No stranger to trouble, I had been to Ms. Robertson’s office several times in the past. In fact, at the time of this story, I was on something of a probationary period for my previous transgressions. Despite my “bad boy” attitude, she always had a way of making me feel uncomfortable under scrutiny. At about 6′ tall and I’d guess 170-180 pounds, she was a fairly imposing figure. It would be wrong to call her “heavy”, as her body was well toned even if a bit large in proportion. She favored knee-length skirts almost exclusively, and often wore sheer nylons whether it was hot or cold outside. Being a foot hound at heart, I had noticed her impeccable taste in heels and wondered from time to time just what she was hiding within them.
My mind rapidly shifted gears as out of the corner of my eye, I watched Ms. Robertson swing her feet up and place them on the corner of her desk. In the blink of an eye, my raging hormones had overtaken my apprehension. Because she was so focused on her phone call, I was afforded the perfect opportunity to get a better look.
As if on cue, she began to dangle a shoe from the toes of one foot while pointing and flexing the other, then alternate to the other foot and repeat the practice. I felt myself begin to swell and throb within the confines of my jeans.
The angle I had was frustrating, but it was clear she had relatively high arches and supple heels, with a surprisingly dainty ankle. My eyes wandered a path up her powerful calves and found her skirt had hiked up a little bit, giving me a maddeningly arousing glance of her well toned thigh. I couldn’t help but to picture those legs wrapped around my head, and to wonder just what type of sounds I could get Ms. Robertson to make.
Without warning, one of her shoes slipped off of her foot and hit the ground with a loud clatter. I swallowed hard as I got a momentary glimpse of her foot– well proportioned, long supple toes, softly wrinkled soles partially obscured by the seam of her nylons. My heart sank as she removed her feet from the desk in what I thought was an effort to retrieve the fallen shoe, but it fluttered up into my throat as she returned them to their place after dropping the second pump alongside the first.
As she fanned her toes out, I found myself leaning a bit to get a better view. I could tell now that her nails were painted the same deep red as her fingers, and from what I could see, she was a woman who took good care of her tootsies. I watched as she rubbed them against each other, flexing and pointing and spreading her toes to loosen them up after their long day within the pointed tips of her heels. Her nylons sang out a sensual tune as she ran one sole half way up her shin, and slowly back down to the ankle.
I was enthralled with my own private foot show, and wiggled in my seat some to free up my now fully erect member. My vision was tunneled on her large, sensual feet, my palms were sweating even as I rubbed them nervously on the legs of my pants, and I could hear my pulse rushing in my eardrums…
And nothing else.
In that flash of realization, I tore my eyes away from her peds and threw them quickly to her face. It hit me then that I had no clue how long she had been off the phone– 10 seconds, 10 minutes? I could only hope she hadn’t noticed my ogling, and searched her expression for clues.
She looked curious, one eyebrow raised and her neck craned as if she were studying my reactions like one might watch an animal in a zoo. And when it was clear that I felt as though my hand had been caught in the cookie jar… she smiled, a cheshire grin that spread slowly from ear to ear. I felt a strange new emotion then, one that had previously been very rare to me. My ears burned hot with embarrassment.
We sat in booming silence for what seemed like an hour, and I did my best not to meet her gaze. Incredibly, I could not stop stealing glances at her feet, and for some odd reason, she had not pulled them from the desk. I began to wonder if she enjoyed my shame or if perhaps I was lucky enough that she didn’t understand my fascination. Finally, she moved them back beneath her desk and I could hear her replacing the blue pumps.
“Do you like my shoes?”
I froze up for a second before trying to don a look of confusion, as if the question didn’t make any sense.
“I saw you looking at them. What do you think?”
“They’re… nice…” I stammered meekly as my throat instantly went dry.
“Nice!” she chuckled, suddenly returning them to their rest position on the desk. “They better be, they cost a fortune! I just got them this weekend. But as pretty as they are… they aren’t very comfortable.”
Slowly, she hooked a finger beneath the surface and slid the leather pump off of her heel and then away from her toes. I was again treated to a mini-show as she worked her digits around to loosen them up.
