Breaking In Girlfriend’s Sister

During the early part of high school, I began dating a girl named Jillian. She was an average height brunette, with green eyes and a slender yet shapely build (between large B’s and smaller C’s). It was a pretty good catch, and I did my best to not take things for granted, even at our young age. I treated her well and we got along great. The problem, if you consider this type of situation trouble, was that she had a pretty attractive younger sister, Jennifer. She was a couple of years younger than us. She was a redhead with pale skin and freckles to go with deep green eyes. Though she was still developing, her breasts were only slightly smaller than her sister’s, even though she had a very petite frame. She was the kind of little sister that always wanted to tag along with her older sis, and she would often watch movies or play games with us when I came over. She was pretty flirty with me at times, which did lead to the occasional cat fight. But Jillian probably thought her sister was too young to be much of a threat. As time went on, my relationship with Jillian continued, although it did settle into that monotonous groove that relationships tend to fall into after time, especially at a younger age. Jennifer was in and out of multiple relationships, and could never seem to keep anybody for any length of time. I guess that’s how things work at that age though. One night, with their parents out for a late evening, I came over to watch a movie. Jillian was playing things comfortably, wearing a white tank top that showed off her figure and short, black cheer shorts. Not wanting to be left out, Jennifer was there too, and dressed very similarly, wearing a blue tank top of similar proportions and green cheer shorts that actually said “cheer” across the back. The movie we watched was a scary one, which worked out fine for me. We were in Jillian’s room, on her bed, and I was in between the two of them, laying back against the headboard. Every time something particularly scary happened, both of them grabbed my arm that was closest to them and hung on. Sometimes they would press their body’s against me too, which I didn’t hate either. After the movie ended, the three of us sat around the bed trying to figure out what to do. “Do you guys want to go out anywhere?” I asked. “No we should probably stay in tonight,” Jennifer said, somewhat excitedly, while Jillian nodded. There seemed to be something going on that I didn’t know about, but I thought I might be reading into things too much. “Come on Jillll,” Jennifer whined a couple of times, to which Jillian kind of waved her off. “Just wait,” she responded. I gave her a puzzled look and her glance in return told me it wasn’t worth asking about. We watched some shows on television, but Jennifer looked over at me and to her sister multiple times throughout. She had an expectant look on her face. “What is this all about?” I finally asked after enough of this had gone on. I asked in a light tone, as I could tell this was causing some awkwardness between those two. “Come on sisss,” Jennifer said again. “Alrighttt,” Jillian finally gave in. “Look, feel free to say no to this (she emphasized this part), but Jennifer has been bugging me lately. She’s been really down about failed relationships and dumb guys she’s seen and she’s really jealous of me. She’s been so pitiful and pathetic that I told her that she could share you, just as long as you two didn’t go crazy, but I’m starting to rethink things.” I had a pretty shocked expression on my face, to which Jillian replied, “See? He’s not into it. Sorry.” “Oh come on,” Jennifer whined again. “You were fine with it this afternoon. I just need to experience things with a nice guy. I’ve never had one of those.” I looked back and forth as the two of them continued to discuss this crazy situation. “Sorry sis,” Jillian said again. “It seems pretty obvious he’s not into it.” “We haven’t even asked him!” Jennifer said and crawled closer to me, bending over to let me get an extra view of her cleavage. “What do you sayyy?” “Well,” I said after a pause, as I continued to look at both of them. “I understand what she’s saying. I wouldn’t necessarily be against helping.” “Oh,” Jillian said with some disappointment. She looked down at the bed for a bit, still considering things. “Well she did promise that you guys weren’t going to go crazy.” “Of course we won’t!” Jennifer said, starting to bounce a little with genuine excitement. “I’ll just be around,” Jillian said, although she seemed to be in a little better spirit, as if coming to terms with something that she had earlier. She got up off the bed and wandered a bit around the room, before going into the hallway.