Best Friend’s Shy Brother Wanted To Use My Butthole To Cum

So I let him.

Little background info and physical description in case anyone cares.

I’m on the taller side (5'8), slender with wide hips and perky C-D cups, a “slim-thick” booty with great Venus dimples, brown hair that was colored blue at the time of this story, big brown eyes, and soft features that most people describe as “elf-like” or “innocent”.

Let’s just say that people seem to enjoy how young my face looks…

Oh yeah, I’m also a total whore, and have been since the day I discovered orgasms!

Anyway, this story happened when I was 18 (I’m 21 now) and living with my best friend and her older brother (21 at the time).

As I said, I’ve always been a whore, and my need and love for dick is constant and severe to the point where, as long as I don’t think you’re going to kill me, you can use my body in basically whatever way you want to get off.

I’m not usually the one to approach people though, as I’m definitely a sub who needs to feel desired in some way for my inner whore to truly come out. Once someone makes it known they want to fuck me, it’s game on.

My friend’s brother definitely had a good idea about how easy I was, but he was such a shy and reserved person that, before this event, he had never overtly approached me for anything sexual, and I never really expected him to.

Apparently, this was just one of those days a lot of guys seem to have where their need to fuck something outweighs their inhibitions, and they get some extra courage to make a move.

I guess jerking off just couldn’t cut it for poor little Jason (the brother) today. Maybe he just couldn’t find a video to get him over the edge, or something I was wearing caught his eye (typically shorts up my ass and a see-through tank top with no bra).

Whatever it was, I was headed to the kitchen to grab a drink and I noticed him not-so-subtly staring at me from his bedroom doorway with a look on his face I hadn’t seen before. It was some mix of hopeful, embarrassed, and hungry…

I guess my whore sense was tingling because my instinctive reaction was to give him a sort of knowing grin, even though I had no way of knowing for sure what he was thinking.

Regardless, I could feel I was being looked at like a prospective piece of meat, and my body perked up and responded immediately. Pushing my ass and chest out just a little bit more than necessary in some sort of pre-fuck, whore courting ritual, I looked at him, grinned, and said,

“Hey Jay”

Apparently, that was all I had to say and do because the first words out of his mouth were,

“Hey Katie… Um, do you think we could fuck?”

My jaw wanted to hit the floor because, despite the fact that some part of me was expecting to at least be hit on, I definitely did not see it going like this lol.

He’s just such a typical gamer, anime-loving, socially awkward person that never seems to make any moves with girls, that I didn’t even think he was capable of propositioning someone for sex, let alone in one sentence, out of nowhere, to his sister’s best friend, who lives with him and has known him for years. I was sort of shocked, but also strangely proud of him lol.

Being the whore that I am, I immediately started anticipating being filled up, and excitement took over. I sort of lightly giggled at his unique brand of confidence and, trying to not overwhelm him I said,

“Yeah, sure. Where do you want to?”

His demeanor changed for just a second, almost as if, up until this point, he didn’t think getting sex could possibly be this easy.

Did he honestly expect me to say no?

It was pretty cute, he just looked like he knew he had succeeded, but realized that he was actually about put his dick inside me, so a brief moment of nervousness crossed his face.

His sister wasn’t home, so I didn’t really care where or how we fucked, and I wanted to leave it up to him.

Honestly, I’m a little awkward myself, so I didn’t really know how to handle the situation without making it more awkward, but my body was committed to making it happen because, once again,

I’m a whore that needs dick.

I figured, this must be some kind of fantasy for him, so I should just make it as easy as possible on him and make sure it goes the way he was hoping. I’m a pleaser!

He straightened up a bit in what appeared to be some forced attempt at wordlessly conveying something like,

“Yeah, of course you said yes, cause I get girls all the time”.

“How about my room?”, he said.

I did a cute little bounce towards his room, maybe a bit too eagerly, and immediately just removed what little clothing I had on and said,

“How do you want me?”.

I think he was really struggling to accept reality at that moment, as 10 seconds ago it was just like any other day where we would cross paths in the house we shared and just go about our days. But, to his credit, he sort of stammered out,

“Can we do doggy?”

Fuck yes, my favorite position. I was struggling to hide my glee and excitement now, this could actually turn out to be a fun experience.

I absolutely love showing what a slut I am when I know a guy is about to fuck me, as their reactions are always so filled with desire, and it’s their desire that fuels me more than anything.

So I turned away from him, climbed on his bed, bent over, and just spread my holes open for him to look at and admire. I’ve been told I have very “tiny” and adorable holes, so I love keeping them shaved and showing them off to people.

I was in this position for about 3 seconds before I realized he might have wanted his dick sucked before just ramming it in, and he had yet to make a move towards me, so I flipped back around real quick and got on my knees to give him the option and show him that I wanted to please him in whatever way he felt like.

He didn’t say anything, as I could only guess by the look on his face that his head was exploding, but he took a step towards me and just pulled his shorts down below his obviously hard dick and looked at me expectantly. I immediately just took the whole thing in my mouth (just above average size, maybe 6'?) and he sort of gasped and flinched.

I got the impression that he was definitely over excited, and that maybe he had been jerking off right before asking me to fuck (was that why he was worked up enough to proposition me?), so I reigned in my enthusiasm a bit and tried to pay attention to his body to make sure I wasn’t going to accidentally make him cum immediately.

I’m pretty proud of my dick sucking skills, and I love giving pornstar-style blowjobs, but I could tell this probably wasn’t the time for that, so I basically just tried to do what I thought he wanted me to, which was get his dick wet and let him feel my warm mouth and tongue for a minute or two — basically just give him a blowjob experience without any intent to make him cum.

