, which caused me to struggle once again, I felt, against my will, my inner self getting turned on by the idea. "I mean, I could just roll you down the hall to the elevators and send you by yourself down to the lobby. Could you imagine what everyone would think about you down there when the doors opened?" she asked mischievously, because she knew that my active imagination would fill in all the details of what such a plight might be like.
She let me stew on that for a few minutes while she reached into my panties and stroked my encased cock, which she could feel trying to push it's way out of the cage.
"Loving being the sissy-in-distress you've fantasized about hubby? With all of this," she teased, running her hands over my bound body, "You probably haven't even wondered where this whole scene might be going, right hon? Or if I have anything else if I have planned for you?"
Jess was right, because given the elaborate scene she had concocted for me, I had very little imagination left over for anything that might come next.
"Well, when I told you that I wouldn't want to be seen outside with you like this, I was telling the truth. As humiliating as you might find that, as you know I'm not the kind of person who likes that kind of attention, so that's not going to happen."
As much as I could through the gag, I breathed a relieved sigh of thanks at avoiding the prospect of that level of shame. I was curious however, to what else could she possible have in store?
"But..." she said with a long pause as I waited for what was to come next, "...I have found a couple of people who really DO love that kind of attention."
My mind spun trying to process what she meant. Our sex life had always been our private world. What had Jess done?
On cue, her cellphone buzzed. She seemed to know who it was as she answered.
"Hi...thanks for checking in right on time...yes, he's all ready to go...how's he feeling about it? Well, he really can't say much now, but I tell from the straining in his cage that he's finding this idea more exciting than he thinks...OK, see you then."
"Well, you are probably curious about what's happening. I mean there you are, with your bra and corset and stockings, in a pretty pink sissy dress and shoes with bows and bells, all bound up in pink and unable to escape. After being married for as long as we have, I know that you find the prospect of public embarrassment to be one your greatest fears. But I also know you like your limits pushed, and your browser history and that erection pushing against your cage right now tells me that being forced into that situation is something you find exciting."
"In about 15 minutes, Mistress Eve and Mistress Natalie will arrive. They are professional dominatrixes who are used to handling sissy slaves like you. They are taking you out for a bit tonight, and there's nothing you can do about it..."
My wide eyes must have communicated my wonderment to Jess, so she continued. "Now hon, you know that I want nothing but the best for my hubby because I love you. These two ladies come highly recommended and in talking with them, I can tell you that they are professionals. It just so happens that their profession involves disciplining and training submissive men like you. They helped me select a few of the pieces that you find yourself restrained by, and unlike me, they really enjoy the attention that comes with living the fetish life...as you will be finding out in a few minutes."
My heart beat rapidly as I spun through the ramifications of what she was saying. Yes, I had always wondered what a session with a pro-domme might be like. But being under their control when I was dressed like this? In public? Bolts of fear ran through me, and I began to truly experience the psychological panic that goes with being a damsel-in-distress, when the fate you dread is revealed to you, but you are helpless to avoid it. For someone with my kink, it was terrifying and exhilarating at the same time.
"On second thought, I will give you the chance to escape your predicament," she declared, "Isn't that generous of me?" With that, she strode over to a chair out of my field of view. As she sat down, she took a few moments to admire the captive displayed in front of her.
From behind the chair, she pulled out a device that I correctly guessed was a wand vibrator, one of our favorite toys. Hiking up her skirt, she continued as I listened intently.
"Seeing this way has me so wet that I've been wanting to come all evening. Tell you what...I'm going to sit here and pleasure myself. However, if you can somehow free yourself before I have an orgasm, I'll let you go and we'll spend a nice night here in the room. Otherwise...you'll be out of this room in about fifteen minutes. Now...struggle for me dear, let's see you try and escape. Struggle."
And with that, she turned on the vibrator.
Although I had fantasized about situations like before, I had always envisioned them as happening to other people, and I was quite sure right now I didn't want to be carted away by two dominant women to do whatever they wanted to with me, especially dressed as I was.
I started to struggle, pulling first on the chain and gloves binding my arms, then against chain on my collar, trying to free myself. As I did so, the bells on my collar, shoes and gag jingled, combining with my gagged "Mmmmph"s to provide a soundtrack to my struggles. With the amount of leather, locks and chains holding me, I knew the chance of getting away was almost zero. But the struggles took me to a deep realm of subspace, and time seemed to stop.
All that I could feel was my helplessness, my bondage, and the thought of my wife's pleasure in watching her husband unable to do anything to avoid the fate that awaited him. The strain of the leather, the sound of my grunts and the tinkling of the bells continued as I, a sissy-in-distress, tried to avoid my fate.
The sighs and moans of my wife's excitement became more pronounced and I knew that time was running out as I redoubled my efforts. Still, the chains and locks held. Finally came the soft cries that I knew well as the sounds of her orgasm, although they continued longer than normal. I heard the vibrator switch off, and heard her shift in the chair.
For some moments, the room was silent. I had lost and I knew it.
