As a young man I was a very frustrated masochist, with no outlet for my extreme thoughts. I often masturbated to fantasies of being a prisoner, in some unnamed foreign land. I would frequently be suspended by my wrists and left hanging nude for hours or days, awaiting torture by one or more beautiful but very sadistic women. I was not guilty of any crime. There seemed to be no point to the torture, except for the sexual gratification it gave my torturers. I would be whipped, threatened with burning cigarettes, my genitals bound extremely tight with wet leather thongs that would further shrink as they dried, extending my agony over multiple hours. My captors would expose themselves to force my cock to become hard, adding to the agony. There was no device, no torture too extreme for my captors.
The pleasure I derived from masturbating to this fantasy was never enough to fully sate my thirst. I began to engage in self bondage, first hog tying myself on my bed, then later attempting to suspend myself from the crossbar in my closet by tying a rope around my ankles and tossing the rope over the bar. I'd then lie down on my back, pulling on the rope, and haul my ankles as high as I could manage, although the best I could do was resting my shoulders on the ground, given the low height of the bar and length of my body.
As unsatisfying and frustrating as that was, I still wanted more. After much searching I found a place I could actually somewhat safely suspend myself. In a nearby park there was a small wooden pergola, just large enough to cover a single park bench. The unlit park was completely deserted at night and the pergola was far from the houses which surrounded the park. Trees and shrubs surrounded all but the front of the pergola, affording at least some measure of privacy.
The top of the pergola consisted of an open criss-cross framework of 2x6 lumber, mounted on edge, overhanging the supporting beams. I found if I stood on the park bench and leaned forward I could reach the far end of one 2x6, hang by my fingers, and swing out free from the bench.
Although hanging by my fingers was interesting, I needed much much more. Returning at 3 AM on a moonless night I removed my belt from my pants and wrapped it several times around each wrist and, using my teeth, managed to get the buckle secure. I unzipped my trousers and let my cock dangle free in the cold night air. After one last look around to make sure the park was deserted I stood on the bench, on tiptoes and reached out to slide my bound wrists over the free end of the 2x6 and swung myself away from the bench.
It was everything I had hoped for. I felt truly suspended and helpless for the first time in my entire life. My cock was instantly as hard as possible and I loved the way it bounced when I twisted my body side to side, imagining that I was trying to avoid the sadistic tortures of my captors. The belt tightened wonderfully around my wrists, guaranteeing I couldn't slip my bonds. I could almost feel my naked flesh being mercilessly whipped, heavy weights tied to my cock, bending against my erection. Whatever cruel indignities popped into my imagination on that night, I went with. In short, I was in heaven.
I never really hung for more than thirty minutes or so before my need to masturbate overcame the thrill of hanging there. I would swing my legs back to the bench, not an easy task as they barely touched, and once my toes were down, it took a bit of effort to slide my belted wrists off the end of the wood. The first time was a bit of a scare as I struggled before I mastered the technique required to free myself. Back on the ground I would sit on the bench, hands still bound, and masturbate to a tremendous orgasm, the sensations of hanging helplessly fresh in my mind.
I did this bit of self bondage two or three times before I became a bit more cautious and decided it was not worth the risk of being caught in public like this. Besides, I had committed the experience to memory and could draw upon it whenever I felt the urge to masturbate. But after a few weeks the uncontrollable urge took hold and I found myself in the park yet again. Another 3 AM adventure.
I had swung myself free of the bench and enjoyed my usual half hour of dark pleasures. But when I swung myself backwards I was unable to reach the bench. Looking over my shoulder after three or four attempts (not an easy thing to do when hanging by your wrists) I notice the bench is not in its usual place. In fact it had been pulled back about two feet, well out of my reach. It was not making any sense at all. How could the bench have moved? I hadn't kicked it when I swung out.
The answer came when a voice emerged from the gloomy darkness behind me. "Hello, Paul" said the most seductive female voice I had ever heard. "It's been a while, but I've been watching and waiting for you, you filthy pervert."
I struggle to force my bound wrists free from the board, but even as light as I am, the full weight of my body made the belt immovable. I wanted to run away before any further humiliation, but I am well and truly helpless.
