Trying It On For Size Ch. 01

I couldn't take it any more, the anticipation, the need to be penetrated, to be fucked was overwhelming. I groaned again in pleasure and tilted my hips up even more in the age old signal of the recipient to "give it to me." But now, Tanya seemed to be in no hurry, seeming to enjoy the exquisite desperation that I felt. She was going to tease me, to enhance her position of power over me. I felt her other hand slip in under my crotch and find the velcro band that was loosely around my cock and balls. I heard the sound of velcro being "torn" and then felt a sudden tightening as she pulled the tab of the strap with the thumb and forefinger of one hand while holding the strap in place with the other.

The effect was immediate. My already engorged and swollen cock and balls seemed to expand under the pressure. I felt tremendous heat in my groin and a distinct pulse as my excited, rapid heart rate pounded my hot, red blood into my dick through deep, unobstructed arterial vessels. With the surface veins constricted by the tightened band, the "exits" blocked, the hot fluid had no place to go but to pressurize and expand my shaft, causing the surface veins to enlarge and bulge through the thin skin. The pressure also caused my entire shaft to become incredibly sensitive as every pleasure nerve ending was pressed and awakened.

Tanya returned her fingers to the top of my scrotum, cupping and lightly massaging my balls. With her the heel of her other hand she pumped some lube onto her fingertips and brought her fingers up the crack of my ass, probing with her middle finger until it found my straining anus. I thrust myself back at the finger, trying to capture it, trying to impale myself on it, almost crazed in anticipation. Tanya laughed:

"My, you are an anxious little slut, aren't you Kelly?"

"Please Mistress, . . . please Mistress," I moaned.

"And just what do you want Kelly?" She asked in mock puzzlement.

"Now Mistress, . . . now," I pleaded, unable to wait a moment longer.

"Tell me exactly what you want Kelly," she said, enjoying my discomfort and her power.

"Fuck me Mistress, . . . please fuck me Mistress." I said nearly out of my mind with sexual excitement.

"Yes Kelly, yes, I will fuck you. And when I'm done, you'll know you've been fucked. No phoney strap-on. This time, you get the real thing," patting me on the ass.

I felt both of her hands on my upturned ass, thumbs digging into the deep crevice of my ass crack as she massage the fleshy cheeks of my butt. Using the length of her thumbs along the inside of my crack she spread them open a little and then gripping me with her powerful fingers jerked them open. They were widely spread and she paused a moment to inspect me.

"Very nice, very clean. I see you shaved yourself. Good, I like a clean hole. Nothing to get in the way," she said, voicing her approval. She slipped a new latex glove on her right hand with a distinct "snap."

I felt good about pleasing her. She released her hold on my cheeks, then picked up the bottle of lube and pumped a healthy glob onto the middle fingers of her right hand. Putting the bottle down, she used the fingers of her left hand to spread open my cheeks and then used the lubed fingers of her other hand to coat the inner part of my cheeks before finding my sensitive anus and circling it with the tip of her middle finger. It felt so good - it was cool and it tickled. Then there was a feeling of pressure as she pressed the tip of her finger in. I didn't resist at all. In fact, I loosened up my pressing outward, as though I was making a bowel movement. Her fingertip slipped in easily.

Her finger slowly penetrated with steady pressure. I felt the finger reaching inside me until it touched the front wall of my clean, lubricated rectum. Then I felt it brush back as she crooked her finger and began a slow back and forth brushing action with her fingertip. It felt very good. She had found the bulge of my prostate and was lightly brushing across it, to and fro, as though tickling me. There was a tingle of pleasure deep in my ass and I shivered in response, moaning softly. She returned to the spot that had elicited my reaction and brushed it again. Again, I felt an almost electrical tingle of pleasure in my ass.

Tanya buried her finger in me and then slowly withdrew it across my prostate. Then again, and again, slowly finger fucking me while lightly brushing the sensitive little mound in my rectal wall. It felt so good - I started meeting her finger, backing into it as I picked up her rhythm. As her finger plunged in and out there was a soft "squelching" sound as the gathered lube on the back of her other fingers slapped into my upturned ass. This went on for several minutes as I closed my eyes and just lost myself in the sensation.

