I originally posted this on sex, and people are telling me that this sexual post would be better appreciated here [warning, a long read!]
I (Female, 28) have always been kind of sexually shy, though I was interested in a lifestyle where I was more open with my sexuality, I just couldn’t do it. As myself, I couldn’t look a guy in the face after a hookup and not feel some type of guilt or shame. The thought that he will see me again in public or something when I’m with my family, it was too much for me to handle. I wasn’t comfortable with that, and pretty much ignored my urges.
Not too long ago, I moved into a house where a transgender woman was my housemate let’s call her Mimi. Well, seeing Mimi live her life was kind of exciting and stressful for me at the same time. Mimi had a LOT of guys over, she had average looks and yet she was bringing some very hot guys overnight every weekend. Firstly, it kind of shocked me that there was so much interest in her from men (not that there’s anything wrong of course), I just didn’t know that there were that many men into transwoman in this rather little and conservative city we’re in. Secondly, after the shock, it made me reassess my life and I got a little jealous, thinking how she’s living these primal pleasures of a woman and all of this time here I am being too shy and afraid to do anything about what I want.
One friday evening, Mimi and I were watching TV, she told me we should go out. It took a lot of dragging me, but she got me to go out with her. At the club, I was just fascinated by how much attention she got from very good looking men. Everyone stared at her, her sexy outfit, super high heels, heavy makeup, and bouncy hair could not be ignored. She was practically shooing men away the whole night.
One week later, she asks me if I want to go out with her again. I say yeah, and I ask her to do my makeup for me like she does hers. I wanted it on heavy, so thick and heavy that I was unrecognizable. I also did my hair in an entirely different manner. After not even being able to recognize my own self in the mirror, I thought to myself wow, I could wear whatever I want and nobody will even know it’s me. So.. we run to forever 21 and pick up a skimpy tube dress I wouldn’t have dreamed of wearing before. So we go out that night.. and that was the first time I was ever really able to enjoy myself. I just let loose on the dance floor, lots of eyes were on me and I felt FREE, free to dance and do whatever I wanted without anyone knowing it was me. I feel free to express myself sexually for the first time.
So some time passes and I have to move from my precious friend Mimi for another job in a different city. It was kind of weird going out without Mimi, so I stayed in and created a dating profile with my alter ego character, and on a whim.. I marked myself as transgender! I was always too shy before to make a profile, simply because I didn’t like the idea that there would be public information about myself out there about me looking for love, didn’t like the idea of people I knew seeing it. So basically on my dating profile I did my makeup in drag, with ridiculous eyelashes and a colored wig and put that I was a transgender woman, I figured it would really help with people not knowing it was me.
I loved playing dressup, and created characters that I thought it would be fun playing. Blonde Russian Instagram brat, Indian bollywood star, tanned SouthEast Asian ladyboy, the Kardashian look, basically I created characters for myself inspired from things like TV shows or movies, characters that I thought would be fun doing while making sure to do the makeup heavy enough so that no one from my personal and professional life could ever recognize me. It’s really amazing what you can do when you know how to mess with makeup.
My phone blew up, guys were very interested and I was not surprised after seeing Mimi’s sexual encounters with men. There’s a guy a block away from my home named Javier. We see each other and wave often as his home is near the mailbox and he’s always working on his car upfront, he’s a very rugged guy that stands 6’5″ tall, in his 30’s, shaved head, tattoos, a chain, and a trimmed beard. I always had a crush on him, seeing him work on his car in a wifebeater and jeans was hot, and when he messaged me promising to show me a good time with his 9″ dick, I couldn’t sit still until I got it. I just waved at him at the mailbox, and because of my alter ego little does he know that I recently sucked his dick.
Javier thinks that last weekend he had sex with an Asian transwoman named Star. Star was dropped off at his place by an Uber, and she wore a polka dot dress with yellow high heels. Along with shimmery eyelids and a little pink blush, her whitened skin was done to create a very pale look like as those of K-pop stars. Her jet black wig with wavy hair, and some eyeglasses completes her look.
When I walked into Javiers place, it was like a flashback into the 90s, I fucking loved it. There was a boombox, old box tv set, the sight and smell of the classic orange Jovan cologne I always remember seeing, roughed up furniture, a lamborghini poster on the wall, 90’s RnB playing, and somehow with me in my Polka Dot dress creating a new person in this new scene, it just felt so right like it was a flashback into the past to have sex with a guy from the 90s. Shortly after a little small talk and admiring his things, Javier grabbed my bottom and started kissing me. It was pure ecstasy as he was fingering my ass and kissing my neck and then my nipples. Before I know it I’m laying in bed and Javier is at the foot of his bed taking his pants off. He climbs up and whips out his indeed 9″ dick. It was beautiful, thick, hairy, hung and uncut, just as I always fantasized as I saw his lower half of his body always sticking out from under his car. He leans in to pull my panties out, but I resisted, instead I closed my legs, and licked my lips for him to know, that I wanted to taste him more than anything right now. He comes up the bed and places his hands on the headboard as he positions his penis for me to suck on, he tries to face fuck me for a little and though I loved his long muscular body towering over me, it was way too much meat for me to handle, and so we get into a 69 position. This lasted for like 45 minutes. His long tongue made me feel like I never felt before and I enjoyed the challenge of trying to fit a 9″ dick in my mouth. I thought I could do better, but I felt like I could only pleasure his big dick one quadrant at time, my favorite part circling my tongue underneath his foreskin at the tip of his penis.
Javier kept having to stop so he wouldn’t cum, and so after oral, he took a walk around his place outside for a little to check on the noise we heard. He came back and immediately he pinned me down, and he stuck his penis inside of me. It was overwhelming, but damn it felt so good as he was trying to fit it in. With his muscular arms he wraps me in a very tight embrace, almost as if I was being constricted by a boa constrictor. Being constricted was like nothing I’ve ever felt before, it was like I was going to have this pleasure no matter what. I felt his warmth and wetness as he cummed inside of me. His heavy breathing in my ears felt comforting. After I was released from his insanely tight embrace, I felt a sense of high and pleasure it was like nothing I felt before, just a pure sense of relief and satisfaction after being in such a hot and tight spot underneath him. I really enjoyed my time with Javier and would love to introduce him to my many other characters, and maybe even have him suggest any fantasies he might have. I love playing dress up now, it’s a new passion of mine.
I can’t believe how much I rambled on… just wanted to share my experience of how I was able to release my inner sexual Lioness by creating characters that I could get in and out of whenever I needed to, sexual characters and personalities that wouldn’t follow me and create any type of reputation for myself. Characters that I could erase in an instance simply with.. makeup remover. Thanks for reading, if you even made it this far!
Source: reddit.com/r/gonewildstories/comments/9cfeaq/fm_what_unconventional_things_do_you_do_to_bring
Bravo! Good for you.