The first time i got caught crossdressing

This story is based on my actual experience.

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. 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. 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 agreed he opened his trousers pulled out his semi hard cock, i stared at (it in secret joy as it was`nt my first cock that i`d sucked etc) Keith told me to hurry up as it was`nt going to suck its self. 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.

He groaned in pleasure as the pre cum started to dribble out of the end, he pushed his cock balls deep into my mouth making me gag continued to fuck my mouth until he came unloading into my mouth throat, he held my head with his cock balls deep in my mouth throat until he`d finished cumming.

While telling me that you`d better swallow the lot, he pulled his rapidly softening cock from my mouth, put it away told me get my own clothes on we'd discuss him keeping my secret at another time. 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 Keith 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 inside), what 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 (even 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. So I'd be ready for a good fucking, even though Keith didn't know I'd already been exploring my lust for cock with other guys this meant i`d already taught myself how to prepare my body for a good fucking.

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. He continued to roughly fuck my throat while i was struggling to breathe tears were streaming down my face, until he unloaded what felt like a endless load of cum, which he told me i`d better swallow. 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.

He told me i`m going to fuck your sweet little pussy till you can`t walk. 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. I said surprise you are not my first i`m ready for you daddy.

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 at you. You fucking little sissy slut. Daddy is making you cum as he fucks your sissy pussy. When i didn`t answer him fast enough he stood me up, span me around to face him, i wobbled a bit due to for the past few minutes i`d been bent over the sofa with my head down.

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.

Cover that pussy up i don`t want you making a mess all over the house. 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. It tasted a bit funky but delicious a mixture of my ass juices Keith`s pre cum lube. 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 then applied some fresh lube to my puffy but drying out hole his cock, while saying don`t want to wreck it till i`m ready.

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. In the morning i was awoken by Keith`s cock probing at my hole which had stopped gaping overnight, but was bruised sore. 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. 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. 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. 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. He returned with a smile saying that was your parents, i told them that i needed your help for another day i`d bring you home monday. So your mine to do with what i want for the next 24 hours. I asked what about your wife. he replied she wont be back till midweek .

He then announced it was time for a shower, then breakfast. As he didn`t want me passing out missing any of the fun, he took me to the bathroom, gave me a complete internal clean out, then we showered together where he shaved any stubble off my body moisturised my whole body afterwards. 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. Bend over show him my pussy. As i was bent over he said this will help for later i felt some thing cold on my swollen bruised hole.

Then i felt something being pushed in that stretched me stopped. He told me that`s a butt plug to stop you going to tight you making me cum too easy. I continued put on the lingerie as i was doing this he told me that there was some clothes for me to wear as well. They turned out to be be a school uniform consisting of knee high white socks, a dark green yellow plaid fitted skirt that finished just above the knee, a white short sleeved blouse a dark green cardigan.

When i finished dressing, i looked over at Keith who was laid on the beg slowly stroking his hard cock i asked him. Does daddy approve? He answered with get over here suck daddy`s cock he`ll show you how much he approves.

I started to suck his cock ,he made me stop a few times as i brought him close to cumming, except for one time when he couldn`t hold back unloaded in my mouth, i swallowed the lot said thank you daddy. He called me a slut told me to strip for him. I stripped slowly when i got as far as the underwear socks.

He told me to stop get on my back on the bed. As i climbed onto the bed i saw Keith applyling lube to his cock, i went to remove the panties he stopped me. He lifted my legs placed both of them together on his shoulder, pulled the crotch of the panties to one side pulled out the butt plug. I gasped at the sensation as i was left open gaping for a few seconds before he pushed his prelubed cock balls deep in me.

He kept it there balls deep i could feel it throb inside me. A few moments later he started to fuck me with a varying rhythmn, speed depth, at times pulling all the way out then shoving it back in balls deep making me groan, moan, gasp wimper. sometimes with pain but mostly with pleasure. Other times he would tease me with just the tip etc.

All this time the cum was dribbling from my soft cock soaking the panties. Keith saw this chuckled while telling what a complete slutty little bitch i`d become. At some point i must of zoned out i felt him tweaking my nipples as he fucked me which made me clench my hole involuntarily, with one last quite vicious tweak he buried himself as deep as he could get inside me.

As i clenched as hard i could he groaned his cock twitched as he unloaded a massive load deep in my ass. When he had finished cumming his cock was still inside me, he leant forward. Put his arms around me rolled onto his back. We ended up with me on top of him as his cock softened i could feel his cum my juices seeping out onto him.

Keith lifted me up a mixed load of cum ass juice splurged out. He laughed said that`s a lot of cum i pumped into your sissy whore cunt, best you clean up the mess don`t waste a drop. I quickly turned around slurped licked up the delicious combination of cum ass juice.

I made sure to be as gentle as possible around the cock as not to arouse Keith make him hard again. He sleepily told me to go shower he would join me in a bit. I finished my shower returned to the bedroom. I was exhausted, my whole body ached, my asshole was wrecked, sore still gaping.

I could easily slide 3 fingers in with minimal resistance. I decided to quietly get in the other side of the bed rest. In the morning Keith woke me by climbing on top of me pushing his cock into my ruined ass. I was already laid on my front he told me that we had time for a bit more fun, before his wife came home this afternoon.

I winced as he went balls deep without stopping after he`d finished fucking me, he told me to go shower as he had to take me home because his wife was due home that afternoon. As he dropped me off he said see you soon slut.