I met S., of all places, in the Ramrod on the evening before New Year's Eve. He was young, just barely old enough to be in the back room, but I could tell he was eager to learn and needed to feel powerful hands on him. At first, he stood trying to imitate the characteristic slouch of other leathermen in the back room, but he failed—his need was too raw, too close to the surface for him to be able to carry off "jaded." Then, I apparently caught his eye in my regulation 1" heeled (so unfair!) knee-high boots, midthigh-length leather skirt, and fitted bar vest that *mostly* hid the lacy brassiere underneath while ideally framing my generous cleavage—all in unrelenting black, of course.

 

Abandoning his absurd posturing, he starting to bounce near me, talking just a little too loudly with his friends about topics he thought I would find interesting but about which he had very little knowledge; it was endearing, in a puppyish way. Ah, fresh meat, desperate to be devoured!

 

However, I was out with my friend A., the only femme I have ever known who can march into the back room at the Ramrod in thigh-high boots and a short, brown velvet spaghetti-strap dress . . . and woe betide any young doorman who would dare try to stop her! She had history in that place for sure—was known for hiking her skirts in the old days and adding her golden stream to the trough. The men loved her, and through her I felt accepted as well, although I was relatively new to the Boston leather scene.

 

A. likened S. to a gnat, the way he kept buzzing around us . . . We both assumed he was interested in her, since she had such a strong dominant personality and was well known as a skilled bondage top. She would glare; he would retreat, but not for long. Eventually, she stepped into the bootblack's chair, running her long, freshly sharpened nails over his gaunt bare back to remind him that extra care was required.

 

As soon as he saw me leaning against the bar alone, to my surprise, he began sidling closer. I caught his eye, raised an eyebrow; he looked away. I kept looking at him until, inevitably, his gaze slid back and was snared by mine. I nodded, tapped my empty can of Red Bull, and looked pointedly at the bartender. Without waiting to make sure he got the message, I turned my back.

 

A few minutes later, there was a tap on my shoulder. I slowly turned to find him holding an open can of Red Bull.

 

"Er, miss, ma'am, w-w—"

 

"Who gave you permission to invade my personal space?"

 

Offering the drink, he stammered, "Er, sorry, I just wanted to, to—"

 

"No one with any sense accepts an open drink from a stranger in a bar, no matter how cute that stranger *thinks* he is. So, enjoy. I hear it gives you wings." There was much snickering from behind the bar as I started to turn away again.

 

"Have some pity on the boy; he's new to all of this. I think he just needs a firm . . . hand." The bartender always thought he was a laugh riot. Someday, he would be on his knees servicing *my* cock—but that night I had other fish to fry, as it were.

 

"New beverage. On your knees. Might as well begin memorizing my boots now."

 

Seconds later, there he was, as specified. I bade him hold the drink higher and with both hands, as I kicked his knees apart. His arms started to shake after only a few moments, but fortunately for him, I was thirsty, so I decided to let that go, for now.

 

"Open it." I flicked him on the forehead between the eyes. "Who told you to raise your head? Keep your eyes on my boots, little man."

 

He struggled to turn the can so that he could grip the tab, and finally managed to open it. I took the opened beverage from his trembling hands; fortunately it hadn't gotten *too* warm.

 

"Hands clasped, behind your head."

 

As I took a long draught of the sweet drink (liquefied Smarties, anyone?), I lifted my boot and brought the toe down on his crotch and felt around a bit. As I suspected, hard but small. Fortunately, I had no use for his equipment, as I had dildos in many sizes on display at home, but it was good that he was erect.

 

My friend A. finished out her time in the bootblack's chair while S. and I stayed at the bar—me leaning comfortably against it, him on his knees with my foot in his groin, getting flicked on the forehead every time he moved his hands or leaned too far forward or back. As she walked toward us, her boots gleaming in the dim light of the bar, I gave the bartender a card with my name and e-mail address on it, told S. to stay right where he was, and left with A. It was close to closing, and we never like to stay for the sidewalk sale.

 

The next day, I received an e-mail asking me to meet him at the bar again that night. I replied that I, clearly unlike him, had plans to spend an intimate evening with friends on New Year's Eve and had no intention of being in a public place. Also, what took him so long to write??

 

After a few e-mails were exchanged and his references were thoroughly checked, I agreed to allow him to make dinner for me. He claimed to be an accomplished cook—I should have known something was up by his use of the word "cook" rather than "chef." The food was palatable, but not particularly well presented or interestingly prepared. ::SIGH:: There was much work ahead.

 

Fortunately, the disappointing meal meant that a satisfying punishment could follow. He said he liked thud but feared single tails (although he hadn't ever experienced one). Thus, after he had removed the dishes, I grabbed him by the back of the neck, thrust him face-first against the wall, and once he had been suitably warmed up by very deep and somewhat painful massage, I began whipping him with my favorite toy, a four-foot sled-dog whip. The initial crack (necessary to get the kinks out of the whip after it had been coiled in my toy bag) made him start and tremble deliciously. I bade him stand very still, not to move a muscle, that this was his punishment for disappointing me. "Yes, ma'am," he whispered.

 

Although I plied the whip for more than an hour, I never really went beyond the level of butterfly kisses much, and only left a few pink stripes on his back (it was his first time; I was never so generous again, and he became a total whip slut over the months).

 

Since he had pleased me by taking his punishment well, I permitted him to place a glove on my right hand and lube it nicely once I was comfortably settled on his bed with a protective cloth over my skirt. I then had him position himself ass up on my legs, with his head pointing toward my feet.

 

I fed three fingers of my right hand into his ass as his cock grew against my legs. Once my fingers were inside, we began the game—I spank each ass cheek with my left hand as he counts, and then I fuck his ass the same number of times . . . first 10 of each, then 20, then 30, et cetera, until he came on my lap. After he licked and sucked his cum from the cloth, he removed and disposed of the glove and kissed my feet.

 

An auspicious start, although he never really learned to prepare meals to my satisfaction—perhaps he enjoyed the punishment too much?