Best Vacation Ever

The summer after I graduated from high school, my parents said I could take a one-month vacation to anywhere I wanted, and they would pay. Naturally, the destination I chose was Hawaii. It was as nice as I thought it would be, and I had a great time. The only problem was, I had absolutely no luck in picking up girls. I had a few girlfriends in school, but none of them let me go all the way, and I was still a virgin. I wanted to lose my virginity on this trip. Unfortunately, most people seemed to be with their families, and there were few single women around. Maybe I just didn't look in the right places.

On the last day of my vacation, I was feeling depressed, mostly because I was leaving and also because I hadn't even managed to kiss anyone, let alone get laid. I was lying on my bed in the hotel suite, watching TV, and was wondering if I should order a porn movie when there was a knock on the door.

"Housekeeping!"

I got up and opened the door, expecting it to be an old lady, as most of the maids were, but I was surprised to see a woman who was maybe in her early 20s. She was a tanned brunette and very attractive. She asked me if she could clean the room, and I indicated that she could. Then, I went back to watching TV.

As the girl moved around, I took the opportunity to check her out. She was wearing the standard housekeeper uniform, a navy blue dress that went down to her knees. I felt myself getting harder as I watched her bend over to clean something. The top of her uniform was very tight, and I could tell that her breasts were ample in size. By the time she was finished, I was horny and fully erect. She went to the door, and I followed her.

"What's your name?" I asked.

"I'm Julia. Will there be anything else?"

"Yes, there is one thing," I said. I reached into my pocket and pulled out a $50 bill.

She seemed shocked but took the money. "Thank you, sir. And what is it that you want?"

"You."

She looked confused. "What?"

I closed the door. "Come on," I said, taking her arm. I walked her to the bed and sat her down on it.

"Sir, I don't..."

"You don't have to do anything," I explained. "Just lie back and relax. I'll do everything."

"No," she said, getting angry. "I don't want to have sex with you."

I sighed. "Please. It'll be quick. You've already taken my money, so you might as well go through with this. Like I said, you don't have to do anything. You don't even have to take your clothes off."

Julia stared at me incredulously. I took her silence as acceptance and started to undress myself. She tried to get up once or twice, but I pushed her back down. I didn't realize it then, but looking back, she didn't put up much of a fight. Maybe she secretly liked being dominated.

By the time I was naked, she was laying back on the bed, looking at my hard cock with some trepidation and also, I think, some excitement. I wasted no time in settling in next to my soon-to-be lover and pushed her dress up to her waist, exposing her nice legs and a pair of black panties. I pulled the underwear off and dropped them on the ground. She shyly kept her legs closed, but I moved them apart and got a good look at her vagina. It was shaved and already a little wet, and I began touching it gently with my fingers.

"You act like you've never seen one before," she said.

"I haven't. This is my first time."

"No way."

"Really," I said. "You should be honored."

She rolled her eyes, but I could tell she was getting turned on, especially when I started rubbing her clit. After a few minutes, I looked up at her, and she nodded somewhat reluctantly. "OK," she whispered.

That was all I needed to hear. I eagerly climbed on top of Julia and positioned my member at her entrance before pushing it in. She groaned, and so did I. After 18 years, I was finally having sex, and it felt wonderful. All I could concentrate on was the feeling of a warm, wet pussy surrounding and caressing my bare cock. I started moving in her slowly, and I was so worked up that I thought I might cum at any moment.

Then, the housekeeper started humping me back. She had her eyes closed, as if she was trying to deny what was happening, but her body obviously liked it. I couldn't hold back any longer and started thrusting into her faster and faster. For the first time in my life, I felt alive. I told Julia I was going to cum soon, and she opened her eyes to look at me.

"Pull out, or you'll get me pregnant," she muttered.

At the thought of knocking up this beautiful Hawaiian girl, I came harder than I ever had, pumping my seed deep inside her fertile snatch, where it belonged. The ride seemed to go on forever. After I was finished, I collapsed on her, tired and completely satisfied, but she pushed me away.

"I told you not to cum in me, you bastard!"

I laughed. "Hey. You shouldn't talk to your guests like that."

Steaming, she just collected her things and left the room. And that's how I lost my virginity. I flew back home the next day. The following summer, I returned to the same hotel for another vacation. Unfortunately, I never saw Julia and finally asked some of the other housekeepers where she was. They told me she was on maternity leave, having given birth a couple months before. That made me feel a little better.