"Wow, that was amazing...to come that strong for that long. I never realized how much of a turn-on a watching you really struggle to escape would be....", she said, her breath starting to return to normal. "I may be even more dominant than I thought I was, and I really love binding up a 'girl' for a change. You may be spending more time in dresses in the future dear." A gentle smile settled on her face as she enjoyed the afterglow.
A few minutes later, there was a knock at the door. Jess stood up, smoothed her skirt, and went to answer the door. As she walked by me, she stopped and kissed the outside of my gag. "Enjoy, my dear," she whispered.
"Welcome. Come in," I heard Jess say, although I could not see the door from where I was.
I heard a female voice reply. "It's good to finally to put a face with a name. Hello Jessica. I'm Mistress Eva, and this is Mistress Natalie." Then another voice. "Good to meet you Jessica. And I see you have our little slave all ready to go as you promised. Did he give you any trouble?"
"No," Jess replied, "as a matter of fact he was quite the willing participant, at least up until I mentioned the little excursion you have planned." The women shared a laugh.
I heard footsteps across the carpet, and suddenly two women came into view, trailed by Jess.
Both of them moved with the confident stride of those accustomed to being in control.
The first, a dark haired Asian woman, wore a leather bustier and tight leather pants, topped with black stilletto-heeled boots. A leather crop hung from one side of a thin belt, a small length of silver chain was looped on the other side. The other was a bit taller, her latex catsuit cinched by a black leather corset, both of which contrasted with her long blonde hair. Like her companion, her footwear was fitting of a dominatrix, with high black heels accented with silver spikes. Both of them seemed to wear makeup as a weapon, their intimidatingly beautiful visages clearly communicating personas that could control one with a smile, with a frown, or even with the lift of an eyebrow.
"Well, well, well, what have we here?" said the Asian dominatrix in a sultry voice that identified her as Mistress Eve. She removed the crop from her belt and dragged it across my body as she slowly examined my restraints.
"You have him secured so nicely to this cart Jessica - it would be so tempting just to wheel him around the hotel like a doll on display, parking him in various places for strangers to gawk at and wonder what kind of man would be so submissive as to allow this to be done to them. One could take him anywhere, down to the meeting rooms, into the hotel lobby, even maybe out the front door."
"Can you imagine it sissy? To be helplessly left in a public area, knowing that everyone could see what a true sissy you are? Knowing you couldn't move, they'd come closer to sate their curiosity, noticing all the details of your dress, your shoes, your stockings. The truly adventurous women might touch you, stroke you, lift your skirt, and laugh as they saw your poor caged cock. You'd want more than anything to escape their attention, but chained to the cart, you would only be able to jingle your little bells as you struggled. But I'd bet that even with that deep humiliation, your poor cock would be straining against the cage, maybe even drooling a bit...because this really excites you doesn't it?"
The prospect caused me to struggle once again, but much as wanted to reject the notion, in my heart I felt her words ring true. Could I really be this submissive? This much of a natural sissy? This desirous of being publicly shamed?
"Look at this Mistress Eve," Mistress Natalie said, "This pretty pink satin dress, so frilly and feminine. I bet you love the feel of this against your skin, don't you sissy?" she asked as she ran her hands over the material of the dress and I could feel the smooth satin caressing me. "Ah, he's wearing a corset, tightly laced, so tight, creating girly curves on this male body. The stockings and garter belt go so nicely with this outfit," she continued as she ran her fingernails up and down my legs, causing me to shiver from the sensations of her touch.
Mistress Eve crouched down to look at my feet. "I love these shoes! They are the ultimate in sissy footwear - I must ask you later where you got them Jessica. Can you imagine the feeling of being forced to stand in high-heeled pink shoes, knowing that they were locked on and you couldn't get them off no matter what? The bells are the perfect finishing touch too. There is nothing like the soft tinkle of little bells like this to remind a sissy of just how humiliating their situation is every time they move."
Lifting the hem of my dress with her crop, Mistress Eve inspected my panties. "Oh look ladies, he IS drooling with excitement, there's a little wet spot on the front of his pink panties." Pulling the front of my underwear down, she grabbed my balls and cage in her hand. "And I see our sissy is kept as all men should be, caged and frustrated." Glancing up at me as she continued, "You know who owns these this cock sissy? You wife does and...while you are with us, we do. Do we having an understanding?" She gave my balls a slight squeeze, causing just enough pain to let me know that she could make it so much worse if she wanted and that I could do nothing to stop it. I nodded my head in agreement.
"And speaking of move, we had better get going," said Mistress Natalie. "My poor little sissy boy. You didn't know this, but your evening has just begun. Let me tell you what's going to happen."
"Mistress Eve and I are experienced professionals - your wife has paid us well and you will be safe under our care. But we also love what we do. Nothing excites us more than using a submissive for our own amusement, however we see fit, and I can tell already we are going to have a grand evening. You see, there's a party tonight at this hotel and pro-dommes from all around the area will be there. The highlight of our parties though, is a kind of show-and-tell. Well, show really, where some of us bring our slaves in to entertain the group. And you, dear sissy, are our contribution to tonight's festivities. We want to give our fellow mistresses a show they won't forget, and you will be the star!"
