First time in a female body

My heels clicked rhythmically on the asphalt as I headed to a remote neighborhood in the south of the city. Today would be my first experience with a man, and I was dressed in women's clothes. I dress like this quite often and constantly fantasize about it. I read about this place in the newspaper – it said men come here for sex with other men. I was shaking all over with excitement and kept looking around, but I kept walking forward.

That evening, I decided not to dress too provocatively: a short gray skirt, a jacket of the same color, and a white blouse. Underneath was silk lingerie: a bra and panties with stockings. Today I wore a light wig, applied peach eyeshadow

and pink lipstick. I also adorned my lips with a special gloss. I felt a growing excitement – with every step, the silk of the panties rubbed against my rising cock.

I turned into a kind of seedy, poorly lit place and stopped, waiting for my eyes to adjust to the light. At the far end of the alley, I noticed a large male figure – he was smoking a cigarette and leaning against the wall. My throat went dry, but I tried to start a conversation:

"Hi, I'm Jeannette."

"Well, hello, Jeannette! What brings you here?"

"I'm not really sure..."

"Then let me help you. Do you give or take?"

"Uh, I... um, I give..."

"Has any cock ever been in that dirty little mouth of yours, Jeannette?"

"No."

"Wow, a virgin," he laughed.

His questions were getting on my nerves, and I was no longer sure I wanted any of this.

"You know, I think I made a mistake... I think I'll go."

"I think it's a bit late for second thoughts, Jeannette."

And then I noticed another man standing behind me, blocking my way out.

"You see, Jeannette, Mark is over there, and I'm here. And we both want to be pleased. And I think a wonderful girl like you will take care of that today."

A shiver ran through my body – I realized there was no way back. I had heard that muggings and assaults were not uncommon in this area, so if I tried to break free, they could seriously hurt me. I had to try to take the initiative.

"Please... I'll do whatever you want, just don't hit me."

"Oh, Jeannette, I'm glad you said that. We really wouldn't want to hit you. Come a little closer and show me how you can make me feel good."

I walked towards him like a robot. Soon I was kneeling on the cement floor, unzipping his pants. I reached in and pulled out his cock. At my touch, it immediately began to grow.

"That's it, Jeannette, that's right. Very nice. Now use your tongue."

I opened my mouth and slowly ran my tongue over the head. It tasted salty, and I could also taste his sweat. I fought back the gag reflex as I tried to run my tongue up and down the shaft. I heard him groan as I licked all over the shaft. Then his hands came down on my head, and now he was in charge.

"You're doing great, baby! Take it in your mouth. Take it in your fucking mouth, you dirty slut!"

I noticed he was getting more aggressive. If I didn't make it feel better for him, he would hurt me.

"Mark, this bitch knows how to suck. How long have you been doing this, huh, Jeannette?"

This was my first time, and I couldn't say I was enjoying it much. I had hoped to find someone better and more decent than these lowlifes. Suddenly, he gripped my head and guided his cock straight into my mouth. I felt it hit the back of my throat and barely held back from vomiting. He started bobbing my head on his tool. I began to whimper with every thrust. Soon, his balls were slapping against my chin, so it was really deep. He kept increasing the pace, tearing my open mouth apart. I felt like a dirty, cheap slut and now understood what women feel when they are pressured into giving a blowjob. His cock began to twitch, and I knew he was about to cum.

"I'm gonna cum right in your mouth, bitch. And you better swallow every last drop! If you spill a single drop – I'll have to beat the shit out of you!"

I positioned my tongue so his cum would go straight down my throat. This would be my first time tasting cum, my first time swallowing it. I hoped I wouldn't throw up. One last thrust, his cock swelled and exploded in my mouth. I squeezed it with my lips and tried to swallow the entire stream. I had never seen anyone cum so much. He held my head, not letting me release his cock from my mouth. He only let go when the last drop had left the tip. I immediately collapsed, exhausted, onto the floor. I lay there completely motionless while he tucked his cock back into his underwear and zipped up.

Time passed, and I hoped they would leave me alone. But there was still the second man, who surely wanted his share. I thought he would also want to use my mouth, but he had other ideas. He grabbed my wrists and dragged me into a toilet stall. There, he positioned me over the toilet and taped my hands to the pipe behind the bowl. I heard him tear off another piece of tape – he immediately used it to cover my mouth.

"That's how you're gonna stand, okay? Otherwise, you'll get it bad. Got it, bitch?"

I nodded my head in agreement. He lifted my skirt and ripped off my panties. Now my ass was exposed, and it became clear he was going to fuck me. This wasn't part of my plan, so I tried to jerk and scream for him not to do it.

"Yeah, bitch, that's exactly what I'm gonna do. I'm gonna fuck your tight little ass, and you're gonna like it."

I started sniffling when I heard the sound of a zipper opening. Then I heard him spit into his palm and lubricate his cock. And then I felt the head pressed against my anus. He slowly began to push it inside.

The pain was unbearable. My sphincter tried to resist the intrusion, but it couldn't hold out for long. The head was already inside and continued to slowly move where its owner wanted it. Inch by inch, the cock sank into my ass, and I thought I would pass out from the pain. He was literally tearing me apart. I knew he would actually tear my ass, and these injuries would be permanent.

"Oh, Jeannette, you have such a tight little ass! I'm so glad I'm the first one in there!"

The pain gradually subsided. He kept drilling my burning ass, and his hand reached for my cock. He tore my stockings and freed my cock – immediately starting to jerk it off in rhythm with his thrusts.

"Come on, baby, get your little friend going. I want you to cum while I'm fucking you!"

My cock filled with blood from his movements. Now I was getting turned on too – I was aroused by this position of a dirty slut being fucked against her will. I started thrusting back, and my whole body became a toy for his desires. I wanted him to fuck me and cum inside. And I wanted to cum too – I began moaning with pleasure into my sticky gag.

The pace increased, and he was close to orgasm. I was also on edge, waiting for him to explode. And then he erupted, accompanying his climax with a wild cry. At that second, I also released my load onto the toilet in front of me. He kept moving inside me – making sure every last drop stayed in me.

Soon, he was spent and pulled out his cock. I felt the cum leaking from my torn anus. He freed my hands, and at that moment, both of them disappeared into the night. I tried to pull myself together and stumbled out of the neighborhood. I somehow made it to the main road, where I managed to catch a taxi. Sitting was difficult because my ass was literally burning after such an anal rape.

At home, I took a shower, washed off all the filth of those men, and collapsed into bed, reliving my first experience. Without a doubt, I would return to that neighborhood very soon to feel like a Woman again.