Much older coworker [F] recognized [M]e

This is a 100% true story, aside from the lady’s name. For the sake of privacy, let’s just call her Flo. I was 28 years old at the time.

I work a blue collar job but every now and then we’re required to attend onsite classes, most of which are safety oriented. One such class was conducted by Flo, an older woman I had never seen before. At least not in person.

Flo was thirty years my senior, a 58 year old redhead who most people would describe as a BBW. Average height but definitely plus sized, including wide hips and a very ample bosom. She wasn’t unattractive but she didn’t exactly ooze sexiness, either. I took notice of her but not much, not initially anyway.

Part of the class had Flo standing up front and speaking, going over a power point presentation and the other portion she dimmed the lights and played a series of instructional videos. During this portion she took a seat in an empty chair in the back of the room which – either by fate or design – happened to be right next to me. A couple of times I could feel her eyes on me but I didn’t think anything of it.

After the first video was done she dismissed us for a break, instructing everyone to return in 15 minutes. As we filed past her she pulled me aside and sorta under her breath said “you’re on INSERT NAME OF POPULAR DATING SITE”. A little surprised I replied that yes, I was. I guess at some point in the past I must have messaged her and she recognized me. We shared a quick “it’s a small world” and both kinda laughed and then I joined my coworkers at break.

As soon as I was outside I pulled out my phone, fired up the dating app, and started scrolling through my messages. And yeah, sure enough, there was Flo. We had talked about two months prior. Her profile only had one picture and it wasn’t that great of a representation, which explains why I didn’t recognize her in person. Reading through our messages it appeared that although she told me that I was way too young, there was a bit of a back and forth flirtation and a few sexual innuendos. Interesting.

Needless to say, I returned to the class viewing Flo – the mature redheaded instructor – in a whole new light.

About 90 minutes later the class was over. We spoke again, briefly. Both of us commenting on how funny it was meeting in such a way. And that was that.

Still, though…I couldn’t stop thinking about her. I’ve always been into older women, which explains why I messaged her in the first place. The dating app, at the time, would let you put age limits on your searches so every now and then I’d set my searches to include women between 50-60, just to see who was out there. I had yet to ever be with anyone Flo’s age, though. I think the oldest lady I had slept with by this point was 52.

I couldn’t resist. Later that night – possibly after drinking a few beers – I fired up the dating app once again. There was a feature that showed who viewed your profile and according to the notification, Flo had viewed mine at some point after our class. I guess we were both curious.

So, I said fuck it and sent Flo a short message. Now that my job was involved I had to play it careful but I think I said something innocent along the lines of “Hey! It was nice meeting you today! It really is a small world.”

To my surprise she messaged me back just minutes later!

And we continued to message back and forth for the next several hours. So much so that I eventually sent her my number, asking her to text me. Which she did.

And we were just texting about all kinds of stuff. Our mutual employer, our past work history, what brought both of us to join the dating site…how successful or unsuccessful we had been on the dating site thus far, etc.

The next day was more of the same. Lots of texting back and forth and then, that night, a long phone call.

And yeah, the texts were gradually growing more and more flirtatious. We sent each other selfies, selfies which also became gradually more revealing. By that Friday – 4 days after we met – I had already texted her a dick pic and we were flat out sexting. By the next night, Saturday, we were having phone sex.

Talk about a rush. Masturbating together. Jerking my cock, listening to a woman 3 decades older than me – and a coworker to boot – cumming loudly into her phone. It was a huge turn on and became almost a nightly occurrence. Flo may have been 58 but she definitely wasn’t lacking as far as sex drive was concerned.

Now, you may be wondering. Why waste time with phone sex? Why not just get together and enjoy the real thing. Well, although Flo only lived about 20 minutes away from me, there was a problem. She was taking care of her young granddaughter, who lived with her. So, unfortunately, the real deal would have to wait.

The sexting continued, however. So did the phone sex, once her granddaughter went to sleep. Our pictures back and forth became more graphic as well. I sent her video clips of me stroking my cock and cumming and she’d send me short videos of her fucking herself with a dildo.

FINALLY about a month and a half after first meeting, we got our chance. Her granddaughter would be gone for an entire night so Flo invited me over.

Needless to say, we were both ready to go at this point. Still, though, we hung out for a bit on her couch, just drinking wine and talking. After the bottle was empty I decided to go in for a kiss. We were sitting very close on the couch, so close our legs were touching.