Hearing that, my eyes went wide and tugged at my restraints - I could not believe what was going to happen to me. The three women laughed at my attempts, and I could see Jess truly enjoying being with these two dominant women. I shuddered, hoping she wouldn't get too many ideas.
"Let's get you off that cart, shall we? Your evening will start with a meandering walk down to the ballroom. We're going to show you off on our way downstairs."
With that, Jess gave them the labeled keys to the locks, and they undid each of the chains holding me to the cart and helped me off to stand in the middle of the room.
Mistress Eve put her hands on each side of my hooded face, turning my head to the left and to the right. "I love this look. He's sucking on a penis gag?" Jess nodded. "The harness - such a nice touch, encasing his head so tightly. And these bells up here and on this sissy collar - what a wonderful touch. Slave, your hood will save you from your identity being known, but I guarantee you that by the end of night, everyone will know what kind of kneeling little sub is wearing this pink outfit."
She continued, whispering quietly in my ear, "and besides, remember to be obedient, because we wouldn't want a 'wardrobe malfunction' to cause your hood to 'fall off' in public, would we?" From the corner of my eye I could see her mocking, devious smile delighting in my helplessness.
"That said, I think this head of yours needs to be restrained a bit more before we leave."
She took a length of chain and snapped one end to the ring at the top of my gag harness. Gently but firmly, she pushed my head backwards until I was looking upwards a bit, with my chin in the air. With a "click", she snapped the other end to the uppermost chain on my arm binders. Unable to turn my head at all, I was just barely able to see in front of me by straining to look there. Having my neck so exposed made me feel even more vulnerable and controlled.
"...and, we'll probably have to lose these panties," said Natalie, "where we're going they won't be needed. I'm guessing he has more pairs Jessica?" Jess nodded yes, and with a snip of scissors I lost my underwear. Although my dress still covered me, it wasn't by much, and I could feel the fabric of the petticoat brushing against my ass. With my head pulled back, the front of the dress just barely covered my caged cock, and I could feel the air against the bare skin of my balls.
I felt a hand on my collar as Mistress Natalie attached a long leash to its front ring, and with a tug, she pulled me forward. Limited to tiny steps because of the chain between my knees I followed as quickly as I could. The bells on my collar and my shoes jingled - there was no way I would go unnoticed.
As Mistress Natalie led me out the door, I heard Eve talking to Jess, finishing with "we will see you later tonight!"
"Have fun!" Jess called to me.
I heard the door click shut behind us. I had truly reached the point of no return, and my mind spun wondering what was in store for me the rest of this night.
"Move along princess!" Mistress Eve ordered, lifting the back of my dress and giving my rear a hard smack with her crop. I did my best, and luckily for me the hotel corridor was empty.
As difficult as the knee restraints had made walking, the sensation of the dress and the stockings moving against my skin as I moved was electrifying. Unpracticed at walking in heels, my gait was unsure and the bells on my ankles jingled noisily down the hall.
Reaching the elevator bank, I waited in fear, hoping desperately that the one that stopped would be empty. I heard a "ding" and the doors opened. Nobody was on, and I counted my blessings. However, my handlers did not move. Surprised, I emitted a "Mmmph mmph" to try and communicate my confusion.
"Oh dear. You thought you'd get away that easy? No, we'll wait for some company." And the doors closed and they pressed the Down button again. About a minute later, another elevator stopped.
The doors opened to reveal a group of three young women, nicely dressed for a night out clubbing in form fitting short dresses. They looked at the three of us incredulously at first, as my mistresses tugged at the leash and led me reluctantly into the elevator. I burned with embarrassment as the women started to giggle. Given my hood, I knew they couldn't know who I was, but right now that bit of rational thinking was lost on me. Impossibly trying to make myself invisible by standing completely still, my efforts were thwarted as I was pushed to the center of the elevator by Mistress Eve.
"Good evening ladies," Mistress Eve said, "we're just taking our sissy boy out for a walk. Pretty outfit isn't it?"
"Oh yes," one of them replied, such beautiful material and they pink is soooo cute!" as they all giggled again.
"Feel free to have a feel," said Mistress Natalie, "he's in no position to object and I think he sort of enjoys it. Besides, it's a chance for we ladies cop a feel for a change."
As the elevator doors closed, I felt a hand tentatively brush the front of my dress, and another gently touched my stocking-clad legs. And in a moment I feared would come, a hand went under my dress. "Oooooh, there's nothing under there!" another of them said, and they giggled again. Hands ran over my ass and other cupped my balls.
"What does he have on down here?" the first girl asked as she encountered my cock cage.
"Oh, that's just a chastity device that locks up his cock to keep him under control - it's the best way to keep any man frustrated and needy and knowing their place. And a sissy like this has no need for a dick anyway," she said laughingly.
I could see the floors counting down as we proceeded towards the ground floor and I continued to have my ass pinched and my caged balls fondled as other hands ran across my legs.