“I hope I can break them in some,” she continued, flicking the other shoe off and caressing the top of her left foot with the wide sole of the right. “I’d like to be able to wear them regularly. It may be these stockings that are causing the problem– they’re new as well.”
I folded my hands in my lap then to keep them from trembling, as well as to hide the tent my raging hardon was creating in my jeans. I couldn’t tell if Ms. Robertson was teasing me, testing me or just making idle conversation– and honestly, I didn’t care. Although I was almost shaking with nervousness, the longer I could lay eyes on her exposed feet, the better.
“And the stockings?” she asked softly, angling her legs so I could get a full view of the bottom of her soles. “What do you think of them?”
“They’re amazing!” I blurted, so distracted by my desire that I couldn’t even begin to hide the truth.
She laughed then, throwing her head back in amusement. I knew then for sure that she was enjoying this treatment, although I still couldn’t say what motivations she had for administering it. I was totally enthralled with this woman, over twice my age, and would do anything she told me to so long as my eyes could find her shapely peds.
“You know, Mr. Black– I can’t promise it will get you out of trouble… But it certainly wouldn’t hurt your case if you agreed to rub my feet.”
I couldn’t believe my ears. At this point in time, my sexual arousal was obvious. Not only was Ms. Robertson using her wiles to taunt me, she was basically demanding that I lay my hands on the source of my desire as well. My head swam so violently that I felt a bit queasy, but I managed to nod my consent just the same.
“Great! I could really use a massage. Pull your chair around here and we’ll see what you can do.”
I jumped from my seat so quickly that I nearly toppled it, and fumbled like a calf on weak legs as I drug the heavy thing across the office. I could feel her gaze boring into me as I arranged the chair, but dared not meet it as I dropped down again onto the cushion. As I settled in, she raised both feet up and placed them gently in my lap, scant inches from my rapidly pulsing dick.
“Now don’t be shy– I’m not ticklish!” she joked. “Start with the right one.”
Having had a foot fetish for as long as I could remember, I had taken every opportunity to practice my massage technique. Without hesitation, I gripped the proffered appendage firmly above the ankle and began to knead the supple skin. The flesh colored stockings, though sheer and new, were very soft and I took care not to bunch them up against her soles. I worked first on the pad of her foot, paying specific attention around the ball and at the base of her toes. As I felt the sinew begin to relax, I moved slowly up her arch towards the heel. Indeed, as I had noticed from afar, Ms. Robertson had obviously treated her feet well. There were no callouses or rough skin to speak of, and no discolored or dry patches in any of the typical places.
“Mmm, that’s nice,” she purred, getting more comfortable in her office chair as my fingers continued to work their magic. “You’re pretty good at this.”
I watched as her eyes closed and her head rolled slightly back, an answer to my firm ministrations to the tense regions of her foot. Her free leg curled a little bit, and I felt the full surface of her sole press against my thigh. Having them in my hands, I marveled at how delicate her peds were despite their size– easily a 10, but with the curves and contours of a much daintier woman.
After a few more seconds, she pulled the foot out of my hands and sat up a bit more. “Oh, you’re not finished!” she promised as my face took on a disappointed look. “My leg is just getting tired. Sit on the floor for me and it’ll be a lot more comfortable.”
I dropped to my backside and slid across the floor until I contacted the base of her chair. She lowered her right foot and placed it on my knee, then offered the left for its turn in my hands. I went through the same routine that seemed to please her so much before, and was rewarded with he sensation of her toes dancing and flexing against my leg, her sole gliding slowly up and down as she groaned softly in pure physical pleasure.
From this new angle, I realized I could see even more of her muscular legs than before and cautiously let my eyes walk up from the top of her foot. Slowly, one maddening inch at a time, I watched her legs part as she relaxed more and more until I could see the very top of her stockings, and the bare leg beyond. It took all of my will power to not reach out and touch that tender flesh, but I pressed on with the massage.
“One second,” she said, abruptly standing and heading out from behind the desk. Although I couldn’t see over the top of the tall wooden surface, I heard a distinct *click* as she locked the door, and managed a wan smile when she returned and retook her seat. “It wouldn’t look very good if someone walked in on us like this.”
