Night out with my older, engaged, coworker [MF]

So I’ve been lurking in these subreddits for awhile and have a lot of stories to tell just haven’t had the time to sit and write them. One of the positives of this whole safer at home policy is I now have time to write these stories down. There’s kind of a lot of backstory so if you want to get to the night of the deed skip to the ****

This is a story about my coworker Jessica and I. I had been working at this office for about a year when Jessica showed up. Now this is a company where the employees somewhat skew older. I myself was 27 at the time and I was one of the youngest there. Jessica herself was 36, a mere 9 years my senior. But let me tell you when I say that she did not look her age. I could swear she was right about my age, and every single guy at the office was looking at her like she was. Jessica was a social butterfly. Within a month she was best friends with everyone here. She had long brown hair and the sweetest and most infectious smile you ever saw. Whenever she looked in your direction and smiled you couldn’t help but smile right back at her. Every single guy would vie for her attention and she would give every single guy the attention she knew they wanted. The main thing stopping any single guy from trying anything was the big diamond ring on her ring finger. Jessica was engaged.

About a year later Jessica and I became friends at work. There was a group of us that we’d all eat lunch together down in the break room and we’d all talk about the weekend and what we did after work. The group of us all became pretty good lunch buddies and we’d notice when one of us was gone for the day. Especially if it was Jessica. She always started the conversation and asked and told us about her weekends. She absolutely loves drinking. Not to the point where it’s obnoxious but you can tell she’s a party girl through and through. She loves any excuse in order to get a group of friends together and do some drinking. So around Thanksgiving she organizes an unofficial company softball game. I was unable to make it due to going out of town so on Monday when we came back from holiday it was the talk of the town. Everyone was talking about and Jessica offered to show me pictures of the game that her fiancé took on his camera after lunch. So later in the day I made my way to her cubicle to ask to see the pictures. She scrolled thru the phone and showed me a hilarious picture of one of our coworkers completely missing the ball. Quickly thinking of a way to get a cute girls number I asked her if she could text me the picture so I could make fun of said co worker. She took my number down and sent me the picture later that day. Step 1 complete.

After she sent me the picture I texted her back later that day and just said a simple “thanks and our coworker is never going to here the end of this!” She didn’t end up replying. I told myself, “Of course she’s not gonna reply. She’s at home with her fiancé.” Clearly, I was thinking bad thoughts about my coworker and rationalized that nothing would ever happen because she’s engaged. But, it was so hard to not let my mind wander. Jessica was about 5’2” with a slim body. She had a cute runners butt with a flat stomach and suspiciously big breasts for her frame. The girls in the office had a weight loss competition for about 4 weeks the first few months she was here and she lost about 15 pounds. She’s already only about 115 so when she lost another 15lbs it was a big change. Her ass got smaller and her clothes fit her looser. But all throughout this time, her breasts didn’t seem to get any smaller. They were as perky as can be, and now with the increased weight loss they seemed even bigger than they were before.

Throughout the months our lunch buddy group of friends would have email chains where we’d goof off and have jokes among us. I always found a way to email just Jessica about something and eventually I started making things flirty. She was always somewhat of a flirt so I didn’t really take it to mean much. But me being me, I kept pushing the line. Seeing just how far I could take it. It got to the point where she ended up texting me for the first time since our initial conversation and she said “Hey, I am kinda scared that IT can see our emails so maybe YOU should slow it down on the flirting lol. I’ve noticed rumors travel fast here…. But in all seriousness I would hate for u or me to get told anything, or in trouble. I know its all in good fun, but you never know ;)” I basically said that I completely understood her concern and that if I’ve said anything that made her uncomfortable that it wasn’t my intention. She quickly responded “Not at all! Believe me you didn’t say anything to make me feel that way, I promise! I rather enjoyed the flirting, plus I like to mess with you ;). I KNEW it was on.

Throughout the new few weeks I kept teasing her and she’d tease me back. She’d tease me about my age and I’d tease her right back. I’d ask her what she’s doing and she’d tell me she was working out because the girls decided to have another weight loss competition. And that was when I took my chance about something I had suspected. Did Jessica have fake boobs? Yes, yes she did. She told me she got them done when she was about 22 years old, that she was a tiny A cup and wanted to go with a nice and perky C cup. I told her I had noticed cause they didn’t seem to get smaller in the last weight loss competition.