When the elevator began to slow they ceased their attention, although the tallest of them whispered to me just before the doors opened, "Oh sweetie, you have a great night and don't get into any trouble" She laughed and dropped a teasing kiss onto the outside of my gagged mouth." The girls exited the elevator, still giggling, as I was lead off across the main foyer.
My mistresses took their time, stopping to look in the hotel shop windows, commenting on the artwork hanging on the walls. Despite the chain holding my head in place, I could shift my eyes sideways to see the others in the foyer.
The reactions to our group of two fetish-clad women leading a bound sissy varied. Some people ignored us (or tried to look like they were) and others just stared. The observers who truly made me want to die of humiliation were those that pointed, made comments and shared a laugh at my plight. I'm sure they couldn't imagine how a man had gotten himself in such a helpless position. Even people who were not initially looking our direction could not ignore the sound of three sets of heels clicking on the tile floor and tinkling of my sissy bells.
We caught the eye of one couple in particular, a striking blonde dressed in a tight black dress and her man in a casual suit. As she had heard the bells she had turned to look, then quickly strode towards us, her partner following closely behind her.
"Wow, as soon as saw this, I had to come take a closer look," she said, "I haven't ever seen a fully dressed sissy in person before. May I examine your - slave - more closely?" she inquired of the mistresses.
"Go right ahead," Mistress Eve replied, "he seems to enjoy the attention...don't you slave?" She tugged my leash and I stepped closer to our visitor.
Her companion looked nearly as embarrassed as I was, but he stood quietly behind her, glancing around to see who was watching and sneaking a few looks at me.
"I'm loving this corset," the woman said to my handlers as she ran her hands over the outside of my waist. How could I have known when I stepped out of the shower only an hour ago that I would be standing in a sissy dress in the lobby being felt up by a strange woman. "It really gives him girlie hips. And these fake breasts look and feel so real," she said, giving my bust a squeeze. "May I check 'under the hood'?"
Mistress Natalie nodded her approval and I felt hands running over my cock cage and stroking my balls. "Nice, you can never let a man have control of his equipment can you ladies? Darren!" she said quietly but authoritatively, "let these ladies get a feel of what you're wearing underneath tonight."
Reluctantly but obediently, her male companion stepped towards the two mistresses. As the woman continued to admire the details of my outfit and restraints, Mistress Natalie discreetly got her hand in the fly of his pants and from his reddening face, you could tell where her long nails were stroking. "Metal is my favorite for a cage," Mistress Natalie said to the woman, all the while staring into the man's eyes. "And the spikes inside are a nice touch." With that, she gave a quick tug or two and Darren's eyes flew open in surprise as he stifled a cry. With a devious smile, she removed her hand and expertly zipped his pants back up.
"Darren! Pay attention! You see honey, look at these shoes locked on his feet, and this collar with the bells. Aren't they just wonderful? We simply must get you into an outfit like this soon."
Stepping back, she thanked the mistresses for sharing their slave with her and they chatted quietly for a minute or two, with a bit of laughing as they occasionally shot looks my way or pointed. With a final nod, the woman turned and walked away, her man trailing subserviently behind her.
"So nice to meet such a natural dominant, isn't it slave? OK, let's move along," Mistress Natalie said as she pulled me forward by my leash and we continued my parade of shame through the hotel.
Eventually, they lead me out of the main area and we started down a hall towards the meeting room area. As we did so the clientele of the hotel began to change. First one, then in small groups, I began to see women dressed in fetish gear befitting the persona of a dominatrix. Many of these women pointed at me, and my mistresses stopped once in a while for brief chats with others they obviously knew.
"Yes, he's ours for the evening."
"You'll see him at the party, yes."
"Great to see you again - it's been so long, we must play together sometime."
"Oh, he'll put on a show you don't want to miss."
"Unfortunately no, we can't lend him out to you. He's sort of new at this and not ready for that yet."
(I was relieved to hear that Jess had given them at least SOME limits).
All the while though, we were proceeding down the hallway, and eventually I saw a wall with a number of sets of doors. "Main Ballroom" the sign read.
Mistress Natalie stopped. "We're here! And if you think you've had an exciting evening so far, well, we're just getting started!" I shuddered at the thought.
They led me over to an area on the edge of the ballroom where they had started to set up before. Two stainless steel metal poles with various attachment points stood, their bases attached to a single piece of flooring that was raised about a foot up like a mini-stage. About eight feet above, another stout metal pipe connected to the two poles, creating a sturdy structure. Two plastic tubs rested on top of a length of table.
"The party starts in just under an hour, so let's get going." Mistress Natalie said.
They started by undoing some of my restraints. Unhooking the chain that held my head back, I felt relief at finally being able to work out the stiffness in my neck and to turn my head. They also removed the chain and the straps from above my knees so that I could walk more smoothly. "How about you take our little gurl here to use the restroom, and I'll get the stuff set out here?" Mistress Eve of her partner.
