How I Was Made A Sissy. True Story free porn video

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I've been dating this girl for about two and half years now. I haven't felt her tight pussy on my dick in about two years though. See, the problem is I have a tiny dick. About 4.5 inches tiny. When my girlfriend and I started having sex, she was nice about it. But the first time we had sex wasn't fulfilling for her, and it just got worse from there.

Our First Time

We were in the living room watching TV at my house. She changed the channel and one of those late night NC17 pornos came on. She said, "I love these, they are so stupid but we have to watch." I instantly became aroused. After watching for a few minutes, I noticed she began moving her legs a lot and could tell she was aroused too. I scooted closer to her, put my arm around her and began kissing her neck. She relaxed and lied back allowing me to lay between her legs and go up her shirt. After a few minutes of making out and dry humping, she got up and walked to the bedroom, stripping naked as she walked. I of course followed. It was dark and we couldn't see much. She lied down on the bed with her arms above her head and her legs spread. Without a word I put her thighs on my shoulders and began tonguing her clit. She began moaning and used her legs to pull me in closer. As I licked at her clit, I put my middle fingers in her and started finger fucking her too. She started moaning even louder and moans turned to screams. All of a sudden, she became very stiff and began convulsing. A gush of cum sprayed out all over my face, hand and bed, then she went limp. I moved from the end of the bed to kneeling beside her head. She instantly turned and took my cock in her mouth. I noticed she didn't seem too into giving me head. We had talked about it before and she said it isn't her favorite thing to do. So after about a minute she stopped and said, "fuck me." I spread her legs apart and moved into position. I slid my dick into her and she let out a little moan. Looking back on it now, I think it was a moan of disappointment. After sliding all 4 inches into her I pulled back and thrust again. As I began pulling back a second time, I knew I was going to cum. I shoved back into her and exploded. I growled, "I'm cumming!" Her response was, "oh" again sounding disappointed. I climbed off of her and she got up and went to the bathroom. She came back to bed already with her panties back on and we went to sleep.

The Second Time

The next morning I woke up and got ready for work. She asked if she could stay while I was gone. I said that was fine. I told her I'd be back around 3:30. When I got home around 3:45, I walked in the door and she yelled for me from the bedroom. She was lying on the bed naked when I walked in and she said, "take me!" I quickly undressed and climbed between her legs and slid my dick in. Within about a minute I was cumming. I felt like a loser. She said, "its okay. We can try again in a little bit. Let's get some food." After dinner, we went back to my place. I again found myself between her legs with my little dick in her cumming after only a minute. She again said it was okay. And so the trend continued. I'd cum, she wouldn't, I'd feel like a piece of crap, she'd say it was okay.

The Turning Point

After about a month of disappointment and frustration for her, she made me do something that I didn't ever think I would like. She lied on the bed on her back with her legs up in the air. She started to giggle as I positioned myself between her thighs. I looked at her and said, "what's so funny." She said, "nothing. But this time, after you cum, I have a surprise for you." She started giggling again. I hesitated for a minute trying to imagine what she meant by surprise. She saw my sitting there thinking and yelled, "hey! Hurry up and fuck me, I want to give you my surprise." She had a big grin on her face and started laughing. I took my dick and about as soon as it entered her tight wet pussy, I came. As soon as I came, I pulled out and looked down at it. I came a lot! More than I have ever came in my life. When I told her how much I had came she started laughing uncontrollably. I asked her what she was laughing about. When she finally calmed down enough from laughing, she said "my surprise." I said, "what about it? What is it?" She looked me in the eye and said, "eat it. Suck up all that cum. Don't miss any of it. And you better get me off while you're doing it. It's been a month since I've cum!" I sat frozen in fear and excitement. She grabbed me by the back of my neck and pulled my face to her dripping wet pussy. I stared at it. Full of white cream. As I gathered the courage I stuck my tongue out and began licking. As soon as my tongue touched the outside of her labia, a thick wad of cum plopped onto my tongue. I took my tongue in and tasted the thick, goo. To my surprise, it wasn't bad. A little salty, but no more than a pretzel. I let out a "mmm." She knew I liked it then. I went back for more. The more I ate, the more there was to eat. Soon, she began adding to it. I could taste my saltiness mixed with her sweetness. She began moaning louder and louder. I reached up and stuck my fingers in her pussy and started thrusting in and out. She again became rigid and then came. As she began squirting, I opened my mouth and let the sweet fluid fill it up before swallowing. She went limp and lied on the bed. She looked at me covered in cum and giggled saying, "you liked that surprise didn't you?" I could not lie. It was great. And so it became the norm. I'd cum and she'd make me eat her out. A month went by and all was well until she got bored and wasn't able to cum. That's when she came home with her toy.

