By Erincd1785

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Tags: crossdressing, first time, oral, anal

Added: 16 Jun 2009 Views: 175491 Avg Score: 4.78

i was caught by my Hated(at the time) Step-father

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine.

Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving place to place. She started dating a man, Rick, which had a daughter, Melissa that was several   years older. We moved in with Rick and Melissa when I was about 8 and had to adjust to both of them and didn't care much for Rick at all. I hated the fact that he was trying to be my dad. And in later years tried to be buddy, buddy with me which I hate because he wasn't my dad and would never see him as such and made it known. (I only say this cause this plays a big part in what is to come later).

Since we started living with Melissa and Rick I started seeing girl clothes in the bathroom more so her hand washed dance clothes that she use to hang dry in the bathroom. I don't know how it started or what lead me to try them on one day when I was suppose to take a bath. My mom started and checked the bath water then I locked the bathroom door starter to undress for my bath. I was staring at her tights, Bra and leotard and decided to put them on. I loved the way they felt against my body so tight and smooth I began to rub myself in the clothes and like the way I felt. I continued to dress every time o got the opportunity too with her clothes over the years touching myself rubbing moaning with the feeling of me rubbing my hard penis in the tight dance clothes. I continued to do this getting braver and daring. Eventually I was stealing my step sister dance clothes and some of her other clothes and hiding them in a broken down van in the garage that use to belong to rick when he was a teen. The van was where I starting doing my dressing adventures it had a bed the back and tinted windows and cur tens. Use to sneak out to the garage at night and dress in the van and touch myself on the bed till I came in the clothes.

Then final the summer came and I was allowed to stay home at the age of 16 by myself. And I had the whole day and the house to myself. I enjoyed weeks of dressing the whole day and walking around the house in my mother’s heels and my step sisters clothes, and even started wearing my mom’s makeup. But then that day came. I was on day in the middle of the week that was dressed and in make and in heels and make and wearing one of my step sisters jean skirt and pink t shirts with stuffed bra makeup tights’ and heels. I had just finished putting on lipstick and was walking back toward the garage when the front door open and Rick saw me. I froze … rick yelled WTF! I ran for my room and he ran after me. He made it to my room before I was able to close the door. He asked forcefully asked                                                                                      “what I hell is what are u doing.” I didn't answer. He yelled “tell me or ill call ur mother.” I started to cry, and said don’t please don't. He looked angrily at me and asked again " what are u doing dressed like this. Watery eyed I told him "I like to dress like this and touch myself" he just stood there for a moment looking at me. It seemed like forever had past with him just staring at me. I was getting more and more worried what he was going to do: was he going to yell more, was he going to hit me or worse tell my mom. He closed the bedroom door and said "show me!” I looked confused and didn't move. He looked sternly at me and said again "show me what you would do!" I then lied back on my bed and began to reach under the skirt and rub myself watching rick watery eyed from my tears wondering what was going to happen. He then walked close and said "don't look at me and do it like u would do it" I closed my eyes and turn my head away and tried to rub myself like he wasn't there but I was still so scared and nervous.

My feelings suddenly changed in an instant, I was Horrified. Rick had thrown my hand out of the way and began reaching under the skirt and rubbing me. Not knowing what do or react and complete uncertain on how I felt. Although, His big hands felt so good rubbing me that I got hard instantly. It felt so good I kept my eyes closed tight and began to moan as he rubbed my legs and my crotch. He rubbed it ever so gently till I exploded in my tights and leotard. He asked if I liked that and I said yes and he said "good now want you to rub me” he unzipped his pants and pulled out his dick and told me to stoke it like he showed me. I stoked his hard dick till he cummed all over my hand and then he said "be a good girl and lick that off and ill keep this our secret. So I started lick his cum off my hand he got up and walked out my room.   Later that evening came and went with me terrified that he was going to tell my mother.                                            It was an uneventful even as ever. My mother tucked me in told me that she loved me, kissed me on the forehead, and told me If I was good maybe Rick would talk me to movies or something. I later found out that rick was laid off from his job and we would be spending a lot more time together. A few minutes after Rick came in sat on the bed told me good night and looked forward to seeing Erin tomorrow. With that he got up walk out the door saying “See u in the morning.”   That night I lied there scared because I was caught and this was the first night that I had laid there in bed not wanting to get up and get dressed.