“Oh so you’ve been looking at my boobs?”, she said. I replied with, “Well it’s really hard not too when they’re as nice as they are.” She replied with a smiley face. “Well thank you and you look pretty good yourself ;)”

Now about me, I’m brown skinned and 5’8”. Completely average height, but I work out 2 hours per day. I alternate days training Brazilian jiu jitus and muay thai along with weight lifting on the weekends. I’m a solid 175-180lbs with about a 4 pack of abs and if I cut weight a six pack. Now, not to sound cocky but I always send pictures of my abs to girls. In my experience girls don’t want dick pics. Girls want to be teased and let their imaginations run wild so shirtless pics usually do the trick.

I reply to her “ehh I’m a little thick right now but a few weeks ago on vacation I looked pretty good.” And I sent her a picture of me at the beach on vacation. She replied “Wow! I had no idea all of that was under your work clothes. It’s going to be hard seeing you at work now and not imagining that!” Normally I’d try and press my luck and reply with it’s only fair I get to see what’s underneath your work clothes now too but I decided against it. Instead, I swung for the fences. I asked her out. I asked her out for Saturday night. To go out dancing with me. (I’m a terrible dancer but I LOVE dancing and making a fool of myself.) She says what weird timing, her fiancé is going to be out of town and she would love to go out with me.

*****
Saturday comes along and I tell her to meet at my place and we’ll go from here. She shows up in a skirt, heels, and a tube top. No bra. I am in awe. She looks incredible. Her calves perfectly accentuated by the heels she’s wearing, her thighs so smooth and toned. Her cute butt just begging to be grabbed , and her boobs looking incredibly perky and tan. She flashes a smile at me and I give her a big hug. She presses her boobs into me with a sneaky smile.

We grab and uber and head out to downtown. The whole drive was surprisingly relaxing and flirty. I thought she’d be nervous or id be nervous but conversation flowed so easily and smoothly. We ended up going into a Spanish restaurant for some tapas and drinks while a flamenco band played. Very relaxing and intimate atmosphere and I took this time to get right up close to her. I put my arm around her and we talked and looked at each other and smiled. Not knowing where the night would take us but and underlying feeling of wanting each other. We finished up at this restaurant and headed out to a bar with speakeasy underground and a club. As we’re walking there I notice that her left hand is different tonight. The ring is gone. The diamond ring her fiancé gave to her 5 years ago is missing from her finger.

We get into the speakeasy and I get us drinks while she finds a spot to sit down. I end up finding her in a dimly lit corner of a lounge and I take a seat next to her. Making sure to nestle myself as close as possible. We take our drinks and cheers. By this point in the night I’ve been touching her all over her thighs and lower back. Touching her hands and running my fingers up and down her arms. We look at each other and we kiss. I can still image the soft touch of her lips and sweet taste of her tongue. From that point on in the night we kiss at every moment we can. We eventually make our way to the dance floor of the club and dance the night away.

I’m grabbing her everywhere and kissing her lips and her neck. She’s grinding her ass into me and making me harder and harder, all the while pushing her ass more and more into me. After a long deep kiss I look at her and say “It’s getting pretty late, you wanna head out?” She bites her lip and nods yes. We make our way out of the club and grab an uber. Surprisingly we’re two for two on non-talkative uber drivers so we get in the car and it’s almost like we’re the only two people in the world. We’re softly making out in the back seat and my hands are all over her legs and ass. I can’t keep my hands off of her and she can’t keep her hands of f of me. Before you know it we’re back at my place.

“I hope you don’t mind if I spend the night, but we’re NOT having sex.” I say of “course not, I’m an angel I only hold hands with girls” and grin. She grabs her overnight bag from the car and we make our way inside and to my room. She goes to the bathroom to change into her pajamas while I undress down to my boxers and a shirt. I turn the tv on and put the office on. She comes out of the bathroom in a tiny thin tank top and some small booty shorts. I can see her nipples poking thru the thin fabric and can see her tight ass peaking out from under the booty shorts. She jumps into my bed and immedialty reiterates “We can make out, but we are NOT having sex.” “Hey, you’re the one all over me!”, I reply. She smiles and we go back to making out.

