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What’s The Worst That Can Happen F/M Intense with Sexual Content

Feather777

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What’s the Worst That Can Happen

Chapter 1 – What’s the Worst That Can Happen
What’s the worst that can happen? A question I wondered to myself as I trolled the personals section of the TMF website. You see, I had been into tickling for as long as I can remember. From playful tickling, to erotic tickling as a form of foreplay; I enjoyed it all. As a tickler, as a ticklee; it made no difference to me, although I found myself more often than not as a tickler of whoever I was dating at the time. I wasn’t sure who or what I was searching for, but I figured what did I have to lose? What was the worst that can happen? It was at that moment I stumbled upon a personal listing from a woman who identified herself as Anne.

The title of the listing intrigued me; “Dominant Female Tickler seeks Strong, Masculine, Male Ticklee for Prolonged Tickle Torture”. I was never really a ticklee before, but I knew from my previous relationships that I was ticklish. As I sat there staring at the posting, I performed a self-assessment to see if I fit the criteria. I was athletic, clean-cut, successful in my chosen career, 34 years old, and reasonably good-looking; at least none of my previous ex-girlfriends ever complained. I decided to send Anne a pm never really expecting a response. To my surprise, she responded.
Anne and I messaged each other back and forth for several days, weeks even, exchanging pictures, and other pertinent details. Anne seemed, as far as I could tell, a fun, free-spirited young woman. She disclosed that she was 29, a Graduate Student studying Occupational Therapy at Penn State University in State College, PA. She was athletic as well and loved to hike and swim. We really didn’t discuss our fetishes. They were sort of the pink elephant in the room; however, we knew we enjoyed the same things by virtue of where and how we met. She did disclose that she was a tickler and a ticklee, but much preferred to be a tickler. After several weeks, we decided to meet in State College while I was away for the weekend on business.
Anne had agreed to pay for the hotel room, not because I refused, but because she had a trove of points that were going to expire. When I arrived, I was wearing my trademark dark blue jeans, gray t-shirt, and well-worn, but comfortable black sneakers. I searched for a few minutes but found our room with relative ease. It was, to my surprise, a one-bedroom suite replete with a living room, kitchenette, bathroom, and bedroom with a king-sized bed; at least that’s what the hotel attendant told me when I presented her with our room number. I knocked on the door and Anne promptly answered. She was wearing blue jeans, a dark-colored t-shirt, and was barefoot. She was 5’2”-5’3”, dark brunette hair, with hazel eyes, and was athletic; that much I could tell. She invited me in, and we made our way to the living room.
Anne offered me a glass of wine, which I accepted, and we began exchanging pleasantries and conversing. What struck me as odd was how normal everything was to that point. There we were discussing everything from the weather to our professions and schooling, to what we like to do in the gym, and everything in between. Anne was truly an amazing woman and a woman I would have loved to have met in college. She was fun-loving, adventurous, and truly a lovely human being. Our conversation lasted for about an hour but seemed to last much longer as talking with her was effortless. Anne motioned to the bedroom, and we both got up and proceeded there in earnest.
The bedroom was dark. The blinds had been drawn closed and the lamp was dimmed. I could see there were things on the counter of the hutch; however, whatever they were was obscured by a sheet. The bed had been modified/prepared as well. There had been a rubber sport sheet laid on top of the sheets and what appeared to be restraints at each of the 4 corners. We had never really discussed restraints, but I had always assumed they would be involved. It was at that moment that Anne spoke. “You can throw your clothes on the chair. Oh, and no shoes or socks on the bed”. I began to disrobe, and, in a few seconds, I was climbing on the bed in my boxer briefs and ankle socks. Anne approached the bed and began adjusting the restraints. First were my wrists, and then my ankles. Upon finishing my ankle cuffs, Anne said “ I told you shoes and socks” and slipped the socks from my feet, but not before she allowed a single, solitary finger to trace the sole of my left foot eliciting a muted laugh and causing my foot to jerk away. Anne then placed a leather bag on each of my hands further limiting my movement. Anne walked over to the hutch, and returned with a blindfold, some black tape, and something else I couldn’t quite see from my vantage point. She quickly applied the blindfold, tapped my mouth shut, and did something I was not expecting. She cut away my boxer briefs, grabbed my cock and scrotum, and applied a tight, rubber, cock ring; the tightest I had ever felt. Within a few minutes of entering the bedroom, I went from my normal self, to being the most vulnerable, helpless I had ever been, and that was Anne’s end goal; to have me completely exposed, vulnerable, and at her mercy.

