Cheating Ch. 07: The Coworker

After spending years in a job I hated, I'd taken a new job that was farther away, paid a little less, but had a better schedule and a better work environment. My new coworkers were great, like anywhere it wasn't perfect but I got along with everybody pretty well.

When I started I was taking over my coworker Mindy's position and she was transitioning into a new role. Mindy and I hit it off almost immediately, which was somewhat surprising considering I was 34 and she was 24. Not a huge age difference, but enough that we were at different points in life. I was married with kids, she had been dating and thinking about marriage but in no rush to get there. She still liked to go out and party, whereas my partying days were behind me (never was a big partier to begin with to be honest).

It was also an interesting dynamic, as she was a decade younger but was the one training me. I've never had an issue with supervisors, trainers, etc. being younger than me like some people do. Age really is just a number, experience and knowledge aren't dependent on it.

It had been about a year, and Mindy was definitely my closest office friend. She'd come to me all the time for life advice and just to vent about things, both in her personal life and related to work. She was comfortable enough that she would just walk into my office, close the door, sit down, and start talking. I didn't mind it when she did, would break up the monotony of the day and she wasn't too bad to look at, either.

Mindy has what I would call a cute-nerdy look. She didn't wear glasses all the time, but when she did it made her look so damn cute. She'd actually done some part time modeling on the side for fun after a friend got her hooked up. You wouldn't mistake her for a supermodel or anything, but she was definitely one of the more attractive women I knew.

She said she was overweight when she was younger, which I wouldn't have guessed except for one thing: her ass. She was pretty thin all the way around with probably B cup tits, but she had wide hips and a nice, heart shaped ass. I'm an ass man through and through so I snuck a peek every chance I got.

She had broken up with her boyfriend recently, I wasn't privy to the details but she was ready to date pretty much right away, and would come talk to me about her dates. I really didn't care to hear about them, but I wasn't going to kick her out of my office or anything. She'd asked my opinion on a dress she was buying to go to a wedding, I thought it would look great on her but suggested one of the other patterns it came in. She found it pretty funny that I actually had an opinion, but ended up getting the pattern I suggested.

One night we were working a late night together. Our mandatory late nights require one employee from each team (there are 2 teams) and one of our secretaries. It's up to each team to decide who has to work the late night, and Mindy and I just so happened to draw the night together. We got some work done, but mostly spent the time BSing with each other and the secretary.

At one point, the secretary talked about setting her up with a family friend of theirs. When Mindy found out he was 32, she responded with, "Sorry, that's too old for me."

"Hey now," I said, "what's that supposed to mean?"

"I'm not saying 32 is old," she tried to save herself, "I'm just saying it's older than I'd want to date someone, too many differences in where you are in life"

"Sure," I said with a smile, "I'll just try to forget you basically called me old."

Close to the end of the night, Mindy went to the office window to start her car, it was pretty hot so she wanted to run the A/C for a bit. All of the sudden I heard, "Shit."

"What's wrong?" I asked.

"Well, I just tried to start my car and nothing. I thought maybe it just wouldn't start, but I just tried to unlock the doors to see if the headlights would flash and still nothing. I think my battery is dead."

"Need a ride home?" I asked.

"If you wouldn't mind," she said, "I know it's out of your way but that would be awesome. I'll make it worth it for you."

I looked at her with a raised eyebrow.

"I know you're a bourbon guy," she said, "my dad gave me a nice bottle of bourbon awhile back. It was supposed to be for Tony, but we broke up before I gave it to him. I'm not going to drink it so you can have it." I wasn't sure what she or her dad considered nice, but I won't turn down free bourbon.

I texted Sara to let her know I'd be running late. She responded back with, "Suuuuuure, I know you're chasing tail!" By this point she was comfortable enough with things she'd joke about it.

After work, we walked to her car just to check for sure, and unfortunately the battery was definitely dead. We walked over to my car, I had to clear off the passenger's seat because that's usually where I toss the stuff I take back and forth between home and work.

"Thanks," she said as she climbed in.

It was about a 20 minute drive to her house, and we mostly talked about work. Once we got to her apartment building, she invited me up to get the bottle of bourbon. Thankfully, the next day was a holiday so I didn't need to worry about getting to bed early. She lived on the second story, so it was a short hike.