At this point she’s straddling me while I’m laying down and grinding herself into my hard cock. Both of our breathing is getting deeper and deeper. My hands are groping her ass and sliding underneat the material of her shorts. Her soft skin and round ass fitting perfectly in my hands. I grab her firmly and move her up and down, grinding her harder and harder. Kissing her and spanking her. Each time my hand meets her ass she lets out a moan. She’s grinding and grinding on me. Breathing deeper and deeper, moaning louder and louder until she lets out a yell with my name. “Sergio!, I’m cumming!” Her legs twitch and she bucks down on top of me. She relaxes for a bit while kissing me chest and my arms are around her.
I can’t take it anymore. I lay her down, grab her by the neck and kiss her deeply. She lifts her chin up to give me more of her neck and I make my way down it kissing her and biting her as I make my way down to her perky tits. The thin fabric is doing nothing to hide her hard nipples from me. Not being able to control myself I pull the top down and go mouth first to her right breast. She let out a deep moan as she pushed her breasts forward. Her hands running thru my hair pushing me harder into her as I lick and suck on her tits. I make my way back up kissing her neck and biting her lips. I take my right hand over her pussy and just cup it. Feeling the warmth being radiated and her wetness thru the shorts. Making out deeper and harder as we let our tongues dance around each other. Sporadically biting each others lips and my hand slowly starts moving on her pussy. She moans and moves her hips up to meet the motion of my hand.

I slide my hand under her waist band down to her pussy and feel just how wet and silky smooth she is. I slide my fingers down and spread her lips to get my fingers covered with her and back up to rub her clit for a tiny bit. I take my hand up to my face and look her in the eye and lick my fingers clean. She bites her lip and I tell her how good she tastes. She kisses me deeply and says “Now I want to see how good you taste.” She pushes me over and I lay down. She sits up and takes her top off finally letting her tits out. The perkiest titties ever.

She kisses my chest and slowly makes her way down. She licks my nipples and licks me all the way down to my belly button. She bites the waistband of my boxers and pulls them down with a little help of her hands. My dick springs up to meet her. My dick is completely average in length (6”) and girth (6” circumference) but she swore it was the biggest dick she’d had in a decade. Given the way she worshipped my cock, I believed her.

She kissed it on the head and licked me down to the balls and back up again. She spit on her hand and slowly stroked it while suck on my head. Her other hand was playing with my balls and her tongue was swirling around underneath my head. It was incredible. I gathered her hair up in my hand and out of her way and she moaned while my cock was in her mouth. She looked right at me as she bobbed up and down . The way she looked me in the eyes was pure lust. I couldn’t believe this sweet and bubbly woman from work had my cock in her mouth. Telling me how big and hard my dick was and how good it tasted. I told her how sexy she looked with my dick in her mouth and she smiled. I told her how badly I wanted her and how much I thought of her sucking my dick. And I told her how badly I wanted to cum in her mouth for being such a good girl.

Her eyes perked up and with a reinvigorated energy she spit on my cock and went to town. She worked my dick like it had never been worked up until that point. She took me all the way down and I held her head there for a few seconds while she looked up at me. Smiling with her eyes. It wasn’t long before I told her I was about to cum. She kept her mouth on my head and stroked me and looked at me. I blew my load straight into her mouth. Over and over my dick twitched as I shot load after load. Some cum came out the sides of her mouth as she moaned and cleaned it all up. I came so hard and so much. I couldn’t believe that we had done this. She was 9 years older than me, engaged, and we worked together. It was everything that we were’t supposed to be. It was so wrong. But it made it so much hotter.

I finished cumming and she kept softly sucking on my dick. Making sure she swallowed every last drop of my cum. My dick was so sensitive I had to tell her to stop, she giggled smiled and said “ You taste really good.”

This is really long now and I have to get a workout in. There’s more to this night and many more meetings between Jessica and I. And I loved writing this. Probably wouldn’t have taken as long if I didn’t have my hand on my dick half the time but this safer at home thing has me going crazy. I’ll definitely be writing more and hope you guys like it!

*EDIT Thought I’d add a picture to give everyone a glimpse of those titties https://imgur.com/jmu9HRD

Source: reddit.com/r/gonewildstories/comments/g6zxou/night_out_with_my_older_engaged_coworker_mf