tagTranssexuals & CrossdressersTrying It On For Size Ch. 02

Trying It On For Size Ch. 02

bykelmag©

[Just wanted to thank all of my readers who took the time to vote and made Chapter 1 of "Trying It On For Size" the number 1 Transsexual story on Literotica. Thanks for all the great feedback too - it seems there are a lot of would be Kellys out there. Enjoy chapter 2. - Kelmag]



I looked up and saw the low slung scrotum swaying above my eyes, the long, thick, curved shaft pointing upward just in front of it. I heard a quiet tearing sound,"schshhhtt," looked further up and saw Tanya opening another one of her black foil Magnum condom wrappers. She placed the large, round circle of latex over her dick and slid it down with one hand as she spread her knees further apart and tilted her hips forward until the cool, soft surface of her scrotum brushed my mouth. My lips parted allowing my tongue to extend upward until just the very tip of it found the bottom of her lower hanging right ball. I made a small circle with it, tickling it with the wet tip.

"Yessssss, Kelly," she hissed, "show'em some love," Tanya whispered huskily.

My tongue extended out further until I could lay the broad, flat of it on the sensitive underside. Then I licked upward, a long, slow stroke. I could feel her immediate reaction, her balls withdrawing upward, her shaft pulsing and jumping as I found one of her hot buttons.

"Yessss, just like that, lick'em slowly Kelly," she instructed, using one hand to grip the base of her swollen cock and pump it slowly up and down.

I continued to lick, reaching down to the bottom edge of her perineum just where it curved into her anal crack and then upward, drawing a wet, broad line with my tongue swiping the bottom and front of her scrotum up to the base of her thick cock. Over and over I retraced the route, every so often taking a detour around one ball and then the other; sometimes drawing them in until they filled my oral cavity, using my lips and tongue to tug and pull on them. I saw her thighs quiver and heard her respiration speed up. Seeing the immediate reaction to everything I did was so hot.

I looked up and saw her lean forward, at first just a little ways and then pitching all the way forward until her forearms came to rest on the mattress straddling my hips. I glanced down and saw her large breasts swaying above my belly. Then back up and saw the rhino horn like dick tilting down towards my waiting lips. With her hand gripped tightly around the base, she pointed it down until the tip was just at my waiting lips. Slowly, I parted them to allow entry, the first time a dick actually entered my mouth. Even through the latex sheath I could feel the heat of her arousal as the heavy shaft pulsed and quivered as it slid over my wet lips.

It came in slowly, filling my mouth with the hot hardness, spreading and stretching my lips as the increasingly thicker shaft entered. About halfway in it bumped the back of my throat and I gagged, instinctively closing my lips tightly around the invading shaft and jerking my head back and forth to evade the assaulting column. It was too much. I couldn't take. I gagged violently, trying with all of my strength to push it out of my mouth. She eased back, pulling back, easing the pressure on my mouth. She paused for a few moments and then slid it back in, again triggering a violent gag reflex. She held it in me for a moment, dick head pressed against the back of my throat.

I felt completely helpless, arms bound behind my back, neck held to the bondage strap by the leather collar around my throat, I began to thrash about violently, trying to dislodge the foreign invader. Thin mucous ran from my nose as my throat closed down trying to stop the invading shaft. My air was cut off and for a moment I thought I was going to die. I jerked my head violently back and forth trying to get out of harms way. She withdrew quickly, easing the shaft all of the way out of my mouth until just the latex covered tip rested on my pursed lips. I was breathing rapidly, a little freightened for the first time.

It wasn't the gagging so much as the sudden realization that I had no idea what was coming and was powerless to control it. During the first part of the session, Tanya had followed the outline of what I had said I wanted to do, using the toys and devices I had brought. This was completely different. Tanya was not bringing my fantasies to life now; she was bringing hers and despite her claim that they complemented mine, I had no idea what they really were.

Moreover, being bound with wrists above me on the mattress, easily accessible and more psychological than real was entirely different from having my wrists bound behind my back and pinioned under my body, my neck solidly attached to a bondage ring. This bondage was real and completely inescapable. I was dependent entirely on Tanya for my safety - and how much did I really know about her? Not much, the thought flashed across my mind; Not nearly enough.

