Helplessly Caught

Helplessly Caught turtleneckfan@hotmail.com Copyright 2007 All rights reserved

The neighbor who moved into the apartment right next to mine pushed virtually every button I have - Jessica had long blond hair, bright blue eyes, a gorgeous smile, small perky breasts, a nice, firm ass, and legs that went on and on and on. To top it all off, her wardrobe was taken right out of my own fetish fantasies - she loved short skirts, tall boots, knee socks, and turtleneck sweaters. Once I even saw her wearing all of these items at the same time, and I almost creamed in my jeans. I will never forget the image: she had on black leather boots with pink knee socks peeking out of the top of the boots, a short pleated miniskirt with a white, grey, pink and black plaid pattern, and a pink cable turtleneck sweater with an enormous collar that hugged her chin. Her hair was pulled back in a ponytail, and she literally knocked the breath right out of me.

We had talked before, and I guess we could be considered as almost friends. On the day she wore that outfit, I could not take my eyes off of her, and when she struck up a conversation, I could barely manage to talk. I desperately hoped that she would not notice the enormous bulge in my pants.

Jessica told me that she was going away for a week, and she asked if I would be willing to water her plants for her while she was gone. Without hesitation, I took her up on it, and I secretly could not wait to check out all of the fabulous clothes in her closet. She gave me a copy of her apartment key, gave me a peck on the cheek, and told me when she would be back. I went back to my apartment and jerked off to visions of Jessica in my head. Not just any visions, mind you, but visions of her in that outfit, being bound and gagged and helpless as I fucked her hard.

That night, I watched Jessica drive away, and I had to restrain myself from bolting over to her apartment. I felt vaguely guilty and dirty for wanting to go through her things, and I actually made it most of the week with just watering her plants as she asked. However, the weekend arrived, and with Jessica due back sometime on Sunday, the urge to go through her things became more than I could handle, and I broke down and went into her closet.

With my heart thumping, I flipped on the light in her walk-in closet, and I was in my own fetish heaven: boots and heels were neatly lined up on the floor; blouses, skirts and dresses lined an entire side of the closet; and the shelves in her closet were overflowing with soft sweaters. On the opposite side of the closet, Jessica had placed a dresser, and in those drawers I found her panties, bras, and a huge collection of knee socks. Tucked away in the back of the closet was a laundry hamper, and I could not help but notice the outfit that she had worn the day she asked me to water her plants laying right on top. Then I noticed a large box wedged behind the hamper, and curiosity got the best of me.

I opened the box and was utterly blown away by what I found - Jessica apparently had not only an enormous collection of sex toys, but she also had a large collection of bondage gear: gags, collars, hoods, handcuffs, manacles, spreader bars, posture bars, and stuff that I honestly had no idea what they were for. I was almost overwhelmed by the thought of Jessica being into this kind of stuff. I would have given almost anything to see her wearing that outfit and helplessly tied up, but she was so out of my league, I did not even consider it to be a vague possibility.

Being careful not to displace anything, I returned to my apartment and fantasized about what I had found. As I thought about ways to secretly get some pictures of Jessica dressed and bound, a twisted thought occurred to me - what if I got someone that looked like Jessica to come over, wear her clothes, let me use the bondage equipment on them, and then take some pictures? I was so excited about the thought until the reality of it all set in. First off, I did not know anyone that looked like Jessica, and second, even if I did, I seriously doubted that they would agree to wear a stranger's clothes, be tied up and gagged, and then photographed.

Then another thought crossed my mind - I was pretty small for a guy, and I really was not much bigger than Jessica. I started to consider the possibility of dressing up like Jessica, trying my hand at some self-bondage, all in front of my camcorder. That way, I could take as many screen shots as I wanted of what I hoped would appear to be Jessica bound and gagged. My face could even be hidden by one of her bondage masks, or even swapped out with my photo image program.

I dismissed the idea almost as soon as it occurred to me. After all, I had no interest whatsoever with wearing women's clothes, nor was I all too interested in being tied up myself. But I could not erase the thoughts of having pictures of a Jessica look-alike dressed, bound and gagged. Finally, my arousal got the best of me, and I impulsively decided to go for it.

