skip to the filthy stuff by searching for &&&& (sorry, I really enjoy writing the background stuff, but if you’re just horny go for it)
A few weeks after I got back from [my last trip to London](https://www.reddit.com/r/gonewildstories/comments/hyltsz/i_24m_fucked_my_longtime_crush_after_she_23f/), I started bartending and DJing full time and decided that PA wasn’t enough fun for me so I decided to move to NYC into a shitty apartment I found on Craigslist. I had 2 roommates in a 5th story walkup in Manhattan, and it was the most exciting thing ever for me. Basically broke and surviving off of money I had saved up from the 6 months I lived at home, I got deep into the Manhattan bar and club scene, trying everything possible to “make it” as a DJ. It was scary and very hard at times thanks to NYC having the most competitive DJ market in the country (sorry LA). Thankfully, I wasn’t a newbie like many other DJs so after proving myself and making the right connections, I started enough working gigs that paid well enough to avoid thinking about a 9-5 and meant I just got to fuck around, gig, and have fun — I was working 4 or 5 nights a week. One of those gigs was a Friday night residency at this club where that was “hip” enough to get me some cred in the city.
What was especially great was one of the bartenders there, Madeleine (Maddy). She was drop-dead gorgeous — practically a dead ringer for Yvonne Strahovski — blonde, 5’9″ or maybe 5’10”, the longest legs, and a wide, gorgeous smile. She served a tour in the Middle East (was a combat veteran) and had a masters degree — a year or two older than me, she was a total badass, but she was just bored with working corporate jobs and bartending was an easy way to make money while trying to find her passion. Not to spoil anything, but she had naturally small breasts and wanted to feel more confident (and let me tell you, she was as confident a woman as I’ve met), so when she got out of the military she had them done. When I started DJing at this club, she and I immediately hit it off — we both loved Calvin Harris and Robyn and Miike Snow and M83 and we would exchange texts about music all the time at random hours. This was simply platonic, and while she was definitely extremely hot, I also knew she had a string of very wealthy boyfriends and I was way outside of her league (I still am, and I’ve done pretty well. She’s an obscenely successful real estate agent now and her fiance is a professional athlete in one of the four major North American sports. Ridiculous.) At the time I met her, she was driving a $60k BMW that an ex-boyfriend gave to her *after* they broke up. The ex didn’t even make her give it back when she started dating someone new. She owned dudes, and for good reason — and it wasn’t like she was manipulating, lying, or deceiving these guys, she just had power because of her beauty and personality. But, we were music buddies. I’d be upstairs in the booth, and she’d text me requests then wait for me to physically acknowledge them and she’d beam a smile or blow a kiss back to me.
For the first nine months we knew one another, when she’d be dating someone I’d be single, and vice versa ([Lisa](https://www.reddit.com/r/gonewildstories/comments/i3dkia/i_22m_finally_fucked_my_fwb_20f_after_a_month_of/) even came over twice during our attempt to stoke the fires of our try at a long-distance relationship). Our romantic lives never synced up (not like I ever thought I had much of a chance, I had roommates, she dated guys who had giant expense accounts). Over that time we got closer, friend-wise, and opened up about personal stuff and life. We offered each other dating advice and once I even bailed her out of a bad date with a fake emergency phone call. After closing one night, we got to talking. She told me she was going to Vegas for a bachelorette party for her sister the next weekend, and asked if I knew anyone out there who might be able to help with lines or bottle service or whatever. Eagerly, I responded that I did! My buddy was (is!) a host out there and I gave her his info. Later, I texted him as well, letting him know he HAD to hook Maddy up with whatever he could on my behalf.
So, the next Sunday I was on an early dinner date with a girl who I’d seen maybe two other times to that point, and I got a text from Maddy. It was a picture of her at one of the pool/beach clubs, smiling and posing in aviators and a jet black bikini. “Thx so much for the hookup, I owe you. :)” was what came next. Immediately, I put my phone away and tried to concentrate on dinner and conversation, but I couldn’t stop thinking about her photo and text all night. When my date ended, I texted her back, “looks like fun! glad it worked out :)” and she sent back a photo of her with two of her friends on a day bed laying down giving the peace sign and smiling. I did truly immoral things to myself that night looking at those photos.
