Easy money [MtF T/M] | 2016

(Note: I'm not sure how to exactly tag the fact that I'm trans in the title, so excuse the ugly format.)

This event may or may not have happened a couple hours ago, and while I'd like to pretend that my slut phase is done and say it was a year ago or something, let's be real.

About 2 1/2 weeks ago I downloaded OKCupid due to my shitty luck with Tinder. Tinder so far has been filled with people who only message me sporadically and at this point, I'm keeping the app on to see how many matches I can collect. As an alternative, I decided to try my luck with OKC.

Being a relatively passing trans girl who is consistently complimented, I thought that maybe my self image is wrong and I am as attractive as people make me out to be. I'm 5'4", 110 lbs, rocking unnatural hair color, and have the smallest boobs in the world, and apparently to some people, all that is attractive. I've got an amazing butt, but I didn't really think that saved my whole image. But people never call me ugly, so take that how you will.

With all that in mind, I signed up for OKC making sure to put that I'm down for casual encounters in my preferences. The app exploded within the week and I suddenly had a bunch of dicks getting thrown at me from every direction.

"I'm okay with this," I thought to myself as I began to wade through all the messages. I began sorting them by people who didn't raise red flags, people who knew I was trans, and people willing to work with the fact that I don't drive yet.

Suddenly the categories grew and grew and I just decided to be more strict in what I was looking for. I've got endurance, but no way in hell am I fucking the like 80 people who want to hook up.

I revamped my profile, mentioning that I only sleep with people in the age range of 18 - 23. That immediately cut down on all the old people propositioning me. I also added in that I only want to do stuff with people willing to pick me up. Finally, as a joke, I added in my profile to message me if you can give me a job. I mentioned I was just fucking around, but in actuality, I can't go somewhere crazy expensive.

Within the next day, my average messages cut down significantly. That made my life a lot easier and it's also when I met Ryan. Now he wasn't the most unattractive of guys. I would rate him a solid 6 on the scale, but mostly because he's just not my type. He's tall and wide, and he's like Indonesian I believe, and quite frankly very dickish looking. I happen to prefer guys who are more on the cute side, but this guy was objectively handsome.

So he messages, "What's up?" on OKC and I respond because I have a rule about responding to every message at least once.

The conversation is super normal for what I usually get. People always start with long drawn out small talk. Suddenly, the tone changes and he messages, "So I read your bio. Do you love sex?"

This is in reference to the fact that my profile is brutally honest about the fact that I am only on the app for cheap hookups.

Before I can even respond, he hits me with something I honestly wasn't expecting. "I can help you out with some money too."

"Isn't that kind of illegal?"

"We'll keep it lowkey."

I'm a straight-edge. I don't do anything illegal. I don't smoke weed. I don't drink because I'm not 21 yet. Things like that is stuff I don't do not really because of morals, but because I probably would get caught. But I'm poor. And interested.

So follow up message. Always have to follow up.

"You know I'm trans, right?"

He says yes.

He says that he can't host. I can't host either. We settle on doing it in his car.

So we set a time for the next day and I shoot him a number for money. I'm not going to specify how much, but it was cheap. Only thing lower than my standards is my self esteem. Only thing lower than my self esteem is the amount of money I have.

The next day comes quick. He set a rather earlier time than I'm usually up, and I got up even earlier than that to allow myself some time to get ready.

I hop into the shower, clean out my butt as best as I can, wash my face, then have the grand idea to insert a butt plug so we don't have to do much prep when we do the deed.

I begin to get ready to insert the butt plug into my ass, lathering it with lube and prodding it at my opening. I take it slow, pushing it in an inch at a time, then constantly removing it. Soon enough I'm at the flared head and my ass is relaxed. I manage to get the whole thing in there and slip over my panties to keep it all in place.

It then hits me that I need to do my makeup. I take a step and immediately I'm met with the feeling of fullness. I can't tell if it feels good or bad, but I'm hyper aware of the plug sitting comfortably in my ass. I waddle towards my vanity to do my makeup and take a seat.

The plug grinds within in my butt as I sit, making my mind go blank. The pressure it's placing down definitely feels good, but my hands are too shaky to deal with makeup. I decide to do fuck all and throw on mascara and smudged eyeliner.

Ryan texts me that he's outside. I head out of my house and hop into his car.

We make incredibly shitty small talk. He asks me personal questions about my past. My family. My name. I don't want to tell him that he's being inconsiderate, because I don't plan on seeing him ever again.

We find a parking lot near a park and I make a mental note that this will officially be the trashiest place I've fucked in.