Still, I was inflamed, aroused beyond sensible thought. When she leaned over, brushed my thighs with her hair, lightly grasped the base of my dick with her large hand, bent lower and enveloped me with her mouth, the brief internal battle between fear and lust was decided. As always, lust won out. It wasn't even close. I moaned softly:

"Oh god - yes, that feels soooo good," I sighed tilting my head back and seeing her balls swaying directly over my eyes.

She used her tongue expertly, laving the top of my dick head, then plunging the shaft deep into her mouth, swallowing me easily until her lips pressed against the top of my scrotum and my pubic mound. She brought her fingers up to my groin and found the velcro strap that was still loosely encircling my cock and balls. She found the ends, held one with her fingers while pulling on the other, tightening it while still sucking on my shaft buried balls deep in her mouth.

The effect on my dick was immediate. It moments it swelled under the pressure of the strap until every vein bulged. Once, twice, three times her head bobbed rapidly up and down, using her lips, tongue and throat muscles to apply maximum suction. Then she held it deep in her throat, the warm breath from her nose tickling my bare pubic mound. She closed her throat muscles around my shaft, then opened them again, squeezing my shaft in pulses in an amazing display of muscle control and oral technique. She tightened the band further until I thought my dick would explode from the pressure. Tanya used one hand to grip and squeeze my balls and the other to play along the edges of my anus with her fingertips.

I was close - so close to cumming. I wanted to release so badly. I was just moments away from the point of no return when suddenly she raised her head up, sliding my dick out of her mouth while simultaneously releasing my balls. She raised up on her forearms and then completely upright still kneeling astride my face. I was shocked at the sudden loss of pleasurable sensation on my shaft and instinctively thrust upward looking for contact. In frustration, I thrust upward again, jerking my hips off the mattress, stabbing the air in a frantic but futile attempt for friction, for release. I groaned loudly.

"Yes, yes, I know how badly you want to cum," Tanya said quietly. "But not now, not yet. I want you on the edge, on the very edge. Part of my fantasy is seeing just how long I can keep you there," she said smiling down at me from between her kneeling legs. "There is so much more - so much more to do."

"Please Mistress, please," I begged. "Let me cum - let me cum."

She ignored my plea, reached over to the corner of the bed where she had placed the items she had taken from her dresser at the beginning and picked up a small, black item. She held it up in front of me. I could not quite make out what it was. It seemed to be rectangular with rounded edges and had an elastic strap. She cleared up the mystery in a moment, slipping the elastic band down over the top of my head and adjusting the rectangular patch over the bridge of my nose and eyes. It was a mask or a half mask - it reminded me of the mask worn by the Lone Ranger; it had small, oval eye holes that allowed me to see but limited my peripheral vision.

I watched as she picked up another small, black item and this time slipped it over her own face. It was also a mask - smaller than mine and more stylish; it was a Catwoman type mask with a dramatically curved shape. The small mask changed her appearance considerably, giving her a mysterious and coldly sensual look - a little dangerous maybe; very sexy - definitely.

Perhaps it is something for the psychologists to figure out but there is something about the anonymity provided by a mask that expands sexual possibilities. Maybe it's one more way of separating oneself from reality; of deepening the fantasy. I don't know but it seemed to remove whatever limits or barriers I had. It seemed to have the same effect on Tanya.

Wordlessly, she rose from me and reached on over to the side table, picking up one of the four foot long tethers I had brought. Climbing back over me, she knelt between my legs, facing me. Then Tanya put her hands under my knees and raised my legs up, placing them on her shoulders while she reached under my raised butt until she found my bound wrists. Using her fingers, she found one of the cuff d-rings and clipped one end of the tether to it. Putting my legs back down on the bed, she slid back drawing the tether with her until she got to the bondage strap at the foot of the bed. Deftly, she clipped the other end of the tether to the center ring. Then steadily pulling on the adjustment strap, made it tight, drawing my wrists down towards the foot of the bed until my hands peeked out under my ass cheeks.

