A Guy With Tits

Part One

I’m a guy with my very own great pair of tits. For whatever reason, Mother Nature decided to bless me with- in addition to the normal body and genitalia of a man- a round, high pair of breasts and sensitive nipples. I’m not an expert in the human anatomy, but part of it is genetic, inherited. My ‘anatomic extras’ developed in high school. Locker rooms were torture and my social life was nonexistent because I couldn’t bear the thought of getting naked and exposing my breasts to a girl, and that’s how I ended up a 36-year-old virgin on the south side of Milwaukee.

Having my very own tits to play with is, naturally, a great convenience- I don’t have to ask some lady on the street if I can play with her tits- all I have to do is reach up under my shirt, and I get the advantage of being both the feeler and the feelee!

At any rate, I’m 6'1" tall, 185 pounds, with hair somewhere between light brown and dark blonde. I have a passable face framed by a short beard. I’ve been single for several years, for reasons that are none of your damn business. And (the item I’m sure you perverts are most interested in) my breasts measure 45 inches over a large rib cage, so when I choose I really fill a 40C bra. I’m no Pam Anderson, but then again I’m not her kid brother, either!

But allow me to spend a moment explaining how I got started on self-tit-bondage, which I’m sure you’re into because you’re finding this story posted on a site which caters to such perversions. Many years ago, when I lived on the south side of Milwaukee, I walked down the street looking for something to do. I found that just down Lisbon Avenue from my apartment was an adult book store and den of iniquity, so of course I wandered in just to scope out the place. It wasn’t a ratty place, actually- it was clean and well-lighted, although it certainly wasn’t the ‘Clean And Well Lighted Place For Books’ many book stores fancy themselves.

After browsing for a while, I picked up a magazine I’ll never forget- ‘Knotty’, a glamour bondage glossy. On the back cover was a lithe young black girl wearing only a vinyl bra and panty set and about fifty feet of rope. Her wrists were tied together in front of her and her elbows were tied, almost touching, behind her. The tension on her elbows thrust her breasts forward, aching to be touched. Her eyes looked directly at me, as if to say “Release me- no, don’t untie me, just release me!” In my imagination, I was her, and from that time on I was never the same. I bought the magazine, a couple of others, and a few toys. In half an hour, I was back at my apartment and was halfway to helpless. I had started out by getting naked, of course, and then pulled on some cherished items of ladies wear- a bra and a pair of control-top pantyhose.

Never mind where these bits of ladies’ wear came from- a guy alone either jacks off or lies about it, and a guy who jacks off collects a few toys, right? I like the control-top pantyhose: on top of being snug, they make my legs feel extra-slippery against each other. After I finished snugging the Queen 4 size pantyhose (the only size that comes close to fitting me for length) up around my waist, I pulled on the bra. This was an old friend, a pushup style which was really too tight at 36B. It really heaped up my tits and made me really feel their presence!

I had cut a wedge out the cups to expose my nipples, since I always wind up doing something or other with them. Yes, I play with myself and my tits a lot, and their sensitivity is something I cherish. This time, I pulled out a pair of spring clothespins and secured them to my breasts, grabbing a fair chunk of breast flesh as well as the nipples. I twanged the clothespins a couple of times, getting used to the sting.

Moving on, I wrapped a length of rope three times around my waist and then continued the wrapping down around my thighs to my knees. Trying to move with my knees bound was very awkward, humiliating, and a real turn-on. Another short length of rope surrounded my ankles, where three more loops held my ankles crossed. I figured out quickly that having my ankles bound crossed meant true immobility- the only way to get around was snake-style.

My wrists were locked together in front of me by my new pair of police-issue handcuffs, heavy chrome steel things; the keys lay on the kitchen table. I knew I was going to jack off right away, and for a first attempt I wasn’t going to attempt prolonged delay, which I was to find out was the prime ingredient to bondage. From my nipples wobbled a pair of wooden spring clothespins, each of them grabbing a big jawful of breast meat. From my crotch jutted a thick, hard erection, but I’m sure you anticipated that!

I knelt down in front of the table and my lovely model friend, who was considerately exposing herself in front of me, As I knelt, the ropes around my thighs and my ankles pulled very very tight, but I was too horny to worry about the discomfort. My two hands together, connected by my handcuffs, I interlaced my fingers to make the familiar “Mrs. Palms and her eight daughters’ configuration.

As I stared down at the photo story (yes, I had read the story, which wasn’t bad), I stroked my erection and in a matter of moments was rewarded with that ol’ familiar feeling as the head of my cock swelled and threatened to explode. I delayed as long as I could, which wasn’t long, and soon thereafter was rewarded with the blessed burning as my sperm guys scorched their way down my shaft and splattered out across the floor.

Of course, once I had finished my orgasm, I still had to go through the mechanics of unbinding myself. My first mistake was reaching up with my cuffed hands and immediately removing both clothespins at the same time. Being a rank beginner at playing with my own tits and with breast bondage, I wasn’t aware that the blood flow to my sensitive flesh had been severely impeded, and right after the pins were removed, the blood rushed back in. This produced a burning sensation that no amount of rubbing could soothe. I just waited until the burning eased, and then I continued to soothe my abused nipples, well, because I could.

