Kelly's Diary 043 - Caught by My Boyfriend's Sister - Cover

Kelly's Diary 043 - Caught by My Boyfriend's Sister

Copyright© 2024 by Kelly85

Chapter 2: Fucked by Randy

Incest Sex Story: Chapter 2: Fucked by Randy - We thought we had the whole house to ourselves so what better place than on his parent's bed? At least it seemed like a good idea... until his older sister showed up.

Caution: This Incest Sex Story contains strong sexual content, including mt/ft   Fa/ft   True Story   Mother   Daughter   Masturbation   Oral Sex   Voyeurism  

I quickly ran down the stairs and sure enough, there was Randy standing at the front door. I called out goodbye to my mom and Randy drove us back to his house. It was only a short drive to the outskirts of town. As he’d promised, the house was empty and given we were both horny as hell neither of us wanted to waste a moment with silly small talk. Randy took my hand and started up the stairs.

“C’mon, let’s go up to my room Kelly.”

He turned into his room and I went through the door and stopped. It was a typical boy’s room - a mess and not exactly the setting I had in mind for the upcoming activities. A sexy idea suddenly came to me and I gave him a naughty grin.

“I have a better idea Randy, let’s do it on your parent’s bed!

As horny as Randy was, he hesitated and I could tell that he wasn’t all that thrilled about this new idea of mine. Randy seemed to live in mortal fear of his mother ever finding out he wasn’t a virgin so I could understand how the thought of doing it in her bed was something totally alien to him. In his mind it had to be almost like we were doing it with her watching. Now THAT would have been hot for me but I’m sure Randy would die on the spot if his mom walked in while he was fucking me.

“But Kelly, what if they find out? My mother would kill us both!”

All his protests did was make me want to do it on his parents’ bed all the more. If his mom was going to be such a prude, what better place to fuck her precious son than in her own bed! I grabbed his hand and pulled him out into the hallway and down to where I figured his parent’s bedroom was. He tried to protest but he came along. Actually I think I could’ve dragged him out to the front lawn at this point if that’s what it took for him to screw me!

We got to their room and I looked around. Typical parent’s room - big pine furniture and pictures all over the place; most of the two of the kids along with a few of themselves from their wedding and vacations. Looking at a few I saw that Randy’s mom was quite cute when she was younger; too bad she had let herself go so badly. She must weigh 250 pounds now - probably at least twice what she did in the pictures. It was the same story for his dad - he was a hunk when they were married but you would never know it today from the beer gut on him. It made me appreciate my parents all the more. My mom was 36 and still looked hot enough in a thong bikini to turn heads. My dad was just a few pounds over his college graduation weight and kept himself fit at the gym playing racquetball.

I also checked out a few pictures of Randy’s sister - she was quite pretty and the family resemblance to Randy was obvious. I could see that Randy was a bit flustered at being in their room and especially with me looking around so I took the initiative to get things moving along. I licked my lips seductively and motioned for him to come to me.

“Don’t just stand there, if you want to fuck me then you will have to undress me Randy.”

From past experience I knew Randy was fascinated with taking off my clothes. After all, I was the only girl that had ever allowed him to undress her and it was obviously something he fantasized about a lot because whenever he did it he would get a massive erection! This was the reason why I wore a bra and panties today - to get him turned on by letting him take them off me.

I stood there by his parents’ bed as we hugged and kissed. As his tongue invaded my mouth I could feel his hands fumbling with my blouse buttons. He finally got them undone and opened my shirt, revealing my little white bra. Randy stepped back and just looked at me, licking his lips subconsciously. All those years of pouring through the bra and lingerie sections in the Sear and Penny’s catalog, dreaming of having a girl wearing nothing but a cute bra just for him, were finally coming true.

Randy pushed my blouse off my shoulders and down my lowered arms, leaving me with just my bra on top. Then he unsnapped my jeans and struggled a bit to get the zipper down. My jeans were pretty tight so it took some work to get them off but eventually he left me standing there in just my bra and white cotton panties. My plan had been to give him that innocent schoolgirl look which is why I chose my plain bra and panties rather than something more sexy like a thong. It seemed to be working from the way he looked at me, not to mention the incredible bulge in his crotch. His face was flushed and I knew he wanted me terribly.

