My First Shemale Stepmom Encounter free porn video

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My name is Hunter, I'm 28, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men on the videos, that turned me on so easily.

I was alone one day jerking off watching a scene of Yasmin Lee dominating a tied up guy when something unexpected happened: my stepmother arrived early from her job, entered the house quietly and caught me. Stephanie married my father some years ago, she is a stunning white 30 years old woman with long black hair and a body to die for. In other words, she is absolutely gorgeous, and I still don't know why she was attracted by my father.

But that goddess was there staring at my hardon and my computer screen. All I could do in my desperation was to pause the full screen video with Yasmin's cock buried inside the guy's mouth. "I didn't know you were into shemales, Rob, and I see you like the big ones, much bigger than that little clitty of you."

"It's not what you're thinking and my cock is not small, it's just that.."

"Cut the crap Hun, this tiny little cock of you can't satisfy a woman, and I bet my ass you'd be rather taking a she-cock in your ass. Now get up and come close to me." I didn't know what to do, so I got up and got closer to her, my pants over my feet. She started jerking my cock and rubbing my ass as I moaned in pleasure. "I bet what your father would think then he comes back knowing that his son is in fact a little sissy boy that loves to suck cock." - My father got a job as an international salesman some weeks ago, we went on his first trip and didn't return yet, so I was there hopeless with Stephanie.

All of a sudden she sat on my chain and pulled me down so I fell over her lap. She unpaused the video and said we were gonna watch it together, still jerking me off. As time passed up, she put a finger inside my mouth and said me to suck it like if it was a cock. "Oh yes baby, suck my cock good, shake that ass for me, yes like this.. from now on we're gonna have lots of fun together." She turned me to face her and kissed my mouth, god, I was in heaven. But that was wrong. She was married with my father, this should not be happening. I pulled off the kiss and said that we should not be doing that.

Then she pulled my hair hard, and said in my ear: "Yes, maybe you are right and we should not be doing this, but I know your dirty secret and I'm going to do whatever I want with you, unless you want me to tell your father. Besides, that little clit of yours turned me on so much that I'm going to turn you into a very submissive slut girl, you like it or not. Did I make myself clear?" She let go my hair and I could see her gaze, her eyes were blazing with desire, yet she had a very dominant look towards me. So I said a yes, followed by a fierce slap on my face. "Yes, M-mi-mistress?" I could see her wide smile now, with a mean look. I couldn't see much though, she buried my head on her big soft boobs until I was out of air.

I decided to go along with her play, a few slaps could make me get a blowjob and even get to fuck her pussy, forgive me father, your wife was too damn hot to refuse. Soon she was wearing only her panties and I was completely naked sitting over her, kissing her mouth and tits like an a****l. She was stroking my cock while the other hand tried to reach my ass. Then she pressed her finger on my hole, I tried to stop her but she grabbed me and kissed me deeply, her finger slowly entering me.

"Fells good, don't you think? Wait until you get a taste of real cock, you're gonna love it. A big had cock fucking your tight virgin hole, erasing any traces of manhood you might ever have." I could do nothing but moan, with two of her fingers inside my ass and other two inside my mouth. Sensing my enjoyment, she grabbed me and put me down on my bed, instantly started to suck on my little cock, so little that she had my entire cock and balls inside her mouth while she finger fucked me. I tried to resist but she had skillful mouth and hands, I kept cumming inside her mouth within minutes. Oh god, that was the best day on my life, my first kiss and blowjob with a stunning woman.. she came close to me again to kiss, I eagerly opened my mouth and we kissed, but my cum went down on my mouth, I thought she had swallowed it, instead she demanded me to swallow my own cum, I felt so humiliated, but I did it anyway. It felt strange but also tested good.

"Good, that's how a good girl takes cum. Soon you'll be addicted to it, Missy.. yes, I think Missy is a nice name for you my sissy slave. Now as a reward, I will let you suck me too, get on your knees now.." Fast enough I was on my knees, her butt all over my face, she said me to slowly remove her panties with my teeth and I eagerly obeyed. "Are you ready for this Missy? When my panties hit the floor I won't let you stop sucking until I cum" I wanted that more than anything, so I just shook my head positively. But as soon as her panties hit the floor, a very big dick hit my chin, my stepmother was a shemale!

