I 35[M] hate fucked my 25[F] enhanced coworker, no regrets.

I worked with Callie for 3 years before we finally hooked up. She was a fitness junkie and vein as hell. She did some modeling while she was a teenager and mentioned it with regularity. In college she alpine skied competitively in winter and water skied in summer. After college she hired a personal trainer, spent a bunch of money on clothing (short, tight dresses and athleisure wear) and managed to gather a decent number of instagram followers (~25k). Within an hour of meeting her I learned that she had one instagram post with over 100k likes…I guess that was supposed to impress me? I’m 36 and don’t give two fucks about social media.

We worked in sales together. Her greatest skill as a sales person was having a wealthy, well connected family, a gorgeous strawberry blonde hair framed face, and a fantastic ass. Her well connected family got her the job, a job which would usually require 4-6 years of real experiences and an existing book of business, but the owner of my company had no problem hiring her, giving her a 6 figure salary and giving her all the runway she could ask for to build her sales book.

I was assigned to her to be her technical sales resource. Most guys fawned over her and the expectations placed on her to succeed were minimal. I found a way to work well enough with her to keep earning a nice commission, but I never gave her any attention outside of a professional interaction. I didn’t care about her social media, I didn’t want to hear about her weekend exploits. I refused to let her see me check her out. I never did her work for her and instead gave her guidance and ignored her attempts to dump work her peers did on to me.

I sat quietly when she’d complain about various racial groups and how much in taxes came out of her 5 figure commission checks. I said nothing when she would complain how hard a certain deal was to close, knowing full well that her role was of the least value, yet she’d make more than anyone else off of it. Plenty of sales people are insufferable, but she was unique in the way she portrayed herself as being a victim *all the damn time*, when in reality she was almost never one. The last straw was her complaining about the car she was driving. It was a luxury car her father gifted her as a graduation present, but it required some kind of maintenance, and rather than deal with it, she complained to her father (she was 25 now, btw) until he agreed to have someone bring her a loaner and take the car in for service. At that point I just wanted a way to not have to work with her anymore.

The closest to inappropriate behavior I had with her was after a golfing event with customers, I was dehydrated from the sun and drank a bit too much in the clubhouse and was bullshitting with a coworker who didn’t have to work with Callie. I was sitting outside enjoying a cigar, and he was giving me shit about how lucky i was to get to spend all that time with Callie. I responded at some point with a comment like, “Ehh, she’s pretty, but she’s so damn entitled, and besides, I like my women to at least need to wear a bra.” It was petty and sexist on my part, but by that point I had my fill of Callie as a coworker, and more than my fill of her as a human being.

I don’t pretend to be overly woke, but I know where I stand and if I just wanted to fuck hot, ditzy women I make enough money to make that happen. I’d rather be single than in a hollow marriage to trophy wife. But, it’s easier to tell the kind of guys I worked with that I didn’t want to sleep with someone because their tits were too small than my lack of respect for them. Not to mention I’m a firm believer in not shitting where you eat.

I never found how it got back to her, for all I know she was eavesdropping on my conversation, but fast forward three months and I’d taken a different job. Much of the reason was to not have to work with Callie anymore (and I let management know that). Nine months further forward and I’m at a big industry conference in Orlando, when who walks into my booth? None other than Callie. She was wearing a modest skirt and a blazer, but she looked _different_ than I remembered, but I couldn’t quite put my finger on it. She greets me and goes in for a hug, and that’s what I felt it: she had tits, and they were not small.

We make some small talk, and she’s being overly friendly, and keeps making contact with me, touching my arm and chest. Eventually she invites me for a drink. For some reason, I said yes, and we made plans to meet up at the bar in her hotel after dinner. In the back of my head, I knew that there was something else going on, but I pushed it aside and just decided to go with it. I didn’t have anything better to do that night, anyways.

Callie didn’t show up until almost a half hour past when we agreed to meet. In hindsight I think this was deliberate, as a way to gauge my interest level. In truth, I was texting with a woman I actually had interest in dating and getting my fantasy football lineup set, something I’d have been doing at the bar of my hotel, so for me it wasn’t the power play she might have thought.

I saw her approach from the elevator bank, and that’s when I knew she was in predator mode. She was wearing a skintight navy minidress with slit up one leg. The dress showed off her newly improved chest, making it clear where she wanted attention to be focused. She was wearing high strappy heels and her toenail polish matched the color of the dress. This was a totally different outfit than she’d worn to the conference, and her hair was now down and blown out, as opposed to pulled back into a ponytail like it had been earlier in the day. This was all a setup.

“Wow, you look incredible!” I say as she gets closer. And she did, easily the hottest woman in the bar. The way she looked she could have picked up any of the many many conference attendees, all of whom are miles away from spouses, and many of whom would love nothing more than to pound some conference strange.
“Thanks, I didn’t know if I’d have a reason to wear this this week.”

We chat for a bit, and the bartender comes by, asking if I want a refill, which I turn down. I wasn’t sure why, but I felt like getting drunk was going to lead somewhere I didn’t want. She gives the bartender her order, “Double Vodka and Red Bull please, and a two shots of Patron with limes.” I give her a look, she smiles and touches my arm.

We catch up on our various careers, and I ignore the shot until she finishes her vodka red bull. Her hand is on my knee, not quite stroking my leg, yet. She holds up the shot, and says, “a toast to the success of each other’s careers and the failures of our love life.” I laugh, and poorly down the shot, just barely managing not to cough.

She motions to the bartender and put up two fingers, wanting another round. In my head I’m having a battle, part of me wants to wind this down ASAP and GTFO. Another part of me wants to buy what Callie is clearly selling. It only took a moment to get confirmation that she’d been working this deal since she saw me, and now she was going to make her closing pitch. The new shots arrive, and she asks me if she can ask me a personal question. Her hand has moved to my shoulder now.