The next Friday I was back at work and went over to the service bar to greet her before we opened — she bounced over from behind and hugged me and kissed my cheek, thanking me for hooking her and her friends up in Vegas. The night went as usual, and Maddy and I were texting throughout it. She sent me a few song requests, but I told her I’d only play them if we did a shot each time (“only a baby shot, okay?” she ordered me), so I’d go down to the bar after each song to do one. It was a very busy night, but around 315a she came up to the DJ booth with one last pair of baby shots because I had played her most recent request of the night. We did them, then she got in the booth with me and draped her hands around the back of my neck over my headphones and I placed a hand on one of her hips. Internally, I had a million thoughts going at once — “She had a boyfriend, right?” “I’m kinda sorta dating someone, so is this ok?” “Wait, isn’t she dating someone on the Rangers or something?” “Hold up, what’s happening??” We both took a beat, looked into each others eyes, she giggled a little, and I… hugged her and rested my cheek on her hair. Yep, a nice friendly hug because that’s what friends do, they hug (HIIIIIGHWAY TO THE FRIENDZONE). After a few seconds she sorta stepped back, looked me directly in the eyes and said something like, “Is there anything else I can do for you?” I told her no, and she went back to the bar. Fuck me sideways, right? Twenty minutes or so later, the lights came up, I went to settle my tab (Maddy comped me), we hugged good night as usual, I got my check and said goodbye to the rest of the bar staff and security, and started my way home (I lived about 20 blocks from the club and figured a walk to clear my head instead of the subway or a cab after my numbskullery would be good).
Ten minutes into my walk, Maddy texted me, asking me why I hugged her in that moment. “I sent you those pictures for a reason, I tried to get you to kiss me in your booth, and you hugged me? You’ve told me yourself that you’re basically single, so what the hell dude?” (As I said earlier: confident.) I stopped dead in my tracks — and let her know I just didn’t want to make things weird (then erased it because I had already made things weird) — and let her know I just didn’t want to screw up our friendship. She texted me back and told me to stop worrying about that, that we’d be friends no matter what — but that she was leaving work in five minutes and she needed someone to walk her home (she lived about 5 blocks from the club in some luxury hi-rise — of course). I wasn’t going to miss this signal too, so I told her I’d wait for her outside and booked it back in the chilly late night air. By the time I got there, she had just walked out and I was a little out of breath. She laughed and we walked to her place, arm in arm at first and then holding hands. It felt weird being in this situation because I honestly thought she was seeing someone — I didn’t need an NHL player trying to stab me with a fucking skate, but fuck it. It was Maddy. She always got what she wanted, though in retrospect I think me “rejecting” her in that moment might have worked towards my benefit.
We got to her place and she asked if I wanted to come up with her, which, duh, yes. She lived on the 40th-something floor of the building — I joked we could go to my place if she wanted to slum it on the 5th floor of a walkup (my room has a fire escape!) and she laughed. Anyway, we got up to her place — and the views were spectacular. Her roommate wasn’t home that night so it was just us. Moments after getting there, she made us each a drink (“and not a baby shot this time”, she said with a grin). We chatted for about three minutes, then she said she had to freshen up and went into her bedroom. Sitting on her couch, I kinda nervously sucked down most of my drink — moments later she opened the door to her bedroom in her bathrobe and asked me if I was going to freshen up as well. Not wasting any time, I got in there — her shower was running hot with steam already accumulating in the bathroom. She insisted that we both shower after work (which I’ve always a habit of anyway after DJing… you get sweaty and a hundred random people try to shake your hand or dap you when you’re DJing. Gross. And this was pre-COVID. Yuck.)
&&&&
She dropped her bathrobe — her bare back, long legs and small but taut ass staring at me but without looking back she got in the shower and told me to get in there with her. I stripped naked, my dick starting to get hard. Her shower that was easily large enough for four people, so giddy-up. She had her back to me and turned her head to see me naked standing there, and smiled. I stepped forward and she turned around, entirely exposing herself to me. My only thoughts were “Holy fuck. Holy fuck. Holy fuck.” She was even better looking naked than I expected, which is saying something — her body was perfectly toned, her breasts — while fake — were really nicely sized for her frame. Her pussy was completely shaved with beautiful lips, and her whole body was lightly tanned. The other thing I noticed — scars. She had one scar on one of her thighs near her pelvis and another a few inches below one of her armpits — both places you wouldn’t see at work, even when the female bartenders and cocktail servers would dress in skimpy clothing. I’ve rarely been surprised by a woman’s body, but Maddy was truly jaw-dropping.
