The Best Way To Get Over Someone

I bartended at Skipper's on Wednesdays and Fridays. My day job paid the bills, but it brought in some extra and play money, plus the crowd was always bustling due to the specials and promotions Chuck ran all the time. Wednesdays were my favorite, however, because they were a little less crazy, and after the Texas Hold Em tournament cleared out around 9:30-ish, things quieted down enough to not run like crazy but still make some money.

I had just reached down to one of the shelves to grab the cherries so I could refill the bar dispenser, when I heard the familiar sweet purr of her voice say "Mich Ultra, babe." I quickly stood up, grabbed a pint glass, poured from the tap, and set it down in front of Rebecca, as she gave me a sweet, slightly sultry smile. A semi-regular here a couple nights a week, she was one of the few customers I truly didn't mind calling me by a pet name--whether she meant anything by it or not, I liked her enough to not care about the mild flirting. I grabbed the three singles she had set down, hit the register, and pulled out a quarter, bouncing it off the mirror into the tip bucket. "Nice!" she called out enthusiastically. "Now, where..." she asked, indicating herself.

I liked this game, especially since she'd been upping the ante a bit without doing anything that would get me in trouble with Chuck. "I'm going to guess your waistband again." She looked me in the eye and shook her head from side to side, her big sapphire eyes fixed on mine.

"Alright, your hair?" Another head shake.

"Your, uh..." I indicated her cleavage, which had a decent few inches exposed in a flattering top tonight, although not necessarily filthy. She grinned, glanced down, and then reached her fingers in, and pulled out a folded dollar for me, smirking as she handed it over. I stifled a giggle and muttered lowly "You naughty girl."

"You have no idea," she bantered back, before giving me a wink and walking back over to the game she'd been watching. I found myself staring a bit as she walked away, as that curvy behind was definitely one that attracted attention in any pair of pants, and I had to quickly adjust myself as I had a faint bit of tightening in my undershorts.

I busied myself with the restocking I needed to do after the poker crowd hit. Still, I kept finding myself sneaking glances at her. She wasn't usually my type, but I had to admit that there was something damn sexy about her. She had a face reminiscent of Farrah Fawcett in her 40's except for a massive mane of thick red hair and a light dusting of freckles in a few different places, and I knew she had just hit 47, though she could have easily pulled off 32. About 5'5", she was curvy as hell, almost to the point where someone might have called her chunky, but I could see very little actual fat on her, except where it mattered most. Her tits were simply gigantic, as big as my head, and her ass was a beautiful round bubble that protruded in the most amazing way. Many of the older guys liked to hit on her, and she would humor them, but never seemed that interested. Chuck said once that she'd kicked her hubby out for cheating years back and had never really settled down since, and I knew they dated for a few months a couple years back, remaining friends, but never really pried beyond that.

I saw a couple guys approaching the bar out of my peripheral vision, so I shook my head to clear it, and got their order going.

The night ended pretty smoothly. Rebecca left after 4 beers, her usual upper limit, and while I'd had to refuse to serve one guy, he hadn't made a huge stink about it, just letting me call him a cab. I made about 250 bucks in tips after tipping the cook and giving some money to the doorman. I ended the night in the usual fashion, doing the till counts with Chuck. We always had an easy banter, despite him being well older than my dad and a slight redneck.

"Damn good night," he mused.

"Yeah, I like the low drama ones," I replied.

"Rebecca seemed friendly tonight."

"Kinda, yeah. She definitely likes to flirt."

"I think she mostly likes you," he batted back.

"You get that? I'm not sure, honestly. Sometimes it seems like it, and other times, I think she just enjoys toying with me."

"I dated her for 4 months, remember? I'm sure she loves toying with you, but I know that woman's M.O. when it comes to pursuit."

"Huh," I verbalized, not knowing how to answer.

"Trust me, if she throws it out there--and if I'm right, she will, soon--you'd do well not to turn her down. That woman will turn your world upside down in bed."

"That good?"

"Earth shattering. She's an oral queen, cums harder than anyone I've ever met, and she'll drain your balls dry then keep on going."

"Wow."

"I've been with literally hundreds of women between the military and being in the bar biz most of my life. She blows them all away."

"Okay. Then why'd you break up with her?"

