Category: Sissy Stories

Jim’s brothers were quick to greet us, both asking how I felt and apologizing for the accident. I thought the boys were going to have a fight over who was going to bring me a drink. As quick as I could say “beer” they took off shoving and trying to trip each other, Jim yelled … Continue reading From city boy to country girl 5

We spotted the cove as the sun was starting to go down. Tom carefully navigated the small entrance. Purely a spectator I watched from the little pulpit thingy that extended out over the bow, taking it all in as we rounded the point. Bending over the railing I was focused on the fish darting to … Continue reading Bill to Billie 7

Jim quickly got out and opened my door, put his hands around my waist and lifted me up onto the seat. Smiling like he had won the lottery he strutted around to the driver’s side and got in then ask “how are you feeling tonight, the knee is bruised but you aren’t limping on it … Continue reading From city boy to country girl 4

I looked into the eyes of the girl looking back from the mirror then said out loud “No turning back now Terri” and headed downstairs. Mom had already made her way to the kitchen and was busy preparing dinner. When I reach the landing I greeted her with the normal “how was your day Mom?”. … Continue reading From city boy to country girl 3

The night was magical, experiencing my wildest fantasies “cum” true and with a person I care for and trust. I was very impressed by his plan but even more so by what it took to bring it together. The time, and someone’s effort to assemble everything and I really mean EVERY THING needed for my … Continue reading Bill to Billie 6

I was married to Jen a nice-looking woman. I was a cross dresser before we married. She knew of my cross dressing and would buy me panties along with other articles of lingerie. I would dress as female when at home, per her requested that I do so. She always told me if I was … Continue reading Sissy husband

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell. My wife Laura welcomed him into the living room then closed the door and came into my room and asked for me to come out. I felt a chill of fear but tottered down the hall … Continue reading Husband turns into sissy wife for another Man

When a Man or Women is looking for a sissy to rent or buy, they come to the Sissy Placement Center or better known as the “SPC.” ATTENSHION: All Sissy’s unless requested otherwise will have small penises and will be on hormonal treatment for them to transition into a shemale. This is all in the … Continue reading The SPC for sissies

I stood in front of Mr. Tyrone in all my pink frilly sissy outfit with no panties by order of my wife. I was seeing Mr. Tryone’s Huge Cock between his legs as he sat on the couch before me. I immediately started to get an erection until it stood straight up. Feeling humiliated being … Continue reading Sissy husband’s new life

Laying on my back dipping my fingers into the puddle of cum on my belly I thought about cosplay party and sucking David’s cock. The taste of his cum, how he moaned as he pumped his load into my mouth I couldn’t help myself I scooped up my cum and Iicked it off my hand. … Continue reading From city boy to country girl 2