Listen to me read to you about exploring assplay here.
Interested in Ass Play
Ass play can be several different things, from pegging, strap-on play, to you fingering yourself to massage your prostate. I’m a fan of all manner of ass play! Is it something you have thought about? Maybe you’ve experimented with it a little?
The First Time
One of the first times many men consider assplay as something they may enjoy is with a woman in their bed. She may lick him, or insert a finger while giving head to him. He’s so into the blow job that she just sneaks that ass play in. She was smart enough to figure out he’d like it!
Getting you Used to It
As that woman, my next step is to introduce my smallest vibrator right into that tight ass, during a blow job again. He finds it mind-blowing, and that’s when the seeds I planted start to grow. He starts thinking about how good it felt to be filled up. How amazing that orgasm was. 
Making it a Habit
The next step is bringing out the big guns for some serious ass play! Whether that is a strapon, a larger dildo, big fat butt plugs, or a partner with a real cock, you are curious, aren’t you? You want the experience of being filled up completely, although you may not be ready to admit it yet.
Enjoying the Fun
That’s what I’m here for. I’m here to help you practice, to guide you in your toy shopping, and in your personal ass play exploration. I’m here to talk you through that first time you press your toys into that tight little hole, nice and easy, so you can have an explosive orgasm unlike any you have ever had. If you are ready to experiment with assplay, we need to talk!
A man rejecting ass play is mostly inexperienced . First time i was introduced to it i rejected it ( my bad). Little did i know I supposed i was really unconsciously sending signals i was only a sunbather back then before my sissification days i would wear colorful thongs & g strings at a secluded beach . I had a wonderful friend who put on rubber gloves lubed & wanted to probe me. When i think back wearing a thong is sending a signal . I have come a long way since then down a rabbit hole pink brick road & yes i would love ass play . Gentle . I am doing it myself right now.I have had my ass eaten twice. That is stimulating. I may eat someone else’s butt. Will see.Speaking of blow jobs. The first blow job i was giving to a man got ruined by ass play. I was just starting on his head a nice beautiful head then he stuck his finger in my ass i felt the finger nail & that ruined the blow job for both of us. So i am open for suggestions & adventure
My goodness Ms Stephanie I cannot keep up with the recent spate of blog posts extolling the virtue of anal play I am falling behind in my comments!
Alerted by the wonderful Mistress Erika and her tweets I run the risk of repeating myself. However being such a “devotee of anal play” I don’t think one more ringing endorsement will hurt. Actually this is a story I haven’t told (how the bug was planted in my ear….something planted in my rear “came” later!)
Years ago (Early 90’s) I visited a woman that provided a Feminization service out of her home. This was a unique service…head to toe transformation…it was elegant.
After several wardrobe changes she began to discuss strap on play! Talk about a virgin fawn in the headlights!
She described the “ins and outs” of this (to me at the time) bizzare practice. She was quite surprised that someone would “ just want to dress up”. She didn’t push it…although many Mistresses have since I rolled over onto my back!
Looking back I regret not having this wonderful woman introduce me to strap on play.
She stopped providing her service before I had the courage to open the back to let in a brand new world!
little davey- it sounds like you had a wonderful experience with the feminization Mistress. How funny that you had that virgin in the headlights look as she described it to you! It’s good that you understand better now, and know better than to refuse a good time! Thanks for stopping by!
I have done it with my vibrator when I got turned on to men.I dressed up as a red head wore red lingerie stockings etc .Set out a dinner plate, a glass of wine for vibe. After dinner Mr Vibe took me.
Ms. Stephanie,
So many men just don’t realize how much pleasure all manner of ass play can bring to them, but it seems like you’ve hit on quite the formula on how to introduce it. Like Ms. Erika wrote, what guy is going to stop her in the middle of a BJ? Especially if she’s really good at sucking cock?
Ms. Delia
Hi Ms. Stephanie!
What a great way to introduce ass play! Of course that BJ is distracting but, also true is he dare not stop her, what if it “breaks the mood” for her? He definitely wants that BJ so what the hell, right!? *winks*
But what he doesn’t realize, as you pointed out it’s hot and FUN and once he’s “into it” why then exploring all the possibilities, with you and toys is in order!
See you around the Empire!