Anyway, the orgasm was incredibly intense, partially because of my new-found fascination with bondage, partially because of my paper girlfriend, and partially because I was discovering a whole new aspect of my personality. Naturally, I continued!

Shortly thereafter, I discovered a new use for a vertical support beam in the basement of my townhouse. The intended use of the 4”-diameter steel beam was to support an 8” steel I-beam which supported the weight of much of the house between the outside walls, and it was indubitably solid. I whacked it with the heel of my hand, and the only sound that came out was a meaty THUD! as I connected. Yes, it was plenty sturdy for what I had in mind.

I collected some things I’ll delicately call ‘implements’, which will be described as they come up, and piled them on a folding chair. I started my self-bondage by getting naked. My second preparatory step was to attach to a sturdy cord a pair of nipple clamps I had just purchased, a pair that were to become long-time favorites- ‘clover clamps’, which resembled small spring-loaded pliers with a devious mechanical linkage. As more pull was applied to its end tab, the jaws were forced together, pinching harder on whatever happened to be between the padded jaws of the clamps.

My two clamps were connected by a three-foot-long cord running through an inch-diameter steel ring, On this ring I clamped a ten-inch Vise-Grip - in addition to being a super tool, it’s a handy heavy chunk of steel weight. I carefully fastened the clamps to my nipples, positioning them carefully so only a small nub of nipple projected from between the jaws of the clamps. They stung, but the sting went away as my nipples became numb.

I backed up against the steel column, reaching behind myself to spread the cheeks of my bare ass so their cleavage embraced the solid, cold steel. I used a nylon strap to fasten my ankles to the column, another to fasten my knees. One more longer strap went around my waist and the column, and finally another strap fastened my chest to the column, across my breasts just above my nipples. This last strap pressed down on my breast flesh, forcing the rest of my breast to bulge out even more. The pressure caused the skin to pull tight, and my clamped and weighted nipples stung even more.

About time for my fantasy dominatrix to take over! Mistress Yolanda seized the cord attached to my nipple clamps and tugged down on it. The clamps pulled my nipples out from my chest. Mistress Yolanda gave the ViseGrip a shove, watching it swing from side to side. It twisted my nipples as it swung, and she smiled a cruelly beautiful smile at the grimace on my lips.

“Lock your hands behind your back, slave. Make yourself helpless for me.” As She commanded, I put my hands behind my back, holding them there as if they were cuffed. This position pulled tighter the skin of my breasts, and I felt even more the pinching of the clamps. (If you’ve had the painful pleasure of having your nipples clamped, you know why this works.) My erect cock projected out rigidly and eagerly.. “Please, Mistress, may I cum?”

“No, you may not cum- you may cum only when I say you can. I want to watch you suffer for a while.” I struggled against the straps for what seemed like an hour, pleading occasionally, until She finally relented.

“Okay, slave, you may spit in your hands and make yourself cum for Me.” Eagerly, I raised my hands to my face and spat. With that pitiful bit of moisture, I clasped my hands together around my aching erection and stroked until my cock exploded, spurting my juices onto the floor

Part Two

My ability to release myself at any time was dampening the whole bondage experience- I was finding out for myself something that any self-bondage fan finds out. Bondage has to be real for it to be satisfying! The ability to free yourself any time you want makes obviously unreal bondage. I knew that if I was to experience the ecstasy of real, inescapable, desperately struggling helpless bondage, I had to either find a real Mistress to take me truly captive or I had to develop some way of simulating one. Since I knew I didn’t know how to find a trustworthy and serious Mistress (I’m not into sex professionals), I put my wits together.

My first thought was to build a battery-operated timer of some sort, but it would have to be totally fail-safe and faultless. (I eventually made such a device, but more on that some other time.) For now, I figured out my first way of binding myself inescapably and still getting loose sometime. I got my idea about this on Gromet’s Plaza, what turned out to be a tried-and-true ice cube trick.

I made a trip to Wal-Mart, where- under the sneering eye of a smirking young sales girl clerk, maybe 19, who made it quite clear she knew that I was buying them for myself for some perverted cross-dressing fetish- I selected several pairs of nylon stockings and a garter belt. Queen 4 fit my long legs quite well, and they’re available in a variety of styles. Queen 4-size ladies need fun stuff so they can look good, too!

Finally home, with my bag of goodies and still feeling humiliated, I disappeared into my basement dungeon. I first hung my dungeon key ring on a cord tacked to the ceiling so I would be able to reach it when I was bound and ready to release myself. The next challenge was to keep the key ring out of my frantic grasp for some predetermined period of time, absolutely unreachable, but yet ensure that they would be accessible after the predetermined period of time had passed. This would act just like my fantasy Mistress- keeping me bound even if I changed my mind and frantically wanted to get free. Here’s where the stockings and some ice cubes came into play.

Into one stocking went a handful of ice cubes (I wasn’t sure how much would be enough, but too many would be better than not enough, right?), and I tied a loose knot to keep them in the foot. I ran the other end of the stocking through one of several eyebolts I had screwed into a ceiling beam. I tied my dungeon key ring, which was hanging from a cord near my final bondage position, to the loose end of the stocking. Since the ice cubes were heavier than the key ring, the keys were pulled up to the eyebolt near the ceiling. When the ice melted, the weight of the key ring would eventually pull the rest of the ice through the eyebolt and drop to the end of its cord, hanging somewhere near my hands.