"I couldn't keep up!" he protested, laughing. "I'm gonna be 63 next month, and look at me, I'm a pudgy bastard. That girl wanted it 3-4 times a day when I saw her. I was raw! Plus, I don't really need or want a steady woman in my life at this point."

I laughed and shook my head. "I'll take it under advisement. Truth be told, I'm still on the rebound and don't know if I'm ready."

"Whatshernameagain, Kaitlyn?"

"Kaylee."

"Yeah, the ripped blonde gal."

"That's her."

"Young girls don't know what they want yet, my friend. Don't take it personal, and don't waste too much time wondering what should or might have been. There's a whole world out there, and you're still young enough to enjoy it for a few more years until settling down."

I nodded my head, and we finished the till, then closed out.

The alarm went off at 5:45. Despite the lack of sleep, I quickly threw on my workout clothes and busted ass to the gym.

Early mornings were my time, I just love the quiet. I blasted through my workout in a little over an hour and then ran behind the counter, quickly consulting my book of clients for the day. Thursdays were usually jam packed, thank god. Personal training really is a hustle business, and the owners of this gym loved me because I was good, willing to network, I looked the part thanks to my ridiculous workout regimen, and, as Rachel, the co-owner had pointed out, I had a "cute, young stud look" that seemed to drive the older Valley trophy wives nuts. I just had to get out the door and back to my apartment to shower, change clothes, and eat before Mrs. Sands at 8am. I ran towards the door, only to have my stomach drop as I saw Kaylee walking up. I breathed deeply, steeled myself, and went out into the parking lot, determined not to avoid this and have her realize I was trying to duck her.

The ensuing conversation was all kinds of awkward, with avoided eye contact galore, and after the obligatory 60 seconds of inquiry about "things," I quickly begged off and got in my car. I ran home, showered, and cursed myself as I jerked off in the shower, with thoughts about Kaylee's taut ass and fake C-cup tits helping to fuel my orgasm. While I didn't want her anymore, and the sex had been mediocre at best, she was gorgeous and the last ass I had touched.

I blasted through five clients, completed some paperwork, and filled in for Denise's self-defense class in the afternoon so she could take her kid to the doctor. All in all, it had been a good day, and as sat at my kitchen counter that evening, finishing the last of my chicken and rice, I fired up my laptop.

I opened my second browser, and pulled up some porn sites, cruising through the normal younger women nearer my age, but nothing was catching my eye. Finally, after about 5 minutes of clicking around, I went back to the categories tab. Curvy Milf caught my eye, and I clicked on it. My heart started beating a bit quicker as a preview of a 40-something with wide, full hips and big, pendulous boobs riding a younger guy who looked about my age. I clicked on it tentatively, and watched as she introduced herself, slowly twirling, then peeling her nightie down, and finally beginning to suck on the cock of a young man. Her body wasn't the perfect hardbody I usually gravitated to, but she seemed to know exactly what she wanted in bed, subtly and kindly guiding the guy on how to eat her pussy, then getting him to fuck her on her back, doggy, on her side, riding him, and then finally putting him into her ass. I stood at the counter with my shorts around my ankles, stroking my thick meat hungrily, and when she took him out and placed him between her tits, commencing with even more filthy talk than she'd been giving before, I came harder than I could recall in quite some time. I stood there leaning against the counter, my still turgid rod in my hand, and glanced at the gigantic mess on my floor and cabinets. I shook my head and reached for the paper towels, a little surprised that this had turned me on as much as it did.

Friday was a light day at the gym with one client, which was appreciated because it gave me adequate time to grab a nap before my bar shift. It was a quieter Friday due to a Metallica concert in town, which was fine by me, I figured we'd get a little post-show rush as well. Around 7pm, Rebecca strolled in with her friend Tiffany from work, both of them still in their biz casual, except today I noticed she'd popped a couple buttons on her striped button-down and had a bit of makeup on. She looked, dare I say, hot. They got a beer, but as she was absorbed with Tiffany, who was a chatterbox of the greatest velocity, we barely got a moment. I let them be at the end of the bar, and attended to the other customers.

About the third time I swung by, they were ready for refreshes on the drinks, and Tiffany got up to use the restroom. I poured her the usual light beer and Tiff a Cosmo, setting them down with a "How's the night treating you two?"