            The next day came. My mother came in my room kissed me goodbye told me to behave and not to get into any trouble, and that Rick had some things to do and would be back later that afternoon.   The whole I day I spent walking on egg shells wondering when rick was coming home and what was going to happen when he did. More so because his comment hung in my head “looking forward to seeing Erin again,” Was he talking about me? Well that morning I decide that I was wasn’t going to dress up because I know he would be home and of course would be the smartest idea after just getting caught. I spent the morning hide my stash of my sister clothes. I took all the clothes that I had accumalated or the years and took them out to the van in the garage stuff them in the bench like carpet covered cabinets and ran along sides inside the van. As I just finished closing the vans double doors and was about to walk out the garage the garage door opened and there was Rick.

            “Now what are u up too out here Erin” he said out loud more to himself then to me. I didn’t say a word. He look around then the garage them open the van doors and start going through it. It didn’t take long for him to come across and find my collection. Pulling clothes out and looking them over piece by piece, until finally settling a few pieces and turning them over to me and said “well Erin I think u better get ready we don’t have much time ur mom will be home in a few hours”. I hurry with my arms full to the clothes shoes and make up. I hurry to my room and start dressing. I put on the pair of red panties and matching bra that belonged to my sister. I then slide on my sister dance tights that are a shinny suntan color and then the black pleaded skirt that belonged to her as well I stuff the bra with water balloons and then put on a white button up blouse that belong to my mother. I finished it off with black pumps and bright red lipstick. I stood ready paused at the door trying to muster up courage to go out there I was nervous and excited at the same time. I took a breath and opened the door not knowing the list of new experience awaiting me.

As I walked down the house towards the garage I saw rick watching porn in the living room. I walk in the room and see him in the arm chair stroking his hard cock that seemed like more than twice the size of mine. I turned and his head as I entered the room and called over to him. “Erin come over here” that name again I like hearing it now that I know he was calling me Erin. I stood in front of him as he ran his hand up and down my legs stopping just short of panty covered cock. He glide me down on my knees in front of him and he stroked his cock now eye level with me.   I thought I know what he wanted after last time so I take his cock in my hand and start stroking it.