That completed, I set up three full-length mirrors, purchases from the thrift shop. One went in front of me, about six feet away. The other two went beside and behind me so I would have a panoramic view of my situation, my bondage, and my naked self. Now I could be both helpless exhibitionist and voyeur!

My construction labors ended, I went about disciplining myself. I stripped naked and collected my toys. I sat down on a steel folding chair, feeling the cold steel against my bare asscheeks as I pulled the smooth stockings up my legs. I got up, slipped on the garter belt, and smoothed the stockings down carefully (I wanted to look as ladylike as possible) before I fastened them to the garter belt.

In my stocking feet, with my ass feeling conspicuously bare between the straps of the garter belt, I stood on another new toy, a homemade implement of restraint. Starting with a 3’ circle of plywood- a table top blank- that I bought at Home Depot, I had bolted to it three eyebolts- one in the center and one at each edge, all in a line. To the outside bolts I bound my ankles with two-foot-long pieces of clothesline; this kept my legs spread wide. My balls dangled vulnerably between my legs.

To the center eyebolt I had attached a short bungee cord with a noose tied in the free end. I pulled this cord up until I could snug the noose closed over my balls. If I stood erect, which of course I did, the cord pulled down sternly at my balls, wedging them down to the bottom of their sack. I wiggled to find that I was in fact quite immobile, although at this stage I could still easily free myself- but I would change that soon enough.

I reached out for my police-standard handcuffs and locked one on my right wrist. Then I reached up for the cord which ran from my nipple clamps up through another eyebolt in the ceiling. The cord ran through that eyebolt to another about eight feet away, then down and sideways a bit to a pipe wrench which lay on another folding chair. I had cut this cord carefully so there wasn’t much slack. Carefully, I attached the clamps to my nipples, jaws down.

I reached out for the cord and pulled slowly down until the Vise-Grip lifted off the chair. It swung sideways away from its support, nothing under it except air and the floor. I slowly paid out the cord until it pulled taut the cord to my nipple clamps. I looked down helplessly at my breasts, my contorted nipples, and the erection protruding stiffly below them.

After a quick check of everything, I put my hands behind me- I wasn’t sure which would be worse, to be trapped in my self-imposed bondage or to be released prematurely! I grabbed the loose cuff and quickly locked it around my left wrist. For the first time, I was truly helpless! I struggled mightily, demonstrating that I had done a very good job of immobilizing myself; I couldn’t move enough to mention. Worse yet, my struggles made the weight of the wrench twist nastily at my defenseless nipples. I looked down to see the distorted shape of my boobs as the clamps tormented my nipples; my breasts were round and firm, but the nipples and surrounding flesh were pulled out into an aching cone.

Just then, my fantasy Mistress Yolanda stepped into my dungeon cell. As always, She was a vision of loveliness. Tonight, She was marginally dressed in a blue nylon halter top, a short short denim shirt, black nylon stockings and 4” heels. “Damn, you fool, you sure have done a number on yourself! I mean, this is sexy as hell, but you just aren’t going to be able to get at Me, are you?” Her nipples poked thick bumps in the thin nylon top; I felt the first aching desire to get my mouth on them, but of course that wasn’t going to happen, was it?

Mistress Yolanda reached down and grabbed the hem of Her tiny little skirt at Her side and lifted it a few inches. Slowly, too slowly, this exposed the tops of Her stocking, the strip of firm bare flesh framed by Her long garters, and finally Her lacy black panties. She smiled as She saw the desire in my face.

She turned and unhooked Her skirt, dropping it to the floor and presenting me with a glorious view of Her swelling butt. Her backside of Her panties disappeared into Her nether cleavage, forming a triangular wedge shape that pointed down to heaven. The garters painted vertical stripes on Her pale flesh. My cock ached with desire for Her, and I let out a groan.

Mistress Yolanda sneered at my desire as She turned back to me, letting me drink in the frontal view of Her and the way Her panties cupped Her… oh god, Her delights…. I struggled against my too-effective self-bondage, and She laughed happily at my futile struggles.

Mistress Yolanda raised Her arms, unhooked the straps of Her halter behind Her neck, and too slowly (it’s always too slow, especially when you’re a helplessly bound observer) lowered the two triangular bits of nylon to the band which circled Her stomach. Her breasts sagged slightly as their minimal support was removed. Slowly, too slowly, Her fleshy globes came into view, Her thick nipples reaching out to me.

“You like these, you horny little boy? You want to taste these nipples? Sorry, but you decided you wouldn’t get at these when you tied yourself up!” She slapped one breast with Her fingers, making the flesh jiggle for my frustrated enticement. “There’s no way you’re getting free, let alone to My goodies, before the ice melts. Just remember- that’s the way you planned it. You wanted helpless restraint, that’s just what you’ll get, and maybe more.”

