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.
That’s how I found myself at her place the next night, after a few drinks on her local high street. I was pleased she was wearing fishnets again. She was pretty brazen about what she wanted and two drinks in she outright asked me back to her place.
It got heated very quickly. The door was barely closed when I pushed her back against it. She was pinned back, my tongue down her throat and my hands wandering wherever they pleased. The waistband of her skirt was tight so I pulled it up instead.
The tights were crotchless and she wasn’t wearing any knickers. Her smooth mound was right there, my fingers running along her lips, spreading the juices that were building from her tight hole. Now when I say tight, I’m not saying this to turn you on. This woman was **tight**. I tried popping a now wet finger in but was met with some resistance. Instead I focussed on working her clit. Judy was so turned on she couldn’t help but buck back against my hand and begin to moan.
She still had her coat on.
I told her to take me to her bedroom and she went ahead, grabbing my hand to pull me along behind her. Her coat and the rest of the clothes on her top half were off quickly. As she was unhooking her bra, I got to my knees in front of her and clamped my mouth onto her cunt. My tongue worked her clit first but I made sure to work it further back, to collect the heat and take the juices from her front entrance. This wasn’t enough for me. I grabbed her hips and turned her around, commanding her to bend over. She still had the crotchless fishnets and her heels on. Her upper body was on the bed and it gave me a perfect view and a perfect angle to lash my tongue against her gaping cunt and her cute little bumhole.
She wasn’t expecting this. Her moans got louder, her breathing notably deeper. She was so clean and smooth down there. I had to get my tongue inside her but it only nudged in a little, both into her pussy and into her bum. She was **so** tight. I had to fuck her so asked for the condom.
*Can we stop for a minute?*
For fuck’s sake. This is never good…
*I’m really tight.*
No kidding…
*It hurts when I have sex.*
We could give it a go: it might not be too bad this time…
I didn’t say these things, but I was carefully weighing up what to say to her. Maybe she’d just suck me off? What she said next floored me.
*Can I get my vibrator and you can fuck my arse instead?*
What!? And then, because maybe she thought it would seal the deal…
*Don’t worry, I’ve got lube in that drawer.*
This was a no brainer. It did occur to me that it felt unlikely her pussy would be tighter than her arse, particularly with lube but I didn’t really want to get into it. I just wanted to give her anal sex. Judy was **fully** prepared. One thing she hadn’t mentioned was that she also had this special cushion to raise her hips up (I later found out this was called a ‘sex wedge’ – it was actually pretty cool).
After rubbering up and applying a ton of lube to my dick and her bumhole, I was fully insider her with only a little build up. As she was on her back I had a fantastic view. She went to town on her hairless pussy with a very shiny silver vibrator, while I filled her arse and took surprisingly deep strokes. I’d given anal several times before and was impressed with how well she took it. The vibrations were so strong I could feel them in my cock. Between that, her fishnets and the sight of her big and slightly sagging tits lying either side of her chest, wobbling gently due to all the action going on below, it didn’t take me long to cum. Her orgasm came seconds later, almost certainly brought about by the combination of her vibrator and knowing I was shooting hot cum inside of her. I pulled out quickly and we got cleaned up.
The chat afterwards was quite interesting. Her dislike of vaginal sex was purely down to the discomfort it brought. A real shame. She said she’d had to learn to tolerate and eventually enjoy anal in order to have some fulfilling sex with previous partners. It was a shame in some ways but she seemed good with it so I was too.
Though we had a round two (she sucked me and had me cum on her tits) we didn’t actually fuck again: it was a one night thing and definitely one of the more unusual ones I’ve had.
Source: reddit.com/r/gonewildstories/comments/yaombo/kinky_supply_teacher_turned_out_to_be_anal_only_mf