Dear Slightly (if I may be so familiar),
I have been suffering alone for months, and I am so glad that finally the right advice columnist has come along to help me with my problem.
With a name like Slightly Slutty Barren Spinster, I know you can help me.
For some time now, I have just been one huge, heaving, full-body lusticle for one of my hot colleagues at work. She is the boss of another section that I have quite a bit to do with. We have a nice flirty thing going but she has, regrettably, almost always kept it more or less clean. There was one time when we took a taxi home together from Friday night drinks and she accidentally tripped and fell and spent the night fucking me at my place, but she took herself home before dawn and there’s been no repeat. She is still pleasantly inappropriate at work and I would love to take it further but it’s all a bit tricky since she is senior to me.
Anyway, that’s not all. Recently, an old flame of mine has started working with us, in her section. Nobody knows that he and I were once an item, or even that I sometimes play on the home team, but everyone knows we are old friends. So, naturally, before you know it he has become very friendly very quickly with his boss: my crush. I mean VERY friendly. I actually caught the lift with my ex at the end of the day last week and there was nobody else with us, so I took the opportunity to give him a quick kiss, and I could clearly taste pussy on his lips. I’m almost certain it was her. Thing is, I wouldn’t mind another romp with him, too – he has a lovely cock (sorry, no photo – maybe if there’s a happy ending I’ll take a picture for you) and he knows how to use it. I’m not jealous of them or anything and I hope they’re having lots of safe fun, but their mutual absorption leaves little room for me. What about ME? Basically I don’t know whether to go for one or the other or even both, or just leave them to it and start looking elsewhere.
What do you advise, oh Slutty Seer?
Yours in slightliness,
Torn Between Two Lovers, Feeling Like a Fool.
We’ve all been there: blindsided by the familiar flavour of the boss’s pussy while surreptitiously pashing an ex in the lift at work. I jest. What a delightful quandary. Thank you for writing. As an aside, I am impressed that you could immediately identify her taste on your former flame’s lips. You, my friend, are a cunt connoisseur.
Let’s start with the boss. It bodes well for a repeat that she is still flirting with you, rather than awkwardly avoiding eye contact after your Friday night fuck. I think she’d happily trip and fall back on your cock but is waiting for you to make the first move. As you note, even if she is not your direct boss, her senior position in the organisation may make her wary of appearing predatory.
Why don’t you casually ask if she’s up for a drink after work. This provides you with plausible deniability. Her inappropriate behaviour in the office suggests she will understand that you’re actually inviting her to get down your pants. If she declines, you can pretend the post-work drink was just an innocent suggestion. If she accepts, I recommend gin as it’s always an effective panty peeler.
Now for the sneaky snatch snuffler with the lovely cock. (Thank you for the photo offer. Yes please. Also, Lord Sutch says can you please cc him at firstname.lastname@example.org). If you genuinely don’t mind sharing, perhaps you could invite him to join you two for that drink? One of the many delights of batting for both teams is that you get to be greedy.
I worry though. Much as you magnanimously wish Lovely Cock and Hot Boss well and profess not to be jealous, that could change if you join the fun. If you’re already feeling ignored, how would you feel if Lovely Cock is too busy for a clandestine bathroom blowjob but can find the time for a closed door ‘meeting’ with Hot Boss in her office?
I feel for you, Torn. All these sexy shenanigans must make going to work so much more exciting. But we both know it can only end awkwardly, at best, or catastrophically at worst. The sensible course would be to find someone to shag who isn’t a colleague. You can still be a “huge, heaving, full-body lusticle” at the office, but then divert all that energy into banging your new fuck friend outside working hours. Where do you live, by the way?
Regardless of your decision, I’m sure many readers appreciate the opportunity to live vicariously via your office exploits. Please write back and report on progress.
Hoping for a happy ending,
Picture courtesy of Erik Benson