Caught crossdressing sex stories

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The first time I got caught cross dressing, I was in my teens still at school. I got caught by a friend of my parents Keith. It happened when I was was visiting him his family, with my parents. I was using the bathroom, pretending to take a shit. But instead I was having a sly wank while wearing his wife's black lacey panties bra that I'd found in the laundry basket.

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He walked into the bathroom because I thought I'd locked the door door, but I hadn't locked it properly. The look of shock bemusement on his face was a picture.

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I still remember it as I panicked tried to cover up. I can remember I started to get a bit upset begged him to not tell anyone. He told me to be quiet, hugged me gently pushed me to my knees. He told me that if i sucked his cock it would buy his silence for now. I opened my mouth sucked his rapidly hardening meat into mouth, as i pulled my mouth away i pulled his foreskin back, swirled my toungue around the head dipped my tongue into the eye of his penis. I was secretly excited by this.

Fast forward to the friday evening of the next weekend it was late may day bank holiday. My mother told me that Keith had phoned asked if I'd like to earn some money helping him clear some overgrown garden ready for a new fence. She told me that she'd already said yes I was to go round to his house on the next day to take a overnight bag because they my parents were going away for the night Keith's wife was away for the weekend visiting her mother.

After a long hot sweaty day in the garden Caught crossdressing sex stories told me to go clean up before dinner. When I got out of the shower. Keith shouted up your stuff is in the guest room. I went into the guest room to find a pair of skimpy black lace panties, bra, suspender belt stockings waiting for me.

With a note telling me to shave my all of my body hair that was covered by my boxer shorts my armpits. I went down stairs wrapped in just a towel demanded angrily but secretly glad insidewhat the fuck was going on with the lingerie. He quietly said to me.

Do you remember when I caught you in the bathroom wearing my wife's underwear our agreement? I sheepishly replied yes, Keith reminded me that he hadn't told anyone also reminded me that we were going to discuss it at a later time. Following with if you want me to tell your parents other people about what I saw. I could get dressed in my own clothes fuck off now.

Or if I wanted my secret kept, I would do as I was told. I sheepishly agreed to do as he wanted Caught crossdressing sex stories though I was excited inside because I already had been exploring my sissyboi side, but that's another story. I returned to the bathroom removed the stubble from the areas that needed shaving as I had already had been regularly shaving those areas anyway, then I gave my guts a good clean out prelubed my hole with a good amount of ky.

I got dressed in the lingerie went down stairs to Keith, who was sat in a arm chair in just a pair of boxer shorts. He told me to give him a twirl said to me mmm you look pretty good bitch now fetch me a beer. When i returned with his beer handed it to him he groped me pushed me to my knees. He then told me to suck his cock, i pulled his boxers down to expose a semi soft cock approximately the size of a redbull can, totally shaved.

I started to suck him as he got hard he grabbed the back of my head forced his cock violently down my throat till my face was pressed against him. After i swallowed Keith grabbed my hair, pulled me over to the sofa, bent me over, pulled the panties to the side, kicked my legs apart pressed the head of his still semi hard cock at the entrance to my asshole. As he pushed the large head of his cock into my hole i winced gasped with pain pleasure. Keith let out a groan of surprise pleasure as he sild balls deep into my clean asshole with little resistance.

He started to fuck me slowly deeply, sometimes pulling all the way out between strokes leaving me gaping then begging him to put his cock back in. After a few minutes Keith started to tease me with some very short strokes some random hard deep thrusts making me cry out in a mixture of pain pleasure. While this was happening i started to cum uncontrolablly in the panties even though my cock stayed soft. Keith noticed this said look Caught crossdressing sex stories you. You Caught crossdressing sex stories little sissy slut.

Daddy is making you cum as he fucks your sissy pussy. He grabbed my soft cock balls squeezed enough to make me cry out. He said to me when daddy asks you something you answer him straight away. I replied yes daddy, sorry daddy. Please fuck me some more daddy. With that he smiled slightly, turned sat on the sofa told me to fetch him a beer. As i went to walk away he said to me. As i pulled the panties back over my still slightly gaping wet hole my fingers nearly slipped in without any resistance.

As i returned with the beer Keith told me to hand him a small box from the sideboard. He took out a small blue pill i later found out was viagra swallowed told me daddy is gonna need a little help to keep fucking that sweet pussy all night. Without being told i dropped to my knees started to clean his cock with my mouth. When it was all clean, Keith had finished his beer started to get hard again, he told me that we were going to continue this upstairs. He told me to go up to the guest room as he followed, slapping my ass as we went up the stairs. In the guest room he pushed me down to my knees proceeded to roughly fuck my mouth, throat, twist my nipples slap my face, until he was fully hard ready to fuck my sissyboipussy.

He told me to lie on my back with a pillow under my ass with my legs in the air. I replied yes daddy eagerly clambered onto the bed assumed the position. He pulled the panties off of me pushed them into my mouth. He put my feet either side of his head slowly pushed his rock hard throbbing cock into me until he was balls deep in me, he started to fuck me in a similar pattern to before sometimes slowly deeply, other times pulling all the way out, teasing me with the tip or just ramming back in till he was balls deep, making me cry out in a mixture of pleasure, pain surprise.

As he was fucking me he started twist pull my nipples. This continued for a few hours with him cumming in my sissypussy or sissy mouth as he called fucking me in various positions, until he was tired the viagra had worn off. I was left gaping dripping with a mixture of cum, ass juice lube.

Keith told me to get some sleep. I told him no i was sore. With that he roughly rolled me facedown on the bed, pinned my hands behind my back held them with one of his hands while he spread my cheeks forced his prelubed rock hard throbbing cock into me.

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I screamed in pain repeatedly told him no begged him to stop with tears streaming down my face as he roughly raped me hard, fast deep until he emptied his cum deep inside me, while he was raping me my body betrayed itself i the cum started to dribble out of me.

When he had finished cumming, he pulled out, dragged me by the back of the neck till my mouth was level with his cock.

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He growled at me to clean his cock, as i did this with tears streaming down my face. He told me that my sissypussy was his he owned it me.

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Then he noticed the cum puddle on the bed laughed, he said you said no but your body said yes now you can clean up your own mess. As i was licking up my cum puddle. The phone rang he went to answer it while he left me recovering on the bed. So your mine to do with what i want for the next 24 hours. I asked what about your wife. He then announced it was time for a shower, then breakfast. We had breakfast then he told me it was time to fuck again again. As we were going up to the bedroom, he told me the less i resisted the better it would be for me.

When we got back into the bedroom Keith handed me some clean white plain underwear, consisting of skimpy but not slutty panties a bra. As i was about to put the panties on he told me to stop.

Caught crossdressing sex stories

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Cd crossdresser sissy caught by mom and dad - Sex Stories