My night with my Gilf Colleague [MF]

I’ve had a lot of fun reading this sub and finally decided to share one of my favorite experiences.

The first job I had after I left college, I started working for a big firm a couple of miles away from where I lived. I found a lot of the woman there were really, really friendly. Now, I’d love to say that this was all because of my dazzling good looks and while I don’t look too shabby, the fact that I was the junior to all of my male colleagues by at least 15 years and the women outnumbered us 4 to 1, might have had something to do with it as well. But, seeing as I was in a relationship and had no interest in cheating on my girlfriend, I kept my distance and soon any romantic interest in me seemed to fade. The one I did keep flirting with, Mona, was an absolutely stunning woman in her early fifties. She was very fit, had a nice natural tan, amazing legs, an astonishing rack, a gorgeous face and dressed perfectly. For, uh, research purposes I’ve tried to find the porn-star gilf that looks most like her and Tori Baker comes really really close (Tori has the bigger rack, Mona has less wrinkles and even nicer legs and ass)

The reason I continued flirting with Mona was mostly because I really didn’t think it would lead to anything, like ever, and saw it as harmlessly blowing of some steam at work. I found that we had pretty similar views on a lot of things and she lived really close to my apartment. So in the following two years we carpooled every now and then, and I started hanging out with her more outside of work as well. In that time I basically got to know everything there was to know about her and her love life. She had been married for over 20 year in an abusive loveless marriage, until her husband died. Then she pretty much vowed to never let a man use her like that again, only to start an affair with a man who would promise to leave his wife for over 2 years, but never did. 

As she started breaking up with her boyfriend, things between me and my girlfriend were far from great as well and Mona and me grew closer together. We talked a lot, started meeting each other even more outside of work and found emotional comfort in each other. We never got to a point where we considered ourselves to be dating or did anything anyone would find too suspicious, but pecks on the cheek to say hello became little kisses on the mouth, hugs would linger that little bit longer,… I really started hoping and pushing for something to happen between us, but she would always find a way to make it sound as if it could never happen. “If you would have been that much older, if it weren’t for our age difference, if people wouldn’t be so judgmental,…” We basically got stuck in a never-ending loop of me trying to convince her that I didn’t give a fuck about her age and Mona trying to convince me that there was no way anything could ever happen between us, to the point where we both became so frustrated with the situation, we had no other choice then to get some distance between us. 

Then one of our co-workers threw a birthday party. We decided to carpool with two other co-workers, who would pick us both up at Mona’s place. When she opened the door, she looked amazing. She wore a white pencil skirt, a red button-down blouse, with one button undone, showing of her magnificent cleavage and she wore a pair of killer heels. She kissed me swiftly on the lips and invited me in. I’d hoped to be the first one there, but found out all too quickly that everyone was already there and eager to get going. As we got closer to the address, I could already hear the party and after we found a parking spot and got out of the car, I was certain of one thing: this would be the kind of party that would either end early because of a huge drunken drama or because of the cops stopping it. Music was ridiculously loud, a lot of shouting going on and even more drinking… We got in, said hello and got a drink. Twenty minutes in, the first angry neighbor shows up, then the second, then the cops show up a first time. All this wholesome fun was just too much, so it didn’t take long for us to decide on getting the hell out of there. Our co-workers dropped Mona and me off at her place and, luckily for me, both of them declined to come in for a nightcap. 

Mona told me to take a seat on her couch as she took of her heels and then took a bottle of wine and two glasses out of the kitchen. She poured us both a glass and sat down next to me, putting her legs on my lap. She wriggled her feet, inviting me to rub them and we started flirting and talking like we had so many times before. I was gently massaging her calves and feet, holding my breath each time I pushed a little further up, until all of a sudden she pulled her legs off of my lap and tells me I better go. When I asked her why, she said: “I have a really hard time fighting against this and I know I need you to leave now or I will regret this.” And this is where I’ve probably said the best lines of my life: “I know you want this as much as you do, and I can tell you a hundred times more that I don’t care about any of the things that are stopping you. You want me to go? fine! But for one second close your eyes. Imagine no outside world, no age difference, nothing holding us back. Now I’m asking you can I kiss you one time for real? Just one real kiss?” 