Immediately, we kissed, both of us having had more than a few drinks at work it was a little sloppy, but the passion was real and earnest — this lasted for a few minutes, with us groping one another as she shoved me against the wall of her shower. Without breaking our embrace, she grabbed her body soap bottle and squirted it on her hands, then pulled back from me and grinned, rubbing herself up and down with the suds — it was fucking hot as hell. I took the bottle from her and started lathering her too, massaging her legs, her stomach and chest, and after turning her around, her ass and back, then her breasts from behind. She gave a slight gasp when I soaped up her nipples and I won’t lie that it made me go from very hard to absolutely rock hard. Her breasts felt pretty real considering I knew they weren’t (she had explained why she got implants before to me in a very matter-of-fact, non-sexual way), and she was clearly enjoying the attention I was giving them. I got closer to her, kissing and nibbling on her neck, with my dick rubbing against her backside, and she took some of the suds off her body and grabbed my dick with one hand and started gently jerking me off. Her hands were stronger than I expected, probably the result of an adulthood of bartending and military service, and it felt amazing.
We both got under her multiple shower heads (again, luxury hi-rise) and got the soap off, all while kissing. At one point I pulled back, the water flowing over us, and asked her what brought this on and told me with a smile that if I asked her this again, she’d lock me on her balcony naked for the night (fair enough). We continued to make out until she broke our kiss and dropped to her knees, smiling up at me. She started jerking my cock while kissing my balls and shaft, until the moment she decided to put it in her mouth, her warm tongue and lips sliding up and down my dick effortless from the head to my pelvis (I’m about 6’5″-7″ hard and about 4″ in girth), looking up at me as the water hit my back. I grabbed the body soap and told her to stop for a second, then squirted it on her tits, “Maddy, I want to fuck your tits” I told her. She smiled and soaped them up, then carefully placed my cock between them and pressed her tits together around me, slowly working my dick at first and then faster. I slipped out a few times, but she was persistent and made sure I got to fuck her gorgeous tits for at least a few minutes — I had fantasized about this moment for such a long time (since the day we met?) and I was very close to blowing my load so I stopped her and pulled her up to face me. We made out under the showerheads as the soap rinsed off our bodes. She said me we should get out and dry off, so she turned the water off and stepped out, covering herself in a towel and tossing one to me. Weirdly, it was nice to have a moment to collect myself as we dried off and I softened up a little bit. We went back to her living room where we finished our drinks and I tried to take charge (which maybe she’d be into since she was *always* in charge).
I picked Maddy up and brought her to her bedroom, laying her down and I began by grabbing her ankles and bringing them together, kissing them, then working my way the inside of her legs until I reached her pelvis, “I fucking love your legs so much, Maddy, they’re incredible”, making sure not to miss her scar, “you really have the sexiest legs I’ve ever seen.” She gave me a huge smile then told me to kiss her, and I did as told. She rolled onto her side, and we spooned, pushing her ass into my crotch. I touched her breasts and nipples playfully before moving one of my hands down across her stomach and eventually touching her pussy. It was soaking wet by now, and I gently rubbed her clit while kissing her neck and shoulders — she instinctively reached back again and grabbed my dick with one hand. Maddy was breathing heavily as I did this, so I moved my hand down and started rubbing her lips and clit — then asked her, “can I?” — she nodded her consent quickly and whispered “please”, so I carefully slid a finger inside of her. Immediately, she arched her back and squeezed my dick even harder than before and I groaned. She grinded herself against my hand and crotch for a minute or two, moaning and grunting as she slowly went faster. I turned her onto her back and started to kiss and lick her nipples, and she let out a soft whimper — I could feel her getting wetter and tighter as I sucked and kissed her nipples while finger-fucking her, so I pushed a second finger in — and she made it clear how much she loved it. “Just keep on doing that, mmmm,” she whispered and I followed her instructions for a few minutes, before I slowly made my way down and started aggressively sucking and tonguing her clit while still fingering her. This lasted for a few minutes, but she asked me to just fuck her (she later told me she thought it might take too long because of the booze and she didn’t want either of us to get frustrated or tired).
