Kinky Sex Stories

Older Woman Boss sex story, part 1

I was only 19 when I began working for Miss Jansen. She was an older woman in her 40’s and lived about a block away from me in a very nice apartment building. She had seen me in the local neighborhood grocery store a few times and one day asked me if I could help with her some things around her condo. Since I was a struggling musician, I needed all the odd jobs I could find. My hair was long and I was thin and it was not always easy to find work.

The first day I showed up at her apartment, she was wearing a sexy long white nightgown worn lose enough for me to catch an eyeful of her large and beckoning breasts. They were the kind of breasts that can distract a man so much, it’s difficult to have a conversation with the face that owns them.

Miss Jansen asked me to clean her kitchen from top to bottom. I went to work but all I could think about were her amazing breasts that seemed to stare at me and call my name. Miss Jansen came into the kitchen and said,

“I want you to bend down there, and get under the sink now. That’s good. Get under the facet and clean around there nice and good for me.”

My ass was up in the air and I was in a very submissive position and very aware of it. It felt good and I thought perhaps it was one step closer to being able to suck on her large perfectly formed nipples.

Once I finished the kitchen I went looking for her and heard her in her bedroom. She was moaning and I thought perhaps she was in pain so I knocked on the door and said,

“ Are you alright in there? I finished the kitchen.”

I heard some commotion and then she opened the door and was very upset.

“Don’t you ever bother me while I am in my bedroom do you understand?” she said.

I agreed and went out on the balcony to pot some plants. When I was finished there, she asked me to clean up her bedroom next.

While I was cleaning her bedroom, something caught my eye in her top draw. I knew I shouldn’t be looking in her stuff but I could not resist. I opened the draw slowly and saw a large collection of dildos and lotions. There were about 10 dildos of all sizes and shapes and I the curiosity got the better of me. I picked one up and just then I heard a loud voice behind me say,

“You like that one don’t you?”

“Um, I’m sorry,” I said and put down the dildo and closed the drawer.

“Don’t be shy she said, it’s ok if you like them, but they are mine, and you are not allowed to touch my things unless I say it is ok. Do you understand”

“Yes ma’am” I cooed.

“ I am going to have to teach you to be more respectful of my things. If you want to enjoy my things, you must earn that privilege first. Do you understand?

“Yes ma’am.” I said.

“Now come over to the bed and lay across my lap”

“Why?” I asked.

“I must punish you for taking without asking. Come here now if you want to keep your job boy.”

I went over to the bed and pay across her lap. She began to spank me very hard. It hurt at first but then I began to like it. I arched my ass and began to moan. I could feel my cock getting hard and she could too.

“I see you like this. The point is for you not to like this. I can feel your little hard on rubbing against my robe. That is a very very bad boy.”

She spanked me harder and harder and then asked me to stand up, spread my legs, and turn around.

“Now this is going to hurt a little. I want you to take it like a man. Do you understand?”

“Yes ma’am” I said.

And then she kneed me in my groin. I fell to the floor in pain. She took the dildo out of the draw and stood over me and said,

“Do you still want this?”

“No ma’am” I said.

She left me on the floor and when I felt better I got up to leave her apartment. As I left she told me to come back tomorrow at the same time. And that she hoped I had learned my lesson.

I debated on returning, but I figured that since the women had spanked me and hit my balls, that there was a good chance more sex would come. I was embarrassed about the dildo, and everything else, but I needed the sex, and the money badly.

The next day, she greeted me in tight sweat pants and a bra. Again, all I could do was stare at her large perfect breasts. She sent me in the kitchen again and asked me to clean her drain. I unscrewed the drain and all the gunk and garbage spilled out on my head, shirt and pants. Miss Jansen saw this and said,

“You idiot. You can’t walk around my apartment with all that crap on your clothes. Now go into the bathroom, take off your clothes and take a shower. I will wash your clothes for you. Now go!”

Ahh, things were getting good now. I undressed, left my dirty clothes on the toilet and got into a hot shower. Miss Jansen came in and took the clothes and said,

“Don’t worry. I am not going to spank you for that. It was an honest mistake. But don’t let it happen again.”

She took my clothes and left. 10 minutes later I got out of the shower and toweled off realizing I had no clothes to wear. Just then she came into the bathroom with a nightgown and panties and said,

“This is all I have for you to wear. Give me your dirty towel. Don’t worry; I have seen it all before. Give me your towel.”

I slowly took my towel off and she took it from my hand smiling.

“Here, now put the panties on first.”

I took the small thong pink panty and slowly inched it up my legs and thighs.

“It’s a perfect fit.” she said.

Now turn around and I will put this pretty night gown on you.

I turned around and she gave me a good slap on my butt.

“My dear, what a cute butt you have there. You look fantastic in those panties. Now come here and look at yourself in the mirror. Aren’t you pretty? I think your pretty. Now sit down and let me put something else on you.”

I was getting pretty hard by this point and would have done anything she asked me.

“Good boy.” She said and applied red-hot lipstick to my lips.

She stood me up and took me into the bed room and she laid down on the bed.

“Just because you are wearing my clothes, does not mean you are still not working. Reach in my drawer and take out the large dildo you were so interested in yesterday.” Miss Jansen said.

I took out the dildo and brought it over to her.

“Good boy. Now come lay down next to me.”

“Do you know what to do with a cock this big? I didn’t think so. So I am going to have to show you.” She said.

She began to suck it, taking it deep in her mouth, and then began licking it while holding the balls very lightly. It was turning me on so much.

“Now your turn bad boy.” She said.

I took it in my mouth and tried to suck it but I almost gagged. She told me to slow down and take it nice and slow. Once I got more comfortable with it, I began to enjoy watching her, watch me such on the dildo. She began to play with herself and exposed her pussy to me and placed my hand on top of hers and is rubbed and massaged her clit, as I kept sucking on the dildo.

She began to cum and climax and make wonderful noises and moans.

“Keep sucking on that cock. It is turning me on so much to see you do that. With your red lipstick, and pink panties. Keep sucking boy.”

Miss Jansen then slipped down my pink panties and began to suck my swollen cock which was fully erect. My mind was completely gone at this point and I came in less than 2 minutes into her mouth.

“Now, wasn’t that better than cleaning the bathroom”

“Yes ma’am” I said.

“Come back tomorrow at the same time. I have a very large friend I want you to meet. I have a feeling you are going to like him.” She said.

“Him?” I asked.

To be continued.