A sudden sense of increased pressure on my anus broke me from the sub revery I had slipped into. Her forefinger was joining her middle finger in penetrating me. There was slight pain as the stretch surprised me and caused me to tighten up. She stopped, allowing me to consciously relax myself before continuing. Her second finger slid in easily once I pushed outward. She reached in with both fingers as far as she could go before spreading them into a "V" shape. Then she slowly drew them out, dragging them along either side of the prostate bulge creating the most deliciously intense feeling of pleasure while also stretching my anal opening as the spread fingers withdrew. Closing her fingers back together, she penetrated me again, this time sliding the lengths of both fingers over the middle part of my prostate. Again, there was an almost vibrating pleasure sensation.

Tanya continued the finger fucking in a slow, steady rhythm, pleasuring me by massaging and manipulating my sensitive prostate while stretching my rectum with her spread fingers. I slipped back into sub space as the waves of pleasure seemed to grow in an expanding wave from deep in my gut. The vibrating pleasure sensation was almost continuos as she stroked me back and forth. I rocked back and forth in time to her pace. I think I was having anal orgasms - I had read about them but never experienced them. It can only be described as continuous pleasure sensation in and around the prostate that expands and seems to engulf the whole area but without spasm or ejaculation. I did feel a slow seepage of seminal fluid from my dick, collecting in the reservoir of the condom.

I felt Tanya shift around behind me, drawing closer, the smoothness of her stockinged thighs pressed against the backs of mine. She slowly withdrew her fingers until they exited my grasping rectum with a soft "plop." Then I felt the heat of her large, thick rod as she placed it lengthwise along the inner part of my ass cheeks. It splitmy cheeks widely apart, then she began to move, thrusting up and dropping back, letting me feel the size and power of her member. Even though I had already seen it close up and touched it with my lips, I wasn't prepared for the feeling of immense heat and size as it plowed its way along the inside of my ass cheeks, up and down, back and forth across my sensitive anus.

At that moment, I was a jumble of contradictory feelings and desires. I wanted it, wanted it badly; wanted it filling me up, taking me, fucking me. I had waited so long - had been teased with it for what seemed hours and now the moment was at hand. At the same time, it's sheer size frightened me. It didn't seem possible that it would fit and if it didn't it would not only hurt me, it could injure me, perhaps badly. And so the two most basic of human emotions - desire and fear clashed within me. The battle ended quickly.

"Fuck me Mistress . . . Please fuck me," I moaned softly, thrusting my ass back as much as I could while bound and spread as I was.

I felt Tanya spread my ass cheeks wide, inserting her thumbs deeply in my crack until their tips touched the rim of my anus. Withdrawing her hips slightly, she positioned the head at my straining anal hole and slowly pushed it in while keeping my ass cheeks spread widely with her thumbs and forefingers. The head stretched me, the slight pain signaling me to push out, to relax. There was one more little stretch as the wider glans passed through. I felt her dick buried in me, holding my anus open. Tanya was still, no thrust or pressure. She allowed me time to accommodate it.

Having been taken many times by strap-ons, I immediately compared the two sensations and found they were completely different. A strap-on dildo feels cold and hard - it feels like a foreign body. This was completely different - it was warm and yielding, and I felt it move and change size as it pulsed and twitched. Also, the shape of Tanya's dick was different from most dildos or other dicks I've seen for that matter in which the head was the widest or thickest part of it. Tanya's was shaped like a large, blunt ended cone. The head was actually the smallest part. The shaft immediately behind the head was as thick as the glans and then it widened from there, gradually getting thicker all the way down the shaft to the base.

That unusual shape accounted for one immediate effect I felt. Unlike all the strap-on dildo's I had taken previously, the stretch and pressure of the head on insertion was not followed by a relaxing close-up and grip of a narrower shaft. My anus remained stretched and under pressure even after the head was already in because the shaft behind it was just as thick and would get continuously thicker. Of course, I wasn't thinking of any of this at the time, inflamed and aroused as I was, I just wanted to get fucked. I leaned back to get it started and realized immediately that I was in trouble. The stretch and pressure increased as it slid in just a little ways.

"Let me," Tanya said as she took a firm grip on my flanks with her large, powerful hands.

She thrust back and forth very slowly, just an inch or so of movement in each direction as she slowly stretched me and allowed the tight band of anal muscle to stretch and accommodate itself to the impaling wedge.