"Oh, I'm good," Rebecca responded, leaning forward, her cleavage on full display tonight. I tried not to stare, but I failed for a second. I looked up, caught, and she smiled, first a smirk, then a full teeth grin of joy, letting me know it was alright. I smiled back. "I think Tiffany is having a hard time at home, though."

"Oh?" I asked noncommittally.

"Yeah. I think she just needs to smoke her husband's pole more."

I snorted with laughter, not entirely expecting that. "Oh yeah? I mean, she'd have to stop talking for a few minutes," I replied, flashing her an evil grin.

"Yeah, well women who love to talk usually have an oral fixation. I definitely do. There's something just fantastic about a good suck, a big fat cock in your mouth, mmm..." she smirked. I looked back at her, not wanting to break away, completely leveled. She'd just put it out there, and I had no peppy comeback ready, completely unlike me. Plus, the sudden talk had me so hot it was ridiculous, and I could feel myself hardening against my leg. The tension hung in the air for a few pregnant moments before Pam, the unaware cocktail waitress, came up to me and barked out a few drinks. I both cursed and thanked her internally.

After that, a quick wave hit, and Tiff returned to talk Rebecca's ear off some more. I refreshed their drinks once more, but when I returned a bit later, they both waved me off, and Rebecca indicated she wanted to close their tab. I ran the card and handed her the receipt, and as she signed it and put a tip on the line, I found myself somewhat bummed out that she wasn't going to reach into her cleavage again. I was ready to wish her a good night, when she paused and leaned in. "Hey, do you have anything going on tomorrow night?"

I thought briefly about the way I had spent the last few Saturdays, cooking at home while watching HBO, and then eventually rubbing one (or two, or even three) out. "No, no real plans," I replied with an attempt at nonchalance.

"Okay. Listen, I have two tickets to a reggae concert. It's some nobody band from down south, but my friend that was supposed to go bowed out. I don't suppose you'd like to come with me? If not, no big, I've just not found anybody who wasn't busy so far."

Was she asking me out? "Yes, I'd like that. Thank you," I replied.

"Okay, great!" she beamed. She leaned in, and her perfume wafted toward me. I felt myself react, and as she reached into the front of her bra and produced a business card, I had to wonder if this was just a friend date, or if Chuck was right. "My cell is on there. Text me." She winked again, turned around, and sauntered toward the exit.

I turned and noticed Chuck glancing at the situation from about 20 feet away as he finished shmoozing a table. He chuckled and gave me a thumbs up. I rolled my eyes and addressed a couple guys approaching the bar. After pouring their beers and giving them their change, he came up to me and said "Looks like somebody's getting laid tomorrow night," jovially.

"I'm just going to a concert with her. She has an extra ticket. Besides, I'm not looking to start anything."

"My guess is she'll start and finish it," he said with a laugh, "It's the best way to get over someone..." as he went into the kitchen to expedite a food order.

Saturday came, and I was a tick nervous. I'd texted Rebecca, and we started an easy back and forth. She was a touch flirty, but nothing too committal. I was seriously psyching myself out on this one, not at all sure what I was getting into. I casually asked her what she was planning on wearing to get a bead on how she was feeling, and she replied just jeans and a tee. We agreed that she'd meet me at my place and we'd take the rail right by my apartment complex to the venue, so we'd save time and parking. At 6:30 sharp, she knocked on my door, and I let her in. Her jeans were snug but not indecently tight, her "tee" was actually a bit more form fitting and low cut, which I was appreciating, and while she hadn't gone heavy on the makeup, she had a deep scarlet lipstick and some eyeliner going that made me pause to wonder what it would be like to have those thick lips wrapped around my cock. As I shut the door, she leaned in, gave me a quick hug that I returned, and kissed me gently on the cheek. "I need to borrow your restroom, and then we should probably get going. I know a great taco place right by the theater, we can grab something beforehand." I directed her down the hall, and she smiled at me over her shoulder.

The train was a short 10 minute jaunt, and dinner was fun, she was a good conversationalist and seemed pretty determined to draw me out. I found out a little bit about her as well, including that she had a grown daughter who lived in Argentina teaching, and about her obsession with bad horror movies. I told her about my current attempts to establish myself as a trainer, and some dreams I had for the future. We had each other laughing pretty steadily and I was thoroughly enjoying myself, especially when she kept reaching forward and lightly touching my arm. After we finished, we walked two doors down to the small hall, which was only about the size of half a basketball court, and as people packed in, the band slowly piled out and started to play.

