First time

By Teigan_andi

Original link:

Tags: first time, crossdressing, thong, cum, anal

Added: 22 Mar 2011 Views: 62504 Avg Score: 4.67

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy girl style.

We arrived in Florida on a Wednesday morning and spent the next few nights parting and having a blast. Then on Saturday evening all the girls wanted to go to a popular gay club. I was against the idea, not because it was a gay club. I wanted the chance to pick up girls myself.

To give a little of origin on me and my sister, one reason we were so close when I was younger she used to make me play dress up and have tea parties with her. Many of weekends I would spend my time in a dress drinking “tea” and having a good time.

That’s where this comes into play. I confined in her that I was nervous about going to this club. Her response was simple, “You’re not going as you.” You’re going as Teigan.

I rejected the offer and left the room, only to have all the other girls start chanting for me to do it. The words of my sister, “We’ve all been looking forward to this all week, please!” So I reluctantly agreed.

I took a shower and shaved all my hair for them. I became silky smooth as they said. I have a small frame and a boyish face, which they loved. I was already tanned, another point they liked.

They sent me into my bedroom where my clothes were laid out. A short white mini skirt, pink top, black lace bra and thong set. A pair of cute black stiletto heels with a strap to go around my ankle. I put them along with a black wig. With the skirt my ass almost came out. I wore a black wig and the girls did my make up. They had accessorized me with bracelets and necklaces and ear rings. Standing in the mirror I looked hot.

The club went fine, I fit right in. After it closed a couple told us of an after party they were having at their place. Lots of people would be there. So we went, me still as Teigan.

I had a few drinks there as well and was feeling pretty tipsy. I noticed there were a few straight guys there and most of them would glance over at me. After the drinks took affect I went to the rest room. I was standing, washing my hands when someone came in behind me. Startled by someone in there they said, “Oh sorry.” But he didn’t shut the door. Instead he locked it.

He instead walked up behind, “I don’t believe we’ve met.” I didn’t know what to say or do, his hands rested firmly on my hips. Then in my ear he whispered, “I know what you are.” I felt a pulse in my panties and said, “I’m sorry, I’m not into guys.”

His hot breath rolled across my neck, “me either.”

He began rubbing my boobs, “No really,” I said “I’m not into guys.”

“Babe, I think you’ll enjoy this. If not I’ll tell everyone you tried to suck my dick and embarrass you in front of your sister and her friends.”

He had me. As much as I didn’t want it, I kinda did.

After a moment, he saw I wasn’t going to deny him. I pulled my ass onto his crotch and could feel his hardness. It felt good against my skirt. He ran his hands down my waist and my thighs and then up my skirt. I heard him unbutton his pants.

He lifted my skirt and with this feet spread mine and pushed me down over the counter. He ran his dick over my thonged girlpussy. I couldn’t help it, I whispered, “I want you in me.”

I heard him spit on his hand an lube his cock up. Then I felt him pull my thong aside and felt the tip of his cock on my girlpussy. The anxiety was killing me as he slowly pushed in. The head was just in and it did hurt but I wanted it all in.

He grabbed my hips and then said in a dark voice, “Now you’re my bitch!”

He pushed the rest of his 8 hard inches in, I screamed in pain. It hurt so bad. Then he started grinding me through the pain. I began to cry with the pain. After five or so minutes it started to feel good, real good. I started grinding back. His cock in my ass were moving in one motion. I loved feeling every inched of him inside me.

The next thing I knew he was pumping faster. “Get ready slut!” he yelled and then he shot loads of hot cum in my ass. As I felt it explode in my body, I creamed my panties with my own cum. I felt his hardness go soft in and he pulled out. “Fix your make-up whore.” And then he left the bathroom.

I was lucky enough to have a purse with make up in it my sister had prepared. As I was fixing it I got a second great sensation. His hot cum running down my thong and legs.

I didn’t see him at the party and didn’t tell anyone what had happened. But it wouldn’t be my last time to feel a man inside me!