Blackmailed To Become A Hot Transgender Slut free porn video

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My name is John Smith. I'm a eighteen year old male who's single. I'm into girls. Quite frankly I'm perfectly straight. I'm about to graduate highschool. I started school a bit early due to my birthday, so my last year of high school was done as an adult. It was a month into highschool when Mrs.Cherry called me into her classroom. I'm not the brightest k**. I was failing her math class for sometime now, so when she called me in I was a bit nervous. She had such a devious look in her eye. Like a cougar about to pounce on a small little gazelle. If I'm being honest she was hot. While I'm being honest I've fapped to her sometime. When I say hot I mean HOT. Huge tits that always struggled to stay in her shirt. An ass that can hold a cup on it. Her legs unbelievably unblemished and perfectly long. Apparently her and the principal are a thing. They have hot sex at least five times a week. She made it a point to exaggerate how perfect his dick is. He's packing something special, a ten inch long dick with exceptional width. He puts it into her and she just orgasms. I'm not too sure how well I believe that part though. I fell like it should be the other way around. I know I would only last, like, two seconds. My dick is only five inchs, when its as hard as gets. I've had a couple of chances to lose my virginity, but out of embaresment I chicken out. I make up some lame excuse. Anyways, apparently her and the principal got into a tiny fight and she might loose her job. He said that she may be able to save her job, but she has to help with one of his fetishes. She has to suck him off while he fills in for her while shes "out sick". Her desk looks like it can do the trick. There's a wall on the front of the desk so you can't even see her feet when she's sitting down. She told me that she simply hates blowjobs. That while she'll take a facial, she refuses to suck or swallow. Apparently thats where I come in. If I come in She'll raise my grade to an A. My first thought was hell no! But if I fail this class I won't be able to graduate. I reluctantly agreed. She smiled, and winked at me. She said "well Mr.Smith, we have a lot to do!" I was a bit confused but she beckoned for me to follow her, so I did. She led me to her car. She told me " we have some preperation to do at my house. I was hesitant, but I went in.
We arrived at her house ten minutes later. I followed her into her house and sat down in the living room. The living room was right as you walk in. Then from the living room there two different hallways. One that led to the garage, and one that led to the room/ bathroom. Right in the living room was a doorway to the kitchen. In the kitchen was a sliding door to the outside. While I was in the living room she told me call and and tell my parents II'm spending the night t a friends house while she went to go get something. I did. They didn't seem too happy bu were ultimately okay with it. She came back with a odd box labeled "fun". She pulled out a dildo, thong, dress, bra, wig, makeup, glue, and silicone breasts. Then she went and got a odd paste from her kitchen. She told me "first item of buisness, undress yourself". On often I would be hesitant about getting naked in front of a teacher, but she was so hot I just did it. She looked at my small dick and smirked she said "as small as it is, I can't risk you getting hard". I looked at her confused. I was about to ask why when she pulled my closer, as she sat down on the couch. She gave me a hand job. Without lube she got me off in one minute flat. I sat down, that was by far the best orgasm of my life. She told me to get up. I tiredly did so. She got a handful of the paste and put it on my dick. I backed away confused, but she pulled me back and told me not to move. With the paste she pulled my dick down, and made the paste look like a pussy. There was a hole for my dick to pee. I was thankful for that. She then put a generous amount of glue on my chest, and glued on the tits. I was hot... hot-ish, but no where near Mrs.Cherry. She then told me to put on the clothing/ wig. I did. She looked agitated, and fixed my wig. I was confused why there was so much detail considering I was going to be under a desk. I didn't think too much about. She looked at my happily and told me to start practicing on the dildo. That was my wake up call that this has gone too far. I started to take off the wig and told her "No Way, I'm done with this. Its gone too far! I'm not gay! She looked at me pissed, and smacked me. I was so shocked, I was going to tell her that I would sue, but then she said "You will do this! Unless you want to do highschool again. Also I'm pretty sure you wouldn't want these pictures to get out." I looked at her confused. She then took a picture of me in all those clothes and fake tits. I was furious, and yelled "delete those right now"! She laughed and said "I will send these all over the school and your shame will never end"! I was defeated, I could call my parents, or the cops, but she would still have time to send those, I was defeated. I reluctantly put the wig back on and grabbed the dildo. I tried to deep throat it and only got half way through. She took the dildo and shoved it down my throat. My gag reflex went into overdrive and it shot out. She told me I had to go all the way down too. She shoved it down again, this time I focused so hard on my gag reflex I didn't even notice when she started squeezing it and puling it out. At first I was relieved, but then I tasted something funny. I realised as she pulled it out that it was cum. I was about to spit it out when she said "uh-uh, you have to swallow it all." It was disgusting, but I focused, and swallowed it. I was lucky I didn't throw it up as my body wanted me too. She then laughed at me and called me a slut. She threw me a blanket and told me to sleep.
I woke up the next morning to her standing over me. Her smile was unsettling. She showed me her phone and it was horrible. Not only did she take more pictures, but she also put me into slutty poses. Such as me grabbing my tits or fingering my pussy, she even managed to make me bite my lip. I don't even know how she did that. I looked liked I was getting off to all that. She blinked at me and said "for... insurance". Now lets get you ready, you have a big day ahead of you! She gave me a shit load of make-up. I looked beautiful. The problem, or was it the good thing, was that you wouldn't be able to recognizes me if you saw me. She told me that to avoid suspicion she can't drop me off, so I will have to be dropped off a block from school. and, walk. She took my shoes and gave me five inch heels. I was horrified. The entire ride to school she gave me specific instructions on how to suck him off. She dropped me off a block away from school and I started to walk. As I walked into the school all eyes turned to me. So much for a low profile. The heels forced me to shake my ass as I walked. Both the heels and the dress made my average ass look huge.I went into Mrs.Cherry's classroom where she sat on her desk, looking at me. She gave me a hot kiss followed by a slap on the ass and left. I went under the desk and waited. After some time I heard people slowly come in. Followed by the bell. After about five minutes the principal walkind in told the students that he will be filling in for Mrs.Cherry today. He told them to read some random chapter and sat down. I was hesitant. He slapped me and whispered to me "Bitch if you din't start sucking I'm filing this termination for you. I pulled his pants down. It was struggle, but I managed to release his dick from his underwear. It was huge! I couldn't believe it. His dick limp is bigger then mine when its at its hardest. I started to lick it. It didn't taste too bad. I decided to try and swallow it. I got half way, and then started to gag. He mumbled something and pushed his lap up. My head hit the table and his dick went in all the way. This routine went on for the next five minutes. Then my throat was stretched enough to handle him. I proceeded to actually be able to swallow him.after about ten minutes of that he finally came. He was so deep in me that I was forced to swallow him all. It was disgusting! He mad some odd noises. I predicted that the students probably got wierded out, but nothing too bad. He whispered for me to lick him till the class ended. I did. It was horrible, but I couldn't risk him getting suspicios and finding me out. After class eneded he whispered "good job slut" and left, after anouncing a sub will be in shortly. After he left I got up from under the table and got some weird looks. But luckily the bell rang and everyone left. Leaving me there with a belly full of cum.