"My roommate is gone for a couple days," she said as she opened the door, "I'm not sure if she cleaned up before she left so I apologize if it's messy." She turned on the light and at least by my standards, it wasn't messy.

"Just have a seat on the couch," she said, "I'll run and grab the bourbon. Want to pop it open and try some?"

"Sure," I said, "why the hell not, don't have to work tomorrow after all."

She came back, and to my shock she was carrying a bottle of Pappy Van Winkle 15 Year as well as a bottle of wine. If you don't know much about bourbon, just know that the Van Winkle line is among the best and very expensive. 15 year is one of the younger ones but still highly sought after.

"Wow," I said, " I appreciate it but I can't take that. That bottle costs more than we make in a month."

"Really?!?" she asked.

"Ya," I answered, "that's some good stuff. If you open it I'll have some, but I can't take it in good conscience. Your dad must have really liked Tony to get that for him."

"Ya, he did, but fuck Tony," she said.

"Fair enough," I laughed.

She poured me a highball glass of the Van Winkle and herself a very full glass of wine. It's obviously an exaggeration to compare a bourbon to sex but... man was that bourbon a pleasurable experience! I milked it for all it was worth, sipping on it in the time it took her to drink three glasses of wine as we talked about her dating life, the wedding she was going to, and just generally about her life honestly. At one point she said, "Oh! I got that dress we talked about, want to see it?"

"Sure," I answered. She ran off to her room, and came back a few minutes later. She was wearing the dress, which was blue and had tie shoulder straps. It was a pretty modest length but had a slit on the left side making it look pretty sexy for how long it was.

"Like it?" she asked.

"Definitely," I answered, looking her up and down.

"I'm glad you talked me into the blue," she said, "I think the darker color looks better."

"It definitely looks good on you, that's for sure," I added.

"Thanks!" she said with a big smile. She sat down on the couch next to me. She was clearly feeling the wine, but not quite what I would call drunk. Without warning she gave me a hug and said, "And thank you for being such a good friend at work." She pulled back and we locked eyes. She has beautiful hazel eyes to go along with her shoulder length brown hair. I thought it was just going to be an awkward "we're to close" moment, but then she leaned in and kissed me.

After a second of shock, I started kissing her back. Suddenly she pulled back.

"Oh my God, I'm so sorry!" she said frantically, "you're married, I don't know what I was thinking."

"Don't worry," I said, "first of all I kissed you back so you're not the only guilty party."

"Ya, I guess," she responded.

"Second... Yes, I am married. But, and this isn't something I want getting out so it doesn't leave this room, my wife is fine with me being with other women."

"Wait, WHAT?" She said in utter shock. "I thought you guys were happy together? What happened?"

"Well," I answered, "to be accurate we are very happy. We had some issues and still do like any couple, but one of the big ones was sex. Her giving me the ok to be with other women solved that one pretty well."

"So are you guys, like, swingers then?" She asked, seemingly excited.

"Well, not really," I said, "she doesn't sleep with anybody else. If she wanted to I wouldn't stop her, but she doesn't want to at this point."

"Ah, so it's just you?" she asked.

"Yep," I answered.

"Pretty sweet deal for you," she said.

"I'm not complaining," I responded with a smile.

She leaned in again for a kiss, and this time it was more passionate. We kissed for a few minutes before she climbed on top of me and straddled me.

"What happened to me being old?" I asked.

"I said I wouldn't DATE anyone that old, I never said anything about hooking up," she said with a devilish grin.

Just then I got a text message. Mindy grabbed my phone and said, "Sara wants to know when you'll be home," she said. Before I could answer, Mindy took a selfie of her on top of me and quickly typed a text back.

"What was that?" I asked.

"I told her when I was done with you," she said.

Shit, I thought. This might be over the line, the picture and text might really piss Sara off.

My phone went off again. This time I grabbed it, and saw a message from Sara.

"Ohhhhh, well have fun you two!" it said. Phew, I thought, she must be comfortable enough with things now that it didn't piss her off..

"Everything ok?" Mindy asked.

"Well no, only because we stopped though," I said with a smile.

Mindy leaned back in to kiss me, and as she did she unbuckled my belt. She reached her hand into my pants and started stroking my cock through my underwear.

