[MF] [MMF] Ann round two. My crazy, hot friend. A quick side story, but then we had a drunk threesome out of town. It didn’t go great for me, but I’ll never forget it.

My first Ann story can be found in my post history. On mobile, I don’t know how to link but will edit later when I figure it out.

And this is SUPER LONG because there’s a middle story. Threesome is WAY down below.

The BACKGROUND: I finally got to have sex with a friend I’d been lusting after for years. We were both bartenders and definitely lived the lifestyle of partying several nights a week. We had lots of free time, disposable cash, and badass attitudes. She was a total fucking bombshell. Crazy as fuck. 5’7”, maybe 105 lbs tops. Long brown hair, very slim frame. Tight ass, perfect tits. I think C cup, but in retrospect mayyyybe a B cup that looked bigger on her small frame. Didn’t matter – they were perfect. So perfect. Little pink nipples. Her tits were perky, “retroussé”, I think they’re called? Beautiful face. Eyes that could destroy you. She always reminded me of a white Rihanna. Sexy and sultry. She was a 9 all day, and she knew exactly the effect she had on guys.

I’m 5’9”, 145 lbs, buzzed my hair back then, musician, punk rock style. My body has never been outstanding, but I’m handsome and occasionally funny and smart in a weird way, with a cocky attitude that girls in their 20s seemed to dig back then. Combine that with a sexy nightclub job and I did alright for a few years, with girls hotter than I would’ve gotten otherwise.

I’m at the death rattle of my 30s now, “California sober,” and reliving the glory days. This story and the previous story took place when I was about 25, and she was 26. We’d known each other for years, she was my best friend’s hot sister. We started getting closer around 22ish and hung out all the time, usually drinking and doing risky stuff at night. Dancing in our underwear in the rain, sneaking into abandoned buildings, getting thrown out of bars because she started a fight. Drunk make outs and tit flashes, not because she wanted me but because it was funny and crazy. Shit like that. I hung in there because I was obsessed with her, as were many many other guys.

I hooked up with other girls. And she always had a boyfriend she was “trying not to cheat on this time.” Her boyfriends usually lived in other towns, for some reason I haven’t yet analyzed.

We drank together A LOT. Like three or four nights a week probably. Usually beers but whenever she switched to cocktails I knew I was in for an unpredictable evening.

She hooked up with lots of guys. I hated it but it also made me think it was possible for it to happen to me. She was not at all the shy type.

OK, NEXT STORY:

We finally fucked one night and it was incredible (hit the post history). If I had it bad before, I was really fucked now after getting a taste. My whole life was trying to fuck her again.

We didn’t acknowledge the night we slept together. The next day it was business as usual for us.

Maybe two/three weeks later, I have a couple guys over at my place, one of them brought coke. I had only done it maybe twice at that point, but I had entered the nightclub lifestyle and it was around. So we’re banging out lines at my place, listening to music and bullshitting. It’s like 7am and we’re still going. I get a text from Ann – she’s still up, fucking WASTED. She’s upset, wants me to come over. I obviously tell the guys it’s time to leave and I race to her apartment as fast as humanly possible. I knock, no answer, I walk in. I’ve been there a thousand times and she invited me. I don’t see her anywhere. I’m thinking this is weird as fuck, suddenly she jumps out of a closet and scares the fuck out of me – I probably screamed like a girl. We laugh, she’s fine, we go lay down in her room. Just on the floor for some drunk reason.

She’s wearing a thin charcoal grey shirt, the really soft, worn-in kind that clinged to her braless tits. Her perfect little nipples were hard. Little shorts. We bullshit for awhile, I’m coked out and trying to play it off, but I have to piss every five seconds. I’d been drinking, too.

So we’re laying there laughing, facing each other. Awkward silence. She suddenly goes “you have a giant dick” and busts out laughing. I laugh too. Truth told – my dick is absolutely not giant. It’s decent, I’m not embarrassed, but definitely not huge. I think she just remembered the shower that way because I was explosively hard for her and we were hammered.

I kiss her, touch her tits, and have to piss again. Then again. The shitty coke is ruining everything. I’ve replayed what should’ve happened a thousand times.

I should’ve asked if she wanted to see it again. I should’ve let her just touch it, play for awhile and see where it leads. I should’ve ripped her shorts down and gone to town on her. I should’ve licked her beautiful pussy right there in the morning light. But I had to piss again and again and the moment was ruined. I hated myself. We went to breakfast instead and I crashed for two days.

