Tyler and Jenny: Part 2

It had been a week since Jenny and I had our first bit of fun together. I walked around with a grin on my face for the entire week, not only because I got my first blowjob, but also because I was anticipating what was coming up. Jenny told me that her younger brother, Liam, had a double-header in his baseball league coming up this week. That meant that Jenny and I could spend at least three completely uninterrupted hours together. Jenny had also made it clear that she was eager to go to the next level in our sexual escapades. She wanted to have full-blown intercourse. My friends at school the past year had started talking about trying to lose their virginities. As far as I knew, none of them had accomplished the task and I could brag about the fact that I lost my virginity first among my friends.

I had tried to think back to the three weeks we had of sex-ed in Health class this past school year. I knew how it was supposed to work and what all would happen. In addition, having seen many of Curt’s stashed porn DVD’s, I knew what moves I could put on to make it a great experience for both Jenny and myself.

I had been waiting close to the phone for the past half hour so I could answer before one of my parents. Finally, the phone rang and Jenny, the young girl that had rocked my world, was on the other end.

“Hey sexy”, she said, making my knees tremble.

My dad was just a few feet away so I had to act like it was Curt and not Jenny.

“Hey, what’s up?” I replied.

“Mom and dad just left with Liam to go to his baseball games. Curt is spending the rest of the day and night with Ken. How fast can you ride that bike?”

Ken, Curt’s uncle, had finished up with the Navy a couple years ago and was now a member of the SWAT team. Curt would often go with Ken to the state range to shoot off some big-time guns.

I turned towards my dad, already knowing what the answer would be. “Dad, is it okay if I go to Curt’s house?”

“Sure. Just be home before dark”, he said.

I turned my attention back to Jenny. “Yeah, I’ll be there in a few.”

I don’t think my feet ever hit the ground as I ran to the garage and mounted my bike. I must have set speed records for a bicycle as I pedaled as hard as my body would let me, fueled by adrenaline and hormones. On the way there, visions of what would take place made riding a little difficult, with the raging boner in my shorts creating a little discomfort. I turned with the curve in the road and Curt’s house came into view, with Jenny sitting on the front porch in her black shorts and her dark blue t-shirt. Her hair was already pulled back into a pony-tail in preparation for our activities. I turned into the driveway and parked next to the garage.

She sat still with her arms crossed over her knees. I walked up to the porch, maintaining eye contact with her the entire time. I stopped just short of the steps where she sat and looked down at her. She looked gorgeous. She was slightly more tanned since last week, and somehow she seemed even sexier to me. After the most rigorous bike ride of my life, I was a sweaty mess, but I didn’t care. I was ready to sweat some more.

She looked at me from top to bottom then said, “That was fast!”

“I know. I think I blew past a few cars on the way here.”

She laughed a little, then grabbed my hand in her’s. She stood up and led me inside. As soon as we got in the door, she closed it and we kissed each other deeply. Our tongues massaged one another’s while our hands rubbed up and down each other’s backs. It seemed like we were locked in the saliva-swapping embrace forever when she finally pulled back. I used my right foot to pry off my left shoe and then vice-versa. I hurried and removed both socks and threw them with the shoes by the door.

“Let’s go to my room”, she said enticingly. I shook my head yes.

Again, she took my hand and led the way. We walked upstairs to the entrance to her room. I had never been in there before. She opened the door to reveal a room with walls painted blue. While normal girls would have posters of young pop singers and boy bands, she had posters of sports teams and cars. No doubting it, she was truly a tomboy. Her bed wasn’t frilly like most girls. It was simple with light blue sheets, pillowcases, and a blanket. The bed frame was black and her headboard was a pattern of vertical bars with six inch gaps in between each bar, almost looking like jail cell bars.

As I trailed behind her, I shut the door and subconsciously attempted to lock the door for fear of being discovered. The fact that there was no lock on the doorknob woke my mind up to the fact that nobody else was around. We were totally alone and free to engage in animal passion. She sat down on the bed and looked up at me. I noticed this was the first time she had ever looked truly unsure, almost scared. I grew concerned.

“Jenny. We don’t have to do anything you don’t want to. I won’t be mad at you.”

She replied, “No, it’s just that all I’ve seen are my brother’s porn videos, I’m nervous about what it will feel like.”

I thought back again to my both my Health class and what I knew about sex from listening to older friends.

“Well, to be honest with you, it will hurt for the first few minutes or so, but it gets better. It will start to feel really good the longer we do it and the more we do it.”

