Let me share just a couple of the Sissy Pegging Stories I have collected over the decades. Yes, I am that old. Yes, I have worn strapons for that long. Now let’s get down to business.
Sissy Pegging Training
It is always a delight when I get a new sissy who has never been fucked before, been near a dildo by itself or a strapon, especially if the strapon is being worn by a Femdom. They can be really intimidated, which, I suspect, is half the point, right?
Once I have the harness and dildo set into a proper strapon position, it is crucial for me to see if the sissy has any pussy experience at all. I put on a glove and lube it up before I bend the sissy over my lap to discover just what size dildo she will need.
Fingering her pussy can make her squirm on my lap, so I have to hold her down harder, which does one of two things; making me stop wiggling my finger or her getting a spanking with my other hand. Sissies need to be good girls for their Mistresses!
When I have gotten the lay of the land (so to speak), I will pick the right sized dildo and slide it into my leather harness around my hips. Then I will find a great position for my sissy to lean over and then s l i d e my “dick” right into her pussy… gently, slowly at first and then when she acclimates, it’s time to pound that sissy cunt.
Pegging in Public
There is nothing so fun as fucking a sissy in a group of folks she doesn’t know.
One of my favorite experiences was taking sissy Sissy to one of my all-female Sex Parties. All the women were friends of mine, but Sissy didn’t know anyone. I giggled thinking what fun I was going to have with her.
One thing you need to know is Sissy was a pegging virgin. We had done some anal play before and she had worn a butt plug a few times, but pegging was going to be a whole new game… and in front of all these people?! Wheeee! I could hardly wait.
While we had introductions, I had Sissy take off those ugly man clothes, in front of everybody, and get dressed in her high cut light blue thong with the matching underboob bra and a fabulous pair of thigh highs with light blue bows. She was a vision!
Yes, those ARE “man” legs wearing these.
One of my besties had set up one of the bedrooms for me to use, the biggest one so everyone could watch who wanted to. And it go so crowded the temperature went up and we had to turn the air conditioner on cooler.
I told Sissy to get on the bed and put her bottom on the firm wedge we had set up for her. One of my friends helped her… and yes, she was still dressed. A lot of the time I like to fuck someone from behind. It is great fun for me to watch my cock slide in and out without an obstructed view.
But this time I wanted Sissy on her back so I could look at her face as I fucked this strapon virgin. I put my harness on then slid a 5,5-inch dildo in… not too fat in the girth. Not yet, anyway.
I slowly pulled her panties down and everyone held their breath as I talked softly to Sissy. I asked her to guide me with her instructions about when to slow down or stop. There is no rush having a girl lose her virginity.
Sissy was able to take the dildo easily and I fucked her for about 15 minutes before I got a bigger dildo… 6.5 inches… and fucked her again. Then the others wanted to take a turn and Sissy because quite the sissy SLUT that night!
Oh, yes… we had LOTS of fun!
Oh Mistress Daphne it has been like such a looooong time since I left you a comment. (Yes I can hear you snicker, “long? What do I know about long??)
What a month! Now you have joined the fun at the tail end!
Comin’ up the rear as it were, but as the saying goes “always room for one more!”
I’ve been spreading myself pretty thin across the Empire during Strap On month, commenting on all these
wonderful blogs about my fondness for “spreading myself pretty wide” for a fulfilling encounter with a well armed, (some of them felt that big too!)
Mistress’s strap on!
Oh what a delightful evening for your sissy to be the guest of honour….or perhaps, the guest of “in her” at the party.
I found myself wishing I could have been in her place, wishing that you could have been in “my place” (wink) that night!
Add to the mix the public humiliation we all crave with all the willing participants gives me cause to paraphrase a song from “My Fair Lady”…..
“I Could’ve Lanced All Night”
Thank you Mistress Daphne, you’ve managed to cram even more naughty thoughts into my mind!
Actually, I have been doing strapon/pegging pieces for the month! Lots of Audios (see my Audios page) and writing for other sites. I just finally got one on MY site! Good things cumming and all. 😉
Thank you for enjoying it!!! That made me smile bigly!
Thanks for all YOUR perusing through our month-long fun!
Wow, wanting to put on a show for a group of people has always been a fantasy of mine be it a group of Women or Men or Women and Men. Jealous of that lucky sissy.
Yes, Stephanie! It really was so much fun!
I hope you get to experience it one day, too.
Thanks for taking the time to comment!
Daphne….I held my breath opening your blog.Just the thought of your girl cock made me erect. My mouth began taste your cock. I tried to imagine how big it was and what it might feel like sliding deep inside my ass.”please don’t stop” I would beg and beg and beg ?
I love that my writing was so descriptive you could “feel” it! I am so happy to know that!
Thank you so much!!! You sure made me happy.
Thank you.
Me Daphne i am so sorry i am a day late. HAPPY BIRTHDAY MISTRESS DAPHNE! May Your birthday be full of joy happiness and everything You desire.
Love,
Your August
And of course i would live to experience Your pegging on display.
Love
Your August
I bet you would, too! Naughty boy!
Thank you!!! I had a GREAT day!
I almost precumed reading this i had to hold back
Good girl!
You by far my favorite every guy should try taking dick cause they would love it is amazing
I vote with YOU!
And thank you!!!