My first online hookup

'm what you might call a "twink" or a "femboy."

That is, I regularly shave all my body hair (except, of course, the soft flippy hair on my head) am a skinny white boy, and I act rather feminine. In addition, I have the cutest, roundest, girliest booty you've ever seen.

Well, when I was... younger, I grew curious about sex. I was definitely gay. Why else would I enjoy shaving my body and fantasizing about getting fucked? I was a horny lil thing, but there's not a whole lot of gay activity in the South. I turned to the internet, hoping it could help me get laid. I didn't want to make an account on some shady hookup site, so I went on Omegle website.

I added my city to my interests.

And I tried.

I tried and chatted and connected and disconnected, but it would seem that there were no interested guys around here.

And then one day, I found him. We exchanged Kick messenger info and talked. He told me that he was thirty, bisexual, and attracted to my enthusiasm (I was a horny lil thing, remember?) "Well," I said, "we should meet up and you can see just how enthusiastic I get ;)" He liked that idea. So he asks for a picture. I send him one of my face.

He said something about how I have soft, almost feminine features to my face and that he loves that. He sends me one. He doesn't look too bad, a little chubby. He asks for a picture of my body.

I send a picture of me, naked, turned around, wearing a pair of my sister's panties that make my juicy lil booty look even juicier.

He loses it. He keeps saying that my ass is perfect and that I'm perfect and I feel so happy.

We agree that he'll pick me up that Saturday under the guise of a sleepover or something to trick my parents. When he drives up, I practically fly to that shitty little car and I'm excited and he waves and I run and I can't believe it's happening.

The drive there is quiet. We just keep smiling at each other as though sharing a secret joke. I rub his leg a little to seem confident even though I've never been so nervous. I try not to consider the possibility that I've been kidnapped. He holds my hand and my stomach flutters.

We arrive at a hotel, which scares me, because he knows where I live but here we are at the Days Inn. No one stares or pays attention. I feel like I'm glowing or something and wondering why they can't tell. My stomach does more flips when we get in the elevator, where I half expect to be murdered.

We arrive at the hotel room and he unlocks it, giving me a sly smile. What's his name? I'm about to have sex with this man and never thought to ask his name. We step inside and I take a tender seat on the couch while he locks the door. He struts over and sits next to me, undressing me with his eyes.

"Here we are," he says, rubbing my thigh (which makes me shake) and I nod. He leans forward to kiss me and I'm not ready I'm not what would my parents think and I'm scared and

and

and our lips meet

and it all melts away.

Suddenly I'm possessed by an animal that holds his face and wraps my tongue around his and doesn't break the kiss while I unbutton his shirt and feel his chest and it's happening and I'm flying.

He breaks the kiss and smiles. He lifts my shirt up over my head and plays with my nipples and kisses my chest. Then his hands are all over my legs again, he touches my crotch, I shiver. He kisses me again and then helps me up and unbuttons my pants and pulls my tight jeans down over the butt they hug so nicely without looking because when he looks

He stops

And I smile

Because I'm wearing those panties.

My pants are off and so are his and he's on top of me on the couch and we're making out. I grope his manhood and he gropes my boyhood. He gets his underwear off and I feel it, I'm actually touching a real penis and it feels so right.

Suddenly he flips me on my front so my booty is in the air and he gasps, I swear to God he gasps. He tells me it's perfect again and squeezes it and kisses it and licks it and smacks it hard, which I actually really like. He licks my ass crack and decides he can't take it anymore and RIPS the panties off, actually RIPS them off my ass and goes at my asshole like it's the most delicious thing he's ever had. He does this a while until I hear him reach and grab what I assume is lube and spreads it on my tight little virgin hole.

Is he wearing a condom?

He's not wearing a condom.

I open my mouth to say this but fuck he enters me.

He lets me get used to it but all I can think is that it's there, his cock is actually in my ass.

And it feels right.

He starts to thrust his hips and I relax my hole somehow so he decides to go deeper and SHIT it burns, it burns and stings, and it's uncomfortable and what's his name?

He sees my discomfort and pulls out. I assume it's over but then IT'S BACK INSIDE ME and he humps and it stings like hell but then

Then

He's fucking my ass

And it feels good

Holy shit, I don't know his name and he's fucking my ass with no condom and it feels GOOD like not just in my ass but like a blanket that spreads over my whole body. I hear his hips POP repeatedly against my bubble butt, which he smacks with his hands and I'm sure is red. My entire body thrusts with him, my ass savoring every inch of his cock.

My own cock has never been so hard and it begs for attention but is drowned out by the amazing sensations going on in my asshole. My ass ripples as he speeds up his thrusts, and I'm in heaven. I keep barely hearing comments from him about how glorious my ass and body is, how cute I am and how my ass cheek has the most adorable little mole on it. I'm so drunk on pure ecstasy that I don't care how loud I moan (and I get pretty loud) or how many of the neighbors hear.

Suddenly he thrusts really hard and with finality. There's a pause and then he goes out and in once more, an action punctuated by a strange warmth that I instantly know is his warm seed filling my insides. He keeps his cock in me for a moment before pulling it out. I suddenly feel empty. I lay down on my side and he lay next to me, his warm naked body making me feel safe. He puts his arms around me and pulls me close. He kisses my cheek and I close my eyes and feel like we're melting together. I ignore the feeling of his cum leaking from my asshole. I get sleepy. Before I fall asleep, I squeak out, "What was your name?"

"John," he says. John. I just got fucked my John. John's cum is inside me.

I fall asleep in John's arms.

This would be the beginning of many sessions with John. I would have sex with him regularly for years afterwards. I still do.