Day One

Another cold smear on my ass, and once again the nozzle and the warm fluid were rushing inside it. It went much quicker the second time. "Release it," he said and once again the basin caught the liquid as it seeped from my quivering ass. A wipe, more lube, and the nozzle again. "This time, bear down as the water flows in; this is just a rinse." He made it sound as ordinary as washing my hair in the shower, lather, rinse, repeat. Perhaps, to him, it was.

By the time he had finished I was completely exhausted. I didn't know what time it was and no clocks were visible on the walls. I had arrived home around 6 pm, 20 minutes or so in my apartment, 40 minutes to drive over. Perhaps it was around 10 o'clock or 10:30. I had no way to check, but no way to escape, either. He exited the room and I was left alone on the table for some time, my eyes open but heavy, my hands behind my head, and my sex fully exposed. I may have dozed off because I didn't hear them come back in the room. A vicious twist of my right nipple and a stinging slap on my labia quickly brought me to full attention.

"Pay attention!" she snapped. There will be consequences for your lapse. It is time to test your anal muscles. As punishment, the stretching will begin without the benefit of anesthetic. When you think you are unable to bear it any further, you WILL bear it and YOU WILL REMAIN ALERT!"

He was opening drawers and getting out numerous phallus shaped objects. Some were metal, some glass, but they all looked ominous as they waited in line. He spoke quietly to me as he worked, "Stand up, turn around, and lean over the table."

I did as he asked, though my legs felt like jelly and I wasn't sure how long I could support myself.

"Not enough exposure," she said as she drew nearer. "Put her on the blocks."

He placed two wooden blocks beside my feet. I stepped onto them, a difficult task while leaning over. My ass was now raised high in the air and my face rested solidly against the table.

"Use your hands and offer your ass to me," she quipped. I did so and noticed that he was once again making notes on the clipboard. Some cold substance was applied to my asshole and some more pushed inside. She was really lubing up my ass. "Keep yourself open" she said as something hard forced itself past my tender ring of muscle. It was barely bigger than a finger and I had no trouble accepting its girth. While I enjoyed anal play, I had never had anything larger than my slim dildo up my ass. I was concerned about how much it would have to stretch.

"Size Two accepted."

"So noted."

One by one, they increased the girth of the dildos they forced into my tortured ass until I was gritting my teeth at the last one. It was only slightly larger than the average cock, by my hole was already so sore that I didn't see how it could go on. "More lube" I heard, and again, some cold jelly was applied to my ass and shoved inside.

I saw the next one before it went into my ass and it was obscenely huge, the size of a soda can. "You're to insert this one yourself," she said. "I'll hold it steady and you push yourself back onto it." I tried, really. "Bear down and DO IT!"

Again, I tried, really. Then a stinging slap to my ass and a forceful shove had the phallus deeply embedded in my bowel as I held on tightly to the table and tried not to sob.

"Resistance met at size five."

"Noted."

"Removing for repetition," I heard and the dildo was quickly slipped from my gaping hole. I was left alone for a few seconds to allow my anus time to return to its normal state and I felt the offending object placed there again. "Take it" she said.

I took a deep breath, steadied myself and pushed back as firmly as I could. The dildo forced itself past my tortured tissue to seat itself solidly in my bottom. "Leave it in for a while. I want to really loosen her up. Go ahead and put her back onto the table on her back," she said and he helped me climb quickly, though not gracefully back up onto the exam table. The stirrups were raised and moved closer and I was scooted down further to further open myself for their manipulation. I was instructed once more to hold myself open.

"Go ahead and apply the anesthetic now," she said.

"Topical or hypodermic?" he asked.

Oh, no! They weren't really going to put a needle into my anus, were they? Please, don't let it happen, anything but that, I thought to myself. "Topical for now, though get the needle out anyway, just in case," she replied. "Thank you," I thought to myself, grateful I had dodged that bullet, yet bereft that the chance was gone to show them how much I wanted to please.

She left the room as he prepared more lube and gel for my bottom. I could feel his fingers wiping off the mixture that was seeping from my ass around the dildo lodged there. When he was satisfied he had cleaned enough of the lube from my ass, he dipped a lotion-like substance from a tub and applied it diligently to my aching ring of muscle.

"Some clitoral stimulation sometimes makes this go faster," he spoke. Both of my hands were still holding my ass open so he started stroking my clit. Despite the pain and humiliation, I could feel desire surging hard and fast as he continued his clitoral ministrations. The stimulation began to loosen me up some and he began very slowly fucking my ass with the instrument placed there.

