Cock Caged by a Big Older Lady Ch. 02

So there I was kneeling, sore, and horny, my tongue between Miss. Simmons's huge ass cheeks. I had lost track of time, and of how many times I'd made her cum with my mouth. By now it was near dawn. Despite my aching knees, back, neck, jaws, and tongue, I kept licking her butt hole. I knew I had no other choice. If I ever wanted to get my cock out of its cage again, I'd have to serve Miss. Simmons's every whim and desire.

A sudden hard slap, let me know to stop licking. I looked up from her hairy bush, past massive tits, to met the goddess's eyes.

She looked me over amazingly, and I flushed. I felt an urge to look sexy and slutty, and I try to pose for like the girls I've seen in bondage pics. My eyes open big, my lips seductively parted, I spread my knees wide, and pushed out my caged package. This drew a mean laughs from Miss. Simmons, and she snapped a few photos, letting me pose.

Miss. Simmons had been drinking steadily, tequila then champagne for hours, and now her eyes have a far off, disconnected look, that made me uneasy. She was grinning, but here eyes looked angry. I started to worry she was gonna do something really fucked up to me, and I was right.

Miss. Simmons told me to get to my feet. I rose as quickly as I could, only to be very ruffly grabbed by the hair. I was quickly led away and bent over a heavy, finely carved table. My face pressed down to the wood, ass up. I was told to hold still and keep my forehead on to the table. I knew better than to disobey.

I dared not look up, but I could hear, Miss Simmons digging in her bag of toys. What was she getting, what was she going to do to me.

A few moments later she was back, and I felt my feet being kicked wide apart, my feet bound to the table legs. Earlier that night, the big breasted goddess bound my hands behind me. Each wrist tied to the other elbow, so I couldn't reach down and protect by sweet bottom.

Then I was yanked by the hair into a standing position, and Miss. Simmons was shoving a bright pink ball gag into my mouth. I struggled as she pulled the straps tight behind my head. Droll ran out of my mouth, and I gagged as the big rubber ball forced my teeth apart. My cries for mercy were cut off, and Miss. Simmons clicked the latch, then stepped back to look at her work.

The ball gag, totally unexpected, choked me and I sputtered trying hard to breath. Miss. Simmons was looking more sadistic by the second, enjoying my terror. Suddenly the big woman was behind me again, to my surprise and short-lived relief, unclipping the gag. For just a moment I thought Miss. Simmons would show me pity, seeing how much the big ball made me suffer. But instead of freedom, my poor jaws were suddenly forced open wider than ever, as the mistress yanked the ball in deeper, and clicked the straps another notch tighter.

Now I was properly gagged, the big orb filling my whole mouth, forcing my teeth apart, the straps cutting into my cheeks. It felt like I was having a tennis ball shoved down my throat, and I coughed, trying to catch my breath. I tried to fight down my panic, and breath as best I could. Soon a steady stream of droll, was flowing down my chin, neck, and smooth belly. I frantically begged to be realised, but of course my please were unintelligible.

Then for a moment, again I was alone. With a withering slap to my ass, Miss. Simmons had gone. I heard her rummaging in her bag, then leaving the room. I waited in fear and anticipation.

I was left with a moment to consider how ridicules must look right now. Gagged with a girly pink ball gag, naked except for the matching pink cage on my poor penis. Nude my athletic legs and buns were forced wide, my hand bound. I was the picture of a helpless boy toy. I though I must look like the gay old bar tenders dream come true, and my dick jumped in its cage at the thought.

When Miss. Simmons finally returned she had made a costume change. Naked before, the tall curvaceous women loomed in front of me, now dressed in heels, fishnets, garter belt, and sexy sheer lingerie. She was also wearing an old-fashioned theater mask that covered the top half of her face, like in the movie Eyes Wide Shut.

Miss. Simmons posed before me, knowing her show, caused my caged cock untold misery. She had on a lacy black bra, that badly covered her huge breasts, and left her pancake size aromas only partially covered. Miss. Simmons turned for a moment, teasing me with her huge ass, shaped by her big sheer panties. Her wide cheeks were framed gorgeously by the undies and stockings, and the panties were transparent every were but over her hairy pussy. She looked so good in her outfit, and my poor penis hurt so bad in its pink cage.