It was not comfortable. Even aroused as I was, I realized that I was being bound further. The image of a spider slowly wrapping up a fly caught in her web flashed in my mind. Bound by the neck at one end of the bed and by my wrists at the other, I knew I wasn't going anywhere. Still, Tanya was right - being bound this way seemed to fit some sort fantasy need of my own. It was very arousing, made doubly so by Tanya moving cooly and expertly in that devilishly sexy black mask.

Again, wordlessly, Tanya moved onto the next phase of her very detailed fantasy. She leaned over and removed first one ankle cuff and then the other, attaching them to adjacent bondage strap rings for easy access. This puzzled me. It seemed a central part of her fantasy was placing me in inescapable bondage and yet she was removing my ankle cuffs. The mystery was solved when she got off the bed, picked up another of the items she had put in the corner and returned.

It was a thin, black, folded square. Holding it by two corners, she flipped it open. I could not have been more surprised at what I saw. It was a pair of panty hose - really more like a one piece garter belt and stockings - there was no "panty" in the pantyhose. Tanya was wearing a similar item and looked very sexy in it. It took a few moments before it dawned on me that she was not going to be putting on the new lingerie. It was intended for me!

I had never worn any article of woman's clothing before and had never had the slightest inclination to do so. Certainly before I had come crashing through all of these sexual barriers, I would have found the idea objectionable. But now - well now, it somehow didn't seem to matter. It seemed like a small thing and if it was part of Tanya's fantasy, well why not.

Tanya didn't ask if it was okay. She didn't say anything. The silence added more mystery and allure. She simply went to work putting them on me. Bunching up one stocking, she wordlessly positioned my right foot to point it sharply downward and then slipped one stocking on it, sliding the attached garter belt up to my thighs and the stocking itself up over my calves. She worked quickly and efficiently without seeming rushed. It was clear she had put this type of lingerie on many a client before. Unrolling each of the smooth, sheer, black stockings up one leg and then the other, she had me raise my hips to bring the garter belt up over my hips to my waist. Then pulling, adjusting and smoothing, it was on me.

It was like no article of clothing I had worn before. Smooth and snug, it seemed to hug my legs, shaping and accentuating the muscles of my calves and thighs. I've always liked the look of stockings - it made a woman's legs appear shapely and sexy. It had the same visual impact looking down at my own legs but added to that was the smooth feel of it against my skin. Tanya ran her hands up and down my legs, sliding hr palms up and down my shapely, smooth limbs, stopping to squeeze and knead the hard, muscled flesh underneath as she went. She looked down and smiled at me, pleased at the result.

Silently, she reattached the cuffs to my ankles, spread my legs and reattached the cuffs to the outer bondage strap rings using two nylon tethers, using the adjustment to pull them tight. The severity of the bondage continued to increase. I was now bound by my neck, wrists and ankles. I looked down and saw my swollen cock pulsing and bobbing, still squeezed tightly by the velcro strap around my package and further inflamed by the sight of my legs encased in sexy, black nylons. I was ready, eager to do anything she wanted if it would bring me blissful relief from the unrelenting sexual tension I felt.

She continued in silence to prepare me for whatever she planned to do, rising up to retrieve another item from the corner of bed. Returning she straddled me, knees hugging my armpits as she settled herself down. Tanya held the item up to show it to me as she made some adjustments to it. Whatever it was, it was evil looking. It was some sort of metal contraption that had two thin, curved metal bars about six inches long, each had an inch wide and deep indentation in the middle of it. The bars were joined at the ends by some sort of lever and ratchet connection. Hanging from one end was an inch wide leather strap. As puzzled as I was, it looked somewhat familiar, like I had seen it before.

I had no idea what it was or how she intended to use it until she slipped a thumb between my lips and curled it over my lower lip and teeth, gripping my lower jaw with her palm and forefinger. In one quick, easy motion she opened my mouth by pulling down on my jaw and then slipped the metal bars between my teeth. I was too entranced and puzzled by the device and she moved so quickly and placed it so deftly, that there was no time to even think about resisting, not that I would have resisted, even if I'd had time.

The indentation of the top bar fit neatly behind my top front teeth; that of the lower bar wedging itself tightly behind my bottom front teeth. Sliding the leather strap attached to one corner of the device around the back of my neck and back up the other side, she buckled it to the corner of the device. She adjusted it so it was snug but not too tight.