My mind raced, and I sprang into action. First I showered, and upon thinking of getting the most realistic shots that I could, I shaved my legs - after all, Jessica had smooth gorgeous legs, and my hairy legs would be a dead give-away. I finished showering, pulled on shorts and a T-shirt, grabbed my camcorder and laptop, and went over to Jessica's apartment.

First I filmed Jessica's closet so I could put everything back the way I had found it. Then I set up the camcorder in Jessica's bedroom, right next to her full-length mirror, and connected it directly to my laptop for easy download. I turned the camcorder on, stripped off my clothes and stepped into Jessica's closet. I had already decided what I was going to wear - the exact same outfit that Jessica was wearing when she asked me to water her plants, and conveniently, that outfit was laying right on top in her hamper.

I carefully removed the outfit and laid it out on Jessica's bed. I lifted a pair of pink satin panties that Jessica had apparently worn up to my nose and inhaled her musky scent, and I immediately was fully aroused. I stepped into the panties and pulled them up my smooth, hairless legs. I tucked my erection inside of her silky panties, hoping the bulge would not stretch them out. The sensation of the silk against my hard-on was almost more than I could handle.

Next I put on the matching bra that she apparently wore. I remembered seeing some silicone breast enhancers in one of her dresser drawers, and I retrieved those and inserted them into the bra to fill me out. Next I put on the pink cable-knit knee socks, and the soft, slightly fuzzy texture of the socks felt incredible against my bare legs. I pulled on her miniskirt, and I was relieved that I was able to fit into it without much trouble. Then I pulled on her turtleneck sweater. It was incredibly soft, and the collar was a good six inches folded over. Finally, I pulled on the black leather boots. The fit was a bit tight, but I did manage to pull them on. I teetered a bit, being unaccustomed to the high heels, but I eventually found my balance.

Next I went through her hidden bondage box. I found it really difficult to decide what to use on myself, and I tested everything out to make sure I could release myself when I finished. I first chose a full leather hood with holes for the eyes and mouth, and a hole at the top for a ponytail. I again returned to the drawer where I found the silicone breast enhancers, and I pulled out a blond ponytail hair extension. I honestly had no idea why Jessica would have this, given her gorgeous long blond hair, but perhaps with was from a time when she had shorter hair.

Regardless, it would work for my purposes.

I went into her bathroom, rummaged around a bit, and found some of her makeup. Because only my eyes and lips would be visible through the bondage hood, I only picked out some lipstick, eye liner, eyeshadow, and mascara. The lips were easy, and I applied several coats of the glossy pink lipstick. The eyes were much harder, and I struggled to apply the eyeliner.

After several attempts, I applied it as well as I could, and then I applied blue eyeshadow and the mascara. I then fastened the blond ponytail to the crown of my head and carefully slipped the bondage hood over my head. After some adjustment, I was able to pull the ponytail through the top of the hood, and I laced it up tight.

I returned to the closet and retrieved some sex toys and the rest of the bondage equipment that I would need, and I walked out into Jessica's bedroom. I stood in front of the camcorder and, for a while, simply stared at my reflection in the mirror. I was blown away by how much I really did look like Jessica, and the image of the "faux" Jessica with a bondage hood made me harder than I think I've ever been.

I got down on my knees and grabbed a large, realistically shaped dildo, complete with veins and balls. I then watched my reflection in the mirror as I licked the shaft of the dildo. It was surreal, and I was able to ignore the fact that it was me licking the dildo, and in my own fantasy-land, I was watching Jessica lick a large cock. I then started to suck on the dildo. The image of Jessica's pink lips wrapped around the thick shaft of the cock was incredible, and I even worked on deep-throating the dildo. I gagged repeatedly, but the end result - a perfect shot of "Jessica" taking an entire cock into her mouth - was priceless.

