My First Time As a Sissy

TLDR: Through some mix of alcohol, emotions from a very recent breakup, longing for an adventure, and sexual frustration, I finally got up the courage to dress up and visit someone. It was significantly more intense than I anticipated, in a scary way...10/10 would do again.

I was crazy horny and decided to dress up, just for myself, while I watched some porn and surfed Grindr just to chat and get pics. After a few minutes, I got a message from a dude with a rocking body, with lots of muscles and tattoos. He liked my slutty pictures and wanted to hook up. I get a lot of these, cuz my pics are sexy af, but usually I just talk dirty with a few folks till I'm too horny to prevent myself from jacking off. That night was different for some unknown combination of reasons. The dude sent me more pics and I decided it was time to kick it up a few notches.

I had tons of my ex's clothes from our recent breakup. She had lots of slutty outfits, jewelry, shoes, makeup, etc., even wigs. We were quite kinky. I completely transformed myself. From head to toe: a blond wig with pigtails, full facial makeup, with rosy pink cheeks and a mixture of blue and gold glittery eyeshadow, mascara, eyeliner, and pink lipstick. For my outfit, I wanted to look like a trashy slut. I wore a glittery gold tube top, some daisy duke jean shorts, fishnets, a pink crop top jacket, and pink heels. I also painted my nails pink, fingers and toes. I was quite pleased with the finished product. I looked like a legit trashy bimbo. Perfect. I wore some of my jeans on top and a collared shirt without the wig when I left, trying to not let the neighbors see anything, though it was already dark, it wasn't that late. I got to my car, drove around the corner, and decided "no guts no glory" and took off the boy clothes and put on the wig. I drove there sissified and it was exhilarating.

I had a few moments of doubt, but finally I grabbed my GoPro and pepper mace and told my new friend to be that I was on my way. He was maybe two miles away. I got there faster than I was ready for. His house was on a nice street, but it was weirdly offset from the rest of the houses. I was poorly lit too, with only a single blue lightbulb lighting up the door way. The rest of the houses had no lights or much more standard lighting. This struck me as a red flag, but I couldn't really think of a good reason that this indicated something bad, so I took a hit of weed, made a drink in the car and had a few sips, then got out and clumsily walked on heels to his front door. I knocked and he opened the door a minute later with a fairly intense look on his face. Scary or hot? Hard to say. Both? I went past him inside and he walked in, leaving the door open and only closing the screen door. This seemed weird, but whatever. It's a better escape route, right?

This house was fucking creepy as shit and I cannot believe I didn't run immediately. He said he was renovating it, but it was more like 2/3 constructed. He had chains hanging from the ceiling and I shit you not, a noose hung up as well. I playfully asked "you're not gonna murder me, right?" He responded that he wasn't sure. Okay...that's scary. This dude was probably 30-40 lbs heavier than me, was very muscular, and was on home turf. He went on to explain that there are many cases in which it might be appropriate to kill me. I couldn't read him. Was he playing or not. I like some good philosophical dark humor as much as anyone. Of course there are reasons you might have to kill someone, but I don't think that's what he was going for. He leads me to the bathroom where he removes a panel off the wall and takes out a baggie. We go out to the living room and he pulls out a pipe and asks if I mind if he smokes. I say no, thinking it's pot. It wasn't pot, it was meth. Fuck. This is not my scene, several times over at this point.

At this very moment, the front door opens and another dude comes in. He seemed very friendly and was very tall. It seemed like they might be acting like they didn't know each other. It was creepy and weird. I'm sitting on the couch next to the first guy, the second guy is across the room, snorting something, coke I think. Guy number one puts down the pipe, unzips his pants and pulls out his beautiful dick. I felt my dick tingle and knew I had to decide to either nope out or get a lot more vulnerable. It's important to know also that I told the dude I wanted to be submissive and him mildly dominant. I mention this because it was at this time he snaps his fingers and points to the floor in front of him. He said something along the lines of "alright sweetheart, it's time." He gently but forcefully grabbed my neck and arm and guided me down on my knees in front of him, in between his legs. This, by the way, was the second dick I've ever sucked and was a lot more impressive than the first one. I stared at it a little nervous, a little in shock at how beautiful it was. He then grabbed my head and slowly but powerfully positioned me to suck, then pulled me into his crotch. He pushed past my lips and I swear I came a little right then. He guided me for a while, then took his hands off and I kept going. His occasional moans made me tingle.

I hadn't really been paying attention to the other guy. I had my back turned to him. Stupid, I know. He walked around though and sat where I had been sitting, dick also pulled out. This dick was even bigger, uncut, and also quite attractive. I kept sucking the first guy but could tell they were communicating something quietly. After a few more minutes, guy one sternly tells me to "suck his dick", grabs my head again and hands it to the other dude who kind of pulls me in front of him by my head, positions me the same and shoves his dick in my mouth. I wasn't really planning on this, but it all happened so aggressively and quickly that I didn't even have time to think about it. His cock was delicious so I was okay. I thought about protesting once or twice, but I was a little scared to resist. i wasn't raped but there was definitely the "implication" that I was not in control at all. They traded my head back and forth a few times, then dude number two pulled my head off and jacked off I guess into his hand or on his belly. Dude one grabbed me and I kept sucking while dude two got up and left.

Once alone with the guy who might kill me, he picks me up, which was quite surprising and a little scary, and caries me to the other couch. He put his dick in my mouth, him on top this time, and fucked my face. This was a first and I loved every bit of it. After who knows how long, he took me to his bedroom, positioned me in between his legs while he laid back and put on some porn behind me. I sucked and licked, jacked, etc. for a seriously long time. I had intended to be home by 2 am and it was 6 am and I was still blowing this dude and loving it. I was worried he wasn't but he said it was perfect and it was just from smoking earlier. After another maybe 30 minutes, he told me to lay down and began to jack himself off fast and hard. He straddled my chest and arms and brought his dick right into my field of vision. I was pinned down pretty good and goddamn it was amazing. He moaned and groaned and then exploded his cum all over my face, neck, wig, chest. I got a few drops on my lips and licked it off. It was sweet and delicious, but I was still a little scared to swallow the rest.

He laid back exhausted and I did too, euphoric. After a few minutes I got up to wash my face but he told me "no" and kept me in bed. He wrapped his arm around me and spooned me a little. I felt his dick getting hard again like 10 minutes later, nuzzled up on my asscrack. Fuck. I had to go home for real though, so after we snuggled and I might have fallen asleep for a bit. Finally, I told him I had to leave. He told me to call him, gave me his number, his "real name" and again refused me the bathroom to let me clean my face. I walked out in daylight on a fairly busy road, fully dressed, covered in cum, and tons of cars drove by as I walked to my car. Again, I was dressed trashy af. People were looking. I got in my car, put on my clothes, and drove home downright giddy. He also wore my GoPro on his head for a little while, so I have kick ass video of me blowing him.