A Painful Test

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As I began to worship my way up the backside of her other boot, Miss Julia began to lightly run the tip of her crop through my hair. Gently tracing through it and playing with one lock of hair and then another. She had told me that she liked that I wore my hair a bit longer than most men, and I had been letting it grow a bit more since then just to please her.

As I circled around her other side, my tongue not breaking contact with the shaft of her boot, Miss Julia continued to caress my naked body with the tip of her riding crop. I'd seen enough femdom video clips on the internet to know that a crop could deliver a lot of pain, and I wouldn't mind taking a few strikes from it to see just how bad it hurt, but for right now I was content. Feeling the tip of her crop gently dragging across my back like a slow massage was wonderful, and extremely arousing.

Miss Julia placed the tip of her riding crop under my chin and without a word gently directed me to raise my head. On my knees directly in front of her, staring up into her dark brown eyes but stealing glances at her firm breasts covered by tight satin and lace, she told me that I had done a good job and that she was pleased.

She then sat on the edge of the bed and quietly ordered me to take off her boots. They had no zippers and appeared to be a snug fit, but kneeling in front of her and cupping one hand around the back of a heel, I was able to pull the first boot easily off her foot.

A plain white ankle sock covered the foot of her nylon stocking, and she held it up to my face as I set her boot on the floor to my side. I held her foot gently in my hands and pressed my nose lightly into the sole, deeply breathing in the faint odor of light sweat. There also seemed to be just a hint of perfume near her ankle, as if she had planned to have her foot in my face all along.

I caressed and lightly kissed her socked foot, inhaling deeply. Miss Julia hadn't ordered me to do this but she didn't object. My cock now hard and straining, she pulled her foot away and presented me with her other boot. When I had removed it, she told me to smell the inside. Placing the open end of the shaft over my nose and mouth, I slowly inhaled the lightly damp perfumed atmosphere.

"How does that smell?" she asked.

"It smells wonderful, Miss Julia," was my muffled reply. I thought I would get to savor the moment longer but then she handed me one her thigh high boots, the tall unlaced shaft flopping open and the long laces draping on the floor threatening to become a tangled mess. She presented her left foot to me, down turned with her toes pointed up, as if wearing a high heeled shoe. This allowed me to easily slip her foot into the leather boot.

I was really nervous about being able to lace up Miss Julia's boots to her satisfaction. All the hooks to loop around and the seemingly mile long laces, it looked like it might take all night. Then she turned slightly and stretched her leg out along the edge of the bed. That way I could position the long unlaced open boot shaft under her smooth nylon sheathed leg. It was now just up to me to lace through all the hooks.

Some time ago I had come across a video on the internet where a dominatrix had her male slave lace up her pair of thigh high boots. Even if the video had been staged with paid actors, I was still envious of the guy, and it was in a way tough to believe I was in that situation right now.

I remembered that he had hooked one of the laces first, and then with both laces off to the same side, he was able to hook the two laces at once. Then in a quick side to side motion he moved up the shaft two hooks at a time. He had made it seem quick and easy. I tried to duplicate the technique, thinking that Miss Julia would be impressed.

My efforts were slow and a bit clumsy, flipping the long laces from one side of her leg to the next, periodically having to draw them out through my fingers to their full length to prevent them from tangling. I was halfway up to her knee when she slapped her riding crop on the back of one of my hands.

"Where did you learn that?" she demanded to know as I recoiled in pain and put the back of my hand to my mouth, sucking on the hot stinging welt. "Have you been putting on another woman's boots? A professional dominatrix perhaps?" she accused.

"Miss Julia, I can explain," I said, and then told her about the video. "Before we first met, I considered trying to find a pro domme," I confessed. "But I couldn't do it. Even if they enjoyed their work, they'd still just be with me for the money. This is..." I fought to find a proper term. "Intimate. You, a girlfriend. We can go out and have a good time, but then you also know how to dominate me. The spankings, licking your boots, I don't want to do that with anyone but you, Miss Julia."

I had sunk down even lower on my knees, my cheek against her leg covered in soft black leather, looking up her face. Her expression looked as if she were deep in thought. After a few long moments she gently tapped her crop on the side of her boot and told me,

"Get back to work."