Every few strokes would have him stopping to apply more numbing lotion and use the dildo to ease it into my ass. Soon, the pain in my sore pucker turned to a warm glow. He removed the offending object from my ass and squirted a vial each of lube and desensitizing agent deep inside. Quickly, he replaced the dildo and smeared some more lube around the perimeter.

"Relax for a minute and give the gel time to work. There's more to come," he chuckled. I felt a straw pressed to my lips. "Drink, it's just water." I hadn't realized how thirsty I was, but the water felt glorious on my parched throat. I swallowed a few sips and the glass was taken away.

"You're doing very well," he said. "I think it's making her mad. Candidates usually crack just a little by now, but you've been real solid. She's probably going to try harder to break your spirit. Rest for a few minutes, she'll be back soon." With those words, he left the room. I did rest, but without closing my eyes.

I heard them returning before they ever got to the door, the click of her heels and his soft-gaited shuffle. When she walked in, followed by him, my eyes locked on hers, as she had requested. Never before had I felt so vulnerable. My pussy was drenched, my nipples were hard and sensitive, my heart was pounding, and my ass was stretched over what felt like a baseball bat. It was bliss, or so I thought.

"The number five plug has been in a while," she said. "Let's see if she's ready to continue." I felt the phallus sliding easily in and out and felt inexplicably pleased with myself. "We'll skip sizes six and seven and go directly to eight. There's still a lot of room for expansion down there. The desensitizing will only help a little, the rest of the stretching will hurt- a lot. I intend to take you to your limit."

The instrument of torture/pleasure she produced next was an insanely huge butt plug, with increments drawn on its side in black ink. "Insert to the number eight mark and hold it still," she said.

He did as she asked and I could feel my ass opening again. The pain and burning returned full force, despite the anesthetic gel.

"Proceed to size nine."

I could feel the chasm that was my ass widening and as I looked at her, I could tell how much she enjoyed being in control.

"Slide it all the way in to ten."

I took a deep breath and as I exhaled, he slowly but forcefully slid the butt plug all the way in. It seated itself deep inside my bottom and remained lodged there.

"Inflate it," she ordered.

How had I missed that? There were tubes and lines anchored to the butt plug. I could feel the whoosh of air enter my ass as he squeezed the hand pump once, twice, then a third time. My ass was stretched to the limit and my rectum was full. It was noted on the clipboard.

"Use your hands and show me your clitoris," I was ordered. I quickly did what she demanded.

My clit felt like it was as large as a walnut and throbbed unmercifully. "How many?" she addressed to him. "Want to make a side bet?"

"Three to five" he muttered.

"She's really wound up, I think six or more," she responded.

"What are the stakes?" he asked. "If I win, you'll take it in the ass to the number ten mark and I'll watch while you jack off. If you win, you'll still get it to the number ten, but you can fuck my ass while the plug is in your ass," she responded. What were they betting on? What did all this mean?

While I was holding my cunt lips open, she squeezed a glob of lube out of a tube and onto my steaming snatch. Then a buzzing attacked my clit. It was a larger version of my favorite toy at home, a pocket rocket. She moved the vibrating head skillfully around my aching clit and an orgasm erupted like Vesuvius from my exposed sex. I was dripping wet from lube and from my own girl juices.

"That's number one," she remarked. Then it dawned on me what the bet was. They were betting on my orgasms. The first one had barely taken the edge off my desire level. She kept up her manipulations on my clit. I climaxed three more times, writhing and gasping with each one. That made four, total. I didn't think I could come any more.

"Let's see if she's a squirter" I heard.

I knew what she was talking about-female ejaculation, but I had never experienced it. Because these were extreme circumstances, anything might happen. She reached a latex-covered hand inside my dripping cunt and as she pressed upwards, stars exploded in my head. I had never felt anything like that. It felt as if I needed to pee, but as she kept massaging what must have been my G-spot, the need to go faded, replaced by a growing desire. She added some attention to my clit and kept focusing her concentrations on my G-spot. The sloshy sounds from my pussy turned into squeaky gushes and I came a fifth time, with a flood of milky, fluid coating her hand.

Through tear soaked eyes, I saw her smile cruelly. My heart turned over. I was in love with this woman. No one had ever made me come so hard. I was even more determined to please her. She continued to pleasure me to one more orgasm. When she had exhausted all my passions, I was led to a small room equipped with a mattress, blanket, and pillow.

"It's two a.m." she whispered. "You have six hours to sleep. You will be awakened at eight o'clock sharp. Do not touch yourself during the night. That part of you belongs to me, now."

I fell deeply asleep within minutes; the butt plug still nestled securely in my ass.