My Sister's Best Friend - Cover

My Sister's Best Friend

Copyright© 2020 by RickSands

Chapter 3

Erotica Sex Story: Chapter 3 - A story of Gary's illicit attempt to spy on his sister and her most beautiful best friend. Much sex and eye opening surprises for Gary, but with him eventually finding love and happiness

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Teenagers   Coercion   Consensual   Reluctant   Heterosexual   Fiction   Sharing   Brother   Sister   Group Sex   Anal Sex   Cream Pie   Oral Sex  

Gary was up and out the door early the next morning, too early to greet Penny and see how she felt about their deep physical connection and conversation of the night before. Mom and Dad were up and moving and gave no hint of hearing the pounding and shaking that went on in Penny’s room just hours before. Gary only had a half-day, his manager ensuring that he never had quite enough hours each week to afford him fringe benefits, and he returned home just after noon. Gary knew he’d have to face Penny and she was there with arms folded and a scowl on her lips.

Only a minute after he had walked through the door she was on him. “OK, so show it to me, the video you say you’ve got. I guess you got what you wanted last night, so now it’s my turn.” Gary shrugged and smiled, having prepared for just this moment of truth. He didn’t go into the region of the web where the two cameras uploaded their daily reports but went straight to where he had stored specific bits of video on his computer. He made sure there was a separate file for the two cameras and he only called up what had been saved via Penny’s computer eye. He got it running and stepped back, allowing her to sit in his chair and watch the two-hour sex scene play out before her eyes.

Penny only spent a few minutes watching the video, fast-forwarding to different parts, assuring herself that Gary really had videoed the entire event with her and Cyn and the two men. “You’re a sick fuck, you know that Gary? A guy at our school got expelled for putting a hidden camera in a girl’s bathroom, right?” She tried clicking on a few other files in that same folder, only pulling up some saved still shots that made Penny shake her head. “So when did you hijack my computer?” she asked. “How long have you been doing this? Do you watch me at night? That is so creepy. I want it gone Gary, and I want you to promise to never do it again. Right?”

Gary was sitting on his bed, watching Penny as she viewed the video of her and Cyn’s twats being undressed, pried open and flooded with cream by the two visitors he had only accidentally caught on video. The entire scene was worthy of being sold for a high sum on any porn site, so no way he’d delete it all, but he knew he’d have to work something out with Penny. As she turned to him and made her demands, Gary thought it out, looking hard at Penny and thinking of how best to get what he wanted without having it blow back in his face.

Gary felt guilty, shamed for what he had done, and still torn about asking Penny to give him more. He then realized that she had been home all morning, and all she had on was a pair of short shorts, riding up high and onto her ass, and her top was the same one he had pulled off of her just the night before, her nipples showing prominently through the thin cloth. Hardly the kind of clothing you wore to a bare-knuckled business meeting with a sexual pervert.

Gary pretended to give in but really gave up nothing, saying, “Fine. Delete it. And all you have to do to keep me from watching you in the future is close your laptop or put a piece of tape over the lens. But we still need to talk. You get to wipe out the video but only if you fill me in on how you and Cyn got into that situation in the first place.”

Penny looked at him sideways, doubtful and unsure of what Gary wanted, saying “Like what? What do you mean?”

“It’s pretty obvious that this wasn’t the first group thing you two have gotten yourselves into. You kept referring back to other times, like they were in-jokes or something.” Gary paused to think of how best to put his many thoughts and finally continued. “I’d blame Cyn for getting you into this, I mean, she looks the part, but you say you have more experience fucking while she has more experience sucking. I don’t know where to even start asking questions about that, so you tell me. What’s up with that?”

Penny smiled, pulled her feet up onto the chair, wrapped her arms around her knees and smiled. “Yeah, she does look the part. Totally stacked. Grown men at the mall can’t take their eyes off of her, even our teachers.” Gary nodded, pretending to listen to what Penny was saying but it was difficult to look into her face when his eyes were being drawn down to her crotch. When she pulled her feet up she left them open, feet and knees and thighs wide open, and he had a full view of her thin short shorts being pulled tight into and outlining her unprotected labia. With little effort he could make out each of her lips, could guess at just where her clit should be hiding, and could even make out thin brown wisps of pubic hair. Gary began to sweat but forced himself to look up and follow Penny’s story.

Pretending to not notice Gary’s predicament, Penny talked on. “So, we’d known each other forever, like since grade school, but really hadn’t connected until she ran up to me after school one day about a year ago and flat out asked if I had ever had sex. She used a really specific phrase, straight out of biology class. She asked, ‘has a guy ever penetrated you during sex?’ I just stepped back and replied with a ‘What? You mean like fucking?’ And we just got to talking. She had done a lot of stuff, a lot of sex stuff, you know, especially sucking guys off, but was new to fucking and she wanted to talk to someone she could trust. She asked about it hurting, if it always hurt, if it would get better, what kind of birth control she should use. All that stuff. Within that one hour we became best friends. Had to. We know way too much about each other to ever become enemies.”

Gary thought for only a moment before making a connection, sitting up and saying, “Wait. This was more than a year ago. And she had already been sucking guys off and was asking about going all the way with some guy. And you were the expert she turned to? How much experience did you have? Did you already have a boyfriend?”

“You don’t say a fucking word to mom or dad, right?” Penny leaned forward, feet back down on the ground and knees together as she made her point. “I’ll fill you in, but this stays quiet, right?” With Gary’s assent, she leaned back in the chair, opened her knees and thighs for Gary’s viewing pleasure and continued.

