I’m new to this subreddit so going through all my slutty experiences and trying to write them down, and oh boy, there have been a lot. But here’s an old goodie in which just like the title says, I let two homeless men finger my ass and pussy at the same time.
A few months ago I was on my way home from drinks with a few friends, nothing too fancy and I was just wearing a pretty casual top and short skirt. The summer gets pretty hot here and I need to wear loose or minimal clothing to keep cool. So, I’m waiting at the bus stop near the mall, just playing around on my phone while I wait. There’s a few homeless men sitting besides the shop behind me, which is pretty normal and sometimes I’ll give them spare change if I’ve got it. They’re usually pretty forward with asking for stuff which I’m fine with, except this time I’d thrown all my cash at the bar from earlier.
So, Homeless Guy A, who I have no idea what his name was but let’s go with Steve, he comes up to me and asks if I’ve got a few spare coins. I don’t, and I feel kind of bad about it when he just walks off. Next comes Homeless Guy B, who I also have no idea what his name could be, but once again let’s go with Dave. So, Dave comes up to me a few minutes after Steve. He says that he knows I don’t have any money, but he wanted to tell me that he likes my cute pink panties that are blowing up from the wind. I hadn’t even fucking noticed. I panicked, of course, and got flustered trying to pull my skirt back in place while Dave kept commenting on how they’d been eyeing off my ass from behind while I’ve been standing the whole time. I totally blame the road design for this, fucking wind draft coming through the city.
I’m pretty embarrassed, but Dave is just chuckling at me while I hold my skirt down. It’s pretty late in the evening so there aren’t many people around to witness my wardrobe issues (thankfully), but it also means that the guys aren’t too worried about hiding their interest in me. Steve comes back up again, this time being a bit more forward by asking what bus I’m catching, where I’m heading, and all that. I tell him all the boring shit, that I’ve had a few drinks and just heading home. And look, I’m usually pretty daring with stuff but I think the drinks relaxed me, took me away from the whole panic thing that I probably should have felt when basically alone with a few rough guys hanging around me. Steve is started getting pretty close to me while he talked, just muttering about late busses while he edged up against me and put a hand around my shoulder. It’s friendly, but his hand was sorta gripping at my skin in a possessive way.
And still, my bus didn’t fucking come.
I noticed the way they get closer while I talked but it didn’t feel threatening, so I just went with it. Here’s the issue with me: being slightly buzzed gets me horny, and so does touching. So my panties became a bit of a wet mess by the time Dave moved behind me and started grinding softly against my skirt covered ass. And then he goes, “you know, instead of money you can always help us out with something else.” And my stupid brain just didn’t connect. Help them out with what? Buy them a house? An apartment? Did they want my makeup? I must have looked pretty dumb because Dave quickly put his hand under my skirt and started rubbing at my pussy lips through my panties. “Shit, you’ve got some fat lips on this little cunt,” he said. Something like that anyway, and then I finally understood. My pussy was fucking soaking through those panties and I was trying not to moan when he pulled the panties aside and sunk a finger into my cunt. It went in so easy. I was embarrassed as fuck. My cunt wasn’t used to getting randomly fingered like that and well, it turned out I liked it. A lot more than I expected.
I can’t remember exactly what I said, but I basically agreed because I was horny, and there was no one else here to witness me degrade myself like this lol. So yep, the three of us went to some public toilets across the street (yes, I still blame my late bus for this), and at that point I just completely gave up on trying to not be such a whore. Steve urged me to the ground, where he pulled my top up and then ripped my bra off. Within 5 seconds he was rolling my puffy nipples into hardness between his fingers and I was already trying to grind my pussy into the floor and Dave’s hand.
Dave was between my legs at that point, he’d shoved my panties off already and was jamming his dirty fingers into my cunt. It made those giveaway squelching sounds and I couldn’t even hide how turned on I was. He was fucking me with two fingers pretty easily, which gradually turned into three while he rubbed my clit harshly with his thumb.
