Shemale First Time Ch. 01

I had just gotten home from the store when it hit me. I looked in the mirror and said to myself, girl you need to get out of the place for a while. I had 2 weeks off from work and decided I would take a trip to a bigger city. I got on the Internet and started doing some research on the gay and lesbian population for different cities. After digging deeper I decided I would take my vacation in Orlando, Florida. I called and made hotel reservations and loaded my stuff into my car. Finally, I thought, I am getting away from this small lifeless city.

I figured it would be best to drive straight through instead of stopping. By the time I got to my hotel I was ready to take a nap. I slept the rest of the night and woke up early the next morning. I was ready to explore Orlando. I spotted a bar and decided to stop and check out the scene. I immediately noticed the bartender. She was tall and slim, long, curly brown hair, and dark brown eyes. She was a total knock out. I walked over to the bar and ordered a coke. She looked at me and said "Honey, we don't serve coke in this bar." I laughed and said " Ok, I'll have a Budweiser." She handed me my beer and I laid the money on the bar. As I was pulling my hand away, she laid her hand on top of mine and winked at me.

I had a few more beers and was feeling pretty good when I felt someone lay their hand on my shoulder. I turned around to see who it was and it was the same bartender. She leaned down and asked me if I wanted to dance. I said " Sure, I'll dance with you." As we danced the songs slowed down and before I knew what was happening we were holding each other tight. She bent down and kissed me softly on the lips and started running her hands over my ass. I broke the kiss and stepped back so I could admire her beauty.

Soon the song ended and we walked back over to the bar and had a seat. She sat beside me and said " By the way, my name is Adriana." I smiled and said " It's about time you told me your name, I'm Tina."

Adriana put her hand on my knee and told me to turn around on the barstool and face her. I did and I felt her hand slide under my skirt. Her hand slid up my thigh and her finger ran across my clit. I jumped. I stopped her and told her we should go back to my hotel. She said she should drive since I had a good bit to drink. I told her where I was staying. On the way there she reach over and rubbed my nipples through my blouse. The sensations of her rubbing my nipples made my pussy tingle. I could feel my panties getting wet and had to open my legs a bit.

She sensed my arousal and said " Let's wait until we get to the hotel or I am going to have to stop this car and take you right here."

I looked at her and said " Well you may have to just take me right here baby." And I slid my hand across her thigh. She stopped me and said " Let's wait, I have something to tell you before we do anything." I worried all of the way back to the hotel about what she could have to tell me.

I opened the door to my room and walked in, Adriana followed behind me. As soon as she got in the door she pinned me against the wall and I felt something push against my stomach. I looked down and saw the biggest cock ever. I pushed her away and said "Oh My God, you're a man." She looked me straight in the eye and said "I'm far from a man baby," and she took her shirt and bra off. Her tits were real and I told her to explain. She said " Fuck now, explain later." I didn't object and she started undressing me. When I was completely naked, she kissed down my neck and chest and took my nipple into her mouth. I was in heaven.

I started begging for more. She picked me up, carried me to the bed and said " You want more baby, you're going to get more!" She licked down my stomach and I felt her tongue slide over my clit. I moaned and she took my clit into her mouth and started sucking it. She pushed her tongue into my virgin pussy and I went wild. I started pushing my pussy onto her tongue. My juice was running down her chin and down my ass. She couldn't lick it up fast enough.

When she was satisfied with how wet I was, she took her jeans off and took something from the pocket. She walked over to me and laid her massive cock on the bed beside me and said " Would you like the pleasure of getting this monster nice and hard so I can shove it in that tight pussy?" I had never sucked a cock before but I gladly accepted and took her head into my mouth. I slowly pushed as much of it as I could into my mouth and began slowly sucking her cock. I knew I couldn't get all of that monster into my mouth so I licked down her shaft to her balls. She moaned and said " If you keep sucking me like that, I'm not even going to be able to get the head of this big cock inside of you before I explode."

She pulled her cock from my mouth and I saw she had a condom in her hand. I looked up at her and said " I have never done this before." She smiled and said " Ohhh a virgin huh, yummy, looks like I got lucky tonight." She rolled the condom down her cock and laid down on the bed beside me. She checked to make sure I was still wet and pushed 2 fingers deep inside me. It hurt and I screamed. She kissed me and told me it would only hurt for a minute. She rolled over on top of me and pushed my legs up to my sides, giving her full access to my pussy. She took the head of her cock into her hand and rubbed it up and down my clit. Then I felt her slide the head inside me. I felt like I was being ripped in half, she was atleast 3 inches thick and 10 inches long. She grabbed my legs and pushed them up a little further and took my hand in hers and said " Are you ready?"

All I could do was nod my head. I felt her push her cock in hard. That hurt like hell. I screamed and started crying. She let go of my leg and reach up to wipe the tears from my eyes and asked me if I was ok. I nodded my head. The pain finally subsided and she slowly started pumping in and out of me. I loved the feeling of her big cock stretching me to the maximum. I moaned and she started thrusting faster. I couldn't handle anymore, I had my first orgasm.

She tightened her grip on my legs and pumped her cock into me harder and faster. She screamed and said " Ohhhhhh God this is so fucking good baby, mmmmm you are sooo tight, I am going to cum in your hot pussy," and with that she came, and so did I for my second time.

She slowly withdrew her cock from me and laid on the bed beside me and kissed me. I rolled over and turned the light out. We fell asleep cuddling.

The next morning I woke up and she was gone. I wondered if I'd ever see her again?