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Transgender Day of Remembrance 2006: Huntington, NY What A Transsexual Goes Through by shalimar What does a transsexual go through that is different from other people? In many ways it is a lonely life. When I was a child I was caught in the middle. The boys didn't want to play with me because I was a sissy. The girls didn't because I was a boy. When I tried to join the other kids I was attacked, teased or at the best, shunned. Although I was pretty good in team sports I was...

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Transgender Sex A Liberating Alternative

Transgender Sex: A Liberating Alternative Sex that involves only men and women, whether it is heterosexual or homosexual, eventually becomes tiresome. Both as entities in themselves and as sexual partners, shemales, as a third sex, so to speak, renew and heighten sex and sensuality by combining some of the attributes of each sex, as such crude terms as "chicks with dicks" and "dudes with boobs" suggest. Just when we begin to think that we know it all about men and women and about sex...

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The Transgender Zone Wishes

You're on a long winding stroll through space and time. You've entered a wondrous land where light is shadow and shadow is light and reality is not expected. You've long ago crossed the rim of the Universe, you've just entered the ..... Transgender Zone. Act One Randall Cummings had just left one of the drag bars in Washington, D.C. Randall is a married crossdresser. When Randall is "en femme", he goes by the feminine name of, "Tracey". His wife, Melinda, knows he's...

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Blackmailed And Got Laid By Hotelmen 8211 Part 1 Bus Incident

Hi, my name is Regina and I am 22 years old. I work as an IT employee in Bangalore. I am a hot busty girl and everyone stare at my curves and my boyfriend loves it a lot. My structure is 36C-32-36. He always says that I have a great figure and I am hotter than his Australian classmates. He studies in Australia and his name is Raj. Coming on to the story, I was getting ready for my office combing my hair and checking out my boobs. It was hanging and big as usual. Although I don’t have a flat...

2 years ago
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Blackmailed Couple Ch 1012

Chapter Ten:No more blackmail – ultimatum completed.Thursday night was here too quickly. Anna had spent every day and every night thinking about her situation. For a while, she tried to take the approach that she was finally free; that the risk, the possibility of losing everything was now finally gone. But even as she thought that, she knew that she was missing the control. She knew this was going to haunt her. But how to comply; my god, how could she be expected to expose her infidelity to...

