A night with Riley's sister. | 2016

Here's my story of how I had sex with Riley Reid's sister. No one seems to believe me when I mention it so here's the story. (changed names for anonymity)

So back in high school I knew Riley as I had English 4 with her sister Lynn. This was about 7 years ago in south florida (holy shit im getting old) and I was a 17 y.o. lanky, still a bit awkward skater boy. First time I saw Lynn (18 y.o.) was of course first day of class and her face was kinda of meh, rosy cheeks, dirty blonde hair. Super white girl. But damn, she had an amazing body. Her chest was large and she had a nice ass. I stared as much as I could until she ended up sitting right in front of my desk. Turns out my friend Frances knew her somehow (I never asked how). Upon hearing them talk, I concluded Lynn was a bit of an air head. She was kinda loud and said dumb things. Really cringey stuff once and awhile. I talked to her sometimes and I noticed she would give me weird looks.

Fast forward to a few weeks later. Me, Frances and Dustin (one of Frances friends who was pretty cool) were gonna go to France's house one day and hangout, smoke cigarettes out back and play guitar when Lynn asked if she could tag along. We were cool with it and didn't think much of her tagging along. So we're hanging out back and I offer her a cig (frances and Dustin never had any) but she didn't really like to. I take a seat as F&D go do something inside and Lynn decides to stay out back with me. So she starts asking me if I have a gf and if she'd get jealous of me being alone with her. I responded simply that I was single and it was cool, the girl i was currently talking to wouldn't mind because nothings official (honestly there was no other girl, I was an awkward teenager and wanted to seem like I hookup with girls to impress Lynn) She smiles and says "So this is fine?" and she sits on my lap. I get an immediate chub and act like it's all cool. "Is this comfortable?" she looks back and smirks "How about now?" She then starts bouncing up and down on my lap. I was on the verge of a full on erection and had to get her off. I curse myself for not making a move then but I was a shy teenager. I laughed and played it off, trying to be "the cool guy" Nothing ended up happening between us that night. Although another night she did hump my leg. God, I couldn't believe I didn't make any advances that night! (teenage years can be painfully cringey huh?)

Towards the end of the school year I had gone to Lynn's house, giving her and Riley a ride home (Riley made us homemade banana pudding from scratch, best I've ever had IMHO) and got to keep keep not making moves. Once we graduated, I had a car and a job so I felt a bit more confident and asked Lynn if she wanted to hang out. She said "Sure, we can hang out at my house". Turns out they moved to Tamarac which was quite far from miami but I was a horny 18 y.o. at that point so it didn't matter to me. So I picked her up at Starbucks, where her mom worked. She was wearing a tight black tee and jeans and I was wondering if i'd be taking them off tonight. It was a bit awkward inside because I think her mom knew what was gonna happen. Her Mom was pretty nice as usual and waved us goodbye and we were off.

So we get to her place and it's like 10 or 11pm. I walk in super nervous into the living room and I notice some kids sleeping on the couch. "Great, kids around" I thought. She leads me like 20 or 30 feet away to her room. So lynn says "we gotta be quiet, my step-dad is sleeping" and I feel quite anxious at the thought of being found in their house with children sleeping close by. We enter her room and turns out she and Riley shared a small bedroom. It was split by a curtain in the middle of the room, I guess for privacy. I looked at all of Riley's stuff, some pictures and shit on her mirror and it was pretty plain. Riley's out to orlando with her friends so we have the room to ourselves. Lynn takes me to her futon/bed and tells me to sit, she's gonna change into something more comfortable. "ok cool" I respond, not sure what she was gonna change into. Lynn comes back wearing small gym shorts and a sports bra and no shoes. Holy shit was she looking hot. First off, Riley had a "girl next door" kinda look, cute but average body. Lynn on the other hand was a blonde bombshell. She was 5/5 had a great ass and DD sized breasts. She had similar eyes but hers were bluer. She comes over and sits next to me and m hearts already thudding. "So you want to watch a movie?" She asks and I said "Sure, whaddya got?" (Why didn't I just get to the point) She had spider-man 1 so I was like "Fuck yeah". So she puts it on and things are bit awkward at first. We're watching and then she eventually asks if I want a massage. Of course I obliged. So I take off my shirt lay down and she sits on my butt, her legs pressed against the sides of my own and starts touching me very slowly. Im getting quite turned on and I roll over, sitting up and stare into her eyes for a moment "What's wrong?" she asks. The sight of having her straddle me was very arousing. I just lean in and start kissing her. We wrap each other in our arms and it's quit the intense make out session. She gets up and I stand and she pulls me to the futon where we kiss more, my hands wandering to her firm ass. I started bringing my hands into her shorts and she pulls away "Could you tell I was super attracted to you?" she gives me a lustful look "Uh, yeah...I could tell" I barely get out. I'm a smooth operator of course. We start kissing and I pull her on top of me and my hands are all over that ass. I could feel how wet she was from the moist spot on her shorts. I ran my fingers to her slit and I could feel a lot of detail. I could feel she was smooth and knew she was expecting sex. I rubbed her for a little bit and she pulls away for a moment. "I'm gonna take my bra off, okay?" She asks. "...Okay" I said, not sure why she needed my permission but I really wanted to see her breasts. she starts removing the sports bra and her boobs pull up a little and for a split second I thought she had some kind of padding but then a pair of double d's pop out and jiggle. If I had an fully erect penis, it was now a raging steel pipe. Her breasts were perfectly round and supple. They were amazingly perky and she had nice tiny nipples. They were easily the best I've ever seen. I didn't waste a second and immediately fondled them. I sucked on those perky beauties and gave them both my undivided attention. During this time Lynn reached her small hands into my pants and starting touching my dick. Her hands were so soft and it felt great against my dick. She was kind of lightly touching, stroking with her finger tips slowly. I thought she was just getting a feel for it because she stopped shortly. "I want to blow you" She said, looking into m eyes. I kissed her with much tongue and took my pants off. "Okay, go ahead" I says as my dick slaps against my happy trail, precum getting all up in my hair trail. She takes me in her mouth and goes at it, spider-man fighting off the green goblin in the background. The blowjob was sub-par but getting to fondle those breasts and seeing those petite hands working my shaft got me aroused enough that I busted in her mouth. She quickly bolted for the back door and spat it out outside. I quickly put my clothes back on, remembering there's a sleeping step-dad in house. She wraps a flow skirt or something around her waist and throws on a tank top and we go outside. I was an asshole and barely said much before she hugged me and I dipped.

We hooked up again after that. Maybe I'll write about when we fucked.