"I've never done this before," he says looking over at me with an awkward expression.

"I've never done it in a car," I reply. "So how do you want to do this?"

"You tell me," he says looking me up and down, clearly checking me out. I wanted to tell him to fuck off. I wanted to remind him it's his car. I instead turn to the back seat, gauging how much space we have. I'm tiny, but he's not.

"You want to do it in the back?" he asks. "The chairs in here move really far forward, so we'd have a lot of space."

Wish he told me earlier. "Yup. Sounds good." We both exit out of the car and head into the back. We move both of the chairs forward and I sit back looking at him. He gives me that look. The predatory one that guys give me when they're undressing me with their eyes. I smile back at him. I fucking love that look.

I crawl over to his side of the car casually dropping myself in between his legs. I barely fit between the car seat and his position, but I'm able to get in comfortably. I lower myself so I'm sitting all the way on the car floor. Fuck. The plug.

My mind goes blank again staring at his now exposed cock. He's not huge, but he's not small either. I'm grateful. I can barely think. I wrap my lips around the tip of his dick, desperately trying to remember how to give head.

My internal monologue reads like an informational booklet.

Keep your tongue above your bottom row of teeth. Long motions. Swirl. Pursed lips.

Even with my jumbled thoughts, I settle into a decent rhythm and routine. He's clearly enjoying himself as he settles further and further into my throat with each bob of my head.

"Fuck," is all I hear from him when he places his hand on the back of my head. He pushes me deeply onto to his penis. I go all the way.

I then continue my routine, making sure to pull out the fancy techniques now that I've regained a bit of composure. My tongue dances along his whole length to compliment my lips dragging along his cock.

I feel him touch my chin. I've come to learn that this is the silent equivalent of, "Slow down or I'll finish." I take his dick out of my mouth with a satisfying pop.

I look up at him with an undoubtedly dirty expression. Guys stop calling me cute when I go down on them. Suddenly when I'm disheveled, it's sexy.

He pulls me up and makes out with me. Why do hook ups always insist on making out with me? I pull back afterwards and sit back down between his legs.

"Want me to keep going, or are we switching to the main event?" I ask bluntly.

"You want to get fucked now?"

"Your choice."

He takes off his pants completely and removes his shoes. I follow and do the same.

He asks if I want to ride him so I know "what's up."

I tell him I don't mind if he wants to be in control as I remove my plug. He smiles.

I take it as a yes and I lube him up, then settle with my knees on the chair and him looming over me. I push my ass back and present myself. He responds by lining up.

He pushes into me. God it hurts. This is what I get for taking a break from anal. I bite down on my hoodie sleeve.

He asks if I feel okay. "I'm good," I say not letting on how much pain I'm in. It just takes a moment to subside. I remind myself of that. Just last the first part. And boy do I last.

Suddenly he begins to move and the pain is completely gone, replaced with the familiar feeling of being filled. He's making it a point to fuck me from every angle and to rearrange me like a rag doll.

He'll have me pick up my leg, raise my butt, lay back down, and all sorts of commands as he ravishes me. I'm annoyed that I enjoy the submission. He picks up pace and I've already grown use to the feeling. I'm glad he waited to be rough. I might have cried.

He pushes his whole length into me over and over again. I hadn't realized how much I was moaning until the roof of my mouth felt dry. Moaning always helped anal feel better faster.

He shoves into me over and over, the slapping of skin can be heard from behind. He reaches over and lifts my midriff. I thought we were re-positioning. He attempts to play with my penis. No. I tell him not to touch me there.

Curious straight guys never respect boundaries.

It clearly didn't bother him that I said no. He went right on back to destroying my ass, but this time with a much more focused conviction. He started to use me more. I loved it. The moaning was back. My ex never fucked me this hard.

"Where do you want me to cum?"

"Anywhere," I say between pants.

And murder she wrote. He buries himself once more into my ass, and I can feel the very faint pulsing at the base of his dick.

I get dressed and he continues to tell me how much he loved it. Amazing, incredible! I felt like I was getting reviewed. Considering the reviews were great, I enjoyed it. Nobody compliments you more than the guy who fucks you.

We talk a bit about how long I've been using OKC and how many people I've hooked up with on the way back. I tell him the truth. He was only my second hookup, but I lie and say I've had the app for 4 months. Such a worthless lie. After he fucked me like that, it's obvious how much of a whore I am, but I like to pretend.

I shift uncomfortably in my seat as he drops me off, making sure I have everything that I brought in. I open the door and he hands me my money. "We should chill sometime."

I nod my head and close his car door. "Probably not," I think to myself.