How to have sex with a coworker?

I’m a male 35 years old. The security lady at my job who is probably in her late 40s always flirts either me and always checking me out. She has a decent face but not very pretty. But her boobs are huge and vast a nice butt as well. I’d love to explore every inch of that body but how do I go about it at my job?

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keep it as a fantasy

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Hello and welcome,

I just love the way some people rate people by physical appearance, as though that matters most to all of us. I have a gym bro neighbour who loves to tell me that I’m not his “type”, and that’s totally cool because he’s not mine either - I don’t date shallow people. That doesn’t stop him wanting to be around me, flirting with me or trying to make me jealous though. He’ll do anything for my attention, and he hates that I have two (I’m polyamorous) partners who love me for me, not my body.

Is she really flirting with you, or is she just being friendly? Is she checking you out, or is she simply being aware of her surroundings? She’s a security officer, that’s kind of the whole gig. What you think is her checking you out might simply be her being aware of your presence. My eyes wander when I’m dealing with my neighbour, but I’m not checking him out, I’m just being aware of his presence. Be careful about overthinking it, and especially careful about acting on it: you’re going to make a fool of yourself if you proposition the taken lady from work for a quick lay, and word can travel fast.

If I were you I’d err on the side of caution and leave her to her job. The poor love deserves someone who loves her more than skin deep anyway.

All the best

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Communication….. ask her on a date …

She may just be playing

Ask her if she’d like to catch a drink with you one day? Take it from there?

So her face is decent but she is not pretty and the only bits you are attracted to are her boobs and her butt. All I can say is the poor woman, to have come across someone as shallow as you. I hope she tells you to get lost.

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It appears you don’t know anything about the lady and you are only concentrating on her physical attraction. I think you need to think again and let this lady find someone who loves her.

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I’m also a fan of vast boobs.

See if you can meet her at a work group social setting. Asking my her out at work comes with many perils. She may have a work persona which she “flirts” and dresses to impress. More than entering get to know her without the pressure of looking like a wolf. If a gal likes you she’ll let you know. I’ve had many lovers whom I worked with, none of those relationships turned sour. I let them come to me.

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I met my husband of 12 years in the office too, and I’m into someone at the moment who I work with :face_with_hand_over_mouth:

I met my OH in the workplace, and witnessing that and others, the ones that worked were generally those where the 2 people chatted and you get the feeling whether you wish to see each other outside of work alone.

Work relations tend to get messy if they don’t pan out or are just for hook up :speak_no_evil_monkey:

If your interested in dating her I’d maybe just ask if she’d like to have a coffee sometime after work.

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“She has a decent face but not very pretty”

What a charmer :roll_eyes:

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Samantha here. Not full on penetration no. I have given a bj to one though. He was a nice guy from Thailand that was always looking out for me at work. I was only 18 at the time. We were all in the pub after work playing pool. He squeezed behind me as I was taking a shot and I could feel his bulge pressed up against me. It felt huge and turned me on. I ended up sucking him off in the toilet. What felt huge turned out to be on the small side but I was horny and it made him happy.

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