As shocking as her dress was, I was more shocked by what Miss. Simmons had in her hands. In one, she held a belt, doubled and ready for a beating, in the other the goddess held a black butt plug and a little bottle of lube. However it was neither Miss. Simmons sexy outfit, nor the spanking belt, nor even the butt plug with its little jewel on the outside end that riveted my attention and stopped my heart.

What shocked, and frightened, and excited me most, what drew my gaze inexorably, was the huge strap-on penis she was now sporting. Strapped around her wide hips, the thick phallus looked well proportioned to the big strong warrior women. It was at least 8 in long, thick vainy and realistic, a bit bigger than my fat cock. The dildo was bright pink, just like my gag, and chastity cage.

She was the big boobed dominatrix out of a comic book, the sexist thing in the world. I felt like the luckiest boy ever, and the most unfortunate. I had fantasized about being bound and dominated by big strong women, but now that was about to be raped by one I started to cry. The tears rolling down my cheeks mixed with my droll, and I moaned with self-pity.

Looking up I saw, Miss. Simmons had put the belt on the table, and was again taking photos, and video. She narrated the video, teasing me like I was a porn star, as she panned back and forth from my blubbering face to her huge pink strap-on.

"Kidnapped boy cries when he sees what's in store for him. Baby you look so cute with your matching pink Chasity cage, and gag. Bright pink cage on your big dick, big pink ball gag in your mouth, and soon a big pink dildo in your bubble butt," she taunted.

Walking around me filming Miss. Simmons, got me from every angle. She showed me off like a piece of meat, my face, my feet and legs, flat belly, caged cock, and swollen balls. She got up behind me and spread my cheeks.

"Were gonna do a little before and after thing here... with this boy toy's ass! Note how nice and smooth the pale skin, no welts. Note the untouched virgin hole," she teased.

The inspection went on and I squealed, and struggled. I didn't want anything in my butt. However all my struggling accomplished was to humiliate me even further before the camera. At the other end of the table, Miss. Simmons propped her phone up against the empty campaign bottle. My deflowering was to be recorded.

Before tonight, I had never done more than kiss a girl. It had been a bit scary, but for the most part I had loved what Miss. Simmons and I had done that night. She had bound, and spanked, and humiliated me, but she had also jerked me off onto her huge tits, and let me lick her from head to toe. Getting to put my lounge in Miss. Simmons's vagina was the best thing I'd ever experienced, I'd do anything to do it again.

I had fantasized and dreamed about meeting a woman like her, but this was too much. I wasn't ready to take a dick in my ass, however it seems I wasn't going to be given a choice in the matter.

Miss. Simmons was behind me now, and I felt cool lube being rubbed on my virgin hole. Taking me by the hair with one hand, I felt something pushing into my tushy. I clenched instinctively, but Miss. Simmons just kept up a steady pressure.

"Just relax boy toy, just let it in. This will go much easier for you if you just relax and breath. You're getting. fucked tonight weather you like it or not, so try and relax," she instructed.

I did my best to obey, willing myself to relax my legs, I snuffled through my

nose and gag, trying desperately to catch my breath. As I slowly opened up Miss. Simmons began to fuck me with the plug, pushing it a little deeper with each thrust.

Then suddenly she shoved the plug to its widest point, holding it there stretching me painfully. I let out a shocked high-pitched squeal, and tried to jerk away, but in her iron grip I was helpless. Miss. Simmons simply holds the dildo there, laughing as I let out my squeaks.

"That's right. Little piggy squeal! Squeal for me piggy," she yells.

At this point the goddess was pulling the plug in and out at a slow diabolic rhythm. Stretching my poor hole to the widest point, then them popping it all the way in. However as much as the first few thrusts hurt, it quickly became more bearable, and my vocalization were now more of shock and humiliation, than of agony.

Finally, Miss. Simmons stopped, and left the plug in me. Coming around front she picked up her phone. Continuing her voice over she circled my, filming me up and down.

"Now as you can see my stunning boy toy is sporting this lovely cock cage, as well as this very cute plug. Now notice the nice jewel butt plug there. Bling. Bling. You can't miss it. A guy could see he's plugged from across the street. And don't worry folks he'll soon be walking the streets in just what he has on now," Miss. Simmons teased.

