Country Club Kids
Chapter 5

Copyright© 2017 by Quinn

Coming of Age Sex Story: Chapter 5 - A couple of affluent siblings are left largely unsupervised, what could possibly go wrong?

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   ft/ft   mt/mt   Mult   Teenagers   Consensual   Reluctant   BiSexual   Heterosexual   Incest   Brother   Sister   Cousins   Light Bond   Rough   Spanking   Group Sex   Anal Sex   Analingus   Cream Pie   Double Penetration   Exhibitionism   First   Oral Sex   Slow  

I was sound asleep when she came in, and crawled into bed with me. I had masturbated twice last night after I put her to bed, but when her naked body came into contact with mine, I rose to the occasion. We snuggled for a while, she was lightly stroking my member, while I fondled her ass.

Her face was buried in my neck, and when she said my name, I could barely hear her. She said it again to get my attention. She told me that she had a big favor to ask. She hem hawed around, and just couldn’t seem to get it out. Finally, I gently grabbed her shoulders, pushed her away so that I could see her face, and I asked her to just spit it out.

She got even more embarrassed, and it a very meek voice, asked if I would do her in the ass. Just as soon as she got it out, she was totally embarrassed, and re-buried her face in my neck. Of course I was going to say yes, but I hesitated while I tried to work out the logistics. She took this to mean reluctance, and started crying in shame. I had to reassure her that I had every intention of complying with her request.

We were both naked so that part was already taken care of, so we put both of my pillows in the center of my bed, placed a towel over them, just in case there was some leakage, and Jill assumed the position.

I gently started to rub lotion around her anus with one hand, while massaging her pussy with the other. This was the first time that we had done this without significant warm-up, so it seemed to go a little slower.

Eventually, her starfish started nibbling at my finger, and I slowly began to insert it. She moaned, and said something like, ‘Crap that really hurts!’ I asked her if she wanted me to stop, and she wanted me to continue, she just wanted me to go slowly.

I began to lightly saw back and forth, and she started moaning. When it started to get a little dry, I added more lotion. Eventually, my finger was going all the way in, then almost all the way out, and she was taking it. Her hips were grinding on the pillow, and my erection was almost painful.

She asked me to add a second finger, and all but screamed when it went in; I don’t know if from pain or pleasure. Another couple of minutes of this, and I had to have relief. I quickly spread some lotion on my dick, and climbed in behind her.

I lined myself up, and started to push. It slipped out, and went down between her legs eliciting a moan. I tried again, and it slipped the other way. I told Jen that she would have to spread’em for me so I could see what I was doing.

She reached back and spread her cheeks. Talk about an erotic sight; her cheeks spread, and her brown eye winking at me. I very carefully lined up, and started to push. I had barely gone in at all, when Jen screamed, I mean really screamed.

I immediately yanked it out. It scared me to death that I had done some sort of permanent damage, but Jen wanted to try again, and asked me to push very very slowly. Also, unless she specifically asked, don’t yank it back out as that hurt almost as much as going in.

She started sucking big gulps of air, I guess to control the pain. I pushed a little harder, and nothing happened unless you count the increased volume of her moans. I pushed even harder, and was rewarded when the head popped in. I froze. She was panting, crying, and frozen in place; she also begged me to not move.

Again with the panting. After a few seconds, she told me to continue, but to go real slow. Eventually with a lot of pushing on my part, and groaning on her part, it went in another inch, and again, she made me stop. Aside from the one blow-job, this was the first time that my dick had ever entered a female.

I was so randy by then that I just wanted to shove it all the way home, and fuck the living daylights out of her. I controlled myself, and did some heavy breathing of my own.

Eventually, she let me continue, and I went in inch by blessed inch accompanied by mews, and cries, squeals, and hiccups. She was in pain, and loved it. Her ass was squeezing my dick so hard that I was in pain, and loved it as well.

Eventually, my public hair came in contact with her beautiful ass, we just lay there panting. I looked down, and the sight of her anus fully gripping my dick almost put me over the edge.

Finally, she agreed that I could start moving, but very gently, I started moving back and forth, accompanied by cries and whimpers. As this went on, I was losing more and more control, and my thrusts became more and more rapid. Of course they were firmer as well.

As much as I wanted to be a complete gentleman, eventually, I couldn’t control myself, and I started to savagely fuck her ass. She was crying, shaking her head back and forth, and saying no over and over again, but I just couldn’t stop; it was like I had been taken over by a demon.

I finally felt my come about to boil over, and rammed into her as hard as I could, and splashed her insides. When I came, I shoved to hard that I think that I found new territory in there, and Jen wailed.

As soon as I came down from my orgasmic bliss, I realized what I had done, and was totally embarrassed. I was still buried to the balls in her ass, and she was sobbing uncontrollably, and saying my name over and over again.

 
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