My First Time Getting Caught

When I was a teen growing up I always had a fetish and it scared me cause I never knew if it meant I was gay or not. When I was at friends,school,camps where ever I loved to sneak into there moms or s****rs dressers and I would dress myself up. I was about Five and a half feet tall growing up 120 with an average body. I would try on Thongs,Booty shorts,Jeans,spandex Pants,skirts,tank tops,dresses,high heels. It was a thrill it made me feel great. I liked how i looked and the clothes felt I had started doing it at about 13 going to the schools gymnasium storage room and taking pairs of girls spandex shorts from the volleyball uniforms, I would be on sports trips for school and always volinteer to load bags on the school bus before we would leave, The team bags had each girls name on them and all the older hotter girls dressed like sluts on sports trips and its pretty easy to take clothes and slip them into your bag. By the time i was 16 I damn near had a full girls wardrobe in my room.

It was my friend Mikes 15th Birthday he was a year younger then me I was already 16 he told me it was just me spending the night and his mom was gone for a few more days working. Perfect! so i thought.. Me him and his dad did the supper and cake thing he opened his presents then we went to his room watched a movie. It was probably midnight I looked over at mike seen he was sl**ping and went to work. I tiptoed to the bottom of his stares his fathers name was Jim he looked passed out in his chair with beer cans all in front of him. I went back up stairs and went into jim and his wifes bedroom slowly closed the door turned on the light and got naked! I loved it everything fit perfect she was in great shape and always dressed nice she had sexy lengiree thongs her jeans fit perfect she had tons of shy ort jean shorts I got so busy trying on shit that i did not realize that jim and one of his friends where walking up the stairs. I remember it like it was yesterday I had on a Bright pink thongs sticking out the top of a pair of jeans a lace purple bra on with a little white tank half pulled down i was bent over in the dresser mirror looking at how my ass looked in her Jeans.

All i heard was ya Tom i have it right in he... The door swung open and Jim and his Friend Tom walked right in. Jim looked at me said what the fuck get up right now Kyle. I stood up and he took his time they where both just staring at me then Jim said 'Those are my wifes clothes kyle are you pretending to be her? Tom chuckled and said it lookes like you wanna be a girl you little fag. I said no i dont they just kept razzing me about being gay tears filled up my eyes and they made fun more I turned around to hide my tears I felt a large hand firmly grasp my ass Then i turned around quick tom was the one grabbing at me they where both standing very close when jim said to me its not ok to be gay we are going to give you a little lesson see if your still wanting to dress like a girl I was so scared I said No please dont But then Tom piped up and said well its either learn your lesson or we tell mike his friends a homo.. He then spoke louder whats it gonna be youd better get in the bathroom Tom took me into the bathroom explained he had 3 daughters and started putting makeup on me he was almost done when jim walked back it he said hear wear this. It was a matching yellow thong and bra a tight very short jean skirt and a white button up shirt. they shaved my legs jim found me a shoulder length brown wig in the basement and some white stocking. When they where done i looked in mirror I didnt see me i seen a little school girl slut. And felt like it being rubbed while being made fun of for being such a sissy fag. I felt like a real little slut and was definetely nervous for what was next I had never been with a man before..

Jim and Tom where both close to 40 but both in very good shape not buff but not fat. Jim was about 6'0 tall and Tom was about 6'4 Jim smiled at me bent over and grabbed my face he wispered whats with the frown hopfully this makes you smile. He undressed pulling down his boxers his dick was soft and about 8 inches long cut. He laughed and said bigger then your lil pussy huh my dick was soft and about almost 3 inches when i had on the thong it was hardly there . My heart was pounding jim was still kissing me when tom was undressing he pulled out a thick 7 1/2 inch cut cock and i thought i was gonna be sick i remember saying you dont have to do this while they laughed saying youll love it you fag. Jim was kissing me his tounge touching mine tom grabbed my head gave me one long kiss then pushed my head to his hard cock.

I ended up doing not to bad he seemed to be loving it then i switched over to jim he was loving it to he f***ed my head down more and more it was sort of gagging me but i could tell he was loving it so i kept on going . Tom grabbed my ass squeezed pulled the yellow thong out of my ass and off to the side then i felt the tip of his big cock going into my ass. i screamed it hurt so bad Jim grabbed my head f***ed me to keep sucking after ten minutes of tom taking it slow i had tears rolling down my face but his cock was feeling ok as he kept on fucking me. He pulled out spun me around and kissed me i looked back at jim he grabbed me and slowly pushed me down onto his cock bent me ahead a bit and smacked my ass while saying bounce slut. Toms cock had just been in my ass but he still grabbed my head and pushed his cock to my throat. For the next 3 and a half Hours they took turns fucking me. I was so happy they inbetween made me switch my clothes up but i always got to keep my thong and bra and wig on they didnt want my cock out at all. i was just enjoying toms cock in my mouth when jim grabbed my hair and shot his load in my mouth it didnt taste good but i swallowed it then sucked the rest out tom went back to making me bounce on his cock i didnt think i would but i felt his load blow inside me he pushed me off smacked my ass again i went down to my knees sucked his cock clean for a couple seconds they both smiled at me and said you still wanna be a girl fag them both laughing I just looked up at them both sucked on the tips of there cocks and said Dont tell mike please boys in the sexiest girl voice i could. They both smiled Jim said go take a shower you little sissy looking fuck I went to the washroom cryed for a couple minutes but showered up and thought about it and My first gay experience was awsome .

For the next year or so once or twice a week I would meet up with that tom dress up how he wanted and let him fuck me like the sissy girl i was. I ended up finding guys in school who thought it was hot and now that im 28 years old I have my steady Man but over the past 12 years since my first time i have been able to please several men dressing up like a girl and not being so scared my first time i loved looking like that and instantly knew I loved Crossdressing and being fucked and giving other men head. The day i got caught dressing up and ended up being made into the little sissy girl i had always dreamed about.

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Categories: Gay Male
Posted by onlyonceihope
1 year ago    Views: 5,400
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6 months ago
love it
12 months ago
Mmmmmm very hot! I love being a littke sissy and remember how much fun I had when I was younger and in shape. Lots of guys used me ie a girl a few even thought they were fucking a girl and to this day don't know they fucked a cross dresser!
1 year ago
1 year ago
beautiful story more plizzz