She reached up and gently stroked Her nipples with Her fingertips, twanging them with Her long red nails. “Oohhh… I bet your nipples are just as sensitive as mine, but then again I bet yours hurt a lot. Those clamps look like they’re squeezing the life out of your nipples, whereas Mine just feel good.” She twanged them again and smiled, Her eyes half closed. She pulled off Her top, Her boobs jiggling for me, and dropped it to the floor on Her skirt, standing before me in only Her panties, Her garter belt, Her stockings and Her high-heeled shoes. She looked more naked than naked!

I lowered my head. Below my outstretched nipples and above my down-stretched balls, my rigid erection jutted out into space, aching. I was stretched between the bondage platform, to which I was bound by ropes and gravity, and the ceiling, to which I was pulled by the wrench’s weight pulling up on my clamped nipples. I struggled mightily against my self-imposed bondage, but it was of course useless- I had been too effective. Even though I now wanted desperately to free myself, I was trapped.

My mind was working in overdrive; Mistress Yolanda kept my bonds cruelly tight, and I lusted mightily at Her display of Her beautiful, enticing body. As She moved around me, She made sure I had many opportunities to drink in the delights of Her body, teasing me mercilessly. She turned slowly, letting me lust after Her lithe body as She postured Her backside for me, them Her breasts, then spreading the cheeks of Her ass, then pulling Her panties aside to show off Her pussy- over and over again. I was nearly in tears.

The more I fought my bonds, straining for freedom and release from my frustrating self-imposed bondage, humiliation and frustration, the more eager grew my cock. Jerking at the implacable steel of my handcuffs, I struggled, gazing wide-eyed at my Mistress’ delights. I stared into the upright mirror at my humiliated reflection for what seemed like an hour- I really didn’t know how long it would take those ice cubes to melt. To make matters worse, I had deliberately placed the ice-packed stocking behind me where I couldn’t see it, and I had no idea how much longer I would have to wait to be free.

The ice finally melted, and I felt my key ring bounce free against my hands. I reached for them, only to have them swing away- damn! After what seemed like another hour, I finally managed to release my wrists. In moments, I dropped to my knees; the wrench rose far up, jerking to a halt when the wrench jammed into the eyebolt. The pull at my tits wouldn’t decrease, but if I leaned back against the cord it could easily become worse. Of course, I leaned back as far as I could. My nipples were flatter and longer than ever before.

I grabbed my aching erection between my palms, and with my lust-inspired sweat as my only lubrication, began to stroke. I kept my grip light for as long as I could until the head of my cock seemed to swell to the size of a grapefruit as it passed between my palms. I surrendered and squeezed tightly with both hands. My nipples burned as the head of my cock finally convulsed and exploded, spurting jet after jet of my juices across the floor.

After my self-induced orgasm finally subsided, I stood up gingerly. When the weight of the wrench finally lay on the floor, I removed the clamps from my nipples. Damn, that burned! It seemed like the clamps had been crushing my nipples for hours, and rubbing the flattened flesh didn’t make the sting go away any faster. That was my most extreme self-bondage experiment for quite a while, although I played with variations like strapping my legs double. But always my tits were at the heart of my auto-erotic ventures.

Part Three

Naturally, having been blessed with such a playtime gift as my boobs, bras are a favorite toy and adornment, and since I’ve gotten entangled in the web of bondage, breast bondage came naturally. I decided, while playing with a collection of my toys and a length of rope, to weave a ‘bondage bra’ for myself. While browsing through the assorted sleazy magazines through which an unattached male usually winds up browsing, I’d seen pictures of babes with their tits bound, with varying degrees of stringency and/or realism. (Usually very bosomy babes- who’s interested in looking at pictures of flat-chested babes with their tits bound?) The worst (which wasn’t exactly miserable) showed a big-boobed bimbo with two ropes draped loosely around her chest, and the best showed serious loving bondage which showcased the lady’s bound breasts. I always read the stories that came with them, which usually described in erotic detail how they dreaded and loved the experience of being bound, and how the bondage made her breasts feel.

So I decided to have a go at it myself. As usual in my basement/dungeon/playroom, I took the center of the rope, conveniently marked with a red marker, and positioned it behind my back. I then pulled the free ends of the rope in front of me, under my breasts and up between them, crossing in the cleavage which was developing as the first strands of rope pressed in on my flesh. I continued weaving. Each loop of rope pressed up, down, and in, bulging my breasts out, forcing my tits into tighter and pinker globes. The friction with the rope (I’m partial to sisal) over my nipples soon had them even harder and stiffer than they usually are. After six or seven wraps of rope, I reached the end of the rope and tied the free ends of the rope in front of me in a tidy square knot.

I looked at myself in the mirror. My breasts, normally firm and high because of their muscular support, had been reshaped by the rope bondage into something worthy of a magazine cover. High on my chest, they were bulging and round, with a prominent valley between them. Best of all, my nipples projected stiffly into the fingers of whoever wanted them!

I opened my ‘toy chest’ (really a toy chest from WalMart!) and removed a pair of stockings, a garter belt, and a frilly pair of bikini panties. I wrapped the garter belt around my waist, slipped the panties on, and tugged them gently up around my waist, pulling the sides high.