"Oh god, . . . Oh god," I said, convinced that she would split me in two if she thrust in hard.

I needn't have worried. Tanya was very patient and obviously experienced in how to handle newbies like me taking her enormous member. She continued her short, slow strokes until she felt some loosening, the lubrication finding its way into every crevice to reduce friction. As the pain and distress of the stretch started to ease, I felt her penetrate and push in slowly just a little bit further. Again, I felt the pain of a greater stretch as the thickening shaft entered me, opening my anal ring as it went.

"Oh god, oh god, slow please Mistress, slow please," I gasped.

"Don't worry, I'll go nice and slow. Just relax, this is going to feel really good in a few minutes," she said with confidence.

"Okay, okay," I said panting like a woman in labor to take my mind off the pain.

I pushed outward and willed myself to relax, aware that I could control only the outer sphincter which was under voluntary muscle control but not the inner sphincter which relaxed, if it did, whenever it was good and ready. The immediate response to my outward push and relaxation was more dick as I felt more of it slide into me, stretching me again. I could see where this was headed. Every time I loosened up a bit, more and thicker shaft followed starting another round of painful stretching. This continued for a couple of more cycles before the endorphins kicked in and each successive round of stretching seemed to involve less pain.

By the time half of her cudgel-like cock was embedded in me, the pendulum seemed to swing a little, just enough away from pain to begin feeling some pleasure. There was something about the feeling of fullness, the sense of being completely taken, not to mention the pressure and friction on my sensitive, activated prostate gland that started a slow but steady progression of building pleasure. With Tanya about half way in me, she stopped, took her hands off my flanks and reached around to my groin, finding the velcro band around my cock and balls and pulling it tight.

I gasped in surprise at the sudden pressure on my cock and balls, shifting my focus away from the pressure on my rectum. She lightly grasped my shaft and the feeling was electric, a bolt of pleasure shot through the shaft down to the base and then spread outward, a gathering sense of warmth and excitement growing in my crotch. My dick, which had gone soft, a common reaction by me and most men upon being anally penetrated, was rapidly stiffening under the effects of the constraining band and the light touch of her lubricated hand. She stroked me slowly, feeling me respond, before resuming her thrusts, back and forth, withdrawing it to just the edge of her glans before slowly thrusting back in to about the halfway point of her ten inch shaft.

It was starting to feel very good now. Although still tight, her dick was moving back and forth easily, filling me and withdrawing, filling me again, in a constant rhythm, pressuring and rubbing my prostate, sliding her fingers up and down my shaft, playing me like a musical instrument. I had lost all fear and now was consumed by desire. It felt so good, sooooo fucking goooood! I started thrusting back, confident that this was how it was going to go until I exploded which I knew would be very soon.

Then the pace of her thrusting picked up. Back and forth, back and forth, like the piston of an engine picking up speed, revving up, she started to go faster and faster. Her hand on my shaft kept pace, sliding up and down faster and faster, her fingers gripping my shaft tighter. As she increased speed, her thrusts started to get a little deeper. I could feel that she was penetrating parts of my rectum that hadn't been reached before and I felt the increased stretch on my anus from the entry of the increasingly thicker lower part of her shaft.

I was picking up speed along with her, rocking back and forth, moaning louder and louder:

"Yes, . . . yessss, . . . yesssssssssss, . . . oh god yess, yesssss, . . . yessssssssss!"

"Yes baby, come on, . . . come on, take all of it, take all of what mama has to give you," she hissed through clenched teeth as her passion rose.

With her dick more than half way in me it hit bottom, striking the top of my rectum with each rapid thrust, trying to find its way past the guarded portal of my colon entrance. My involuntary sphincter wouldn't yield and so the beast was limited to my rectum despite the constant banging at my door. It hurt some, the pressure on the colon sphincter, but it was so intermixed with the pleasure of the fucking, and the hand job on my shaft, that the pain effectively disappeared, merged into much more intense, pleasurable sensations.

