** Listen to the Ms Olivia audio prostate milking and chastity **
Welcome back to our Winter Fest and today’s Mistress blog posting for this holiday season.
I told you in the first blog that I wrote, 3 sissy maids, that I have that 12 days of Christmas song stuck in my head, so today on day 8, I’m thinking of 8 maids a milking …. Prostate milking! ~laughs~
Chastity for Mistress
I have you locked in chastity. If you’re on long term chastity, then I will have your chastity schedule that includes a prostate milking schedule. Today I have 8 of my Mistress trainees working on you. The Experienced Mistress will, of course, supervise and do your prostate milking.
Bend over for your prostate milking
Many people know they adore anal play. Some men in chastity are nervous about the no orgasm part of chastity but anal play is a perfect solution. Perfect for you and perfect for Mistress. I walk you over to the kneeling bench and tie you up. This will be a dry balling prostate milking. Dry balling can be done without chastity as you can hear in the Ms Olivia audio on dry balling on our free audio site Tease Mania.
Mistress in slave’s ass
I might use my fingers. My favorite gloves for anal play are red latex. Red and black are my Domme colors and I might color coordinate by giving you a bare bottom spanking first. OR …. I might use a prostate massager like a Rude Boy or the aneros. There are so many options and my Mistress trainee’s will begin by moving their hands all over your body with some wicked tease and denial. Then, the milking begins.
Still locked in chastity
You stay cock locked … your cock is so swollen inside that chastity cage as you feel your ass penetrated and then ….
What happens then? You’re never going to hear the 8 maids a milking part of that song the same …. Ever again. Are you now singing, “It’s going to be a blue (balls) Christmas …. ” ~laughs~
Your Experienced Mistress,
For the NEXT Winter Fest Mistress blog from LDW Group click on Beg for Mistress Delia — today you have an orgasm experiment …. tomorrow what what happens when that turkey gets stuffed …. So to speak. Happy holidays! ~grinz~
Now you have me tied up in knots lol!! I won’t be able to get that song out my head either! Every time I hear 8 maids a milking I am going to crack up! Seriously though this sounds like something that will happen on our honeymoon 🙂 Over and over again 🙂
With YOU yvonne, 8 maids milking could happen on your crossdresser bridal shower! ~grinz~ Remember you’re in chastity from the engagement, though the crossdresser wedding and then …. oh then …. maybe even LONGER! ~grinz~ You will be the best femme wife ever ~sweet smile~.
Great Post Mistress Olivia. I’ve never been milked but would love to be along with being locked in chastity. But being a closeted married sissy it’s difficult for that to happen.
Thanks Stephanie …. do you have privacy to get a Rude Boy or an Aneros? They are amazing! And there ARE ways to experience chastity even while being married. I’m the Mistress of the work-around! ~grinz~
I bought Prostate massagers in the past but never was able to hit the spot. Think the one I bought was too big for a little thing like me.
I’d be interested in hearing your suggestions on how to experience chastity while being married.
Thank you so much for your feedback. It’s greatly appreciated. 🙂
There are wonderful prostate massagers and I know there’s one that is right for you. Actually, THIS is why it’s always best to get a personalized phone sex session because I can give all my experience and guidance to make sure it’s right. Otherwise, you’re sort of shooting in the dark …. so to speak. I don’t think we’ve done a call before. Have you ever called phone sex?
Hi Mistress Olivia,
You are correct that we have not done a phone sex call before. Because I am a married closeted sissy whose wife controls the finances (yeah I am a bitch) I am not sure I am able to do one w/out being caught. I’m open to ideas for a work around.
Thank you so much for your feedback. It’s greatly appreciated.
You’re more than welcome! I love blog comments and will absolutely answer to the best of my time and ability. A session, though is totally different …. it’s personal and targeted just to you … so, the blog will only take you so far. Now, that might be enough. It often is and there are lots of people who are blog friends who don’t call phone sex.
I suggest a prepaid gift card. That works really well. Here’s a blog post about phone sex and privacy that might help.
Based upon my comments in your pieces how long of a session do you would need? The reason I ask is to get an idea of how much of a gift card I would need to purchase.
Thanks in advance.
The time totally depends on you …. I’d do a gift card for an hour but remember you will only get charged for the time you use so you can always use the gift card again. Does that make sense? BTW, I’m away tomorrow (Wed) but I will be around Thurs & Fri and probably this weekend.
