It was just another day at the office until Alfonso realized he had feeling for his sexy female co-worker. Little did he know that he was a she. After the initial shock was over Alfonso decided to pound his sissy secretary up the ass on his lunch break. They had hot office sissy sex for about an hour.
It was time for strapon lessons for sissy boy. He just went shopping and got some new jeans. They fit snugly against his sissy buttocks. The cheeks that will soon be abused by a hefty strapon cock !
Sheila was upset his high heels looked better then hers. After a quick scolding she told sissy boy to start feeling his breasts. This is a great sissy strapon movie right here. She looked at him strangely right before it was time to insert her fake dick into his hungry hole !
It would soon be strapon sexy time ! The anticipation was in the air. She stripped off his jeans and told him they were hers now. He had to walk home without them. First things first though. He grabbed his ankles with a quickness. Lightning fast ! Lubed up his ass and went to town! Sissyboy squeeled like a sissy !
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They first noticed his potential when he dressed up for Halloween as a girl? He was just so good at it ! Tammy wanted him to be her sissy boyfriend immediately! She invited him over to her place to watch a few videos.
Bitch boy Sissy Tom was having few problems getting his makeup on correctly. Tammy said she would help out. He wanted to do straight scenes when he showed up at the modeling agency. I guess he didn’t have what it takes. Namely, a small pee pee. 
The good news is he’s a sissy now getting the strapon dildo right where it counts … up his ass ! Gee wiz, everyone was shocked how pretty he looked after dressup time. After Tammy was done punishing his butthole his makeup was all smeared and he looked like …
She was so amazed about how well he did his makeup. It was dressup time and the sissy was about to piss off his girlfriend. She told him numerous times the blush goes on last. He needed to be punished with a strapon !
It was time for Clarence the sissy to pay the price.
She grabbed him by the wig and demanded he bend over. Clarence was feeling so hot his butthole puckered up too tight. She had to use some KY Jelly on his anal cavity. Sissyboy took the hard strapon cock ! Afterwards his lipstick was smeared all over his sissy face and it was time for cleanup.