With that, I felt a tug on my collar and I was led towards the bathrooms at the edge of the ballroom. As we neared the doors, I headed towards the men's room, but a sharp tug on my collar stopped me. "Where do you think you're going sissy? That bathroom is for men. You are just a sissy. Come with me!" and she led me towards the ladies room.
My mind rebelled against the idea but I submissively followed her in without resistance. Because the party hadn't started yet the bathroom was unoccupied. She pulled me up short in front of a stall.
"Helpless boy, not even able to relieve himself without help. Now turn around. Men stand to pee. Sissies sit." She lifted my dress and I sat down, feeling my shame as I urinated through my cock cage. When I was done, she pulled me out of the stall. "Stand still." Surprisingly, she unlocked and removed my chastity cage. Using a damp cloth, she wiped down my cock and balls. "There. Now you're all fresh and clean. Let's go!"
As we returned to Mistress Natalie, I could see that she had been busy. The tubs had been mainly unpacked and there were various pieces of gear, some I recognized and some I didn't.
"Now, if you thought you were done with the chastity cage, you were quite wrong. In fact, this cage," and she held up a metal cage where I could see it, "is one of our most devious. You see, this short flexible metal piece here is a sound, which we will insert into your urethra." I "mmmphed," behind the gag, mortified at the cruel device I was looking at. "Then this part locks around your balls and keeps the cage on. And these little metal screw holes? That's where the electrical leads attach." She chucked wickedly at my wide-eyed fear.
That fear had deflated my erection for now, which made the encasement of my flaccid member in the cage rather easy. After lubricating the sound, Mistress Eve disappeared from my view as Mistress Natalie held up my dress. The sensation as she inserted the sound was not one I had felt before, not really painful as much as a sensation of movement and friction on a part of my body that I had never felt touched before. As the sound reached it's full depth, the front of the cage rested near the head of my cock. With a practiced hand, she pulled my cock and balls through a metal ring, and with a gentle push and the snap of a lock, the cage was fastened in place.
"Now, we're going to remove the gag for just a few moments - you will be silent, or things will go badly for you, do you understand?" I nodded yes.
Unlocking the back of the harness, they undid enough of the straps to tilt the harness off the back of my head, and the penis gag popped out of my mouth. Examining it, Mistress Natalie noted with approval that Jessica had gotten the exact gag model they had specified and that it would make changing out the gag easy when they needed to.
"I don't think you've ever sucked cock, have you slave?" Mistress Eve asked. I shook my head - besides penis gags I had not.
As she told me it was time to get me "fitted" I noticed she had a selection of realistic dildos in increasing sizes on the table. After commanding me to kneel, she took the smallest, only about four inches in length, and inserted it into my mouth. "Open those lips slave, no touching this with your teeth!"
As she slowly pushed it in to its full length, I concentrated on breathing so I wouldn't gag and soon, the fake balls touched my lips. Removing it, she exclaimed "Good! Although that tiny one was not much bigger than the gag you've been sucking on all night."
She grabbed the next size up, this one being larger in all dimensions. Although it was more of a struggle and I was at the edge of panic as she by time she had inserted the phallus to it's full depth, I handled it without major gagging. The humiliation of what I was going through now began to swell my member against its cage once again. My mind refocused briefly as I felt the novel sensation of the sound's subtle sliding inside the urethra of my expanding cock.
The next dildo increased in size once more, and this time with still an inch to go I found myself unable to take any more of its length, shaking my head as Mistress quickly removed it. "Wonderful, not bad for a beginner. Now that we know your capabilities, we can move on."
Mistress Natalie had pulled a wig of flowing black hair from the tub, and she arranged it on my head over my hood, sticking it on with some sort of adhesive. There seemed to be no end to this process of feminization. As one of them held the wig in place, the other replaced the harness over my head and tightened it back down, once again locking it in place and securing the girlish wig.
The front of the muzzle had a circular opening where the previous gag had been removed. Into this opening they forced another penis gag, slightly larger than the previous one had been, forcing me to spread my lips and to suck at it to relieve the saliva. After snapping it in place, they again tightened the strap under my chin, forcing my jaw shut around the intruder and rendering me speechless once more.
Guiding me up onto the platform, I was directed to stand under the crosspiece. From the table of toys, Mistress Eve retrieved a large piece of curved stainless steel. I recognized it as an ass hook. "This, dear sissy, will keep you standing straight, and these..." she noted, as she pointed to the metal spheres at the end of the hook, "will remind you with every movement how you are being displayed like a helpless play doll. What you don't see is that this very special hook has electrical connections too."
My wife and I had done some anal play, but nothing like this fearsome device. Lifting the back of my dress, Mistress Eve placed the lubricated end against my rectum. "Relax, relax" she softly whispered, and with her calm encouragement, I was able to will myself to allow the device to penetrate me anally. I could feel the end of the hook moving up inside me to rest near my prostate at full insertion.
A chain attached to a loose ring on the bar above me was clipped to the end of the anal hook. The mistresses adjusted its length so that the chain was taut. I would the freedom of movement to be able walk along the length of the platform, but with the high heels locked onto my feet, there was no way I could raise myself up any higher to relieve pressure on the hook, much less to lift myself off the hook entirely.
