I don’t do relationships or commitment, but one time I fell for a puppy. Of course, he wasn’t just a puppy… he had other amazing talents that would, quite frankly, make me blush. What can I say, I am weak when it comes to anal sluts.
One time I took him with me to London for a fetish weekender. I wanted to make the most of him so it took a few months to organise the trip. I’m not talking hotels and travel, but arrangements with other kinky people. To pull together a fantasy trip, I need to check who’s in town, who can travel to the city I’ll be in and scout for any extras I need for the in-betweens. A kinky weekend is a whole theatrical production to produce. But this story is just about one night…
We arrived at the club night – there was a long line and it was cold, but we were in our street clothes… and had a huge bag of toys. Inside we made it to the bathrooms to change into our kink gear. My puppy wore his mask, of course, but was fully naked except for his jockstrap, collar and leash. We danced, we perved, and we did some puppy play… all the while waiting to meet up with my friends from the north.
Suddenly in the crowd I saw her – the biggest pain slut I’d ever had! She was a beautiful blonde this time with a slutty dress. She towered over me in her stilettos, her masculine body submitting to her femininity.
‘Lucia’ has always been my dream masochist. We have met several times in London – and she is gorgeous inside and out. Lucia was with her new Mistress, a cute, gentle girl – let’s call her ‘Miss Vivian’. We had all played before at another club but then we had different dynamics.
When I first met her, Miss Vivian was new to the scene and a submissive. She was there on Lucia’s invitation and I was drawn to her from the start. I am always a Domme, of course, but I had the pleasure of a triple impact session with Lucia, Miss Vivian and one of my toyboys… their asses all lined up for me to belt. We were in a delightful sadistic blood-fest with other amazing Dommes and their subs from around the country. There is a reason some walls are painted red. The crowd we drew was intimidating. I digress…
I was excited to see Lucia and Miss Vivian together. With these two wonderful people, anything was possible! We danced for a little bit, and then I realised Lucia and Miss Vivian had a strange little man with them. They seemed to be fine with it so I just let it go. Then it was time for some extra fun. We went to the larger play room to scout for a corner. Many were already using the facilities to the max, and they were more hardcore than usual, but still surface-level shit.
We were lucky enough to find a corner vacant. The floor was padded and it had a jungle frame over it – good for stomping, impact and other torturous play. I retrieved my tools from the cloak room….
As a warmup, Miss Vivian and I lined up our three against the frame. We smacked, we flogged, and we caned their asses like three bears. My dear little puppy was a pussy at pain so we gave him enough to make him feel included.
Lucy was as fantastic as ever – I thrashed her ass like I was hitting sixers out of the stadium.
The man in the middle was this stranger that I didn’t not like, but there was just something about him that pissed me off and I wanted to hurt him badly. I discovered his threshold early, and I raised it by ten. I belted him enough that he would need recovery for at lease five minutes before another hit because I preferred to spend all my attention on my puppy and Lucia.
My puppy’s little cute ass would wobble so sweetly, and no matter how lightly I struck, it hurt him. But that gave me the chance to come in close and squeeze his ass cheek in my hand while I whispered all the naughty things I wanted to do to him.
Lucia kept stars in my eyes. I would belt her the hardest I could and she would psych me out, telling me it was only a 5 out of 10 pain for her. So I would belt even harder than I could possible image. You can certainly understand how a sadist and a masochist are each other’s drug of choice.
After the different ‘shades of red’ session, it was time to open up. The stranger had disappeared, so it was my puppy, Miss Vivian and Lucia. We do enjoy each other so much, so we wanted to make this special. Miss Vivian, was new to Mistressing, so I thought to give her an experience she would never forget (that would also benefit Lucia). Lucia was more than happy to just watch her Mistress learn how to fist.
My puppy readied himself. It is always a delight to have a conscientiously clean boy – it means I am confident and eager to share him. He laid down for us on his back, legs up to present his perfectly used asshole. You can tell when an ass is well trained by the way the moon is spread.
Miss Vivian and I gloved up. (In club situations, it is always appropriate to wear protective clothes and gloves, and to have your own towels, etc.) We lubed, and I went about preparing my puppy’s ass for entry.
It didn’t take long for him to fit my fist in. I showed Miss Vivian how to twist and slide in. The surprise on her face when she entered! Yes, my puppy was warm and soft and tight… like a perfect hug. When my puppy relaxed even more, I took Miss Vivian by the hand… It was delicate and small, and fitted in mine… and I tingled at all the naughty things I would do to her if she was mine. Miss Vivian is a fantastic girl. There are not many women I lust after, but Miss Vivian is one of them. I would devour her. But, I digress…
With her hand in mine, we slowly felt our way into my puppy’s secret place. Holding hands inside my puppy, we suspended, so his body could adjust to us. The joy and the giggles Miss Vivian and I shared, while my puppy felt the ecstasy…
When ready, we began to fuck him together, in and out slowly but surely. The precum that was spurting out of my boy was to die for. We pulled out, and then I showed Miss Vivian how to give my sub multiple ass-gasms. Him squeezing her little hand made her sweetly gasp every time.
I gave her another glove, so she could double fist on her own… while I attended to other things. I laid long on the cushioned floor so I could lap up my puppy’s precum off his belly like a thirsty kitten. Sucking up all his stuff, it lured me to his cock, and I put him in my mouth. Watching my puppy, his breathing was ferocious and his head was thrashing side-to-side. Just sometimes, pleasure is too much to bear.
I pulled myself up and looked back to Lucia sitting close watching us. She was enthralled, and I was happy to see it. Whispering in my puppy’s ear, I checked in on him. His ass was becoming spent. I didn’t blame him… we had already had two days of play… and we had one more to go.
We finished our play, and cleaned up. As I was collecting the house cleaning spray from the station, I was stopped several times by different people – Dom/mes who appreciated the play they had just witnessed. I was thanked many times. A few complimented that they had never seen anything like it. It must have been a fantastical sight! A burly crossdresser watching two Dommes double hand-hold fist a skinny puppy, isn’t something you see every day.