I took a seat on a chair, the steel cold against my barely-covered ass, so I could slip the stockings up over my legs, smoothing them carefully. Then I stood up again to fasten the stockings to the garters. After adjusting everything, I looked at myself in the mirror again. Not bad, but my erection- straining heavily against the flimsy panties- was clearly out of place. I pressed it down between my thighs and snugged the panties back up to keep it in place. It ached, not at all appreciating being bent backward. Although this position is said to ruin an erection (at least that’s what I’ve read while reading about male chastity belts), my cock remained fat and eager in spite of its position.

I took a minute or two to retrieve some ice cubes and prepare my self-bondage auto-Mistress. That done, I reached into my toy chest for a ball gag, a recent construction. I had taken a red rubber ball, slid it to the center of a stocking, and tied the stocking to hold the ball centered. I then tied a steel ring in one end of the stocking and a steel S-hook in the other. I stuffed the ball into my mouth and hooked it behind my head; the ball was fat enough so that I couldn’t have pushed it out with my tongue, but the stocking and the clip made doubly sure. Besides, the snugness felt good! I made a few tentative cries for help and found that all that came out was mumbles- just right! My cock strained at its fabric prison.

I retrieved a chain with a slip hook and fastened the free end of the chain to a hook in the ceiling. Using a chain makes it easy to adjust its length, and it’s certainly stronger than an equivalent piece of rope. Moving on, I grabbed a pair of ankle cuffs from the chest. I bent over to lock them around my ankles and pressed them closed until they pressed in on my Achilles’’ tendon. If you’ve ever had the pleasure of being hampered by ankle cuffs, you know how difficult it is to take any kind of steps at all with a band of steel clamped around your ankle. I decided this was miserable and too much, which added to my heat, and of course I left them on and continued.

Next, of course, came a pair of nipple clamps. (Me being me, with a great and sensitive pair of tits, doing something to my nipples is always a high point of my games.) While perusing the ‘toys’ at a local adult video and toy shop, I immediately and perhaps hastily decided ‘we’ve got to have those!”. (The ‘we’, of course, referred to me and my two eager if somewhat worried nipples.) These clamps would, after this scene, be reserved for drunken masturbation games, because they turned out to me in the Most Severe category and which worked best with some degree of local anesthesia.

Each jaw was about an inch wide, with five sharp teeth curved inward, clearly to get a serious grip. The jaws were forced closed by an industrial-strength spring, and two adjusting screws kept the heavy spring from driving the teeth all the way through my skin. I knew from the get-go that these clamps were going to be nasty- I tried closing them on a finger (not having the balls to try them on my tits in the store)- but I underestimated just how nasty!

I held the clamp in my right hand, holding it open wide against its spring, while with my left I gently squeezed my right breast to make its nipple protrude. At first I closed the jaws right behind the nipple, but that hurt so much it threatened to ruin my fun. I backed up and took a bigger bite of tit meat while I closed the clamp and adjusted the screw. Two tries later, I had both clamps attached securely to my nipples- damn, these clamps were vicious! I knew I didn’t want these things to skid off, clawing all the way- that had happened once while I was first trying them out, and it hurt an awful lot. I adjusted the screws so the teeth bit in and were securely anchored in my breasts, with no possibility of the teeth sliding off. I slipped a little finger tip between the jaws from the side and stroked my already-miserable nipple, telling it wordlessly that I appreciated its sacrifice for my pleasure.

I leaned back, which pulled on the cord attached to my nipple clamps. The cord ran up from the clamps through an eyebolt in the ceiling, across about eight feet, and through another eyebolt. From there, the cord descended to a folding chair, on which lay a pipe wrench. (Pipe wrenches of any size are heavy, and that ‘heavy’ is the point here). I pulled down on the cord and the wrench almost immediately started to lift off the chair- I hadn’t left much slack. Because the chair was off to the side of the eyebolt in the ceiling, the wrench swung away from the chair. This was the first commitment point; I could still abort the whole thing and free myself, which I obviously didn’t want to do. Short of totally bailing out, I was now committed to a sustained period of nipple torment.

Taking a deep breath, I slowly let the cord slide through my fingers until finally the weight of the wrench hung from my suffering nipples. I looked down at the jaws of the clamp, firmly seated in my breasts; a good-sized chunk of my flesh was imprisoned in the cruel jaws. The steel teeth were firmly embedded in my tits, and squirming just made them twist from side to side and dig in deeper. With some misgivings, I backed out the adjusting screws to allow for the depth to which the teeth had sunk into me, to keep them firmly attached to my breasts. Naturally, I struggled, because that’s what I enjoy!

Eventually, I relaxed and picked up my favorite handcuffs from the chest. After another quick check to verify that my release would happen as planned, I locked one securely around my left wrist. I slipped the hanging hook into the ropes of my bra where they crossed in my cleavage and adjusted the chain so I had no slack at all- I had to stand on my toes, almost.

After a quick stroke of my straining cock through my panties, I reached behind myself and locked my wrists together. With a CLACK-CLACK-CLACK, I became totally helpless! The muscular effort of bending my arms behind me made the skin of my breasts pull tight, which emphasized that said skin was being chewed on by the clamps. Looking downward, I surveyed the damage to my favorite breasts and kept right on. I looked at the mirror and saw a six-foot tall babe bound and gagged, her tits aching for attention, her nylon-clad legs spread for a touch that wasn’t going to happen, at least not soon enough.