Then I decided to do something a bit more daring. Keeping the dildo in my mouth, I pulled out yet another realistically-shaped dildo. I bent over, lifted my skirt, and lowered my pink panties just enough to expose my ass (but not enough to ruin the effect my exposing my own balls and cock). I placed that dildo between the cheeks of my ass and simply stared at my reflection - there was Jessica with a cock in her mouth and a cock at her ass. I decided that I just had to go further with that image, and I pulled out a tube of lubricating jelly. I rubbed some around my sphincter and all over the dildo. With the first dildo still firmly in my mouth, I reached around and placed the second dildo against my sphincter. I braced myself for the pain that would follow, and I slowly pushed the dildo into my ass. I was so aroused by the reflection in the mirror that I barely noticed the pain as I inserted its entire length deep into my ass. Then I fucked myself with the dildo for a good five minutes.

I was ecstatic with the images that I had already recorded, and I decided that it was time for the bondage. I proceeded to assemble a piece of bondage furniture that I had only seen on-line: it had metal bars in the shape of a capital "I" that I placed on the floor, with each cross-piece having cuffs fastened to the end of them. Once in place, it would force me into a doggie position. There were also two vertical bars, one placed near where my stomach would be, and the other near where my head would be. The bar near my stomach had a large U-shaped support and a locking leather strap, and the bar near my head had an attachment that would secure one of the dildos in my mouth. Finally, a fucking machine was bolted to the rear of the contraption, and once adjusted, it would force a dildo in and out of my ass.

With my heart pounding in my chest, I first locked both of my ankles in the rear cross-piece. After some adjustment, I set up the fucking machine so that, once locked into the bondage gear, it would be impossible for me to remove the thrusting dildo from my ass until I unlocked myself from the contraption. I inserted the dildo attached to the fucking machine into my ass, turned the machine on so that it slowly worked the dildo, which also vibrated, in and out of my ass, and then knelt down and rested my stomach over the first vertical support. I fastened and locked that strap securely around my waist. I tested everything out, and I had essentially immobilized myself from the waist down, and sure enough, there would be no way for me to wriggle out from the dildo sliding in and out of my ass. I then reached forward and securely locked my left wrist into the front cross-piece. I opened my mouth and took a large portion of the dildo attached to the front vertical support into my mouth, and I then locked the collar attached to that support to the back of my bondage hood. I tested that out, and there would be no way for me to pull back far enough to eject the dildo from my mouth. Now came the hard part - securing my right hand without the use of my left hand. I first threaded the strap for my wrist through its buckle, leaving just enough room for me to wiggle my hand through. I was then able to grab the strap and, after some finessing, tighten it and buckle it securely in place. I grabbed the final lock, and with a deep breath, I snapped the lock closed.

I had angled myself in such a way that I could see most of my profile in Jessica's mirror. Although I had not considered the fact that my head would be essentially immobilized with the dildo in my mouth, I was luckily able to get a glimpse of myself in the mirror. I was so unbelievable aroused by what I saw - I saw what appeared to be Jessica dressed up in my favorite outfit and helplessly bound, with a vibrating dildo sliding in and out of her ass and with a dildo firmly locked in her mouth. I even struggled for effect and made desperate noises through the dildo in my mouth, and then something happened to me that has never, ever happened to me before - I actually had an orgasm without even touching myself. It was utterly surreal to watch "Jessica" in the mirror moan and buck with the orgasm, and to have the orgasm myself. By the time I finished shooting my load into Jessica's panties, I was lightheaded and dizzy.

After recovering from one of the most intense orgasms of my life, I grabbed the key that was strategically placed next to my right hand to unlock myself. I had not practiced unlocking the key in the position I was in, and I found it to be very difficult. I could not really see the lock because my head was virtually immobilized, and I probably spent 20 minutes struggling to get the key into the lock. I figured that I could eventually get it unlocked, and I suppressed the urge to panic - until I heard Jessica's front door being opened.

I thought I would have a heart attack, and I frantically struggled to get the key into the lock. My mind raced on how I was going to extract myself from this predicament, and in my panic, the unimaginable happened - I dropped the key, and I watched as it bounced off just out of reach.