"For the last step, we'll get you wired up."
Each of them had a rectangular box that spouted thin black electrical wires. I could feel one of them clipping the wires onto leads on the anal hook, while the other attached wires to my cock cage, and added a pair of stick-on conductive pads, one to each of my balls. When they were done, an elastic band fastened the boxes onto my upper thighs, out of sight for safekeeping.
Grabbing a remote with a small screen on it, Mistress Eve said, "Make a small noise when you feel any sensation," and began tapping options on the screen. Within a few seconds a small tingle, like someone was stroking my prostate with a feather, tickled inside my rectum, and I made a small grunt.
Nodding in approval, she proceeded, and I felt a similar sequence of tingles on my balls, on my shaft, and finally, inside my cock. Having never done any electrical play before, I was surprised at how physical the feeling of the current flowing across my nerve endings was.
"Great, let's see how you like this level slave," and the sensations switched to a feeling of being stroked, although this felt like the strokes were inside my cock and in my ass. I closed my eyes at the intensely intimate stimulation, and after a few moments began to moan involuntarily.
Mistress Natalie exclaimed, "Look at our horny little slut. If he wasn't stoppered up I bet his little sissy clit would be drooling all over."
And it was true. As my cock expanded as much as it could within the confines of the cage, my being was moving towards something that felt like it might be an orgasm, but at an even deeper level. As my captors watched, the carnal torment continued as my hips writhed sensually in response to the overwhelming sexual forces building inside me.
Suddenly the sensations ceased. I looked pleadingly towards the women, begging them with my eyes to resume. As embarrassing as it was to be performing in front of them, an overwhelming sense of lust and desire filled my entire being, especially as I had felt myself edging so close to an orgasm.
"I'll bet you could do that all night couldn't you sissy?" said Mistress Eve, as my ragged breathing slowly began to return to normal. "Well, I hope you enjoyed that, because THIS is what you'll feeling most of tonight."
With an evil tap of her finger on the remote, I felt a different, sharper electrical sensation ramping up in intensity, from light sensation to something that felt like my cock and ass were being forced to spasm in contractions. The wave continued to build, going from slightly painful to finally an all-encompassing agony as I cried "MMMMMPH! MMMMMPH!" against the gag and involuntarily struggled and moved, trying hopelessly to escape the torment.
And then it stopped. Continuing to try and gasp as much air as I could through the nose holes and against the constraints of my tight corset, I opened my eyes to see the two mistresses staring at me, soft hands stroking themselves. They truly did find pleasure in my pain, and my struggles were a turn-on for them.
"Wow, that was even hotter than we could have expected! You are going to put on the quite the show tonight. My dear, when those doors open in just a few minutes, dominatrixes will come streaming into this ballroom for our party. We promised them a dancing sissy, and you are going be perfect. Every one of them loves seeing a submissive suffer, so you can be assured you will have a constant and appreciative audience. There is nowhere for you to hide. There is no way to relieve your humiliation and embarrassment. It will just be you, on this little stage, uncontrollably performing for these wonderful ladies."
At that I hung my head, defeated. But as I did so, the part of me that sought the fantasy of humiliation stirred and my deep submissive brain went into another realm.
My mistresses hadn't lied. After the doors opened, dominant women cascaded into the ballroom. The variety of fetish dress ran the gamut, but clearly these ladies were out in their finest tonight. There seemed to be every variety of leather and latex outfits, and even in my predicament a stocking fetishist like myself could not help but be impressed by the beautifully encased legs of some of these women.
This gathering was a submissive's dream, and if the circumstances had been different I would have found myself mesmerized by this collection of powerful pro-dommes. As it was though, my mind was frantically cycling through a mix of nervousness, humiliation and a deep apprehension of what was to come.
As the crowd picked up their first round of food and drinks, they began to disperse around the room. Mistress Natalie stepped over to me. "Well sissy, it's show time! Enjoy your evening!" and, stepping back, she pressed the remote and the electrical shocks hit. I jumped, my bells jingled, and I groaned. My night of suffering had begun.
There were other slaves on display in the room - some being tied into intricate rope work, some being caned or whipped, some worshipping feet. But through it all, there always seemed to be a crowd watching me and talking with Mistresses Eve and Natalie.
As I endured the continuous cycle of incredibly intense painful electrical sensations and brief interludes of relief, I could not help but struggle and groan in my agony. As I involuntarily moved back and forth on the stage, the bells on my feet and neck had me jingling like the dancing slave-gurl I was, and the ass hook rocked inside me, massaging my prostate and layering on a level of sexual pleasure in the midst of my torment.
The dominatrixes gathered, some with their own slaves being lead on leashes and chains, and laughed and pointed at the dancing sissy performing for them. My shame was constant, but pushed to the background by the series of electrical sensations and shocks.
The electrical hook inside my ass caused a pain deep inside my bowels, but even that did not compare to the eye-rolling intensity of what the electrics on the sound and the cage were doing to my cock, inside and out. The current flow violently massaged every inch as the sensitive nerve endings there were relentlessly jolted again and again.
