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My teenage years as a sissy

1056 words | 5 |4.32
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I wa 12 when I was a exhibitionist and got caught by a older boy

When I was 12/13 I used to be a exhibitionist always doing private flashing and at night I would go in the local bowling club (it was closed) they had trees around and I would strip off and run between the trees and then have a great wank , I had done this for weeks and never been seen .
Then one day a older boy he was 17 from the neighbourhood he was a gang leader came up to me as I was leaving school, he said your that lad who lived near the park I said yes then he said I know your secret at night I felt shocked scared incase he told everyone but he whispered its cool I’ve watched you , I said don’t tell I will stop he said don’t stop I want watch see you tonight and walked away.
I didn’t know what to do but it turned me on someone else had watched me I ran home to have a wank.
That night I went out as usual looked around no-one there so I did my usual strip off and run around the trees and when I went back to my clothes and he was there my cock went hard he said finish your fun let me watch as I wanked he undone his zip and got his cock out and I watched as it went hard as I cum he then said wank me, I hadn’t even seen a cock before never mind touched one but I did as he asked and wanked him he didn’t take long to cum and he thanked me and said see you tomorrow night .
I got ready went home and wanked most of the night the next day the same happened and did for a week.
Then he told me he liked me but he wanted me to be his sissy I didn’t know what it meant he told me that it meant he wanted me dress as a girl in the trees, I was shocked but excited as I always wanted wear girls clothes but I didn’t have he said he would bring done of his sisters, the next night I turned up undressed and he turned up with a bag and pulled out a school skirt and blouse I put on and went through the trees did my wank and he had his cock out and as I reached forward his hand went under my skirt and grabbed my cock ohh it felt so good I instantly went hard and my hand was wanking him so quick and he was me too I shot my cum over his sisters skirt he also cam and his shot over the front of the skirt , he looked at me saying if you tell anyone your dead it’s our secret, take these clothes home and i will see you tomorrow.
He left i went home and went to my room as never anyone in mums at work nights and dad never hardly comes home as I dress up in the skirt and blouse I walk around the house it feels so good the feel of the clothes different from my boys clothes, I went in my mums room and took a pair of her panties and wore them too it made me hard time for another wank, I lay on the sofa wanking feeling the clothes it was amazing.
The next few night the same happened and on the Friday he brought me some of his sisters panties bra and tights I couldn’t wait to put them on but I had a plan I told him that my house was empty if he wanted to come as no-one home till morning he agreed and we went I hadn’t changed till we got to mine and he waited as I went up stairs to get changed I came down with the whole lot on tights everything he reached and pulled me over his hand went up my skirt into my tights them panties and he pulled my cock out I was like putty in his hands as he bent down and started to suck my cock, it felt amazing as he sucked and I shot my cum in his mouth and he swallowed it all then he grabbed me turned me around pulled my tights and panties down bent me over and I could feel his cock against my bum hole he was pushing he was going to fuck me I felt my hole open and pop his head was in he pushed a bit more then he pulled out and pushed back in then he was thrusting his cock in and out of me it hurt so much but felt so good he pulled my head back as he thrusted in me and he was getting faster then he pushed hard and I felt a warm liquid in my bum he was cumming I had been fucked by a boy and I liked it dressed as a girl he pulled me backwards towards him as his cock pumped his cum into me then he pulled out with a plop and I could feel the cum dripping out of my hole running to my balls and down my legs.
He turned me over and said from now on that’s what we do and don’t tell anyone as I have a girlfriend too.
He didn’t leave straight away he stayed for a while and I was still dressed in my girl clothes he made me wank him while he videos it and then he did the same to me, he told me I was a good looking girl maybe grow my hair longer, it wasn’t short it was quite long anyway but I agreed and said I could get a wig from fancy dress shop till its grown .
He agreed and said he would get me more of his sisters clothes and I could dress up properly he said he could borrow his older brothers car and drive me around somewhere no one knows him and I could be dressed as a girl .
That made me hard and I started wanking and he said that’s my job and wanked me again I felt so good his big strong hands on my cock I was like a little girl compared to him.

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5 Comments

  • Reply Can’t-tellU ID:1cl4goj6ytxv

    OMG yes.. this is almost like me.. I’m 13 skinny 90lbs 5’5” I would get naked running around this Park Friday nights when a older man caught me grabbing my naked body feeling me all over telling me how young sexy pretty I was like a little girl he kissed me his tongue sliding in my mouth I never kissed anyone b4 but before I knew what was happening we were French kissing swapping tongues he sucked me I sucked my first cock falling in love with it.. I go to his house every Friday night he dresses me like his little girl

  • Reply [email protected] ID:5vn3j3z0m9c

    You need BBC .

    • D ID:1cl4goj6ytxv

      K.. I’ve always wanted to try a BBC fulfilling my darkest deepest desires secrets.. I’m not the boy who posted this story ..I’m 13 white boy 95lbs 5’5” n kinda addicted watching porn especially fembois I love wearing panties short shorts secretly cruising the park at night hoping to find someone.. if u live kinda close or.. maybe we could cum someplace n meet secretly discreetly I can’t get caught mom/friends would freak.. dannypartyka @icloud.com i wanted to email u but got scared

  • Reply Wolfe ID:1ebmcvx9b7qa

    I love to cross dress. And that made my little sissy cock hard. Little boy cum yummy

  • Reply Barney ID:1ctsc2ezmgbt

    Wow you’re a lunky guy your story is so close to my own fantasy I always wanted to enjoy a man dressing aas a women