First time posting so please be kind!
Backstory
We work at this international technology company and work in the same division, I am 24M, south east Asian and in a management role and she is 36F European and an administrator /personal assistant for the GM. We see each other most days and I get her to do normal errands for me and in the past year she has always serviced me well with little things such as upgrading to higher end hotels or renting the fancier cars for my trips. Eventually I catch on that not everyone gets the same treatment and it started with a coffee break with just us two.
Coffee Break that started it all.
I wouldn’t forget this day if my life dependent on it. As we walked to coffee she was all smiley and shaking with her hands, wearing a black tight skirt, white button up shirt, heels, full face of makeup and thin long hair.
We sat down at the bench in the corner coffee store and when we sat down the conversation went a little like this
“I wonder when you’d notice and take me out for lunch” as she rubs her heels on the back of my leg. “I thought I’d take you out to show my appreciation”. She laughs and puts her hand on mine “you didn’t have to” ending with” but you could show it a different way” in a seductive tone. I was genuinely confused at this point in time, her being 36F, divorced with kids asking me to do something with her?
“I’m not sure what you mean?” she rubs my hands and proceeds with rubbing my thigh with her heels. “Why don’t you come to mine when you get the chance? I’ll make you something”. “Not tonight, but I’ll let you know. Will I really let her know I thought? This feels a little creepy, but I didn’t mind her because her body was thin, she didn’t look her age and joyful personality. We walk back to work and she jiggles and puts her hand through mine.
I never was into MILF porn or anything like that, I spoke to my best friend about it and considered the fact that I also have a long-term girlfriend. Eventually a week later I texted her for her address and she said come at 8pm. Having thought, okay I’ll have to get home, have dinner, change and clean up – I’ll make it on time.
The First night
As I rung the doorbell to her two-storey terrace, she’s dressed in this black see-through lace dress and I barely make out that there was some lingerie underneath. She welcomes me in and her house is quite nice with modern furniture and fittings. She brings me to the lounge room with Brooklyn Nine Nine playing, goes to the kitchen and asks wine? I am like sure as I see a cheese platter on the table.
She brings it over and puts her hand on my thigh “why’d it take you so long to reply?” I flinch, move back take a sip of the white and look at her. “I’m not sure”. She smile and moves closer, “you know I always had a thing for you at work, I love the way you wear your suit. Flattered, I gasp “thanks, you’re always so kind to me when I travel, I really like the accommodation”. “If only I could stay with you” she mumbles. I thought what?!, “oh okay” I let out. She moves closer on the chair as I’m eating an olive. She puts my left hand on her chest and says “I notice you looking at these sometimes at work, I hoped you wanted to touch them too”. Naturally as a guy I look at all titties, but damn this is unreal?! Without knowing what to say she starts to take off her dress and I am staring at her exposed skin with a black lace thong and matching bra. “Like what you see?” she looks at me smiling. I assume I am flushed, because she kisses me on the cheek and says, let me show you more. She drags my hand into her bedroom, this is all happening so quickly.
She closes the door, locks it, slowly walks to me and groin and says “this is how you can show your appreciation. As she grabs unzips my pants, goes down on her knees, and starts holding on to my member. I look at her as she opens her mouth and takes it all, her eyes stare at me as she does it. I gasp in joy as she goes deeper and faster. I naturally move myself close to the bed as her mouth follows me, I begin to lay down as she takes off all of my pants. “I hope this is okay with you” as she unbuttons my shirt. As I am shocked and also hard at the same time I didn’t want this to stop, her body was definitely better than I’ve imagined.
I will not bother you all with the rest of the night but let’s just say lots of sex. As we finish, she sits next to me and points at my nose with a cute face, I hope this does not change anything at work. I nod obediently as I dress and begin to leave.
This happened months ago, and we still do it from time to time, especially now in sneakier places and times. Our work dynamic hasn’t changed other than the fact that she winks at me a lot more and always upgrades my travel and stationary which I am fond of.
If this post gets more upvotes I will post another one of our (crazy?) stories
Source: reddit.com/r/gonewildstories/comments/kqsaak/24_m_gets_seduced_by_36_f_milf_work_colleague
By all means, bother us with the mundane, awkward details but skip over the actual “gone wild” part.
>I will not bother you all with the rest of the night but let’s just say lots of sex.
Let’s not bother you with an upvote then.
That was a decent setup, but you skipped all the good stuff ;)
Also, that’s a really awkward and risky situation when you think about the real life implications. Even though you went along with it, you’re playing with fire here, as she’s put both of you in a potentially compromising situation at work.