Dating Mom

"Hey mom I got something to ask you," I said as I she passed me by and went for the fridge and proceeded to bend over. Her ass wasn't facing me, but from the side, no panty line was visible. Was she wearing one of her thongs? Was she wearing anything under that spandex?

"Oh yeah, what's that?" She asked as she pulled out a big liter bottle of coconut water.

"I..." My mind went blank. Her nipples were hard to the point where I could make out each nub perfectly. They looked two eraser tips protruding from her chest, almost to the point where they were comically long. I looked down at my lunch to focus on what I was trying to say. "Umm, so one of my stories got picked for this anthology and I'm supposed to give a reading for it next week."

"That's incredible! Congratulations!" She said as I looked up. I tried to look into her eyes, but her nipples were just too long. I wanted to pinch them. Suck them. Cum all over those fleshy nubs. "You're such a great writer! But what do you need to ask me?"

"Ah, this is kind of awkward. So I've been to a few of these things, and when it comes to this stuff, being able to impress publishers and agents is bigger than just your story. Like they want you to look and act a certain way."

"Hmmm, so do you need some fancy clothes are something? You should wear the same thing you wore when we went out for drinks. You looked so handsome."

"I'm alright with clothes, but this is something else you can help me with. So these publishers and agents consider at author's personal appeal, and because of that I was hoping you would pretend to be my date for it."

Mom started to laugh and she said, "Oh Jeremy! There's no way anyone would believe that!"

"They totally will! I mean, it already happened to us twice."

Mom squinted her eyes like she was thinking it through. It took every ounce of my energy to look her in the face and not her extra long nipples. I added, "It'll just be for show and I think these people will really be impressed. None of them know who you are and we could give you a fake name and backstory and stuff."

She smiled. "Okay, but keep things reasonable! And don't mention this to anyone. I mean it. It's been so long since I was on a date, I don't want people to think I corrupted my son because of it. And you should have no problem finding a girlfriend for next time!"

At that point, I was over the moon. I'm fairly certain my voice cracked with excitement when I answered "Okay, I promise!"

"Nice! Send me the details when you get them. I'm off to take a shower and relax. That ride kicked me ass."

"Okay," I said as I envisioned her nipples poking through a soapy chest. I watched as she walked into her bedroom. Each ass cheek inside her red spandex rising and falling independently. Yep, she definitely was wearing either a thong or nothing at all.

I quickly finished my lunch and went straight to the bathroom where I proceeded to cum my brains out at the memory of her nipples and the prospect of our upcoming pretend date.

In the week leading up to the event, mom wanted a backstory and alias to make it fun for her and so we settled on Renee, age 45, a divorce attorney (She learned enough from her divorce with my dad that she felt she could answer any questions that may come up). We met on a dating site and this was our third date. In the beginning, I had to repeatedly go after her since I was a little younger than she normally dates, but she had a good time for the first two dates which led into this one.

I met her outside of the reading event about ten minutes before it was set to start. She had on the dress from the first night. The low-cut(for her) one that showed off actual cleavage. Her lipstick was a darker shade of red than normal too. She looked like an actual mature woman out on a date which made me all the hornier for her. We made our way inside and I found the host. I held out a hand, "Hi I'm Jeremy blahblah and this is my date Renee."

I looked over at my mom and she gave a hi and a nod to him. He gave us instructions for the drinks, food, reading event, etc. and we proceeded to walk side by side to a little wine table they had setup in the corner. I would've loved to hold her hand or put my arm around her, but having a first physical contact turned out to be much harder than just saying she was my date.

We took our seats as mom said, "There's alot of people here. Aren't you nervous?"

As I gulped down my wine, I thought my nervousness was apparent. I answered, "Yeah, I'd say so."

To tell the truth, I was nervous. I haven't done that many of them, but public readings made me fairly nervous. That combined with all the horniness I was feeling about roleplaying a date with my mom had distilled into this pure essence of shaky nervous energy. I finished off the glass of wine, even though I knew the effects wouldn't be felt right away.

Mom touched my arm, "Your stories are great though. Everyone is gonna love it."

Whenever I get really nervous, I try to joke my way out of reliving the situation. So I responded for melodramatically, "What's important is that you love it, my darling Renee."

She laughed and swatted me away.

