My first M/M spanking

You may have noticed this blog hasn't been too active recently. Well, that's because I am attempting to start a new chapter in my life - one where instead of just writing about spanking, cuckolds and bi I am attempting to live it.

My wife and I have fun in the sack but she has decided she's reached the limits of her kink (whereas I feel I'm just getting started!) so she has said that I am free to explore my curiosities outside the relationship. Talk about an early Christmas present!

So I took the plunge and posted a picture of myself bare bottomed and dressed as a naughty schoolboy on the Spank This hookup site, announcing that I wanted to find out what it was like to be spanked by a man...

And that's how I found myself knocking on the door of an ex-teacher who was my dream spanker come true (older, balder, stockier). My idea was I would first have just an introductory spanking in normal clothes (or possibly naked) to see if I liked it. But when strictlyyours (hereafter referred to as 'Sir') commented that 'Having you over my knee in your school uniform socks would be ace' I felt I just had to wear my favorite uniform!

I arrived as nervous (and as late!) as the stereotypical naughty schoolboy. All through the day Sir had tantalized me with this email exchange:

Sir: I shall expect you later today and no doubt there will be a bad report to be settled following your discovery in the library stacks with your trousers down, engaging in inappropriate behaviour with the young French teaching assistant, who has now been sacked. This afternoon your trousers will be coming down to feel the extent of my displeasure for that indiscretion..

Me: But it wasn't my fault sir she blackmailed me!

Sir: Save your excuse, lad; you know full well that sixth formers will be treated much like juniors if they transgress the behavioural code. Oh yes and I should add that the IT department have traced the instigator of an unsavoury websIte relating to 'cuckolding' or some such debauchery, to your school internet account. I can see that your visit to my study this afternoon is going to be both embarrassing and painful.....for one of us.

The scenario made me very keen to finish work and get going (especially as it reminded me of a story on Strict Julie's blog about a young gentleman and a serving girl caught 'at it' and punished by his mother and the groundsman. Although I always felt the son got off scot free in that scenario compared to what happened to the poor serving girl!)

Once inside the house I was very nervous (it turns out 'spank' is a difficult word to say when you're tense!) but Sir took charge and provided a room for me to change into my sixth former uniform (grey knee socks, shoes, trousers, white shirt, school tie, straw boater - and a dressy strap watch of course!) 

Then I had the classic schoolboy experience of knocking on the study door before being led down to the 'punishment room', where after some mild scolding Sir ordered me to remove my shoes, hat and glasses, then put me across my knee and proceeded to spank the seat of my tight trousers.

As he spanked my nerves melted away and I enjoyed it as much as when I've been spanked by my wife. It wasn't long before Sir was commenting  on the feeling of something hard against his leg and I was sent to the corner in disgrace with my hands on my head.

After some more scolding I was called back and then had the thrill of having my trousers taken down (my wife always makes me do it myself) before going back over his knee for more whacks on my white briefs.

This gradual buildup of intensity was great for easing me into the spanking fun, but it did nothing to calm my hardon. When my underpants were pulled down my cock stood shamelessly. It was the first time I'd been erect in the presence of a man, but it felt perfectly natural. Sir commented repeatedly on the effect and tested the firmness of my erection by hanging his cane from it! Then he put a towel across his lap, put me back across his knee and went on walloping my bare bottom.

I had made clear that I was not averse to wandering hands during my punishment and I was intensely stimulated as Sir caressed and squeezed my cheeks and teased my perineum and arse crack between (and sometimes as well as) spanks. So this wasn't just my first M/M spanking, it was my first gay experience!

My bottom was now bright pink and my cock was still hard. Sir ordered me to go upstairs, change into my striped blue pyjamas and wait on the end of the bed. (I confess I snuck a look at my bottom in the mirror - that's how I know it was pink!)

After a nerve-wracking few minutes Sir entered brandishing a size 12 plimsoll, and I went across his lap with my jim jams down for my first ever slippering.

At one point I accidentally let slip that he wasn't spanking much harder than my wife did and he certainly took that as a challenge - from then on I was given a good sound walloping with plenty of double hand spanks. Throughout the session I couldn't decide whether to play the good student who's being punished for something he didn't do, or the classic cheeky schoolboy. I guess that's what introductory sessions are for - later we decided I could be a shy, innocent boy who comes out of his shell whenever he's spanked.

I did enjoy the slipper - it's a nice medium between the hand and the harsher implements, and it left a wonderful sole-shaped mark on my bottom that showed up in some of the pictures Sir took.

Oh yes the pictures - after my slippering Sir had me kneel on the bed for some intimate shots of my well-spanked bottom, after which he rubbed cream into my rosy cheeks and firmly caressed my 'underside'. I honestly would have let him do anything he wanted at that point.

He settled for bringing out a few more of his implements to show me this wasn't all about caressing hand-spanks. Sure enough, after six strokes each with a wooden paddle, a triple tongued leather strap and a short cane, my erection had long since vanished!

Sir wasn't finished with me yet though, as I was stripped naked and put back across his lap for an extremely intimate hand spanking, with my dick trapped between his legs.

 

This is where I really entered spanking heaven and I'm pretty sure I moaned like a complete slut as his palm cracked down. My backside felt like it was glowing and the pain moved from a warm sting to a hot, prickly, peeling-sunburn kind of sensation.

Of course my erection had long since returned and when he had finished Sir had me stand at the end of the bed stark naked and wank my dick while he continued spanking my ass. I couldn't cum - maybe it was the nerves or the fact I've been trained never to cum before my partner - but Sir assured me this was something we could work on...

And that was it, at least for now. Afterwards I changed back into my day-to-day clothes (sadly noting that the ordeal had been too much for the strap of my wristwatch) and Sir and I had a nice talk about culture, sport, Jonathan's spanking art, and whether there will be a next time. I certainly hope so!

Postscript: Unfortunately there was an accident while I was transferring the pictures to my computer later, and I lost all of them apart from a few tiny thumbnails. So not only am I facing inevitable punishment for failing my first ever homework assignment, we're also going to have to recreate the photos all over again!