3 years ago
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Blackmailed Couple Ch 0406

Chapter Four:Learning to obey – the show of enjoying.Three days later, Anna received another envelope via courier. It was Thursday morning, and she had just settled into the normal routine of the morning. Normal, considering the turmoil that she'd been going through. Monday, after Mark had dropped her back off at work, she'd been very aware of her violation. She'd pulled way back from me that night, telling me that she'd had a bad day and was in a bad mood. She spent the night doing some...

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Blackmailed Crossdresser part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier,...

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Blackmailed by Grandfather

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Blackmailed And Forced Sex

Hi everyone,me (ram) a naughty and good boy.An average body with a long and thicker dick (7 inch and 1.8inch).Coming to the story I got several mails from the readers of my before story which I was published.Some mail were fake and some were real .I got a mail from a name called divya. I was impressed about her comment about the previous story and started to chat very decently about her details and mine .After few days we become close started to sex chat …During one of the chat session I asked...

1 year ago
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Blackmailed a young waitress in trouble

It was the come in mouth fantasy that gave me the most pleasure.   Celine’s silky golden hair made by belly tingle at the same time as her pink tongue played sexy games with the tip of my cock, circling one way then the other, flicking on the ridge and just under. One delicate little hand holding my shaft firmly, and my balls ready to burst, gently cupped and fondled in the other.   My wife Mildred was tossing. But I was too deeply into Celine to be disturbed. I squeezed...

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Blackmailed my neighbor girl

Blackmailed my neighbor girlIt was around 2 pm on Saturday afternoon, the door bell rang as I expected. I was waiting for this moment from past 2 days and I had sent my wife to her parent’s house anticipating the arrival of my special guest. I opened the door and was not surprised to see Alia standing near my door. She was looking very upset as I had anticipated; she quickly came inside and closed the door herself. Alia’s eyes were red and she looked like she was out of breath. Alia was wearing...

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Tribulations of a Transgendered Christian

This story contains some material that may be considered offensive to the closed-minded. If you are under 18 years of age, or whatever the legal age is where you live, you should close this page immediately. The same goes for all you folks who happen to be offended by transgendered ideas and references. With that said, to those few of you who remain, enjoy what's here. Author's Note: First of all, forgive the writing. This is my very first attempt. For the most part, this is the story...

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Hotwife Kim Such a Kinky Slut

Chapter 1Given just how revealing the slutty little outfits are that my hotwife wears to pubs, clubs and bars,I'm amazed that she's never been arrested for indecent exposure, breach of the peace or grossindecency! She constantly pushes out the boundaries of what she wears and what she gets up to.I first met Kim four years ago at a property exhibition I'd rented a stand at. Through an agency I'dhired four promotions girls to help out on the stand. They were all in their twenties,...

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Blackmailed Ch 02

A Literotica reader who sent me feed back on my story ‘Camping with Anna’ presented me with this challenge. ‘I want to see you write a story which is completely fictional. It’s more difficult than writing something based on events that actually happened, but you have complete free rein, and can explore your hidden depths and fantasies.’ Well I’m always up for a challenge so here goes. This is a fantasy from my hidden depths. I hope you enjoy it. The story takes up where ‘Blackmailed’ left...

3 years ago
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Blackmailed By My Teenaged Daughter0

Blackmailed By My Teenaged Daughter Teen, Group, Mff, Incest by po469 I am a happily married man of 38. My wife, 18-year-old daughter and I live in Phoenix. I fool around a little bit but what my wife Sue doesn't know won't hurt her. Sue was really into bridge so she is away playing cards several afternoons and evenings each week. This gives me time, when no one is going to be home, to go out and have some fun or bring someone home for a little romp. Maybe I fooled...

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Blackmailed

I show up where and when he told me to. He’s standing right in front of me. He knows everything, I know I’m about to be blackmailed but don’t know yet what he wants. First thing he does is tell me to hold both hands out in front of me. I figure he wants to see I don’t have anything in them but as soon as I do he slaps a pair of handcuffs on them. Before I can register what’s happening he’s gotten my cuffed hands over my head attached to a hook on the ceiling. Oh fuck! What just happened! This...

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Blackmailed

Blackmailed!! Pete was an executive with ADB Corp. Millie had gotten a job in the secretarial pool. Millie was a dark red hair Italian girl, she was 33 years old had three kids and a pain in the ass husband. She had 40D tits a tight ass great hip and was always horny. Pete had discovered her on day as he was telling the head of her department what one of the top executives was looking for. Millie flirted with him and was shocked that the department head said nothing to him. When he left the...

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Blackmailed Wife

Blackmailed Wife----------The morning air was already oppressively humid as I stepped out into the barnyard and headed to the office from the house. The sun was already above the horizon casting shadows that moved as I walked. By the time I got to the office door, rivulets of sweat were soaking the thin material of my blouse. I pulled open the closet door to block my dad's office window view and removed my blouse and bra realizing that it was going to be a scorcher today. Grabbing a towel from...

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