Sissy Farm

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Brianna was a 23 year old biological male. But years of watching shemale porn, she became a sissy. Her days were filled with watching sissy hypno and riding her toys. She kept her cock caged away and never played with it. Her days, like most sissies were spent scrolling Tumblr looking for someone to take her in. She wanted to be somebody's person. She was cute but chubby, she was also a virgin in both departments. One day she happened upon a ad. "Sissy maid wanted in Pa", living right in New Jersey, she quickly replied.

Brianna was lazy, in her depressed mind she thought being a maid would be easy. The laziness was the reason she was chubby and a virgin. She also was a bit bi-polar.

Tim the creator of the ad replied to Brianna. They started discussing what he was looking for and she agreed without even thinking about what he was saying. The talking continued for 3 weeks. Then Tim invited her to the farm.
Brianna was so excited she wore a black skirt, thigh high stockings and heels with a white blouse. Did her makeup, hair and nails. And she looked very cute. It took her two hours to get to the farm. When she arrived, she drove through the gate, the driveway was 300 yards long to the quaint farm house. It was a rancher 4 bedrooms 2 1/2 bathrooms. It was sage green with black accents. And it had a wrap around porch. On the other side was 2 barns and a 8 car garage. Brianna was ecstatic about the property.
Tim walked out to greet Brianna. He stood 6'7 about 240 pounds. He had a stocky build and short brown hair covered with a white cowboy hat.

First Tim took Brianna around showing her the farm. The chickens, the horses and the pigs. He showed her the massive vegetable garden and the tobacco field. Then they went inside and he showed her the house and her bedroom. Finally they reached the dining room and sat down at the table. Once again Tim went over everything he needed from Brianna. Without thinking she agreed. Then there was paperwork. Agreements, tax info and a contract. Brianna read everything and signed it. To celebrate Tim poured some drinks and they toasted to her new lifestyle and career.

Brianna had the weekend to get her affairs in order and move to the farm. Monday morning she was there ready for her new life.

After unloading her bags into her room she met Tim in the dining room. He prepared a good hearty breakfast for the two of them. On the empty wood chair laid a maid outfit, they ate there breakfast . After Tim told Brianna to strip naked. She did quickly. He looked her over then bent her over the table. Brianna was excited she was about to be fucked by a real cock. Little did she know Tim was packing a 10" thick dong. He reached down to the table and grabbed a stick of butter. Coating her virgin asshole and his massive cock. Slowly he pushed onto her hole. He was bigger than her biggest toy, but she wanted it so bad. He pushed harder and her asshole started opening. Finally his mushroom head popped in, Brianna squealed like a pig. He continues to enter her as tears rolled down her face. Once he was balls deep he paused for a moment. Then slowly he started fucking her virgin ass.

Tim put his right leg on the table and started pounding away at Brianna. Her tears and cries turned to moaning and begging for cum. Tim started forcefully slamming his body into hers. Her fat ass cheeks shaking from the pounding. His cock brushing over her prostate just right as her caged cock was spurting cum all over the table. A few more hard pumps and Tim flooded Brianna's bowels with cum. He pulled his cum soaked cock from her gaped hole. Pushing her to her knees she sucked him dry. After he told her to clean up her mess with her tongue. Brianna began licking her cum from the table and then the floor. After it was all cleaned he told her to put on the outfit. It was a maid outfit with a very short skirt and no panties.

Tim tells her, every morning you have a list to go through and here it is . He slides a folder to her. It reads:

Wake up: 5am
No clothes
Make coffee
Make breakfast
Clean up
Be waiting for me at 5:45 with coffee
I drink you suck
Eat breakfast
Bend over
Clean up the mess
Clean kitchen
Get dressed
Feed chickens, horse and pigs
Exercise
Make lunch
Miss any of these and you will be punished.

Brianna realizes she probably should of read everything, but she wanted a new life so she happily says no problem sir. But what kind of exercise?
Tim informs her that she will have a trainer to get in shape.

After Cleaning up, Brianna heads to the chicken coop where Tim is waiting for her. He shows her how to feed all the animals. Then takes her to the garden to get some lettuce and tomato for lunch. After they head to the garage and go up the stairs to a state of art gym where her trainer is waiting for her. The trainer is a woman and gives her yoga pants and a sports bra. After Tim leaves the trainer Kim informs Brianna that she is overweight and sloppy looking. And she was there to get her in shape.
After the hard work out Brianna heads back to the house gets a quick shower and makes lunch. She rings the dinner bell and waits on Tim to return.
They eat lunch and Tim slides her another folder.
It reads:
Clean house
Do laundry
Get mail
Prepare dinner
Clean up
Dinner
Training
Brianna takes the list and follows it. After they eat dinner that night, Brianna reports to the training bedroom.