First Night Out As A Sissy free porn video

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Nervously, I came out of the restroom. I had never come out side fully dressed in my girly outfits. Rickey was about meet me in 15 minutes so I hurried. I found out what cross-dressing is when I was in high school and that was the time when I, with a slim and little frame started doing it. Inside house and at various encounters I had brought the dresses with me in bags. But outside among people dressed as a girl?! Now way, never…till now! I could not believe that I was outside wearing a tank top and hot pants! Every step I took gave me goosebumps. Every time Ilifted my head and saw any one looking towards my direction my dicky twitched. I had learned that I not only liked sucking cock--it was my life's purpose. I needed to be mouth-fucked, and I had nowhere to turn. So I muttered my purpose and stepped into the bar.

Rickey and I had exchanged pictures before but this was our first meeting. For once I thought of turning away but my semi hard clit lead me towards destiny. I walked up to the bar, and ordered a shot of Patron. I didn't drink much, but when I did, good tequila was it. I slowly spun my chair around, and looked around as I leaned against the bar. That’s when I saw him! Already here and sitting at a table in the corner. He was smiling and waved at me! I signaled him to wait at the table. The place was packed, and I want Everything Tonight was playing on the radio. The song echoed my feelings so much.
As the tequila took effect, I started to get up my courage. And I really just wanted to give, so it was a win-win. Rickey was young, short hair, and looked like he was built well. He was wearing a brown shirt, and jeans. After another shot, I started towards the table. His smile broadened as I reached him.

"Hi Rickey. I'm your Kitty," I said calmly (thanks to the tequila), as I reached out my hand.

Rickey reached down and kissed my hand, as he would do for a woman.

"So, what brings you beautiful??" he said with a wink. We both knew what we were up to. But it was feeling good to act as a play!

"I am here to do just that. I, well, I just love cock, and I thought I might get some here" I said. Even though I was buzzed, I still felt some adrenaline from making such a bold statement.

"Oooh OOh! I've got one!" Rickey said, mockingly.

We both laughed, and I was becoming more comfortable. We talked and laughed. I was starting to like Rickey, and after awhile, I told Rickey a summarized story of one of my early adventures. After the story, Rickey looked like he was getting excited, and he finally popped the question.

"Look, I have a room at the Tim’s across the street. Wanna go have some fun?" he asked, in a surprisingly calm voice.

"I thought you'd never ask! Let's go" I said as I winked.

We left the bar, crossed the street, and rode the elevator up to the seventh floor. I was getting excited. As he was unlocking the door, Rickey grabbed my ass with the other hand and made me jump.

"Wow, you have a nice ass!" Rickey said, rolling his eyes and smiling.

"Thanks! I hear my mouth is nice also!" I said grinning.

We walked in, and Rickey backed me against the wall, wrapped his arms around me and started kissing me, with extra tongue. I was surprised. He had been kissed by a man, but it was never this nice. During our embrace, my hands wandered down Rickey, and slowly reached in front, and down his leg. I felt a stiffening cock in there, and I couldn't resist. I backed Rickey up in front of the bed, went down on his knees, and started undoing his pants. He stripped off his shirt, and shimmied out of his shoes and pants. He had average hair on his body. I stood up and took off my hot pants as well. I could see his cock clearly through is underwear, and it was nice sized. I knelt down in front of him, and slowly pulled down his underwear. His beautiful 7" cock sprung out. It was lovely. Circumcised, fat and beautiful, long head. I wasted no time. I gently reached up and grabbed his cock by the base, and flicked tongue on the slit.

"MMMmmm." he said as he winced slightly.

I started licking his head like it was a lollipop.

"Oooooh, that's nice! Mmmmmmm."

He slowly backed up, sat back near the edge of the bed, and held one of his legs up with his arm, giving me good access to his package. I moved in, gently grabbed his cock by the head, and raised it straight up. His balls slowly shifted out, and I started licking them, one at a time, while gently rolling his cockhead between my fingers. He was starting to gyrate. I leaned in, and sucked his sack into his mouth. Yum, they felt so good in my mouth. They were puffy with cum, and I could feel each vein inside his sack. I began to roll each one around with his tongue, as I fondled his puffy cock head.

"OOooh. MMMMMM! Oh god that is sooooo good" he said slowly, gyrating his hips.

I kept up massaging and sucking his sack. I knew from experience that I seemed to get more cum if I did this first. I began sucking his balls in deep, and slipping my tongue out behind his sack, and tickling his spot.

"AYY Yess! OOoh that tickles! WOW you're good" he said as trembled at the tickle attack.

After tongue bathing His sack, I raised my head up, and let his cock go. It stood tall, with the long puffy head all precummed up.

