I've always been into older girls. Even from when I was a teenager, I would almost never imagine girls my own age in sexual ways but always girls older, more experienced. Of course, porn stars were older than me as well, so it gave me a natural look at things.
My sister Katie is 5 years older than me, so of course I would peek at her when she showered or walked around without clothes on, but I didn't have much time to do it. When I turned 13, she turned 18, and shortly after that she moved away to college. It wasn't far – the college is across town – but she got a dorm room and moved into it, eager to get out on her own.
I missed her around the house – we had always been close and had fun together. We liked a lot of the same movies and TV shows, and it just wasn't the same without her. Sometimes, we'd schedule a weekend and go to her dorm room, watching a season of a TV show on DVD. Those days were always special.
Katie had a boyfriend, off and on, for a few years. They would break it off, then get back together and be perfectly happy, then break up again. I never quite comprehended their relationship, because when they were together, they were great. But, as I found out, there was things going on I didn't know.
When I turned 18, I was planning to start college soon myself. To prepare for it, I got an account at the college's intranet system to start planning what classes I wanted to take. I was excited when I found out that the system was not only academic, but also social – there were several chatrooms where students met up and talked. I began going to these, feeling like I was already getting into the college experience.
Some of the chatrooms were academic or serious, while others were...of a more erotic nature. I also found out that there were lots of people from the town who went to those chats, trying to hook up with college students. They were pretty good at keeping the underage kids out, but since I was over 18, I had no problem.
Sometimes, I'd go on the site and there would be college girls looking for guys to hook up with. They always seemed to bail in the last minute, though – I never got further than swapping pictures on cam or email. On the night I want to tell you about, I was home alone, since mom had gone off to her lady dinner with some friends. I logged in, and checked the chatroom for interesting partners. It was pretty full, about a hundred people, and I noticed a girl with the nickname "GreatAss23". Her avatar was what looked like a picture of her ass in a thong, although it was hard to see, since it was so small.
I clicked on her icon and wrote her a private message, or as they say on chats, a PM:
Hi there...I'm an 18 year old boy, looking for something fun..are you in here for the same? And if so, how far do you go?
A few moments later, a PM returned to me:
Hi! I'm definitely looking for fun...of the naughty kind. I'm really horny tonight, and I'm sick of masturbating by myself....
Wow, I thought. She's pretty direct! I like it!
Cool! Well, I'd be glad to help you out with that. Are you ok with my age and everything?
Of course! Why wouldn't I be. In fact, you might be exactly what I want.
What do you mean?
Well, I'm kind of looking to fulfill a fantasy, and for that, I need a guy younger than me. So, are you ok with hooking up with a girl older than you?
I smiled, as I typed back to her:
Of course I am! Why don't you tell me what your fantasy is?
Well....here is the thing. My boyfriend and I have sort of an open relationship. But...he did some things that were against the rules we set up, and I'm pretty pissed. We just broke up, in fact. So I want to try something that I've always wanted to do, and he thought was against.
What is that? I was very curious now. Her reply came an instant later:
I really have this thing for younger guys...young cock turns me on. And I want to get fucked by a young guy, just completely banged through. In all holes. I want him to cum inside me, without condoms on, and I want him to just do all the dirtiest things he can think of.
Does that shock you?
No I typed back. That was a lie. I was a little shocked, but also intrigued. Was this girl for real? So are you looking for this to happen for real?
Yes. I am. Tonight, if at all possible.
It's kind of weird hearing you talk like this...you're the same age as my sister! I wrote to her. The thought of her exited me, but she was obviously more advanced than I ever had been. I'd slept with 2 girls, and both had been pretty ordinary experiences, missionary style, nothing fancy. I had never had anal with a girl, or had her blow me.
Do you have fantasies about her?
I hesitated a moment, but then wrote:
Doesn't every boy? A little bit.
I have fantasies about my brother, and he's 18. So it's OK if you have.
You do? What kind of fantasies?
Sort of the same as above. I want him to fuck me in my pussy, ass and mouth and cum there. I fantasize about lying in a dark room on all fours, naked, and he comes in and just walks up to me and fucks me.