“Really?”, she asked with a hopeful smile.

“Yeah. And I promise that I won’t hurt you”, I reassured her.

With that, her renewed sense of confidence brought her hands to mine. She grabbed my wrists and fell back onto the bed, dragging me down on the mattress with her. I lied on top of her, kissing her hungrily. I grabbed her hands and forced them over top of her head onto the bed and held them there. Our heavy breathing and our lips in motion were the only sounds that I could perceive. I pulled up from her slightly and took off my shirt and flung it to the floor. I moved my head down, lifted her shirt a little and kissed around her navel. Slowly I began raising her shirt above her shoulders and over her head before tossing it next to her bedroom window. I leaned back in and licked and sucked her still-budding breasts. She moaned in delight.

I repositioned her so that her ass was on the edge of her bed with her legs hanging down to the floor. I got down to my knees on the floor and put my hands on the waistband of her shorts. I pulled then down gently, exposing her innocent-looking white underwear. I finished removing her shorts from her legs and hurled them aside. I was anxious to see her pussy for the very first time. I moved my hands to the top of her panties and began pulling them down. I gazed with pleasure at the sight of her bare mound and her beautifully tight pussy lips. I finished taking down her underwear and refocused my eyes on her slit.

I looked up to see her staring longingly back at me, waiting for me to take action. I leaned in and gently licked the top of her crevasse. Remembering back to the porn I had seen, I rubbed my tongue up and down her lips. As I picked up speed, she indicated her gratification with a soft moaning. I recalled that the clit was near the top of her slit and would stimulate her even more, so I focused my tongue there. Almost instantly, her moaning grew louder. I continued working my tongue, exploring her perfect pussy with it. At one point, I used my hands to spread out her lips. I recognized that her hymen was still intact and that when I did finally get inside of her, I would have to break it. I was concerned for her because it would be very painful.

I knew that the time was right. I had been rock-hard from the moment I entered her bedroom and I could tell she was ready for my cock. I stood up and dropped my shorts on the floor. Seeing that I was prepared, she moved herself completely on the bed in anticipation. I pulled down my boxers and revealed my familiar throbbing erection to her.

I crawled onto the bed and position myself between her legs, then grabbed my dick and slowly moved the head up and down her slit. She started to breathe very heavily, nervous about what was going to happen.

I had to ask her, “Are you ready?”

“Yeah” she replied anxiously.

“Let me know if it hurts too bad and if you want me to slow down or stop.”

She nodded and held her breath for a moment.

Using both hands to brace myself on the bed and hover above her, I pushed my body forward enough so that the head of my cock went inside of her. I pulled it out and put it in a few times and she enjoyed it, but I knew I had to get the rest in. I inserted the head again and, as gently and slowly as I could, I attempted to push the rest of it in her. I couldn’t believe how tight she was. I felt for a moment that it wasn’t going to work. I looked at her and she was on the verge of crying. I was hurting her. Maybe she was too young for sex. Maybe I had to find another way to loosen her up, but as I was pushing my way forward I felt something give way. At the same time, Jenny let out a small cry and her face was beet red. What happened? I looked down and saw blood and almost panicked, but I figured out that I had just broken her hymen. There were a few drops of blood on the top of my dick and some on the sheet below. I didn’t know what to do next. As I paused there, hovering above her with my cock a little more than halfway in, I decided that I should finish the job.

I pushed my dick the rest of the way in and eased back out. I began to thrust repeatedly and very gently. I couldn’t believe the feeling. Her pussy squeezed my dick tightly with every thrust. I couldn’t even enjoy this because Jenny was shedding tears. We shouldn’t have done this. But why I was thinking about all of this, I managed to keep moving myself in and out of her and I started to notice that it was getting easier. The pressure on my rod was not as strong and her inner resistance was loosening. I looked up at Jenny and she had stopped shedding tears. After a few more thrusts, she looked at me and smiled. Finally, after a totally miserable handful of minutes which seemed like an eternity, we could both start enjoying this.

I continued thrusting steadily, pumping my cock in and out of her. She reached her hands around me and grabbed on to my back. Instead of whimpering, she was now moaning, enjoying every thrust into her now receptive pussy. More than ever, she needed my dick. My ultimate goal of pleasuring her was all that I was focused on. My humping became faster and more furious. I could feel her grip getting tighter on my back. I knew I could cum at any time, but I wanted to make sure she had reached her orgasm too. I tried to think about other things so I wouldn’t go off too soon, letting my body get into a self-sustaining rhythm. But it wasn’t long until I realized that she was close. Her moaning grew louder and longer with each thrust.

