How I Lost My Virginity

Friday, December 21st

The Ocean looked beautiful from the veranda of the room that my brother Scott and I shared on the cruise ship. I was 18 years old and he was 22. Our parents were sending us on a week long vacation in the Carribean on an amazing cruise ship. I had decided long before we got there that I had to lose my virginity on this trip. I was so tired of being a virgin, so I decided that this was my chance.

After spending two days just lounging in the sun and meeting tons of hot guys, I had finally picked the one that I wanted to take my virginity. Brad was a gorgeous 19 year old with blue eyes and brown hair, tan, tall, with a great smile. I'm not so bad myself. I'm' about 5'4, 120 pounds, 34 c chest, a nice ass with long almost black hair and green eyes. We flirted by the pool and made a plan to meet later that night in the bar on the ship.

That night my brother was having a massage, so I took my time getting ready. I showered and shaved my pussy bare as it always is. I was so excited for the night to come, I couldn't help but slide a finger in my pussy and start swirling it around. It felt so good, but I knew that if I waited for that night it would be so much better.

I made my long hair straight so that it was cascading down my back. I put on just a hint of black eyeliner to accentuate my eyes. Then came the black lace thong, the strapless push up bra and the red short strapless dress. I looked hot. My brother came back to the room as I was leaving to meet Brad.

"If you weren't my sister, you'd have to watch out Carly!" He joked with me.

I gave him a wink and said "Don't wait up for me big bro."

I walked into the club and took a look around. I got more than just a few appreciative glances. It was dark and smokey, and I felt someone come up behind me and put their arm around me. "Hey gorgeous" Brad said as he looked at me with those sparkling blue eyes. "Want a drink?"

"Sure. Rum and Coke." I replied. As he walked away to get us our drinks, I watched his cute ass thinking to myself, this is it babe.

Brad came back and we drank, laughed, talked and danced all night. Around 12:30, we were dancing and I was getting really hot. I could feel his big cock pressing up against me, and I couldn't take it anymore.

"Want to go back to your room?" I asked in a sultry voice.

"More than anything" Brad replied. He took my hand and we quickly left the bar and headed back to his room.

Now, just because I was a virgin didn't mean that I didn't have any experience. I had been with lots of guys, and I've been told I am a pretty good cock sucker.

Once we were in his room, Brad grabbed me and kissed me hard. Our tongues danced with each other and his hands roamed all over my body. He slowly took my dress off, leaving me in my high heels, thong and strapless bra.

"You are so beautiful" he said.

"Brad, I'm still a virgin, I want you to take my virginity, please!" I said to him.

"Are you sure?" he asked.

"More than anything." I said.

He quickly began pushing me down on his bed, kissing me with even more fervor than before. He took off his shirt, and then my bra. I was so hot feeling us skin to skin. My pussy began to moisten. His hand began to pull at my nipples, making then become erect. His mouth moved to my neck as he began to kiss it while still fondling my breasts.

I began to moan from the feelings of desire that were being brought about by being this close to Brad. He sensed this, as he began licking and sucking on my nipples. It felt sooooo good that I didn't know what to do with myself.

"Please touch my pussy Brad, I need you to touch me" I said between moans.

He moved up to my mouth and then with a sly look he pulled away and grabbed the top of my thong with his teeth and pulled it down over my legs. His eyes lit up when he saw my bare pussy come into view. He suddenly grabbed my hips and pulled me towards him as he stuck his face in my pussy. He started to lick up and down my vaginal lips, every now and then poking his tongue in between them for a taste of my hot, wet hole. He was such a tease! Finally he began to lick my clit. It felt so good. I was really close to cumming. But, he could sense whenever I got close and then he would pull away. Finally, he flicked my clit with his tongue and jammed two fingers up my pussy. This was too much for me and I started cumming like crazy. He kept this up until I came down from my orgasm. His face glistening with pussy juices, he grinned up at me.

"Two can tease" I said to him as I sat up and pushed him on his back. I expertly undid his pants and pulled down his pants and boxers with one quick pull. I kissed his neck as my hand began to glide over his hard 8 inch dick. He began moaning.

"Oh baby, that feels so good, but please, suck my cock" He begged.

With a wink, I was down in between his legs. Then, with one quick gulp, I engulfed his entire cock. As it slid into my throat, I began using my throat muscles to massage his dick. His moaning got louder and louder, and when I thought he was near to cumming, I stopped and just licked around the head. I did this until he calmed down a bit, then I took him in my throat again. After about 15 minutes, I reached under him and started massaging his balls. It was too much for him and with a groan he emptied his load into my throat.

"God, you are the best cocksucker Carly" Brad said with a satisfied look on his face. "But now, it's time to make you into a woman."

Brad took out a condom and rolled it over his penis. With a few looks at me, he was hard as a rock again. I laid back on the bed and he positioned himself over me. He guided the head of his cock to my dripping pussy. Since I was so wet, it didn't take much for him to get it in. I felt so consumed, that he had to stop for a minute to let me get adjusted.

"You are so tight baby" he said.

"your cock feels so good in my tight pussy" I responded. "Now Fuck me"

With that, he slowly pulled back and pushed his cock into my pussy. He went slow, until I said to him "fuck me hard brad, I want to come." With that he began to slam in and out of me like a piston. I could feel his hard cock rubbing against my g-spot, giving me several mini orgasms. Finally, he reached down and began playing with my clit. I began cumming and I could feel my pussy muscles become even tighter on his cock. He couldn't take it anymore and he came at the same time as me.

"That was incredible" he whispered in my ear.

Shortly after we fell into a deep sleep, until I awoke feeling his cock in me again. "good morning" he said while still pushing in to me.

I wrapped my legs around his body and fucked him back for all I was worth. It didn't take long for either of us to come that morning. WE continued fucking for the rest of the week. I never did see him afterwards, but I will definitely never forget him.