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[M] The time I hooked up with my Manager (long)
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Spotlightontheslide is a male
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Amanda and I used to chat about our past hookups a lot. We worked as closers at a big chain coffee shop where the only things they cared about were whether it made money and that it didn't burn down. We worked late usually, closing at 10, out by 11. There were supposed to be three of us but the store always had a hard time keeping a third closer so usually it was just Amanda and I. I'd run the drive thru and she'd handle most of the closing tasks herself. At the time, I was freshly single and desperate to fuck anyone, even at the possible expense of my job. The drivethru had a camera so you could see the customers and Amanda always got a kick out of hearing my voice shift into a flirtier tone, even more so when the woman on the other end would flirt back. Sometimes I got a number. Usually they just wanted their coffee or enjoyed the attention. Not many people wanted to fuck someone in a stained apron, it turned out.

Amanda had been with her girlfriend for a little less than a year at that time and was starting to feel it. Her gf was pushing for a move in and Amanda was starting to get the itch to move on. It was a tough situation where they felt it was right but never right enough, and every nudge closer seemed to nudge Amanda further away. Usually our nights would start with us bitching about dating and eventually turn to our past hookups. She told me about gay bars around town, which ones were worth a damn, which ones she had any luck at. We'd compare and contrast our hookup stories, most of which was her arguing that she could make a woman cum harder than I ever could. I've never been one to brag, so I let her puff herself up and shine her little gold star that she guarded so jealously. I'd talk about the nuclear waste void of dating apps, my craven attempts to sleep with anyone who would look at me, and eventually, I'd somehow end up trying to barter with her over who would scrub the mats on Deep Clean Night. It was a task both of us hated and almost always fell to me, but sometimes if I played my cards exactly right, I could convince her to trade tasks with me. 

The joy of it wasn't just in handing off a task I hated to someone else though. Amanda was thick with three c's. To watch her move around the bar was to watch a 5'1 tree trunk with thighs the size of my head and bigger tits than two hands could possibly hold. Her ass was enormous and seemed perpetually on the verge of ripped whatever pants she was in. I envied her sports bras when she scrubbed those mats. Many a night after work was spent repurposing the mental image of her huge brown tits bouncing while she scrubbed into images of her body shaking and jiggling in every direction while we fucked. It was a task that had to be done out in the parking lot, which meant in order to steal a look, I had to find reasons to go outside when she happened to be doing it. By the time we were working together, I knew exactly which tasks those were and would usually save them up until she had to scrub the mats. I would have broken down cardboard for hours if it meant I gotta see her fat ass bounce in yoga pants for even ten minutes, which she knew and often used against me. On nights where she would be scrubbing the mats, mysteriously there always seemed to be more cardboard than usual, or more trash to be taken out, or more windows that needed to be cleaned. I'd watch as she worked. Diligently, intently. Using a thick, long handled brush, she'd scrub in small patches repeatedly. The collar of her button up work shirt drooping with her heavy cleavage. Her wide hips gently shifting back and forth.

She never looked up at me, but sometimes she'd smile to herself. Maybe she'd glanced out of the corner of her eye and caught me trying to hide the immense hard on I had. Or maybe she just knew that she was being watched and didn't mind the attention. After a few months of working together, we'd started to chat about more than just our hookups. She'd tell me about her favorite hookups, what they did, and what her fantasies were. She told me she loved to top women but had always wondered about bottoming. One night she joked that straight women who wanted to experiment were always bottoms. I told her that most of the women I had hooked up with wanted to be submissive and liked being told what to do. We compared notes. She told me about a recent experience trying to bottom and ended up power bottoming the hook up. She guessed that if she were to try it again, it'd have to be with someone who could force her to "shut the fuck up and take it." A shiver ran down the shaft of my cock, situating itself inside my balls. I let out an exhale and started scrubbing anything I could get my hands on. That night, I jerked off from the moment I got home until the sun rose.

Her shirts seemed to get tighter, more see through, or show more cleavage after that. She was the only manager on staff for closing so it's not like anyone was around to check her. Coupled with her decision to finally break things off with her girlfriend, her return to the dating market seemed to be going reasonably well. Or at least she seemed determined to showcase her wares, as it were. I stopped trying to hold back from looking by this point- it was clear that she knew she was being looked at by a lot of people, not just me, and she didn't mind any of it. She developed tiny splotches on parts of her cleavage where dots of steamed milk had popped out of the pitcher and burned her. I wanted to test if fucking her senseless and cumming on her fat brown titties was an effective medication. Our conversations became more crass; sometimes she would even catch me looking and pretend to adjust the collar of her shirt as though something just wasn't quite fitting right. She'd jiggle softly, "fix it" and go back to what she was doing, smiling. She liked the power she had, especially when she started to follow it up with "bumping" into me in the back room. 