At just that point, my fantasy Mistress Yolanda entered the dungeon. This time, She was wearing a French-cut T-shirt over hot pants and 3” heels- short for Her. The hot pants were unexpectedly hot because they were made of rubber. She turned once for me to show off the way the shorts cupped Her ass cheeks and showed off the sexy fold at the between Her thigh and Her cheeks.

“Well, I see you’ve done it again, you foolish man! You’re totally helpless, gagged, and you have no way to get at all these goodies that are just waiting for you. You’ll suffer for that, you know!”

Stepping in front of me, She reached down to Her waist and began to lift Her T-shirt. As it rose, She displayed Her smooth belly, then Her lower chest, and finally Her glorious tits bobbled free. She pulled the T-shirt over Her head and tossed it on top of my clothes.

Taking both breasts in Her hands, She cupped them and stroked Her nipples with Her fingers. “Ohhh… that feels good. Do yours feel this good with those clamps biting into them?” She reached up and tugged on the cord; this dragged my suffering boobs upward at least an inch. She smiled cruelly at the agonized grimace on my face. I wiggled and struggled and found that, the more weight I threw on the chain, the righter my bra pulled across my breasts. I bent my knees and watched my reflection in the mirror as the babe’s breasts lifted higher as she struggled. I continued, feeling my erection strain at the flimsy cloth of the panties as they pulled my cock up against my crotch.

Mistress Yolanda smiled at my useless struggles. As I continued to squirm, She peeled down Her pants, revealing that under them She wore only the flimsies thong I have ever seen. In front, the filmy nylon cupped Her pussy. It was so thin I could see Her pussy lips. I struggled harder, and She smiled even more cruelly, if that were possible. She turned slowly and bent for my frustrated viewing pleasure. Her thong was a tiny stretchy strap of cloth that encircled Her waist, and from the center of its back was fastened a slender scrap of cloth which descended to disappear between Her plump asscheeks. As She bent, She separated Her asscheeks with Her hands, giving me a delightful view of how the scrap crossed Her puckered asshole and disappeared between Her pussy lips.

She looked back at me in the mirror and then reached down with one hand to grab the front of Her panties. “It’s a shame you’re so helpless. Otherwise, you might be able to pleasure me so I wouldn’t have to do this.”

Mistress Yolanda began to saw Her panty crotch back and forth through Her pussy, dragging the strip of cloth between Her swollen and sensitive lips. “Oh damn… that feels so good… almost as good as your tongue on me… if only you weren’t tied up so you could get to me….” My straining cock bulged earnestly, eager to push into Her pussy. “Ohhh… that feels good… I’m so wet for you….” She turned to face me, driving one hand into Her panties from the side, and raising the other to an eager breast. Her face contorted in eager delight as She masturbated for my delight.

“Ohhh… ohhh… I wish you weren’t tied up so you could do this for me- I want a cock in me so bad- I’m going to cum without you! Don’t you wish you could fuck me instead of waiting tied up like that? Ohhh!” She dropped to Her knees, one hand gripping Her barely-covered pussy so hard I could see Her hand go white. Her other hand gripped Her right nipple, crushing Her flesh and bending it far from its normal round shape, as She shuddered through Her orgasm.

With a few more titanic strains, I saw the babe’s penis slip out of Her panties. Hard and erect, it waved darkly in the air, its fat shaft rubbing against the hem of the panties. I cried out for Mistress Yolanda to help me and struggled mightily. I felt a familiar burning in the head of my cock, and my Mistress extended Her hand, stroking it lightly. I bent my knees and almost lifted my feet from the floor, feeling my ribs flex as my weight hung from the rope bra tormenting my tits. The head of my cock swelled in Her gentle grasp, and She stroked gently. In seconds the babe’s penis erupted, spurting sperm across the floor, and I almost passed out!

It seemed like an hour before the ice finally melted and released me- it always takes longer after you cum! After I finally released myself, I sat down to plan: even though this had been a tremendous orgasm, did I want to delay release even further? I did!

Part Four

My first move was to make another trip to Wal-Mart, where I looked for a big lady’s girdle. Amazingly, considering the number of big ladies around, big lady girdles are hard to find- I guess they all rely on control-top pantyhose! Unable to find an appropriate girdle, I went down the street to a thrift shop. After shopping around, I managed to find a big black girdle- a long-legged model with a high waist and six garters under the legs. The lady who donated this one must have been a real armful! The girdle looked like it had enough double-layered Lycra to make a really ample lady look like a model, and so I bought it.

While I was humiliating myself in the lingerie department, I browsed through the bras. I found one I really liked: a long-line pink model which, although it was a 36C, would stretch to fit, I thought.

Naturally, the kid at the checkout sneered wordlessly, not having to say that he knew that I was buying a bra and girdle to take home and wear myself as I pranced around the house. I blushed and bit my tongue.

Soon back in my dungeon basement, I got naked and started making preparations for a great scene. First, I positioned a pair of full-length mirrors (another thrift-shop prize) in front of and to the sides of me. While I was dressing, I would get to enjoy the humiliating view and also be able to check out my clothes carefully. Once I was bound, I would have no choice but to examine my submissive situation!

