I was in bonny Glasgow Scotland last week visiting a sissy who arranged for me to go up on the train to meet him there.
He came to my holiday rental apartment for an afternoon of sissification, humiliation, poppers and pegging.
He arrived looking like a strapping athlete. Built like a wrestler. Wearing a tracksuit. Fit and energetic.
Once we’d discussed details of what he wanted, any limits, boundaries, he’d had a quick shower and we were ready for action.
I had my strap-on harness and a variety of dildos with me.
The dildo I used on him is called “The Boss”.
He looked like a proper wee slut once I’d dressed him up in his sissy outfit. Stockings, heels, latex mini dress, corset and wig.
I gave sissy a make over with red lipstick, lashes and eye-liner. The transformation wasn’t exactly Cinderella. Wouldn’t have looked the part waltzing with Prince charming. More like the butch Queen category at a drag ball.
Not the prettiest feminisation but what sissy lacked in looks he made up for in enthusiasm for taking a big cock. Bent over and begging for my strap on, sissy was my kind of lassie.
Before fucking him, I moved the full length mirror to face the bed so sissy could watch himself getting used.
I told sissy he had to give me plenty of warning if he was getting close to cumming. With my big pink dildo cock ramming his sensitive prostate, it wasn’t long before sissy was getting close to the point of no return.
I stopped pounding his ass and made my sissy tell me exactly what he saw in the mirror. Then when his legs had stopped shaking, I started hammering him again.
Each time he got close to cumming, I denied him, distracted him, drugged him with more poppers, and then fucked him some more.
Edged in this way, sissy became delirious from the overwhelming sensations, deep in sub space. Completely at my mercy.
Then at the perfect moment of my choosing, I gave sissy permission to cum and rode him hard until he finally spurted. Must have been an orgasm and a half. A few drops even hit the mirror over a metre away.
Now every time sissy looks in the mirror, he’ll be reminded of the image of himself with cum dripping down his sissified reflection.
Back in London
After returning to London I had an overnight with a gentlemen who requested latex outfits and big toys for anal play.
He wanted me to take some big dildos up my ass and also wanted to sit on the big dildos himself.
We played at his hotel, went out for dinner. Then spent a few hours at a dungeon together and then back to his hotel again.
He was kind enough to give all the dildos he brought with him to me as a gift. So now I have a beautiful collection of XXL John Thomas silicone dildos.