Chapter 2 – All Tied Up and Nowhere to Go / The Test
I couldn’t see anything, and I could barely move. My movement was restricted to lifting my head and moving my hands and feet in their respective cuffs. The air had been turned on; that much I could tell by the movement of the air across my freshly bared skin. I could also hear that Anne had temporarily left the bedroom by the sound that the door made when it opened and closed. She had returned, as now I could smell her perfume and hear her footsteps traverse the floor. Anne finally spoke after several minutes of painstakingly quiet nothingness. This time her words seemed different, more cold, more direct, less empathetic, and far more sadistic. “Mark, I am going to torture you today, tonight, and for as long as I want. Your pleasure is irrelevant to me, and I will tease and torture every square inch of your body from head, to your cute ticklish toes. Your body is mine. I will decide if, and when, I allow you to orgasm, and when you do, you will not enjoy it”.
I was truly scared. But it was an odd combination of feelings. I was scared, excited, nervous, and truth be told, I really didn’t know what to expect. Anne spoke again, “I have many fetishes, but my three favorites are, and in no particular order: tickling strong, masculine men, edging and milking them, and reducing them into a quivering, begging mess”. I was completely shocked. That was the paradox of Anne. She was quiet, reserved, and angelic and at the same time devious and sadistic. She had done this before as I had come to find out. She knew what she was doing. She was a painter of sorts and I was her blank canvas; and she was about to paint her masterpiece.
The room fell silent again. I could only surmise that Anne was still in the bedroom with me as I did not hear the door open or close. It was at that moment I felt something, almost imperceptible at first. Light and wispy, it was a long feather. Slowly, methodically, she made it dance across my ears and nose, down the nape of my neck, and across my chest. She spent a few seconds twirling it against my nipples and transitioned to my armpits where she twirled it in earnest. You see, Anne was making mental notes. If I was feather ticklish in certain areas, then those areas would be susceptible to much, much worse as I would later find out. She slowly made her way down the flanks of my sides to my stomach where she twirled the feather in my belly button as my body tried to shift away but couldn’t. She then dragged it across my waist, and feather tickled my cock and groin for what seemed like an eternity. She had me throbbing in no time; desperate for more attention, but none would ever come. She gave my balls a quick, playful smack, before she moved down my inner thighs. I then felt the feather move slowly up the sole of my left foot and across and in between my toes. My foot tried to kick it away but couldn’t. She then moved to my right foot as I involuntarily pulled against the restraints. She must have been pleased by the results of the test because I heard her say under her breath, “how cute, his feet are feather ticklish”. Anne had completed her test. She now had an idea of where I was most vulnerable. My torture would be forthcoming.

Chapter 3 – The Pits of Despair
For the moment, the room was still; quiet, ominous, foreboding even. I was still very much erect, but slowly I was becoming more flaccid; my breathing beginning to stabilize. I knew more was to come, but for the moment it seemed that I was afforded a few seconds of respite. The few seconds didn’t last long as I soon felt Anne climb onto the bed with me, and on top of me, straddling my waist facing me. I could tell her direction because I could feel her cold toes against my thighs. And then it started.
I felt her nails against my skin. She lightly teased my neck with her right hand and feather tickled my nipples with her left hand. Her weight in combination with the sport sheet kept me firmly in place. It didn’t really tickle yet; more annoying than anything else, but the constant nipple tickling made me rock hard. I was throbbing again. Anne discarded the feather, reached back, and began to stroke me off with her left hand. It felt so good. But then I felt something else. Anne began tickling my right armpit with her free hand. The combination was almost unbearable. She slowed her stroking, occasionally teasing the head, but increased the tickling under my arm. I tried to move but couldn’t. My hips were gyrating and thrusting beneath her weight. The stroking was driving me insane; not enough to get me off, but more than enough to keep me erect and aching for relief. She was now playing and twirling with my armpit hair and dragging her nails up and down my right side. I was laughing into my gag now and begging for it to stop; she couldn’t hear me and wouldn’t even if she did. She was an expert, a modern-day Marque de Sade.
She stopped the stroking and began attacking both armpits now. Her touch was light, but deliberate. Her nails expertly hit their targets. She was enjoying my suffering. That much I could tell; she was soaking wet. She never said a word. Anne was meticulous in my suffering. No inch of my armpits was left untouched. She just continued tickling, occasionally reaching back, and teasing my shaft. I pulled at the restraints, shifted left and right as much as I could, but it was no use; I was trapped. Anne must have applied some baby oil to her fingertips because I could feel the slippery substance against my sensitive armpits. She was also teasing my nipples now and alternating back and forth. The constant edging, the constant nipple play, the constant tickling, it was almost too much to take. But Anne new my limits, probably better than I did. She knew when to back off, or alternate, or stop altogether. And she did.

