[MF] Hooking up with an older coworker [long]

I’ve been a long-time lurker in this sub and finally decided perhaps it was time I shared one or two stories of my own. I apologize if this story is on the longer side especially the set-up.

So, I’ve always had a thing for older women, at least for as long as I can remember and to this day that has not changed. I used to work for a company where I was almost always the youngest employee there. I would see gorgeous older women get hired and quit frequently, the job was demanding I guess until one finally stuck. My company owns several offices across the city, and I would mainly work out of the main one while she worked out of a different one on the opposite side of town. Every now and then I would be lucky enough to work side by side with her but that was very rare.

I’m not the best at painting a mental picture but I’ll give it a try. At the time I was 22 and she was 34. She was about 5’3” with a very curvy body, large breasts big C maybe D I never really looked at her bra and she had a nice round ass that she liked to shake around the few times we were together. She was a dancer in her younger days and claimed to go to the gym frequently. She did have signs of having had children but that did not take away from her beauty. She also had a few tattoos across her body that hinted at her past dance training. Short light brown hair sometimes dyed in different colors.

Initially, we started flirting through the messenger we used on the computer at work to communicate with the other offices. This got us into trouble more than once because one of the managers read what we were saying and did not appreciate. Needless to say, after this we started doing all our flirting through text instead and that is when things started to get a little heavier. One day we were texting just casually nothing too serious or flirtatious. She once claimed to give an amazing back massage and I thought I’d tease her a little.

“Hey you said you give great massages didn’t you?” I said

“Yeah… why do you ask?” she replied

I could feel she knew where I was headed with this and it was too late to go back now so I pushed on.

“Well I just ask because it’s been a stressful few days at work and I could really use a back rub ;)” I replied. She knew it had been rough at work so at least that wasn’t a lie. And yes, I did throw in that winky face at the end.

“Oh really…. and you think a back rub is going to relieve that stress?” she said

“We won’t know unless we try right? ;)” I said. I now regret so many winky faces but I was young and horny. Anyways…

“And let me guess you’ll also want a happy ending afterwards?” she guessed correctly

‘My god this woman is a psychic!’ I thought to myself. We’ve been flirting for a while and I’m pretty sure she could guess I wanted to get into her pants by now, so I guess it wasn’t too hard for her to guess that’s what I wanted.

“I mean if you’re offering, I’m definitely not going to say no ;)” I said now wishing I could take back all those winky faces.

Several things happened at once after her next message. My heart skipped a beat, jaw dropped, eyes opened wide and my dick began to come to life. She had sent me a picture of herself in nothing but her bra and panties and a puzzled look on her face and a message that read “are you sure you still want that “massage”?”

After a few seconds of stroking my dick until it got as hard as it possibly could I collected myself and began to reply. “are you serious? Fuck yes! Can I come over right now?!” I managed to reply without telling her straight up I wanted to fuck her.

“Haha yeah sure you have my address, right?” she said and without replying I was on my way to her house.

She’s separated and the kids were with the dad for the weekend, so I knew this was going to be fun. I ran up to her door and rang the doorbell a few times, desperate and eager to see what was waiting for me on the other side. Finally, she opened the door wearing a robe tied just enough to barely cover the bra and panties from the picture.

“What the hell? How many red lights did you run to get here so fast?” she teased me. “It’s fine I wasn’t pulled over so it’s ok. Can I come in?” I said as I looked her up and down trying to mentally disrobe her. She closed the door behind us and let the robe fall off as she walked back to her room. I quietly said to myself “fuck me” and she laughed and turned to look at me “geez not here… in the bedroom” winked at me. I couldn’t take it anymore; my dick was rock hard, and it needed some release. I quickly ran up behind her, cupped both of her tits in my hands and pressed my stiff cock against her back.

I’m not sure if it was my playing with her tits or the feeling of my hard cock against her back that caused her to moan, or perhaps a combination of both, but I needed to be inside of her one way or another. I carried her the rest of the way to her bedroom and began to make out with her, holding her up with my hands on her panty clad ass and my bulge pushing against her.

I should also mention that one of my biggest turn-ons is eating pussy until she’s cumming all over my face.

