Training Sissy Michelle free porn video

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my attention: "Submissive Sissy Slut desperate to serve horny men." "I am a kink-crazed sissy, always pantied and body-shaved and locked in a chastity for 8 months now. I NEED to meet some men who will push me into becoming the biggest slut in town. I NEED to meet some brutal men who will stop by late at night and find me tied up in bed, blindfolded, gagged and listening to some sissy hypnosis files while I sleep. You walk in, untie me, take some pictures and then feed me your midnight snack. Basically, use me however you want and then tie me back up so that I'm ready for the next guy." "If you're not a night owl, you can stop by early mornings to wake me with a delicious breakfast sausage. Or come visit me on my lunchbreak. The point is that I NEED to meet that group of men who want a sissy slut they can use whenever they get the urge." "I am interested in almost any kink you can think of, and if I'm not, who cares? I am a sissy slut which means that I will willing obey your most- depraved orders. I obviously LOVE bondage and group sex, but I also get turned on by posing for erotic photography, being exposed online, being blackmailed, submitting to long hours in a glory hole, water sports, electro-sex and even being a bitch for you and your animals. Whatever your kinky mind can dream up--I will happily obey. Don't believe me? Stop by and let me prove to you just how serious I am about this." "Thank you in advance for your consideration of allowing me the honor of serving you. xoxox Sissy Michelle." I won't lie, her ads always got me excited. That being said, I dismissed them as being little more than fantasy and assumed that Sissy Michelle was a fake because her ads kept popping up weekend after weekend. If she was serious, she surely would have found somebody by now. Plus, I already had a sissy serving me, so I would read the ads to get worked up and then take it out on Candy, my own sissy slut. Candy never knew why I would get extra horny some nights, but had I divulged the cause of my ardor, I'm sure that she would be the first to thank Sissy Michelle for giving her man so many kinky ideas. Fast forward two years and Candy was transferred out of state for a work promotion. I didn't begrudge her the opportunity, especially as she decided to officially transition as part of her move to California. Still, I selfishly wondered who would take care of me when she was gone. I went on the prowl. I found an ad posted in FetLife from a sissy who begged to have a Master train her to be "the biggest sissy cock slut in town." There was something about her writing that struck a familiar chord. Perusing her profile, I found several pictures that I had seen before in Sissy Michelle's Craigslist posts. She had some new shots that were promising, but I wondered why she hadn't been claimed after so many years of looking for men to serve. Donning my Sherlock Holmes' hat, I decided to investigate the slut. I read all of her posts, and more importantly, I noticed whenever somebody responded to her posts. I sent these users private messages asking about Sissy Michelle. Most of them didn't respond, but a few decided to answer my questions. It turns out that she had met with a few of these guys, but wasn't available to serve them on a regular basis. A lot of these guys were only free during the work day, but the sissy had a regular job, so things had petered out. Still, I was starting to get a picture of who Sissy Michelle was, and who she wanted to become. I also started to see why she hadn't been collared by now. So many of these men where obviously married and only looking for a side piece. Most of them balked at the idea of fucking the sissy when somebody else would walk in to fill her other hole. Still, there were a few who had stopped by to sample her services. One of the men confessed that he still fantasized about using the slut. "She got off sleeping blindfolded and tied up in bed," he wrote, "and leaving her door unlocked so I could stop by in the middle of the night and fuck her. It was amazing until I came over one night and found another dude who was already balls-deep in her." "She kind of freaked me out," he admitted, "but also got me hard as a rock. I jerked off on her back porch. Shot my load all over her screen door before I left. I still think of her when I jack off, but I'm not down with sharing my bitches" Okay, so this guy was an idiot. He had a sissy in the palm of his hand, but got freaked out about having to share her. Still, I played the role of an interested friend, and convinced David0678 to share a few pictures with me. My favorite was a picture of Sissy Michelle's face, her mouth agape and filled with a puddle of cum. She was blindfolded in the picture, so her identity wasn't exposed. Well, that's what David0678 thought. The picture had attached meta data