The Virgin Maid

We met online, and I was upfront that I was looking for my first time with a man. We agreed on a roleplay, and arranged a meeting. When we met we recognized one another instantly, even though we'd never even shared pictures, but it was late enough that there weren't many people around and we'd shared what we'd be wearing. We barely talked, just confirmed we were the right guy, and we walked away towards his place.

Neither one of us would've stood out in a crowd. He was a young white man of average build, with dark hair. I was a young Mexican guy with latte-colored skin and straight jet-black hair. We were walking side by side, not holding hands or anything - he was a stranger after all, not my boyfriend. I was, however, glad it was dark out - the darkness conveniently hid my erection and my overall excitement.

It was a short walk to his place. When we got there, we had drinks, we didn't really talk much. I did ask him something on my mind, though.

-Have you fucked guys before?

-I'm no expert, but yeah, I've fucked guys before.

-I've never done it with a man before.

-Yeah, you told me.

He handed me the clothes for the roleplay we'd agreed on.

I changed into them quickly. They consisted of black flat women's shoes, a knee-length black skirt, plain white panties and a matching bra, which I stuffed with my socks, a plain woman's t-shirt.

I started pretending I was cleaning, pretending to dust the couch. Almost immediately, I felt a hand on my ass. I froze, letting him fondle me at his leisure.

He lifted up my skirt, feeling up my thighs. He feigned surprise.

-Does your boyfriend not mind you not shaving? When you spread your hairy legs for him?

-He - I-I'm a virgin, sir.

-Really? Well, not for long. But first, go shave.

I obeyed and went into the bathroom. I undressed as fast as I could, splashed water on my legs and armpits, found a razor and shaved them as fast as I could, which was intensely erotic - I was shaving on the orders of a man - it wasn't the first time I shaved, and it had always had an intensely erotic feminizing quality for me, but it was enhanced by being done on a man's orders.

I'd barely finished when he barged in. He'd already stripped down to his boxers.

-Are you done yet?

-Yes, sir, just finished...

He led me by the hand to his room, to his bed. I laid on my back, as if by instinct. He put his hands on my chest, massaging it.

-I love your big tits.

I nodded, unsure what to say. He pulled down his boxers.

I stared, checking out what was going to be my first cock. It was long, uncut and rock hard.

He grabbed a condom.

-I'm not going to knock up the help.

He put on the condom. I laid on my back again. It was time to face the music.

He grabbed my ankles, lifted my legs, and put them on his shoulders. As my now smooth, latte-colored ankles touched his white shoulders, I knew this was showtime, there was no backing out now, I was truly going to take a cock in my ass, get my ass cherry popped, get my boypussy deflowered.

I felt the tip of his cock pressing against my ass, I felt the increasing pressure of his cockhead. For a moment, I thought it would never enter me, that he was too thick or I was too tight, and then I felt him slowly, bit by bit, enter me.

I kept pushing against his cock and it slowly went inside me, deeper and deeper. For just a moment he stopped, and then began thrusting in and out, even as my ass began to get used to his cock, and my mind completely focused on the sensations of being fucked.

Eventually he grunted and came. He pulled out and we were soon lying side by side. As he laid beside me, he kissed me on the lips, and I kissed back. It was also my first time kissing a man.

-So did anyone else contact you from that site?

-Yeah, several guys.

-Are you going to meet up with them?

-Yes.

I did meet up with more men. It had been my first time taking cock, but certainly not my last.