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. Clearly she was going to keep an eye on us from time to time, but didn’t want to watch every little detail.
I looked at Jennifer and returned the excited grin that she gave me. The first thing she did was climb onto my lap and pull down the top of her tank top, showing me more of her breasts. I started to get hard, which excited her as I bumped against her ass, between our clothing.
“I’m so excited,” she whispered. “I’ve fooled around with boys but we haven’t done a ton. I’m still a virgin but I masturbate all the time. Don’t worry about breaking me in!”
She was driving me crazy already with the talk, although I couldn’t help but laugh at the last line. I wasn’t sure she knew exactly what she had here, although I also wasn’t sure what it meant. Did she mean she wanted to fuck me? I’m sure that wasn’t part of the agreement they had reached.
“What are you waiting for?” she smiled innocently at me. “Take my clothes off.”
I didn’t want to disappoint her. I started by pulling off her tank top, which exposed her cute, blue bra. I was pretty impressed by her breasts’ size, given that she was still early in development.
Then she pulled off my shirt. As she did that, she grinded down on my cock and let out a moan as the friction hit her where she wanted it. I saw Jillian walk by and quickly check things out. She didn’t look too worried so far, at least from what I could tell.
Jennifer looked at me seductively, one eyebrow slightly raised, as she reached behind her back and unclasped her bra. She never took her eyes off of mine as she let it drop. I was a big sucker for breasts (both literally and figuratively) so I lost the brief staring contest. My eyes locked onto her average but perky breasts. She nodded and I gave them a squeeze, before moving into suck on her nipples. She threw her head back and moaned as I let my tongue swirl all over her stiffening nipples. I grabbed her ass against her cheer shorts, feeling the lettering of the imprinted ‘cheer’ against my fingers. She had a small ass, as could be expected of a young girl with a petite body.
“Okay okay,” she giggled, still moaning a little from the wet sensation on her nipples. “I’ve got to see this.” She eagerly pulled off my shorts and boxers in one big grab and stared at my cock with hunger in her eyes. Her hands immediately grabbed it as she played with it, gently stroking with her small, soft hands.
Jillian walked by again and this time had a more concerned look on her face. She stayed out of the room, but it appeared that this was about as far as she wanted things to go.
As Jennifer continued to explore and rub my shaft, I grabbed the waist band of her shorts and slowly pulled them down her slender legs. She giggled again, left in nothing but her black panties. Those were next to go. She stood up on the bed and gave me easy access to slide them down her legs.
I hadn’t gone into the night expecting to be naked, at least not with Jillian’s sister of all people, but I was pretty aroused. I still didn’t know what Jennifer’s exact plan was, but I was pretty ready to go along with whatever it was.
“So you’re going to help me try things, riiiight?” Jennifer said with more cute excitement.
“Yeah, of course,” I laughed.
“Okay,” she smiled. “The first thing I always wanted to try was that 69 position that I always see when I watch porn.”
With that, she bent down and gave my cock a few licks. Then she turned her body and let herself rest on top of me. Her breasts pressed on my stomach, which turned me on more, as her tiny pussy came in front of my eyes. She opened her legs up as she plunged her mouth onto my cock. She wasn’t perfect, as could be expected given her youth and the difficult position, but this was more for her. I opened up her lips and pushed my tongue against her clit, flicking against it. She started to moan loudly, and stopped sucking my cock, although it remained in her mouth. That only served to muffle her moans as I danced my tongue across her clit.
The moaning sounds had drawn the attention of Jillian, who looked in and seemed to gasp a little. She restrained herself, but said, “Don’t go any further,” and left again. This caused Jennifer to giggle, clearly proud that she was getting a chance with her big sister’s boyfriend. “We’ll see,” she whisper, barely audibly, before resuming her moans. I was alternating between flicking her clit and letting my tongue explore her opening. It didn’t seem to matter what I did because Jennifer was loving every second.
“I’m cumminggg” she whispered and moaned as her tight stomach rippled and her pussy muscles contracted. I licked her clit hard throughout the orgasm, which had Jennifer struggling to remain on top of me. Clearly she hadn’t been brought to orgasm by another person too many times, and she giggled and flopped around. I reached up and cupped her breasts, tugging her nipples, while she came down from her euphoric state.