She returned the foot to my hands, but this time, placed its partner firmly on my chest and curled her toes around my collar bone. Although I could no longer see the full length of her legs in this position, my cock jumped nonetheless as her foot explored ever more parts of my body. As I continued to rub, I lowered my face closer to her foot and pretended to accidentally brush my cheek across her ankle.
“They’re soft, aren’t they?” she responded. “They’re pricey, but they feel soooo good… I won’t wear any other brand anymore. See how nice?”
She lifted her foot from my shoulder and began to run it slowly up my cheek, first with just the very edge of her instep. After a couple of passes, I instinctively cocked my head in that direction, exposing more surface area. In turn, she angled her foot so that the silky surface of her sole was pressed fully into my face, caressing slowly as the nylon whispered against my skin. She held it in place for a moment, curling her toes over the bridge of my nose as my eyes closed in pure ecstasy. When I opened them again, our eyes met and she ran her tongue quickly around her lips.
“Oh, I hope they don’t smell!” she said playfully, although she clearly wasn’t concerned. “They don’t, do they?”
I shook my head slowly as she continued to drag her foot along my face, now working across my forehead and then back underneath my chin. Totally lost in the moment, and having all but stopped with the massage, I dropped a hand to my crotch and adjusted my dick, which was pressing so painfully against my pants that it was starting to become a health risk.
“Are you sure?” she purred, adding the second sole to the mix and pressing both of the soft surfaces directly into my nostrils. “They don’t smell at all? Or you LIKE how they smell?”
I didn’t like it– I loved it! They were only soft with a slight perspiration, but combined with the nylon and the leather, her feet gave off a sweet and subtle musk that introduced me in that moment to a whole new aspect of my fetish. The full implication of what I was doing hit me then– kneeling at the feet of an authority figure, hornier than I’d ever been before while she too found pleasure in using my face as a footstool.
“Kiss them for me, Mr. Black. I want to feel that infamous mouth on my feet,” she instructed softly, hovering the balls of both feet directly over my lips.
I reached out to take them and was met with a clucking of her tongue. “No hands– I’ll bring them to you.”
Slowly, she lowered one foot until it pressed gently against my chin. I craned my neck up and planted a soft kiss on the ball, right along the seam of her stockings. She cooed and pressed it firmly against my lips, moving it slowly up and down until I had covered everything from the bottom of her toes to the back of her heel. She then switched feet and repeated the process.
As more time passed, I settled down a bit and did my best to enjoy every second spent beneath her feet. As my heart slowed some, I became aware of a soft rustling sound that had escaped me up until that point. Although curious, I continued my work on her soles, now curling my lips gentle against her flesh and occasionally flicking my tongue against the surface of her nylons. I longed to reach down and give my dick some attention, but held off for fear of going too far.
As if she were reading my thoughts, Ms. Robertson lowered one of her feet to my lap and rested her toes against my pulsating meat. “Hmm, you’re enjoying this as much as I am,” she said as she began to slowly move up and down against the bottom of my shaft. I could feel my pre-cum now, cold and wet where it had spread across the front of my boxers.
With a less obscured view, I realized then that source of the mysterious sound was her hand between her legs, tracing a steady path up and down the face of her panty-clad sex. With her skirt now raised almost all the way past her waist, I could clearly see the sensual lines of her hips, covered though they were by her tan lace panties. Her eyes rolled around slightly in her head as she continued to play with herself, and I felt her toes curl simultaneously against my lips and around the tip of my dick.
“Mmmm, let’s get these stockings off. I want to feel that hot mouth wrapped around my toes.” She pressed the ball of her foot against my forehead and began to slowly take down the nylons, her eyes locked sensually with mine. Once removed, she placed them gently aside and sank deeper still into her chair, legs now splayed almost as wide as they would go. Her mound pressed outward against the satin material of her panties and I could trace the outline clearly with my eyes, even as she returned her fingertips to her clit.