She looked at me and paused for what seemed an eternity and then nodded. I put my left hand on her cheek and softly kissed her on the lips and she gently started kissing me back. It was a soft loving kiss that grew more intense every time our lips met. Then I flicked her upper lip with my tongue, which she answered with slipping her tongue into my mouth. As our kiss got more heated, my hand started wandering from her knee up to between her thighs, until I reached her panties. I could feel she was getting wet, her breathing got heavier as I gently started stroking her through the fabric. She pulled out of our kiss and looked into my eyes: “Tomorrow, this never happened, OK?”. I nodded as she straddled me. She pulled off my shirt and started kissing me again. I unbuttoned her blouse and exposed her gorgeous chest, sealed in a lacy dark purple bra. While my hands started sliding the bra straps down from her shoulders, I started kissing her neck. Then I worked my way down to her collar bone. She started grinding her hips on my lap as I took off her bra. What a magnificent pair of breasts. She had a full round pair of tits, a bit pale, revealing she had been tanning in a strapless bikini, with small darkish pink nipples. As I sucked down one of her her erect nipples, I couldn’t help but admire how much time and gravity really had been on her side. They weren’t the least bit saggy. This was a full pair of firm proud voluptuous breasts that would make most teenage girls jealous. I got lost kissing and squeezing her tits while her grinding made my cock harder than I’ve ever felt it.

I put my hands on her hips and pushed her off of me and down into the sofa. Then I kneeled down in front of her and undid the zipper of her skirt. Without saying a word she lifted her hips to help me pull it down. I parted her legs slightly and started kissing my way back up. I took my time kissing every inch of her calves, her knees, the inside of her thighs, while my hands explored the road ahead. As soon as my hands approached her purple lace panties she pushed them down to her knees me and let me take them further off for her.  I wrapped my arms around her thighs, pulling her closer to the edge of the sofa. With her legs up on my shoulders my lips were now inches away from her immaculately trimmed pussy. There was no denying she was turned on and she shivered slightly when I pressed my lips on her mound and started kissing her pussy. I parted her lips with my fingers and then slowly traced the outline of her pussy with my tongue. When I got to her clit the second time I circled it a few times, which made her moan a little. I decided to tease her some more, licking my way down and then up again, gently sucking her clit between my lips and flicking it with my tongue every passage. She started really getting into it and grabbed a firm hold of my hair. She pushed her pussy firmly against my mouth and slowly started gyrating her hips.

As her breathing got more intense, she pushed me off of her and sat up. She pulled down my jeans and boxers and then into the sofa next to her. I don’t know if it was eagerness or just her style, but without buildup she bent forward and slid her lips over my hard cock, taking him almost completely into her mouth. I let out this huge sigh part enjoyment part surprise. She looked up at me playfully and started deep-throating my cock. She would alternate between fast long up and down movements where she would take almost all of my cock in her mouth and then all the way back up and slower strokes to catch her breath, it was the best blowjob I’ve ever had by far. After a few minutes I was about ready to explode, when she took my cock out of her mouth and straddled my lap, pushing her pussy as close to my dick as she could. I could feel how wet she was as she teased my cock rubbing it with her soaking pussy, almost as if she was daring me to push my cock in.

We started making out again fiercely and when I moved down to kiss her perfect tits again she sighed “I’m so fucking wet, fuck me already”. Like I wasn’t trying to… She reached around with one hand and worked my throbbing cock into her pussy. She really was ridiculously wet. As she started riding me faster and faster, I played with her bouncing tits and took in the awesome sight in front of me. I could feel I was close to coming, but decided to try and make her come first. I put one hand on her hip slowing her down and then placed my other hand on her mound, my thumb perfectly positioned on her clit. I barely had to move it, she started grinding her clit onto my hand as her breathing got deep, moaning with every forward thrust she did. As she started speeding up a little I started rubbing her clit faster which made her moan even louder. She really took up the pace grinding me until her moans turned into this high pitched gasp and her body shuddered on top of me. She made another few pushes forward with her hips and then fell down on top of my chest. I could feel her heart pounding on top my chest as she tried to catch her breath, my hard cock still inside her. “That was amazing” she sighed.