"Damn," she said.

"What?" I asked.

"You're thick," she answered. "Alot thicker than Tony was, that's for sure."

I started kissing her neck as she continued to stroke my cock, "Speaking of Tony," I asked between kisses, "why did you guys break up?"

"Remember when we went to Mexico? Well, while we were down there I caught him with one of the resort employees," she said.

"Ah, that makes sense now," I replied.

She climbed off of me and pulled my pants and underwear down. She grabbed my cock and started stroking it while looking up at me with a smile. She has pretty small hands which made my cock seem even thicker, and the fact she was still wearing her glasses made her look even hotter.

At this point I asked her, "You've been drinking, are you sure you want to keep going?"

"Look at you," she laughed, "so chivalrous. Yes, I want your cock. No, I'm not that drunk." With that she licked the head of my cock as I leaned back and relaxed on the couch. She proceeded to lick up and down the length of my cock as well, before taking it into her mouth. She stopped without saying a word, and reached into a box on the coffee table behind her. She grabbed a hair tie and pulled her hair back in a ponytail. Always a good sign.

She stroked my cock again momentarily before taking it back into her mouth. She bobbed her head up and down, occasionally looking up and making eye contact with me. There really is nothing like a woman making eye contact with your cock in their mouth. Then, suddenly, she took my cock all the way down her throat.

"Woah," I said in both shock and pleasure.

She took my cock out of her mouth and said, "what, never been deepthroated before?"

"Well, I have," I answered, "just didn't know it was in your repertoire."

"Glad you liked it," she said, "because when you cum I want you to cum down my throat."

Hearing that almost made me cum right then and there. I knew I wouldn't last much longer like this, so I pulled her up and kissed her. "Stand over me on the couch," I said.

She climbed on the couch and was standing over me. I went to remove her underwear and found she wasn't wearing any. She was still wearing her dress, so I hadn't thought to check. She was completely shaved, which seems to me more common with younger women these days. She put one leg on the back of the couch to give me better access, and I licked the length of her slit. She let out a moan as I did. I did that a few more times before I flicked her clit with my tongue, which caused her to pull my face harder into her pussy. I grabbed her amazing ass to hold her in place, and swirled my tongue around her clit.

"Fuuuuuuck," she said, "I never would have expected this from you."

I wished I could see the look on her face, but my own face was buried in her pussy underneath her dress. I continued to alternate between swirling around her clit with my tongue and flicking it, and I could feel her getting wetter and wetter. I started sucking in her clit, figuring that would finally push her over the edge.

"Fuck me, fuck me..." she moaned, "I wanna cum with your cock inside me."

With that I slid out from under her and got behind her. She dropped to her knees on the couch, holding onto the back of it and sticking her ass up. I guided the tip of my cock to her pussy and slid it up and down her slit a few times to get the head nice and wet. I pushed the head of my cock inside her. I paused for a second as she gasped, and then slowly pushed in until I was balls deep inside her.

She must have been really close beforehand, because as soon as I was completely inside her she started to cum.

"Shiiiiiiit!" She exclaimed. I felt her pussy throbbing, doing its best to try to milk my cock. I withdrew most of the way and pushed back in again as her orgasm continued. I held it in this time, savoring every muscle contraction of her pussy on my cock. Finally, her orgasm subsided.

"Keep fucking me," she demanded. "Stretch me out."

I started fucking her with slow, deliberate strokes as I held her waist. I slowly picked up my pace, and she was pushing her beautiful ass back into me with each stroke. I smacked her ass at one point, and she moaned in approval.

After a few minutes, pulled out and rolled her over so she was on her back. I leaned in and gave her a passionate kiss. As I kissed her, I slid my cock inside her pussy, not stopping until it was balls deep. She moaned as we kissed, and started kissing me back more forcefully.

She broke our kiss and whispered in my ear, "I want you to fuck my ass." Don't have to tell me twice. I pulled out and lined my cock up with her asshole.

"Wait!" she said, grabbing her phone from the end table. I wasn't sure what was going on until I heard the telltale FaceTime ring. "Once I tell you to, stick it in my ass. I'm going to make Tony watch."

I heard Tony answer, "Hey Mindy, what's up?"

