“You really are ready for me,” he said as he slid his hand down and felt the slick heat waiting for him.
I cringed a little inside with embarrassment but also marvel at his confidence as he immediately began tugging my pants down over my hips and off, not even pausing to undo the button at my waist.
I was something of a late bloomer. Well, probably more of a withered vine, stuck in hibernation by that point. People call 19 or 20 year olds late bloomers – to be a virgin at 27 was beyond all reckoning. I mean, I’m a fan of Jane Austen but I never really expected to be one of her ‘aged out’ characters, left behind and not knowing how to get back in the mix when everyone had moved so far along.
Thankfully I met someone who got my blood racing – after some fairly disastrous relationships early on, I had almost resigned myself to spinsterhood. Until he came along and I felt nauseous with excitement each time I knew I’d see him, and found myself imagining his hands on my body as I drove home from work. Little by little but also all at once, we fell in love.
But I had my shameful secret. I knew he was experienced and I was terrified finding out about my little secret would ruin everything. One day, I screwed up my courage and texted him to say I had something awkward to tell him before things went further. After initial relief that my news wasn’t that I used to be a man (not his jam, baby!) he was understandably concerned that anything we did would mean too much and was reluctant. I assured him that it wouldn’t, I was honestly not ‘waiting’ for anything, it just hadn’t happened and I wanted it to!
One night after drinks with colleagues and a friend of his, the three of us headed to a strip club. No surprise, I’d never been before, but I was curious and wanted to see what it was like. It was both hot and sad – I enjoyed watching the girls and having lingerie clad ladies chatting us up. But also felt sorry for the solo men there, lapping up whatever dregs of attention they could buy for the night.
Afterwards I drove the guys home to his house. We hung out for a bit and then he asked for my help making his bed. I nervously agreed and we got busy with the sheets. As I was wrestling a pillow into its case, he told me it was time, that we were doing this tonight. I protested a little – his mate was in the guest bedroom just down the hall – but he said not to worry about that. My pulse started racing and I was a big bundle of anticipation and fear. Next command – take off my bra. I hesitated but reached back and unclipped, sliding it down and out but keeping my top on. We kept making the bed, him staring at me and me thrilling at the challenge in his eyes, alternating between bending forward to show my cleavage at a better angle and scurrying to hide behind sheets and doona covers when overwhelmed by my audacity.
That’s when he scooched over the bed and smoothly cupped my breasts and smoothed his thumbs over my hard nipples. I gasped a little at the pleasure that shot from my head to deep in my belly. Expertly, he pulled my naked tits from my top and continued his firm but gentle squeezing and tweaking. Pausing with a hot grin and darkened eyes, he then slid his hand down my pants and confirmed for us both that I wanted this, that I was ready.
In one swift movement, he pulled my pants down over my hips, taking my panties with them. My top shimmied down to follow them a second later and he laid me down on that freshly made bed. We kissed and his hands were all over me, and then back to my virgin mound. Gently, he inserted a finger, then two. Slowly but surely, he moved them in and up, and put again, preparing me for what was coming next. He sat up and one rapid disrobing later, he was on top of me as I trembled internally with the weight of what was about to happen. I felt shy and unsure of what to do but my overwhelming feeling was of relief – at last, this was happening and with someone so handsome, smart and funny. What more could a girl want? For the fear of disappointing him to bugger off, probably!
Without further ado, he lined himself up at my entrance, paused for a moment to check I was ok and then gradually but forcefully pushed his way in. My walls resisted and there was stinging pain as he stretched me in ways I’d never been before. His fingers had not been enough to prepare me for his size. I breathed through it as I’d read about this moment so many times and knew if I could tolerate the pain for long enough, it would start to feel good.
And feel good it did. As he began to move in me, the sensations blended together – pain and pleasure formed a warm heady feeling I was so glad to finally experience. I tried moving my hips in time but couldn’t get the rhythm right and mucked it up so I stopped and lay back and let him take the lead, just running my hands all over his beautiful body as he explored mine.
As we worked towards the crescendo, I reminded him that I was not yet on the pill (proof positive I hadn’t expected this evening to go this far!) but he wasn’t worried. Sliding out of me he said we could finish this way instead. I grabbed his cock in my hand and ran my fingers up and down the length of him. He taught me to grip firmly and pump, and I loved hearing his breathing race when I mixed things up with pressure from different fingers. After a while I wanted to try something else and shimmied myself down until I was just below his manhood. Looking him in the eye I ran my tongue up his cock and licked the top, before popping it into my mouth and plunging it towards the back of my throat and back up again, swirling my tongue at the base of the tip. He grinned and said ‘well, that’s something you’ve done before!’ I said nope, never, I’ve just read a lot of things. He gave a quiet cheer – ‘hooray for writers!’ and laid back to enjoy my new skills.
After returning to his chest and continuing my education in how best to jerk off a cock, i was rewarded with my first encounter with cum. I loved it, knowing I brought that pleasure to him and to be a part of that moment of vulnerable abandon right as he came.
I scurried off to the bathroom and stared at myself in the mirror. I’d done it. At last. I was a bit sore but I’d enjoyed it. I couldn’t stop trembling, with the joy and shock of it. I didn’t sleep a wink when I went back to bed – the foreign feeling of sharing a bed with someone freaked me out so I lay there, still, eyes open and reliving all the moments I’d just experienced. I was so glad, that even if nothing more happened, that I’d done it at last. And done it with him.