“Oh wow Kelly, you look so cute and sexy! I’ve dreamed of seeing you in a bra and panties so many times that I can’t believe it’s actually happening for real!”

Since he seemed so turned on by my underwear I decided to keep it on for a while longer and turned my attention to him.

“So are you going to stay in those clothes while I’m standing here in just my underwear?”

Randy took the hint and quickly stripped down to his jockey shorts - no loose boxers for him. His cock was so hard already it was practically spilling out from them. Much as he looked so damn hot already, it only made me want more.

“Hey guy,” I scolded him, “All of it off! I want to see that sexy body without anything in the way.”

I got a kick out of Randy’s modesty. Randy was always shy about me seeing him naked even though he looked great! Even if I hadn’t already known, it was obvious he had grown up in a family that viewed nudity entirely different than mine. He turned away as he dropped his shorts and I got a long look at his firm ass when he bent over to take them off.

Mmmmmmm, I wanted to reach out and just hold that firm butt in my hands! He turned around and kept one hand in front of his crotch. I looked at him and frowned. He once again took the hint and removed his hand, revealing his nice cock, hanging from a thick bush of black pubic hair.

“That’s MUCH better Randy. Trust me, you have nothing to be modest about - I just love your hairy crotch! Now finish undressing me.”

Randy fumbled as usual with my bra. This time I’d picked out one that clasped in the front, hoping it would be easier for him to undo. Finally he got it and spread the cups apart, setting my small white breasts free with my nipples already hard with anticipation. I could hear Randy as he sucked in a breath and let it out slowly. He just stared at my boobs until finally I couldn’t help but giggle a bit.

“See something you like Randy ... earth to Randy ... HELLO!”

Randy shook his head as if to snapped out of whatever dirty fantasy was running through his mind. I took his hand and held it to my breast, moving it in small circles to massage me gently. I loved the way his palm felt moving across my sensitive nipple, sending tingles though me each time he rubbed against it. I looked him in the eyes and whispered to him. “Aren’t you forgetting something?”

Randy gave me a questioning look and so I looked down at my panties that, much to my chagrin, were still on. Randy followed my eyes and finally realized what I was referring to. Without another word he put his hands on my hips and spun me around. As he slowly worked my panties down I could feel my butt being exposed and I pictured him staring at my ass. Even though I wasn’t into anal sex I still loved my butt to be played with.

I stepped out of my panties as he lowered them to the floor and we faced each other, both now totally naked as the day we were born. He reached out for me but I stepped back and ran over to his mother’s dresser, giggling and smiling like a little girl, except I was a nude and horny little girl.

“What in the world are you doing Kelly?” Randy asked anxiously, holding his hands up and obviously wondering why they weren’t all over me by now.

“I just thought of a surprise for you. Hang on a second!”

I started rummaging through his mom’s drawers as Randy just stared at me, simultaneously lusting for me but at the same time totally flabbergasted at what I was doing. Finally I found what I was looking for - a black silk robe. Every woman, no matter what size, has to have at least one sexy nightie or robe. Giggling, I pulled it out and slipped it on. It was way too big for me but the silk felt nice against my bare skin. I walked towards Randy, leaving the robe open to allow him to see my boobs and pussy. Randy just stared at me with his mouth wide open.

“Oh ... my ... god! Kelly, that’s my mom’s! Put it back. You can’t wear that!”

So he thought ... I gave him an evil grin and reached out for his cock. “What’s the matter Randy? Admit it - doesn’t it turn you on to think about fucking me in your mom’s clothes? After all, if you’re going to fuck me in her bed, shouldn’t I be wearing her clothes”

Randy’s cock was still hard as it could be in my hand so I knew he wanted me no matter what I was wearing. He just shook his head in disbelief. “I don’t know Kelly. I just never dreamed I would ever even SEE my mom’s lingerie let alone fuck someone wearing it!”

Somehow I had a feeling Randy was turned on more than he admitted or perhaps even knew himself. At the same time I was 100% positive he could never have even dreamed of doing anything with his mom (I certainly couldn’t blame him for that!) but the thought of rebelling against her by doing something naughty like this was a sure-fire turn-on for him.

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