Trying It On For Size Ch. 02

Tanya smiled, seeming to read my thoughts as they occurred. She tilted her hips forward and down until the head of her dick was directly over my wide open mouth, just an inch or so above it; her hot, heavy shaft resting on my nose.

"Yes, you must get used to this my little slut. After all, a good slut must learn to swallow," she said with a small giggle, enjoying the moment as she turned the used condom upside down over her dick head.

I watched, cross-eyed, as the almost clear, syrupy fluid flowed out of the used condom and plopped onto the top of her dick head before continuing to run in small rivulets around it until it collected underneath the head. When enough of it gathered together to break the surface tension, it dripped down in a long strand from her dick into my wide open mouth. I felt it hit my tongue and then roll down my throat. I used my tongue to swallow it as more and more came dripping in. I knew I had gone four days without cumming before our session, but was still surprised by the quantity, if it was indeed mine. It kept oozing down in a thin, steady stream, rolling down the back of my throat.

Finally, as it slowed, Tanya leaned forward and tilted her hips up to angle her dick so it was pointed straight down. Easing her hips forward, I felt her hot dick head cross my lips and saw the impossibly thick column of flesh making its way down behind it. I was still trying to swallow the last of the cum when the head hit my tongue in mid swallow causing me to gag slightly. She slid her knees back and leaned forward with her arms, flattening herself on top of me. Using her powerful thighs, she continued to hold my head in a vise-like grip as she entered my oral cavity.

"Use your tongue slut - use your tongue to guide and swallow me. It will go down a lot easier," she said as she slowly eased herself into me.

It took me a moment to understand what she wanted me to do but I responded as best I could, experimenting with a swallowing motion with my tongue as it guided the underside of the enormous shaft sliding into me. She was right, it did seem to help. It also gave me something to do, something to try when the gag reflex hit which occurred as soon as the head cleared the back of my tongue and mouth and hit the top of my throat.

I was gagging, choking and my first instinct was to fight it, try to reject it, cough it up, do something to dislodge it. But there was no dislodging it. With my mouth held wide open and her thighs gripping my head, making it impossible to turn away, resistence was useless. I had to figure out how to swallow it without choking to death. Frantically, I tried swallowing with my tongue, with my air completely cut-off I knew I had about a minute or so before I passed out.

It was the longest twenty seconds of my life before I felt the pressure against the back of my throat ease and the log like shaft slide part way out of my mouth. I took a deep breath, exhaled quickly and then took another breath, filling my lungs just in time for the next slow thrust, this one pushing down against the top of my throat. I tried to swallow again with my tongue, frantically working to get it down. I felt it slide down a little further this time, freeze a moment and then withdraw. Then a third time, thrusting in just as I was able to fill my lungs, getting just a little bit deeper, her balls bouncing up and down on the bridge of my nose before withdrawing.

As I gained confidence that she would withdraw in time for me to get air into my lungs and as I perfected the swallowing technique of easing the shaft down my throat, I developed a rhythm with Tanya. The thrust and withdrawals continued, slow at first and then with increasing speed. I had to adjust on the fly to keep pace with her, to get air into my lungs on the out strokes before she thrust herself back in.

"Ahhhh, that's it, now you're getting it. Mmmmmmm, that feels so good. Now, use your throat muscles to squeeze me when I'm in," she said moaning again in pleasure.

I didn't really know what she meant, but I experimented again, trying to close my throat muscles around the shaft when it was in, before releasing it just as I felt the reverse movement of a withdrawal. I didn't know if I was doing anything at all with my throat muscles, let alone doing it right until I heard Tanya hiss through clenched teeth:

"Yesssssssssss, . . . yessssssssssssss, . . . yessssssssssss, . . . that's it."

Tanya's pace picked up again and she was going deeper and deeper, the ever thickening shaft pressing against my lips and tongue as it made its way in. I adjusted my breathing to accommodate her and found once she settled on a steady pace that it wasn't that difficult to follow her. The curvature of her hard dick seemed to follow the curvature of my throat when entering from the "69" position. It seemed to just slide further and further down my throat without hard impacts against the sensitive walls of my esophagus.