While I had been lacing her boot nice and snug, when I got to her knee I tried to leave a bit of slack, thinking that might be needed so she could comfortably bend her leg. I wasn't sure how much slack to leave, and was concerned about what might happen if the laces were too loose and popped off one or more of the hooks. The bright red mark on the back of my hand still stung. If that was the price I paid for showing off, the punishment for screwing up the job would be harsh.

After passing the laces around the last of the hooks, there was still plenty left over. Miss Julia bent her knee, raising it off the bed, giving me room to wrap the excess laces around the top of her boot, where I tied them neatly.

Her mini skirt had ridden up exposing the dark border of her stocking top, a bright silver clasp from her garter belt locked firmly to it in the front. I could also see a tight triangular patch of black lace covering her crotch. She was unshaven, perhaps even untrimmed, given the number of stray dark pubic hairs which peeked around the edges of the fabric.

"Enjoying the view?" she teased, lightly grasping a handful of my hair and pulling my face in for a closer look.

"Yes, Miss Julia," I answered, my mouth feeling dry and my penis throbbing.

"This is my favorite garter belt," she said. "It's a six-shooter." Miss Julia gave a low laugh and pulled up her skirt some more so I could see that there were three straps holding up each stocking. It might also be some sort of inside joke as I remembered she owned a gun of some kind, but couldn't recall how I knew that. I lost my focus and only heard the last bit of a sentence, something about a garter belt leaving her easily accessible.

Miss Julia placed the sole of her boot squarely on my chest and gently but firmly pushed me back away from the edge of the bed. She then placed her other leg up on the bed, and callously tossed me her other unlaced boot.

Now having a bit of experience, I could have probably laced up the second boot faster, but I worked as slowly as I dared to enjoy the task. When I had finished, she stood up and adjusted her skirt back into place.

"I know you want to lick these boots, Eric. Right now though, all you'll get is a small taste. Place one light kiss on the toe of each boot and don't linger," she ordered.

I did as I was told, the scent of new leather strong as I lightly pressed my lips against the toes of her boots.

"Now one kiss at the base of each heel," she commanded, and started to caress my back with her riding crop as I lay one cheek against the wooden floor to kiss the tip of a tall spiked heel.

"Very well," Miss Julia said after I had kissed the heel of her other boot. She stood in front of me as I remained kneeling on the floor.

"You've been very attentive and obedient so far, Eric. You haven't been foolish enough to intentionally be disrespectful or refuse an order to see what you could get away with. A smart move," she emphasized. "I've had no reason to punish you, but perhaps that is why you are still willing to go out me. You are here in my bedroom and should consider that to be a privilege. I'm ready to take our relationship to the next level, and can see that you are ready too."

Miss Julia started to gently stroke the underside of my hard penis with the tip of her riding crop. I shuddered, having been so strongly aroused for what seemed like eternity, and I thought I would shoot multiple bursts of cum all over her boots. She must have sensed I was close to the point of no return, so she tucked her crop under one arm and strutted slowly around behind me, the new leather boots making soft creaking noises.

"However, before we can take things any further, you need to be tested," she said in a soft menacing voice. "I need to know if you can handle being punished by me. Stand up, and hold onto that shelf," she ordered.

While I wanted a few lashes with the crop, to feel the difference in the pain compared to a paddle or belt, I sensed that she was about to give me a severe whipping. I was terrified, yet I wanted to roll with her onto the bed later this evening, so I slowly rose to my feet.

"Please, Miss Julia," I begged in a weak voice. "Be merciful."

"Shut up!" she yelled from behind me, and I flinched at her suddenly raised voice. "Do as I say!"

The bedroom had no closet. Instead, an entire wall had been covered with an assortment of brackets, scrap pieces of plywood, and lengths of used piping, arranged as a system of shelving and rods for clothes hangers. I lightly gripped the edge of a shelf that was at shoulder level. Thick plywood that at one time was painted a light blue color that I associate with swimming pools. Upon it were several plastic milk crates loaded with shoes and boots. Different heel heights and colors, most of them pretty sexy in some way, all jumbled together with no sense of order.