Despite the discomfort of the plug, it was stimulating me and my penis was twitching in its cage. Premium oozed out the tip and dripped on the fancy wood table.

Putting the phone back down, still filming us Miss. Simmons came back around behind me. First she grabbed me by the hips playfully dry humping me, the big strap-on rubbing between my bubble cheeks. Gently taking my cage and aching balls in her big hands she addressed the camera, "He acts like he dosn't like it. The boy toy cries and begs, but look at this premium dripping out his little cage. He can't get enough. You love it don't you boy toy, you love having that little plug in you ass."

I shook my head vehemently, begging through my gag. Pantomiming for the camera Miss. Simmons opened her eyes wide with shock, sarcastically pretending surprise, "You mean you don't like the plug in your little booty? You don't want me to fuck you like a kidnapped little school girl? Then why did you let me tie you up silly? Now that you tied I can do anything I like."

I nodded jerking my head up and down, begging with my eyes.

"Look I'll make you a deal boy toy. Im gonna take off that cage of your. Nice penis, and if your not turned on, I'll take the plug out and leave your little butt hole intact. However if your hard, Im gonna fuck you like a kidnapped little school girl," she bargained.

With that, Miss. Simmons was pulled the key from where it hung between her massive jugs. She unlocked the chastity device, and my hard young cock sprang out. I couldn't help it, of course I was stiff. My penis had bet raid me.

Toying with my over stimulated cock, Miss. Simmons teased, "Looks like he likes it folks, looks like we got a real slut on our hands. Oh too bad for you boy toy, more fun for me. And look at his nice thick young penis. I don't think it could stretch anymore, do you folks? So fat and yummy, Im so glad it's my property."

Then sliding next to me and grabbing her strap-on in one hand, my cock in the other, she kept teasing. Playing with my penis, displaying me to the camera, as she went on.

"Lets do a comparison shall we. A dick measuring contest. Wow will you look at that, mines bigger. I guess I'll be the man in the relationship then. But before I butt, fuck you..." she mocked.

Miss. Simmons was all ready reaching for the doubled up belt, and my stomach dropped. The terror I felt over the fate of my poor hole, had temporally made me forget I was about to flog. I guess Miss. Simmons wanted to send me home with my ass sore inside and out.

I'd been spanked on my bare bottom many times before by my mommy, but only with a hand. I knew the belt would hurt, but I was totally unprepared for the withering pain that came with the first hard smack.

The force of the blow made me feel like I'd been punched, the strap cutting into my pale tushy and leaving a welt. I bucked my hips forward involuntary, bruising them on the hard wood table. I bellowed into my ball gag, spit flying, a little squirt of premium forced out of my rigid dick, tears streaking my cheeks.

I tried to take a breath, but before I could Miss. Simmons smacked me again, this time even harder. She hit me again and again and again, until I lost count. I screamed and begged, Miss. Simmons whipped me and laughed, and her camera phone recorded every moment of it.

Finally, the big women stopped beating me, and I slumped forward on my belly broken and exhausted. Eventually my sobbing slowed down, I tried to catch my breath. In this position, the camera was close up to my head, and there was no way I could turn my shame filled face away.

As I felt Miss. Simmons rubbing my butt, no longer smooth but criss-crossed with angry welts, I knew I was broken. She had beaten the fight out of me, like a dog. Miss. Simmons had turned me from a man into a crying child, and at that moment I would have let her fuck me, even if I hadn't been bound and gagged. I would have just stood there and taken it.

Again behind me, I could feel Miss. Simmons drawing out my butt plug. She held it at its widest point stretching my hole, her other hand gently caressing my rigid penis. More premium oozes onto the table, and I moan as she pops the toy out.

I felt more lube being rubbed on my hole, and I tried to relax. Next I feel the tip of the strap-on pushing against my opening, and I moan as it slips in. Miss. Simmons had a hand on my hip another guiding in the shaft. I try and arch my back, giving her a better angle. Rocking back and forth, Miss. Simmons slowly forces more of the big pink dildo up my tight ass.