that revealed all sorts of useful details. The pictures didn't reveal an exact address for the slut, but I could narrow it down to a neighborhood. I found another user who responded to my queries. BBCfoSure gave me a lot of useful details including links to her other online accounts at ALT and Collar Space. It also turns out that she had been posting erotic fiction to Fictionmania.com and Nifty.org. I must admit that I spent the next several days jerking off while I read her stories. They were super-kinky fantasies, and I decided that I would make them all come true. Okay, yes, I was getting a little obsessed with the sissy. The breakthrough came when I found a selfie taken late at night with the sissy sitting in her car. It was dark, but I could just make out the background details. I already knew the general location, so I got in my car for a scouting expedition. Jackpot. Not only did I find Sissy Michelle's house with relative ease, but she was outside mowing her lawn. She looked like a normal guy doing yard work except that his legs were completely shaven and there was the hint of a bra strap peaking out from underneath his work shirt. I was parked across the street where I wasn't seen, so a few pictures later and a plan started to take shape. First, I had to go home and jerk off. I had so many ideas running around in my head. Truth be told, her fiction stories had given me a lot of ideas, and I was very anxious to put my plan into motion. Step one was to initiate contact and get her attention. I left a comment on one of her stories. "Hey Slut," I wrote. "I love your stories. Wish I lived close enough to make them come true for you." Sissy Michelle didn't know that I lived less than three minutes away, so she responded, "I wish that was true as well. I would kill to have even part of this happen to me." Be careful what you ask for. I suggested that perhaps we should take our conversation out of the public forum. She readily agreed and gave me her kik address. I was rock hard in anticipation of my new conquest when I pinged her. After a little small talk, I sent her a picture of my cock. Now I need to explain, I am blessed to have a 9" pipe, so I always get complimented when I send a picture. Sissy Michelle was no exception, she practically squealed in delight when she saw my python. "OMG, Daddy," she wrote, "I wish you lived close enough to come fuck me with that monster." I demanded that she show me her cock. It was laughably small, and knowing that she loved to be humiliated from her erotic stories, I decided to make her fantasy come true. "What the fuck is that little thing?" I asked. "My sissy clitty," she replied. "That's fucking embarrassing," I said. "It should be locked up in a chastity so nobody will ever have to see it again." She took the bait. "Yes, Daddy, I used to keep it locked up in a cage, but couldn't find anybody to hold the key. I wish you lived here so that you could lock up my little sissy clit and throw away the key." She was obviously fantasizing, not knowing that real-life danger lived just down the street. "Prove it, slut," I wrote. "Prove to me that you're serious and I might just magically show up one day and make all of your sissy dreams come true." "Anything you want, daddy," was her immediate reply. I'd read her fiction and seen her Craigslist ads, so I knew what would get her exited. "Do you have a back yard that's private," I asked, already knowing the answer. When she answered that she did, I told her to put on some naughty lingerie and then send me a picture of her outside. She seemed a little hesitant, so I went to town on her, once again knowing what she had been fantasizing about all of these years. "Sissy sluts don't ask questions. Sluts obey! Prove to me that you are serious and get your sissy ass dressed and into your backyard. I expect to see a picture in 5 minutes!" As a seeming afterthought I added, "I want you blindfolded, gagged, hands handcuffed behind your back, wearing nothing but bra and panties outside. Send me a picture then spend the next 15 minutes thinking about what would happen if I lived closer. Wish on a shooting star and we might magically make it happen." "Yes, Sir," she replied and I logged off, while I gathered my gear and started driving. Within 5 minutes I got a notification that Sissy Michelle had invited me to view her livestream video. I clicked accept and was happy to watch her get ready for me. Slut was wearing a red bra and panty set, plus she had a corset tied tight enough to give her a pretty impressive figure. She set her phone to broadcast as she walked out into the yard. She was wearing a leather hood that hid her face. She strapped in a ball gag, pulled out two pairs of handcuffs and proceeded to lock her ankles and hands together. It was go time. I parked my car and walked over to her house. I had to jump the fence. The noise startled my new sissy, but she couldn't flee in time