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ShavedSeniorSissy
My first anal sex - being fucked like a sissy.
My instructions were clear... 'Remove all the body hair you can, then dress like a girl!' So I did.
It felt so naughty and stimulating to be completely shaved for the first time in my life. My legs and genitals felt so sensitive in the lingerie I was wearing, and my penis leaked precum in to the panties I had on, tenting the material with my throbbing erection.
I could hear the floorboards in the passageway creaking as he approached my room, my heart was thumping in my chest with adrenaline, the blood in my head rushing with excitement, bringing a flush to my face. I was going to be fucked for the very first time up my asshole and I couldn't wait.

I'd spent a bit of time dressing my girly smooth body. Black patent school shoes, white knee length socks, my favorite pair of white cotton panties with matching trainer bra underneath a black pleated miniskirt and white school blouse with tie, all topped with a black cardigan. I was young, smooth and lean, and I thought I made quite a good schoolgirl in my sisters clothes. There was simply no going back now, as the bedroom door opened and he walked in.
'Is your cock stiff?' He asked.
'Yes!' I said.
'Show me.' Came the reply.
I stood from the bed where I had been perched, and lifted the front of the skirt, the bulge in the panties immediately obvious. Pulling the cloth to one side, my erection sprang out and I held it forwards for him to see, proud and excited.
'You know what is about to happen, don't you?' He asked.
'Yes.' I said.
'Good.' He carried on. 'Now, come over here and suck my cock. Get me wet for your asshole!'
He unzipped his trousers and fumbled for his own erection, slowly pulling it free of his pants to show me a larger member than my own, with its long dark foreskin and profusion of hair.
Licking my lips, I walked over to him. Kneeling before his lovely cock, I held its hot wrinkly shaft and instantly took the head of his penis into my mouth as ordered.

I have to say here and now, that I think I was born to be a cock sucker. I love the sensation of another mans penis in my mouth, where I can also taste and smell him as I suck. I love giving oral sex and having my lips parted and fucked by a strong cock. If he'd chosen to just fuck my mouth like a cunt, till he spunked down my throat, I'd have been happy - but I knew this was just foreplay to the main event.
I could hear him grunt with pleasure as I attended to his hard penis, making sure I left as much moisture round his cock head as I could (as I knew exactly where he was going to stick it in a few seconds).
It wasn't long before he told me he was ready.
'Go and put your hands on the edge of the bed, pull up your school skirt and pull down your panties to your knees - I'm going to fuck you.'
Again, I did as I was told.

I didn't have to wait, exposed like he had requested, my smooth balls hanging below my puckered anus, my stiff erection throbbing as it pointed forwards. I then felt a wet finger being pushed inside my bumhole, opening my rectum with his digits. As he grabbed my hips roughly, I guessed what was coming next, and the searing pain of him pushing the head of his penis inside me for the very first time mad me yelp. But there was no let up, he pushed as I protested, pulling me on to his shaft and impaling my on his fat dick.
With a final grunt, his cock was buried balls deep inside my rectum, and then he started to really fuck me.
The pain subsided as I relaxed onto his cock, relishing the fact that I was being sodomised for the very first time. Here I was, having my first anal sex, and loving the fact I was being fucked like a girl up my anus.
All I needed now was for him to spunk inside me, to show me how much he loved me. That's what I concentrated on next. I wanted to milk his sperm from his balls and have his hot cum spurt inside my rectum. That's what he soon did, as he held my hips and thrust up me hard and repeatedly, buggering me till he shot his load deep inside my hole. My first time being fucked like a sissy.

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Member Since: 29-Feb-16
Location: US
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sissy cum slut
Love to have my sissy dress up as a maid in a satin frilly outfit. Tie her leash to the bedpost so her ass is in the air. then I rub my throbbing cock on her frilly panties and get so hard that I cum all over them, Then i pull then off her and put them in her mouth. then I spank that cute ass till it is red then lick it all over and rim that ass. then I am so hard again I pull up that skirt and slowly insert my cock into that ass. then as I go deeper I start to rem her hard so that my balls are bouncing off her ass. I cum so hard but i hold part of it so I can finish it on her face. now I got to pee so I untie her and get her on her knees so I can piss on her face and in her mouth

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ShavedSeniorSissy
Love to dress en femme to be used. So good to be in sexy lingerie as I have my mouth and anus fucked hard and deep.

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SissySlutFiona
I saw an advert in a contact mag (we didn`t have the luxury of the internet and mobiles in those days) it read something like `Mature man seeks younger to dress and be used as a sex object`. I went through the contact details and arranged to meet his at his home. Doing this was new to me and I was a little nervous, when he opened the door I saw a huge smile on his face and a very welcoming hello. Sat in his living room he asked why I had replied to his advert, when I told him that I so want to become a sissy woman but did not know how to and was hoping he would help me.

He asked me to stand up and strip which I did, when he saw that I was wearing a bra and knickers that were miles to big for me he chuckled. He told me to remove the said clothes, `come with me` he said, he held my hand and we went to his bedroom, he opened up a wardrobe which was full of beautiful dresses, high heel shoes, wigs etc. He pulled out a couple of dresses for me to try on, the first one was a perfect fit, next came the heels and then the Blonde wig. I looked in the mirror and I felt fantastic and looked so sexy. He said `that will do for now and he took me in his arms and we kissed passionately, I felt for his cock and it was huge and very hard so I played with it. We got onto his bed and rolled around kissing and sucking on each others cocks.

I felt his fingers playing with my hole, I was a virgin and told him so, `don`t worry` he said `I am an expert at this and you will be fine`. He picked up some lub from the side cabinet and smeared it in and around my hole, getting me on my back and pushing my legs above his shoulders he put his cock at the entrance of my hole.

`Relax` he said ` it will hurt a little but will become enjoyable, you will like it`, he was right it did hurt as he pushed into me, so much so I was nearly in tears, he began to kiss me which helped a lot as he pushed deeper into me. When he was fully inside me he said ` we must give you a name, how about Fiona after my wife?`. I nodded and he began to fuck me, oh it was wonderful, I was so loving it then all of a sudden I shot my load, I looked at him and he was as happy as a pig in shit, `Fiona` he said `you have just had your first orgasm as a Sissy without anyone or anything touching your clitty`. He then went into fuck this slut mode and pounded me, I felt him cum inside me, that was also fantastic. He carried on untill he became soft and it dropped out of me.

I agreed to meet up with him on a regular basis and he dressed me including make-up on every visit. It was the best thing that could of happened to me, he introduced me to other guys who also liked and had me, quite often due to the heavy meetings I was totally knackered when I got home but was never late for work the next day.

Yes he changed my life completely, I became a Sissy and got the name of Fiona which still is my name, the added good point when I married Sandra she liked the name Fiona. Thank you all for reading. xxx

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cissybiboi
Fantastic read Fiona xx

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Member Since: 9-May-21
Location: UA
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Переодевание
Я тоже люблю одевать женское белье и одежду. Єто меня заводит

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