Kinky supply teacher turned out to be anal only [MF]

One of the perks of being a teacher was the number of women it brings you into contact with. For a young and single guy it could be a lot of fun. It wasn’t just the regular permanent staff, there were often fresh faces in the form of supply teachers and students.

As an aside, some of the kinkiest girls and women I’ve been with were teachers. Maybe it’s the persistent veneer of professionalism they needed to have all day, bottling up their wilder sides until they get uncorked. Judy definitely fits into this category.

She was a supply teacher. About 10 years older than me. I helped her out with a few things when she first arrived. I checked her out, mainly her legs due to the fishnets she was wearing, and at first glance I thought she otherwise wasn’t my type: a little plain, dare I even say dowdy. We got chatting though and she was funny. And flirty. She made it very clear in our conversation that she lived alone. Maybe she thought she was being subtle but I knew she wanted me to know she was single. I saw her at break and lunchtime too. We got on well. Really well. Home time comes around and I check in, wondering if I should invite her out. I needn’t have wondered as she asked me.

I know how she fucks: meeting my mate’s new girlfriend [MF]

Aaron’s new girlfriend reacted more quickly than I did. Made out we didn’t even know each other.

Good thinking.

The last time I’d seen Laura was when she stormed out of my house in the early hours of the morning. My cum was probably still dripping out of her.

*No, you can’t stay over. Yes, it was just a fuck I was after.*

OK, so I was a dick to her. We met in the club one night, kissed, felt each other up and came back to my place to fuck.

She wasn’t my usual type. To be honest, I didn’t even fancy her that much. A long face. A long *everything* really. Tall, with droopy tubular tits.

Still, she had looked fantastic when bent over on all fours on my bed. I could smell her wet cunt, see it glisten. It was obvious how much she wanted it.

Before fucking her, I teased her pussy for a while with my fingers. Her clit was solid. Laura’s moans were deafening, her loud nasal voice giving way to a series of high-pitched squeals.

*Fuck me, now!*

Cheating housemate gives me a birthday gift to remember. [MF]

We’d flirted every since I moved into the house share. She had a boyfriend who lived in another city and they saw each other once a month at best. Suzy was hot: a tight body, sure, but an absolutely killer attitude. Smart and funny. Not necessarily the most beautiful but the kind of girl that guys just find sexy. Up to that point, I’d had my hands over her whenever I could. In my defence, she was pretty hands on too. It was clear we both wanted it. Cuddles in the kitchen meant my hands could explore her back. A helping hand to get up from the mat at the gym and our fingers lingered together just a little too long.

Then, one night, it was on.

We’d had a house party to celebrate my birthday. Frankly, it was a bit of a washout. Things dwindled by about 1am, leaving me, Suzy and another housemate in the living room drinking and joking around. Our other housemate was wasted and he ended up falling asleep on the sofa, snoring loudly. Suzy and I decided to leave him to it and call it a night. Our rooms were just along the corridor from each other. It’d been this way before. Saying ‘goodnight’ and the tension that came with it.

Bangin’ Bo Peep in the Black Morph Suit [MF]

I have to say first, and I realise this may not be a commonly shared opinion amongst readers of this month’s contest, I’ve always hated fancy dress parties. Personally, I feel they’re the most contrived ‘forced fun’ thing going: just not for me. Still, a group of university friends used to have them regularly. No exaggeration, it was every month or two. It got so frequent that they briefly went through a letters theme. The first party required costumes linked to ‘A’, the next party was ‘B’ and so on. It was at the ‘B’ party this happened. As much as I hated them, my fear of missing out was generally greater so I’d inevitably find myself in attendance.

Something else to get out of the way now: I went as ‘Black’. To set your mind at ease, this simply consisted of a one-piece black morph suit. A friend also planning to attend had a number of morph suits (from a video project he was working on). He went as ‘Blue’ and I went as ‘Black’. They were unused, before anyone asks. Though I’d seen people wear them before and wondered about logistics, I’d not quite anticipated exactly how clingy it would be. I thanked my lucky stars that the Black suit was the only one of the two that vaguely fit me, as it at least had the advantage of masking some of the less flattering parts of my physique, not least the bulge that protruded worryingly far even when I was totally flaccid.