She asked me if I had a condom, and I excused myself to grab it from my DJ bag (always be prepared, right?) and came back — she took the wrapper off and unrolled it on my dick, then spit on her hand to lube it up a little bit. She laid on her back and I gently pushed my dick inside her — she was dripping wet, so lubrication wasn’t going to be a problem. She held my face with two hands and we deeply kissed as I started thrusting at a more rapid pace, only breaking the kiss for one of us (or both of us) to moan. I pushed back and we looked into each others eyes — we both smiled at each other in a way that wasn’t too far off from when I’d play her requests and she’d be beaming — we had a connection then and we had a connection this moment, too. In one motion, I turned her to the side and spun behind her and started fucking her with one of my hands on her clit, rubbing it in circles as I started to pump her hard. Maddy started squeak-moaning (it was cute) as her breaths got faster and shorter. Pulling her leg back, with deep thrusts and the proper angle, I could hit her g-spot from this position and she started gripping my arm — “dontstopdontstopdontstopdontstop”, she cooed as I kept going. A moment later, she shuddered and came hard, vocalizing her pleasure with a few repeated moans.
I could feel myself getting close again, too, but wanted to fuck her standing up (I’m 6’6″ and don’t often get to comfortably have sex standing up thanks to height differences). After her orgasm subsided and we made out for a minute or two as we gently fucked, I asked if I could fuck her standing up. She gave me a grin and pulled me out and stood up, taking my hand and walking us over to her door frame, and stuck her ass out, “like this?” she said, looking back at me. That was invitation enough — I dropped to my knees and licked and sucked on her pussy for a minute or two, then stood back up and entered her pussy from behind, one hand on her shoulder, one hand on her hip. I pumped her hard (this was the first time having sex in this position for me where I didn’t have to bend my legs to a degree that my thighs burned within a minute, or my partner had to be on her tip-toes, which is honestly probably more exhausting), and it felt fucking amazing. “Maddy, holy fuck, I can’t believe we’re doing this,” I told her, “you’re fucking amazing, you know that?” She looked back, gave me a little giggle and smile, and kept bouncing back into me — the friction at this point was good enough to get me to come. I let her know and that intensified her efforts, “you want to blow your load, don’t you, give it to me, please come inside me” she begged, and that was enough. I gripped her body and frantically pumped her until I came with serious intensity into the rubber.
We both stood there for a moment me, holding her, Maddy kissing my neck and ear, then I carried her (still inside) back to her bed and we laid there until I softened enough to slip out of her. “All that because I got you a few perks in Vegas?”, I joked, “Jesus, I should have done that months ago.” She playfully slapped my face and laughed, “that’s not why this happened, but that was very nice of you. And how many condoms do you have in your DJ bag, you creeper!” I corrected her to let her know I had “one condom”, and it was in case of emergency. We spent the next 45 minutes talking — I asked her if it was okay to talk about her scars, and she let me know the story about her injuries — she really is a badass. And she finally gave in and explained that her boyfriend had been emotionally and physically distant for the last month (something to do with having a poor season?), and after a few attempts to bridge that gap, she told him she needed a break so he could try and figure out what was wrong (they did get back together from the break, but it didn’t last long). We hooked up a few more times, but it never really got past the physical level with us (even with our emotional “friendship” connection, romance wasn’t in the cards). It was always late nights after work or booty calls, we never went on a proper date or anything (though one time we went and got a slice after hooking up and I was asked by a homeless guy “how much are you paying that fine lady to walk next to you??” …well played homeless guy, well played). She told me after our last hookup that she and her boyfriend were going to try again, and I respected that decision (though, boy, what a fucking bummer). We worked together for a while longer (two more years, actually, before she decided to go on a six month trip to the Balaerics) and there was never any awkwardness. We mostly lost touch (still occasionally sending each other new music to check out), but would run into one another at random industry nights and hug and catch up, her even congratulating me a few months before COVID for getting married (yes, that happened last summer, and no, I didn’t tell her so she must have figured it out from catching that from my social media or something).
Source: reddit.com/r/gonewildstories/comments/i7gc4j/i_25m_fucked_the_hot_bartender_27f_after_she
That. Was. Very. Hot.
Holy shit. This is so good. You’re a good writer, man.