[MF] [Cheating] Escalating with an ex

This is longer than I thought it would be, so I’ll post part 2 tomorrow.

I suppose I should start out saying I know that cheating is wrong, and I’m a terrible person. Let’s move past that.

Now, some background. I dated a girl in high school for a few weeks. It didn’t really get too serious because her family ended up moving to Florida. The craziest we ever got was making out on a couch at a church New Year’s party. I got a handful of her ass, and some under the shirt over the bra boob. She got to feel an outline of my erection through some blue jeans. Her name was Sara. In high school she was as skinny as a rail. Dark blonde hair, blue eyes. Her boobs were smaller than I’d prefer, but man did she have an ass.

Fast forward about 8 years. I’m working full time as an assistant supervisor in a health care facility, and engaged to the girl I started dating after Sara. On this particular day I was doing some paperwork in some of the living areas when HR brings in a class of new hires for a tour of the campus. It was basically a couple administration buildings and then a bunch of group homes for the patients.  I see a familiar face in the crowd, and her enthusiastic wave lets me know that Sara recognized me too. She hasn’t changed much over the years. She was a little bit thicker, not in a fat way. She looked healthy. Her tits had grown some, but were still a bit in the small side. Her ass was still amazing. It filled out her blue jeans perfectly.

A few weeks later I was sitting in the office I inherit every time my supervisor calls out sick. The job wasn’t too bad. When I was in charge I was responsible for making the following days schedule for the direct care staff and making sure everyone was doing what they were supposed to be doing. There’s a sharp knock on the door, and Sara comes strolling in, obviously upset about something.  

“What’s up?”, I asked her.

“Can you tell Jane that she’s supposed to be training me, not cutting out coupons? She’s been sitting at the table for like 3 hours, and I’m sure there’s something I need to be doing.”

I laughed, and explained that there was a lot of downtime at our job.  That seemed to cut the tension and she looked more relaxed. We talked for a few more minutes before I suggested it was probably time for her to get back to the home.

“You cool?” I asked. “No more getting your panties in a bunch?”

She got a devilish look in her eyes before responding “I’d have to be wearing them to get them in a bunch!”

Before I could reply she was gone, leaving me to ponder on what was under her pants.

A few hours later she returned to get some supplies for the home. We made some small talk for a bit. The usual: how’s your night going? Any plans after work? Nothing too exciting, but I was bored out of my mind, so having some company was nice. She was wearing a black shirt that hung low enough to show cleavage, but was pretty tight across her stomach, and some grey workout pants that really showed off her ass. As she bent over to pick up the supplies the fabric of her pants was pulled tight across her perky ass. I quickly scanned my eyes across her checks, searching g for signs of panties, boy shorts, a thong. I found nothing. This piqued my interest. I just couldn’t help it.

“So, no panties, huh? None at all? I blurted.
She looked at me and smiled. “None.”
“Prove it!” I really needed to find a cork for my mouth. At the best she’d take it as flirting, which an engaged man shouldn’t be doing. At worst, she’d take it as sexual harassment, which would cost me my job.

Without hesitation, she hooked her thumb into the waistband of her pants and tugged them down. Not at the sides, or even the back, but right in front. As she pulled down more and more of her freshly shaven mound appeared before my eyes. She stopped just shy of me getting a peak her lips.  I was stunned, and couldn’t find any words for a response. I felt myself swelling instantly. It’s a good thing I had a desk to hide behind. She looked at my flushed face, turned on her heel, and strutted out of the office. It may have been my imagination, but I swear she put some extra effort into making sure her ass swayed as she left the room.

I fought down the feeling of guilt that bubbled up from my gut. It wasn’t cheating, just innocent work flirtation.  I’d just have to take care to make sure it didn’t get out of hand. No big deal. Everyone flirts at work.

After shift change I packed up my things and headed out to the parking lot. As I approached my car I heard someone call out my name. I turned, and there was Sara, leaning against her car. Waiting for…me? Why would she wait for me?

“Hey Sara, what are you still doing here?
“Didn’t feel like going home yet, thought I’d see if you wanted to hang out for a bit”
“Oh…uh. What did you have in mind?” I asked cautiously.
“We can just chill here and talk.”
“Yeah, I got a few.”

We didn’t talk about anything of worth. Just caught up in each other’s lives. She had to move back from Florida because her grandma got sick. She had a few relationships but none of them turned into anything serious. She said she was young and still wanted to have fun.  She couldn’t believe I was engaged. She said she was kinda sad the two of us never really had a chance to play out.