Miss Julia was standing behind me speaking in a low voice, though I confess it was difficult to concentrate on her exact words, essentially telling me that I was about to get a fierce whipping, and would receive a similar one if I ever displeased her.

Her riding crop made a loud snap as the leather tip made contact with my bare ass. I flinched and stifled a cry of pain in a hiss through gritted teeth.

"Hold still, bitch," Miss Julia said in a warning tone.

The crop landed at random on my buttocks in a series of loud snaps, and each time I recoiled in pain. The impact reminded me of a time several years ago when some friends and I rented CO2 powered guns and shot paintballs at each other in some local woods. I had several good bruises and welts after that day despite wearing several layers of clothing for protection. There was no doubt in my mind that she would be leaving marks on me this evening.

Suddenly the tip of her crop snapped me on the back of my right thigh. I couldn't help jumping and crying out.

"I didn't tell you to dance," she said. "Hold still or I'll have to restrain you."

There was no doubt in my mind that she would have something on hand to anchor me to the wall. The open bedroom door was to my right, and even though I was naked I preferred to not be bound and have the option of making an escape if I felt that the situation was getting out of hand.

I was almost glad when she resumed whipping me on the ass and I tried to hold as still as possible. Though my eyes were tearing up with the pain, I looked down the improvised clothing rack. It looked like she had a lot of nice clothes for the office. Living rent free would be an advantage for a woman who liked to shop. Through watery eyes her clothes were a blur of satin and other fabric that looked expensive, mostly in conservative colors.

"Ahh!" I cried out, jumping and howling as another blow landed on the back of a thigh. "I'm sorry, Miss Julia," I offered as a quick apology, planted my feet and gripped the shelf again with white knuckles.

There was a long pause and I heard her slender boot heels click on the wooden floor a few times. Perhaps she was reaching for a roll of duct tape that I might not have noticed on her cluttered dresser. I was getting really nervous when suddenly three sharp blows snapped the back of my left thigh, almost all of them in the same location. Groaning quietly, I managed to keep my feet planted on the floor, though I thought my left leg was going to collapse under me from the pain.

Bowing my head and assuming the worst, the next loud snaps across my buttocks felt lighter, though that was probably my imagination. Down at the far end of the wall of clothes I could see some dresses on hangers. The ones against the corner were bright colors and looked out of place. Then I remembered my sister had kept all of the bridesmaid dresses she had worn, and looked as if Miss Julia did the same. My sister eventually married, but the way Miss Julia liked to dish out pain, it was easy to imagine her as a bachelorette for many years to come.

The next painful blow landed on my right shoulder blade. It was so unexpected that one hand lost its grip and I had to stifle a yelp of pain.

"You just can't take it," she said under her breath before the riding crop snapped again on the opposite shoulder blade.

I glanced to my right through the open bedroom door. It would be one long stride from there to the front door, which was standing open. The screen door beyond would offer little resistance, but without my clothes where would I go?

Bowing my head and bracing myself, I squinted back the tears. As she whipped my ass some more I tried to detach myself from the moment, recalling the last trip I had taken with my previous girlfriend to the Smoky Mountains.

In my mind I tried to bring back ever detail of our little rental chalet with the round bed and heart-shaped whirlpool tub. The balcony overlooked the wooded mountainside and the tourist town of Gatlinburg below. Over those few days we only drove down in the evenings to dine at restaurants. The rest of the time we spent in bed, or in the tub, on the balcony, making love wherever and whenever we pleased.

How had that relationship gone bad? Pressured to marry and settle down, had it been too predictable or normal for my kinky desires? Was it worth abandoning to end up here in some shack taking a painful test administered by a beautiful but potentially dangerous woman?

If I passed the test and got Miss Julia into bed she probably wouldn't bother taking off her thigh high boots, and I tried to imagine what the soft leather would feel like with her legs wrapped around my waist as I got to bang her for the first time, convincing myself that it would be worth enduring the pain.

