My Escapades As A Sissy Sub #1 free porn video

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When I was watching porn I’d just fast-forward through the warm up with the girl. I just want to get to the action, I told myself. Here’s the truth: I just wanted to get to the cock. That big reveal moment when the girl unzips some really hung dude and a cock springs into her face.

This story is about my first time actually doing something about it when I was 19 years old.

I made a profile on one of those adult dating sites for men and started talking to this older guy (50s) named George. It didn’t take long for him to convince me that he wasn’t crazy. About 2 days later, I was driving to his place with my heart thumping in my chest. I was terrified, but I knew I had to try. I walked up to his house and knocked on the front door. I felt like such a slut. Here I was, going to another man’s house to play with his cock. George opened the door with a smile trying to make me feel at ease. He asked me a little about my life and tried to get me comfortable as we sat on his couch.
His arm moved to my leg and started massaging.

“Is this okay?” He asked. I nervously replied that it was.

“Can I kiss you?” Yeah. The kiss wasn’t bad, but I can’t say I enjoyed it that much. The kiss did embolden me enough to move my hand to his crotch where I felt my first cock. George was wearing sweats and it was easy to massage his bulge through them. Just touching another cock sent electric bolts through my body and I immediately started getting hard.

“ohoho” George laughed, “I can see what you want”. He said as he noticed my cock instantly start to inflate, “you want some cock, don’t you?”

“Yes!” I blurted out. “Can I suck your big cock?” I could hardly believe myself. Had I just said that? It felt relieving.

“You sure can” said George.

I immediately tugged at the waistband of his pants to reveal his cock. It was fully erect, circumcised and maybe 6 inches long. I immediately bent over and put it in my mouth. It felt right, to be bent over and pleasuring a hard cock. I was in heaven. Suddenly George started to get up with his cock still in my mouth. I sucked him a little more while he stood in front of me and I sat. Then he suggested we move to the bedroom.
I stripped down and he did the same. Unceremoniously, he pushed me onto my stomach and mounted me. I felt his cock at the entrance to my hole, and I was hard as a rock. He pushed into me rather roughly and I moaned. I could hardly believe how much it hurt. Soon, he got a rhythm going and it started to feel good. I mean really good. I came from the friction of my ass getting pounded.
When he saw what I had done he laughed and called me his slut. I guess I was. Soon after he grunted and shot his load down my ass.

Experience #2
My next experience took place a few months later. I was somewhat of an aficionado when it came to sissy sites on the net. I used to rub myself off to those sites that promise to make you a sissy if you come to them. Well, I got up the courage to email one and I sent them some pictures. They liked what they saw and I soon was on a bus off to the town where they lived with butterflies in my stomach and a raging hard on the whole time.

I ended up walking about 20 minutes from the bus stop to their house. It was a ranch style house in a non-descript looking neighborhood. I felt so naughty and excited walking up to the door. I didn’t bring any luggage, per instruction. Everything was to be provided for me here.The person who greeted me at the door told me his name was Ron and he took hold of my hand and led me to the couch. Ron was fairly tall and in good shape, and about 45 years old. There was one other guy on the couch who turned and smiled at me as we walked in. He was a little bit older with a bit of a belly but he looked like a really big and tall guy, even sitting down. He introduced himself as Rex.Ron led me over and sat down, patting the empty space between him and George to indicate my seat.

As I sat down I immediately felt a hand on each one of my knees.We chatted for a little while like that. They kinda took turns asking me general questions about my life.
“Do you like cock?” Ron suddenly interjected?

“Yes” I shyly replied with a not-so-subtle glance at first Ron’s crotch, and then Rex’s.

“Well, why don’t you take off your clothes for us” he replied.

I stood up and first peeled off my long sleeve shirt. Rex whistled appreciatively and asked me to spin around. As I did, he grabbed hold of my ass. It surprised me to feel his big hand engulfing half my ass, but in a good way and I immediately felt blood rushing to my little cock.I had never done anything like this before, but I tried to be sexy as I unbuckled my belt and slid my jeans down to my ankles. I again turned around in a little circle to show off my ass and as I did so I felt both their hands squeezing my buttocks and murmuring appreciatively. My cock was so hard it was almost burning. I bent over a little further to stick my ass out and I felt one of the hands move up the waistband on my underwear and pull it down over my buttocks.

