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New Little Sissy

New Little Sissy

... for sissies like you."

She held them up and showed him the little hole in the front of the
panties ... to have magically disappeared.

"Come along little sissy boy, it's time for lots of feminine ... a big
helping on the brush and then held it under his nose. "Yes my little
sissy faggot breath... Continue»
Posted by liam6969 5 years ago  |  Categories: First Time  |  
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Mommies little sissy slut

... on purpose just to catchmy little sissy son and I left that underwear which you seem to be enjoying ... beautiful girl arnt you sissy?" "now enough of this nonsense I need to put on your new dress. knowing I ... girlfriend said has our little sissy got a name yet?" and my mum replied "no good idea can you think of one... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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A New Sissy Maid

... , not used to her new sl**pwear, but within fifteen minutes she was sl**ping like a little girl after ... garter belt, with a little pink rose on the front. And a black choker around his neck which his ... turtleneck once covered. There he stood in shame and mortification, as the sissy he knew he was and had... Continue»
Posted by NancyBerlin 22 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Little Sissy Boy (written by request for a reader)

... involuntarily.
“Well? Isn’t that true you’re a little sissy slut?” She said as she glanced over ... was a little sissy and had been caught cross dressing. I was so ashamed.

“You know Peter, when I met you ... .”

“I want you to lay over my lap and stick that little sissy butt up in the air. Do it now.” She... Continue»
Posted by justrealgirls69 2 years ago  |  Categories: Fetish, Masturbation, Hardcore  |  
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Prison Bitch (for all my little sissy fag boys)

... behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I’ll now share ... for contraband. Once showered and in my new orange numbered uniform, I was lead into this giant mess hall ... a fair share of the inmate population viewed me then, as a new exciting sexy desirable young piece... Continue»
Posted by plumprumpbrat 1 year ago  |  Categories: Anal, First Time, Gay Male  |  
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moms new sissy

... because she is doing the same to mine. I've had long hair my whole life. When I was little my mom ... a little. 'Calm down Dan!' I thought. I had to act before I lost my nerve.

I shifted myself ... audibly. She looked a little disappointed which I was sad about but seriously, what can a girl expect? I... Continue»
Posted by momandboys 2 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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Sissies New Years Surprise – Part 2 –

... of cummies?” sissy gulps, knowing how she has to answer and also knowing it has an entirely new meaning ... some time only stopping when Mistress would lift up a little to allow sissy to catch her breath ... Chapter 2

Sissies Opportunity Blown

Sissy was dead tired. It had been a long and tiring day... Continue»
Posted by JSissy206 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sissies New Years Surprise – Part 1 –

... tomorrow.

Its New Years Eve and She had told sissy that T/they would be having a quiet New Years Eve ... spent a ton on all new clothes and uniforms. She loved to dress sissy up in various outfits, so ... in her new room.

Sissy barely audible spills out, “A Man Mistress.”

“Speak up, I can barely... Continue»
Posted by JSissy206 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Daddy's Little Sissy Cock Sleeve.

... and ankles to the corners of my bed in leather lined steel resrraints, face down, with my little sissy ... a silly little sissy faggot I am. Not many people watch, which he would say that I was lucky to have ... an owner like him, because nobody has any interest in silly little sissy faggot who only wear pastel... Continue»
Posted by AniGirl81 6 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Sissies New Years Surprise – Part 3 –

... , but what about you? Why don’t you find a new girlfriend?”

Sissy barely audible replies, “Because I ... with a big bow.

“There Your all done you little hotty”, Mistress said. Sissy blushed and curtseyed ... Chapter 3

The Decision

Sissy got out of bed at her usual time and went about her morning... Continue»
Posted by JSissy206 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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My Little Toy Sissy-boi - Ch 1

... My Little Toy Sissy-boi

Chapter 1

By CDJackie


I was standing at the sink with my ... later when I returned to the bedroom.

“Well, my little sissy, having fun?” I asked as I sat ... of her tight little ass. When I closed the door and she turned to face me I gazed up and down her... Continue»
Posted by CDJackie 9 months ago  |  Categories: Fetish, Shemales  |  
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My new ladyboy- LittleLi - Part 1

... It was nice to meet my new freind littleLi. I met her at the library at college one day ... was wairing a little cropped T shirt with a hello kitty picture on it, showing off her smooth honey ... to myself, only an asian girl could wair little frilly laced ankle socks and mary janes and get away... Continue»
Posted by igglepiggle 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Little sissy bitch

... want a little toy to play with and I've decided it's going to be you. Get naked, now. On your hands ... and knees. Want you in front of me. I've got a little present to give to you today. Hmmmm....very ... against your cock, pulled tight over your balls, that little string gliding through your back channel... Continue»
Posted by cummymummy 2 years ago  |  Categories: Anal, Mature, Taboo  |  
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A little role play sex chat session with a new f

... pussy to you begging you to take it

MR.x fuck yes yes,i want you my beautiful gay sissy tranny wife ... dick flying under your skirt.....ahhhh my gay sissy wife cock waiting for me to stroke it while i slide ... come here and fuck your gay sissy wife's asshoel all night long and fill me up with your cum... Continue»
Posted by freakyerica 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Sissy Boy Slave and His NEW Playmate, Sadie

... and His friends get in the Mood for Young Sissy Boy meat to strip and abuse on the livingroom floor ... , inside the 'Big House'!

I'm f******n and have been His Secret Sissy, Piss-Whore Slave since He ... , with the gifts and clothes His friends give me after Sunday afternoon's Party.

I am His Sissy Boy, Sex Slave... Continue»
Posted by sharleesisterboy 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Femdom Strapon

... my legs meant that my tight little hole was at full view.

Before I knew what was happening I felt ... for it to stop.

Before I knew what was happening the pain did stop to be replaced with a new sensation ... of a rubber gloved hand inserting 2 fingers into my tight little arse. I was being lubed up good... Continue»
Posted by redz245 2 years ago  |  Categories: Fetish  |  
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A SHORT SHORT STORY part 3

... at this strange new person standing before me and tried to absorb all the revalations I had encountered ... all within the span of a few hours.
"I'm a senior citizen sissy," he calmly and quietly ... to?"
"Yes. Mr Luther is an old black guy. He must be about sixty-five. We met at a little party. He has... Continue»
Posted by slappywag64 2 years ago  |  Categories: Anal, First Time, Gay Male  |  
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Cuckold in Milwaukee Has Fun

... would you like your little sissy to wear?” Judy said, “I would like for him to have something ... of screaming as they came. The whole situation gave new meaning to the term, when the van’s ... .

A sexy woman dressed a little like a goth cam to the door and saw Kris and smiled and said... Continue»
Posted by toothmedic 1 year ago  |  Categories: Fetish, Group Sex  |  
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Reina's Story

... in the mirror. I nearly blow my wad at the sight before me! I have never seen such a sexier little sissy slut ... .

Laughing “Just look at you…..my little sissy is all grown up!” She laughs more…..

“Thank you ... then, sissy reina?"

"Ah...there you are" she says as she snickers loudly. For some reason she just... Continue»
Posted by sissy_reina 3 years ago  |  Categories: BDSM, Fetish, First Time  |  
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Making of My Sissy (Part Three)

... shyness about who he was. As time went by my sissy was really enjoying his new role around ... and I would call my sissy to tell him I will be a little late tonight. A good sissy he was as dinner ... One day I was home to see, first hand, how my sissy's day progressed. The day went as I thought... Continue»
Posted by sissymishel 2 years ago  |  Categories: Fetish  |  
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