“That was awesome!” she said and popped back up in front of me. She looked back to make sure that Jillian wasn’t watching and then planted a kiss on my lips. “Thank you, this is so much fun,” she smiled. “Jillian isn’t the only one that can make you happy.”
“Wouldn’t it be fun if we fucked?” she asked, catching me by surprise.
“Really?” I asked. “I mean it would, but really?”
“I told you, I wanted to experience things with a great guy,” she said. “You’re the best! You’re always so nice to me. I want to fuck you. Pleaseee.”
I looked around her to see if I could spot Jillian, but couldn’t.
“I don’t know,” I started. “I mean I’d love to, but your sister would flip.”
“Let’s just do it!” she said excitedly. “By the time she checks, we’ll be too far along to stop. You can even say you tried to stop me.”
Again, I could only laugh. That was certainly a lame excuse, but maybe it was worth a try to experience this.
Just then, Jillian stuck her head in. “You guys done yet?” she asked.
“Almost,” Jennifer said. “Just give us some more time.” Jill sighed and walked away again.
“Hurry!” Jennifer smiled. “Let’s just fuck. Worry about it later.”
I was still trying to come to terms with the potential guilt as Jennifer climbed on top of me. She spread her legs out far with her flexibility, one on either side of me, and let my cock head rest against her pussy. She reached down and centered it, so that the head was pointing right at her opening. Without removing her hand from the center of my shaft, she impaled herself on my cock, slowly sliding down as her hand lowered too.
“Fuck yeah!” she said with tons of excitement, but still in a whisper. She really wanted this and slid down as much of my cock as her petite frame would handle. Then she grabbed my legs and started to ride me, moaning but keeping things as hushed as possible. I reached up and grabbed her breasts as they bounced, trying to control my own breathing as well.
“Oh I love this,” she smiled as her pussy started to squeeze me. “I’m cumming and I love it. I’m so much better than Jill. Her boyfriend’s cock is inside me, not even with a condom, and she can’t do anything about it.”
Her words continued to build herself up as she came again quickly, her pussy going into another series of heavy contractions. I loved how tight she felt on me, and I had to work hard too to keep from making too much noise.
She slowed to a stop with my cock still buried inside her. “She’ll be here any second,” she said. Jennifer pulled a blanket to block out any view. Then she waited to here her sister approach. As she heard noise, Jennifer looked to the side, so that Jillian could see her face, and put on a bored look.
“Done yet?” Jillian asked.
“No, almost,” Jennifer said. “Just go away, he’s explaining things to me.”
This was enough for her and she left.
Jennifer immediately started giggling again and gave me a high five. Then she tossed away the blanket and started to ride me again. She grabbed her hair and pulled it up as she bounced wildly on my shaft. It was a sight to see her petite body bounce on me.
“I know sometimes they do it like this,” Jennifer said and turned around. She then started to ride me reverse cowgirl style. That was our generation; you could learn almost everything on porn before trying it.
She was really going for this, grabbing the bed and slamming her tiny pussy down on my cock over and over again. I saw her pinch one of her own nipples and I had to give her ass a playful slap. She giggled and then turned back around again so we could watch each other.
“I still…love this,” she said between breaths. “I don’t…want to…stop.”
Right then, Jillian popped her head back in and breathed hard. “What the fuck!” she yelled, although this wasn’t enough to distract her sister. Jennifer knew what she wanted and she wasn’t about to stop. She continued to ride me hard as Jillian came closer to us.
“I can’t believe this,” she said. “You guys are really fucking?”
Her sister only answered her with more moaning.
“I thought you promised not to go crazy!” she yelled.
“I’m not…going crazy!” Jennifer called out between her increasingly heavy breathing. “He’s just teaching…me how to fuck. Yeah!!”
“Did you at least put a condom on?” she asked, still upset but coming to grips with the current reality.
Again she was met with silence, but could see there wasn’t anything on whenever her sister bounced up.
“You guys suck!” she yelled again.
