I had to attend some boring work training and the lady teaching the course was an older (59) redhead and on the thick side…almost what some might consider a BBW.
For the most part the short course was all just video presentations so when they played the instructor sat down next to me, as there just so happened to be an empty seat available.
We stopped after about an hour and she announced that it was break time and for us all to be back in 15 minutes. As I stood up to join my coworkers she quickly turned to me and half whispered “you’re on (insert popular dating app)!” I almost didn’t hear her and I guess I looked confused so she repeated it again and it finally clicked in my head who she was.
So, I’ve always been into older women. And, when the apps allow it, I’ll change my age limit all the way up to 60. As you can imagine, being in my 20’s, many of the women I reach out to tell me that I’m “too young.”
Well, she was one such woman. Still, though, we had messaged back and forth a little a month prior. Just friendly flirting, almost completely on my part.
Anyway, we came back from break and I took my seat as we resumed the class. Once everything was over I said goodbye and commented something along the lines of “small world, huh?” before leaving.
That afternoon I couldn’t help myself, though. I saw her again before I left work, walking with the plant manager. Her big soft ass looked amazing in those dress pants.
Finally I fired up the app. It had a feature where you could see who had viewed your profile and she had viewed mine since that morning’s training class. So, I sent her a message…kind of a “nice to have finally met you” note. Short and sweet.
To my delight she messaged me back and she wasn’t so dismissive due to my age anymore. Matter of fact within just a few hours we exchanged numbers and ended up talking on the phone that very night. Mostly work gossip (she had just transferred to my facility) but I did toss a few compliments her way as well.
This continued for about a week. We’d text/flirt during the day. Send each other selfies and stuff. And sometimes at night we’d talk on the phone. I had already told her that I loved older women and soon enough our flirtations took a more erotic turn.
What started as us asking each other questions… you know the ones…”how long has it been?”, “what’s your favorite position?” etc etc turned into us sending risque pictures. She texted me her tits (yes, they were huge) and I texted her a dick pic. The next night we masturbated together over the phone for the first time, moaning and cumming together.
FINALLY the night came. We were both available and she had the house to herself and invited me over. We hung out for a while on her couch, just talking, before I went in for a kiss. And she was an amazing kisser.
We stayed there for a while, just making out as things got hotter and hotter. She was rubbing me over my jeans and my hand had already found its way under her bra before she finally led me to her bedroom.
She had one of those massive king sized beds that older women tend to have and we wasted no time in undressing and climbing on top, just laying there kissing some more as our hands explored each others bodies
As a redhead she had alot of freckles on her chest but her big soft tits were milky white, with large pink nipples that I took into my mouth one at a time.
She stroked my cock as I suckled her, my fingers finding her pussy already wet as I slide one, then two fingers in. Finally she said “I need you inside me” as she laid back.
At this point my cock was throbbing. I raised myself above her and eased myself inside, watching her gasp and seeing her face and chest blush red.
I started pumping slowly at first but we were both already so turned on that in a matter of a minute or I was thrusting with all I had, both of us moaning loudly…her hands cupping my ass, pulling me into her harder.
The whole thing lasted maybe 6 minutes before I came, emptying myself inside this woman who was over 30 years older than myself.
We lay there for a while, catching our breath and finally just talking. Hands idly touching each other.
Within an hour, though, she was on her hands and knees on the mattress, that big ass in the air, me standing behind her thrusting into her yet again.
This time I lasted longer and she came twice before I did, once again filling her up with my young cum.
And that was my first night with “Flo”. Sadly, we only had a few repeats before her granddaughter moved in with her. Shortly after that I began dating some my age. But we do still talk every now and then. To this day she’s the oldest woman I’ve ever been with.
Source: reddit.com/r/gonewildstories/comments/on8el2/much_older_coworker_f_recognizes_me
That was a hot story! Thanks for helping me while I rubbed my pussy! 😏🤤
Fucking brilliant man! Any pics or someone she might look like? What size were her breasts?
What app?