THREESOME STORY TIME:

It’s probably two months later, early Fall. One of our mutual favorite bands was playing two nights in a row, a few hours away in Chicago. I buy two tickets for each night and book a very nice hotel room (with one bed, cause I’m so slick) for two nights. She’s gonna go with me. Day of show rolls around – she cancels. She’s hungover as usual, can’t get out of bed. I’m floored by the disappointment, but I go alone.

I get to town, get the room, go to the show. As I’m walking out of the venue, she texts me. She’s here. She felt bad and drove in. She missed the first night but fuck it – she came! I’m so excited.

We immediately go out bar hopping. We get fucking hammered, running around the city like big shots, acting obnoxious, asking bartenders where we should go next. Chatting up anyone who would listen. Nonstop laughing and we’re acting like it’s New Years Eve. I’m very drunk but hanging in there because she’s acting crazy, flirting with other girls, and I’m thinking this has to lead somewhere, we’re basically on vacay, and holy fuck what if we end up in a threesome. She’s done it before, she’d told me once.

We go to a loungey nightclub. It’s a weekday so it wasn’t super busy and we had lots of time to buddy up with people. It was perfect. We chat up a male bartender, tall, handsome white guy, well built, kind of a stud. He asks what we’re doing later, she tells him we’re staying at this nice hotel and we’re going to drink until the bars close then go back and smoke the weed I had brought. We invite him to join us, almost as just a thing you say, not really expecting it to happen.

Bartender guy gets our numbers. I’m picking up on a vibe, not what I had in mind, another guy, but I’m not thinking right. All I want to do is fuck Ann again – I don’t give a shit how it happens. I assume we’ll never hear from him and we move on to another bar. We’re running around drunk in the streets, laughing, yelling at cars, bullshit like that. So So Drunk. But we do this shit a lot and have huge tolerances.

We head back to the hotel, def time to smoke weed and pass out. I obviously hope we’ll fuck but that’s her call – our relationship wasn’t one where I could lead there. We get a text from the dude bartender – are we still up? Do we want to hang? That shit. She invites him over to smoke weed. That’s all that’s discussed.

He soon joins us, it’s gotta be 4am by now. I sit in the desk chair while she lays on the bed close to me. Dude is chilling on the other side of her. I roll a joint, we just chill. I’m just staring at her, lost in my drunken desire for her. The dude obviously reads the situation and is getting ideas. I’m down with literally any event that leads to fucking her.

We towel the door and smoke the joint. There’s a vibe in the room. I join them on the bed, she’s in the middle. There’s an air of anticipation as two horny dudes flank a beautiful girl in a hotel. He looks to me to see if I’m ok with a little touching. I nod. He starts slow and just kind of puts his hand on her hip, testing the waters. I scoot closer to her. She’s just laying there with a little smirk. She must’ve been getting a kick out of watching us nervously navigate the vibe.

He looks at me again for permission: I look at him and nod again. He starts feeling around a bit more. I might’ve been getting slightly handsy too.

Suddenly, she sits straight up, arms behind her, thinks for a second, stands up at the foot of the bed. Hands on hips. She looks at us with her dimpled little smirk.

Ladies and gentlemen, I will never, ever, EVER forget the following words:

“Alright, boys. Strip.”

She giggles and rips her shirt off. Bra off. Pants and panties down at the same time. Blink of a fucking eye she’s naked. Within milliseconds we boys followed her instructions. We take off our clothes like they were on fire. Her body is so lean and beautiful. Her tits are fucking insane. Her smile is electric. She’s very charismatic.

His body is much nicer than mine. Well built, not chiseled like a model but very manly. Light hair on his chest. He’s probably late-20s, easily 6 foot, slightly longer hair. And this dude had a fucking giant dick. An actual giant dick. He was as big limp as I was hard. I mean, I couldn’t help staring at the fucking thing. Part of me wanted to hold it in my hand just to feel the weight of it. I felt so fucking insecure. He was just overall much more of a stud than me. I could’ve cried if I wasn’t so horny too.

Now I don’t know where I got the mental guidance to lay out a couple rules, because I had no right to. She was not my girlfriend. I was not in charge – she was calling the shots. But I told him “two things: you’ve gotta wear a condom, and you’ve gotta leave when it’s over.”

Fair enough.

She crawls back to lay in between us. She is 100% in charge and enjoying every second of it. She knows exactly what she’s doing.