"No way, you're a sh-" I tried to say my surprise but her enormous cock filled my mouth. I wanted to suck her pussy, but her cock was a marvelous surprise, so I started sucking her as if my life depends on that. My stepmother. My shemale stepmother, fucking my face. I started to imagine how many times my father would have sucked him, and if she fucked him. She probably fucked him good, that cock was just like the ones I like in the movies. Now I understood why she called my cock a clit. That was a real cock, not mine and I hoped it soon would be fucking my ass, finally I would have sex with a shemale, the way I wanted.

Suddenly she pulled it out of my mouth, and I instantly bent forward to put it in my mouth again, but she didn't allow it. Instead, she hit my face with her cock and rubbed it on me, making me all gooey. "Beg for it, bitch, beg. I want to see how much you want a cock." "Please mistress Stephanie, allow me to suck your cock, I learned my role on this as a submissive sissy girl, I just want to taste your cum."

Somehow that made her horny, as she put her cock again in my mouth, this time thrusting with sheer force, I started to gag but she won't let me go. She kept fucking my face for minutes, when I felt her body trembling, she started to scream and her cum flooded my mouth, some of it escaping. I tried to swallow all, but that was too much, also much tastier than mine.

I stood there on the floor, cum all over my chin and chest, she sat by my side and kissed me deep. "Your clit is hard again, you can't deny how much you liked to be used like this, huh? I bet your ass is much better, I would love to take away your virginity." Just by hearing that I came again, she took my cum in her fingers and let them to my mouth, I just knew what to do and licked them clean. "Please fuck me Mistress."

"I see you are addicted to cum already, but you won't have a taste of my dick in your ass yet, honey. Maybe another day, when you earn it. Now just take some rest my daughter."

And so she left my room, I jerked many times thinking about what happened and wishing she was fucking me until I slept.

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Author notes: I wrote several stories back in about 1995 or so, but due to certain circumstances, I ended up purging them off of my computer. Over the years I have found those stories on the net and resaved them to my hard drive. The story you are about to read is the most recent story that I have found. It was harder to find because it has been posted to a site (Kristen's Archives) by someone else claiming it to be their writing. It is not. It is my story and I am now reclaiming it...

1 year ago
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Fucking Stepmom sequel

The thing that woke me was my phone ringing.I checked who was calling an found that it was my Mom,I did backtrack and remembered i was to go see her today.Standing there nude with my semi erect dick watching my naked step mom sleeping like a baby in the bed, who had been fucked 9 times or so in the last 18 hrs or so by me. I picked up my moms call greeting her,she was a bit mad because this was not the first call she made to me, other thing she made clear for me was it was 2 in the noon and...

4 years ago
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Seduced by Stepmom

Before I begin, I want to point out that the events of this story were a long time ago. I'm now firmly established in middle-age, whereas I had only just turned 18 when this happened. But as you might expect, these memories have stayed in my mind!I'll start by saying I don't hate my dad. We had a good relationship and if he was still alive I wouldn't have shared this story with anyone, even anonymously. My mom and dad had me in their early 30s, and my twin siblings in their mid 30s. However,...

2 years ago
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My Stepmom Girlfriend and I At the Pool

My girlfriend, Tori, caught me cheating and immediately had me feeling like shit. As I already felt depleted physically too, I fell back into the pool. I was down under the water for about thirty seconds. During that time, I felt much better physically. As if I went from massive pain, to none at all in a matter of seconds. I came back up to them both glaring at me on their knees. Tori put her hand out. "I think we need to talk, Eric." We exchanged looks. Her eyebrows were down and her teeth...