The situation was driving me crazy, and I could feel my orgasm build and my cock swell. Her tight pussy lips split open each time she dropped down on me, driving me crazy.
“Oh fuck,” Jennifer moan. “What’s it mean when his cock gets thicker?”
“What?!” Jill screamed. “That means he’s going to cum! Get the fuck off him! Stop her!”
“Ohhhh man!” Jennifer cooed. “He’s going to cum? I want to feel that!”
“Don’t you fucking dare!” Jill said.
I pretended to try to raise my body as my cock continued to get thicker inside Jennifer’s pussy. “I can’t get her off” I said.
“Be a fucking man!” she yelled again. “Sis, stop fucking him now.”
“Back up bitch,” Jennifer said and only went faster in response. Actually, she shifted her face to show Jillian every inch of pleasure plastered on her face. I was too turned on at this point, and I felt the first twitch in my cock, and knew any attempt to hold back would be futile now. I shuddered as shot after pleasure filled shot blasted into Jennifer’s tight pussy.
“Oh my, fucking…” Jennifer moaned loudly. “I think he’s cumming! He’s cumming in my pussy!”
“No!” Jill yelled. “He better not be!” She seemed to be in a bit of denial, as ropes of hot cum filled her sister’s hole.
“Oh yes!” Jennifer screamed. “It’s so fucking hot! It’s warming my insides. Keep cumming in my pussy!” She was still riding me and it wasn’t long until my cum was running back down my shaft, only adding lubrication, while Jennifer continued to moan from the hot spurts. After my balls had emptied, I had to hold her in place to stop the sensitivity. She still had much to learn.
“Fuck you guys,” Jillian said and left again. Jennifer fell onto my body and we started to kiss. Cum oozed from her tiny pussy and down her thighs.
“That was perfect!” Jennifer sighed contently. “Don’t worry, she’ll get over it. I know my sister.”
At this point I wasn’t overly worried. Whatever happened would happen. I felt bad, but I was young and dumb. Plus, she was pretty stupid to share me in the first place.
“You know,” I started. “I didn’t really get to show you what a crazy fuck is like.”
Jennifer’s eyes lit up. “Get that fucking thing back up then!” she yelled and started to suck on my cock, which was mixed with our cum. She was a little better in this position and had me back up after a little effort.
“Why don’t you bend over and put your hands against your dresser?” I asked.
Jennifer eagerly ran over to her dresser and bent over, wiggling her tiny but firm ass at me. She turned her head around. “Come get me.”
Quickly, I positioned myself behind her and rubbed my cock head against her soaked and swollen pussy lips. I reached around and grabbed her breasts, which felt fuller from her bent over angle. She was getting antsy, and without warning, I drove my cock into her tight pussy again. She screamed out this time, not worried about anybody hearing anymore. I grabbed onto her hips, and started to fuck her at a crazy speed. I wanted her to know what a real fuck was like, since she was so eager to learn.
“Oh. My. Fucking. Goodness,” she panted as I split her pussy with each thrust. “Don’t. Fucking. Stop.”
Jennifer seemed to be in a constant orgasm now, as her pussy clamped down on my cock constantly, threatening to slow down the fuck if not for my desire to make it tough for her to walk afterwards. She was doing her best to meet my thrusts, pushing back to meet me, but not fast enough to keep up with my animalistic pace. I took one hand off of her hip and moved it to her clit, rubbing her hard and setting off a larger set of orgasms. She lost her balance and her hands slid further down the dresser. This only gave me easier access, and I responded by slamming my cock into her pussy deeper, aiming for her g-spot.
“OH FUCK, ” she was screaming at the top of her lungs. “OH FUCK OH FUCK.”
She had given up meeting my thrusts due to exhaustion but I was still ramming her. Finally, I shoved my cock as deep inside her pussy as I could get, and shot another huge load of cum right off her cervix and deepest pussy walls.
“Oh fuck I love this part!” she moaned as I shot my seed into her. “More more!”
Her pussy milked my cock for all it was worth, and I made sure to give her every drop of cum that I had. I let my cock drop out of her and cum spilled down her leg. She fell to the floor, completely spent for energy.
“I want that every night,” she said breathlessly.
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