Next, I set up another new invention- a length of rope hung between two bolts in the ceiling about eight feet apart. The rope hung down in the middle, of course, forming what an engineer would call a ‘catenary curve’. The low point of the rope was just above crotch height, and I’ll explain its function when it becomes necessary.

And finally, the last step in the setup of my devious devices, I stuffed a large handful of ice cubes into my ice-driven restraint timer and attached my dungeon key ring. It would take a few minutes to get dressed and to complete my bondage and I needed to allow for that time.

Okay, that took care of the setup- now to dress up! I retrieved my ‘new’ girdle and slipped it up my legs. After much squirming (which I was forced to watch in the mirrors), I eventually had the girdle up around my hips. I turned around to watch my ‘rear view’ as I fought to get the zipper up and locked. My ass cheeks were delightfully poised, firmly squeezed up and together inside the garment. I know there’s not much visual appeal in a no-cleavage tightly-girdled ‘monobuttock’, but at least to me it looked and felt great!

I slipped on my new bra and let out the shoulder straps as far as they would go; there’s something about a man’s build that always makes it necessary to do that. I wrapped it around myself and, with the hooks in front, managed to get all six fastened. I twisted it around, pulled it into position, and slipped my arms under the shoulder straps. The bra cups were a little snug, like the entire garment, but that was just fine with me because the end result was a push-up effect. My breasts rested on top of the small bra cups, heaped up roundly, my nipples projecting stiffly and vulnerably. Emphasize vulnerability!

I took a moment to slip my stockings up my legs. Taking a seat on a folding chair, I rolled up the bottom edges of the girdle’s legs, fastened the tops of the stockings to the garters, and pulled the girdle down to cover the tops of the stockings and the garters. Then I slipped my feet into a pair of high-heeled shoes I bought at the same thrift shop- red and with 3" heels. They were a bit too tight for me, but the discomfort just added to the thrill of the whole affair.

I reached up to my new bra, wondering about the woman who had donated it to her ‘worthy cause’- I wonder if she thought about how her underwear might give so much pleasure to an anonymous pervert? I rolled the top edge of the cups down to expose my nipples. Did she ever play with her nipples, too? Later, I would cut out the tip of the bra cup to expose my nipples, but that was later. Now, with the cups folded down, the bra lifted my breasts even more and, as I examined myself in the mirrors, gave me a really enticing cleavage.

I reached out for my clover clamps, already hanging from a cord near what would be my bondage position. I had a lot of practice by this time and in a few moments had my tender nipples securely clamped. From now on, my range of motion was quite limited.

My cock was stiff, pressed up against my belly, and pleading for my attention. It would get it, certainly, but not just yet! I forced my hand down the stiff, heavy-paneled front of my girdle and pressed my cock down and back between my thighs. (I’d read about this position while studying male chastity belts on the Internet- I wanted to restrain myself and my erection big-time.) The extra-control girdle fabric sprang back into my crotch, firmly pinning my fat cock up in the channel between my thighs and my crotch, hemmed in on the sides by smooth, slippery Lycra. It was trapped, just like I wanted!

I moved into a new phase of my ‘game’ by picking up another recent purchase from the local porn shop/toy store- a butt plug. This one was black, maybe five inches long and two inches wide, and claimed it was a ‘medium’. After I smeared some slippery stuff on its tapered shaft, I unzipped the back of the girdle and eased it down to clear my ass cheeks. I bent over, watching my every move in the mirrors, and slipped its blunt point up into my ass. I pressed until its widest point approached my asshole, which protested that the intruder was too big! I tried to relax as I twisted and pressed. I was rewarded as the plug slipped in and was suddenly buried too deep inside me. With determination, I screwed the plug home until its flared base was snugly buried between the cheeks of my ass. I felt full!

I pulled the girdle back into position and reached behind myself to pull its zipper snug; the stretchy ladies’ self-bondage garment squeezed me tightly all around. From that moment on, every movement I made during my self-bondage setup reminded me that a fat chunk of rubber was jammed up my ass! I reached out for my nipple clamps- my favorite clover clamps- and carefully attached them to my nipples. As always, it took a bit for me to get used to the sting, a time during which I wondered why the fuck I did this to myself! But I kept on, of course.

I picked up my hand-made ball gag and pushed it into my mouth, pulling its strap snugly around my head and clipping it. I’ve seen pictures of inflatable penis gags that really turn me on- the idea of having my head strapped into a harness and my mouth plugged by an oversized, inflated cock really turns me on, although I am quite straight. But I haven’t figured out where to buy one, so for now I’ll stick with the ball gag.

A pair of size-medium bikini panties were next- not lady-scented, sadly, so I had worn them myself for several days running and jerked off with them twice. I pulled them down over my head, leaving the poop-and-cum stained crotch right over my nose. I wrapped a three-inch ACE bandage around my head several times to compress everything snugly together. My head felt like it was in a vice! Walking awkwardly in this strange selection of clothing, I knew I looked like a ‘fag hag’ but I felt incredibly sexy as I proceeded on. I straddled the rope, feeling the butt plug twist inside my well-packed ass as I lifted my leg.

Next came my ankle cuffs- I felt the plug even more as I bent deep to press the steel manacles closed, teetering on the unaccustomedly tall heels. The keys were on my dungeon key ring, held hopelessly far out of my grasp by my ice-cube timer. I knew I could still back out just by crawling forward until I could unhook the rope from its bolts, although it would be difficult, but for some reason that I’m sure you’ll understand, I didn’t.

