Fun Starts at the Farm

Sherry's Sherry's dream becomes a reality while at the farm.

Terry always wished he had been born a female. He was a pretty baby and people were always mistaking him for a little girl. So his mother would dress him in cute little dresses. She let his natural curly hair grow out to enhance his feminine look. She taught him to walk and talk like a little girl because she always wanted a girl. In school this caused him a lot of grief. Other kids made fun of him and called him names. When he returned home, his mother would wipe his tears and would encourage him to put on some girly things to soothe things out. As he grew so did his wardrobe. His mother bought him all the girly things. She taught him well. So at home he was the daughter his mother always wanted. He had a nice girly figure and stood 5’ 2” tall. His legs were slender and hairless. He also had small hands. His total weight was around 120. There were many times when he would go out dressed as Sherry with his mother and many males would turn and look at him.

So Terry became Sherry, the person that became the dominant one. Now at nineteen and still holding the youthful look of a girl of thirteen, she was packing to go visit the farm that she had inherited from her mother's parents. She packed some skirts and dresses, slips and petticoats, and her bras and panties. She planned to drive dressed as Sherry. The trip there was uneventful and she had to open up the windows to air out the house. She did some grocery shopping and settled in for a long stay. She had been there a week when a visitor showed up.

She was sitting on the front porch when a car pulled into the driveway. She watched as a handsome older man got out of the car and walked up.

“You must be Sherry. I'm your neighbor Mike Semore. Oooh my, they didn't tell me you were so pretty!” Mike said as he took in the lovely looking legs that were showing.

She noticed him looking at her legs but made no attempt to hide them. She smiled and said,
“Yes I am Sherry and thank you for the nice compliment. It's nice to meet you Mike.”

She invited him in and they sat on the sofa together. They visited for some time after Sherry got them a cold drink. Sherry couldn't keep her eyes off him and he was doing the same with her. “Your grandmother told me all about you. She knew who I was and what I liked. And she hoped we would be okay with each other.”

“What do you mean, she told you all about me. I don't understand.”

Mike sighed and said, “Hear me out before you say anything okay? First of all your grandmother and I were good friends. She knew all about who and what I was about. And it didn't bother her and so she told me all there is to know about who and what you are.” He looked deep into Sherry's eyes and continued saying, “She told me how your mother raised you to be her daughter. Your secret is safe with me because I've always hoped to meet someone as pretty as you. Do you understand what I am trying to say?”

Sherry began to tear up and she moved closer to him. She didn't know why but she leaned her head on his shoulder and between sobs she told him, “Oooh Mike, Mike if what I think you are telling me is, I mean, I think you're someone I always dreamed of meeting. What you are saying to me is that you don't care if I am a male dressed as a 8woman? Oooh if that's true, you have made me so happy!”

Mike turned and lifted her face and wiped her eyes. He smiled at her and gave her a quick kiss on the lips then said to her. “That is exactly what I wanted you to know. I was really praying that you and I would hit it off.”.

They began kissing long deep kisses. Mike held her close and then dropped one hand onto her leg. He started moving it slowly up her leg. Sherry shuddered and sighed at feeling the hand move up her leg and under her dress. Mike was igniting a long time hidden intimacy. A desire to be taken in her femininity. Her breathing was becoming so labored. As she responded to his advances.

“Oooooh Mike Oooooh god Mike. Mmmmm mmmmmm yeeesss, ooooh my god yeeesss Mike, make love to me! Oooh aaaaah aaaah,ooooh yeeesss!” Sherry said breathlessly.

“Mmmmm you sweet sexy little creature. I want to male passionate love to you but let's go to my house where I have everything.”

“Not everything, you don't have me,” Sherry said giggling then added, “well at least not yet!” Then kissed him.

At the house Mike led her to the bedroom. She wanted to be fucked in a dress or in her petticoats and slip. Mike opted for the petticoats and slip. His cock was rock hard as he placed it at the entrance to her pussy. Sherry trembled at the touch of the hard cock. With her legs raised up high, she looked deep into his eyes waiting for him to start to push in. Finally he started to push into the tight virgin pussy. Sherry gasped as his cock fought with the sphincter to gain entry to her pussy. The pain was excruciating but she didn't want to discourage him so she bearded it as best she could. Soon the pain started to ease up and she started to enjoy the feel of his cock as it slid along the side of her pussy. It was total bliss and she pushed up to meet him as he thrust down. They stopped and he turned her over and again began to bang away at the tight pussy. Sherry was moaning loudly in ecstasy.

“Oooh Mike I can't believe how wonderful this feels. Fuck me harder, ooooh yeeesss please fuck me harder. Mmmmmm aaaaah aaaah, ooooh god yeeesss fuck my pussy! I love it, I love it!” She cried.

Mike fucked her pussy so hard that he brought to a huge orgasm. He kept fucking her until he shoot load after load of hot cum into her. Sherry felt the hot cum hit the back of her pussy and it sent lusty shivers through her. She felt totally girly at last and she silently wept tears of joy.

They cleaned up and went out to dinner and later that night they slept together in the nude. Mike told Sherry that she would become his fuck princess. And Sherry threw her arms around him and said that it was what she wanted also. In time they wanted more spice in their lives so they tried out some fuck parties. Sherry really liked playing musical cock at the parties. The ladies would take their panties off and then they would tuck their dresses at the waist, the music would start and the men would sit with their pants and underwear off and of course hard cocks and when the music stopped whoever you sat on, was the person that had you for the night. Usually it was played last. The parties were a lot of fun with the men always wanting to slip their hands under the lady's dress or skirt. The ladies were just as bad, grabbing a man by his cock. Sherry and Mike truly enjoyed their relationship.