One Of Many Sissy Fantasies free porn video

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I pull the lacy red G string up to cover my tiny manhood. I clip the back of my sexy red bra. I pull my sexy, black, lacy stockings up and clip them to my suspenders. I pull on my nice tight red one piece miniskirt and slip into some sexy black 6 inch heels. I apply the foundation to match my skin, the eye liner to match my eyes and a nice bright red lipstick. Now I am ready. The transformation from man to woman.

Looking like a natural woman, I park my car at the reserve and text him to let him know I’m here. It’s midnight and dark so I dont want to be on my own for too long. I get a reply “Walk into the public toilets, go inside the last cubicle and lock the door, I’ll be there in 5 ;) “ I do as I’m asked. 5 minutes passes and I hear someone walking into the bathroom. A masculine voice says “daddies here baby”. I unlock the cubicle door and he walks in. “Wow you look even better in person than you do online” he tells me. He leans in and kisses me on the lips, I kiss back. I had mixed feelings. I was nervous but excited at what was about to happen. I felt my cock twitch and it started to get hard. I feel his hands running down my body, to my hips, then on to my ass. He squeezes my ass and moans a little “mmm” I reack to his dick and he is already rock hard. I unzip and un button the front of his jeans. The drop the the floor. This perfect, nicely shaven 7 inch cock stands to attention. I start rubbing his dick while we still passionately kiss.I feel a hand on my head and he is pushing me down, I drop to my knees and give his cock a kiss. I then lick his whole shaft from the bottom, right to the tip of his knob. His hands go on the back of my head and I instinctively start sucking his throbbing cock. I salivate all over his cock making it wetter and wetter. I push my head all the way forward to deep throat his cock. I hold it there for a few seconds before gagging and pulling back. “Thats right bitch” He says. I grab his cock with my hand, pull it up to face him a take his nicely shaven balls in my mouth while still rubbing his cock with my hand. “Ooo yes baby” he moans. He grabs me signalling me to stand up. I stand up and we passionately kiss again for a few seconds. He pulls my skirt off so I’m left standing there in my lingerie. He turns me around, I put my hands on the wall and spread me feet apart a little bit and bend over. He spanks my ass and then kneels down. I feel his masculine hands pull my g string out of my ass and push it aside and then he pulls my sissy cheeks apart and his moist tounge enters my asshole. He starts eating my ass. I let out a little moan “oh yes” about a minute goes by and he stand up. He pulls my panties down and the hit the floor. He spanks me once again. I feel his hard dick up against my cheeks. Pushing up against my hole, pushing in my hole, then it was in. We both moaned. He starts slowly fucking my ass and the painful pleasure hits me. I turn around and he leans over and kisses me. He increases his rythm and starts fucking me harder. He places one hand on my shoulder and one hand pulling my hair. He increases his rythm once again, he lets my hair go and reaches around and starts playing with my hard cock. “You like that you little slut?” He says in a dominant voice “yes daddy” I reply. He keeps fucking me for a little while longer. He pulls his cock out of my ass and I turn around. He lifts me up into his nice strong arms and slams me up against the wall. Still in his arms, he slides his cock back in my arms and contnues fucking me. This was my dream, to be dressed like a wiman, and fucked like a woman. He pounded my ass and both our moans got louder and louder. “No cumming before daddy you little slut” he says to me. His rythm increases and increses. He pulls his cock out of my ass and puts my down and says “now taste yourself you usless bitch” I get pack on my knees and he pulls my hair out of my face and I take his head in my mouth. I take more and more of his hard dick in my mouth until I have the whole thing in. I can taste the pre cun on his knob. He forcefully pushes my head down to deepthroat him, holds my there for a few seconds and pulls my head back. Again, he forcefully makes me deep throat his 7 inch cock and pulls me off. The slight gag reflex makes my eyes water a bit and my eye make up starts to run down my face a little. I look up at him and He looks down at me and says “If you want to dress like a sexy little slut, I’m going to treat you like one. Now suck my fucken dick bitch” and forces my head into his cock once again. My eyes water a little more and more make up runs down my face. I put a hand on his dick continue serving him for a little while longer. He then grabs my hair in a bunch and pulls me off his dick. He says “get up!” I fo as I’m told. He puts the toilet seat down and sits down. He says to me “turn around” i do so. My ass is facing him and I am facing the opposite direction. He grabs my hips and pulls me towards him. He lifts his dick up, and grabs my shoulder, actioning me to sit down. I slowly sit diwn and again, I feel his dick penetrate my tight asshole. Not before long his whole cock is again inside me so I start riding him in a ‘reverse cowgirl’ position. I lean forward and start bouncing on his dick and he thrusts it in out of my asshole harder and harder. He spanks my ass once again and lets out a nice loud moan. He says to me “Are you going to be a food girl and swallow daddies cum?” I say “yes daddy” he says to me “good! Get off my dick and start sucking then you slut” I stand up, turn around, pull my hair out of my face and look him in the eyes. He slaps me on the cheek, grabs the back of my head and forces it into his crotch. I take his meat into my mouth once again and start sucking. Faster and faster. He starts pounding my face. His moaning gets louder and louder. “Don’t stop bitch I’m gonna cum! I’m gonna cum!” I suck faster and faster and then he lets out a loud moan and I feel a shot of warm, salty liquid hit the back of my throat, followed by about 8 more shots. I take his dick out of my mouth and my mouth was so full of cum that it was dripping diwn my chin. I make eye contact with him, and swallow it all and smile. He then wipes his finger along my chin and puts his finger in my mouth so I lick the remaining cum. He looks at me and says. ”Stand up, It’s your turn.” I stand up and he says. “Start stroking, sissies don’t deserve it to be done for them” I start striking my hard cock and within a matter of seconds I am ready to cum. “I’m gonna cum for you daddy!” I moan. He cups his hand and places it in front of my dick and catches every drop of my cum. With the other hand, he grabs the back of my hand and forces it towards his hand filled with cum. “Clean up your mess like a good sissy” he says. So I start licking my own cum out of his hand. After I had licked about half of my load, he slaps my face with that hand and my own cum goes all over my face. He stands up, slaps my ass once again and puts his pants back on. He turns to me and says “you look so sexy dressed in your lingerie like a little pathetic sissy. We should do it again” he winks at me and walks off leaving me in a public toilet, covered in my own cum.

And that is one of my many sissy fantasies.

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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...

2 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...

4 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...

2 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...

1 year 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 himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

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