Okay, helplessness time!

I reached behind myself, feeling the clamps biting at my breasts, and cuffed my wrists together. The CLACK-CLACK-CLACK of the ratchet as the cuffs closed behind my back was very loud indeed. By design, the ratchet only went one way- closed- and each CLACK of the ratchet took me one step away from freedom. After two CLACKs, the cuffs were closed for me to withdraw my wrists, and closing them more was just for my own satisfaction. This was the first stage of commitment- no way was I getting free before my timer released me.

Next came the second stage of commitment, forcing on myself ‘stimulation’ during my period of bondage. I backed up on the rope; the cord to my nipple clamps pulled tight and lifted the weight off the chair; my nipples burned as it rose. The weight swung free, away from the chair so I couldn’t move forward to drop the weight on the chair- a cheap out, anyway. The weight was suspended from my tits, and the clamps pinched down hard on my nipples.

I felt the clamps digging into my flesh and seriously doubted whether I wanted to go through with this, but of course I no longer had any choice in the matter. I groaned loudly into my gag; nothing much came out, which was tremendously exciting to me. I was already committed to a sustained period of self-bondage, and now I had just committed myself to the tit bondage too, with no way back. That’s the great part about self-bondage- you make a choice not to have a choice!

My backing up, in addition to dropping the pipe wrench on my nipples, also forced the hanging rope firmly up into my crotch. It both jammed the butt plug farther up into my suffering asshole and also rubbed firmly against my bent-back cock, which was pinned down by the slippery Lycra of the girdle. Damn, that felt good!

Here I was, watching my humiliation in a pair of full-length mirrors. I was handcuffed and anklecuffed. My reflection showed me wearing a bra and a too-snug girdle that was jamming a butt plug too far up into my bowels, leaning back against a cord that was stretching my breasts out by my clamped nipples. My mouth was stuffed and my head was completely bound, leaving me mute and able to see only a little out to the mirrors which reflected my humiliating position. And the rope stretched between my nylon-sheathed thighs was rubbing through the slippery Lycra of the too-tight long-legged girdle against my bloated cockhead and driving me mad!

I found that if I bent my knees, the pain at my nipples stayed pretty much constant, or at least got no worse. When I bent my knees, my weight on the rope ground it harder into my crotch. I bobbed up and down on the rope, back and forth, savoring the feeling as the rope ground against my erection through the slippery Lycra.

I felt the head of my cock swelling. Even rigidly bound as I was, I was going to cum! I strained against my handcuffs and dragged the rope through my crotch, fantasizing about being a hijacked young maiden who was being roughly abused aboard a pirate ship. I struggled and strained against the rough ropes that bound me and cried for help that wasn’t coming. My struggles ground the rope into my crotch. The brutes had exposed my breasts and done all sorts of cruel things to my nipples. The more I squirmed, the more they laughed at my helplessness. The rope ground into my sensitive flesh, and despite myself I began to feel a stirring in my belly.

I didn’t have to work at prolonging the affair and delaying my orgasm- my bondage, the chastity-belt-style position of my cock, and the agony at my nipples made an orgasm difficult as it was. I felt the key chain slap against my back, but I ignored it and kept rocking on the rope. I wanted an orgasm so fucking bad- not just an orgasm, but this orgasm, with everything that went with and into it! As I squeezed tight with my ass muscles, the butt plug twisted and pressed deep into my bowels. Fighting against my gag, I bellowed out muffled protests against my captors and pulled back against my nipple clamps.

Finally I felt the first surges of my orgasm. I threw my weight against the rope, grinding hard against my restrained and sheathed cock, and finally felt my balls convulse as my cum blasted down through my cock. The spasmodic throbbing of my orgasm seemed to go on for half an hour, and when it finally stopped my head was spinning.

I clumsily fumbled for my keychain and finally managed to get my handcuffs off. After that, I stumbled forward to release the pressure against my crotch. Using a bit of restraint, I first reached for the girdle’s zipper and eased it down. Leaning back against the nipple clamps, I pushed the girdle down and gently reached down to wiggle the butt plug out of my sensitive ass. Dropping it aside, I fumbled with the key ring until I could reached the key to my ankle cuffs. I leaned down, feeling the nipple clamps twist at my breasts, until I could unlock one cuff.

That done, I pulled the girdle back up, primarily so I could walk without having my thighs strapped together by Lycra, and stepped awkwardly over the rope. As I raised my leg to step over the rope, the butt plug twisted again at my bowels. (After you cum, all the paraphernalia seems much more irritating than just before you cum!) At long last, I finally allowed myself to remove the nipple clamps. My tits had been crushed for so long and stretched so far that they felt like they were on fire! They were crushed and flat and red and looked like they would stay that way for hours. I soothed them for what seemed like ten minutes before the burning went away.

Finally, I unwrapped the bandage from my head and removed the panties and the gag, setting them aside for next time. Now wearing only my underwear, I sat wearily on the chair which had supported the pipe wrench. God, this had been so severe, I don’t think I’ll do it again for days!

 

 

02.07.06 reposted: 17.07.10