Sissy Situation free porn video

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Sissy Situation By Ellen (It has been a long time since my last contribution to Fictionmania - I hope this helps give you readers something very erotic to read.) Her arms were up against the doorway as she stood staring at me as I was dressed in my silky pink bra, panties, garter belt, stockings, and high heels. My long blonde hair wig cascading over my shoulders, with a touch of make-up, the usual lipstick, blush and eye shadow. When training with Mistress, I am not given much time to prepare for her when she comes over to the house. When she had called me to tell me to prepare for a visit, I was anxious as to what she had in mind today. As I demurely gazed back at her drinking in the Thigh High leather boots she wore, tight black leather skirt, and a studded leather corset, laced very tight, and accentuating her breasts. "My Darling little Sissy, you know what time it is?" she asked smiling at me. I was aroused by her tone when she continued. "It's time to learn how to suck cock," Mistress stated in a serious tone to her voice. I froze in disbelief did I just hear her right. "If You're going to be my sissy, it's goes far beyond just dressing up in those frilly bra and panties and women's undergarments, it's not just about dressing up, you have to learn to be a perfect little slut." She explained. By this time I felt my heart racing, I figured this was just her way of teasing me, like a joke. "That means having to suck cock," she said. Her hands would go to her sides and Mistress slowly pressed her fingers against the hem of her skirt, and slowly raised it up revealing a pink strap on dildo. The smile on her mouth was saying it all, she was serious and ready to take my training to a new level. I had never thought my relationship would take this turn. It all began a few months back; it's when I first met Mistress. I was out with some friends at a bar in the neighborhood. It was Monday Night Football as I remember, I have to admit, I was not really that much into watching the game that night, I did go just to hang with a few of my guy friends. Grab a drink, eat some bar food, talk about the usual crap. That night my mind seemed to wonder as there were several ladies in the bar whom were just wearing the sexiest clothes, and I will confess right now, I am a crossdresser, so I was really eyeing them out of envy more than lust. I couldn't tell you how often I would find myself admiring the pretty things women got to wear. This is when Irene noticed me, she was a bartender at the place, and as she was pouring libations to the customers, she would give me these glances, and I saw that she had seemed to take an interest in me. She poured a draft beer and slide it to me, as she leaned in smiling. She introduced herself, which never ever happened to me before. I found it very flattering, she was pretty also. Wearing skin tight jeans, and a scoop neck top revealing the tops of her female attributes. Her shoulder length red hair, tied back in a ponytail. During the night as the guys were really into the game, I pretty much found myself making small talk with Irene, she was giving me free drinks, and I was leaving her nice tips. I was never hit on before, and honestly it may have been over my head, but the more I drank, the more open I became, and the faster time seemed to pass us by. Before I even knew it one of my friends tapped me on the shoulder. "That game sucked," he grimaced. "My fantasy football went down the toilet. I'll catch you later." I don't even think he realized that for most of the night I was at the bar talking to this nice woman, as the bar emptied out at the end of the game. Irene boldly asked me if I was interested in going out on a date with her. Mistress walked towards me and my eyes fixated on that Strap on cock, My heart still pounding as she came closer to me placing her hands on my shoulder, finger playfully flicking at the strap of my bra. "I see your lips starting to quiver," she said. "Your pretty lipstick covered lips." She paused and stared at me. "You want to suck cock for me don't you?" I found myself breathing heavier, and her presentation was hypnotic in ways that I just was compelled to agree with anything, everything, that she had to say. "Secretly you fantasized about it, how it would feel to have a cock sliding in and out of that slutty mouth of yours." She guided me down on my knees in front of her, with my face right in front of her sex toy, I looked up at her as she looked down, and I knew, I knew how much I was in this woman's control. "Come on stick out your tongue and get your lips wet for me." She moved her tongue over her lips to demonstrate what she wanted me to do. "That's a good girl." I felt the room spinning a little, the way she was talking to me, it was so sexy, so enticing. "Look at you already such a good slut, dressed up like that, on your knees, with your mouth open and tongue hanging out, like a cock hungry little whore. You want it so badly, my perfect sissy, so eager to please, such a good girl, now let's put that mouth to work." Mistress was ready to expand my mind. Irene and I had gone out a few times together, they were really pleasant dates, I was the perfect gentleman. You know the type, open the doors for the lady, pulls out her chair, waits for her to sit down first, stands up when she needs to get up. I guess deep down if I were a woman, I too would of wanted to be treated that way to. In my mindset my secret desires which I had thought were hidden from society and merely presented themselves in the privacy of my own home, I guess you could say I had great empathy for women. I was always complimenting her on her outfits, shoes, even if I noticed something she did with her eyes, I was very attentive. Maybe that is what attracted her to me in the first place, she saw potential. We had gone for a walk along the lakeshore after dinner; it was a beautiful night, clear skies, and the orange glow in the West from where the sun was just beginning to hide itself. I looked at Irene and she looked at me, it seemed like a romantic moment. I have to honest I felt compelled to want to kiss her, but then she beat me to it, and her taking the lead, kind of offset me in a way that I felt vulnerable and even trembled. The kiss was gentle and as she pulled away she had a look on her face, as if she knew things about me, which no one ever knew. I have to say it took my breath away when she said, "I think you have a little bit of girl in you." "Now hold out that tongue and swirl it around inside your mouth, Watch me, a nice wet tongue get a lot of spit on there," she instructed. As she spoke she demonstrated exactly what I needed to do. "Good, now do that, just around the tip of my cock, lots of spit, I want you to love that cock show it just how much you love it, now pucker up and gently kiss around the tip." I felt her hand on my head, her fingers running through the strands of hair from my wig, it was sending