Throughout the course of the first few readers, we sat side by side, not really saying much since the event was pretty much non-stop. I grabbed one more glass of wine for us and then it was my turn to speak. I read my story, and really crushed it. No slip-ups and the crowd gave a really good response, including my mom who stood up to applaud. Before I sat down, I said, "That one was for my beautiful date, Renee." and then returned to my seat where my mom was smiling from ear to ear.

She hugged me when I returned and I pressed her in close. Her perfume left me feeling more intoxicated than the wine and I swear my hand felt a ripple in her dress by her hips. I had enough exposure to her panty drawer to know the exact thong she was wearing. Thoughts of cumming all over it and having her put it back on swirled in my head as she exclaimed, "That was amazing!"

I said, "Whew, glad that's over." as we broke from the hug. We took our seats again as I sat back in my chair, full of confidence and alcohol and horniness, and just went for it. I put my arm around her shoulder and she leaned in to me. The perfume ensconcing my body.

I looked over and then down involuntarily. The cleavage was right there. I could've counted the freckles and the gradual wrinkles where her tits met. We stayed like that till the end of the show where we stood up and began to head out. I grabbed her hand, and she interlocked her hand in mind.

Mom smirked: "What a romantic!"

Me: "Anything for a woman as gorgeous as yourself, Renee."

She leaned over and whispered, "You're so good at this! I keep forgetting I'm in character."

"Jeremy!" A man yelled out at me while we were walking to the door. He was an editor with a small indie house and just wanted to say hi and give me his card. I let go of mom's hand to get it, and when I returned I put my arm around her waist. I could feel the seam of that thong against my hand.

We walked out the door with my arm still around her waist. Once we got outside, we separated and began to walk back to our cars. The deal was only to pretend we were dating during the event so sadly it was over.

My mom said, "That was alot of fun! And you did so good! Next time though, find a date who isn't your mother."

Me: "Thanks, and what are you talking about? You were a great girlfriend!"

Mom: "Nope, not healthy. I want grandkids one day haha!"

As we walked, we passed by a wine bar and I asked, "Care for one more glass of wine?"

Mom: "Hmm, I'd say we can do one more. No more Renee though."

We went inside and took our seats at the bar and promptly ordered two more glasses. We talked about the reading, and worked on our glasses until somehow the topic of dating came up.

Mom: "Seriously now, when was your last date?"

Me: "Tonight."

Mom: "Who wasn't..." And this was the awesome part. She looked at the bartender who was right in front of us and said, "Who wasn't twenty years older than you?"

She didn't say 'who wasn't your mom' and so I decided to have a little fun with this. "What are you talking about? You only have fifteen years on me, Renee. And I doubt anyone would even notice." I spoke up to the bartender. "Hey, how big do you think our age difference is?"

He already was listening into our conversation so I trusted him to help me out.

He smiled, "Yep, I wouldn't guess over ten."

Mom smirked in my direction and said, "Fine, I guess it's okay, but I have an important divorce case this week and need to get home soon." She looked at the bartender and said, "We'll close out after this one."

The bartender nodded and walked away when she returned to me and said, "Smooth stuff, mister. Fine, we can play date for this place, but that's it. We both need to date people our own age." And she whispered, "And aren't mother/son."

I reached down and grabbed her hand and she reciprocated. She said, "Ten years difference. Hah! I'll take it. You're a really good date though. Seriously though, you'd be into an older woman?"

Me: "Oh yeah, definitely. I mean, I'd date girls my age too."

Mom: "So that night in the cougar bar..."

I felt my face grow red. "Guilty as charged."

Mom: "Have you had luck with that before?"

Me: "I don't do it often. Only once or twice."

Mom: "How old of a woman?"

I don't know why, but this almost felt like a brag: "50."

She audibly gasped.

Me: "When I was 19."

In a hushed exclamation, Mom said, "She could have been your grandmother!"

Me: "Well, she didn't look 50. Just like you don't look 52," The bartender walked back over and handed the check. "I mean, you're fucking smoking, Renee."

One more audible gasp.

Mom: "Fucking smoking, eh?" God it was so hot to hear her use that language, even if it was pretty tame by today's standards. The bartender walked away and she said, "Well you're quite the young stud too, you sexy motherfucker."

Me: "Emphasis on the mother."

She busted out laughing and quickly said, "Hahah annnddddd I think about closes us up for the night. Here, I'll grab these drinks."