Chapter 4 – On the Edge
Anne repositioned herself, this time facing away from me. I could feel her toes near my armpits. She then, without warning, attacked my waist with both hands. Kneading my hips and teasing the sensitive area beneath my belly button. My hips thrashed wildly as I tried to throw her off but again it was no use. I laughed and laughed and laughed as she continued her assault. After a few minutes she stopped. And then I felt it. A feather running up my groin. Dancing over my balls and up and down my shaft. I didn’t know my cock was ticklish, but the sensations were driving me mad. She alternated speeds, changed directions, changed pressure, and occasionally would hold my manhood still so she could exact her torture.
​She discarded the feather in favor of her lubed fingers. She teased the head and shaft and tickled my balls for what seemed like an eternity. I was desperate for release. My balls were blue and ached. My cock was swollen and red. Anne began stroking. Faster, and faster, and faster yet. My hips thrusted upward. Her body on top of mine. It felt so good. All the teasing, all the edging, was soon coming to a dramatic conclusion. I was so close. But then, without warning, Anne just – well just stopped.
​I moaned into my gag for release. My cock soaked with lube and precum. My body soaked with sweat. I was a desperate, broken man. Broken by a woman’s touch. My cock throbbed against the cool air of the air conditioning unit. I then felt Anne’s hand again. This time, she applied yet another cock ring; this one at the base of the head near the top of the shaft. After a few seconds of adjusting, it was in its place. Anne then turned on the vibrations. Again, not enough to get me off but more than enough to keep me rock hard and longing for release. Anne then got off my body and lowered herself off the bed. She then spoke in a calm, matter-of-fact demeanor “remember I told you that this is about my pleasure, not yours”. I moaned again, but Anne didn’t care. She then said, “I told you no shoes or socks on the bed and you disobeyed me”, “now, you are being punished for your transgression”. “Speaking of socks”.

Chapter 5 – Agony of The Feet
The room fell silent again except for the constant buzzing of the vibrator. I could hear Anne in the distance collecting items from the hutch. I then heard a chair being slid across the carpeted floor. Anne finally spoke, “Of all the areas I enjoy tickling, I love tickling a man’s cock and feet the most. His cock because of how desperate for relief he becomes. His feet because regardless of how big and strong he is, I can break him down and turn him into a quivering mess just by torturing his soles. I’m going to uncuff your ankles and reposition your feet. If you move, or kick, I’ll turn up the vibrator and leave you like that for a while so you can reflect on your actions”. To be fair, I was too exhausted to move. I just complied; resistance was futile. Anne repositioned my feet together at the foot of the bed where they were slid into cuffs and fastened tightly to a strap beneath the mattress. She then placed an elastic strap just above my knees and a heavy zip tie around my ankles. After a few more adjustments, she was ready to begin.
I didn’t have to wait long. I felt an all-too-familiar feeling of a stiff feather being drawn lazily up the sole of my left foot, and then my right foot; over and over and over again, alternating speed and pressure. Once Anne reached my toes, my laughing picked up dramatically. She was pleased. I could only imagine Anne sitting at the foot of the bed, in the large, over-stuffed armchair ubiquitous to all hotel rooms, eye-level to two very bare, ticklish feet, feather tickling them, and laughing at my suffering. My feet darted away as much as possible, but it was of no use. Anne must have become annoyed with all the movement because she discarded the feather, tied my big toes together, and then bent my feet back and tied them off of the zip tie forcing my feet into a taut, hyper-flexed position exposing my soles. Anne said, “that’s much better. When tickling feet, you want as little movement as possible”.
I then felt the feather again, this time though in an entirely different way. You see as most ticklees know, and as I soon found out, the quill of the feather is the business end. Anne started from my heels, tracing a path up my arches, all the way to just beneath my toes. I was laughing, harder than I had laughed the entire time. She tickled beneath my toes, between my toes, and each individual toe pad. At one point, I could swear I heard her laugh at my suffering. I was moving as much as I could, which wasn’t much. My feet twisted in their bindings, but no relief was found. All I could do was laugh. All the while that damn vibrator kept me on edge. After 15 minutes or so, Anne stopped. I heard the pop of a lid or cap, and then felt baby oil being applied liberally to my feet. She rubbed it deep into my soles and toes. It would have felt great if not for the fact that she also increased the speed and intensity of the vibrator. Still not enough to get me off but more than enough to keep me hard as a rock and desperate for relief. My balls were blue and sore to the touch. My cock throbbing and red from the hours of teasing and torment. I then heard a sound, a sound I immediately recognized from a different context; the sound of a highspeed, vibrating toothbrush.
Within seconds of hearing it, I felt it, and I damn near hit the ceiling if I wasn’t restrained. I laughed, and laughed, and begged for the tickling to stop into my gag. I thrashed about but didn’t move and inch. I tried to move my feet away but couldn’t evade that damn toothbrush. Anne was an expert at her craft, destroying ticklish men. She focused on the desperately ticklish toe beds; allowing the toothbrush to linger there for several minutes. She also added a second toothbrush at some point; it was all a blur to me. She tickled each toe, toe pad, and toe stem. The louder I laughed, the more intensity she attacked my feet. She also increased the speed and intensity of the vibrator. I was almost there. So close but not close enough. I tried to shake the vibrator off to no avail. I was desperate. Desperate for the tickling to stop. Desperate for relief. And then, without warning, the tickling stopped.
I could feel Anne massaging and kneading my feet again. She calmly said, “You can’t just keep tickling feet, you have to back off a bit, so they regain their sensitivity”. She then reapplied more oil. Anne had to know that our time together was coming to an end, or she just took mercy on me, or a combination of both, because she increased the speed and intensity of the vibrator to its maximum setting. Now I was close. I could feel that all-too-familiar feeling building deep inside of me. My hips started to thrust upward. My toes tried to curl against the bindings. This was it. After hours of teasing and edging, I was finally going to get my release. And just at the precipice of orgasm, Anne said, “my pleasure, not yours. You are not going to enjoy this”, and she began to scrub the soles of my feet with the Widow maker; a large hairbrush with several hundred bristles each coated with a plastic nub. I laughed and screamed as she tickled me through orgasm. I had never felt anything like that before. I think I was even more hyper-sensitive after orgasm because it tickled so much worse. The combination of the tickling and the vibrator after orgasm was just too much; I must have blacked out for a few seconds.

