Hello all! Thought it was about story time! Had to copy and paste from a reblog of my old deleted blog, but this is about me losing my virginity to a real man! I’ve cum a long way since then!
Reblog & help expose me 😘
So without further ado…
It was about 3 years ago the first time I got fucked by a man. Until then, I had been only fantasizing about meeting up with a guy. I toyed with the idea of Craigslist and placed a few ads. But never followed through on any responses.
As most of you know, us sissies tend to go through a purging phase, otherwise known as ‘anger’. But every time a sissy purges she is pushing herself further down the rabbit hole.
Anyway, I had just come off a purge, and hadn’t masturbated for a few days… so naturally, I lost control. I went to the local sex shop and bought myself a skimpy maids uniform, a glass dildo, a butt plug, and some new makeup. As well as a wig.
Once I had gotten home to my new apartment, I told my roommates I was gonna go take a long shower (which I did). I shaved my thighs, my ass, my clitty, and my face.
I then put in my new plug, and raced off to my room for the night, locking the door behind me.
For whatever reason, I decided to drop some LSD. Which honestly was a fantastic idea because not only was it some good shit, but i took the time to get all dressed and dolled up as I came up.
Once I started to actually trip out, I started watching Hypnos and started fucking myself. I watched all 1-4 episodes of deepslutpuppy’ series (the others weren’t out at the time). Along with a million other videos. All the while using the glass dildo on myself.
Next time I know it was about 3 in the morning, I’m not tripping nearly as hard, but I’m still hopelessly horny, and at this point, all I could think about was trying my very first cock.
So I put up a Craigslist ad, seeing if anyone wanted a shot at my virginity!
After weeding through several responses I find a 26 year old guy, handsome and hung, who lives downtown. He wanted me to come over.
Afraid of being seen in town, I wore my maid set, and plug under my boy clothes, and didn’t bring my wig…
I timidly/carefully drive to his house downtown. He greets me out at my car. I’m taller than he is but he is definitely more muscular. He takes me by the hand, offers me a cigarette, and leads me up some steps. We eventually end up on a rooftop, and he led me though a window into his home. He said he only rented a room here and that we had to be quiet.
Upon entering the room, which was a bed towards the back with a window over top, a table on the middle of the floor and two couches/futons on opposite ends of the table. Caddy-cornered near the door was a television set with a bunch of movies.
We sit across from eachother, me on one couch, him on the other. And start to smoke some pot, he wanted to bring my nerves down. After smoking and some small talk, he tells me to get on my hands and knees, which I do of course. He tells me to crawl over to him. I crawl slowly towards him, making sure my sweatpants and panty covered ass swing in the air for him to see.
I start getting closer to him and my face is inches away from the bulge in his pants.
I start to unzip and unbutton him, but I’m so nervous that my hands just fumble around and I couldn’t get he button undone. He takes me cheeks in his hands and tells me to calm down. I just tell him that I’m nervous… but mainly excited.
He unbuttons and unzips his pants for me, and I pull them down his thighs a bit. He is wearing boxer breifs, which just accentuated his large bulge and I got so turned on just by the site of it…
I kiss his bulge through his pants, smelling his sweaty musk, and then pull down his boxers. His 6" rock hard cock pops out, nearly hitting my in the chin.
I start kissing the tip of his cock, staring at it, and remembering all the programming and training my brain has gone through, remembering that I have been perfectly trained to be a good cock sucker. I knew I had to live up to my potential…
I start taking his head into my mouth, it was just like I had thought it would be. Warm and soft, but with sturdyness to it. It felt like heaven as I swirled my toungue around his head and then moved my mouth down further onto his cock.
He takes me by my short hair with one of his hands and gets a grip on me, gently pulsing his cock into my mouth with a very slow, sensual rhythm. With his other hand, he grabbed my arm and guided my hand towards his balls. I grabbed them lightly and started pulling gently on them. I then slowly lifted my head off his shaft and head, running my toungue along the underside, and then licked back down the shaft to get to his sack. I started to kiss and lick the balls that hold exactly what I wanted. His creamy cum. My first taste of another mans cum…
I started to suck on his balls, one at a time, feeling his warm skin stretch in my mouth as I sucked. All the while my nose is buried right between his balls and his cock, it smells like spit and dick and sweat and I start precumming in my panties. I tell him that I want him to fuck me. That I want to feel a mans cock in my ass. That dildos aren’t enough.
He smiles at me and shoves his cock back in my mouth, gripping my hair once again and pushing a little further into my throats this time.
He then pulls me off of his cock and tells me to stand up and show him my outfit.
I pull down my sweatpants and reaveal my panty covered ass, and my maid top as well. He stands up and comes up behind me, his naked hard cock pressing against my skin, takes me by the waist and whispers in my ear “Put your head against the floor and your ass in the air”
I do as he says and put my face against the hardwood floor, using my hands to keep my full weight from hurting myself. He grabs my hips, pulls my panties down around my ankles, and positions his slobber covered cock over my ass.
He grips me tighter and slowly pulls me into him, I can feel his head pop in pretty easily, after all I had been fucking myself all night with a dildo.
He starts pushing in an inch at a time, while my face moves up and down against the hardwood. Trying to keep a grip with my sweaty hands.
My hard cock is just swinging back and forth against his balls as he starts fucking me faster and faster.
He eventually pulls out of me, making a loud popping sound, and pulls me over on the couch. He sets me so my back is on my couch while my legs rest up against and over the arm. He comes in from the side of the couch and lifts my legs over his head, as he stares down at me.
He pushes his cock back inside my ass with ease and starts fucking me equally as hard as he was before we had moved.
I remember the moment where I turned my head, moaning with pleasure, and saw the time. It read about 5:00 AM, and I couldn’t believe it had gotten so late… it triggered a burst of thought within me.
Here I was, at a mans house, in the most public part of town. Dressed in a maid blouse, staring up at a man who had my legs over his shoulders, and his cock buried in my ass. I look at my hard cock slamming against my stomach as he fucks me. I think this really was the point of no return for me…
He tells me to open my mouth, pulls out of my ass and brings his cock towards my face…i was nervous/in euphoria and said “I don’t do ass to mouth” (it was my first time, I just wasn’t ready for it… things have changed ;) )
Next thing I know as I’m looking up at his face, trying to gauge a response, I feel a rope of something hot hit my eyelid and cheek. I then knew why I should never question opening my mouth again… I opened my mouth as he continued cumming on my face, catching whatever I could with my toungue…
I look up at him as I am tasting his cum, real cum, for the first time… he grunts back at me. I can only imagine what I looked like in that moment.
But the end game is to look like that quite a bit, and make sure ALL of it, is on camera.
We smoked again and made small talk about hormones and how long I’ve been dressing (13 years), and he eventually showed me out.
I drove the rest of the way home at 5:30 AM with cum on my face from the man who had just taken my virginity… I knew that I would never be the same again.
we’ve tried communicating several times after, but it ended up being a game of message tag, and we never got to do anything again.
I really wish one day, I’ll meet him again and I can show him how far I’ve come, and I mean realllly show him ;)
Thanks again for following!
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