      “Mmmm yes Erin you got the idea but I want u to do what girl on TV are doing” rick moans. I turn my head and look over my shoulder and see this girl licking and suck on the cock like a Popsicle. I turn back and look at Rick who is now smiling and guiding my head slowly down. I think I can do this I say to myself. I start to slide my mouth up and down Rick’s hard dick like a big stick Popsicle. I tasted great and I enjoyed it the more my head bobbed up and down Rick cock sucking and slurping as my wet mouth moistening his cock. I look up every now and then to see rick with his head back moaning “faster Erin “I start to bob on his cock faster but then he put his hands on my head getting a fist full of my hair and forcing me down faster and his hard cock deeper down my mouth banging it on the back of my mouth. He continues this for a few more minutes making me gag every now and then. I start to taste it the creamy taste that I licked off my hands the other day. I didn’t know it but it was his pre come and he was about to cum. His cock started to spasm and jerk and then Rick force his cock deep down to the back of my throat. He cum shoots at the back of my throat I gag a little as it fills my mouth and starts to flow out the sides. I swallow all that I can feeling proud of myself Rick just sits there and moan with a few deep breaths or relief as I lick the cum that spilled out of my mouth up.                                                                                                                                                              “Mmmm good girl Erin clean that up then we will go play in that van that u like to sneak off in to play in” said Rick. After cleaning my face licking every bit of cum off rick cock we make or way to the garage as rick smacks my ass and grabs it. Once we climb in the van he shuts the door and we crawl our way to the bed and there on the bench is an arrangement of items that I soon find out to be Lubricant, some anal balls, and butt plug, vibrating dildo, and Restraint cuffs or collars. Rick noticing that I saw these said we were going to have a little fun and guides me on my hands and knees on the bed in the back with my ass facing him. He starts rub his hand up and down my legs. The feeling is great I can feel my cock growing in the red silky panties I’m wearing. He then vigorously rubs my crotch and I get hard immediately moaning stick my ass higher in the air for him. He then smack my ass telling me “What a cute like pussy u have, I think we need to brake that in.” not knowing what he meant and still moaning from him rubbing my cock I didn’t really care.   HE them moves up on the bed past me parting the cuffs on my wrist and clipping the ends to frame of the van wear the curtain hung to cover the back two windows. Then he somehow ties my ankles to the bed frame so I’m on my knees tied at the ankle with my feet just hanging over the edge of the bed. With arms tied and hanging in the air my body force to ark my back sticking my ass up in the air. I’m able to squirm but not much. He then start to rub and caress my legs in the tights and rub my crotch making me jerk in my restraints.   “Now let’s see if we can break in that young tight pussy of ur Erin”                                                          He now flips up the skirt and rips the tight at the ass area exposing the red silky panty covered ass and slip his finger in from the side and apply some lube and sliding his finger in my ass It hurts so I try to squirm away but can’t. Then pulls down the red panties and lubes up my ass say again, “Oh that’s tight we need to loosen that up a bit.” He then take an anal ball and slowly pushes one ball up into my ass. I let out a scream. “Its ok. Lets see if we can get a few more in there.” He tells me and as he pushes the next ball in I scream again. After four balls in me I started to rub my legs again as I can see him rubbing his cock as I turn my head. “Please take them out” I moan. He smiles and slow pulls them out while rubbing his growing cock. I continue to moan as my asshole grapes as the balls exits ass hurting less and less. I give a final loud moan as the last balls is pull out slowly just as I’m starting to relaxing I let out a loud moan as the tip of the dildo is push up into my ass he strokes it in and out for a few then going deeper and faster smacking my ass as I moan louder and louder. He then pushes the dildo deep I’m my ass, I scream. Then he turns on the vibrating action. And slides the panties over the dildo holding it from sliding out my ass as I buck from the sensation Cuming in the panties.                                                                                                     Rick then leaves the van confused scared but at same time lost in the ecstasy or the vibrating dildo I’m my ass I continue to buck and moan loudly. The back doors open and my arm are force to be out stretched further. Forcing me to almost lie on my belly rick standing there with his hard cock in his hand and moves it so I can take it in my mouth. I suck on his hard cock for all its worth my body still orgasisming form the sensation. I can taste rick sweet cum again and am preparing for him to explode in my mouth as he then pulls out and makes his way back into the van behind me. He pulls down the red Panties and the dildo slides out almost immediately. He spits on my gaping asshole and then grabs my waist and pulls my ass towards him force my arms to stretch out more from the doors till being open. I slide cock in me slowly. It still hurts a little from the difference in size and I moan loudly as he begins to fuck my ass. Rick starts pound away faster and deeper with each trust. I feel him jerking wildly as he continues to trust his cock deep in me and he cocking twitching as he cumms deep in my asshole. I cumm again from the whole experience. He then unties my ankles I fall freely to the bed on my belly feeling my wet cumm filled panties pressed against me and feeling the cumm dribbling out of my ass I could almost pass out.

Rick unties my wrist and whispers in my ear, “Erin ur tight light pussy felt so much better then when I fucked ur mother there.” He kisses me on the forehead,” this is going to be some summer. And he walks out of the garage. I lay there feeling amazing, confused, scared and hoping that tomorrow is just as fun.