before I was suddenly upon her. "Hello, sissy," I hissed into her ears. "I told you I would make all of your fantasies come true." I laughed as sissy started to shake in fear. She thought this was just a fantasy roleplay. She thought I lived far away in another town. She thought wrong. Taking out her gag, I demanded to know where the keys to her handcuffs were and she told me that they were on the porch. I quickly uncuffed her, but pulled her hands behind her back and through her ankle chain. Two click later and she was hogtied. I removed her hood so I could see her face. I laughed at the look of fear that played across her face. I started recording. "Okay, sissy," I said. "I've been watching you. You say you want to be a sissy cock slut, so I'm going to make that come true." She started to protest, so I slapped her across the face. "Sluts don't talk unless they are asked a direct question. Is that clear, slut!?" She took a deep breath and answered, "Yes, Sir." Satisfied, I told her to, "Stay right here. I'll be right back." I let myself into sissy's house. It didn't take long before I found her drivers license in her wallet, her cell phone and her lap top. I had everything I would need to make her into my new sissy cum dump. Using her thumb, I logged onto her phone and started flipping through her address book. I quickly found all of her contact information, as well as the email addresses for her family, friends and work. I took a picture of her hogtied in the backyard with her face clearly visible. She flinched as the flash went off. I began composing an email to her mother, asking, "You want to say anything to your mother when I send this picture?" Sissy started to cry and I took pity on her for a moment. But then I remembered that I was giving her what she wanted. I was making her fantasy come to life, so I pressed on. "Shut the fuck up, bitch," I hissed. "I've been following you for years, and I know this is what you want. All those perverted fantasies of yours, they are all about to come true, and you're going to love every minute of it, aren't you slut?" She audibly gulped, resigned to her fate and said, "Yes, Sir." And so we began. First things first, I locked her into a chastity cage. She got hard as soon as I pulled her balls through the base ring, but I squeezed them tightly and her erection subsided. I quickly had her locked in a steel ball-trap cage with a chain around her waist, making sure that she couldn't pull free from the device. "This will have to do until I can get you pierced and locked into something more permanent," I told her and smiled as her clitty twitched inside of her cage. "Doesn't that sound great?" I asked, and the stupid slut dared to say that, "No, please Sir, I'm scared." I laughed loudly. I was hoping I'd wake the neighbors. "Tough titty, sissy," I said. "Time to make your sissy fantasies come true." I explained how her new life would work. I began by reading off the names, phone numbers and email addresses of her family members, work contact and friends so that she knew I was serious. That got her full attention. "I remember your Craigslist ads. I've read your online fiction. It's all about to come true. Isn't that exciting, sissy?" I asked. "Yes, sir," she wisely answered. I could see in her eyes that she was resigned to her fate, so I instructed her to look at her camera phone and tell the world why she wanted to be the biggest sissy in town. Her first effort didn't meet my standards, so I dragged her over my lap and spanked her until she was crying out in pain. I pressed record on the phone and told her to try again. It took four tries until I had the video I was looking for. "My name is sissy Michelle," she said with a mixture of fear and erotic desire in her eyes. "I have been claimed by my Master who has promised to make me into the biggest sissy cum dump in town. I am begging to serve any horny men who wants to use me whenever they feel the need. Anytime you're horny, this sissy is here to satisfy your needs. All I ask is that you take pictures each time and send them to my Master so that he knows I am being a good sissy slut." I gestured for her to continue. "I am yours to command, so if you have a kinky fantasy, I am your slut," she confessed. "Use me as your urinal, tie me up and leave me helpless until the next man shows up to breed me. Bitch me out to your dogs. Force me to walk the streets as a sissy whore. As long as it is okay with my Master, I will obey your every command." Well damn, that was better than I expected. I instructed to reveal her boi name, phone number, address and social media contacts on camera. Then we were done and her new life would truly begin. I dragged her over and had her suck my cock. She was okay, but nothing special. No worries. Practice makes perfect and she would be getting lots and lots of practice in from here on out. I flipped her over and pounded into her sissy pussy. It