Steve was watching from behind, his hands still tugging at my tits while he made comments about what Dave was doing. Gross comments like: “bet she’d fuck a bottle if we gave her one right now” and “look how hard that pink little clit is just for us.” I was like, BURNING with shame, but being degraded like that somehow turned me on even more. Steve reached down and gave my clit a few sharp smacks while Dave kept fingering me and that was it. I came so fucking hard from getting my clit slapped. Like a goddamn whore. I was gasping through it while Dave just fingered my pussy even rougher. But they really weren’t done with me at all. After that, they insisted I help them get off too, and I was down for it even if I found it kinda gross. Who the hell knows when the last time they showered was, but yeah, I ended up with both their cocks in my mouth. Same time and all. Trust me, I tried really hard not to breathe while they fucked my throat like that. My whole mouth was sore and my lips felt stretched to the max. I can assume my lipstick probably looked like absolute shit by this point as well. But like, fuck. It took them a while to cum, which meant I had to keep stroking the base of their cocks while sucking (hello, dead arms), and then finally, FINALLY they were almost there. Until Dave piped up with his request: “let us cum on your asshole and pussy, and then you get to cum again.”
Which, yeah. I was still wet and horny as fuck. And at least then I wouldn’t end up with their cum in my mouth and have to hold myself back from spitting it out instantly. Pussy and ass? Easy, I’m on protection and the rest I can just wash off and never have to think about again. I was sold. So they pulled out of my mouth, grabbed my legs and sorta yanked me upside down so that my cunt and ass was in the air. Steve lined up behind my cunt while Dave pressed his cock up against my asshole.
They jerked themselves off like that for a moment before literally cumming on top of both my holes. Not in, but on top. I felt really disgusting and gross but fuck, it felt incredibly hot. My holes were still begging for attention though, and that was dealt with pretty quickly too. They didn’t let me move from that awkward position, still holding my legs in the air like that while Dave knelt down and start swirling his fingers in his cum on my asshole. He gave me a look, like checking if playing with my ass was okay, but even if I said no I don’t think it would have really done anything. I was down for it though, nodded, and then he pressed one finger slightly into tight little hole, just using his own cum as lube.
And fuck, that felt so invasive since I haven’t really done much anal play before, but I loved it. I felt like a completely disgusting set of holes and it made me horny. Again. Steve basically did the same thing with my cunt, except he wasn’t so gentle about it since Dave had already blasted my pussy with three fingers before. My clit and pussy lips were getting red from all the slapping before but I could still feel myself edging closer to my second orgasm.
They kept it up like that, double penetrating my asshole and pussy with their fingers together while I reached up to rub my clit. God, I was so fucking turned on. My asshole was tight as fuck, even though Dave kept it really slow while he added a second finger, and then a third. Their cum worked disgustingly well as lube despite it all, and my cunt was wet enough to let Steve finger fuck my pussy with four fingers while I worked at my clit. Four fingers is a lot, okay? Add that with the fingers in my ass and I was basically just a set of holes for these homeless guys to have their fun with. I tried to slap my own clit to get myself to cum again, but it didn’t feel the same as when they did it. Steve laughed when he saw me try to do it, and that’s when he shoved my hand aside so that he could pull my clithood back and rub at it really, really hard. So fucking hard and rough that I came again within just a few seconds. My pussy and ass clenched around their fingers while Steve abused my clit like that. God, I felt so raw down there later but it was worth it.
I don’t really remember what happened much after that, but the guys let me calm down after that second orgasm. I was feeling boneless and just needed to breathe. They left me in the bathroom while I struggled to shove my apparently useless panties and bra back on, I was so fucking tired from all of that. But it was good, and thankfully not a single soul was around to see me do that: letting two homeless guys abuse my cunt and ass in a public toilet, and let’s hope it stays that way!
Source: reddit.com/r/eroticliterature/comments/vfa3xi/i_let_2_homeless_guys_finger_my_ass_and_pussy_mf
Did you take STD tests after that?
I’ve been in a similar situation in a bar. So hot.