I've never been a huge reggae fan, but the band was decent, and as the room crowded, we got closer, and Rebecca leaned back into me as we both swayed to the music. She smelled fantastic, and I was treated to a great view down her shirt of her absolutely stupendous tits. Our hips swayed together, and I put my hand on her hip lightly, trying not to be too forward, even though she was starting to show some interest.

She leaned in to me a bit harder, gently grabbing my hand and leading my arm around her midsection, and was really molding her body into mine. My member began to inflate, struggling against the thickness of my pants. At first I was horrified, as I didn't want to push thing too far too fast, but as I felt her butt scoot back firmly against my hardening length, she tilted her head back, then around to kiss me. It was a medium-length peck at first, but then she leaned in and opened her mouth, pushing her tongue into mine. We explored each other's mouths for a few moments, then she pulled back, whispering "Is that for me?" huskily into my ear as she ground her ass back into me again.

"That's up to you, but you're definitely the cause of it," I shot back.

She kissed me fiercely again. "Goody."

She looked forward again, still pressed against me. We swayed for a few moments, her ass pressed against my insistent length. I groaned internally, both with frustration and need. She looked back at me and smirked, then leaned into my ear. "You want to get out of here?"

"Hell yeah," I replied.

We made a beeline for the door, with her fussing with her phone to order an Uber. Apparently the gods were on our side, because we didn't even wait 2 minutes before one pulled up. As we got in, she called out to the gent driving "I've got two extra $20s with your name on it if you get us there in 5 minutes." He hit the pedal hard, and sure enough, earned his money. She took the time to tease me, make out, lightly stroke my pole through my jeans, kiss my neck, and generally drive me nuts.

We exited the Uber, me fumbling with my keys as she made out with me and grabbed my cock firmly through my jeans. I unlocked my door, and we burst through it, slamming it behind and quickly launching into each other again. We were all over each other, kissing madly as our hands each roamed, and groped, mine settling on her butt, which was big and firm while also being the perfect amount of squishy. She pulled back slightly, leading me over to the couch by my belt loops, then pushing me back against it so I fell into it. She straddled me and we made out as she made quick work of my belt and undid my jeans. She slid down and prompted me to lift my hips so that she could pull my pants down, allowing my straining cock to come flying out. She paused to grab it in her delicate hand, giving it a soft squeeze while very subtly licking her lips, then looking up at me and smirking with lust in her eyes. Quickly she dispatched my shoes and socks, pulling my pants completely off before she stood up and undid her own, pulling them down, then lifting her shirt over her head, and reaching behind to unclasp her bra.

I've always been an ass man, but when her rack came into full view, I felt my cock stiffen and my breath leave my body temporarily. Her tits were gigantic, so big that even her areolae, which were approximately a little smaller than the surface of my palms, didn't look overly large on her. My mouth salivated a bit as my eyes bugged out.

"You like them?" she asked, bringing her hands underneath to cradle them.

"Holy shit, yes..." I managed to get out.

"I'm a 40G," she said with a grin, "and my nipples are so sensitive I can almost have an orgasm playing with them alone. In case you wanted to test that out at some point." I smiled and nodded at her, trying and failing to keep my cool. She giggled, and did a slow twirl for me. Her legs were toned and well muscled from being in heels day after day, and her butt beautifully formed, with wide, flared hips. Her tummy had barely the smallest pooch, but it only seemed to add to her amazing curves and sex appeal.

I pulled my shirt off, and as she climbed on the couch to straddle me, she began to run her hands over my chest and kiss me with fervor again. I grabbed her hips, enjoying the feel of her soft, glorious skin. She reached down and grabbed my rod, gently jacking me, then pulling a bit harder. I grabbed her hips firmly and said "We should go into the bedroom, I need a..."

"No, this first round is all for you." she said, kissing me again, then sinking to her knees on the floor. She grabbed my cock firmly again, kissing up the underside very deliberately, then swirling her tongue over my head. I moved forward to try and tell her it wan't necessary, but she pushed forward, putting her hand in the middle of my chest and gently but firmly forcing me back against the sofa. "Sit back and relax. Because I'm dying to suck you off."