didn't take long before I filled her up with a geyser of my cum. She moaned in appreciation as I came. Well, if that's what she wanted, who was I to deny her? I told her then and there--"I am your Master. I will breed you anytime I want, and you will thank me for the honor of receiving my cum." I gathered her breath and said, "Thank you daddy for fucking me and helping to make me into the perfect sissy slut." It was getting late so I dragged her into her bedroom. I threw her across the bed and tied her spread eagle to the four posts. I added a fifth rope around her sissy balls so that there would be something tugging at her all night long. I then downloaded a sissy hypnosis playlist onto her phone. I pressed play and put it on repeat. "Nighty night, sissy," I said as I put the earbuds in and blindfolded her. "Be a good sissy cum dump and we'll start your training in the morning." And I left. Well, she thought I left. I actuality I slept on her couch, but I wanted to get her used to her new sissy schedule. I have a friend that works overnights at the plant. I texted him and told him to stop by when he got off work. I'm not sure that sissy got any sleep that night, but who cares? At 6:15am we dragged her out of bed and gave her the most brutal spit-roasting we could manage. We took lots of pictures. Then we abruptly left. Well, kind of left. AT 9:15am I started sending emails to sissy at work. I attached a picture of sissy being used this morning. I told her that I was going to send this picture to her boss unless she sent me a video thanking me for helping her become a perfect sissy cum dump. Sure enough, five minutes later I received a video of sissy in the bathroom stall, writhing around as she recorded, "Thank you Master. This morning I was honored to serve Master and his friend. I don't know who he was, but he had a big cock. Not as big as Master's, but it still felt wonderful. Thank you, Master, for finally making me become the perfect sissy cum dump. Please make this happen every day!" It was better than I'd expected, but you can't go too easy on a new slut, so I instructed her to try again, but this time make it kinkier. Five minutes later she complied. I loved the look of fear in her eyes as she started the recording. She began with her given male name, cell phone, Facebook and street address and the proceeded to describe how much she loved this morning's spit-roasting. I turns out that she had a large flashlight there at work, and she rode it like a street whore while she confessed her darkest fantasies. Damn. I knew I had broken the slut. I also feared that she might be kinkier than I had thought. No worries. I was up to the challenge. I sent her a text, asking when she got a lunch. At noon I pulled up to her work and she practically skipped over to my car. She didn't say a word as I drove off. I pushed her down onto my cock and she bobbed up and down on me until I had to pull over into a parking lot as I filled her stomach with my cream. After I recovered, I directed her to the glove compartment where she found a large butt plug. I had her pull down her panties and lodge the plug in place, then I kicked her out of the car and made her walk back to work. Yes, this was going to work out just fine. So, Craigslist is gone, but there are other places to find local kinksters who might be interested in using a sissy on a regular basis. I spent my day tracking them down and judging their interest. In a bit of a surprise, most of them seemed to be a little flaky. Still, there were more than a few men who seemed like they wanted to play. I only needed a few to begin with. Once we started posting videos online, I'm sure that men would start lining up to use the slut. BangMaster127 was the first to sign up. I'd met him at a munch before, so I was happy to enlist him in my plan. He already had a sissy of his own, a slut who hadn't earned her name yet, so he just called her Cunt of Slut or whatever degrading name he could think up. I met him at a coffee shop and we made some plans for sissy Michelle. Cunt hid under the table and serving us while we spoke. BangMaster mostly wanted a slut he could use as a toilet. It's not really my thing, but I am certainly interested in having a sissy who can swallow gallons of piss. I promised that Sissy Michelle would be available to be used as BangMaster's personal toilet and he immediately signed on. He took the opportunity to prove how serious he was when he started pissing down Cunt's throat. I told me what he was doing, and I was certainly attracted to the decadence of using a slut as toilet--in public no less! Sensing my interest, he motioned Cunt over to me and invited me to let loose. This was my first time to piss into a slut. Cunt swallowed every drop of my stream, and I decided to make this a part of Sissy Michelle's regular training as well. I was so turned on that I allowed Cunt to service me to completion right