I worked as a teacher a number of years ago. Senior leaders in schools in our area were invited to a two-day leadership conference every year, always including an overnight stay. While there was a professional development element, most people who attended used it more as a social opportunity. Lots of drinking and a fair amount of sex/infidelity going on. Stories of conquests were rife. Now bear in mind we’re talking about head teachers, their deputies, senior educational professionals in the region: classic prim and professional in the day but capable of absolute filth at night.
I was thrilled to get an invite to this conference in the first year of my new job, working as Julie’s deputy. Julie was late 40s at the time, around 15 years older than me, and quite tidy. Dirty blonde hair, slim figure. Not much in the way of tits but a fantastic pert backside. She wasn’t beautiful but there was definitely something sexy about her. Julie was also very much married, though without kids.
Things went broadly as expected: serious sessions in the day, a big meal to round things off and plenty of drinks to get the night going. It got wilder than I expected at the time but looking back it makes total sense: a bunch of 30/40 something having a night away from their work responsibilities and (in some cases) family responsibilities.
I was new to a lot of these people and it wasn’t my natural environment: still, I managed to do the rounds, meet and flirt with some of the prettier women (in one case laying the groundwork for a fantastic fuck with one of them that will be a story for another day). At around 2am, Julie was drunk and I was only still lightly buzzed. We were sat talking, nothing sexual, when she asked for some help heading upstairs after I said I was calling it a night. She leaned on me as we left the room and took the lift to our floor. Her room was first. There was a shift in the atmosphere when she arrived.
“I saw you talking to Nicola for a while. You must be disappointed you weren’t coming up here with her”.
I laughed this off. No big deal. There’d be other opportunities with Nicola. Other girls altogether…
Julie was having none of it and started saying how lucky she’d have been and she should have taken her chance (buttering me up really: I wasn’t *that* good of a catch!).
“…and I mean if she doesn’t want it, I’ll have it.”
I couldn’t help but grin. I pressed her for what she meant and she said I should come in. I didn’t hesitate.
Once inside, she beckoned me over to the bed and pushed me down so I was sat on the edge.
“I’m not going to make a habit of this but I’m going to suck your dick, OK?”
I wasn’t interested in having a conversation.
Julie had my trousers and underwear off almost before I knew it and was on her knees, using her lips to work the full length of my cock. It was sublime. They gripped me, warm and tight, as she bobbed up and down, taking nearly all of me inside her mouth. The muffled groans told me she was enjoying it. I propped myself up so that I could have a good look at her. This was my boss. She was married. It was amazing. I wanted more.
When I pushed myself up further, she stopped and looked at me quizzically. I think she was worried I wanted to stop or had got freaked out so I reassured her that it was amazing but I wanted to return the favour. She wasn’t having any of it.
“You’re just getting a blowjob. Sit back down…”
Her hand was on my stomach, gently pushing me back, definitely stopping me from reaching down. I knew this was it for tonight and was *almost* happy with my lot. I told her to take her top off. She paused a moment and I wondered if I’d pushed too far but then she lifted her shirt over her head before unclipping her bra. I asked if I could have a feel and she pulled my hand down, telling me to squeeze hard. Soon, she made it clear that she wanted to finish the blowjob. Hearing my boss tell me I could cum in her mouth meant that once she restarted I didn’t last long. With her hands on my hips I held them in place. Then I met every bob of her head with a firm thrust. She was moaning and this tipped me over the edge.
I swear it was an accident. Just as I came, she pulled her head slightly further back than she’d done before. Accompanied by my loud groans, several thick ropes of cum covered her face, shooting up her cheeks, slightly over her eyes and onto her hair. She stayed kneeling, wide eyed and quiet until I’d completely finished. Julie raised her eyebrows, forced both eyes open after wiping the bulk of the cum away and broke the awkward silence.
“Well that was unexpected. You should probably go to bed now. I definitely need to clean up. Goodnight”
I pulled my trousers up and got out of there sharpish. I jerked off twice once I was in my room, thinking about what had just happened but then the fear kicked in. This was my married boss, after all. I needn’t have worried. At breakfast the next morning, it was like nothing had happened. And we just never talked about it again… at least not *exactly*.
The next year, the next conference and it’s late in the evening. We head up. I’m full of expectation this time. We get to my room first this time and I hear the magic words she would repeat the next two years too: “Do you want another one?”
Over the four years I worked with Julie, she sucked me off at all four of the conferences we attended. Every single time she got a facial. Any worries about her being disgusted by the first one were unfounded.
That second time, we went into my room and she again stripped to the waist, pulling the straps of her dress down to reveal fully her little bra-less tits. I was much more assertive that time and grabbed her hair firmly as she sucked me, telling her how good she was. When I started to groan, she was crystal clear: “On my face”. I didn’t disappoint her and fired another heavy load onto her. The initial shocked look was still there but soon followed by a smile.
The third year, I told her outright (while my dick was in my mouth) that I wanted to fuck her and make her cum. No dice. She made clear it was still just a blowjob, though she did strip down to her black panties and tights so I could get a better look at her body. That year I held her hair tight in my hands while I blasted her face and tits.
The final year I had already secured a new post so she knew the conference would be our last together. Sadly, still no sex. She did, however, suck me off multiple times and let me cum in her mouth, including as soon as we’d checked in to the hotel, once in the disabled bathroom at the end of the daytime session, our usual late evening rendezvous and, finally, once more in the morning before we went down for breakfast.
She recently took early retirement recently. Much deserved. Hopefully she now has the time to explore more of her abundant slutty side.
Source: reddit.com/r/gonewildstories/comments/xstdcr/my_boss_gets_her_yearly_facial_at_the_annual
Very sexy
Super hot, though it’s a shame you never got to make her cum