A Sissy Maid Finally Caught free porn video

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What does a crossdresser do when they have just got home from yet another boring day, packing boxes at a factory for minimum wage, dressed in boring man's clothes? It's a rhetorical question, because we all know what comes next. I shaved myself and went to my bedroom to put on a full face of makeup, following an online tutorial. It looked great, more convincing than ever, with dashing crimson lipstick and matching fake nails, and a stunning blonde wig. And then, to the wardrobe, containing all kinds of secret sissy delights. A full matching set was in there by now... Black stockings and suspender belt went on first, followed by a small black satin corset, tightened for impressive curves. Over that went matching black satin panties and a padded retro satin bra. All of this had me hard already, but my eyes then fell on the finishing touch, a brand new black and white French sissy maid outfit. This slipped on easily over the top, a perfect fit, and beautiful too.

As I admired my reflection I heard the front door bang shut.

Oh no. Oh no no no. How could I forget about that?

A builder had let himself in. He was supposed to come yesterday to fix the leaky roof, but never showed up. Now he was here and I totally forgot about it. My heart fell through the bottom of my chest as I connected the dots. He had to come to my room to fix it. The sound of footsteps confirmed the inevitable. What can you do in that situation? I didn't have any time to figure it out and decided to try and own it.

"Hi!" I said loudly as he came round the corner, laid eyes on me and stopped in his tracks. "Sorry you caught me like this... You're here for the roof, right?"

"Yeah... I'll just get on with that and stay out of your way..." said the worker, awkwardly and with shifty eyes. "Tea?" I asked casually. "Sure," came the response. Maybe he didn't care, I thought.

I scuttled out of the room, more embarrassed than I've ever been, and made a cup of tea. I've been doing this for years, and finally got sloppy enough to get caught. I brought him back his tea. As I passed a mirror on the way back, I noticed that the reality had shrunk my earlier excitement, leaving a completely feminine figure.

"Kneel." Said my guest sternly, when I arrived back in the bedroom. His tone had completely changed from sheepish to dominant and strong.

"Uhh, what?"

"You heard," he said. "Get on your knees now and I won't tell anyone what I just saw. I put down the cup of tea and kneeled down, a bit scared.

"Nobody has ever seen me like this before," I said, in a half-whisper. He walked right up to me, sandwiching me next to a wall with no escape, and he then undid his trousers.

"Maid, clean this up." His hands quickly removed his undergarments, and the large half-erect member left a glistening mark of pre-cum where it flopped out on my highlighted cheek. I had never done this before and I was a bit scared. As he guided his cock roughly into my mouth, I gagged slightly as I savoured the new experience and took the penis inside. It wasn't so big, 5-6", pretty average in size, I thought to myself. It filled my mouth and left a pleasant taste as it passed back and forth. I found myself enjoying it and a little turned on.

"I like it," I said seductively, looking up to him after I managed to pull away from his thrusting temporarily.

"Yeah, you like my hot dick? Suck it you hot slut." By this point he had pinned me against a wall, so there was nowhere for my face to go but to submissively accept his full erection once more. I continued to take it and saw that I too had become hard. When my new partner noticed this the thrusting sped up and he moaned softly.

Gasping for air after several more minutes of impromptu throat fucking, I felt what I knew to be an orgasm, as his member pulsated and unleashed seemingly endless hot sticky goodness into my mouth. It wasn't as bad as I heard that it tasted. I smiled up at him from the floor as I cleaned him up, acting like a natural as I left a lipstick mark at the base of his shaft.

"Good work, maid," he said, allowing a moment to compose himself before walking to the desk and picking up his phone. My heart sank again as I saw where the phone had been sitting, and realised he had recorded the whole thing. He looked at my shocked face, laughed, and came back over to me, and squatted down.

"Looks like I don't have the tools to finish this job right now," he said with a grin, "But I'll have to bring some extra help next time."

And then just like that, he was gone. I sat on my bed feeling confused, fuzzy, and apparently still solid underneath my lingerie. It only took a few strokes before I came, harder than I'd ever been before, with my load landing on my own face. My first taste of being a true sissy, I thought.

And it felt great.

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3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Of The Lamp Finale

Taking a bowl of potpourri from the table she emptied the contents on the floor, then clicked her fingers. Davina gasped as her attire was instantly changed from that of rubber assistant to French maid. Black glossy eight inch stilettos, opaque black stocking with a seam meticulously straight up the back. Black satin dress the skirt held up horizontal by the froth of petticoats. The waist waspishly tight and of course her tits thrust out on display like two melons. Was it her imagination...

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