Milking Boy Stories

119,036 results
Orientation
Length
Source
Infinite Scroll

Mrs. Swanson's Boarding House Ch. 02

by 0ra11yfix8ed on Sep 25, 2017
Exhibitionist & Voyeur

Miss Bridgeway led Carl out of the parlor and down the hall to the kitchen using his penis as a joy stick of sorts. "Did you enjoy your first session with Mrs. Swanson?" Carl had just been masturbated by one of the founding Sisters of The Sisterhood a group of progressive women who advocated CFNM as a way of controlling the sexual urges of men, young men in...

Milky Boy Ch. 01

by Subone1 on Sep 16, 2017
Toys & Masturbation

In the way of background, I am a 48 year old male. I'm in good shape for my age and have been married for 27 years to my college sweet heart. Like most couples at this stage of our lives, we have struggled with keeping our sex life interesting and active. Over the years we have explored my many fetishes, dappled in BDSM and most recently, enjoyed the excitem...

A Momma's Boy

by a real jrkoff on Sep 25, 2017
Fetish

Some men are just born dickheads. Tom was a 32 year old dickhead... or at least his wife certainly thought so. He had just lost his job of ten years and now he was having trouble pleasing his young better half. It wasn't the sex... they didn't do that anymore. It was just that Tom had a bad habit of getting into his wife's things. Basically timid in natur...

Milking The Bull Ch. 03

by DamienDeath20 on Nov 18, 2019
Transgender & Crossdressers

A.N. MOOOOOOOOO!! CHAPTER THREEEEE YAAAAAAYYYY!! Lol I hope you guys are excited to see the next installment of the lovely couple on the farm :3 It took a while but this one was crazy fun to write! The Following Contains: Bull dickgirl fucking the fuuuuuuuuuuuuuuuuuuck out of a blonde femboy with her horse cock. Resulting in slight belly inflation fro...

Breaking Benny: Dark Elf's Slave

by EstebanMamono on Jun 19, 2018
NonHuman

I have been extremely sick these days, so sorry, my 20 drafts are being made one by one. Please enjoy another Dark Elf scribble. Sorry about spacing in case something pops up. ***** Aranis Van Rose, and her daughter Phaeliss, or Filly-kun maintained their secret village with strict fairness. Worked by their throng of human slaves, The Rose family was prosp...

Cup of Coffee

by mrmayhem121 on Sep 13, 2017
BDSM

It starts in the morning; I wake up and notice that my sub isn't beside me in bed. Her spot is cool to the touch, letting me know that she has been gone for some time. This is unusual as I tend to let her sleep in as much as possible. Seeing the bed empty has me wondering what is going on and as a fairly assertive Dom, I don't like to be kept in the dark. I...

Milky Boy Ch. 02

by Subone1 on Sep 16, 2017
Toys & Masturbation

The next day I got in the car to head for work and turned my cell phone on. I had a text message waiting for me from Lauren. The message was short and to the point: "Milking today at 9:00 A.M. Pick me up in front of school. Be on time. Don't forget the gloves and my money!" Oh shit, I thought, how do I get away from work at 9:00 A.M.? I mentally scanned my c...

The Contest

by Little Johnnie on Sep 25, 2017
Fetish

"OK., I'll bite. What's a toilet roll test?" I asked. Little did I know what fate asking that one question would lead me to. My name is Charlie, and that night I found myself at a party with my girlfriend and three other couples. We had been drinking all night and the conversations had gotten onto the topic of sex. Just prior to asking that question, we had...

Dirty Farm Yard Adventure

by rbbrbootjake on Sep 12, 2017
Fetish

Teresa was the oldest of three, 18 years old and dreaming of the day she could leave the farm and move to the city for school. Growing up on a dairy farm was hard work, and as the oldest she had a lot of responsibility she wasn't so crazy about. The early mornings and long days were particularly unbearable for her, and she had better ideas of where she wante...

My First Milking

by Bakeboss on Sep 13, 2017
Fetish

When Mistress first put me into chastity, she said it was for a trail period. She soon found out it not only keeps me from abusing my worm while she is out it also keeps me more attentive to her needs. Another plus was that now I had to sit to pee, I have always had to relieve myself this way while Mistress was around, but she suspected when she was away I d...