Late Night Sissy Turns Into Live In free porn video

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Short story my first one! I ran to the store to get some smokes and a few beers and found a new friend.I saw what I thought was a girl riding a scooter stop so I said hello then I realized it was a very sexy dressed guy.He says hello and goes inside I wait for him to exit. He comes out and I just smile and make small talk.I see he is very feminine and that gets me hot.We talk for a bit then he asked me if he can have a beer I said sure,we drink a beer and I then ask if he would like to come over he says sure.
We get to my place he gets in my van and says lets just sit and drink a few beers,hell I was cool with that.I told him he looked damn hot dressed in those shorts he tells me he gets the urge to go out late at night dressed as girly as he can.He just hit me right so I ask him if he would like to be my girly boy he does not say a word just leans over and kisses me.
He has shoulder length brown hair tight shorts and flip flops on and such pretty feet.I told him I would like to play with his feet and bang he was into that his toes at my lips.I kissed and licked his feet and toes then asked if I could see his cock.Oh my god what a sweet 5 inch uncut smooth cock it is.I enjoyed every bit of his cock balls and tongued his ass right there n front of my house in the van.
By now we both are into it full swing and he says would I please call him Jesse it makes him feel much more like a slut,I said yes!He asks me if I would like to be sucked and if so would I cum in his mouth I said yes I want that very much.
We slide to the back area and stripped down and he sucked my cock until I came in his mouth and he asked if we could kiss my cum away I was like hell yeah.It was so very sexy kissing Jesse each of us taking my cum back and forth until we licked every bit of it and swallowed it.
After we just laid back kissing and looking into each others eyes until I asked if he would like to fuck me and cum inside my ass.Jesse was up to that and with our spit and a little effort his cock was inside me.I had to prop my ass up so he could get his cock in my ass but when he did it was fucking great.We would kiss and he spit our own lube on his cock until I was feeling so good I was ready to fuck my new girl Jesse.After about 15 minutes he told me he was about to cum I told him to go right ahead and cum inside my ass.I wanted this so bad and then he did he came I felt his cock throb and spurt inside me.I asked him to just lay on top of me and not to pull out just slowly keep fucking me.When he did pull out he went down and sucked the cum from my ass and asked if we could kiss I said oh hell yes.
We just laid there holding each other until I said I wanted to feel my cock inside him he told as long as I do him while he is on his belly.I was trying to figure out how to lube my cock up and he just says fuck me dry he would lube up once I started to fuck his ass.So I spit a bit on the head and got it inside him though it did take a bit before he could take me all.Once I did though it was heaven he softly moaned and told me to fuck him harder.I said that would make me cum soon he said that was cool it makes him feel much more sexual that way.So I did as we got sweating more and more I could not hold back any more I came inside him.
After we just laid face to face for the next hour kissing and talking softly about what we did.He asked if he could stay over and just sleep with me holding each other for the rest of the night and I was into that for sure.
In the morning I was awake first and just stood there looking at this Jesse a 23 year old crossdresser.He woke up and looked at me smiled and asked if I would like him to be my girl I said yes I would love that.
Jesse went off to work and has called me 11 times today asking if I am serious about us being together I of course told "her" yes.By the way she just finished moving her stuff in about 1 hour ago and I hope this turns out to be the true love I have needed.She did tell me that for now on I need to see her as my girl as she wants to live only as a female.I agreed!

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My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven 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...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met 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. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - 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...

2 years ago
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Sissy Hypnosis Fun

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...

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