I say that because as soon as I knew we were safely over her bad I dropped her and dropped to my knees and began to eat her out like it was my last meal. Her panties were already wet and I began to lick the wet spot, taking in the taste and the aroma with every lap of my tongue. This made her moan even more but I wanted more, I needed her to moan my name as she came all over my face thanks to my tongue. I moved the panties to the side and began to lick her bare pussy already dripping with her delicious juices. I stuck my tongue in and fucked her with my tongue moving it in every way I could possibly think of. Remembering to rub her clit with one hand while the other explored her ass a little more. I removed her panties and dove right back into her pussy, eating her out while my thumb rubbed her clit at a steady pace. My other hand found its way to her asshole and I wanted to see how she felt about it. I put a little pressure against her tight hole making her groan and she let me know she didn’t like that. I was fine with it, so I continued eating her out until she finally came. She squeezed my head with her thighs, grabbed handfuls of my hair and held me tight against her as rode out the wave of the first orgasm of the night.

After she finally released me, I crawled up over her and she looked at me and trying to catch her breath she said, “we’re not done yet” I smiled and said, “we better not be” and I kissed her. Sliding my tongue into her mouth and making her taste or own juices seemed to have turned her on because before I knew it, I was on my back and she was working feverishly on my pants and boxers. Finally free of its constraints, my dick sprung up to attention and like the hungry cougar she was, launched herself at me taking as much as she could in her mouth at once. I threw my head back and place a hand on the back of her head occasionally thrusting upwards causing her to gag. It had been a long time since the last time I had cum so it didn’t take long for her sucking to get me off. After swallowing my entire load, she continued sucking my cock making sure to keep hard enough for the main act. She climbed on to the bed next to me and looked at me with lust in her eyes “fuck me now! Please I need that cock inside of me now!” she demanded.

If I wasn’t already rock hard that request would have definitely gotten me there. I climbed up on the bed and crawled up behind her. I teased her pussy with the head of my dick, running the tip up and down her slit coating it in her juices. “Oh god finally” I heard her say softly and I’m still not sure if she had been craving my dick for a while or she was just craving some dick in general. Either way, I slowly pushed the head in past her lips and slid the rest of the shaft in until I was balls deep inside of her. I held it in place enjoying the feeling of her wet pussy around my cock for the first time before looking down at her. “Fuck me… don’t be gentle… please fuck me” she cried out and she didn’t need to tell me twice. I grabbed her waist on either side and began to thrust into her at a steady pace. I would slap it as hard as I could getting a squeal out of her with every hit and I would grab a handful of her ass after each hit. By the time it was time to change positions her pale ass was red, and I was proud of myself for that.

Once I knew I was getting closer to cumming I flipped her over and pulled her to the edge of the bed. I quickly shoved my cock back into her warm wet pussy and bent down over her and whispered, “where do you want me to cum” she wrapped her arms around my neck and said, “anywhere except inside of me” and pulled me in for another kiss. I was a little disappointed because that’s exactly where I wanted to cum but I wasn’t going to complain now. So, I continued to fuck her for a little longer before I had to pull. I climbed up on the bed, straddled her and began to stroke my dick over her big tits. With her mouth wide open I shot out string after string of cum on her face, in her mouth and the final few landing between her chest.

Once the wave had passed, I sat next to her and looked at her cum covered face “fuck…’ is all I could say as this time I tried to catch my breath. She looked at me with a smile on her face “still feeling stressed?” she asked and with a smile on my face I answered “well I didn’t get my massage so…” and we both laughed before she called me an asshole and she stood up to clean the mess on her face.

After that work became a little more fun, knowing we had a little secret that nobody could know. I know people had their suspicion that something had happened, but nobody ever knew for a fact that we had fucked. And yes, I did eventually fuck her tits and came between them but that’s a story for another time.

Sorry for the long story I’m not very good writing and I tend to make stories longer than they have to. I hope you all enjoyed the good parts even though the set up was kind of long.

Source: reddit.com/r/gonewildstories/comments/btjarb/mf_hooking_up_with_an_older_coworker_long