When I was first getting started

by Famsammie

14 Apr 2023 3372 readers Score 7.1 (12 votes) PDF Mobi ePub Txt


Just a quick short story about when I first started dressing. One night when I was 19 I was really starting to get into crossdressing more and was super horny. I put on my long straight red hair wig (hair was still short at the time) did just some plan make up red lipstick eyeliner and some dark eye shadow, put on my breast plate and threw on a tight hoodie so they popped out more and you can see my skinny figure with them. Put on my new red jockstrap and my new latex style legging and start cruising through a good hookup app to see if I could get some action. I was really feeling myself that night outfit was so plan but looked so good and the legging really made my ass pop out was in love with it. I started messaging people that were close by to see what was out there. Now it's 11 pm and I was still living with my parents they are asleep so when I finally got a good conversation going with someone I had to sneak out all dressed to go meet them. Was talking to this cute muscular Italian daddy, we exchanged pics and he had a nice thick 8" Italian sausage that I was just dying to have. At the time I haven't had any action in 6 months since I was still hiding my crossdressing from everyone. I was supposed to meet at the end of my road in a little pull off area now it's about 11:30 by the time I went to meet him. It was a October night and a little brisk walking to meet him, never forget the feeling I got when I was first walking around outside all dressed up felt so freeing and was just getting turned on by the thought that I was about to get used and abused by a older muscular daddy. As I got closer I saw the truck he described that he drove pull in I walked down and he rolled down his window and said you look even more passable in person. That made me feel so good about myself I open the door to his truck hop right in with a smile on my face and said I can't wait to have fun with you he smiled and goes oh yeah I lean into kiss him and before I knew he was shoving my head right into his lap. He pulls out his thick 8" cock and immediately shoves it down my throat. I wasn't even upset I just started throating him down and sucking as much as I can. I was so excited he cock was so thick and I was so turned on from the rough start literally shoving my head all the down his shaft just face fucking me. Each time I went to pick my head up he would just shove my head right back down on it I'm taking all of him twirling my tongue around his hard cock and I mean harder than a rock, he finally let's go my head I kept bobbing my head up and down on him couldn't get enough I get my knees up the seat fully bent over throating him I arch ass back he starts smacking my ass as I'm twirling my tongue all over his dick ready to taste some cum he smacks my ass again licks his fingers then reaches under my leggings and starts fingering me as he does that I take his cock all the way down my throat again and feel him shoot a huge load in my mouth at this point I'm rock hard and feel myself bulging from my leggings I clean him up suck and lick all the cum off of him he is still fingering me I pick my head up and sit up fully then he grabs my waste and completely pulls me to his side with my ass facing him with no warning he pulls my leggings down and sticks his still hard cock right in me and starts going full bore off the bat, at this point I'm leaning at the window as he keeps pulling my ass back just ramming that hard thick 8in cock in me I can't help but moan and start working my hips back towards him as he smacking my ass ramming away I'm at awww my eyes start to roll back and cum in my jockstrap literally leaking cum out at this point he rammed me like that for a solid 10 minutes before he pulled out and came all over my ass. He just falls back into the seat catching his breath I'm still leaning out the window shaking a bit, I pull my pants back up didn't even clean myself and just sit down catching my breathe next to him all he says while panting sorry has been awhile since I got to fuck someone hot. I just smile panting catching my breathe and say save my contact, open the door to the truck get out and slowly walk/limp home after being destroyed like that. I love that app sometimes I have the greatest experiences from it, plus knowing I looked like a passable girl enough to get rammed like that only boosted my confidence to keeping doing it as I was walking. Never forget when I walked back in and one of my parents were in the bathroom, had to dart to my room completely stripped down and cleaned myself up. Then wait a bit to go the bathroom just to clean the makeup off, even though I would end up doing this exact thing several times more lol