Tanya had reached the pace she wanted and she was thrusting into me like a metronome, back and forth, back and forth, her dick sliding further and further down my throat with each thrust, her hips slapping my cheeks, balls bouncing and jangling on top my nose. At some point, she entered me all the way, balls deep and held it there while I closed my throat muscles around the shaft.

"Oh god, . . . Oh god, that is so good, . . . Sooooo fuckinnnnng good!" she cried.

She went balls deep a half a dozen more times before I felt her ball sack crinkle up and shrink, a sure sign she was about to blow. Tanya felt the impending explosion too and pulled out until she was completely out of my mouth. I felt a tinge of regret. I wanted to experience what it felt like for a dick, her dick, to orgasm in my mouth. Even with a condom on it, I thought it would be an experience to behold. Perhaps another time.

She was on the edge now, herself frantic, wanting to release, needing to release, desperate to cum, when I felt her quickly rise up, reach down and release the ratchet, moving it one spot down, back to the second position. My mouth was still held widely open but the relief of pressure on my strained jaw joints felt so good that I barely noticed that it was still held open. She climbed up off of me, swung by the side table and picked up a bottle of lube and a new disposable glove, putting the items down between my widely stretched legs.

In a moment, she climbed back on the bed, between my legs, facing down towards my feet. Leaning over, she released one tether and then the other from the bondage strap rings. She adjusted both tethers to their maximum length and then took one of my legs and raised it up until it was perpendicular to my body. Then bending it at the knee, spread it wide and brought it back until she was able to reach the outside ring on the bondage strap at the head of the bed with the other end of the tether dangling from my ankle. In just a few moments, she was able to do the same thing with my other leg, splaying me out widely, legs folded back, bent at the knees.

She was moving quickly now, perspiration pored off of her soaking the top and sides of her mask and making her body shine in the dim light. Tanya was breathing quickly, almost panting from excitement and exertion as she raised my hips up and slid another pillow on top of the first one, pressing it into the small of my back before reaching over for the adjustment straps of the tethers holding my ankles back, spread widely behind me. Pulling on each adjustment strap, she removed the slack that had developed when she raised my hips with another pillow. I was now held in that position, My ass tilted up to the point where my anus was pointed straight up.

Tanya wasn't done tightening my bondage. Reaching down between her knees, she found the tether pulling my wrists down towards the center ring of the bondage strap at the foot of the bed and pulled it taught, then pulled it again, until I moaned in pain at the awful stretch on my wrists and shoulders. Then she leaned into the backs of my upraised legs, one at a time and pushed them back to the absolute limit of my flexibility, and a little beyond it, before tugging on the adjustment straps to remove all slack from the ankle tethers.

I can't even describe what it felt like to be so strictly and impossibly widely splayed open, while I watched her slip on the latex glove, smiling at me the whole time. Time seemed to stand still as she slowly, deliberately pumped glob after glob of lubricant onto the upturned fingers of her gloved hand. She was enjoying the moment. It must have been the moment she had played over and over again in her mind. This was the moment that was central to it all.

I was shaking, shaking with cold, shaking with fear, shaking with lust. As widely splayed as I was, there was no need to hold my ass cheeks open as she moved her gloved fingers to my anal entrance, formed two fingers into a hardened dart and plunged them in.

"Oh god, . . . Oh god," I moaned loudly, tilting my head back as far as it would go, bound as it was by the neck to the center bondage strap ring.

She reached in with a third finger and joined it to the first two to form a thickened dagger, plunging the digits in as far as they would go. This time, she wasn't going to waste time pleasuring me with a prostate massage. This was about her. She was going to take me and she was going to take me now. She plunged her fingers in and out, turning them and twisting them to ensure every part of my rectum was lubricated. Slowly she slid her fingers out until they exited with a slightly audible "plop." She held up her gloved hand, glistening in the soft light, hooked a thumb from her other hand at the cuff and pulled it off. Then, reaching over to the side table, she picked up a velcro cock strap. Not one of the smaller, eight inch ones like the one that was tied tightly around my own cock and balls, but one of the larger, twelve inch ones.

Tanya put the strap around herself, finding the slit in one end through which to pull the tapered part of the other end. She pulled it tight, then pulled it tight some more. She picked up the bottle of lube and pumped it, squirting it directly on her massive shaft, now growing before my eyes, lengthening slightly but definitely thickening as a result of the pressurizing effect of the strap. With her large hand, she spread the thick, white lubricant all over her shaft, covering every part of it, with extra at the head and the base.