"Oh, not much," Mindy responded.

"Before you say anything else," he said, "I want to apologize again for what happened in Mexico. It was stupid."

"Ya, it definitely was," she said, "speaking of that, I have something I want to show you."

"Ok..." he said.

She flipped the camera to rear facing and gave me the thumbs up. My cock was still wet with the juice from her pussy, so I slowly pushed against her asshole and the head of my cock finally popped in.

"Oh God," she said, "I can't believe it's in my ass."

"What the fuck, who is that?" Tony asked frantically.

Mindy ignored him and instead said to me, "push it all the way in, stretch me out like Tony never could." With that I slowly pushed my cock in until I was balls deep in her ass.

"Holy shit!" she exclaimed. She flipped the camera back around to front facing and said, "Fuck you Tony, he's going to fuck my ass like you never could." With that she threw the phone aside and said, "Take it slow, I haven't had my ass fucked in awhile."

"Bring your legs together," I told her, "it'll make your asshole not quite as tight, should make it easier for you to take it."

She did as I said, and I put her legs over my right shoulder. I slowly pulled out before pushing back in again.

She let out a moan and said, "You're right... that helps a lot."

I continued to very slowly fuck her ass, gradually increasing my speed based on her reactions. Once she was more relaxed, I moved her right leg so that one of her legs was on each shoulder. I continued to slowly thrust in and out of her ass, and I slipped two fingers in her pussy.

"What the..." She said. I started stroking her G-spot with my fingers with the old "come hither" motion as I continued to fuck her ass.

"Fuck. FUCK. Keep going," she demanded. I added my thumb rubbing her clit to the mixture, so now she had my cock filling her ass, fingers in her pussy, and my thumb striking her clit.

"FUCK! I'm cumming!" she exclaimed. I felt her ass contract in my cock and her pussy on my fingers. She came so hard she squirted a bit on me, but I wasn't about to complain. She came for what seemed like an eternity before pushing me back and dropping to her knees, taking my cock in her mouth directly from her ass.

"Wow, you're a dirty fucking slut, aren't you," I said as she sucked my cock.

"I'm not normally like this," she said, taking my cock out of her mouth for a moment, "but you apparently bring it out in me. Now cum down my throat like I told you."

She went back to work, stroking my cock furiously with her hand and sucking in the head. As I got closer, she continued stroking my cock and opened her mouth.

"Come on, cum for me," she demanded as she looked me in the eye.

That pushed me over the edge, I shot one rope of cum across her face and then she took me balls deep down her throat and bobbed her head, basically fucking me with her face and draining every drop of cum from me. I finally finished cumming and she came up for air.

"Holy shit," I said

"Glad you enjoyed it," she said with a smile as she wiped my cum off her face and licked it from her hand.

"Bet you've never been happier to have a car battery dead, huh?" I said with a laugh.

"Damn right," she said.

"You didn't ruin your dress, did you?" I asked. It occurred to me she never had taken it off.

"Nah, it's still good, I'll probably dry clean it after all that, but no damage done," she responded.

"Well, I hate to fuck and run, but I better get going," I said.

"No worries," she said, "and hey, next time we work a late night, maybe we could find a quiet place..."

"I wouldn't mind that at all, and I could always come over for some more bourbon too," I said with a smirk.

I got dressed and drove home. When I finally got home, my wife was waiting in the living room watching TV.

"Well, well," she said, "look who finally came home."

"Ya, sorry," I responded, "ended up being a longer trip than I expected."

"Go take a shower, you SMELL like sex," she said with a laugh.

I took a quick shower, and when I hopped out I found Sara on her knees in our bedroom with a blindfold. She must have heard me coming.

"I know I said before I wasn't into the cuckquean thing, but I kinda wanna dip my toe in it. Make me suck your cock while you tell me about you and Mindy.

I walked over and out my cock in her open mouth, and she started sucking.

"Well," I started, "it started out as just a drink. She drank a bit more than I did, though."

"Did she start things or did you?" she asked, taking a brief break.

"She did," I answered, grabbing the back of her head as she went back to sucking, "she kissed me, apologized, and that led to us talking about our arrangement."

I continued, "we kissed for awhile, we went down on each other, then she demanded I fuck her because she wanted to cum on my cock."