First Blowjob Attempt

I found someone online (great choice, by the way…) a couple of weeks ago who was looking for almost exactly what I was ready to provide. He wanted an actual TG person but said he would settle for anything from a feminine male to a Crossdresser if that’s all he could find. Well, he happened to be in my area, about 15 minutes away, so I figured I’d toss myself into the ring and see if luck was on my side. Turns out he wasn’t getting any hits matching what he wanted, and I was the only person who fit his description at all.

Initially we planned to meet that same night, but then he started doubting whether I was real because it seemed too good to be true: looking like this, having never done it before, yet being so excited. Understandable enough, so we backed off a bit and slowed things down. I want to make a complete point here that both he (I’ll call him “Dave” even though that wasn’t his actual name) and I did our best to convince ourselves the other person was genuine. Please do this if you ever feel the need to meet someone from online… Common sense is a powerful tool.

Also, I had a couple of people who knew what I was doing, where I was going, when it would happen, and a specific codephrase I’d text them once safe at home; if the phrase wasn’t exactly as agreed upon within our set timeframe, they were to alert the cops that I was missing. I’m so lucky to have such support in my life…

Anyways - About a week and a half after Dave and I tentatively decided on this whim, we had convinced ourselves of each other’s seriousness and realism. That brings me to last night. We agreed to meet on a side street familiar to both of us, roughly 5-10 minutes from our respective houses. My plan was simple: give him a blowjob, then part ways.

It didn’t take long for me to get ready that evening. I’d been wanting to do this for nearly two weeks and was overjoyed that I was finally preparing for something like it! When I arrived, I parked in the back of the business parking lot, facing the street we agreed upon, just about 15 feet from the road. We arrived only a couple minutes apart.

As soon as Dave got there, I started to get hard. The most intense thoughts were running through my head! We stepped out of our cars and exchanged quick hellos, but then he motioned for me into his car. I tried stalling for just a minute to gather myself and process what was happening, but by how fast he had his pants down, I assumed he was ready to go immediately.

I said, “Hey, I told you this is my first time, right?” He replied, “Yeah, can’t hurt to jump straight in though, ya know?”

And there I sat for about 15-20 seconds while he started stroking himself. Then I spoke up: “Second thoughts… I don’t know about this. Not really the way I pictured it going; have to be honest…” I was still okay with the idea, but I hoped he’d slow down since it seemed like he was trying to rush me into starting.

Huge turn-off here: right after that, Dave’s response was, “Cmon, I was hoping I could make you my like cocksucking bitch for the night.” To which I said, “Nope, not for me. I can’t do this right now. Sorry,” and got out of the car.

That felt too much for a first time, even though in fantasy it’s an awesome line. We agreed to take it as slow as I wanted since I admitted I was new to it and wanted to ensure it felt right, despite my excitement. I felt he was too eager to get his blowjob on his terms rather than mine.

What that means is I didn’t go through with it. As soon as he left, I started regretting not just saying, “Hey, I wanna do this, but can we go at my pace?” But the more I thought about it, I’m okay with how it happened (well, didn’t happen). I don’t think I’ll be turned off from trying again later. After reflecting on it for a bit afterward, I just need to try another time, perhaps in a different place. And like I originally thought, he wasn’t a bad person. He didn’t try to tempt me or force the issue after I said no.

All he said when I got out was, “C’mon, I thought you were serious about trying this. I know I was excited myself.” And I replied, “I was honestly ready until just now… Something hit me though, and I can’t do it right then. Sorry.” Dave said, “Alright, then. Don’t know what else to say. Night.”

He started way too fast, and I didn’t appreciate the whole “be my cocksucking bitch for the night” line in that specific context… Even if he had waited until I initiated, I would have just let it pass and laughed a little inside (or maybe even been turned on by it), no joke. But it was probably the most wrong timing possible since I was still processing my surroundings to get a feel for how things were going down (pun intended). Plus, his back seat isn’t in great condition for what we planned to do, which made it harder for me to relax—I had intended on using his SUV.

Bottom line: he didn’t ruin the whole thing; he just strayed too far from my desired image and comfort zone too quickly without giving me time to adjust.

As excited as I was for this adventure, I couldn’t make it happen given how things played out at that moment. I was literally a turn and a bend away from making one of my fantasies come true, and it’s SUPER frustrating knowing I couldn’t go through with it. But common sense, which has never misled me in the past, said to hold off for now. I had to listen to it; it’s been pretty much always right before, so for that reason alone, I don’t regret last night. Even if it is a bit frustrating (don’t confuse the two)…

Well, just like my first Long Walk story posted here, it was mostly uneventful. I love stopping by anytime I make progress and maybe motivate a few people to try new things, or let them know that thinking things through thoroughly is an important part of Self-Bondage, Crossdressing, or anything else in life really.

Take this little story for what it is, but thanks for reading and being here while I express it.:)