I'd known Rena for a long time. In fact, she was in high school when I'd first met her on the bus. My college and her school had an arrangement where year 11 and 12 students could take classes in the college curriculum. She was cool and smart, and the conversations were always easy, so we became friends. She eventually married one of my classmates, and eventually that dissolved. So many years had passed before she hinted one day via DM that she was keen to catch up for casual sex.
Was I interested? Of course.
So around she came to my place, and despite our initial confidences, neither of us quite knew how to initiate. After all, we'd been friends for over a decade now, though I hadn't actually seen her for much of that time.
So, we watched a movie, sitting side-by-side on the couch with a glass of wine and each wondering if and when we'd get to the deed. Honestly, it was all I could think about the whole film, but I didn't want to come across as uncool, so I stayed my hand. This is probably the problem with a friendship as long as ours: there was already an unspoken barrier that needed crossing, and we weren't familiar enough to knock that wall down.
In our DM we'd made some jokes about measuring my penis, and the ways in which it could be done to determine my size. One of the ideas thrown so flippantly out there had been that we use a pen and paper, and so after the movie I steered us toward this little game, starting us off with our hands (for reasons I cannot now recall). We were sitting on the floor, legs crossed, all for the world like innocents play-drawing. But I was getting hard with anticipation, feeling my breath shallow as my pace quickened. Reminding Rena of the exchange on DM, I stretched myself into a kneeling position and just went for it, pulling my shorts down far enough until my erection sprung into view.
"Hello!" said Rena, a mixture of uncertainty and delight.
Playing it cool, as though this were an everyday thing, I pressed my hard dick down onto the paper and tried to draw around it.
"I think you're going to have to help me," I suggested.
Mawkishly, Rena took the pen from me and traced an outline around my dick. It was all she needed to adjust to the shift in dynamics, and she considered my erection calmly, deciding it was rather attractive. I get this a lot, and can only wonder at how many ugly dicks are out there and what these girls must feel upon seeing them.
With me now exposed, it was quid-pro-quo time.
"Now to see how big your boobs are," I reminded her, referencing the DM exchange we'd had.
She nodded, remembering, and with a sly smile she slipped her shirt down and released a breast from her bra. Rena has a very slight olive complexion, and her nipple was dark and nubby. She leaned over the paper and taking up the pen, I drew a line around her boob as best I could. We didn't get the full measure of it, being difficult as it was for her to press it down on the paper, but the hard part was over. We'd found a way to hurdle the divide between friendship and sex.
We relinquished the drawing game and began making out, her hand straying to my exposed cock, running her fingers along my shaft.
I tugged her shirt up over her head, dragging her bra with it. Some laughter as it tangled in her hair. Then my shirt was off and my shorts down.