"Alice, you find Luke attractive, don't you?"
An innocuous enough question on the face of it, but for a few crucial factors;
Firstly, Luke was an incredibly handsome guy. Irritatingly so. If you were to draw 'chiseled', you'd draw Luke. This rendered it something of a rhetorical question. Of course I found Luke attractive. There couldn't be many who wouldn't. Which meant it was obviously a question leading somewhere.
Secondly, Luke was not a single man. Indeed, he was in a relationship of several years. Not that there's any harm in finding a partnered up man attractive - but it did frame the question in a slightly loaded fashion.
Thirdly and perhaps most significantly; the question was being asked to me *by* his girlfriend. The very same girlfriend whom I'd been close friends with myself for longer than the pair of them had been an item. A dear friend who I knew didn't pose highly loaded and leading questions purely for the sake of being hypothetical.
Little did I know at the time - though I do feel I immediately did suspect on some innate level - that it would ultimately lead to one of the most arse-clenchingly awkward encounters in my short but colourful life thus far.
I'll not repeat the conversation in its totality as this was a number of years ago and, ever wise, Charlie, the friend in question, had spent the evening plying me with alcohol to lubricate my mind in preparation for the upcoming crucial question.
Which is to say; she got me sufficiently hammered that, while I can't necessarily remember the specifics of the conversation itself, the broad strokes are forever lodged in my mind.
The brief version is thus: Luke's birthday was coming up and, as is often the case more than a couple of years into a relationship, ideas for gifts were already running low. In the absence of a newly released Xbox game he fancied, Charlie had settled instead on the other age old birthday cliche; a sexual exploit of sufficient significance that it could be offered in place of a gift.
The issue she was having was that as something of a sexual adventuress herself, there wasn't a great many options that hadn't already been enjoyed in earlier sessions. So, she was having to cast a wider net.
You'll have already guessed where this is going, so I'll save the unnecessary build up of suspense:
Charlie was asking me if I'd consider joining her and her boyfriend for some fun as a birthday treat for him.
Why had I been selected you may wonder? Well, one sentence in the conversation has remained very clearly burned into my mind:
"I'm pretty sure he thinks you're hot, and I figured you'd be most likely to say yes..."
High praise indeed.
There would be rules of course; I'd not actually be fucking Luke as it was felt that would be going a little too far. Instead Charlie suggested we'd just kiss a little to turn him on, deliver a double blowjob as his 'present', she'd take the cum to save any awkwardness, and then I could leave them to the rest of their night.
I commended her for having planned it all so thoroughly.
Nevertheless, I had some reservations. I knew there'd be no awkwardness on mine or Charlie's part; we'd dabbled on a few occasions by this point, several of which I've already chronicled elsewhere, but I had concerns for poor Luke. For all he was infuriatingly attractive, I wasn't especially convinced that his confidence was robust enough to be able to deal with suddenly being allowed and indeed encouraged to get intimate with one of his girlfriend's best friends.
Charlie told me not to worry. He'd be too turned on to care.
Realising I'd now be able to blame her if anything did go wrong; I agreed, telling her she now owed me a sizeable 'one'. She tactfully reminded me quite how many times I already owed her, and the subject of who owed who what was swiftly dropped.
She intended not to tell him of his upcoming surprise, and instead formulated a plan wherein they'd go out for drinks on his birthday night and i'd 'accidentally' gatecrash. We'd all share a few drinks and, with the alcohol going right to our heads, Charlie and I might get a little flirty. After some teasing, we'd take him home for the night of his life. A perfect plan. What could go wrong?
As it turned out; everything.