That sounds...very very hot! I wrote, and meant it. The thought of Katie lying like that, and me coming in, actually made my cock hard. My cheeks flushed...I wasn't supposed to think that way about my sister. But it still was hot to think of it.
Do you really think so? You don't think it's weird and dirty?
Well, this is a sex chat. Weird and dirty is kind of the idea, right?
Right! I'd actually think it would be wildly hot to meet a young guy who'd be into something like that.
What part? The incest part, or the you lying in a dark room?
Both...kind of. What do you think? Would you be up for it?
I swallowed spit. She really did seem direct about this, so different from the kind of chat's I'd had before.
I don't even know what you look like...and you me.
Honestly I don't care what you look like if you're as young as you say, and if your cock is big. Is it?
It's pretty big, I guess....8 inches.
Wow. Really? My boyfriend was only around 7...that's pretty big!
Hell no. I've just got some doubts if I could get it all up my ass, but...I'd love to try! :-D
Look...are you serious about this? You really want some guy you haven't even see to fuck your ass?
Yes I really do. It turns me on so much. But if you're worried that I don't turn you on, do you want to see a pic? I won't show you my face, though...
Okay I wrote. I didn't have to wait long – a picture appeared in my PM. It was a naked girl, her breasts big and shapely, half turned away from the camera so her ass was showing. She was naked, and the curve of her back and ass was incredible. She wasn't skinny, but had feminine curves – in fact, her body looked almost as hot as my sister's Her face was blurred, but I could tell she had long, reddish-brown hair.
Wow...you look terrific! I wrote to her.
Thanks! J Nice of you to say so.
You are sure you don't want to see a picture of me?
Well, if you have one of your cock, it's not like I'd refuse...;-)
I looked in my picture folder and sure enough, I had a picture showing my body and cock in a mirror. I figured to keep the same level, I would send her one without my face on it. I moved it through Photoshop, cut my head off the picture, and then sent it to her. Her reaction was:
Thank you. I take that as a compliment...
You should. God, I want that up inside me. Have you ever fucked a girl's ass before?
Did you want to? ;-)
Of course I did...do...whatever.
There is no of course in that. Some guys, including my ex boyfriend, thinks it's dirty. Every time I want it, I've had to go find someone else to do it to me.
I can't believe he wouldn't do it if you liked it...
There's lots of things guys won't do. Girls too. So, how are you on the issue of cumming in me? Is that cool with you as well? I can promise you, I'm healthy. Normally I've used condoms with other guys than my boyfriend, but I just feel so wicked about this fantasy and I want it all the way. I want sperm to fill me up inside. And if you're so young...there's a good chance you're not sick either, right?
I'm totally healthy. Absolutely. And I'd be okay with it, I guess. Will you be ok, I mean, pregnancy-wise?
Don't worry about that. It shouldn't be a problem. Can you cum more than one time, then feel free to do so.
The thought of actually cumming inside this hot older girl, to do stuff with her the girls my age would never do...it seemed too good to be true. She then wrote something, that made me blink:
About the thing before with my brother and my fantasy...would you be open to doing something like that? Would you think it was weird if you called me "sis" while you fucked me? And I call you "Bro?" We could each imagine our sister or brother in the dark...
I hesitated. It deed seem incredibly hot, but at the same time, really really taboo. But how could I refuse her?
Okay, I think I could do that! Like I said, I've had thoughts about my sis myself, so...won't be so difficult, I guess.
Yes! *does a fistpump!*
I laughed. She was great.
So where do you want to meet? If you want to do this dark room thing?
Well...my friend is out of town, and she's lent me the key to her apartment. We could meet there? That way, you also won't know MY name and where I live. Is that all right with you?
Can you be at Glendower Street in an hour? It's number 43, 3rd floor. I'll leave the door unlocked. The apartment will be dark, but the bedroom is just across from the front door. You will be able to see it when you open the door.
An hour? I think so. Gives me time to shower at least.
When you come in, I'll be on the bed in the bedroom, and you should just come in, take your clothes off and take me. Touch me, kiss my body, shove your cock right in...that's up to you. I'll lube up before you get there (but probably won't need it...I'm soaked already!) And I don't mind going back and forth from one hole to the other – I'm clean. Just so you know.