It definitely had the desired effect, as he seemed to relax and find himself a bit — settling into the reality of the moment and just enjoying the feeling of my tongue repeatedly flexing and relaxing against the bottom of his shaft, slowly milking his now noticeably throbbing cock.

He definitely enjoyed the view too, as I made sure to stick my ass out and look up at him with eager and hungry eyes.

After a minute or two he suddenly pulled his dick out of my mouth, took a step back and offered his hand out to me (so cute). Assuming this was the sign it was time to start fucking, I took his hand to stand back up and resume my doggy position, my now dripping pussy basically cramping for something to fill it.

Honestly, my holes have minds of their own, and when they are hungry it’s quite literally like an actual hunger pain — kinda hard to describe, but I just feel painfully empty and wanting, and it doesn’t take me much to get there. If my body knows a cock is about to be forced inside of me, it prepares accordingly.

I spread my holes open for him again and this time there was no waiting. I immediately felt him move up behind me and aggressively drag the head of his spit-soaked cock from the top of my butthole, all the way down to my clit, then back up to my pussy, where he pretty forcefully shoved it in balls deep in one stroke.

Right before he pushed into me I thought to myself,

“Oh shit, was he about to go for my asshole instead?”.

My thoughts were pretty abruptly cut off though once I felt him bottom out in my pussy and immediately start taking long strokes, replacing my hands with his, and spreading my ass cheeks open so he could admire the view.

I was actually pretty surprised at how well he was fucking me at this point, getting into a steady rhythm and spreading me with a firm grasp and a clear intention to make me feel like I was his little slut to use.

Gone was the shy and reserved, seemingly asexual brother of my friend, and in his place was a man whose instincts to breed took over and was intent on pumping this desperate whore full of his cum. He was definitely in the moment now, and I could feel it.

His pace started to increase a bit and I was expecting him to cum soon, until he suddenly slowed down and readjusted his hands so that his thumbs were right next to my asshole, spreading it open with a clear intent to get as good a view of it as possible as he slowly thrust in and out of me. The thought popped back in my head,

“Is he thinking about fucking my ass? God I hope so”.

My whore instincts must be pretty good, because only a few seconds later he paused and said,

“you like anal right?”.

Oh yeah, I forgot he probably knows that about me, as it’s 100% true and I talk about it with his sister constantly (she hates it, poor girl).

For me, anal is pretty much a guarantee whenever I fuck as long as the guy makes it known he wants to. I cum insanely hard from it and I often prefer it to vaginal, so I pretty much never turn it down, and few things turn me on more than a guy who wants to use my asshole to cum.

It’s just so primal and naughty. It’s like, you desire me so much you want to force your cock into my tight little butt where it doesn’t belong and just blast my insides with wasted cum that can’t even get me pregnant? Yes please, thank you, daddy!

In response to his question regarding whether I like anal, I said, “Yeah why?”, obviously knowing why lol.

“Think I could try? I’ve never done it before”

Don’t have to ask me twice. Knowing that this was probably part of his fantasy I asked again,

“How do you want me?”

Apparently, I was right, because he immediately had me stand up against the wall, ass out, hands spreading my cute little butthole open for him. He even had some lube ready!

How long had he been planning this?

He put some on himself but, being the anal pro I am, I reached out for some of my own and slipped a few fingers inside my ass. I don’t need long to prepare, which is a huge plus for someone who loves anal as much as I do, and as soon as my fingers got inside of me I could tell I was ready. As I said, when my holes are hungry, they do what needs to be done.

I resumed my position and felt him come up behind me,

rubbing the head of his cock on my tight and eager asshole. He seemed a bit hesitant to actually go in though, maybe he had heard that you need to go really slow, or else it’s really painful for the girl?

Very sweet of you, but I’m a fuck toy and you don’t need to take your time with me, please just use my butthole so I can feel like the good whore that I am. I inched my ass back, making it as obvious as possible that I needed him to just fill my ass at this point and not worry so much about hurting me, and he got the point.

Again, in one long stroke, he just buried his cock balls deep,

almost like he was testing me to see if my gesture of moving my ass back to get him inside of me as soon as possible was sincere. I think he expected to prove me wrong and make me regret it, but instead, he got a groan from me that was unmistakably the signal to keep going and to make it count.

He quickly picked up a rhythm similar to how he had been fucking my pussy, but I think he could tell by the sounds I was making that I was dying for him to just slam into my asshole as hard as he wanted, and so he did just that.

I don’t know how long it lasted, as I tend to almost blackout from pleasure when my ass is being railed hard like this, and I was basically just trying to stay standing up against the wall instead of collapse to the floor.

My legs tend to go weak when I cum this hard, which I almost always do from some good butt-fucking.

He was just hammering into me in a frenzy,

spreading my ass hard himself, as my hands were now dedicated to holding myself against the wall.

He must have really enjoyed the view of my cute little butthole gripping his cock as it convulsed with my nonstop orgasm because he started breathing heavy and almost grunting as he gripped and spread my ass cheeks almost painfully hard.

He made a final thrust into me and just unloaded into my guts. The feeling of hot cum flooding the inside of my asshole is one of my all-time favorite things. It’s sort of indescribable for me, but it gives me goosebumps every time.

I’ve also literally trained my asshole to squeeze in rhythm with a guy as he cums, basically milking him as much as possible. I’ve been told it’s a pretty amazing feeling lol.

After he finishes, he pulls out of me and, as if this experience weren’t strange and unexpected enough (as amazing as it was), he says,

“I just fucked a butt”. LMAO.

Yes sir, yes you did.

Despite the fact I could tell he thoroughly enjoyed himself, that was the one and only time he ever had the courage to basically ask to use my holes to cum.

No worries though, I have lots of other ways to get the dick! :D

More to cum?

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I’m sending you so much love 💋 Olivia

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