My First Night Of Being A Sissy Cumdump free porn video

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Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved to college that all changed though. As soon as I got settled into my private dorm room, I thought it would be nice to spend the evening dressed like a little slut. I decided to wear my schoolgirl outfit that night. So I took a nice hot shower and shaved myself smooth from the neck down. I went back to my room and started to get dressed. First I rolled my white stockings up my legs. The nylon felt great on my smooth skin. Then I put on my mini-skirt which barely covers my ass and pulled on a pair of white cotton panties with pink trim with the word slut written across the ass. I put on my button up schoolgirl top with my hot pink bra underneath. I slipped on my short black wig and was almost ready. Next I topped off the outfit with my 5 inch stripper heels. I looked in the mirror and saw a slut begging to be fucked. I knew right then I needed to be filled so I pulled out my butt plug, and after lubing it and myself up, I slowly began to insert the plug into my wet hole. As soon as it was fully inside of me I sat down at my computer and the slut inside of me took over.

I got on craigslist and created an ad that said I was a total cumslut and needed a daddy to put me in my place. I included a picture of my ass bent over ready to be fucked. It was only about 20 min later when I got my first reply. It was a guy in his mid fifties with an 8 in cock and a place to host. That was all I needed to hear to reply that I was ready to come right over. While I waited for his address I took off my wig and heels and put them in my backpack. I slipped on a pair of sweat pants and a hoodie over my schoolgirl outfit and I was ready to go. I checked my mail and there was his address. I picked up my backpack replied that I was on my way and walked out the door. About 10 minutes later I was pulling into his driveway. I walked up to the door and it opened before I even knocked and I was greeted by a middle aged man with dark hair and glasses. I walked in and he pointed me to the bathroom to get ready. It didn't take long since I only had to put on my wig and heels. I also put on some bright red lip-gloss for the finishing touch. I walked out of the bathroom and found him on the couch rubbing his obviously hard cock through his shorts while watching a porno on the TV.

I waste no time and get down on my knees in front of him. First I licked and sucked on his smooth balls then I licked up the shaft till I made it to the tip. Then I took all of him that I could down my throat in one quick motion. I was about an inch away from taking the whole thing down my throat. I eased off and gave him a nice wet blowjob for about 10 minutes. Around that time he wanted to get a little rougher and grabbed my head and forced me all the way down on his dick until his balls were pressed on my chin and I was choking. He released me and shoved his 8 inches back down my throat about 10 times and the said "its time for you to get fucked." I was so ready to be fucked.

I stood up and reached around to make sure I was still well lubed and realized that the butt plug from earlier was still inside me. I was so excited to come get fucked that I forgot to take it out before I left. I slipped it out and got on all fours on the couch. He handed me a bottle of poppers and I took 4 huge whiffs and held it in. just as I was exhaling he shoved the full length of his cock inside of me in one swift motion. I closed my eyes and let the poppers work their magic. It felt absolutely great. He was fucking me hard, fast and deep. The whole time he was calling me names like slut, cunt, whore, and slapping my ass hard. He pulled all the way out and plunged all 8inches deep inside of me, where I felt him twitch and let loose stream after stream of hot cum filling me up. I collapsed feeling the cum trickle out of me little by little. I thank him for the cum and shoved my plug back into my freshly fucked cum soaked hole. After getting dressed I said goodbye and told him to email me anytime he needed a cumdump. I got into my car and picked up my phone to see 3 new messages all from guys who want an ass to use. At that point I made it a goal to fuck until I was completely exhausted and filled with cum. I replied yes to all three messages and got back 3 addresses. It was time to really exercise my inner slut.

So I was driving to the next guy's house and I still had my wig on and I was also still wearing my heels. Right then I decided to not even try to hide the fact that I was a cross-dresser cruising for cock. I pulled over about 10 minutes from the next guys house and took off what i had on top of my schoolgirl outfit. I thought I might as well go all out. As I walked up to the next house, I could feel the cum from the last guy soaking my panties. I love having a wet slippery butt. It is my favorite feeling, especially when it's a nice big load of cum that is making me slippery. So the second guy answered the door fully naked and hard as a rock. This was my favorite stop of the night because he wasted no time at all. He took my hand and led me to the couch, bent me over and took out my plug and dropped it on the ground. I swear that before the plug hit the ground he was balls deep in me with a nice 7 inch tool. He never said a word the entire time he was violating my ass as hard as he could. I felt right at home with my face buried in the couch cushions while he was drilling me. He must have fucked me for at least 10 min and it was deep and hard the whole time. This guy's balls were rock hard so I figured he was packing a pretty big load. So I couldn't wait for him to fill me up. When he finally blew, I felt like a rocket had gone off inside me. There was no way to keep it all in, and I immediately felt it running down my legs. He picked up my butt plug and put it back in my wet dripping hole. His first and last words to me were "thanks slut". I said you’re welcome and walked out the door as I pulled up my cum soaked panties.