shivers down my back, as I continued to listen and perform her instructions. "Get your lipstick on the tip," she said. I kiss the tip of her strap on, looking up into her eyes for approval as to what I was doing. I could not conceal the arousal in my panties either. Mistress continued, "Look at you, you're so pretty when you get hard, this is making horny isn't it?" I would nod to let her know that I was very horny. Then she went there. "Just imagine sucking a cock for real, my hand on the back of your head, guiding you." I was increasingly getting excited; the thought of her taking me to that level was just driving me wild. Then she said, "Coaching You, instructing you, my hand pushing your head deeper." And as she said all this I felt her hand doing it, "telling you to take it deeper, but not yet, to be a good cocksucker you can't be too eager, can't jump on that dick and just start hammering it in your mouth just deep throating it. You have to take it nice and slow and sensual. Take in the tip into your mouth, just the tip, and work it in your mouth, swirl your tongue around it, that's it. Hold it gently in your mouth, no teeth." The moment I felt everything, from the heels, stockings, to my own penis throbbing inside the confines of my panties, the way my wig brushed against the bare skin of my shoulders, I was in tune with my femininity and here I was getting cock sucking instruction from my Mistress, it was so surreal. She complimented me, "That's a good girl, such a good girl." She noticed things were raging under my panties, "There you go, oh your clittie is getting so hard isn't it?" I would nod to her, feeling so at ease so calm so collected, her soothing voice, beckoning me. Mistress continued, "I want this to be a good experience for you, a positive horny experience for you, so as you continue to suck my dick, my lady cock, with your little whore mouth." She would laugh softly, " I want you to stroke yourself, I want to see you cum and make a big mess in your panties, with that cock in your mouth." Her hand continued to hold the back of my head making sure there was no backing out as she educated me. "I'm going to brainwash you, trained you to be so turned on by sucking cock, you can barely control yourself, that you will need to suck cock, after cock, after cock, never getting tired of it because it makes you so horny." My hand was rubbing the front of my panties as I was following her cock sucking instructions, and it was certainly taking me to an orgasmic height that I could no longer see myself being able to get aroused without the thought of my lips wrapped around a cock. Irene and I sat down on a bench, I was finding trouble speaking, what she had said after the kiss sent me for a loop, I couldn't tell if she had seen through my soul or not, that's when she placed her hand on my knee, and told me to relax. She was a very intuitive woman and from the first time she noticed how I seemed to be looking at the other women in the bar that night, not as a predator looking to mate, but as person who had envy in there heart, she read me like a book. I was confessing my life to her, how I first started wearing women's clothing at a young age in secret. She was comforting; she was quite the take charge woman. Before the night was up, she had me back at my place, modeling my stash of ladies clothes for her. That's when before she left; she made it clear that from that night on. I could no longer call her Irene, that I must address her with respect and call her Mistress, and she would help me experience how to express the woman within me. That's exactly what she did to me. Each time she would come over I was taught something new, tips on shaving, applying make-up; brushing out my wigs, even how to wear my breast forms. I was hooked on her. I loved her. "So stroke yourself, stroke yourself through those panties, and Suck," she continued. "Suck and stroke at the same time." I could feel her hand pressing on the back of my head now. "While I slowly push that cock deeper into your mouth, down your throat, now slowly and sensually deep throat that cock, you dirty cock sucking whore, such a little cock whore aren't you?" I was feeling myself so ready to explode but I knew I could not without her permission her words sent me further and further into a frenzy of wanting to cum so bad. "Taking that deeper, perfect little cocksucking sissy, "Keep stroking, keep sucking, I want your spit dripping off that cock. Feel that cock hitting the back of your throat, keep stroking yourself!" "That's a good girl!" The compliments, and the tone of her sultry sexy voice were oh so mind controlling me I was feeling so ready..oh so ready. Mistress ordered, "I want you to fucking cum for me, with my ladycock in your mouth." "That's a good girl that a my good sissy slut, I want to see how much you can cum for me, now choke on it!" I could feel her hand push my head harder and I had to take it all in, almost gagging on her strap on, it was too much. "Now cum for me!" she ordered. I lost it, I had my orgasm my legs almost cramping up from being in that kneeling position so long, my mouth aching. I could feel the warm streams of cum soak through my panties and onto my fingers. She smiled down at me as I looked back up at her. "Your first cock sucking lesson, such a good girl, such a pretty girl, drool running down your chin, with your lipstick all smeared, and cum all over your panties, such a sight to see. My Pretty little slut sissy." As I raised my fingers to my mouth to lick them clean. I do love this woman, My Mistress. In the back of my mind I knew she would come walking through that door next time, with a man for me to blow. I could see it in her eyes.

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Sissy Farm - Chapter 19 - 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...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

3 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

2 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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...

1 year ago
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Sissy Gets A Black Master

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

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

3 years ago
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Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

2 years ago
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Sissy hypno The beginnings

The beginnings of cock lust – Sissy Hypno pornFOR THOSE NOT INTO STORY OR BUILD UP, SCROLL DOWN TO THE ******** MARKER FOR EROTIC ACTION!Felicity heard Billy come rushing down the stairs from his home quarters above the pub, he swung around the doorframe and appeared behind the bar area calling out to the Indian beauty who was sat looking out the window for a moment.Felicity stood in an empty pub window looking out at the welsh countryside. As far as her Indian eyes could see, were blankets of...

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