Hi pals, figured I would put this story in here, felt like a good place for it! This is a true story I wrote down ~3 years ago back on Reddit, but obviously wanted to have it here, too ☺️

Like a lot of people, the early days of the pandemic gave me a chance to explore my sexuality. I’ve always been into anal and recently been into chastity. Before the pandemic, I would’ve told you I was more or less straight. I’d have dated a trans woman or a femme non-binary person without hesitation but the idea of actually being with a masculine dick? It hadn’t even crossed my mind. But then: social isolation. Living alone and working from home was tough. However…

Exploring femininity had been on my mind for a few years. Like any socially-conscious person these days, I view gender as malleable. I started off slow by ordering a pair of panties online. My desire grew from there. I felt comfortable enough to go into the makeup section at Target and buy a few things. Mascara, lipstick, foundation, you know the stuff. I also felt comfortable sneaking into the women’s section to grab another pair of panties! For people like us, the self-checkout machines are a GODSEND.

I did more and more dressing up and things continued to escalate. I bought a wig, bought some lingerie, bought a skirt and a dress, and more! I kept dressing up, locking myself up, and fucking my ass. Soon I started taking pictures to put here and chatting with people on kik. I loved it. Talking to other people who dress, talking to people who were into people who dress, it was all amazing. When I received my first dick pic, I mean… There’s something so hot about knowing that you turned someone on. I wanted to keep doing it.

Eventually, I built up the courage to start looking around and posting on Reddit looking for something that could be… a bit more. One day, I found a bit more. A guy who had posted on one of the local R4R subreddits looking for someone like me. He posted one pic, a faceless mirror shot of a guy in decent shape with his thick cock out. I felt something deep in my stomach.

One day, he posted a specific request on that subreddit. It was a fantasy about getting his dick sucked by a good friend. Reading it made me so horny I had to message him. I asked if he liked what he saw and if he had any interest once the lockdown lifted. He did! We talked more and more about how it would happen and what ground rules there would be. For safety’s sake, we did a discreet share to make sure we were both real people and met up (in separate cars) in a park. It was on.

He asked me to let him know when I wanted him to come over and feed me. I was getting antsy. The numbers were waning and we both worked from home. I told him we could do it if he wore a mask and he agreed. We set a day and time and decided to do what we had talked about, which was more or less his fantasy.

First things first, I locked up my cock and put a plug in my ass. From there, I dressed and did makeup. Red lipstick, lightly glittering eyeshadow, eyeliner, nail polish, and more. I wore a strappy bralette, a pair of lacy panties, thigh high socks, and a red see-thru negligee. I was shaking this whole time but I was so, so ready. I unlocked my front door.

Once it got close to the time he arrived, I put on some porn and started fucking my ass. I heard a car turn off, the door open, and light footsteps. Throughout all this, I was moaning loudly. My heart was pounding. He walked through the bedroom door (with his dick out) and said “what’s up?”. I acted embarrassed that he’d caught me doing this. He said “you should’ve told me you were into that since we’re good friends”. I said I was just embarrassed and thought he wouldn’t like it, but then I asked if I could suck his dick. He said yes and I got down on my knees.

On my knees, I took his circumcised, semi-hard cock into my hand and started to lightly stroke it. Even not at full hardness, his cock was big. It ended up being about 8" long and wonderfully thick. I took a second to realize that I had finally done it. I was so happy. Even if I didn’t end up liking it, I knew I would be glad I tried it.

I started to gently kiss and lick his cock all over. He definitely liked this! I started to jerk it a little bit while I licked and lightly sucked on his balls. A little bit of hair, but not too much. I took his dick in my mouth and started bobbing back and forth on it a little. Nothing too serious yet. He didn’t taste like much, but that was fine by me.

Thinking back to head I’d gotten in the past, I started to try a few things. I balled up my fist and tried to take him as far back as I could. It wasn’t very far, but I was still proud of it and he seemed to like it. I took my mouth off and started flicking my tongue across the tip of his dick, right on the frenulum. This went down very well.

I kept sucking his dick and gathered a rhythm as I did. It was working for him and I was having fun doing it. Eventually he said “don’t stop”. I kept going, a little faster than I had been going. He started to gently moan and I kept going, back and forth, taking his dick into my mouth. He started to moan even more. We’d talked beforehand about how I wanted to swallow. Then he said those magical words. “I’m gonna cum”.

I went even faster as he started moaning loud and deep. He reached a crescendo and I started to feel it. He was cumming into my mouth. I just made a guy cum into my mouth while dressed up en femme. It felt amazing. As soon as I recognized it was happening, I shoved his dick as far down my throat as I could. I kept rhythmically moving back and forth on it. His cum felt SO fucking warm and I loved every second of it. It didn’t taste great, but I was still so happy.

After I was sure he’d finished, I pulled his dick out of my mouth. I showed him all his cum in my mouth, swallowed, then opened my mouth again. I felt like the luckiest little cumslut around. He pulled up his pants, thanked me, and left. I took a shower right after (it was harder work than I expected, no pun intended). After that, I started to ride my dildo and jerk off while thinking about what just happened. Suffice to say, it didn’t take long for me to have a fucking intense orgasm.