Five Reasons Why Sissy Needs Strap-on Play
So you want to be, or are currently identifying as a sissy! Good for you! Now it’s time to decide if strap on pegging will be a part of your feminine repertoire. Take a look at some of the reasons below. I am sure you can identify with one , or all of them.
I know part of your trepidation may include hygiene and pain. Others are concerned about what it means if you really enjoy or don’t enjoy this kind of sexy stimulation. Let’s address these two things now, before we go further.

Sissy Needs Strap-on Play
Hygiene and Pain with Pegging
These are very valid concerns and Mistress is ready willing and able to guide you through these two topics. Learning about anal sex and various toys we can use during your journey can help quell some of those concerns. Contrary to what you see online with porn you should not start off a virgin hole with big dong schlong. Trust Mistress, we always take very good care of all of our toys. Breathing and non breathing toys, that is. (laughs)
I know, and perhaps some of the readers of this blog know, just because you enjoy pegging it doesn’t mean you want to be with a man. I know, I know, there are a lot of false ideas that if you are into feminization or being a sissy that automatically means you want to please a male. Not so. Some of you reading this may feel that way. You were born to please a man and his cock, but not all of you do. I get it.
Reason One Why Sissy Needs Strap-on Play
You want to experience as much as the Feminine experience as possible. In our conventional world males were made for penetrating and females were made for being penetrated. Sans an operation your cute little ass will be a good place to experience what it’s like to be penetrated. Some (pointing at self) might make the argument that our conventional wisdom is full of cock-a-doodle-doody. Cisgender males have a lovely P-spot, which is your prostate and it’s filled with nerves which often ignite with delight with stimulation. Therefore, what a waste would it be not to explore and experience those erotic sensations!
Second Reason Why
Just as I mentioned above, sissy or no sissy your prostate can be the source of some great explosive orgasms! Some enjoy just a little mild stimulation with a finger or a slender toy. There are a ton of various , non intimidating toys that can provide that sexy feeling and priming those naughty bits for more! Others , particularly sissy’s with a bit more experience enjoy some vibrating stimulation. Strap-on dildos can come with a vibrating option.
Reason Number Three
A very good reason why sissy needs strap-on play is to explore your submissive side! More times than not the sissy’s I play with have a component of submission. Giving up control of what they might wear, how they will walk , from soup to nuts feminization helps you feel your best feminine submissive self. Many sissy’s I play with say there’s nothing more submissive and feminine feeling than giving up your sissy pussy for Mistresses pleasure.
Reason Number Four Why Sissy Needs Strap-on Play
Often, but not all the time sissy needs strap-on humiliation can be part of sissy humiliation. Remember when I said above that just because you are into feminization or being a sissy, that it doesn’t mean you want to be with a male? Well , what better stimulus to humiliate a naughty sissy than to make you suck my girl cock? How about bouncing on one in a chair? There are a lot of fun and humiliating things we can do with sissy pegging play than just the peg part. But be warned! If you are unsure check with Mistress how to do this safely!

Sissy Needs Strap-on play
The Fifth Reason
Because you are a naughty kinky soul! Look, I know not 100% of sissy’s are going to enjoy sissy pegging. That just isn’t realistic. Sometimes we can overcome the trepidation, other times we are not patient enough through the process to really relax and enjoy. But that doesn’t mean you shouldn’t try! Believe me when I tell you that out of all the people I’ve enjoyed over the years, a very and I mean very few of them decline this kind of play when introduced to it through Femdom- pegging training.
Look, you wear Women’s clothes, you might even be altering your body, shaving off all that male hair. Learning to walk, talk and do most anything like a Female, that my friend is pretty kinky. Are you really going to sit there and because of “Whatever reason” you can fathom depart this blue planet without trying? NO! You want, you need to enrich your human experience to the nth degree!
Pegging Phone Sex for Sissy’s
There you have it. Some of the reasons why you, sissy needs strap-on play. Doing so discreetly with Mistress is safe sane and consensual. You can learn new skills and have a lot of fun doing so. Not only are phone sessions are available, we can utilize other platforms as well. I use skype for sexy texting sessions, viewing you on cam and even email packages to discuss your strap on journey! We also have multiple Mistress sessions at a discount , after all the more the merrier!
I would love to hear your comments, newbies and experienced a like!
Until We Chat ????
Sissy Mistress Erika
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My goodness Mistress Erika, indeed the influx…(spell check insists on putting that letter “L” in there!) of blogs re: Strap on bliss!
So many of the wonderful LDW Mistresses are extolling the virtues of this peccadillo and I am wholeheartedly “firmly behind” the push to to celebrate the benefits of a good poke!
Who’s kidding who? Mistress Erika you know I’m not “firm” and when it comes to your strap on I wouldn’t be behind, but eagerly in the forefront, displaying my openness for the cause!
