Femdom with Roommate's Mom

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?"

"I do!" I said. I licked them and kissed them as much as I could, though she retained control of my hands.

"Good, just want to start easy for you. Tell me how much you like mommy's breasts!" she demanded.

This was a little weird to me, but since it was my first time I didn't know what to think and was intensely turned on regardless. I replied, "I like mommy's breasts a lot!"

"Good boy, quick learner," she said.

She let go, and started to lean backwards. I tried to lean forward to continue licking her breasts, but she started to pull off her jeans and panties awkwardly while she was on me, and threw them off the bed. Then she climbed up towards my face and pushed my head towards her vagina. I started licking it, trying to penetrate her with my tongue. She started to adjust herself so that she was straddling my face, and then she leaned back and with one hand pushed my head deeper into her. This made me start licking her more aggressively in return. I loved the warmth, the moisture, everything about her vagina and wanted to hear her orgasm so bad. I heard her moaning, and felt like I needed to be more dominant, since she mentioned domination earlier. I tried to grab her ass, but she grabbed my hands and pinned them down with her knees and I let it go at that. She reached for my penis area, and rubbed it through my pants. I was so hard, this little action made me start squirming intensely.

"Did I say you can stop?" She pulled my head more deep into her, but started laughing when she realized I was cumming.

"Oh you dirty boy! You weren't supposed to do that!" she asserted while giggling.

"Sorry, I'll get hard again," I mumbled embarrassed.

"Shut up, just take a shower and clean it up you dirty boy."

I got up out of the bed, and started to take off my clothes. But she interrupted, "change in the bathroom. I don't want to see your filthy mess."

It kind of hurt hearing that, but I loved the attitude at the same time. I walked into the shower, and took off my clothes quickly.

I showered quickly, and found my clothes were missing. I went back to the bedroom with the towel wrapped around me.

Lisa said, "I took your clothes and put them in the washer. Come lay down with me." She put her hand where she wanted me to sit, and so I sat there, next to her. I watched her look up and down at my body as I got on her bed. She demanded, "stand back up and let me see you from behind."

I did as requested, turning around to see her looking at me.

She slid her fingers up along my legs, around my hips, and up to my waist. "You have nice, soft curves, and a cute bubble butt. And from what I can tell you're definitely the submissive one in bed."

"Have you ever wanted to explore your feminine side before?" she asked.

"I guess so," I said nervously. I had thought about it before a little maybe, but never more than just a brief thought, but was comfortable enough to tell her yes, hoping to proceed further.

"Let's see how this goes. If it's too much for you at any moment, just say so. Deal? Say 'yes, mommy'," she demanded, seductively.

I was so turned on, and just willing to go along with anything she demanded of me, so I said right away, "yes, mommy."

"Good boy," she said. First, I don't want to see that thing you call a penis, so turn around so I don't have to see it any longer and I'll get something for you to cover it up with."

I turned so that I was facing the other direction, and she went through her dresser, until she found something and threw it to me. It landed on my shoulder, a pair of black panties.

I put them on, and she breathed a sign of relief.

She whispered, "if you cum in my clothes, I'm going to make sure you'll never cum again." I didn't reply, but I think she realized this turned me on for some reason even more. I knew that I knew nothing about sex, but didn't expect anything like this.

"Do they fit you?" she asked with a perky attitude.

"They do." I answered.

"Good, they look good on you."

She reached into a dresser drawer, and asked, "have you ever seen a real man's cock?" Then I saw what she was reaching for - a large, realistic looking strap-on.

I silently said, "well, I've watched porn."

She laughed a little, "porn stars aren't really the norm, pull your little thing out."

I pulled it out from the panties, and she put the strap-on next to it.

"See how small you are? This is just an average size. Put your thingy away now."

"Lay down," she asserted now. And she got on the bed just as I did, but she started to crawl up towards where my head was, while putting the strap-on around her waist. "Show me see what you can handle. Open your throat for mommy," she said, now hovering over my head with the strap-on just above my lips.

I hesitated, and she repeated, "open!"

I reached out with my tongue to lick it, just as she started to thrust it downwards and in my mouth. I gagged immediately, but started to get into the rhythm of her thrusting.

I saw her rubbing her breasts while rocking back and forth, and she looked right at me and demanded, "don't look at my breasts, look at the cock! This is what you need to focus on!" Then she aggressively thrusted it deeper into my mouth, making me gag and get saliva all over it and watery eyes.

She slapped my face gently, and asked, "do you like what mommy's feeding you? Are you hungry for more?"

I tried to confirm and did all I could do, and mumble, "mm hmm," enthusiastically.

"Good, I'm going to train you to be a good cock sucker" she said.

My face was all messy from watery eyes and drool. When she pulled the strap-on out of my mouth all I could do was take a few deep breaths.

She pinched one of my nipples, and said, "would you like to have a pair of breasts, like I do? I think they'd look good on you."

I mumbled, "yes," just as she was placing the strap-on in my mouth one last time, causing me to erupt in a little more drool and saliva.

She got up, and demanded, "turn around," and I did as instructed. She went to the other end of the bed, behind me, and then grabbed my waist, and helped me adjust my position so that I was on my knees, bent over in front of her on the bed. I was still a little out of breath, but under her control and command.

She pulled down the panties to around my knees, and said, "from back here I won't have to see your little thing. This may hurt a little, but so far you've handled yourself well, so make mommy proud."

She slapped my ass a couple times, and then started to guide the strap-on to my anus. I was nervous, but it seemed to glide right into me. She grabbed hold of my hips with both hands, and started to thrust herself into me. I let out some big moans, not expecting the euphoria this gave me.

She slowly increased the speed, and went deeper with each stroke, until she was going all the way. She felt around for my penis, or thingy as she called it, and started tugging on it. "Mommy decided you deserve-"

I started cumming quickly, and intensely, which made her stop her mid sentence, though she was still in the rhythm with the tugging and thrusting.

I felt like I was cumming a puddle on her bed, I had never came so much in my life. I moaned through the process too, involuntarily.

Lisa let go of my penis, and then slowed down with her thrusting movements, until she pulled the strap-on all the way out, and took it off and threw it on the floor, and laid down. I laid down next to her.

I told her, "sorry for the mess," unsure how she'd react.

"Don't worry, that can be cleaned."

She got up, and started to put on the clothes she had before.

I got up too, and started to pull the panties down, but Lisa grabbed my arm, and said, "you can keep these. I don't want to see you wearing anything other than panties over your private area from now on. Is that fine with you?"

"Yes, mommy," I answered.

Lisa smiled, knowing full well how she had changed my attitude towards sex.