Chapter 1 - looking for a kinky mommy

Brian didn't want a long term relationship, he just wanted sex and he figured now was the time to explore and find his kinky side. At age 23, Brian was not the type of guy to sleep with any girl that came his way, he had only had sex with long term girlfriends which was all well and good but now he felt it was time to explore. He wasn't sure what he was looking for but he figured that when he found it he would jump on it. The idea of roleplaying with a sexual partner sounded very attractive to him and he thought it was a good place to start, especially the idea of being the submissive in a BDSM kind of relationship. The only problem Brian encountered was that the idea of having a cruel mistress was not appealing at all. He wanted someone soothing and gentle, someone who would love and accept him but form him into what she wanted him to be. He filtered his search again and the first profile he saw hit the jackpot. The profile pic was of an attractive woman with black hair who didn't live far from Brian. He was especially enticed by her profile.

Headline: Mommy looking for her little boy
Name: M
Age: 41

About me: I'm a divorced woman with no children looking for a special little boy willing to let me be his mommy. We will have all sorts of fun games to play and I promise you will get lots of tender love and care.

Brian immediately sent her a message, "I'm a lost little boy looking for my mommy..." He was surprised to receive a response so quickly they chatted for an hour before taking the chat off the site. He discovered that the woman's name was Meredith and he was already enthralled. Meredith asked him questions about what exactly Brian wanted and was looking for. Even online Meredith seemed like a warm and inviting person. Brian had a hard time believing that someone like her would be on a site like this but at the same time the idea of having a kinky Mommy who was so accepting and loving was something he lacked in his day to day life and he wanted to explore that side of him. He didn't grow up in that type of household, his mother was a trophy wife and pretty much only had a child because it was expected of her and was extremely controlling forcing Brian to be active, get good grades and not embarrass her. His father wasn't much better. He had constantly worked and when he was home he drank heavily but made it clear that he expected his only son to take over the family business, something Brian had no desire to do. Brian kept his mouth shut while he was in their home and during his college years telling his parents he was majoring in business so they would continue to pay for school but was actually working towards becoming a high school history teacher. It was quite the shock to his parents when he was called to the stage as a history and education graduate and an even bigger shock when he said he would not be returning home to take on a job as VP of the company his father had built. His parents all but disowned him that day, something he was okay with, they never accepted him for who he was and now he was free. He was happy and was more than two-thirds of the way through his first year teaching at one of the local high schools.
A few days later, Brian went to the address that Meredith gave him and found himself looking at a small but comfortable cottage house in one of the more affluent neighbourhoods in town. He knocked on the door and was about to knock again when he heard someone say, "Brian is that you?"
"Yeah."
"Come on in!"
He walked in to immediately see the most beautifully voluptuous woman wearing nothing but an apron. She was extremely pale and her makeup was flawless. She had the most clear blue eyes he had ever seen. The fact her hair was slightly gray in certain areas seemed to add to her beauty and not subtract from it. Her breasts were extremely large and inviting. Brian was going to enjoy playing games with her.
"Oh mommy's little boy is home!" Meredith exclaimed as she walked over and gave him a kiss on the forehead. Brian was surprised that she went into the roleplay immediately, "would my little boy like a brownie?"
"Yes, Mommy," Brian said meekly. He was already getting hard just looking at Meredith.
The night went on like that, with no stops in the roleplay between Meredith and Brian. Brian was extremely horny and was looking for release but also enjoyed having Meredith mother him. She filled him with all sorts of treats, gave him a bath made him put on a pair of overgrown little boy pajamas before having him follow her into the bedroom.
"My little boy has had such a long day. He deserves a special treat."
At that moment Meredith undid her apron and walked over to the bed putting her breasts right in Brian's face. He immediately put a nipple in his mouth and began suckling. He was extremely surprised that her nipples immediately began leaking milk. This got Brian even more turned on and he immediately began drinking her warm and sweet milk. The more milk he drank, the hornier he got. Eventually he came just from suckling on Meredith's tits but that did not stop him from drinking even more milk. Eventually, the moment came when his belly felt far too full and he had grown sleepy. He fell asleep on Meredith's chest and whispered "Mommy."
"I think I found the perfect little boy," Meredith said stroking his brown hair.
Brian dreamt of being fed all sorts of goodies from Meredith from a crib in a baby nursery. He was a happy adult baby wearing a bonnet and bib laughing and gurgling. Meredith was singing children's songs to him such as Twinkle Twinkle Little Star and was clapping as a baby would. Then much like the events from the night before, he was happily feeding from Meredith's breasts again.
Upon awakening, Brian felt foggy, almost like he was hungover. He was also extremely horny from the dream he had. The smell of pancakes wafted into the room from the kitchen. Brian walked in there to see a naked Meredith cooking and making breakfast and he realized that despite drinking large amounts of Meredith's milk the night before, he was starving.
"Is my little boy, hungry?"
"Yes, mommy."
Meredith put a huge plate of pancakes, scrambled eggs with cheese and 5 sausage links in front of Brian. He was about to pick up a fork but Meredith slapped his hand away.
"Good little boys let Mommy feed them."
Brian had no choice but lay back and let Meredith feed him. Normally, he would have coffee and a muffin on his way to work but he was surprised that he still felt hungry after finishing Meredith's large breakfast.
"Is my little boy still hungry?"
Brian nodded his head while staring at Meredith's large and leaky breasts.
"I thought so," Meredith replied shoving a nipple in Brian's mouth.

After the next feeding, Brian went back to bed and didn't wake up until lunch. The cycle repeated itself all day Saturday and Sunday. Brian tried several times to break out of the roleplay to find out more about Meredith but to no avail. Meredith stayed completely in character of Mommy and expected him to stay in character of Brian being her little boy. Much to Meredith's protests about wanting her little boy to stay with him he left on Sunday evening promising to return the next weekend. Brian drove home, feeling very good about the weekend and happy he decided to explore his sexuality further. He did find it odd that Meredith never broke character but assumed that's the way it worked as he found it likely she was far more experienced than he was at these sorts of games. It wasn't until he got home that realized the only time he came was when he was suckling on Meredith's breasts. They never had sex once. Surprisingly to Brian, it didn't matter. He was satisfied if they never actually had sex. This was not that type of relationship. He was quite happy to be Meredith's little boy and wondered if that was what Meredith would be like if she was really his Mommy. Right before he was about to go to bed for the evening he received a text from Meredith,

"I hope you enjoyed our weekend together. XOXO, Mommy."

Brian closed his eyes. He certainly did enjoy the weekend and he was slightly sad it was over. Meredith was the mom he always wanted, the kind loving mother, not the bitchy over-bearing mom he actually had. Deep down inside, he wished it was possible to become Meredith's little boy forever and that frightened him.