She set her card down as I apologized for being so forward, but she said it was all in good fun.

As we walked out, she grabbed my hand and I reached up and kissed it.

Mom grinned and rubbed my thumb with hers. "And that's the closest thing, you'll get to a kiss."

As soon as we got to our cars, mom said, "This week, I want you to make an online dating account and start meeting girls your age."

Me: "What?"

Mom: "Whatever it the current thing popular service is, I want you to sign up for it and start having dates. One per week. I know full well you're capable of that."

Me: "Okay, you did me this favor tonight so I owe you(I already had one of those hookup app accounts so mission accomplished). So no more dates then?"

Mom: "We can still get drinks, but the roleplaying stuff isn't helpful. For either of us. Do you know how long it's been since I had a date?"

Me: "Tonight?"

She busted out laughing again.

I'm not sure why I suggested it, maybe because it was fresh in my mind. I said, "Why don't you try online dating too? We can use the same app. Like moral support and stuff."

Mom: "That's not a bad idea at all."

And so that's where we left it. Later that night, I deleted my profile in the dating app and decided to start fresh as a fresh fantasy developed around matching with her and sending filthy messages that would lead to lewd pictures.

Chapter 7

A couple weeks had gone by since the reading and subsequent agreement to start finding people via a dating app. I set my age range to 22-55 on the hopes that I could maybe come across my mom, but so far there's been no luck. She refused to show me her profile, even though I showed her mine with the prominent "age range 22-55" displayed on it. Besides that, the dating app experience went pretty well. I had a few dates and they all seemed pretty interesting, even though they paled in comparison to the erotic taboo of fantasizing about my mom.

It was a Saturday night, and I just getting ready to go out on one of those dates when a text from her arrived.

Mom: I'm done with this app! I just got back from my second date and it was a disaster. All these old men just lie about their age. 52 my ass! He showed up with a walker!

Me: Well I could give you the name of a cougar site haha

Mom: I bet you can!

Mom: Mr. 22 - 55 ;)

Me: Well I've had a few good dates, haven't I?

Me: ;)

Mom: Very funny, I guess we'll have to see. I have another date tomorrow so hopefully this will be better than the last one.

Me: If not, I wouldn't mind going out with Renee again

Mom: Hah! There's no way that's gonna happen again.

The next night, her text arrived right on cue.

Mom: Yep, another total disaster.

Me: The date?

Mom: Self-absorbed asshole. I'm officially done with this and all dating.

Me: Nonsense! You're too much of a catch, mom.

Mom: You're too sweet!

Me: Again, I wouldn't mind going out with Renee again ;)

Mom: Tough Luck!

From there, I let it be for a bit until this came in two hours later

Mom: Fine, we can roleplay dating this weekend. Nothing sexual though! I just want to have a good time out with a guy.

I went from nothing to an erection in what felt like record time.

Me: Seriously?!

Mom: Sure, but I'm warning you. Any sign that you're getting corrupted and I'll end it immediately! We can meet in the city again. How about that bar we went to a couple of weeks ago?

Me: That would be incredible!

And then I decided to test things out.

Me: What if you wore something like this?

I sent her a picture of a dark green club dress. The type that barely covers the ass and cuts the cleavage almost down to the navel.

Mom: You're out of your mind! I couldn't wear something like that in public.

Me: Of course you could! You have a killer body, mom.

Mom: I suppose I'll go shopping for something new to wear, but it definitely will cover more than that!

After that, we set some ground rules. No kissing. Arm around shoulder or waist only. I can't say anything to my sister since she'll be seeing my mom leave the house for a date. Suffice to say, I was ecstatic. I spent the entire next day just jacking off the fantasy of what she would wear. I had a date with my mom.

Chapter 8

In the days ahead, we talked on and off about the upcoming date. She backed out several times, only to cave once again after showing proof that I was in fact going out on dates with other girls and would continue to do so and that our thing was just to have some fun. Our date wound up being the same bar we were at before for our last meet-up. I arrived a half-hour early in order to get us a good spot in the corner on this plush couch. Had a quick cocktail before she arrived because my nerves were through the roof. Despite that, when she walked through the door, holy shit.

