My first time

By crossdresser4fun

Original link: https://www.lushstories.com/stories/crossdressing/my-first-time-2.aspx

Tags: sissy, fag, slut, crossdresser, anal

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Sissy a night out
I started cross dressing when I was about 12 im 16 now and my stepsister is 19 I would always steal my stepsisters clothes so last summer my parents where on vacation to Cuba and it was only me and her for a week , one of the days I was wearing a thong under my shorts and I guess my stepsister must of saw because she called me into her room and showed me a leopard print bra and asked if I liked it (I did) so I acted confused but I knew I was caught, she said she knew I was wearing my clothes and she doesn't really care , she asked if I liked guys, I told her I was bi so she asked if I want to come to a party with her but dressed as a girl, I hesitated but agreed she said she would do my makeup and dress me , she said while I shave everything she will go out and get some things to help so after I got rid off ALL of my body hair I walked into her room and there was a pink thong with bows on it and the same leopard print bra, she gave me a extra small black backless dress with white stalkings and a black garter belt when I was all dresses she came in with pink nail polish and a pair of bright pink high heals finally she did my make up and gave me a blonde wig , me and her looked almost like twins. After about 30 minute drive we arrived to a open house party and we both looked so fuckable it would have drove boys crazy, because I don't have a good girl voice she told people me and her had a bet that I wouldn't talk the whole night I went to the living room and danced by my self for less then a minute before guys started coming over and dancing with me, it made me and them so Horney the way I would rub my ass on there dick so I gave my stepsister the look and she came and told him about the bet and then whispered something in his ear I was confused then he grabbed my hand and pulled me up to the master bed room. She sat down on the bed and told me how my stepsister told him that I'm on my period but I give great head and love anal, I was really nervous but I took the hint and started to undo his pants slowly and I reached into his boxers and pulled out his 10" hard dick I began by kissing the head and licking his balls he had a musky smell about him that I loved . I sucked him off for about 20 minutes before he grabbed my neck and turned me around pulled my thong to the side and fucked my ass I cried because he was so big and it felt so good I started to moan he fucked me for about 10 minutes and I already cam in my panties and he said he was coming and pulled out and forced his big cock back in my mouth and cam 6 long ropes of cum in my mouth I didn't swallow right away because I wanted to savour the taste he got dressed and pulled a maker off the bedside table and wrote his number on my arm, when I came back Down stairs my sister was gone so I called a cab and the driver kept looking at me it was weird but I think he wanted to fuck when I got into the house I saw my stepsisters shoes so I went to her room and she was getting fucked by her boyfriend she saw me and smiled so I left quietly when I got to my room I saw a dildo and there was some random guy in my bed sleeping so I got In bed and he woke up and wanted to fuck but I was so sore, I told him no but he pushed me down grabbed my hands lifted my legs over his shoulders and fucked me and cam In my ass in the morning I woke up to someone coming In my room it was my stepsister who had the biggest grin on her face and just told me there was another party tonight when she left I was so happy, I got unchanged put more girl clothes on took the makeup off went back to room and used the 13" black dildo on my self till I cummed on the head of the dildo and licked it off. Now I go to party's with her when ever we get the chance.