“I suppose.”

“Why didn’t we ever get together when we were working together?”

I laugh, and say something along the lines of not wanting to mix work and personal life.

“Bullshit. I know the real reason. I’m was hot, but you were right, my tits were tiny, but they’re not so small now, are they?”

I laughed, more incredulously than I meant. Up until that point I’d been wrestling with whether I shut this all down, but with that comment I decided the opposite. She was so shallow that she couldn’t stand me not wanting to get with her. She felt _owed_ that level of affection. I downed the shot, now determined that I’d have my way with her. I’d play along, let her think she’d “won”. I’d fuck her, and then I’d ghost her.

**Sexy stuff starts here**

“Fine, let’s head upstairs then.” She seemed almost surprised by that, but she packed up her clutch and stood. I threw cash on the bar and grabbed her hand, motioning toward the elevator. As the doors closed and we began to ascend, I pulled her into a kiss, letting my hand roam to her ass squeezing it.

I’d be lying if I said she was anything other than hot-as-fuck. She keyed into her room, and I ran my hands over her while kissing down her neck. I pulled back, and took my shirt off and undid my belt. I was fully hard and I entwined my hand in her hair, palming her entire head easily, closing my fist and pulling her hair tight, making it clear I was in control. I think at this point it finally occurred to her that I really dwarfed her. I’m about 6’ and 230lbs. She was maybe 5’2”, and lithe enough for me to easily manhandle.

I pushed her down and put my cock directly in front of her face. She grasped it and took it in her mouth, and the second my tip was past her lips I pushed her entire face toward it, until I felt the back of her throat. I didn’t really let her blow me so much as I face-fucked her. She gagged a few times in the process, but her resolve was firm, and no matter how uncomfortable I might have been making her she kept playing along.

I decided I’d had enough, and pulled her away from me, releasing her head. She stood up, looking disheveled and not overly thrilled. I kissed her again, pulling her in to me, groping her chest. I spun her around and unzipped her dress. I stepped back as she turned to face me, and she pulled the dress down. She was wearing a very black thong and a matching bra. “Well, what are you waiting for?” A tone of impatience in my voice. She smiled and unclasped the bra, dropping it to the floor and scooting up the bed.

She must have spent a lot, because I saw no signs of scars and her tits were a very generous B or C cup and she was *flat* before, so this was quite the upgrade. Combined with her very toned body, she looked incredible. She had visible abs and it was clear she spent a lot of time keeping in shape. I didn’t tell her that, of course, and instead climbed on the bed, pressing myself on top of her. I teased one of her nipples with my tongue and groped the other, feeling it’s new size and heft. I went back and forth between her tits. Her breathing intensified and I felt her wrap her legs around me.

I leaned back and grabbed her hips, flipped her over, and pulled her onto her knees. Her asshole visible behind a small strip of fabric. I pulled it to the side, running my middle and ring finger down between her ass and over her smooth pussy and pushing inside of her.

Her pussy was tight and wet, and while normally there’s few things I love more than eating a girl out, this situation was about getting myself off, nothing more. I worked my fingers in and out a few times, just enough to get them wet. She was tight and my fingers barely fit.

I grabbed my cock and lined it up with her slit, pushed into her while pulling her hips back toward me until I bottomed out. I’m not the longest out there, maybe 6.5” on a good day, but I’ve got a better than average girth. I’ve had more than one woman complain if they don’t “work up” before taking me inside. As my balls met her clit, she let out a very loud gasp. I was stretching her and it sounded like it didn’t feel great. I didn’t care, and I grabbed her hips and went to town fucking her.

She tried to reposition at one point, but I used my size to instead press her down into the bed. I pressed my hands down onto her ass, pinning her while I slowed down on the withdrawal, only to slam back into her. She felt really good, almost good enough that I entertained the idea of being a bit nicer in hopes of being able to repeat this, but I pushed those thoughts aside.

I kept pounding her until I felt the familiar sensation of an oncoming orgasm. I wanted to fill her, but the risk of getting her pregnant was just too much. I exploited her small size and pulled out and grabbed her hips and pulled her up, as though I was going to resume doggy style. Instead, I grabbed her hair and pulled her upright to face me cock.

It was then I saw her face. Her mascara was running and her lipstick wrecked. She looked disheveled and almost dazed. She saw my hard on, and looked at me again, I pulled her closer and she without needing to ask, started blowing me again. I was fairly close to coming already, so as I reached the edge of the cliff, I grabbed her again and held her face in front of me. Thick ropes sprayed toward her face. The first one landed in her hair, the second her forehead. She was lucky to have closed her eyes as the it ran down her forehead, oozing into her brow. The last large spurt covered her lips.

After I finished, I fought the lethargy that came on, and staggered into the bathroom, holding myself up with the vanity. I used a towel to wipe myself off and walked out of the bathroom, tossing the come and crotch sweat soaked towel to Callie. She had one eye still closed and still looked dazed. I went to the pile of my clothes on the floor and started getting dressed while she started cleaning her face.

As I slipped my shoes and buckled my belt, I think it finally dawned on her that this was ending. The expression on her face hardened and she stuttered out, “What the fuck, you’re leaving?”

I grabbed my suit jacket (which had my phone in it), and shrugged and said, “I guess.” in a non-committal tone, and left.

Later that night I got a text from her, it just said, “WTF WAS THAT ASSHOLE?”

I replied back with ??

Source: reddit.com/r/gonewildstories/comments/fww07k/i_35m_hate_fucked_my_25f_enhanced_coworker_no