Well at that point I had no intention of stopping and cock number 3 was only about 5 min away from the second guy. So I was there and ready in no time but this guy had special instructions because his wife was asleep inside, so he wanted to fuck me in his garage. Who am I to say no to some late night cock in a garage? I parked two houses down in the driveway of a home-for-sale. Then I walked down the alley to his house. Anyone could have looked out their back window to see me walking down the alley dressed like a slut. I got to his back gate and he was there waiting to let me in. The next thing I knew I was on my knees getting him hard so he could use my ass. I got him hard pretty fast but I like sucking dick so I gave him a nice slow blow job for about 10 min. After that he was ready to ram me. He laid me down on an air mattress and put my heels on his shoulders. I left the butt plug in the car so there wouldn't be anything in his way. The only reason I was even wearing panties at that point was to soak up some of the cum. He pulled my wet panties aside and plunged all the way into me. It felt so good I could barely stay quiet. Then he pinned my arms down and went to town on my now loose hole. I love feeling helpless and controlled, so being pinned down was a huge turn on. After plowing me for about 5 min I could tell he was getting close, so I clenched up to make myself as tight as possible. About 3 seconds later he let loose in my slutty hole. His was probably the smallest load of the night but it was still enough to drip down my leg. I pulled up my panties to soak up some more cum and I was off to guy number 4.

On the walk back to my car as I felt cum running down my ankle, I looked down to see multiple very visible cum stains running all the way down my stockings on to my shoes. Even my shoes were covered in cum. Now the events of the night were really setting in and I realized how nasty I had been up until that point. Just as I was about to call it a night and go home to rest my soaked hole, guy number 4 messaged me asking if I was still up for another load. He also said he had a friend who could give me a load too if I wanted. At that moment any guilt I felt for the cum in my ass and panties was gone and I was ready to add to it. The whole drive over to cocks number 4 and 5 I was examining all of the places on my clothes and body that were soaked with cum. By the time I got there the list was pretty big, and now included my car seat and any other place i sat down. I walked up to the door ready to be double teamed and was about to get just that. When I knocked at the door I just heard a guy yell COME IN! I was really hoping I wasn't at the wrong house. As soon as I walked in I knew it was the right place because I could hear the porn already. I walked into the living room and there were two rock hard cocks waiting for me. They were both around 6 and a half inches but really thick. I wasn't worried though. I probably could have fit a fist at that point. I was ready to go and neither of them wanted a blow job. They were very clear in the email that they only wanted to fuck my ass. I take orders very well so I went down to the floor and put my face down and ass up to let them decide who was first. I am still not sure who was first but it was deep and hard, I know that much. One guy would fuck me as hard as he could for about 5 min and then pull out for the other guy to pound for a while. These guys really worked my ass over. It’s like they had gotten together beforehand and planned out the best way to use me. This went on for about 45 min. We were all covered in sweat and breathing heavily. Both of these guys promised me huge loads so I was really anxious to feel them unload inside me. When the first guy came I couldn't believe what I was feeling. I didn't know someone could produce that much cum. I looked down and there were already two little puddles of cum forming at the bottom of my heels. I was lubed with a fresh load and ready to take my last filling of the night. There was still a lot of cum inside me that was dripping out when guy number 5 shoved his hard on as far as he could into me. I felt the cum being forced out of my hole as he fucked me as hard as he was able to fuck. His load was just as big as the other guy but it came out in huge spurts. I tried to keep all of that last load in until I was in my car so I could enjoy feeling it slowly trickle into my panties the entire way home. I thanked both of the guys and told them to email me when they needed a cum slut.

After that night there was no turning back. Since then I have had a lot of nights ending in cum soaked panties. One thing is for sure I will always be a cross-dressing cum slut.

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This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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I Want To Be A Sissy Part 4

After my intense and strangely satisfying lipstick application initiation, all the women and young girls and the male pharmacist drifted off, allowing Judy to take control of her cute little pansy customer once again. I was dumbfounded that the woman I first saw coming towards me with what I thought was disgust in her eyes, was really a rougher, blunted extension of my darling wife, my Mistress Claire. Judy seemed perfectly happy to take command of me and my sissy needs. She proved...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

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