This is how my long term sexual relationship with my coworker got started. We worked at a professional company, so everyone was always on their best behavior, which as we all know is just a front for most people. On the surface, people would be the most professional but behind the scenes you would find out that people were hooking up after happy hour, cheating on their spouses with their “work husband”, etc.
Jenny was in her early 40s and I my mid 30s. We’d always gotten along great as coworkers, and the entire time we knew each other, there was always flirty tension between us, but I never in a hundred years would have guessed we’d end up fucking in the conference room (a story for another day).
Jenny is a latina milf that you’d do damn near anything to sleep with. She is about 5’7, with long, jet black hair, big beautiful brown eyes, a smile that would melt your heart, bouncy c up tits, a slim waist and a HUGE ass. The kind that gets stares everywhere she goes. At this point I had seen it countless times in passing and at events like happy hour or lunch, and I still would snap my neck – every. single. time – she walked by. She just oozes sexuality. In heels she is easily 5’10, making her a certifiable Amazon.
She and I would be on group email chains, and always spin off into our own convo after one of us would say something funny. One of these chains ended up delving into sexually suggestive territory, and before you know it, by the end of the day we were daring each other to show the other our goods. At this point I suggested we hop off the work emails (and delete the existing chain) and switch to texting. She immediately texted me that she wanted “some chocolate” and was getting really worked up. I (jokingly) told her to come to my office and I’d give her some since it was now after hours and everyone had left. I really didn’t expect her to do it because, I mean, its work. Even though I was alone, if one of my office mates came back for some reason, it would be hard to explain and she knew that. But a few minutes later I hear a knock on our office door, and there Jenny is standing there in a white sundress with a cardigan, looking demure but with that mischievous smile that lets you know she’s not here to work on the Excel spreadsheet.
Surprised, I stammered for words but immediately let her in before anyone saw her enter. She followed me to my desk, and began flirting.
“So…you got some chocolate for me?” she asked coyly, staring at the bulge I now had in my slacks.
“Oh, do you really think you are ready for dessert?” I replied in the corniest but first answer that came to mind.
She started tracing her finger across my chest and I could feel my heart racing, as I had NEVER done anything this risky before.
“SO are you going to show me or what?” She asked impatiently.
“Wow, I didn’t think you would actually come” I told her, nervously trying to buy myself time to decide if this was a smart idea or not.
“Well I did and you BETTER not be teasing me”. She said in that jokey but *actually* serious way.
But I figured “fuck it” so I pulled out my cock and held it in my hand. And at this point it was like she got tired of waiting to unwrap a present. She instantly reached for it and began stroking me. She complimented me on my size and how smooth it was “all things I assume I most women say to stroke a man’s ego but I didn’t care. I was literally in my office with a woman I’d masturbated to before now actually STROKING MY COCK.
“You should kiss it” I smirked and looked at her. She looked at me and smiled.
“Oh yea? You’d like that wouldn’t you?” She grinned. Hungry eyes fixated on my cock.
“Yes I would. Just a peck”.
She smiled, tossed her hair over her shoulder, bent over and put my now dripping cock on her tongue. Capturing that bead of pre-cum and watching it stretch then snap. She began sucking on me and it blew my mind not only because of the situation but because she worked it like a pro. Sucking, jerking, twisting her wrist and spitting just enough to make the perfect level of friction. This was hands down the best head I had ever received. Not one to be stingy, I tried to reciprocate by lifting up her dress, revealing that perfect ass, and sliding my fingers inside of her from above. She was drenched. I have reasonably long fingers so I worked my way in and she began to moan through the sucking.
But then all of a sudden she stopped.
“ Fingers are great but I want it inside of me so bad” she told me and stood.
“Are you on birth control?” I asked.
Jenny frowned. “No”. Do you have a condom?”
“I had NO idea this was going to happen so, umm no”. As fun as spontaneous sex is, I still like to play it safe so it was a no go for me. “Well I don’t think you want to risk having another baby daddy so maybe we try again next time” I suggested and she just laughed.
“Well, I still want to feel it”. So she lifted up her dress, backed against me, pulled aside her thong and (not so dry) humped my cock while I squeezed and spread her perfect, tanned ass cheeks. After a while I think this was just teasing her too much because she said if we kept going she would have to slide it in anyway so she stopped, got on her knees and went back to sucking me off. Between the hotness of the situation and how fucking good she was, it didn’t take long for me to announce that I was about to cum. Trying not to make a mess at my office desk, I reached for a Kleenex but she pushed my hand away, insisting on me cumming in her hand. I came so hard I overshot her hand, and some landed on the carpet. She laughed but caught the rest, licking her lips as she watched. After the last drops she kissed my dick a few times and used the Kleenexes to clean her hands up. I collected myself and apologized for not having a condom on me and offered to help her get off but she said to “just be ready next time”.
Next time came a few weeks later in the back of my car lol. In between was a whole lot of under the table flirting, fingering and crotch rubbing that only served to increase the sexual tension before we finally had sex.
Source: reddit.com/r/gonewildstories/comments/k5p659/when_my_milf_coworker_turned_an_email_into_the
L
Very hot