The Toy

She called me over to her placed to see her "new toy." She had been talking about getting a new TV since we started dating and I thought that was what it was going to be. When I arrived, she was lying naked in her bed. The bed and her were soaking wet. It looked like someone had dumped buckets of water on her. I said, "what happened?" She said, "my new toy is amazing!" She reached down and pulled up a hard plastic thing that had a curved head and vibrates. "It's a g-spot stimulator," she said handing it to me. I turned the little knob on the end and it started to vibrate. I turned it a little more and it vibrated more. As I turned the knob as far as it would go, I was vibrating fiercely, she dropped her knees to the side and spread open for me. I placed it on her clit and let it massage her for a minute before thrusting the bulbous head into her tight slit. She immediately started screaming and began squirting. I realized then, why she and the bed were so wet. After that, it became routine for me to cum in her then get the toy and make her cum over and over, after going down and eating her out of course. So for about 2 weeks, I would cum in her twat, eat her out and make her squirt with her little toy. Then she decided it was time for surprise number two.

The Next Surprise

One day as we were about to have sex, she changed up the routine on me. I was about to slide my dick in her and she said "NO!". She handed me her little toy and said, "fuck me with this. There's no point in using your little dick there, it doesn't do anything for me." "Okay" I said as I took the toy and began pounding her with it. After making her squirt a few times, I stopped and said, "so can I fuck you now?" "NO! I said, there's no point in it. You're pathetic little dick can't do anything for me so you don't get to use it on me. As a matter of fact, since the only way you can get me off is by using a toy, I've decided that is the only way you will get off from now on." "What do you mean," I said? She went over to her closet and got something from the top shelf. She turned to me and said, "I got you a surprise." She then walked to the bathroom and closed the door. About 5 minutes later she returned to the bedroom with a harness around her waist holding a massive looking dildo. I sat paralyzed watching as the massive cock dangled up and down. "I can only cum from you using toys on me, so now if you want to cum, it's going to be from a toy." I said, "why did you get that? They make plastic pussies..." She said, "but those are made for real cocks, not little tiny clits like yours." She walked over to where I was lying on the bed and said "lick it." I reached up and grabbed the massive shaft. She smacked my hand away and said, "I said lick it, not hold it. Open you mouth and let it slide down you throat." As I opened my mouth, she slid all 8 inches of the dildo down my throat. To my surprise, I didn't gag once. "That's what a real cock looks like" she said. She used it to fuck my throat for a minute then she stopped and pulled it out and began laughing. "Look at your little dick trying to cum. Sucking dick really turns you on, huh?" As I looked down, my dick was rock hard and throbbing. I knew if she touched it I would cum. She walked to the foot of the bed and grabbed my feet. She spread my legs open and kneeled between my thighs, letting the massive cock rest on mine. "look at how big it is compared to that." She reached over to the bedside table and grabbed a hand full of lube. She began stroking the dildo and moaning. I was about to cum and she knew it. She put her hands under my thighs and lowered her mouth to my cock. I thought she was about to suck it, it would surely make me cum. Just as she got her mouth to it, she raised her eyes up and looked at me and grinned. "Nope, you're not that lucky" she said as she sat back up. Her arms were still under my thighs. She lifted my legs up so my knees were on her shoulders and she said "take it" as she thrust the huge dildo in my ass. I remember grabbing the sheets of the bed and feeling a horrible pain. After she had it in she stopped and rested and said, "you have to relax." As she sat there for a minute I began to relax. The pain began to ease and she slipped a little more in. As she could see that I wasn't in anymore pain, she did one last thrust. Her thighs slapped my ass and I felt a sensation, like electric, go from the base of my dick to the tip and I let a moan. As she withdrew and thrusted again, I felt that electricity again. I reached up and grabbed my dick as she began thrusting harder and faster. She slapped my hand and pulled it off my cock. "If you want to cum, it'll be from the toy only!" Faster and harder, she started pounding. Her thighs slapping my ass with every thrust. "Yeah baby, take that cock like the little slut you are!" she said as cum shot out of me like a gun landing on my face, hair and chest. She pulled out and flicked my trembling little dick and said, "you're my little bitch from now on."

Like I said at the beginning of the story, I haven't felt a tight pussy on my dick for about 2 years. I've felt many fat dildos in my ass though, and I cum every time. She has talked about bringing real men over and letting me watch as they fuck her. She has said that after they get done, she would have them fuck me. She says that if I'm really good, while they are fucking my ass, I could eat her out. That's what I want. That's my wish. I want to eat a cum filled pussy while a hot, hung guy fills my sissy pussy with cum. Maybe one day we will find the right guy to fulfill our dreams.

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THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

2 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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How I Became a Cuckolded Sissy Part 2

How I Became a Cuckolded Sissy: Part 2 By willow619 "Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Allie, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Mike. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completed the transformation. Allie had found a magazine I'd left on the bedroom floor, showing a...

3 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

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. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

1 year ago
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Training Sissy Michelle

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...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

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...

2 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...

3 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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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...

3 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,...

3 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...

2 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."...

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