Okay. I really hope you're not going to pull a joke on me ;-)
I promise. I'm serious. One hour? And don't forget to call me sis ;-)
I'll be there!
See you then!
She logged off the chat, and I sat for a moment, just unable to believe what I had just experienced. She seemed incredible, sexy, kinky and hopefully, genuine. I got to my feet, and pulled my clothes off and jumped into the shower. I cleaned myself off, put deodorant on, and put some clothes on that was easy to get out of. It didn't matter what it looked like, since I was going to strip down in the dark anyway. I couldn't believe that she wanted something as anonymous as this...but if that was her fantasy, who was I to argue? I would be having sex with a hot 23 year old...I'd even get to do her without condoms, and cum inside all her holes, as she had said several times.
I got on my bike, and headed downtown – mom had the car, but I didn't have far to go. Glendower street was in the nice student neighborhood close to the walking streets, and I parked outside the house with 5 minutes to spare.
Looking up, I could see the apartment in question, and see a single light on in one window...and then, I saw it being turned off. She was there. She was ready.
I opened the front door, and headed up the stairs. When I reached the 3rd floor, there was only one door. I took a deep breath and gripped the handle...the door slid open.
The light from the corridor wasn't very strong, but my shadow still fell into the dark apartment. Across from the door was an open door to the bedroom, and on the bed, I saw a naked girl. She had her ass turned towards me, and the two white globes of her ass looked amazing. My shadow fell over her, and I could see her trembling a little.
I stepped inside, and closed the door, letting my eyes adjust to the dark. I could still sort of see the white skin, but only as an after image.
"Sis...?" I said, my voice sounding thick to my own ears.
"In here, little brother!" came the reply. I was imagining that it was Katie's voice I was hearing, and seeming to do a pretty good job. It sounded a lot like her.
I walked into the room, and close to the bed. I could see the shape of her on the bed, the outline faint.
"You're still...sure...?" I asked, just making sure one last time.
"SO sure. Come on...get naked...little brother...!"
I pulled my jacket off quickly, and then my T-shirt underneath. My jeans and boxers fell to the floor, and I stood completely naked next to the bed. I reached a hand out and put it on the small of her back, feeling her tremble as I touched her.
"Oh sis...!" I whispered. My fingers caressed her ass cheeks, and slid up and down her back. My cock was standing like a hard rock between my legs. As I caressed her, I felt it pressing against her shoulder, and she shuddered. She lifted one hand and gripped it, making me give a little gasp.
"Oh wow...it's so big...and hard..." she whispered.
"You want to suck it?" I asked, and then, trying to keep in part, I added "you want to suck...your little brother's cock?"
"God...I'd love to...!" she said, and again I was struck with how much her voice sounded like Katie's. Then, I felt a soft, hot pair of lips closing around my cock, as she took in into her mouth and began sucking as she sat on all four.
"Ooohhh....!" I moaned. My hands found down to her asscrack again, and slid down to her pussy – I felt she had not been lying. She was soaking wet.
My fingers slid up inside her pussy – I could tell she wasn't shaved, but trimmed – and they went right in, without resistance. Her mouth was filled with my cock, but I could feel her moaning.
She was incredible at sucking – as I've said, my cock's pretty big. But she was sucking down on it like she had the intention to devour it, and she actually almost got it all into her throat, gagging a bit as she did it. I could feel her drooling a bit from the deep penetration, and her spit ran out over my balls.
I fingered her, first with one finger, then with two...and her body was writhing in pleasure. Her pussy trembled slightly, and I decided I'd fulfill a bit of her fantasy right away – I took moisture from her pussy and added it to her asshole, before sticking a 3rd finger in there. That made her almost whimper with pleasure.
As I pulled the fingers in and out of her, I could feel how she eagerly sucked my cock. She was filled in all holes now, and it was what she'd dreamed of. She sucked faster and faster, taking one hand up to jerk the root of my cock, and this made my balls tighten up in pleasure. I knew I never could last long the first time, but at least I know I would stay hard.
I gave a moan, and said "oohh fuck sis...I'm gonna cum!"