Once in a while, my mistresses would let another dominatrix run the remote control, and as they adjusted the controls they caused me to writhe, jump and groan on cue, to their obvious delight.
A number of times during the evening, they switched to the "stroking" setting for prolonged periods, and I was forced into the humiliation of moaning in unsatisfied edging and desire as the electrical patterns mimicked gentle fingers massaging my most intimate and erotic areas. My mind was a sexual slave of my own body as I helplessly performed sensual gyrations and desperately humped the empty air as the eyes of the crowd witnessed my complete submission.
In the few moments when I gathered myself up enough to glance at my audience, it was apparent how much of a thrill these women were getting out of watching my torment. Their eyes glinted gleefully, like sexual lionesses playing with their prey.
After what seemed like an eternity of public suffering, Mistress Eve shut off the shocks and walked up to me.
"My dear sissy boy, you have provided such entertainment for us. But you must be so tired of being on your feet."
I nodded affirmatively.
"Let's get you off of those heels, shall we?" She began by unhooking the anal hook from the bar above, and then gently removed it from my behind. My ordeal was finally over...or so I thought.
While I was being unhooked, Mistress Natalie had been attaching something about two feet off the ground on one of the poles and had placed a padded mat in front of it. "Come here and kneel slave," she said, guiding me to where she wanted me. She stepped aside to reveal a dildo sticking straight out at me. I quietly whimpered, understanding now that my night was far from over.
Unlocking and unsnapping the chains holding my arms behind my back, she had me put my hands out underneath me. As got onto my hands and knees, she relocked the rings on the fingers of the gloves to rings attached to the floor. The dildo was nearly touching my face and I had to lean back a bit on my heels to avoid it.
Unfastening and removing the penis gag from my muzzle, she wiped the saliva from around my mouth. She pulled on my collar, forcing my face towards the dildo.
As I did so, a brief sideways glance showed that there was still a large group watching me. As shaming as my 'dance' had been, being made into a porn star in front of a group of strangers reached a new level of sexual humiliation.
"Open!" she ordered, forcing my mouth around the phallus.
She slowly but firmly pushed my head forward, forcing the dildo farther between my lips, until my mouth was invaded by a few inches. She then attached two short chains from the post to either side of my head harness, and another stout chain from the post to my collar.
As she did so, Mistress Eve was inserting another post in the floor behind me. Once my head had been positioned, I felt my dress flipped up behind me, and latex-covered fingers probing my anus with lube. Second later, I felt the gentle push of what must have been the head of a dildo start to enter me. Relaxing as much as I could, the intruder slid in deeply as I felt it fill me, followed by the tingles of sensation inside my ass as they tested the electrical leads there. Satisfied, both of them came to squat down next to my face.
"You are about to be our demonstration in training a sissy cock sucker. In this spit-roast position, you'll be able to move forward or back, but you won't be able to escape either of these rubber cocks. Just try it slave." she ordered.
I tried to pull backwards, but the chain on my collar kept my mouth around the face dildo, and when I moved forward a bit, I could feel the rubber cock sliding in my ass. She was right, there was no way I would able to dislodge either of them.
"On this dildo," she said, pointing at the one in my mouth, "are three metal rings. The first will turn off the electricity to your ass. The second, farther up here, will turn off the electricity to your cock cage. This last one will set both of them into that stroking pleasure mode you seem to enjoy so much, so if you can hold that one, you may even be able to make yourself come. The cock you have your lips wrapped around is another size up from the one that you couldn't quite handle, so it will be a challenge. But by the time you're done, we guarantee you'll be much more ready to be a full sissy....oh, and we want you to focus on the cock, so...," and she placed a pink leather blindfold over my eyes and buckled it tightly.
I heard the click of their heels as they stepped off the platform, followed by the feeling of the ramp-up of both electrical boxes into the painful zone. My struggles were useless as I again pulled back on the chains on my head - I could not remove my mouth from the dildo. As I squirmed, I pushed forward, trying to stop the shocks. The cock pushed into my mouth, and as I neared my limit I felt my lips pass over a metal ring. The electrical shocks in my ass stopped, although the sensations of the dildo moving out of my ass remained. As the cock penetrated deeper into my throat, I could feel the muscles tighten up, and I had to pull back.
As I did so, I was again impaled deeply from the rear, and the electrical torture began anew. Pushing forward, I tried to suck deeper once more, successful in turning the first ring off a bit longer before being forced to retreat. Encouraged, I pushed farther with my next attempt. This time my lips touched the second ring, briefly ending all the torment, but I knew was reaching my limit. I could not hold myself there and I pulled back.
Each time I plunged forward I tried to relax my throat a bit more, but I could not hold the dildo that deep for more than a second or two. This caused me to get into a cock sucking rhythm with the pain pushing me forward but the gagging forcing me back to breath again.
At the same time I was fucking myself in my ass, which I had never experienced before. Admittedly the pain from the electricity was difficult, but as my rectum relaxed, but I was astonished to discover how pleasurable I found being anally penetrated. Mentally of course, being forcibly impaled on both ends was about as sexually submissive as a sissy could get.