Her eyes had been closed for a couple minutes, but they opened suddenly and were very wide. When I looked into them, they looked part stunned and part crazed, at points rolling back to the point where you could only see the whites. Combined that with her shaking and a death grip on my back, I knew she was climaxing. I let myself go, paying attention to our bodies rubbing against each other, the feel of my cock inside of her, and her incessant moaning. Within a dozen or so more thrusts, I began to feel my cum shooting inside of her. I let out my own loud groan, continuing to pump in and out of her. Her sounds quieted to a sigh. With my load shot, I slowed down and eventually stopped with my dick still inside. I fell onto her in exhaustion and she embraced me. I picked myself up slightly, leaned in, and we started kissing madly.

I felt my dick go flaccid and I pulled it completely out of her. I looked down and saw my cum dripping out of her pussy and covering her lips. I rolled over and laid beside her, her head resting on my chest, my right arm curled around her in an embrace. We both were still breathing heavily and trying to cool down on a hot day. The air conditioner in her room said 70 degrees, but after that effort I felt it was more like 100.

I kissed her on her forehead. “That was great.”

She smiled. “Yeah it was, but not at first.”

I laughed. “Yeah, we might have some cleaning up to do before your parents get home.”

“Nah”, she replied. “I’ll just tell mom I got a nosebleed.”

We both giggled and our lips locked again.

When she laid her head back on my chest, thoughts began to run through my head. “I know you and my sister hang out, but you have to promise not to tell her. If she found out, she’ll tell mom and I’m screwed.”

“She won’t tell”, Jenny replied. “If she did you could just blackmail her back.”

I was confused. My sister was pretty innocent. “Blackmail Allie with what? She’s kind of a goody-goody.”
Jenny laughed. “Yeah, that’s what everyone thinks about her. But I know better.”

“What do you mean?” I asked.
“You should see the stuff she wrote on the computer when we hung out one time. It was anything but innocent.”

“What? She told me that you wrote all of it and she thought it was disgusting.”

Jenny gave a laughing snort. “Wow, she really does have you all fooled. No, it was her.”

I couldn’t believe it. “Where did she learn about that stuff?”

Jenny answered, “Well, I kind of helped there. I brought over one of Curt’s movies and watched it at your house with her. She loved it. Now all she talks about when we hang out is sex stuff.”

I was in shock. I would never have guessed it. Jenny looked up at me and could tell I was in shock.

“Do you want to hear more?”, Jenny asked.

It occurred to me that blackmailing my sister may be a good way to protect myself. “Sure.”

“You know when we just did it and I started bleeding?”

“How could I forget?” I said.

“Well, that already happened to Allie.”

“What?” I almost shouted it for the whole world to hear.

Jenny explained. “She found a dildo in your mom’s closet and started using it. She told me the first time it made her bleed and she got scared, but she started using it more and she started to love it.”

I laid there trying to wrap my head around this. How did Allie hide this so well?

“I can’t believe it. Has she had sex or anything though?” I asked.

“No, but she wants to really bad. She… well, nevermind” said Jenny.

“No, go ahead. What?” I asked anxiously.

“You’ll be upset.”

I shook my head. “No I won’t. Tell me.”

Jenny continued. “She told me that she would like to get with my brother.”

“Really?” I asked. ”She wants to have sex with Curt?”

“That, or give him head, or have him go down on her. Really anything.”

Jenny must have revved herself up with this talk because she reached down and started to rub my dick. Maybe she was trying to distract me from the idea of Curt turning the tables and fucking my sister.

My resting member began to make a comeback as Jenny rubbed up and down from the head to the balls. As the blood began to flow to it, Jenny reached down and pulled up a blanket and covered my bottom half. She moved to the foot of the bed and disappeared underneath the covers. Once again I felt her hand moving up and down on my cock. Before long, I felt a hot, wet sensation on my dick, but all I could see was the blanket bobbing up and down over top of it. I put my hands behind my head and enjoyed the blind blowjob I was getting. She hadn’t forgotten how to do it. Her tongue massaged the underside of my shaft as her mouth made its way from the tip down to the balls. It was wonderful.

