Sissy Tranny Annie Slutty Fantasy free porn video

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I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me.
My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved wearing hold ups, thongs, and best of all she loved to wear really high heels and she was the same size feet as me which was even better. I dressed up nearly everyday pretending to be her getting fucked by me, she loved taking my thick 8" cock in her arse and in the end she preferred arse sex more than my cock up her smooth pussy. Whenever I fucked arse I would think it was me on all fours dressed as a slut taking a big cock up my tight arse hard.
I was gutted when the relationship ended as I no longer had the high heels to wear, so for the first I went and purchased my own. My god it made me feel so horny ask the shop assistant for a size 7 high heeled shoe, I first thought that she didn't know they were for me, that was until she came back with the sexy black strappy heels, she looked me in the eye and said "would you like to try them on". I smiled and made some shitty excuse about them being for a friend and she told me to come back soon.
These were the days before the internet and sites like this which pisses me off because if I was on this site back then, then I would by now be a permanent sissy, worshipping a sexy guys cock.
I stopped dressing for a while trying to stop my urges to want cock, but I just couldn't stop. Putting on black hold up stockings and heels just made me want cock more and more. Whenever I wear them I forget im a guy and I instantly turn into Annie, a siisy tranny that is just a pure slut that would do anything for a cock.
A few years later I moved in with my current wife, I started to collect and buy more nylons and heels and was struggling to keep it all hidden, so I had to make my collection smaller and I just started to buy her lots of sexy underwear and clothes, knowing that they would fit me. I started to take pictures of myself which turned into an even bigger slut wanting to suck and fuck guys more and more.
I then bought my wife a massive 12" dildo wishing that 1 day I will force it up my virgin arse and pretend it was a real cock. This is what I did after I got chatting to guy when I first got on the internet. He was a fellow tranny and he wondered why I hadn't ever shaved my legs and told me I should. I did this and I felt amazing, so fucking slutty, I knew then this is how I wanted to be. Smooth from hair all over my body in slutty sexy underwear with a cock in my arse. The dildo felt good when it was buried in me but it still wasn't right, I want a guy, a real cock who could make me his slutty tranny bitch.
I have had to let my hair grow back now as my wife got sus and especially now that she has found all my sissy photos.
Since she has found my photos my cravings for cock have got worse and all I can think of is being fucked.
I have been chatting to a real sexy guy on here who lives close to me and says that he wants to fuck. I really want to be his bitch slut, it was he who gave me my tranny name Annie. I have told him my fantasy is to wear some black seamed hold ups, high heels, my wives underwear and sexy tight dress. meet up with him where he can do whatever he wants to me... I would be his total sissy sex toy. to face fuck me, make me gag, choke, puke. lick his arse. then I want him to fuck me with his hard cock so fucking hard that I cant sit down for weeks. I want my tranny arsehole ruined by his cock. I want to fuck for hours by him and for him to fill my arse with sexy warm cum. then make me go home in my shitty boy clothes but still in my hold ups and panties. Telling my wife what a great day ive had as I can feel my masters cum running down my legs. then I will fuck him whenever he wants, in my bed. I hope to get fucked by him in my marital bed, then whilst im dressed as annie the slut, riding his cock, saying how much I love his cock and all I ever want is his cock in my arse because im a gay sissy tranny. As we change positions we both see my wife standing there. she just stays there as he tells her to watch him humiliate me.
I am looking forward to our meeting very much and hope it comes sooner rather than later.

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Annie Goes Skiing

“You’ll look fine Annie,” Jeff assured her. “What are you a mind reader? “You’re not that hard to figure out sometimes,” he replied. Annie pondered those words for a moment after they got in the car and started off. She wondered to herself how she let Jeff talk her into this ski trip anyway. Annie, ice and cold weather did not mix. It was not a big secret that the only time Annie liked ice was if it was crushed and blended with liberal doses of tequila, and perhaps, a lime wedge...

