Author: DebonairDebauchery

Ti[M]e with my [F]ucktoy

I’ve been feeling particularly filthy over the last week for various reasons, and finally found myself free of festive obligations on Friday night. I dropped a line to one of my most obliging hook-ups, and she was similarly available. We arranged to meet.

I picked a bar in the centre of the city, likely to be quite empty this time of year. It was. I was able to pick the table I had intended, a secluded booth at the back. I took my place and she soon arrived, wearing a tight, short dress as I had requested.

We caught up over a first round of drinks and swiftly moved on to the second. Our conversation rapidly became more raunchy, and we kissed a little. Taking advantage of our discreet spot, I slid my hand under her dress. I had told her not to wear any underwear, and she had obliged. Her cunt was smooth and slightly wet, emanating an enticing heat. I played with her under the table, stroking her lips and clit with my finger as she whispered filthy things in my ear. Finally, I slid my fingers into her warm, sodden pussy and brought her to the edge of climax before making her lick her taste off my fingers. Read more »

[M]eeting up with a [F]light attendant

This is a more recent story, from a month or so ago. I am now in a job which requires quite a bit of travel, often taking two or three flights a week. As someone who identifies as “not an arse-hole”, I try to be as pleasant as possible to the plane staff. Turns out this can pay off.

I’d been flying to the States a few times in quick succession, and had been served by the same attended on a couple of flights. Our timetables had obviously synced, and I found myself on her shift again. We both recognised each other and had enjoyed small talk on each of our journeys.

We will call her Anna, but that wasn’t her name. She was the sort of air hostess you imagine from the sixties. Tall, brunette, with a slender frame. Pert B-cup breasts and legs to die for, not to mention an adorably cute laugh.

Towards the end of our flight, embolded by the rounds of free drinks she’d been bringing me, I pulled the classic sleazy businessman move and handed her my number. I’d almost forgotten about doing it, until around half ten that night when my phone buzzed with an unknown number. “Hey, its Anna xx” read the text. Read more »

The ti[M]e I [F]ucked one of my college students

A few years ago now, I was a post grad at university. I’d reached the stage where I had teaching responsibilities and was supervising a group of four students for a paper. We would meet every week for an hour or so, discussing their work. They were good, smart students and at 19 or so, only a few years younger than me. We worked hard, but our classes were fun, people bouncing ideas off one another and generally sharp conversation. Though one of them stood out.

Alice, let’s call her, always brought a slightly flirtatious edge to our sessions. Sometimes she’d steer the class discussion to sexual things. Sometimes she would tease me with saying shocking things. I was never quite sure whether it was in my head or not, but she also seemed to dress quite provocatively for our meet ups. Whilst the other three would be in typical student attire, she would often show a little more cleavage or leg than you might expect. However, like I said, I thought nothing of it.

Anyway, towards the end of the year, I invited the four of them round for drinks to celebrate finishing the course. The uni was quite liberal on things like that, and it was a nice thing to do for a group of students I liked. Read more »