In a flash, she had her toes in my mouth and I suckled them tenderly as I might other sensitive parts of her anatomy. With renewed determination, I threaded my tongue between each individual digit, swirled it around and traced the contours of the ball of her foot. When she withdrew it for a moment to hover it over my mouth, I instinctively stuck my tongue out and was thrilled as she slowly ran her sole over its surface. There too I closed my lips, dragging my tongue along between them and flicking it teasingly against her sensitive flesh. All the while, she continued to increase the speed of the hand between her legs and that of the foot pressed against my cock. We were both spiraling quickly out of control.
She began to switch feet periodically, and based on the sound of her moans, I figured out what she seemed to like the best. The toe next to her pinky got express attention from that point onward, and I was careful to run my tongue as firmly as possible against the base of her toes when she placed them against my lips. For my efforts, I was rewarded by seeing her hand disappear beneath the waistband of the soft satin panties and hear the sloppy wet sound it made against her pussy.
“Fuck this,” she said suddenly, pressing both feet firmly against my face. I heard her shifting in the chair and felt a lot of her weight supported against my cheeks for a moment, then heard her press back down against the cushion. The silky material of her panties brushed against my forehead and I realized she had just removed them.
“Help me get them off,” she commanded in a hoarse whisper, pressing them firmly over my face and against my mouth.
I could feel the warmth that had radiated from her mound into the material, as well as the slippery wetness she had leaked into them. I gingerly closed my teeth around one of the seams and eased them over and off of her feet. No sooner did they drop than she pressed her toes back into my mouth and renewed the efforts between her thighs. I now had a full view of her fingers as they worked quick little circles over her clit, occasionally alternating to a vertical motion that ran the full length of her slit.
My own fun spot had been totally neglected as she slipped deeper into her throes, but I was unconcerned at that pont with everything other than giving her pleasure. Ms. Robertson was using me to make herself feel good, and that thought alone had me on the verge of my own orgasm. I would do or give anything to make her cum– a sex toy for the Dean of Students.
She hooked a foot behind my head then and drew me violently towards her crotch, reaching out to take hold of my head and guide it where she wanted it to go. Draping her legs over the arms of the chair and around my shoulders, she pressed the soles of her feet into my back and brought her hips up to meet my face.
I felt her toes curl against my skin as I passed my tongue between her labia for the first time, and felt her shiver slightly as I flicked it in a firm circle over her clit. Her pussy was soaking wet, like a drenched fold of silk that someone had warmed in the oven. The juices ran down her thighs so that I could feel it against my cheeks, and trickled down my chin where it began to pool against the chair in thin puddles.
Focused now, I gently teased her hungry sex for several seconds before she added a second hand to he back of my head and pressed my face more firmly into place. “Harder,” she cooed, angling her hips upward so that I could reach as deeply as possible with my eager tongue.
I began to work her pussy in earnest then, drawing deep circles with the meat of my tongue against the flesh covering her clit, driving the tip into her depths and tracing it all the way up her slit to ease past the hood and give the bare nub itself a little flick. This woman already knew I liked to go down– now I would show her that it was a mutually beneficial arrangement.
Looking up, I could barely see her face over the folds of her skirt, but that narrow glimpse was more than enough. Her head was thrown back, mouth agape, eyes going wide for a few moments before slamming shut, and animal noises climbing out of her throat. Her breathing was short and quick, her hips beginning to move aggressively against my face, and every now and again she gave a violent buck and let out a sharp squeal. I was worried in the back of my mind that we would be discovered, but quickly decided that I really didn’t give a fuck.
She pushed me away suddenly and got quickly to her feet. On shaky legs, she all but skipped across the room, half dragging me by the shirt as we headed towards the little love seat on the far wall. With fingers half-numb with raw ecstasy, she fumbled with my belt and the button on my jeans, then quickly tore them and my boxers down from my hips in one swift tug. I kicked my shoes off as she fell to her knees, fully stripped me of the jeans, and took me into her eager mouth.
“Fuuuck,” I muttered as I felt her full lips close around the tip of my cock and slowly work their way down to the base. I’m not porn star hung by any means, but definitely endowed more generously than the average person. Still, Ms. Robertson didn’t struggle at all to get the vast majority of my length down her throat.
