Sissy Spanking Day Out

Sissy Boy Outing With Step Mom & Step Sister

Sissy Boy Ryan and his Step Mom and Step Sis

Ryan’s first Sissy Boy outing with step Mom & Step Sister. They have a very naughty, side. For instance. Dressing him up in girly clothes and spanking his bottom. Embarrassing enough at home. His step Sister watching Mom spank him. Even more embarrassing when they go on their little outings. 

His new young attractive Mom has a real thing about spanking and punishment games. Furthermore, he refers to her as “Mommy”. If he refuses she has promised to smack his bottom in public, like a little girl. With the outfit to match. 

Step-Sis is really a saucy little minx as well. Always dressed to tease. She has a very odd incestual relationship with her Mom. Enjoys the odd bit of spanking play. Usually giving him a spanking, caning, or a good hard dose of the paddle, belt, or switch. However, she does like a trip over Mommies lap or so the sounds from her bedroom would suggest. Read More… 

Embarrassing Road Trip

This little trip out started from home where some suitcases were loaded into the car. Usually, the ladies would take more clothes than Ryan. But this time there is an extra case in the trunk with a tag on it saying ” Ryan”. This one will be ram-packed with panties, dresses, and cute little girly stuff. Outfits, wigs, accessories, shoes, and makeup.  He left the house with the giggling pair in his normal clothes, wearing a pair of jeans with a T-shirt, sneakers, etc. The first stop was along a deserted highway, in a derelict Gas Station. They made him dress in a cute little schoolgirl outfit. Including, red nylon panties and knee-high socks. Read More…

bottom spanking day out for Sissy Ryan

First Spanking Of The Day

Egged on by his slutty little Step Sis, Ryan was quickly put across Mom’s lap on one of the tables in what used to be the picnic area. In full view of the road. Sis watched and laughed at his discomfort and shame. She would offer words of encouragement, like: “Stop complaining, stop being a baby, we dress you like a little girl cos you act like one, and let me spank him, Mom!”. Read More…

More top sissy artwork and animations.

Top 3D Sites

Step Mom spanks Sissy Ryan in front of Step SisMom decided to be a little bit sympathetic and told her it was time to move on and give Rian a break. It was going to be a long weekend. Sis was ever so slightly disappointed. Above all, jealous. However, this is going to be a whole weekend of naughty red bottom games. She could get her Step-Bro to do almost anything, with the promise of a good milking or more.

For instance, she usually acts like a little slut around the boys and teases them whenever she gets the opportunity. Usually by wearing something provocative, like a short skirt or a pair of those high cut Hot Pants and a very revealing top. She has been seen on numerous occasions with bright red cheeks which were applied by her Mom. Sometimes with red stripes on top.

This is one of many sissy stories inside the Full Members Area of Inside you will find thousands of images, videos, animations, and photos. 

Join Now

Sissy Boy Outing Updates

More updates to this particular story will be added this week. See how red and hot Ryans’ girlish little bottom gets. From his Mom, Step Sister, and the odd passer-by. In conclusion, find out exactly what his naughty Sis gets up to. With dear old Mom a cane and a few beers and any lucky man that happens to catch them. Read More…

Members Enter Here

Join Now