Keri and Jimmy's First Time
by Slippery Saddle Bum
Copyright© 2026 by Slippery Saddle Bum
Coming of Age Sex Story: With only each other for company, a brother and sister are closer than most, so when they overhear an interesting conversation, they decide to try what they heard and get something straight between themselves.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft Consensual Romantic Incest Brother Sister Cream Pie .
My sister and I played together because where we lived, there was no one else for us to play with. Lucky for us and unlike most brothers and sisters, we were true friends. We really liked each other and enjoyed being with each other. We’d just grown up like that. She was smart as a whip and was anything but a pain in the ass ... not at all the way my friends described their younger brothers and sisters as being. Our parents had hired an eighteen-year-old sitter, despite us being more than old enough to take care of ourselves, who spent the days by the pool with her iPod and cell phone totally ignoring us except to make us a quick lunch, which seemed to be an inconvenience to her but was okay with us. Actually, we liked her because she left us alone and didn’t boss us around the way all our past sitters had so we didn’t hesitate to tell our parents how much we liked Sally ... just not why we liked her.
On Monday of her first full week, Sally was standing just outside the open kitchen window when we overheard her talking excitedly to one of her girlfriends on her cell about putting a squirt of KY jelly in her pussy hole the night before so it’d be easy for her boyfriend’s big cock to go into her.
Keri and I were in the kitchen eating our lunch and heard every word as clear as if she was standing right next to us. We heard the excited sound in her voice when she told her friend how it felt so good when he got it all in and started fucking her. She said she never had a big cock like his in her before.
We listened as she went on with dreamy excitement in her voice, “He fucked me for a really long time and made me cum sooooo hard ... TWICE!!! And then he came inside of me and made me cum again!! I thought I was going to die!! It was so HOT!! I felt his cock start swelling up inside of me so I knew he was getting ready to cum and I went crazy. I was fucking his ass off and then I felt his cum squirting in my pussy!! Oh, God!! I was in heaven!! ... and there was so much of it!!! It’s a good thing I’m on the pill. His cum has been running out of me all morning long! I just love it!!”
There was a pause while whoever she was talking to said something and then she said, “Yeah, I’m seeing him again tonight.”
Another pause... “Damned right I am! I love how his cock feels inside of me. I’ve never felt anything like it before. I’m getting as much of it as I can get. Who’d have ever guessed his cock is that big? I’m glad I knew Mom and Dad always have KY jelly in their bedroom. I put some in my pussy and made it real slippery so he wouldn’t kill me getting it in. Now that I’m used to him, I might not need to use it tonight. I’m so wet right now, just thinking about it ... I’m gonna try without it, first.”
When we’d finished our lunch, Keri and I went back upstairs, and Sally, with her phone still up to her ear, had gone back to her lawn chair, next to the pool. When we got upstairs, Keri said, “Jimmy, did you hear what Sally was talking about and telling somebody on her phone? She did the nasty with some boy last night!”
I said, “So what? People do it all the time. But why’s it nasty? It can’t be nasty, or they wouldn’t do it, would they? They must like doing it. It sounded like Sally does.”
Keri thought for a minute and then said, “Yeah, I guess. She sounded really excited about how good it felt and told her friend she’s going to do it again tonight.”
I was starting my computer when Keri said, “I wonder what it feels like.”
Looking over at her, I asked, “What feels like?”
She said, “What Sally was talking about ... doing the nasty. Mom and Dad have two or three tubes of that KY jelly stuff in the drawer in their nightstand. I saw it when I was looking for a headband yesterday. They always have some in there. Want to use some like Sally did so we can try doing it, just to find out what it feels like? I won’t tell anybody if you don’t.”
I felt a twinge of guilt because Keri is my sister, but she’s pretty, and ever since my buddy’s had begun teasing me about my big cock and telling me what I could do with it, I’d definitely become interested in sex.
“You mean put my thing in your hole, like the guy put his in Sally’s?”
“Yeah, just to see what it feels like. You want to?”
“I guess so. Where do you want to do it, here?” I asked.
“I don’t know ... Mom and Dad’s bedroom is across the hall from my room, and that’s where the KY stuff is, so let’s do it in my room. Mine’s the farthest from downstairs, too, so if we hear Sally coming, we’ll have more time to cover up so she doesn’t see anything. We can have some books open and say we were reading.”
I’d been waking up with a hard-on just about every morning for months and had begun noticing pretty girls. Keri is definitely a pretty girl, and though I’d felt guilty about it because she’s my sister, I’d been noticing her, too. Until recently, most of my conversations with my friends had been about what it would be like to fuck girls and talking about the ones we wished we could do it to. After a lot of teasing about the size of my cock, one of my buddies had brought a ruler into the bathroom and told me to get a hard-on so they could measure it to see how long it was. They all knew that mine was a lot thicker and longer than any of theirs, even when it was soft. Now they were cheering me on to get it hard to see how big it is when it’s hard.
With the five-guy audience, I couldn’t get it fully hard. When Larry figured it was as close to hard as it was going to get, he held the ruler up to measure it, and it was just under six inches long. Two of the guys said “Wow!” and the way they said it made me feel proud. One of them asked if I’d ever fucked it into a girl’s pussy hole. I told the truth, which was no.