Near the edge of my consciousness I could hear my audience buzzing about my predicament, some of them cheering me on. Occasionally I would hear one of them close to my ear whispering to me what a cock sucking slut I was, or how much they would love to see me suck their strap on.
To be on humiliating public display, being forced to suck a fake cock and simultaneously be fucked in the ass put me in a head space that took me to another level of submission, scratching a deep itch somewhere inside my psyche.
As my trials continued, Mistress Eve knelt on one knee beside me. Putting her mouth near my ear, she said quietly, "You are doing a wonderful job sissy, easily the most popular show of the evening. Some of the mistresses watching you are so turned on it's all they can do to keep from jumping you themselves. And do you know what's even better? I don't think you noticed as we were setting you up, but there are cameras sending this live back to your room for Jessica to watch."
At that, my eyes went wide behind the blindfold. I stopped momentarily, stunned. What would Jess think of her husband, watching me being publicly displayed like this, exposed as a cock sucking and fucking slut for dozens of people to see? The sharp jolts on my cock and in my ass forced me back into my rhythmic rocking between the dildos.
"Oh, and I can tell you dear, from what Jessica has been texting us, she's finding your show an incredible turn on. I'm guessing that she's probably lying back and pleasuring herself while watching you suffer...and I'd also guess that you might find yourself on the receiving end of her strap-on in the near future sissy-boy!"
As minutes went by and my slurping and sucking attack on the cock continued, I became able to spend more seconds without pain. I could feel myself becoming able to accommodate more and more of the dildo in my throat.
At some point, my lips touched the third ring, and just briefly I felt the flow of stroking pleasure from the electricity massage me. I redoubled my efforts, able to keep the painful shocks off for longer periods of time, and sometimes trigging the pleasure for a few seconds.
However, I could not rest - every break for a breath made me jump and squirm from the torment of the shocks.
Again and again my lips moved up and down the shaft and now that I was sucking deeper, the thrusts into my ass were getting longer and faster. How could I both so humiliated and so turned on at the same time?
Taking a strong breath in, I moved up the cock and my lips covered the third ring. Pleasure flooded my cock and ass and I moaned. Could I hold this long enough to come? I quivered as I heard the crowd cheer at my utter submission, their volume increasing the longer I held this position. After what seemed like forever, but must have been only some tens of seconds, I had to retreat back, and the electrical torment resumed.
Once again I steeled my resolve, took a deep breath and plunged forward. As I held the third ring in my mouth, the sexual pleasure coursing through me, Mistress Eve whispered in my ear. "Oh sissy, you are becoming quite an accomplished cock slut. I'm sure Jessica will be so impressed and pleased with your new skills."
For the remaining minutes of the party, most of the guests were gathered around me, collectively shouting and counting the seconds that I could hold the dildo deepest and moan and writhe in pleasure in front of them. After each attempt however, my retreat back into the shocks reset my arousal, and my performance became a very public display of edging and denial.
Eventually, I could hear the sounds of party breaking up as the number of voices diminished. The electrical boxes were turned off, and I heard two sets of feet walking over to me.
"Wow, that was an unbelievable performance sissy - that was a spectacle our friends here will be talking about for a long time. You are natural cock slut, and we think Jessica is going to have a wonderful time using a strap-on in that ass of yours. But you look exhausted and zoned out, as we expected, and you are going to start coming down out of subspace. So from here on out, you just let us handle things."
They were right. My brain was awash in a confusing mix of emotions, elation and exhaustion.
I felt hands on both sides of my head removing the chains. The dildo popped out of my mouth and my blindfold was removed. As deep as I had gone, my lipstick remained unblemished, as I had been unable to ever fit the entire length into my mouth. "With more training...maybe I could make it next time..." I thought fuzzily.
I was rocked gently forward, and the dildo popped out of my rectum as a gloved hand wiped the lubricant from my ass. Another set of hands unlocked the chastity cage and I felt to unique sensation of the sound sliding out of my urethra. Both mistresses helped me to my feet and on wobbly legs, guided me gently towards a waiting hotel luggage cart. With the click of a few chains, I was bound kneeling on the cart.
The trip back to our room went by in a daze. Finally, I heard a knock on a door. Jess answered and I was wheeled in. Three sets of hands unlocked me and removed my restraints.
As they undressed me, they shared what the experience of the evening had been like from their points of view. Naked, I was guided to the warm bed and tucked in under the covers as Jess said goodbye to Mistress Eve and Mistress Natalie.
I heard my wonderful wife pull off her dress, and she slid into bed beside me, rubbing her slinky pantyhose-clad legs against me, and she held me closely as her breasts pressed against my back.
"Thank you Jess...that was one of the most incredible experiences of my life." I quietly mumbled, slowly drifting off towards sleep.
"You're welcome dear. As you know, I watched the whole thing on video from up here, and I had more orgasms than any night I can remember. Maybe the next time I'll take you to the party myself," she said quietly.