“Cyn didn’t know anything about what I’d been up to, but I had talked with a couple of other girls about stuff and she kind of heard about it. You get a lot more info from other kids than from your parents, you know?”

Gary felt he was being given a runaround and injected with a quick “And you had experience you were willing to share. Like what?” Penny turned her head away from Gary, looking blankly at his wall and pulling her feet back up onto the chair, thinly clothed pussy still easily visible to his eyes, and finally got to the story.

“You remember Simon, the Mormon guy who lived just a block over? He graduated high school way before you.” Gary nodded, having a vague memory of an older boy who was a senior just as Gary entered as a freshman. The guy’s family lived just down the street but Gary and him, Simon, had never really connected. Just the occasional wave of recognition and that was it.

“Anyway, it was like three years ago and I was walking home from somebody’s house or something and the weather turned from late spring sun to thunder and rain. It started slow and then the sky just opened up, huge rain drops and even a bit of hail. It was crazy. I was soaked in an instant but began running for home anyway and almost ran right into Simon as he got out of his car. We both pulled back, looked at each other and he just took my arm and said ‘Quick, up to the house’ and I just followed him up to his front porch. For some reason he remembered me, called me by name, and told me I could wait out the rain in his house. He opened the door and I followed, both of us dripping water all over the floor.

“And, it happened. I don’t know what else to tell you. We looked at all the water, at how wet we both were, started laughing, and he bent down to kiss me. Then he knelt in front of me, pushed up my blouse, I think it was just a t-shirt, and he sucked in one of my nipples. No real tits back then, but what he did with his mouth sure hit me like a jolt of electricity. I didn’t know what to do, but he sure did. He picked me up as though we were on our honeymoon and walked me two steps over to his family’s couch, lay me down, and reached under my dress and pulled my panties off in one move. In another second he had pushed down his pants, pulled his cock out and went to town.”

Penny paused, her breath quickening to short gasps, biting her lips and looking back into time in a way Gary couldn’t follow. Then she looked from the wall over to Gary and said, “Every time I think of it I relive it in a way I don’t with any of the other sex we had. I mean, we wound up fucking a hundred times, and none of it was like that one afternoon. He was really fast at first, I mean, two minutes inside of me and he climaxed, unloaded his balls and collapsed on top of me with a groan.

“After a minute he came to and realized we were drenching the couch in rain water and sex stuff, so he got up and asked if I was OK. It wasn’t great, if anything the whole thing was kind of uncomfortable, but it was also the biggest turn on and most memorable sex I think I’ll ever have.” Here Penny smiled and looked over at Gary to say “I was wet even back then. He didn’t break my hymen or anything, just slipped past it and right into me. I mean, no intense pain or blood like what Cyn had to go through, but his was the first cock to force it’s way up into me, to fuck me and cream me. It was really uncomfortable, but I didn’t mind. I mean, this big tall handsome guy ravishing me like that, it was straight out of a romance novel, and he didn’t disappoint.”

Gary nodded some more, worried that Penny would see the sweat he could feel forming on his face, but he needed to know more and came right out and asked the most obvious question. “A hundred times? You mean you kept doing it with the guy? You were only what, barely fourteen?”

“Oh yeah, sweet fourteen and only been kissed, until then. And he was way old, like right back from his Mormon mission and starting college. A big older guy and let me tell you big bro, it was pretty good. Every girl should have it so good. He didn’t just walk away and pretend he hadn’t done anything. He pulled me up, got the both of us naked and our clothes into the dryer, and threw me down on his bed and did it again, and for a lot longer that time. I may have been leaking cum and wet all on my own from wanting him but it was still really uncomfortable, even as he ploughed me into his bed and unloaded inside me again. And he kissed me. I mean, like no boy had ever kissed me. Being naked together sure helped, and him pounding away inside my virgin pussy. Still uncomfortable, but I never wanted it to stop. Being with him, alone under the covers with a nice handsome guy and for the first time, it was really special. I was afraid that he’d just push me out the door and thank me for my time, but he acted like I was the most special girl on earth. I remember that I had to leave because his parents always came home together about the same time, and he walked me part way down the block and held my hand and said he had to see me again. You’ll never know how magical that is.”

Gary’s jaw had dropped open, hardly able to take in all the meaning behind what his sister was telling him, but before he could say something, Penny jumped in and said, “And I know what you’re thinking. A grown man with a girl, but fuck that. High school boyfriends are shit. I knew we couldn’t walk around like boyfriend and girlfriend or anything, that we’d have to keep it secret. Sure, but I have no regrets.”

Gary finally closed his mouth and took a deep breath and found the means to ask, “So, you saw him a bunch of times after that. Like a hundred times? Really?”

“Are you kidding?” Penny put her feet back down on the floor and leaned over toward Gary as though disclosing a dark but wonderful secret. “I was at his house at the same time the next day and the day after that. And let me tell you, by the end of the month I had my first full on orgasm. Simon helped me figure out birth control, used a condom when he needed to, and did everything a real caring lover does for a girl. And get this Gary. I was at his place at least four or five afternoons a week, maybe some mornings, and every weekend. He even came here. Sometimes just for quickies, just so he could empty his balls into me and be on his way, but more often we met at his house or at a friend’s and just enjoyed each other’s bodies.

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