Although the black dress she wore was more modest than the slutty club dress I sent her, this one was still smoking. It clung to her so tight and was cut low enough that her freckled tits were on prominent display. I was speechless as she grinned and walked over. I stood up from my seat and reached out my arms for a hug. It was weird for a moment when I had to remind myself not to give her a hug like she was my mom. She came close and once we were almost eye to eye, I realized she had on heels which probably put her around the 6'2 range.

She said my alias as I closed my arms around her and pressed her tight.

"oooh oooh" she was startled from the closeness. "I definitely need a drink!"

We ordered a round from the cocktail waitress and sat back in our couch. She leaned in to me a little and I was amazed my hardon was staying concealed.

For the first two drinks, we just talked about our normal life stuff, although it had this twist where we be telling it like we were dating. So instead of being like "School is going decent, mom" It was "School is going decent, babe." It was minor, but goddamn was it hot when she called me a stud.

Around our third drink, another couple came over and sat across from us and we started up a conversation. They were mid 30's somewhere between mine and my mom's age. It was awesome to introduce her as my date renee and her eager to play along. We made up a story that we were a freelance pair of road bike and travel magazine magazine writers who were in town to report on the city. It was a pretty good lie on my part and gave mom alot to work with since she was so familiar with road biking and traveling. I think she really liked the "roleplaying while roleplaying" thing because that's when her hand shifted onto my knee. I'm positive she had to notice my erection at that point but it didn't seem to stop her from talking to the couple about the importance of a good derailer for a bike.

I was pretty tipsy by the time we left. Our hands were interlocked and she was close. "Ugh, it's not fair. Why do you have to be my... ssssss" She began to hiss out and then started to laugh.

I busted out laughing too. "You're saying?"

"You know," My mom said and came close to me. "Our rules. You aren't going to grow up with some sex disorder about your" she looked around and said quietly. "mom."

As I thought about seeing her naked body, her firm tits, her pussy, even going so far as her asshole, all I could thing was that it was way too late to prevent some sex disorder toward my mom.

And here's where it gets good.

We were walking around looking for a night cap when we came across this dance club. It was this college dance club where the average age was my age, 22. I wanted to try for it though so I asked her if she wanted to go dance there. She protested at first that she couldn't dance, but after telling her that it would be great, I could lead, etc, she grinned and said, "Alright, but only for one song"

We went in to an incredible amount of noise and flashing lights. The dance floor was packed, but with my mom's hand in mine, I led her to the bar, got two vodka sodas, and we proceeded onto the dance floor. I grabbed her waist and began to dance. The music was pretty clubby and definitely warranted some grinding, but mom maintained her distance even though her hands kept running up and down my chest. I was drunk, but I could swear a few other guys were checking out my mom while they danced with their girls. I felt validation in a sense that I wasn't the only one who found her sexy.

"You're a good dancer!" She shouted as she put her arms around me and came close. "Everyone here is so young!"

"You are too!" I shouted back. "And just think of it as you being a cougar!"

My mom backed off for a minute and gave me a sideways look. I forgot that she didn't want to be associated with anything cougar-like.

She stepped forward and shouted, "Would a cougar do this?" and then turned around and began to grind into me. Holy shit, it only lasted a second, long enough for me to grab her hips before she backed away. Yep, she definitely felt my boner.

"This is so fucked up," Mom shouted. "You've had that this entire time!"

"It comes and it goes?" I joked. I had no idea how she felt. "What can I say? I'm 22. I'm dancing with a beautiful cougar. You have a better chance of stopping time than stopping this."

"A beautiful cougar eh?" She was back to dancing again, although at a distance.

"Absolutely, you have any idea how many guys have been oggling you tonight?"

"No way"

"Here, try this. Go to the bar. I'm going to go over there. If you get hit on in five minutes, you have to do a dare of my choosing"

"And if I don't get hit on?"

"Ummmm.... I'll clean the garage?"

"It's on!" she said and walked over to the bar. I went to the other end to try to view. She posted up and looked over at me, giving a wink. She leaned back and put both elbows on the bar to look playful in an attempt to jab me, but sure enough, these two young guys immediately walked up and began talking to her. It was an actual convo too. She was smiling and engaged and I wondered when I needed to step in. Not that I was jealous, but I was so incredibly horny from the entire date up to that point and it felt unbearable to be apart. As I watched up, she seized up for a second. It was almost too quick to notice, and then proceeded to turn around and race over to me.