It feels like Im being split in half. I bellow, I squeal. I try to breath, I try to relax and take it in. Inch by inch as I'm violated, the panic in me raises. Now Miss. Simmons has, both her hands on my hips now. She leans in nipping my neck, and I feel her boozy breath on my neck as she whispers, "Half way there boy toy, how's that feel?"

It feels like I'm being impaled, ripped in half, forced open, and it feels wonderful. My penis is rock hard, stretched out, premium dripping from its chubby tip. I'm opening up now, my muscles relaxing as the well lubed strap-on humps into me deeper and deeper.

Finally, I feel Miss. Simmons crotch bumping against my buttocks, and I know she has it in all the way. For a moment, the big sexy women simply held her silicon cock there, slowly grinding it into me at it's very deepest, enjoying my moans of anguish and humiliation. Miss. Simmons rasped with pleasure, "That's right boy toy, take it! Take it all the way up that little virgin ass. I know you love it."

Then Miss. Simmons started fucking me for real. She went slowly at first, but once I opened up, she started pounding me. It no longer hurt, my moans were of pleasure and the deepest shame. I was being butted raped, and as much as my mind and dignity tried to fight against it, my cock loved it.

Through my ordeal I had been terribly aware of the camera phone capturing my humiliation, and now I was struck with another terrifying development. I was about to cum, and it was all gonna be on camera.

As if reading my thoughts Miss. Simmons took me by the hair, making me face the camera directly, and saying, "He loves it folks, he really loves it. Cum for our viewers now. Show them how much you like Mommy's dick in your ass."

My young penis was rock hard, standing out from body oozing. My balls ached, I tried to hold it in. More than anything I didn't want to orgasm like that, but Miss. Simmons knew what she was doing. The amazon goddess knew, just where to grind that dildo into me. It was hopeless, resist as I tried, within a few moments I was cumming.

At the last moment, Miss. Simmons expertly took my penis and aimed my semen, downward, making a neat puddle on the table in front of her camera phone. With one big, and she wrung out my cock, humping me hard as she did so, to force out the last drops.

Then it was the terrible, empty feeling, as she jerked the strap-on ruffly out of my sore rectum. I was gently shuddering, my chin, neck and chest, streaked with droll from my gagged mouth. I looked down at the camera phone, next to the pile of me semen, and wept. I felt so humiliated, used and worthless, and I liked it.

In no time Miss. Simmons had my penis back in its pink chastity cage, and my legs were unbound from the table legs. However I had no chance to slump down on the table, as Miss. Simmons held me by the hair with one had and un-gagged me with the other.

It was a such a relief to relax my jaws, I tried to thank her, but was immediately cut off.

"You'll speak when spoke to boy toy, now lick up that mess," Miss. Simmons said as she pushed my face towards the cum on the table. I was beyond resisting, beyond fighting back in any way, broken. I move hastily towards the mess. I felt empty inside, too beaten even to feel shame, as I lick up my semen for the camera.

Miss. Simmons picks up the camera phone a final time and I lay forward on the table, spreading my legs as wide as possible. I know what's coming. I allowed her to get her "after" shot of my abused cheeks and anus. She comes around again, finishing the video off with a close up of my tear streaked face, and the chilling words, "Well you've seen the before and after on this virgin boy. Thanks for tuning in folks. That was fun, and well have lots more next time."

I had drank a lot that night, losing track of time, and by then the sun was rising. The early light was coming in under the blinds and Miss. Simmons was untying me, yanking my briefs up over my caged dick and sore ass, then shoving me out the front door.

Stumbling off the porch I fell to my knees, and looked up as she threw the rest of my clothes, wallet, keys, everything, out across the morning lawn. Some time after fucking me Miss. Simmons had draped her gorgeous bulk in an untied bath robe. Looking back, I caught my finally glimpse of her lingerie, pink strap-on, and robe framed body as she, addressed me, "By boy toy, I'll see you next Friday... If I feel like it."

From her porch, shaking the key to my cage with one had, she stroked her strap-on cock, and went on, "Take care of that ass. I'll let you know how people respond to your first video!"

With that Miss. Simmons slammed the door, and I heard bolts turning in the lock. I scrambled to get on the rest of my clothes, as the Mexican gardeners across the street hooted and whistled at me like I was a stripper.