I was literally frozen in terror as I heard footsteps approaching Jessica's bedroom, and my eyes were wide as saucers when Jessica stepped into her bedroom and laid her eyes upon me. The incredible part was that, even in my panic-stricken and helpless state, I was still blown away by Jessica's beauty - she was wearing a tight-fitting angora turtleneck dress and four-inch fuck-me heels and again had her hair pulled back in a high ponytail.

Jessica froze when she saw me, and she had a look of pure shock on her face.

She took it all in, and then she said, "What the fuck??? Who in the hell are you, and why are you dressed in my clothes and using my toys? How did you get in here?"

Well, all I could do is grunt through the penis in my mouth, and I looked pleadingly up at her. Apparently, either my grunts must have sounded familiar to Jessica or something else gave me away, and her hand flew up to her mouth as she gasped, "Oh my god!!! Steven, is that really you?" I affirmatively grunted that it was, in fact, me.

I was a bit relieved when Jessica giggled at the sight of me, as I was initially terrified that she would be furious. Then Jessica said something that I entirely did not expect: "Hey Craig! Hey Anthony! Come in here! Just wait til you see what I found!"

I gave out a little desperate moan of renewed terror as I heard more footsteps approaching, and I again looked pleadingly up into Jessica's amused eyes. Then Craig and Anthony entered the room.

"Get a load of this, guys!" said Jessica with glee. "Craig, Anthony, I'd like you to meet my next- door neighbor, Steven. Steven, meet my friends, Craig and Anthony."

Craig and Anthony were clearly amused, but also puzzled. Jessica told them both that she had no idea what I was doing, dressed up in her clothes, securely bound, with a cock in my mouth and a cock sliding in and out of my ass, and that she was just as surprised and puzzled as they were. Craig pointed to the camcorder and suggested that they rewind the tape to see what was up. None of them moved to unlock me or remove the dildo from my mouth, and I helplessly watched as they rewound the tape and hit play.

The tape clearly showed me stripping off my shorts and t-shirt, and then laying out Jessica's outfit on the bed. I was mortified as they watched me sniff Jessica's panties, and even more humiliated as they watched me put on Jessica's outfit, suck on the dildo and fuck myself up my ass with the second dildo. Then they watched as I set up the bondage equipment, locked myself in, and then struggled and squealed. I wanted to close my eyes at the next part, but it was like watching a train wreck, and I watched the tape of me shaking, bucking and moaning as my orgasm over took me. Jessica laughed out loud and said, "Holy crap, guys! I think he just came in his panties! Well, actually, my panties. Ewwww." If my cheeks had not been hidden by the bondage hood, they could have seen them flush bright red with humiliation. The tape continued with my struggles to release myself, and it showed me dropping the key and Jessica's entrance into the room.

When the tape ended, Jessica told Craig and Anthony that she needed to talk to them in the other room. She retrieved the key to my locks, slapped my ass, and she winked at me as she told me not to go anywhere. I struggled to get free while they were gone, but to no avail. All the while, the vibrating dildo continued to slide in and out of my ass.

Jessica returned after a while, and to my surprise, Jessica turned the camcorder back on. She got down to my eye level and rhetorically asked me why I had done this to myself. She then asked if I wanted to be her, or if I just wanted to see what it would look like to have her bound and fucked. It was like she read my mind with the last question, and I managed to utter an affirmative grunt through my gag. Jessica smiled when I did, and told me that she would do one better for me - she would show me exactly what she liked to be done to her when she was tied up. Jessica saw the confusion in my eyes and just laughed. Then she said, "I hope you enjoy it as much as I do!"

Still confused, I watched in shock and horror as Craig and Anthony entered the room completely naked and both with massive hard-ons. Jessica again chuckled and whispered in my ear that she simply loved to get double-teamed when she was tied up, and now I would get to experience it up close and personal, but this time with some real cock. I shook my head no and tried to protest through the penis in my mouth, but Jessica jumped up and slapped my ass, hard. She informed me that I really did not have a choice in the matter - I had done this all to myself, and I had violated her privacy, and as I clearly did not mind having a cock in my mouth and buried up my ass, she would give me what I apparently wanted so badly. She then noted that I was hardly in a position to object.

