Maggie's Punishment - Cover

Maggie's Punishment

Copyright© 2022 by Master Jonathan

Chapter 1

BDSM Sex Story: Chapter 1 - He has met a girl with a strange "kink" - she gets off being spanked and punished! Can he give her what she needs and be the Sir she desires?

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   MaleDom   Spanking   Oral Sex   Caution   Violence   Illustrated  

I have known Maggie Anderson for several years now and we regularly see each other. We aren’t committed to each other in any way, but we both enjoy each other’s company and see a lot of one another. I understand her and she apparently gets what she needs from me.

Maggie has had a troubled past and it has lead to some very unusual needs for her. As a child she had less than ideal parents – her mother was a bitter, cruel, and heartless woman who blamed her for all the trouble she had and for ruining what she imagined her life should have been like. She was abusive both in word and deed, never giving Maggie any kind of praise or credit for doing anything right and always belittling and degrading her. She slapped her and punished her severely for the slightest infraction.

Maggie’s father was no better; a spineless pussy of a man who wouldn’t go up against his wife no matter what she did. He would rather stay away from the house, working or out at the bars, than go home to face his bitch of a wife. When he did come home, he was drunk and he, too, was abusive to Maggie. But rather than hit her and cuss at her, he used his daughter to get the gratification that he could not get from his harpy of a wife. Maggie was molested by her father on several occasions which caused her mother to rant on about what kind of a whore would sleep with her own father and other equally hurtful things.

Maggie’s abusive childhood caused her to have very low self esteem and she always thought that she was more trouble than she was worth and wondered why any man would put up with her. Consequently she didn’t date (not that she could – her mother would pounce on her and call her a whore if she even smiled at a boy!) and so she never knew what it meant to be loved.

Maggie lived her sad life not knowing what it was like to be cared for not knowing her own worth until she was 26 years old. That’s when I met her. She was working as a waitress in a small-time cafe; a job that was far beneath her and which did nothing to raise her opinion of her self-worth. I had just taken a job with a large company whose office was just down the street a couple blocks and I stopped into her cafe for lunch one day. She waited on me that day and I saw something in her eyes when she looked at me. She was very shy and didn’t speak much except to take my order. When she brought my food I asked her what days she usually worked. They coincided pretty much with the days I was at the office so I decided to make this cafe a regular lunch thing and see if I could get this shy, reserved woman to open up a little.

Slowly over the next three months or so she began to relax when talking to me and I could see the walls slowly crumbling. I had even got her to sit with me when she took her breaks and we could talk a bit. One day I was in the cafe for my regular lunch break when Maggie came to take my order. I ordered the special as usual and as I finished Maggie came back to give me the check. This time, though as she began to walk away I grabbed her wrist to stop her.

“Maggie, go out with me this weekend. We could go to a movie, to dinner, or whatever you’d like,” I said. Maggie looked at me, stunned, like I had just walked into the cafe naked with a clown’s multicolored wig on!

“You want to go out with me?” she said.

“Yeah if you’d like to – unless you have a boyfriend or something,” I said.

“No, I don’t have a boyfriend. But why me?” she asked. This was my first hint of Maggie’s self-esteem issues.

“Well I have been coming in here for awhile now, and I always ask for you. I thought maybe we could get to know each other a little so we would have more to talk about when I come to see you than the weather or the daily special here,” I said, smiling.

“I don’t know...” she said looking around. I think she was looking for a reason to rush off. I had to move quick and seal the deal.

“Aw c’mon Maggie. Look, I like coming here and I like talking to you. I would just like to get to know my favorite waitress is all. Please say you’ll go out with me,” I said.

She thought about it for a bit. “Okay, I’ll go out with you. Dinner sounds nice,” she said looking down and fiddling with her hands nervously.

We decided that weekend we would go out. Saturday evening I drove to the address she gave me. It turned out to be a small trailer court and as I drove past the rows of trailers I noticed that almost all of them were older and in rather well-used condition. Frankly some of them barely passed as living quarters! I drove on looking at some of the depressing conditions of some of the trailers until I got to the end of the row. There sitting by itself (the lot next to it was vacant) was Maggie’s trailer.

Maggie’s trailer was a small 14’ x 60’ built back in the early 70’s. It had two bedrooms (well one bedroom and one very small room that could work as a child’s room in a pinch). It, too, was in dire need of work, although she had made some attempts to decorate the yard with some garden pieces and there were curtains on the windows. But I could tell this place was haggard and time-worn. I put it out of my mind and concentrated on the girl inside. I went up her old wooden walkway and knocked on her door.

“Hi John, come on in I’m just about ready,” she said as she opened the door. I opened the screen door and went inside. The inside of the place was sparsely decorated with a hodgepodge assortment of second hand store furniture and accessories. I could tell that very few things in her small trailer were for ornamentation alone – most everything had a purpose. There simply wasn’t room in her small trailer or her life for fancy frills.

“Did you have any trouble finding my place?” she asked.

“No, no problem,” I said.

“That’s good. Well, give me a minute and I will be ready,” she said. As I sat on the old worn love seat in her living room, she went back to the bedroom to finish getting dressed. She came back out after about five minutes. “I’m ready now, John. I hope this is okay ... I don’t go out much, really, and you never said where we were going to eat,” she said. Her deportment was one of apprehension and embarrassment. She was ashamed of her trailer and her station in life.

“You look fine, Maggie. I thought we would go to Barron’s. Their steaks are really hard to beat!” I told her. She smiled and we left for the restaurant.

After a nice dinner and conversation we headed back to her trailer. I was sensing that she was nervous about how the good night would go – whether to invite me in or not and what would happen either way. Maggie knew that I was a businessman and I would come into the cafe in a suit. She was a waitress and not even the head waitress. She didn’t feel she had much to offer.

Inevitably the moment of truth came and I walked her up her walkway to her door. She stood there trembling, still not knowing what to do next. But I knew what to do. Knowing this was our first date, and wanting to see her again, I let her off easy.

“I had a wonderful time tonight. I’m glad you decided to go out with me. And I’d really like to see you again,” I said.

“Y-you would?” she said. “John you know that I...” she let her words trail off. I knew what she meant.

“Maggie, sweetheart, I don’t care that you are a waitress. I don’t care that you live here, I don’t care about any of that. I enjoy your company and I like being with you. And you are very pretty when you dress up. So don’t worry about any of that stuff. You have a lot to offer and I’m interested, okay?” I said.

We kissed there at her door and I let her get inside before I turned and went home myself. As I turned to get in my car, I saw her peeking out through the curtain of her trailer window. I waved goodbye and saw the curtain suddenly close – I had caught her watching me. I smiled and left for home.

We went out four more times after that, each time I picked her up and dropped her off. I made no moves to try anything with her; as shy and reserved as she was, I didn’t want to move too fast and scare her off. I figured that as long as we were dating, she would let me know when the time was right. On our fifth date we had gone to the movies – some sappy romantic love story she wanted to see – and then to a restaurant for a little dinner. It was at the restaurant that I learned a lot more about my Maggie.

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