Taboo
2 years ago
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Stolen Stockings Pt 1 SHEMALE LESBIAN PORN

WELCOME TO CHURCH OF RUBBER - STOLEN STOCKING CONFESSION .the sign read above My study doorway.My transex very leggy young secretary nurse led the new prospect in to My parlor and knocked on my door and I said "COME"the heavy gothic arch door swung open and there stood the two stunning transexual stocking sluts in ultimate sissy wear. One happened to be My private nurse and secretary, the other was a specially chosen pretty thing who had been in communication with ME for some time now. My...

3 years ago
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My Shemale Stepmother

My Shemale Stepmother by Richard-to-Rachel My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my...

2 years ago
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SHEMALE FAVORS

"LATE NIGHTS EARLY MORNINGS" FRIDAY NOVEMBER 27TH 2020 - SHEMALE ASKS ME FOR A FAVOR YEARS AGO .. I WROTE MY FIRST XHAMSTER LIFE EXPERIENCE STORY ON HERE. IF YOU HAVENT READ OR SEEN IT, I WOULD MAYBE SUGGEST YOU CHECK IT OUT FIRST BEFORE YOU READ THIS. HERE IS THE LINK FOR SOME BACK STORY OF MY OLD ROOMMATE AND THAI TS LADYBOY LOVER “ NINA “ https://xhamster.com/stories/what-a-week-anal-debauchery-at-its-finest-449485 But fast forward to a few days ago now, the following scripture is based on...

4 years ago
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Autobiography of a Shemale

Autobiography of a Shemale Dominatrix By Barbi Satin Introduction Among many in the transgender world the term shemale is offensive. Transsexual in considered a proper, politically correct term. Transsexuals are persons born into the wrong gender and have the psychology and even brain structures of the opposite gender. They go...

1 year ago
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xHamster Shemale

While I am pretty sure that you already heard about xHamster before, I am not here to talk about that site as much as I am here to tell you more about a certain section that I really like on xHamster. This site is filled with many hot videos featuring the hottest trannies, and you are more than welcome to check them all out.So, do you think that chicks with dicks are hot? If you do, then you have come to the right section, because that is exactly what xHamster has to offer. Now, do not get me...

Shemale Porn Sites
3 years ago
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly...

4 years ago
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly...

1 year ago
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My Shemale Stepmother

Note : This story is completely fictional! My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the...

Incest
3 years ago
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First time fucked by a shemale

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.Her hair was dirty blond...

2 years ago
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How I became a Slave to a Shemale

Hey readers, This is Karan, back with another . I am sure that you guys will love it. I lost my asshole virginity to a shemale I met at a massage parlour. She took me to her place and fucked the wits out of me. So let me give you my brief intro again. I am 5 foot 10 inches tall, have a fluffy personality, and have a dark complexion, but attractive. I have a tool of 6 inches, and I am a pansexual from Hyderabad. I am shemale lover and would have sex with shemales only. I am flexible with both...

2 years ago
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The Diary of a Shemale Whore on Tour

This one comes by popular request and is dedicated to all you naughty people who fe-mailed me and complained that whilst you enjoyed my stories you felt that I could perhaps be a little more filthy instead of being suggestive! Well, I've always said that I'll give you what you want, well, you got it and I hope you like it! Disclaimer; (seriously!) The following story does not reflect the writers personal tastes and depicts entirely fictitious characters and fantasy scenes of an...

3 years ago
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A Shemale Fantasy and my Wife Part 1

Our relationship has always been good. We love each other, and the life we have built. But lately our sex life and our life in general has become some what stagnant. We get up go to work, come home have dinner, then go to bed. It's the same thing you've heard from couples who have been married for ten years. The excitement level no longer exceeds sexual intercourse more then once a week. It becomes frustrating at times because I've always been the type who wants to try new...

2 years ago
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A Shemale Fantasy and my Wife Part 1

Introduction: I didnt know what I was in for. But what a ride. I was always a sexually open individual. But in my world sexual expression wasnt really part of my routine. Im a 35 year old married man. My wife and I met back in high school and have been together ever since. Our relationship has always been good. We love each other, and the life we have built. But lately our sex life and our life in general has become some what stagnant. We get up go to work, come home have dinner, then go to...

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