She takes Mr Monster Dick in one hand, and Mr Trying His Best in the other, just playing around with our cocks, laughing at the situation a little.

The vibe for her was never about being horny, it was always about doing something crazy.

Anyway, she lays there smiling and with a dick in each hand. Other dude gets up on his knees on the bed, almost behind her, next to her face. She leans her head back and takes that giant cock into her mouth. Sucking upward to him. I watch for a minute. Half of me is heartbroken seeing her with another dudes dick in her mouth, but I’m also incredibly turned on by it, getting to watch her in action from that perspective.

She spreads her legs. I kiss her beautiful tits. Suck her nipples, kiss her stomach, her thighs, and finally dive into her majestic pussy with my tongue.

I could literally eat her pussy for hours – I fucking loved this girl and her body was just fire. I just lick and lick away while she slides his impressive dick in and out of her mouth, lifting her chin up to him. I don’t want to stop cause I just closed my eyes and tried to ignore how insecure the other dude has made me. Focus on her.

After several minutes of this, she rolls over and gets on all fours. Mr Stud grabs a condom he’d brought – he’s no fool. He knew what he was getting into. He puts it on the baby arm he calls a dick and enters her from behind, starts fucking her slowly.

I did not care for this at all. I thought I would but now I’m watching a girl I think I’m in love with get fucked by a stranger and I’m getting sad.

She reads this on me immediately. I’m just watching. She snaps to reality for a second and looks at me and says “hey come here.” But like sweetly.

She takes my cock into her mouth. This is the first time she’s gone down on me so I’m trying to focus on this, her lips around my very hard but not-the-biggest-in-the-room dick. Of course, it was world-class. She’s got more experience than the both of us dudes put together.

But I just can’t do it. I’m drunk. I love her. This is killing me.

I pull my cock out of her mouth and just let them go. He fucks her how he wants to. Hard from behind. As she’s getting drilled, I look at her and say the most pathetic thing in the history of pussy-ass-ness: “I love you.”

She laughs, says “what?”, with the tone of “dude get real”

I basically try to black out what’s happening. She’s fucking some other dude. Missionary. Back to behind. He’s just going to town on her. She’s getting loud, he picks up speed and finally cums. And I’m so glad it’s over.

He briefly recovers while we all just kinda chill. He starts to get dressed, probably assuming that she’s my girlfriend but I enjoy watching her with others. Mr Big Dick would’ve been wrong. But he goes to leave pretty quickly afterwards. Ann laughs and says something like “good to meet you. I’m gonna fuck my dude now.”

I perk up. Get this fucking guy out of here. He leaves. Never caught his name.

She attacks me. She’s not even close to done. She sucks my dick for about a minute until I’m fully hard again, and without a condom – we didn’t do that shit – she straddles me and slides my cock into her pussy.

She rides me, I just admire her body. I roll her over still inside her. I fuck her missionary, her pussy is the whole world to me. Everything about her was actually. I don’t last much longer and pull out to come on her stomach. Hard. It’s a mess. We don’t really stop, though. I power through because I’m young enough to get hard again soon, and I have to get another taste of her. Who knows if this will ever happen again? It took me almost a decade to get with her.

I lay her back and dive my face into her pussy. I won’t stop until I’m dragged away.

She drags me away. Brings me up to her for a kiss, tasting her pussy on my lips, and puts my dick back inside her. I’m not rock hard, but it’s enough to keep going.

I fuck her missionary for a few minutes and get hard enough again. She rides me, I fuck her from behind, stuck a finger in her ass. She reaches back to rub her pussy. It’s pretty animalistic at this point. She comes. Hearing her pretty much sends me over the edge and I come again. This time on her ass. Not nearly as much volume but I’m fucking spent.

We collapse. She wants to keep going. I don’t know if she even realized I came again. She said “I want you to fuck me in my ass.”

Dear reader, I’d love to tell you I had another one in me. But I’ll tell you what I told her:

“Honey, you’ve made me come twice in the last half hour. I can’t. Im sorry. I’m done.”

We fall asleep.

The next day was probably among the worst hangovers either of us had ever had. We later walked around, got dinner, went to the second night of the show, and that was that. We drove home individually of course and I was left with hours of alone time to process what had happened the night before.

It would be another two years before i got to touch her body again.

Source: reddit.com/r/gonewildstories/comments/cvj0on/mf_mmf_ann_round_two_my_crazy_hot_friend_a_quick