Chapter 6 – The Climax / Finale
The next thing I felt was Anne’s empathetic hand cleaning me up. I was still restrained, blindfolded, and gagged, but the vibrating cock ring was removed. Anne had a damp washcloth which she had applied to my groin and midsection. I was still soaked with sweat, my hair matted down to my forehead, my armpits, and feet slick with oil. I could hear Anne fumbling with something cumbersome; something heavy. I then felt something heavy being placed on the bed near my waist. After a few minutes, Anne spoke, “Are you familiar with a Venus Milker”? I shook my head indicating no. She said, “it’s for men who can’t get off”. I was still confused. Anne said, “you see, you came without my approval so know you will be punished”. Punished?! How much more can I be punished I thought to myself. I had been edged and teased for hours, exhausted from endless tickling. I tried to pick myself up but couldn’t. I tired to speak into my gag, but nothing came out. I then felt Anne’s lubed hand gently stroking me again. Alternating speed and pressure. Just enough to get me rock hard again. She then stopped. I felt something being slipped on my erect cock and then I heard a buzzing and vacuum sound; I then felt it.
It was a feeling I had never experienced before. It was like a blowjob, but more powerful. Anne said, “I’m going to milk you until there is nothing left of you; until you dread the thought of another orgasm”. My blood ran cold. Anne then took her place at the foot of the bed and began applying more oil to my feet. I almost didn’t feel it over the constant sucking, but the oil was cool, and she tickled my toes when she applied it between them. Anne then scrubbed my feet with a vibrating hairbrush, and I lost it. I laughed, and screamed, and orgasmed over and over and over again; three times in a row. I must have passed out again.
When I awoke, my blindfold and gag was removed, and my arms were freed. The Venus Milker was removed as was the remaining cock ring. My feet were still tied together, but I could see that Anne was cleaning up and collecting her belongings. She then went to the foot of the bed, gave my soles a final tickle, and released them from their cuffs. I just rested there for a few minutes regaining my strength and taking stock in the experience I just went through. Anne said, “there is a bathroom over there (gesturing to the bathroom) if you want to get cleaned up”. I showered, dried off, slipped on my t-shirt and jeans, and proceeded out to the living room. Anne said, “so how do you feel”? “Exhausted” I responded. Anne said, “you were by far my most favorite, and sensitive victim”. We exchanged a few more pleasantries and Anne said, “if you are ever in State College again, hit me up and I’ll make it worth your while”. I said “Absolutely” as I searched for my shoes and socks. Anne said, “your sneakers are at the door, but your socks and boxers are mine, to remember you”. As I left the room that we had shared together for the past several hours, I reflected on the experience a bit more, chuckled, and thought to myself “what’s the worst that can happen”.
 
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