I live in a wealthy family. We’re not carefree by any means, but we don’t have to worry. And I’ll admit it, people with money are strange sometimes. My father is the president of a company, and we live in a really nice neighborhood. Our house is very big , but it’s more than enough for the four of us, including my sister Haily, who is two years older than me. She has long bleached hair, and a nice tanned, tight body. And back to my point about people with money, we’re a lot different than the other families around us. We don’t have dark family secrets, we don’t lie to each other or squabble constantly.
In fact, we all get along really well. My parents are very open with us, and my sister and I were unusually close. Even after my parents gave me the sex talk, my sister told me all of the things they left out, like all of the positions and various activities people did during sex. I always felt close to her, and she genuinely liked me. Sometimes she would come in my room just to be around me, and we would listen to music or talk.
As I neared eighteen, Haily started joking around with me about sex. Sometimes she would come into my room without knocking, to see if I was jerking off. Stuff like that, she was just playing around. Once I was eighteen, and I felt like I could do anything I wanted, I decided to pull that prank on her.
Our parents left for a business trip, and we would be alone for a whole week, and I knew that Haily would occasionally sneak boys up to her room. I never really gave it another thought, I guess I just assumed she was having sex, and it wasn’t a big deal. I wasn’t going to tell our parents, my sister and I trusted each other.
But one day, late in the afternoon, I waited until Haily had been in her room for a while, and I figured I would burst into her room. So I snuck up the stairs to her bedroom and listened through the door. To my delight, I heard distinct sexual sounds. She must have been masturbating, I was so lucky! I quickly opened the door.
Haily was on all fours on her bed, naked and facing me with her eyes closed, and to my surprise there was a young man not much older than me slamming into her from behind. I just froze, I had not expected to find Haily fucking someone in her room. She opened her eyes when she heard me enter, but she didn’t act embarrassed or angry. She kind of smiled at me while I just stood there. The guy stuffing her didn’t let up, he looked questioningly at me, and then down at Haily.
“Who’s this?” he asked casually.
Haily seemed to really be enjoying herself, and she was obviously approaching an orgasm. Her face contorted a bit.
“My brother,” she answered.
The guy kept slamming her, unaffected by my presence. I just stared as he pumped into her, and after a few moments Haily squealed and gripped the bed tightly. She lowered her face into the mattress and cried out into the sheets as she came. The guy was not far behind, and he soon grunted and hunched over her as he shot deep inside of her. After a minute of catching their breath, Haily looked up at me and smiled.
“Hey,” she said. “Don’t just stand there, come over here.”
I cautiously approached the bed. The guy leaned back against the bed, and Haily sat up on her knees. She pulled me over to her.
“You got quite the show,” she said.
I didn’t know what to say. I felt weird with the guy who I didn’t know laying naked next to me. He probably felt the same way, although fucking my sister in front of me didn’t seem to bother him, so he pulled his dick coverd in cum out and got dressed and left quickly.
“He comes over once in a while,” Haily said.
Haily didn’t seem to mind being naked in front of me, in fact she was kind of touchy feely with me on her bed.
“Did you like what you saw?” she asked with a smile.
I looked her up and down. “I like what I’m still seeing.”
She leaned back on her elbows, giving me a great view of her body.
“Why don’t you take your clothes off too? Then we can be nudie buddies.”
I shrugged and quickly stripped down. I didn’t feel shy at all, I wasn’t worried that she wouldn’t like seeing me naked or anything like that, I wasn’t even embarrassed about my erection. She smiled when she saw it, and reached out to touch it. I was taken by surprise, and jumped.
She giggled. “Does that feel good?”
I sighed. “Oh yeah. But, why are you doing that?”
Haily cocked her head. “You don’t like it?”
“No, I love it.”
“Then just let it happen.”
Those were the best words I’d ever heard in my life. For the next few minutes, I had my first handjob. Haily was an expert in the manipulation of male genitals. She fondled and rubbed and caressed, I thought I would cum immediately. She lovingly jacked me off, while I relaxed on the bed. Finally, I came in her hands, and it was the most blissful feeling I had ever experienced. She smiled up at me.
“Feel good?” she said cheerily.
I nodded. “I’m a virgin,” I blurted out.
She seemed surprised, and then she gave me a big smile.
“How about we take care of that?”
I couldn’t believe what she was saying, did she really want to have sex with me? She crawled on top of me and moved her hips over mine. She lowered her face to mine and kissed me very sensually. It was so erotic, and the thought of fucking my sister was really arousing. So I let it happen, as she had suggested.
She rubbed her crotch against my dick, I could feel his cum against my rock hard penis. She circled her hips around on me, and pressed her tits against my chest while she kissed. She was really experienced, I could tell. She sucked my tongue into her mouth and swirled it around, and I was too overwhelmed to do anything back. She kept humping me and kissing me until she had her fill and then she raised her hips.
She moved my dick to her warm hole and I sunk right in. She was really wet and I slid all the way in. It felt so good filling her up, I came right away. I was so embarrassed, I was worried she would be mad. She just smiled and kissed me.
“It’s okay,” she said. “It was your first time.”
She squeezed me inside of her and started to ride me, and I was still hard. It felt so good, and since I had cum twice already, I could really enjoy it without worrying about finishing too soon. I squeezed her tits and played with them while she rode me. She came after a few minutes, and it felt so good to have her climax around my dick.
Then she rolled over and I fucked her missionary. I slid in and out of her hot pussy, which was full of my cum and his. She had two more orgasms, and she loved it when we kissed. We were both full of lust, we couldn’t get enough of each others’ bodies. Finally I came with a deep groan inside of her. She held me tightly against her as I released my cum inside her pussy. I was exhausted, and we just laid there, still joined.
“Did it feel good?” she asked.
“It was fantastic,” I sighed.
“Do you like how my pussy feels?” she asked.
“It was so warm and tight.”
“You filled me so full of cum, I love letting guys cum inside me.
I looked up at her. “Really? Why don’t your worry about getting pregnant?
“Because I love you, silly.”
She smiled. “Don’t worry about that. Just relax, and we’ll fuck again when you’re ready.”
After a few minutes, we fucked again, and I came inside of her. I loved filling her up with my cum. Afterwards, she gave me a nice long blowjob, and I came in her mouth. I loved knowing that I lost my virginity with my sister.