The kiss began slowly, sensually. Both of us moaning into each others mouths as our tongues danced. This didn’t last too long, however, and soon gave way to unbridled lust as our hands began pawing at each other. Finally, inbetwen kisses she asked if I’d like to go to her bedroom, to which I readily agreed.

What happened next was a blur. I can’t remember what she was wearing…I don’t even remember what I was wearing. We were both so worked up after weeks of build up that we both stripped down immediately and hopped up on her bed.

I’d like to say that what followed was plenty of foreplay, but I’d be lying. I was in awe of her breasts, though. Huge with large pink aerolas and equally large erect almost red nipples. Her upper chest and shoulders were freckled but her tits were milky white.  I took turns on her nipples, cupping each heavy breast and sucking, nibbling. My free hand found it’s way between her legs (she wasn’t shaved but it wasn’t a huge bush, either) as she wrapped her fingers around my cock, which at this point was THROBBING and literally dripping with precum.

Two of my fingers slid easily into her as she began stroking my cock. I worked my fingers back and forth as I sucked her nipples until I felt her press against me and heard her say for me to lay back.

I obeyed and Flo straddled me, her hand still around my cock as she held it steady and lowered herself down upon it. We both moaned loudly as she slowly settled down and then began to ride me. My hands cupped her massive soft ass as those heavy tits swung in my face, my hips thrusting up as I matched her rhythm.

Once again I’d like to lie and say that Flo had orgasm after orgasm as I fucked her for hours on end. Truth is I only lasted about 2 minutes!

It was sensory overload, the whole thing was just so fucking…I don’t know…erotic. My coworker, old enough to be my own mother, riding me (She had kids older than me, by the way. This somehow made the whole situation that much hotter, more taboo).

Those big soft saggy tits with the rose colored nipples swaying just inches away from my face as Flow grinded down on me. When I saw her face and chest flush red, I could hold back no longer and emptied myself inside her. My fingertips digging into her soft ass cheeks, my hips lifting off the bed, her hands pressed down against my chest as I came.

We just laid there for a while, both of us catching our breath. I was still inside her, and still hard, as she laid across my chest, her red hair splayed out. After a little bit I could feel my cum, thick and warm, dripping out.

Finally she got up and went to the rest room, reemerging a few minutes later with a wet, warm towel she used to clean me up. And yeah, I was still hard! This has only happened to me 2 other times (once before and once after Flo) where I’m so turned on that I remain hard even after I cum. I mean, it’s REALLY sensitive and I still need time to recuperate but it’s still hard.

Once both of us were cleaned up Flo laid down next to me and this time it was more gradual and we both took our time. We cuddled for a while and just talked as our hands roamed freely, then we began kissing. More fingering and stroking until I raised myself above Flo. She guided my cock inside her once again and this time I was much more calm. Patient.

A lot of people think missionary is boring, but I disagree. Take me and Flo. Bodies pressed together, face to face. My hand roaming up and down her thighs, cupping her ass. Leaning down to kiss her as my thrusts grew deeper and faster. Feeling her hump up to meet me, her nails across my back as she finally came, moaning loudly. The whole while my cock is thrusting in and out.

I was able to make her cum again the next morning. Flo bent over, huge ass in the air. Me behind her, hands on each hip as I pounded away. My belly slapping loudly against her ass cheeks with each thrust. Those heavy soft milky white breasts swaying. We came at almost the same moment, her body seizing up…freezing for just a second, followed by other worldly moans. Moans that drove me over the edge as I once again emptied myself inside her, filling this women 30 years my senior. Overflowing with my young cum.

I would later discover that I was her first in the past two years.

This fling with Flo was pretty short lived however, mostly due to scheduling and her lack of availability due to taking care of her granddaughter.

We did hook up a couple more times, once during lunch break at work at a roadside rest spot just down the street. She straddled me in the back seat of her Jeep Cherokee and once again I came inside her. I never wore a condom with Flo…we never even discussed it. It just felt natural.

And yeah, I still think about her sometimes when I masturbate. I even still have her number, but we haven’t talked in forever. You have any similar experience? Fucking a much older or younger coworker? Tell me about it!

Source: reddit.com/r/gonewildstories/comments/tpevh8/much_older_coworker_f_recognized_me