Jessica then turned off the machine fucking my ass, unbolted it, and removed the dildo from my ass. She grabbed the lubricating jelly and slowly spread it all over Anthony's engorged cock. I watched in the mirror as Anthony then walked behind me and placed the tip of his cock between the cheeks of my ass and against my sphincter. I whimpered through my penis gag as Anthony grabbed my hips and slowly pushed forward. I squealed in pain as he forced the head of his cock into my ass, and I was entirely helpless to stop him. He slowly worked his entire shaft into my ass until I could feel his balls brush up against my own balls.

Then Craig stepped up in front of me and placed the tip of his cock inches from my face. I could see pre-cum glistening from the tip of his cock, and he brushed it onto my lips, which were still obscenely stretched around the dildo in my mouth. Jessica then unlocked my neck from the front vertical support, and as she did, she warned me that I had best do what I was told. She removed the dildo from my mouth, and she told me to open wide. Feeling utterly trapped and not seeing any other options, I did as I was told, and Craig inserted his cock into my mouth. He ordered me to suck as he slowly pumped his cock in and out of my mouth, and Anthony then began to slowly fuck my ass.

As they both fucked me, I could not help but see my reflection in the mirror. Much to my dismay, I actually started to get hard again - the vision of what appeared to be Jessica tied up and being double-teamed was turning me on. At that moment, it occurred to me that there might me something wrong with me - after all, it was not Jessica who was tied up with a guy fucking her ass and a guy fucking her ass - it was me. Regardless, I could not take my eyes off of the mirror, and I was soon rock-hard, and I let out a little moan.

Jessica heard me moan, and she reached beneath my skirt. She just chuckled when she felt my raging hard-on, and even though I was utterly humiliated and was being fucked by two men, her touch was like electricity. She then started to jerk me off as I was double-teamed. The guys fucked me for at least fifteen minutes, and Jessica patiently stroked my cock. I could not hold back, and I was powerless to prevent my impending orgasm. I started to moan through the cock in my mouth, and Jessica picked up the pace. In seconds, I had what was hands down the most intense orgasm of my life, and I almost passed out from the intensity of it all.

The involuntary constriction of my sphincter around Anthony's cock apparently was more than he could handle, and as I ejaculated, I heard Anthony start to moan. As Anthony shot an enormous load deep inside of my ass, Craig also started to moan. I first felt his cock twitch, and suddenly cum started to flood into my mouth. I reflexively swallowed, and at the same time, my own orgasm completely overtook me, and I moaned in pure ecstacy. Craig pulled out at that very moment and shot the rest of his load into my open mouth. The humiliation of having the most intense orgasm of my life at the very same time as having a man shoot his seed deep in my ass and another man shoot his seed deep in my mouth was almost more than I could handle.

Anthony pulled his cock out of my ass, and then Craig pulled his cock out of my mouth. Jessica first told me to lick Craig clean, and then she placed her cupped hand, which had caught my own semen, to my lips. She ordered me to lick her hand clean, and when I had finished, semen coated my pink lips and dribbled down my chin.

Jessica then lifted her sweater dress and lowered her panties. She shoved her crotch into my face and ordered me to lick her pussy. Watching me get fucked by two guys must have really turned her on, and she was dripping with her juices. I lapped at her the best I could given my restricted movements. After several minutes, I apparently hit her sweet spot, and she grabbed my head and ground her crotch into my face. I licked furiously, and she came hard.

Jessica regained her composure and told me to open wide again, and she inserted a large ball-gag in my mouth and tightly buckled it in place. She turned off the camcorder and sat down at my laptop. She opened my e-mail account, and she proceeded to forward my entire address book to her own e-mail, and then she forwarded the entire file downloaded from my camcorder to her e- mail. She told me that the tape would be her insurance that I would be a good little sissy for her, and slapping me on the ass, she winked and told me that she had always dreamed of owning her very own sissy boy, and now I had made her dreams come true....