there in the coffee shop. We were in a booth and Cunt was hidden by our legs, but I was convinced that if we had dragged her out into the open, she would have still willingly sucked us off right there in public. That's exactly what I wanted for my new sissy. And since she kept saying that she wanted to be the biggest sissy slut in town, we decided to quickly put her into a competition with Cunt. It was getting late, so I texted Sissy Michelle and told her that I'd pick her up from work. I pulled into her company's parking lot at 5pm and found her already outside, waiting for me. She pranced over to my car, but I had my doors locked. I popped the trunk and after a moment's hesitation, she lowered her head and climbed into the trunk. I heard the trunk latch closed just as I looked over to see one of her co-workers watching us. Perfect! I drove a few miles to a gas station. I parked and went inside to buy a roll of duct tape. Popping the trunk, I found sissy shaking in fear in the trunk. I threw the duct tape into the trunk and told her that when we stopped next, I expected to find her naked and tightly bound in nothing but tape. She just said, "Yes, Master," as I slammed the trunk closed and drove off. I pulled over fifteen minutes later to check on her. She had been a good sissy. Her clothes were neatly folded at one side of the trunk. She had wrapped the tape around her ankles, knees and upper thighs. She had also fashioned the tape into a rope of sorts, attaching her chastity firmly to an exposed bit of metal at the rear of the trunk. She had also used the tape to cover her mouth and eyes, and in a fit of enthusiasm (that I absolutely approved of) she had wrapped the tape around her head so it was firmly stuck to her hair. Finally, she had managed to wrap the tape around her wrists. It wasn't very secure, so when I pulled over to check on her, I put some extra tape around her wrists. I did a wrap around her elbows as well, and adding to sissy's initiative, I used the rest of the roll to completely encase her head in duct tape. I decided to let her stew. I went to the movie theater and parked in the lot. I popped the trunk and told her to be very quiet while I enjoyed the film. Before I left, I took her phone and pressed play on the sissy hypnosis file. I had to rip the tape a bit so I could press it up against her hear. Then I taped her phone down and slammed the trunk shut. I returned three hours later to find sissy writhing in the trunk. It's a good think I had parked on the upper level, as sissy's motions were causing my car to bounce up and down by this point. Now I hadn't been a good theater patron, and had spent most of the movie on my phone, looking for men to help me train my new sissy. By the time the final credits rolled, I had my night planned out. I went to my car and made sure that sissy was still tied up before I drove off. It was getting dark when I pulled into the driveway of sissy's first appointment. An older man stepped out as I pulled into his driveway. He motioned me to pull into his garage where we would have some privacy. I did so and popped the trunk. The man stepped forward and smiled when he opened the trunk. "Nice," he said. "So, this would be a regular thing?" he asked. "Whenever you get the urge to use a sissy," I replied. We dragged Sissy Michelle out and into the man's backyard. He pulled out a knife and cut away the duct tape, He didn't seem to care that a lot of sissy's hair was pulled out as we unwrapped her head. Nor did I. In order to make certain that sissy was cleaned out and ready for cock, we put the garden hose up her sissy hole. The man turned on the faucet and we both laughed as sissy struggled to take the torrent of water into her sissy pussy. We had to hold the hose in place as the water made certain that her sissy pussy was clean and ready for cock. I was a bit surprised that this old man was ready to provide my sissy with multiple cocks. He dragged her out into the backyard and put her down on her knees. He went over and unlocked his kennel, and I get excited when I watch his German shepherd bound out and immediately start lapping at sissy's hole. The old man mounted her face while his dog climbed up on her back. It took a minute before the dog found sissy's hole, but once he was inside, he began breeding her like the animal he was. This was when the old man started assaulting sissy from the other end in earnest. This is also when I pulled out my phone and started recording everything. Old man and beast pounded into sissy until it was obvious that she was being knotted. Her cries of pain are what pushed the old man over the edge and he filled sissy's mouth with his cum. I took this moment to record sissy's total depravation. I trained my phone on her face and instructed sissy to say what was happening. "I am sissy slut Michelle," she confessed. "I have just serviced one man while his dog fucked me like the