Deep Clean Night was torture that month, not least of all because management finally hired a third barista to work nights. Amanda wore her most professional slutty shirt, a tight black polo that she left two buttons undone on, paired with yoga pants that she'd recently complained had started to develop a small hole in the crotch. I'd seen it when she was doing the food inventory that night. I'd been in the middle of training the new guy when she caught me looking. She smiled and adjusted her crouched position, just happening to spread her legs just a smidge wider, revealing the lip of her brown pussy peeking out from behind a thin yellow thong. I nearly passed out.

We were both thrilled to be able to hand off scrubbing the mats to the new guy, however, which left more time for flirting and banter back inside. A joke about the milk count turned into a running gag about her wondering the taste of every type of milk we served turned into a conversation about how "thirsty" she was after somehow hitting a dry spell. She'd had a FWB following the breakup, but they'd been gone and she was struggling. Even at her worst with her ex, they'd still had sex at least several times a week. The two week she had to wait for her FWB was entirely unreasonable. I joked that I was having better luck than she was at that point, having recently had something of a hot streak. "jealous" she said, holding on to the S for just a little too long. She turned around, bumped me with her ass, and returned to work. I'd played dumb for long enough. The time was now.

We closed out the store for the night around 1am, high fived the new guy, and sent him on home. Amanda and I lingered, kicking rocks, both of us sensing the vibe. I asked her what she was up to. She told me she was probably gonna go home, smoke a bowl, masturbate, and crash out. "Sounds like fun" I said "Mostly the masturbation part." She laughed. "Why? You wanna help?" I shrunk, trying to play it off. "I didn't think you swung that way." "Right now I'd swing any way if it knew how to make me cum." My whole body was vibrating. She glanced down at the bulge in my shorts. "Looks like you might feel the same." she said

I threw her against the door of her apartment as I kissed her. The two minute drive to her place had been agony. I needed release. I wrapped my fingers around her throat and pulled her face into mine, forcefully inserting my leg in between hers as I did it. Instantly I felt the wetness of her cunt seeping on to my leg as she grinded into me. The fabric of her yoga pants, let alone her thong, was completely soaked through. My cock was damn near bursting out of my shorts as she feverishly felt about for me, her short fake nails clacking on the plastic button keeping them affixed to my body. Her keys jingled in her hand as she turned and unlocked the door. We plunged into the darkness of her apartment.

"Can I rip this?" I asked, already halfway doing so. She breathed out an affirmation as I buried my tongue inside her fat, neatly trimmed pussy. "Oh my god" she moaned, writhing into the carpet. "How the fuck are you doing that? Jesus Christ!" I laughed. "Practice". My hands mapped out every inch of her skin, the shape and depth of her thighs, the weight of her breasts, the soft crest of her tummy. I slid my fingers inside her without even the slightest friction as my teeth dug into her the meat of her inner thigh. "Bruise me, please." I pulled my face away and slapped where I'd just bitten. Hard. She flinched, letting out a shocked moan. "Fuck that was so hot. Do that again." I followed the instruction, this time on the other leg, one hand still two fingers knuckle deep and come hithering deep inside her. This time she screamed, flinched, briefly sat up then fell back on to her back. "You've gotta teach me how to do that so I can use it." she laughed. "Do what?" I asked as I simultaneously finger fucked, bit, then slapped her thigh. Her whole body seized as her eyes briefly retreated to the back of her head. "That." She said

I lined the head of my cock up with her drenched slit. "So you're a lesbian, huh?" I asked. "Fuck off." she laughed. "I want you to say it." I told her. "Of course you do." I slapped the full weight of my throbbing cock against the lips of her pussy, running the head in between them. Her brain barely able to function. "If you don't say it, I won't fuck you." She vented her frustration. "Alright, fine. I'm a les-" I pushed my  cock all the way into her. She didn't finish the sentence. My hands returned to their rightful place on her throat and mouth respectively. "You like when daddy uses you like this don't you?" She nodded. "You're gonna be a good little dyke fuckdoll for daddy, aren't you?" She nodded again. "Teasing me at work with your fat dyke tits. You really thought you wouldn't end up on your back like this? You thought you'd keep your gold star if you kept teasing me?" I removed my hand from her mouth. She eeked out a "no sir." I slapped her across the face as I pounded her dripping hole, her fat ass slapping against my thighs. "Thank you sir." she moaned.

I felt her pussy start to clench up. The desire that had been building in both of us for so long seemed completely overwhelming. I flipped her over, knowing that I had to pound her fat ass at least once before I filled her with my cum. I slipped my fingers into her silky black hair. "Beg for it bitch". "Please sir, cum inside me. Please sir. Please I need it so bad. Please I'll be your little fuck doll please just cum inside me." I emptied myself inside her, months of build up in a single load. We collapsed on the floor.

"Holy fuck" I said. We both burst into laughter.

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