O-O-O-Olivia! You have a way of enticing men to try something new and kinky. After reading that, I picture a line of men waiting to beg for their chance of being milked by you. Especially after reading that part about your finger in their ass. *grin* Hot…sizzling hot!
Actually Ms Violet I was thinking of a scene …. you know I’m a very visual person. Imagine a hallway …. chastity slaves lined up on both sides of the hall. We both appear at one end of the hallway for the Mistress inspection. I’m on one side of the hall and you are on the other. We are going down the line of the chastity pets …. looking for the man in chastity who has the biggest swollen balls who is aching to cum …. and then ……
oh wait, too naughty for the blog, let’s talk about this privately! ~grinz~
Hey Olivia, this is off-topic, but I need to ask you a question. I have I fantasy in mind I’d like to do with you. But to know if it will work I need to know if by any chance you are familar with the character of Daisy Duke from that old TV show “The Dukes of Hazzard”. Please let me know so I can know if I should call or not.
Hi there! Hmmm, I’ve never seen the show but I can youtube it and check it out. I think of Daisy Duke’s as the ripped up shorty shorts! ~laughs~ Send me an email olivia AT enchantrixempire.com — we’ll sort it out and I do love erotic role-play!
Ms Olivia, rofl!
The more blogs for LDW winterfest that I read, the more I am SURE I will never hear that song again and NOT laugh. 5 golden rings are now always going to be in my head as golden cock rings! 8 maids a milking…well, of COURSE it is prostate milking! Right? 🙂
This is too much fun! Oh, and the blog is QUITE sexy too!
🙂 Ms. Delia
I know! Ms Delia, we really are joined because I thought about doing a 5 cock rings holiday themed post! When I’m out and about I often hear that song and I do start laughing! I’m thinking very naughty thoughts …. aren’t the financial thoughts FUN!
Ms Olivia ~ I will say it again, listening to the radio this holiday season hasn’t been the same! I am just picturing your little sissy maids all dressed up and ~ nowhere to go so to speak! lol. I think all men, sissy or no should experience prostate milking & chastity. And you, the experienced Mistress are the perfect one to give them that!! Thank you for this stop in the Kinky Wonderland! I will smile every time I hear this song and thing about you and your sissy maids!
Thanks Ms Kay Marie! I do know some guys aren’t into anal play and I try to judge just how “not into it” they are with a little perineum massage. Since that is the taint ( it taint the ass and it taint the balls) it’s a nice close place to see just how immune he is to even trying ass play. I’m thinking of one guy in particular who had a bad experience with a unskilled “Mistress” and a strap on who is totally turned off the idea of strap on play so he’s a no go with prostate milking…..but then again, he doesn’t like chastity either! I guess the moral is, everyone is different, unique and when it’s HOT SEXY it’s off the charts hot sexy!
Oh Olivia, you have hit on one of my favorite fantasies – an experienced mistress using me to teach a younger Mistress how to prostrate milk a submissive.
There I am on my hands and knees on a table, a beautiful gorgeous Mistress from my generation along with a beautiful gorgeous Mistress that would get carded for alcohol – but they aren’t there to play with me or even tease me, no, the experienced Mistress is teaching the younger Mistress how to milk me in a humiliating clinical way, I am just a teaching prop.
I would pick Princess Kellie! ~laughs~ She’s young but ohhhhhhhhh naughty and feisty! ~grinz~ Thanks for telling me your favorite fantasy!
OH MY GOD!!!!!! Mistress!!! This made me SOOO hard!!!!!Its like you read my mind!!!
~giggles~ Now Jakey, you know …….. you’re on orgasm denial for the time being. Be a good stroker boy for Mistress.
I love that the 12 days of Christmas is stuck in that sexy head of yours Ms. Olivia, just as it is in mine. We can come up with some seriously fun stuff with regard to that tune, uh?
Like your 8 maids a milking… what a great take on the song and orgasm control… I love it. And as I read I couldn’t help but wonder, are any of those “maids” sissies? lol – but then Yvonne beat me to the thought (sorta)… 😉
~laughs~ Oh the maids are sissies….but, you know I was going to make at least one a Mistress in training …. but then I thought, hmmmm, that will be another post and got distracted by the song in my head!