I looked down between my widely splayed legs at the club standing rigidly up at a forty-five degree angle and felt a blend of raw fear and raw lust all mixed together to create something else that really can't be described as anything other than a crazed, animalistic passion. I wanted it. At that moment, I needed it more than life itself, yet I knew from looking at it that there would be a terrible price in pain to pay for it. At that moment I was willing to pay that price.

Tanya slid up close to my upturned ass, took her well lubricated dick in one hand and guided it to my anal entrance. There would be no teasing this time, no more foreplay. She had one, overriding goal at his point: release, complete, explosive release.

I felt the pressure of her dick head pressing in and I gasped, knowing that the moment had finally arrived. I was going to be fucked, fucked like never before. And I wanted it, needed it, badly. The pressure built until the well lubricated and stretched entrance yielded to the modestly sized head. Even the wider glans passing through provided only a momentary sensation of stretching. Then, there was that strange feeling of not being able to close up behind the head where the shaft was normally thinner than the head. The shaft kept me stretched open and continued to stretch me as it entered me further, filling me up, sliding into me.

I felt the delicious heat of the shaft as it entered me, then the warm pressure on my prostate bulge as the dick head went sliding over it. The thicker shaft behind it pressed on it more and I felt the stirrings of pleasure, a kind of vibrating, electrical zing growing in intensity, emanating from deep in my ass. Tanya leaned forward, her heavy breasts dangling in front of her, reaching for the mattress astride my torso. She fed me more and more of her shaft and I seemed to absorb it, loving the feeling of being filled up, entered and taken, bound and splayed open, helpless.

I grunted in pleasure through my still widely open mouth as her thick shaft kept up a constant pressure, a constant friction on my prostate bulge. I couldn't believe how good this felt. I looked up and saw Tanya's eyes closed, she was equally in bliss. Tanya was right - our fantasies complemented each other's perfectly. I had often fantasized about being bound wide open like this and being fucked, being used to pleasure somebody else. Most of the time, it had been a strap-on wielding domme. Of late, it had been a dominant, top transsexual. This was at the very core of me.

I didn't feel pain until her dick head began pressing on the top of my rectum. Like the first session, the involuntary sphincter between my rectum colon just wasn't opening. Also, her shaft was far enough into me that the thickest part, at the base was really starting to stretch my anal opening beyond its previous limits.

"Ugh ugh," I cried in response to the pain starting to increase in severity.

Tanya withdrew a little, knowing that once the pleasure really got going, the pain of opening me up further would be masked. She had a big dick, always had a big dick, and after a number of years, had learned just how to use it. Tanya withdrew a little more and then slid it back in, retracing a path of pleasure across my prostate, her belly brushing against my incredibly sensitive dick. She repeated the short thrusts over and over, fucking me in two inch strokes like a one piston engine on high rev. Then she lengthened the stroke as I rose up to meet the thrusts, raising my ass up off the pillows as best I could.

Tanya leaned forward more, sliding her hands under my armpits and bringing her fingers up and over my shoulders from underneath, gripping me tightly, using me for leverage, squeezing my shoulders with her powerful hands as she thrust in. She was on top of me, flat, her large breasts pressed against my own chest, her shaved pubic mound rubbing against the underside of my swollen shaft as she thrust back and forth, in and out.

"Mmmmmm, . . . you are so tight, so tight slut. It feels so good, sooooo fucking good," she moaned."

"Yes, fuck me Mistress, fuck me, I want all of it, give me all of it," I pleaded, now approaching insanity at the intensity of lust that had built within me.

Tanya redoubled her efforts, pressing herself into me deeply and making circular movements with her hips, grinding herself into me before withdrawing. I was rising up with every thrust, launching my ass up to meet the straight, downward thrust.

My eyes had been closed as she began fucking me in earnest, disappearing into subspace, lost to the real world. When she began nuzzling and licking my neck and ear lobe, I opened my eyes and looked down over her broad back to see her hips rising and falling, rising and falling, machine-like as she fucked me at a steady pace. I looked back up and saw my own stockinged legs up in the air, severely pulled back, heels up and bouncing every time Tanya's powerful hips pounded into me.