I still hadn’t cum, and as she had a tendency to boast about being much fitter than a lot of 20-year old girls, I’d thought I’d remind her of just that:  “We’re not finished yet, I thought you were still fitter than a 20-year old” She answered me a devious smile raising her eyebrows. I pushed myself up and laid her down on her back on the couch. Then I worked my way back up between her legs and pushed my cock inside her once more. My left hand was on her hips and my with my right I grabbed hold of her hair.  We kissed in a passionate embrace as I slowly started pushing my cock deeper inside her with every thrust. She put her hand on my cheek and kind of pushed me back to look into my eyes, her other hand on my back started controlling the pace. This was something completely different, as we stared into each-others’ eyes I pushed into her, slower, deeper and more intently than I ever had. It was like I was trying to feel her as closely as I could and she was trying to feel me as deep as she could. Then after a couple of minutes she pulled up her legs and wrapped them around my hips.  I picked up the pace and she used her feet to pull me in with each stroke, as if she was helping me to thrust deeper into her. I pulled her close, hugging her tightly as I started pumping into her as deep and hard as I possibly could and it didn’t take long before exploded into her. I never came as long and hard as I did right then.

I stayed on top of her slowly rocking back and forth and started kissing her again. It’s hard to say how long we stayed like that, but it was long. Kissing each other, my semi-erect cock still inside of her. I think we both felt that as soon as I was no longer inside her, everything would end. We stayed like that long enough for us to get heated up once more. Those innocent loving afterglow-kisses grew more passionate once more. Neither of us wanted this night to stop, ever. I could feel my dick growing hard inside of her, as her pussy started to get wetter. She started pushing her hips back into me and soon we were making love once more. After some light thrusting from my side, she motioned me to get off and had me stand up. 

She got on her knees on the couch and bent over placing her hands on the back of the sofa. Then she pushed her ass up and looked back at me seductively, pushing her delicious pussy invitingly back towards me. I placed my hand on her hips and pushed my hardness inside of her. If I was thinking I would be in control like that, I was sorely mistaken, before I could even try pushing into her she started pushing her pussy back and forth over my cock. All I had to do was stand back and enjoy her gorgeous ass as she was sliding up and down my cock. I started pushing back into her and she grabbed one of my hands and moved it from her hips up to her tits. I followed with my other hand and now really started riding her squeezing her breasts firmly. I let her erect nipples slide between my fingers and picked up the pace in my thrusts. She started moaning again and as I started fucking her as hard as I could, I squeezed both her nipples between my thumb and index fingers. She went absolutely wild, pushing back into me as hard as she could, which meant I was mainly trying to stay inside of her with every push. The moaning changed into that high-pitched sigh as she started shaking feverishly once again. 

I slowed down the pace a little as she tried got her bearings back. Every time I heard her catch her breath again, I started thrusting into her deeper and faster until that little shriek came back and then I would slow down once more. The fourth time I picked up the pace again, she didn’t start shrieking. So I kept speeding up until I was pretty much jack-hammering into her, until she let out a deep long moan, an almost desperate plee-ee-eee-eeee-ease. Now it may seem like I was just pushing her limits, but mine had been pushed just as far. With my own cock begging for another release, I got lost in the motion. I couldn’t even tell if she was still enjoying it, everything warped into one long mix of moans and sighs as I came hard inside of her. Then we both fell down in the sofa next to each other. She nestled herself close to me as my little spoon. I held her tightly, my arm wrapped around her and kissed the back of her head. We stayed lying down just like that: kissing, caressing, but mainly just holding each other tight without saying a word. 

Source: reddit.com/r/gonewildstories/comments/l20k1h/my_night_with_my_gilf_colleague_mf