Her tongue pressed firmly against the sensitive underside of my dick with each pass, and she swirled it around the head from time to time on the upstroke. Unable to stand, I collapsed heavily onto the love seat as this older woman worked my meat with her steamy mouth. I noticed then that she had returned her hand to her own sex, and shivered each time the vibrations of her moaning passed through her lips and up the sides of my cock.
She stood up abruptly and pushed all but the plushest pillow from the love seat. “Upside down,” she whispered, setting it up at the edge as I swung my legs over the back and positioned my head as she wanted it.
Turning around, she placed her muscular thighs on either side of my head and slowly lowered herself into place, snatching the chair that I had once occupied to brace some of her weight against. My tongue was out and ready as her sopping wet opening pressed firmly into place, although this time, no movement was needed. Ms. Robertson settled herself onto my face and began to work her pussy up and down against my tongue. As her pace began to quicken, she twisted slightly from side to side, rubbing herself in a circular motion as she began to try in earnest to cum.
“Work your dick for me, baby,” she groaned– an instruction I was all too happy to comply with. I knew that her own shuddering orgasm would bring me to my peak, and I paced myself accordingly.
The pillow and love seat cushions began to sink as she rested more and more of her weight on my face, and I could hear the chair legs scraping against the carpet as the speed and range of her bucking hips increased. I caught brief gasps of air through my nose and cast my eyes upward, watching my disciplinarian use my tongue as her personal play thing. She lowered a hand to my forehead for balance and pumped her hips so hard that I could feel the friction building between her inner thighs and my cheeks.
“Oh fuck, oh fuck, oh fuck,” she began to say, a never ending and ever quickening litany indicating her rapidly approaching climax.
The love seat was shifting now with each powerful thrust, and it took all of my effort to keep my tongue from folding up against the silky walls of her wide open pussy. The once consistent humping turned into an erratic, jerky pattern that seemed to crest the speed of light, and I felt her fingers curl in my hair. She lifted her feet off the ground and focused almost all of her weight on the spot where her clit met my tongue, grinding as if she intended to scour the flesh from my face. I felt the hood retract fully from her clit, and a sudden rush of fluid spilled into my mouth.
“Unnnggggh!” she almost screamed, sitting bolt upright for a split second before pumping and gyrating her hips in a dizzyingly fast pattern. Her entire body quivered with the force of the orgasm, the lightning bolts of pleasure forcing uncontrollable twitches throughout her body. She arched her back for a second, hunched over and pumped her hips for all she was worth, then repeated the same process several times.
I lost control then as well, arching my hips upward as my own climax raced up the length of my shaft and exploded in torrential gouts over my stomach and onto the small of her back. My arousal was so intense and prolonged that my dick seemed to emit and endless stream of milky white cum. Every time I thought it was about to end, the sensation only intensified. It continued for so long that my abs began to cramp.
Ms. Robertson was panting heavily and still working her hips, having returned to a more steady (although still fast) pace. Slowly, her grinding began to lessen until only a rare and unpredictable twitch sent her moving against my face. We began to recover from the effects of such an intense experience, although the memory of the climax made it feel at times like we were still cumming. A full minute passed, then two, and finally she lifted her weight from me and began to stand up. I dared not move, for fear of spilling the massive load I’d expelled all over her office.
Quietly, she crossed to her desk and pulled several tissues from a box near the center. After cleaning herself of both of our juices, she carried the box over to me and dropped it in my hands.
“I hope you’ve got another one in you,” she said sternly. “Now that we’ve got that thing under control, I’m going to see how long I can ride it.”
As I began to wipe myself off, I thought there was no way in Hell I had any more left after that, the hardest cum of my life. I sat up and deposited the trash in the waste bin, just in time to see her crossing back over to me, now fully nude but with her stockings in hand.
“This time,” she said as she guided me back into position on the love seat and began to straddle my head, “I’m going to keep the stockings on.”
Once she had settled back into place, her shifting weight and the slinky sound of the nylons let me know she was pulling them back over those sultry feet, up those powerful calves and to the top of her shapely thighs. My cock had not yet emptied itself of blood, but I felt it stir anew.
“Well?” she said. “What are you waiting for?”
I slowly eased my tongue back into her mound and ran it firmly up the face of her still-swollen clit.
“Mmm,” she purred. “That’s a good boy.”
