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Showing posts with the label cross dressing

The Story Of Maids - Checking Up {sex toys} UPDATE

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Mother asked me to check everyone on the list she gave me to make sure that they were preparing for their role at the party that we are having in two days time. We call it a party. Some people call it an orgy. But what is an orgy but a big party? At least the ones we have are big. “Ok, Casey. You’re good," I tell him as I move his underwear back into place. "If you feel it getting loose let us know ok,” I told him as I ticked off his box and wrote down the size of his butt plug.  “Yes Miss Kat,” he said as he stood upright in the uniform of the day. The top looked normal if not old fashioned while the bottom was just a pair of white panties and white thigh high stockings that were paired some with black flats.  There was an apron, just to let you know that they were maids. It only covered the panties, so for a moment, you are tricked into believing that they weren’t wearing anything until they turned around and you saw that triangle of white fabric.  “You ma...

The Story Of The Maids - Lilly {Cunnilingus} UPDATED

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   I felt the door as it opened and closed causing the air in the room to move, as much as I heard the wood scraping, in that one spot, and the hinges creaking from the weight they now had to support. Whoever it was, walked across the floor in silence. I exhaled and spread my legs a little more before sucking on my lower lip. "What are you are reading?" Aaron asked Al who was spending some time with me between his lessons. I told him that he didn't have to stay since I was busy, but Al said that he didn't mind waiting. "Just looking at the pictures," he answered his older brother. "I like this one," Al said, and in my head I saw how he would have pointed it out to Aaron as he looked at the book from his side of the chair. "That is a good one," Aaron answered him as the boys drifted from my mind. “Mom,” my son said to get my attention. “Yes, Aaron,” I answered on an exhaled as I opened my eyes and tapped Penni. “I don’t ...

The Story Of The Maids - Wake Up Assignment {cross dressing} UPDATED

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"One of our daughters, Patrishia, was present when he, Sally, had his interview," the Countess pointed out as she handed me a photo of one of her maids. The young man in the photo was- "Excuse me Countess," I broke into her story with. "Is Sally a-" I stopped as I tried to think of a more polite way of asking my question.  "A third kind, intersexed?" she provided. "An O? A girl with a breaker? A boy with the curves?" she continued.  "Intersexed," I picked.  "Yes," she agreed before she held her hand out for the photo. I quickly gave it back.  "Patrishia was so impressed by his size, that she assigned him to wake up calls. I don't remember if that was before or after she took this photo," the Countess tried to recall. I had no problem remembering the photo that I just handed over. Even though Sally seemed to prefer being called he/him he was dressed in a maid's attire instea...

The Story Of The Maids - A New One {shota/age gap} - updated

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“Mom? Are you in here?” Julie called out before she turned the corner. “Yes dear,” I answered as she looked into the room. I was seated in a straight back chair with my dress collected around my torso leaving the rest of me accessible for my current activity. “A new one for Dad or Frank?” Julie asked as she leaned against the door frame watching us. “He’s an anniversary gift to your father and kinda for myself also,” I explained as I slowly pushed the dildo into his mouth. He’s been doing great all morning. He could almost swallow the whole thing. It is a little bigger than my husband’s, but this way he will be more than ready. “You wanted something Julie?” I asked my second oldest as she continued to stand there looking on. My arm that went around his neck held his head up as he sat on my lap. As I got the head past his lips again, I stopped as I felt him shake a little. I looked down and saw as some cum bloomed from his stiff cock. “Oh yes,” Julie remarked as she remem...

The Story Of The Maids - The Book {gay/cross dressing} - Updated.

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Hanna, one of my husband's daughters was sitting at the table carefully eating her lunch as she leafed through  The  Book. Once in a while, her hand would find its way to one of her breasts where she would squeeze it for a moment or two before turning the page.  "Who is this tall redhead in the old fashioned outfit?" she asked as she held up a photo to look at more closely. Al leaned over to have a look at it also.  “That shouldn’t be in the book,” Al said as he pulled the picture from his sister's fingers. “Which one dear?” I asked as I now looked in his direction. He pushes back his chair to stand and walk over to show me. I look down, and I see him when he was seventeen. About seven years ago, when he liked trying out some of the uniforms. He was bent over at the waist, with his hand and face pressed against a wall as a man in a white dress shirt and slacks stood behind as they fucked. From what little you could see of his eyes, from his longish h...

Two Habits {Gay/Religion}

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“He’s not a girl and he’s doing it in the safety of our walls and only with fellows of his standing. There is nothing to be guilty about,” one priest told the other. “Then why are you taking him a habit?” The other asked as they walked into the dorm. “He requested it. He said he liked feeling it on his neck,” the first priest replied with a shrug. “He wears the rest of it under his clothes already, so what harm could it do to let him have this once in a while?” They look at each other for a moment as they continue walking down the hall before looking away. “I’ll admit, it suits his face,” the second priest confessed before they stopped outside their destination. The first priest knocked twice, paused, knocked twice, paused and knocked twice again before the door was opened to the junior priest’s quarters. A position the young man of their conversion has held since he turned 17 two years ago. Once the door was closed, they saw him off to their right wearing a habit that s...

Why {cross dressing/yaoi}

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I said that I wouldn’t do this anymore, so why am I here again? Being dressed up as a girl to get past the coach is embarrassing. I don’t care that they all say I look cute in the skirt. “Ohh…,” I try to keep my eyes from rolling back. This is only the third guy. I have at least ten others to go today. I continue to move my hips back into his crotch. Ok. I know why I’m still doing this as I feel him slam into my ass and stir up all the cum that was already in me. ===== I seemed to have missed this one. Maybe I thought it was too short at the time. 

The Story Of Maids - Out For Lunch {public ejaculation/cross dressing}

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“Sorry, I forgot to ask if you wanted any cream,” the waiter said as I looked up from my almost ruined cup of tea. “It’s my first day wearing the new outfit,” he explained as he pulled the front down even harder pushing the rest of his cum through the fabric and into my cup as I continued to watch him. His body must have spasmed at least three times before he was able to walk away. “Did you catch his name,” I asked my wife. “I think he said Janet,” she informed me before she took another bite of her sandwich. === I know, my time is running out to get these things all together. But first I have to save them from the death of my tumblr account. ===

Are You Guys Ok? {cross dressing/trap}

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“Are you guys…ok?” The woman looking down at us asked after Ki fell on me. She blushed as her eyes took in the whole scene. And what a scene it must have been. Until Ki turned around and slipped causing him to fall unto me, we looked like every other couple on the beach.  He in his cute little purple bikini and I in a pair of swimming briefs and light hoody to hide the tan lines she now saw across my chest.  ===  I feel like I may add more to this in the future.  ===

Chocolate Banana {Crossdressing Boy}

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A cute boy got dressed to go outside. It was a warm day. He picked a light and short dress, but nothing flowy since he was horny and slid a butt plug in before he left the house. During his walk he bought a popsicle. He walked around a bit more and attracted a few stairs and even some very long ones, but no one really caught his fancy. When his popsicle finished he found an Asian eatery selling chocolate covered bananas. He had only seen them in mangas and animes and couldn’t pass up buying one himself. A block or two later his sexual buzz was almost gone and he hadn’t cum once during his time out. He now started to look for a place and or person to help with that. He walked until he found a store that mostly sold clothing to gay guys with some sex toy in the back and stood in front of their window. He slowly slid down the window until it had pulled the back of his dress up and over his butt. Now he looks back and sees you watching him. How long have you b...