bitch I am. He is still knotted in me, and I love being full of his doggy cum, because I am a kinky sissy slut and I am willing to do anything to please my Master." As if on cue, the old man began pissing in sissy. I got it all on camera. I made arrangements to come back before I left. I noticed that sissy had several hunks of hair missing when I shoved her back into the trunk. So, I stopped by the grocery store before our next appointment. I bought a pair of hair clippers, a razon and some shaving cream. I figured it was time to shave sissy's head, as she had already messed it up beyond repair when she wrapped the tape around her head, I pulled into the next address and was once again met in the driveway. This time it was two men who couldn't wait to drag sissy out of the trunk and begin pounding into her holes. She was impaled on their cocks in seconds, and I took this opportunity to begin shaving sissy's head. To her credit, she didn't stop sucking cock or slamming back into the cock behind her while I removed all of her hair and then using a razor, I shaved her as smooth as possible while she was slurping down on cock like a sissy possessed. Two cum loads later and I loaded sissy back into the trunk, but not before giving these two men her home address and letting them know that they could stop by anytime they wanted to use this slut. It was nearly midnight so I decided that our next stop would be the tattoo parlor. There were quite a few people in the shop when we pulled up, and they gawked when I popped the trunk and dragged a naked sissy into the shop. I made sissy stand naked in the lobby while I went to search out the manager. By the time I returned, sissy was surrounded by several men and already had one cock down her throat. I let her finish the man off and gave him sissy's phone number before taking her into a back room. I had already told the manager what I wanted, but I let Sissy Michelle tell him what she was looking for. And so I unlocked sissy so she could get a Prince Albert ring in her clitty head. We also replaced the bars in her nipples with 0 gauge rings that were immediately JBWelded shut. I also put a ring in her nose--just because I could. I had sissy's nipples tattooed a bright pinkish red, and I used the same color to write "Sissy Cock Slut" in big letters across her groin. For her part, sissy seemed to love it, and begged me to do even more. She was already out of her cage, so we tattooed "Sissy Slut" down the shaft of her cock. We gave her a tramp stamp that read "Insert cock here," with an arrow pointing down to her sissy pussy. And because sissy was still begging for more, we shaved off her eyebrows and tattooed high arches onto her face. Since we were already there, I had her eyes outlined with a sultry black line as well. I would have left it at that, but sissy was so desperate by then that she was begging to service everybody in the shop. Who was I to deny her? We took her into a back room and she blew the tattoo artist, the shop manager and the four customers. I filed it all. I gave all of the customers her home address and cell phone number. We had two more stops before the night was finished. The first was a man who just wanted to fuck her. It seemed so anti-climactic, given what hap happened earlier in the night, Still, his cock was pretty big, so I figured that sissy would like seeing him in the regular rotation. I gave him sissy's contact details. Our last stop proved to be the kinkiest stop of the night. I drove out to a farmhouse on the outskirts of town. I was met by a farmer and his two sons, all of whom seemed very excited to meet Sissy Michelle. The farmer shook my hand and told me that he's been looking for a new sissy for several years now. Without preamble, his son put a collar around sissy's neck and dragged her out to the barn. I followed them out and laughed while I watched sissy being tied down to a fucking bench. The farmer called on his sons to "release the hounds." There were fours dogs that fucked sissy that night, while the farmer and his sons fucked her throat. I filmed it all. We left the farm around 7am, promising to return to sample some of the larger animals. I took pity of sissy and let her ride upfront with me, Unbidden, she sucked my cock as we drove back into the city. She was a mess when we pulled into her driveway--naked and stinking of cum. I took pity on her and asked her if this was truly what she was looking for? She had been balls deep on my cock when I asked, but she immediately popped up and asked to see my phone. I complied and watched as she opened up mu photo album, Selecting the videos that showed her sucking cock and being fucked by dogs, she chose the export function and sent it to both her boss and her mother. I laughed. There's no coming back from that. I knew then and there that I had found my new sissy cum slut and my mind filled with all sorts of kinky plans for my new slut.