2 years ago
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Lip and Annie Ch 09

Their first week back they were both very anxious to hear each other’s voices on a daily basis, so their phone calls back and forth became routine. Annie was working a lot of night shifts and trying to sleep in the day, and they usually talked in the late afternoon. Robert was busy too, but he was fortunate that his business didn’t run on set hours, and he could usually make time for Annie whenever she was available. She had told him that the first available appointment with Dr. Maier would be...

3 years ago
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Annie

I was just getting ready to close up the shop for the day when this gal came in. Oh who am I k**ding, this was no gal, this was a lady. She was my height as I looked straight into her eyes, but she was also wearing heels, so she was probably more like 5’5” to my 5’9”. No more than 25.Black straight hair that flowed to the small of her back, and a gray dress that fit her slender body perfectly. As I saw her walk to my desk I could see her hips swaying and moving back and forth, and found myself...

3 years ago
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ANNIE AND NINA

My little sister Nina sounded so excited to hear that I was finally about to come home, and even though it was late she said she would wait up for me. I was using the phone in the Pastor's office to let her know that we had driven into the night, and the bus had just pulled into the church parking lot.And just before I hung up, I whispered her that "IT" had finally happened, and she literally squealed with excitement.She gasped, "Annie, are you serious? You mean you really 'IT' really...

2 years ago
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Annie A Noblewoman in lust

Annie, or to give her her full name, the honourable Annabel Eizabeth Mary Weatherby-Hanines, strode across the meadow in the afternoon sun. The village lay before her in deep shadow as the sun began its slow descent to the western horizon. She barely considered that everything she could see she owned. She just felt lonely and persecuted. A woman alone in a man’s world. She knew everyone on her estate were taking advantage of her. It was pure luck that she had inherited the estate as back...

4 years ago
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Annie A Noblewoman in Lust

She saw the village forge at the village edge. No smoke issued from the chimney, the idle blacksmith had obviously gone home early. Annie decided he needed a lesson. She had known Tom for years, why she even had a crush on him as a young girl, nearly lost her virginity to him in an apple orchard one summers day many years ago, but that was then and this was now. She was the boss and he a labourer. She never married, with no living father and an idiotic mother she had had to fend off...

3 years ago
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Annie in Atlanta

Annie Bradford, a highly respected College Dean from Minneapolis, Minnesota, was visiting some colleagues at Emory University in Atlanta, in hope of enticing one of them to accept a position at her university. Annie was a very young forty and divorced with no children. Her husband had left her for a younger woman four years before and, heartbroken, she'd thrown herself into her work.We meet her as she’s just finished watching a porno movie in her hotel room. She’s horny, almost desperate for...

Quickie Sex
2 years ago
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Lip and Annie Ch 07

Angus managed to maintain a straight face for several seconds while he watched Robert’s face turn white. That mission accomplished, he quickly added, laughing as he did so, ‘I’m just having fun with you, Robert. Annie is a big girl now, and she makes those decisions on her own.’ ‘She has told us a lot about you, and just how good you have been to her. She also explained that the room will have two double beds.’ Robert was immediately put at ease by the older man’s words, and he quickly said,...

2 years ago
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Saving Annie Part 3

Her body ached and throbbed with longing. Ivey was caught in the rapids of the current now, rushed along with no control and no hope of regaining control. Ivey wasn't even sure she wanted to regain control. This was too good, the feelings were too good in Annie's body. Whatever was different about her body, and there was plenty different, Ivey hadn't expected this. Annie's body was more reactive, more sensitive, than Ivey's old body ever had been. If kissing in Ivey's male body had...

4 years ago
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Pam and Annie

This is an excerpt from an unposted story, 'Windfall' Pam learns early Pam went on to describe to me, in detail, her childhood awareness of sex and her early fascination with it. She was fortunate that she grew up in a close-knit household with a great extended family and parents that were stern but doted on her. But she had discovered when she was about six that playing with herself brought on the greatest pleasures she had ever experienced, and she was masturbating from that time...

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