"Where do you think you are going, Paul? Or should I call you pervy Paul? I'm really not done with you. In fact I've hardly begun." She wickedly circles me, taking in every inch of my hanging form. Her hands massaging my aching shoulders, then moving around and down to examine my cock, her lips inches away.
"Paul, I had no idea you were so well hung. I can't wait to see this bulging painfully through the stainless steel ribs of my smallest cock cage" She muses as her red fingernails scrape down the sides of my shaft. She then flicks her index finger on the underside of my helmet, watching amused as I jump. "Don't worry, I train you down to the size you rightly deserve, you fucking pervert."
I recognize her now, Sasha, a raven-haired beauty with pale skin, a slender body with ample curves in all the right places, and slight smile that seemed to hide secrets known only to her. A woman from the neighborhood I'd never dare approach in a million years. So far out of my league I'd never stand a chance a hell with her. Yet now here she is, inches from my exposed cock and I'm completely at her mercy.
"Please, Sasha. Let me down. Please. Listen, I'll move away. You'll never see me again. Just let me down. Please" I plead desperately.
"Let you down? Now that wouldn't be any fun, would it, Paul? Besides, I haven't even begun the interrogation of my new prisoner. That would be you, Paul, in case you haven't figured that out. Now, let's start with a simple question and see if you'll cooperate or not. Why do you come here night after night and hang yourself like this?" She asked as her fingers deftly unbutton my jeans and she slips her fingers under the waist band and begins lowering them. She stops when the pants are bunched at my ankles and pulls my shorts down on top of them, effectively preventing me from kicking out.
"It's nothing Sasha. Just having a bit of fun. Really." I say nervously, watching her.
"Hmmm...that doesn't sound like an honest answer Paul. We're not getting off to a very good start. You are going to learn there are punishments for dishonesty." She explains, dropping her backpack and pulling out two 20 foot lengths of rope. She quickly loops one rope around each ankle, just above my bunched up shorts. The knots are pulled tight and the ropes led and tied to the vertical posts at either side of the pergola.
"If we are going to get to the truth, the real truth, the core of your depravity, I can see you are going to need some encouragement." She gives me a wicked smile as she pulls my shoes, socks, jeans and shorts free from my legs and throws them in a pile on the nearby bench.
Now naked from the waist down I feel more vulnerable than ever, but that feeling is soon replaced with dread as she pulls and reties the ankle ropes, working one side then the other, making sure my legs are spread as wide as they stretch, until she is satisfied my bondage is as strenuous as possible.
My balls swing free below me as she returns to tickle them with those red fingernails. "Is that tight enough for you, Paul? Or should we bring out a winch to put you in real agony? I have a better idea. Some instant and highly effective torture" she states matter of factly, her fingernails putting small scratches in my ball sack.
She wraps my hanging balls with the palm of her hand, pulling downward until I gasp in pain. She stares directly at me with piercing eyes. "Now, you've been warned once Paul. Another wrong answer and you will really begin to suffer. Now, why have I seen you from the window of my house, right over there, suspending yourself then jerking off?" She nods in the direction of a house across from the park, a lone window illuminated in a dim light.
"You can't have seen anything, it's too dark, too far." I protest.
"Paul, Paul, Paul. What ever is it going to take to get a good answer out of you? It's the 21st century. Night vision binoculars are a thing. And of all the sickos I've seen in this park, you are by far the most interesting. I suspect I know what you are all about, Paul, but I need you to confess it. Right now." She scowls as she tightens her grip on my balls and twists eliciting a howl of pain, but she does not release me. Instead she takes her other hand, forms a fist, and punches my squeezed balls, again and again. The pain is excruciating as my eyes roll back into my head. She looks into my face with a vicious smile and laughs.
As I recover she pulls out and lights a cigarette. Instead of extinguishing the flame she holds the lighter under my cock and balls and swings the flame around, not lingering long enough to burn, but long enough for me to feel the heat and understand the implied threat. I yelp and curse under my breath, afraid of her cruelty. "This is just a sample, Paul, a mild sample. There are so many far worse things that could happen to you. I'm sure you know this." She says calmly, looking at the amber tip of her cigarette, then into my eyes again.