As she reached down for the device adjustment levers, I remembered where I had seen it before. It was on one of the many bondage sites I frequented on the internet. It was some kind of medical device, actually a dental device, used to keep a patient's mouth, perhaps an unconscious patient's mouth opened while the dentist worked . Somewhere in my attic mind, the name Jennings clamp popped up. It was used in bondage scenes to keep a sub's mouth wide open for whatever a domme wished to put in there.

I looked up at Tanya and she was smiling, her eyes seeming to twinkle and light up behind the sexy, Catwoman mask. She seemed completely immersed in her fantasy. She made no eye contact with me, or showed the slightest interest in how I was feeling. Whatever personhood I may have had at the start of the session had disappeared. I was now just an anonymous, masked object to be used for her pleasure. The realization sent a ripple of fear through me, and, I must confess, an almost electric spark of lust and arousal that made me quiver in anticipation.

The first setting on the corner ratchets opened my mouth about half way. I was surprised at how powerful the device was. She had used just the slightest pressure to move the levers of the ratchets and the mechanical advantage had effortlessly opened my mouth. I was completely bound and helpless. I had no idea just how wide she was going force my mouth to open. I decided to see If I had any control over it. I decided to resist the next attempt to widen the opening.

Feeling her fingers move and tighten on the levers, I clamped down hard, determined to keep my mouth from being opened further. It didn't make the slightest difference. The second ratchet, a smaller movement than the first, opened my jaws wider with no indication that Tanya even noticed my resistence. In a flash it hit me that she could rip my jaws apart and, bound as I was, I could not do anything to stop it. I was not even sure she would notice any opposition given the enormous power of the device.

Tanya shifted her hips forward until the head of her latex covered dick rested on my chin and lower lip. I could feel the heat even through the latex and the pulse of the thick shaft behind the head beat against my upturned chin. With the second ratchet, my mouth felt wide open but not uncomfortably so. It was like I was getting ready to bite into a large apple. The fear hit when I felt her reach for the levers again and slowly apply pressure to them, sliding the catches into the third ratchet.

The pain was immediate and intense. It felt like my jaw was being dislocated. It was stretched wider than it had ever been before. I tried as hard as I could to bite down and reduce the pressure on my jaw joints but it was useless. I was biting into stainless steel and there was no give. I began thrashing around both in actual response to the pain and to signal that I was in distress. With my mouth clamped open impossibly wide, there was no way to use one of the prearranged safety words - "yellow," or "red." That important safety device was lost as soon as she went to the first ratchet. I stopped thrashing when I felt her fingers moving to adjust something. I didn't want to slow her down so I forced myself to remain motionless.

I was waiting, waiting for the relief of the device being moved back to the second ratchet. Instead, I felt the leather strap tighten behind my neck and then at the corners of my mouth, as she pulled tightly on it, digging it into my skin to make the clamp completely rigid and immovable. I began thrashing again, realizing that the tightened strap removed the last possibility of possibly ejecting the device myself with violent enough head jerks. It was now effectively part of my face and no movement on my part was going to dislodge it.

"Yes, yes little one, it hurts when it's stretched wide for the first time. But be patient, you will adjust, your jaw muscles will adjust and stretch to accommodate it," she said, breaking the long silence.

I was still thrashing about when she reached over to the side table and picked something up before climbing over my face, reversing direction and straddling my head with her knees. Tanya looked up towards my feet, inspecting my body before looking down at me, smiling again as she took in my distress. She tightened her grip with her knees on the side of my head, keeping me from turning it side to side. Her large dick and balls dangled above my eyes as she reached down with a finger and ran it across my stretched lower lip. It felt wet and slippery.

Tanya poked her finger down into my widely stretched mouth and then ran the back side of it against my tongue. I tasted the salty, bleachy flavor and looked up in recognition and puzzlement. It was pre-cum or semen. I recognized the taste from our first session when she wiped a bit of my own pre-cum on my lips and tongue. I looked up first at her dick which seemed to be still securely wrapped and isolated by the condom. Then, I saw in her hand the wrinkled, latex sleeve. It was a used condom. I hoped it was mine.

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bykelmag© 3 comments/ 56832 views/ 27 favorites

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