Here I was, letting two strange older men fondle my naked ass, I thought. I had to admit, I loved it. What came next surprised me.Both hands left my ass and as I turned around I saw that both men had sat back on the couch.I turned to face them as Rex said “Nice”, to Ron, “but she needs a shave”It felt odd to be addressed and spoken about in such a degrading manner, but it also made my cock twitch. I itched to touch it and jerk off.Ron nodded back to Rex and then turned to me and barked a laugh upon seeing my cock twitch.

“She doesn’t need any lesson in eagerness” he laughed.

I was being referred to as a girl, and I loved it. With that he grabbed my ass and pulled me forward so I was leaning on an incline between the two men and he grabbed my dick firmly in his fist and started to jack me off. I couldn’t believe how good it felt and I gasped in pleasure. I soon felt Rex’s hand start fondling my ass, his finger circling my hole. I don’t know how long I lasted but I doubt it was more than a minute.

“I’m going to cum!” I gasped.

“Hold out your hand to catch it when you squirt” Rex said.

I did as I was told and held out my hand as Ron’s firm hand made me ejaculate.

“Now clean up after yourself like a good girl” said Ron.

I knew what he meant, and I tentatively licked my cum off my fingers. As I did so, I noticed the bulges in both men’s pants. I felt so dirty and horny that my dick didn’t even go down. Rex then informed me that I needed to be waxed, and that he knew a guy. They said payment had already been arranged. Next, I was given a pair of pink panties to put on. That was all I was given, and my hard cock clearly showed through them.
Both men got up and beckoned me to follow. We walked through a door in the kitchen and out into the garage where we got into a car. We only drove about 5 minutes to another little ranch house with a sign out front advertising body waxing. I was nervous to get of the car in only my panties, but Ron and Rex just laughed and told me to run. I did so, and I could hear their whistles as I ran to the front door and knocked. For an agonizing few moments I waited for the door to open in just a pair of panties and a hard cock. When the door did open, I immediately stepped inside.

“whoa, whoa” said the man who opened the door.

“They did tell me you were eager. My name’s Mike” He said. I tried my best to smile up at him and as I did I noticed his large and burly frame.

“looking sexy!” he said as he grinned at me, “now lets get that hair off and turn you into a nice little slut”.

My cock twitched again at his words. I stripped off my pink panties and laid down on the table, facedown. I felt him slathering warm wax over my arse, followed by a tug and pain. It hurt like hell. I lost my boner pretty quickly, but I got through it. When he was finally finished he told me to stand up and look in the mirror. My god I thought, as I turned around checking out my smooth hairless ass. My hairless little cock instantly started inflating.

“so” I said as I turned to Mike, “how do I pay for this?”

He just grinned and placed a hand on the top of my head to gently push me down to my knees in front of him. I didn’t need any further encouragement. I undid his belt and pulled his jeans to the floor, revealing a pair of briefs with the clear outline of what looked like a big cock visible. I rubbed his shaft through the briefs before reaching up the right pant leg and grasping his cock with my bare hand. It felt so good to have my hand there that I let out a little sigh and I felt my cock jump.I pulled his briefs down and, placed my hands behind my back, and licked up and down his shaft.

“God you love this, you little slut. Look at how hard you are!” he said as he flicked my cock with his foot.

“now suck this cock!” he barked.

Immediately I placed my head on the tip and began bobbing back and forth, letting some drool fall as I did. Soon, Mike was matching my bobbing with thrusts of his own and looking down at me with desire in his eyes. Suddenly, he grabbed my head and forced it still, his cock still halfway in my mouth, and began thrusting in and out. I almost gagged a few times but my hand, seemingly of its own accord, moved to my groin to begin jerking myself off. Mike was moaning now and I could tell he was close. His strokes became more erratic and soon he began to cum. The first spurt was all in my mouth and for the rest of his orgasm he pulled out of me and came on my face. I was so enraptured with his orgasm that I didn’t cum myself.

“nicely done!” I heard Rex’s voice from behind me, “You look cute with cum all over your face” he said.

I didn’t know how long he had been standing there, but the bulge in his pants indicated he had seen enough.

“why don’t you clean Mike up a little and then I’ll drive you home”.

I was still on my knees, so it was easy to move my head to Mike’s semi-erect cock and like a good slut I cleaned the cum off his dick with only my mouth.

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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...

2 years 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...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 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. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

3 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - 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 Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

3 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

5 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Jamie Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

3 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

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