How my mature married TA became my fuck buddy [MF]

About 10 years ago, I had an affair with my TA Melissa.

I was in my mid-20s, single and playing the field as much as possible. She was in her mid-40s and very unhappily married to a guy she’d met while she was working in mainland Europe. They’d returned to the UK, had a couple of kids and then the cultural differences kicked in big time: she had to do everything for all three of them. This had gone on for years before I even met her.

From me starting my job, she showed a lot of interest. We worked in an environment where there weren’t many men so I assumed it was novelty. We got on well enough and after about 7 or 8 months of working with her, I decided to make more of an effort and took her out for a meal one night during the school holidays as a ‘thank you’ for all the extra work she’d done to help me. She was great at her job – it was the least I could do.

My boss gets her yearly facial at the annual conference. [MF]

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.

Thai Massage girl goes all the way on her last day. [MF]

I occasionally visit Asian massage parlours in my area. The massage is great but there is always an added edge when visiting a new place to see what ‘extras’ are offered.

My last regular place, now sadly closed down, was very close to my old house. I was single when this happened so would visit every couple of weeks. I built up a good connection with a girl working there called Miko. Across my first few visits the happy ending progressed to her being nude through the massage, to allowing touching (including fingering). She never finished, with things always wrapping up when I came. This was fine – I was under no illusions it was anything other than an easy source of cash for her.

Miko’s body was **tight**. Her pussy was always shaved and her tiny tits were in perfect proportion to the rest of her frame. She was cute on her own merits but, compared to the other girl who gave massages and services (the buck-toothed owner, worthy of her own story another day), she was stunning.

An Olympic conquest with my oldest friend. [MMF]

2012 was an excellent year for me for a number of reasons. I want to tell a story about that summer, one that I probably wouldn’t have shared other than for the prompt for this month’s competition.

I live in the UK and (arguably) the most notable thing to happen in the UK in 2012 was the London Olympics. Summers were a particularly good time for me back then because I was working as a teacher and had a long (6 or 7) week holiday.

Being young and single with a little bit of money in my pocket, I tended to spend very little time at home during this extended period off work and would head off seeking adventure. An old friend from my own school days, Simon, was living in London at the time and we’d had a plan for a couple of years that I would come down to stay at his place and take in as many of the events as we could get to during the day and go out and have some fun each night.

Shared young uni student with a buddy. [MF]

When completing my postgraduate degree several years ago, quite a few of us got tight. The cohort was large enough to be split into three groups. Within these groups, and later across them, we spent a lot of time together. The nature of the course meant that there were a lot of shared experiences and, frankly, a lot of fucking. Lets just say that many of those in relationships at the start of the course were single or in a different relationship by the time it ended 12 months later. Lots of youngish people, lots of sex, lots of gossip and lots of fun.

In the initial weeks I befriended a girl called Anna and we became really close. There was a lot of simmering sexual tension that wasn’t acted on for one reason or another. Anna was (maybe still is, I don’t know…) the type of girl that wouldn’t necessarily turn heads in the streets but when you stop a speak to her she’s just wicked fun and really sex. A glint in the eye, big smile, lots of flirting, highly confident. While she carried a few extra lbs, she carried them well -and it added to her appeal even when her tops weren’t particularly low cut it wasn’t unusual to see other guys on our course checking out her tits, such was their size.

Door-to-door sales girl watches me jerk for her [MF]

For some reason, we get a lot of door-to-door salespeople where I live. I answered the door today to find a really pretty girl, very early 20s, with incredibly light blonde hair. She was stunning. The uniform she was wearing was clearly hiding a tight trim body too.

Before the doorbell rang, I’d been jerking off in the living room in just my shorts and a t-shirt. The only reason I stopped was because I knew a delivery was due to arrive and didn’t want to miss it. Result was I was stood at the door with my hard dick in the waistband of my shorts, under my t-shirt.

The girl started her spiel. I tried to let on that I wasn’t interested but she was relentless. Her sales pitch was actually really good. It went on long enough that my dick, still hard, slipped from under the elastic and was nestled quite clearly making a tent in my shorts. I saw her eyes flick down, then back up, then back down a couple of times. She didn’t break from her pitch even for a beat.