Date 2 – sissy boy

By Kendra Holliday | August 26, 2013

Sticks and stones may break my bones, but whips and chains excite me

Sticks and stones may break my bones, but whips and chains excite me

I got ready for my date with sissy boy and went over to his house. Matthew had given me some Domming tips – back seat Domming, ha!

sissy boy greeted me at the door wearing a silky black robe. He had prepped for our date with an enema.

I was in charge. I asked him for a glass of wine, but all he had was vodka. He made us cocktails and we sat and chatted for a bit. He asked if he could take his robe off. I said sure. So then we were sitting on the couch, me fully clothed, him nude.

I had seen him nude before a couple days prior at a local event – he had worshiped a beautiful woman’s feet in front of the entire dungeon of people, crawling around on the floor licking her feet and playing silly cock games. He was a regular sissy slut! And cute, too. He’s about my age, but very boyish and sweet, with shoulder length dark curly hair.

After our cocktail, we moved on to the first course. In his living room, he had a cookie sheet of potting soil set up for me. I removed my stockings so I was barefoot. I rubbed my feet in the dirt. He turned on the video camera.

Then he crawled over and started licking my feet clean.

It felt lovely and strange having my feet worshiped that way. I made him show the camera his dirty tongue, and he called me Goddess.

It took him a few minutes, but he absolutely licked both my feet clean. I like when he nibbled on them, too. His favorite part of a woman’s feet are her soles.

I thanked him for a job well done, and then we moved to the second course – to the bedroom we went.

He showed me his ball parachute – it snaps over testicles and then you yank on it, stretching them. He attached a metal dog leash to it and let me try it out. He lay on the bed on his back and pulled up his legs. I pulled slowly on it so I could test where he liked the tension best.

It was fun watching The Rainbow Ball Show – they went from tan to ruby to purple – family jewels indeed! I talked to him as I pulled, teasing him a litte. “I literally have you by the balls, you know.”

He knew.

I twisted the leash around so his cock would flop about like a fish.

After we had our fun with the ball stretcher, it was time for the next course – I was going to take his ass.

We turned the video camera back on, and he assumed the position – on his back, legs drawn up, fully exposed to me.

First I took a red studded glass dildo and lubed it up, and worked the ball end into his asshole. I fucked him with that in order to prep him for my enormous cock.

Then I strapped on my cock (good ol’ Biggie!), sheathed it with a condom and told him, “You know why I’m doing this, don’t you?”

He said in a small voice, “Yes, Goddess.”

“Here we were, out there having a tea party with all of my guests, and you dropped a glass. So I had to excuse myself from the party so I could take you back here and teach you a lesson. They’re all out there, and they know what I’m doing to you.”

I told him to turn around and face me. He was on his hands and knees. I grabbed him by the hair and forced him to look up at me. “This is for your own good, you know.”

“Yes, Goddess. You know what’s best. Thank you for teaching me.” His eyes were sparkling with tears.

Suck it.

Suck it.

“Now suck my cock. You have to get it lubed for your little sissy hole.”

He did his best to lick and suck the monster dick, but it was awful big. After I was satisfied with his cock worship, I told him to turn back around again. He was still on his hands and knees. I lubed my fat cock up good.

With the video camera in mind, I tried mounting him with one leg up high – that ol’ porn star weird leg angle move so you can see the doggy style action, but it didn’t work so well; the camera was on a tripod, we needed someone there to move around with it and get good shots.

I pushed up against his hairy little asshole. I got the head in, he moaned. I let him get used to it, and kept giving him more and more until I was all the way in his ass.

I grabbed on to his hips and looked down at his cute ass as I pounded it. OK, I only went medium with the pounding – it was our first time, after all. He LOVED it. We kept up a dialog about how he deserved this, I was teaching him a lesson, he promised he would do better next time…

I got warm and tingly doing it, I was into it, as I thrust in and out of his warm, vulnerable body, I felt the urge to CUM IN HIS ASS. I wished I could mark the cute little bitch.

I stopped with my big dick all the way in his hole and said in a low, even tone, “Remember how this feels, because if you mess up again, it’s gonna be worse next time. I’m gonna let my guests line up out the door to ALL have a turn fucking your ass. I have to be a good hostess, after all.”

He gasped, “Yes, Goddess, I understand!”

I pulled out of his ass, he got up to turn off the video camera, and then we smiled and high fived each other. My dick bobbed up and down.

Then he showed me his extensive collective of BDSM toys – chastity belts, penis pumps, paddles – a dresser drawer and a basket full. He even had a large dog crate in his bedroom for people play!

We got dressed and went to Thai for dinner and had a great time getting to know each other over curry and wine. He’s SOO cute and sweet!

A couple days later, I watched the video with Matthew. I was self-conscious for him to see me like that, but it was amusing, too. As always, he was very supportive and positive of my latest adventure. It was fun!

All right, who’s next?


Amy L. 2013-08-26 23:00:17

Loved reading this. I really appreciate the erotic prose, yet you still let the reader in on the various challenges you encounter in scenes. Refreshingly honest. Thanks, Kendra.


Britney 2013-08-27 15:03:06

Thats one lucky sissy! Next? Wheres the line??


Al 2013-08-27 18:07:31

My cock was leaking pre cum after reading this… I would love to have a sexy woman bang me with a strapon!


    Kendra Holliday 2013-08-28 07:39:51



The Barbarian 2013-08-28 15:46:46

Mmmm, pegging, one of the great joys in life! Not just for sissy boys either, makes for great role reversal fun in any relationship.


Al 2013-08-29 11:01:23

The shame is that the majority of women are turned off to the whole pegging & dominance thing.


polynewb 2013-08-31 16:47:15

Super hot! Thanks for sharing. 😛


gisellepetticoats 2013-09-11 23:40:51



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