With each deep thrust, Tanya was yanking down hard on my shaft in a stabbing like motion, as though she was trying to drive my penis through my groin. Impossibly, her speed picked up and she was a blur of motion. Fucking me with complete abandon, a machine running wild, pistoning in and out of me like car engine revved up to the red zone, her hand keeping pace on my straining, turgid staff. It couldn't go on much longer. My senses were being overwhelmed. I couldn't separate out one electric, vibrating zinig of pleasure from another. They seemed to be coming from everywhere, rectum, prostate, penis shaft, dick head, even my balls seem to be drenched in pleasure. I somehow sensed that Tanya was also close, her breathing was so rapid I thought she would hyperventilate. Both of us were slick with sweat. The only sounds were our moans of pleasure and the soft "slap, slap, slap," of her wet hips against my equally wet ass.

I knew I was close but even so it caught me by surprise. Whenever I've orgasmed in the past, it's ignited from one spot - usually the sensitive spot below the head on the underside; occasionally, the deep base of my shaft lights it off. This was something completely different. It ignited everywhere at once - all along my shaft, my balls, prostate, you name it; it all exploded at once. It felt like the top of my head was blowing off.

"Agggggg. . . aaahhhhhhhhhhhhhhhhhhhh! Ungkkk-ahhhhhhhhhhhhhhhhh! AAAAHHHHHHHHHH! Aaahhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!

Even bound and spread as I was, I bucked violently and spasmed like an epileptic, crazily, wildly, every muscle twitching, my dick exploding, shooting rope after rope of thick, white jism into the condom, filling the reservoir, stretching it. As I came, I felt my anus slam shut gripping the enormous shaft embedded in me so tightly that I could feel every bump and ridge on it. Just after my first gigantic spasm, I felt the shaft grow in me suddenly, then she went off:

"AAAgggggggggggkkkkkkkkkkkk! Aaahhhhhhhhhhhggkkkkkkkkk! Aggggghhhhhhhhhhhhhhhh! Aaahhhhhhhhhhhhhhhhhhhhhhhhhhhh!

She had my flanks in a death grip and she flailed about wildly, thrusting and pumping, thrusting and pumping. I had never felt anything like it - no strap-on felt like this. She was incredibly strong and I felt like she would rip me open as she thrust harder and harder at my unyielding colon sphincter. As my own crashing orgasm subsided, I was able to focus on hers; to feel that special sort of satisfaction that comes with bringing orgasmic pleasure to another. Later I thought, "so that's what it feels like for a woman when a man comes inside of her."

I felt every pulse of her thick dick in me, shooting out stream after of stream of hot cum into her oversized condom, filling the reservoir. The whole shaft was so hot that it actually felt like she was burning my insides. Then she collapsed on top of me, sweaty breasts pressed into my equally sweaty back. My knees gave way and I collapsed flat on the bed, her hot, wet, slippery body on top of me, still panting loudly, her warm breath blowing in my ear, her dick still pulsing inside of me. I felt the hot weight of her body on top of me, pressing me into the mattress as I drifted off.

I don't know how long I was out. It must have been only minutes but I had no sense of the amount of time that had passed. It was as though a switch had been thrown shutting my brain down for a time and then thrown again starting it up. The interval in between was entirely lost. I felt her weight shift on top of me. Then hot, slippery movement in my ass as her softened dick slid out of me finally exiting with a barely audible "plop." She dismounted me then slid down towards my feet. Fingers went to my ankles, first one and then the other, disconnecting my ankles from the bondage band, allowing me to move my legs closer together. It felt so good to relieve the strain of the stretch on my hips that I sighed. The mattress shifted under me, tilted as she slid over towards the edge and then off. I heard the click of the bathroom door knob being turned and then the sound of the door closing.

I was drifting somewhere between sleep and wakefulness when I heard the bathroom door open again. With difficulty, I turned over, rolling over on my back, my wrists still clipped to the center ring of the bondage band near the head of the bed. The room suddenly brightened from the bathroom light before dimming again as she closed the door. Tanya was still in stockings and she looked lovely silhouetted against the dim desk lamp, her dark red hair highlighted at the edges giving it a halo effect. I looked up at her as she approached, watching as she knelt down on the bed and slid close beside me.

"How are you doing Kelly," she said, a note of concern in her voice.

"Fantastic," I whispered sleepily, unable to keep myself from grinning. "You were incredible."

"Thanks - so were you," she said, returning my grin with a broad smile of her own.

There was silence. Tanya looked down at me as I took deep breaths, my chest rising and falling with each one. Finally, I broke the silence.