Miss Julia's riding crop landed a few sharp snaps on my tender shoulder blades, and one hit on the back of a thigh that almost made me lose my balance. Out of a corner of my eye I saw her riding crop land on the bed as if tossed carelessly to the side. Her spike heeled boots clicked on the plank floor and leather creaked as if she were pacing slowly. I was silently crying, and slightly trembling, and there was no way that she couldn't notice. Was the test over? Did I pass? I couldn't help thinking that she was simply taking a break. Maybe she would bind my wrists to some of the shelf brackets because I had moved around too much. Her wooden paddle was surely close at hand so maybe I still had to endure a number of painful swats, or get whipped with one of the many belts that hung close by on a makeshift rack assembled from scrap wood and mismatched screws.

Thinking of femdom porn I had looked at, the most brutal instrument of all seemed to be the cane. The slim bamboo wand that sliced through the air and left bright red stripes on a bare bottom and sometimes even broke the skin. It would make sense that Miss Julia would own such a thing, and I hated to think of one in her hand. If she did pull out a cane and only wanted to give my sore ass one stroke I would have to bolt out the front door. Running barefoot on the gravel road would be painless in comparison to what I had just survived.

"Turn around and get on your knees," she ordered, breaking the dreadful silence. I readily complied, the test hopefully over.

Miss Julia stood at the foot of the bed with her back turned to me, her ass just inches from my face. After a few moments she reached for the narrow zipper that ran up the backside of her skirt, and to my surprise she slowly lowered it. She let her mini skirt fall to the floor with a slight rustle of black fabric, where she stepped out of it and kicked it off to one side.

The pale skin of her perfectly shaped ass was enticingly framed by the rear straps of her garter belt, which was made of wide heavy looking cloth and had none of the usual lace trim. The stocking clips and strap adjustments were robust shiny chrome. Not the usual cheap lingerie garter belt, this one seemed like it was made for regular use, and it was easy to envision her wearing it under a conservative skirt to work.

The panties I had caught a glimpse of earlier were a thong, and a thin strip of black lace was firmly clenched between her butt cheeks. I had no idea if I had lost my erection during the painful whipping, but my cock was straining now, my scrotum feeling tight with denial.

"Kiss my ass," Miss Julia said quietly. While that phrase is normally an insult, coming from her lips I knew it was an order, and I willingly obeyed.

Using a combination of soft gentle kisses, and light nibbling ones that I might normally apply to a woman's neck or earlobes, I worshiped her sweet ass for what seemed like a long time. Listening to her slow deep breathing, I tried to gauge what she liked.

Then she reached behind her and grabbed a handful of my hair, positioning my nose right in the crack of her ass.

"Lick it," she commanded, spreading her legs a bit so that my nose was enveloped between her soft cheeks.

I'd never done such a thing before. Maybe under different circumstances I'd find such a task repulsive, but she had showered not long ago and smelled of soap and light perfume. Also, I didn't dare disobey her. That would call for a real punishment session, and right after my so-called test, I knew I wouldn't be able to handle it.

Starting as low as I could, I gave a slow continuous lick upwards to the waistband of her thong, the lace strip between her cheeks coarse on the tip of my tongue. After doing this a few times, I concentrated lower, where I knew her asshole was barely hidden by the fabric. I assumed she would tell me to do this soon enough, and while I was a bit unsure about it, I felt it best to make the move when I was ready instead of risking hesitating when given the order.

Miss Julia responded with a soft moan. Her high heels scraped on the floor as she spread her legs some more, then bent over the edge of her bed giving me better access. Reaching around and hooking an index finger under the thong's vertical strip of lace, she pulled it off to one side, fully exposing herself.

Sensing what she wanted, I gave a few tentative licks at her small puckered asshole and hearing her gasps and moans in response, I moved in more aggressively. There was no foul taste or odor as I might have guessed, still I couldn't help but thinking that what I was doing was nasty. At the same time I was more turned on than any time I had gone down on a woman in the usual way.

Soon she was breathing quickly, occasionally punctuated by low moans or hissing gasps. I felt a subtle rhythmic movement in her body and I realized that she was fingering herself. She probably had her whole hand down the front of her panties, pleasuring herself while I worshiped her asshole.

Sensing her tension building, I didn't let up, swirling around the small indentation, occasionally probing her with the tip of my tongue. She came with a series of hard stifled grunts. I tried to maintain contact while her hips bucked involuntarily, and then I slowed to light teasing licks as her spasms subsided. Her breathing was now loud slow exhales, like a steam locomotive throttling down as it pulls into a train station.