"Your cock is so beautiful," I said, as if in a trance.

"Thank you! Climb up here, and let's see yours!" he said so cheerfully, he was almost singing.

I slithered out of my paty full of wet sopts, and climbed up on the bed, as he slid up into a laying position. Rickey reached for my cock, and gently took hold of my stiffness. I twitched with delight, and he gently grabbed mine. We gently stroked each other, gyrating, twitching and moaning, while looking each other in the eye.

Finally, he sat up sideways and laid down so that his head was down by my cock, and his cock was right in my face. He grabbed my cock at the base, aimed it at his mouth, and started tongue-bathing me. My hips involuntarily flexed towards him. Seeing the beautiful, huge cock in front of me, I went to work. Without even using my hands, I impaled myself onto his dry cock. He twitched, and pumped forward, making his cock hit the back of my throat. I missed this so much, and I was so thankful to have a cock in my mouth again! I slowly covered the cock in spit, and started humping in and out, easily hitting the back of my throat with his cock. As I was doing this, Rickey easily had my whole cock in his mouth, and he was sucking me hard. I reached a hand back and cupped His balls, and gently pumped them as he was sucking, and his hips were matching his rhythm.

Rickey was an expert cocksucker, and I was so close to the edge. Suddenly, he cupped my balls as he was sucking and pumping my cock. The warmth of his hand, the hardness of his sucking, and his expert cum was too much for Me. I shot a load right into His mouth. I was cumming so hard, and I stuffed my cock all the way down his throat as I pumped cum into his mouth.

"MMMMMM MMMMMM!!! MMMM HMMMM! ACHGGG!! MMMM HMMMM!!!" I moaned, his mouth filled with cock. This was the only way to cum. With a stiff cock deep in my throat, I thought as I fed his hunger. Load after load was met with more sucking and pumping. My legs were jiggling and spasming uncontrollably. After some time, Rickey finally withdrew my cock.

"mmmmmmm" he moaned as he swished my cum in his mouth, swallowing with a smile, "I love cum!"

"MMM HMMMM!" I moaned in agreement.

"You want some too?" he asked in a slow, sexy voice.

"Mmmm HMMMM!" I moaned with mouth full of cock.

He sat up and gently pulled my head off of his cock. He pushed me onto my back, scooted up in the bed, and mounted my chest. Leaning his body up, he extended his legs, braced him on the headboard, and slowly rose up over me, lowering his cock onto my face. I opened up, my arms pinned down by my sides, and Rickey guided his swollen cockhead right into my mouth.

"Open wide, I cum a lot," he laughed.

I obeyed, and he slid his cock deep into my mouth, until it was pressing the back of my throat. He pulled himself up further, causing his cock to bend backwards a bit, and I bent his neck back. This allowed Rickey to enter my throat. He then started humping my face, fucking the back of my throat, and moaning.

"Ooooh that's it baby, that's it," he said sexily as he humped my throat.

My face and throat was being used as a fuck-toy again, and it was my favorite position to be in. All I could do, pinned down as I was, was tighten, and lick what I could, as his cock was pleasuring itself deep in my throat. He moaned. And I moaned. I was in so much heaven, as hearing the sloppy sucking sounds of his cock going in and out. I started moaning in rhythm with his pumping, and extending my neck backward and up to meet each thrust. Soon, Rickey was moaning in rhythm also, and his cock was getting even harder, his swollen head entering and exiting my throat faster and faster. He started to twitch at each stroke, and I knew what that meant. Soon, he backed is cock out so that just the mushroom head was in my mouth, and reached down to stroke with one hand.

"Oooh oooh OOOH! OOOH! AAAAAAAHH!!!!!" Rickey screamed as he let go a load of cum right into my mouth. I sucked and licked his head as he pumped each liquid load of cum into his mouth, hot man-juice delivered right into my mouth. I greedily sucked the head, and began trying to tongue his slit. I could feel the heat from each load as he fired the salty sticky goodness into my mouth. I wanted it all. And he kept giving, as his body became less and less controllable, until he was just a wild a****l relentlessly fucking my face. I had swallowed mouthful after mouthful, and wanted more. I kept sucking, until he finally gave up, and rolled off and laid next to him.

I was lying on his side, swishing his cum around his mouth. I was savoring the taste, looking deep into his eyes, watching Rickey panting, his mouth wide open.

"Oooh, that was so good!" he said, out of breath from the mouth-fucking he gave to me.

I slowly swallowed, closed his eyes, and then looked deeply into his eyes.

"Thank you." I said, laying there in his happy place.

"MMmm, thank you! Let's take a nap, and do it again! I have plenty more where that came from!" he said, and we two kissed and drifted off to sleep.

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Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

4 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

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