Hello there anal toys!
My sub has been having his share of fun in Vegas this week! We have our own wager, a bet of sorts. I bet that I could milk him dry. Poor jack did not think it possible to completely dry him out. Take a peek at his thoughts about prostate stimulation, then after read on to see how are bet is going!
Jack says:
One of the things that always fascinated me about anal play was the idea of prostate milking. It can be worked into so many different types of scenes. Medical, anal play, even chastity and cuckolding. Even though you’re in chastity, your balls are still producing cum. Many chastity Mistresses will practice prostate milking to make sure their subs don’t have any “accidents”. All the cum, with none of the pleasure. And just think about you Mistress being serviced by her Bull, and you’re only getting milked. Humiliating, no?
I can teach you Anal Play
Ms. Delia has used Prostate stimulators with me for a variety of reasons. Smaller ones can be used to train a sub’s ass, allowing them to get used to the feeling of having something in there and practicing muscle control, almost like Kegels for your ass. They can also be used for pleasure, nestled up against my P-spot, as I stroke or am stroked, the precum leaking out and making everything all slick. My cock gets harder and harder, my balls tighter, as Ms. Delia edges me over and over. The edging, and the vibrations on my prostate combine and give me the hardest, most sexy and explosive orgasms! It can sometimes take me hours to recover!
Milking
I started off this post talking about milking though. Ms. Delia loves ruined orgasms, and prostate milking is the ultimate ruined orgasm – because there really isn’t one. She’ll start out by tying me up on my hands and knees, a cup underneath my cock to catch every drop. Then the slow insertion of The Naughty Boy. I’m usually already leaking pre-cum, but the volume only increases as the vibrations start. Sometimes, she slide it in and out of my fuckhole and stroke my throbbing dick slowly, limiting the stimulation, but coaxing my jism out. Before long, I’m begging her to do it faster, to let me cum, but she just laughs, and says “Not this time, my slutty little cum cow”. As my sexual frenzy builds, I’m begging her for release, but it won’t happened. It’ll sometimes take a long time before we’re done with Ms. Delia squeezing my balls at the end to get out every last drop. The final humiliation is when she picks up the cup, puts it to my lips and says “Drink your cum up like a good little bitch.”
About that bet:
I hope you liked jack’s thoughts! Now that bet has been hot. Every day, on our vacation so far, I have rolled a pair of dice. Each number is multiplied by 10 and is the number of milking minutes. The lowest would be 20 minutes and the highest 120 minutes! We have had both of those and also a very sexy bunch of other minute scenes. I have jack get up on a table with a measuring cup under his cock. I so enjoy the excitement mixed with embarassment! I lube up the prostate toy for fun and I rub that walnut sized gland for the number of minutes the dice have rolled, and watch the fluid drip and ooze from him. Over the past week, the level of fluid has decreased. This morning, none came out! None! I was one very pleased Mistress. My jack did have a dry orgasm, the first of this kind. He had spasms that made his whole body jerk. I love having this type of cock control! Tune in next week for more anal play!
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