My Sister Takes My Virginity

I hated that I was still a virgin. All of my friends had gotten laid before me and several of them were fucking many girls. I would listen to them brag about what they did with these girls almost every day when I hung out with them after school. They would even show me nudes and videos of the girls too which made me insanely jealous.

I think the problem with why I wasn't getting laid was that I was too much of a nice guy. Many of my friends that were girls were exactly that: "friends." All of the girls that I was interested in had friend-zoned me from the get-go due to my nice guy behavior. My friends were more aggressive than me and a few were complete players and yet they got the girls.

The only action that I got was when I would jerk off to porn at night or even sometimes in the early morning hours. Whenever I was in my room, my hand would become glued to my cock as I would jerk off constantly. I shot my wad to many pornstars that were my favorites and I would also jerk off to girls at school and those that were my friends. I filled socks and tissues with my horny cum.

I was always pent up from my sexual frustration and the only outlet at the moment was beating my meat to oblivion. My cock was always hard, especially at school where the girls would wear shorts and skirts that showed off nice legs and great asses. Where I lived it was always warm, so girls would wear revealing clothes everywhere. It drove me crazy with lust as I watched girls that I had crushes on walking around with barely any clothes. Their lovely tits and butts made my cock jump around all day.

My sexual frustration seemed like it was never going away and I worried that I would be a virgin forever. However, that all changed one day when my older sister and I hooked up. Jillian was older than me by two years. She was 20 years old and worked as a secretary for a law firm. She had her own apartment and lived about 10 minutes away from our parents' house. Jillian was drop-dead gorgeous. She looked like a young Jennifer Connelly. So many guys wanted her, including many of my friends.

I knew that she was beautiful and had a nice body. It was impossible not to notice. Jillian had a nice rack that I had seen several times whenever she would walk around the house in her bra when she lived at home. I would always look away and tell myself not to have these crazy thoughts about my sister.

Jillian had even caught me looking at her one day when she was doing laundry and had on nothing but her bra and shorts. My eyes had absentmindedly strayed to her tits and my dick had moved in my pants. Jillian caught me looking and I expected her to lash out at me. I tensed up as I waited for her to call me a pervert or something but the words never came. Instead, she smiled at me. I smiled back at her awkwardly and made sure to keep my eyes on the television.

The day, when everything changed for me, happened like any Saturday. Jillian would come over and hang with my parents and me for the day. However this Saturday, our parents left to go to a friend's get-together so my sister and I were alone for the rest of the day.

"What's been going on with you? Anything new?" she asked me.

I shook my head. "Not really. I'm hoping to get a job for the summer so I can stack some money before I start at the community college."

"What kind of job were you thinking about?"

"I've been applying at retail stores mostly. I figured it would give me the flexibility to go to school too."

"That's good. Did you ever ask that girl out that you liked? Betty? Was that her name?"

I blushed. I had told my sister about Betty a few weeks ago after I had had a few beers. She had told me to ask Betty out and to not be afraid. I told her I would but of course I didn't.

"Nah, we're just friends," I said.

"What? You said you really liked her? Why haven't you asked her out?"

"You know...I just want to wait until the right time." I knew that this was a lie. Betty had friendzoned me months ago and I knew there was no way that I could ask her out without making it weird.

"The right time? There is never a right time! You just have to do it!"

"Yeah," I said with a sigh.

My sister looked at me curiously. "Are you still a virgin?"

I looked at her in surprise at her question. "What?"

"You heard me? Are you still a virgin?"

"Nah," I said even though my face got redder.

Jillian laughed. "I don't believe you. Not that there's anything wrong with being a virgin. Are you saving yourself for someone?"

"No, I'm not a virgin!" I said defensively.

"Come on, you don't have to lie to me. We have always talked about everything together," Jillian said with a warm smile.

That smile broke down my defenses. I let out a sigh. "Yeah, I'm a virgin."

"Ok. Have you met anyone that you want to lose it to?"

"There are so many girls that I want to lose it to," I said with a frustrated laugh. "At this point I would fuck anyone. I would even pay a prostitute!"

It was a joke but I saw my sister's face change. She looked at me with a frown. "What? You shouldn't have to do that. There are many girls that would be happy to fuck you and be your first. Shit, I would be your first."

I looked at my sister in surprise. "What?"

A smile came back to her lips. "I said I would be happy to be your first. I would love to take your virginity."

I didn't know what to say as I looked at my sister. This was so out of left field that my brain was having difficulty processing it. Jillian could see the surprise on my face and she got up and took off her shirt. I looked at her rack in shock. My mouth fell open and my cock started to grow.

"What are you doing?!" I asked her.

"What does it look like?" Jillian took off her shorts and my eyes went to her pink panties. She took off her bra and panties and my eyes grew large as I stared at her. My sister had nice tits with light pink nipples that stuck out from each boob. Her pussy was shaved and I could see her amazing pink labia between her legs.

She then walked over to me and got on top of me. She pulled down my pants and then took my cock out of my underwear all in a rapid movement. My dick was hard in my sister's hand.

"You have a nice cock. Don't you think it deserves to finally feel a pussy?'' Jillian asked me. She rubbed my cockhead against her pussy lips. There was precum already leaking out from my cockhead. "If you don't want to do this, I will stop."

"No! We can do this!" I shouted. There was no way that I was going to stop this. I could care less if it was incest. My sister was hot and I wanted her to take my virginity. I needed her to.

Jillian slowly put my cock to her entrance and then sat down on it. I let out a deep groan as my cock went deep inside of my sister's pussy. It was unlike any sensation that I had ever felt. Her pussy was warm and wet.

She put her hands on the back of the couch and began to ride me. I looked up at her as I moaned. My moans were very loud as the pleasure was unlike anything I had ever experienced. I slowly raised my hands and put them on my sister's hips. She was moaning herself which made my cock twitch like crazy inside of her. Her moans sounded so fucking hot.

Jillian increased the speed until she was now literally bouncing up and down on me. It was a wonderful sight to see. My very hot sister was riding my cock!

I could not hold my cum any longer. I let out a groan and grabbed her tightly. My cock jumped inside of her and my jizz spurted out rapidly. My entire body trembled against my sister as she continued to ride me. It took a few more seconds until I was done cumming. I looked up at my sister who was smiling down at me. She stopped riding me.

"So, how was it? Was it everything you hoped it would be?"

I let out a satisfied laugh. "It was so much better than I hoped. It felt so good! I can't believe that we did that!"

"Are you feeling guilty about it?"

"No way! I loved it! Actually, can we do it again?" I asked my sister with a grin. Jillian laughed and began to ride my still-hard cock again.