Your first experience of strapon sex doesn’t have to be painful
I know someone who was curious about being pegged. His experience was his first and last with anything anal. Here’s what happened. An escort who played around with being a Dominatrix knew he wanted to try it. She put on her strapon and tried to force that girl cock in his ass and …. nooooooooooo that hurts! It ruined him for anal.
I get it. I was curious about anal and admitted that to a very vanilla boyfriend. His reaction made me reluctant to share my desires with my next lover. One bad experience can change things but it doesn’t have to limit you for all time. Today I love anal – giving AND receiving.
What you need to know before you try anal
There is a misconception that anal sex will hurt. That’s not true, but you also need to take some steps before trying anal. The bottom line (pun intended) is: go slow, start small, use lots of lube and be with someone who knows what she is doing.
Pegging pleasure is also in the mind
Your mind and arousal levels have a lot to do with how receptive you are to being a little anal bitch for your Mistress. I got this question from a caller:
“Does pegging a sub male regularly maintain him in a more submissive mindset?”
I love strapon sex as part of Woman in Charge and Female Domination scenes because I literally penetrate you. I take you from the inside
Psychological aspects of pegging
Creating a scene that gets the submissive into subspace is a great way to try new things and gently push the limits of the submissive. I don’t push the totally hard off limits play but I do like to push boundaries. It’s a great way to exert my control as a Domme.
Ms Erika and I have a podcast about strapon play from the woman’s point of view. The Scarlet Mistress joins us as we weave some kinky scenes that we thoroughly enjoy. An earlier podcast with me and Ms Delia has the Femdom Guide to Strapon Sex and Pegging.
Anal as the end point or part of the experience
Remember, anal sex can be a stand alone pleasure or incorporated into any BDSM scene to enhance physical and emotional sensations. Here’s an example from a caller. I describe the position where he is on his back,, legs spread and I’m in the missionary position on top of him. He says:
“Ms. Olivia; I think you described my sexual identity with your favorite strap on sex position. Not only was it a complete turn on but listening to you detailing the sensuality of becoming the alpha to a partner, made me realize that that is the exact feeling I’ve been trying to emulate as a submissive to my Domme wife.”
Are you curious about strapon play?
I have lots of questions for you. When did you first try anal? What inspired you to give it a try? How did you start? Maybe you are curious but haven’t tried it yet. In that case, what’s stopping you?
Your Experienced Mistress,
Ms Olivia
Podcast: Play in new window | Download
Subscribe: RSS
Memories….????…lol! Hi Ms. Olivia. I will never put my first time behind me. Wait.. I did! Someone was, also, however, to open up a whole new world to the pleasures of pegging.
Forgive me if you’ve read versions of this virgin as she eagerly leapt onto the linen in her desire to get drilled on the duvet!
My deflowering was exquisite! No lie. Really, no lie she took me doggie style…(although my submissive nature took over and just laid back ever since)
Yes…listen to Ms Olivia! Start small….lots of lube…don’t rush it!
So…how did I get this bug in my rear?
Went to this wonderful wonderful woman years ago.
She advertised her service in the local alt ads.
I went. It was incredible. I just wanted the crossdressing service and when she told me guys wanted to be pegged..(yes, she had to explain what that was) while dressed, it seemed interesting.
We never did, which I regret.
Over the years many Mistresses I visited obliged my desires. Some not so pleasant. Heed once again, do your due diligence and listen to Ms Olivia’s advice. I get the feeling she wants to drill this advice until it hits home! Hey Ms. Olivia…I missed you❤️
What an awesome comment lil peg — oh yeah people should heed my advice about anal. I ALWAYS know what I’m talking about (unless I don’t and then I can tap dance about it until I learn! LOL)
You bring up a really great point – having a great experience with pegging or any kind of anal depends on so many things — including and not limited to the skill of your partner.
Dear Miss Olivia (or do you prefer ‘Ms Olivia’?), That is a powerful picture at the top of this page. One could say the following about the lady who is posing for the picture: 1) She has a ‘black belt’, so she can defend herself with her martial arts skills; 2) She has ‘black underpants’ – a lady who wears black underpants can be strong and confident because she might have to cope with unwanted attention if her underpants show through light clothes; 3) She has strong and powerful legs, so she’s very athletic; 4) She oozes ‘power’ in every way; 5) She’s certainly unconventional!!
Ms Olivia is fine. You’re loving that martial arts skills theme aren’t you?
Well, Ms Olivia, you’ve used your martial arts skills on me a time or two in role plays (e.g. to overpower me, put me under citizen’s arrest, throw me into a swimming pool, etc.), so there is a link.
I love having my way with you!
And, of course, overpowering you.
Ms Olivia, I’m delighted that you have some martial arts skills so that you have an extra way of dealing with any unwanted attention from males who can’t keep their hands to themselves! You are a very good-looking lady, so I can imagine that some guys might try to go too far!
Thank you!
You’re welcome, Ms Olivia, ma’am! One other point about you having some martial arts skills. It acts as a deterrent to any of your male friends and relatives who feel like giving you some trouble for whatever reason! If they know you are capable of putting them flat on their back, they’re likely to back off first!
For the longest time I was opposed to even thinking about pegging until my current gf eased me into it slowly. I realized that at heart I’m actually a sub and my gf is the domme. There have been many times where she pegs me while I’m in chastity. We have gone from me being on top to her topping me ALL the time. Most times I don’t get to cum
Oh good — I think when a submissive doesn’t get to cum, it makes you so much easier to control and dominate!
Goddess “O”:
As I know you are aware I’m experienced in the passive position pertaining to anal sex. This being the case, I would consider yourself or my Owner (Empress Lilly) to take me anytime you wish to maintain my submissive nature. I know both of you are very knowledgeable about being in the Domme position and would never hurt me. However, I am well aware that neither of you I will never meet in person so dreaming of it or speaking to you while performing such on myself would be oh so pleasurable. Looking forward to talking to you soon and I’m sure you are so, so glad ???? that it is baseball season again (Go Mets).
Sissy slut,
Jizzelle
LFGM !!!!!!!
So far 3 – 0 …. woo hoooooooo!
Hope does spring eternal!
Ohhhhhh I would love to peg you while you’re wearing some of your super cute lingerie!
Goddess Olivia knows my story very well. After having it done to me many times in a certain environment .its a wonder I can walk or stand up straight. Heck, it’s a miracle I was able to get a woman to marry me
hahahahahaha
Your new name would be “Bendova” —- LOL
I had tried real cock before strap on and I had to stop because it did hurt. But then I sucked him and let him come in my mouth it was the nicest cock I ever had
Was your first cock really or thick? Is that part of why a slim strapon felt better?
He was a perfect size . I had sucked him on the beach and the first date. Next time we fucked on the beach . He wore panties and his navel was pierced so is mine that is how we started our meeting conversation most men don’t have a pierced navel it’s so hot. We fucked without lube it felt awesome for a while until the thrust. My suction cup dildo is same size as he was. And I love it of course I use my jeweled butt plugs first them lube up for suction cup dildo. I tried to get women on line to peg me conversation on Twitter and Sissy Meet .com I even begged for it????????????Sissy Meet women are willing but it’s just talk and exchange photos and talk of chastity etc but I guess hooking up was difficult with distance and Pandemic. I like dick more than I like most men . There are a few sweetie pie guys out there smooth and circumcised I will be on the lookout for some on the beach Friday. I have also been thinking of how to discuss with women in real life
Oh I love those jeweled butt plugs! Very pretty and ohhhh shiny!