"Uuuuuuuhhhh!" she groaned, and kept her mouth clamped to my cock. I knew she wanted it in her mouth, but I thought she needed a warning anyway. I felt the cock tightening, and then a hot load of sperm shot out of the head and into her mouth. She made a sound of pleasure as she swallowed it all.
I felt her tongue lick round the head inside her mouth, and shuddered, then pulled the cock from her mouth. I could hear her lips smacking closed.
"Fuck me...!" she gasped. "Fuck me now, little brother...fuck your sister!"
I was speechless for a moment, but then whispered "Okay, sis!"
I climbed onto the bed, behind her upturned ass. She bent her torso down, and I could tell she was relaxing her ass cheeks.
"Put it in there, little brother...!" she said, her voice louder now. "Put it in your sister's ass. Fuck me!"
I grabbed my cock in my hand, aiming it between the white globes. My eyes had now adjusted more, and I could see her a little clearer.
I could feel the asshole against my cock's head, and felt her relax...she took a deep breath, obviously trying to make herself relax even more. She reached behind her, and put a hand on my hip, pulling me forward.
I felt the asshole opening more, and then the head slid into her. It felt totally effortless, she had lubed herself up, as she said. She gave a loud moan, and her body shook with pleasure.
"Fuck...it's...so big...come on..go slow...slowly....!" She said, her voice strained, but full of pleasure.
I pushed slowly forward. My cock's shaft slid a little deeper in, deeper and deeper. I could feel her body taking me deeper in, feeling the walls of her ass being widened. I could see the arch of her back, and again imagined my sister Katie's face and voice.
"Ooohh Katie...fuck you're so tight...!" I groaned, letting my fantasy go a little further and forgetting I promised to say "sis".
She moaned back, but then I heard her say something that made me gasp:
"How...do you..know..uuuhhnnn...my name???"
I stopped moving inside her ass for a second, but then thrust forward again. She moved her head, her long hair moving against the pillow.
"I...I didn't...I just...said...my sister's...name...!"
That was the last straw. I now was sure. The girl who had my cock buried in her ass WAS my sister Katie. The odd thing was, it didn't make me want to stop.
"Katie...Katie...I...I didn't...know...!" I gasped, as I felt how I now had entered even deeper into her ass. My cock was almost buried in it, and I felt her fingers coming up under her, beginning to rub her clit.
"I...know...keep...fucking..me...little brother!!!" she gasped, "God...this is...the hottest..EVER!" Her hand rubbed her clit fiercely, her fingertips brushing my balls. "Ooooohh GOD!" she screamed, and her ass tightened around my ass like a vice. She squeezed me, as she climaxed so hard, I was afraid she was in pain.
"Fuck...fuck....keep going Chris...please...fuck me...ooohh shit, I'm cumming...fuuuucck!"
Her entire body shook, and I could tell from the sprays of liquid hitting my balls that she was squirting.
I took her hips in my hands, and began fucking her harder, going in and out in deep, long thrusts, really feeling how she was now opened for it. As I fucked her, she kept rubbing herself, and gasping, the orgasm apparently continuing to carry her from peak to peak.
"I...want you...to shoot...inside my ass Chris...Please!" she moaned. That was all the encouragement I needed. I pushed deep inside her...as deep as I could go – and felt like my cock exploded inside her. Sperm flooded inside her ass, coating her bowels with hot white cum.
I could hear her gasp as it hit her insides, and her ass clamped down again, obviously reaching another orgasmic high.
I collapsed over her naked back, and she groaned. Then, as I pulled my cock out of her ass, she turned around and looked at me in the darkness.
"Chris..." she whispered, "What the hell...were you doing on a college chat?"
"I've joined...to meet new people..." I said, as truth were.
"Well...I'd say that worked!" She gave a giggle. "I can't believe we did this!"
"Me neither...but it felt amazing!" I smiled at her, as I lay next to her, feeling both weird and normal at the same time.
"It really did. You have no idea how long I've fantasized about this, though."
"Since...oh, since before I moved." She smiled. "And now we did it."
"Are you sorry?"
"No, not at all..." she smiled, and her hand grabbed my cock. It was still half hard. "In fact...there's something we didn't do....that we should. If you're up for it. We've gone this far..."