For some reason, looking up at my legs spread wide, heels up and bouncing in rhythm to the thrusts of Tanya on top of me, I had a sudden flash of "deja vu," that feeling you get when something looks or feels very familiar, like you've done it before. Maybe it was one of those Shirley McClain, "past life" moments, who knows, but the view I had from that perspective, was somehow deeply familiar to me.

I closed my eyes again and tilted my head back in pleasure as I felt strong, spark-like vibrations of pleasure deep in my ass. I also felt something inside me give way, release as she plunged into me. It took me a moment to recognize but it came to me. That sphincter separating colon from rectum had given way. Her dick head was sliding into me, deeper than she had ever gone during this or the first session. Tanya's thick shaft was immediately behind that invading head and it opened up that tight ring in short order; at first painfully and then gradually the feeling merged into pleasure as I felt it reach deeper and deeper into my bowel.

For the first time, my anal sphincter experienced the full thickness of the base of her dick as the remaining few inches plunged into me with every thrust. Swollen even further by the tight band she had put around her cock and balls, her veins bulging under the pressure, I could feel every irregular bump and turn of her gnarled shaft. With a series of powerful thrusts, augmented by her powerful hands gripping and pulling on my shoulders, she went balls deep into me. I couldn't believe I had taken it all. She plunged in hard and held it there, allowing me to thrust back up at the spearing pole, plunged in like a pile driver, straight down into my soft, yielding, bowel. I felt her balls banging into my upturned ass crack as she began gyrating her hips, literally screwing me.

At that moment, I wished that I could throw my arms around her and hug her tightly to me, pull in every last millimeter of that incredible pleasure stick but I couldn't. I had to content myself with reverse crunch like thrusts upward. Tanya withdrew just a few inches, gasped and paused, frozen in space and time. I froze with her. The only movement I felt was a subtle swelling of the shaft as it pulsed deep in my gut and then she came, . . . hard:

"Arrrrrggggggghhhhhhhhhhhh, Agggggghhhhhhhhhhhhhhhhhhh, Ugggrrrhhhhhkkkkkk! Goddddddddddddddddddddd! Ahhhhhhhhhhh! Ahhhhhhh! Ahhhh!"

I felt her powerful spasms in my belly, even felt the impact of her high pressure jism hitting the tip of the condom which was pressed deeply into my colon wall. She came and she came and she came, jerking spasmodically as though she was being electrocuted, writhing and crying out, gripping me so tightly that I thought she would crush my shoulders, spearing me deeply, thrusting and thrusting like a wild animal.

Just as her orgasm was ending, the jerking fits of her belly against my dick and the pulsing spasms of her dick against my prostate ignited me and off I went:

"Yaaaaaaahhhhhhhh, Kkkkeekkkkkkkkk, Argghhhhhhhhhhhhhhhh! Ahhhhhhhhhhhhhhhhh! Good God Yesssssssssssssss! So Good! So Fucking Goooood! Can't stand it - Can't stand it!"

It was like nothing I had ever felt before. Utterly penetrated, impaled, speared, jerking helplessly on her pole, the orgasmic contractions seemed to convulse every muscle. Even my hair seemed to tighten up at the roots. It was a full body orgasm, curling me from my toes to my hair, bursting from my groin and gut like sparks from a shorted car battery - incandescent, impossibly exquisite.

I was conscious just long enough to feel her collapse on top of me, crushing me underneath her, blanketed by her hot, wet body, before I went completely limp. I was not completely unconscious, just shut down - insensitive to the world outside of my own skin. I was awash in endorphins, bathing every part of my brain. Every part of me still vibrated at that special frequency of pleasure and I floated, drifting through time and space somewhere in my inner world.

. . .

I don't know how long I was gone. I do know that I never felt her move or pull out of me or feel her release my bindings, but when I finally returned to the reality existing outside of my own skin, I found the room still dark, barely lit by the low wattage desk lamp and heard the sound of a shower going in the bathroom. It took me a few moments to get my bearings, remember where I was, before slowly sitting up. I started to gather up my belongings before I looked down and realized that I still had on the stockings. I laughed a little at the sight, looking down at my sleek, shapely legs and then stopped laughing, remembering that deja vu moment I'd had as we were fucking. Was it possible? I stripped them off, folded them into a neat square and left them on the bed.