He said, “You should get one and do it. She’ll be real tight when you put it in, but you’ll stretch her pussy out real good while you’re fucking her.”
One of the other guys said, “Yeah, and ruin her for the rest of us. She’d never fuck any of us after he’s fucked her. That’s a brilliant idea, asshole.”
They’d all kept their mouths shut about the size of my cock after that. They didn’t want to advertise for me.
Keri headed down to Mom and Dad’s bedroom for the KY while I went to the bathroom to take a pee. When I was finished, I came into Keri’s room, closed the door, and pressed the lock button. She was sitting on her bed with a half-empty tube of KY jelly lying next to her.
Looking up at me, she said, “One of my friends told me that guys and their girlfriends do things to each other with their mouths, sometimes. It’s oral sex, but she said she looked it up online and it’s called cunnilingus. She said it says if it’s done nicely, licking and sucking feels really good, too. Maybe that’s something else we could try doing, couldn’t we? This KY stuff might not taste so good after we have it on us, so do you want to try licking and sucking each other, first, before we get it on us?”
I said, “OK, but we better take our clothes off, first. We have to be undressed anyway, so it’ll give us a chance to start getting used to seeing each other without clothes on. Want to just take ‘em off fast so it’s all done? Then we can get on the bed and look at each other as much as we want, afterward.” I was nervous, so my cock was soft, but I was excited about seeing Keri’s pussy and having a chance to fuck it.
Keri stood up, put the tube of KY on her nightstand, and pulled her bed covers down. I could see that she was nervous, too, when she looked up at me and said, “OK, let’s do it fast. I’ll race you.” And she whipped her jersey over her head, tossing it onto the floor.
I reached for mine while she started unbuttoning the bright red shorts she was wearing. By the time I had it over my head, her shorts and panties were down at her ankles. Even as I raced to get undressed, I couldn’t help noticing that she has a nice little bubble butt ass. She was stepping out of her shorts while I was just sliding mine down over my hips. She was on the bed a second ahead of me... both of us stark naked. She looked up at me with an excited game grin, “I won.”
The actual game was about to begin, and Keri hadn’t won it yet ... but then, neither of us knew WHAT had just begun.
I lay next to her, looking at her little boobies. They were big bumps ... half grapefruits on her chest, and the nipples were raised about quarter of an inch above the swells and looked like tasty little pale rose-colored morsels. My cock was still soft. I was lying on my side, so it was hanging down partway over my hip. Keri’s eyes caught sight of it, and she stopped grinning. “Gosh, Jimmy. Your thing looks ... nice. It’s kind of big, though. Sally said the guy she did it with has a big one, too, and the KY stuff is what made it go in.”
I changed the subject asking, “Your boobies look nice, Keri. Can I lick them and suck on them a little?”
She looked down at them and said, “OK, but do it easy. They’re starting to get big, but they’re kind of sore.”
I gently pushed her over onto her back and leaned over her suddenly heaving chest and quivering belly. That’s when I noticed the pronounced, puffy mound between her legs. I couldn’t get a very good look at her pussy from where I was, but I planned to get a close-up view as soon as I’d licked and sucked on her titties for a while.
Putting my arm around Keri, I pulled her body up until her tit was at my mouth and licked across it. She jerked, made a surprised ‘nnnnhh’ sound, sucked in a breath, and shivered.
“Does that feel good?” I asked.
In a breathless whisper, she answered, “Yeah. Wow. I never felt anything like that before. Janice wasn’t kidding about this stuff feeling good. Do it to my other one.”
I lifted myself over her and lowered my mouth to her other tit. Keri was holding it up for me as I licked all the way across it, sweeping over the nipple that was now standing a good quarter of an inch taller than it had been. Both of them were. She reacted the same way she did when I licked her first tit. I licked it again and again and then went back to the first tit and gave it several licks. Keri was squirming around and pushing her tits up to my mouth. When I sucked on one of them, she let out a loud moan.
“Ohhhhh, Jimmy. That feels good. Do that to the other one, too.”
I sucked her other tit the same way and got another long, drawn-out moan while Keri pushed her tit up into my mouth. When I looked up at her, her face was all red.
“You really like that, huh, Keri?” I asked, softly.
Looking straight at me, she said, “Oh, Jimmy ... You can do that to me anytime you want to. They’re a little sore, but you did it just nicely. It kind of tickles, but it feels so good. It even makes me feel funny down between my legs when you do it. It’s better than any feeling I’ve ever felt ... ever, EVER!”
Looking at me, she asked, “Can I lick and suck on yours like you did mine?”
I lay back on the bed, and Keri sat up. I could see that her titties were definitely sticking out more than they had been, and I liked what I was seeing. My pretty little sister looked excited and sexy. She moved over my chest and eagerly started licking my tits. After she’d licked over and around them for a minute or so, I told her that it tickled and felt good but didn’t do anything like what it did to her. I told her to try licking my belly and down lower. She looked down and saw my cock at half mast. It was getting bigger and thicker. Skipping my belly, she headed straight for it, licking all over it and around the base of it. Her tongue is soft, and she was definitely having an effect on my cock.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.