Big Boss

When I was in my late 20s I had an office job that even back then allowed hybrid working so I could spend the odd week working from home. My boss was an older man, early 50s but still looked good for his age. One of my weeks when I was working from home my boss asked me over email if I preferred home or office and I confessed I prefer office but home means I don’t have to wear a bra. I was aware when I said it it might not have been an exactly appropriate thing to say, but I had somewhat occasional flirty banter with my boss, he didn't seem to mind. He fired back “You go commando too?” “No, I have a mint thong” “Is that green?” “Yeah, a pale green” “I wasn’t expecting so much detail, thanks :) Lace?” “No, just cotton” “So you can’t see any pubes through it?” “No” “I’d ask how you tend your garden but that’d probably be too personal? :)” “If you asked that I’d be sending this conversation straight to HR :)”

The next day he said to me it was lucky he was working from home too as our conversation meant he had to “take things in hand”. I asked him, “You do that during work?” “If I have to, don’t you?” “No” “Do you do it though?” “I’m an evening person” “After work evening or later?” “Later, in bed, it helps me sleep” “Every night?” “No, but most” “Last night?” “Yes” “Really? That’s pretty hot LOL again thanks for the detail” “Hot? Are you just finding out that women masturbate? :)” “They don’t always talk about it though, I like it ;) We really shouldn’t be having this conversation though”

I was in the office a few weeks later and he suggested going to his place for lunch. I had an idea he wasn’t just thinking about cucumber sandwiches though. I weighed up the pros and cons, cons being I didn’t want him thinking he could just fuck me any time he wanted, and also the thought of me lying naked, legs apart with my pale wobbly flesh on show, granny panties lying on the floor. The pros were that I hadn’t had it in (quite) a while and I’d heard on the gr**evine among ladies in the office that he was fairly well endowed. I said I’d think about it, and then I sent him an email saying if we were just eating we could do it today, but otherwise we should to it tomorrow, to which he responded tomorrow was fine.

I made sure my legs were shaved, pussy was trimmed and I at least had on underwear that wouldn’t shame me to death if I had to be stripped and rushed to hospital. Lunch came and he lived in a nice house and indicated he’d like us to move to the bedroom, but whilst my knickers were acceptable and legs smooth I still didn’t much fancy him seeing literally everything and I didn’t particularly want to see his everything either, so “Right here will do” I told him coyly, dropping my trousers to the floor, my knickers came off next and I gripped the back of a chair, legs slightly apart. From behind I heard him remove his own trousers and next came some probing with the end of his c**k until he finally found the entrance and pushed it in.

It was definitely big, bigger than I’d ever had and despite my best intentions I couldn’t help but moan loudly as he filled me up. He started slow then got faster, one hand on my hip and one on my shoulder as he rammed the length of his thick c**k inside me, he had me barking like a seal, it felt so good. He was pushing me towards orgasm, I knew if he kept going I’d cum, even with no clit stimulation at all. And keep going he did, f**king me over and over, his body slapping up against mine. I pushed against the back of the chair with my arms so I wasn’t rammed up against it, he moved his hand from my shoulder to under my blouse to grab at my boob, clumsily pushing my bra up so they fell out and with unfettered access he started to pinch and rub my nipple. That was enough to push me over the edge, I just let myself go and orgasmed, legs trembling, fighting hard to keep standing while his huge c**k continued to relentlessly pound into me. Soon after my own orgasm had faded his kicked in, it was his turn to moan as he shot his cum inside me, and we were finished.

I went to the bathroom to clean myself up, my inner thighs were covered in juices, I even put some toilet paper in the crotch of my knickers, and just took a bit of a breather. When I returned he’d already got dressed. “Well?” he asked, “Well what?” “Did you enjoy it?” I just gave him a peck on the lips and said “We need to get back to work”.