All of the sudden she threw off the blanket savagely and took my dick her in her hand. She scooted herself up until she was on her knees over the top of my cock. Slowly, she began to let herself down until my dick was once again inside of her. Then, letting go of it, she slid down all the way. At first she began to bounce very slowly, but the pace started to pick up until she was full-on riding my throbbing cock. I reached out and massaged her tiny tits. She threw her head back and began to moan so loud that it seemed like screaming. I did my part on the bottom, thrusting my hips up into the air, acting like a trampoline every time she came back down.

I grabbed her by her sides and threw her to my left side and got behind her. I raised her up onto the bed until she was on all fours. I reached down and guided my pulsating cock into her pussy and began to thrust maniacally. All I could see was the back of her head, her arching back, and her young, innocent ass and I continued to push in and out of her.

She took her hands and grabbed the bars on her headboard. This made it even better as she could push and pull herself along with me. Both of us erupted into a chorus of moans and gasps. Our motion picked up more pace until the headboard starting banging up against her wall, creating a noisy thud every time I plunged into her.

With so much noise going on and the immense future orgasm I was focused on, I didn’t hear anything else. I didn’t hear the car that pulled into the driveway. I didn’t hear the front door open and close. I didn’t hear the footsteps coming up the stairs. I didn’t notice anything that I should have been concerned about until, right in the middle of the moaning, screaming, and groaning, with me still thrusting my cock into Jenny from behind, Jenny’s door opened. Out of the corner of my eye, I saw the figure in the doorway. Jenny must have seen it at the same time. We both turned to look. Standing there, watching us fuck our brains out, was Jenny’s brother Curt.

His eyes were as big as dinner plates. Jenny and I quickly stopped our lovemaking and scrambled under the sheets. Curt never moved. He was in total shock. Finally, after what seemed like forever, his look went from shock to rage.

He looked straight at me. “What the FUCK are you doing? Jesus Christ!”

He left the room and I heard him sprint downstairs. I panicked. I knew his next move would be to the phone in the kitchen to dial his mom or dad’s cell. I had to stop him. I grabbed only my shorts and put them on so fast that they were backwards. I ran downstairs. When I reached the kitchen, I felt a hard fist impact the left side of my face. I fell to the floor. I looked up to see Curt, both hands balled into fists and a fighting posture.

“Stay the fuck down!”, Curt yelled.

He walked over to the phone and I jumped. I ran over and yanked the cord from the wall.

“Wait. Please don’t call your parents.”, I pleaded.

“Fuck you”, he replied. “You are so fucked, you have no idea.”

I begged again. “Please don’t call them.”

He stared at me with a rage I had never seen before. “Give me one fucking reason why I shouldn’t call them and then beat the living shit out of you!”

“I can make it up to you”, I told him.

“How the fuck are you going to make up for screwing my little sister? You don’t have enough money in the world.”

“I can make a deal” I replied.

“What kind of deal?”, he asked.

I was desperate. I was scared. I needed to do anything to make sure nobody else found out about this. I offered the only thing that I could think of.

“I’ll let you fuck my sister”, I said.

He looked at me as if I were crazy. He didn’t say anything for the longest time, then he seemed to ease up.

“Wait. You’d let me fuck your sister?

“Yes.”

“And you wouldn’t tell anyone?”

“I wouldn’t.”

He pondered for a second. “But what makes you think that she’ll want to fuck me?”

“Let me work on that. If she doesn’t agree to let you fuck her, you can tell your parents what I did. No hard feelings. I swear.”

I could tell the deal was more than he could pass up. In our previous talks, he told me that he couldn’t wait to lose his virginity. This was his opportunity.

“Fine. Get her to say yes, and I won’t tell.”

I was relieved. “Deal.”

I came to find out that Curt’s uncle Ken had been called in an emergency SWAT assignment, so Ken had to rush Curt home. Curt later told me that as soon as he walked inside the house, he could hear two voices screaming and something thudding upstairs. When he realized it was coming from Jenny’s room, he thought she was dying or something so he opened her door to find us doggystyle on her bed. Needless to say he was pissed at the time, but if I made good on our deal, all would be forgiven. What he didn’t know was that my sister had already talked about fucking him, so I knew I had a decent change of convincing her.

As I rode my bike back home, I rehearsed what I was going to say to Allie. I knew I had to be coy about it. I just couldn’t say “Hey Allie, wanna fuck Curt?” The ride wasn’t easy. My conscience beat me up the entire way. Was I really going to sell out my sister’s virginity and innocence to save my own skin? As I pulled into my driveway, the devil on my shoulder won: hell yes I was.

To be continued…

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