Reasons one through five all raise valid points….hah! how Freudian!
Years (and years) ago there were telephone booths and I booked a feminization session with a most incredible woman.
She described to me that men, once dressed by her, would want to be penetrated by this very imposing faux phallic!
I was intrigued yet somewhat aghast! Really? Up there?
As time passed, and regrettably, this wonderful woman, I did finally venture into this world.
There was just a certainty I felt that something extraordinary was about to occur with each thrust of Mistress’s enthusiasm.
Not wrong…not wrong!
Please try this if you haven’t.
My regret is that I didn’t have the trust in this kind woman who “put the bug in my ear” but alas, nothing in the rear!
Little Peg! I’m glad you enjoyed my post! You are right Many lovely ladies here at Enchantrix who love pegging/strapon play!
LOL “Firmly behind” I just adore your prose, and encouragement to others to explore and experience the pleasures of strap-on play! ????
Looks so real and delicious ??
I love being bent over and a Mistress as strong and beautiful as you lifting my skirt and penetrating my gay ass is absolutely a true act of submission and totally makes me bring out the inner woman I so desire to be
Hi Mistress,
I was pegged once by a girl I was madly in love with but she didn’t want to leave her boyfriend for me. I found it so humiliating and exhilarating. It wasn’t physically pleasurable for me though. We didn’t really warm into it
Fabulous post and audio of your voice…..I feel blessed to hear you read this post from your own lips! …..And YES!…..i need to be pegged for ALL the reasons you stated….and for one more…..While locked in chastity it is my ONLY chance for sexual pleasure and release (if a dripping clitty is considered relief)
This is very interesting. It is a good discussion of why some people either have fantasies about this, or feel the need to take things a bit further.
Very interesting article.
I think it’s a necessity for all sissy girls and panty princesses to get the full feminine experience. So I think having her little girls pussy tapped and opened by a dildo , then it should follow a real alpha dick whenever she is ready to prove that she is worthy of her role as a sissy girl needs to be addressed. My plans have been disrupted due to this crazy virus but being part of the female experience should be required by all sissy girls so they can earn their lingerie and their status as a feminine male.
My mother had a rule as I grew up she said a sissy girl shouldn’t be allowed to wear anything pink until she sucked a cock to full completion. She says that the girls shouldn’t be forced to continue this act if she truly dislikes this activity but she should be forced to perform this if she wants to wear pink lingerie it’s a symbol of her commitment to her femininity. This will also separate the wannabe and poser there’s to many of these types in the vanilla world so making the sissy girl lifestyle more real it’s easier to recognize a panty princess in pink lingerie as the type of girl who a alpha male can see right away as a active pussy girl who is serious about her status and dedication in fulfilling her role and place as a sissy girl! I still agree with her assessment on this task so I can show the world I’m the real deal and I’m searching for the deepest emotional experiences of accepting my femininity.
Excellent article about this important and socially popular subject. ? This is being done world ? wide .! Are you a part of the Sissy Pandemic going on????️⛱️?
Just look at the Internet and you will see video of this subject and Mistress Erika gives you straight up the cold hard facts. I would trust my ?????️?? with Mistress Erika and you should too she knows her ?.
Oh oh oh shivers in trepidation
I haven’t had any luck in finding anyone suitable to peg me. I do know of someone who doesn’t live really all that far away from me. Should I ask her to peg me? Currently I am not doing anything on the back porch I have purged ally toys for a good reason. So I seek an experienced Misstress to have her enjoyment in my submission. Hopefully she will enjoy thrusting her red ? dildo in my tight sissy gurly hole
I want to be pegged& trained to suck COCK by a mistress to make me ready for the real thing!!
I am going to make a story short
I have met a Dominatrix socially at the nude resort. When I first noticed her she was with some very old guy her husband I suspected her to be a strap on Dominatrix. Years later my suspension was confirmed
She told me she was a Dom. She has seen me naked numerous times so she knows I have a tiny dick and her.neighbor may have told her I when out crossdressing. She had a friend who also a Dom and she asked me if I knew her I didn’t know her
So this woman says that she got Dom stuff from this other woman who recently passed away .This Dom conversation came out of nowhere. . She tells me she is a Dom So I inquire pleasure or pay. She replied both depends on who it is. I ? wonder ?. A few years ago she was walking one way and I the other direction I was naked she had on Daisy Dukes and a bra
We exchanged Happy New Year’s she walked on and I walked on in the other direction
I just had to turn around to check out her ass well she turned around too we both smiled . I wonder if I will be a pegging bottom for her???
Love these comments! Thank you! it seems I was notified once!
Grr they don’t give me the option to reply to each of you!
Thank you for reading, and looking forward to hearing from you over at my personal blog!
I am looking forwards to taking your strap on it’s not rocket ? science