I was about 23 years old when this happened. I barely had any sexual experience to speak of. I had only slept with one girl, and she out right told me I disappointed her in bed, and on top of that she wanted a dominant, alpha male type boyfriend, and that clearly was not me. Either way, I had my first job outside of college, and had a roommate. My roommate's name was Chris, and he was pretty similar to me.
This started when Chris's mom came to make a special meal for his birthday. Her name was Lisa. Lisa was more energetic than Chris and I combined. She was probably 48 or 49 years old, but looked good for her age, though a little masculine looking, but I still found her hot. She was a little on the thick side, kind of tall (maybe 5'9"), with a nice ass, and I tried to catch a shot of her cleavage whenever I could. I pretended to be looking at her tattoos she had on her upper chest area but I think she didn't mind the attention. She had been divorced for a while from what I understood, and embraced being single. She flirted with me once in a while, and whenever she came over, I'd be masturbating to thoughts of her later that night.
It was just the three of us for Chris's birthday. She flirted lightly, asked if I was single, and pretended to be surprised when I said that I am. She complimented me on my figure before she left, which seemed strange to me. The night that she left I masturbated so much thinking about her.
A few weeks went by, and when Chris was out of town fishing with his dad, I heard a knock on the door. It was Lisa.
"Hi hon," she said.
I was shocked, and could barely speak. "Hi, oh, Chris isn't here," I said.
"Oh," she said, and then added "mind if I come in?" while already walking inside.
I opened the door wider, and closed the door behind her.
"Do you want to get some brunch with me?" she asked.
"Uh, sure," I answered, hesitatingly.
"You don't sound so sure. You sure none of your girlfriends would be too jealous if we went out together?" she quizzed me.
I wasn't sure if she was serious. I laughed, and said, "no, let's go."
I got into her car, and we drove to a small diner.
We had a lot of small talk, and she started smiling at me more I noticed. She quizzed me on my sex life, and seemed to totally not be surprised when I told her I had only been with one girl, one time. Then she finally said, "how about we go to my place next? would you like that? I have a dessert in the fridge that needs to be eaten. If you want to pass this time I understand."
"Yeah, we can go to your place" I answered quickly, but nervously, "wherever you want."
"Good, that makes me happy to hear," she said, smiling.
She was wearing a tank top and jeans. I kept thinking about her breasts. I followed her to her car. She was a little more silent now on the way there. We got there, and she unlocked the door.
She got me a beer from the fridge. I was anticipated some sort of dessert, but didn't say anything.
She told me, "I think you have a very nice, feminine figure and obedient personality. If you're up for it, I'd like you to experiment with me a little. If any of it makes you uncomfortable, let me know, and we can stop. I'll understand."
"Okay," I said slightly confused, wondering where this is going.
"I don't know if Chris has told you, but I'm usually into girls. What he doesn't know is that I'm into a little domination and submission. Is that okay with you?"
"Sure," I nervously answered, only to hear Lisa giggle in return.
She grabbed my hand, and led me to her bedroom. She pushed me on the bed.
"Just let me know if it's too much, at any point."
My heart was pounding. She get on top of me, and pulled her breasts so that they were out of her tank top and I could see them fully. I reached up to touch them, but she grabbed my hands and held them, then leaned forward so that her breasts were rubbing against my mouth.
"Do you like that? Do you like them? Do you like mommy's breasts?"
