Lets Just Make Sure
by Sam (Seattle, Wa)
Since i was young and started to think about sex i have always wonder what it would be like to be a girl. i would sneak into my older sisters room and try on her clothes and panties every chance i got and in hind sight knowing what i know now, I got caught a couple times. This story begins in my 20s though, many years after i had started to experiment.
I had started to take the dressing up further and further and eventually show men and experimented with them. i acquired and entire wardrobe and full makeup set and false boobs before i realized i was trans.
About a year later I moved in with my sister and started to secretly date men and dress in public. eventually one of these men convinced me to come out completely and the first person i would tell would be my sister because we lived together and it would be the easiest person to open up to in my family.
So the day came that i was to tell my sister.i told her that day that i wanted to tell her something later that night and to try and not come home super drunk and if possible alone that night. she came home alone but was pretty buzzed.
my sister came in the door loudly and started yelling my name for me to come share the thing i needed to tell her. I calmed her down a bit and sat on the couch. I started to ramble about her lgbtq friends and eventually just blurted out that i thought i was trans and like men.
There was a long pause and finally a little giggle from her.
she told me she had caught me "pretending" to be a girl a couple times in here clothes when i was young and thought there might be something there. then she asked if i was sure. like sure sure that i didn't like girls and asked how i knew. i told her that i had been with guys and really liked that.
she then brought up the fact the last gf i had was almost 10 years ago and i probably should try it as an adult to see if my experience as a kid just wasn't very good.
I laughed at the idea audibly, which cause my sister to give me a confused look followed by a small alcohol hiccup.
she asked why i laughed, so i explained i don't think i could find a girl to even try that with now.
this is when she lifted one of her legs up on the couch letting her skirt open a little and she said she definitely could find someone to come over if i wanted. so i jokingly said yeah, thinking she was just drunk and saying things.
she turned away and picked up her phone and asked me if i cared who it was as she started scrolling and one again i jokingly said no i didn't care.
after about 5 mins she turned back to me and said i need to take a dick pic to send to a girl or two so whip it out.
That's when i was like uhhh what (i was currently wearing panties also) and started to blush. my sister just said cmon if we are gonna be sisters you have to be comfortable changing and stuff in front of each other, she said it with a mocking tone.
I started to try and explain that i was wearing panties when she just pulled my shorts to to expose them. she let out a very loud 'Oh!' and giggled a little and said they were super cute, after being embarrassed like that she insisted it be fine to take it out and that she wouldn't be able to find someone if she didn't get the pic.
I told her to turn around till i got hard and she did. it didn't take very long sitting next to my sister in my panties was really turning me on. once i got hard i told her i was ready and she turned around and her eyes got huge. she whispered wow as she started to take 1, 2, 3 pictures, getting closer and closer to it.. the third picture i closed my eyes and turned away trying not think about my sister that close to my dick. 4, i heard the photo click again, that's when i felt her hand grab it and hold it up to get a better picture, 5 click.
That's when i opened my eyes and looked back down to see why she touched it. she was taking pictures still but her panties were completely visible and starting to get wet. and then i must have made a noise or something cause she just came out and offered to sit on my cock, that's when i stepped back and was like woahhh what?
She stood up and dropped her panties to the floor and stepped closer to me and said oh come on it'll just be for a minute or two to see if pussy isn't for you. ill just sit on it, if it'll fit, and ill do the work (she continued to step closer making me stubble back on the couch, my hard dick popping out of my panties). as i feel back she seized the moment and straddled me. i felt her wet pussy brush against my hard dick in the process. she sat down on my lap, my hard shaft in between her pussy lips popping up above her clit.
She said see we are so close just sit back and ill pop it right in.
I could feel my balls getting soaked being nestled right on her pussy and as i started to say uuuhhh i don't know she leaned forward and pushed my whole cock in.
We both immediately moaned and i felt my cock get bigger inside her. as she sat all the way down she said you seemed to have liked that little brother, maybe my pussy will change your mind. my mind was racing feeling a tight warm pussy slide all the way down my dick. she must have felt my dick throbbing in her cause she smiled and said you wanted this for a while didn't you, i know it all started smelling my panties.
That got my dick even harder. i started to wonder if she knew i had taken pics of her drunk upskirts and let her kiss me on the lips the one time she was blacked out. i tried to ask but couldn't stop moaning and watching my 120 lbs sisters pussy hide my 7" cock inside her. i blurted out i have upskirts pics of her from when she was drunk and sh giggles and starts to sit up and back down, riding my dick. i started to moan loud.
As she was riding she said she had seen me dressed up on a dating app already and catches me jacking off a lot and has wanted to fuck me for a while to change my mind back to girls. she said she was gonna tell our mom and dad soon if i didn't talk to her about it.
That's when it really hit me that my sister was riding my cock like a pornstar and i was like oh shit and tried pushing her off saying like fuck mom and dad what if they find out what if they know and she just giggled and moaned more and some how managed to stay on my hips with my cock deep in her and then said mom would probably jealous of this dick and dad would kill both of us, isn't that hot hehe. my mind in all the pleasure raced back to the pictures my sister took and insisted as she was still riding my cock that she delete them...that's when she said her and my mom talk about her sex life and she was thinking about sending them to her and telling her its her bf and not her son just to see what see says.
The second she finished that sentence i felt an eruption of cum ready to burst for some reason so i told her she had to stop i was going to cum and couldn't hold it back, my sister smile and moan loudly and said finally and slide my cock as deep as possible inside her pussy and started to grind back and forth. i couldn't hold back any more and couldn't push her off and my cock exploded inside her as she moaned and giggled and screamed yessss my brother is cumming in me.