So once upon a time I had milking mistress. Literally her kink was milking cum out of my cock(just hands) typically cfnm style.

So after some awesome times examples; worked as valet for hotel with a shuttle service. She once called for a ride to hotel. Then milked me in the van, she worked at a different hotel and would block out a room and milk me in it. Then sometime leave me there and do it again hours later, etc. so much fun was had but then I got into a serious relationship out side the kink world and she moved shortly after. But she did keep my info. Well she returned and literally wrote…

“It’s milking time my boy. Clean your self up and make a appointment for these 3 days and various times. I will be gone for ever if you don’t comply”

I guess she was in town for the weekend. Here I am super excited and nervous and wondering. But you only live once. So I did as told shave.

Shaved bare down below and hole/gooch as instructed ( no ass play “really “ has ever happened). Now mistress and I don’t talk about real life and she couldn’t host in her hotel, neither could I. So we met in my truck. Big pick up 4 door. She told me where to drive and park and then stripped in the back ( super dark tent). And omg I was not ready but so ready for the milking I had coming. She had me nude in the back and legs up her inbetween she lubed up her hands and started milking me. Jay stroking at first but soon on hand working my nipples the balls, I started to really sink in. She asked if I misssed her my little pet. And of course I was puddy in her hands “yes goddess, yes”. Good little puppy

She keep at this stroke, balls, nipple rub till I was going to pop. Then she stopped quickly slapping the interior of both thighs hard 3/4 time or so. Then she asked me for some toys I was asked to bring basically she tied up my nuts in a way they were exposed but still tied. So pressure was constant but also manageable. Then back to the tug,balls, nipple play over and over. Now 45 minutes in I’m barely functioning I am so hard and on edge “ready”. She in ties me slowly. Which made my go half down again I think she did so with intention. So when when she went to get me hard once more I figured same routine but no. She got more lube and her thumb started now playing with my asshole. Fuck it felt amazing (this was new for all parties lol). Is my puppy ok she asked me? To which i replied with a mhmmmm. That’s when her character really kicked in. Up till then she liked ma’am, mistress, goddes, etc. (also had not heard the “puppy” thing yet till this day too) and never really asked much from me vocally beyond that. But then when I answered with no actual words it sparked something)

“Ohh is my little puppy boy in to much shock to answered with words, or is it bliss” Stroking and fingering my hole I was actually struggling it felt so good & I wanted to play along so… “Ahh uhuh” is all that came out. “Say yes puppy boy” “Yes mistress” “Woof for me little puppy” “Woof” “Haha———-haha” She was super amused and happy as I’m in bliss getting closer and closer to busting. “Oh my puppy feels like he might pop. Hold on puppy” She stops stroking(I have only seen her D tits come out once ever) she has this tank top thin on that she can easily slide to the center and both toys popped out. “Is this what puppy wants” I just shook my head. So she pulls me up my legs are over hers were sitting face to face and she pulls me to her breasts. “Suck puppy” I’m sucking and moaning she is stroking me and still has a hand in my ass/goouch My moans grow She direct me “Don’t moan puppy I want you to suckle and bit them while you whimper” I whimper once “Just like that puppy”

Now I’m whimpering super hard over and over until “ whimperrrrrrrrr “ I pop. The first shoot exploding higher than ever maybe would have gone 3 feet up had it not blasted my chin. She was Laughing in bliss and fun. “What a good puppy you are”