“So…” her devilish look was back, ” you like what you saw earlier?”

“W-what, what do you mean?” I stammered, stupidly.

She cocked an eyebrow at me.

“Uh. I mean, I didn’t really see anything but a bit of skin. The lighting in there was crap haha.”

She moved closer to me, almost touching her lips to my ear, “Well, if you wanna see more, all you gotta do is ask.”

“Tempting. Tempting. But I’m with someone, and that wouldn’t go over well.  I should get going. Have a good night.”

I got in my car and I drove home. My fiancé was asleep when I got home, like she usually was. She worked days, I worked evenings. I went through my normal routine. I grabbed a snack, washed a few dishes, and went and took a shower. I fought to keep from fantasizing about Sara’s big ass, or the smooth mound she teased me with. I got out and went and turned on the TV, looking for something to watch.  The notification light on my phone was blinking. Something from Facebook.

*1 new friend request* Sara didn’t waste much time adding me. Against my better judgment, I accepted it. *Buzz buzz*. New messages from Facebook Messenger

Sara: Hey! Hopefully I didn’t scare you off earlier. I was just having a bit of fun!
Me: It’s OK, just not used to girls messing with me like that.
S: Oh, I wasn’t playing. I meant it. All you have to do is ask.
M: lol, good one.

I went back to watching TV. A few minutes later I heard my phone buzz twice. Then twice more. Then a few more times.  

*4 new messages from Sara* I opened my phone, thinking she’d changed the subject. I was wrong. Instead, I had picture messages from her.  The first one wasn’t too wild. Her standing in front of a full length mirror in the same outfit she was wearing at work. She was leaning to the right slightly, biting her lower lip. There was a bit more cleavage showing. Her thumb was looped through her waistband, pulling it down.  I could barely make out the folds of her pussy lips.

The second image was from the back. She’d rolled her pants off the back of her ass, as she was bent away from the camera. Her ass was perfect. I hesitated.  I was so turned on I was already throbbing against my boxers, but I didn’t want to do something I’d regret. In the third photo she was naked, on her knees, leaning back slightly, showing off her perky tits and flat stomach. The hand not holding the phone was laying lightly in front of her pussy, obstructing my view.

Picture number 4 showed Sara laying down, with the phone over her head. She was looking up sweetly with her pretty blue eyes. The twin peaks of her perky chest in full view. Her legs crossed tightly against themselves, once again hiding what I was so eager to see.

S: More?

I couldn’t reply. I wanted more, I wanted to see the delicate folds of her pussy lips, I wanted to see more of her magnificent ass. Instead, with these fresh images burnt into my mind, I wrapped my hand around my swollen member and took care of myself. I went to bed with new fantasies playing through my mind.

The next day at work started pretty uneventful. It wasn’t until close to the end of the shift when I was working on the next day’s schedule that Sara bounced into my office, looking pretty cheerful.

“Ooh, where am I at tomorrow?” she asked as she walked to my side of the desk.
“You’re with Jane again.” I replied, trying to keep my eyes off her shapely rear end, which was hovering a few feet to my left while she leaned over the desk inspecting my schedule.  

I scooted away from the desk to grab some paperwork. As I pulled myself back, Sara shifted into my path.

“Oops. I dropped my pin.” She bent over, making sure to push her ass out. I stopped in my tracks, eyes glued to her. She snapped back up just as quick as she bent down. She took a step back, pretending to lose her balance, she missed her next step and landed in my lap. “I’m so clumsy!” She giggled. My breathing got heavy. She leaned back and ground herself into my crotch. I felt myself lengthening in response. She pushed harder against me. She angled the bulge in my lap between her spectacular cheeks. She laid herself back against my chest. My hands grabbed her hips as she continued to tease me with the lap dance.  

And then, it was over.  She got up, shot her devilish smile, and left the office, leaving me alone with my pitched tent.  I sat there reeling, thoughts of what just transpired swirling through my mind. I was heavily distracted the rest of the night.  I finally managed to finish my paperwork as the 3rd shift supervisor walked in. I gave shift report and hurried out. I went home, showered without thinking about Sara too much, and sat down to watch some tv.

Source: reddit.com/r/gonewildstories/comments/66egym/mf_cheating_escalating_with_an_ex